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    Chemistry

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    Also known as: Chenodiol, 474-25-9, Chenix, Chenic acid, Cdca, Chenodeoxycholate
    Molecular Formula
    C24H40O4
    Molecular Weight
    392.6  g/mol
    InChI Key
    RUDATBOHQWOJDD-BSWAIDMHSA-N
    FDA UNII
    0GEI24LG0J
    Chenodeoxycholic Acid
    A bile acid, usually conjugated with either glycine or taurine. It acts as a detergent to solubilize fats for intestinal absorption and is reabsorbed by the small intestine. It is used as cholagogue, a choleretic laxative, and to prevent or dissolve gallstones.
    1 2D Structure

    Chenodeoxycholic Acid

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (4R)-4-[(3R,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
    2.1.2 InChI
    InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17-,18+,19+,20-,22+,23+,24-/m1/s1
    2.1.3 InChI Key
    RUDATBOHQWOJDD-BSWAIDMHSA-N
    2.1.4 Canonical SMILES
    CC(CCC(=O)O)C1CCC2C1(CCC3C2C(CC4C3(CCC(C4)O)C)O)C
    2.1.5 Isomeric SMILES
    C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2[C@@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)C
    2.2 Other Identifiers
    2.2.1 UNII
    0GEI24LG0J
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Acid, Chenic

    2. Acid, Chenique

    3. Acid, Chenodeoxycholic

    4. Acid, Gallodesoxycholic

    5. Chenic Acid

    6. Chenique Acid

    7. Chenix

    8. Chenodeoxycholate

    9. Chenodeoxycholate, Sodium

    10. Chenodiol

    11. Chenofalk

    12. Chenophalk

    13. Gallodesoxycholic Acid

    14. Henohol

    15. Quenobilan

    16. Quenocol

    17. Sodium Chenodeoxycholate

    2.3.2 Depositor-Supplied Synonyms

    1. Chenodiol

    2. 474-25-9

    3. Chenix

    4. Chenic Acid

    5. Cdca

    6. Chenodeoxycholate

    7. Chenodesoxycholic Acid

    8. Gallodesoxycholic Acid

    9. Chendol

    10. Anthropodeoxycholic Acid

    11. Anthropodesoxycholic Acid

    12. Chenofalk

    13. Anthropododesoxycholic Acid

    14. Chenodesoxycholsaeure

    15. Chenodiol [usan]

    16. Chenocol

    17. Chenossil

    18. Cholanorm

    19. Fluibil

    20. Xenbilox

    21. Chenocholic Acid

    22. 3alpha,7alpha-dihydroxy-5beta-cholan-24-oic Acid

    23. Acido Chenodeoxicholico

    24. 3alpha,7alpha-dihydroxy-5beta-cholanic Acid

    25. Chenodesoxycholsaeure [german]

    26. Acide Chenodeoxycholique

    27. 7-alpha-hydroxylithocholic Acid

    28. Acidum Chenodeoxycholicum

    29. 7alpha-hydroxylithocholic Acid

    30. Acide Chenodeoxycholique [inn-french]

    31. Acido Chenodeoxicholico [inn-spanish]

    32. Acidum Chenodeoxycholicum [inn-latin]

    33. 3-alpha,7-alpha-dihydroxycholanic Acid

    34. 3-alpha,7-alpha-dihydroxycholansaeure [german]

    35. (4r)-4-[(3r,5s,7r,8r,9s,10s,13r,14s,17r)-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]pentanoic Acid

    36. 3-alpha,7-alpha-dihydroxycholansaeure

    37. 0gei24lg0j

    38. Chenodeoxycholic Acid [inn]

    39. 3-alpha,7-alpha-dihydroxy-5-beta-cholan-24-oic Acid

    40. Chebi:16755

    41. Cholan-24-oic Acid, 3,7-dihydroxy-, (3alpha,5beta,7alpha)-

    42. Chenodiol (usan)

    43. Cholan-24-oic Acid, 3,7-dihydroxy-, (3a,5b,7a)-

    44. Nsc-657949

    45. Nsc-757798

    46. (3alpha,5beta,7alpha)-3,7-dihydroxycholan-24-oic Acid

    47. 5-beta-cholan-24-oic Acid, 3-alpha,7-alpha-dihydroxy-

    48. (3alpha,5beta,7alpha,8xi)-3,7-dihydroxycholan-24-oic Acid

    49. Henohol

    50. Chenique Acid

    51. Cholan-24-oic Acid, 3,7-dihydroxy-, (3-alpha,5-beta,7-alpha)-

    52. Dsstox_cid_260

    53. Dsstox_rid_75469

    54. Dsstox_gsid_20260

    55. 3.alpha.,7.alpha.-dihydroxy-5.beta.-cholan-24-oic Acid

    56. (4r)-4-[(1s,2s,5r,7s,9r,10r,11s,14r,15r)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic Acid

    57. Chendeoxycholic Acid

    58. Ccris 2195

    59. Einecs 207-481-8

    60. Unii-0gei24lg0j

    61. Nsc 657949

    62. Chenocedon

    63. Chendal

    64. Chenodex

    65. Chenorm

    66. Hekbilin

    67. Kebilis

    68. Mfcd00064142

    69. Nsc657949

    70. Ncgc00016387-02

    71. (r)-4-((3r,5s,7r,8r,9s,10s,13r,14s,17r)-3,7-dihydroxy-10,13-dimethylhexadecahydro-1h-cyclopenta[a]phenanthren-17-yl)pentanoic Acid

    72. Cas-474-25-9

    73. Jn3

    74. Chenodeoxycholic-acid

    75. (+)-chenodeoxycholate

    76. Chenodiol [mi]

    77. Prestwick0_000285

    78. Prestwick1_000285

    79. Prestwick2_000285

    80. Prestwick3_000285

    81. Spectrum5_002009

    82. Chenix (tn)

    83. Chenodiol [vandf]

    84. (+)-chenodeoxycholic Acid

    85. Bmse000908

    86. 7a-hydroxy-desoxycholsaeure

    87. Ec 207-481-8

    88. Bidd:pxr0056

    89. Schembl25055

    90. Bspbio_000190

    91. Gtpl608

    92. Mls002154253

    93. 3a,7a-dihydroxy-5b-cholanate

    94. Spbio_002409

    95. 3,7-dihydroxy-5-cholanicacid

    96. Bpbio1_000210

    97. Chembl240597

    98. Chenodeoxycholic Acid, >=97%

    99. Chenodiol [orange Book]

    100. Dtxsid2020260

    101. 7.alpha.-hydroxylithocholic Acid

    102. Bdbm21674

    103. Chenodeoxycholic Acid, Free Acid

    104. 3a,7a-dihydroxy-5b-cholanic Acid

    105. Hms1568j12

    106. Hms2095j12

    107. Hms2234i22

    108. Hms3712j12

    109. Chenodeoxycholic Acid (jp16/inn)

    110. Chenodeoxycholic Acid (jp17/inn)

    111. Chenodeoxycholic Acid [jan]

    112. Zinc3914808

    113. Tox21_110412

    114. Tox21_200491

    115. (3beta,7beta,8xi,9xi,14xi,17alpha)-3,7-dihydroxycholan-24-oic Acid

    116. 3a,7a-dihydroxy-5b-cholan-24-oate

    117. Cholan-24-oic Acid, 3,7-dihydroxy-, (3.alpha.,5.beta.,7.alpha.)-

    118. Hsci1_000210

    119. Lmst04010032

    120. Chenodeoxycholic Acid [mart.]

    121. Akos024280614

    122. Chenodeoxycholic Acid [who-dd]

    123. Ccg-220285

    124. Cs-0834

    125. Db06777

    126. 5beta-cholanic Acid-3alpha,7alpha-diol

    127. Smp1_000064

    128. 3.alpha.,7.alpha.-dihydroxycholansaeure

    129. 3a,7a-dihydroxy-5b,14a,17b-cholanate

    130. 3a,7a-dihydroxy-5b-cholan-24-oic Acid

    131. Ncgc00142400-03

    132. Ncgc00142400-04

    133. Ncgc00142400-08

    134. Ncgc00258045-01

    135. (4r)-4-((1s,2s,7s,11s,5r,9r,10r,14r,15r)-5,9-dihydroxy-2,15-dimethyltetracyclo [8.7.0.0<2,7>.0<11,15>]heptadec-14-yl)pentanoic Acid

    136. 24404-86-2

    137. 3.alpha.,7.alpha.-dihydroxycholanic Acid

    138. As-13636

    139. Hy-76847

    140. Smr000857194

    141. Chenodeoxycholic Acid [ep Impurity]

    142. Chenodeoxycholic Acid [ep Monograph]

    143. 3a,7a-dihydroxy-5b,14a,17b-cholanic Acid

    144. Ab00513822

    145. S1843

    146. (3a,5b,7a)-3,7-dihydroxy-cholan-24-oate

    147. 3alpha, 7alpha-dihydroxy-5beta-cholanoic Acid

    148. 3alpha, 7alpha,-dihydroxy-5beta-cholanic Acid

    149. C-2900

    150. C02528

    151. D00163

    152. (3a,5b,7a)-3,7-dihydroxy-cholan-24-oic Acid

    153. Ab00513822-06

    154. Ab00513822_07

    155. A827222

    156. Q419028

    157. 3.alpha.,7.alpha.-dihydroxy-5.beta.-cholanic Acid

    158. Dihydroxy-3.alpha.,7.alpha.(5.beta.)cholanic Acid

    159. Leadiant (formerly Chenodeoxycholic Acid Sigma-tau)

    160. (3

    161. A,5

    162. A,7

    163. A)-3,7-dihydroxycholan-24-oic Acid

    164. 3.alpha.,7.alpha.-dihydroxy-5.beta.-cholanoic Acid

    165. Brd-k18135438-001-16-7

    166. Ursodeoxycholic Acid Impurity A [ep Impurity]

    167. 0dbbbc66-0cfa-4db9-97f4-5b1492756a02

    168. Z1270387252

    169. 5.beta.-cholan-24-oic Acid, 3.alpha.,7.alpha.-dihydroxy-

    170. (3alpha,5alpha,7beta,8alpha,17alpha)-3,7-dihydroxycholan-24-oic Acid

    171. 3,7-dihydroxycholan-24-oic Acid, (3.alpha.,5.beta.,7.alpha.)- #

    172. Chenodeoxycholic Acid, 500 Mug/ml In Methanol, Certified Reference Material

    173. Chenodeoxycholic Acid, European Pharmacopoeia (ep) Reference Standard

    174. Cholan-24-oic Acid, 3,7-dihydroxy-, (3-.alpha., 5-.beta., 7-.alpha.)-

    175. Cholan-24-oic Acid, 3,7-dihydroxy-, (3-alpha,5-beta,7-alpha)- (9ci)

    176. Cholan-24-oic Acid, 3,7-dihydroxy-, (3.alpha.,5.beta.,7.alpha.)

    177. (4r)-4-[(1s,2s,5r,7s,9r,10r,11s,14r,15r)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0?,?.0??,??]heptadecan-14-yl]pentanoic Acid

    2.4 Create Date
    2004-09-16
    3 Chemical and Physical Properties
    Molecular Weight 392.6 g/mol
    Molecular Formula C24H40O4
    XLogP34.9
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count4
    Exact Mass392.29265975 g/mol
    Monoisotopic Mass392.29265975 g/mol
    Topological Polar Surface Area77.8 Ų
    Heavy Atom Count28
    Formal Charge0
    Complexity605
    Isotope Atom Count0
    Defined Atom Stereocenter Count10
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameChenodiol
    PubMed HealthChenodiol (By mouth)
    Drug ClassesGastrointestinal Agent
    Drug LabelChenodiol is the non-proprietary name for chenodeoxycholic acid, a naturally occurring human bile acid. It is a bitter-tasting white powder consisting of crystalline and amorphous particles freely soluble in methanol, acetone and acetic acid and prac...
    Active IngredientChenodiol
    Dosage FormTablet
    RouteOral
    Strength250mg
    Market StatusPrescription
    CompanyNexgen Pharma

    2 of 2  
    Drug NameChenodiol
    PubMed HealthChenodiol (By mouth)
    Drug ClassesGastrointestinal Agent
    Drug LabelChenodiol is the non-proprietary name for chenodeoxycholic acid, a naturally occurring human bile acid. It is a bitter-tasting white powder consisting of crystalline and amorphous particles freely soluble in methanol, acetone and acetic acid and prac...
    Active IngredientChenodiol
    Dosage FormTablet
    RouteOral
    Strength250mg
    Market StatusPrescription
    CompanyNexgen Pharma

    4.2 Drug Indication

    Chenodiol is indicated for patients with radiolucent stones in well-opacifying gallbladders, in whom selective surgery would be undertaken except for the presence of increased surgical risk due to systemic disease or age. Chenodiol will not dissolve calcified (radiopaque) or radiolucent bile pigment stones.

    FDA Label

    Chenodeoxycholic acid is indicated for the treatment of inborn errors of primary bile acid synthesis due to sterol 27 hydroxylase deficiency (presenting as cerebrotendinous xanthomatosis (CTX)) in infants, children and adolescents aged 1 month to 18 years and adults.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    It acts by reducing levels of cholesterol in the bile, helping gallstones that are made predominantly of cholesterol to dissolve. Chenodeoxycholic acid is ineffective with stones of a high calcium or bile acid content.

    5.2 MeSH Pharmacological Classification

    Cathartics

    Agents that are used to stimulate evacuation of the bowels. (See all compounds classified as Cathartics.)

    Gastrointestinal Agents

    Drugs used for their effects on the gastrointestinal system, as to control gastric acidity, regulate gastrointestinal motility and water flow, and improve digestion. (See all compounds classified as Gastrointestinal Agents.)

    5.3 ATC Code

    A05AA01

    A - Alimentary tract and metabolism

    A05 - Bile and liver therapy

    A05A - Bile therapy

    A05AA - Bile acids and derivatives

    A05AA01 - Chenodeoxycholic acid

    5.4 Absorption, Distribution and Excretion

    Absorption

    Chenodiol is well absorbed from the small intestine.

    Route of Elimination

    About 80% of its bacterial metabolite lithocholate is excreted in the feces.

    5.5 Metabolism/Metabolites

    Chenodiol is well absorbed from the small intestine and taken up by the liver where it is converted to its taurine and glycine conjugates and secreted in bile. At steady-state, an amount of chenodiol near the daily dose escapes to the colon and is converted by bacterial action to lithocholic acid. About 80% of the lithocholate is excreted in the feces; the remainder is absorbed and converted in the liver to its poorly absorbed sulfolithocholyl conjugates. During chenodiol therapy there is only a minor increase in biliary lithocholate, while fecal bile acids are increased three- to fourfold.

    5.6 Mechanism of Action

    Chenodiol suppresses hepatic synthesis of both cholesterol and cholic acid, gradually replacing the latter and its metabolite, deoxycholic acid in an expanded bile acid pool. These actions contribute to biliary cholesterol desaturation and gradual dissolution of radiolucent cholesterol gallstones in the presence of a gall-bladder visualized by oral cholecystography. Bile acids may also bind the the bile acid receptor (FXR) which regulates the synthesis and transport of bile acids.

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\/ CHENODEOXYCHOLIC ACID (ORGANIC CHEMICALS) (FORLABORATORY ANALYTICAL TESTING PURPOSE )","address":"17 LOTUS BUSINESS PARK,NEW LINK RD ANDHERI W","city":"MUMBAI,MAHARASHTRA","supplier":"ACDIMA BIO CENTER","supplierCountry":"INDIA","foreign_port":"NA","customer":"CLEARSYNTH LABS LIMITED","customerCountry":"INDIA","quantity":"0.00","actualQuantity":"200","unit":"MGS","unitRateFc":"0.3","totalValueFC":"61.2","currency":"EUR","unitRateINR":"24.5","date":"20-Sep-2022","totalValueINR":"4902.54","totalValueInUsd":"61.2","indian_port":"BOMBAY AIR","hs_no":"29419090","bill_no":"2522715","productDescription":"Re-Import","marketType":"REGULATED MARKET","country":"INDIA","selfForZScoreResived":"Pharma Grade","supplierPort":"NA","supplierAddress":"","customerAddress":"17 LOTUS BUSINESS PARK,NEW LINK RD ANDHERI W"},{"dataSource":"API Import","activeIngredients":"","year":"2022","qtr":"Q4","strtotime":1668018600,"product":"CHENODEOXYCHOLIC ACID(4R)-4-(3R,55,7R,8R,10S,13R,14S,17R)-3-7DIHYDROXY-10-13DIMITHYLHEXADEHYDRO-1H-CYCLOPENTA PHENATHREN","address":"8-3-166\/182, A BLOCK, NORTH WING,, 105-108, IST FLOOR CHALLA ESTATES,","city":"ERRADADDA,TELANGANA","supplier":"QINGDAO HAOSAIL SCIENCE","supplierCountry":"CHINA","foreign_port":"NA","customer":"DASAMI LAB PRIVATE ","customerCountry":"INDIA","quantity":"700.00","actualQuantity":"700","unit":"KGS","unitRateFc":"95","totalValueFC":"68282.3","currency":"USD","unitRateINR":"7961","date":"10-Nov-2022","totalValueINR":"5572700","totalValueInUsd":"68282.3","indian_port":"MADRAS AIR","hs_no":"29349990","bill_no":"3245034","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"NA","supplierAddress":"","customerAddress":"8-3-166\/182, A BLOCK, NORTH WING,, 105-108, IST FLOOR CHALLA ESTATES,"},{"dataSource":"API Import","activeIngredients":"","year":"2023","qtr":"Q3","strtotime":1695321000,"product":"CHENODEOXYCHOLIC ACID (40 DRUMS)","address":"TRIDENT GROUP COMPLEX,","city":"TEHSIL BARNALA","supplier":"HIGH HOPE INT'L GROUP JIANGSU MEDICINES","supplierCountry":"CHINA","foreign_port":"BEIJING","customer":"IOL CHEMICALS AND PHARMACEUTICALS","customerCountry":"INDIA","quantity":"1000.00","actualQuantity":"1000","unit":"KGS","unitRateFc":"86","totalValueFC":"87079.3","currency":"USD","unitRateINR":"7228.3","date":"22-Sep-2023","totalValueINR":"7228300","totalValueInUsd":"87079.3","indian_port":"Delhi Air","hs_no":"29181990","bill_no":"7964063","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"BEIJING","supplierAddress":"PRODUCTS IMP.&EXP.CORP.LTD. 10-11 FLOOR, HIGH HOPE BUILDING , 91 BAI XIA ROAD, NANJING JIANGSU CHINA P.C: CHINA","customerAddress":"TRIDENT GROUP COMPLEX,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q1","strtotime":1709749800,"product":"CHENODEOXYCHOLIC ACID 95% (QTY=1 CTN\/2 KGS)","address":"11\/2, KIADB AREA,","city":"ANEKAL TQ. BANGALORE","supplier":"INFOARK INTERNATIONAL CO. ","supplierCountry":"CHINA","foreign_port":"BEIJING","customer":"SONIA ORGANICS","customerCountry":"INDIA","quantity":"2.00","actualQuantity":"2","unit":"KGS","unitRateFc":"150","totalValueFC":"303.1","currency":"USD","unitRateINR":"12585","date":"07-Mar-2024","totalValueINR":"25170","totalValueInUsd":"303.1","indian_port":"Bangalore Air","hs_no":"29181990","bill_no":"2464473","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"BEIJING","supplierAddress":"ROOM 807B NEW LAND PLAZA,58 FUCHENG ROAD, HAIDIAN DISTRICT,BEIJING CHINA CN","customerAddress":"11\/2, KIADB AREA,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q2","strtotime":1716489000,"product":"CHENODEOXYCHOLIC ACID","address":"HETERO CORPORATE, NO. 7-2-A2,","city":"HYDERABAD","supplier":"HANGZHOU QICHUANG CHEMICAL","supplierCountry":"CHINA","foreign_port":"HANGCHOW (HANGZHOU)","customer":"HETERO DRUGS","customerCountry":"INDIA","quantity":"2.00","actualQuantity":"2","unit":"KGS","unitRateFc":"200","totalValueFC":"404.8","currency":"USD","unitRateINR":"16870","date":"24-May-2024","totalValueINR":"33740","totalValueInUsd":"404.8","indian_port":"Madras Air","hs_no":"29189990","bill_no":"3649934","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"HANGCHOW (HANGZHOU)","supplierAddress":"ROOM 1204, NO.46, TIANMUSHAN ROAD,XIHU DISTRICT, HANGZHOUSDNF CHINA","customerAddress":"HETERO CORPORATE, NO. 7-2-A2,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q4","strtotime":1729276200,"product":"CHENODEOXYCHOLIC ACID(3ALPHA,7ALPHA-DIHYDROXY-5 BETA-CHOLAN-24-OIC ACID)(CAS NO:474-25-9)","address":"CISONS COMPLEX,SHOPNO.77, 1ST FLOOR","city":"ROAD, EGMORE, CHENNAI, TAMIL NADU","supplier":"ZHEJIANG Z-STAR PHARMA CO.,LTD, ROOM 1507,","supplierCountry":"CHINA","foreign_port":"SHANGHAI","customer":"SYMBIO GENERRICS INDIA ","customerCountry":"INDIA","quantity":"1000.00","actualQuantity":"1000","unit":"KGS","unitRateFc":"67","totalValueFC":"67695.9","currency":"USD","unitRateINR":"5688.3","date":"19-Oct-2024","totalValueINR":"5688252","totalValueInUsd":"67695.9","indian_port":"Madras Sea","hs_no":"29181990","bill_no":"6218243","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"SHANGHAI","supplierAddress":"EAST NO.1, BULDING TENGDA,CENTRAL, NO.1800 DONGHAI ROAD, BAIYUN STREET JIAOJIANG DST, TAIZHOU CITY ZHEJIAN CN","customerAddress":"CISONS COMPLEX,SHOPNO.77, 1ST FLOOR"}]
    06-Aug-2021
    19-Oct-2024
    KGS
    overview
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    Average Price (USD/KGS)

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    Quantity (KGS) & Unit rate (USD/KGS) over time

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    Importing Country Total Quantity
    (KGS)    		 Average Price
    (USD/KGS)    		 Number of Transactions

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