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RGI-2001

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Synopsis

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Chemistry

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Also known as: Krn7000, 158021-47-7, Krn 7000, Krn-7000, Alpha-galactosylceramide, .alpha.-galcer

Molecular Formula

C₅₀H₉₉NO₉

Molecular Weight

858.3 g/mol

InChI Key

VQFKFAKEUMHBLV-BYSUZVQFSA-N

FDA UNII

WX671898JF

Alpha Galactosylceramide is a potent alpha galactosylceramide modified from marine-sponge that stimulates the immune system to exhibit antitumor activity.

1 2D Structure

RGI-2001

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-[(2S,3S,4R)-3,4-dihydroxy-1-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadecan-2-yl]hexacosanamide

2.1.2 InChI

InChI=1S/C50H99NO9/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-25-26-27-29-31-33-35-37-39-45(54)51-42(41-59-50-49(58)48(57)47(56)44(40-52)60-50)46(55)43(53)38-36-34-32-30-28-16-14-12-10-8-6-4-2/h42-44,46-50,52-53,55-58H,3-41H2,1-2H3,(H,51,54)/t42-,43+,44+,46-,47-,48-,49+,50-/m0/s1

2.1.3 InChI Key

VQFKFAKEUMHBLV-BYSUZVQFSA-N

2.1.4 Canonical SMILES

CCCCCCCCCCCCCCCCCCCCCCCCCC(=O)NC(COC1C(C(C(C(O1)CO)O)O)O)C(C(CCCCCCCCCCCCCC)O)O

2.1.5 Isomeric SMILES

CCCCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO[C@@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)O)O)[C@@H]([C@@H](CCCCCCCCCCCCCC)O)O

2.2 Other Identifiers

2.2.1 UNII

WX671898JF

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Krn 7000

2. Krn 7000, 1s-(1r*,2r*,3s*)-beta-d-galacto Isomer

3. Krn-7000

4. Krn7000

2.3.2 Depositor-Supplied Synonyms

1. Krn7000

2. 158021-47-7

3. Krn 7000

4. Krn-7000

5. Alpha-galactosylceramide

6. .alpha.-galcer

7. Ccris 8968

8. Agl-582

9. Galalpha-cer(t18:0/26:0)

10. Chebi:466659

11. 1-o-(alpha-d-galactopyranosyl)-n-hexacosanoylphytosphingosine

12. Alpha-galcer(t18:0/26:0)

13. Wx671898jf

14. Rgi-7000

15. (2s,3s,4r)-1-o-(alpha-d-galactosyl)-n-hexacosanoyl-2-amino-1,3,4-octadecanetriol

16. N-{(1s,2r,3s)-1-[(alpha-d-galactopyranosyloxy)methyl]-2,3-dihydroxyheptadecyl}hexacosanamide

17. N-[(2s,3s,4r)-1-(alpha-d-galactopyranosyloxy)-3,4-dihydroxyoctadecan-2-yl]hexacosanamide

18. N-((2s,3s,4r)-3,4-dihydroxy-1-(((2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yl)oxy)octadecan-2-yl)hexacosanamide

19. Unii-wx671898jf

20. Rgi-2001

21. Alpha-gc(c26)

22. Alpha-gc (c26)

23. Alpha-galactosyl Ceramide

24. Epitope Id:130694

25. Schembl512949

26. Chembl384200

27. Dtxsid40935847

28. Chemid158021477

29. Glxc-26234

30. Ex-a5755

31. Mfcd00939559

32. Zinc87496076

33. Db12232

34. Ac-31508

35. N-[(2s,3s,4r)-3,4-dihydroxy-1-[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadecan-2-yl]hexacosanamide

36. C16892

37. Alpha-galactosylceramide(a-gal-cer) (synthetic)

38. Q27105159

39. 1-o-(alpha-d-galactosyl)-n-hexacosanoylphytosphingosine

40. (2s,3s,4r)-1-o-(alpha-d-galactosyl)-n-hexacosanoyl-2-amino-1,3,4-octadecanetriol, >=95% (tlc)

41. Hexacosanamide, N-((1s,2s,3r)-1-((.alpha.-d-galactopyranosyloxy)methyl)-2,3-dihydroxyheptadecyl)-

42. Hexacosanamide, N-(1-((alpha-d-galactopyranosyloxy)methyl)-2,3-dihdyroxyheptadecyl)-, (1s-(1r*,2r*,3s*))-

43. Hexacosanamide, N-[(1s,2s,3r)-1-[(alpha-d-galactopyranosyloxy)methyl]-2,3-dihydroxyheptadecyl]-

44. Hexacosanamide, N-[(1s,2s,3r)-1-[(alpha-d-galactopyranosyloxy)methyl]-2,3-dihydroxyheptadecyl]- (9ci)

45. Hexacosanamide, N-[1-[(alpha-d-galactopyranosyloxy)methyl]-2,3-dihydroxyheptadecyl]-, [1s-(1r*,2r*,3s*)]-

46. N-((2s,3s,4r)-3,4-dihydroxy-1-(3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yloxy)octadecan-2-yl)hexaicosanamide

47. N-{(1s,2s,3r)-1-[(alpha-d-galactopyranosyloxy)methyl]-2,3-dihydroxyheptadecyl}hexacosanamide

48. Wurcs=2.0/1,1,0/[a2112h-1a_1-5_1*occ^sc^sc^rcccccccccccccc/6o/5o/4ncccccccccccccccccccccccccc/24=o]/1/

2.4 Create Date

2005-07-20

3 Chemical and Physical Properties

Molecular Formula	C₅₀H₉₉NO₉
Molecular Weight	858.3 g/mol
XLogP3	16
Hydrogen Bond Donor Count	7
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	44
Exact Mass	857.73198374 g/mol
Monoisotopic Mass	857.73198374 g/mol
Topological Polar Surface Area	169 Å²
Heavy Atom Count	60
Formal Charge	0
Complexity	928
Isotope Atom Count	0
Defined Atom Stereocenter Count	8
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Adjuvants, Immunologic

Substances that augment, stimulate, activate, potentiate, or modulate the immune response at either the cellular or humoral level. The classical agents (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contain bacterial antigens. Some are endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Their mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy of many biological response modifiers is related to their antigen-specific immunoadjuvanticity. (See all compounds classified as Adjuvants, Immunologic.)

Antineoplastic Agents

Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

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