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2D Structure
Also known as: 1-aminocyclopentanecarboxylic acid, 52-52-8, Cycloleucin, 1-aminocyclopentane-1-carboxylic acid, 1-amino-1-cyclopentanecarboxylic acid, 1-amino-1-carboxycyclopentane
Molecular Formula
C6H11NO2
Molecular Weight
129.16  g/mol
InChI Key
NILQLFBWTXNUOE-UHFFFAOYSA-N
FDA UNII
0TQU7668EI

An amino acid formed by cyclization of leucine. It has cytostatic, immunosuppressive and antineoplastic activities.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
1-aminocyclopentane-1-carboxylic acid
2.1.2 InChI
InChI=1S/C6H11NO2/c7-6(5(8)9)3-1-2-4-6/h1-4,7H2,(H,8,9)
2.1.3 InChI Key
NILQLFBWTXNUOE-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1CCC(C1)(C(=O)O)N
2.2 Other Identifiers
2.2.1 UNII
0TQU7668EI
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 1 Aminocyclopentanecarboxylic Acid

2. 1-aminocyclopentanecarboxylic Acid

3. Acid, 1-aminocyclopentanecarboxylic

4. Acid, Aminocyclopentanecarboxylic

5. Aminocyclopentanecarboxylic Acid

6. Nsc 1026

2.3.2 Depositor-Supplied Synonyms

1. 1-aminocyclopentanecarboxylic Acid

2. 52-52-8

3. Cycloleucin

4. 1-aminocyclopentane-1-carboxylic Acid

5. 1-amino-1-cyclopentanecarboxylic Acid

6. 1-amino-1-carboxycyclopentane

7. Cyclo-leucine

8. 1-amino-cyclopentanecarboxylic Acid

9. Cyclopentanecarboxylic Acid, 1-amino-

10. Nsc 1026

11. Cb 1639

12. X 201

13. 1-aminocyclopentanecarboxylate

14. Wr 14,997

15. Nsc1026

16. Mfcd00001381

17. Aminocyclopentanecarboxylic Acid

18. 0tqu7668ei

19. Chembl295830

20. Chebi:40547

21. Cycloleucine1-amino-cyclopentanecarboxylic Acid

22. 1-amino-1-cyclopentanecarboxylate

23. Nsc-1026

24. 1-amino-1-cyclopentane Carboxylic Acid

25. Wr 14997

26. 1-aminocyclopentane-1-carboxylate

27. 1-ammonio-1-cyclopentanecarboxylate

28. Hsdb 5195

29. 1-amino Cyclopentane Carboxylic Acid

30. Einecs 200-144-6

31. Brn 0636626

32. Unii-0tqu7668ei

33. A829129

34. Ai3-26442

35. Cyclopentanecarboxylic Acid, 1-amino-, L-

36. Leucine, Cyclo-

37. 1-aminocyclopentane Carboxylic Acid

38. Cycloleucine, 97%

39. (2e)-decenoyl-acp

40. Spectrum_001268

41. 1y1m

42. H-nh(1)cpen-oh

43. Ac1ocg3t

44. Spectrum2_000931

45. Spectrum3_001514

46. Spectrum4_000340

47. Spectrum5_001136

48. Cycloleucine [mi]

49. Biomol-nt_000201

50. Cycloleucine [hsdb]

51. Ncimech_000677

52. Wln: L5tj Az Avq

53. Schembl8495

54. Bspbio_003187

55. Cycloleucin [who-dd]

56. Kbiogr_000719

57. Kbioss_001748

58. 4-14-00-00974 (beilstein Handbook Reference)

59. Divk1c_000723

60. Spectrum1502128

61. Spbio_000862

62. 1-amino-cyclopentanecarboxylate

63. Bpbio1_001084

64. Zinc1234

65. Cyclopentanecarboxylic Acid, L-

66. 1-aminocyclopentanecarboxylicacid

67. Acid, Aminocyclopentanecarboxylic

68. Dtxsid5024475

69. Hms502e05

70. Kbio1_000723

71. Kbio2_001748

72. Kbio2_004316

73. Kbio2_006884

74. Kbio3_002687

75. Nilqlfbwtxnuoe-uhfffaoysa-

76. 1 Aminocyclopentanecarboxylic Acid

77. Ninds_000723

78. Hms1921l08

79. Acid, 1-aminocyclopentanecarboxylic

80. Act04362

81. Albb-035361

82. Cs-b0093

83. 1-amino-cyclopentane Carboxylic Acid

84. Bbl020454

85. Bdbm50070638

86. Ccg-35835

87. Fd1031

88. Stk133034

89. Zinc00001234

90. Akos000183252

91. Ac-2700

92. Cb-1639

93. Db04620

94. Idi1_000723

95. Ncgc00094966-01

96. Ncgc00094966-02

97. Ncgc00094966-03

98. Ncgc00094966-04

99. Ncgc00163268-01

100. Ncgc00178218-01

101. Ac5

102. As-11677

103. Hy-30008

104. Nci60_000070

105. Sy002601

106. Cycloleucine1-amino-cyclopentanecarboxylate

107. Cyclopentanecarboxylic Acid, L-amino

108. Db-031284

109. Am20100281

110. Ft-0607341

111. En300-39470

112. C03969

113. 001c381

114. Q607775

115. J-504199

116. J-802019

117. F8881-4536

118. 3dd7e30b-2149-43d9-a44b-7a59d546a28b

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 129.16 g/mol
Molecular Formula C6H11NO2
XLogP3-2.6
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count3
Rotatable Bond Count1
Exact Mass129.078978594 g/mol
Monoisotopic Mass129.078978594 g/mol
Topological Polar Surface Area63.3 Ų
Heavy Atom Count9
Formal Charge0
Complexity127
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

EXPTL USE (VET): SINGLE DOSES OF ANTILYMPHOCYTE SERUM, CYCLOPHOSPHAMIDE, CYCLOLEUCINE DELAYED ONSET OF HYPERACUTE FORM OF EXPTL ALLERGIC ENCEPHALOMYELITIS IN RATS. CYCLOLEUCINE & TILORONE-HCL WERE PROVEN TO HAVE SYNERGISTIC RELATIONSHIP.

LEVINE S, SOWINSKI R; PROC SOC EXP BIOL MED 156(3) 457 (1977)


EXPTL USE: (11)C-CYCLOLEUCINE WAS EVALUATED AS TUMOR SCANNING AGENT IN 38 PT. EXTRAPOLATION FROM ANIMAL DATA GIVES 0.01 RAD/UCI FOR WHOLE BODY & LESS THAN 0.06 RAD/UCI FOR PANCREAS. 33/38 HAS GALLIUM CITRATE (67)GA SCANS ALSO; RESULTS 19 POS FORMER & 24 POS (67)GA SCANS.

HUBNER ET AL; J NUCL MED 18(DEC) 1215 (1977)


MEDICATION (VET): CARBOXYL-LABELED (11)C-CYCLOLEUCINE WAS PREPD IN MULTIMILLICURIE AMT. TISSUE DISTRIBUTION (750 MICROCURIE, IV) IN MORRIS 5123 C HEPATOMA BEARING RATS INDICATED THE COMPD HAS POTENTIAL AS TUMOR-LOCALIZING AGENT FOR DETECTING CANCER IN HUMANS.

HAYES ET AL; J NUCL MED 17(8) 748 (1976)


MEDICATION (VET): CYCLOLEUCINE PROTECTED RATS AGAINST SEIZURES IN MAXIMAL ELECTROSHOCK TEST BUT OFFERED NO PROTECTION AGAINST METRAZOL-(PENTYLENETETRAZOL) INDUCED SEIZURES IN MICE.

ZAN R, IZQUIERDO I; NEUROCHEM RES 5(1) 1 (1980)


5 Pharmacology and Biochemistry
5.1 Pharmacology

Cycloleucine has cytostatic, immunosuppressive and antineoplastic activities.


5.2 Absorption, Distribution and Excretion

LEVELS OF (14)C IN LIVER & PANCREAS WERE RESPECTIVELY EIGHTFOLD & TWOFOLD THOSE IN BLOOD, 15 MIN AFTER IV DOSE OF [(14)C]-1-AMINOCYCLOPENTANECARBOXYLIC ACID TO RHESUS MONKEYS. (14)C LEVELS IN THESE TISSUES WERE SIMILAR TO THOSE IN BLOOD AFTER 24 HR.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 2: A Review of the Literature Published Between 1970 and 1971. London: The Chemical Society, 1972., p. 122


WHEN ADMIN TO MICE CYCLOLEUCINE ACCUM IN TISSUES AT LEVELS BETWEEN 0.02 & 1.29 MG/ML. MOST OF REMAINING 2% WAS ASSOC WITH PROTEIN. ACCUM AGAINST CONCN GRADIENT OCCURRED IN KIDNEY, IN SPLEEN TO GREATER EXTENT & TO MUCH GREATER DEGREE IN PANCREAS. THE DISTRIBUTION RATIOS FOR CNS TISSUE, KIDNEY & SPLEEN DID NOT CHANGE AS FUNCTION OF PLASMA CYCLOLEUCINE CONCN OR OF TIME BETWEEN 4 & 40 DAYS AFTER ADMIN TO MICE. 5 DAYS AFTER ADMIN OF CYCLOLEUCINE TO MICE, HEPATIC CYCLOLEUCINE DISTRIBUTION RATIO WAS CONSIDERABLY GREATER THAN UNITY AT THE LOWEST DOSES & INCR VARIABLY WITH INCR CYCLOLEUCINE PLASMA LEVELS.

NIXON RA; BIOCHEM PHARMACOL 25(6) 726 (1976)


5.3 Biological Half-Life

AT 0.4-0.5 MG/G PLASMA LEVEL AT 24 DAYS WAS NOT SIGNIFICANTLY DIFFERENT FROM THAT AT 1 DAY. HIGHEST DOSES (1-3 MG/G) RESULTED IN NEARLY SIMILAR PLASMA LEVELS BY 4TH DAY. T/2 IN PLASMA WAS EXTREMELY LONG.

NIXON RA; BIOCHEM PHARMACOL 25(6) 726 (1976)


5.4 Mechanism of Action

SYNTHETIC AMINO ACID THOUGHT TO ACT AS VALINE ANTAGONIST.

The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 357