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Prestwick3_000089

Prestwick3_000089

Synopsis, Chemistry

APIs // Active Pharmaceutical Ingredients

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1 USP Standards, 3 Other Ref. Standards

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Also known as: 77-52-1, Prunol, Malol, Urson, 3beta-hydroxyurs-12-en-28-oic acid, (3beta)-3-hydroxyurs-12-en-28-oic acid

Molecular Formula

C₃₀H₄₈O₃

Molecular Weight

456.7 g/mol

InChI Key

WCGUUGGRBIKTOS-GPOJBZKASA-N

FDA UNII

P3M2575F3F

Ursolic Acid is a pentacyclic triterpenoid found in various fruits, vegetables and medicinal herbs, with a variety of potential pharmacologic activities including anti-inflammatory, antioxidative, antiviral, serum lipid-lowering, and antineoplastic activities. Upon administration, ursolic acid may promote apoptosis and inhibit cancer cell proliferation through multiple mechanisms. This may include the regulation of mitochondrial function through various pathways including the ROCK/PTEN and p53 pathways, the suppression of the nuclear factor-kappa B (NF-kB) pathways, and the increase in caspase-3, caspase-8 and caspase-9 activities.

1 2D Structure

Prestwick3_000089

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1S,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid

2.1.2 InChI

InChI=1S/C30H48O3/c1-18-10-15-30(25(32)33)17-16-28(6)20(24(30)19(18)2)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h8,18-19,21-24,31H,9-17H2,1-7H3,(H,32,33)/t18-,19+,21+,22-,23+,24+,27+,28-,29-,30+/m1/s1

2.1.3 InChI Key

WCGUUGGRBIKTOS-GPOJBZKASA-N

2.1.4 Canonical SMILES

CC1CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)O)C)C)C2C1C)C)C(=O)O

2.1.5 Isomeric SMILES

C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)O)C)C)[C@@H]2[C@H]1C)C)C(=O)O

2.2 Other Identifiers

2.2.1 UNII

P3M2575F3F

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (+)-ursolic Acid

2. (3 Beta)-3-hydroxyurs-12-en-28-oic Acid

3. 3-epi-ursolic Acid

4. 3-epiursolic Acid

5. 3alpha-ursolic Acid

6. 3beta-ursolic Acid

7. Merotaine

8. Olean-12-en-28-oic Acid, 3-hydroxy-, Sodium Salt (1:1), (3beta)-

9. Sodium Oleanolate

10. Ursolic Acid Monosodium Salt

11. Ursolic Acid Sodium Salt

12. Ursolic Acid, (3beta)-isomer, 2-(14)c-labeled

13. Ursolic Acid, (3beta)-isomer, Monopotassium Salt

2.3.2 Depositor-Supplied Synonyms

1. 77-52-1

2. Prunol

3. Malol

4. Urson

5. 3beta-hydroxyurs-12-en-28-oic Acid

6. (3beta)-3-hydroxyurs-12-en-28-oic Acid

7. Micromerol

8. Ursolic-acid

9. Nsc-4060

10. Nsc 167406

11. (+)-ursolic Acid

12. Chebi:9908

13. Chembl169

14. Nsc-167406

15. P3m2575f3f

16. .beta.-ursolic Acid

17. (1s,2r,4as,6ar,6as,6br,8ar,10s,12ar,14bs)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1h-picene-4a-carboxylic Acid

18. 3b-hydroxyurs-12-en-28-oic Acid

19. Nsc 4060

20. Bungeolic Acid

21. 3beta-hydroxy-12-ursen-28-ic Acid

22. Nsc4060

23. Mfcd00009621

24. Smr000445681

25. Sr-01000779684

26. Einecs 201-034-0

27. Urs-12-en-28-oic Acid, 3-hydroxy-, (3.beta.)-

28. Tnp00103

29. Unii-p3m2575f3f

30. Uosolic Acid

31. Ai3-03109

32. Hsdb 7685

33. 6q5

34. Urs-12-en-28-oic Acid, 3-hydroxy-, (3beta)-

35. Urs-12-en-28-oic Acid, 3beta-hydroxy-

36. Prestwick3_000089

37. Ursolic Acid, >=90%

38. Ursolic Acid [mi]

39. Ursolic Acid [hsdb]

40. Ursolic Acid [inci]

41. Schembl70205

42. Bspbio_000018

43. Mls000728569

44. Mls002154196

45. Mls002207073

46. Ursolic Acid [usp-rs]

47. Ursolic Acid [who-dd]

48. Bpbio1_000020

49. N-ethylhydroxylaminehydrochloride

50. Dtxsid70883221

51. Ursolic Acid, Analytical Standard

52. 3beta-hydroxyurs-12-en-28-oate

53. Hms2095a20

54. Hms2231p19

55. (1s,2r,4as,6as,6br,8ar,10s,12ar,12br,14bs)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic Acid

56. 3beta-hydroxy-urs-12-en-28-oate

57. Hy-n0140

58. Zinc3978827

59. Bdbm50148911

60. 3beta-hydroxy-12-ursen-28-oic Acid

61. Akos005228010

62. Akos016023773

63. 3.beta.-hydroxy-urs-12-en-28-oate

64. Ccg-208282

65. Cs-3799

66. Db15588

67. Lmpr0106180007

68. (3beta)-3-hydroxyurs-12-en-28-oate

69. 3beta-hydroxy-urs-12-en-28-oic Acid

70. (3beta)-3-hydroxy-urs-12-en-28-oate

71. As-35119

72. 3.beta.-hydroxy-urs-12-en-28-oic Acid

73. (3beta)-3-hydroxy-urs-12-en-28-oic Acid

74. Ab00513802

75. N1823

76. U0065

77. C08988

78. 009u621

79. A839123

80. Q416260

81. Q-201916

82. Sr-01000779684-4

83. Sr-01000779684-5

84. (3.beta.)-3-hydroxyurs-12-en-28-oic Acid

85. Brd-k68185022-001-02-3

86. Brd-k68185022-001-14-8

87. Ursolic Acid, Primary Pharmaceutical Reference Standard

88. Af479d19-631e-48f1-8aba-fb2a806046fa

89. Ursolic Acid (constituent Of Holy Basil Leaf) [dsc]

90. (3beta,5beta,18alpha,20beta)-3-hydroxyurs-12-en-28-oic Acid

91. Ursolic Acid, European Pharmacopoeia (ep) Reference Standard

92. Ursolic Acid, United States Pharmacopeia (usp) Reference Standard

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₃₀H₄₈O₃
Molecular Weight	456.7 g/mol
XLogP3	7.3
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	1
Exact Mass	456.36034539 g/mol
Monoisotopic Mass	456.36034539 g/mol
Topological Polar Surface Area	57.5 Å²
Heavy Atom Count	33
Formal Charge	0
Complexity	874
Isotope Atom Count	0
Defined Atom Stereocenter Count	10
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Therapeutic Uses

/EXPL/ The methanol extract (ME) and the n-butanol fractions of methanolic extract of Alstonia macrophylla Wall ex A. DC leaves were investigated on the forward motility (FM) of mammalian (goat and human) spermatozoa. The ME at 600 ug/mL as well as fraction B at 100 ug/mL concentrations showed marked inhibition of sperm FM in both goat and human species ... .. Approximately 60-80% of the goat spermatozoa lost their FM when treated with 600 ug/mL of ME and 100 ug/mL of fraction B. At 100 ug/mL concentration, fraction B showed 90% loss of FM in human spermatozoa, while fraction B at 400 ug/mL concentration showed complete inhibition of sperm FM at 0 min. The inhibitory activity of fraction B increases with increasing concentration in a dose-dependent manner. ... Fraction B (ursolic acid), a pentacyclic triterpene, has the potential of sperm motility inhibition and can serve as a topical vaginal contraceptive.

PMID:15854639 Chattopadhyay D et al; Contraception 71 (5): 372-8 (2005)

Both oleanolic acid and ursolic acid are effective in protecting against chemically induced liver injury in laboratory animals. Oleanolic acid has been marketed in China as an oral drug for human liver disorders.

PMID:8847885 Liu J; J Ethnopharmacol 49 (2): 57-68 (1995)

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Antineoplastic Agents, Phytogenic

Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity. (See all compounds classified as Antineoplastic Agents, Phytogenic.)

Cyclooxygenase Inhibitors

Compounds or agents that combine with cyclooxygenase (PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES) and thereby prevent its substrate-enzyme combination with arachidonic acid and the formation of eicosanoids, prostaglandins, and thromboxanes. (See all compounds classified as Cyclooxygenase Inhibitors.)

Anti-Infective Agents

Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection. (See all compounds classified as Anti-Infective Agents.)

5.2 Mechanism of Action

/The authors/ previously reported that ursolic acid, a pentacyclic triterpene acid, inhibited the invasion of HT1080 human fibrosarcoma cells by reducing the expression of matrix metalloproteinase-9. Since the chemical structure of ursolic acid is very similar to that of dexamethasone, a synthetic glucocorticoid, ... whether ursolic acid acts through the glucocorticoid receptor /was investigated/. The expression of matrix metalloproteinase-9 is thought to be regulated similarly with matrix metalloproteinase-1 and matrix metalloproteinase-3 as containing common 2-O-tetradecanoylphorbol-acetate responsible region, where AP-1 proteins can bind. Dexamethasone has been studied to repress the 2-O-tetradecanoylphorbol-acetate-induced expression of matrix metalloproteinase-1 and matrix metalloproteinase-3 through a glucocorticoid receptor-mediated manner. In Northern blot analysis, we found that ursolic acid reduced the expression of matrix metalloproteinase-1 and matrix metalloproteinase-3 induced by 2-O-tetradecanoylphorbol-acetate. Similarly, ursolic acid down-regulated 2-O-tetradecanoylphorbol-acetate-induction of matrix metalloproteinase-9 gene in the same manner of dexamethasone. RU486, a potent glucocorticoid receptor antagonist, was used for identifying that ursolic acid-induced down-regulation of matrix metalloproteinase-9 expression is mediated by its binding to glucocorticoid receptor. The effect of ursolic acid on the matrix metalloproteinase-9 expression was blocked by RU486, suggesting that ursolic acid acts via a glucocorticoid receptor in the regulation of matrix metalloproteinase-9. Western blot analysis and immunocytochemistry showed that ursolic acid increased glucocorticoid receptor fraction in the nucleus, although it decreased the synthesis of glucocorticoid receptor mRNA. In addition, ursolic acid did not decrease the expression of c-jun and DNA-binding activity of AP-1 to its cognate sequences. Taken together, ... ursolic acid may induce the repression of matrix metalloproteinase-9 by stimulating the nuclear translocation of glucocorticoid receptor, and the translocated glucocorticoid receptor probably down-modulating the trans-activating function of AP-1 to 2-O-tetradecanoylphorbol-acetate responsible element of matrix metalloproteinase-9 promoter region.

PMID:9488041 Cha HJ et al; Oncogene 16 (6): 771-8 (1998)

... Ursolic acid suppressed NF-kappaB activation induced by various carcinogens including tumor necrosis factor (TNF), phorbol ester, okadaic acid, H2O2, and cigarette smoke. These effects were not cell type specific. Ursolic acid inhibited DNA binding of NF-kappaB consisting of p50 and p65. Ursolic acid inhibited IkappaBalpha degradation, IkappaBalpha phosphorylation, IkappaBalpha kinase activation, p65 phosphorylation, p65 nuclear translocation, and NF-kappaB-dependent reporter gene expression. Ursolic acid also inhibited NF-kappaB-dependent reporter gene expression activated by TNF receptor, TNF receptor-associated death domain, TNF receptor-associated factor, NF-kappaB-inducing kinase, IkappaBalpha kinase, and p65. The inhibition of NF-kappaB activation correlated with suppression of NF-kappaB-dependent cyclin D1, cyclooxygenase 2, and matrix metalloproteinase 9 expression. Thus, overall, /the/ results indicate that ursolic acid inhibits IkappaBalpha kinase and p65 phosphorylation, leading to the suppression of NF-kappaB activation induced by various carcinogens. These actions of ursolic acid may mediate its antitumorigenic and chemosensitizing effects.

PMID:12907607 Shishodia S et al; Cancer Res 63 (15): 4375-83 (2003)