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Beta-Boswellic Acid

Synopsis, Chemistry

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Also known as: 631-69-6, B-boswellic acid, (3r,4r,4ar,6ar,6bs,8ar,11r,12s,12ar,14ar,14br)-3-hydroxy-4,6a,6b,8a,11,12,14b-heptamethyl-2,3,4a,5,6,7,8,9,10,11,12,12a,14,14a-tetradecahydro-1h-picene-4-carboxylic acid, B252m1yo2v, Chembl267225, (4r)-3alpha-hydroxyurs-12-en-24-oic acid

Molecular Formula

C₃₀H₄₈O₃

Molecular Weight

456.7 g/mol

InChI Key

NBGQZFQREPIKMG-PONOSELZSA-N

FDA UNII

B252M1YO2V

-boswellic acid is a natural product found in Cyclocarya paliurus, Boswellia papyrifera, and other organisms with data available.

1 2D Structure

Beta-Boswellic Acid

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

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

2.1.2 InChI

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

2.1.3 InChI Key

NBGQZFQREPIKMG-PONOSELZSA-N

2.1.4 Canonical SMILES

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

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]([C@]5(C)C(=O)O)O)C)C)[C@@H]2[C@H]1C)C)C

2.2 Other Identifiers

2.2.1 UNII

B252M1YO2V

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Boswellic Acid

2.3.2 Depositor-Supplied Synonyms

1. 631-69-6

2. B-boswellic Acid

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

4. B252m1yo2v

5. Chembl267225

6. (4r)-3alpha-hydroxyurs-12-en-24-oic Acid

7. Unii-b252m1yo2v

8. Mfcd04039448

9. Urs-12-en-24-oic Acid, 3.alpha.-hydroxy-

10. Mls000697685

11. .beta.-boswellic Acid

12. Schembl4385785

13. Dtxsid2057578

14. Urs-12-en-23-oic Acid, 3-hydroxy-, (3alpha,4beta)-

15. Beta-boswellic Acid, Hplc Grade

16. Chebi:192014

17. Urs-12-en-23-oic Acid, 3-hydroxy-, (3.alpha.,4.beta.)-

18. 3-hydroxy-12-ursen-24-oic Acid

19. (3r,4r,4ar,6ar,6bs,8ar,11r,12s,12ar,14ar,14br)-3-hydroxy-4,6a,6b,8a,11,12,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4-carboxylic Acid

20. Hy-n2513

21. .beta.-boswellic Acid [mi]

22. Bdbm50241260

23. Zinc14089743

24. Akos015897120

25. Lmpr0106180011

26. Beta-boswellic Acid, Analytical Standard

27. Ncgc00247633-01

28. Ac-30252

29. Smr000445587

30. Boswellia Serrata Hexane Extract In Hexane

31. Cs-0022784

32. (3alpha,4beta)-3-hydroxy-urs-12-en-23-oate

33. 3.alpha.-hydroxyurs-12-en-24-oic Acid

34. 631b696

35. (3alpha,4beta)-3-hydroxy-urs-12-en-23-oic Acid

36. Q27274271

37. .beta.-boswellic Acid (constituent Of Boswellia Serrata) [dsc]

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₃₀H₄₈O₃
Molecular Weight	456.7 g/mol
XLogP3	8.3
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	878
Isotope Atom Count	0
Defined Atom Stereocenter Count	11
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

Anti-Inflammatory Agents, Non-Steroidal

Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)