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

ID: ALA437964

Chembl Id: CHEMBL437964

Cas Number: 17019-92-0

PubChem CID: 9847548

Product Number: K138359

Max Phase: Preclinical

Molecular Formula: C30H46O4

Molecular Weight: 470.69

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 11-Keto Boswellic Acid | 11-Keto-beta-boswellic acid|17019-92-0|Keto-b-boswellic acid|11-keto-beta-boswellicacid|UNII-0S3BIF6H0Q|0S3BIF6H0Q|11-?Keto-?beta-?boswellic acid|11-Keto Boswellic Acid|BETA-BOSWELLIC ACID,11-KETO|CHEMBL437964|11-Oxo-beta-boswellic acid|(3alpha,4beta)-3-Hydroxy-11-oxours-12-en-23-oic acid|(4R)-3alpha-hydroxy-11-oxo-urs-12-en-23-oic acid|3alpha-Hydroxy-11-oxours-12-en-24-oic acid|11-Oxo-.beta.-boswellic acid|11-Keto-.beta.-boswellic acid|3.alpha.-Hydroxy-11-oxours-12-en-2Show More⌵

Canonical SMILES:  C[C@H]1[C@H](C)CC[C@]2(C)CC[C@]3(C)C(=CC(=O)[C@@H]4[C@@]5(C)CC[C@@H](O)[C@](C)(C(=O)O)[C@@H]5CC[C@]43C)[C@H]12

Standard InChI:  InChI=1S/C30H46O4/c1-17-8-11-26(3)14-15-28(5)19(23(26)18(17)2)16-20(31)24-27(4)12-10-22(32)30(7,25(33)34)21(27)9-13-29(24,28)6/h16-18,21-24,32H,8-15H2,1-7H3,(H,33,34)/t17-,18+,21-,22-,23+,24-,26-,27+,28-,29-,30-/m1/s1

Standard InChI Key:  YIMHGPSYDOGBPI-YZCVQEKWSA-N

Alternative Forms

1. Parent:

   

   ALA437964

   11-KETO BOSWELLIC ACID

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 470.69

Molecular Weight (Monoisotopic): 470.3396

AlogP: 6.27

#Rotatable Bonds: 1

Polar Surface Area: 74.60

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.40

CX Basic pKa: ┄

CX LogP: 6.02

CX LogD: 3.13

Aromatic Rings: ┄

Heavy Atoms: 34

QED Weighted: 0.47

Np Likeness Score: 3.14

References

1. Shah BA, Kumar A, Gupta P, Sharma M, Sethi VK, Saxena AK, Singh J, Qazi GN, Taneja SC..  (2007)  Cytotoxic and apoptotic activities of novel amino analogues of boswellic acids.,  17  (23): [PMID:17950603] [10.1016/j.bmcl.2007.10.011]

2. Singh S, Khajuria A, Taneja SC, Khajuria RK, Singh J, Qazi GN..  (2007)  Boswellic acids and glucosamine show synergistic effect in preclinical anti-inflammatory study in rats.,  17  (13): [PMID:17481895] [10.1016/j.bmcl.2007.04.034]

3. Schweizer S, von Brocke AF, Boden SE, Bayer E, Ammon HP, Safayhi H..  (2000)  Workup-dependent formation of 5-lipoxygenase inhibitory boswellic acid analogues.,  63  (8): [PMID:10978197] [10.1021/np000069k]

4. Zhang YN, Zhang W, Hong D, Shi L, Shen Q, Li JY, Li J, Hu LH..  (2008)  Oleanolic acid and its derivatives: new inhibitor of protein tyrosine phosphatase 1B with cellular activities.,  16  (18): [PMID:18707891] [10.1016/j.bmc.2008.07.080]

5. Atta-ur-Rahman, Naz H, Fadimatou, Makhmoor T, Yasin A, Fatima N, Ngounou FN, Kimbu SF, Sondengam BL, Choudhary MI..  (2005)  Bioactive constituents from Boswellia papyrifera.,  68  (2): [PMID:15730241] [10.1021/np040142x]

6. Rollinger JM, Kratschmar DV, Schuster D, Pfisterer PH, Gumy C, Aubry EM, Brandstötter S, Stuppner H, Wolber G, Odermatt A..  (2010)  11beta-Hydroxysteroid dehydrogenase 1 inhibiting constituents from Eriobotrya japonica revealed by bioactivity-guided isolation and computational approaches.,  18  (4): [PMID:20100662] [10.1016/j.bmc.2010.01.010]

7. Kaur R, Khan S, Chib R, Kaur T, Sharma PR, Singh J, Shah BA, Taneja SC..  (2011)  A comparative study of proapoptotic potential of cyano analogues of boswellic acid and 11-keto-boswellic acid.,  46  (4): [PMID:21334793] [10.1016/j.ejmech.2011.01.061]

8. Kumar A, Shah BA, Singh S, Hamid A, Singh SK, Sethi VK, Saxena AK, Singh J, Taneja SC..  (2012)  Acyl derivatives of boswellic acids as inhibitors of NF-κB and STATs.,  22  (1): [PMID:22123322] [10.1016/j.bmcl.2011.10.112]

9. Hüsch J, Gerbeth K, Fricker G, Setzer C, Zirkel J, Rebmann H, Schubert-Zsilavecz M, Abdel-Tawab M..  (2012)  Effect of phospholipid-based formulations of Boswellia serrata extract on the solubility, permeability, and absorption of the individual boswellic acid constituents present.,  75  (10): [PMID:23013292] [10.1021/np300009w]

10. Joshi P, Tanwar O, Rambhade S, Bhaisare M, Jain D.  (2012)  2-D QSAR studies of steroidal natural products oleanic acid and their semisynthetic derivatives as potent protein tyrosine phosphatase 1B inhibitors,  21  (3): [10.1007/s00044-010-9529-5]

11. Verhoff M, Seitz S, Paul M, Noha SM, Jauch J, Schuster D, Werz O..  (2014)  Tetra- and pentacyclic triterpene acids from the ancient anti-inflammatory remedy frankincense as inhibitors of microsomal prostaglandin E(2) synthase-1.,  77  (6): [PMID:24844534] [10.1021/np500198g]

12. Csuk R, Niesen-Barthel A, Schäfer R, Barthel A, Al-Harrasi A..  (2015)  Synthesis and antitumor activity of ring A modified 11-keto-β-boswellic acid derivatives.,  92  [PMID:25618017] [10.1016/j.ejmech.2015.01.039]

13. Shenvi S, Kiran KR, Kumar K, Diwakar L, Reddy GC..  (2015)  Synthesis and biological evaluation of boswellic acid-NSAID hybrid molecules as anti-inflammatory and anti-arthritic agents.,  98  [PMID:26010018] [10.1016/j.ejmech.2015.05.001]

14. Sharma S, Gupta S, Khajuria V, Bhagat A, Ahmed Z, Shah BA..  (2016)  Analogues of boswellic acids as inhibitors of pro-inflammatory cytokines TNF-α and IL-6.,  26  (2): [PMID:26711891] [10.1016/j.bmcl.2015.11.035]

15. Khan H, Rengasamy KRR, Pervaiz A, Nabavi SM, Atanasov AG, Kamal MA..  (2018)  Plant-derived mPGES-1 inhibitors or suppressors: A new emerging trend in the search for small molecules to combat inflammation.,  153  [PMID:29329790] [10.1016/j.ejmech.2017.12.059]

16. Vo NNQ, Nomura Y, Muranaka T, Fukushima EO..  (2019)  Structure-Activity Relationships of Pentacyclic Triterpenoids as Inhibitors of Cyclooxygenase and Lipoxygenase Enzymes.,  82  (12): [PMID:31774676] [10.1021/acs.jnatprod.9b00538]

17. Wei H, Guo J, Sun X, Gou W, Ning H, Shang H, Liu Q, Hou W, Li Y..  (2022)  Discovery of Natural Ursane-type SENP1 Inhibitors and the Platinum Resistance Reversal Activity Against Human Ovarian Cancer Cells: A Structure-Activity Relationship Study.,  85  (5.0): [PMID:35500202] [10.1021/acs.jnatprod.1c01166]

Source

Source(1):

• Scientific Literature