beta-amyrin

ID: ALA455098

Chembl Id: CHEMBL455098

Cas Number: 559-70-6

PubChem CID: 73145

Product Number: A122374

Max Phase: Preclinical

Molecular Formula: C30H50O

Molecular Weight: 426.73

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Beta-Amyrin | beta-Amyrin|559-70-6|Amyrin|beta-Amyrenol|Olean-12-en-3beta-ol|B-Amyrin|UNII-KM8353IPSO|3beta-hydroxyolean-12-ene|KM8353IPSO|CHEBI:10352|AMYRIN, BETA-|EINECS 209-204-6|(3S,4aR,6aR,6bS,8aR,12aR,14aR,14bR)-4,4,6a,6b,8a,11,11,14b-octamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-ol|NSC 527971|CHEMBL455098|(3beta)-olean-12-en-3-ol|Olean-12-en-3-ol, (3beta)-|NSC-527971|-amyrin|beta.-Amyrenol|beta -Amyrin|beta.-Amyrin|Olean-12-en-3-ol, (3b)-|(3S,4aR,6aR,6bS,8aR,12aR,14Show More⌵

Canonical SMILES:  CC1(C)CC[C@]2(C)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]2C1

Standard InChI:  InChI=1S/C30H50O/c1-25(2)15-16-27(5)17-18-29(7)20(21(27)19-25)9-10-23-28(6)13-12-24(31)26(3,4)22(28)11-14-30(23,29)8/h9,21-24,31H,10-19H2,1-8H3/t21-,22-,23+,24-,27+,28-,29+,30+/m0/s1

Standard InChI Key:  JFSHUTJDVKUMTJ-QHPUVITPSA-N

Alternative Forms

1. Parent:

   

   ALA455098

   beta-AMYRIN

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: 426.73

Molecular Weight (Monoisotopic): 426.3862

AlogP: 8.17

#Rotatable Bonds: 0

Polar Surface Area: 20.23

Molecular Species: NEUTRAL

HBA: 1

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 1

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa:

CX Basic pKa:

CX LogP: 7.40

CX LogD: 7.40

Aromatic Rings: 0

Heavy Atoms: 31

QED Weighted: 0.39

Np Likeness Score: 3.29

References

1. Hoet S, Pieters L, Muccioli GG, Habib-Jiwan JL, Opperdoes FR, Quetin-Leclercq J..  (2007)  Antitrypanosomal activity of triterpenoids and sterols from the leaves of Strychnos spinosa and related compounds.,  70  (8): [PMID:17637068] [10.1021/np070038q]

2. Nes WD, Patterson GW.  (1981)  Effects of Tetracyclic and Pentacyclic Triterpenoids on Growth of Phytophthora cactorum,  44  (2): [10.1021/np50014a012]

3. Morikawa T, Kishi A, Pongpiriyadacha Y, Matsuda H, Yoshikawa M..  (2003)  Structures of new friedelane-type triterpenes and eudesmane-type sesquiterpene and aldose reductase inhibitors from Salacia chinensis.,  66  (9): [PMID:14510595] [10.1021/np0301543]

4. Woldemichael GM, Gutierrez-Lugo MT, Franzblau SG, Wang Y, Suarez E, Timmermann BN..  (2004)  Mycobacterium tuberculosis growth inhibition by constituents of Sapium haematospermum.,  67  (4): [PMID:15104489] [10.1021/np0303411]

5. Hata K, Hori K, Takahashi S..  (2002)  Differentiation- and apoptosis-inducing activities by pentacyclic triterpenes on a mouse melanoma cell line.,  65  (5): [PMID:12027734] [10.1021/np0104673]

6. Ding Y, Nguyen HT, Kim SI, Kim HW, Kim YH..  (2009)  The regulation of inflammatory cytokine secretion in macrophage cell line by the chemical constituents of Rhus sylvestris.,  19  (13): [PMID:19447618] [10.1016/j.bmcl.2009.04.129]

7. Tan GT, Pezzuto JM, Kinghorn AD, Hughes SH..  (1991)  Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.,  54  (1): [PMID:1710653] [10.1021/np50073a012]

8. Bibi N, Tanoli SA, Farheen S, Afza N, Siddiqi S, Zhang Y, Kazmi SU, Malik A..  (2010)  In vitro antituberculosis activities of the constituents isolated from Haloxylon salicornicum.,  20  (14): [PMID:20542692] [10.1016/j.bmcl.2010.05.061]

9. De Bruyn T, van Westen GJ, Ijzerman AP, Stieger B, de Witte P, Augustijns PF, Annaert PP..  (2013)  Structure-based identification of OATP1B1/3 inhibitors.,  83  (6): [PMID:23571415] [10.1124/mol.112.084152]

10. Vieira Pde B, Silva NL, da Silva GN, Silva DB, Lopes NP, Gnoatto SC, da Silva MV, Macedo AJ, Bastida J, Tasca T..  (2016)  Caatinga plants: Natural and semi-synthetic compounds potentially active against Trichomonas vaginalis.,  26  (9): [PMID:27020521] [10.1016/j.bmcl.2016.03.061]

11. Xiong J, Wan J, Ding J, Wang PP, Ma GL, Li J, Hu JF..  (2017)  Camellianols A-G, Barrigenol-like Triterpenoids with PTP1B Inhibitory Effects from the Endangered Ornamental Plant Camellia crapnelliana.,  80  (11): [PMID:29064696] [10.1021/acs.jnatprod.7b00241]

12. Reddy SD, Siva B, Phani Babu VS, Vijaya M, Nayak VL, Mandal R, Tiwari AK, Shashikala P, Babu KS..  (2017)  New cycloartane type-triterpenoids from the areal parts of Caragana sukiensis and their biological activities.,  136  [PMID:28482219] [10.1016/j.ejmech.2017.04.065]

13. 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]

14. Qin N, Lu X, Liu Y, Qiao Y, Qu W, Feng F, Sun H..  (2021)  Recent research progress of Uncaria spp. based on alkaloids: phytochemistry, pharmacology and structural chemistry.,  210  [PMID:33148492] [10.1016/j.ejmech.2020.112960]

15. Kumar G, Kiran Tudu A..  (2023)  Tackling multidrug-resistant Staphylococcus aureus by natural products and their analogues acting as NorA efflux pump inhibitors.,  80  [PMID:36731248] [10.1016/j.bmc.2023.117187]

16. Xu GB, Xiao YH, Zhang QY, Zhou M, Liao SG..  (2018)  Hepatoprotective natural triterpenoids.,  145  [PMID:29353722] [10.1016/j.ejmech.2018.01.011]

Source

Source(1):

• Scientific Literature