3beta,12beta-dihydroxy-15-oxo-16-en-20,21,22,23,24,25,26,27-octanordammarane

ID: ALA3422415

Chembl Id: CHEMBL3422415

PubChem CID: 101911914

Max Phase: Preclinical

Molecular Formula: C22H34O3

Molecular Weight: 346.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)[C@@H](O)CC[C@]2(C)[C@H]3C[C@@H](O)[C@@H]4C=CC(=O)[C@@]4(C)[C@]3(C)CC[C@@H]12

Standard InChI:  InChI=1S/C22H34O3/c1-19(2)15-8-11-21(4)16(20(15,3)10-9-17(19)24)12-14(23)13-6-7-18(25)22(13,21)5/h6-7,13-17,23-24H,8-12H2,1-5H3/t13-,14+,15-,16+,17-,20-,21+,22-/m0/s1

Standard InChI Key:  UUHVPIJALZYQLA-LNRMMRAHSA-N

Alternative Forms

1. Parent:

   

   ALA3422415

   (3S,5R,8R,9R,10R,12R,13R,14R)-3,12-dihydroxy-4,4,8,10,14-pentamethyl-1,2,3,5,6,7,9,11,12,13-decahydrocyclopenta[a]phenanthren-15-one

Molecule Features

Natural Product: No

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: 346.51

Molecular Weight (Monoisotopic): 346.2508

AlogP: 3.73

#Rotatable Bonds: ┄

Polar Surface Area: 57.53

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.50

CX LogD: 3.50

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.70

Np Likeness Score: 3.16

References

1. Chen XQ, Shao LD, Pal M, Shen Y, Cheng X, Xu G, Peng LY, Wang K, Pan ZH, Li MM, Leng Y, He J, Zhao QS..  (2015)  Hupehenols A-E, selective 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitors from Viburnum hupehense.,  78  (2): [PMID:25590374] [10.1021/np500896n]

2. Nguyen TT, Truong BN, Doan Thi Mai H, Litaudon M, Nguyen VH, Do Thi T, Chau VM, Pham VC..  (2017)  Cytotoxic dammarane-type triterpenoids from the leaves of Viburnum sambucinum.,  27  (8): [PMID:28318944] [10.1016/j.bmcl.2017.03.014]

Source

Source(1):

• Scientific Literature