3beta,12beta-dihydroxy-17alpha-methoxy-15-oxo-20,21,22,23,24,25,26,27-octanordammarane

ID: ALA3422264

Chembl Id: CHEMBL3422264

PubChem CID: 101911911

Max Phase: Preclinical

Molecular Formula: C23H38O4

Molecular Weight: 378.55

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C23H38O4/c1-20(2)15-7-10-22(4)16(21(15,3)9-8-17(20)25)11-13(24)19-14(27-6)12-18(26)23(19,22)5/h13-17,19,24-25H,7-12H2,1-6H3/t13-,14-,15+,16-,17+,19-,21+,22-,23-/m1/s1

Standard InChI Key:  ZENVSCKOBKOTSJ-RTFSNDOKSA-N

Alternative Forms

1. Parent:

   

   ALA3422264

   (3S,5R,8R,9R,10R,12R,13R,14R,17R)-3,12-dihydroxy-17-methoxy-4,4,8,10,14-pentamethyl-1,2,3,5,6,7,9,11,12,13,16,17-dodecahydrocyclopenta[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: 378.55

Molecular Weight (Monoisotopic): 378.2770

AlogP: 3.58

#Rotatable Bonds: 1

Polar Surface Area: 66.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.96

CX LogD: 2.96

Aromatic Rings: ┄

Heavy Atoms: 27

QED Weighted: 0.73

Np Likeness Score: 3.08

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