ent-Kaur-16-en-19-ol

ID: ALA512447

Chembl Id: CHEMBL512447

PubChem CID: 24883422

Max Phase: Preclinical

Molecular Formula: C20H32O

Molecular Weight: 288.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1C[C@@]23CC[C@@H]4[C@](C)(CO)CCC[C@@]4(C)[C@@H]2CC[C@H]1C3

Standard InChI:  InChI=1S/C20H32O/c1-14-11-20-10-7-16-18(2,13-21)8-4-9-19(16,3)17(20)6-5-15(14)12-20/h15-17,21H,1,4-13H2,2-3H3/t15-,16+,17-,18-,19+,20+/m0/s1

Standard InChI Key:  TUJQVRFWMWRMIO-GNVSMLMZSA-N

Alternative Forms

1. Parent:

   

   ALA512447

   ent-Kaurenol

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: 288.48

Molecular Weight (Monoisotopic): 288.2453

AlogP: 4.95

#Rotatable Bonds: 1

Polar Surface Area: 20.23

Molecular Species: NEUTRAL

HBA: 1

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 1

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.34

CX LogD: 4.34

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.68

Np Likeness Score: 3.31

References

1. Batista R, Humberto JL, Chiari E, de Oliveira AB..  (2007)  Synthesis and trypanocidal activity of ent-kaurane glycosides.,  15  (1): [PMID:17055730] [10.1016/j.bmc.2006.09.048]

2. Wu YC, Hung YC, Chang FR, Cosentino M, Wang HK, Lee KH..  (1996)  Identification of ent-16 beta, 17-dihydroxykauran-19-oic acid as an anti-HIV principle and isolation of the new diterpenoids annosquamosins A and B from Annona squamosa.,  59  (6): [PMID:8786370] [10.1021/np960416j]

3. Chang FR, Yang PY, Lin JY, Lee KH, Wu YC..  (1998)  Bioactive kaurane diterpenoids from Annona glabra.,  61  (4): [PMID:9584397] [10.1021/np970497z]

4. Han L, Huang X, Sattler I, Dahse HM, Fu H, Lin W, Grabley S..  (2004)  New diterpenoids from the marine mangrove Bruguiera gymnorrhiza.,  67  (9): [PMID:15387677] [10.1021/np040062t]

5. Deng X, Shen Y, Yang J, He J, Zhao Y, Peng LY, Leng Y, Zhao QS..  (2013)  Discovery and structure-activity relationships of ent-Kaurene diterpenoids as potent and selective 11β-HSD1 inhibitors: potential impact in diabetes.,  65  [PMID:23747808] [10.1016/j.ejmech.2013.05.010]

Source

Source(1):

• Scientific Literature