ID: ALA461615

Max Phase: Preclinical

Molecular Formula: C20H28O3

Molecular Weight: 316.44

Molecule Type: Small molecule

Representations

Synonyms (2): (-)-Hardwickic Acid | (-)-Hardwickiic Acid
Synonyms from Alternative Forms(2):

Canonical SMILES:  C[C@@H]1CC[C@@]2(C)C(C(=O)O)=CCC[C@@H]2[C@@]1(C)CCc1ccoc1

Standard InChI:  InChI=1S/C20H28O3/c1-14-7-10-20(3)16(18(21)22)5-4-6-17(20)19(14,2)11-8-15-9-12-23-13-15/h5,9,12-14,17H,4,6-8,10-11H2,1-3H3,(H,21,22)/t14-,17-,19+,20+/m1/s1

Standard InChI Key:  HHWOKJDCJVESIF-JBCDFXQESA-N

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

Properties

Molecular Weight: 316.44

Molecular Weight (Monoisotopic): 316.2038

AlogP: 5.08

#Rotatable Bonds: 4

Polar Surface Area: 50.44

Molecular Species: ACID

HBA: 2

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.26

CX Basic pKa:

CX LogP: 5.08

CX LogD: 2.09

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.84

Np Likeness Score: 2.86

References

1. Bigham AK, Munro TA, Rizzacasa MA, Robins-Browne RM..  (2003)  Divinatorins A-C, new neoclerodane diterpenoids from the controlled sage Salvia divinorum.,  66  (9): [PMID:14510607] [10.1021/np030313i]

2. McChesney JD, Clark AM, Silveira ER..  (1991)  Antimicrobial diterpenes of Croton sonderianus, 1. Hardwickic and 3,4-secotrachylobanoic acids.,  54  (6): [PMID:1812213] [10.1021/np50078a021]

3. Idippily ND, Zheng Q, Gan C, Quamine A, Ashcraft MM, Zhong B, Su B..  (2017)  Copalic acid analogs down-regulate androgen receptor and inhibit small chaperone protein.,  27  (11): [PMID:28442254] [10.1016/j.bmcl.2017.04.046]

Source

Source(1):

• Scientific Literature