neoavarol

ID: ALA3965313

Chembl Id: CHEMBL3965313

PubChem CID: 11392873

Max Phase: Preclinical

Molecular Formula: C21H30O2

Molecular Weight: 314.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1CCC[C@H]2[C@](C)(Cc3cc(O)ccc3O)[C@@H](C)CC[C@]12C

Standard InChI:  InChI=1S/C21H30O2/c1-14-6-5-7-19-20(14,3)11-10-15(2)21(19,4)13-16-12-17(22)8-9-18(16)23/h8-9,12,15,19,22-23H,1,5-7,10-11,13H2,2-4H3/t15-,19+,20+,21+/m0/s1

Standard InChI Key:  FBMAHDGTCDISLJ-LWILDLIXSA-N

Alternative Forms

1. Parent:

   

   ALA3965313

   2-[[(1R,2S,4aS,8aS)-1,2,4a-trimethyl-5-methylidene-3,4,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]methyl]benzene-1,4-diol

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: 314.47

Molecular Weight (Monoisotopic): 314.2246

AlogP: 5.44

#Rotatable Bonds: 2

Polar Surface Area: 40.46

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.85

CX Basic pKa: ┄

CX LogP: 5.75

CX LogD: 5.75

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.56

Np Likeness Score: 2.89

References

1. Abdjul DB, Yamazaki H, Takahashi O, Kirikoshi R, Ukai K, Namikoshi M..  (2016)  Sesquiterpene Hydroquinones with Protein Tyrosine Phosphatase 1B Inhibitory Activities from a Dysidea sp. Marine Sponge Collected in Okinawa.,  79  (7): [PMID:27336796] [10.1021/acs.jnatprod.6b00367]

2. Ohshiro T, Kobayashi K, Suzuki A, Yamazaki H, Uchida R, Namikoshi M, Tomoda H..  (2019)  Inhibition of neutral lipid synthesis by avarols from a marine sponge.,  29  (16): [PMID:31253530] [10.1016/j.bmcl.2019.06.026]

Source

Source(1):

• Scientific Literature