(8S,8'S)-Dihydroguaiaretic acid

ID: ALA3810128

Chembl Id: CHEMBL3810128

Cas Number: 174291-55-5

PubChem CID: 12898412

Max Phase: Preclinical

Molecular Formula: C20H26O4

Molecular Weight: 330.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(C[C@H](C)[C@@H](C)Cc2ccc(O)c(OC)c2)ccc1O

Standard InChI:  InChI=1S/C20H26O4/c1-13(9-15-5-7-17(21)19(11-15)23-3)14(2)10-16-6-8-18(22)20(12-16)24-4/h5-8,11-14,21-22H,9-10H2,1-4H3/t13-,14-/m0/s1

Standard InChI Key:  ADFOLUXMYYCTRR-KBPBESRZSA-N

Alternative Forms

1. Parent:

   

   ALA3810128

   (+)-Dihydroguaiaretic acid

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: 330.42

Molecular Weight (Monoisotopic): 330.1831

AlogP: 4.17

#Rotatable Bonds: 7

Polar Surface Area: 58.92

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 9.97

CX Basic pKa:

CX LogP: 5.05

CX LogD: 5.05

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.80

Np Likeness Score: 0.57

References

1. Yamauchi S, Tanimura R, Nishiwaki H, Nishi K, Sugahara T, Maruyama M, Ano Y, Akiyama K, Kishida T..  (2016)  Enantioselective syntheses of both enantiomers of 9'-dehydroxyimperanene and 7,8-dihydro-9'-dehydroxyimperanene and the comparison of biological activity between 9-norlignans and dihydroguaiaretic acids.,  26  (13): [PMID:27210431] [10.1016/j.bmcl.2016.05.020]

2. Reyes-Melo K, García A, Romo-Mancillas A, Garza-González E, Rivas-Galindo VM, Miranda LD, Vargas-Villarreal J, Favela-Hernández JMJ, Camacho-Corona MDR..  (2017)  meso-Dihydroguaiaretic acid derivatives with antibacterial and antimycobacterial activity.,  25  (20): [PMID:28844400] [10.1016/j.bmc.2017.07.047]

Source

Source(1):

• Scientific Literature