ID: ALA520792

Max Phase: Preclinical

Molecular Formula: C22H28O3

Molecular Weight: 340.46

Molecule Type: Small molecule

Representations

Synonyms (1): (+)-(S)-Gaudichaudianic Acid
Synonyms from Alternative Forms(1):

Canonical SMILES:  CC(C)=CCC[C@@]1(C)C=Cc2cc(C(=O)O)cc(CC=C(C)C)c2O1

Standard InChI:  InChI=1S/C22H28O3/c1-15(2)7-6-11-22(5)12-10-18-14-19(21(23)24)13-17(20(18)25-22)9-8-16(3)4/h7-8,10,12-14H,6,9,11H2,1-5H3,(H,23,24)/t22-/m0/s1

Standard InChI Key:  TXHBNVYFCZMCPB-QFIPXVFZSA-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: 340.46

Molecular Weight (Monoisotopic): 340.2038

AlogP: 5.80

#Rotatable Bonds: 6

Polar Surface Area: 46.53

Molecular Species: ACID

HBA: 2

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.27

CX Basic pKa:

CX LogP: 6.00

CX LogD: 3.01

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.67

Np Likeness Score: 2.73

References

1. Lago JH, Ramos CS, Casanova DC, Morandim Ade A, Bergamo DC, Cavalheiro AJ, Bolzani Vda S, Furlan M, Guimarães EF, Young MC, Kato MJ..  (2004)  Benzoic acid derivatives from Piper species and their fungitoxic activity against Cladosporium cladosporioides and C. sphaerospermum.,  67  (11): [PMID:15568762] [10.1021/np030530j]

2. Batista JM, Batista AN, Rinaldo D, Vilegas W, Ambrósio DL, Cicarelli RM, Bolzani VS, Kato MJ, Nafie LA, López SN, Furlan M..  (2011)  Absolute configuration and selective trypanocidal activity of gaudichaudianic acid enantiomers.,  74  (5): [PMID:21506530] [10.1021/np200085h]

Source

Source(1):

• Scientific Literature