[(2S)-2-methyl-2-(4'-methyl-3'-pentenyl)-8-(3''-methyl-2''-butenyl)-2H-1-benzopyran-6-carboxylic acid]

ID: ALA520792

PubChem CID: 11221505

Max Phase: Preclinical

Molecular Formula: C22H28O3

Molecular Weight: 340.46

Molecule Type: Small molecule

Names and Identifiers

Synonyms: (+)-(S)-Gaudichaudianic Acid | Gaudichaudianic Acid|CHEMBL520792|(+)-(S)-Gaudichaudianic Acid|(2S)-2-methyl-8-(3-methylbut-2-enyl)-2-(4-methylpent-3-enyl)chromene-6-carboxylic Acid

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

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
    7.1279   -5.8434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4083   -6.2578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6954   -5.8473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9763   -6.2601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2548   -5.8472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2571   -5.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9764   -4.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6932   -5.0177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4038   -4.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1256   -5.0138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1223   -6.6639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8485   -5.4416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9768   -7.0851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2626   -7.4980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2630   -8.3230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5489   -8.7359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9778   -8.7351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5429   -4.5981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5454   -3.7731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8271   -5.0084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5566   -5.8648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2772   -5.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9854   -5.8864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7060   -5.4847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9730   -6.7112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  1  0
  2  3  1  0
  4 13  1  0
  3  4  1  0
 13 14  1  0
  4  5  2  0
 14 15  2  0
  5  6  1  0
 15 16  1  0
  6  7  2  0
 15 17  1  0
  7  8  1  0
  8  3  2  0
  8  9  1  0
 18 19  1  0
 18 20  2  0
  6 18  1  0
  9 10  2  0
 12 21  1  0
 10  1  1  0
 21 22  1  0
 22 23  2  0
  1 11  1  1
 23 24  1  0
  1  2  1  0
 23 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA520792

   Gaudichaudianic 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: 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