5-hydroxy-2-methyl-2-(4-methylpent-3-enyl)-7-propyl-2H-chromene-6-carboxylic acid

ID: ALA4875095

Cas Number: 64898-02-8

PubChem CID: 11110322

Max Phase: Preclinical

Molecular Formula: C20H26O4

Molecular Weight: 330.42

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCc1cc2c(c(O)c1C(=O)O)C=CC(C)(CCC=C(C)C)O2

Standard InChI:  InChI=1S/C20H26O4/c1-5-7-14-12-16-15(18(21)17(14)19(22)23)9-11-20(4,24-16)10-6-8-13(2)3/h8-9,11-12,21H,5-7,10H2,1-4H3,(H,22,23)

Standard InChI Key:  OIVPAQDCMDYIIL-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
   11.7177   -8.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7683   -9.4803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3401   -7.8278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9203   -9.0716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2001   -7.8187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3024   -8.6021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9112   -7.8281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6258   -8.2404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9187   -8.2360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4716   -9.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0547   -8.2401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0536   -9.0674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4808   -9.0695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4797   -8.7537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7680  -10.3053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7666   -7.8273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4820   -8.2365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0988   -8.3869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1977   -9.4848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6833   -8.9689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1312   -7.4360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3428   -9.4773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6355   -9.0681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3422  -10.2945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9 21  1  0
  1  9  1  0
  4  9  1  0
  2 13  2  0
  9  5  1  0
 13 19  1  0
 17  5  1  0
  6 18  1  0
 20 14  1  0
 11  3  1  0
 12  2  1  0
 11 12  2  0
 17 16  2  0
 19  4  2  0
 16 11  1  0
 20 10  1  0
 18 20  2  0
  2 15  1  0
  1  6  1  0
 17 13  1  0
  3  8  1  0
  8  7  1  0
 22 23  1  0
 22 24  2  0
 12 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4875095

   Cannabichromevarinic acid

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

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: 4.95

#Rotatable Bonds: 6

Polar Surface Area: 66.76

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.87

CX Basic pKa: ┄

CX LogP: 6.02

CX LogD: 2.53

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.72

Np Likeness Score: 2.91

References

1. Martin LJ, Cairns EA, Heblinski M, Fletcher C, Krycer JR, Arnold JC, McGregor IS, Bowen MT, Anderson LL..  (2021)  Cannabichromene and Δ⁹-Tetrahydrocannabinolic Acid Identified as Lactate Dehydrogenase-A Inhibitors by in Silico and in Vitro Screening.,  84  (5.0): [PMID:33887133] [10.1021/acs.jnatprod.0c01281]

Source

Source(1):

• Scientific Literature