Tetrahydrocannabinol acid

ID: ALA1086558

Cas Number: 23978-84-9

PubChem CID: 46889976

Max Phase: Preclinical

Molecular Formula: C22H30O4

Molecular Weight: 358.48

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Tetrahydrocannabinol Acid | Thca-b|Cannabinolic acid B|23978-84-9|Q2682Q3DXB|delta9-Thca-C4 B|Tetrahydrocannabinol acid|delta-9-Tetrahydrocannabinolic acid-C4 B|CHEMBL1086558|delta9-Tetrahydrocannabinoic acid B|delta1-Tetrahydrocannabinolic acid B|1delta9-Tetrahydrocannabinoic acid B|(6aR,10aR)-6a,7,8,10a-Tetrahydro-1-hydroxy-6,6,9-trimethyl-3-pentyl-6H-dibenzo(b,d)pyran-4-carboxylic acid|6H-Dibenzo(b,d)pyran-4-carboxylic acid, 6a,7,8,10a-tetrahydro-1-hydroxy-6,6,9-trimethyl-3-pentyl-, (6aR,10aRShow More⌵

Canonical SMILES:  CCCCCc1cc(O)c2c(c1C(=O)O)OC(C)(C)[C@@H]1CCC(C)=C[C@@H]21

Standard InChI:  InChI=1S/C22H30O4/c1-5-6-7-8-14-12-17(23)19-15-11-13(2)9-10-16(15)22(3,4)26-20(19)18(14)21(24)25/h11-12,15-16,23H,5-10H2,1-4H3,(H,24,25)/t15-,16-/m1/s1

Standard InChI Key:  VITZNDKHSIWPSR-HZPDHXFCSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    6.1724   -0.1484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8887    0.2647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8858    1.0949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1706    1.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4579    0.2642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4575    1.0913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0286    0.2635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7458   -0.1519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0282    1.0906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7458    1.5069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7441    2.3319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0264    2.7469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3089    2.3305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3090    1.4993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0257    3.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3113    0.6831    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2280    0.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8111   -0.5290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4563    1.9243    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1686    2.3286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6035   -0.1465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3171    0.2670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0319   -0.1442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7454    0.2692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4604   -0.1420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1730   -0.9761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4588   -1.3883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8872   -1.3886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
  5  8  1  0
  9 16  1  1
  6 10  1  0
  7 17  1  0
  9  7  1  0
  7 18  1  0
  7  8  1  0
 10 19  1  6
  9 10  1  0
  4 20  1  0
  3  4  2  0
  2 21  1  0
  4  6  1  0
 21 22  1  0
  5  6  2  0
 22 23  1  0
  1  2  2  0
 23 24  1  0
  5  1  1  0
 24 25  1  0
  2  3  1  0
  9 14  1  0
 10 11  1  0
 26 27  1  0
 26 28  2  0
  1 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1086558

   TETRAHYDROCANNABINOL 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: 358.48

Molecular Weight (Monoisotopic): 358.2144

AlogP: 5.43

#Rotatable Bonds: 5

Polar Surface Area: 66.76

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.83

CX Basic pKa: ┄

CX LogP: 5.60

CX LogD: 2.35

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.54

Np Likeness Score: 2.30

References

1. Baraldi PG, Preti D, Materazzi S, Geppetti P..  (2010)  Transient receptor potential ankyrin 1 (TRPA1) channel as emerging target for novel analgesics and anti-inflammatory agents.,  53  (14): [PMID:20356305] [10.1021/jm100062h]

Source

Source(1):

• Scientific Literature