3-acetoxycopalic acid

ID: ALA4095841

PubChem CID: 101892773

Max Phase: Preclinical

Molecular Formula: C22H34O4

Molecular Weight: 362.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1CC[C@@H]2C(C)(C)C(OC(C)=O)CC[C@@]2(C)[C@@H]1CC/C(C)=C/C(=O)O

Standard InChI:  InChI=1S/C22H34O4/c1-14(13-20(24)25)7-9-17-15(2)8-10-18-21(4,5)19(26-16(3)23)11-12-22(17,18)6/h13,17-19H,2,7-12H2,1,3-6H3,(H,24,25)/b14-13+/t17-,18-,19?,22+/m1/s1

Standard InChI Key:  OMNJRQNCWHCCBZ-AVIKLCGHSA-N

Molfile:  

     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
   16.6421   -7.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2879   -6.4501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8751   -7.1601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6259   -5.1951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5902   -6.0193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3595   -4.8055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0527   -5.2567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0136   -6.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7038   -6.5202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4376   -6.1485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4768   -5.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7822   -4.8719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8202   -4.0478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5530   -3.6729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5910   -2.8487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3238   -2.4654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8964   -2.3996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9343   -1.5754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2355   -1.1346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6671   -1.2004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2104   -4.9429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0463   -4.4335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1046   -6.9085    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.8611   -6.4056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1621   -5.9673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4331   -6.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1922   -5.1429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  1  0
  4  6  1  0
  5  2  1  0
  2  8  1  0
  7  6  1  0
  7  8  1  0
  7 12  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  6
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 11 21  2  0
  7 22  1  6
  8 23  1  1
  5 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4095841

   (E)-5-[(1R,4aS,8aS)-6-acetyloxy-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-2-enoic acid

Molecule Features

Natural Product: No

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: 362.51

Molecular Weight (Monoisotopic): 362.2457

AlogP: 5.14

#Rotatable Bonds: 5

Polar Surface Area: 63.60

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.62

CX Basic pKa: ┄

CX LogP: 4.69

CX LogD: 1.98

Aromatic Rings: ┄

Heavy Atoms: 26

QED Weighted: 0.42

Np Likeness Score: 3.01

References

1. Idippily ND, Zheng Q, Gan C, Quamine A, Ashcraft MM, Zhong B, Su B..  (2017)  Copalic acid analogs down-regulate androgen receptor and inhibit small chaperone protein.,  27  (11): [PMID:28442254] [10.1016/j.bmcl.2017.04.046]

Source

Source(1):

• Scientific Literature