(1S,2E,4R,6R, 7E,11E)-2,7,11-cembratriene-4,6-diol

ID: ALA564595

PubChem CID: 5281356

Max Phase: Preclinical

Molecular Formula: C20H34O2

Molecular Weight: 306.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C/C1=C\[C@H](O)C[C@](C)(O)/C=C\[C@@H](C(C)C)CC/C(C)=C/CC1

Standard InChI:  InChI=1S/C20H34O2/c1-15(2)18-10-9-16(3)7-6-8-17(4)13-19(21)14-20(5,22)12-11-18/h7,11-13,15,18-19,21-22H,6,8-10,14H2,1-5H3/b12-11-,16-7+,17-13-/t18-,19-,20+/m0/s1

Standard InChI Key:  RIVKDDXPCFBMOV-MGVZDCCKSA-N

Molfile:  

     RDKit          2D

 22 22  0  0  0  0  0  0  0  0999 V2000
   21.8385  -26.2203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5483  -25.7786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1480  -25.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4527  -24.9591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2707  -24.9586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2151  -24.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5116  -24.6155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2191  -23.8002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5184  -23.7899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4560  -23.4704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2778  -23.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5727  -22.6611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1748  -22.6535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8771  -22.2128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3954  -26.1087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1625  -25.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1608  -26.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8778  -24.9598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7360  -23.8731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5583  -23.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8821  -21.3878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0375  -22.8792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  9  1  0
  8 10  1  0
  9 11  1  0
 10 12  1  0
 11 13  2  0
 12 14  1  0
 13 14  1  0
  3 15  1  0
  1  2  1  0
  4 16  1  6
  1  3  1  0
 16 17  1  0
  2  4  1  0
 16 18  1  0
  3  5  2  0
 10 19  1  1
  4  6  1  0
 11 20  1  0
  5  7  1  0
 14 21  1  6
  6  8  2  0
 10 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA564595

   (1S,3R,4E,8E,12R,13Z)-1,5,9-trimethyl-12-propan-2-ylcyclotetradeca-4,8,13-triene-1,3-diol

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: 306.49

Molecular Weight (Monoisotopic): 306.2559

AlogP: 4.78

#Rotatable Bonds: 1

Polar Surface Area: 40.46

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.39

CX LogD: 4.39

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.68

Np Likeness Score: 3.33

References

1. Yu BZ, Kaimal R, Bai S, El Sayed KA, Tatulian SA, Apitz RJ, Jain MK, Deng R, Berg OG..  (2009)  Effect of guggulsterone and cembranoids of Commiphora mukul on pancreatic phospholipase A(2): role in hypocholesterolemia.,  72  (1): [PMID:19102680] [10.1021/np8004453]

Source

Source(1):

• Scientific Literature