14-hydroxy-4,5-dihydro-beta-caryophyllene

ID: ALA501643

PubChem CID: 10036514

Max Phase: Preclinical

Molecular Formula: C15H26O

Molecular Weight: 222.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1CCC[C@H](CO)CC[C@@H]2[C@@H]1CC2(C)C

Standard InChI:  InChI=1S/C15H26O/c1-11-5-4-6-12(10-16)7-8-14-13(11)9-15(14,2)3/h12-14,16H,1,4-10H2,2-3H3/t12-,13+,14+/m0/s1

Standard InChI Key:  QPKKKWDNDWSIRV-BFHYXJOUSA-N

Molfile:  

     RDKit          2D

 18 19  0  0  0  0  0  0  0  0999 V2000
   -2.8887   -0.8673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8417   -1.6907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0128   -0.3506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3092   -1.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0649   -1.9072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7518    0.0251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5670   -0.1628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0654   -0.8203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0198   -1.6474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6341   -2.3550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4588   -2.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5273   -0.1262    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5916    0.2106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3797   -0.0322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8350   -2.9838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1926   -2.4475    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3505   -0.1733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6774   -1.1189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
 10  5  1  0
 10 11  1  0
 11  9  1  0
  1  2  1  0
  8 12  1  1
  2  9  1  0
  3 13  1  1
  8  1  1  0
 13 14  1  0
 11 15  2  0
  3  4  1  0
  9 16  1  6
  4  5  1  0
  1 17  1  0
  3  6  1  0
  1 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA501643

   [(1R,4S,9S)-11,11-dimethyl-8-methylidene-4-bicyclo[7.2.0]undecanyl]methanol

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: 222.37

Molecular Weight (Monoisotopic): 222.1984

AlogP: 3.78

#Rotatable Bonds: 1

Polar Surface Area: 20.23

Molecular Species: NEUTRAL

HBA: 1

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 1

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.57

CX LogD: 3.57

Aromatic Rings: ┄

Heavy Atoms: 16

QED Weighted: 0.67

Np Likeness Score: 2.41

References

1. Demirci B, Başer KH, Demirci F, Hamann MT..  (2000)  New caryophyllene derivatives from Betula litwinowii.,  63  (7): [PMID:10924162] [10.1021/np990438g]

Source

Source(1):

• Scientific Literature