[(-)-10alpha-bromo-9beta-hydroxy-alpha-chamigrene

ID: ALA463612

PubChem CID: 10494359

Max Phase: Preclinical

Molecular Formula: C15H23BrO

Molecular Weight: 299.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=CC[C@]2(CC1)C(C)=C[C@@H](O)[C@H](Br)C2(C)C

Standard InChI:  InChI=1S/C15H23BrO/c1-10-5-7-15(8-6-10)11(2)9-12(17)13(16)14(15,3)4/h5,9,12-13,17H,6-8H2,1-4H3/t12-,13+,15+/m1/s1

Standard InChI Key:  GBUVGHSRKIJUDI-IPYPFGDCSA-N

Molfile:  

     RDKit          2D

 17 18  0  0  0  0  0  0  0  0999 V2000
    6.8448   -0.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5609   -0.5487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2682   -0.1386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2731    0.6859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6456    0.3016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8404    0.6893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4232   -0.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4232   -0.9605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1343   -1.3703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8496   -0.9605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1343    0.2815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5427    0.9996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7148    0.9996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7066    0.2761    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.7093   -1.3740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0575    0.4235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5648   -1.3761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  7  8  1  0
  7 11  1  0
  8  9  1  0
  9 10  2  0
 10  1  1  0
  1 11  1  0
 11 12  1  0
 11 13  1  0
  7 14  1  6
  8 15  1  1
  4 16  1  0
 10 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA463612

   (3R,4R,6R)-4-bromo-1,5,5,9-tetramethylspiro[5.5]undeca-1,9-dien-3-ol

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: 299.25

Molecular Weight (Monoisotopic): 298.0932

AlogP: 4.21

#Rotatable Bonds: ┄

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: 13.74

CX Basic pKa: ┄

CX LogP: 3.86

CX LogD: 3.86

Aromatic Rings: ┄

Heavy Atoms: 17

QED Weighted: 0.52

Np Likeness Score: 3.26

References

1. König GM, Wright AD..  (1997)  Laurencia rigida: chemical investigations of its antifouling dichloromethane extract.,  60  (10): [PMID:9358636] [10.1021/np970181r]

Source

Source(1):

• Scientific Literature