(2S,3R,6S,E)-2-bromo-9-(bromomethylene)-1,1-dimethyl-5-methylenespiro[5.5]undec-7-en-3-ol

ID: ALA113677

PubChem CID: 44576245

Max Phase: Preclinical

Molecular Formula: C15H20Br2O

Molecular Weight: 376.13

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1C[C@@H](O)[C@@H](Br)C(C)(C)[C@@]12C=C/C(=C/Br)CC2

Standard InChI:  InChI=1S/C15H20Br2O/c1-10-8-12(18)13(17)14(2,3)15(10)6-4-11(9-16)5-7-15/h4,6,9,12-13,18H,1,5,7-8H2,2-3H3/b11-9-/t12-,13-,15-/m1/s1

Standard InChI Key:  BERVNSMGLDGYPR-IGRCQTSTSA-N

Molfile:  

     RDKit          2D

 18 19  0  0  0  0  0  0  0  0999 V2000
   10.9819   -6.8705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6924   -7.2830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4009   -6.8764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4052   -6.0554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6947   -5.6429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9800   -6.0513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5518   -6.8705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5518   -7.7002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2664   -8.1127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9854   -7.7002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2664   -6.4535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6702   -5.7385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6756   -5.8668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8364   -6.4598    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   11.7002   -8.1121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1212   -5.6457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8374   -8.1127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1244   -4.8206    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
  7 11  1  0
  8  9  1  0
  9 10  1  0
 10  1  1  0
  1 11  1  0
  4  5  1  0
 11 12  1  0
  5  6  1  0
 11 13  1  0
  7  8  1  0
  7 14  1  1
 10 15  2  0
  1  2  1  1
  4 16  2  0
  1  6  1  0
  8 17  1  1
  2  3  2  0
 16 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA113677

   (3R,4S,6S,9E)-4-bromo-9-(bromomethylidene)-5,5-dimethyl-1-methylidenespiro[5.5]undec-10-en-3-ol

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: 376.13

Molecular Weight (Monoisotopic): 373.9881

AlogP: 4.71

#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: ┄

CX Basic pKa: ┄

CX LogP: 3.94

CX LogD: 3.94

Aromatic Rings: ┄

Heavy Atoms: 18

QED Weighted: 0.48

Np Likeness Score: 3.62

References

1. Davyt D, Fernandez R, Suescun L, Mombrú AW, Saldaña J, Domínguez L, Coll J, Fujii MT, Manta E..  (2001)  New sesquiterpene derivatives from the red alga Laurencia scoparia. Isolation, structure determination, and anthelmintic activity.,  64  (12): [PMID:11754610] [10.1021/np0102307]

2. Chen JY, Huang CY, Lin YS, Hwang TL, Wang WL, Chiou SF, Sheu JH..  (2016)  Halogenated Sesquiterpenoids from the Red Alga Laurencia tristicha Collected in Taiwan.,  79  (9): [PMID:27536968] [10.1021/acs.jnatprod.6b00452]

Source

Source(1):

• Scientific Literature