(-)-(2S,3S,6S,9R)-2-bromo-1,1,9-trimethyl-5-methylidenespiro[5.5]undec-7-ene-3,9-diol

ID: ALA448376

PubChem CID: 10969077

Max Phase: Preclinical

Molecular Formula: C15H23BrO2

Molecular Weight: 315.25

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Isorigidol | Isorigidol|CHEMBL448376|(3S,4S,6S,9R)-4-bromo-5,5,9-trimethyl-1-methylidenespiro[5.5]undec-10-ene-3,9-diol

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

Standard InChI:  InChI=1S/C15H23BrO2/c1-10-9-11(17)12(16)13(2,3)15(10)7-5-14(4,18)6-8-15/h5,7,11-12,17-18H,1,6,8-9H2,2-4H3/t11-,12+,14-,15+/m0/s1

Standard InChI Key:  RLCBOPJHZRVMGC-MYZSUADSSA-N

Molfile:  

     RDKit          2D

 18 19  0  0  0  0  0  0  0  0999 V2000
    5.0280   -0.6141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7385   -1.0267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4470   -0.6200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4513    0.2010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7408    0.6135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0261    0.2050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5980   -0.6141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5980   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3125   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0315   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3125   -0.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1593   -0.2109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4443    1.0267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7164    0.5179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7217    0.3896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8825   -0.2034    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.8835   -1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7463   -1.8557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  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
  4 12  1  0
  5  6  1  0
  4 13  1  1
  7  8  1  0
 11 14  1  0
 11 15  1  0
  1  2  1  1
  7 16  1  1
  1  6  1  0
  8 17  1  6
  2  3  2  0
 10 18  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA448376

   ISORIGIDOL

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: 315.25

Molecular Weight (Monoisotopic): 314.0881

AlogP: 3.18

#Rotatable Bonds: ┄

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: 2.57

CX LogD: 2.57

Aromatic Rings: ┄

Heavy Atoms: 18

QED Weighted: 0.53

Np Likeness Score: 3.29

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