zerumbone epoxide

ID: ALA512339

PubChem CID: 11368318

Max Phase: Preclinical

Molecular Formula: C15H22O2

Molecular Weight: 234.34

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Zerumbone Epoxide | Zerumbone epoxide|CHEMBL512339|BDBM50242109

Canonical SMILES:  C/C1=C\CC[C@@]2(C)O[C@@H]2CC(C)(C)/C=C/C1=O

Standard InChI:  InChI=1S/C15H22O2/c1-11-6-5-8-15(4)13(17-15)10-14(2,3)9-7-12(11)16/h6-7,9,13H,5,8,10H2,1-4H3/b9-7+,11-6+/t13-,15-/m1/s1

Standard InChI Key:  UXYYOHOTPOQJPD-OEPOZYLCSA-N

Molfile:  

     RDKit          2D

 18 19  0  0  0  0  0  0  0  0999 V2000
    6.4330  -15.3463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4330  -16.1673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8525  -16.1673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8525  -15.3463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1449  -14.9293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5681  -14.9359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1449  -14.1084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5669  -16.5843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5669  -17.4053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8532  -17.8239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1423  -17.4053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4299  -17.8138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7135  -17.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8911  -17.3966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1299  -17.9743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8536  -18.6753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1106  -18.2436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1367  -16.5496    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0
 11 10  1  0
  4  5  1  0
  1  2  2  0
  4  6  1  0
 11 12  1  0
 12 13  1  0
  2 13  1  0
  5  7  2  0
 13 14  1  0
  1  5  1  0
 13 15  1  0
  3  8  1  0
 10 16  1  6
 11 17  1  0
  3  4  2  0
 10 17  1  0
  8  9  1  0
 11 18  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA512339

   ZERUMBONE EPOXIDE

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: 234.34

Molecular Weight (Monoisotopic): 234.1620

AlogP: 3.43

#Rotatable Bonds: ┄

Polar Surface Area: 29.60

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.67

CX LogD: 3.67

Aromatic Rings: ┄

Heavy Atoms: 17

QED Weighted: 0.60

Np Likeness Score: 3.14

References

1. Usia T, Iwata H, Hiratsuka A, Watabe T, Kadota S, Tezuka Y..  (2004)  Sesquiterpenes and flavonol glycosides from Zingiber aromaticum and their CYP3A4 and CYP2D6 inhibitory activities.,  67  (7): [PMID:15270556] [10.1021/np030556a]

2. Zhang R, Feng X, Su G, Mu Z, Zhang H, Zhao Y, Jiao S, Cao L, Chen S, Tu P, Chai X..  (2018)  Bioactive Sesquiterpenoids from the Peeled Stems of Syringa pinnatifolia.,  81  (8): [PMID:30024153] [10.1021/acs.jnatprod.7b01071]

3. Tan YP, Savchenko AI, Agnew-Francis KA, Boyle GM, Bernhardt PV, Fraser JA, Williams CM..  (2020)  Kalparinol, a Salvialane (Isodaucane) Sesquiterpenoid Derived from Native Australian Dysphania Species That Suggests a Putative Biogenetic Link to Zerumbone.,  83  (5): [PMID:32302147] [10.1021/acs.jnatprod.9b01039]

Source

Source(1):

• Scientific Literature