SCS-C001068
methyl 6-[(2R,3R,4R,5S)-5-[(3Z,5Z)-4,6-dibromohexa-3,5-dienyl]-3-hydroxy-4-methoxyoxolan-2-yl]hex-5-ynoate
Pathway: Fatty acids
Superclass: Fatty Acids and Conjugates
Class: Epoxy fatty acids
Chemical Structure
![Structure of methyl 6-[(2R,3R,4R,5S)-5-[(3Z,5Z)-4,6-dibromohexa-3,5-dienyl]-3-hydroxy-4-methoxyoxolan-2-yl]hex-5-ynoate](/scsmarinenp/static/images/structures/SCS-C001068.png)
Loading 3D structure...
3D conformers are computationally generated from SMILES by RDKit for visualization and download; they are not experimental crystal or NMR structures.
Source Information
Xestospongia testudinaria
(sponge)
Kingdom
Metazoa
Phylum
Porifera
Class
Demospongiae
Order
Haplosclerida
Family
Petrosiidae
Genus
Xestospongia
Species
Xestospongia testudinaria
Weizhou Island
· 20°54′N, 109°06′E
DOI:
10.1016/j.tet.2010.11.045
· Tetrahedron
Drug-likeness (Lipinski Ro5)
Molecular Weight
480.2 Da
Threshold ≤ 500
ALogP
3.44
Threshold ≤ 5
H-Bond Donors
1
Threshold ≤ 5
H-Bond Acceptors
5
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C18H24Br2O5
Molecular Weight:
480.1930 Da
SMILES:
COC(=O)CCCC#C[C@H]1O[C@@H](CC/C=C(Br)/C=C\Br)[C@H](OC)[C@@H]1O
InChIKey:
HAIBUKPIWAWTQQ-NTKKDDFQSA-N
InChI:
InChI=1S/C18H24Br2O5/c1-23-16(21)10-5-3-4-8-14-17(22)18(24-2)15(25-14)9-6-7-13(20)11-12-19/h7,11-12,14-15,17-18,22H,3,5-6,9-10H2,1-2H3/b12-11-,13-7-/t14-,15+,17-,18+/m1/s1
Calculated Properties
ALogP:
3.444 lipophilicity
TPSA:
64.99 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
5
Rotatable Bonds:
8
Ring Count:
1
(0 aromatic)
Chiral Centers:
4
Fsp³:
0.6111 fraction sp³ carbon
Database Information
Compound ID:
SCS-C001068
NPClassifier Pathway:
Fatty acids
NPClassifier Superclass:
Fatty Acids and Conjugates
NPClassifier Class:
Epoxy fatty acids
Glycoside:
No
NPClassifier Status:
Classified
External Links:
General chemistry
Natural product databases
Biological Activity Data
No bioactivity data available for this compound.