alchivemycin A   Click here for help

GtoPdb Ligand ID: 13437

Compound class: Natural product
Comment: Alchivemycin A is a polycyclic polyketide that was isolated from a plant-associated actinomycete Streptomyces species [2]. Spectroscopic analysis and X-ray crystallography were used to define its structure and absolute stereo configuration. We drew the structure as depicted in [2], and the resulting SMILES mapped to the PubChem CID listed below. Alchivemycin A has antimicrobial and anticancer properties in vitro [2-5]. A complex total synthesis that integrated traditional chemical methods and biocatalysis using enzymes engineered from the source bacterium, has been reported [1].
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 9
Hydrogen bond donors 5
Rotatable bonds 3
Topological polar surface area 172.82
Molecular weight 647.8
XLogP 3.26
No. Lipinski's rules broken 1

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

SMILES / InChI / InChIKey
Click here for help
Canonical SMILES C/C=C(\C)/[C@@H]([C@@H]([C@H]1[C@H]([C@@H]([C@@H](C)CCCC[C@H]2[C@@](C)([C@]3([H])[C@H]([C@]4([H])[C@H](C)C[C@H](C)C[C@]4([H])[C@@H]5[C@H]3O5)C(=O)C6=C(CN1OC6=O)O)O2)O)O)O)O
Isomeric SMILES [H][C@]12C[C@@H](C)C[C@@H](C)[C@@]1([H])[C@@H]3C(=O)C4=C(O)CN(OC4=O)[C@@H]([C@@H](O)[C@@H](O)\C(\C)=C\C)[C@@H](O)[C@H](O)[C@@H](C)CCCC[C@@H]5O[C@]5(C)[C@@]3([H])[C@@H]6O[C@H]26
InChI InChI=1S/C35H53NO10/c1-7-16(3)27(38)30(41)26-31(42)28(39)17(4)10-8-9-11-21-35(6,45-21)25-24(29(40)23-20(37)14-36(26)46-34(23)43)22-18(5)12-15(2)13-19(22)32-33(25)44-32/h7,15,17-19,21-22,24-28,30-33,37-39,41-42H,8-14H2,1-6H3/b16-7+/t15-,17-,18+,19-,21-,22+,24-,25+,26-,27-,28+,30+,31+,32+,33-,35-/m0/s1
InChI Key ZEXKBCGEARGIOX-IGRLKBMTSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

Classification Click here for help
Compound class Natural product
Database Links Click here for help
GtoPdb PubChem SID 500839847
PubChem CID 163195538
Search Google for chemical match using the InChIKey ZEXKBCGEARGIOX-IGRLKBMTSA-N
Search Google for chemicals with the same backbone ZEXKBCGEARGIOX
UniChem Compound Search for chemical match using the InChIKey ZEXKBCGEARGIOX-IGRLKBMTSA-N
UniChem Connectivity Search for chemical match using the InChIKey ZEXKBCGEARGIOX-IGRLKBMTSA-N