alchivemycin A

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Ligands
alchivemycin A

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

Physico-chemical Properties

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

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/)