Macquarimicin A   Click here for help

GtoPdb Ligand ID: 10978

Compound class: Synthetic organic
Comment: Macquarimicin A was originally isolated as a microbial metabolite from Micromonospora chalcea [1]. A synthetic pathway to generate the Macquarimicin A structure has subsequently been reported [2]. It has some limited antibacterial activity, and has actvity as a neutral sphingomyelinase (N-SMase, sphingomyelin phosphodiesterase) inhibitor [3].
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were 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/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 0
Topological polar surface area 80.67
Molecular weight 330.15
XLogP 0.76
No. Lipinski's rules broken 0

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
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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/)

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Canonical SMILES O[C@H]1C[C@@H]2CC(=O)/C(=C\[C@H]3[C@@H](C1)C=C[C@H]1[C@@H]3C[C@H](C1=O)C)/C(=O)O2
Isomeric SMILES O[C@H]1C[C@@H]2CC(=O)/C(=C\[C@H]3[C@@H](C1)C=C[C@H]1[C@@H]3C[C@H](C1=O)C)/C(=O)O2
InChI InChI=1S/C19H22O5/c1-9-4-15-13(18(9)22)3-2-10-5-11(20)6-12-7-17(21)16(8-14(10)15)19(23)24-12/h2-3,8-15,20H,4-7H2,1H3/b16-8+/t9-,10-,11-,12-,13+,14+,15+/m1/s1
InChI Key BYUKEFZLYIFNCB-MDRYBKLPSA-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/)
References
1. Jackson M, Karwowski JP, Theriault RJ, Rasmussen RR, Hensey DM, Humphrey PE, Swanson SJ, Barlow GJ, Premachandran U, McAlpine JB. (1995)
Macquarimicins, microbial metabolites from Micromonospora. I. Discovery, taxonomy, fermentation and biological properties.
J Antibiot, 48 (6): 462-6. [PMID:7622430]
2. Munakata R, Katakai H, Ueki T, Kurosaka J, Takao K, Tadano K. (2003)
Total synthesis of (+)-macquarimicin A.
J Am Chem Soc, 125 (48): 14722-3. [PMID:14640644]
3. Tanaka M, Nara F, Yamasato Y, Masuda-Inoue S, Doi-Yoshioka H, Kumakura S, Enokita R, Ogita T. (1999)
Macquarimicin A inhibits membrane-bound neutral sphingomyelinase from rat brain.
J Antibiot, 52 (7): 670-3. [PMID:10513848]