Metabolomics Structure Database

MDLMOL SDF CSV TSV

MW REGNO:	50605
Common Name:	6-aminopenicillanic acid
Systematic Name:	6-amino-2,2-dimethylpenam-3alpha-carboxylic acid
RefMet Name:	6-Aminopenicillanic acid
Synonyms:	(2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; 6-APA; 6-Aminopenicillamine acid; 6-Apa; 6-Aps; Aminopenicillanic acid; Penicin; Penin; Phenacyl 6-aminopenicillinate [PubChem Synonyms]
Exact Mass:	216.0569 (neutral)    Calculate m/z: (Choose adduct) [M+H]+ [M+H-H2O]+ [M.]+ [M+2H]2+ [M+3H]3+ [M+4H]4+ [M+K]+ [M+2K]2+ [M-H+2K]+ [M+Na]+ [M+2Na]2+ [M-H+2Na]+ [M+Li]+ [M+2Li]2+ [M+NH4]+ [M-H]- [M-2H]2- [M-3H]3- [M-4H]4- [M+Cl]- [M+OAc]- [M+HCOO]- M(neutral)
Formula:	C8H12N2O3S
InChIKey:	NGHVIOIJCVXTGV-ALEPSDHESA-N
ClassyFire superclass:	Organic acids and derivatives [C0000264]
ClassyFire class:	Carboxylic acids and derivatives [C0000265]
ClassyFire subclass:	Amino acids, peptides, and analogues [C0000013]
ClassyFire direct parent:	Dipeptides [C0004830]
NP-MRD NMR spectra:	View NMR spectra
SMILES:	CC1(C)[C@H](C(=O)O)N2C(=O)[C@H]([C@H]2S1)N
Studies:	Available studies (via RefMet name)

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External database links:

PubChem CID:	11082
CHEBI ID:	16705
HMDB ID:	HMDB0060618
KEGG ID:	C02954
BMRB ID:	bmse000312
MetaCyc ID:	6-AMINOPENICILLANATE
Natural Products Atlas ID:	NP016008
NP-MRD ID(NMR):	NP0002695
Plant Metabolite Hub(Pmhub):	MS000011189

Calculated physicochemical properties (?):

Heavy Atoms:	14
Rings:	2
Aromatic Rings:	0
Rotatable Bonds:	1
van der Waals Molecular volume:	183.84 Å3 molecule-1
Toplogical Polar Sufrace Area:	83.63 Å2 molecule-1
Hydrogen Bond Donors:	2
Hydrogen Bond Acceptors:	4
logP:	0.61
Molar Refractivity:	53.75
Fraction sp3 Carbons:	0.75
sp3 Carbons:	6

References

LIPID MAPS classification: "Update of the LIPID MAPS comprehensive classification system for lipids", Fahy E, Subramaniam S, Murphy RC, Nishijima M, Raetz CR, Shimizu T, Spener F, van Meer G, Wakelam MJ, and Dennis EA, J. Lipid Res. (2009) 50: S9-S14. DOI: 10.1194/jlr.R800095-JLR200
ClassyFire classification: "ClassyFire: automated chemical classification with a comprehensive, computable taxonomy", Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS, J. Cheminformatics (2016) 8:61. DOI: 10.1186/s13321-016-0174-y