Metabolomics Structure Database

MDLMOL SDF CSV TSV

MW REGNO:	38412
Common Name:	Protopine
Systematic Name:	15-methyl-7,9,19,21-tetraoxa-15-azapentacyclo[15.7.0.0^{4,12}.0^{6,10}.0^{18,22}]tetracosa-1(24),4(12),5,10,17,22-hexaen-3-one
RefMet Name:	Protopine
Synonyms:	[PubChem Synonyms]
Exact Mass:	353.1263 (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:	C20H19NO5
InChIKey:	GPTFURBXHJWNHR-UHFFFAOYSA-N
ClassyFire superclass:	Alkaloids and derivatives
ClassyFire class:	Protopine alkaloids
ClassyFire subclass:	Protopine alkaloids
ClassyFire direct parent:	Aromatic heteropolycyclic compounds
Massbank MS spectra:	View MS spectra
NP-MRD NMR spectra:	View NMR spectra
SMILES:	CN1CCc2cc3c(cc2C(=O)Cc2ccc4c(c2C1)OCO4)OCO3
Studies:	Available studies (via RefMet name)

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All Database Links Calculated Properties Human Pathways

External database links:

PubChem CID:	4970
CHEBI ID:	16415
HMDB ID:	HMDB0003920
KEGG ID:	C05189
Chemspider ID:	4799
METLIN ID:	6988
MetaCyc ID:	PROTOPINE
NP-MRD ID(NMR):	NP0030595
EPA CompTox DB:	DTXCID7078773
Plant Metabolite Hub(Pmhub):	MS000000472

Calculated physicochemical properties (?):

Heavy Atoms:	26
Rings:	5
Aromatic Rings:	2
Rotatable Bonds:	0
van der Waals Molecular volume:	307.43 Å3 molecule-1
Toplogical Polar Sufrace Area:	65.51 Å2 molecule-1
Hydrogen Bond Donors:	0
Hydrogen Bond Acceptors:	6
logP:	2.84
Molar Refractivity:	93.69
Fraction sp3 Carbons:	0.35
sp3 Carbons:	7

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
NPClassifier classification: "NPClassifier: A Deep Neural Network-Based Structural Classification Tool for Natural Products", Kim HW, Wang M, Leber CA, Nothias LF, Reher R, Kang KB, van der Hooft JJJ, Dorrestein PC, Gerwick WH and Cottrell GW. J Nat Prod. 2021 Nov 26;84(11):2795-2807.DOI: 10.1021/acs.jnatprod.1c00399.