Metabolomics Structure Database

MDLMOL SDF CSV TSV

MW REGNO:	54399
Common Name:	Cyclic ADP-ribose
Systematic Name:	(2R,3R,4S,5R,13R,14S,15R,16R)-8,10-dihydroxy-24-imino-8,10-dioxo-7,9,11,25,26-pentaoxa-1,17,19,22-tetraza-8lambda5,10lambda5-diphosphapentacyclo[18.3.1.12,5.113,16.017,21]hexacosa-18,20,22-triene-3,4,14,15-tetrol
RefMet Name:	Cyclic ADP-ribose
Synonyms:	Cyclic ADP-ribose; E-NAD; Enzyme-activated NAD; cADPR; cyclic ADP-D-ribose; cyclic adenosine diphosphate ribose [PubChem Synonyms]
Exact Mass:	541.0611 (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:	C15H21N5O13P2
InChIKey:	BQOHYSXSASDCEA-KEOHHSTQSA-N
ClassyFire superclass:	Organic oxygen compounds
ClassyFire class:	Organooxygen compounds
ClassyFire subclass:	Carbohydrates and carbohydrate conjugates
ClassyFire direct parent:	Pentose phosphates
SMILES:	C1[C@@H]2[C@H]([C@H]([C@H](n3cnc4c(c3=N)ncn4[C@H]3[C@@H]([C@@H]([C@@H](COP(=O)(O)OP(=O)(O)O1)O3)O)O)O2)O)O
Studies:	Available studies (via RefMet name)

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External database links:

PubChem CID:	123847
CHEBI ID:	31445
HMDB ID:	HMDB0249529
MetaCyc ID:	CPD-14880
EPA CompTox DB:	DTXCID301333005

Calculated physicochemical properties (?):

Heavy Atoms:	35
Rings:	6
Aromatic Rings:	2
Rotatable Bonds:	0
van der Waals Molecular volume:	379.03 Å3 molecule-1
Toplogical Polar Sufrace Area:	271.51 Å2 molecule-1
Hydrogen Bond Donors:	7
Hydrogen Bond Acceptors:	17
logP:	0.74
Molar Refractivity:	109.74
Fraction sp3 Carbons:	0.67
sp3 Carbons:	10

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.