Cannabis Compound Database: Showing Compound Card for NADHX (CDB005056)

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Record Information

Version

1.0

Created at

2020-04-17 19:04:53 UTC

Updated at

2020-11-18 16:39:15 UTC

CannabisDB ID

CDB005056

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

NADHX

Description

(6S)-6-beta-hydroxy-1,4,5,6-tetrahydronicotinamide-adenine dinucleotide, also known as (S)-nadh-hydrate or (S)-nadhx, belongs to the class of organic compounds known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group. A tetrahydronicotinamide adenine dinucleotide obtained by formal stereo- and regioselective hydration across the 5,6-double bond in the nicotinyl ring of NADH, with the hydroxy group located at position 6, having (S)-configuration (6S)-6-beta-hydroxy-1,4,5,6-tetrahydronicotinamide-adenine dinucleotide is a very strong basic compound (based on its pKa) (6S)-6-beta-hydroxy-1,4,5,6-tetrahydronicotinamide-adenine dinucleotide exists in all living organisms, ranging from bacteria to humans. Outside of the human body, (6S)-6-beta-hydroxy-1,4,5,6-tetrahydronicotinamide-adenine dinucleotide has been detected, but not quantified in, several different foods, such as pineapples, fireweeds, silver lindens, mentha (mint), and broad beans. This could make (6S)-6-beta-hydroxy-1,4,5,6-tetrahydronicotinamide-adenine dinucleotide a potential biomarker for the consumption of these foods. NADHX is expected to be in Cannabis as all living plants are known to produce and metabolize it.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(6S)-6beta-Hydroxy-1,4,5,6-tetrahydronicotinamide adenine dinucleotide	ChEBI
6beta-Hydroxy-1,4,5,6-tetrahydronicotinamide-adenine dinucleotide	ChEBI
BETA-6-HYDROXY-1,4,5,6-tetrhydronicotinamide adenine dinucleotide	ChEBI
(6S)-6b-Hydroxy-1,4,5,6-tetrahydronicotinamide adenine dinucleotide	Generator
(6S)-6β-hydroxy-1,4,5,6-tetrahydronicotinamide adenine dinucleotide	Generator
6b-Hydroxy-1,4,5,6-tetrahydronicotinamide-adenine dinucleotide	Generator
6β-hydroxy-1,4,5,6-tetrahydronicotinamide-adenine dinucleotide	Generator
b-6-HYDROXY-1,4,5,6-tetrhydronicotinamide adenine dinucleotide	Generator
β-6-hydroxy-1,4,5,6-tetrhydronicotinamide adenine dinucleotide	Generator
(S)-NADH-hydrate	KEGG
(S)-NADHX	KEGG
(6S)-6-Hydroxy-1,4,5,6-tetrahydronicotinamide-adenine dinucleotide	KEGG
(S)-NADH-hydric acid	Generator
(6S)-6b-Hydroxy-1,4,5,6-tetrahydronicotinamide-adenine dinucleotide	Generator
(6S)-6Β-hydroxy-1,4,5,6-tetrahydronicotinamide-adenine dinucleotide	Generator
(6S)-6-b-Hydroxy-1,4,5,6-tetrahydronicotinamide-adenine dinucleotide	Generator
(6S)-6-Β-hydroxy-1,4,5,6-tetrahydronicotinamide-adenine dinucleotide	Generator
Monohydroxytetrahydronicotinamide adenine dinucleotide	HMDB
NADHX	HMDB

Chemical Formula

C₂₁H₃₁N₇O₁₅P₂

Average Molecular Weight

683.46

Monoisotopic Molecular Weight

683.1353

IUPAC Name

[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4R,5R)-5-[(2S)-5-carbamoyl-2-hydroxy-1,2,3,4-tetrahydropyridin-1-yl]-3,4-dihydroxyoxolan-2-yl]methoxy})phosphinic acid

Traditional Name

(S)-nadhx

CAS Registry Number

116561-22-9

SMILES

NC(=O)C1=CN([C@@H]2O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]3O[C@H]([C@H](O)[C@@H]3O)N3C=NC4=C(N)N=CN=C34)[C@@H](O)[C@H]2O)[C@@H](O)CC1

InChI Identifier

InChI=1S/C21H31N7O15P2/c22-17-12-19(25-6-24-17)28(7-26-12)21-16(33)14(31)10(42-21)5-40-45(37,38)43-44(35,36)39-4-9-13(30)15(32)20(41-9)27-3-8(18(23)34)1-2-11(27)29/h3,6-7,9-11,13-16,20-21,29-33H,1-2,4-5H2,(H2,23,34)(H,35,36)(H,37,38)(H2,22,24,25)/t9-,10-,11+,13-,14-,15-,16-,20-,21-/m1/s1

InChI Key

IDBZKGQRLBFUFQ-VPHRTNKSSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Purine nucleotide sugars

Direct Parent

Purine nucleotide sugars

Alternative Parents

Substituents

Purine nucleotide sugar
Purine ribonucleoside diphosphate
Purine ribonucleoside monophosphate
Nicotinamide-nucleotide
Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
6-aminopurine
Monosaccharide phosphate
Organic pyrophosphate
Imidazopyrimidine
Purine
Aminopyrimidine
Monoalkyl phosphate
Tetrahydropyridine
Imidolactam
Alkyl phosphate
Hydropyridine
Pyrimidine
Monosaccharide
N-substituted imidazole
Organic phosphoric acid derivative
Phosphoric acid ester
Azole
Vinylogous amide
Tetrahydrofuran
Imidazole
Heteroaromatic compound
Primary carboxylic acid amide
Carboxamide group
Secondary alcohol
Amino acid or derivatives
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Azacycle
Alkanolamine
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Organopnictogen compound
Alcohol
Primary amine
Amine
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

hemiaminal (CHEBI:44236 )
tetrahydronicotinamide adenine dinucleotide (CHEBI:44236 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-1.9	ALOGPS
logP	-6.5	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	1.85	ChemAxon
pKa (Strongest Basic)	4.01	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	337.85 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	144.05 m³·mol⁻¹	ChemAxon
Polarizability	58.68 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	NADHX, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-017m-1211913000-25814eadfd52e71a50a2	Spectrum
Predicted GC-MS	NADHX, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	NADHX, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	NADHX, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	NADHX, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	NADHX, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	NADHX, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	NADHX, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	NADHX, TMS_1_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	NADHX, TMS_1_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	NADHX, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	NADHX, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	NADHX, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	NADHX, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	NADHX, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	NADHX, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	NADHX, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	NADHX, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	NADHX, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	NADHX, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	NADHX, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	NADHX, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	NADHX, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	NADHX, TMS_2_14, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	NADHX, TMS_2_15, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0920104000-1528abc2c0a942f49031	2015-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-d2229364feb237809db1	2015-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1900000000-c059fcd5287ebb902662	2015-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900316000-b56bcca46a39880ba531	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-1900100000-fd7ebe873ef8a790e710	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a7l-3900000000-e65fb28b52244d9bf64b	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00lu-0700009000-84c79a506933cd12dcfe	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00lr-0613159000-d52e45cdb114fde72b48	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0922100000-1592b6a3cfff1659a174	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03e9-0000009000-4a10771d72bd52ae30c5	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-057i-6000069000-2683c91f3d01d3ae1e5c	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0bvi-6915704000-3bb96fcd514c7f9b7fa8	2021-09-24	View Spectrum

NMR

Not Available

Pathways

Not Available

Protein Targets

Enzymes

Not Available

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0059644

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB030173

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C04856

BioCyc ID

CPD-653

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440516

PDB ID

NAX

ChEBI ID

44236

References

General References

Not Available

Showing Compound Card for NADHX (CDB005056)

Structure for CDB005056 (NADHX)