ChemFOnt: Showing chemical card for N6-(delta2-isopentenyl)-adenosine 5'-monophosphate (CFc000283949)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:37:41 UTC

Chemfont ID

CFc000283949

Molecule Identification

Common Name

N6-(delta2-isopentenyl)-adenosine 5'-monophosphate

Definition

N6-(delta2-isopentenyl)-adenosine 5'-monophosphate, also known as n6-(dimethylallyl)adenosine 5'-phosphate or isopentenyl-amp, is a member of the class of compounds known as purine ribonucleoside monophosphates. Purine ribonucleoside monophosphates are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached. N6-(delta2-isopentenyl)-adenosine 5'-monophosphate is slightly soluble (in water) and a moderately acidic compound (based on its pKa). N6-(delta2-isopentenyl)-adenosine 5'-monophosphate can be found in a number of food items such as arctic blackberry, japanese pumpkin, lichee, and acorn, which makes n6-(delta2-isopentenyl)-adenosine 5'-monophosphate a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Isopentenyl-AMP	ChEBI
Isopentenyladenosine riboside-5'-monophosphate	ChEBI
Isopentenyladenosine-5'-monophosphate	ChEBI
N-(3-Methyl-2-butenyl)-5'-adenylic acid	ChEBI
N6-(delta(2)-Isopentenyl)adenosine 5'-monophosphate	ChEBI
N6-(delta2-Isopentenyl)-adenosine 5'-monophosphate	ChEBI
N(6)-(Delta(2)-Isopentenyl)adenosine 5'-monophosphate	ChEBI
N(6)-(Dimethylallyl)adenosine 5'-(dihydrogen phosphate)	ChEBI
N6-(Dimethylallyl)adenosine 5'-phosphate	ChEBI
N(6)-(Dimethylallyl)adenosine 5'-phosphate	ChEBI
N(6)-Dimethylallyl-5'-adenylic acid	ChEBI
N(6)-Dimethylallyl-AMP	ChEBI
N(6)-Isopentenyladenosine-5'-monophosphate	ChEBI
Isopentenyladenosine riboside-5'-monophosphoric acid	Generator
Isopentenyladenosine-5'-monophosphoric acid	Generator
N-(3-Methyl-2-butenyl)-5'-adenylate	Generator
N6-(delta(2)-Isopentenyl)adenosine 5'-monophosphoric acid	Generator
N6-(Δ(2)-isopentenyl)adenosine 5'-monophosphate	Generator
N6-(Δ(2)-isopentenyl)adenosine 5'-monophosphoric acid	Generator
N6-(delta2-Isopentenyl)-adenosine 5'-monophosphoric acid	Generator
N6-(Δ2-isopentenyl)-adenosine 5'-monophosphate	Generator
N6-(Δ2-isopentenyl)-adenosine 5'-monophosphoric acid	Generator
N(6)-(delta(2)-Isopentenyl)adenosine 5'-monophosphoric acid	Generator
N(6)-(Δ(2)-isopentenyl)adenosine 5'-monophosphate	Generator
N(6)-(Δ(2)-isopentenyl)adenosine 5'-monophosphoric acid	Generator
N(6)-(Dimethylallyl)adenosine 5'-(dihydrogen phosphoric acid)	Generator
N6-(Dimethylallyl)adenosine 5'-phosphoric acid	Generator
N(6)-(Dimethylallyl)adenosine 5'-phosphoric acid	Generator
N(6)-Dimethylallyl-5'-adenylate	Generator
N(6)-Isopentenyladenosine-5'-monophosphoric acid	Generator
N(6)-(Dimethylallyl)adenosine 5'-monophosphoric acid	Generator

Chemical Formula

C₁₅H₂₂N₅O₇P

Average Molecular Weight

415.343

Monoisotopic Molecular Weight

415.125685066

IUPAC Name

{[(2R,3S,4R,5R)-3,4-dihydroxy-5-{6-[(3-methylbut-2-en-1-yl)amino]-9H-purin-9-yl}oxolan-2-yl]methoxy}phosphonic acid

Traditional Name

Isopentenyl-AMP

CAS Registry Number

20268-93-3

SMILES

CC(C)=CCNC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O

InChI Identifier

InChI=1S/C15H22N5O7P/c1-8(2)3-4-16-13-10-14(18-6-17-13)20(7-19-10)15-12(22)11(21)9(27-15)5-26-28(23,24)25/h3,6-7,9,11-12,15,21-22H,4-5H2,1-2H3,(H,16,17,18)(H2,23,24,25)/t9-,11-,12-,15-/m1/s1

InChI Key

DUISZFLWBAPRBR-SDBHATRESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as nicotinamide nucleotides. These are pyridine nucleotides, in which the pyridine base is nicotinamide or a derivative thereof.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyridine nucleotides

Sub Class

Nicotinamide nucleotides

Direct Parent

Nicotinamide nucleotides

Alternative Parents

Substituents

Nicotinamide-nucleotide
Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
Monosaccharide phosphate
N-substituted nicotinamide
Pentose monosaccharide
Dihydropyridine
Hydropyridine
Monosaccharide
Alkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Vinylogous amide
Tetrahydrofuran
Carboxamide group
1,2-diol
Secondary alcohol
Primary carboxylic acid amide
Organoheterocyclic compound
Azacycle
Enamine
Oxacycle
Carboxylic acid derivative
Carbonyl group
Organic nitrogen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Organopnictogen compound
Organic anion
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

a small molecule (NMNH )

Functional Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.83 g/L	ALOGPS
logP	-0.32	ALOGPS
logP	-2.9	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	1.22	ChemAxon
pKa (Strongest Basic)	3.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	172.08 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	98.68 m³·mol⁻¹	ChemAxon
Polarizability	39.74 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0304433

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB031049

KNApSAcK ID

Not Available

Chemspider ID

90571

KEGG Compound ID

C04713

BioCyc ID

CPD-4205

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

15819

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for N6-(delta2-isopentenyl)-adenosine 5'-monophosphate (CFc000283949)

MOL for CFc000283949 (N6-(delta2-isopentenyl)-adenosine 5'-monophosphate)

3D MOL for CFc000283949 (N6-(delta2-isopentenyl)-adenosine 5'-monophosphate)

3D SDF for CFc000283949 (N6-(delta2-isopentenyl)-adenosine 5'-monophosphate)

3D-SDF for CFc000283949 (N6-(delta2-isopentenyl)-adenosine 5'-monophosphate)

PDB for CFc000283949 (N6-(delta2-isopentenyl)-adenosine 5'-monophosphate)

3D PDB for CFc000283949 (N6-(delta2-isopentenyl)-adenosine 5'-monophosphate)

SMILES for CFc000283949 (N6-(delta2-isopentenyl)-adenosine 5'-monophosphate)

INCHI for CFc000283949 (N6-(delta2-isopentenyl)-adenosine 5'-monophosphate)

Structure for CFc000283949 (N6-(delta2-isopentenyl)-adenosine 5'-monophosphate)

3D Structure for CFc000283949 (N6-(delta2-isopentenyl)-adenosine 5'-monophosphate)