ContaminantDB: Riboprine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 07:27:55 UTC

Update Date

2016-11-09 01:16:16 UTC

Accession Number

CHEM020821

Identification

Common Name

Riboprine

Class

Small Molecule

Description

A nucleoside analogue in which adenosine has been modified by substitution at the 6-amino nitrogen by a Delta(2)-isopentenyl group.

Contaminant Sources

FooDB Chemicals
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-IPA	ChEBI
2IPA	ChEBI
6-(3-Methyl-2-butenylamino)purine riboside	ChEBI
6-(gamma,gamma-Dimethylallylamino)purine riboside	ChEBI
i6a	ChEBI
Isopentenyladenosine	ChEBI
Isopentenyladenosine riboside	ChEBI
N-(3-Methylbut-2-enyl)adenosine	ChEBI
N(6)-(2-Isopentenyl)adenosine	ChEBI
N(6)-(3-Methyl-2-butenyl)adenosine	ChEBI
Riboprina	ChEBI
Riboprine	ChEBI
Riboprinum	ChEBI
6-(g,g-Dimethylallylamino)purine riboside	Generator
6-(Γ,γ-dimethylallylamino)purine riboside	Generator
N(6)-(delta(2)-Isopentenyl)adenosine	MeSH
N-(3-Methyl-2-buten-1-yl)adenosine	PhytoBank
2iPR	PhytoBank
6-(2-Isopentenyl)adenosine	PhytoBank
6-(3-Methyl-2-butenylamino)-9-beta-D-ribofuranosylpurine	PhytoBank
6-(3-Methyl-2-butenylamino)-9-β-D-ribofuranosylpurine	PhytoBank
6-(3-Methyl-2-butenylamino)-9-beta-ribofuranosylpurine	PhytoBank
6-(3-Methyl-2-butenylamino)-9-β-ribofuranosylpurine	PhytoBank
6-(3-Methyl-2-butenylamino)-beta,D-ribofuranosylpurine	PhytoBank
6-(3-Methyl-2-butenylamino)-β,D-ribofuranosylpurine	PhytoBank
IPA	PhytoBank
Isopentenyladenine riboside	PhytoBank
N-(3-Methyl-2-butenyl)adenosine	PhytoBank
N-Isopentenyladenosine	PhytoBank
N6-(2-Isopentenyl)adenosine	PhytoBank
N6-(3-Methyl-2-butenyl)adenosine	PhytoBank
N6-(Dimethylallyl)adenosine	PhytoBank
N6-(delta2-Isopentenyl)adenine riboside	PhytoBank
N6-(Δ2-Isopentenyl)adenine riboside	PhytoBank
N6-(delta2-Isopentenyl)adenosine	PhytoBank
N6-(Δ2-Isopentenyl)adenosine	PhytoBank
N6-(gamma,gamma-Dimethylallyl)adenosine	PhytoBank
N6-(γ,γ-Dimethylallyl)adenosine	PhytoBank
N6-Isopentenyladenosine	PhytoBank
Isopentenyl adenosine	PhytoBank

Chemical Formula

C₁₅H₂₁N₅O₄

Average Molecular Mass

335.358 g/mol

Monoisotopic Mass

335.159 g/mol

CAS Registry Number

7724-76-7

IUPAC Name

(2R,3S,4R,5R)-2-(hydroxymethyl)-5-{6-[(3-methylbut-2-en-1-yl)amino]-9H-purin-9-yl}oxolane-3,4-diol

Traditional Name

isopentenyladenosine

SMILES

[H][C@]1(CO)O[C@@]([H])(N2C=NC3=C(NCC=C(C)C)N=CN=C23)[C@]([H])(O)[C@]1([H])O

InChI Identifier

InChI=1S/C15H21N5O4/c1-8(2)3-4-16-13-10-14(18-6-17-13)20(7-19-10)15-12(23)11(22)9(5-21)24-15/h3,6-7,9,11-12,15,21-23H,4-5H2,1-2H3,(H,16,17,18)/t9-,11-,12-,15-/m1/s1

InChI Key

USVMJSALORZVDV-SDBHATRESA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleosides

Sub Class

Not Available

Direct Parent

Purine nucleosides

Alternative Parents

Substituents

Purine nucleoside
Glycosyl compound
N-glycosyl compound
6-alkylaminopurine
6-aminopurine
Pentose monosaccharide
Imidazopyrimidine
Purine
Aminopyrimidine
Secondary aliphatic/aromatic amine
Monosaccharide
N-substituted imidazole
Pyrimidine
Imidolactam
Tetrahydrofuran
Azole
Imidazole
Heteroaromatic compound
Secondary alcohol
Organoheterocyclic compound
Azacycle
Secondary amine
Oxacycle
Amine
Organic nitrogen compound
Alcohol
Hydrocarbon derivative
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Primary alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

nucleoside analogue (CHEBI:62881 )
N-ribosyl-N(6)-isopentenyladenine (CHEBI:62881 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	4.23 g/L	ALOGPS
logP	0.25	ALOGPS
logP	-0.43	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	12.45	ChemAxon
pKa (Strongest Basic)	3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	125.55 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	87.81 m³·mol⁻¹	ChemAxon
Polarizability	34.1 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0w30-0960000000-0035fb65e8672a86a8e4	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-001i-3980000000-8a77d79fb39101eb35b1	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9740000000-fef11b9cca0d66b260ec	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0f89-0971000000-8df58b6063424f35a1af	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0f89-0961000000-e57cf833c2dc4f96fcc4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-03dl-0195000000-bb1c98cdfb4dd8bcbcf6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0udi-0291000000-5d247df3981e5a6e1e3b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000i-0039000000-4b317606d25e8dde70f7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0udr-0890000000-592e5a2a1e483e6e96c6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000i-0900000000-ea249daf88f035efbbc9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000j-0921000000-aa0e302b67b3d15cc148	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-1094000000-36a2ac96899c7345379b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-5590000000-4ffae206d270237bc743	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gc0-9640000000-998c5d223e675bf5ce87	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0f89-1179000000-30ba1ff67a425cfbb2f3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-1390000000-4cb3ddc6acbd6135a3de	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-1910000000-02115299433b6f3d4532	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0092000000-e8f3541125a895d0e198	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udr-0690000000-c3d598e1b897f8be2f50	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1920000000-8336f37e1ca1564fa7a8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0029000000-9c5472896f864fba8e44	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zgi-1391000000-70044ff17099de729367	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-0900000000-e42c4160c718b294fcef	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB11933

HMDB ID

HMDB0304396

FooDB ID

FDB030945

Phenol Explorer ID

Not Available

KNApSAcK ID

C00007324

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

22815

ChEBI ID

62881

PubChem Compound ID

Not Available

Kegg Compound ID

C16427

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=20494583

Riboprine (CHEM020821)

Structure for CHEM020821: Riboprine