ContaminantDB: Pirarubicin

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

Record Information

Version

1.0

Creation Date

2016-05-22 05:56:06 UTC

Update Date

2016-11-09 01:15:57 UTC

Accession Number

CHEM019229

Identification

Common Name

Pirarubicin

Class

Small Molecule

Description

Contaminant Sources

ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4'-O-Tetrahydropyranyladriamycin	MeSH
4'-O-Tetrahydropyranyldoxorubicin	MeSH
4'-O-Tetrapyranyldoxorubicin	MeSH
Aventis brand OF pirarubicin	MeSH
THP-ADM	MeSH
THP-DOX	MeSH
THP-Adriamycin	MeSH
THP-Doxorubicin	MeSH
Theprubicin	MeSH
Théprubicine	MeSH
Pirarubicin	MeSH
Pirarubicin hydrochloride	MeSH
Thepirubicin	MeSH
Therarubicin	MeSH

Chemical Formula

C₃₂H₃₇NO₁₂

Average Molecular Mass

627.643 g/mol

Monoisotopic Mass

627.232 g/mol

CAS Registry Number

72496-41-4

IUPAC Name

(8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-6-methyl-5-[(2R)-oxan-2-yloxy]oxan-2-yl]oxy}-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

Traditional Name

(8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-6-methyl-5-[(2R)-oxan-2-yloxy]oxan-2-yl]oxy}-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-9,10-dihydro-7H-tetracene-5,12-dione

SMILES

[H][C@]1(N)C[C@]([H])(O[C@@]2([H])C[C@@](O)(CC3=C(O)C4=C(C(O)=C23)C(=O)C2=C(C=CC=C2OC)C4=O)C(=O)CO)O[C@@]([H])(C)[C@@]1([H])O[C@]1([H])CCCCO1

InChI Identifier

InChI=1S/C32H37NO12/c1-14-31(45-21-8-3-4-9-42-21)17(33)10-22(43-14)44-19-12-32(40,20(35)13-34)11-16-24(19)30(39)26-25(28(16)37)27(36)15-6-5-7-18(41-2)23(15)29(26)38/h5-7,14,17,19,21-22,31,34,37,39-40H,3-4,8-13,33H2,1-2H3/t14-,17-,19-,21+,22-,31+,32-/m0/s1

InChI Key

KMSKQZKKOZQFFG-YXRRJAAWSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as anthracyclines. These are polyketides containing a tetracenequinone ring structure with a sugar attached by glycosidic linkage.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Anthracyclines

Sub Class

Not Available

Direct Parent

Anthracyclines

Alternative Parents

Substituents

Anthracycline
Anthracyclinone-skeleton
Aminoglycoside core
Tetracenequinone
9,10-anthraquinone
1,4-anthraquinone
Anthracene
Glycosyl compound
O-glycosyl compound
Tetralin
Anisole
Aryl ketone
Alkyl aryl ether
Amino saccharide
Benzenoid
Monosaccharide
Oxane
Alpha-hydroxy ketone
Vinylogous acid
Tertiary alcohol
Ketone
Polyol
Oxacycle
Organoheterocyclic compound
Acetal
Ether
Organonitrogen compound
Carbonyl group
Organooxygen compound
Primary amine
Primary aliphatic amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Amine
Organic nitrogen compound
Alcohol
Primary alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	0.3 g/L	ALOGPS
logP	2.06	ALOGPS
logP	2.05	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	7.99	ChemAxon
pKa (Strongest Basic)	9.09	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	204.3 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	157.38 m³·mol⁻¹	ChemAxon
Polarizability	64.85 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-02dj-1007489000-6eb463e623aa0db37827	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014s-4208940000-7f186b794a716fbf5dd7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05od-9106510000-3401a72ae62b0b79f454	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004j-1203179000-54240d835e28f8b0d4b6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bu0-4119543000-25f9cac5328d24f799b7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0nn9-9504510000-1e870dd326773f28c4cc	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

DB11616

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Pirarubicin

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

11296583

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Pirarubicin (CHEM019229)

Structure for CHEM019229: Pirarubicin