ContaminantDB: Adriamycin hydrochloride

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

Record Information

Version

1.0

Creation Date

2016-05-22 04:14:11 UTC

Update Date

2016-11-09 01:15:34 UTC

Accession Number

CHEM017312

Identification

Common Name

Adriamycin hydrochloride

Class

Small Molecule

Description

Not Available

Contaminant Sources

ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Adriacin	Kegg
Adriamycin	Kegg
Doxil	Kegg
Rubex	Kegg
Adriablastin	MeSH
Adriablastine	MeSH
Baxter brand OF doxorubicin hydrochloride	MeSH
Bristol-myers squibb brand OF doxorubicin hydrochloride	MeSH
Ferrer brand OF doxorubicin hydrochloride	MeSH
Hydrochloride, doxorubicin	MeSH
Adriblastina	MeSH
Doxorubicin	MeSH
Doxorubicin NC	MeSH
Doxorubicina ferrer farm	MeSH
Doxorubicina funk	MeSH
Doxotec	MeSH
Kenfarma brand OF doxorubicin hydrochloride	MeSH
Myocet	MeSH
Doxorubicina tedec	MeSH
Hexal brand OF doxorubicin hydrochloride	MeSH
Doxolem	MeSH
Neocorp brand OF doxorubicin hydrochloride	MeSH
Pfizer brand OF doxorubicin hydrochloride	MeSH
Urokit doxo-cell	MeSH
Medac brand OF doxorubicin hydrochloride	MeSH
Ribosepharm brand OF doxorubicin hydrochloride	MeSH
Adriblastin	MeSH
Doxorubicine baxter	MeSH
Onkoworks brand OF doxorubicin hydrochloride	MeSH
Urokit doxo cell	MeSH
Adrimedac	MeSH
Bedford brand OF doxorubicin hydrochloride	MeSH
doxo Cell	MeSH
Elan brand OF doxorubicin hydrochloride	MeSH
Prasfarma brand OF doxorubicin hydrochloride	MeSH
Lemery brand OF doxorubicin hydrochloride	MeSH
Onkodox	MeSH
Ribodoxo	MeSH
Tedec meiji brand OF doxorubicin hydrochloride	MeSH
Adriblastine	MeSH
Columbia brand OF doxorubicin hydrochloride	MeSH
doxo-Cell	MeSH
Doxorubicin hexal	MeSH
Farmiblastina	MeSH
Cell pharm brand OF doxorubicin hydrochloride	MeSH

Chemical Formula

C₂₇H₃₀ClNO₁₁

Average Molecular Mass

579.980 g/mol

Monoisotopic Mass

579.151 g/mol

CAS Registry Number

25316-40-9

IUPAC Name

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

Traditional Name

doxorubicin hydrochloride

SMILES

Cl.[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

InChI Identifier

InChI=1S/C27H29NO11.ClH/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34;/h3-5,10,13,15,17,22,29,31,33,35-36H,6-9,28H2,1-2H3;1H/t10-,13-,15-,17-,22+,27-;/m0./s1

InChI Key

MWWSFMDVAYGXBV-RUELKSSGSA-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
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Tetralin
Anisole
Aryl ketone
Alkyl aryl ether
Amino saccharide
Benzenoid
Monosaccharide
Oxane
Alpha-hydroxy ketone
Tertiary alcohol
Vinylogous acid
Secondary alcohol
Ketone
1,2-aminoalcohol
Polyol
Oxacycle
Acetal
Organoheterocyclic compound
Ether
Alcohol
Carbonyl group
Primary aliphatic amine
Hydrochloride
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Amine
Organooxygen compound
Organic nitrogen compound
Primary alcohol
Primary amine
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	1.18 g/L	ALOGPS
logP	1.41	ALOGPS
logP	0.53	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	8	ChemAxon
pKa (Strongest Basic)	9.93	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	206.07 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	134.59 m³·mol⁻¹	ChemAxon
Polarizability	54.65 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0000090000-deac82977e6ad326c74a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0000090000-deac82977e6ad326c74a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-0000090000-deac82977e6ad326c74a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0000090000-d14c313940169cb76d20	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0000090000-d14c313940169cb76d20	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-0000090000-d14c313940169cb76d20	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

Not Available

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

Not Available

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

443939

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

Adriamycin hydrochloride (CHEM017312)

Structure for CHEM017312: Adriamycin hydrochloride