ChemFOnt: Showing chemical card for (9S)-9-Acetyl-7-[(2R,4S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione (CFc000232939)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 02:02:32 UTC

Chemfont ID

CFc000232939

Molecule Identification

Common Name

(9S)-9-Acetyl-7-[(2R,4S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione

Definition

9-acetyl-7-[(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy]-6,9,11-trihydroxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione 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. 9-acetyl-7-[(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy]-6,9,11-trihydroxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione is a very strong basic compound (based on its pKa). 9-acetyl-7-[(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy]-6,9,11-trihydroxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4 Demethoxydaunorubicin	MeSH
4-Demethoxydaunorubicin	MeSH
IMI 30	MeSH
IMI-30	MeSH
4 Desmethoxydaunorubicin	MeSH
IMI30	MeSH
4-Desmethoxydaunorubicin	MeSH
Hydrochloride, idarubicin	MeSH
Idarubicin	MeSH
Idarubicin hydrochloride	MeSH

Chemical Formula

C₂₆H₂₇NO₉

Average Molecular Weight

497.4939

Monoisotopic Molecular Weight

497.168581467

IUPAC Name

9-acetyl-7-[(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy]-6,9,11-trihydroxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

Traditional Name

idarubicin

CAS Registry Number

57852-57-0

SMILES

CC1OC(CC(N)C1O)OC1CC(O)(CC2=C(O)C3=C(C(O)=C12)C(=O)C1=CC=CC=C1C3=O)C(C)=O

InChI Identifier

InChI=1S/C26H27NO9/c1-10-21(29)15(27)7-17(35-10)36-16-9-26(34,11(2)28)8-14-18(16)25(33)20-19(24(14)32)22(30)12-5-3-4-6-13(12)23(20)31/h3-6,10,15-17,21,29,32-34H,7-9,27H2,1-2H3

InChI Key

XDXDZDZNSLXDNA-UHFFFAOYSA-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
Aryl ketone
Amino saccharide
Oxane
Benzenoid
Monosaccharide
Tertiary alcohol
Alpha-hydroxy ketone
Vinylogous acid
Secondary alcohol
1,2-aminoalcohol
Ketone
Polyol
Acetal
Oxacycle
Organoheterocyclic compound
Primary amine
Carbonyl group
Primary aliphatic amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Organonitrogen compound
Alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.77 g/L	ALOGPS
logP	1.69	ALOGPS
logP	1.9	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	9.55	ChemAxon
pKa (Strongest Basic)	8.95	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	176.61 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	126.43 m³·mol⁻¹	ChemAxon
Polarizability	51.6 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3685

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for (9S)-9-Acetyl-7-[(2R,4S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione (CFc000232939)

MOL for CFc000232939 ((9S)-9-Acetyl-7-[(2R,4S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione)

3D MOL for CFc000232939 ((9S)-9-Acetyl-7-[(2R,4S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione)

3D SDF for CFc000232939 ((9S)-9-Acetyl-7-[(2R,4S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione)

3D-SDF for CFc000232939 ((9S)-9-Acetyl-7-[(2R,4S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione)

PDB for CFc000232939 ((9S)-9-Acetyl-7-[(2R,4S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione)

3D PDB for CFc000232939 ((9S)-9-Acetyl-7-[(2R,4S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione)

SMILES for CFc000232939 ((9S)-9-Acetyl-7-[(2R,4S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione)

INCHI for CFc000232939 ((9S)-9-Acetyl-7-[(2R,4S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione)

Structure for CFc000232939 ((9S)-9-Acetyl-7-[(2R,4S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione)

3D Structure for CFc000232939 ((9S)-9-Acetyl-7-[(2R,4S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione)