ChemFOnt: Showing chemical card for Clarithromycin (CFc000009622)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:49 UTC

Chemfont ID

CFc000009622

Molecule Identification

Common Name

Clarithromycin

Definition

Clarithromycin, a semisynthetic macrolide antibiotic derived from erythromycin, inhibits bacterial protein synthesis by binding to the bacterial 50S ribosomal subunit. Binding inhibits peptidyl transferase activity and interferes with amino acid translocation during the translation and protein assembly process. Clarithromycin may be bacteriostatic or bactericidal depending on the organism and drug concentration.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
6-O-Methylerythromycin	ChEBI
6-O-Methylerythromycin a	ChEBI
CLA	ChEBI
Clarithromycina	ChEBI
Clarithromycine	ChEBI
Clarithromycinum	ChEBI
CAM	Kegg
Biaxin	Kegg
Clathromycin	HMDB

Chemical Formula

C₃₈H₆₉NO₁₃

Average Molecular Weight

747.9534

Monoisotopic Molecular Weight

747.476891299

IUPAC Name

(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-12,13-dihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-7-methoxy-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecane-2,10-dione

Traditional Name

clarithromycin

CAS Registry Number

81103-11-9

SMILES

[H][C@@]1(C[C@@](C)(OC)[C@@H](O)[C@H](C)O1)O[C@H]1[C@H](C)[C@@H](O[C@]2([H])O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@@](C)(C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@](C)(O)[C@@H](CC)OC(=O)[C@@H]1C)OC

InChI Identifier

InChI=1S/C38H69NO13/c1-15-26-38(10,45)31(42)21(4)28(40)19(2)17-37(9,47-14)33(52-35-29(41)25(39(11)12)16-20(3)48-35)22(5)30(23(6)34(44)50-26)51-27-18-36(8,46-13)32(43)24(7)49-27/h19-27,29-33,35,41-43,45H,15-18H2,1-14H3/t19-,20-,21+,22+,23-,24+,25+,26-,27+,29-,30+,31-,32+,33-,35+,36-,37-,38-/m1/s1

InChI Key

AGOYDEPGAOXOCK-KCBOHYOISA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Aminoglycosides

Alternative Parents

Substituents

Aminoglycoside core
Macrolide
Glycosyl compound
O-glycosyl compound
Oxane
Monosaccharide
Tertiary alcohol
1,2-aminoalcohol
Amino acid or derivatives
Carboxylic acid ester
Ketone
Cyclic ketone
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Lactone
Acetal
Carboxylic acid derivative
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
Amine
Organopnictogen compound
Organonitrogen compound
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

macrolide antibiotic (CHEBI:3732 )
Macrolides and lactone polyketides (C06912 )
Macrolides and lactone polyketides (LMPK04000014 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015342)

Source

Exogenous

Exogenous (HMDB: HMDB0015342)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Clarithromycin Action Pathway (PathBank: SMP0000248)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.22 g/L	ALOGPS
logP	3.18	ALOGPS
logP	3.24	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	12.46	ChemAxon
pKa (Strongest Basic)	8.38	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	182.91 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	190.79 m³·mol⁻¹	ChemAxon
Polarizability	82.03 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon