Doripenem (CED0004328)

Record Information

Version

1.0

Creation Date

2016-05-22 05:52:45 UTC

Update Date

2026-08-19 12:39:13 UTC

Accession Number

CHEM019169

Identification

Common Name

Doripenem

Class

Small Molecule

Description

Doripenem is an organic compound with the chemical formula C15H24N4O6S2 and an average molecular weight of 420.50 g/mol. Doripenem belongs to the beta lactams, a subclass of lactams within the organic compounds. It is further categorized under the superclass of organoheterocyclic compounds. The compound is found in or released from two recorded sources: antennas within electrical and electronic equipment, and beta-lactam antibacterials used in healthcare, pharmaceuticals, and veterinary products. The recorded exposure route for this substance is intravenous. Doripenem interacts with six recorded protein targets. It acts as an antagonist and an inhibitor of several specific proteins, including penicillin-binding protein 1A (mrcA), penicillin-binding protein 1B (mrcB), peptidoglycan D,D-transpeptidase MrdA (mrdA), and peptidoglycan D,D-transpeptidase FtsI (pbpB), as well as two other proteins.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Doribax	HMDB
Doripenem hydrate	HMDB
2-(5-Sulfamoylaminomethylpyrrolidin-3-ylthio)-6-(1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylic acid	HMDB

Chemical Formula

C₁₅H₂₄N₄O₆S₂

Average Molecular Mass

420.504 g/mol

Monoisotopic Mass

420.114 g/mol

CAS Registry Number

148016-81-3

IUPAC Name

(4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-{[(3S,5S)-5-[(sulfamoylamino)methyl]pyrrolidin-3-yl]sulfanyl}-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

Traditional Name

doripenem

SMILES

[H][C@]12[C@@H](C)C(S[C@]3([H])CN[C@H](CNS(N)(=O)=O)C3)=C(N1C(=O)[C@]2([H])[C@@H](C)O)C(O)=O

InChI Identifier

InChI=1S/C15H24N4O6S2/c1-6-11-10(7(2)20)14(21)19(11)12(15(22)23)13(6)26-9-3-8(17-5-9)4-18-27(16,24)25/h6-11,17-18,20H,3-5H2,1-2H3,(H,22,23)(H2,16,24,25)/t6-,7-,8+,9+,10-,11-/m1/s1

InChI Key

AVAACINZEOAHHE-VFZPANTDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as thienamycins. These are beta-lactam antibiotics that differ from penicillins in having the thiazolidine sulfur atom replaced by carbon, the sulfur then becoming the first atom in the side chain.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactams

Sub Class

Beta lactams

Direct Parent

Thienamycins

Alternative Parents

Substituents

Thienamycin
Alpha-amino acid or derivatives
Pyrroline carboxylic acid
Pyrroline carboxylic acid or derivatives
Azepine
Vinylogous thioester
Sulfuric acid diamide
Pyrroline
Pyrrolidine
Tertiary carboxylic acid amide
Organic sulfuric acid or derivatives
Amino acid or derivatives
Azetidine
Thioenolether
Amino acid
Secondary alcohol
Carboxamide group
Carboxylic acid derivative
Carboxylic acid
Secondary aliphatic amine
Monocarboxylic acid or derivatives
Azacycle
Sulfenyl compound
Secondary amine
Organic nitrogen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Amine
Organic oxygen compound
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Organosulfur compound
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

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	3.13 g/L	ALOGPS
logP	-1.3	ALOGPS
logP	-5.6	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	3.54	ChemAxon
pKa (Strongest Basic)	9.51	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	162.06 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	99.88 m³·mol⁻¹	ChemAxon
Polarizability	42.37 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0f6w-9326200000-4861cde5290eee720492	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0592-7512950000-658532e2981499cd6edc	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0it9-1943600000-f374d4830cbecd50a979	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a6r-2639000000-ff276497c5a02d2eafd5	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-8910000000-2dfefb21cf2232ae72ac	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-3119300000-37362f663b8286e96c13	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-9422000000-ba6e1cfe0c79c1e49b32	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004m-8910000000-dbf716b9b6fe4631d837	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0000900000-d0feed1f0dac6e4a2b5d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014j-0849700000-36f5a3df0235209ecea8	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-9261100000-7a9967815e8062e33fc2	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0000900000-ac68f4c92b25764c0e48	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0uk9-0003900000-bc7509b063baf56ca276	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0v00-3900000000-7822c9c5ed2340eee046	Not Available	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
5307.0	Log mg/kg	[3000:9400]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
341	Beta-lactam antibacterials	Healthcare, pharmaceuticals & veterinary products	Not Available
506	Antennas	Electrical & Electronic Equipment	Not Available

Pathways

1 pathway

Doripenem Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Carbonic anhydrase 2	P00918	Humans	Predicted (SEA)	6256.2
Click to view 3D structure	Carbonic anhydrase 4	P22748	Humans	Predicted (SEA)	4747.48
Click to view 3D structure	Carbonic anhydrase 13	Q8N1Q1	Humans	Predicted (SEA)	3305.32
Click to view 3D structure	Carbonic anhydrase 6	P23280	Humans	Predicted (SEA)	4200.43
Click to view 3D structure	Carbonic anhydrase 5B, mitochondrial	Q9Y2D0	Humans	Predicted (SEA)	3916.75
Click to view 3D structure	Replicase polyprotein 1ab	Q98VG9	Feline coronavirus (strain FIPV WSU-79/1146)	Predicted (SEA)	198.126
Click to view 3D structure	Beta-1 adrenergic receptor	P08588	Humans	Predicted (SEA)	6183.02
Click to view 3D structure	D(2) dopamine receptor	Q9GJU1	Canis lupus familiaris	Predicted (SEA)	1308.57
Click to view 3D structure	Cytochrome P450 2D6	P10635	Humans	Predicted (SEA)	7628.76
Click to view 3D structure	Carbonic anhydrase 5A, mitochondrial	P35218	Humans	Predicted (SEA)	4676.32
Click to view 3D structure	Solute carrier family 22 member 11	Q9NSA0	Humans	Predicted (SEA)	85.4784
Click to view 3D structure	Xaa-Pro aminopeptidase 2	Q99MA2	Rattus norvegicus	Predicted (SEA)	680.636
Click to view 3D structure	Beta-lactamase GES-13	D1MIX9	Pseudomonas aeruginosa	Predicted (SEA)	4.35956
Click to view 3D structure	Beta-lactamase OXA-48	Q6XEC0	Klebsiella pneumoniae	Predicted (SEA)	0.0778492
Click to view 3D structure	Streptokinase A	P10520	Streptococcus pyogenes serotype M1	Predicted (SEA)	439.381
Click to view 3D structure	Solute carrier family 22 member 6	Q4U2R8	Humans	Predicted (SEA)	706.404
Click to view 3D structure	Organic anion transporter 3	Q8TCC7	Humans	Predicted (SEA)	279.401
Click to view 3D structure	Prothrombin	P00734	Humans	Predicted (SEA)	5889.99
Click to view 3D structure	Speckle-type POZ protein	O43791	Humans	Predicted (SEA)	262.43
Click to view 3D structure	PER-2 beta-lactamase	A2RP81	Citrobacter freundii	Predicted (SEA)	3.89246
Click to view 3D structure	Melanocortin receptor 5	G7PWB2	Macaca fascicularis	Predicted (SEA)	616.566
Click to view 3D structure	Carbonic anhydrase 7	P43166	Humans	Predicted (SEA)	5054.98
Click to view 3D structure	Carbonic anhydrase 1	P00915	Humans	Predicted (SEA)	5808.33
Click to view 3D structure	Carbonic anhydrase 12	O43570	Humans	Predicted (SEA)	5597.36
Click to view 3D structure	Carbonic anhydrase 9	Q16790	Humans	Predicted (SEA)	5827.95