Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:40 UTC
HMDB IDHMDB0014559
Secondary Accession Numbers
  • HMDB0030484
  • HMDB14559
  • HMDB30484
Metabolite Identification
Common NameAmpicillin
DescriptionAmpicillin is found in common pea. It is also a potential contaminant of cow's milk arising from its veterinary use. Ampicillin is a semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic. It has been used extensively to treat bacterial infections since 1961. It is considered part of the aminopenicillin family and is roughly equivalent to amoxicillin in terms of spectrum and level of activity
Structure
Data?1582753193
Synonyms
ValueSource
(2S,5R,6R)-6-{[(2R)-2-amino-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acidChEBI
(2S,5R,6R)-6-{[(2R)-2-amino-2-phenylethanoyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylIC ACIDChEBI
(2S,6R)-6-{[(2R)-2-amino-2-phenylethanoyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acidChEBI
6-(D-(2-Amino-2-phenylacetamido))-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acidChEBI
ABPCChEBI
AminobenzylpenicillinChEBI
AMPChEBI
AmpicilinaChEBI
Ampicillin acidChEBI
Ampicillin anhydrousChEBI
AmpicillineChEBI
AmpicillinumChEBI
Anhydrous ampicillinChEBI
APChEBI
D-(-)-6-(alpha-Aminophenylacetamido)penicillanic acidChEBI
D-(-)-AmpicillinChEBI
OmnipenKegg
(2S,5R,6R)-6-{[(2R)-2-amino-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylateGenerator
(2S,5R,6R)-6-{[(2R)-2-amino-2-phenylethanoyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylateGenerator
(2S,6R)-6-{[(2R)-2-amino-2-phenylethanoyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylateGenerator
6-(D-(2-Amino-2-phenylacetamido))-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylateGenerator
D-(-)-6-(a-Aminophenylacetamido)penicillanateGenerator
D-(-)-6-(a-Aminophenylacetamido)penicillanic acidGenerator
D-(-)-6-(alpha-Aminophenylacetamido)penicillanateGenerator
D-(-)-6-(Α-aminophenylacetamido)penicillanateGenerator
D-(-)-6-(Α-aminophenylacetamido)penicillanic acidGenerator
(2S,5R,6R)-6-[[(2R)-2-Amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acidHMDB
6-(a-Aminophenylacetamido)penicillanic acidHMDB
6-(D(-)-alpha-Aminophenylacetamido)penicillanic acidHMDB
6-D(-)-alpha-Aminophenylacetamido-penicillanic acidHMDB
6-[(Aminophenylacetyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 9ciHMDB
AcillinHMDB
AdobacillinHMDB
AlpenHMDB
alpha-AminobenzylpenicillinHMDB
AmblosinHMDB
AmcillHMDB
AmfipenHMDB
Amfipen VHMDB
Amipenix SHMDB
AmpenHMDB
AMPIHMDB
Ampi-bolHMDB
Ampi-coHMDB
Ampi-tabHMDB
AmpichelHMDB
AmpicilHMDB
Ampicillin anhydrateHMDB
Ampicillin baseHMDB
Ampicillin sodiumHMDB
Ampicillin trihydrateHMDB
AmpicillinaHMDB
AmpifarmHMDB
AmpikelHMDB
AmpimedHMDB
AmpipeninHMDB
AmpiscelHMDB
AmpisynHMDB
AmpivaxHMDB
AmpivetHMDB
AmplacilinaHMDB
AmplinHMDB
AmplipenylHMDB
AmplisomHMDB
AmplitalHMDB
AustrapenHMDB
AY 6108HMDB
Bayer 5427HMDB
BinotalHMDB
BonapicillinHMDB
BritacilHMDB
BRL 1341HMDB
CampicillinHMDB
CimexHMDB
CopharcilinHMDB
D-(-)-alpha-AminobenzylpenicillinHMDB
D-(-)-alpha-AminopenicillinHMDB
D-a-AminobenzylpenicillinHMDB
D-AmpicillinHMDB
D-CillinHMDB
DelcillinHMDB
DeripenHMDB
DivercillinHMDB
DoktacillinHMDB
DuphacillinHMDB
GeocillinHMDB
GrampenilHMDB
GuicitrinaHMDB
GuicitrineHMDB
KS-R1HMDB
LifeampilHMDB
MagnapenHMDB
MarcillinHMDB
MorepenHMDB
NorobrittinHMDB
Novo-ampicillinHMDB
NSC 528986HMDB
NuvapenHMDB
Olin kidHMDB
OrbicilinaHMDB
Pen aHMDB
Pen ampilHMDB
PenbristolHMDB
PenbritinHMDB
PenbrockHMDB
PeniclineHMDB
PenimicHMDB
PensynHMDB
PentrexHMDB
PentrexlHMDB
PentrexylHMDB
PentritinHMDB
Pfizerpen aHMDB
PolycillinHMDB
PonecilHMDB
PrincillinHMDB
PrincipenHMDB
QidampHMDB
RacenacillinHMDB
Ro-ampenHMDB
RosamplineHMDB
RoscillinHMDB
SemicillinHMDB
ServicillinHMDB
SK-AmpicillinHMDB
SumipantoHMDB
SupenHMDB
SynpeninHMDB
TexcillinHMDB
TokiocillinHMDB
TolomolHMDB
TotacillinHMDB
TotalciclinaHMDB
TotapenHMDB
TrifacilinaHMDB
UkapenHMDB
UltrabionHMDB
UltrabronHMDB
VampenHMDB
ViccillinHMDB
VidocillinHMDB
VidopenHMDB
WypicilHMDB
Aminobenzyl penicillinHMDB
Antibiotic KS R1HMDB
KS-R1, AntibioticHMDB
Sodium, ampicillinHMDB
Antibiotic KS-R1HMDB
Penicillin, aminobenzylHMDB
Trihydrate, ampicillinHMDB
Chemical FormulaC16H19N3O4S
Average Molecular Weight349.405
Monoisotopic Molecular Weight349.109626801
IUPAC Name(2S,5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Traditional Nameampicillin
CAS Registry Number69-53-4
SMILES
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=CC=C1)C(O)=O
InChI Identifier
InChI=1S/C16H19N3O4S/c1-16(2)11(15(22)23)19-13(21)10(14(19)24-16)18-12(20)9(17)8-6-4-3-5-7-8/h3-7,9-11,14H,17H2,1-2H3,(H,18,20)(H,22,23)/t9-,10-,11+,14-/m1/s1
InChI KeyAVKUERGKIZMTKX-NJBDSQKTSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as penicillins. These are organic compounds containing the penicillin core structure, which is structurally characterized by a penam ring bearing two methyl groups at position 2, and an amide group at position 6 [starting from the sulfur atom at position 1].
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassBeta lactams
Direct ParentPenicillins
Alternative Parents
Substituents
  • Penicillin
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Phenylacetamide
  • Aralkylamine
  • Monocyclic benzene moiety
  • Benzenoid
  • Thiazolidine
  • Tertiary carboxylic acid amide
  • Amino acid or derivatives
  • Azetidine
  • Amino acid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Dialkylthioether
  • Hemithioaminal
  • Thioether
  • Primary aliphatic amine
  • Amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Primary amine
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point208 °CPhysProp
Boiling PointNot AvailableNot Available
Water Solubility10100 mg/L (at 21 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
LogP1.35SANGSTER (1994)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Baker191.230932474
[M+H]+Baker193.16730932474
[M-H]-Not Available191.2http://allccs.zhulab.cn/database/detail?ID=AllCCS00000942
[M+H]+Not Available179.109http://allccs.zhulab.cn/database/detail?ID=AllCCS00000942
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.6 g/LALOGPS
logP0.88ALOGPS
logP-2ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)3.24ChemAxon
pKa (Strongest Basic)7.44ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area112.73 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity87.52 m³·mol⁻¹ChemAxon
Polarizability34.54 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+179.08131661259
DarkChem[M-H]-173.71131661259
DeepCCS[M-2H]-214.99430932474
DeepCCS[M+Na]+190.16130932474
AllCCS[M+H]+177.932859911
AllCCS[M+H-H2O]+175.332859911
AllCCS[M+NH4]+180.432859911
AllCCS[M+Na]+181.132859911
AllCCS[M-H]-179.632859911
AllCCS[M+Na-2H]-179.632859911
AllCCS[M+HCOO]-179.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Ampicillin[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=CC=C1)C(O)=O4056.3Standard polar33892256
Ampicillin[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=CC=C1)C(O)=O2354.4Standard non polar33892256
Ampicillin[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=CC=C1)C(O)=O3004.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Ampicillin,1TMS,isomer #1CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)C3=CC=CC=C3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C2750.9Semi standard non polar33892256
Ampicillin,1TMS,isomer #2CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N[Si](C)(C)C)C3=CC=CC=C3)C(=O)N2[C@H]1C(=O)O2790.8Semi standard non polar33892256
Ampicillin,1TMS,isomer #3CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N)C3=CC=CC=C3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O2725.7Semi standard non polar33892256
Ampicillin,2TMS,isomer #1CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N[Si](C)(C)C)C3=CC=CC=C3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C2759.1Semi standard non polar33892256
Ampicillin,2TMS,isomer #1CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N[Si](C)(C)C)C3=CC=CC=C3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C2736.6Standard non polar33892256
Ampicillin,2TMS,isomer #1CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N[Si](C)(C)C)C3=CC=CC=C3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C3734.1Standard polar33892256
Ampicillin,2TMS,isomer #2CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N)C3=CC=CC=C3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C2691.0Semi standard non polar33892256
Ampicillin,2TMS,isomer #2CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N)C3=CC=CC=C3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C2743.2Standard non polar33892256
Ampicillin,2TMS,isomer #2CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N)C3=CC=CC=C3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C3879.3Standard polar33892256
Ampicillin,2TMS,isomer #3CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N[Si](C)(C)C)C3=CC=CC=C3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O2747.4Semi standard non polar33892256
Ampicillin,2TMS,isomer #3CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N[Si](C)(C)C)C3=CC=CC=C3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O2764.6Standard non polar33892256
Ampicillin,2TMS,isomer #3CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N[Si](C)(C)C)C3=CC=CC=C3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O3674.5Standard polar33892256
Ampicillin,2TMS,isomer #4CC1(C)S[C@@H]2[C@H](NC(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O2785.4Semi standard non polar33892256
Ampicillin,2TMS,isomer #4CC1(C)S[C@@H]2[C@H](NC(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O2841.4Standard non polar33892256
Ampicillin,2TMS,isomer #4CC1(C)S[C@@H]2[C@H](NC(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O3830.0Standard polar33892256
Ampicillin,3TMS,isomer #1CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N[Si](C)(C)C)C3=CC=CC=C3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C2740.6Semi standard non polar33892256
Ampicillin,3TMS,isomer #1CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N[Si](C)(C)C)C3=CC=CC=C3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C2824.2Standard non polar33892256
Ampicillin,3TMS,isomer #1CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N[Si](C)(C)C)C3=CC=CC=C3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C3369.9Standard polar33892256
Ampicillin,3TMS,isomer #2CC1(C)S[C@@H]2[C@H](NC(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C2800.0Semi standard non polar33892256
Ampicillin,3TMS,isomer #2CC1(C)S[C@@H]2[C@H](NC(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C2883.2Standard non polar33892256
Ampicillin,3TMS,isomer #2CC1(C)S[C@@H]2[C@H](NC(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C3538.3Standard polar33892256
Ampicillin,3TMS,isomer #3CC1(C)S[C@@H]2[C@H](N(C(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O2817.7Semi standard non polar33892256
Ampicillin,3TMS,isomer #3CC1(C)S[C@@H]2[C@H](N(C(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O2925.3Standard non polar33892256
Ampicillin,3TMS,isomer #3CC1(C)S[C@@H]2[C@H](N(C(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O3516.9Standard polar33892256
Ampicillin,4TMS,isomer #1CC1(C)S[C@@H]2[C@H](N(C(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C2848.1Semi standard non polar33892256
Ampicillin,4TMS,isomer #1CC1(C)S[C@@H]2[C@H](N(C(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C2975.4Standard non polar33892256
Ampicillin,4TMS,isomer #1CC1(C)S[C@@H]2[C@H](N(C(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C3229.5Standard polar33892256
Ampicillin,1TBDMS,isomer #1CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)C3=CC=CC=C3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C3023.3Semi standard non polar33892256
Ampicillin,1TBDMS,isomer #2CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CC=CC=C3)C(=O)N2[C@H]1C(=O)O3002.5Semi standard non polar33892256
Ampicillin,1TBDMS,isomer #3CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N)C3=CC=CC=C3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O2966.9Semi standard non polar33892256
Ampicillin,2TBDMS,isomer #1CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CC=CC=C3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C3200.4Semi standard non polar33892256
Ampicillin,2TBDMS,isomer #1CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CC=CC=C3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C3193.3Standard non polar33892256
Ampicillin,2TBDMS,isomer #1CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CC=CC=C3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C3863.6Standard polar33892256
Ampicillin,2TBDMS,isomer #2CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N)C3=CC=CC=C3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C3141.9Semi standard non polar33892256
Ampicillin,2TBDMS,isomer #2CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N)C3=CC=CC=C3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C3189.2Standard non polar33892256
Ampicillin,2TBDMS,isomer #2CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N)C3=CC=CC=C3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C3979.0Standard polar33892256
Ampicillin,2TBDMS,isomer #3CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CC=CC=C3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O3151.5Semi standard non polar33892256
Ampicillin,2TBDMS,isomer #3CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CC=CC=C3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O3198.8Standard non polar33892256
Ampicillin,2TBDMS,isomer #3CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CC=CC=C3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O3822.5Standard polar33892256
Ampicillin,2TBDMS,isomer #4CC1(C)S[C@@H]2[C@H](NC(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O3305.2Semi standard non polar33892256
Ampicillin,2TBDMS,isomer #4CC1(C)S[C@@H]2[C@H](NC(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O3239.0Standard non polar33892256
Ampicillin,2TBDMS,isomer #4CC1(C)S[C@@H]2[C@H](NC(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O3915.3Standard polar33892256
Ampicillin,3TBDMS,isomer #1CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CC=CC=C3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C3305.2Semi standard non polar33892256
Ampicillin,3TBDMS,isomer #1CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CC=CC=C3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C3446.6Standard non polar33892256
Ampicillin,3TBDMS,isomer #1CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N[Si](C)(C)C(C)(C)C)C3=CC=CC=C3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C3648.8Standard polar33892256
Ampicillin,3TBDMS,isomer #2CC1(C)S[C@@H]2[C@H](NC(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C3464.9Semi standard non polar33892256
Ampicillin,3TBDMS,isomer #2CC1(C)S[C@@H]2[C@H](NC(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C3480.2Standard non polar33892256
Ampicillin,3TBDMS,isomer #2CC1(C)S[C@@H]2[C@H](NC(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C3738.6Standard polar33892256
Ampicillin,3TBDMS,isomer #3CC1(C)S[C@@H]2[C@H](N(C(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O3482.6Semi standard non polar33892256
Ampicillin,3TBDMS,isomer #3CC1(C)S[C@@H]2[C@H](N(C(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O3507.3Standard non polar33892256
Ampicillin,3TBDMS,isomer #3CC1(C)S[C@@H]2[C@H](N(C(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O3735.5Standard polar33892256
Ampicillin,4TBDMS,isomer #1CC1(C)S[C@@H]2[C@H](N(C(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C3629.9Semi standard non polar33892256
Ampicillin,4TBDMS,isomer #1CC1(C)S[C@@H]2[C@H](N(C(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C3733.1Standard non polar33892256
Ampicillin,4TBDMS,isomer #1CC1(C)S[C@@H]2[C@H](N(C(=O)[C@@H](C3=CC=CC=C3)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C3552.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Ampicillin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-1900000000-328e5756b2a2047f34012017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ampicillin GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-1900000000-49339d5b1f688b0249b72017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ampicillin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ampicillin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Ampicillin LC-ESI-QQ , positive-QTOFsplash10-0udi-1349000000-51be76a1d965184221c82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ampicillin LC-ESI-QQ , positive-QTOFsplash10-0006-9810000000-75530784e97a116633e52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ampicillin LC-ESI-QQ , positive-QTOFsplash10-0006-9600000000-0f235a2c675944bd7f8a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ampicillin LC-ESI-QQ , positive-QTOFsplash10-006x-9300000000-766d3a6fea596a3f18a82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ampicillin LC-ESI-QQ , positive-QTOFsplash10-00di-9100000000-147bdc3aaa0be3d0b4192017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ampicillin 20V, Positive-QTOFsplash10-0a4i-1900000000-b00e3e20b6b67bd66c272021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ampicillin 40V, Positive-QTOFsplash10-0a4i-2900000000-7b6c3a7162ec9326a2462021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ampicillin 40V, Negative-QTOFsplash10-00di-9000000000-f6004cc4fde6cc54c5452021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ampicillin 10V, Negative-QTOFsplash10-0a4i-0090000000-3446c37197fd7dc36a632021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ampicillin 40V, Positive-QTOFsplash10-0a4i-2900000000-3160040d30aba58277312021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ampicillin 10V, Positive-QTOFsplash10-0a4i-0901000000-9e9e3230339584136a972021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ampicillin 20V, Positive-QTOFsplash10-0a4i-0900000000-b7dcea08c5f689065c5c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ampicillin 10V, Positive-QTOFsplash10-0a4i-0901000000-c9400241d2ecd802485e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ampicillin 20V, Negative-QTOFsplash10-0ab9-6090000000-e84a46f7b56ca97f62652021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ampicillin 10V, Positive-QTOFsplash10-0bt9-1912000000-75f97354ed9ba956615b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ampicillin 20V, Positive-QTOFsplash10-0bt9-2910000000-96d30028da61376db9b32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ampicillin 40V, Positive-QTOFsplash10-0a4i-7900000000-eff889c1fe387a2133192016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ampicillin 10V, Negative-QTOFsplash10-0a4i-0291000000-98a4e819f450d352aea42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ampicillin 20V, Negative-QTOFsplash10-0a4i-1591000000-eaed25e7ad3d86ca15642016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ampicillin 40V, Negative-QTOFsplash10-05di-9520000000-3b6aedcd44ff9d287dc02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ampicillin 10V, Negative-QTOFsplash10-0002-0009000000-07647be2cf284515b3662021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ampicillin 20V, Negative-QTOFsplash10-052n-6924000000-83d903205df987b0b6992021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ampicillin 40V, Negative-QTOFsplash10-0006-9300000000-d97c7cfdd5c84d70b4932021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ampicillin 10V, Positive-QTOFsplash10-0f89-0219000000-39936cb3e2a60642fccd2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ampicillin 20V, Positive-QTOFsplash10-01x0-0914000000-4ad13ad2ef6dba0dd8f72021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00415 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00415 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00415
Phenol Explorer Compound IDNot Available
FooDB IDFDB020748
KNApSAcK IDNot Available
Chemspider ID6013
KEGG Compound IDC06574
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAmpicillin
METLIN IDNot Available
PubChem Compound6249
PDB IDAIC
ChEBI ID28971
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Mo BH: [Clinical analysis of 410 cases of drug eruption]. Di Yi Jun Yi Da Xue Xue Bao. 2003 Feb;23(2):183, 186. [PubMed:12581979 ]
  2. Rodevand E, Sletvold O, Kvande KT: [Side effects off allopurinol]. Tidsskr Nor Laegeforen. 2004 Oct 21;124(20):2618-9. [PubMed:15534635 ]
  3. Kadurugamuwa JL, Hengstler B, Zak O: Cerebrospinal fluid protein profile in experimental pneumococcal meningitis and its alteration by ampicillin and anti-inflammatory agents. J Infect Dis. 1989 Jan;159(1):26-34. [PubMed:2462602 ]
  4. Crivaro V, Bagattini M, Salza MF, Raimondi F, Rossano F, Triassi M, Zarrilli R: Risk factors for extended-spectrum beta-lactamase-producing Serratia marcescens and Klebsiella pneumoniae acquisition in a neonatal intensive care unit. J Hosp Infect. 2007 Oct;67(2):135-41. Epub 2007 Sep 19. [PubMed:17884248 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Transporters

General function:
Involved in ion transmembrane transporter activity
Specific function:
Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also relative uptake activity ratio of carnitine to TEA is 11.3
Gene Name:
SLC22A5
Uniprot ID:
O76082
Molecular weight:
62751.1
References
  1. Ganapathy ME, Huang W, Rajan DP, Carter AL, Sugawara M, Iseki K, Leibach FH, Ganapathy V: beta-lactam antibiotics as substrates for OCTN2, an organic cation/carnitine transporter. J Biol Chem. 2000 Jan 21;275(3):1699-707. [PubMed:10636865 ]
General function:
Involved in transporter activity
Specific function:
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products
Gene Name:
SLC15A1
Uniprot ID:
P46059
Molecular weight:
78805.3
References
  1. Covitz KM, Amidon GL, Sadee W: Human dipeptide transporter, hPEPT1, stably transfected into Chinese hamster ovary cells. Pharm Res. 1996 Nov;13(11):1631-4. [PubMed:8956326 ]
  2. Guo A, Hu P, Balimane PV, Leibach FH, Sinko PJ: Interactions of a nonpeptidic drug, valacyclovir, with the human intestinal peptide transporter (hPEPT1) expressed in a mammalian cell line. J Pharmacol Exp Ther. 1999 Apr;289(1):448-54. [PubMed:10087037 ]
  3. Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [PubMed:15567297 ]
  4. Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. [PubMed:9374833 ]
General function:
Involved in transporter activity
Specific function:
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides
Gene Name:
SLC15A2
Uniprot ID:
Q16348
Molecular weight:
81782.8
References
  1. Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. [PubMed:9374833 ]
  2. Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [PubMed:15567297 ]