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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:52 UTC
HMDB IDHMDB0015135
Secondary Accession Numbers
  • HMDB15135
Metabolite Identification
Common NameCyclacillin
DescriptionCyclacillin, also known as cyclapen-W or vastcillin, 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]. A large randomized, double-blind clinical trial published in 1978 also showed that ciclacillin is associated with significantly fewer and milder adverse effects than ampicillin; later studies seemed to confirm this improved tolerability, at least in children. Ciclacillin has been superseded by newer antibiotics and is no longer in clinical use, at least in the United States. Cyclacillin is a drug which is used for the treatment of bacterial infections caused by susceptible organisms. Its spectrum of activity is similar to that of ampicillin, although it is less susceptible to beta-lactamases than ampicillin and has much higher bioavailability. Reaction of cyclohexanone with ammonium carbonate and KCN under the conditions of the Bucherer-Bergs reaction led to hydantoin 1. Treatment with phosgene both protected the amino group and activated the carboxyl group toward amide formation (as 3) and reaction with 6-aminopenicillanic acid (6-APA) gave cyclacillin (4). Cyclacillin is a very strong basic compound (based on its pKa). On acid hydrolysis, α-amino acid 2 resulted. This artifice seems to have worked, since cyclacillin is more active in vivo than its in vitro spectrum suggests. Ciclacillin (INN) or cyclacillin (USAN), trade names Cyclapen, Cyclapen-W, Vastcillin, and others, is an aminopenicillin antibiotic.
Structure
Data?1582753262
Synonyms
ValueSource
(1-Aminocyclohexyl)penicillinChEBI
(2S,5R,6R)-6-{[(1-aminocyclohexyl)carbonyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acidChEBI
6-(1-Aminocyclohexanecarboxamido)penicillanic acidChEBI
6-(1-Aminocyclohexylcarboxamido)penicillanic acidChEBI
BastcillinChEBI
CalthorChEBI
CiclacilinaChEBI
CiclacillinChEBI
CiclacillineChEBI
CiclacillinumChEBI
CitosarinChEBI
CyclapenChEBI
Cyclapen-WChEBI
SyngacillinChEBI
UltracillinChEBI
VastcillinChEBI
VipicilChEBI
WyvitalChEBI
ACPCKegg
(2S,5R,6R)-6-{[(1-aminocyclohexyl)carbonyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylateGenerator
6-(1-Aminocyclohexanecarboxamido)penicillanateGenerator
6-(1-Aminocyclohexylcarboxamido)penicillanateGenerator
AminocyclohexylpenicillinHMDB
CiclacillumHMDB
Chemical FormulaC15H23N3O4S
Average Molecular Weight341.426
Monoisotopic Molecular Weight341.140926929
IUPAC Name(2S,5R,6R)-6-(1-aminocyclohexaneamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Traditional Namecyclacillin
CAS Registry Number3485-14-1
SMILES
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1(N)CCCCC1)C(O)=O
InChI Identifier
InChI=1S/C15H23N3O4S/c1-14(2)9(12(20)21)18-10(19)8(11(18)23-14)17-13(22)15(16)6-4-3-5-7-15/h8-9,11H,3-7,16H2,1-2H3,(H,17,22)(H,20,21)/t8-,9+,11-/m1/s1
InChI KeyHGBLNBBNRORJKI-WCABBAIRSA-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
  • Cyclohexylamine
  • Thiazolidine
  • Tertiary carboxylic acid amide
  • Amino acid or derivatives
  • Azetidine
  • Amino acid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Carboxylic acid
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Dialkylthioether
  • Hemithioaminal
  • Thioether
  • Primary aliphatic amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Amine
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Primary amine
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.9 g/LNot Available
LogP0.4Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.9 g/LALOGPS
logP0.56ALOGPS
logP-1.9ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)3.3ChemAxon
pKa (Strongest Basic)8.45ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area112.73 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity84.22 m³·mol⁻¹ChemAxon
Polarizability34.81 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]+177.15831661259
DarkChem[M-H]-168.5931661259
DeepCCS[M-2H]-218.52830932474
DeepCCS[M+Na]+193.69230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Cyclacillin[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1(N)CCCCC1)C(O)=O3646.8Standard polar33892256
Cyclacillin[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1(N)CCCCC1)C(O)=O2653.8Standard non polar33892256
Cyclacillin[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1(N)CCCCC1)C(O)=O2820.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cyclacillin,1TMS,isomer #1CC1(C)S[C@@H]2[C@H](NC(=O)C3(N)CCCCC3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C2641.2Semi standard non polar33892256
Cyclacillin,1TMS,isomer #2CC1(C)S[C@@H]2[C@H](NC(=O)C3(N[Si](C)(C)C)CCCCC3)C(=O)N2[C@H]1C(=O)O2733.2Semi standard non polar33892256
Cyclacillin,1TMS,isomer #3CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N)CCCCC3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O2605.1Semi standard non polar33892256
Cyclacillin,2TMS,isomer #1CC1(C)S[C@@H]2[C@H](NC(=O)C3(N[Si](C)(C)C)CCCCC3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C2693.7Semi standard non polar33892256
Cyclacillin,2TMS,isomer #1CC1(C)S[C@@H]2[C@H](NC(=O)C3(N[Si](C)(C)C)CCCCC3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C2724.0Standard non polar33892256
Cyclacillin,2TMS,isomer #1CC1(C)S[C@@H]2[C@H](NC(=O)C3(N[Si](C)(C)C)CCCCC3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C3883.2Standard polar33892256
Cyclacillin,2TMS,isomer #2CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N)CCCCC3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C2598.4Semi standard non polar33892256
Cyclacillin,2TMS,isomer #2CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N)CCCCC3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C2641.0Standard non polar33892256
Cyclacillin,2TMS,isomer #2CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N)CCCCC3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C4057.4Standard polar33892256
Cyclacillin,2TMS,isomer #3CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N[Si](C)(C)C)CCCCC3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O2665.7Semi standard non polar33892256
Cyclacillin,2TMS,isomer #3CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N[Si](C)(C)C)CCCCC3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O2725.2Standard non polar33892256
Cyclacillin,2TMS,isomer #3CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N[Si](C)(C)C)CCCCC3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O3713.9Standard polar33892256
Cyclacillin,2TMS,isomer #4CC1(C)S[C@@H]2[C@H](NC(=O)C3(N([Si](C)(C)C)[Si](C)(C)C)CCCCC3)C(=O)N2[C@H]1C(=O)O2763.5Semi standard non polar33892256
Cyclacillin,2TMS,isomer #4CC1(C)S[C@@H]2[C@H](NC(=O)C3(N([Si](C)(C)C)[Si](C)(C)C)CCCCC3)C(=O)N2[C@H]1C(=O)O2790.1Standard non polar33892256
Cyclacillin,2TMS,isomer #4CC1(C)S[C@@H]2[C@H](NC(=O)C3(N([Si](C)(C)C)[Si](C)(C)C)CCCCC3)C(=O)N2[C@H]1C(=O)O3997.9Standard polar33892256
Cyclacillin,3TMS,isomer #1CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N[Si](C)(C)C)CCCCC3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C2682.1Semi standard non polar33892256
Cyclacillin,3TMS,isomer #1CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N[Si](C)(C)C)CCCCC3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C2796.5Standard non polar33892256
Cyclacillin,3TMS,isomer #1CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N[Si](C)(C)C)CCCCC3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C3405.3Standard polar33892256
Cyclacillin,3TMS,isomer #2CC1(C)S[C@@H]2[C@H](NC(=O)C3(N([Si](C)(C)C)[Si](C)(C)C)CCCCC3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C2746.1Semi standard non polar33892256
Cyclacillin,3TMS,isomer #2CC1(C)S[C@@H]2[C@H](NC(=O)C3(N([Si](C)(C)C)[Si](C)(C)C)CCCCC3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C2863.9Standard non polar33892256
Cyclacillin,3TMS,isomer #2CC1(C)S[C@@H]2[C@H](NC(=O)C3(N([Si](C)(C)C)[Si](C)(C)C)CCCCC3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C3717.3Standard polar33892256
Cyclacillin,3TMS,isomer #3CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N([Si](C)(C)C)[Si](C)(C)C)CCCCC3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O2764.0Semi standard non polar33892256
Cyclacillin,3TMS,isomer #3CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N([Si](C)(C)C)[Si](C)(C)C)CCCCC3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O2883.3Standard non polar33892256
Cyclacillin,3TMS,isomer #3CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N([Si](C)(C)C)[Si](C)(C)C)CCCCC3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O3584.4Standard polar33892256
Cyclacillin,4TMS,isomer #1CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N([Si](C)(C)C)[Si](C)(C)C)CCCCC3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C2778.2Semi standard non polar33892256
Cyclacillin,4TMS,isomer #1CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N([Si](C)(C)C)[Si](C)(C)C)CCCCC3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C2919.7Standard non polar33892256
Cyclacillin,4TMS,isomer #1CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N([Si](C)(C)C)[Si](C)(C)C)CCCCC3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C3257.5Standard polar33892256
Cyclacillin,1TBDMS,isomer #1CC1(C)S[C@@H]2[C@H](NC(=O)C3(N)CCCCC3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C2882.6Semi standard non polar33892256
Cyclacillin,1TBDMS,isomer #2CC1(C)S[C@@H]2[C@H](NC(=O)C3(N[Si](C)(C)C(C)(C)C)CCCCC3)C(=O)N2[C@H]1C(=O)O2943.7Semi standard non polar33892256
Cyclacillin,1TBDMS,isomer #3CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N)CCCCC3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O2832.0Semi standard non polar33892256
Cyclacillin,2TBDMS,isomer #1CC1(C)S[C@@H]2[C@H](NC(=O)C3(N[Si](C)(C)C(C)(C)C)CCCCC3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C3120.9Semi standard non polar33892256
Cyclacillin,2TBDMS,isomer #1CC1(C)S[C@@H]2[C@H](NC(=O)C3(N[Si](C)(C)C(C)(C)C)CCCCC3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C3143.2Standard non polar33892256
Cyclacillin,2TBDMS,isomer #1CC1(C)S[C@@H]2[C@H](NC(=O)C3(N[Si](C)(C)C(C)(C)C)CCCCC3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C3910.1Standard polar33892256
Cyclacillin,2TBDMS,isomer #2CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N)CCCCC3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C3035.3Semi standard non polar33892256
Cyclacillin,2TBDMS,isomer #2CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N)CCCCC3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C3067.0Standard non polar33892256
Cyclacillin,2TBDMS,isomer #2CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N)CCCCC3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C4099.8Standard polar33892256
Cyclacillin,2TBDMS,isomer #3CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N[Si](C)(C)C(C)(C)C)CCCCC3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O3096.1Semi standard non polar33892256
Cyclacillin,2TBDMS,isomer #3CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N[Si](C)(C)C(C)(C)C)CCCCC3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O3133.6Standard non polar33892256
Cyclacillin,2TBDMS,isomer #3CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N[Si](C)(C)C(C)(C)C)CCCCC3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O3771.7Standard polar33892256
Cyclacillin,2TBDMS,isomer #4CC1(C)S[C@@H]2[C@H](NC(=O)C3(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CCCCC3)C(=O)N2[C@H]1C(=O)O3227.8Semi standard non polar33892256
Cyclacillin,2TBDMS,isomer #4CC1(C)S[C@@H]2[C@H](NC(=O)C3(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CCCCC3)C(=O)N2[C@H]1C(=O)O3200.0Standard non polar33892256
Cyclacillin,2TBDMS,isomer #4CC1(C)S[C@@H]2[C@H](NC(=O)C3(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CCCCC3)C(=O)N2[C@H]1C(=O)O3987.5Standard polar33892256
Cyclacillin,3TBDMS,isomer #1CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N[Si](C)(C)C(C)(C)C)CCCCC3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C3282.0Semi standard non polar33892256
Cyclacillin,3TBDMS,isomer #1CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N[Si](C)(C)C(C)(C)C)CCCCC3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C3379.0Standard non polar33892256
Cyclacillin,3TBDMS,isomer #1CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N[Si](C)(C)C(C)(C)C)CCCCC3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C3591.9Standard polar33892256
Cyclacillin,3TBDMS,isomer #2CC1(C)S[C@@H]2[C@H](NC(=O)C3(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CCCCC3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C3383.1Semi standard non polar33892256
Cyclacillin,3TBDMS,isomer #2CC1(C)S[C@@H]2[C@H](NC(=O)C3(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CCCCC3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C3433.6Standard non polar33892256
Cyclacillin,3TBDMS,isomer #2CC1(C)S[C@@H]2[C@H](NC(=O)C3(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CCCCC3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C3778.7Standard polar33892256
Cyclacillin,3TBDMS,isomer #3CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CCCCC3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O3406.4Semi standard non polar33892256
Cyclacillin,3TBDMS,isomer #3CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CCCCC3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O3448.7Standard non polar33892256
Cyclacillin,3TBDMS,isomer #3CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CCCCC3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O3711.3Standard polar33892256
Cyclacillin,4TBDMS,isomer #1CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CCCCC3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C3583.0Semi standard non polar33892256
Cyclacillin,4TBDMS,isomer #1CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CCCCC3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C3635.2Standard non polar33892256
Cyclacillin,4TBDMS,isomer #1CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CCCCC3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C3497.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cyclacillin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9110000000-880dc522fc28c1bba7cb2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyclacillin GC-MS (1 TMS) - 70eV, Positivesplash10-0002-9000000000-68fd157b54c0f0c04c1a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyclacillin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyclacillin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclacillin 10V, Positive-QTOFsplash10-03ea-3913000000-e1b225a6069c25031e802016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclacillin 20V, Positive-QTOFsplash10-01pk-6900000000-9015a0229a34616fbc412016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclacillin 40V, Positive-QTOFsplash10-05u5-9100000000-ebbfbef8f7baae6dadba2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclacillin 10V, Negative-QTOFsplash10-0002-0911000000-0b9e6a3d9d3b19d46cac2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclacillin 20V, Negative-QTOFsplash10-0002-0930000000-738172cee45fa138ecea2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclacillin 40V, Negative-QTOFsplash10-002b-9400000000-e5e5efd7b191cd291cea2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclacillin 10V, Positive-QTOFsplash10-0006-0009000000-f94d572cb27dd62c44952021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclacillin 20V, Positive-QTOFsplash10-004l-4529000000-90a2bebebc953a6db79c2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclacillin 40V, Positive-QTOFsplash10-0a59-7922000000-40fa844297d16d9e505b2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclacillin 10V, Negative-QTOFsplash10-0006-0019000000-02832c883fa4bd6dfa392021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclacillin 20V, Negative-QTOFsplash10-0007-9834000000-12493a6db58de235a70b2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclacillin 40V, Negative-QTOFsplash10-00di-8901000000-5c2d54fc89ea21fd80a12021-10-11Wishart 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
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01000 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01000 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01000
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID17941
KEGG Compound IDC12766
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCiclacillin
METLIN IDNot Available
PubChem Compound19003
PDB IDNot Available
ChEBI ID31444
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

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. Ganapathy ME, Brandsch M, Prasad PD, Ganapathy V, Leibach FH: Differential recognition of beta -lactam antibiotics by intestinal and renal peptide transporters, PEPT 1 and PEPT 2. J Biol Chem. 1995 Oct 27;270(43):25672-7. [PubMed:7592745 ]
  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 ]
  3. 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. Ganapathy ME, Brandsch M, Prasad PD, Ganapathy V, Leibach FH: Differential recognition of beta -lactam antibiotics by intestinal and renal peptide transporters, PEPT 1 and PEPT 2. J Biol Chem. 1995 Oct 27;270(43):25672-7. [PubMed:7592745 ]
  2. 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 ]
  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 ]