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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:39 UTC
HMDB IDHMDB0014539
Secondary Accession Numbers
  • HMDB14539
Metabolite Identification
Common NameCarisoprodol
DescriptionCarisoprodol, also known as soma or isoprotane, belongs to the class of organic compounds known as carbamate esters. Carbamate esters are compounds containing an ester of carbamic acid with the general structure R2NC(=O)OR' (R' not H). They are esters of carbamic acids. Based on a literature review a small amount of articles have been published on Carisoprodol.
Structure
Data?1582753190
Synonyms
ValueSource
(+-)-2-Methyl-2-propyl-1,3-propanediol carbamate isopropylcarbamateChEBI
(1-Methylethyl)carbamic acid 2-(((aminocarbonyl)oxy)methyl)-2-methylpentyl esterChEBI
2-Methyl-2-propyl-1,3-propanediol carbamate isopropylcarbamateChEBI
2-Methyl-2-propyltrimethylene carbamate isopropylcarbamateChEBI
Carbamic acid 2-isopropylcarbamoyloxymethyl-2-methyl-pentyl esterChEBI
CarisoprodolumChEBI
Isopropyl meprobamateChEBI
N-Isopropy-2-methyl-2-propyl-1,3-propanediol dicarbamateChEBI
SomaKegg
(+-)-2-Methyl-2-propyl-1,3-propanediol carbamic acid isopropylcarbamic acidGenerator
(1-Methylethyl)carbamate 2-(((aminocarbonyl)oxy)methyl)-2-methylpentyl esterGenerator
2-Methyl-2-propyl-1,3-propanediol carbamic acid isopropylcarbamic acidGenerator
2-Methyl-2-propyltrimethylene carbamic acid isopropylcarbamic acidGenerator
Carbamate 2-isopropylcarbamoyloxymethyl-2-methyl-pentyl esterGenerator
Isopropyl meprobamic acidGenerator
N-Isopropy-2-methyl-2-propyl-1,3-propanediol dicarbamic acidGenerator
CarisoprodateHMDB
CarisoprodatumHMDB
IsomeprobamateHMDB
IsoprotaneHMDB
IsoprothaneHMDB
IsopropylmeprobamateHMDB
Mio relaxHMDB
Schein brand OF carisoprodolHMDB
SomalgitHMDB
SoprodolHMDB
VanadomHMDB
Wallace brand 1 OF carisoprodolHMDB
Belmac brand OF carisoprodolHMDB
CarisomaHMDB
Forest brand OF carisoprodolHMDB
GM Pharmaceuticals brand OF carisoprodolHMDB
IsobamateHMDB
Carter horner brand OF carisoprodolHMDB
Wallace brand 2 OF carisoprodolHMDB
Wallace brand 3 OF carisoprodolHMDB
Chemical FormulaC12H24N2O4
Average Molecular Weight260.33
Monoisotopic Molecular Weight260.173607266
IUPAC Name2-[(carbamoyloxy)methyl]-2-methylpentyl N-(propan-2-yl)carbamate
Traditional NameSoma
CAS Registry Number78-44-4
SMILES
CCCC(C)(COC(N)=O)COC(=O)NC(C)C
InChI Identifier
InChI=1S/C12H24N2O4/c1-5-6-12(4,7-17-10(13)15)8-18-11(16)14-9(2)3/h9H,5-8H2,1-4H3,(H2,13,15)(H,14,16)
InChI KeyOFZCIYFFPZCNJE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as carbamate esters. Carbamate esters are compounds containing an ester of carbamic acid with the general structure R2NC(=O)OR' (R' not H). They are esters of carbamic acids.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentCarbamate esters
Alternative Parents
Substituents
  • Carbamic acid ester
  • Carbonic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point92 - 93 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.79 g/LNot Available
LogP2.1Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available149.065http://allccs.zhulab.cn/database/detail?ID=AllCCS00001281
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.79 g/LALOGPS
logP1.76ALOGPS
logP1.92ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)15.06ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area90.65 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity67.1 m³·mol⁻¹ChemAxon
Polarizability28.77 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+160.20431661259
DarkChem[M-H]-157.25831661259
DeepCCS[M+H]+166.15730932474
DeepCCS[M-H]-163.79930932474
DeepCCS[M-2H]-196.68530932474
DeepCCS[M+Na]+172.2530932474
AllCCS[M+H]+164.732859911
AllCCS[M+H-H2O]+161.632859911
AllCCS[M+NH4]+167.532859911
AllCCS[M+Na]+168.332859911
AllCCS[M-H]-163.232859911
AllCCS[M+Na-2H]-164.332859911
AllCCS[M+HCOO]-165.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CarisoprodolCCCC(C)(COC(N)=O)COC(=O)NC(C)C2733.5Standard polar33892256
CarisoprodolCCCC(C)(COC(N)=O)COC(=O)NC(C)C1814.0Standard non polar33892256
CarisoprodolCCCC(C)(COC(N)=O)COC(=O)NC(C)C1897.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Carisoprodol,1TMS,isomer #1CCCC(C)(COC(=O)NC(C)C)COC(=O)N[Si](C)(C)C1990.9Semi standard non polar33892256
Carisoprodol,1TMS,isomer #1CCCC(C)(COC(=O)NC(C)C)COC(=O)N[Si](C)(C)C1956.5Standard non polar33892256
Carisoprodol,1TMS,isomer #1CCCC(C)(COC(=O)NC(C)C)COC(=O)N[Si](C)(C)C2590.3Standard polar33892256
Carisoprodol,1TMS,isomer #2CCCC(C)(COC(N)=O)COC(=O)N(C(C)C)[Si](C)(C)C1978.9Semi standard non polar33892256
Carisoprodol,1TMS,isomer #2CCCC(C)(COC(N)=O)COC(=O)N(C(C)C)[Si](C)(C)C1898.2Standard non polar33892256
Carisoprodol,1TMS,isomer #2CCCC(C)(COC(N)=O)COC(=O)N(C(C)C)[Si](C)(C)C2951.2Standard polar33892256
Carisoprodol,2TMS,isomer #1CCCC(C)(COC(=O)N[Si](C)(C)C)COC(=O)N(C(C)C)[Si](C)(C)C2056.0Semi standard non polar33892256
Carisoprodol,2TMS,isomer #1CCCC(C)(COC(=O)N[Si](C)(C)C)COC(=O)N(C(C)C)[Si](C)(C)C2040.5Standard non polar33892256
Carisoprodol,2TMS,isomer #1CCCC(C)(COC(=O)N[Si](C)(C)C)COC(=O)N(C(C)C)[Si](C)(C)C2337.0Standard polar33892256
Carisoprodol,2TMS,isomer #2CCCC(C)(COC(=O)NC(C)C)COC(=O)N([Si](C)(C)C)[Si](C)(C)C2057.1Semi standard non polar33892256
Carisoprodol,2TMS,isomer #2CCCC(C)(COC(=O)NC(C)C)COC(=O)N([Si](C)(C)C)[Si](C)(C)C2048.3Standard non polar33892256
Carisoprodol,2TMS,isomer #2CCCC(C)(COC(=O)NC(C)C)COC(=O)N([Si](C)(C)C)[Si](C)(C)C2378.5Standard polar33892256
Carisoprodol,3TMS,isomer #1CCCC(C)(COC(=O)N(C(C)C)[Si](C)(C)C)COC(=O)N([Si](C)(C)C)[Si](C)(C)C2089.4Semi standard non polar33892256
Carisoprodol,3TMS,isomer #1CCCC(C)(COC(=O)N(C(C)C)[Si](C)(C)C)COC(=O)N([Si](C)(C)C)[Si](C)(C)C2148.2Standard non polar33892256
Carisoprodol,3TMS,isomer #1CCCC(C)(COC(=O)N(C(C)C)[Si](C)(C)C)COC(=O)N([Si](C)(C)C)[Si](C)(C)C2151.1Standard polar33892256
Carisoprodol,1TBDMS,isomer #1CCCC(C)(COC(=O)NC(C)C)COC(=O)N[Si](C)(C)C(C)(C)C2205.6Semi standard non polar33892256
Carisoprodol,1TBDMS,isomer #1CCCC(C)(COC(=O)NC(C)C)COC(=O)N[Si](C)(C)C(C)(C)C2124.0Standard non polar33892256
Carisoprodol,1TBDMS,isomer #1CCCC(C)(COC(=O)NC(C)C)COC(=O)N[Si](C)(C)C(C)(C)C2623.7Standard polar33892256
Carisoprodol,1TBDMS,isomer #2CCCC(C)(COC(N)=O)COC(=O)N(C(C)C)[Si](C)(C)C(C)(C)C2225.9Semi standard non polar33892256
Carisoprodol,1TBDMS,isomer #2CCCC(C)(COC(N)=O)COC(=O)N(C(C)C)[Si](C)(C)C(C)(C)C2119.0Standard non polar33892256
Carisoprodol,1TBDMS,isomer #2CCCC(C)(COC(N)=O)COC(=O)N(C(C)C)[Si](C)(C)C(C)(C)C2955.3Standard polar33892256
Carisoprodol,2TBDMS,isomer #1CCCC(C)(COC(=O)N[Si](C)(C)C(C)(C)C)COC(=O)N(C(C)C)[Si](C)(C)C(C)(C)C2505.2Semi standard non polar33892256
Carisoprodol,2TBDMS,isomer #1CCCC(C)(COC(=O)N[Si](C)(C)C(C)(C)C)COC(=O)N(C(C)C)[Si](C)(C)C(C)(C)C2389.0Standard non polar33892256
Carisoprodol,2TBDMS,isomer #1CCCC(C)(COC(=O)N[Si](C)(C)C(C)(C)C)COC(=O)N(C(C)C)[Si](C)(C)C(C)(C)C2526.8Standard polar33892256
Carisoprodol,2TBDMS,isomer #2CCCC(C)(COC(=O)NC(C)C)COC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2514.5Semi standard non polar33892256
Carisoprodol,2TBDMS,isomer #2CCCC(C)(COC(=O)NC(C)C)COC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2410.0Standard non polar33892256
Carisoprodol,2TBDMS,isomer #2CCCC(C)(COC(=O)NC(C)C)COC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2530.4Standard polar33892256
Carisoprodol,3TBDMS,isomer #1CCCC(C)(COC(=O)N(C(C)C)[Si](C)(C)C(C)(C)C)COC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2758.1Semi standard non polar33892256
Carisoprodol,3TBDMS,isomer #1CCCC(C)(COC(=O)N(C(C)C)[Si](C)(C)C(C)(C)C)COC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2677.9Standard non polar33892256
Carisoprodol,3TBDMS,isomer #1CCCC(C)(COC(=O)N(C(C)C)[Si](C)(C)C(C)(C)C)COC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2484.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Carisoprodol EI-B (Non-derivatized)splash10-0a4i-9200000000-7ee2bc67a583d40d99b82017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Carisoprodol EI-B (Non-derivatized)splash10-0a4i-9200000000-7ee2bc67a583d40d99b82018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Carisoprodol GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9320000000-ea5623d29b47a08ec3162017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Carisoprodol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Carisoprodol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4l-9200000000-84ceb4ca447a62939b632014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Carisoprodol LC-ESI-qTof , Positive-QTOFsplash10-056r-1920000000-df362ad4c912b7d0fb432017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carisoprodol LC-ESI-QFT , positive-QTOFsplash10-004i-4910000000-0fe5eef3c39360c36d382017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carisoprodol LC-ESI-QFT , positive-QTOFsplash10-01ot-9300000000-94d7b1adea0d831c09502017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carisoprodol LC-ESI-QFT , positive-QTOFsplash10-03dj-9100000000-a99d65f53726ca3b61162017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carisoprodol LC-ESI-QFT , positive-QTOFsplash10-03di-9000000000-618eb5a23da29ec51cb62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carisoprodol LC-ESI-QFT , positive-QTOFsplash10-03di-9000000000-d2d07fc2a5972fd4e9f82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carisoprodol LC-ESI-QFT , positive-QTOFsplash10-03di-9000000000-007521fa65c254bad2b62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carisoprodol , positive-QTOFsplash10-056r-1920000000-df362ad4c912b7d0fb432017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carisoprodol 90V, Positive-QTOFsplash10-03di-9000000000-bf1fe057c44420039b3a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carisoprodol 15V, Positive-QTOFsplash10-004i-4910000000-e7f506802140a9e5d5f62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carisoprodol 45V, Positive-QTOFsplash10-03dj-9100000000-ab0f09b2ddbd1ef810902021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carisoprodol 30V, Positive-QTOFsplash10-01ot-9300000000-1ebfa5d842a1f8d546732021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carisoprodol 60V, Positive-QTOFsplash10-03di-9000000000-ef44fb81f70af0bfd4652021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carisoprodol 75V, Positive-QTOFsplash10-03di-9000000000-a7cb3ad99f7b8bfb6ed92021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carisoprodol 10V, Negative-QTOFsplash10-000x-9010000000-548142f811b5a3632f8d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carisoprodol 20V, Negative-QTOFsplash10-0006-9000000000-37215ebd46867ac40f9f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carisoprodol 40V, Negative-QTOFsplash10-052f-9100000000-46650c3ec5dedc27b7ec2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carisoprodol 10V, Negative-QTOFsplash10-0adi-2960000000-0132a40d2da121a224712021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carisoprodol 20V, Negative-QTOFsplash10-003r-3900000000-5ed690941e48fd4fa3172021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carisoprodol 40V, Negative-QTOFsplash10-001u-9100000000-80c4a93a61d1de508e942021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carisoprodol 10V, Positive-QTOFsplash10-03di-6490000000-046fd220fa245140ddab2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carisoprodol 20V, Positive-QTOFsplash10-0a4i-9320000000-b08ca9d93b628ea8b4f32016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carisoprodol 40V, Positive-QTOFsplash10-052f-9100000000-4f09dfa1c188e3251a652016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carisoprodol 10V, Positive-QTOFsplash10-0lxt-7970000000-bf2aa9b29774479d4c052021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carisoprodol 20V, Positive-QTOFsplash10-0f6t-9410000000-9352c9b82fc7d1079dd72021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00395 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00395 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00395
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00032142
Chemspider ID2478
KEGG Compound IDC07927
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCarisoprodol
METLIN IDNot Available
PubChem Compound2576
PDB IDNot Available
ChEBI ID3419
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. Littrell RA, Hayes LR, Stillner V: Carisoprodol (Soma): a new and cautious perspective on an old agent. South Med J. 1993 Jul;86(7):753-6. [PubMed:8322081 ]
  2. Chou R, Peterson K, Helfand M: Comparative efficacy and safety of skeletal muscle relaxants for spasticity and musculoskeletal conditions: a systematic review. J Pain Symptom Manage. 2004 Aug;28(2):140-75. [PubMed:15276195 ]
  3. Toth PP, Urtis J: Commonly used muscle relaxant therapies for acute low back pain: a review of carisoprodol, cyclobenzaprine hydrochloride, and metaxalone. Clin Ther. 2004 Sep;26(9):1355-67. [PubMed:15530999 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]