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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:43 UTC
Update Date2021-10-13 04:40:59 UTC
HMDB IDHMDB0003236
Secondary Accession Numbers
  • HMDB03236
Metabolite Identification
Common NameSolanidine
DescriptionSolanidine, also known as solatubin or solanid-5-en-3-ol, belongs to the class of organic compounds known as solanidines and derivatives. These are steroids with a structure based on the solanidane skeleton. Solanidane arises from the conversion of a cholestane side-chain into a bicyclic system. Thus, solanidine is considered to be a sterol. Based on a literature review a significant number of articles have been published on Solanidine.
Structure
Data?1582752267
Synonyms
ValueSource
(-)-SolanidineChEBI
(22R,25S)-SolanidanineChEBI
(22R,25S)-SolanidineChEBI
(2S,4AR,4BS,6as,6BR,7S,7ar,10S,12as,13as,13BS)-4a,6a,7,10-tetramethyl-2,3,4,4a,4b,5,6,6a,6b,7,7a,8,9,10,11,12a,13,13a,13b,14-icosahydro-1H-naphtho[2',1':4,5]indeno[1,2-b]indolizin-2-olChEBI
(3beta)-Solanid-5-en-3-olChEBI
3-beta-Solanid-5-en-3-olChEBI
Solanid-5-en-3-beta-olChEBI
SolanidinChEBI
SolatubinChEBI
SolatubineChEBI
(3b)-Solanid-5-en-3-olGenerator
(3Β)-solanid-5-en-3-olGenerator
3-b-Solanid-5-en-3-olGenerator
3-Β-solanid-5-en-3-olGenerator
Solanid-5-en-3-b-olGenerator
Solanid-5-en-3-β-olGenerator
Solanid-5-en-3beta-olHMDB
Solanid-5-en-3b-olHMDB
Solanid-5-en-3β-olHMDB
22R,25S-SolanidanineHMDB
22R,25S-SolanidineHMDB
3-b-Solanid-5-en-3-ol(9CL)HMDB
3-beta-Solanid-5-en-3-ol(9CL)HMDB
Solanid-5-en-3-olHMDB
Solanid-5-en-3-ol (acd/name 4.0)HMDB
Solanid-5-en-3.beta.-olHMDB
Solanid-5-en-3beta-ol(8ci)HMDB
Chemical FormulaC27H43NO
Average Molecular Weight397.6364
Monoisotopic Molecular Weight397.334465003
IUPAC Name(1S,2S,7S,10R,11S,14S,15R,16S,17R,20S,23S)-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁷,²²]tetracos-4-en-7-ol
Traditional Namesolanidine
CAS Registry Number80-78-4
SMILES
[H][C@]12CC[C@H](C)CN1[C@@]1([H])C[C@@]3([H])[C@]4([H])CC=C5C[C@@H](O)CC[C@]5(C)[C@@]4([H])CC[C@]3(C)[C@@]1([H])[C@@H]2C
InChI Identifier
InChI=1S/C27H43NO/c1-16-5-8-23-17(2)25-24(28(23)15-16)14-22-20-7-6-18-13-19(29)9-11-26(18,3)21(20)10-12-27(22,25)4/h6,16-17,19-25,29H,5,7-15H2,1-4H3/t16-,17+,19-,20+,21-,22-,23+,24-,25-,26-,27-/m0/s1
InChI KeyJVKYZPBMZPJNAJ-OQFNDJACSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as solanidines and derivatives. These are steroids with a structure based on the solanidane skeleton. Solanidane arises from the conversion of a cholestane side-chain into a bicyclic system.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroidal alkaloids
Direct ParentSolanidines and derivatives
Alternative Parents
Substituents
  • Solanidane skeleton
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Azasteroid
  • Delta-5-steroid
  • Alkaloid or derivatives
  • Indolizidine
  • N-alkylpyrrolidine
  • Piperidine
  • Cyclic alcohol
  • Pyrrolidine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • Organoheterocyclic compound
  • Azacycle
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Amine
  • Organooxygen compound
  • Organic oxygen compound
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point218.5 °CNot Available
Boiling Point503.10 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.02 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP5.372Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0004 g/LALOGPS
logP10(4.93) g/LALOGPS
logP10(4.88) g/LChemAxon
logS10(-6) g/LALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)12.47ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area23.47 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity120.86 m³·mol⁻¹ChemAxon
Polarizability50.43 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+194.14231661259
DarkChem[M-H]-191.19631661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Solanidine[H][C@]12CC[C@H](C)CN1[C@@]1([H])C[C@@]3([H])[C@]4([H])CC=C5C[C@@H](O)CC[C@]5(C)[C@@]4([H])CC[C@]3(C)[C@@]1([H])[C@@H]2C2879.2Standard polar33892256
Solanidine[H][C@]12CC[C@H](C)CN1[C@@]1([H])C[C@@]3([H])[C@]4([H])CC=C5C[C@@H](O)CC[C@]5(C)[C@@]4([H])CC[C@]3(C)[C@@]1([H])[C@@H]2C3280.0Standard non polar33892256
Solanidine[H][C@]12CC[C@H](C)CN1[C@@]1([H])C[C@@]3([H])[C@]4([H])CC=C5C[C@@H](O)CC[C@]5(C)[C@@]4([H])CC[C@]3(C)[C@@]1([H])[C@@H]2C3418.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Solanidine,1TMS,isomer #1C[C@H]1CC[C@@H]2[C@@H](C)[C@H]3[C@H](C[C@H]4[C@@H]5CC=C6C[C@@H](O[Si](C)(C)C)CC[C@]6(C)[C@H]5CC[C@@]43C)N2C13181.3Semi standard non polar33892256
Solanidine,1TBDMS,isomer #1C[C@H]1CC[C@@H]2[C@@H](C)[C@H]3[C@H](C[C@H]4[C@@H]5CC=C6C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]6(C)[C@H]5CC[C@@]43C)N2C13460.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Solanidine GC-MS (Non-derivatized) - 70eV, Positivesplash10-00lr-0119000000-09758005bcbc04782ff42017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Solanidine GC-MS (1 TMS) - 70eV, Positivesplash10-0udl-1213900000-9122bd157f18325b320b2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Solanidine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Solanidine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0udi-5910000000-da12df0b66b01e4989802015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Solanidine 10V, Positive-QTOFsplash10-001j-0009000000-5b0fb24be88683d068b52017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Solanidine 20V, Positive-QTOFsplash10-001j-0139000000-911def26f967b66af0fa2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Solanidine 40V, Positive-QTOFsplash10-0wti-1159000000-e91adb85d8cc7c4803c12017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Solanidine 10V, Negative-QTOFsplash10-0002-0009000000-b7424d5bd5a12fdf98d92017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Solanidine 20V, Negative-QTOFsplash10-0002-0009000000-68f4c5d2355e9a863c722017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Solanidine 40V, Negative-QTOFsplash10-003u-5009000000-1267a2feb79a6babccfd2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Solanidine 10V, Negative-QTOFsplash10-0002-0009000000-9adef56b5a2ae287a34c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Solanidine 20V, Negative-QTOFsplash10-0002-0009000000-9adef56b5a2ae287a34c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Solanidine 40V, Negative-QTOFsplash10-0006-0009000000-7801b00b472dd0fa1eca2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Solanidine 10V, Positive-QTOFsplash10-0002-0009000000-99dc14115be2ec86a8442021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Solanidine 20V, Positive-QTOFsplash10-0002-0139000000-2f8e89fdf0e2e16b82222021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Solanidine 40V, Positive-QTOFsplash10-002b-5921000000-d4f1d4372fb4151969282021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00318 +/- 0.00243 uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012098
KNApSAcK IDC00002261
Chemspider ID59150
KEGG Compound IDC06543
BioCyc IDCPD-9217
BiGG IDNot Available
Wikipedia LinkSolanidine
METLIN ID3517
PubChem Compound65727
PDB IDNot Available
ChEBI ID28374
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1586081
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. FARHI LE, EDWARDS AW, HOMMA T: Determination of dissolved N2 in blood by gas chromatography and (a-A)N2 difference. J Appl Physiol. 1963 Jan;18:97-106. [PubMed:13944363 ]
  2. Harvey MH, McMillan M, Morgan MR, Chan HW: Solanidine is present in sera of healthy individuals and in amounts dependent on their dietary potato consumption. Hum Toxicol. 1985 Mar;4(2):187-94. [PubMed:4007882 ]