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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:04:11 UTC
Update Date2022-03-07 02:54:22 UTC
HMDB IDHMDB0035125
Secondary Accession Numbers
  • HMDB35125
Metabolite Identification
Common NameDarwinol
DescriptionDarwinol belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Based on a literature review a small amount of articles have been published on Darwinol.
Structure
Data?1563862669
Synonyms
ValueSource
(+)-MyrtenolHMDB
(+)-Pin-2-ene-10-olHMDB
(1S)-(+)-MyrtenolHMDB
(1S)-2-Pinen-10-olHMDB
(1S)-6,6-dimethylbicyclo[3.1.1]Hept-2-ene-2-methanolHMDB
2-Pinen-10-ol, (1S,5R)-(+)- (8ci)HMDB
6,6-Dimethyl-(1S)-bicyclo(3.1.1)hept-2-ene-2-methanolHMDB
6,6-Dimethyl-(1S)-bicyclo[3.1.1]hept-2-ene-2-methanolHMDB
6,6-Dimethyl-(1S,5R)-bicyclo[3.1.1]hept-2-ene-2-methanolHMDB
Chemical FormulaC10H16O
Average Molecular Weight152.2334
Monoisotopic Molecular Weight152.120115134
IUPAC Name[(1S,5R)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]methanol
Traditional Name[(1S,5R)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]methanol
CAS Registry Number6712-78-3
SMILES
CC1(C)[C@H]2C[C@@H]1C(CO)=CC2
InChI Identifier
InChI=1S/C10H16O/c1-10(2)8-4-3-7(6-11)9(10)5-8/h3,8-9,11H,4-6H2,1-2H3/t8-,9-/m1/s1
InChI KeyRXBQNMWIQKOSCS-RKDXNWHRSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentBicyclic monoterpenoids
Alternative Parents
Substituents
  • Pinane monoterpenoid
  • Bicyclic monoterpenoid
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point106.00 to 107.00 °C. @ 14.00 mm HgThe Good Scents Company Information System
Water Solubility426.9 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.845 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.67 g/LALOGPS
logP2.71ALOGPS
logP1.52ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)17.1ChemAxon
pKa (Strongest Basic)-1.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity46.5 m³·mol⁻¹ChemAxon
Polarizability18.12 ųChemAxon
Number of Rings2ChemAxon
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]+136.48231661259
DarkChem[M-H]-130.83531661259
DeepCCS[M+H]+142.03230932474
DeepCCS[M-H]-139.67430932474
DeepCCS[M-2H]-173.83330932474
DeepCCS[M+Na]+148.67830932474
AllCCS[M+H]+132.632859911
AllCCS[M+H-H2O]+128.232859911
AllCCS[M+NH4]+136.632859911
AllCCS[M+Na]+137.832859911
AllCCS[M-H]-136.632859911
AllCCS[M+Na-2H]-137.832859911
AllCCS[M+HCOO]-139.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DarwinolCC1(C)[C@H]2C[C@@H]1C(CO)=CC21807.2Standard polar33892256
DarwinolCC1(C)[C@H]2C[C@@H]1C(CO)=CC21201.2Standard non polar33892256
DarwinolCC1(C)[C@H]2C[C@@H]1C(CO)=CC21226.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Darwinol,1TMS,isomer #1CC1(C)[C@@H]2CC=C(CO[Si](C)(C)C)[C@H]1C21312.3Semi standard non polar33892256
Darwinol,1TBDMS,isomer #1CC1(C)[C@@H]2CC=C(CO[Si](C)(C)C(C)(C)C)[C@H]1C21578.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Darwinol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fl0-4900000000-94dac4a63ebff63742462017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Darwinol GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9420000000-ca6d4e365a12ebd1b2f32017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Darwinol 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 - Darwinol 10V, Positive-QTOFsplash10-0udr-0900000000-b19ea4150917a6bafd942016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Darwinol 20V, Positive-QTOFsplash10-000i-0900000000-aec595a21a1484e269cb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Darwinol 40V, Positive-QTOFsplash10-00kr-0900000000-a4ed5627231523db689b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Darwinol 10V, Negative-QTOFsplash10-0udi-0900000000-3c298e096851b5f5f3c62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Darwinol 20V, Negative-QTOFsplash10-0uk9-0900000000-431fc5e7bd81c6899b0d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Darwinol 40V, Negative-QTOFsplash10-00di-0900000000-13dd05855689717c22262016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Darwinol 10V, Negative-QTOFsplash10-0udi-0900000000-c373c9eea3cebf186f532021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Darwinol 20V, Negative-QTOFsplash10-0udi-0900000000-705283d393728bb3f1e32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Darwinol 40V, Negative-QTOFsplash10-0udi-0900000000-1d76e4e74ba5204cba1a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Darwinol 10V, Positive-QTOFsplash10-0udi-0900000000-0dd01a232778d34915e72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Darwinol 20V, Positive-QTOFsplash10-000i-0900000000-90e520208520180a8a6f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Darwinol 40V, Positive-QTOFsplash10-0a4i-0900000000-2a50defe3cd69eac1ca42021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB013760
KNApSAcK IDC00011041
Chemspider ID552247
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound636475
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1108501
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.