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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:04:11 UTC

Update Date

2022-03-07 02:54:22 UTC

HMDB ID

HMDB0035125

Secondary Accession Numbers

HMDB35125

Metabolite Identification

Common Name

Darwinol

Description

Darwinol 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

COMPND    HMDB0035125
HETATM    1  C1  UNL     1      -2.341  -1.159   0.485  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.187  -0.245   0.197  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.391   0.546  -1.051  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.748   0.560   1.409  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.101   1.715   0.982  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.248   1.175   0.156  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.248  -0.100  -0.183  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.316  -0.647  -1.031  1.00  0.00           C  
HETATM    9  O1  UNL     1       3.259   0.294  -1.400  1.00  0.00           O  
HETATM   10  C9  UNL     1       0.160  -0.960   0.303  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.057  -0.661   1.810  1.00  0.00           C  
HETATM   12  H1  UNL     1      -3.267  -0.654   0.083  1.00  0.00           H  
HETATM   13  H2  UNL     1      -2.207  -2.112  -0.041  1.00  0.00           H  
HETATM   14  H3  UNL     1      -2.543  -1.291   1.569  1.00  0.00           H  
HETATM   15  H4  UNL     1      -1.958  -0.112  -1.768  1.00  0.00           H  
HETATM   16  H5  UNL     1      -0.481   0.848  -1.570  1.00  0.00           H  
HETATM   17  H6  UNL     1      -2.088   1.382  -0.823  1.00  0.00           H  
HETATM   18  H7  UNL     1      -1.548   0.780   2.129  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.483   2.442   0.421  1.00  0.00           H  
HETATM   20  H9  UNL     1       0.583   2.174   1.880  1.00  0.00           H  
HETATM   21  H10 UNL     1       2.038   1.872  -0.128  1.00  0.00           H  
HETATM   22  H11 UNL     1       1.872  -1.048  -1.988  1.00  0.00           H  
HETATM   23  H12 UNL     1       2.827  -1.529  -0.559  1.00  0.00           H  
HETATM   24  H13 UNL     1       3.845   0.521  -0.658  1.00  0.00           H  
HETATM   25  H14 UNL     1       0.165  -2.008   0.039  1.00  0.00           H  
HETATM   26  H15 UNL     1      -0.533  -1.387   2.368  1.00  0.00           H  
HETATM   27  H16 UNL     1       1.054  -0.395   2.254  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    4   10
CONECT    3   15   16   17
CONECT    4    5   11   18
CONECT    5    6   19   20
CONECT    6    7    7   21
CONECT    7    8   10
CONECT    8    9   22   23
CONECT    9   24
CONECT   10   11   25
CONECT   11   26   27
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(+)-Myrtenol	HMDB
(+)-Pin-2-ene-10-ol	HMDB
(1S)-(+)-Myrtenol	HMDB
(1S)-2-Pinen-10-ol	HMDB
(1S)-6,6-dimethylbicyclo[3.1.1]Hept-2-ene-2-methanol	HMDB
2-Pinen-10-ol, (1S,5R)-(+)- (8ci)	HMDB
6,6-Dimethyl-(1S)-bicyclo(3.1.1)hept-2-ene-2-methanol	HMDB
6,6-Dimethyl-(1S)-bicyclo[3.1.1]hept-2-ene-2-methanol	HMDB
6,6-Dimethyl-(1S,5R)-bicyclo[3.1.1]hept-2-ene-2-methanol	HMDB

Chemical Formula

C₁₀H₁₆O

Average Molecular Weight

152.2334

Monoisotopic Molecular Weight

152.120115134

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 Number

6712-78-3

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 Key

RXBQNMWIQKOSCS-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Bicyclic monoterpenoids

Alternative Parents

Substituents

Pinane monoterpenoid
Bicyclic monoterpenoid
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0035125)
Cell membrane (HMDB: HMDB0035125)

Cellular substructure

Extracellular (HMDB: HMDB0035125)
Membrane (HMDB: HMDB0035125)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035125)

Source

Endogenous

Endogenous (HMDB: HMDB0035125)

Plant

Plant (HMDB: HMDB0035125)

Animal

Animal (HMDB: HMDB0035125)

Exogenous

Food

Food (HMDB: HMDB0035125)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0035125)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0035125)

Cellular process

Cell signaling (HMDB: HMDB0035125)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0035125)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0035125)

Nutrient

Nutrient (HMDB: HMDB0035125)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0035125)

Emulsifier (HMDB: HMDB0035125)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	106.00 to 107.00 °C. @ 14.00 mm Hg	The Good Scents Company Information System
Water Solubility	426.9 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.845 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.67 g/L	ALOGPS
logP	2.71	ALOGPS
logP	1.52	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	17.1	ChemAxon
pKa (Strongest Basic)	-1.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	46.5 m³·mol⁻¹	ChemAxon
Polarizability	18.12 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	136.482	31661259
DarkChem	[M-H]-	130.835	31661259
DeepCCS	[M+H]+	142.032	30932474
DeepCCS	[M-H]-	139.674	30932474
DeepCCS	[M-2H]-	173.833	30932474
DeepCCS	[M+Na]+	148.678	30932474
AllCCS	[M+H]+	132.6	32859911
AllCCS	[M+H-H2O]+	128.2	32859911
AllCCS	[M+NH4]+	136.6	32859911
AllCCS	[M+Na]+	137.8	32859911
AllCCS	[M-H]-	136.6	32859911
AllCCS	[M+Na-2H]-	137.8	32859911
AllCCS	[M+HCOO]-	139.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Darwinol	CC1(C)[C@H]2C[C@@H]1C(CO)=CC2	1807.2	Standard polar	33892256
Darwinol	CC1(C)[C@H]2C[C@@H]1C(CO)=CC2	1201.2	Standard non polar	33892256
Darwinol	CC1(C)[C@H]2C[C@@H]1C(CO)=CC2	1226.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Darwinol,1TMS,isomer #1	CC1(C)[C@@H]2CC=C(CO[Si](C)(C)C)[C@H]1C2	1312.3	Semi standard non polar	33892256
Darwinol,1TBDMS,isomer #1	CC1(C)[C@@H]2CC=C(CO[Si](C)(C)C(C)(C)C)[C@H]1C2	1578.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Darwinol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fl0-4900000000-94dac4a63ebff6374246	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Darwinol GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9420000000-ca6d4e365a12ebd1b2f3	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Darwinol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Darwinol 10V, Positive-QTOF	splash10-0udr-0900000000-b19ea4150917a6bafd94	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Darwinol 20V, Positive-QTOF	splash10-000i-0900000000-aec595a21a1484e269cb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Darwinol 40V, Positive-QTOF	splash10-00kr-0900000000-a4ed5627231523db689b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Darwinol 10V, Negative-QTOF	splash10-0udi-0900000000-3c298e096851b5f5f3c6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Darwinol 20V, Negative-QTOF	splash10-0uk9-0900000000-431fc5e7bd81c6899b0d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Darwinol 40V, Negative-QTOF	splash10-00di-0900000000-13dd05855689717c2226	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Darwinol 10V, Negative-QTOF	splash10-0udi-0900000000-c373c9eea3cebf186f53	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Darwinol 20V, Negative-QTOF	splash10-0udi-0900000000-705283d393728bb3f1e3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Darwinol 40V, Negative-QTOF	splash10-0udi-0900000000-1d76e4e74ba5204cba1a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Darwinol 10V, Positive-QTOF	splash10-0udi-0900000000-0dd01a232778d34915e7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Darwinol 20V, Positive-QTOF	splash10-000i-0900000000-90e520208520180a8a6f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Darwinol 40V, Positive-QTOF	splash10-0a4i-0900000000-2a50defe3cd69eac1ca4	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB013760

KNApSAcK ID

C00011041

Chemspider ID

552247

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

636475

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1108501

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
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 ]
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 ]
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 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Darwinol (HMDB0035125)

MOL for HMDB0035125 (Darwinol)

3D MOL for HMDB0035125 (Darwinol)

3D SDF for HMDB0035125 (Darwinol)

3D-SDF for HMDB0035125 (Darwinol)

PDB for HMDB0035125 (Darwinol)

3D PDB for HMDB0035125 (Darwinol)

SMILES for HMDB0035125 (Darwinol)

INCHI for HMDB0035125 (Darwinol)

Structure for HMDB0035125 (Darwinol)

3D Structure for HMDB0035125 (Darwinol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra