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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2013-02-25 18:03:56 UTC

Update Date

2021-09-14 15:39:06 UTC

HMDB ID

HMDB0059726

Secondary Accession Numbers

HMDB59726

Metabolite Identification

Common Name

(+)-4-Carene

Description

(+)-4-Carene belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other (+)-4-Carene is possibly neutral.

Structure

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
Δ-4-carene	Generator

Chemical Formula

C₁₀H₁₆

Average Molecular Weight

136.234

Monoisotopic Molecular Weight

136.125200512

IUPAC Name

4,7,7-trimethylbicyclo[4.1.0]hept-2-ene

Traditional Name

4,7,7-trimethylbicyclo[4.1.0]hept-2-ene

CAS Registry Number

Not Available

SMILES

CC1CC2C(C=C1)C2(C)C

InChI Identifier

InChI=1S/C10H16/c1-7-4-5-8-9(6-7)10(8,2)3/h4-5,7-9H,6H2,1-3H3

InChI Key

LGNSZMLHOYDATP-UHFFFAOYSA-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

Carane monoterpenoid
Bicyclic monoterpenoid
Polycyclic hydrocarbon
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0059726)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0059726)

Source

Endogenous

Endogenous (HMDB: HMDB0059726)

Animal

Animal (HMDB: HMDB0059726)

Exogenous

Food

Food (HMDB: HMDB0059726)

Herb and spice

Herb

Rosemary (FooDB: FOOD00159)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0059726)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0059726)

Lipid metabolism pathway (HMDB: HMDB0059726)

Cellular process

Cell signaling (HMDB: HMDB0059726)

Biochemical process

Lipid transport (HMDB: HMDB0059726)

Role

Biological role

Energy source (HMDB: HMDB0059726)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.007 g/L	ALOGPS
logP	3.46	ALOGPS
logP	2.85	ChemAxon
logS	-4.3	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	44.99 m³·mol⁻¹	ChemAxon
Polarizability	17.12 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]+	131.372	31661259
DarkChem	[M-H]-	126.185	31661259
DeepCCS	[M+H]+	134.872	30932474
DeepCCS	[M-H]-	131.711	30932474
DeepCCS	[M-2H]-	168.672	30932474
DeepCCS	[M+Na]+	144.159	30932474
AllCCS	[M+H]+	126.7	32859911
AllCCS	[M+H-H2O]+	122.1	32859911
AllCCS	[M+NH4]+	131.0	32859911
AllCCS	[M+Na]+	132.3	32859911
AllCCS	[M-H]-	134.0	32859911
AllCCS	[M+Na-2H]-	135.5	32859911
AllCCS	[M+HCOO]-	137.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.59 minutes	32390414
Predicted by Siyang on May 30, 2022	17.1445 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.81 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2151.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	652.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	227.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	393.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	344.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	645.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	707.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	139.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1353.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	465.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1333.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	485.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	431.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	526.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	582.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	21.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(+)-4-Carene	CC1CC2C(C=C1)C2(C)C	1137.1	Standard polar	33892256
(+)-4-Carene	CC1CC2C(C=C1)C2(C)C	989.8	Standard non polar	33892256
(+)-4-Carene	CC1CC2C(C=C1)C2(C)C	958.0	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 - (+)-4-Carene GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9200000000-ef78cf551bb07a80132e	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (+)-4-Carene 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 - (+)-4-Carene 10V, Positive-QTOF	splash10-000i-1900000000-60cf49c31d59d8307899	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-4-Carene 20V, Positive-QTOF	splash10-000i-7900000000-bd5679dbbd583e30cbfc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-4-Carene 40V, Positive-QTOF	splash10-0gbc-9000000000-49492007d5600c7fdd36	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-4-Carene 10V, Negative-QTOF	splash10-000i-0900000000-ccefcd220bb56db1d092	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-4-Carene 20V, Negative-QTOF	splash10-000i-1900000000-1201510f9278b73aebb9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-4-Carene 40V, Negative-QTOF	splash10-014u-5900000000-93cd0afa2fb56ce2af87	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-4-Carene 10V, Positive-QTOF	splash10-00ls-9100000000-1fc79287338e87be098f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-4-Carene 20V, Positive-QTOF	splash10-0005-9100000000-149ebcceef370a423c17	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-4-Carene 40V, Positive-QTOF	splash10-0006-9000000000-5b4169d6d952616fec0b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-4-Carene 10V, Negative-QTOF	splash10-000i-0900000000-a013b4ae27f975ab5621	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-4-Carene 20V, Negative-QTOF	splash10-000i-0900000000-a013b4ae27f975ab5621	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-4-Carene 40V, Negative-QTOF	splash10-001i-0900000000-79d3cc22ff9944c64255	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	22284503	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Breast cancer	22284503	details

Associated Disorders and Diseases

Disease References

Perillyl alcohol administration for cancer treatment
Silva CL, Passos M, Camara JS: Solid phase microextraction, mass spectrometry and metabolomic approaches for detection of potential urinary cancer biomarkers--a powerful strategy for breast cancer diagnosis. Talanta. 2012 Jan 30;89:360-8. doi: 10.1016/j.talanta.2011.12.041. Epub 2011 Dec 22. [PubMed:22284503 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB006928

KNApSAcK ID

Not Available

Chemspider ID

462024

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

530422

PDB ID

Not Available

ChEBI ID

89934

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

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 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for (+)-4-Carene (HMDB0059726)

MOL for HMDB0059726 ((+)-4-Carene)

3D MOL for HMDB0059726 ((+)-4-Carene)

3D SDF for HMDB0059726 ((+)-4-Carene)

3D-SDF for HMDB0059726 ((+)-4-Carene)

PDB for HMDB0059726 ((+)-4-Carene)

3D PDB for HMDB0059726 ((+)-4-Carene)

SMILES for HMDB0059726 ((+)-4-Carene)

INCHI for HMDB0059726 ((+)-4-Carene)

Structure for HMDB0059726 ((+)-4-Carene)

3D Structure for HMDB0059726 ((+)-4-Carene)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra