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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:09:07 UTC

Update Date

2023-02-21 17:24:40 UTC

HMDB ID

HMDB0035203

Secondary Accession Numbers

HMDB35203

Metabolite Identification

Common Name

(S)-9,10-Cyclo-p-menth-1-en-4-ol

Description

(S)-9,10-Cyclo-p-menth-1-en-4-ol belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ) (S)-9,10-Cyclo-p-menth-1-en-4-ol has been detected, but not quantified in, nuts and pistachios (Pistacia vera). This could make (S)-9,10-cyclo-p-menth-1-en-4-ol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (S)-9,10-Cyclo-p-menth-1-en-4-ol.

Structure

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

COMPND    HMDB0035203
HETATM    1  C1  UNL     1       3.553   0.135   0.204  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.092   0.153   0.403  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.428  -0.904   0.843  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.057  -0.696   0.982  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.548  -0.206  -0.339  1.00  0.00           C  
HETATM    6  O1  UNL     1      -0.350  -1.240  -1.267  1.00  0.00           O  
HETATM    7  C6  UNL     1      -2.021   0.146  -0.320  1.00  0.00           C  
HETATM    8  C7  UNL     1      -3.032  -0.889   0.016  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.767   0.254   0.935  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.208   0.986  -0.842  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.317   1.381   0.107  1.00  0.00           C  
HETATM   12  H1  UNL     1       3.965   1.049   0.672  1.00  0.00           H  
HETATM   13  H2  UNL     1       4.016  -0.775   0.635  1.00  0.00           H  
HETATM   14  H3  UNL     1       3.737   0.229  -0.893  1.00  0.00           H  
HETATM   15  H4  UNL     1       1.917  -1.850   1.086  1.00  0.00           H  
HETATM   16  H5  UNL     1      -0.170   0.050   1.801  1.00  0.00           H  
HETATM   17  H6  UNL     1      -0.535  -1.614   1.315  1.00  0.00           H  
HETATM   18  H7  UNL     1      -0.914  -2.025  -1.060  1.00  0.00           H  
HETATM   19  H8  UNL     1      -2.309   0.821  -1.152  1.00  0.00           H  
HETATM   20  H9  UNL     1      -2.701  -1.906   0.240  1.00  0.00           H  
HETATM   21  H10 UNL     1      -4.030  -0.857  -0.495  1.00  0.00           H  
HETATM   22  H11 UNL     1      -3.512   1.072   1.037  1.00  0.00           H  
HETATM   23  H12 UNL     1      -2.335  -0.037   1.918  1.00  0.00           H  
HETATM   24  H13 UNL     1       0.653   0.831  -1.845  1.00  0.00           H  
HETATM   25  H14 UNL     1      -0.459   1.892  -0.942  1.00  0.00           H  
HETATM   26  H15 UNL     1       0.910   1.836   1.037  1.00  0.00           H  
HETATM   27  H16 UNL     1       1.945   2.165  -0.367  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    3   11
CONECT    3    4   15
CONECT    4    5   16   17
CONECT    5    6    7   10
CONECT    6   18
CONECT    7    8    9   19
CONECT    8    9   20   21
CONECT    9   22   23
CONECT   10   11   24   25
CONECT   11   26   27
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
9,10-cyclo-P-Menth-1-en-4-ol	HMDB

Chemical Formula

C₁₀H₁₆O

Average Molecular Weight

152.2334

Monoisotopic Molecular Weight

152.120115134

IUPAC Name

1-cyclopropyl-4-methylcyclohex-3-en-1-ol

Traditional Name

1-cyclopropyl-4-methylcyclohex-3-en-1-ol

CAS Registry Number

83133-20-4

SMILES

CC1=CCC(O)(CC1)C1CC1

InChI Identifier

InChI=1S/C10H16O/c1-8-4-6-10(11,7-5-8)9-2-3-9/h4,9,11H,2-3,5-7H2,1H3

InChI Key

FTEUSHRMTWTVTP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Tertiary alcohols

Alternative Parents

Hydrocarbon derivatives

Substituents

Tertiary alcohol
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0035203)
Cytoplasm (HMDB: HMDB0035203)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035203)

Source

Exogenous

Exogenous (HMDB: HMDB0035203)

Food

Food (HMDB: HMDB0035203)

Nut

Pistachio (FooDB: FOOD00140)
Nuts (FooDB: FOOD00869)

Endogenous

Plant

Plant (HMDB: HMDB0035203)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Emulsifier (HMDB: HMDB0035203)

Biological role

Nutrient (HMDB: HMDB0035203)

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	1.85 g/L	ALOGPS
logP	2.31	ALOGPS
logP	1.87	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	19.76	ChemAxon
pKa (Strongest Basic)	-0.72	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	46.51 m³·mol⁻¹	ChemAxon
Polarizability	18.26 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]+	134.504	31661259
DarkChem	[M-H]-	131.461	31661259
DeepCCS	[M+H]+	136.49	30932474
DeepCCS	[M-H]-	133.823	30932474
DeepCCS	[M-2H]-	170.031	30932474
DeepCCS	[M+Na]+	145.359	30932474
AllCCS	[M+H]+	134.8	32859911
AllCCS	[M+H-H2O]+	130.2	32859911
AllCCS	[M+NH4]+	139.0	32859911
AllCCS	[M+Na]+	140.2	32859911
AllCCS	[M-H]-	138.2	32859911
AllCCS	[M+Na-2H]-	139.3	32859911
AllCCS	[M+HCOO]-	140.6	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.	4.07 minutes	32390414
Predicted by Siyang on May 30, 2022	11.0935 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	1782.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	300.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	143.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	185.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	138.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	480.2 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	492.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	95.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	986.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	315.9 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	913.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	333.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	292.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	414.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	405.3 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	105.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(S)-9,10-Cyclo-p-menth-1-en-4-ol	CC1=CCC(O)(CC1)C1CC1	1785.3	Standard polar	33892256
(S)-9,10-Cyclo-p-menth-1-en-4-ol	CC1=CCC(O)(CC1)C1CC1	1268.8	Standard non polar	33892256
(S)-9,10-Cyclo-p-menth-1-en-4-ol	CC1=CCC(O)(CC1)C1CC1	1250.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(S)-9,10-Cyclo-p-menth-1-en-4-ol,1TMS,isomer #1	CC1=CCC(O[Si](C)(C)C)(C2CC2)CC1	1361.1	Semi standard non polar	33892256
(S)-9,10-Cyclo-p-menth-1-en-4-ol,1TBDMS,isomer #1	CC1=CCC(O[Si](C)(C)C(C)(C)C)(C2CC2)CC1	1614.0	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 - (S)-9,10-Cyclo-p-menth-1-en-4-ol GC-MS (Non-derivatized) - 70eV, Positive	splash10-00ko-9300000000-8e2bc4279686f7c0a8ee	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-9,10-Cyclo-p-menth-1-en-4-ol GC-MS (1 TMS) - 70eV, Positive	splash10-0adu-9620000000-2990aee96b2ef038a5ce	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-9,10-Cyclo-p-menth-1-en-4-ol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-9,10-Cyclo-p-menth-1-en-4-ol 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 - (S)-9,10-Cyclo-p-menth-1-en-4-ol 10V, Positive-QTOF	splash10-0f79-0900000000-947d06b60bc521ad2709	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-9,10-Cyclo-p-menth-1-en-4-ol 20V, Positive-QTOF	splash10-0f79-6900000000-73bc9022f9b7481de9f9	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-9,10-Cyclo-p-menth-1-en-4-ol 40V, Positive-QTOF	splash10-0lec-9100000000-6690f439797b013e5f04	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-9,10-Cyclo-p-menth-1-en-4-ol 10V, Negative-QTOF	splash10-0udi-0900000000-f4d281f202563d3f3cf1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-9,10-Cyclo-p-menth-1-en-4-ol 20V, Negative-QTOF	splash10-0udi-2900000000-8a47ce2b598628dbd2d1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-9,10-Cyclo-p-menth-1-en-4-ol 40V, Negative-QTOF	splash10-0006-9300000000-78ff9d93e31b107cde78	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-9,10-Cyclo-p-menth-1-en-4-ol 10V, Positive-QTOF	splash10-0uds-6900000000-5a70c733ca768cc87fa7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-9,10-Cyclo-p-menth-1-en-4-ol 20V, Positive-QTOF	splash10-0002-9200000000-04eb2a0f15c99cebcec5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-9,10-Cyclo-p-menth-1-en-4-ol 40V, Positive-QTOF	splash10-0006-9000000000-c0fc474a97c93f8be7d6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-9,10-Cyclo-p-menth-1-en-4-ol 10V, Negative-QTOF	splash10-0udi-0900000000-c373c9eea3cebf186f53	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-9,10-Cyclo-p-menth-1-en-4-ol 20V, Negative-QTOF	splash10-0udi-0900000000-ce1ad17fe4f8c7ad918a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-9,10-Cyclo-p-menth-1-en-4-ol 40V, Negative-QTOF	splash10-0006-9400000000-cafdfa060ab7aae2c1c4	2021-09-23	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

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB013849

KNApSAcK ID

C00010810

Chemspider ID

35013874

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73815132

PDB ID

Not Available

ChEBI ID

171958

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for (S)-9,10-Cyclo-p-menth-1-en-4-ol (HMDB0035203)

MOL for HMDB0035203 ((S)-9,10-Cyclo-p-menth-1-en-4-ol)

3D MOL for HMDB0035203 ((S)-9,10-Cyclo-p-menth-1-en-4-ol)

3D SDF for HMDB0035203 ((S)-9,10-Cyclo-p-menth-1-en-4-ol)

3D-SDF for HMDB0035203 ((S)-9,10-Cyclo-p-menth-1-en-4-ol)

PDB for HMDB0035203 ((S)-9,10-Cyclo-p-menth-1-en-4-ol)

3D PDB for HMDB0035203 ((S)-9,10-Cyclo-p-menth-1-en-4-ol)

SMILES for HMDB0035203 ((S)-9,10-Cyclo-p-menth-1-en-4-ol)

INCHI for HMDB0035203 ((S)-9,10-Cyclo-p-menth-1-en-4-ol)

Structure for HMDB0035203 ((S)-9,10-Cyclo-p-menth-1-en-4-ol)

3D Structure for HMDB0035203 ((S)-9,10-Cyclo-p-menth-1-en-4-ol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra