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

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 16:31:12 UTC

Update Date

2021-09-23 16:31:12 UTC

HMDB ID

HMDB0302276

Secondary Accession Numbers

None

Metabolite Identification

Common Name

trans-p-Mentha-1(7),8-dien-2-ol

Description

Trans-p-mentha-1(7),8-dien-2-ol is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Trans-p-mentha-1(7),8-dien-2-ol is slightly soluble (in water) and an extremely weak acidic compound (based on its pKa). Trans-p-mentha-1(7),8-dien-2-ol can be found in wild celery, which makes trans-p-mentha-1(7),8-dien-2-ol a potential biomarker for the consumption of this food product.

Structure

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


  Mrv1533007141517462D          

 13 13  0  0  1  0            999 V2000
   -0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  7  1  2  0  0  0  0
  7  2  1  0  0  0  0
  8  3  2  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
  9  6  1  0  0  0  0
  9  7  1  1  0  0  0
 10  6  1  0  0  0  0
 10  8  1  0  0  0  0
 10 11  1  1  0  0  0
  9 12  1  6  0  0  0
 10 13  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0302276

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]1(O)C[C@]([H])(CCC1=C)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)10(11)6-9/h9-11H,1,3-6H2,2H3/t9-,10-/m0/s1

> <INCHI_KEY>
PNVTXOFNJFHXOK-UWVGGRQHSA-N

> <FORMULA>
C10H16O

> <MOLECULAR_WEIGHT>
152.237

> <EXACT_MASS>
152.120115135

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
18.20097268851014

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,5S)-2-methylidene-5-(prop-1-en-2-yl)cyclohexan-1-ol

> <ALOGPS_LOGP>
2.47

> <JCHEM_LOGP>
2.046935255

> <ALOGPS_LOGS>
-1.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.207319420009814

> <JCHEM_PKA_STRONGEST_BASIC>
-1.395918485687707

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
46.9233

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.71e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,5S)-2-methylidene-5-(prop-1-en-2-yl)cyclohexan-1-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 14-JUL-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-JUL-15         0                                  
HETATM    1  C   UNK     0      -0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   12  H   UNK     0       2.667   3.080   0.000  0.00  0.00           H+0
HETATM   13  H   UNK     0      -1.334   0.770   0.000  0.00  0.00           H+0
CONECT    1    7                                                            
CONECT    2    7                                                            
CONECT    3    8                                                            
CONECT    4    5    8                                                       
CONECT    5    4    9                                                       
CONECT    6    9   10                                                       
CONECT    7    1    2    9                                                  
CONECT    8    3    4   10                                                  
CONECT    9    5    6    7   12                                             
CONECT   10    6    8   11   13                                             
CONECT   11   10                                                            
CONECT   12    9                                                            
CONECT   13   10                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

COMPND    HMDB0302276
HETATM    1  C1  UNL     1       3.045   1.046   0.484  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.070   0.369  -0.086  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.428   0.858  -1.337  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.052   0.729  -1.344  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.585  -0.457  -0.605  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.052  -0.288  -0.438  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.903  -1.129  -1.000  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.590   0.833   0.367  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.064  -0.646   0.753  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.539  -0.914   0.461  1.00  0.00           C  
HETATM   11  O1  UNL     1       2.215  -1.351   1.571  1.00  0.00           O  
HETATM   12  H1  UNL     1       3.385   1.964   0.044  1.00  0.00           H  
HETATM   13  H2  UNL     1       3.505   0.690   1.386  1.00  0.00           H  
HETATM   14  H3  UNL     1       1.677   1.946  -1.503  1.00  0.00           H  
HETATM   15  H4  UNL     1       1.898   0.297  -2.171  1.00  0.00           H  
HETATM   16  H5  UNL     1      -0.560   1.671  -1.013  1.00  0.00           H  
HETATM   17  H6  UNL     1      -0.371   0.606  -2.421  1.00  0.00           H  
HETATM   18  H7  UNL     1      -0.343  -1.365  -1.194  1.00  0.00           H  
HETATM   19  H8  UNL     1      -2.502  -1.945  -1.586  1.00  0.00           H  
HETATM   20  H9  UNL     1      -3.971  -1.025  -0.891  1.00  0.00           H  
HETATM   21  H10 UNL     1      -2.892   1.652  -0.325  1.00  0.00           H  
HETATM   22  H11 UNL     1      -3.509   0.550   0.939  1.00  0.00           H  
HETATM   23  H12 UNL     1      -1.839   1.209   1.079  1.00  0.00           H  
HETATM   24  H13 UNL     1      -0.058   0.256   1.376  1.00  0.00           H  
HETATM   25  H14 UNL     1      -0.385  -1.549   1.203  1.00  0.00           H  
HETATM   26  H15 UNL     1       1.565  -1.648  -0.376  1.00  0.00           H  
HETATM   27  H16 UNL     1       2.220  -2.356   1.547  1.00  0.00           H  
CONECT    1    2    2   12   13
CONECT    2    3   10
CONECT    3    4   14   15
CONECT    4    5   16   17
CONECT    5    6    9   18
CONECT    6    7    7    8
CONECT    7   19   20
CONECT    8   21   22   23
CONECT    9   10   24   25
CONECT   10   11   26
CONECT   11   27
END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₀H₁₆O

Average Molecular Weight

152.237

Monoisotopic Molecular Weight

152.120115135

IUPAC Name

(1S,5S)-2-methylidene-5-(prop-1-en-2-yl)cyclohexan-1-ol

Traditional Name

(1S,5S)-2-methylidene-5-(prop-1-en-2-yl)cyclohexan-1-ol

CAS Registry Number

Not Available

SMILES

[H][C@]1(O)C[C@]([H])(CCC1=C)C(C)=C

InChI Identifier

InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)10(11)6-9/h9-11H,1,3-6H2,2H3/t9-,10-/m0/s1

InChI Key

PNVTXOFNJFHXOK-UWVGGRQHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Menthane monoterpenoids

Alternative Parents

Substituents

P-menthane monoterpenoid
Monocyclic monoterpenoid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0302276)

Food

Herb and spice

Spice

Wild celery (FooDB: FOOD00015)

Process

Not Available

Role

Not Available

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
logP	2.47	ALOGPS
logP	2.05	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	18.21	ChemAxon
pKa (Strongest Basic)	-1.4	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	46.92 m³·mol⁻¹	ChemAxon
Polarizability	18.2 Å³	ChemAxon
Number of Rings	1	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
AllCCS	[M+H]+	134.784	32859911
AllCCS	[M+H-H2O]+	130.399	32859911
AllCCS	[M+Na]+	140.05	32859911
AllCCS	[M+NH4]+	138.871	32859911
AllCCS	[M-H]-	136.085	32859911
AllCCS	[M+Na-2H]-	137.615	32859911
AllCCS	[M+HCOO]-	139.365	32859911
DeepCCS	[M+H]+	140.089	30932474
DeepCCS	[M-H]-	137.82	30932474
DeepCCS	[M-2H]-	171.49	30932474
DeepCCS	[M+Na]+	146.016	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	12.7077 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.7 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1820.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	407.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	152.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	217.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	107.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	448.3 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	598.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	114.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1000.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	365.5 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	1243.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	310.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	350.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	410.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	407.3 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	31.3 seconds	40023050

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-p-Mentha-1(7),8-dien-2-ol 10V, Positive-QTOF	splash10-0f79-0900000000-442b26e08081df3fa5b7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-p-Mentha-1(7),8-dien-2-ol 20V, Positive-QTOF	splash10-0f79-6900000000-5653625557b18bc92d4f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-p-Mentha-1(7),8-dien-2-ol 40V, Positive-QTOF	splash10-100r-9100000000-fc8ca7849be90c729370	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-p-Mentha-1(7),8-dien-2-ol 10V, Negative-QTOF	splash10-0udi-0900000000-888106e384dd13208c5c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-p-Mentha-1(7),8-dien-2-ol 20V, Negative-QTOF	splash10-0udi-0900000000-99ff0708557c327947f6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-p-Mentha-1(7),8-dien-2-ol 40V, Negative-QTOF	splash10-000l-7900000000-d024f501e35469182157	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-p-Mentha-1(7),8-dien-2-ol 10V, Positive-QTOF	splash10-01oy-9600000000-8bea452dada4b0402cca	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-p-Mentha-1(7),8-dien-2-ol 20V, Positive-QTOF	splash10-00nf-9100000000-20876405108eedf8dcf7	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-p-Mentha-1(7),8-dien-2-ol 40V, Positive-QTOF	splash10-0006-9000000000-c4677e64733a20ed4bb6	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-p-Mentha-1(7),8-dien-2-ol 10V, Negative-QTOF	splash10-0udi-0900000000-c373c9eea3cebf186f53	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-p-Mentha-1(7),8-dien-2-ol 20V, Negative-QTOF	splash10-0ue9-0900000000-5d328822628d4a11cd17	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-p-Mentha-1(7),8-dien-2-ol 40V, Negative-QTOF	splash10-0159-6900000000-a46644dfeaa01da6171c	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB004001

KNApSAcK ID

Not Available

Chemspider ID

10276004

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12642439

PDB ID

Not Available

ChEBI ID

Not Available

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

Not Available

Showing metabocard for trans-p-Mentha-1(7),8-dien-2-ol (HMDB0302276)

MOL for HMDB0302276 (trans-p-Mentha-1(7),8-dien-2-ol)

3D MOL for HMDB0302276 (trans-p-Mentha-1(7),8-dien-2-ol)

3D SDF for HMDB0302276 (trans-p-Mentha-1(7),8-dien-2-ol)

3D-SDF for HMDB0302276 (trans-p-Mentha-1(7),8-dien-2-ol)

PDB for HMDB0302276 (trans-p-Mentha-1(7),8-dien-2-ol)

3D PDB for HMDB0302276 (trans-p-Mentha-1(7),8-dien-2-ol)

SMILES for HMDB0302276 (trans-p-Mentha-1(7),8-dien-2-ol)

INCHI for HMDB0302276 (trans-p-Mentha-1(7),8-dien-2-ol)

Structure for HMDB0302276 (trans-p-Mentha-1(7),8-dien-2-ol)

3D Structure for HMDB0302276 (trans-p-Mentha-1(7),8-dien-2-ol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

MS/MS Spectra