NP-MRD: Showing NP-Card for Menthyl lactate (NP0333415)

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Record Information

Version

1.0

Created at

2024-06-17 21:56:37 UTC

Updated at

2024-06-19 00:03:39 UTC

NP-MRD ID

NP0333415

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Menthyl lactate

Description

Menthyl lactate, also known as fema 3748, 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. Menthyl lactate is an extremely weak basic (essentially neutral) compound (based on its pKa). Menthyl lactate is a mild cooling, alcohol, and camphoraceous tasting compound. Outside of the human body,.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241218362D          

 16 16  0  0  0  0            999 V2000
   -1.4306   -0.6173    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1443   -0.2048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1443    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4306    1.0326    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4306    1.8562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7156    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7156   -0.2048    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0007   -0.6173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1443   -1.8562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4306   -1.4423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7156   -1.8562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7142   -0.2048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7142    0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4293   -0.6173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1443   -0.2048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4293   -1.4423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  0  0  0  0
  1 10  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8 12  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333415

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H24O3/c1-8(2)11-6-5-9(3)7-12(11)16-13(15)10(4)14/h8-12,14H,5-7H2,1-4H3/t9-,10?,11+,12-/m1/s1

> <INCHI_KEY>
UJNOLBSYLSYIBM-SGUBAKSOSA-N

> <FORMULA>
C13H24O3

> <MOLECULAR_WEIGHT>
228.3279

> <EXACT_MASS>
228.172544634

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
26.34443951205739

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl 2-hydroxypropanoate

> <ALOGPS_LOGP>
2.78

> <JCHEM_LOGP>
2.8569147536666657

> <ALOGPS_LOGS>
-3.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.998140822941853

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6744132040452335

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
62.79290000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.92e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-hydroxypropanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -2.670  -1.152   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.003  -0.382   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.003   1.155   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.670   1.928   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.670   3.465   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.336   1.155   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.336  -0.382   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.001  -1.152   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -4.003  -3.465   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.670  -2.692   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.336  -3.465   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.333  -0.382   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.333   1.155   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.668  -1.152   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.003  -0.382   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.668  -2.692   0.000  0.00  0.00           O+0
CONECT    1    2    7   10                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    1    6    8                                                  
CONECT    8    7   12                                                       
CONECT    9   10                                                            
CONECT   10    1    9   11                                                  
CONECT   11   10                                                            
CONECT   12    8   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Value	Source
Menthyl lactic acid	Generator
(-)-p-Menthan-3-yl lactate	HMDB
FEMA 3748	HMDB
L-Menthyl lactate	HMDB
(1R,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexyl 2-hydroxypropanoic acid	Generator

Chemical Formula

C₁₃H₂₄O₃

Average Mass

228.3279 Da

Monoisotopic Mass

228.17254 Da

IUPAC Name

(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl 2-hydroxypropanoate

Traditional Name

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-hydroxypropanoate

CAS Registry Number

Not Available

SMILES

CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(=O)C(C)O

InChI Identifier

InChI=1S/C13H24O3/c1-8(2)11-6-5-9(3)7-12(11)16-13(15)10(4)14/h8-12,14H,5-7H2,1-4H3/t9-,10?,11+,12-/m1/s1

InChI Key

UJNOLBSYLSYIBM-SGUBAKSOSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-17	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-17	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-17	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600, CD₃OD, simulated)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-17	View Spectrum

Species

Species of Origin

Not Available

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
Secondary alcohol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	2.78	ALOGPS
logP	2.86	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	13	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	62.79 m³·mol⁻¹	ChemAxon
Polarizability	26.34 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0037212

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016219

KNApSAcK ID

Not Available

Chemspider ID

55982

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

62151

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Menthyl lactate (NP0333415)

MOL for NP0333415 (Menthyl lactate)

3D MOL for NP0333415 (Menthyl lactate)

3D SDF for NP0333415 (Menthyl lactate)

3D-SDF for NP0333415 (Menthyl lactate)

PDB for NP0333415 (Menthyl lactate)

3D PDB for NP0333415 (Menthyl lactate)

SMILES for NP0333415 (Menthyl lactate)

INCHI for NP0333415 (Menthyl lactate)

Structure for NP0333415 (Menthyl lactate)

3D Structure for NP0333415 (Menthyl lactate)