NP-MRD: Showing NP-Card for 5-{2,3-dimethyltricyclo[2.2.1.0²,⁶]heptan-3-yl}-2-methylpentanoic acid (NP0225599)

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Record Information

Version

2.0

Created at

2022-09-06 04:21:53 UTC

Updated at

2022-09-06 04:21:53 UTC

NP-MRD ID

NP0225599

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-{2,3-dimethyltricyclo[2.2.1.0²,⁶]heptan-3-yl}-2-methylpentanoic acid

Description

Isomelitric acid A, also known as isomelitrate a or isoschizotenuin e, belongs to the class of organic compounds known as phenylpyruvic acid derivatives. Phenylpyruvic acid derivatives are compounds containing a phenylpyruvic acid moiety, which consists of a phenyl group substituted at the second position by an pyruvic acid. Isomelitric acid A is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Isomelitric acid A has been detected, but not quantified in, herbs and spices. 5-{2,3-dimethyltricyclo[2.2.1.0²,⁶]heptan-3-yl}-2-methylpentanoic acid is found in Santalum album. This could make isomelitric acid a a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 08271307342D          

 17 19  0  0  0  0            999 V2000
    4.0071   -3.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7216   -2.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4361   -3.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4196   -2.5266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8486   -2.5266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1341   -2.1141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7216   -3.6536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6351   -0.9047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9206   -1.3172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2061   -0.9047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4916   -1.3172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7772   -0.9047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0627   -1.3172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0627   -2.1422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6338   -1.3172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3482   -0.9047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3482   -0.0797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  1  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  6  1  0  0  0  0
  1  3  1  0  0  0  0
  6  9  1  0  0  0  0
  2  9  1  0  0  0  0
  2  7  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 16  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0225599

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CCCC1(C)C2CC3C(C2)C13C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O2/c1-9(13(16)17)5-4-6-14(2)10-7-11-12(8-10)15(11,14)3/h9-12H,4-8H2,1-3H3,(H,16,17)

> <INCHI_KEY>
GDGGAJNITUJKMP-UHFFFAOYSA-N

> <FORMULA>
C15H24O2

> <MOLECULAR_WEIGHT>
236.3499

> <EXACT_MASS>
236.177630012

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.83247115808753

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-{2,3-dimethyltricyclo[2.2.1.0²,⁶]heptan-3-yl}-2-methylpentanoic acid

> <ALOGPS_LOGP>
3.56

> <JCHEM_LOGP>
3.442463084666666

> <ALOGPS_LOGS>
-4.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.884444638757874

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
66.53569999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.02e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-{2,3-dimethyltricyclo[2.2.1.0²,⁶]heptan-3-yl}-2-methylpentanoic acid

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 27-AUG-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-AUG-13         0                                  
HETATM    1  C   UNK     0       7.480  -6.050   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.814  -5.280   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.147  -6.050   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.250  -4.716   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.917  -4.716   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.584  -3.946   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.814  -6.820   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.519  -1.689   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.185  -2.459   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.851  -1.689   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.518  -2.459   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.184  -1.689   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.850  -2.459   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.850  -3.999   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.183  -2.459   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.517  -1.689   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.517  -0.149   0.000  0.00  0.00           O+0
CONECT    1    2    4    3                                                  
CONECT    2    1    3    9    7                                             
CONECT    3    2    5    1                                                  
CONECT    4    1    6                                                       
CONECT    5    3    6                                                       
CONECT    6    4    5    9                                                  
CONECT    7    2                                                            
CONECT    8    9                                                            
CONECT    9    6    2    8   10                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13                                                            
CONECT   15   16                                                            
CONECT   16   13   15   17                                                  
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

View in JSmol

Synonyms

Value	Source
Isomelitrate a	Generator
3'-O-(8''-Z-Caffeoyl)rosmarinic acid	HMDB
Isoschizotenuin e	HMDB
a-Santalan-12-Oic acid	HMDB
dihydro-a-Santalic acid	HMDB, Generator
5-{2,3-dimethyltricyclo[2.2.1.0²,⁶]heptan-3-yl}-2-methylpentanoate	Generator
Dihydro-a-santalate	Generator
Dihydro-alpha-santalate	Generator
Dihydro-α-santalate	Generator
Dihydro-α-santalic acid	Generator

Chemical Formula

C₁₅H₂₄O₂

Average Mass

236.3499 Da

Monoisotopic Mass

236.17763 Da

IUPAC Name

5-{2,3-dimethyltricyclo[2.2.1.0²,⁶]heptan-3-yl}-2-methylpentanoic acid

Traditional Name

5-{2,3-dimethyltricyclo[2.2.1.0²,⁶]heptan-3-yl}-2-methylpentanoic acid

CAS Registry Number

Not Available

SMILES

CC(CCCC1(C)C2CC3C(C2)C13C)C(O)=O

InChI Identifier

InChI=1S/C15H24O2/c1-9(13(16)17)5-4-6-14(2)10-7-11-12(8-10)15(11,14)3/h9-12H,4-8H2,1-3H3,(H,16,17)

InChI Key

GDGGAJNITUJKMP-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Santalum album	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpyruvic acid derivatives. Phenylpyruvic acid derivatives are compounds containing a phenylpyruvic acid moiety, which consists of a phenyl group substituted at the second position by an pyruvic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylpyruvic acid derivatives

Direct Parent

Phenylpyruvic acid derivatives

Alternative Parents

Substituents

Cinnamic acid
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid
Hydroxycinnamic acid or derivatives
Enol-phenylpyruvate
Cinnamic acid ester
Phenoxyacetate
3-phenylpropanoic-acid
Tricarboxylic acid or derivatives
Styrene
Catechol
Phenoxy compound
Phenol
Fatty acid ester
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Carboxylic acid derivative
Carboxylic acid
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic 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	3.56	ALOGPS
logP	3.44	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	4.88	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	66.54 m³·mol⁻¹	ChemAxon
Polarizability	27.83 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0039523

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB019134

KNApSAcK ID

Not Available

Chemspider ID

10197108

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21582559

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-{2,3-dimethyltricyclo[2.2.1.0²,⁶]heptan-3-yl}-2-methylpentanoic acid (NP0225599)

MOL for NP0225599 (5-{2,3-dimethyltricyclo[2.2.1.0²,⁶]heptan-3-yl}-2-methylpentanoic acid)

3D MOL for NP0225599 (5-{2,3-dimethyltricyclo[2.2.1.0²,⁶]heptan-3-yl}-2-methylpentanoic acid)

3D SDF for NP0225599 (5-{2,3-dimethyltricyclo[2.2.1.0²,⁶]heptan-3-yl}-2-methylpentanoic acid)

3D-SDF for NP0225599 (5-{2,3-dimethyltricyclo[2.2.1.0²,⁶]heptan-3-yl}-2-methylpentanoic acid)

PDB for NP0225599 (5-{2,3-dimethyltricyclo[2.2.1.0²,⁶]heptan-3-yl}-2-methylpentanoic acid)

3D PDB for NP0225599 (5-{2,3-dimethyltricyclo[2.2.1.0²,⁶]heptan-3-yl}-2-methylpentanoic acid)

SMILES for NP0225599 (5-{2,3-dimethyltricyclo[2.2.1.0²,⁶]heptan-3-yl}-2-methylpentanoic acid)

INCHI for NP0225599 (5-{2,3-dimethyltricyclo[2.2.1.0²,⁶]heptan-3-yl}-2-methylpentanoic acid)

Structure for NP0225599 (5-{2,3-dimethyltricyclo[2.2.1.0²,⁶]heptan-3-yl}-2-methylpentanoic acid)

3D Structure for NP0225599 (5-{2,3-dimethyltricyclo[2.2.1.0²,⁶]heptan-3-yl}-2-methylpentanoic acid)