NP-MRD: Showing NP-Card for 3-(2-{2-[6-(2-carboxyethyl)-2,6-dimethyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-yl]ethyl}-1-methyl-3-methylidene-6-(prop-1-en-2-yl)cyclohexyl)propanoic acid (NP0211127)

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Record Information

Version

2.0

Created at

2022-09-05 09:15:20 UTC

Updated at

2022-09-05 09:15:21 UTC

NP-MRD ID

NP0211127

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(2-{2-[6-(2-carboxyethyl)-2,6-dimethyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-yl]ethyl}-1-methyl-3-methylidene-6-(prop-1-en-2-yl)cyclohexyl)propanoic acid

Description

Lansic acid, also known as lansate, 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. Lansic acid is a weakly acidic compound (based on its pKa). Outside of the human body, Lansic acid has been detected, but not quantified in, fruits. 3-(2-{2-[6-(2-carboxyethyl)-2,6-dimethyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-yl]ethyl}-1-methyl-3-methylidene-6-(prop-1-en-2-yl)cyclohexyl)propanoic acid is found in Lansium domesticum. This could make lansic acid a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061309202D          

 34 35  0  0  0  0            999 V2000
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 34 28  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv0541 05061309202D          

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 17 15  1  0  0  0  0
 18 16  1  0  0  0  0
 19  1  2  0  0  0  0
 19  2  1  0  0  0  0
 20  3  2  0  0  0  0
 20  4  1  0  0  0  0
 21  5  2  0  0  0  0
 21  9  1  0  0  0  0
 22  6  1  0  0  0  0
 22 10  2  0  0  0  0
 23 11  1  0  0  0  0
 23 19  1  0  0  0  0
 24 12  1  0  0  0  0
 24 20  1  0  0  0  0
 25 13  1  0  0  0  0
 25 21  1  0  0  0  0
 26 14  1  0  0  0  0
 26 22  1  0  0  0  0
 27 15  1  0  0  0  0
 28 16  1  0  0  0  0
 29  7  1  0  0  0  0
 29 17  1  0  0  0  0
 29 23  1  0  0  0  0
 29 25  1  0  0  0  0
 30  8  1  0  0  0  0
 30 18  1  0  0  0  0
 30 24  1  0  0  0  0
 30 26  1  0  0  0  0
 31 27  2  0  0  0  0
 32 27  1  0  0  0  0
 33 28  2  0  0  0  0
 34 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0211127

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)C1CCC(=C)C(CCC2C(C)=CCC(C(C)=C)C2(C)CCC(O)=O)C1(C)CCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O4/c1-19(2)23-11-9-21(5)25(29(23,7)17-15-27(31)32)13-14-26-22(6)10-12-24(20(3)4)30(26,8)18-16-28(33)34/h10,23-26H,1,3,5,9,11-18H2,2,4,6-8H3,(H,31,32)(H,33,34)

> <INCHI_KEY>
SYTWWAZKYVYTTQ-UHFFFAOYSA-N

> <FORMULA>
C30H46O4

> <MOLECULAR_WEIGHT>
470.6838

> <EXACT_MASS>
470.33960996

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
55.18946766830627

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(2-{2-[6-(2-carboxyethyl)-2,6-dimethyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-yl]ethyl}-1-methyl-3-methylidene-6-(prop-1-en-2-yl)cyclohexyl)propanoic acid

> <ALOGPS_LOGP>
6.35

> <JCHEM_LOGP>
6.919794826333334

> <ALOGPS_LOGS>
-5.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.91781871363391

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.315758722305947

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
138.96529999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.00e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(2-{2-[6-(2-carboxyethyl)-2,6-dimethyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-yl]ethyl}-1-methyl-3-methylidene-6-(prop-1-en-2-yl)cyclohexyl)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       5.335  10.780   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.668  11.550   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335   9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  13.860   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.657  10.420   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.657   9.600   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667  13.860   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001  13.090   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  10.780   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.204  11.867   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.204   8.153   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.677  10.420   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.677   9.600   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.335  10.780   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.334  13.090   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.001  11.550   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.334  11.550   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.214  13.047   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.214   6.973   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.667  10.780   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.741  14.494   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -0.302  12.779   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       0.302   7.241   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -1.741   5.526   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2   19                                                            
CONECT    3   20                                                            
CONECT    4   20                                                            
CONECT    5   21                                                            
CONECT    6   22                                                            
CONECT    7   29                                                            
CONECT    8   30                                                            
CONECT    9   11   21                                                       
CONECT   10   12   22                                                       
CONECT   11    9   23                                                       
CONECT   12   10   24                                                       
CONECT   13   14   25                                                       
CONECT   14   13   26                                                       
CONECT   15   17   27                                                       
CONECT   16   18   28                                                       
CONECT   17   15   29                                                       
CONECT   18   16   30                                                       
CONECT   19    1    2   23                                                  
CONECT   20    3    4   24                                                  
CONECT   21    5    9   25                                                  
CONECT   22    6   10   26                                                  
CONECT   23   11   19   29                                                  
CONECT   24   12   20   30                                                  
CONECT   25   13   21   29                                                  
CONECT   26   14   22   30                                                  
CONECT   27   15   31   32                                                  
CONECT   28   16   33   34                                                  
CONECT   29    7   17   23   25                                             
CONECT   30    8   18   24   26                                             
CONECT   31   27                                                            
CONECT   32   27                                                            
CONECT   33   28                                                            
CONECT   34   28                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   70    0
END

View in JSmol

Synonyms

Value	Source
Lansate	Generator
3,4;21,22-bisseco-4(23),7,14(27),22(29)-onoceratetraene-3,21-dioic acid	HMDB
3-(2-{2-[6-(2-carboxyethyl)-2,6-dimethyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-yl]ethyl}-1-methyl-3-methylidene-6-(prop-1-en-2-yl)cyclohexyl)propanoate	Generator

Chemical Formula

C₃₀H₄₆O₄

Average Mass

470.6838 Da

Monoisotopic Mass

470.33961 Da

IUPAC Name

3-(2-{2-[6-(2-carboxyethyl)-2,6-dimethyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-yl]ethyl}-1-methyl-3-methylidene-6-(prop-1-en-2-yl)cyclohexyl)propanoic acid

Traditional Name

3-(2-{2-[6-(2-carboxyethyl)-2,6-dimethyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-yl]ethyl}-1-methyl-3-methylidene-6-(prop-1-en-2-yl)cyclohexyl)propanoic acid

CAS Registry Number

Not Available

SMILES

CC(=C)C1CCC(=C)C(CCC2C(C)=CCC(C(C)=C)C2(C)CCC(O)=O)C1(C)CCC(O)=O

InChI Identifier

InChI=1S/C30H46O4/c1-19(2)23-11-9-21(5)25(29(23,7)17-15-27(31)32)13-14-26-22(6)10-12-24(20(3)4)30(26,8)18-16-28(33)34/h10,23-26H,1,3,5,9,11-18H2,2,4,6-8H3,(H,31,32)(H,33,34)

InChI Key

SYTWWAZKYVYTTQ-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
Lansium domesticum	LOTUS Database	35616633

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
Carbocyclic fatty acid
Fatty acyl
Dicarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	6.35	ALOGPS
logP	6.92	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	4.32	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	138.97 m³·mol⁻¹	ChemAxon
Polarizability	55.19 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0036786

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB015728

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15560072

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-(2-{2-[6-(2-carboxyethyl)-2,6-dimethyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-yl]ethyl}-1-methyl-3-methylidene-6-(prop-1-en-2-yl)cyclohexyl)propanoic acid (NP0211127)

MOL for NP0211127 (3-(2-{2-[6-(2-carboxyethyl)-2,6-dimethyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-yl]ethyl}-1-methyl-3-methylidene-6-(prop-1-en-2-yl)cyclohexyl)propanoic acid)

3D MOL for NP0211127 (3-(2-{2-[6-(2-carboxyethyl)-2,6-dimethyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-yl]ethyl}-1-methyl-3-methylidene-6-(prop-1-en-2-yl)cyclohexyl)propanoic acid)

3D SDF for NP0211127 (3-(2-{2-[6-(2-carboxyethyl)-2,6-dimethyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-yl]ethyl}-1-methyl-3-methylidene-6-(prop-1-en-2-yl)cyclohexyl)propanoic acid)

3D-SDF for NP0211127 (3-(2-{2-[6-(2-carboxyethyl)-2,6-dimethyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-yl]ethyl}-1-methyl-3-methylidene-6-(prop-1-en-2-yl)cyclohexyl)propanoic acid)

PDB for NP0211127 (3-(2-{2-[6-(2-carboxyethyl)-2,6-dimethyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-yl]ethyl}-1-methyl-3-methylidene-6-(prop-1-en-2-yl)cyclohexyl)propanoic acid)

3D PDB for NP0211127 (3-(2-{2-[6-(2-carboxyethyl)-2,6-dimethyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-yl]ethyl}-1-methyl-3-methylidene-6-(prop-1-en-2-yl)cyclohexyl)propanoic acid)

SMILES for NP0211127 (3-(2-{2-[6-(2-carboxyethyl)-2,6-dimethyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-yl]ethyl}-1-methyl-3-methylidene-6-(prop-1-en-2-yl)cyclohexyl)propanoic acid)

INCHI for NP0211127 (3-(2-{2-[6-(2-carboxyethyl)-2,6-dimethyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-yl]ethyl}-1-methyl-3-methylidene-6-(prop-1-en-2-yl)cyclohexyl)propanoic acid)

Structure for NP0211127 (3-(2-{2-[6-(2-carboxyethyl)-2,6-dimethyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-yl]ethyl}-1-methyl-3-methylidene-6-(prop-1-en-2-yl)cyclohexyl)propanoic acid)

3D Structure for NP0211127 (3-(2-{2-[6-(2-carboxyethyl)-2,6-dimethyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-yl]ethyl}-1-methyl-3-methylidene-6-(prop-1-en-2-yl)cyclohexyl)propanoic acid)