NP-MRD: Showing NP-Card for 5-{2,6-dimethylbicyclo[3.1.1]hept-2-en-6-yl}-2-methylpent-2-enoic acid (NP0262192)

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Record Information

Version

2.0

Created at

2022-09-08 04:51:57 UTC

Updated at

2022-09-08 04:51:58 UTC

NP-MRD ID

NP0262192

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-{2,6-dimethylbicyclo[3.1.1]hept-2-en-6-yl}-2-methylpent-2-enoic acid

Description

5-{2,6-Dimethylbicyclo[3.1.1]Hept-2-en-6-yl}-2-methylpent-2-enoic acid belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. 5-{2,6-dimethylbicyclo[3.1.1]hept-2-en-6-yl}-2-methylpent-2-enoic acid is found in Solanum habrochaites. 5-{2,6-Dimethylbicyclo[3.1.1]Hept-2-en-6-yl}-2-methylpent-2-enoic acid is a very weakly acidic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
   -4.0397    1.7623   -0.4589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2121    0.6095   -0.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6057   -0.6309   -0.2902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6790   -1.7447    0.1059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4473   -1.1842    0.7855 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8897   -0.1321    1.7818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9010    0.8347    0.5866 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8324   -0.0724   -0.0215 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9634   -0.2189   -1.5174 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5241    0.2983    0.4596 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5815   -0.7208    0.0811 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8723   -0.2205    0.6238 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9084    0.0443   -0.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7613   -0.1702   -1.6071 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1613    0.5321    0.3948 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1151    0.7686   -0.3832 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3395    0.7469    1.7599 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0904    1.4851   -0.6932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6133    2.3455   -1.3085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1170    2.4813    0.4053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5489   -0.9231   -0.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3484   -2.3252   -0.7703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1565   -2.4447    0.8156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7799   -1.9509    1.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1106    0.0920    2.5042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9117   -0.2870    2.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6059    1.8516    0.8022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9002    0.2182   -1.8547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8536   -1.2919   -1.7538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0582    0.2889   -1.9565 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6154    0.4582    1.5473 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8459    1.2554   -0.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6010   -0.8534   -1.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3697   -1.6857    0.6233 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9722   -0.0664    1.6873 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4767   -1.2406   -1.7775 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6775    0.0975   -2.1669 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8972    0.4265   -1.9442 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9461    1.5668    2.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 12  2  0
 12 11  1  0
 11 10  1  0
  8 10  1  6
  8  9  1  0
  8  5  1  0
  5  6  1  0
  6  7  1  0
  7  2  1  0
  2  1  1  0
  2  3  2  0
  3  4  1  0
 13 15  1  0
 15 17  1  0
 15 16  2  0
  7  8  1  0
  4  5  1  0
 14 36  1  0
 14 37  1  0
 14 38  1  0
 12 35  1  0
 11 33  1  0
 11 34  1  0
 10 31  1  0
 10 32  1  0
  9 28  1  0
  9 29  1  0
  9 30  1  0
  5 24  1  1
  6 25  1  0
  6 26  1  0
  7 27  1  1
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
 17 39  1  0
M  END


  Mrv1533004161522102D          

 17 18  0  0  0  0            999 V2000
   -0.2496    3.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0249    2.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1681    2.0501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5362    1.5198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6794    0.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0474    0.1770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6794   -0.3533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3651    0.8915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1901    0.8915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6026    0.1770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1901   -0.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6026   -1.2519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3651   -0.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5437    0.1770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6569    3.3928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4321    3.1107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5136    4.2053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  4  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  0  0  0  0
  8 14  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0262192

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=CCCC1(C)C2CC1C(C)=CC2)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O2/c1-10-6-7-12-9-13(10)15(12,3)8-4-5-11(2)14(16)17/h5-6,12-13H,4,7-9H2,1-3H3,(H,16,17)

> <INCHI_KEY>
CTORLPNPQPAKGI-UHFFFAOYSA-N

> <FORMULA>
C15H22O2

> <MOLECULAR_WEIGHT>
234.339

> <EXACT_MASS>
234.161979948

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
27.45506319881186

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-{2,6-dimethylbicyclo[3.1.1]hept-2-en-6-yl}-2-methylpent-2-enoic acid

> <ALOGPS_LOGP>
4.50

> <JCHEM_LOGP>
3.6530683203333334

> <ALOGPS_LOGS>
-3.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.058317348962378

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
70.2421

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.48e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-{2,6-dimethylbicyclo[3.1.1]hept-2-en-6-yl}-2-methylpent-2-enoic acid

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      -0.466   5.870   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.913   5.343   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.181   3.827   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.001   2.837   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.268   1.320   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.089   0.330   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.268  -0.659   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.681   1.664   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.221   1.664   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.991   0.330   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.221  -1.003   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.991  -2.337   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.681  -1.003   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.015   0.330   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.093   6.333   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -4.540   5.807   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -2.825   7.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   13                                             
CONECT    7    6                                                            
CONECT    8    6    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    6   14                                                  
CONECT   14   13    8                                                       
CONECT   15    2   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Value	Source
5-{2,6-dimethylbicyclo[3.1.1]hept-2-en-6-yl}-2-methylpent-2-enoate	Generator

Chemical Formula

C₁₅H₂₂O₂

Average Mass

234.3390 Da

Monoisotopic Mass

234.16198 Da

IUPAC Name

5-{2,6-dimethylbicyclo[3.1.1]hept-2-en-6-yl}-2-methylpent-2-enoic acid

Traditional Name

5-{2,6-dimethylbicyclo[3.1.1]hept-2-en-6-yl}-2-methylpent-2-enoic acid

CAS Registry Number

Not Available

SMILES

CC(=CCCC1(C)C2CC1C(C)=CC2)C(O)=O

InChI Identifier

InChI=1S/C15H22O2/c1-10-6-7-12-9-13(10)15(12,3)8-4-5-11(2)14(16)17/h5-6,12-13H,4,7-9H2,1-3H3,(H,16,17)

InChI Key

CTORLPNPQPAKGI-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
Solanum habrochaites	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Bicyclic monoterpenoids

Alternative Parents

Substituents

Bicyclic monoterpenoid
Pinane monoterpenoid
Medium-chain fatty acid
Branched fatty acid
Methyl-branched fatty acid
Fatty acyl
Fatty acid
Unsaturated fatty acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Carboxylic acid
Organic oxygen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	4.5	ALOGPS
logP	3.65	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	5.06	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	4	ChemAxon
Refractivity	70.24 m³·mol⁻¹	ChemAxon
Polarizability	27.46 Å³	ChemAxon
Number of Rings	2	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

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

73832369

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-{2,6-dimethylbicyclo[3.1.1]hept-2-en-6-yl}-2-methylpent-2-enoic acid (NP0262192)

MOL for NP0262192 (5-{2,6-dimethylbicyclo[3.1.1]hept-2-en-6-yl}-2-methylpent-2-enoic acid)

3D MOL for NP0262192 (5-{2,6-dimethylbicyclo[3.1.1]hept-2-en-6-yl}-2-methylpent-2-enoic acid)

3D SDF for NP0262192 (5-{2,6-dimethylbicyclo[3.1.1]hept-2-en-6-yl}-2-methylpent-2-enoic acid)

3D-SDF for NP0262192 (5-{2,6-dimethylbicyclo[3.1.1]hept-2-en-6-yl}-2-methylpent-2-enoic acid)

PDB for NP0262192 (5-{2,6-dimethylbicyclo[3.1.1]hept-2-en-6-yl}-2-methylpent-2-enoic acid)

3D PDB for NP0262192 (5-{2,6-dimethylbicyclo[3.1.1]hept-2-en-6-yl}-2-methylpent-2-enoic acid)

SMILES for NP0262192 (5-{2,6-dimethylbicyclo[3.1.1]hept-2-en-6-yl}-2-methylpent-2-enoic acid)

INCHI for NP0262192 (5-{2,6-dimethylbicyclo[3.1.1]hept-2-en-6-yl}-2-methylpent-2-enoic acid)

Structure for NP0262192 (5-{2,6-dimethylbicyclo[3.1.1]hept-2-en-6-yl}-2-methylpent-2-enoic acid)

3D Structure for NP0262192 (5-{2,6-dimethylbicyclo[3.1.1]hept-2-en-6-yl}-2-methylpent-2-enoic acid)