NP-MRD: Showing NP-Card for 4-[(1s,2s)-3-oxo-2-[(2z)-pent-2-en-1-yl]cyclopentyl]butanoic acid (NP0309107)

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Record Information

Version

2.0

Created at

2022-09-11 03:27:29 UTC

Updated at

2022-09-11 03:27:29 UTC

NP-MRD ID

NP0309107

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-[(1s,2s)-3-oxo-2-[(2z)-pent-2-en-1-yl]cyclopentyl]butanoic acid

Description

(9S,13s)-1a,1b-dihomo-jasmonic acid belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety. 4-[(1s,2s)-3-oxo-2-[(2z)-pent-2-en-1-yl]cyclopentyl]butanoic acid is found in Lasiodiplodia theobromae. Based on a literature review very few articles have been published on (9s,13s)-1a,1b-dihomo-jasmonic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 39  0  0  0  0  0  0  0  0999 V2000
   -4.5764    0.3276   -0.5049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5595   -0.7409   -0.9511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1337   -1.4812    0.2465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8894   -1.4993    0.6395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7830   -0.8088   -0.0379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2241    0.1729    0.9877 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2960    1.2388    1.0806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2662    1.1778    1.7770 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9417    2.3582    0.1697 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3366    1.8809   -0.5243 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9280    0.9734    0.5101 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0300    0.1632   -0.1064 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6084   -0.8509    0.8438 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6812   -1.6250    0.1141 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7997   -0.8104   -0.3556 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9131   -0.9201    0.2497 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6894    0.0523   -1.4027 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0807    1.3013   -0.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0599   -0.0548    0.4040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3300    0.4990   -1.2957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8223   -0.2136   -1.5259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1634   -1.4004   -1.6433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9198   -2.0409    0.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6563   -2.0871    1.5627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0541   -0.3172   -0.9556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0109   -1.6163   -0.2586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0923   -0.3528    1.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6535    3.2653    0.7362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7264    2.5724   -0.5857 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9925    2.7458   -0.7664 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0951    1.3218   -1.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3102    1.5692    1.3504 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7474   -0.2932   -1.0447 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8606    0.9042   -0.3024 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8052   -1.4787    1.2343 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0715   -0.3240    1.7203 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0460   -2.4609    0.7935 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2667   -2.1681   -0.7663 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0579    1.0205   -1.3734 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 17  1  0
 15 16  2  0
 11 10  1  0
 10  9  1  0
  9  7  1  0
  7  8  2  0
  7  6  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  1
 11 32  1  1
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 17 39  1  0
 10 30  1  0
 10 31  1  0
  9 28  1  0
  9 29  1  0
M  END


  Mrv1652309112205272D          

 17 17  0  0  1  0            999 V2000
   -0.6156    1.5325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2287    2.0846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0572    2.8915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2726    3.1465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3405    2.5945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1251    2.8494    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3801    3.6340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8952    4.3015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2051    3.6340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4600    2.8494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7926    2.3645    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7926    1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5070    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2215    1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9360    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6505    1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9360    0.3020    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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0309107

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC\C=C/C[C@H]1[C@@H](CCCC(O)=O)CCC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H22O3/c1-2-3-4-7-12-11(9-10-13(12)15)6-5-8-14(16)17/h3-4,11-12H,2,5-10H2,1H3,(H,16,17)/b4-3-/t11-,12-/m0/s1

> <INCHI_KEY>
LVQJNKFFJNUFNY-WGPFEIJOSA-N

> <FORMULA>
C14H22O3

> <MOLECULAR_WEIGHT>
238.327

> <EXACT_MASS>
238.156894568

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
27.40942027092806

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(1S,2S)-3-oxo-2-[(2Z)-pent-2-en-1-yl]cyclopentyl]butanoic acid

> <JCHEM_LOGP>
3.303448207666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.5503986026215895

> <JCHEM_PKA_STRONGEST_BASIC>
-7.4221175740983405

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
67.7585

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4-[(1S,2S)-3-oxo-2-[(2Z)-pent-2-en-1-yl]cyclopentyl]butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.149   2.861   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.294   3.891   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.973   5.398   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.509   5.873   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.636   4.843   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.100   5.319   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.576   6.783   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.671   8.029   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.116   6.783   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.592   5.319   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.346   4.414   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.346   2.874   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.680   2.104   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.013   2.874   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.347   2.104   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.681   2.874   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       7.347   0.564   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    6   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

View in JSmol

Synonyms

Value	Source
(9S,13S)-1a,1b-Dihomo-jasmonate	Generator

Chemical Formula

C₁₄H₂₂O₃

Average Mass

238.3270 Da

Monoisotopic Mass

238.15689 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC\C=C/C[C@H]1[C@@H](CCCC(O)=O)CCC1=O

InChI Identifier

InChI=1S/C14H22O3/c1-2-3-4-7-12-11(9-10-13(12)15)6-5-8-14(16)17/h3-4,11-12H,2,5-10H2,1H3,(H,16,17)/b4-3-/t11-,12-/m0/s1

InChI Key

LVQJNKFFJNUFNY-WGPFEIJOSA-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
Lasiodiplodia theobromae	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclic ketones

Alternative Parents

Substituents

Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

12-oxophytodienoic acid metabolites (LMFA02010011 )

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

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

24822051

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14311116

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-[(1s,2s)-3-oxo-2-[(2z)-pent-2-en-1-yl]cyclopentyl]butanoic acid (NP0309107)

MOL for NP0309107 (4-[(1s,2s)-3-oxo-2-[(2z)-pent-2-en-1-yl]cyclopentyl]butanoic acid)

3D MOL for NP0309107 (4-[(1s,2s)-3-oxo-2-[(2z)-pent-2-en-1-yl]cyclopentyl]butanoic acid)

3D SDF for NP0309107 (4-[(1s,2s)-3-oxo-2-[(2z)-pent-2-en-1-yl]cyclopentyl]butanoic acid)

3D-SDF for NP0309107 (4-[(1s,2s)-3-oxo-2-[(2z)-pent-2-en-1-yl]cyclopentyl]butanoic acid)

PDB for NP0309107 (4-[(1s,2s)-3-oxo-2-[(2z)-pent-2-en-1-yl]cyclopentyl]butanoic acid)

3D PDB for NP0309107 (4-[(1s,2s)-3-oxo-2-[(2z)-pent-2-en-1-yl]cyclopentyl]butanoic acid)

SMILES for NP0309107 (4-[(1s,2s)-3-oxo-2-[(2z)-pent-2-en-1-yl]cyclopentyl]butanoic acid)

INCHI for NP0309107 (4-[(1s,2s)-3-oxo-2-[(2z)-pent-2-en-1-yl]cyclopentyl]butanoic acid)

Structure for NP0309107 (4-[(1s,2s)-3-oxo-2-[(2z)-pent-2-en-1-yl]cyclopentyl]butanoic acid)

3D Structure for NP0309107 (4-[(1s,2s)-3-oxo-2-[(2z)-pent-2-en-1-yl]cyclopentyl]butanoic acid)