NP-MRD: Showing NP-Card for 12-Hydroxyjasmonic acid (NP0140042)

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Record Information

Version

2.0

Created at

2022-06-29 20:43:22 UTC

Updated at

2022-06-29 20:43:22 UTC

NP-MRD ID

NP0140042

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12-Hydroxyjasmonic acid

Description

12-Hydroxyjasmonic acid, also known as (1R,2R)-12-hydroxyjasmonate or 12oh-ja, belongs to the class of organic compounds known as jasmonic acids. These are lipids containing or derived from a jasmonic acid, with a structure characterized by the presence of an alkene chain linked to a 2-(3-oxocyclopentyl)acetic acid moiety. 12-Hydroxyjasmonic acid is found in Lasiodiplodia theobromae, Origanum dictamnus and Origanum vulgare. 12-Hydroxyjasmonic acid was first documented in 2013 (PMID: 24052260). Based on a literature review a small amount of articles have been published on 12-hydroxyjasmonic acid (PMID: 35508503) (PMID: 31975729) (PMID: 27713750) (PMID: 23852442).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 34  0  0  0  0  0  0  0  0999 V2000
   -4.1965   -0.6396   -1.5122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0586   -0.2719   -1.8990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9550    0.6123   -2.9486 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8471   -0.7798   -1.2386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6869   -0.0483    0.0726 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8365   -0.4386    1.0103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2024   -0.1416    2.3539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9018   -0.8172    2.1947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3439   -1.4733    3.0239 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4455   -0.5181    0.8257 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5316    0.6682    0.9142 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8629    1.0662   -0.4438 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0747    1.0568   -0.9173 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2407    0.6498   -0.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9149   -0.5418   -0.8197 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0372   -0.9565   -0.1083 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0649    1.6100   -2.7754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9350   -1.8598   -0.9974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9440   -0.6624   -1.8429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7024    1.0459   -0.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7367    0.1532    0.8147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9516   -1.5198    0.9343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8038   -0.5344    3.1940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0527    0.9690    2.4500 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0538   -1.3582    0.3274 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3174    0.3277    1.5681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0459    1.5309    1.3685 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0284    1.3877   -1.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2557    1.3712   -1.9576 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0031    1.4861   -0.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1535    0.5151    0.9136 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2420   -0.2153   -1.8305 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2338   -1.4048   -0.8973 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7615   -0.2686   -0.2058 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13 12  2  0
 12 11  1  0
 11 10  1  0
 10  5  1  0
  5  4  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 16 34  1  0
 15 32  1  0
 15 33  1  0
 14 30  1  0
 14 31  1  0
 13 29  1  0
 12 28  1  0
 11 26  1  0
 11 27  1  0
 10 25  1  6
  5 20  1  6
  4 18  1  0
  4 19  1  0
  3 17  1  0
  6 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
M  END


  Mrv1652306292222432D          

 16 16  0  0  1  0            999 V2000
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9967    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    3.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0558    1.6913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8405    1.9462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4535    1.3942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2382    1.6491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8513    1.0971    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
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  5 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0140042

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H18O4/c13-7-3-1-2-4-10-9(8-12(15)16)5-6-11(10)14/h1-2,9-10,13H,3-8H2,(H,15,16)/b2-1-/t9-,10-/m1/s1

> <INCHI_KEY>
RZGFUGXQKMEMOO-BSANDHCLSA-N

> <FORMULA>
C12H18O4

> <MOLECULAR_WEIGHT>
226.272

> <EXACT_MASS>
226.12050906

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
24.086268559906337

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(1R,2R)-2-[(2Z)-5-hydroxypent-2-en-1-yl]-3-oxocyclopentyl]acetic acid

> <ALOGPS_LOGP>
0.87

> <JCHEM_LOGP>
0.9776322610000004

> <ALOGPS_LOGS>
-2.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.791594249561193

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.462628719201375

> <JCHEM_PKA_STRONGEST_BASIC>
-2.0150707610109873

> <JCHEM_POLAR_SURFACE_AREA>
74.60000000000001

> <JCHEM_REFRACTIVITY>
60.485200000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.28e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12-hydroxyjasmonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.615  -1.536   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.393   4.390   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.727   3.620   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       2.393   5.930   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.651   1.651   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.971   3.157   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.436   3.633   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.580   2.602   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.045   3.078   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -7.189   2.048   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   11                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    5   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Value	Source
(-)-12-Hydroxyjasmonic acid	ChEBI
(1R,2R)-12-Hydroxyjasmonic acid	ChEBI
12oh-JA	ChEBI
Tuberonic acid	ChEBI
(-)-12-Hydroxyjasmonate	Generator
(1R,2R)-12-Hydroxyjasmonate	Generator
Tuberonate	Generator
12-Hydroxyjasmonate	Generator

Chemical Formula

C₁₂H₁₈O₄

Average Mass

226.2720 Da

Monoisotopic Mass

226.12051 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C12H18O4/c13-7-3-1-2-4-10-9(8-12(15)16)5-6-11(10)14/h1-2,9-10,13H,3-8H2,(H,15,16)/b2-1-/t9-,10-/m1/s1

InChI Key

RZGFUGXQKMEMOO-BSANDHCLSA-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
Origanum dictamnus	LOTUS Database	35616633
Origanum vulgare	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as jasmonic acids. These are lipids containing or derived from a jasmonic acid, with a structure characterized by the presence of an alkene chain linked to a 2-(3-oxocyclopentyl)acetic acid moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Lineolic acids and derivatives

Direct Parent

Jasmonic acids

Alternative Parents

Substituents

Jasmonic acid
Fatty alcohol
Cyclic ketone
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

oxo carboxylic acid (CHEBI:37420 )
Jasmonic acids (LMFA02020011 )

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

C00000232

Chemspider ID

4593697

KEGG Compound ID

Not Available

BioCyc ID

CPD-11253

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5497122

PDB ID

Not Available

ChEBI ID

37420

Good Scents ID

Not Available

References

General References

Yang G, Ishimaru Y, Hoshino S, Muraoka Y, Uozumi N, Ueda M: 12-Hydroxyjasmonic acid glucoside causes leaf-folding of Samanea saman through ROS accumulation. Sci Rep. 2022 May 4;12(1):7232. doi: 10.1038/s41598-022-11414-2. [PubMed:35508503 ]
Son Y, Lee KY, Gu S, Park JY, Choi SG, Kim HJ: Quality changes in perilla seed powder related to storage duration and temperature. J Food Sci Technol. 2020 Jan;57(1):263-273. doi: 10.1007/s13197-019-04056-2. Epub 2019 Aug 26. [PubMed:31975729 ]
Arens N, Backhaus A, Doll S, Fischer S, Seiffert U, Mock HP: Non-invasive Presymptomatic Detection of Cercospora beticola Infection and Identification of Early Metabolic Responses in Sugar Beet. Front Plant Sci. 2016 Sep 22;7:1377. doi: 10.3389/fpls.2016.01377. eCollection 2016. [PubMed:27713750 ]
Widemann E, Miesch L, Lugan R, Holder E, Heinrich C, Aubert Y, Miesch M, Pinot F, Heitz T: The amidohydrolases IAR3 and ILL6 contribute to jasmonoyl-isoleucine hormone turnover and generate 12-hydroxyjasmonic acid upon wounding in Arabidopsis leaves. J Biol Chem. 2013 Nov 1;288(44):31701-14. doi: 10.1074/jbc.M113.499228. Epub 2013 Sep 19. [PubMed:24052260 ]
Sasaki-Sekimoto Y, Jikumaru Y, Obayashi T, Saito H, Masuda S, Kamiya Y, Ohta H, Shirasu K: Basic helix-loop-helix transcription factors JASMONATE-ASSOCIATED MYC2-LIKE1 (JAM1), JAM2, and JAM3 are negative regulators of jasmonate responses in Arabidopsis. Plant Physiol. 2013 Sep;163(1):291-304. doi: 10.1104/pp.113.220129. Epub 2013 Jul 12. [PubMed:23852442 ]

Showing NP-Card for 12-Hydroxyjasmonic acid (NP0140042)

MOL for NP0140042 (12-Hydroxyjasmonic acid)

3D MOL for NP0140042 (12-Hydroxyjasmonic acid)

3D SDF for NP0140042 (12-Hydroxyjasmonic acid)

3D-SDF for NP0140042 (12-Hydroxyjasmonic acid)

PDB for NP0140042 (12-Hydroxyjasmonic acid)

3D PDB for NP0140042 (12-Hydroxyjasmonic acid)

SMILES for NP0140042 (12-Hydroxyjasmonic acid)

INCHI for NP0140042 (12-Hydroxyjasmonic acid)

Structure for NP0140042 (12-Hydroxyjasmonic acid)

3D Structure for NP0140042 (12-Hydroxyjasmonic acid)