NP-MRD: Showing NP-Card for eucomic acid, (-)- (NP0259530)

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Record Information

Version

2.0

Created at

2022-09-08 01:26:00 UTC

Updated at

2022-09-08 01:26:00 UTC

NP-MRD ID

NP0259530

Secondary Accession Numbers

None

Natural Product Identification

Common Name

eucomic acid, (-)-

Description

Eucomic acid, also known as eucomate, belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid. eucomic acid, (-)- is found in Crotalaria sessiliflora, Lotus corniculatus and Papilionanthe teres. eucomic acid, (-)- was first documented in 2017 (PMID: 28276764). Based on a literature review a significant number of articles have been published on Eucomic acid (PMID: 35053894) (PMID: 34068519) (PMID: 33803279) (PMID: 31816895) (PMID: 31052535) (PMID: 30757900).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 29  0  0  0  0  0  0  0  0999 V2000
    0.2208    0.1165   -2.9066 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7090    0.4530   -2.1372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8812    1.8035   -1.8497 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6059   -0.5485   -1.5443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6721   -0.6109   -0.0700 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1009    0.6709    0.3703 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4851   -1.0189    0.7006 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7314   -0.2348    0.5973 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8996    0.8721    1.4050 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0673    1.5980    1.3326 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0923    1.2695    0.4812 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2814    2.0167    0.4142 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9340    0.1602   -0.3345 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7537   -0.5680   -0.2570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8445   -1.5173    0.2779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8677   -1.0570    0.8159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7538   -2.8625   -0.0145 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7515    2.2942   -2.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6475   -0.2513   -1.8957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4631   -1.5459   -2.0300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4386    0.5649    1.3024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2838   -2.1095    0.4312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7403   -1.1140    1.8075 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1170    1.1901    2.1115 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2032    2.4740    1.9696 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3802    2.8168    1.0129 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7429   -0.0892   -0.9996 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6764   -1.4234   -0.9107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8552   -3.3491    0.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  1
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
  5 15  1  0
 15 17  1  0
 15 16  2  0
 14  8  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  9 24  1  0
 10 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 17 29  1  0
M  END


  Mrv1652309082203262D          

 17 17  0  0  1  0            999 V2000
   -2.1434    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4125    1.7605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    3.1895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.9039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  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
 13 14  2  0  0  0  0
  8 14  1  0  0  0  0
  5 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0259530

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C[C@](O)(CC1=CC=C(O)C=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H12O6/c12-8-3-1-7(2-4-8)5-11(17,10(15)16)6-9(13)14/h1-4,12,17H,5-6H2,(H,13,14)(H,15,16)/t11-/m1/s1

> <INCHI_KEY>
XLGKDRSWPCQYAB-LLVKDONJSA-N

> <FORMULA>
C11H12O6

> <MOLECULAR_WEIGHT>
240.211

> <EXACT_MASS>
240.063388106

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
22.245498344174994

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R)-2-hydroxy-2-[(4-hydroxyphenyl)methyl]butanedioic acid

> <JCHEM_LOGP>
0.671885504

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.2466996506254455

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.353941380062546

> <JCHEM_PKA_STRONGEST_BASIC>
-4.103071730863957

> <JCHEM_POLAR_SURFACE_AREA>
115.06000000000002

> <JCHEM_REFRACTIVITY>
56.1884

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-hydroxy-2-[(4-hydroxyphenyl)methyl]butanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  O   UNK     0      -4.001   5.390   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.667   3.080   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.334   5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.770   3.286   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.770   5.954   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.310   5.954   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.000   7.287   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7   15                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    8                                                       
CONECT   15    5   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
Eucomate	Generator

Chemical Formula

C₁₁H₁₂O₆

Average Mass

240.2110 Da

Monoisotopic Mass

240.06339 Da

IUPAC Name

(2R)-2-hydroxy-2-[(4-hydroxyphenyl)methyl]butanedioic acid

Traditional Name

(2R)-2-hydroxy-2-[(4-hydroxyphenyl)methyl]butanedioic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C[C@](O)(CC1=CC=C(O)C=C1)C(O)=O

InChI Identifier

InChI=1S/C11H12O6/c12-8-3-1-7(2-4-8)5-11(17,10(15)16)6-9(13)14/h1-4,12,17H,5-6H2,(H,13,14)(H,15,16)/t11-/m1/s1

InChI Key

XLGKDRSWPCQYAB-LLVKDONJSA-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
Crotalaria sessiliflora	LOTUS Database	35616633
Lotus corniculatus	LOTUS Database	35616633
Papilionanthe teres	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Phenylpropanoic acids

Sub Class

Not Available

Direct Parent

Phenylpropanoic acids

Alternative Parents

Substituents

3-phenylpropanoic-acid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alpha-hydroxy acid
Monocyclic benzene moiety
Benzenoid
Hydroxy acid
Dicarboxylic acid or derivatives
Tertiary alcohol
Carboxylic acid derivative
Carboxylic acid
Alcohol
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:67353 )

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	0.67	ChemAxon
pKa (Strongest Acidic)	3.35	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	115.06 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	56.19 m³·mol⁻¹	ChemAxon
Polarizability	22.25 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	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

C00053116

Chemspider ID

23551038

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23757219

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hernandez F, Andreu-Coll L, Bento-Silva A, Serra AT, Mena P, Legua P, Bronze MR: Phytochemical Profile of Opuntia ficus-indica (L.) Mill Fruits (cv. 'Orito') Stored at Different Conditions. Foods. 2022 Jan 8;11(2):160. doi: 10.3390/foods11020160. [PubMed:35053894 ]
Tomani JCD, Bonnet O, Nyirimigabo A, Deschamps W, Tchinda AT, Jansen O, Ledoux A, Mukazayire MJ, Vanhamme L, Frederich M, Muganga R, Souopgui J: In Vitro Antiplasmodial and Cytotoxic Activities of Compounds from the Roots of Eriosema montanum Baker f. (Fabaceae). Molecules. 2021 May 10;26(9):2795. doi: 10.3390/molecules26092795. [PubMed:34068519 ]
Alexandre EMC, Coelho MC, Ozcan K, Pinto CA, Teixeira JA, Saraiva JA, Pintado M: Emergent Technologies for the Extraction of Antioxidants from Prickly Pear Peel and Their Antimicrobial Activity. Foods. 2021 Mar 9;10(3):570. doi: 10.3390/foods10030570. [PubMed:33803279 ]
Aremu AO, Masondo NA, Gruz J, Dolezal K, Van Staden J: Potential of Smoke-Water and One of Its Active Compounds (karrikinolide, KAR(1)) on the Phytochemical and Antioxidant Activity of Eucomis autumnalis. Antioxidants (Basel). 2019 Dec 3;8(12):611. doi: 10.3390/antiox8120611. [PubMed:31816895 ]
Blando F, Russo R, Negro C, De Bellis L, Frassinetti S: Antimicrobial and Antibiofilm Activity against Staphylococcus aureus of Opuntia ficus-indica (L.) Mill. Cladode Polyphenolic Extracts. Antioxidants (Basel). 2019 May 2;8(5):117. doi: 10.3390/antiox8050117. [PubMed:31052535 ]
De Santiago E, Gill CIR, Carafa I, Tuohy KM, De Pena MP, Cid C: Digestion and Colonic Fermentation of Raw and Cooked Opuntia ficus-indica Cladodes Impacts Bioaccessibility and Bioactivity. J Agric Food Chem. 2019 Mar 6;67(9):2490-2499. doi: 10.1021/acs.jafc.8b06480. Epub 2019 Feb 25. [PubMed:30757900 ]
Khan H, Marya, Belwal T, Mohd Tariq, Atanasov AG, Devkota HP: Genus Vanda: A review on traditional uses, bioactive chemical constituents and pharmacological activities. J Ethnopharmacol. 2019 Jan 30;229:46-53. doi: 10.1016/j.jep.2018.09.031. Epub 2018 Sep 27. [PubMed:30268653 ]
Belloto AC, Souza GK, Perin PC, Schuquel ITA, Santin SMO, Chiavelli LUR, Garcia FP, Kaplum V, Rodrigues JHS, Scariot DB, Delvecchio R, Machado-Ferreira E, Santana Aguiar R, Soares CAG, Nakamura CV, Pomini AM: Crispoic acid, a new compound from Laelia marginata (Orchidaceae), and biological evaluations against parasites, human cancer cell lines and Zika virus. Nat Prod Res. 2018 Dec;32(24):2916-2921. doi: 10.1080/14786419.2017.1395428. Epub 2017 Nov 8. [PubMed:29117727 ]
Wang LN, He YZ, Zhao QD, Deng YR, Wu PQ, Zhang YJ: Phenolic compounds from Bletilla striata. J Asian Nat Prod Res. 2017 Oct;19(10):981-986. doi: 10.1080/10286020.2017.1281911. Epub 2017 Feb 17. [PubMed:28276764 ]
LOTUS database [Link]

Showing NP-Card for eucomic acid, (-)- (NP0259530)

MOL for NP0259530 (eucomic acid, (-)-)

3D MOL for NP0259530 (eucomic acid, (-)-)

3D SDF for NP0259530 (eucomic acid, (-)-)

3D-SDF for NP0259530 (eucomic acid, (-)-)

PDB for NP0259530 (eucomic acid, (-)-)

3D PDB for NP0259530 (eucomic acid, (-)-)

SMILES for NP0259530 (eucomic acid, (-)-)

INCHI for NP0259530 (eucomic acid, (-)-)

Structure for NP0259530 (eucomic acid, (-)-)

3D Structure for NP0259530 (eucomic acid, (-)-)