NP-MRD: Showing NP-Card for Luteic acid (NP0046967)

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Record Information

Version

2.0

Created at

2022-03-17 20:32:26 UTC

Updated at

2022-03-17 20:32:27 UTC

NP-MRD ID

NP0046967

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Luteic acid

Description

3,4,8,9,10-Pentahydroxy-6-oxo-6H-benzo[c]chromene-1-carboxylic acid belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. 3,4,8,9,10-Pentahydroxy-6-oxo-6H-benzo[c]chromene-1-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 3,4,8,9,10-pentahydroxy-6-oxo-6H-benzo[c]chromene-1-carboxylic acid has been detected, but not quantified in, guava. This could make 3,4,8,9,10-pentahydroxy-6-oxo-6H-benzo[c]chromene-1-carboxylic acid a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309131710502D          

 23 25  0  0  0  0            999 V2000
    1.7309    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0309   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2059   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3184    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0309    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2059    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2684    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4934    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4434    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3184   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6359    2.3264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2059   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  5  2  1  0  0  0  0
  6  1  1  0  0  0  0
  7  4  1  0  0  0  0
  8  3  1  0  0  0  0
  8  7  1  0  0  0  0
  9  5  2  0  0  0  0
 10  6  2  0  0  0  0
 11  7  2  0  0  0  0
 11  9  1  0  0  0  0
 12  8  2  0  0  0  0
 12 10  1  0  0  0  0
 13  3  1  0  0  0  0
 14  4  1  0  0  0  0
 15  5  1  0  0  0  0
 16  6  1  0  0  0  0
 17  9  1  0  0  0  0
 18 10  1  0  0  0  0
 19 11  1  0  0  0  0
 20 13  2  0  0  0  0
 21 13  1  0  0  0  0
 22 14  2  0  0  0  0
 23 12  1  0  0  0  0
 23 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046967

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1=CC(O)=C(O)C2=C1C1=C(O)C(O)=C(O)C=C1C(=O)O2

> <INCHI_IDENTIFIER>
InChI=1S/C14H8O9/c15-5-2-4-7(11(19)9(5)17)8-3(13(20)21)1-6(16)10(18)12(8)23-14(4)22/h1-2,15-19H,(H,20,21)

> <INCHI_KEY>
FLZGFQFYDGHWLR-UHFFFAOYSA-N

> <FORMULA>
C14H8O9

> <MOLECULAR_WEIGHT>
320.2079

> <EXACT_MASS>
320.016831854

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
27.857877307297134

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,4,8,9,10-pentahydroxy-6-oxo-6H-benzo[c]chromene-1-carboxylic acid

> <ALOGPS_LOGP>
1.97

> <JCHEM_LOGP>
1.7150837409999997

> <ALOGPS_LOGS>
-2.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
7.049985505419112

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.446168580859518

> <JCHEM_PKA_STRONGEST_BASIC>
-4.79103852268332

> <JCHEM_POLAR_SURFACE_AREA>
164.74999999999997

> <JCHEM_REFRACTIVITY>
74.0998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.74e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4,8,9,10-pentahydroxy-6-oxobenzo[c]chromene-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-SEP-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-SEP-17         0                                  
HETATM    1  C   UNK     0       3.231   2.104   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.391  -0.564   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.771   2.104   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.851  -0.564   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.161   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.461   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.081   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.541   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.391   2.104   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.231  -0.564   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.851   2.104   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.771  -0.564   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.541   3.437   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.081  -1.897   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      11.701   0.770   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.921   0.770   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      10.161   3.437   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.461  -1.897   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       7.081   3.437   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.787   4.343   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.771   4.771   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       7.851  -3.231   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.541  -1.897   0.000  0.00  0.00           O+0
CONECT    1    3    6                                                       
CONECT    2    4    5                                                       
CONECT    3    1    8   13                                                  
CONECT    4    2    7   14                                                  
CONECT    5    2    9   15                                                  
CONECT    6    1   10   16                                                  
CONECT    7    4    8   11                                                  
CONECT    8    3    7   12                                                  
CONECT    9    5   11   17                                                  
CONECT   10    6   12   18                                                  
CONECT   11    7    9   19                                                  
CONECT   12    8   10   23                                                  
CONECT   13    3   20   21                                                  
CONECT   14    4   22   23                                                  
CONECT   15    5                                                            
CONECT   16    6                                                            
CONECT   17    9                                                            
CONECT   18   10                                                            
CONECT   19   11                                                            
CONECT   20   13                                                            
CONECT   21   13                                                            
CONECT   22   14                                                            
CONECT   23   12   14                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Value	Source
3,4,8,9,10-Pentahydroxy-6-oxo-6H-benzo[c]chromene-1-carboxylate	Generator
Luteate	Generator

Chemical Formula

C₁₄H₈O₉

Average Mass

320.2079 Da

Monoisotopic Mass

320.01683 Da

IUPAC Name

3,4,8,9,10-pentahydroxy-6-oxo-6H-benzo[c]chromene-1-carboxylic acid

Traditional Name

3,4,8,9,10-pentahydroxy-6-oxobenzo[c]chromene-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C1=CC(O)=C(O)C2=C1C1=C(O)C(O)=C(O)C=C1C(=O)O2

InChI Identifier

InChI=1S/C14H8O9/c15-5-2-4-7(11(19)9(5)17)8-3(13(20)21)1-6(16)10(18)12(8)23-14(4)22/h1-2,15-19H,(H,20,21)

InChI Key

FLZGFQFYDGHWLR-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Psidium guajava	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Hydrolyzable tannins

Direct Parent

Hydrolyzable tannins

Alternative Parents

Substituents

Hydrolyzable tannin
7,8-dihydroxycoumarin
Gallic acid or derivatives
Isocoumarin
Dihydroxybenzoic acid
Coumarin
Benzopyran
Hydroxybenzoic acid
1-benzopyran
2-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Lactone
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	1.97	ALOGPS
logP	1.72	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	3.45	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	164.75 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	74.1 m³·mol⁻¹	ChemAxon
Polarizability	27.86 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0126633

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB006735

KNApSAcK ID

Not Available

Chemspider ID

4477499

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5319108

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Luteic acid (NP0046967)

MOL for NP0046967 (Luteic acid)

3D MOL for NP0046967 (Luteic acid)

3D SDF for NP0046967 (Luteic acid)

3D-SDF for NP0046967 (Luteic acid)

PDB for NP0046967 (Luteic acid)

3D PDB for NP0046967 (Luteic acid)

SMILES for NP0046967 (Luteic acid)

INCHI for NP0046967 (Luteic acid)

Structure for NP0046967 (Luteic acid)

3D Structure for NP0046967 (Luteic acid)