NP-MRD: Showing NP-Card for Luteolinidin (NP0045244)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-03-17 19:16:33 UTC

Updated at

2022-03-17 19:16:33 UTC

NP-MRD ID

NP0045244

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Luteolinidin

Description

Luteolinidin belongs to the class of organic compounds known as 7-hydroxyflavonoids. These are flavonoids that bear one hydroxyl group at the C-7 position of the flavonoid skeleton. Luteolinidin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Luteolinidin has been detected, but not quantified in, corns. This could make luteolinidin a potential biomarker for the consumption of these foods. Luteolinidin is found in Bryum cryophilum, Hyparrhenia filipendula, Rechsteineria cardinalis and Sinningia cardinalis. Luteolinidin is a chemical compound belonging to the 3-deoxyanthocyanidins and that can be found in Sorghum bicolor.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 33  0  0  0  0  0  0  0  0999 V2000
   -4.4618    3.0299   -0.0925 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8143    1.8029   -0.1035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5245    0.6284   -0.1660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8292   -0.5889   -0.1747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5543   -1.7471   -0.2374 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4532   -0.6067   -0.1214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7328   -1.7791   -0.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3374   -1.7093   -0.0711 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3269   -0.5079   -0.0096 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7842   -0.4129    0.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6258   -1.4957    0.0513 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9903   -1.4069    0.1074 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5801   -0.1582    0.1673 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9563    0.0008    0.2258 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7702    0.9775    0.1690 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3870    2.2190    0.2298 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3985    0.8462    0.1115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4127    0.5758   -0.0065 O   0  0  0  0  0  3  0  0  0  0  0  0
   -1.7198    0.5768   -0.0577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4381    1.7773   -0.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7560    3.5006    0.7465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6073    0.6436   -0.2079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2113   -2.6835   -0.2516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2434   -2.7220   -0.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1942   -2.6366   -0.0777 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1942   -2.4805    0.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5865   -2.3083    0.1041 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5270   -0.8345    0.2235 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8998    3.0827    0.2361 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7706    1.7175    0.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8956    2.6990   -0.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2 20  2  0
 20 19  1  0
 19 18  2  0
 18  9  1  0
  9  8  2  0
  8  7  1  0
  7  6  2  0
  6  4  1  0
  4  5  1  0
  4  3  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
  3  2  1  0
 17 10  1  0
  6 19  1  0
  1 21  1  0
 20 31  1  0
  8 25  1  0
  7 24  1  0
  5 23  1  0
  3 22  1  0
 11 26  1  0
 12 27  1  0
 14 28  1  0
 16 29  1  0
 17 30  1  0
M  CHG  1  18   1
M  END


  Mrv0541 02241221462D          

 20 22  0  0  0  0            999 V2000
   -2.1434    1.2375    0.0000 O   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
   -0.7145    1.2375    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
    0.0000    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
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   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
    1.4289    0.0000    0.0000 O   0  3  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  5  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
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 11 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
  9 20  2  0  0  0  0
M  CHG  1  10   1
M  END
> <DATABASE_ID>
NP0045244

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC2=[O+]C(=CC=C2C(O)=C1)C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O5/c16-9-6-12(18)10-2-4-14(20-15(10)7-9)8-1-3-11(17)13(19)5-8/h1-7H,(H3-,16,17,18,19)/p+1

> <INCHI_KEY>
GDNIGMNXEKGFIP-UHFFFAOYSA-O

> <FORMULA>
C15H11O5

> <MOLECULAR_WEIGHT>
271.2448

> <EXACT_MASS>
271.060648462

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
27.27934287380412

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1λ⁴-chromen-1-ylium

> <ALOGPS_LOGP>
2.50

> <JCHEM_LOGP>
3.3346999999999998

> <ALOGPS_LOGS>
-3.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.642200949760783

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.579730432589524

> <JCHEM_PKA_STRONGEST_BASIC>
-5.857312343323941

> <JCHEM_POLAR_SURFACE_AREA>
94.06

> <JCHEM_REFRACTIVITY>
82.1322

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.31e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
luteolinidin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+1
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    2    8                                                  
CONECT    8    7                                                            
CONECT    9    5   10   20                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   18                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   11   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19    9                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Value	Source
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-1-benzopyrylium(1+), 9ci	HMDB
5,7,3',4'-Tetrahydroxyflavylium	HMDB
Luteolidin	HMDB

Chemical Formula

C₁₅H₁₁O₅

Average Mass

271.2448 Da

Monoisotopic Mass

271.06065 Da

IUPAC Name

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1λ⁴-chromen-1-ylium

Traditional Name

luteolinidin

CAS Registry Number

1154-78-5

SMILES

OC1=CC2=[O+]C(=CC=C2C(O)=C1)C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C15H10O5/c16-9-6-12(18)10-2-4-14(20-15(10)7-9)8-1-3-11(17)13(19)5-8/h1-7H,(H3-,16,17,18,19)/p+1

InChI Key

GDNIGMNXEKGFIP-UHFFFAOYSA-O

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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Bryum cryophilum	-	KNApSAcK
Hyparrhenia filipendula	LOTUS Database	35616633
Rechsteineria cardinalis	Plant	KNApSAcK
Sinningia cardinalis	LOTUS Database	35616633
Zea mays L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-hydroxyflavonoids. These are flavonoids that bear one hydroxyl group at the C-7 position of the flavonoid skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Hydroxyflavonoids

Direct Parent

7-hydroxyflavonoids

Alternative Parents

Substituents

3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Anthocyanidin
1-benzopyran
Benzopyran
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Heteroaromatic compound
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

anthocyanidin cation (CHEBI:6584 )
Anthocyanidins and anthocyanins (C08652 )
a small molecule (CPD-11945 )

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	2.5	ALOGPS
logP	3.33	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	6.58	ChemAxon
pKa (Strongest Basic)	-5.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	94.06 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	82.13 m³·mol⁻¹	ChemAxon
Polarizability	27.28 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon