NP-MRD: Showing NP-Card for Leucodelphinidin (NP0049251)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-03-17 21:09:29 UTC

Updated at

2022-03-17 21:09:29 UTC

NP-MRD ID

NP0049251

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Leucodelphinidin

Description

2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4,5,7-tetrol, also known as 3,4,5,7,3',4',5'-heptahydroxyflavan or leucoanthocyanidin, belongs to the class of organic compounds known as epigallocatechins. Epigallocatechins are compounds containing epigallocatechin or a derivative. Epigallocatechin is a flavan-3-ol containing a benzopyran-3,5,7-triol linked to a 3,4,5-hydroxyphenyl moiety. 2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4,5,7-tetrol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4,5,7-tetrol has been detected, but not quantified in, several different foods, such as teffs, arctic blackberries, alaska blueberries, salmonberries, and guava. This could make 2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4,5,7-tetrol a potential biomarker for the consumption of these foods. Leucodelphinidin is found in Alhagi maurorum , Caesalpinia pulcherrima , Cleistanthus collinus, Ephedra sinica , Eucalyptus pilularis, Euscaphis konishii, Gentiana lutea L. var. aurantiaca , Gossypium hirsutum, Hypocalyptus sophoroides, Koenigia coriaria, Medicago truncatula, Nympaea spp., Petunia hybrida, Punica granatum L. , Rumex hymenosepalus, Taxus chinensis, Taxus fuana, Taxus yunnanensis and Terminalia elliptica. A flavanol that is 3,4-dihydro-2H-chromene which is substituted at positions 3, 4, 5, and 7 by hydroxy groups, and at position 2 by a 3,4,5-trihydroxyphenyl group.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309181719392D          

 23 25  0  0  0  0            999 V2000
    2.8579    0.8250    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
   -0.7145   -1.2375    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
    2.8579    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
    0.0000   -1.6500    0.0000 C   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
    4.2868    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    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
    2.1434   -1.2375    0.0000 C   0  0  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
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  2  0  0  0  0
  5  2  1  0  0  0  0
  6  3  2  0  0  0  0
  6  4  1  0  0  0  0
  7  3  1  0  0  0  0
  8  1  1  0  0  0  0
  9  2  2  0  0  0  0
 10  4  2  0  0  0  0
 11  7  2  0  0  0  0
 11 10  1  0  0  0  0
 12  8  2  0  0  0  0
 12  9  1  0  0  0  0
 13 11  1  0  0  0  0
 14 13  1  0  0  0  0
 15  5  1  0  0  0  0
 15 14  1  0  0  0  0
 16  6  1  0  0  0  0
 17  7  1  0  0  0  0
 18  8  1  0  0  0  0
 19  9  1  0  0  0  0
 20 12  1  0  0  0  0
 21 13  1  0  0  0  0
 22 14  1  0  0  0  0
 23 10  1  0  0  0  0
 23 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049251

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1C(O)C2=C(O)C=C(O)C=C2OC1C1=CC(O)=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O8/c16-6-3-7(17)11-10(4-6)23-15(14(22)13(11)21)5-1-8(18)12(20)9(19)2-5/h1-4,13-22H

> <INCHI_KEY>
ZEACOKJOQLAYTD-UHFFFAOYSA-N

> <FORMULA>
C15H14O8

> <MOLECULAR_WEIGHT>
322.2669

> <EXACT_MASS>
322.068867424

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
30.536648402962687

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4,5,7-tetrol

> <ALOGPS_LOGP>
0.40

> <JCHEM_LOGP>
0.5725455466666667

> <ALOGPS_LOGS>
-2.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.413963364060358

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.699021481287094

> <JCHEM_PKA_STRONGEST_BASIC>
-3.696693299000584

> <JCHEM_POLAR_SURFACE_AREA>
150.84

> <JCHEM_REFRACTIVITY>
77.1881

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.53e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
leucodelphinidin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-SEP-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-SEP-17         0                                  
HETATM    1  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668  -0.770   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   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   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       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1    5    8                                                       
CONECT    2    5    9                                                       
CONECT    3    6    7                                                       
CONECT    4    6   10                                                       
CONECT    5    1    2   15                                                  
CONECT    6    3    4   16                                                  
CONECT    7    3   11   17                                                  
CONECT    8    1   12   18                                                  
CONECT    9    2   12   19                                                  
CONECT   10    4   11   23                                                  
CONECT   11    7   10   13                                                  
CONECT   12    8    9   20                                                  
CONECT   13   11   14   21                                                  
CONECT   14   13   15   22                                                  
CONECT   15    5   14   23                                                  
CONECT   16    6                                                            
CONECT   17    7                                                            
CONECT   18    8                                                            
CONECT   19    9                                                            
CONECT   20   12                                                            
CONECT   21   13                                                            
CONECT   22   14                                                            
CONECT   23   10   15                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Value	Source
3,4,5,7,3',4',5'-Heptahydroxyflavan	ChEBI
Leucoanthocyanidin	ChEBI
Leucodelphinidin	ChEBI
Leucoefdin	ChEBI
Leucoephdine	ChEBI
Leukoefdin	ChEBI
Leukoephdin	ChEBI

Chemical Formula

C₁₅H₁₄O₈

Average Mass

322.2669 Da

Monoisotopic Mass

322.06887 Da

IUPAC Name

2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4,5,7-tetrol

Traditional Name

leucodelphinidin

CAS Registry Number

491-52-1

SMILES

OC1C(O)C2=C(O)C=C(O)C=C2OC1C1=CC(O)=C(O)C(O)=C1

InChI Identifier

InChI=1S/C15H14O8/c16-6-3-7(17)11-10(4-6)23-15(14(22)13(11)21)5-1-8(18)12(20)9(19)2-5/h1-4,13-22H

InChI Key

ZEACOKJOQLAYTD-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Alhagi maurorum	Plant	KNApSAcK
Arachis hypogaea	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Caesalpinia pulcherrima	Plant	KNApSAcK
Ceratonia siliqua	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cleistanthus collinus	Plant	KNApSAcK
Ephedra sinica	Plant	KNApSAcK
Eucalyptus pilularis	Plant	KNApSAcK
Euscaphis konishii	Plant	KNApSAcK
Gentiana lutea L. var. aurantiaca	Plant	KNApSAcK
Gossypium hirsutum	LOTUS Database	35616633
Hippophae rhamnoides	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Hypocalyptus sophoroides	Plant	KNApSAcK
Koenigia coriaria	LOTUS Database	35616633
Medicago truncatula	Plant	KNApSAcK
Musa x paradisiaca	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Nelumbo nucifera	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Nympaea spp.	-	KNApSAcK
Petunia hybrida	LOTUS Database	35616633
Punica granatum	Plant	KNApSAcK
Rumex hymenosepalus	Plant	KNApSAcK
Taxus chinensis	Plant	KNApSAcK
Taxus fuana	Plant	KNApSAcK
Taxus wallichiana var. yunnanensis	Plant	KNApSAcK
Terminalia elliptica	LOTUS Database	35616633
Vicia faba	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as epigallocatechins. Epigallocatechins are compounds containing epigallocatechin or a derivative. Epigallocatechin is a flavan-3-ol containing a benzopyran-3,5,7-triol linked to a 3,4,5-hydroxyphenyl moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Epigallocatechins

Alternative Parents

Substituents

Epigallocatechin
Leucoanthocyanidin-skeleton
7-hydroxyflavonoid
Hydroxyflavonoid
5-hydroxyflavonoid
4-hydroxyflavonoid
4'-hydroxyflavonoid
3-hydroxyflavonoid
3'-hydroxyflavonoid
Chromane
1-benzopyran
Benzopyran
Pyrogallol derivative
Benzenetriol
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Secondary alcohol
1,2-diol
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

secondary alcohol (CHEBI:71216 )
catechols (CHEBI:71216 )
polyphenol (CHEBI:71216 )
resorcinols (CHEBI:71216 )
glycol (CHEBI:71216 )
hydroxyflavan (CHEBI:71216 )
a leucoanthocyanidin (CPD-7088 )

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	0.4	ALOGPS
logP	0.57	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	8.7	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	150.84 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	77.19 m³·mol⁻¹	ChemAxon
Polarizability	30.54 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

HMDB0136090

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB018307

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Leucodelphinidin

METLIN ID

Not Available

PubChem Compound

3081374

PDB ID

Not Available

ChEBI ID

71216

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Leucodelphinidin (NP0049251)

MOL for NP0049251 (Leucodelphinidin)

3D MOL for NP0049251 (Leucodelphinidin)

3D SDF for NP0049251 (Leucodelphinidin)

3D-SDF for NP0049251 (Leucodelphinidin)

PDB for NP0049251 (Leucodelphinidin)

3D PDB for NP0049251 (Leucodelphinidin)

SMILES for NP0049251 (Leucodelphinidin)

INCHI for NP0049251 (Leucodelphinidin)

Structure for NP0049251 (Leucodelphinidin)

3D Structure for NP0049251 (Leucodelphinidin)