NP-MRD: Showing NP-Card for Procyanidin A1 (NP0137384)

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Record Information

Version

2.0

Created at

2022-05-30 16:50:55 UTC

Updated at

2022-05-30 16:50:55 UTC

NP-MRD ID

NP0137384

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Procyanidin A1

Description

Procyanidin A1 is found in Aesculus hippocastanum, Ceratiola ericoides, Cinchona pubescens, Cinnamomum aromaticum, Crataegus sinaica, Cupania latifolia, Dimocarpus longan, Garcinia mangostana, Ixora coccinea, Litchi chinensis, Lupinus angustifolius, Parameria laevigata, Paullinia cupana, Pavetta owariensis, Prunus spinosa, Rhododendron spiciferum, Rumex acetosa and Vaccinium vitis-idaea.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241216392D          

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M  END

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  Mrv0541 02241216392D          

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  2  7  1  0  0  0  0
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  3 10  1  0  0  0  0
  4  5  1  0  0  0  0
  4 18  1  0  0  0  0
  5  6  2  0  0  0  0
  6 19  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 11  1  0  0  0  0
  9 10  1  0  0  0  0
  9 17  1  0  0  0  0
 11 12  2  0  0  0  0
 11 16  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 41  1  0  0  0  0
 15 16  2  0  0  0  0
 15 42  1  0  0  0  0
 19 27  1  0  0  0  0
 20 21  2  0  0  0  0
 20 25  1  0  0  0  0
 21 22  1  0  0  0  0
 21 26  1  0  0  0  0
 22 23  2  0  0  0  0
 22 29  1  0  0  0  0
 23 24  1  0  0  0  0
 23 37  1  0  0  0  0
 24 25  2  0  0  0  0
 25 38  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 30  1  0  0  0  0
 28 29  1  0  0  0  0
 28 36  1  0  0  0  0
 30 31  2  0  0  0  0
 30 35  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 33 39  1  0  0  0  0
 34 35  2  0  0  0  0
 34 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137384

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1CC2=C(O)C=C3OC4(OC5=CC(O)=CC(O)=C5C(C4O)C3=C2OC1C1=CC=C(O)C(O)=C1)C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H24O12/c31-13-7-20(37)24-22(8-13)41-30(12-2-4-16(33)19(36)6-12)29(39)26(24)25-23(42-30)10-17(34)14-9-21(38)27(40-28(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,21,26-27,29,31-39H,9H2

> <INCHI_KEY>
NSEWTSAADLNHNH-UHFFFAOYSA-N

> <FORMULA>
C30H24O12

> <MOLECULAR_WEIGHT>
576.5044

> <EXACT_MASS>
576.126776232

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
56.77277359515675

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5,13-bis(3,4-dihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol

> <ALOGPS_LOGP>
2.43

> <JCHEM_LOGP>
3.590532096666666

> <ALOGPS_LOGS>
-3.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.10475378074171

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.663185265721914

> <JCHEM_PKA_STRONGEST_BASIC>
-3.877330901014532

> <JCHEM_POLAR_SURFACE_AREA>
209.75999999999996

> <JCHEM_REFRACTIVITY>
144.1963000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.27e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
proanthocyanidin A2

> <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  C   UNK     0       2.676  -0.308   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.676  -1.848   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.008  -2.618   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.338  -1.848   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.338  -0.308   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.008   0.460   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.341  -2.618   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.341  -4.161   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.676  -4.934   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.008  -4.161   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.007  -4.931   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.328  -4.164   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.661  -4.931   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.661  -6.471   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.328  -7.242   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.007  -6.471   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.676  -6.474   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.673  -2.618   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.008   2.000   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -4.365   2.110   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.825   2.108   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.058   0.778   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.825  -0.555   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.365  -0.552   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.133   0.775   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.058   3.443   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -0.512   3.440   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.258   2.108   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.512   0.775   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.255   4.777   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.510   6.112   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.255   7.444   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.798   7.447   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.568   6.109   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.796   4.780   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       1.801   1.594   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -2.058  -1.889   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -6.673   0.778   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       2.568   8.782   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       4.108   6.107   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -3.995  -7.242   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      -1.328  -8.782   0.000  0.00  0.00           O+0
CONECT    1    2    6   29                                                  
CONECT    2    1    3    7                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5   18                                                  
CONECT    5    4    6                                                       
CONECT    6    1    5   19                                                  
CONECT    7    2    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10   17                                                  
CONECT   10    3    9                                                       
CONECT   11    8   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   41                                                  
CONECT   15   14   16   42                                                  
CONECT   16   11   15                                                       
CONECT   17    9                                                            
CONECT   18    4                                                            
CONECT   19    6   27                                                       
CONECT   20   21   25                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23   29                                                  
CONECT   23   22   24   37                                                  
CONECT   24   23   25                                                       
CONECT   25   20   24   38                                                  
CONECT   26   21   27                                                       
CONECT   27   19   26   28   30                                             
CONECT   28   27   29   36                                                  
CONECT   29    1   22   28                                                  
CONECT   30   27   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   39                                                  
CONECT   34   33   35   40                                                  
CONECT   35   30   34                                                       
CONECT   36   28                                                            
CONECT   37   23                                                            
CONECT   38   25                                                            
CONECT   39   33                                                            
CONECT   40   34                                                            
CONECT   41   14                                                            
CONECT   42   15                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   96    0
END

View in JSmol

Synonyms

Value	Source
Proanthocyanidin a2	MeSH

Chemical Formula

C₃₀H₂₄O₁₂

Average Mass

576.5044 Da

Monoisotopic Mass

576.12678 Da

IUPAC Name

5,13-bis(3,4-dihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol

Traditional Name

proanthocyanidin A2

CAS Registry Number

Not Available

SMILES

OC1CC2=C(O)C=C3OC4(OC5=CC(O)=CC(O)=C5C(C4O)C3=C2OC1C1=CC=C(O)C(O)=C1)C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C30H24O12/c31-13-7-20(37)24-22(8-13)41-30(12-2-4-16(33)19(36)6-12)29(39)26(24)25-23(42-30)10-17(34)14-9-21(38)27(40-28(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,21,26-27,29,31-39H,9H2

InChI Key

NSEWTSAADLNHNH-UHFFFAOYSA-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
Aesculus hippocastanum	LOTUS Database	35616633
Ceratiola ericoides	LOTUS Database	35616633
Cinchona pubescens	LOTUS Database	35616633
Cinnamomum aromaticum	LOTUS Database	35616633
Crataegus sinaica	LOTUS Database	35616633
Cupania latifolia	LOTUS Database	35616633
Dimocarpus longan	LOTUS Database	35616633
Garcinia mangostana	LOTUS Database	35616633
Ixora coccinea	LOTUS Database	35616633
Litchi chinensis	LOTUS Database	35616633
Lupinus angustifolius	LOTUS Database	35616633
Parameria laevigata	LOTUS Database	35616633
Paullinia cupana	LOTUS Database	35616633
Pavetta owariensis	LOTUS Database	35616633
Prunus spinosa	LOTUS Database	35616633
Rhododendron spiciferum	LOTUS Database	35616633
Rumex acetosa	LOTUS Database	35616633
Vaccinium vitis-idaea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Biflavonoids and polyflavonoids

Direct Parent

Biflavonoids and polyflavonoids

Alternative Parents

Substituents

A-type proanthocyanidin
Bi- and polyflavonoid skeleton
Proanthocyanidin
Catechin
Pyranoflavonoid
Flavan-3-ol
Hydroxyflavonoid
3'-hydroxyflavonoid
7-hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
3-hydroxyflavonoid
Flavan
Pyranochromene
Chromane
1-benzopyran
Benzopyran
Catechol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Ketal
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Polyol
Acetal
Organoheterocyclic compound
Oxacycle
Ether
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organooxygen compound
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	2.43	ALOGPS
logP	3.59	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	8.66	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	209.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	144.2 m³·mol⁻¹	ChemAxon
Polarizability	56.77 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

FDB016777

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Procyanidin A1

METLIN ID

Not Available

PubChem Compound

5089889

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Procyanidin A1 (NP0137384)

MOL for NP0137384 (Procyanidin A1)

3D MOL for NP0137384 (Procyanidin A1)

3D SDF for NP0137384 (Procyanidin A1)

3D-SDF for NP0137384 (Procyanidin A1)

PDB for NP0137384 (Procyanidin A1)

3D PDB for NP0137384 (Procyanidin A1)

SMILES for NP0137384 (Procyanidin A1)

INCHI for NP0137384 (Procyanidin A1)

Structure for NP0137384 (Procyanidin A1)

3D Structure for NP0137384 (Procyanidin A1)