NP-MRD: Showing NP-Card for Apigeniflavan (NP0056022)

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Record Information

Version

2.0

Created at

2022-04-28 01:55:09 UTC

Updated at

2022-04-28 01:55:09 UTC

NP-MRD ID

NP0056022

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Apigeniflavan

Description

Apigeniflavan 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. Thus, apigeniflavan is considered to be a flavonoid. Apigeniflavan is found in Faramea guianensis . Apigeniflavan was first documented in 2015 (PMID: 25652784). Based on a literature review very few articles have been published on Apigeniflavan.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 35  0  0  0  0  0  0  0  0999 V2000
    6.0566    0.2484   -0.6383 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7012    0.1425   -0.3884 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8894    1.2406   -0.1750 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5378    1.0673    0.0704 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9453   -0.1705    0.1143 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4968   -0.2494    0.3832 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0662   -1.6303    0.1154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5142   -1.6349    0.4446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2398   -0.3988    0.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6372   -0.3360    0.2031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3267   -1.4731    0.6105 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3425    0.8110   -0.0997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6763    1.9441   -0.5040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4080    3.0746   -0.7996 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3078    1.8815   -0.5901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5806    0.7359   -0.2894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1990    0.7095   -0.3882 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7509   -1.2708   -0.0981 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1081   -1.1026   -0.3449 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7706    0.2471    0.0788 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3656    2.2139   -0.2114 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9257    1.9572    0.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3521   -0.0599    1.4743 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4690   -2.3161    0.8331 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1846   -2.0067   -0.8924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9811   -2.5032   -0.0962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6884   -1.8508    1.5386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8306   -2.3208    0.8362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4298    0.7653   -0.0015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6128    3.7581   -0.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7444    2.7426   -0.9019 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3000   -2.2396   -0.0662 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7316   -1.9762   -0.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5 18  1  0
 18 19  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 19  2  1  0
 17  6  1  0
 16  9  1  0
  1 20  1  0
  3 21  1  0
  4 22  1  0
 18 32  1  0
 19 33  1  0
  6 23  1  1
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
 11 28  1  0
 12 29  1  0
 14 30  1  0
 15 31  1  0
M  END


  Mrv1652304282203552D          

 19 21  0  0  1  0            999 V2000
   -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
    0.0000   -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
    0.7145   -0.4125    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
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  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
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    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    0.8250    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
    3.5724   -0.4125    0.0000 C   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
    0.0000   -2.4750    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
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
  8 11  1  6  0  0  0
 11 12  2  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
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 14 17  1  0  0  0  0
  3 18  1  0  0  0  0
  1 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0056022

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(C=C1)[C@@H]1CCC2=C(O)C=C(O)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O4/c16-10-3-1-9(2-4-10)14-6-5-12-13(18)7-11(17)8-15(12)19-14/h1-4,7-8,14,16-18H,5-6H2/t14-/m0/s1

> <INCHI_KEY>
MDDPZOZWEZNMTK-AWEZNQCLSA-N

> <FORMULA>
C15H14O4

> <MOLECULAR_WEIGHT>
258.273

> <EXACT_MASS>
258.089208931

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
26.490222024263694

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-5,7-diol

> <ALOGPS_LOGP>
2.29

> <JCHEM_LOGP>
3.1735759440000004

> <ALOGPS_LOGS>
-3.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.80096112576244

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.210459361059193

> <JCHEM_PKA_STRONGEST_BASIC>
-4.899742170443311

> <JCHEM_POLAR_SURFACE_AREA>
69.92

> <JCHEM_REFRACTIVITY>
70.6573

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.51e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
apigeniflavan

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    6   19                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   18                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4                                                       
CONECT   11    8   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17   14                                                            
CONECT   18    3                                                            
CONECT   19    1                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₄O₄

Average Mass

258.2730 Da

Monoisotopic Mass

258.08921 Da

IUPAC Name

(2S)-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-5,7-diol

Traditional Name

apigeniflavan

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C=C1)[C@@H]1CCC2=C(O)C=C(O)C=C2O1

InChI Identifier

InChI=1S/C15H14O4/c16-10-3-1-9(2-4-10)14-6-5-12-13(18)7-11(17)8-15(12)19-14/h1-4,7-8,14,16-18H,5-6H2/t14-/m0/s1

InChI Key

MDDPZOZWEZNMTK-AWEZNQCLSA-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, 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
Faramea guianensis	Plant	KNApSAcK

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

4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavan
1-benzopyran
Chromane
Benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
Monocyclic benzene moiety
Oxacycle
Organoheterocyclic compound
Ether
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavans, Flavanols and Leucoanthocyanidins (LMPK12020262 )

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	2.29	ALOGPS
logP	3.17	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.92 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	70.66 m³·mol⁻¹	ChemAxon
Polarizability	26.49 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00008753

Chemspider ID

24842655

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44257189

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Costa G, Gonzalez-Manzano S, Gonzalez-Paramas A, Figueiredo IV, Santos-Buelga C, Batista MT: Flavan hetero-dimers in the Cymbopogon citratus infusion tannin fraction and their contribution to the antioxidant activity. Food Funct. 2015 Mar;6(3):932-7. doi: 10.1039/c5fo00042d. [PubMed:25652784 ]

Showing NP-Card for Apigeniflavan (NP0056022)

MOL for NP0056022 (Apigeniflavan)

3D MOL for NP0056022 (Apigeniflavan)

3D SDF for NP0056022 (Apigeniflavan)

3D-SDF for NP0056022 (Apigeniflavan)

PDB for NP0056022 (Apigeniflavan)

3D PDB for NP0056022 (Apigeniflavan)

SMILES for NP0056022 (Apigeniflavan)

INCHI for NP0056022 (Apigeniflavan)

Structure for NP0056022 (Apigeniflavan)

3D Structure for NP0056022 (Apigeniflavan)