NP-MRD: Showing NP-Card for flavan (NP0174394)

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Record Information

Version

2.0

Created at

2022-09-03 11:38:21 UTC

Updated at

2022-09-03 11:38:21 UTC

NP-MRD ID

NP0174394

Secondary Accession Numbers

None

Natural Product Identification

Common Name

flavan

Description

Flavan belongs to the class of organic compounds known as flavans. Flavans are compounds containing a flavan moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran skeleton. A C-glycosidic flavan can be isolated from cocoa liquor. They may be found in plants. Flavan is an extremely weak basic (essentially neutral) compound (based on its pKa). Casuarina glauca is an actinorhizal plant producing root nitrogen-fixing nodules infested by Frankia. There is a regular pattern of cell layers containing flavans. The flavans are benzopyran derivatives that use the 2-phenyl-3,4-dihydro-2H-chromene skeleton. flavan is found in Morus alba. These compounds include the flavan-3-ols, flavan-4-ols and flavan-3,4-diols (leucoanthocyanidin).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 32  0  0  0  0  0  0  0  0999 V2000
    4.2765    0.8375    0.1398 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1648   -0.4369   -0.3993 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9166   -0.9827   -0.6137 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7504   -0.3203   -0.3167 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4573   -0.9608   -0.5708 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0462   -1.5898    0.6984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9123   -0.6805    1.5194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9607   -0.0513    0.6518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1945    0.2698    1.1732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1937    0.8519    0.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9369    1.1176   -0.9220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7079    0.8044   -1.4656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7144    0.2181   -0.6793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4779   -0.1077   -1.1871 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8628    0.9519    0.2215 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1028    1.5107    0.4415 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2397    1.2725    0.3111 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0776   -0.9981   -0.6499 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9151   -1.9962   -1.0437 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6109   -1.8121   -1.2975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6138   -2.5213    0.4604 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8581   -1.8540    1.3100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3609    0.0612    2.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4394   -1.3362    2.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3749    0.0530    2.2199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1709    1.0985    0.8512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7319    1.5735   -1.5025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5117    1.0167   -2.5179 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9446    1.4992    0.4663 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1706    2.5113    0.8651 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14  5  1  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  2  0
  1 16  1  0
 16 15  2  0
  5  6  1  0
 15  4  1  0
 13  8  1  0
  6 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
  5 20  1  6
  3 19  1  0
  2 18  1  0
  1 17  1  0
 16 30  1  0
 15 29  1  0
M  END


  Mrv1533004261502282D          

 16 18  0  0  0  0            999 V2000
    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 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
    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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   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
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    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  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
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  1 10  1  0  0  0  0
 10 11  1  0  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
M  END
> <DATABASE_ID>
NP0174394

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C1CC2=CC=CC=C2OC1C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O/c1-2-6-12(7-3-1)15-11-10-13-8-4-5-9-14(13)16-15/h1-9,15H,10-11H2

> <INCHI_KEY>
QOLIPNRNLBQTAU-UHFFFAOYSA-N

> <FORMULA>
C15H14O

> <MOLECULAR_WEIGHT>
210.276

> <EXACT_MASS>
210.104465071

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
24.216669922348917

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-phenyl-3,4-dihydro-2H-1-benzopyran

> <ALOGPS_LOGP>
4.39

> <JCHEM_LOGP>
4.084271909

> <ALOGPS_LOGS>
-4.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.8774452328580145

> <JCHEM_POLAR_SURFACE_AREA>
9.23

> <JCHEM_REFRACTIVITY>
64.71460000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.13e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
flavan

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2   10                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9    1   11                                                  
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

View in JSmol

Synonyms

Value	Source
3,4-Dihydro-2-phenyl-2H-1-benzopyran	ChEBI

Chemical Formula

C₁₅H₁₄O

Average Mass

210.2760 Da

Monoisotopic Mass

210.10447 Da

IUPAC Name

2-phenyl-3,4-dihydro-2H-1-benzopyran

Traditional Name

flavan

CAS Registry Number

Not Available

SMILES

C1CC2=CC=CC=C2OC1C1=CC=CC=C1

InChI Identifier

InChI=1S/C15H14O/c1-2-6-12(7-3-1)15-11-10-13-8-4-5-9-14(13)16-15/h1-9,15H,10-11H2

InChI Key

QOLIPNRNLBQTAU-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
Morus alba	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavans. Flavans are compounds containing a flavan moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Flavans

Alternative Parents

Substituents

Flavan
1-benzopyran
Benzopyran
Chromane
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

flavans (CHEBI:38691 )
a flavanoid (CPD-13729 )

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	4.39	ALOGPS
logP	4.08	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	9.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	64.71 m³·mol⁻¹	ChemAxon
Polarizability	24.22 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

CPD-13729

BiGG ID

Not Available

Wikipedia Link

Flavan

METLIN ID

Not Available

PubChem Compound

94156

PDB ID

Not Available

ChEBI ID

38691

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for flavan (NP0174394)

MOL for NP0174394 (flavan)

3D MOL for NP0174394 (flavan)

3D SDF for NP0174394 (flavan)

3D-SDF for NP0174394 (flavan)

PDB for NP0174394 (flavan)

3D PDB for NP0174394 (flavan)

SMILES for NP0174394 (flavan)

INCHI for NP0174394 (flavan)

Structure for NP0174394 (flavan)

3D Structure for NP0174394 (flavan)