NP-MRD: Showing NP-Card for (+)-Tephrorin B (NP0060530)

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Record Information

Version

2.0

Created at

2022-04-28 05:33:45 UTC

Updated at

2022-04-28 05:33:45 UTC

NP-MRD ID

NP0060530

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Tephrorin B

Description

(+)-Tephrorin B belongs to the class of organic compounds known as 8-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 8-position. Thus, (+)-tephrorin b is considered to be a flavonoid (+)-tephrorin B is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (+)-Tephrorin B is found in Tephrosia purpurea . Based on a literature review very few articles have been published on (+)-tephrorin B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282207332D          

 36 40  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304282207332D          

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  1 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0060530

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)OC[C@@H]([C@@H]1OC(=O)\C=C\C1=CC=CC=C1)C1=C(O)C=CC2=C1O[C@@H](CC2=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H28O6/c1-30(2)29(36-26(33)16-13-19-9-5-3-6-10-19)22(18-34-30)27-23(31)15-14-21-24(32)17-25(35-28(21)27)20-11-7-4-8-12-20/h3-16,22,25,29,31H,17-18H2,1-2H3/b16-13+/t22-,25+,29+/m1/s1

> <INCHI_KEY>
QBEVDWJGVNNOGT-NTWNTOQNSA-N

> <FORMULA>
C30H28O6

> <MOLECULAR_WEIGHT>
484.548

> <EXACT_MASS>
484.188588622

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
51.13360256769787

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,4S)-4-[(2S)-7-hydroxy-4-oxo-2-phenyl-3,4-dihydro-2H-1-benzopyran-8-yl]-2,2-dimethyloxolan-3-yl (2E)-3-phenylprop-2-enoate

> <ALOGPS_LOGP>
5.40

> <JCHEM_LOGP>
5.545812109333333

> <ALOGPS_LOGS>
-5.51

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.97523915146489

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.569508186258286

> <JCHEM_PKA_STRONGEST_BASIC>
-4.116241064187479

> <JCHEM_POLAR_SURFACE_AREA>
82.06

> <JCHEM_REFRACTIVITY>
136.27750000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.49e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+)-tephrorin B

> <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  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -3.080   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       1.334  -0.770   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       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.335  -3.080   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  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.246  -5.525   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.770  -6.990   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.770  -6.990   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.246  -5.525   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.711  -5.049   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -3.855  -6.080   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -3.535  -7.586   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -5.320  -5.604   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -6.464  -6.634   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -7.929  -6.158   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -9.073  -7.189   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -10.538  -6.713   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -10.858  -5.207   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -9.713  -4.176   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -8.249  -4.652   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.947  -8.520   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.170  -7.631   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2    6   36                                                  
CONECT    2    1    3   18                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10    3                                                       
CONECT   12   10   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18    2   19   22                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   34   35                                             
CONECT   22   21   18   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   28                                                       
CONECT   34   21                                                            
CONECT   35   21                                                            
CONECT   36    1                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Value	Source
(3S,4S)-4-[(2S)-3,4-Dihydro-7-hydroxy-4-oxo-2-phenyl-2H-1-benzopyran-8-yl]tetrahydro-2,2-dimethyl-3-furanyl(2E)-3-phenyl-2-propenoate	ChEBI
(3S,4S)-4-[(2S)-3,4-Dihydro-7-hydroxy-4-oxo-2-phenyl-2H-1-benzopyran-8-yl]tetrahydro-2,2-dimethyl-3-furanyl(2E)-3-phenyl-2-propenoic acid	Generator

Chemical Formula

C₃₀H₂₈O₆

Average Mass

484.5480 Da

Monoisotopic Mass

484.18859 Da

IUPAC Name

(3S,4S)-4-[(2S)-7-hydroxy-4-oxo-2-phenyl-3,4-dihydro-2H-1-benzopyran-8-yl]-2,2-dimethyloxolan-3-yl (2E)-3-phenylprop-2-enoate

Traditional Name

(+)-tephrorin B

CAS Registry Number

Not Available

SMILES

CC1(C)OC[C@@H]([C@@H]1OC(=O)\C=C\C1=CC=CC=C1)C1=C(O)C=CC2=C1O[C@@H](CC2=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C30H28O6/c1-30(2)29(36-26(33)16-13-19-9-5-3-6-10-19)22(18-34-30)27-23(31)15-14-21-24(32)17-25(35-28(21)27)20-11-7-4-8-12-20/h3-16,22,25,29,31H,17-18H2,1-2H3/b16-13+/t22-,25+,29+/m1/s1

InChI Key

QBEVDWJGVNNOGT-NTWNTOQNSA-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
Tephrosia purpurea	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 8-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 8-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

8-prenylated flavanones

Alternative Parents

Substituents

8-prenylated flavanone
7-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Cinnamic acid or derivatives
Cinnamic acid ester
Chromone
Chromane
Benzopyran
1-benzopyran
Styrene
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Benzenoid
Monocyclic benzene moiety
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Tetrahydrofuran
Enoate ester
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Carboxylic acid derivative
Ether
Oxacycle
Dialkyl ether
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

cinnamate ester (CHEBI:66200 )
oxolanes (CHEBI:66200 )
monohydroxyflavanone (CHEBI:66200 )
Flavanones (LMPK12140009 )

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	5.4	ALOGPS
logP	5.55	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	7.57	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	82.06 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	136.28 m³·mol⁻¹	ChemAxon
Polarizability	51.13 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

8800084

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10624721

PDB ID

Not Available

ChEBI ID

66200

Good Scents ID

Not Available

References

General References

Showing NP-Card for (+)-Tephrorin B (NP0060530)

MOL for NP0060530 ((+)-Tephrorin B)

3D MOL for NP0060530 ((+)-Tephrorin B)

3D SDF for NP0060530 ((+)-Tephrorin B)

3D-SDF for NP0060530 ((+)-Tephrorin B)

PDB for NP0060530 ((+)-Tephrorin B)

3D PDB for NP0060530 ((+)-Tephrorin B)

SMILES for NP0060530 ((+)-Tephrorin B)

INCHI for NP0060530 ((+)-Tephrorin B)

Structure for NP0060530 ((+)-Tephrorin B)

3D Structure for NP0060530 ((+)-Tephrorin B)