NP-MRD: Showing NP-Card for (S)-2',3',6'-Trihydroxy-8-prenyl-5'-(2,4-dihydroxyphenyl)-6'',6''-dimethylpyrano[2'',3'':7,6]flavanone (NP0060502)

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Record Information

Version

2.0

Created at

2022-04-28 05:32:32 UTC

Updated at

2022-04-28 05:32:33 UTC

NP-MRD ID

NP0060502

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(S)-2',3',6'-Trihydroxy-8-prenyl-5'-(2,4-dihydroxyphenyl)-6'',6''-dimethylpyrano[2'',3'':7,6]flavanone

Description

Eriosemaone C 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, eriosemaone C is considered to be a flavonoid. Eriosemaone C 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. (S)-2',3',6'-Trihydroxy-8-prenyl-5'-(2,4-dihydroxyphenyl)-6'',6''-dimethylpyrano[2'',3'':7,6]flavanone is found in Eriosema tuberosum and Trypanosoma brucei. Based on a literature review very few articles have been published on eriosemaone C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282207322D          

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M  END

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  Mrv1652304282207322D          

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  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 10 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 19 23  1  0  0  0  0
  9 24  1  0  0  0  0
  2 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
  1 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 26 32  1  0  0  0  0
 31 33  1  0  0  0  0
 31 34  1  0  0  0  0
 25 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0060502

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C2OC(C)(C)C=CC2=CC2=C1O[C@@H](CC2=O)C1=C(O)C(=CC(O)=C1O)C1=CC=C(O)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C31H30O8/c1-15(2)5-7-19-29-16(9-10-31(3,4)39-29)11-21-23(34)14-25(38-30(19)21)26-27(36)20(13-24(35)28(26)37)18-8-6-17(32)12-22(18)33/h5-6,8-13,25,32-33,35-37H,7,14H2,1-4H3/t25-/m0/s1

> <INCHI_KEY>
XFFLLCTVQRLAND-VWLOTQADSA-N

> <FORMULA>
C31H30O8

> <MOLECULAR_WEIGHT>
530.573

> <EXACT_MASS>
530.194067926

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
54.664282542435785

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5S)-13,13-dimethyl-2-(3-methylbut-2-en-1-yl)-5-{2,2',4,4',5-pentahydroxy-[1,1'-biphenyl]-3-yl}-4,14-dioxatricyclo[8.4.0.0^{3,8}]tetradeca-1,3(8),9,11-tetraen-7-one

> <ALOGPS_LOGP>
4.84

> <JCHEM_LOGP>
5.854393170333332

> <ALOGPS_LOGS>
-5.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.232472369651653

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.539810987658106

> <JCHEM_PKA_STRONGEST_BASIC>
-4.642715926047493

> <JCHEM_POLAR_SURFACE_AREA>
136.68

> <JCHEM_REFRACTIVITY>
149.02400000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.51e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5S)-13,13-dimethyl-2-(3-methylbut-2-en-1-yl)-5-{2,2',4,4',5-pentahydroxy-[1,1'-biphenyl]-3-yl}-4,14-dioxatricyclo[8.4.0.0^{3,8}]tetradeca-1,3(8),9,11-tetraen-7-one

> <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       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      10.669  -0.000   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      13.337   1.540   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.336   8.470   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.669   9.240   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.003   8.470   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.003   6.930   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      13.337   6.160   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      10.669  10.780   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -1.539   1.594   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.816   2.846   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
CONECT    1    2    6   28                                                  
CONECT    2    1    3   25                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    4    9   13                                                  
CONECT    9    8   10   24                                                  
CONECT   10    9   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12    8   14                                                  
CONECT   14   13                                                            
CONECT   15   12                                                            
CONECT   16   10   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   23                                                  
CONECT   20   19   21                                                       
CONECT   21   20   16   22                                                  
CONECT   22   21                                                            
CONECT   23   19                                                            
CONECT   24    9                                                            
CONECT   25    2   26   35                                                  
CONECT   26   25   27   32                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27    1                                                       
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33   34                                             
CONECT   32   31   26                                                       
CONECT   33   31                                                            
CONECT   34   31                                                            
CONECT   35   25   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

Value	Source
(S)-2',3',6'-Trihydroxy-8-prenyl-5'-(2,4-dihydroxyphenyl)-6'',6''-dimethylpyrano[2'',3'':7,6]flavanone	ChEBI

Chemical Formula

C₃₁H₃₀O₈

Average Mass

530.5730 Da

Monoisotopic Mass

530.19407 Da

IUPAC Name

(5S)-13,13-dimethyl-2-(3-methylbut-2-en-1-yl)-5-{2,2',4,4',5-pentahydroxy-[1,1'-biphenyl]-3-yl}-4,14-dioxatricyclo[8.4.0.0^{3,8}]tetradeca-1,3(8),9,11-tetraen-7-one

Traditional Name

(5S)-13,13-dimethyl-2-(3-methylbut-2-en-1-yl)-5-{2,2',4,4',5-pentahydroxy-[1,1'-biphenyl]-3-yl}-4,14-dioxatricyclo[8.4.0.0^{3,8}]tetradeca-1,3(8),9,11-tetraen-7-one

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=C2OC(C)(C)C=CC2=CC2=C1O[C@@H](CC2=O)C1=C(O)C(=CC(O)=C1O)C1=CC=C(O)C=C1O

InChI Identifier

InChI=1S/C31H30O8/c1-15(2)5-7-19-29-16(9-10-31(3,4)39-29)11-21-23(34)14-25(38-30(19)21)26-27(36)20(13-24(35)28(26)37)18-8-6-17(32)12-22(18)33/h5-6,8-13,25,32-33,35-37H,7,14H2,1-4H3/t25-/m0/s1

InChI Key

XFFLLCTVQRLAND-VWLOTQADSA-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
Eriosema tuberosum	Plant	KNApSAcK
Trypanosoma brucei	LOTUS Database	35616633

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
Pyranoflavonoid
3'-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Monohydroxyflavonoid
Biphenol
Pyranochromene
Biphenyl
2,2-dimethyl-1-benzopyran
Chromone
Chromane
Benzopyran
1-benzopyran
Hydroxyquinol derivative
Aryl alkyl ketone
Aryl ketone
Resorcinol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Ketone
Organoheterocyclic compound
Ether
Oxacycle
Polyol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

resorcinols (CHEBI:73778 )
trihydroxyflavanone (CHEBI:73778 )
extended flavonoid (CHEBI:73778 )
pyranochromane (CHEBI:73778 )
Flavanones (LMPK12140004 )

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	4.84	ALOGPS
logP	5.85	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	8.54	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	136.68 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	149.02 m³·mol⁻¹	ChemAxon
Polarizability	54.66 Å³	ChemAxon
Number of Rings	5	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

Not Available

KNApSAcK ID

C00014262

Chemspider ID

8635071

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10459657

PDB ID

Not Available

ChEBI ID

73778

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (S)-2',3',6'-Trihydroxy-8-prenyl-5'-(2,4-dihydroxyphenyl)-6'',6''-dimethylpyrano[2'',3'':7,6]flavanone (NP0060502)

MOL for NP0060502 ((S)-2',3',6'-Trihydroxy-8-prenyl-5'-(2,4-dihydroxyphenyl)-6'',6''-dimethylpyrano[2'',3'':7,6]flavanone)

3D MOL for NP0060502 ((S)-2',3',6'-Trihydroxy-8-prenyl-5'-(2,4-dihydroxyphenyl)-6'',6''-dimethylpyrano[2'',3'':7,6]flavanone)

3D SDF for NP0060502 ((S)-2',3',6'-Trihydroxy-8-prenyl-5'-(2,4-dihydroxyphenyl)-6'',6''-dimethylpyrano[2'',3'':7,6]flavanone)

3D-SDF for NP0060502 ((S)-2',3',6'-Trihydroxy-8-prenyl-5'-(2,4-dihydroxyphenyl)-6'',6''-dimethylpyrano[2'',3'':7,6]flavanone)

PDB for NP0060502 ((S)-2',3',6'-Trihydroxy-8-prenyl-5'-(2,4-dihydroxyphenyl)-6'',6''-dimethylpyrano[2'',3'':7,6]flavanone)

3D PDB for NP0060502 ((S)-2',3',6'-Trihydroxy-8-prenyl-5'-(2,4-dihydroxyphenyl)-6'',6''-dimethylpyrano[2'',3'':7,6]flavanone)

SMILES for NP0060502 ((S)-2',3',6'-Trihydroxy-8-prenyl-5'-(2,4-dihydroxyphenyl)-6'',6''-dimethylpyrano[2'',3'':7,6]flavanone)

INCHI for NP0060502 ((S)-2',3',6'-Trihydroxy-8-prenyl-5'-(2,4-dihydroxyphenyl)-6'',6''-dimethylpyrano[2'',3'':7,6]flavanone)

Structure for NP0060502 ((S)-2',3',6'-Trihydroxy-8-prenyl-5'-(2,4-dihydroxyphenyl)-6'',6''-dimethylpyrano[2'',3'':7,6]flavanone)

3D Structure for NP0060502 ((S)-2',3',6'-Trihydroxy-8-prenyl-5'-(2,4-dihydroxyphenyl)-6'',6''-dimethylpyrano[2'',3'':7,6]flavanone)