NP-MRD: Showing NP-Card for 6-[7-hydroxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-3-yl]-2,2-dimethylchromen-5-ol (NP0304399)

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Record Information

Version

2.0

Created at

2022-09-10 19:27:39 UTC

Updated at

2022-09-10 19:27:39 UTC

NP-MRD ID

NP0304399

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-[7-hydroxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-3-yl]-2,2-dimethylchromen-5-ol

Description

(S)-8-Prenylphaseollinisoflavan belongs to the class of organic compounds known as pyranoisoflavonoids. These are isoflavonoids that contain a pyran ring fused to either of the A, B, or C ring of the isoflavonoid skeleton (S)-8-Prenylphaseollinisoflavan is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (S)-8-Prenylphaseollinisoflavan has been detected, but not quantified in, herbs and spices and tea. 6-[7-hydroxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-3-yl]-2,2-dimethylchromen-5-ol is found in Glycyrrhiza glabra. This could make (S)-8-prenylphaseollinisoflavan a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061312382D          

 29 32  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv0541 05061312382D          

 29 32  0  0  0  0            999 V2000
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    3.1401    6.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0304399

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C(O)C=CC2=C1OCC(C2)C1=C(O)C2=C(OC(C)(C)C=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C25H28O4/c1-15(2)5-7-19-21(26)9-6-16-13-17(14-28-24(16)19)18-8-10-22-20(23(18)27)11-12-25(3,4)29-22/h5-6,8-12,17,26-27H,7,13-14H2,1-4H3

> <INCHI_KEY>
PPYSNAHBRHGTLI-UHFFFAOYSA-N

> <FORMULA>
C25H28O4

> <MOLECULAR_WEIGHT>
392.4874

> <EXACT_MASS>
392.198759384

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
45.35592993657841

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-[7-hydroxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-3-yl]-2,2-dimethyl-2H-chromen-5-ol

> <ALOGPS_LOGP>
5.19

> <JCHEM_LOGP>
5.820868278666666

> <ALOGPS_LOGS>
-5.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.95458873583718

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.339626475706016

> <JCHEM_PKA_STRONGEST_BASIC>
-4.58511488272242

> <JCHEM_POLAR_SURFACE_AREA>
58.92

> <JCHEM_REFRACTIVITY>
117.59639999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.07e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-[7-hydroxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-3-yl]-2,2-dimethylchromen-5-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.851  10.513   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.862  12.227   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.335   9.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  10.780   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.668   8.470   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  11.550   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -6.668   6.930   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667  10.780   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.335  10.780   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -8.002   6.160   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       4.001  11.550   0.000  0.00  0.00           O+0
CONECT    1   15                                                            
CONECT    2   15                                                            
CONECT    3   25                                                            
CONECT    4   25                                                            
CONECT    5    7   15                                                       
CONECT    6    9   16                                                       
CONECT    7    5   19                                                       
CONECT    8   10   18                                                       
CONECT    9    6   21                                                       
CONECT   10    8   22                                                       
CONECT   11   12   20                                                       
CONECT   12   11   25                                                       
CONECT   13   16   17                                                       
CONECT   14   17   28                                                       
CONECT   15    1    2    5                                                  
CONECT   16    6   13   24                                                  
CONECT   17   13   14   18                                                  
CONECT   18    8   17   23                                                  
CONECT   19    7   21   24                                                  
CONECT   20   11   22   23                                                  
CONECT   21    9   19   26                                                  
CONECT   22   10   20   29                                                  
CONECT   23   18   20   27                                                  
CONECT   24   16   19   28                                                  
CONECT   25    3    4   12   29                                             
CONECT   26   21                                                            
CONECT   27   23                                                            
CONECT   28   14   24                                                       
CONECT   29   22   25                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₈O₄

Average Mass

392.4874 Da

Monoisotopic Mass

392.19876 Da

IUPAC Name

6-[7-hydroxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-3-yl]-2,2-dimethyl-2H-chromen-5-ol

Traditional Name

6-[7-hydroxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-3-yl]-2,2-dimethylchromen-5-ol

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=C(O)C=CC2=C1OCC(C2)C1=C(O)C2=C(OC(C)(C)C=C2)C=C1

InChI Identifier

InChI=1S/C25H28O4/c1-15(2)5-7-19-21(26)9-6-16-13-17(14-28-24(16)19)18-8-10-22-20(23(18)27)11-12-25(3,4)29-22/h5-6,8-12,17,26-27H,7,13-14H2,1-4H3

InChI Key

PPYSNAHBRHGTLI-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
Glycyrrhiza glabra	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranoisoflavonoids. These are isoflavonoids that contain a pyran ring fused to either of the A, B, or C ring of the isoflavonoid skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Pyranoisoflavonoids

Direct Parent

Pyranoisoflavonoids

Alternative Parents

Substituents

Pyranoisoflavonoid
Hydroxyisoflavonoid
Isoflavanol
Isoflavan
2,2-dimethyl-1-benzopyran
Chromane
Benzopyran
1-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Oxacycle
Ether
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
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	5.19	ALOGPS
logP	5.82	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	9.34	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.92 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	117.6 m³·mol⁻¹	ChemAxon
Polarizability	45.36 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0041382

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021313

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15228660

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-[7-hydroxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-3-yl]-2,2-dimethylchromen-5-ol (NP0304399)

MOL for NP0304399 (6-[7-hydroxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-3-yl]-2,2-dimethylchromen-5-ol)

3D MOL for NP0304399 (6-[7-hydroxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-3-yl]-2,2-dimethylchromen-5-ol)

3D SDF for NP0304399 (6-[7-hydroxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-3-yl]-2,2-dimethylchromen-5-ol)

3D-SDF for NP0304399 (6-[7-hydroxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-3-yl]-2,2-dimethylchromen-5-ol)

PDB for NP0304399 (6-[7-hydroxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-3-yl]-2,2-dimethylchromen-5-ol)

3D PDB for NP0304399 (6-[7-hydroxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-3-yl]-2,2-dimethylchromen-5-ol)

SMILES for NP0304399 (6-[7-hydroxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-3-yl]-2,2-dimethylchromen-5-ol)

INCHI for NP0304399 (6-[7-hydroxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-3-yl]-2,2-dimethylchromen-5-ol)

Structure for NP0304399 (6-[7-hydroxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-3-yl]-2,2-dimethylchromen-5-ol)

3D Structure for NP0304399 (6-[7-hydroxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-3-yl]-2,2-dimethylchromen-5-ol)