NP-MRD: Showing NP-Card for (4s)-4-[8-(3-hydroxy-3-methylbutyl)-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]-12,12-dimethyl-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1,7,9-trien-6-one (NP0198137)

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Record Information

Version

2.0

Created at

2022-09-04 16:31:37 UTC

Updated at

2022-09-04 16:31:37 UTC

NP-MRD ID

NP0198137

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4s)-4-[8-(3-hydroxy-3-methylbutyl)-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]-12,12-dimethyl-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1,7,9-trien-6-one

Description

Tonkinochromane D 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. (4s)-4-[8-(3-hydroxy-3-methylbutyl)-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]-12,12-dimethyl-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1,7,9-trien-6-one is found in Sophora tonkinensis. Based on a literature review very few articles have been published on Tonkinochromane D.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042218312D          

 35 39  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309042218312D          

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 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 10 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 23 26  1  0  0  0  0
 17 26  1  0  0  0  0
  9 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
  7 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 31 34  1  0  0  0  0
 34 35  1  0  0  0  0
 28 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0198137

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(O)CCC1=CC(=CC2=C1OC(C)(C)CC2)[C@@H]1CC(=O)C2=CC=C3OC(C)(C)CCC3=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C30H38O5/c1-28(2,32)12-9-18-15-20(16-19-10-13-30(5,6)35-26(18)19)25-17-23(31)21-7-8-24-22(27(21)33-25)11-14-29(3,4)34-24/h7-8,15-16,25,32H,9-14,17H2,1-6H3/t25-/m0/s1

> <INCHI_KEY>
FINRXOPONMGFIH-VWLOTQADSA-N

> <FORMULA>
C30H38O5

> <MOLECULAR_WEIGHT>
478.629

> <EXACT_MASS>
478.271924324

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
55.90895763214695

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4S)-4-[8-(3-hydroxy-3-methylbutyl)-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-6-yl]-12,12-dimethyl-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1,7,9-trien-6-one

> <JCHEM_LOGP>
5.806711008333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.477130486562

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.666396736261213

> <JCHEM_PKA_STRONGEST_BASIC>
-2.630404916710221

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
137.4376

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(4S)-4-[8-(3-hydroxy-3-methylbutyl)-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]-12,12-dimethyl-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1,7,9-trien-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -5.335   7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.875   6.160   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -3.795   6.160   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -8.002   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -10.669   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0     -13.337  -0.000   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0     -12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -13.337  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -9.680  -8.880   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -11.659  -8.880   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0     -12.003  -6.930   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.141   2.987   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.151   1.273   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   29                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   27                                                  
CONECT   10    9   11   20                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   26                                                  
CONECT   18   17   19   21                                                  
CONECT   19   18   14   20                                                  
CONECT   20   19   10                                                       
CONECT   21   18   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25   26                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   23   17                                                       
CONECT   27    9   28                                                       
CONECT   28   27   29   35                                                  
CONECT   29   28    7   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33   34                                             
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   31   35                                                       
CONECT   35   34   28                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₈O₅

Average Mass

478.6290 Da

Monoisotopic Mass

478.27192 Da

IUPAC Name

(4S)-4-[8-(3-hydroxy-3-methylbutyl)-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-6-yl]-12,12-dimethyl-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1,7,9-trien-6-one

Traditional Name

(4S)-4-[8-(3-hydroxy-3-methylbutyl)-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]-12,12-dimethyl-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1,7,9-trien-6-one

CAS Registry Number

Not Available

SMILES

CC(C)(O)CCC1=CC(=CC2=C1OC(C)(C)CC2)[C@@H]1CC(=O)C2=CC=C3OC(C)(C)CCC3=C2O1

InChI Identifier

InChI=1S/C30H38O5/c1-28(2,32)12-9-18-15-20(16-19-10-13-30(5,6)35-26(18)19)25-17-23(31)21-7-8-24-22(27(21)33-25)11-14-29(3,4)34-24/h7-8,15-16,25,32H,9-14,17H2,1-6H3/t25-/m0/s1

InChI Key

FINRXOPONMGFIH-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, 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
Sophora tonkinensis	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

3'-prenylated flavanone
8-prenylated flavanone
Pyranoflavonoid
3'-prenylated flavan
Flavanone
Pyranochromene
2,2-dimethyl-1-benzopyran
Chromone
Chromane
Benzopyran
1-benzopyran
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
Benzenoid
Tertiary alcohol
Ketone
Organoheterocyclic compound
Oxacycle
Ether
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen 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	5.81	ChemAxon
pKa (Strongest Acidic)	14.67	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	137.44 m³·mol⁻¹	ChemAxon
Polarizability	55.91 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	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

28284663

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23730688

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4s)-4-[8-(3-hydroxy-3-methylbutyl)-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]-12,12-dimethyl-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1,7,9-trien-6-one (NP0198137)

MOL for NP0198137 ((4s)-4-[8-(3-hydroxy-3-methylbutyl)-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]-12,12-dimethyl-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1,7,9-trien-6-one)

3D MOL for NP0198137 ((4s)-4-[8-(3-hydroxy-3-methylbutyl)-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]-12,12-dimethyl-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1,7,9-trien-6-one)

3D SDF for NP0198137 ((4s)-4-[8-(3-hydroxy-3-methylbutyl)-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]-12,12-dimethyl-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1,7,9-trien-6-one)

3D-SDF for NP0198137 ((4s)-4-[8-(3-hydroxy-3-methylbutyl)-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]-12,12-dimethyl-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1,7,9-trien-6-one)

PDB for NP0198137 ((4s)-4-[8-(3-hydroxy-3-methylbutyl)-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]-12,12-dimethyl-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1,7,9-trien-6-one)

3D PDB for NP0198137 ((4s)-4-[8-(3-hydroxy-3-methylbutyl)-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]-12,12-dimethyl-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1,7,9-trien-6-one)

SMILES for NP0198137 ((4s)-4-[8-(3-hydroxy-3-methylbutyl)-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]-12,12-dimethyl-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1,7,9-trien-6-one)

INCHI for NP0198137 ((4s)-4-[8-(3-hydroxy-3-methylbutyl)-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]-12,12-dimethyl-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1,7,9-trien-6-one)

Structure for NP0198137 ((4s)-4-[8-(3-hydroxy-3-methylbutyl)-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]-12,12-dimethyl-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1,7,9-trien-6-one)

3D Structure for NP0198137 ((4s)-4-[8-(3-hydroxy-3-methylbutyl)-2,2-dimethyl-3,4-dihydro-1-benzopyran-6-yl]-12,12-dimethyl-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1,7,9-trien-6-one)