NP-MRD: Showing NP-Card for Isosativan (NP0137006)

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Record Information

Version

2.0

Created at

2022-05-30 16:38:47 UTC

Updated at

2022-05-30 16:38:47 UTC

NP-MRD ID

NP0137006

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isosativan

Description

Isosativan belongs to the class of organic compounds known as 7-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C7 atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one. Thus, isosativan is considered to be a flavonoid lipid molecule. Isosativan is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Isosativan has been detected, but not quantified in, pulses. Isosativan is found in Dalbergia ecastaphyllum. This could make isosativan a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
   -5.1350    2.3439   -0.2843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9384    0.9706   -0.1409 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7922    0.2558    0.0237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5291    0.8299    0.0997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4166    0.0347    0.2722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4955   -1.3260    0.3745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2910   -2.1988    0.3851 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4524   -2.0726    1.6752 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7760   -1.6849    1.6320 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2337   -0.7490    0.7236 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1925    0.1396    1.0551 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6368    1.1064    0.1186 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5879    1.9505    0.5124 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3377    2.9794    0.0825 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0289    1.0547   -1.1147 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0417    0.1375   -1.4629 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6251   -0.7925   -0.5347 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6156   -1.8124   -0.8052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7708   -1.9010    0.2973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9307   -3.2658    0.4163 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8909   -1.1239    0.1237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5129    2.7765    0.6882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9730    2.5096   -1.0193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2716    2.9354   -0.5830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4291    1.9010    0.0186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4805    0.5310    0.3046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5517   -3.2275    0.2071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1322   -1.3741    2.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3583   -3.0645    2.2544 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6661    0.1826    2.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8181    3.8249   -0.4352 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1685    2.5762   -0.5755 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9577    3.4267    0.9475 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3904    1.8027   -1.8354 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6069    0.1656   -2.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0633   -1.6158   -1.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1673   -2.7466   -1.0931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2106   -3.8784    0.6339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8466   -1.6014    0.0657 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 21  2  0
 21 19  1  0
 19 20  1  0
 19  6  2  0
  6  5  1  0
  5  4  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 17  2  0
 17 18  1  0
 17 16  1  0
 16 15  2  0
 15 12  1  0
 12 13  1  0
 13 14  1  0
 12 11  2  0
  4  3  1  0
 18  7  1  0
 11 10  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
 21 39  1  0
 20 38  1  0
  5 26  1  0
  4 25  1  0
  7 27  1  6
  8 28  1  0
  8 29  1  0
 18 36  1  0
 18 37  1  0
 16 35  1  0
 15 34  1  0
 14 31  1  0
 14 32  1  0
 14 33  1  0
 11 30  1  0
M  END


  Mrv0541 05061307302D          

 21 23  0  0  0  0            999 V2000
    7.1447    0.8250    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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    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
    5.7158    0.0000    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
    3.5724   -1.2375    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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    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
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    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
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  6  5  2  0  0  0  0
 11  3  1  0  0  0  0
 11  7  1  0  0  0  0
 12  7  1  0  0  0  0
 12 10  1  0  0  0  0
 13  5  1  0  0  0  0
 13  8  2  0  0  0  0
 14  4  1  0  0  0  0
 14  9  2  0  0  0  0
 15  6  1  0  0  0  0
 15 12  1  0  0  0  0
 16  8  1  0  0  0  0
 16 15  2  0  0  0  0
 17  9  1  0  0  0  0
 17 11  2  0  0  0  0
 18 16  1  0  0  0  0
 19  1  1  0  0  0  0
 19 13  1  0  0  0  0
 20  2  1  0  0  0  0
 20 14  1  0  0  0  0
 21 10  1  0  0  0  0
 21 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137006

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C(C=C1)C1COC2=C(C1)C=CC(OC)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C17H18O4/c1-19-13-5-6-15(16(18)8-13)12-7-11-3-4-14(20-2)9-17(11)21-10-12/h3-6,8-9,12,18H,7,10H2,1-2H3

> <INCHI_KEY>
FWAWTPASGRNXTO-UHFFFAOYSA-N

> <FORMULA>
C17H18O4

> <MOLECULAR_WEIGHT>
286.3224

> <EXACT_MASS>
286.120509064

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
31.40173095491271

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-methoxy-2-(7-methoxy-3,4-dihydro-2H-1-benzopyran-3-yl)phenol

> <ALOGPS_LOGP>
3.10

> <JCHEM_LOGP>
3.179900667666667

> <ALOGPS_LOGS>
-4.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.780514465620708

> <JCHEM_PKA_STRONGEST_BASIC>
-4.360837020811598

> <JCHEM_POLAR_SURFACE_AREA>
47.92

> <JCHEM_REFRACTIVITY>
79.90570000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.76e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isosativan

> <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      13.337   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   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       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -0.770   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  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2   20                                                            
CONECT    3    4   11                                                       
CONECT    4    3   14                                                       
CONECT    5    6   13                                                       
CONECT    6    5   15                                                       
CONECT    7   11   12                                                       
CONECT    8   13   16                                                       
CONECT    9   14   17                                                       
CONECT   10   12   21                                                       
CONECT   11    3    7   17                                                  
CONECT   12    7   10   15                                                  
CONECT   13    5    8   19                                                  
CONECT   14    4    9   20                                                  
CONECT   15    6   12   16                                                  
CONECT   16    8   15   18                                                  
CONECT   17    9   11   21                                                  
CONECT   18   16                                                            
CONECT   19    1   13                                                       
CONECT   20    2   14                                                       
CONECT   21   10   17                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Value	Source
2'-Hydroxy-4',7-dimethoxyisoflavan	HMDB
2'-Hydroxy-7,4'-dimethoxyisoflavan	HMDB

Chemical Formula

C₁₇H₁₈O₄

Average Mass

286.3224 Da

Monoisotopic Mass

286.12051 Da

IUPAC Name

5-methoxy-2-(7-methoxy-3,4-dihydro-2H-1-benzopyran-3-yl)phenol

Traditional Name

isosativan

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C(C=C1)C1COC2=C(C1)C=CC(OC)=C2

InChI Identifier

InChI=1S/C17H18O4/c1-19-13-5-6-15(16(18)8-13)12-7-11-3-4-14(20-2)9-17(11)21-10-12/h3-6,8-9,12,18H,7,10H2,1-2H3

InChI Key

FWAWTPASGRNXTO-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
Dalbergia ecastaphyllum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C7 atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

O-methylated isoflavonoids

Direct Parent

7-O-methylated isoflavonoids

Alternative Parents

Substituents

4p-methoxyisoflavonoid
7-methoxyisoflavonoid-skeleton
Hydroxyisoflavonoid
Isoflavanol
Isoflavan
Chromane
Benzopyran
Methoxyphenol
1-benzopyran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Oxacycle
Ether
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Isoflavans (LMPK12080030 )

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	3.1	ALOGPS
logP	3.18	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	9.78	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	47.92 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	79.91 m³·mol⁻¹	ChemAxon
Polarizability	31.4 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0034024

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012262

KNApSAcK ID

C00009711

Chemspider ID

514319

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

591624

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Isosativan (NP0137006)

MOL for NP0137006 (Isosativan)

3D MOL for NP0137006 (Isosativan)

3D SDF for NP0137006 (Isosativan)

3D-SDF for NP0137006 (Isosativan)

PDB for NP0137006 (Isosativan)

3D PDB for NP0137006 (Isosativan)

SMILES for NP0137006 (Isosativan)

INCHI for NP0137006 (Isosativan)

Structure for NP0137006 (Isosativan)

3D Structure for NP0137006 (Isosativan)