NP-MRD: Showing NP-Card for 3'-Deoxy-4-O-methylepisappanol (NP0138806)

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Record Information

Version

1.0

Created at

2022-06-29 19:17:56 UTC

Updated at

2022-06-29 19:17:56 UTC

NP-MRD ID

NP0138806

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3'-Deoxy-4-O-methylepisappanol

Description

3'-Deoxy-4-O-methylepisappanol belongs to the class of organic compounds known as homoisoflavans. These are homoisoflavonoids with a structure based on the chromane system. Chromone is a bicyclic compound consisting of a 3,4-dihydro-1-benzopyran. It was first documented in 2008 (PMID: 18794793). Based on a literature review a small amount of articles have been published on 3'-Deoxy-4-O-methylepisappanol (PMID: 20105050) (PMID: 19777498).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 42  0  0  0  0  0  0  0  0999 V2000
    0.4793    2.3936    1.5415 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3895    1.1414    0.9371 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6716    1.1082    0.0779 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7469    0.1529    0.4947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7175   -0.5029    1.6983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7516   -1.3623    1.9988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7846   -1.5523    1.1075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8212   -2.4188    1.4174 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8110   -0.8922   -0.1005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7769   -0.0307   -0.4045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7161    0.6771   -1.5931 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5047    0.9934   -2.2493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3095    0.8619   -1.3441 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5995    1.8816   -1.7145 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3999   -0.4372   -1.6078 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6830   -0.5848   -0.8915 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8818   -0.1391   -1.4258 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0561   -0.3014   -0.7327 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0792   -0.8999    0.4902 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2978   -1.0526    1.1778 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9103   -1.3479    1.0385 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7204   -1.1880    0.3453 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6183    3.1772    0.7682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4162    2.6139    2.1664 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3541    2.4581    2.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1980    2.1128    0.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8896   -0.3255    2.3679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7157   -1.8827    2.9689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8122   -3.4123    1.1826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5962   -1.0049   -0.8334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3923    0.2595   -3.0988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5783    1.9884   -2.7331 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1488    2.5737   -2.2515 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6611   -0.4436   -2.7060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2607   -1.3187   -1.4725 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8962    0.3434   -2.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9925    0.0592   -1.1755 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5782   -0.3022    1.7991 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9007   -1.8281    2.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8242   -1.5681    0.8349 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 10  9  1  0
  9  7  2  0
  7  8  1  0
  7  6  1  0
  6  5  2  0
 13  3  1  0
 22 16  1  0
  5  4  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  6
 12 31  1  0
 12 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 17 36  1  0
 18 37  1  0
 20 38  1  0
 21 39  1  0
 22 40  1  0
  9 30  1  0
  8 29  1  0
  6 28  1  0
  5 27  1  0
M  END


  Mrv1652306292221172D          

 22 24  0  0  1  0            999 V2000
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 C   0  0  2  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
    0.7145   -0.4125    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
    2.1434   -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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 O   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
   -0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5390   -1.2663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9762   -0.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8006   -0.5954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2378    0.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8505    0.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0260    0.8614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5888    0.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2877    1.5323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1517   -1.9371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  7 10  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  3 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
 18 21  1  0  0  0  0
 13 22  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0138806

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1C2=C(OC[C@]1(O)CC1=CC=C(O)C=C1)C=C(O)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C17H18O5/c1-21-16-14-7-6-13(19)8-15(14)22-10-17(16,20)9-11-2-4-12(18)5-3-11/h2-8,16,18-20H,9-10H2,1H3/t16-,17-/m1/s1

> <INCHI_KEY>
NRDMATSOBGRQDO-IAGOWNOFSA-N

> <FORMULA>
C17H18O5

> <MOLECULAR_WEIGHT>
302.326

> <EXACT_MASS>
302.11542368

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
31.480934165733306

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,4R)-3-[(4-hydroxyphenyl)methyl]-4-methoxy-3,4-dihydro-2H-1-benzopyran-3,7-diol

> <ALOGPS_LOGP>
1.79

> <JCHEM_LOGP>
2.279030864

> <ALOGPS_LOGS>
-3.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.226853027611524

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.34293541968734

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7530981593819854

> <JCHEM_POLAR_SURFACE_AREA>
79.15

> <JCHEM_REFRACTIVITY>
80.971

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.37e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,4R)-3-[(4-hydroxyphenyl)methyl]-4-methoxy-2,4-dihydro-1-benzopyran-3,7-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -2.310   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  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.000  -0.000   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.873  -2.364   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.689  -1.058   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.228  -1.111   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -6.044   0.194   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.321   1.554   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.782   1.608   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.966   0.302   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -6.137   2.860   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -2.150  -3.616   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8    4                                                       
CONECT   10    7                                                            
CONECT   11    5   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    3   14   22                                             
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19   15                                                       
CONECT   21   18                                                            
CONECT   22   13                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₈O₅

Average Mass

302.3260 Da

Monoisotopic Mass

302.11542 Da

IUPAC Name

(3R,4R)-3-[(4-hydroxyphenyl)methyl]-4-methoxy-3,4-dihydro-2H-1-benzopyran-3,7-diol

Traditional Name

(3R,4R)-3-[(4-hydroxyphenyl)methyl]-4-methoxy-2,4-dihydro-1-benzopyran-3,7-diol

CAS Registry Number

1052714-12-1

SMILES

CO[C@@H]1C2=C(OC[C@]1(O)CC1=CC=C(O)C=C1)C=C(O)C=C2

InChI Identifier

InChI=1S/C17H18O5/c1-21-16-14-7-6-13(19)8-15(14)22-10-17(16,20)9-11-2-4-12(18)5-3-11/h2-8,16,18-20H,9-10H2,1H3/t16-,17-/m1/s1

InChI Key

NRDMATSOBGRQDO-IAGOWNOFSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as homoisoflavans. These are homoisoflavonoids with a structure based on the chromane system. Chromone is a bicyclic compound consisting of a 3,4-dihydro-1-benzopyran.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Homoisoflavonoids

Sub Class

Homoisoflavans

Direct Parent

Homoisoflavans

Alternative Parents

Substituents

Homoisoflavan
Chromane
Benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Tertiary alcohol
Organoheterocyclic compound
Ether
Dialkyl ether
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Alcohol
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	1.79	ALOGPS
logP	2.28	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	9.34	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	79.15 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	80.97 m³·mol⁻¹	ChemAxon
Polarizability	31.48 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28650735

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71463283

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Fu LC, Huang XA, Lai ZY, Hu YJ, Liu HJ, Cai XL: A new 3-benzylchroman derivative from Sappan Lignum (Caesalpinia sappan). Molecules. 2008 Aug 28;13(8):1923-30. doi: 10.3390/molecules13081923. [PubMed:18794793 ]
Lee MJ, Lee HS, Kim H, Yi HS, Park SD, Moon HI, Park WH: Antioxidant properties of benzylchroman derivatives from Caesalpinia sappan L. against oxidative stress evaluated in vitro. J Enzyme Inhib Med Chem. 2010 Oct;25(5):608-14. doi: 10.3109/14756360903373376. [PubMed:20105050 ]
Moon HI, Chung IM, Seo SH, Kang EY: Protective effects of 3'-deoxy-4-O-methylepisappanol from Caesalpinia sappan against glutamate-induced neurotoxicity in primary cultured rat cortical cells. Phytother Res. 2010 Mar;24(3):463-5. doi: 10.1002/ptr.2982. [PubMed:19777498 ]

Showing NP-Card for 3'-Deoxy-4-O-methylepisappanol (NP0138806)

MOL for NP0138806 (3'-Deoxy-4-O-methylepisappanol)

3D MOL for NP0138806 (3'-Deoxy-4-O-methylepisappanol)

3D SDF for NP0138806 (3'-Deoxy-4-O-methylepisappanol)

3D-SDF for NP0138806 (3'-Deoxy-4-O-methylepisappanol)

PDB for NP0138806 (3'-Deoxy-4-O-methylepisappanol)

3D PDB for NP0138806 (3'-Deoxy-4-O-methylepisappanol)

SMILES for NP0138806 (3'-Deoxy-4-O-methylepisappanol)

INCHI for NP0138806 (3'-Deoxy-4-O-methylepisappanol)

Structure for NP0138806 (3'-Deoxy-4-O-methylepisappanol)

3D Structure for NP0138806 (3'-Deoxy-4-O-methylepisappanol)