NP-MRD: Showing NP-Card for Rhinacanthin E (NP0050474)

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Record Information

Version

2.0

Created at

2022-04-27 21:44:53 UTC

Updated at

2022-04-27 21:44:54 UTC

NP-MRD ID

NP0050474

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Rhinacanthin E

Description

1,4-Dimethyl (2Z,3S)-2-[(2H-1,3-benzodioxol-5-yl)methylidene]-3-[(7-methoxy-2H-1,3-benzodioxol-5-yl)methyl]butanedioate belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed. Rhinacanthin E is found in Rhinacanthus nasutus. Based on a literature review very few articles have been published on 1,4-dimethyl (2Z,3S)-2-[(2H-1,3-benzodioxol-5-yl)methylidene]-3-[(7-methoxy-2H-1,3-benzodioxol-5-yl)methyl]butanedioate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304272223442D          

 32 35  0  0  1  0            999 V2000
    7.6391    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3536    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3536    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6391    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9667    3.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6311    4.4787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8106    4.3924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  1  0  0  0  0
  9 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
  8 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
  2 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
  1 32  1  0  0  0  0
M  END


  Mrv1652304272223442D          

 32 35  0  0  1  0            999 V2000
    7.6391    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3536    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3536    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6391    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9667    3.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6311    4.4787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8106    4.3924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  1  0  0  0  0
  9 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
  8 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
  2 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
  1 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050474

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@H](CC1=CC(OC)=C2OCOC2=C1)C(=C\C1=CC2=C(OCO2)C=C1)\C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C23H22O9/c1-26-19-9-14(10-20-21(19)32-12-31-20)7-16(23(25)28-3)15(22(24)27-2)6-13-4-5-17-18(8-13)30-11-29-17/h4-6,8-10,16H,7,11-12H2,1-3H3/b15-6-/t16-/m0/s1

> <INCHI_KEY>
QOUBFZQTKRLGGJ-PJVYJYFWSA-N

> <FORMULA>
C23H22O9

> <MOLECULAR_WEIGHT>
442.42

> <EXACT_MASS>
442.126382288

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
45.055879288086864

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,4-dimethyl (2Z,3S)-2-[(2H-1,3-benzodioxol-5-yl)methylidene]-3-[(7-methoxy-2H-1,3-benzodioxol-5-yl)methyl]butanedioate

> <ALOGPS_LOGP>
2.84

> <JCHEM_LOGP>
3.3912396803333333

> <ALOGPS_LOGS>
-4.91

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.325709310733791

> <JCHEM_POLAR_SURFACE_AREA>
98.75000000000001

> <JCHEM_REFRACTIVITY>
110.48909999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.39e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,4-dimethyl (2Z,3S)-2-(2H-1,3-benzodioxol-5-ylmethylidene)-3-[(7-methoxy-2H-1,3-benzodioxol-5-yl)methyl]butanedioate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-22         0                                  
HETATM    1  C   UNK     0      14.260   6.693   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.593   5.923   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.593   4.383   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.260   3.613   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.926   4.383   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.926   5.923   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.592   3.613   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.259   4.383   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.925   3.613   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.126   1.597   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.924  -0.237   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.590  -1.007   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.925   2.073   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       7.591   1.303   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      10.259   1.303   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      10.259  -0.237   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.259   5.923   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      11.592   6.693   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       8.925   6.693   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       8.925   8.233   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      16.738   6.953   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      16.111   8.360   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      14.580   8.199   0.000  0.00  0.00           O+0
CONECT    1    2    6   32                                                  
CONECT    2    1    3   30                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   26                                                  
CONECT    9    8   10   22                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   20                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15   11                                                       
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20   13   21                                                       
CONECT   21   20                                                            
CONECT   22    9   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24                                                            
CONECT   26    8   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28                                                            
CONECT   30    2   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31    1                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
1,4-Dimethyl (2Z,3S)-2-[(2H-1,3-benzodioxol-5-yl)methylidene]-3-[(7-methoxy-2H-1,3-benzodioxol-5-yl)methyl]butanedioic acid	Generator

Chemical Formula

C₂₃H₂₂O₉

Average Mass

442.4200 Da

Monoisotopic Mass

442.12638 Da

IUPAC Name

1,4-dimethyl (2Z,3S)-2-[(2H-1,3-benzodioxol-5-yl)methylidene]-3-[(7-methoxy-2H-1,3-benzodioxol-5-yl)methyl]butanedioate

Traditional Name

1,4-dimethyl (2Z,3S)-2-(2H-1,3-benzodioxol-5-ylmethylidene)-3-[(7-methoxy-2H-1,3-benzodioxol-5-yl)methyl]butanedioate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@H](CC1=CC(OC)=C2OCOC2=C1)C(=C\C1=CC2=C(OCO2)C=C1)\C(=O)OC

InChI Identifier

InChI=1S/C23H22O9/c1-26-19-9-14(10-20-21(19)32-12-31-20)7-16(23(25)28-3)15(22(24)27-2)6-13-4-5-17-18(8-13)30-11-29-17/h4-6,8-10,16H,7,11-12H2,1-3H3/b15-6-/t16-/m0/s1

InChI Key

QOUBFZQTKRLGGJ-PJVYJYFWSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Rhinacanthus nasutus	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Not Available

Sub Class

Not Available

Direct Parent

Lignans, neolignans and related compounds

Alternative Parents

Substituents

Norlignan skeleton
Coumaric acid or derivatives
Benzodioxole
Anisole
Alkyl aryl ether
Fatty acid ester
Fatty acyl
Benzenoid
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Carboxylic acid ester
Acetal
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Ether
Carbonyl group
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
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	2.84	ALOGPS
logP	3.39	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	98.75 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	110.49 m³·mol⁻¹	ChemAxon
Polarizability	45.06 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

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

163089309

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Rhinacanthin E (NP0050474)

MOL for NP0050474 (Rhinacanthin E)

3D MOL for NP0050474 (Rhinacanthin E)

3D SDF for NP0050474 (Rhinacanthin E)

3D-SDF for NP0050474 (Rhinacanthin E)

PDB for NP0050474 (Rhinacanthin E)

3D PDB for NP0050474 (Rhinacanthin E)

SMILES for NP0050474 (Rhinacanthin E)

INCHI for NP0050474 (Rhinacanthin E)

Structure for NP0050474 (Rhinacanthin E)

3D Structure for NP0050474 (Rhinacanthin E)