Np mrd loader

Showing NP-Card for Hypophyllanthin (NP0050473)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2022-04-27 21:44:49 UTC
Updated at2022-04-27 21:44:49 UTC
NP-MRD IDNP0050473
Secondary Accession NumbersNone
Natural Product Identification
Common NameHypophyllanthin
DescriptionHypophyllanthin belongs to the class of organic compounds known as aryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton. Hypophyllanthin is found in Phyllanthus amarus Schum. & Thonn. , Phyllanthus niruri , Phyllanthus urinaria and Phyllanthus urinaria L. . Hypophyllanthin was first documented in 2020 (PMID: 32716561). Based on a literature review a small amount of articles have been published on Hypophyllanthin (PMID: 33259591) (PMID: 34214339) (PMID: 33525733).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0050473 (Hypophyllanthin)


  Mrv1652304272223442D          

 31 34  0  0  1  0            999 V2000
    4.0004    2.5677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5658    1.8665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7412    1.8923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3512    2.6193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7858    3.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6104    3.2948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3959    4.0475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8305    4.7488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266    2.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1366    3.3720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9558    1.1395    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5212    0.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9112   -0.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4766   -0.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520   -0.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2620   -0.2372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6966    0.4640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1640    1.0941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4002    0.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4608   -0.0406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2174   -1.6655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6073   -2.3925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7358   -0.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1704    0.3867    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7804    1.1137    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2150    1.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8250    2.5420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2596    3.2432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9950    0.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4296    1.0622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2542    1.0365    0.0000 C   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  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11  2  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 16 20  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
 13 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 11 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 24 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END
Download

3D MOL for NP0050473 (Hypophyllanthin)

Download
3D SDF for NP0050473 (Hypophyllanthin)

  Mrv1652304272223442D          

 31 34  0  0  1  0            999 V2000
    4.0004    2.5677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5658    1.8665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7412    1.8923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3512    2.6193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7858    3.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6104    3.2948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3959    4.0475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8305    4.7488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266    2.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1366    3.3720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9558    1.1395    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5212    0.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9112   -0.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4766   -0.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520   -0.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2620   -0.2372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6966    0.4640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1640    1.0941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4002    0.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4608   -0.0406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2174   -1.6655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6073   -2.3925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7358   -0.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1704    0.3867    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7804    1.1137    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2150    1.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8250    2.5420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2596    3.2432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9950    0.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4296    1.0622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2542    1.0365    0.0000 C   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  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11  2  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 16 20  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
 13 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 11 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 24 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050473

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC[C@@H]1CC2=C([C@@H]([C@H]1COC)C1=CC=C(OC)C(OC)=C1)C1=C(OCO1)C(OC)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C24H30O7/c1-25-11-16-8-15-10-20(29-5)23-24(31-13-30-23)22(15)21(17(16)12-26-2)14-6-7-18(27-3)19(9-14)28-4/h6-7,9-10,16-17,21H,8,11-13H2,1-5H3/t16-,17-,21+/m0/s1

> <INCHI_KEY>
LBJCUHLNHSKZBW-XGHQBKJUSA-N

> <FORMULA>
C24H30O7

> <MOLECULAR_WEIGHT>
430.497

> <EXACT_MASS>
430.199153306

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
46.801937923169596

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(7R,8R,9S)-9-(3,4-dimethoxyphenyl)-4-methoxy-7,8-bis(methoxymethyl)-2H,6H,7H,8H,9H-naphtho[1,2-d][1,3]dioxole

> <ALOGPS_LOGP>
3.20

> <JCHEM_LOGP>
3.1393841883333335

> <ALOGPS_LOGS>
-4.93

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6724434828985415

> <JCHEM_POLAR_SURFACE_AREA>
64.61000000000001

> <JCHEM_REFRACTIVITY>
115.64330000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.08e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(7R,8R,9S)-9-(3,4-dimethoxyphenyl)-4-methoxy-7,8-bis(methoxymethyl)-2H,6H,7H,8H,9H-naphtho[1,2-d][1,3]dioxole

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0050473 (Hypophyllanthin)
Download
PDB for NP0050473 (Hypophyllanthin)
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       7.467   4.793   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.656   3.484   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.117   3.532   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.389   4.889   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.200   6.198   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.739   6.150   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.472   7.555   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.284   8.864   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.850   4.937   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.122   6.294   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.384   2.127   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.573   0.818   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.301  -0.539   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.490  -1.848   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.950  -1.800   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.222  -0.443   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.034   0.866   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.039   2.042   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.614   1.460   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.727  -0.076   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.139  -3.109   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.867  -4.466   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.840  -0.587   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.651   0.722   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.923   2.079   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.735   3.388   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       9.007   4.745   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       9.818   6.054   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.191   0.674   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      12.002   1.983   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      13.541   1.935   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7                                                            
CONECT    9    4   10                                                       
CONECT   10    9                                                            
CONECT   11    2   12   25                                                  
CONECT   12   11   13   17                                                  
CONECT   13   12   14   23                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15   17   20                                                  
CONECT   17   16   12   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   16                                                       
CONECT   21   15   22                                                       
CONECT   22   21                                                            
CONECT   23   13   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   11   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   24   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

Download
3D PDB for NP0050473 (Hypophyllanthin)
Download
SMILES for NP0050473 (Hypophyllanthin)
COC[C@@H]1CC2=C([C@@H]([C@H]1COC)C1=CC=C(OC)C(OC)=C1)C1=C(OCO1)C(OC)=C2
Download
INCHI for NP0050473 (Hypophyllanthin)
InChI=1S/C24H30O7/c1-25-11-16-8-15-10-20(29-5)23-24(31-13-30-23)22(15)21(17(16)12-26-2)14-6-7-18(27-3)19(9-14)28-4/h6-7,9-10,16-17,21H,8,11-13H2,1-5H3/t16-,17-,21+/m0/s1
Download
View in JSmol
Synonyms
ValueSource
(7R,8R,9S)-9-(3,4-Dimethoxyphenyl)-4-methoxy-7,8-bis(methoxymethyl)-6,7,8,9-tetrahydronaphtho(1,2-D)(1,3)dioxoleMeSH
Chemical FormulaC24H30O7
Average Mass430.4970 Da
Monoisotopic Mass430.19915 Da
IUPAC Name(7R,8R,9S)-9-(3,4-dimethoxyphenyl)-4-methoxy-7,8-bis(methoxymethyl)-2H,6H,7H,8H,9H-naphtho[1,2-d][1,3]dioxole
Traditional Name(7R,8R,9S)-9-(3,4-dimethoxyphenyl)-4-methoxy-7,8-bis(methoxymethyl)-2H,6H,7H,8H,9H-naphtho[1,2-d][1,3]dioxole
CAS Registry NumberNot Available
SMILES
COC[C@@H]1CC2=C([C@@H]([C@H]1COC)C1=CC=C(OC)C(OC)=C1)C1=C(OCO1)C(OC)=C2
InChI Identifier
InChI=1S/C24H30O7/c1-25-11-16-8-15-10-20(29-5)23-24(31-13-30-23)22(15)21(17(16)12-26-2)14-6-7-18(27-3)19(9-14)28-4/h6-7,9-10,16-17,21H,8,11-13H2,1-5H3/t16-,17-,21+/m0/s1
InChI KeyLBJCUHLNHSKZBW-XGHQBKJUSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Phyllanthus amarus Schum. & Thonn.Plant
Phyllanthus niruriPlant
Phyllanthus urinariaLOTUS Database
Phyllanthus urinaria L.Plant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton.
KingdomOrganic compounds  
Super ClassLignans, neolignans and related compounds  
ClassAryltetralin lignans  
Sub ClassNot Available
Direct ParentAryltetralin lignans  
Alternative Parents
Substituents
  • 1-aryltetralin lignan
    • 

  • Tetralin
    • 

  • Dimethoxybenzene
    • 

  • O-dimethoxybenzene
    • 

  • Benzodioxole
    • 

  • Methoxybenzene
    • 

  • Anisole
    • 

  • Phenol ether
    • 

  • Phenoxy compound
    • 

  • Alkyl aryl ether
    • 

  • Monocyclic benzene moiety
    • 

  • Benzenoid
    • 

  • Ether
    • 

  • Dialkyl ether
    • 

  • Organoheterocyclic compound
    • 

  • Oxacycle
    • 

  • Acetal
    • 

  • Organooxygen compound
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.2ALOGPS
logP3.14ChemAxon
logS-4.9ALOGPS
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area64.61 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity115.64 m³·mol⁻¹ChemAxon
Polarizability46.8 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00000707  
Chemspider ID158417  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound182140  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Patel J, Nagar PS, Pal K, Singh R, Dhanani T, Patel V, Srivastava S, Kumar S: Comparative Profiling of Four Lignans (Phyllanthin, Hypophyllanthin, Nirtetralin, and Niranthin) in Nine Phyllanthus Species from India Using a Validated Reversed Phase HPLC-PDA Detection Method. J AOAC Int. 2021 May 21;104(2):485-497. doi: 10.1093/jaoacint/qsaa133. [PubMed:33259591  ] 
  2. Marhaeny HD, Widyawaruyanti A, Widiandani T, Fuad Hafid A, Wahyuni TS: Phyllanthin and hypophyllanthin, the isolated compounds of Phyllanthus niruri inhibit protein receptor of corona virus (COVID-19) through in silico approach. J Basic Clin Physiol Pharmacol. 2021 Jun 25;32(4):809-815. doi:  10.1515/jbcpp-2020-0473. [PubMed:34214339  ] 
  3. Abd Rani NZ, Lam KW, Jalil J, Mohamad HF, Mat Ali MS, Husain K: Mechanistic Studies of the Antiallergic Activity of Phyllanthus amarus Schum. & Thonn. and Its Compounds. Molecules. 2021 Jan 28;26(3):695. doi: 10.3390/molecules26030695. [PubMed:33525733  ] 
  4. Boonyong C, Vardhanabhuti N, Jianmongkol S: Modulation of non-steroidal anti-inflammatory drug-induced, ER stress-mediated apoptosis in Caco-2 cells by different polyphenolic antioxidants: a mechanistic study. J Pharm Pharmacol. 2020 Nov;72(11):1574-1584. doi: 10.1111/jphp.13343. Epub 2020  Jul 27. [PubMed:32716561  ]