NP-MRD: Showing NP-Card for Forsythoside I (NP0140620)

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Record Information

Version

1.0

Created at

2022-06-29 21:43:28 UTC

Updated at

2022-06-29 21:43:28 UTC

NP-MRD ID

NP0140620

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Forsythoside I

Description

Forsythoside I, also known as isoforsythiaside, belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. It was first documented in 2016 (PMID: 27165571). Based on a literature review a significant number of articles have been published on Forsythoside I (PMID: 33812251) (PMID: 33072499) (PMID: 30798212) (PMID: 28946767).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306292223432D          

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M  END

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M  END


  Mrv1652306292223432D          

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   -5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013  -10.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434  -16.0875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145  -15.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434  -10.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  6  8  1  6  0  0  0
  8  9  1  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 10 15  1  0  0  0  0
 14 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 19 24  1  0  0  0  0
 22 25  1  0  0  0  0
 21 26  1  0  0  0  0
 13 27  1  1  0  0  0
 12 28  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 33 38  1  0  0  0  0
 36 39  1  0  0  0  0
 35 40  1  0  0  0  0
 11 41  1  1  0  0  0
  5 42  1  1  0  0  0
  4 43  1  1  0  0  0
  3 44  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0140620

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](OCCC3=CC(O)=C(O)C=C3)[C@H](O)[C@@H](OC(=O)\C=C\C3=CC(O)=C(O)C=C3)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C29H36O15/c1-13-22(35)24(37)25(38)28(42-13)41-12-20-23(36)27(44-21(34)7-4-14-2-5-16(30)18(32)10-14)26(39)29(43-20)40-9-8-15-3-6-17(31)19(33)11-15/h2-7,10-11,13,20,22-33,35-39H,8-9,12H2,1H3/b7-4+/t13-,20+,22-,23+,24+,25+,26+,27-,28+,29+/m0/s1

> <INCHI_KEY>
GKRBWXABVALDGQ-GCELSKRESA-N

> <FORMULA>
C29H36O15

> <MOLECULAR_WEIGHT>
624.592

> <EXACT_MASS>
624.205420459

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
61.00096359741434

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4S,5R,6R)-2-[2-(3,4-dihydroxyphenyl)ethoxy]-3,5-dihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-4-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
1.10

> <JCHEM_LOGP>
0.8194253603333341

> <ALOGPS_LOGS>
-2.88

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.643084009454745

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.010173270666062

> <JCHEM_PKA_STRONGEST_BASIC>
-3.663724193271162

> <JCHEM_POLAR_SURFACE_AREA>
245.28999999999996

> <JCHEM_REFRACTIVITY>
148.40310000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.17e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4S,5R,6R)-2-[2-(3,4-dihydroxyphenyl)ethoxy]-3,5-dihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-4-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <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 -10.010   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334 -14.630   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667 -13.860   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.667 -12.320   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -4.001 -14.630   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -4.001 -16.170   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.335 -16.940   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.335 -18.480   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.668 -19.250   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -8.002 -18.480   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -8.002 -16.940   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -6.668 -16.170   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -9.336 -16.170   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -9.336 -14.630   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -10.669 -12.320   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -12.003 -11.550   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0     -10.669  -7.700   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0     -13.337  -9.240   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -9.336 -19.250   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -6.668 -20.790   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -5.335 -21.560   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -4.001 -20.790   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -5.335 -23.100   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.001 -23.870   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -4.001 -25.410   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.667 -26.180   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.667 -27.720   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -4.001 -28.490   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -5.335 -27.720   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -5.335 -26.180   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -4.001 -30.030   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -1.334 -28.490   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -4.001 -19.250   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      -1.334 -16.170   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       1.334 -14.630   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       1.334 -11.550   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4   44                                                  
CONECT    4    3    5   43                                                  
CONECT    5    4    6   42                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    2                                                       
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12   41                                                  
CONECT   12   11   13   28                                                  
CONECT   13   12   14   27                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14   10                                                       
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23   19                                                       
CONECT   25   22                                                            
CONECT   26   21                                                            
CONECT   27   13                                                            
CONECT   28   12   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   38                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   40                                                  
CONECT   36   35   37   39                                                  
CONECT   37   36   38                                                       
CONECT   38   37   33                                                       
CONECT   39   36                                                            
CONECT   40   35                                                            
CONECT   41   11                                                            
CONECT   42    5                                                            
CONECT   43    4                                                            
CONECT   44    3                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   94    0
END

View in JSmol

Synonyms

Value	Source
Isoforsythiaside	MeSH

Chemical Formula

C₂₉H₃₆O₁₅

Average Mass

624.5920 Da

Monoisotopic Mass

624.20542 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](OCCC3=CC(O)=C(O)C=C3)[C@H](O)[C@@H](OC(=O)\C=C\C3=CC(O)=C(O)C=C3)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C29H36O15/c1-13-22(35)24(37)25(38)28(42-13)41-12-20-23(36)27(44-21(34)7-4-14-2-5-16(30)18(32)10-14)26(39)29(43-20)40-9-8-15-3-6-17(31)19(33)11-15/h2-7,10-11,13,20,22-33,35-39H,8-9,12H2,1H3/b7-4+/t13-,20+,22-,23+,24+,25+,26+,27-,28+,29+/m0/s1

InChI Key

GKRBWXABVALDGQ-GCELSKRESA-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 coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Coumaric acid or derivatives
Cinnamic acid ester
Disaccharide
Glycosyl compound
O-glycosyl compound
Tyrosol derivative
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Oxacycle
Polyol
Organoheterocyclic compound
Carboxylic acid derivative
Acetal
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Carbonyl group
Alcohol
Organic oxygen compound
Organic oxide
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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

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

22913197

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23958169

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Liang H, Liu K, Zhuang Z, Sun H, Sun B, Jiao M, Cai Y, Cai G: Potential of Forsythoside I as a therapeutic approach for acute lung injury: Involvement of TXNIP/NLRP3 inflammasome. Mol Immunol. 2021 Jun;134:192-201. doi: 10.1016/j.molimm.2021.03.004. Epub 2021 Apr 1. [PubMed:33812251 ]
Chen X, Wu Y, Chen C, Gu Y, Zhu C, Wang S, Chen J, Zhang L, Lv L, Zhang G, Yuan Y, Chai Y, Zhu M, Wu C: Identifying potential anti-COVID-19 pharmacological components of traditional Chinese medicine Lianhuaqingwen capsule based on human exposure and ACE2 biochromatography screening. Acta Pharm Sin B. 2021 Jan;11(1):222-236. doi: 10.1016/j.apsb.2020.10.002. Epub 2020 Oct 10. [PubMed:33072499 ]
Li Y, Guo Q, Yan Y, Chen T, Du C, Du H: Different effects of Forsythia suspensa metabolites on bovine serum albumin (BSA). Spectrochim Acta A Mol Biomol Spectrosc. 2019 May 5;214:309-319. doi: 10.1016/j.saa.2019.02.076. Epub 2019 Feb 18. [PubMed:30798212 ]
Bao J, Ding RB, Liang Y, Liu F, Wang K, Jia X, Zhang C, Chen M, Li P, Su H, Wan JB, Wang Y, He C: Differences in Chemical Component and Anticancer Activity of Green and Ripe Forsythiae Fructus. Am J Chin Med. 2017;45(7):1513-1536. doi: 10.1142/S0192415X17500823. Epub 2017 Sep 25. [PubMed:28946767 ]
Sun Y, Hou Z, Liu Z, Wang J: Ionic Liquid-Based Ultrasonic-Assisted Extraction of Forsythosides from the Leaf of Forsythia suspensa (Thunb.) Vahl and Subsequent Separation and Purification by High-Speed Counter-Current Chromatography. J Chromatogr Sci. 2016 Sep;54(8):1445-52. doi: 10.1093/chromsci/bmw069. Epub 2016 May 10. [PubMed:27165571 ]

Showing NP-Card for Forsythoside I (NP0140620)

MOL for NP0140620 (Forsythoside I)

3D MOL for NP0140620 (Forsythoside I)

3D SDF for NP0140620 (Forsythoside I)

3D-SDF for NP0140620 (Forsythoside I)

PDB for NP0140620 (Forsythoside I)

3D PDB for NP0140620 (Forsythoside I)

SMILES for NP0140620 (Forsythoside I)

INCHI for NP0140620 (Forsythoside I)

Structure for NP0140620 (Forsythoside I)

3D Structure for NP0140620 (Forsythoside I)