NP-MRD: Showing NP-Card for (-)-Aurantoside H (NP0078319)

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Record Information

Version

2.0

Created at

2022-04-28 23:25:09 UTC

Updated at

2022-04-28 23:25:09 UTC

NP-MRD ID

NP0078319

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Aurantoside H

Description

2-[(2S,4Z)-4-[(2E,4E,6E,8E,10E)-11-chloro-1-hydroxydodeca-2,4,6,8,10-pentaen-1-ylidene]-1-[(2S,3R,4R,5R)-4,5-dihydroxy-3-{[(2S,3S,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]-3,5-dioxopyrrolidin-2-yl]ethanimidic acid belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. (-)-Aurantoside H is found in Theonella swinhoei. Based on a literature review very few articles have been published on 2-[(2S,4Z)-4-[(2E,4E,6E,8E,10E)-11-chloro-1-hydroxydodeca-2,4,6,8,10-pentaen-1-ylidene]-1-[(2S,3R,4R,5R)-4,5-dihydroxy-3-{[(2S,3S,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]-3,5-dioxopyrrolidin-2-yl]ethanimidic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292201252D          

 43 45  0  0  1  0            999 V2000
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  1 40  1  1  0  0  0
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 41 43  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304292201252D          

 43 45  0  0  1  0            999 V2000
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   -1.9584   -3.3186    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7431   -3.0637    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9146   -2.2567    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3015   -1.7047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5169   -1.9596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6992   -2.0018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3562   -3.6157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7869   -4.1256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4000   -4.6776    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2285   -5.4846    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8416   -6.0366    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6262   -5.7817    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7977   -4.9747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1846   -4.4227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2393   -6.3337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6701   -6.8436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4439   -5.7395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1067   -1.7116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8212   -1.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5356   -1.7116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8212   -0.4741    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  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
  9 10  1  0  0  0  0
 10 11  2  0  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
 15 17  1  0  0  0  0
  5 18  1  0  0  0  0
  4 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
  1 21  1  0  0  0  0
 22 21  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 22 27  1  0  0  0  0
 25 28  1  6  0  0  0
 24 29  1  6  0  0  0
 23 30  1  6  0  0  0
 31 30  1  1  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 31 36  1  0  0  0  0
 34 37  1  6  0  0  0
 33 38  1  6  0  0  0
 32 39  1  1  0  0  0
  1 40  1  1  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0078319

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(Cl)=C/C=C/C=C/C=C/C=C/C(/O)=C1\C(=O)[C@H](CC(N)=O)N([C@H]2OC[C@@H](O)[C@@H](O)[C@H]2O[C@@H]2OC[C@@H](O)[C@@H](O)[C@@H]2O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H35ClN2O12/c1-14(29)9-7-5-3-2-4-6-8-10-16(32)20-21(36)15(11-19(30)35)31(26(20)40)27-25(23(38)18(34)12-41-27)43-28-24(39)22(37)17(33)13-42-28/h2-10,15,17-18,22-25,27-28,32-34,37-39H,11-13H2,1H3,(H2,30,35)/b3-2+,6-4+,7-5+,10-8+,14-9+,20-16-/t15-,17+,18+,22+,23+,24-,25+,27-,28-/m0/s1

> <INCHI_KEY>
LIMKXWLGCNDCHO-IZAQBDLYSA-N

> <FORMULA>
C28H35ClN2O12

> <MOLECULAR_WEIGHT>
627.04

> <EXACT_MASS>
626.1878523

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
63.64615072281201

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(2S,4Z)-4-[(2E,4E,6E,8E,10E)-11-chloro-1-hydroxydodeca-2,4,6,8,10-pentaen-1-ylidene]-1-[(2S,3R,4R,5R)-4,5-dihydroxy-3-{[(2S,3S,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]-3,5-dioxopyrrolidin-2-yl]acetamide

> <ALOGPS_LOGP>
0.51

> <JCHEM_LOGP>
-1.6577953769999993

> <ALOGPS_LOGS>
-3.41

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.25408161664

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.067490489552296

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5251481974583667

> <JCHEM_POLAR_SURFACE_AREA>
229.54

> <JCHEM_REFRACTIVITY>
156.58120000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.42e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(2S,4Z)-4-[(2E,4E,6E,8E,10E)-11-chloro-1-hydroxydodeca-2,4,6,8,10-pentaen-1-ylidene]-1-[(2S,3R,4R,5R)-4,5-dihydroxy-3-{[(2S,3S,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]-3,5-dioxopyrrolidin-2-yl]acetamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       0.199  -4.735   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.445  -5.640   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.910  -5.164   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.969  -7.105   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.874  -8.351   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.406  -8.190   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.032  -6.783   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.564  -6.622   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.190  -5.215   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.722  -5.054   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.348  -3.647   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.880  -3.486   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.506  -2.079   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.038  -1.918   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.664  -0.512   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.759   0.734   0.000  0.00  0.00           C+0
HETATM   17 Cl   UNK     0      14.196  -0.351   0.000  0.00  0.00          Cl+0
HETATM   18  O   UNK     0       1.248  -9.758   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.571  -7.105   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.476  -8.351   0.000  0.00  0.00           O+0
HETATM   21  N   UNK     0      -1.047  -5.640   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0      -2.511  -5.164   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.656  -6.195   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.120  -5.719   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.441  -4.213   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.296  -3.182   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -2.832  -3.658   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -6.905  -3.737   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -6.265  -6.749   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -3.336  -7.701   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -4.480  -8.732   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.160 -10.238   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -5.304 -11.268   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -6.769 -10.792   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -7.089  -9.286   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -5.945  -8.256   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -7.913 -11.823   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -4.984 -12.775   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -2.695 -10.714   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       0.199  -3.195   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       1.533  -2.425   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       2.867  -3.195   0.000  0.00  0.00           O+0
HETATM   43  N   UNK     0       1.533  -0.885   0.000  0.00  0.00           N+0
CONECT    1    2   21   40                                                  
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   19                                                  
CONECT    5    4    6   18                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    5                                                            
CONECT   19    4   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    1   22                                                  
CONECT   22   21   23   27                                                  
CONECT   23   22   24   30                                                  
CONECT   24   23   25   29                                                  
CONECT   25   24   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26   22                                                       
CONECT   28   25                                                            
CONECT   29   24                                                            
CONECT   30   23   31                                                       
CONECT   31   30   32   36                                                  
CONECT   32   31   33   39                                                  
CONECT   33   32   34   38                                                  
CONECT   34   33   35   37                                                  
CONECT   35   34   36                                                       
CONECT   36   35   31                                                       
CONECT   37   34                                                            
CONECT   38   33                                                            
CONECT   39   32                                                            
CONECT   40    1   41                                                       
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   90    0
END

View in JSmol

Synonyms

Value	Source
2-[(2S,4Z)-4-[(2E,4E,6E,8E,10E)-11-Chloro-1-hydroxydodeca-2,4,6,8,10-pentaen-1-ylidene]-1-[(2S,3R,4R,5R)-4,5-dihydroxy-3-{[(2S,3S,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]-3,5-dioxopyrrolidin-2-yl]ethanimidate	Generator

Chemical Formula

C₂₈H₃₅ClN₂O₁₂

Average Mass

627.0400 Da

Monoisotopic Mass

626.18785 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

C\C(Cl)=C/C=C/C=C/C=C/C=C/C(/O)=C1\C(=O)[C@H](CC(N)=O)N([C@H]2OC[C@@H](O)[C@@H](O)[C@H]2O[C@@H]2OC[C@@H](O)[C@@H](O)[C@@H]2O)C1=O

InChI Identifier

InChI=1S/C28H35ClN2O12/c1-14(29)9-7-5-3-2-4-6-8-10-16(32)20-21(36)15(11-19(30)35)31(26(20)40)27-25(23(38)18(34)12-41-27)43-28-24(39)22(37)17(33)13-42-28/h2-10,15,17-18,22-25,27-28,32-34,37-39H,11-13H2,1H3,(H2,30,35)/b3-2+,6-4+,7-5+,10-8+,14-9+,20-16-/t15-,17+,18+,22+,23+,24-,25+,27-,28-/m0/s1

InChI Key

LIMKXWLGCNDCHO-IZAQBDLYSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Theonella swinhoei	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

O-glycosyl compound
N-glycosyl compound
Disaccharide
N-alkylpyrrolidine
3-pyrrolidone
2-pyrrolidone
Pyrrolidone
Oxane
Vinylogous acid
Tertiary carboxylic acid amide
Pyrrolidine
Cyclic ketone
Secondary alcohol
Lactam
Ketone
Carboxamide group
Oxacycle
Azacycle
Chloroalkene
Haloalkene
Organoheterocyclic compound
Vinyl halide
Vinyl chloride
Polyol
Enol
Carboxylic acid derivative
Carboximidic acid derivative
Carboximidic acid
Acetal
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Organochloride
Organohalogen compound
Carbonyl group
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic 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
logP	0.51	ALOGPS
logP	-1.7	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	5.07	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	229.54 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	156.58 m³·mol⁻¹	ChemAxon
Polarizability	63.65 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

163039418

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Aurantoside H (NP0078319)

MOL for NP0078319 ((-)-Aurantoside H)

3D MOL for NP0078319 ((-)-Aurantoside H)

3D SDF for NP0078319 ((-)-Aurantoside H)

3D-SDF for NP0078319 ((-)-Aurantoside H)

PDB for NP0078319 ((-)-Aurantoside H)

3D PDB for NP0078319 ((-)-Aurantoside H)

SMILES for NP0078319 ((-)-Aurantoside H)

INCHI for NP0078319 ((-)-Aurantoside H)

Structure for NP0078319 ((-)-Aurantoside H)

3D Structure for NP0078319 ((-)-Aurantoside H)