NP-MRD: Showing NP-Card for Sennoside E (NP0338560)

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Record Information

Version

2.0

Created at

2024-09-11 16:03:16 UTC

Updated at

2024-09-11 16:03:16 UTC

NP-MRD ID

NP0338560

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sennoside E

Description

Sennoside E belongs to the class of organic compounds known as anthracenecarboxylic acids. These are organic compounds containing a carboxylic acid group attached to an anthracene ring system. Sennoside E is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Sennoside E has been detected, but not quantified in, green vegetables. This could make sennoside e a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241221312D          

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M  END


  Mrv0541 02241221312D          

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 65 66  2  0  0  0  0
 58 66  1  0  0  0  0
 66 67  1  0  0  0  0
 32 68  1  1  0  0  0
 29 69  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0338560

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(C2=CC(=CC(O)=C2C(=O)C2=C1C=CC=C2O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C(O)=O)[C@]1([H])C2=C(C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3OC(=O)C(O)=O)=CC=C2)C(=O)C2=C1C=C(C=C2O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C44H38O23/c45-11-23-31(49)35(53)37(55)43(65-23)63-21-5-1-3-15-25(17-7-13(39(56)57)9-19(47)27(17)33(51)29(15)21)26-16-4-2-6-22(30(16)34(52)28-18(26)8-14(40(58)59)10-20(28)48)64-44-38(67-42(62)41(60)61)36(54)32(50)24(12-46)66-44/h1-10,23-26,31-32,35-38,43-50,53-55H,11-12H2,(H,56,57)(H,58,59)(H,60,61)/t23-,24-,25-,26-,31-,32-,35+,36+,37-,38-,43-,44-/m1/s1

> <INCHI_KEY>
WCXZMEMQOKTKSI-WENVHRLESA-N

> <FORMULA>
C44H38O23

> <MOLECULAR_WEIGHT>
934.7587

> <EXACT_MASS>
934.180387522

> <JCHEM_ACCEPTOR_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
87.33274555625094

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
12

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(9R)-9-[(9R)-2-carboxy-5-{[(2S,3R,4S,5S,6R)-3-[(carboxycarbonyl)oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-10-oxo-9,10-dihydroanthracen-9-yl]-4-hydroxy-10-oxo-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9,10-dihydroanthracene-2-carboxylic acid

> <ALOGPS_LOGP>
1.00

> <JCHEM_LOGP>
1.8222903199999996

> <ALOGPS_LOGS>
-3.32

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
3.23753069662448

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.745645448200713

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9540754237026876

> <JCHEM_POLAR_SURFACE_AREA>
391.33

> <JCHEM_REFRACTIVITY>
216.38960000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.48e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9R)-9-[(9R)-2-carboxy-5-{[(2S,3R,4S,5S,6R)-3-[(carboxycarbonyl)oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-10-oxo-9H-anthracen-9-yl]-4-hydroxy-10-oxo-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9H-anthracene-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -2.628  -3.080   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.294  -2.310   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.294  -0.770   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.040  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.040  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.373  -5.390   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.373  -6.930   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.707  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.041  -5.390   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.041  -6.930   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.375  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.375  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.708  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.042  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.042  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.708  -5.390   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.708  -6.930   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.042  -7.700   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.042  -9.240   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.376 -10.010   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.376 -11.550   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      10.709 -12.320   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      10.709  -9.240   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      12.043 -10.010   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      10.709  -7.700   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      12.043  -6.930   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       9.376  -6.930   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       9.376  -5.390   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.041  -2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.707  -3.080   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.373  -2.310   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.041  -0.770   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.707   0.000   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.707   1.540   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.373   2.310   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       1.373   3.850   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       0.040   4.620   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -1.294   3.850   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -2.628   4.620   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -2.628   6.160   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -3.961   6.930   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -1.294   6.930   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      -1.294   8.470   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       0.040   6.160   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       1.373   6.930   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       2.707   6.160   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0       2.707   4.620   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0       4.041   6.930   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0       4.041   8.470   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0       5.375   6.160   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      -3.961   3.850   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      -5.295   4.620   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0       0.040   1.540   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       0.040   0.000   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       1.373  -0.770   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       4.041   2.310   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0       4.041   3.850   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0       5.375   1.540   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       5.375   0.000   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0       6.708  -0.770   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0       8.042   0.000   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0       9.376  -0.770   0.000  0.00  0.00           C+0
HETATM   63  O   UNK     0      10.709   0.000   0.000  0.00  0.00           O+0
HETATM   64  O   UNK     0       9.376  -2.310   0.000  0.00  0.00           O+0
HETATM   65  C   UNK     0       8.042   1.540   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0       6.708   2.310   0.000  0.00  0.00           C+0
HETATM   67  O   UNK     0       6.708   3.850   0.000  0.00  0.00           O+0
HETATM   68  H   UNK     0       2.707  -1.540   0.000  0.00  0.00           H+0
HETATM   69  H   UNK     0       5.375  -1.540   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   31                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   30                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   16                                                  
CONECT   12   11   13   29                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   27                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   18   28                                                  
CONECT   28   27                                                            
CONECT   29   12   30   32   69                                             
CONECT   30   29    8   31                                                  
CONECT   31   30    4                                                       
CONECT   32   29   33   59   68                                             
CONECT   33   32   34   55                                                  
CONECT   34   33   35   56                                                  
CONECT   35   34   36   53                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   44                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   51                                                  
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   37   45                                                  
CONECT   45   44   46                                                       
CONECT   46   45   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48                                                            
CONECT   51   39   52                                                       
CONECT   52   51                                                            
CONECT   53   35   54                                                       
CONECT   54   53   55                                                       
CONECT   55   54   33                                                       
CONECT   56   34   57   58                                                  
CONECT   57   56                                                            
CONECT   58   56   59   66                                                  
CONECT   59   58   32   60                                                  
CONECT   60   59   61                                                       
CONECT   61   60   62   65                                                  
CONECT   62   61   63   64                                                  
CONECT   63   62                                                            
CONECT   64   62                                                            
CONECT   65   61   66                                                       
CONECT   66   65   58   67                                                  
CONECT   67   66                                                            
CONECT   68   32                                                            
CONECT   69   29                                                            
MASTER        0    0    0    0    0    0    0    0   69    0  152    0
END

View in JSmol

Synonyms

Value	Source
(9R,9'r)-5-{[(2S,3R,4S,5S,6R)-3-[(carboxycarbonyl)oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,4'-dihydroxy-10,10'-dioxo-5'-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9H,9'H,10H,10'H-[9,9'-bianthracene]-2,2'-dicarboxylate	Generator
Sennoside e	MeSH
Sennoside F	MeSH

Chemical Formula

C₄₄H₃₈O₂₃

Average Mass

934.7587 Da

Monoisotopic Mass

934.18039 Da

IUPAC Name

(9R)-9-[(9R)-2-carboxy-5-{[(2S,3R,4S,5S,6R)-3-[(carboxycarbonyl)oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-10-oxo-9,10-dihydroanthracen-9-yl]-4-hydroxy-10-oxo-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9,10-dihydroanthracene-2-carboxylic acid

Traditional Name

(9R)-9-[(9R)-2-carboxy-5-{[(2S,3R,4S,5S,6R)-3-[(carboxycarbonyl)oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-10-oxo-9H-anthracen-9-yl]-4-hydroxy-10-oxo-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9H-anthracene-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]1(C2=CC(=CC(O)=C2C(=O)C2=C1C=CC=C2O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C(O)=O)[C@]1([H])C2=C(C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3OC(=O)C(O)=O)=CC=C2)C(=O)C2=C1C=C(C=C2O)C(O)=O

InChI Identifier

InChI=1S/C44H38O23/c45-11-23-31(49)35(53)37(55)43(65-23)63-21-5-1-3-15-25(17-7-13(39(56)57)9-19(47)27(17)33(51)29(15)21)26-16-4-2-6-22(30(16)34(52)28-18(26)8-14(40(58)59)10-20(28)48)64-44-38(67-42(62)41(60)61)36(54)32(50)24(12-46)66-44/h1-10,23-26,31-32,35-38,43-50,53-55H,11-12H2,(H,56,57)(H,58,59)(H,60,61)/t23-,24-,25-,26-,31-,32-,35+,36+,37-,38-,43-,44-/m1/s1

InChI Key

WCXZMEMQOKTKSI-WENVHRLESA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthracenecarboxylic acids. These are organic compounds containing a carboxylic acid group attached to an anthracene ring system.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Anthracenes

Sub Class

Anthracenecarboxylic acids and derivatives

Direct Parent

Anthracenecarboxylic acids

Alternative Parents

Substituents

Anthracene carboxylic acid
Phenolic glycoside
2-naphthalenecarboxylic acid or derivatives
2-naphthalenecarboxylic acid
Tetracarboxylic acid or derivatives
O-glycosyl compound
Glycosyl compound
Hydroxybenzoic acid
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Oxane
Monosaccharide
Vinylogous acid
Carboxylic acid ester
Ketone
Secondary alcohol
Acetal
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Polyol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Primary alcohol
Alcohol
Organooxygen 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	ALOGPS
logP	1.82	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	1.75	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	22	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	391.33 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	216.39 m³·mol⁻¹	ChemAxon
Polarizability	87.33 Å³	ChemAxon
Number of Rings	8	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

HMDB0033144

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011146

KNApSAcK ID

Not Available

Chemspider ID

30776977

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751381

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Sennoside E (NP0338560)

MOL for NP0338560 (Sennoside E)

3D MOL for NP0338560 (Sennoside E)

3D SDF for NP0338560 (Sennoside E)

3D-SDF for NP0338560 (Sennoside E)

PDB for NP0338560 (Sennoside E)

3D PDB for NP0338560 (Sennoside E)

SMILES for NP0338560 (Sennoside E)

INCHI for NP0338560 (Sennoside E)

Structure for NP0338560 (Sennoside E)

3D Structure for NP0338560 (Sennoside E)