NP-MRD: Showing NP-Card for Sennoside F (NP0338529)

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Record Information

Version

2.0

Created at

2024-09-11 15:54:22 UTC

Updated at

2024-09-11 15:54:22 UTC

NP-MRD ID

NP0338529

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sennoside F

Description

Sennoside F 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 F is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Sennoside F has been detected, but not quantified in, green vegetables. This could make sennoside F a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241221232D          

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M  END


  Mrv0541 02241221232D          

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 63 64  1  0  0  0  0
 61 65  1  0  0  0  0
 65 66  2  0  0  0  0
 65 67  1  0  0  0  0
 24 68  1  6  0  0  0
 23 69  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0338529

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]1(C2=C(C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=CC=C2)C(=O)C2=C1C=C(C=C2O)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-ODLWGOIJSA-N

> <FORMULA>
C44H38O23

> <MOLECULAR_WEIGHT>
934.7587

> <EXACT_MASS>
934.180387522

> <JCHEM_ACCEPTOR_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
87.21643331932087

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
12

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(9R)-9-[(9S)-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>
3.237530696624481

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.745645448200713

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9540754237026876

> <JCHEM_POLAR_SURFACE_AREA>
391.33000000000004

> <JCHEM_REFRACTIVITY>
216.3896000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.48e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9R)-9-[(9S)-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  C   UNK     0       8.281  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.947  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.613  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.613  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.947  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.281  -4.620   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.947  -6.930   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.281  -7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.281  -9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.614 -10.010   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.948  -9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.948  -7.700   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.614  -6.930   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      12.282  -6.930   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      12.282  -5.390   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      12.282 -10.010   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       9.614 -11.550   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.947 -10.010   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.280  -5.390   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.280  -6.930   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.946  -4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.946  -3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.280  -2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.280  -0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.946   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.946   1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.612   2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.279   1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.279   0.000   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.612  -0.770   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.612   3.850   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       0.279   4.620   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.279   6.160   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.055   6.930   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.389   6.160   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -2.389   4.620   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -1.055   3.850   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -3.722   3.850   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -3.722   2.310   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -3.722   6.930   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -1.055   8.470   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       1.612   6.930   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       1.612   8.470   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       0.279   9.240   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       2.946   9.240   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       4.280   8.470   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0       2.946  10.780   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0       4.280   2.310   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0       4.280   3.850   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0       5.613   1.540   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       5.613   0.000   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       6.947  -0.770   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       8.281   0.000   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       8.281   1.540   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       6.947   2.310   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0       6.947   3.850   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0       9.614  -0.770   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0      10.948   0.000   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0       9.614  -2.310   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0       1.612  -2.310   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0       0.279  -3.080   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0       0.279  -4.620   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0       1.612  -5.390   0.000  0.00  0.00           C+0
HETATM   64  O   UNK     0       1.612  -6.930   0.000  0.00  0.00           O+0
HETATM   65  C   UNK     0      -1.055  -2.310   0.000  0.00  0.00           C+0
HETATM   66  O   UNK     0      -2.389  -3.080   0.000  0.00  0.00           O+0
HETATM   67  O   UNK     0      -1.055  -0.770   0.000  0.00  0.00           O+0
HETATM   68  H   UNK     0       2.946  -1.540   0.000  0.00  0.00           H+0
HETATM   69  H   UNK     0       5.613  -1.540   0.000  0.00  0.00           H+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5   19                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10   18                                                  
CONECT   10    9   11   17                                                  
CONECT   11   10   12   16                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12    8                                                       
CONECT   14   12   15                                                       
CONECT   15   14                                                            
CONECT   16   11                                                            
CONECT   17   10                                                            
CONECT   18    9                                                            
CONECT   19    4   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   63                                                  
CONECT   22   21   23   60                                                  
CONECT   23   22    3   24   69                                             
CONECT   24   23   25   51   68                                             
CONECT   25   24   26   30                                                  
CONECT   26   25   27   48                                                  
CONECT   27   26   28   31                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   25                                                       
CONECT   31   27   32                                                       
CONECT   32   31   33   37                                                  
CONECT   33   32   34   42                                                  
CONECT   34   33   35   41                                                  
CONECT   35   34   36   40                                                  
CONECT   36   35   37   38                                                  
CONECT   37   36   32                                                       
CONECT   38   36   39                                                       
CONECT   39   38                                                            
CONECT   40   35                                                            
CONECT   41   34                                                            
CONECT   42   33   43                                                       
CONECT   43   42   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45                                                            
CONECT   48   26   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48   51   55                                                  
CONECT   51   50   24   52                                                  
CONECT   52   51   53                                                       
CONECT   53   52   54   57                                                  
CONECT   54   53   55                                                       
CONECT   55   54   50   56                                                  
CONECT   56   55                                                            
CONECT   57   53   58   59                                                  
CONECT   58   57                                                            
CONECT   59   57                                                            
CONECT   60   22   61                                                       
CONECT   61   60   62   65                                                  
CONECT   62   61   63                                                       
CONECT   63   62   21   64                                                  
CONECT   64   63                                                            
CONECT   65   61   66   67                                                  
CONECT   66   65                                                            
CONECT   67   65                                                            
CONECT   68   24                                                            
CONECT   69   23                                                            
MASTER        0    0    0    0    0    0    0    0   69    0  152    0
END

View in JSmol

Synonyms

Value	Source
(9S,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-[(9S)-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-[(9S)-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=C(C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=CC=C2)C(=O)C2=C1C=C(C=C2O)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-ODLWGOIJSA-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	87.22 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

HMDB0034311

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012659

KNApSAcK ID

Not Available

Chemspider ID

30777047

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751545

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Sennoside F (NP0338529)

MOL for NP0338529 (Sennoside F)

3D MOL for NP0338529 (Sennoside F)

3D SDF for NP0338529 (Sennoside F)

3D-SDF for NP0338529 (Sennoside F)

PDB for NP0338529 (Sennoside F)

3D PDB for NP0338529 (Sennoside F)

SMILES for NP0338529 (Sennoside F)

INCHI for NP0338529 (Sennoside F)

Structure for NP0338529 (Sennoside F)

3D Structure for NP0338529 (Sennoside F)