NP-MRD: Showing NP-Card for Gulsamanin (NP0076607)

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Record Information

Version

2.0

Created at

2022-04-28 21:47:59 UTC

Updated at

2022-04-28 21:47:59 UTC

NP-MRD ID

NP0076607

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Gulsamanin

Description

Gulsamanin belongs to the class of organic compounds known as coumarin glycosides. These are aromatic compounds containing a carbohydrate moiety glycosidically bound to a coumarin moiety. Gulsamanin is found in Daphne oleoides . Based on a literature review very few articles have been published on Gulsamanin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282223472D          

 38 42  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304282223472D          

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M  END
> <DATABASE_ID>
NP0076607

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=CC(O)=C(O)C(=C2OC1=O)C1=C2OC(=O)C=CC2=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H22O13/c1-34-13-7-10-6-11(27)18(29)17(23(10)38-24(13)33)16-12(4-2-9-3-5-15(28)37-22(9)16)35-25-21(32)20(31)19(30)14(8-26)36-25/h2-7,14,19-21,25-27,29-32H,8H2,1H3/t14-,19-,20+,21-,25-/m1/s1

> <INCHI_KEY>
NOSNPRHQZMFYES-KCZVUXFOSA-N

> <FORMULA>
C25H22O13

> <MOLECULAR_WEIGHT>
530.438

> <EXACT_MASS>
530.106040768

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
49.38382550962234

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6,7-dihydroxy-3-methoxy-7'-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H,2'H-[8,8'-bichromene]-2,2'-dione

> <ALOGPS_LOGP>
1.01

> <JCHEM_LOGP>
-0.07206224033333308

> <ALOGPS_LOGS>
-2.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.757497615144464

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.2568509639440455

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923462287393

> <JCHEM_POLAR_SURFACE_AREA>
201.67

> <JCHEM_REFRACTIVITY>
126.98109999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.06e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,7-dihydroxy-3-methoxy-7'-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-[8,8'-bichromene]-2,2'-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0     -12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0     -13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0     -12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -6.668   2.310   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
CONECT    1    2   25   29                                                  
CONECT    2    1    3    7                                                  
CONECT    3    2    4   13                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11    6                                                       
CONECT   13    3   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16   24                                                  
CONECT   16   15   17   23                                                  
CONECT   17   16   18   22                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   14                                                       
CONECT   20   18   21                                                       
CONECT   21   20                                                            
CONECT   22   17                                                            
CONECT   23   16                                                            
CONECT   24   15                                                            
CONECT   25    1   26   36                                                  
CONECT   26   25   27   32                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   31                                                  
CONECT   29   28    1   30                                                  
CONECT   30   29                                                            
CONECT   31   28                                                            
CONECT   32   26   33                                                       
CONECT   33   32   34   37                                                  
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   25                                                       
CONECT   37   33   38                                                       
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₂O₁₃

Average Mass

530.4380 Da

Monoisotopic Mass

530.10604 Da

IUPAC Name

6,7-dihydroxy-3-methoxy-7'-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H,2'H-[8,8'-bichromene]-2,2'-dione

Traditional Name

6,7-dihydroxy-3-methoxy-7'-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-[8,8'-bichromene]-2,2'-dione

CAS Registry Number

Not Available

SMILES

COC1=CC2=CC(O)=C(O)C(=C2OC1=O)C1=C2OC(=O)C=CC2=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C25H22O13/c1-34-13-7-10-6-11(27)18(29)17(23(10)38-24(13)33)16-12(4-2-9-3-5-15(28)37-22(9)16)35-25-21(32)20(31)19(30)14(8-26)36-25/h2-7,14,19-21,25-27,29-32H,8H2,1H3/t14-,19-,20+,21-,25-/m1/s1

InChI Key

NOSNPRHQZMFYES-KCZVUXFOSA-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
Daphne oleoides	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarin glycosides. These are aromatic compounds containing a carbohydrate moiety glycosidically bound to a coumarin moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Coumarin glycosides

Direct Parent

Coumarin glycosides

Alternative Parents

Substituents

Coumarin-7-o-glycoside
Coumarin o-glycoside
Phenolic glycoside
6,7-dihydroxycoumarin
7-hydroxycoumarin
Hexose monosaccharide
Hydroxycoumarin
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Monosaccharide
Oxane
Heteroaromatic compound
Lactone
Secondary alcohol
Acetal
Ether
Organoheterocyclic compound
Oxacycle
Polyol
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
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	1.01	ALOGPS
logP	-0.072	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	7.26	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	201.67 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	126.98 m³·mol⁻¹	ChemAxon
Polarizability	49.38 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00039301

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

100968115

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Gulsamanin (NP0076607)

MOL for NP0076607 (Gulsamanin)

3D MOL for NP0076607 (Gulsamanin)

3D SDF for NP0076607 (Gulsamanin)

3D-SDF for NP0076607 (Gulsamanin)

PDB for NP0076607 (Gulsamanin)

3D PDB for NP0076607 (Gulsamanin)

SMILES for NP0076607 (Gulsamanin)

INCHI for NP0076607 (Gulsamanin)

Structure for NP0076607 (Gulsamanin)

3D Structure for NP0076607 (Gulsamanin)