NP-MRD: Showing NP-Card for (2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1r,4as,5r,8ar)-1,4a-dimethyl-6-methylidene-5-[2-(2-oxo-5h-furan-3-yl)ethyl]-hexahydro-2h-naphthalene-1-carboxylate (NP0197963)

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Record Information

Version

2.0

Created at

2022-09-04 16:19:36 UTC

Updated at

2022-09-04 16:19:36 UTC

NP-MRD ID

NP0197963

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1r,4as,5r,8ar)-1,4a-dimethyl-6-methylidene-5-[2-(2-oxo-5h-furan-3-yl)ethyl]-hexahydro-2h-naphthalene-1-carboxylate

Description

ZINC238777809 belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated. (2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1r,4as,5r,8ar)-1,4a-dimethyl-6-methylidene-5-[2-(2-oxo-5h-furan-3-yl)ethyl]-hexahydro-2h-naphthalene-1-carboxylate is found in Andrographis paniculata. Based on a literature review very few articles have been published on ZINC238777809.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042218192D          

 35 38  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309042218192D          

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 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  1  1  0  0  0
  6 27  1  0  0  0  0
  2 27  1  0  0  0  0
 27 28  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 30 34  1  0  0  0  0
 34 35  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0197963

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]12CCC[C@](C)([C@@H]1CCC(=C)[C@H]2CCC1=CCOC1=O)C(=O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H38O9/c1-14-5-8-18-25(2,16(14)7-6-15-9-12-33-22(15)31)10-4-11-26(18,3)24(32)35-23-21(30)20(29)19(28)17(13-27)34-23/h9,16-21,23,27-30H,1,4-8,10-13H2,2-3H3/t16-,17-,18-,19-,20+,21-,23+,25+,26-/m1/s1

> <INCHI_KEY>
WWMGXPVENJOYMP-QHIQVHBBSA-N

> <FORMULA>
C26H38O9

> <MOLECULAR_WEIGHT>
494.581

> <EXACT_MASS>
494.251582804

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
51.469196263701775

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1R,4aS,5R,8aR)-1,4a-dimethyl-6-methylidene-5-[2-(2-oxo-2,5-dihydrofuran-3-yl)ethyl]-decahydronaphthalene-1-carboxylate

> <JCHEM_LOGP>
2.1724320089999987

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.00865187751419

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.169448315133106

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981093680169468

> <JCHEM_POLAR_SURFACE_AREA>
142.75000000000003

> <JCHEM_REFRACTIVITY>
124.4272

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1R,4aS,5R,8aR)-1,4a-dimethyl-6-methylidene-5-[2-(2-oxo-5H-furan-3-yl)ethyl]-hexahydro-2H-naphthalene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.390  -4.440   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.944  -4.440   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.760  -5.746   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       0.405  -4.493   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.318  -5.853   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.498  -7.159   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.225  -8.519   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.591  -9.825   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.131 -11.185   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.764  -8.573   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.487  -9.932   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.580  -7.267   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -4.119  -7.320   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.857  -5.907   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.673  -4.601   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.580   4.755   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.104   6.220   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -0.564   6.220   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -0.088   4.755   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       1.377   4.279   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   27                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7    8   27                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    5   12   13                                             
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   25                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   16   26                                                  
CONECT   26   25                                                            
CONECT   27    6    2   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   34                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   30   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₈O₉

Average Mass

494.5810 Da

Monoisotopic Mass

494.25158 Da

IUPAC Name

(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1R,4aS,5R,8aR)-1,4a-dimethyl-6-methylidene-5-[2-(2-oxo-2,5-dihydrofuran-3-yl)ethyl]-decahydronaphthalene-1-carboxylate

Traditional Name

(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1R,4aS,5R,8aR)-1,4a-dimethyl-6-methylidene-5-[2-(2-oxo-5H-furan-3-yl)ethyl]-hexahydro-2H-naphthalene-1-carboxylate

CAS Registry Number

Not Available

SMILES

C[C@@]12CCC[C@](C)([C@@H]1CCC(=C)[C@H]2CCC1=CCOC1=O)C(=O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C26H38O9/c1-14-5-8-18-25(2,16(14)7-6-15-9-12-33-22(15)31)10-4-11-26(18,3)24(32)35-23-21(30)20(29)19(28)17(13-27)34-23/h9,16-21,23,27-30H,1,4-8,10-13H2,2-3H3/t16-,17-,18-,19-,20+,21-,23+,25+,26-/m1/s1

InChI Key

WWMGXPVENJOYMP-QHIQVHBBSA-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

Species Name	Source	Reference
Andrographis paniculata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Diterpene glycosides

Alternative Parents

Substituents

Diterpene glycoside
Diterpene lactone
Diterpenoid
Clerodane diterpenoid
Hexose monosaccharide
2-furanone
Dicarboxylic acid or derivatives
Monosaccharide
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Dihydrofuran
Lactone
Secondary alcohol
Carboxylic acid ester
Polyol
Acetal
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Primary alcohol
Alcohol
Organic oxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	2.17	ChemAxon
pKa (Strongest Acidic)	12.17	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	142.75 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	124.43 m³·mol⁻¹	ChemAxon
Polarizability	51.47 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

124708191

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1r,4as,5r,8ar)-1,4a-dimethyl-6-methylidene-5-[2-(2-oxo-5h-furan-3-yl)ethyl]-hexahydro-2h-naphthalene-1-carboxylate (NP0197963)

MOL for NP0197963 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1r,4as,5r,8ar)-1,4a-dimethyl-6-methylidene-5-[2-(2-oxo-5h-furan-3-yl)ethyl]-hexahydro-2h-naphthalene-1-carboxylate)

3D MOL for NP0197963 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1r,4as,5r,8ar)-1,4a-dimethyl-6-methylidene-5-[2-(2-oxo-5h-furan-3-yl)ethyl]-hexahydro-2h-naphthalene-1-carboxylate)

3D SDF for NP0197963 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1r,4as,5r,8ar)-1,4a-dimethyl-6-methylidene-5-[2-(2-oxo-5h-furan-3-yl)ethyl]-hexahydro-2h-naphthalene-1-carboxylate)

3D-SDF for NP0197963 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1r,4as,5r,8ar)-1,4a-dimethyl-6-methylidene-5-[2-(2-oxo-5h-furan-3-yl)ethyl]-hexahydro-2h-naphthalene-1-carboxylate)

PDB for NP0197963 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1r,4as,5r,8ar)-1,4a-dimethyl-6-methylidene-5-[2-(2-oxo-5h-furan-3-yl)ethyl]-hexahydro-2h-naphthalene-1-carboxylate)

3D PDB for NP0197963 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1r,4as,5r,8ar)-1,4a-dimethyl-6-methylidene-5-[2-(2-oxo-5h-furan-3-yl)ethyl]-hexahydro-2h-naphthalene-1-carboxylate)

SMILES for NP0197963 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1r,4as,5r,8ar)-1,4a-dimethyl-6-methylidene-5-[2-(2-oxo-5h-furan-3-yl)ethyl]-hexahydro-2h-naphthalene-1-carboxylate)

INCHI for NP0197963 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1r,4as,5r,8ar)-1,4a-dimethyl-6-methylidene-5-[2-(2-oxo-5h-furan-3-yl)ethyl]-hexahydro-2h-naphthalene-1-carboxylate)

Structure for NP0197963 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1r,4as,5r,8ar)-1,4a-dimethyl-6-methylidene-5-[2-(2-oxo-5h-furan-3-yl)ethyl]-hexahydro-2h-naphthalene-1-carboxylate)

3D Structure for NP0197963 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1r,4as,5r,8ar)-1,4a-dimethyl-6-methylidene-5-[2-(2-oxo-5h-furan-3-yl)ethyl]-hexahydro-2h-naphthalene-1-carboxylate)