NP-MRD: Showing NP-Card for Tinosposinenside C (NP0077261)

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Record Information

Version

2.0

Created at

2022-04-28 22:25:36 UTC

Updated at

2022-04-28 22:25:36 UTC

NP-MRD ID

NP0077261

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tinosposinenside C

Description

(2S,4aR,6aS,7R,9S,10R,10aR,10bS)-2-(furan-3-yl)-9-hydroxy-10b-methyl-4-oxo-7-{[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1H-naphtho[2,1-c]pyran-10-yl acetate belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. Tinosposinenside C is found in Tinospora sinensis . Based on a literature review very few articles have been published on (2S,4aR,6aS,7R,9S,10R,10aR,10bS)-2-(furan-3-yl)-9-hydroxy-10b-methyl-4-oxo-7-{[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1H-naphtho[2,1-c]pyran-10-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292200252D          

 38 42  0  0  1  0            999 V2000
    1.5395   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652304292200252D          

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    4.8395   -2.4454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -3.8743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.8743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  6  8  1  1  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  9 14  1  0  0  0  0
 13 15  1  1  0  0  0
 12 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
 10 23  1  1  0  0  0
 21 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 20 28  1  0  0  0  0
 27 29  1  6  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 29 33  1  0  0  0  0
 20 34  1  6  0  0  0
  5 35  1  6  0  0  0
  4 36  1  1  0  0  0
  3 37  1  6  0  0  0
  1 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0077261

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1[C@@H](O)C[C@@H](O[C@@H]2O[C@@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]2CC[C@H]3C(=O)O[C@@H](C[C@@]3(C)[C@H]12)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H36O12/c1-11(28)35-23-15(29)7-16(37-25-22(32)21(31)20(30)18(9-27)38-25)13-3-4-14-24(33)36-17(12-5-6-34-10-12)8-26(14,2)19(13)23/h5-6,10,13-23,25,27,29-32H,3-4,7-9H2,1-2H3/t13-,14+,15+,16-,17+,18+,19+,20-,21+,22-,23+,25-,26-/m1/s1

> <INCHI_KEY>
WAJJNHUEVQGAOS-QDMZWKJISA-N

> <FORMULA>
C26H36O12

> <MOLECULAR_WEIGHT>
540.562

> <EXACT_MASS>
540.220676599

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
53.37390536590002

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,4aR,6aS,7R,9S,10R,10aR,10bS)-2-(furan-3-yl)-9-hydroxy-10b-methyl-4-oxo-7-{[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1H-naphtho[2,1-c]pyran-10-yl acetate

> <ALOGPS_LOGP>
-0.45

> <JCHEM_LOGP>
-1.0214182220000008

> <ALOGPS_LOGS>
-2.20

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.15226640979817

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.204751724007021

> <JCHEM_PKA_STRONGEST_BASIC>
-2.861267262372732

> <JCHEM_POLAR_SURFACE_AREA>
185.35

> <JCHEM_REFRACTIVITY>
125.26799999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.39e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,4aR,6aS,7R,9S,10R,10aR,10bS)-2-(furan-3-yl)-9-hydroxy-10b-methyl-4-oxo-7-{[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydro-1H-naphtho[2,1-c]pyran-10-yl acetate

> <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       2.874  -4.565   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.414  -4.565   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.184  -5.898   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.724  -5.898   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.494  -4.565   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.724  -3.231   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.184  -3.231   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       7.494  -1.897   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.494   3.437   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       4.414   3.437   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.184   4.771   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.414   6.105   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.724   4.771   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.206  -1.897   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -0.206   0.770   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.206   3.437   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.738   3.598   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -2.058   5.105   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -0.724   5.875   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.420   4.844   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       9.034  -4.565   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       7.494  -7.232   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       4.414  -7.232   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       2.104  -3.231   0.000  0.00  0.00           O+0
CONECT    1    2   38                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4   37                                                  
CONECT    4    3    5   36                                                  
CONECT    5    4    6   35                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    2                                                       
CONECT    8    6    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11   23                                                  
CONECT   11   10   12   20                                                  
CONECT   12   11   13   16                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13    9                                                       
CONECT   15   13                                                            
CONECT   16   12   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   11   21   28   34                                             
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22   10                                                       
CONECT   24   21   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27   20                                                       
CONECT   29   27   30   33                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   29                                                       
CONECT   34   20                                                            
CONECT   35    5                                                            
CONECT   36    4                                                            
CONECT   37    3                                                            
CONECT   38    1                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Value	Source
(2S,4AR,6as,7R,9S,10R,10ar,10BS)-2-(furan-3-yl)-9-hydroxy-10b-methyl-4-oxo-7-{[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1H-naphtho[2,1-c]pyran-10-yl acetic acid	Generator

Chemical Formula

C₂₆H₃₆O₁₂

Average Mass

540.5620 Da

Monoisotopic Mass

540.22068 Da

IUPAC Name

(2S,4aR,6aS,7R,9S,10R,10aR,10bS)-2-(furan-3-yl)-9-hydroxy-10b-methyl-4-oxo-7-{[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1H-naphtho[2,1-c]pyran-10-yl acetate

Traditional Name

(2S,4aR,6aS,7R,9S,10R,10aR,10bS)-2-(furan-3-yl)-9-hydroxy-10b-methyl-4-oxo-7-{[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydro-1H-naphtho[2,1-c]pyran-10-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1[C@@H](O)C[C@@H](O[C@@H]2O[C@@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]2CC[C@H]3C(=O)O[C@@H](C[C@@]3(C)[C@H]12)C1=COC=C1

InChI Identifier

InChI=1S/C26H36O12/c1-11(28)35-23-15(29)7-16(37-25-22(32)21(31)20(30)18(9-27)38-25)13-3-4-14-24(33)36-17(12-5-6-34-10-12)8-26(14,2)19(13)23/h5-6,10,13-23,25,27,29-32H,3-4,7-9H2,1-2H3/t13-,14+,15+,16-,17+,18+,19+,20-,21+,22-,23+,25-,26-/m1/s1

InChI Key

WAJJNHUEVQGAOS-QDMZWKJISA-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
Tinospora sinensis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Substituents

Naphthopyran
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Naphthalene
Delta_valerolactone
Delta valerolactone
Pyran
Oxane
Monosaccharide
Dicarboxylic acid or derivatives
Cyclitol or derivatives
Heteroaromatic compound
Furan
Cyclic alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Polyol
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
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	-0.45	ALOGPS
logP	-1	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	185.35 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	125.27 m³·mol⁻¹	ChemAxon
Polarizability	53.37 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	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

163039263

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Tinosposinenside C (NP0077261)

MOL for NP0077261 (Tinosposinenside C)

3D MOL for NP0077261 (Tinosposinenside C)

3D SDF for NP0077261 (Tinosposinenside C)

3D-SDF for NP0077261 (Tinosposinenside C)

PDB for NP0077261 (Tinosposinenside C)

3D PDB for NP0077261 (Tinosposinenside C)

SMILES for NP0077261 (Tinosposinenside C)

INCHI for NP0077261 (Tinosposinenside C)

Structure for NP0077261 (Tinosposinenside C)

3D Structure for NP0077261 (Tinosposinenside C)