NP-MRD: Showing NP-Card for (1r,2s,3s,5s,8r,11r,12r)-5-[(2r,3r,4r,5r)-3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl]-12-hydroxy-3,11-dimethyl-6,14-dioxatetracyclo[10.2.2.0²,¹¹.0³,⁸]hexadec-15-ene-7,13-dione (NP0296978)

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Record Information

Version

2.0

Created at

2022-09-10 06:54:12 UTC

Updated at

2022-09-10 06:54:12 UTC

NP-MRD ID

NP0296978

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,3s,5s,8r,11r,12r)-5-[(2r,3r,4r,5r)-3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl]-12-hydroxy-3,11-dimethyl-6,14-dioxatetracyclo[10.2.2.0²,¹¹.0³,⁸]hexadec-15-ene-7,13-dione

Description

(1R,2S,3S,5S,8R,11R,12R)-5-[(2R,3R,4R,5R)-3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl]-12-hydroxy-3,11-dimethyl-6,14-dioxatetracyclo[10.2.2.0²,¹¹.0³,⁸]Hexadec-15-ene-7,13-dione 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. (1r,2s,3s,5s,8r,11r,12r)-5-[(2r,3r,4r,5r)-3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl]-12-hydroxy-3,11-dimethyl-6,14-dioxatetracyclo[10.2.2.0²,¹¹.0³,⁸]hexadec-15-ene-7,13-dione is found in Tinospora smilacina. Based on a literature review very few articles have been published on (1R,2S,3S,5S,8R,11R,12R)-5-[(2R,3R,4R,5R)-3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl]-12-hydroxy-3,11-dimethyl-6,14-dioxatetracyclo[10.2.2.0²,¹¹.0³,⁸]Hexadec-15-ene-7,13-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102208542D          

 32 36  0  0  1  0            999 V2000
   -4.8917    1.0841    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


  Mrv1652309102208542D          

 32 36  0  0  1  0            999 V2000
   -4.8917    1.0841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0296978

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1O[C@@H](OC)[C@@](O)([C@H]1O)[C@@H]1C[C@]2(C)[C@@H](CC[C@]3(C)[C@H]2[C@@H]2OC(=O)[C@@]3(O)C=C2)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O10/c1-19-9-12(22(27)14(23)16(28-3)32-18(22)29-4)31-15(24)10(19)5-7-20(2)13(19)11-6-8-21(20,26)17(25)30-11/h6,8,10-14,16,18,23,26-27H,5,7,9H2,1-4H3/t10-,11+,12-,13-,14-,16+,18+,19+,20+,21-,22-/m0/s1

> <INCHI_KEY>
VEJSKYWCJMGHFY-XZQFGHCISA-N

> <FORMULA>
C22H30O10

> <MOLECULAR_WEIGHT>
454.472

> <EXACT_MASS>
454.183897166

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
44.74588248165176

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,3S,5S,8R,11R,12R)-5-[(2R,3R,4R,5R)-3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl]-12-hydroxy-3,11-dimethyl-6,14-dioxatetracyclo[10.2.2.0^{2,11}.0^{3,8}]hexadec-15-ene-7,13-dione

> <JCHEM_LOGP>
0.2921701859999997

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.708120778308347

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.963445120332123

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9035265463299695

> <JCHEM_POLAR_SURFACE_AREA>
140.98000000000002

> <JCHEM_REFRACTIVITY>
105.54949999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,3S,5S,8R,11R,12R)-5-[(2R,3R,4R,5R)-3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl]-12-hydroxy-3,11-dimethyl-6,14-dioxatetracyclo[10.2.2.0^{2,11}.0^{3,8}]hexadec-15-ene-7,13-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -9.131   2.024   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -8.042   0.935   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -6.555   1.334   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -6.003   2.772   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -4.465   2.691   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -3.496   3.888   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.975   3.648   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.066   1.204   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.629   1.756   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -3.367  -0.168   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.829  -0.248   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.129  -1.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.291  -0.329   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.408  -1.701   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.247  -0.409   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.942  -1.207   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.408  -2.122   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.646  -3.153   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.345  -4.525   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.484  -1.861   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.022  -1.941   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.785  -0.489   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.108  -3.073   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.946  -1.781   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.269  -4.364   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.268  -4.284   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.968  -2.912   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.506  -2.832   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -4.344  -4.123   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -4.205  -1.460   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -5.358   0.365   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -5.438  -1.173   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   31                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9   10   31                                             
CONECT    9    8                                                            
CONECT   10    8   11   30                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14   27                                             
CONECT   13   12                                                            
CONECT   14   12   15   23                                                  
CONECT   15   14   16   22                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20   23                                             
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   15                                                       
CONECT   23   18   14   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   12   28                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   10                                                       
CONECT   31    8    3   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₀O₁₀

Average Mass

454.4720 Da

Monoisotopic Mass

454.18390 Da

IUPAC Name

(1R,2S,3S,5S,8R,11R,12R)-5-[(2R,3R,4R,5R)-3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl]-12-hydroxy-3,11-dimethyl-6,14-dioxatetracyclo[10.2.2.0^{2,11}.0^{3,8}]hexadec-15-ene-7,13-dione

Traditional Name

(1R,2S,3S,5S,8R,11R,12R)-5-[(2R,3R,4R,5R)-3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl]-12-hydroxy-3,11-dimethyl-6,14-dioxatetracyclo[10.2.2.0^{2,11}.0^{3,8}]hexadec-15-ene-7,13-dione

CAS Registry Number

Not Available

SMILES

CO[C@@H]1O[C@@H](OC)[C@@](O)([C@H]1O)[C@@H]1C[C@]2(C)[C@@H](CC[C@]3(C)[C@H]2[C@@H]2OC(=O)[C@@]3(O)C=C2)C(=O)O1

InChI Identifier

InChI=1S/C22H30O10/c1-19-9-12(22(27)14(23)16(28-3)32-18(22)29-4)31-15(24)10(19)5-7-20(2)13(19)11-6-8-21(20,26)17(25)30-11/h6,8,10-14,16,18,23,26-27H,5,7,9H2,1-4H3/t10-,11+,12-,13-,14-,16+,18+,19+,20+,21-,22-/m0/s1

InChI Key

VEJSKYWCJMGHFY-XZQFGHCISA-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
Tinospora smilacina	LOTUS Database	35616633

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
Glycosyl compound
O-glycosyl compound
Naphthalene
Pentose monosaccharide
Delta valerolactone
Dihydropyranone
Delta_valerolactone
Oxane
Pyran
Monosaccharide
Dicarboxylic acid or derivatives
Tetrahydrofuran
Tertiary alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Acetal
Organooxygen compound
Alcohol
Organic oxygen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
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	0.29	ChemAxon
pKa (Strongest Acidic)	10.96	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	140.98 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	105.55 m³·mol⁻¹	ChemAxon
Polarizability	44.75 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

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

162972721

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2s,3s,5s,8r,11r,12r)-5-[(2r,3r,4r,5r)-3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl]-12-hydroxy-3,11-dimethyl-6,14-dioxatetracyclo[10.2.2.0²,¹¹.0³,⁸]hexadec-15-ene-7,13-dione (NP0296978)

MOL for NP0296978 ((1r,2s,3s,5s,8r,11r,12r)-5-[(2r,3r,4r,5r)-3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl]-12-hydroxy-3,11-dimethyl-6,14-dioxatetracyclo[10.2.2.0²,¹¹.0³,⁸]hexadec-15-ene-7,13-dione)

3D MOL for NP0296978 ((1r,2s,3s,5s,8r,11r,12r)-5-[(2r,3r,4r,5r)-3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl]-12-hydroxy-3,11-dimethyl-6,14-dioxatetracyclo[10.2.2.0²,¹¹.0³,⁸]hexadec-15-ene-7,13-dione)

3D SDF for NP0296978 ((1r,2s,3s,5s,8r,11r,12r)-5-[(2r,3r,4r,5r)-3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl]-12-hydroxy-3,11-dimethyl-6,14-dioxatetracyclo[10.2.2.0²,¹¹.0³,⁸]hexadec-15-ene-7,13-dione)

3D-SDF for NP0296978 ((1r,2s,3s,5s,8r,11r,12r)-5-[(2r,3r,4r,5r)-3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl]-12-hydroxy-3,11-dimethyl-6,14-dioxatetracyclo[10.2.2.0²,¹¹.0³,⁸]hexadec-15-ene-7,13-dione)

PDB for NP0296978 ((1r,2s,3s,5s,8r,11r,12r)-5-[(2r,3r,4r,5r)-3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl]-12-hydroxy-3,11-dimethyl-6,14-dioxatetracyclo[10.2.2.0²,¹¹.0³,⁸]hexadec-15-ene-7,13-dione)

3D PDB for NP0296978 ((1r,2s,3s,5s,8r,11r,12r)-5-[(2r,3r,4r,5r)-3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl]-12-hydroxy-3,11-dimethyl-6,14-dioxatetracyclo[10.2.2.0²,¹¹.0³,⁸]hexadec-15-ene-7,13-dione)

SMILES for NP0296978 ((1r,2s,3s,5s,8r,11r,12r)-5-[(2r,3r,4r,5r)-3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl]-12-hydroxy-3,11-dimethyl-6,14-dioxatetracyclo[10.2.2.0²,¹¹.0³,⁸]hexadec-15-ene-7,13-dione)

INCHI for NP0296978 ((1r,2s,3s,5s,8r,11r,12r)-5-[(2r,3r,4r,5r)-3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl]-12-hydroxy-3,11-dimethyl-6,14-dioxatetracyclo[10.2.2.0²,¹¹.0³,⁸]hexadec-15-ene-7,13-dione)

Structure for NP0296978 ((1r,2s,3s,5s,8r,11r,12r)-5-[(2r,3r,4r,5r)-3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl]-12-hydroxy-3,11-dimethyl-6,14-dioxatetracyclo[10.2.2.0²,¹¹.0³,⁸]hexadec-15-ene-7,13-dione)

3D Structure for NP0296978 ((1r,2s,3s,5s,8r,11r,12r)-5-[(2r,3r,4r,5r)-3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl]-12-hydroxy-3,11-dimethyl-6,14-dioxatetracyclo[10.2.2.0²,¹¹.0³,⁸]hexadec-15-ene-7,13-dione)