NP-MRD: Showing NP-Card for (2r,2''r,4'as,5's,5''s,6's,8'r,8'ar)-2''-(acetyloxy)-5''-(furan-3-yl)-8'-hydroxy-6'-methyl-7'-oxo-hexahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolan]-8'a-ylmethyl acetate (NP0302827)

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Record Information

Version

2.0

Created at

2022-09-10 16:39:14 UTC

Updated at

2022-09-10 16:39:15 UTC

NP-MRD ID

NP0302827

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,2''r,4'as,5's,5''s,6's,8'r,8'ar)-2''-(acetyloxy)-5''-(furan-3-yl)-8'-hydroxy-6'-methyl-7'-oxo-hexahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolan]-8'a-ylmethyl acetate

Description

[(2R,2''R,4'aS,5'S,5''S,6'S,8'R,8'aR)-2''-(acetyloxy)-5''-(furan-3-yl)-8'-hydroxy-6'-methyl-7'-oxo-octahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolane]-8'a-yl]methyl acetate belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. (2r,2''r,4'as,5's,5''s,6's,8'r,8'ar)-2''-(acetyloxy)-5''-(furan-3-yl)-8'-hydroxy-6'-methyl-7'-oxo-hexahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolan]-8'a-ylmethyl acetate is found in Teucrium polium. Based on a literature review very few articles have been published on [(2R,2''R,4'aS,5'S,5''S,6'S,8'R,8'aR)-2''-(acetyloxy)-5''-(furan-3-yl)-8'-hydroxy-6'-methyl-7'-oxo-octahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolane]-8'a-yl]methyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102218392D          

 33 37  0  0  1  0            999 V2000
    3.8474    2.9611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0234    2.9208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6464    2.1870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8224    2.1466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4453    1.4128    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7090    1.0407    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6630    0.2170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3534   -0.2347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2276    2.6085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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  6 32  1  0  0  0  0
 32 33  1  6  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309102218392D          

 33 37  0  0  1  0            999 V2000
    3.8474    2.9611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0234    2.9208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0302827

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C(=O)[C@H](O)[C@]2(COC(C)=O)[C@H](CCC[C@]22CO2)[C@@]11C[C@H](O[C@@H]1OC(C)=O)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C24H30O9/c1-13-19(27)20(28)24(12-30-14(2)25)18(5-4-7-22(24)11-31-22)23(13)9-17(16-6-8-29-10-16)33-21(23)32-15(3)26/h6,8,10,13,17-18,20-21,28H,4-5,7,9,11-12H2,1-3H3/t13-,17+,18-,20+,21+,22+,23-,24+/m1/s1

> <INCHI_KEY>
FYIKMNJCJWVGLP-YBKUINJNSA-N

> <FORMULA>
C24H30O9

> <MOLECULAR_WEIGHT>
462.495

> <EXACT_MASS>
462.188982546

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
46.864702485864726

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(2R,2''R,4'aS,5'S,5''S,6'S,8'R,8'aR)-2''-(acetyloxy)-5''-(furan-3-yl)-8'-hydroxy-6'-methyl-7'-oxo-octahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolane]-8'a-yl]methyl acetate

> <JCHEM_LOGP>
1.4177081396666669

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.091800357841713

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.782299451864208

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8548875555963096

> <JCHEM_POLAR_SURFACE_AREA>
124.8

> <JCHEM_REFRACTIVITY>
111.04129999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,2''R,4'aS,5'S,5''S,6'S,8'R,8'aR)-2''-(acetyloxy)-5''-(furan-3-yl)-8'-hydroxy-6'-methyl-7'-oxo-hexahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolane]-8'a-ylmethyl acetate

> <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       7.182   5.527   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.644   5.452   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.809   6.746   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.940   4.082   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.402   4.007   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.698   2.637   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.323   1.943   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.238   0.405   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.526  -0.438   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.901   0.256   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.987   1.794   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.830   3.083   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.524   1.708   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.035   2.786   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.211   1.266   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.733   1.030   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.437  -0.340   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.742  -1.714   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.835  -2.800   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -4.205  -2.096   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -3.959  -0.576   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.428   2.404   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.335   3.490   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.571   5.011   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -3.007   5.568   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.207   4.603   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -3.242   7.090   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.121   4.323   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.845   5.523   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.495   5.018   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.581   6.555   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       2.784   4.175   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.158   4.869   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   11   32                                             
CONECT    7    6    8   14                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    6   12   13                                             
CONECT   12   11   13                                                       
CONECT   13   12   11                                                       
CONECT   14    7   15   23   28                                             
CONECT   15   14   16                                                       
CONECT   16   15   17   22                                                  
CONECT   17   16   18   21                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   17                                                       
CONECT   22   16   23                                                       
CONECT   23   22   14   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   14   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30    6   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Value	Source
[(2R,2''R,4'as,5's,5''s,6's,8'r,8'ar)-2''-(acetyloxy)-5''-(furan-3-yl)-8'-hydroxy-6'-methyl-7'-oxo-octahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolane]-8'a-yl]methyl acetic acid	Generator

Chemical Formula

C₂₄H₃₀O₉

Average Mass

462.4950 Da

Monoisotopic Mass

462.18898 Da

IUPAC Name

[(2R,2''R,4'aS,5'S,5''S,6'S,8'R,8'aR)-2''-(acetyloxy)-5''-(furan-3-yl)-8'-hydroxy-6'-methyl-7'-oxo-octahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolane]-8'a-yl]methyl acetate

Traditional Name

(2R,2''R,4'aS,5'S,5''S,6'S,8'R,8'aR)-2''-(acetyloxy)-5''-(furan-3-yl)-8'-hydroxy-6'-methyl-7'-oxo-hexahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolane]-8'a-ylmethyl acetate

CAS Registry Number

Not Available

SMILES

C[C@@H]1C(=O)[C@H](O)[C@]2(COC(C)=O)[C@H](CCC[C@]22CO2)[C@@]11C[C@H](O[C@@H]1OC(C)=O)C1=COC=C1

InChI Identifier

InChI=1S/C24H30O9/c1-13-19(27)20(28)24(12-30-14(2)25)18(5-4-7-22(24)11-31-22)23(13)9-17(16-6-8-29-10-16)33-21(23)32-15(3)26/h6,8,10,13,17-18,20-21,28H,4-5,7,9,11-12H2,1-3H3/t13-,17+,18-,20+,21+,22+,23-,24+/m1/s1

InChI Key

FYIKMNJCJWVGLP-YBKUINJNSA-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
Teucrium polium	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Dicarboxylic acids and derivatives

Direct Parent

Dicarboxylic acids and derivatives

Alternative Parents

Substituents

Dicarboxylic acid or derivatives
Cyclic alcohol
Furan
Heteroaromatic compound
Tetrahydrofuran
Carboxylic acid ester
Ketone
Secondary alcohol
Cyclic ketone
Ether
Oxirane
Dialkyl ether
Acetal
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
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	1.42	ChemAxon
pKa (Strongest Acidic)	12.78	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	124.8 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	111.04 m³·mol⁻¹	ChemAxon
Polarizability	46.86 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	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

162850952

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,2''r,4'as,5's,5''s,6's,8'r,8'ar)-2''-(acetyloxy)-5''-(furan-3-yl)-8'-hydroxy-6'-methyl-7'-oxo-hexahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolan]-8'a-ylmethyl acetate (NP0302827)

MOL for NP0302827 ((2r,2''r,4'as,5's,5''s,6's,8'r,8'ar)-2''-(acetyloxy)-5''-(furan-3-yl)-8'-hydroxy-6'-methyl-7'-oxo-hexahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolan]-8'a-ylmethyl acetate)

3D MOL for NP0302827 ((2r,2''r,4'as,5's,5''s,6's,8'r,8'ar)-2''-(acetyloxy)-5''-(furan-3-yl)-8'-hydroxy-6'-methyl-7'-oxo-hexahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolan]-8'a-ylmethyl acetate)

3D SDF for NP0302827 ((2r,2''r,4'as,5's,5''s,6's,8'r,8'ar)-2''-(acetyloxy)-5''-(furan-3-yl)-8'-hydroxy-6'-methyl-7'-oxo-hexahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolan]-8'a-ylmethyl acetate)

3D-SDF for NP0302827 ((2r,2''r,4'as,5's,5''s,6's,8'r,8'ar)-2''-(acetyloxy)-5''-(furan-3-yl)-8'-hydroxy-6'-methyl-7'-oxo-hexahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolan]-8'a-ylmethyl acetate)

PDB for NP0302827 ((2r,2''r,4'as,5's,5''s,6's,8'r,8'ar)-2''-(acetyloxy)-5''-(furan-3-yl)-8'-hydroxy-6'-methyl-7'-oxo-hexahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolan]-8'a-ylmethyl acetate)

3D PDB for NP0302827 ((2r,2''r,4'as,5's,5''s,6's,8'r,8'ar)-2''-(acetyloxy)-5''-(furan-3-yl)-8'-hydroxy-6'-methyl-7'-oxo-hexahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolan]-8'a-ylmethyl acetate)

SMILES for NP0302827 ((2r,2''r,4'as,5's,5''s,6's,8'r,8'ar)-2''-(acetyloxy)-5''-(furan-3-yl)-8'-hydroxy-6'-methyl-7'-oxo-hexahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolan]-8'a-ylmethyl acetate)

INCHI for NP0302827 ((2r,2''r,4'as,5's,5''s,6's,8'r,8'ar)-2''-(acetyloxy)-5''-(furan-3-yl)-8'-hydroxy-6'-methyl-7'-oxo-hexahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolan]-8'a-ylmethyl acetate)

Structure for NP0302827 ((2r,2''r,4'as,5's,5''s,6's,8'r,8'ar)-2''-(acetyloxy)-5''-(furan-3-yl)-8'-hydroxy-6'-methyl-7'-oxo-hexahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolan]-8'a-ylmethyl acetate)

3D Structure for NP0302827 ((2r,2''r,4'as,5's,5''s,6's,8'r,8'ar)-2''-(acetyloxy)-5''-(furan-3-yl)-8'-hydroxy-6'-methyl-7'-oxo-hexahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolan]-8'a-ylmethyl acetate)