NP-MRD: Showing NP-Card for (1r,2s,4as,5r,6r,8r,8ar)-2-(acetyloxy)-5-[2-(furan-3-yl)ethyl]-4a,6,8-trihydroxy-5,6-dimethyl-7-oxo-tetrahydrospiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate (NP0212554)

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Record Information

Version

2.0

Created at

2022-09-05 11:15:17 UTC

Updated at

2022-09-05 11:15:18 UTC

NP-MRD ID

NP0212554

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,4as,5r,6r,8r,8ar)-2-(acetyloxy)-5-[2-(furan-3-yl)ethyl]-4a,6,8-trihydroxy-5,6-dimethyl-7-oxo-tetrahydrospiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate

Description

[(1R,2S,4aS,5R,6R,8R,8aR)-2-(acetyloxy)-5-[2-(furan-3-yl)ethyl]-4a,6,8-trihydroxy-5,6-dimethyl-7-oxo-octahydro-2H-spiro[naphthalene-1,2'-oxirane]-8a-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. (1r,2s,4as,5r,6r,8r,8ar)-2-(acetyloxy)-5-[2-(furan-3-yl)ethyl]-4a,6,8-trihydroxy-5,6-dimethyl-7-oxo-tetrahydrospiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate is found in Teucrium orientale. Based on a literature review very few articles have been published on [(1R,2S,4aS,5R,6R,8R,8aR)-2-(acetyloxy)-5-[2-(furan-3-yl)ethyl]-4a,6,8-trihydroxy-5,6-dimethyl-7-oxo-octahydro-2H-spiro[naphthalene-1,2'-oxirane]-8a-yl]methyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052213152D          

 34 37  0  0  1  0            999 V2000
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M  END

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M  END


  Mrv1652309052213152D          

 34 37  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0212554

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC[C@@]12[C@@H](O)C(=O)[C@](C)(O)[C@](C)(CCC3=COC=C3)[C@@]1(O)CC[C@H](OC(C)=O)[C@]21CO1

> <INCHI_IDENTIFIER>
InChI=1S/C24H32O10/c1-14(25)32-12-22-19(28)18(27)21(4,29)20(3,8-5-16-7-10-31-11-16)24(22,30)9-6-17(34-15(2)26)23(22)13-33-23/h7,10-11,17,19,28-30H,5-6,8-9,12-13H2,1-4H3/t17-,19-,20-,21-,22-,23+,24-/m0/s1

> <INCHI_KEY>
AHBOQICKWFLQLC-PQURANIKSA-N

> <FORMULA>
C24H32O10

> <MOLECULAR_WEIGHT>
480.51

> <EXACT_MASS>
480.19954723

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
48.524909878427195

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1R,2S,4aS,5R,6R,8R,8aR)-2-(acetyloxy)-5-[2-(furan-3-yl)ethyl]-4a,6,8-trihydroxy-5,6-dimethyl-7-oxo-octahydro-2H-spiro[naphthalene-1,2'-oxirane]-8a-yl]methyl acetate

> <JCHEM_LOGP>
0.22813596766666613

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.255814369092693

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.649156735631202

> <JCHEM_PKA_STRONGEST_BASIC>
-2.768914191558206

> <JCHEM_POLAR_SURFACE_AREA>
156.03

> <JCHEM_REFRACTIVITY>
114.44389999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,4aS,5R,6R,8R,8aR)-2-(acetyloxy)-5-[2-(furan-3-yl)ethyl]-4a,6,8-trihydroxy-5,6-dimethyl-7-oxo-tetrahydrospiro[naphthalene-1,2'-oxirane]-8a-ylmethyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       2.381   3.525   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.791   2.906   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.032   3.819   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.961   1.376   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.371   0.757   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.541  -0.773   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.008   0.694   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.971   1.833   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       7.513   1.023   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.980   2.490   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       8.550  -0.116   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.491   1.103   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.913  -0.831   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.082  -1.583   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.144  -3.122   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.608  -1.789   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.193  -3.213   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.719  -3.419   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.783  -2.305   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.171  -2.973   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      13.965  -4.499   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      12.450  -4.775   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.577  -1.912   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       7.614  -3.050   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.110  -3.379   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.605  -3.708   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.568  -2.569   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.064  -2.898   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.596  -4.365   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.633  -5.504   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       0.092  -4.694   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.036  -1.102   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.569  -0.634   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       3.707   0.403   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   23   32                                             
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11   15   16   23                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   22                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   18                                                       
CONECT   23   14    6   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   27    6   33   34                                             
CONECT   33   32   34                                                       
CONECT   34   33   32                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
[(1R,2S,4AS,5R,6R,8R,8ar)-2-(acetyloxy)-5-[2-(furan-3-yl)ethyl]-4a,6,8-trihydroxy-5,6-dimethyl-7-oxo-octahydro-2H-spiro[naphthalene-1,2'-oxirane]-8a-yl]methyl acetic acid	Generator

Chemical Formula

C₂₄H₃₂O₁₀

Average Mass

480.5100 Da

Monoisotopic Mass

480.19955 Da

IUPAC Name

[(1R,2S,4aS,5R,6R,8R,8aR)-2-(acetyloxy)-5-[2-(furan-3-yl)ethyl]-4a,6,8-trihydroxy-5,6-dimethyl-7-oxo-octahydro-2H-spiro[naphthalene-1,2'-oxirane]-8a-yl]methyl acetate

Traditional Name

(1R,2S,4aS,5R,6R,8R,8aR)-2-(acetyloxy)-5-[2-(furan-3-yl)ethyl]-4a,6,8-trihydroxy-5,6-dimethyl-7-oxo-tetrahydrospiro[naphthalene-1,2'-oxirane]-8a-ylmethyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC[C@@]12[C@@H](O)C(=O)[C@](C)(O)[C@](C)(CCC3=COC=C3)[C@@]1(O)CC[C@H](OC(C)=O)[C@]21CO1

InChI Identifier

InChI=1S/C24H32O10/c1-14(25)32-12-22-19(28)18(27)21(4,29)20(3,8-5-16-7-10-31-11-16)24(22,30)9-6-17(34-15(2)26)23(22)13-33-23/h7,10-11,17,19,28-30H,5-6,8-9,12-13H2,1-4H3/t17-,19-,20-,21-,22-,23+,24-/m0/s1

InChI Key

AHBOQICKWFLQLC-PQURANIKSA-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 orientale	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

Acyloin
Dicarboxylic acid or derivatives
Cyclic alcohol
Heteroaromatic compound
Furan
Tertiary alcohol
Carboxylic acid ester
Ketone
Secondary alcohol
Cyclic ketone
Oxacycle
Ether
Oxirane
Dialkyl ether
Polyol
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	0.23	ChemAxon
pKa (Strongest Acidic)	9.65	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	156.03 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	114.44 m³·mol⁻¹	ChemAxon
Polarizability	48.52 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

9663292

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11488480

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,4as,5r,6r,8r,8ar)-2-(acetyloxy)-5-[2-(furan-3-yl)ethyl]-4a,6,8-trihydroxy-5,6-dimethyl-7-oxo-tetrahydrospiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate (NP0212554)

MOL for NP0212554 ((1r,2s,4as,5r,6r,8r,8ar)-2-(acetyloxy)-5-[2-(furan-3-yl)ethyl]-4a,6,8-trihydroxy-5,6-dimethyl-7-oxo-tetrahydrospiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate)

3D MOL for NP0212554 ((1r,2s,4as,5r,6r,8r,8ar)-2-(acetyloxy)-5-[2-(furan-3-yl)ethyl]-4a,6,8-trihydroxy-5,6-dimethyl-7-oxo-tetrahydrospiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate)

3D SDF for NP0212554 ((1r,2s,4as,5r,6r,8r,8ar)-2-(acetyloxy)-5-[2-(furan-3-yl)ethyl]-4a,6,8-trihydroxy-5,6-dimethyl-7-oxo-tetrahydrospiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate)

3D-SDF for NP0212554 ((1r,2s,4as,5r,6r,8r,8ar)-2-(acetyloxy)-5-[2-(furan-3-yl)ethyl]-4a,6,8-trihydroxy-5,6-dimethyl-7-oxo-tetrahydrospiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate)

PDB for NP0212554 ((1r,2s,4as,5r,6r,8r,8ar)-2-(acetyloxy)-5-[2-(furan-3-yl)ethyl]-4a,6,8-trihydroxy-5,6-dimethyl-7-oxo-tetrahydrospiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate)

3D PDB for NP0212554 ((1r,2s,4as,5r,6r,8r,8ar)-2-(acetyloxy)-5-[2-(furan-3-yl)ethyl]-4a,6,8-trihydroxy-5,6-dimethyl-7-oxo-tetrahydrospiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate)

SMILES for NP0212554 ((1r,2s,4as,5r,6r,8r,8ar)-2-(acetyloxy)-5-[2-(furan-3-yl)ethyl]-4a,6,8-trihydroxy-5,6-dimethyl-7-oxo-tetrahydrospiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate)

INCHI for NP0212554 ((1r,2s,4as,5r,6r,8r,8ar)-2-(acetyloxy)-5-[2-(furan-3-yl)ethyl]-4a,6,8-trihydroxy-5,6-dimethyl-7-oxo-tetrahydrospiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate)

Structure for NP0212554 ((1r,2s,4as,5r,6r,8r,8ar)-2-(acetyloxy)-5-[2-(furan-3-yl)ethyl]-4a,6,8-trihydroxy-5,6-dimethyl-7-oxo-tetrahydrospiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate)

3D Structure for NP0212554 ((1r,2s,4as,5r,6r,8r,8ar)-2-(acetyloxy)-5-[2-(furan-3-yl)ethyl]-4a,6,8-trihydroxy-5,6-dimethyl-7-oxo-tetrahydrospiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate)