NP-MRD: Showing NP-Card for 2'-(acetyloxy)-5''-(furan-3-yl)-4'a,6'-dihydroxy-6'-methyl-2'',8'-dioxo-tetrahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolan]-8'a-ylmethyl acetate (NP0328454)

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Record Information

Version

1.0

Created at

2022-09-12 11:56:28 UTC

Updated at

2022-09-12 11:56:28 UTC

NP-MRD ID

NP0328454

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2'-(acetyloxy)-5''-(furan-3-yl)-4'a,6'-dihydroxy-6'-methyl-2'',8'-dioxo-tetrahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolan]-8'a-ylmethyl acetate

Description

[2'-(Acetyloxy)-5''-(furan-3-yl)-4'a,6'-dihydroxy-6'-methyl-2'',8'-dioxo-octahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolane]-8'a-yl]methyl acetate belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. 2'-(acetyloxy)-5''-(furan-3-yl)-4'a,6'-dihydroxy-6'-methyl-2'',8'-dioxo-tetrahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolan]-8'a-ylmethyl acetate is found in Teucrium brevifolium. [2'-(Acetyloxy)-5''-(furan-3-yl)-4'a,6'-dihydroxy-6'-methyl-2'',8'-dioxo-octahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolane]-8'a-yl]methyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231514532D          

 35 39  0  0  0  0            999 V2000
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    1.3789    1.5067    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


  Mrv1533004231514532D          

 35 39  0  0  0  0            999 V2000
    0.5549    1.5471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3789    1.5067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0328454

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OCC12C(=O)CC(C)(O)C3(CC(OC3=O)C3=COC=C3)C1(O)CCC(OC(C)=O)C21CO1

> <INCHI_IDENTIFIER>
InChI=1S/C24H28O11/c1-13(25)32-11-22-17(27)9-20(3,29)21(8-16(35-19(21)28)15-5-7-31-10-15)24(22,30)6-4-18(34-14(2)26)23(22)12-33-23/h5,7,10,16,18,29-30H,4,6,8-9,11-12H2,1-3H3

> <INCHI_KEY>
SWXQXGCDVLZWRF-UHFFFAOYSA-N

> <FORMULA>
C24H28O11

> <MOLECULAR_WEIGHT>
492.477

> <EXACT_MASS>
492.163161722

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
46.76065679944896

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[2'-(acetyloxy)-5''-(furan-3-yl)-4'a,6'-dihydroxy-6'-methyl-2'',8'-dioxo-octahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolane]-8'a-yl]methyl acetate

> <ALOGPS_LOGP>
0.58

> <JCHEM_LOGP>
-0.4313529150000008

> <ALOGPS_LOGS>
-2.41

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.149566806059092

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.126780519167141

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8692285600583234

> <JCHEM_POLAR_SURFACE_AREA>
162.1

> <JCHEM_REFRACTIVITY>
112.8462

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.90e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2'-(acetyloxy)-5''-(furan-3-yl)-4'a,6'-dihydroxy-6'-methyl-2'',8'-dioxo-tetrahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolane]-8'a-ylmethyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0       1.036   2.888   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.574   2.813   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.408   4.107   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.278   1.443   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.816   1.367   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.520  -0.002   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.434   1.535   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.059   2.230   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.723   2.378   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.097   1.684   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.542   3.158   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.626   1.501   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.183   0.146   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.553   0.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.645  -0.235   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.951  -1.610   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.429  -1.374   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       7.734  -2.749   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      12.165   0.011   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.258  -1.074   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      14.628  -0.371   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      14.382   1.150   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.860   1.385   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.894  -0.697   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       7.598  -2.067   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.980  -2.235   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.691  -3.078   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.317  -2.383   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       3.028  -3.226   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.114  -4.764   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.488  -5.458   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       1.825  -5.607   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.231  -0.846   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.693  -0.931   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       3.388   0.443   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   24   33                                             
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10   14   17   24                                             
CONECT   14   13   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   15   17                                                       
CONECT   17   16   13   18                                                  
CONECT   18   17                                                            
CONECT   19   15   20   23                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   19                                                       
CONECT   24   13    6   25   26                                             
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   28    6   34   35                                             
CONECT   34   33   35                                                       
CONECT   35   34   33                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Value	Source
[2'-(Acetyloxy)-5''-(furan-3-yl)-4'a,6'-dihydroxy-6'-methyl-2'',8'-dioxo-octahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolane]-8'a-yl]methyl acetic acid	Generator

Chemical Formula

C₂₄H₂₈O₁₁

Average Mass

492.4770 Da

Monoisotopic Mass

492.16316 Da

IUPAC Name

[2'-(acetyloxy)-5''-(furan-3-yl)-4'a,6'-dihydroxy-6'-methyl-2'',8'-dioxo-octahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolane]-8'a-yl]methyl acetate

Traditional Name

2'-(acetyloxy)-5''-(furan-3-yl)-4'a,6'-dihydroxy-6'-methyl-2'',8'-dioxo-tetrahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolane]-8'a-ylmethyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OCC12C(=O)CC(C)(O)C3(CC(OC3=O)C3=COC=C3)C1(O)CCC(OC(C)=O)C21CO1

InChI Identifier

InChI=1S/C24H28O11/c1-13(25)32-11-22-17(27)9-20(3,29)21(8-16(35-19(21)28)15-5-7-31-10-15)24(22,30)6-4-18(34-14(2)26)23(22)12-33-23/h5,7,10,16,18,29-30H,4,6,8-9,11-12H2,1-3H3

InChI Key

SWXQXGCDVLZWRF-UHFFFAOYSA-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 brevifolium	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Clerodane diterpenoid
Tricarboxylic acid or derivatives
Gamma butyrolactone
Cyclic alcohol
Heteroaromatic compound
Furan
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Ketone
Lactone
Organoheterocyclic compound
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Organooxygen compound
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	0.58	ALOGPS
logP	-0.43	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	13.13	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	162.1 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	112.85 m³·mol⁻¹	ChemAxon
Polarizability	46.76 Å³	ChemAxon
Number of Rings	5	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2'-(acetyloxy)-5''-(furan-3-yl)-4'a,6'-dihydroxy-6'-methyl-2'',8'-dioxo-tetrahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolan]-8'a-ylmethyl acetate (NP0328454)

MOL for NP0328454 (2'-(acetyloxy)-5''-(furan-3-yl)-4'a,6'-dihydroxy-6'-methyl-2'',8'-dioxo-tetrahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolan]-8'a-ylmethyl acetate)

3D MOL for NP0328454 (2'-(acetyloxy)-5''-(furan-3-yl)-4'a,6'-dihydroxy-6'-methyl-2'',8'-dioxo-tetrahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolan]-8'a-ylmethyl acetate)

3D SDF for NP0328454 (2'-(acetyloxy)-5''-(furan-3-yl)-4'a,6'-dihydroxy-6'-methyl-2'',8'-dioxo-tetrahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolan]-8'a-ylmethyl acetate)

3D-SDF for NP0328454 (2'-(acetyloxy)-5''-(furan-3-yl)-4'a,6'-dihydroxy-6'-methyl-2'',8'-dioxo-tetrahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolan]-8'a-ylmethyl acetate)

PDB for NP0328454 (2'-(acetyloxy)-5''-(furan-3-yl)-4'a,6'-dihydroxy-6'-methyl-2'',8'-dioxo-tetrahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolan]-8'a-ylmethyl acetate)

3D PDB for NP0328454 (2'-(acetyloxy)-5''-(furan-3-yl)-4'a,6'-dihydroxy-6'-methyl-2'',8'-dioxo-tetrahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolan]-8'a-ylmethyl acetate)

SMILES for NP0328454 (2'-(acetyloxy)-5''-(furan-3-yl)-4'a,6'-dihydroxy-6'-methyl-2'',8'-dioxo-tetrahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolan]-8'a-ylmethyl acetate)

INCHI for NP0328454 (2'-(acetyloxy)-5''-(furan-3-yl)-4'a,6'-dihydroxy-6'-methyl-2'',8'-dioxo-tetrahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolan]-8'a-ylmethyl acetate)

Structure for NP0328454 (2'-(acetyloxy)-5''-(furan-3-yl)-4'a,6'-dihydroxy-6'-methyl-2'',8'-dioxo-tetrahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolan]-8'a-ylmethyl acetate)

3D Structure for NP0328454 (2'-(acetyloxy)-5''-(furan-3-yl)-4'a,6'-dihydroxy-6'-methyl-2'',8'-dioxo-tetrahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolan]-8'a-ylmethyl acetate)