NP-MRD: Showing NP-Card for (1r,4ar,5s,6r,8s,8ar)-8-(acetyloxy)-5,6-dimethyl-5-[2-(5-oxo-2h-furan-3-yl)ethyl]-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-8a-ylmethyl 3-hydroxy-2-methylidenebutanoate (NP0201695)

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Record Information

Version

2.0

Created at

2022-09-04 20:47:28 UTC

Updated at

2022-09-04 20:47:28 UTC

NP-MRD ID

NP0201695

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,4ar,5s,6r,8s,8ar)-8-(acetyloxy)-5,6-dimethyl-5-[2-(5-oxo-2h-furan-3-yl)ethyl]-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-8a-ylmethyl 3-hydroxy-2-methylidenebutanoate

Description

Ajugacumbin G belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. (1r,4ar,5s,6r,8s,8ar)-8-(acetyloxy)-5,6-dimethyl-5-[2-(5-oxo-2h-furan-3-yl)ethyl]-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-8a-ylmethyl 3-hydroxy-2-methylidenebutanoate is found in Ajuga decumbens. Based on a literature review very few articles have been published on Ajugacumbin G.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042222472D          

 35 38  0  0  1  0            999 V2000
    3.4099    0.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4099   -0.6131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6954   -1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6954   -1.8506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9810   -0.6131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665   -1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595   -0.8541    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9445   -1.5215    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7649   -1.4353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  2 33  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309042222472D          

 35 38  0  0  1  0            999 V2000
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 16 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 20 25  1  0  0  0  0
 16 26  1  0  0  0  0
  7 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
  7 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 30 32  1  1  0  0  0
  2 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0201695

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)C(=C)C(=O)OC[C@@]12[C@H](C[C@@H](C)[C@](C)(CCC3=CC(=O)OC3)[C@H]1CCC[C@]21CO1)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H38O8/c1-16-11-22(35-19(4)29)27(15-33-24(31)17(2)18(3)28)21(7-6-9-26(27)14-34-26)25(16,5)10-8-20-12-23(30)32-13-20/h12,16,18,21-22,28H,2,6-11,13-15H2,1,3-5H3/t16-,18?,21-,22+,25+,26+,27+/m1/s1

> <INCHI_KEY>
KACNHTHLIACRKY-GTKADIPGSA-N

> <FORMULA>
C27H38O8

> <MOLECULAR_WEIGHT>
490.593

> <EXACT_MASS>
490.256668184

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
52.89788003156106

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
3.2134535019999992

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.669771784610443

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.471544797867325

> <JCHEM_PKA_STRONGEST_BASIC>
-2.943241833446116

> <JCHEM_POLAR_SURFACE_AREA>
111.66000000000001

> <JCHEM_REFRACTIVITY>
126.85639999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4aR,5S,6R,8S,8aR)-8-(acetyloxy)-5,6-dimethyl-5-[2-(5-oxo-2H-furan-3-yl)ethyl]-hexahydro-2H-spiro[naphthalene-1,2'-oxirane]-8a-ylmethyl 3-hydroxy-2-methylidenebutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       6.365   0.396   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.365  -1.144   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.031  -1.914   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.031  -3.454   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       3.698  -1.144   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.364  -1.914   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.858  -1.594   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.763  -2.840   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.295  -2.679   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.200  -3.925   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.731  -3.764   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.573  -5.332   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.137  -4.247   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.395  -4.408   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.021  -5.815   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.300  -3.162   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.577  -2.301   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.370  -4.270   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.864  -3.897   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.934  -5.005   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.667  -6.522   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -6.026  -7.245   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -6.241  -8.770   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -7.134  -6.175   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -6.459  -4.791   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.674  -1.755   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.579  -0.509   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.953   0.898   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.579   1.058   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.484  -0.187   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.730   0.718   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.891  -0.814   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       7.699  -1.914   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.033  -1.144   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       7.699  -3.454   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   33                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   26   30                                             
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    8   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18   26                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   20                                                       
CONECT   26   16    7   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29    7   31   32                                             
CONECT   31   30   32                                                       
CONECT   32   31   30                                                       
CONECT   33    2   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₈O₈

Average Mass

490.5930 Da

Monoisotopic Mass

490.25667 Da

IUPAC Name

[(1R,4aR,5S,6R,8S,8aR)-8-(acetyloxy)-5,6-dimethyl-5-[2-(5-oxo-2,5-dihydrofuran-3-yl)ethyl]-octahydro-2H-spiro[naphthalene-1,2'-oxirane]-8a-yl]methyl 3-hydroxy-2-methylidenebutanoate

Traditional Name

(1R,4aR,5S,6R,8S,8aR)-8-(acetyloxy)-5,6-dimethyl-5-[2-(5-oxo-2H-furan-3-yl)ethyl]-hexahydro-2H-spiro[naphthalene-1,2'-oxirane]-8a-ylmethyl 3-hydroxy-2-methylidenebutanoate

CAS Registry Number

Not Available

SMILES

CC(O)C(=C)C(=O)OC[C@@]12[C@H](C[C@@H](C)[C@](C)(CCC3=CC(=O)OC3)[C@H]1CCC[C@]21CO1)OC(C)=O

InChI Identifier

InChI=1S/C27H38O8/c1-16-11-22(35-19(4)29)27(15-33-24(31)17(2)18(3)28)21(7-6-9-26(27)14-34-26)25(16,5)10-8-20-12-23(30)32-13-20/h12,16,18,21-22,28H,2,6-11,13-15H2,1,3-5H3/t16-,18?,21-,22+,25+,26+,27+/m1/s1

InChI Key

KACNHTHLIACRKY-GTKADIPGSA-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
Ajuga decumbens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Beta-hydroxy acid
Fatty acid ester
2-furanone
Fatty acyl
Hydroxy acid
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Lactone
Dialkyl ether
Oxacycle
Oxirane
Ether
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Carbonyl group
Organooxygen compound
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	3.21	ChemAxon
pKa (Strongest Acidic)	7.47	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	111.66 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	126.86 m³·mol⁻¹	ChemAxon
Polarizability	52.9 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

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

15276268

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,4ar,5s,6r,8s,8ar)-8-(acetyloxy)-5,6-dimethyl-5-[2-(5-oxo-2h-furan-3-yl)ethyl]-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-8a-ylmethyl 3-hydroxy-2-methylidenebutanoate (NP0201695)

MOL for NP0201695 ((1r,4ar,5s,6r,8s,8ar)-8-(acetyloxy)-5,6-dimethyl-5-[2-(5-oxo-2h-furan-3-yl)ethyl]-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-8a-ylmethyl 3-hydroxy-2-methylidenebutanoate)

3D MOL for NP0201695 ((1r,4ar,5s,6r,8s,8ar)-8-(acetyloxy)-5,6-dimethyl-5-[2-(5-oxo-2h-furan-3-yl)ethyl]-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-8a-ylmethyl 3-hydroxy-2-methylidenebutanoate)

3D SDF for NP0201695 ((1r,4ar,5s,6r,8s,8ar)-8-(acetyloxy)-5,6-dimethyl-5-[2-(5-oxo-2h-furan-3-yl)ethyl]-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-8a-ylmethyl 3-hydroxy-2-methylidenebutanoate)

3D-SDF for NP0201695 ((1r,4ar,5s,6r,8s,8ar)-8-(acetyloxy)-5,6-dimethyl-5-[2-(5-oxo-2h-furan-3-yl)ethyl]-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-8a-ylmethyl 3-hydroxy-2-methylidenebutanoate)

PDB for NP0201695 ((1r,4ar,5s,6r,8s,8ar)-8-(acetyloxy)-5,6-dimethyl-5-[2-(5-oxo-2h-furan-3-yl)ethyl]-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-8a-ylmethyl 3-hydroxy-2-methylidenebutanoate)

3D PDB for NP0201695 ((1r,4ar,5s,6r,8s,8ar)-8-(acetyloxy)-5,6-dimethyl-5-[2-(5-oxo-2h-furan-3-yl)ethyl]-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-8a-ylmethyl 3-hydroxy-2-methylidenebutanoate)

SMILES for NP0201695 ((1r,4ar,5s,6r,8s,8ar)-8-(acetyloxy)-5,6-dimethyl-5-[2-(5-oxo-2h-furan-3-yl)ethyl]-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-8a-ylmethyl 3-hydroxy-2-methylidenebutanoate)

INCHI for NP0201695 ((1r,4ar,5s,6r,8s,8ar)-8-(acetyloxy)-5,6-dimethyl-5-[2-(5-oxo-2h-furan-3-yl)ethyl]-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-8a-ylmethyl 3-hydroxy-2-methylidenebutanoate)

Structure for NP0201695 ((1r,4ar,5s,6r,8s,8ar)-8-(acetyloxy)-5,6-dimethyl-5-[2-(5-oxo-2h-furan-3-yl)ethyl]-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-8a-ylmethyl 3-hydroxy-2-methylidenebutanoate)

3D Structure for NP0201695 ((1r,4ar,5s,6r,8s,8ar)-8-(acetyloxy)-5,6-dimethyl-5-[2-(5-oxo-2h-furan-3-yl)ethyl]-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-8a-ylmethyl 3-hydroxy-2-methylidenebutanoate)