NP-MRD: Showing NP-Card for (1s)-2-[(1r,4ar,5s,6r,8s,8ar)-8-hydroxy-8a-(hydroxymethyl)-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-5-yl]-1-(5-oxo-2h-furan-3-yl)ethyl (2s)-2-methylbutanoate (NP0206445)

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Record Information

Version

2.0

Created at

2022-09-05 02:41:42 UTC

Updated at

2022-09-05 02:41:42 UTC

NP-MRD ID

NP0206445

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

(1S)-2-[(1R,4aR,5S,6R,8S,8aR)-8-hydroxy-8a-(hydroxymethyl)-5,6-dimethyl-octahydro-2H-spiro[naphthalene-1,2'-oxirane]-5-yl]-1-(5-oxo-2,5-dihydrofuran-3-yl)ethyl (2S)-2-methylbutanoate belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. (1s)-2-[(1r,4ar,5s,6r,8s,8ar)-8-hydroxy-8a-(hydroxymethyl)-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-5-yl]-1-(5-oxo-2h-furan-3-yl)ethyl (2s)-2-methylbutanoate is found in Ajuga ciliata. Based on a literature review very few articles have been published on (1S)-2-[(1R,4aR,5S,6R,8S,8aR)-8-hydroxy-8a-(hydroxymethyl)-5,6-dimethyl-octahydro-2H-spiro[naphthalene-1,2'-oxirane]-5-yl]-1-(5-oxo-2,5-dihydrofuran-3-yl)ethyl (2S)-2-methylbutanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052204412D          

 32 35  0  0  1  0            999 V2000
   -4.6148    2.1998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9004    1.7873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1859    2.1998    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1859    3.0248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4714    1.7873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4714    0.9623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7570    2.1998    0.0000 O   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


  Mrv1652309052204412D          

 32 35  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0206445

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](C)C(=O)O[C@@H](C[C@@]1(C)[C@H](C)C[C@H](O)[C@]2(CO)[C@@H]1CCC[C@]21CO1)C1=CC(=O)OC1

> <INCHI_IDENTIFIER>
InChI=1S/C25H38O7/c1-5-15(2)22(29)32-18(17-10-21(28)30-12-17)11-23(4)16(3)9-20(27)25(13-26)19(23)7-6-8-24(25)14-31-24/h10,15-16,18-20,26-27H,5-9,11-14H2,1-4H3/t15-,16+,18-,19+,20-,23-,24-,25-/m0/s1

> <INCHI_KEY>
NTIOVLZNHFUWFE-RXQXNILTSA-N

> <FORMULA>
C25H38O7

> <MOLECULAR_WEIGHT>
450.572

> <EXACT_MASS>
450.261753564

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
48.79231678681524

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
2.7086271173333336

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.378915343758301

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.593896837482715

> <JCHEM_PKA_STRONGEST_BASIC>
-2.829635892931867

> <JCHEM_POLAR_SURFACE_AREA>
105.59000000000002

> <JCHEM_REFRACTIVITY>
117.82449999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

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

> <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      -8.614   4.106   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.281   3.336   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.947   4.106   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.947   5.646   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.613   3.336   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -4.613   1.796   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -3.280   4.106   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.946   3.336   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.612   4.106   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.721   3.336   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.269   2.157   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.711   2.157   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.185   0.709   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.228   2.424   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.755   3.871   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.271   4.138   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.765   5.051   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.281   5.318   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.558   6.179   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.248   4.783   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.258   5.963   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.785   7.410   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.302   7.678   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.291   6.498   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.471   7.488   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.739   5.971   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -1.946   1.796   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.700   0.891   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.176  -0.574   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -0.271  -1.819   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -2.716  -0.574   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -3.192   0.891   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   27                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12   20                                             
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   20   24                                             
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17   10   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   17   25   26                                             
CONECT   25   24   26                                                       
CONECT   26   25   24                                                       
CONECT   27    8   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   27                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
(1S)-2-[(1R,4AR,5S,6R,8S,8ar)-8-hydroxy-8a-(hydroxymethyl)-5,6-dimethyl-octahydro-2H-spiro[naphthalene-1,2'-oxirane]-5-yl]-1-(5-oxo-2,5-dihydrofuran-3-yl)ethyl (2S)-2-methylbutanoic acid	Generator

Chemical Formula

C₂₅H₃₈O₇

Average Mass

450.5720 Da

Monoisotopic Mass

450.26175 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC[C@H](C)C(=O)O[C@@H](C[C@@]1(C)[C@H](C)C[C@H](O)[C@]2(CO)[C@@H]1CCC[C@]21CO1)C1=CC(=O)OC1

InChI Identifier

InChI=1S/C25H38O7/c1-5-15(2)22(29)32-18(17-10-21(28)30-12-17)11-23(4)16(3)9-20(27)25(13-26)19(23)7-6-8-24(25)14-31-24/h10,15-16,18-20,26-27H,5-9,11-14H2,1-4H3/t15-,16+,18-,19+,20-,23-,24-,25-/m0/s1

InChI Key

NTIOVLZNHFUWFE-RXQXNILTSA-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 ciliata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Fatty acid esters

Alternative Parents

Substituents

Fatty acid ester
2-furanone
Dicarboxylic acid or derivatives
Cyclic alcohol
Dihydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Ether
Oxirane
Dialkyl ether
Primary alcohol
Organic oxide
Alcohol
Hydrocarbon derivative
Organic oxygen compound
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	2.71	ChemAxon
pKa (Strongest Acidic)	5.59	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	105.59 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	117.82 m³·mol⁻¹	ChemAxon
Polarizability	48.79 Å³	ChemAxon
Number of Rings	4	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

10258987

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14356981

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s)-2-[(1r,4ar,5s,6r,8s,8ar)-8-hydroxy-8a-(hydroxymethyl)-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-5-yl]-1-(5-oxo-2h-furan-3-yl)ethyl (2s)-2-methylbutanoate (NP0206445)

MOL for NP0206445 ((1s)-2-[(1r,4ar,5s,6r,8s,8ar)-8-hydroxy-8a-(hydroxymethyl)-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-5-yl]-1-(5-oxo-2h-furan-3-yl)ethyl (2s)-2-methylbutanoate)

3D MOL for NP0206445 ((1s)-2-[(1r,4ar,5s,6r,8s,8ar)-8-hydroxy-8a-(hydroxymethyl)-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-5-yl]-1-(5-oxo-2h-furan-3-yl)ethyl (2s)-2-methylbutanoate)

3D SDF for NP0206445 ((1s)-2-[(1r,4ar,5s,6r,8s,8ar)-8-hydroxy-8a-(hydroxymethyl)-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-5-yl]-1-(5-oxo-2h-furan-3-yl)ethyl (2s)-2-methylbutanoate)

3D-SDF for NP0206445 ((1s)-2-[(1r,4ar,5s,6r,8s,8ar)-8-hydroxy-8a-(hydroxymethyl)-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-5-yl]-1-(5-oxo-2h-furan-3-yl)ethyl (2s)-2-methylbutanoate)

PDB for NP0206445 ((1s)-2-[(1r,4ar,5s,6r,8s,8ar)-8-hydroxy-8a-(hydroxymethyl)-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-5-yl]-1-(5-oxo-2h-furan-3-yl)ethyl (2s)-2-methylbutanoate)

3D PDB for NP0206445 ((1s)-2-[(1r,4ar,5s,6r,8s,8ar)-8-hydroxy-8a-(hydroxymethyl)-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-5-yl]-1-(5-oxo-2h-furan-3-yl)ethyl (2s)-2-methylbutanoate)

SMILES for NP0206445 ((1s)-2-[(1r,4ar,5s,6r,8s,8ar)-8-hydroxy-8a-(hydroxymethyl)-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-5-yl]-1-(5-oxo-2h-furan-3-yl)ethyl (2s)-2-methylbutanoate)

INCHI for NP0206445 ((1s)-2-[(1r,4ar,5s,6r,8s,8ar)-8-hydroxy-8a-(hydroxymethyl)-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-5-yl]-1-(5-oxo-2h-furan-3-yl)ethyl (2s)-2-methylbutanoate)

Structure for NP0206445 ((1s)-2-[(1r,4ar,5s,6r,8s,8ar)-8-hydroxy-8a-(hydroxymethyl)-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-5-yl]-1-(5-oxo-2h-furan-3-yl)ethyl (2s)-2-methylbutanoate)

3D Structure for NP0206445 ((1s)-2-[(1r,4ar,5s,6r,8s,8ar)-8-hydroxy-8a-(hydroxymethyl)-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-5-yl]-1-(5-oxo-2h-furan-3-yl)ethyl (2s)-2-methylbutanoate)