NP-MRD: Showing NP-Card for [(1s,2s,4ar,8as)-2,5,5,8a-tetramethyl-6-oxo-2-(2-oxopropanoyl)-hexahydronaphthalen-1-yl]acetic acid (NP0224492)

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Record Information

Version

2.0

Created at

2022-09-06 02:51:59 UTC

Updated at

2022-09-06 02:51:59 UTC

NP-MRD ID

NP0224492

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1s,2s,4ar,8as)-2,5,5,8a-tetramethyl-6-oxo-2-(2-oxopropanoyl)-hexahydronaphthalen-1-yl]acetic acid

Description

2-[(1S,2S,4aR,8aS)-2,5,5,8a-tetramethyl-6-oxo-2-(2-oxopropanoyl)-decahydronaphthalen-1-yl]acetic acid belongs to the class of organic compounds known as alpha-diketones. These are organic compounds containing two ketone groups on two adjacent carbon atoms. [(1s,2s,4ar,8as)-2,5,5,8a-tetramethyl-6-oxo-2-(2-oxopropanoyl)-hexahydronaphthalen-1-yl]acetic acid is found in Rhabdastrella globostellata. Based on a literature review very few articles have been published on 2-[(1S,2S,4aR,8aS)-2,5,5,8a-tetramethyl-6-oxo-2-(2-oxopropanoyl)-decahydronaphthalen-1-yl]acetic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062204522D          

 24 25  0  0  1  0            999 V2000
   -1.1926   -0.1757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3802   -0.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1501    0.3130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0980   -1.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6283   -1.7262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4323   -2.0127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3276    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  6  4  1  1  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
  6 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0224492

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)C(=O)[C@@]1(C)CC[C@H]2C(C)(C)C(=O)CC[C@]2(C)[C@@H]1CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H28O5/c1-11(20)16(24)19(5)8-6-12-17(2,3)14(21)7-9-18(12,4)13(19)10-15(22)23/h12-13H,6-10H2,1-5H3,(H,22,23)/t12-,13-,18-,19-/m0/s1

> <INCHI_KEY>
QWLGLRAGSFVBDI-OYUDYFSCSA-N

> <FORMULA>
C19H28O5

> <MOLECULAR_WEIGHT>
336.428

> <EXACT_MASS>
336.193674002

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
35.639957440011464

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(1S,2S,4aR,8aS)-2,5,5,8a-tetramethyl-6-oxo-2-(2-oxopropanoyl)-decahydronaphthalen-1-yl]acetic acid

> <JCHEM_LOGP>
3.695641586999998

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.21360685342421

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.503183036045995

> <JCHEM_PKA_STRONGEST_BASIC>
-7.438120605627377

> <JCHEM_POLAR_SURFACE_AREA>
88.51

> <JCHEM_REFRACTIVITY>
88.74799999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,2S,4aR,8aS)-2,5,5,8a-tetramethyl-6-oxo-2-(2-oxopropanoyl)-hexahydronaphthalen-1-yl]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.226  -0.328   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.710  -0.595   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.280   0.584   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.183  -2.043   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.173  -3.222   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.807  -3.757   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.345   1.180   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.325   1.180   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8   20                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   18                                                  
CONECT   11   10   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   10   19   20                                             
CONECT   19   18                                                            
CONECT   20   18    6   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

View in JSmol

Synonyms

Value	Source
2-[(1S,2S,4AR,8as)-2,5,5,8a-tetramethyl-6-oxo-2-(2-oxopropanoyl)-decahydronaphthalen-1-yl]acetate	Generator

Chemical Formula

C₁₉H₂₈O₅

Average Mass

336.4280 Da

Monoisotopic Mass

336.19367 Da

IUPAC Name

2-[(1S,2S,4aR,8aS)-2,5,5,8a-tetramethyl-6-oxo-2-(2-oxopropanoyl)-decahydronaphthalen-1-yl]acetic acid

Traditional Name

[(1S,2S,4aR,8aS)-2,5,5,8a-tetramethyl-6-oxo-2-(2-oxopropanoyl)-hexahydronaphthalen-1-yl]acetic acid

CAS Registry Number

Not Available

SMILES

CC(=O)C(=O)[C@@]1(C)CC[C@H]2C(C)(C)C(=O)CC[C@]2(C)[C@@H]1CC(O)=O

InChI Identifier

InChI=1S/C19H28O5/c1-11(20)16(24)19(5)8-6-12-17(2,3)14(21)7-9-18(12,4)13(19)10-15(22)23/h12-13H,6-10H2,1-5H3,(H,22,23)/t12-,13-,18-,19-/m0/s1

InChI Key

QWLGLRAGSFVBDI-OYUDYFSCSA-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
Rhabdastrella globostellata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha-diketones. These are organic compounds containing two ketone groups on two adjacent carbon atoms.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alpha-diketones

Alternative Parents

Substituents

Alpha-diketone
Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	3.7	ChemAxon
pKa (Strongest Acidic)	4.5	ChemAxon
pKa (Strongest Basic)	-7.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	88.51 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	88.75 m³·mol⁻¹	ChemAxon
Polarizability	35.64 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

27026655

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162872064

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(1s,2s,4ar,8as)-2,5,5,8a-tetramethyl-6-oxo-2-(2-oxopropanoyl)-hexahydronaphthalen-1-yl]acetic acid (NP0224492)

MOL for NP0224492 ([(1s,2s,4ar,8as)-2,5,5,8a-tetramethyl-6-oxo-2-(2-oxopropanoyl)-hexahydronaphthalen-1-yl]acetic acid)

3D MOL for NP0224492 ([(1s,2s,4ar,8as)-2,5,5,8a-tetramethyl-6-oxo-2-(2-oxopropanoyl)-hexahydronaphthalen-1-yl]acetic acid)

3D SDF for NP0224492 ([(1s,2s,4ar,8as)-2,5,5,8a-tetramethyl-6-oxo-2-(2-oxopropanoyl)-hexahydronaphthalen-1-yl]acetic acid)

3D-SDF for NP0224492 ([(1s,2s,4ar,8as)-2,5,5,8a-tetramethyl-6-oxo-2-(2-oxopropanoyl)-hexahydronaphthalen-1-yl]acetic acid)

PDB for NP0224492 ([(1s,2s,4ar,8as)-2,5,5,8a-tetramethyl-6-oxo-2-(2-oxopropanoyl)-hexahydronaphthalen-1-yl]acetic acid)

3D PDB for NP0224492 ([(1s,2s,4ar,8as)-2,5,5,8a-tetramethyl-6-oxo-2-(2-oxopropanoyl)-hexahydronaphthalen-1-yl]acetic acid)

SMILES for NP0224492 ([(1s,2s,4ar,8as)-2,5,5,8a-tetramethyl-6-oxo-2-(2-oxopropanoyl)-hexahydronaphthalen-1-yl]acetic acid)

INCHI for NP0224492 ([(1s,2s,4ar,8as)-2,5,5,8a-tetramethyl-6-oxo-2-(2-oxopropanoyl)-hexahydronaphthalen-1-yl]acetic acid)

Structure for NP0224492 ([(1s,2s,4ar,8as)-2,5,5,8a-tetramethyl-6-oxo-2-(2-oxopropanoyl)-hexahydronaphthalen-1-yl]acetic acid)

3D Structure for NP0224492 ([(1s,2s,4ar,8as)-2,5,5,8a-tetramethyl-6-oxo-2-(2-oxopropanoyl)-hexahydronaphthalen-1-yl]acetic acid)