NP-MRD: Showing NP-Card for 1-[(1s,2r,4as,8ar)-1-[(3r)-4-methoxy-3-methyl-4-oxobutyl]-1,2,5-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methyl 4-methyl butanedioate (NP0145557)

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Record Information

Version

2.0

Created at

2022-09-02 00:47:06 UTC

Updated at

2022-09-02 00:47:06 UTC

NP-MRD ID

NP0145557

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-[(1s,2r,4as,8ar)-1-[(3r)-4-methoxy-3-methyl-4-oxobutyl]-1,2,5-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methyl 4-methyl butanedioate

Description

1-[(1S,2R,4aS,8aR)-1-[(3R)-4-methoxy-3-methyl-4-oxobutyl]-1,2,5-trimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-4a-yl]methyl 4-methyl butanedioate belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. 1-[(1s,2r,4as,8ar)-1-[(3r)-4-methoxy-3-methyl-4-oxobutyl]-1,2,5-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methyl 4-methyl butanedioate is found in Chrysothamnus stylosus. Based on a literature review very few articles have been published on 1-[(1S,2R,4aS,8aR)-1-[(3R)-4-methoxy-3-methyl-4-oxobutyl]-1,2,5-trimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-4a-yl]methyl 4-methyl butanedioate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022202472D          

 31 32  0  0  1  0            999 V2000
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6585   -3.8701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  1  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
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  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
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  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
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 29 30  2  0  0  0  0
 11 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309022202472D          

 31 32  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0145557

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)CCC(=O)OC[C@@]12CC[C@@H](C)[C@](C)(CC[C@@H](C)C(=O)OC)[C@H]1CCC=C2C

> <INCHI_IDENTIFIER>
InChI=1S/C25H40O6/c1-17(23(28)30-6)12-14-24(4)18(2)13-15-25(19(3)8-7-9-20(24)25)16-31-22(27)11-10-21(26)29-5/h8,17-18,20H,7,9-16H2,1-6H3/t17-,18-,20-,24+,25-/m1/s1

> <INCHI_KEY>
LFPNFHFVASKHJS-RLFCIGJUSA-N

> <FORMULA>
C25H40O6

> <MOLECULAR_WEIGHT>
436.589

> <EXACT_MASS>
436.282489008

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
49.59034611685766

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-[(1S,2R,4aS,8aR)-1-[(3R)-4-methoxy-3-methyl-4-oxobutyl]-1,2,5-trimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-4a-yl]methyl 4-methyl butanedioate

> <ALOGPS_LOGP>
5.39

> <JCHEM_LOGP>
4.555889278666665

> <ALOGPS_LOGS>
-5.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.566033641307569

> <JCHEM_POLAR_SURFACE_AREA>
78.90000000000002

> <JCHEM_REFRACTIVITY>
118.94959999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.50e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[(1S,2R,4aS,8aR)-1-[(3R)-4-methoxy-3-methyl-4-oxobutyl]-1,2,5-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methyl 4-methyl butanedioate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.334  -8.470   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.000 -10.780   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.334  -8.470   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -8.470   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.096  -7.224   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.668  -8.470   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.345  -3.440   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.325  -3.440   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.798  -1.993   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.788  -0.813   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.304  -1.081   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.261   0.634   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.744   0.901   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       7.251   1.813   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.724   3.261   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.002  -9.240   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                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   26   30                                             
CONECT   12   11   13                                                       
CONECT   13   12   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   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24                                                            
CONECT   26   16   11   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   11   31                                                  
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   64    0
END

View in JSmol

Synonyms

Value	Source
1-[(1S,2R,4AS,8ar)-1-[(3R)-4-methoxy-3-methyl-4-oxobutyl]-1,2,5-trimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-4a-yl]methyl 4-methyl butanedioic acid	Generator

Chemical Formula

C₂₅H₄₀O₆

Average Mass

436.5890 Da

Monoisotopic Mass

436.28249 Da

IUPAC Name

1-[(1S,2R,4aS,8aR)-1-[(3R)-4-methoxy-3-methyl-4-oxobutyl]-1,2,5-trimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-4a-yl]methyl 4-methyl butanedioate

Traditional Name

1-[(1S,2R,4aS,8aR)-1-[(3R)-4-methoxy-3-methyl-4-oxobutyl]-1,2,5-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methyl 4-methyl butanedioate

CAS Registry Number

Not Available

SMILES

COC(=O)CCC(=O)OC[C@@]12CC[C@@H](C)[C@](C)(CC[C@@H](C)C(=O)OC)[C@H]1CCC=C2C

InChI Identifier

InChI=1S/C25H40O6/c1-17(23(28)30-6)12-14-24(4)18(2)13-15-25(19(3)8-7-9-20(24)25)16-31-22(27)11-10-21(26)29-5/h8,17-18,20H,7,9-16H2,1-6H3/t17-,18-,20-,24+,25-/m1/s1

InChI Key

LFPNFHFVASKHJS-RLFCIGJUSA-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
Chrysothamnus stylosus	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
Fatty acid methyl ester
Fatty acid ester
Fatty acyl
Methyl ester
Carboxylic acid ester
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	5.39	ALOGPS
logP	4.56	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Basic)	-6.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	78.9 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	118.95 m³·mol⁻¹	ChemAxon
Polarizability	49.59 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

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

162905011

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-[(1s,2r,4as,8ar)-1-[(3r)-4-methoxy-3-methyl-4-oxobutyl]-1,2,5-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methyl 4-methyl butanedioate (NP0145557)

MOL for NP0145557 (1-[(1s,2r,4as,8ar)-1-[(3r)-4-methoxy-3-methyl-4-oxobutyl]-1,2,5-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methyl 4-methyl butanedioate)

3D MOL for NP0145557 (1-[(1s,2r,4as,8ar)-1-[(3r)-4-methoxy-3-methyl-4-oxobutyl]-1,2,5-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methyl 4-methyl butanedioate)

3D SDF for NP0145557 (1-[(1s,2r,4as,8ar)-1-[(3r)-4-methoxy-3-methyl-4-oxobutyl]-1,2,5-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methyl 4-methyl butanedioate)

3D-SDF for NP0145557 (1-[(1s,2r,4as,8ar)-1-[(3r)-4-methoxy-3-methyl-4-oxobutyl]-1,2,5-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methyl 4-methyl butanedioate)

PDB for NP0145557 (1-[(1s,2r,4as,8ar)-1-[(3r)-4-methoxy-3-methyl-4-oxobutyl]-1,2,5-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methyl 4-methyl butanedioate)

3D PDB for NP0145557 (1-[(1s,2r,4as,8ar)-1-[(3r)-4-methoxy-3-methyl-4-oxobutyl]-1,2,5-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methyl 4-methyl butanedioate)

SMILES for NP0145557 (1-[(1s,2r,4as,8ar)-1-[(3r)-4-methoxy-3-methyl-4-oxobutyl]-1,2,5-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methyl 4-methyl butanedioate)

INCHI for NP0145557 (1-[(1s,2r,4as,8ar)-1-[(3r)-4-methoxy-3-methyl-4-oxobutyl]-1,2,5-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methyl 4-methyl butanedioate)

Structure for NP0145557 (1-[(1s,2r,4as,8ar)-1-[(3r)-4-methoxy-3-methyl-4-oxobutyl]-1,2,5-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methyl 4-methyl butanedioate)

3D Structure for NP0145557 (1-[(1s,2r,4as,8ar)-1-[(3r)-4-methoxy-3-methyl-4-oxobutyl]-1,2,5-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methyl 4-methyl butanedioate)