NP-MRD: Showing NP-Card for 1,2,3-trimethyl (1r,2s)-1-{[(1s,4ar,5r,8as)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methoxy}propane-1,2,3-tricarboxylate (NP0177971)

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Record Information

Version

2.0

Created at

2022-09-03 15:53:08 UTC

Updated at

2022-09-03 15:53:09 UTC

NP-MRD ID

NP0177971

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,2,3-trimethyl (1r,2s)-1-{[(1s,4ar,5r,8as)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methoxy}propane-1,2,3-tricarboxylate

Description

(1R,2S)-1-[[[(1S,4aalpha)-Decahydro-5,8abeta-dimethyl-5alpha-(hydroxymethyl)-2-methylenenaphthalene]-1beta-yl]methoxy]propane-1,2,3-tricarboxylic acid trimethyl ester belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. Based on a literature review very few articles have been published on (1R,2S)-1-[[[(1S,4aalpha)-Decahydro-5,8abeta-dimethyl-5alpha-(hydroxymethyl)-2-methylenenaphthalene]-1beta-yl]methoxy]propane-1,2,3-tricarboxylic acid trimethyl ester.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032217532D          

 32 33  0  0  1  0            999 V2000
   -3.9849    4.8099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8099    4.8099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2224    5.5243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0474    5.5243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4599    4.8099    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0474    4.0954    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6349    3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.9845    5.2470    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


  Mrv1652309032217532D          

 32 33  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0177971

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C[C@@H]([C@@H](OC[C@H]1C(=C)CC[C@H]2[C@](C)(CO)CCC[C@]12C)C(=O)OC)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C24H38O8/c1-15-8-9-18-23(2,14-25)10-7-11-24(18,3)17(15)13-32-20(22(28)31-6)16(21(27)30-5)12-19(26)29-4/h16-18,20,25H,1,7-14H2,2-6H3/t16-,17-,18-,20+,23-,24+/m0/s1

> <INCHI_KEY>
YCEDLUKLAQSNAA-NVZATTGYSA-N

> <FORMULA>
C24H38O8

> <MOLECULAR_WEIGHT>
454.56

> <EXACT_MASS>
454.256668184

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
49.42441780491383

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,2,3-trimethyl (1R,2S)-1-{[(1S,4aR,5R,8aS)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-decahydronaphthalen-1-yl]methoxy}propane-1,2,3-tricarboxylate

> <JCHEM_LOGP>
2.2939287753333337

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.59233662010812

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.619569952548115

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2270739239073496

> <JCHEM_POLAR_SURFACE_AREA>
108.36000000000003

> <JCHEM_REFRACTIVITY>
116.61619999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
1,2,3-trimethyl (1R,2S)-1-{[(1S,4aR,5R,8aS)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1H-naphthalen-1-yl]methoxy}propane-1,2,3-tricarboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -7.438   8.978   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.978   8.978   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.748  10.312   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -11.288  10.312   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -12.058   8.978   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -11.288   7.645   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -10.518   6.311   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -12.058   6.311   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -13.598   6.311   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -14.368   7.645   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -13.598   8.978   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -14.904   9.794   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -13.652  10.517   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0     -12.346  11.334   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -9.748   7.645   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -8.978   6.311   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -7.438   6.311   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -6.668   4.977   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -7.438   3.644   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -8.978   3.644   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -6.668   2.310   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -7.438   0.976   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.128   4.977   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.358   3.644   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.818   3.644   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.048   4.977   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -2.048   2.310   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -0.508   2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -4.358   6.311   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -2.818   6.311   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -5.128   7.645   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -4.358   8.978   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7    8   15                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    5   12   13                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13                                                            
CONECT   15    6    2   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21                                                            
CONECT   23   18   24   29                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27                                                            
CONECT   29   23   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   66    0
END

View in JSmol

Synonyms

Value	Source
(1R,2S)-1-[[[(1S,4Aalpha)-decahydro-5,8abeta-dimethyl-5a-(hydroxymethyl)-2-methylenenaphthalene]-1b-yl]methoxy]propane-1,2,3-tricarboxylate trimethyl ester	Generator
(1R,2S)-1-[[[(1S,4Aalpha)-decahydro-5,8abeta-dimethyl-5a-(hydroxymethyl)-2-methylenenaphthalene]-1b-yl]methoxy]propane-1,2,3-tricarboxylic acid trimethyl ester	Generator
(1R,2S)-1-[[[(1S,4Aalpha)-decahydro-5,8abeta-dimethyl-5alpha-(hydroxymethyl)-2-methylenenaphthalene]-1beta-yl]methoxy]propane-1,2,3-tricarboxylate trimethyl ester	Generator
(1R,2S)-1-[[[(1S,4Aalpha)-decahydro-5,8abeta-dimethyl-5α-(hydroxymethyl)-2-methylenenaphthalene]-1β-yl]methoxy]propane-1,2,3-tricarboxylate trimethyl ester	Generator
(1R,2S)-1-[[[(1S,4Aalpha)-decahydro-5,8abeta-dimethyl-5α-(hydroxymethyl)-2-methylenenaphthalene]-1β-yl]methoxy]propane-1,2,3-tricarboxylic acid trimethyl ester	Generator

Chemical Formula

C₂₄H₃₈O₈

Average Mass

454.5600 Da

Monoisotopic Mass

454.25667 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC(=O)C[C@@H]([C@@H](OC[C@H]1C(=C)CC[C@H]2[C@](C)(CO)CCC[C@]12C)C(=O)OC)C(=O)OC

InChI Identifier

InChI=1S/C24H38O8/c1-15-8-9-18-23(2,14-25)10-7-11-24(18,3)17(15)13-32-20(22(28)31-6)16(21(27)30-5)12-19(26)29-4/h16-18,20,25H,1,7-14H2,2-6H3/t16-,17-,18-,20+,23-,24+/m0/s1

InChI Key

YCEDLUKLAQSNAA-NVZATTGYSA-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

Not Available

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 ester
Fatty acid methyl ester
Monosaccharide
Fatty acyl
Methyl ester
Carboxylic acid ester
Dialkyl ether
Ether
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
Carbonyl group
Organooxygen compound
Primary alcohol
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

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

13993294

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1,2,3-trimethyl (1r,2s)-1-{[(1s,4ar,5r,8as)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methoxy}propane-1,2,3-tricarboxylate (NP0177971)

MOL for NP0177971 (1,2,3-trimethyl (1r,2s)-1-{[(1s,4ar,5r,8as)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methoxy}propane-1,2,3-tricarboxylate)

3D MOL for NP0177971 (1,2,3-trimethyl (1r,2s)-1-{[(1s,4ar,5r,8as)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methoxy}propane-1,2,3-tricarboxylate)

3D SDF for NP0177971 (1,2,3-trimethyl (1r,2s)-1-{[(1s,4ar,5r,8as)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methoxy}propane-1,2,3-tricarboxylate)

3D-SDF for NP0177971 (1,2,3-trimethyl (1r,2s)-1-{[(1s,4ar,5r,8as)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methoxy}propane-1,2,3-tricarboxylate)

PDB for NP0177971 (1,2,3-trimethyl (1r,2s)-1-{[(1s,4ar,5r,8as)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methoxy}propane-1,2,3-tricarboxylate)

3D PDB for NP0177971 (1,2,3-trimethyl (1r,2s)-1-{[(1s,4ar,5r,8as)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methoxy}propane-1,2,3-tricarboxylate)

SMILES for NP0177971 (1,2,3-trimethyl (1r,2s)-1-{[(1s,4ar,5r,8as)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methoxy}propane-1,2,3-tricarboxylate)

INCHI for NP0177971 (1,2,3-trimethyl (1r,2s)-1-{[(1s,4ar,5r,8as)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methoxy}propane-1,2,3-tricarboxylate)

Structure for NP0177971 (1,2,3-trimethyl (1r,2s)-1-{[(1s,4ar,5r,8as)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methoxy}propane-1,2,3-tricarboxylate)

3D Structure for NP0177971 (1,2,3-trimethyl (1r,2s)-1-{[(1s,4ar,5r,8as)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methoxy}propane-1,2,3-tricarboxylate)