NP-MRD: Showing NP-Card for 2-({4-[(2e)-3-[(1s,2s,4ar,8as)-2-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-1-hydroxyprop-2-en-1-ylidene]-1-methyl-3,5-dioxopyrrolidin-2-yl}methyl)-2-hydroxy-3-methylbutanoic acid (NP0195232)

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Record Information

Version

2.0

Created at

2022-09-04 13:03:22 UTC

Updated at

2022-09-04 13:03:22 UTC

NP-MRD ID

NP0195232

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-({4-[(2e)-3-[(1s,2s,4ar,8as)-2-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-1-hydroxyprop-2-en-1-ylidene]-1-methyl-3,5-dioxopyrrolidin-2-yl}methyl)-2-hydroxy-3-methylbutanoic acid

Description

2-({4-[(2E)-3-[(1S,2S,4aR,8aS)-2-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-1-hydroxyprop-2-en-1-ylidene]-1-methyl-3,5-dioxopyrrolidin-2-yl}methyl)-2-hydroxy-3-methylbutanoic acid belongs to the class of organic compounds known as heterocyclic fatty acids. These are fatty acids containing a heterocyclic attached to the acyl chain. 2-({4-[(2e)-3-[(1s,2s,4ar,8as)-2-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-1-hydroxyprop-2-en-1-ylidene]-1-methyl-3,5-dioxopyrrolidin-2-yl}methyl)-2-hydroxy-3-methylbutanoic acid is found in Zopfiella latipes. Based on a literature review very few articles have been published on 2-({4-[(2E)-3-[(1S,2S,4aR,8aS)-2-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-1-hydroxyprop-2-en-1-ylidene]-1-methyl-3,5-dioxopyrrolidin-2-yl}methyl)-2-hydroxy-3-methylbutanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042215032D          

 32 34  0  0  1  0            999 V2000
    5.3455    3.9149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5250    4.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1894    4.7549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0401    3.3337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3726    3.8187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5551    2.6663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7346    2.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1826    2.1394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3541    1.3325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9021    3.8475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6577    4.2207    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
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M  END

     RDKit          3D

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M  END


  Mrv1652309042215032D          

 32 34  0  0  1  0            999 V2000
    5.3455    3.9149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0195232

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(O)(CC1N(C)C(=O)C(=C(O)\C=C\[C@H]2[C@@H](C)C=C[C@H]3CCCC[C@H]23)C1=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H35NO6/c1-14(2)25(32,24(30)31)13-19-22(28)21(23(29)26(19)4)20(27)12-11-17-15(3)9-10-16-7-5-6-8-18(16)17/h9-12,14-19,27,32H,5-8,13H2,1-4H3,(H,30,31)/b12-11+,21-20?/t15-,16+,17-,18-,19?,25?/m0/s1

> <INCHI_KEY>
HYGFSUQJOBSOGP-YBIQCROSSA-N

> <FORMULA>
C25H35NO6

> <MOLECULAR_WEIGHT>
445.556

> <EXACT_MASS>
445.246437851

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
48.471128009542255

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-({4-[(2E)-3-[(1S,2S,4aR,8aS)-2-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-1-hydroxyprop-2-en-1-ylidene]-1-methyl-3,5-dioxopyrrolidin-2-yl}methyl)-2-hydroxy-3-methylbutanoic acid

> <JCHEM_LOGP>
3.1526878443333337

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.732844050949913

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6593348563495836

> <JCHEM_PKA_STRONGEST_BASIC>
-1.0187259538382887

> <JCHEM_POLAR_SURFACE_AREA>
115.14

> <JCHEM_REFRACTIVITY>
123.61209999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-({4-[(2E)-3-[(1S,2S,4aR,8aS)-2-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-1-hydroxyprop-2-en-1-ylidene]-1-methyl-3,5-dioxopyrrolidin-2-yl}methyl)-2-hydroxy-3-methylbutanoic acid

> <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       9.978   7.308   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.447   7.469   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.820   8.876   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.541   6.223   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       6.296   7.128   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.636   4.977   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.105   5.138   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.074   3.994   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.394   2.487   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.828   6.152   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.684   7.182   0.000  0.00  0.00           O+0
HETATM   28  N   UNK     0       4.335   6.472   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0       4.961   7.879   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.787   5.318   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       8.626   3.786   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      10.194   5.944   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6   30                                             
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   28                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   26                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   24                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   15   25                                                  
CONECT   25   24                                                            
CONECT   26   10   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26    7   29                                                  
CONECT   29   28                                                            
CONECT   30    4   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Value	Source
2-({4-[(2E)-3-[(1S,2S,4ar,8as)-2-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-1-hydroxyprop-2-en-1-ylidene]-1-methyl-3,5-dioxopyrrolidin-2-yl}methyl)-2-hydroxy-3-methylbutanoate	Generator

Chemical Formula

C₂₅H₃₅NO₆

Average Mass

445.5560 Da

Monoisotopic Mass

445.24644 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(C)C(O)(CC1N(C)C(=O)C(=C(O)\C=C\[C@H]2[C@@H](C)C=C[C@H]3CCCC[C@H]23)C1=O)C(O)=O

InChI Identifier

InChI=1S/C25H35NO6/c1-14(2)25(32,24(30)31)13-19-22(28)21(23(29)26(19)4)20(27)12-11-17-15(3)9-10-16-7-5-6-8-18(16)17/h9-12,14-19,27,32H,5-8,13H2,1-4H3,(H,30,31)/b12-11+,21-20?/t15-,16+,17-,18-,19?,25?/m0/s1

InChI Key

HYGFSUQJOBSOGP-YBIQCROSSA-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
Zopfiella latipes	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as heterocyclic fatty acids. These are fatty acids containing a heterocyclic attached to the acyl chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Heterocyclic fatty acids

Alternative Parents

Substituents

Methyl-branched fatty acid
Hydroxy fatty acid
Heterocyclic fatty acid
Branched fatty acid
N-alkylpyrrolidine
3-pyrrolidone
2-pyrrolidone
Pyrrolidone
Hydroxy acid
Alpha-hydroxy acid
Vinylogous acid
Tertiary carboxylic acid amide
Tertiary alcohol
Pyrrolidine
Cyclic ketone
Lactam
Ketone
Carboxamide group
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Enol
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
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	3.15	ChemAxon
pKa (Strongest Acidic)	3.66	ChemAxon
pKa (Strongest Basic)	-1	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

78437530

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139586046

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-({4-[(2e)-3-[(1s,2s,4ar,8as)-2-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-1-hydroxyprop-2-en-1-ylidene]-1-methyl-3,5-dioxopyrrolidin-2-yl}methyl)-2-hydroxy-3-methylbutanoic acid (NP0195232)

MOL for NP0195232 (2-({4-[(2e)-3-[(1s,2s,4ar,8as)-2-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-1-hydroxyprop-2-en-1-ylidene]-1-methyl-3,5-dioxopyrrolidin-2-yl}methyl)-2-hydroxy-3-methylbutanoic acid)

3D MOL for NP0195232 (2-({4-[(2e)-3-[(1s,2s,4ar,8as)-2-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-1-hydroxyprop-2-en-1-ylidene]-1-methyl-3,5-dioxopyrrolidin-2-yl}methyl)-2-hydroxy-3-methylbutanoic acid)

3D SDF for NP0195232 (2-({4-[(2e)-3-[(1s,2s,4ar,8as)-2-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-1-hydroxyprop-2-en-1-ylidene]-1-methyl-3,5-dioxopyrrolidin-2-yl}methyl)-2-hydroxy-3-methylbutanoic acid)

3D-SDF for NP0195232 (2-({4-[(2e)-3-[(1s,2s,4ar,8as)-2-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-1-hydroxyprop-2-en-1-ylidene]-1-methyl-3,5-dioxopyrrolidin-2-yl}methyl)-2-hydroxy-3-methylbutanoic acid)

PDB for NP0195232 (2-({4-[(2e)-3-[(1s,2s,4ar,8as)-2-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-1-hydroxyprop-2-en-1-ylidene]-1-methyl-3,5-dioxopyrrolidin-2-yl}methyl)-2-hydroxy-3-methylbutanoic acid)

3D PDB for NP0195232 (2-({4-[(2e)-3-[(1s,2s,4ar,8as)-2-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-1-hydroxyprop-2-en-1-ylidene]-1-methyl-3,5-dioxopyrrolidin-2-yl}methyl)-2-hydroxy-3-methylbutanoic acid)

SMILES for NP0195232 (2-({4-[(2e)-3-[(1s,2s,4ar,8as)-2-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-1-hydroxyprop-2-en-1-ylidene]-1-methyl-3,5-dioxopyrrolidin-2-yl}methyl)-2-hydroxy-3-methylbutanoic acid)

INCHI for NP0195232 (2-({4-[(2e)-3-[(1s,2s,4ar,8as)-2-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-1-hydroxyprop-2-en-1-ylidene]-1-methyl-3,5-dioxopyrrolidin-2-yl}methyl)-2-hydroxy-3-methylbutanoic acid)

Structure for NP0195232 (2-({4-[(2e)-3-[(1s,2s,4ar,8as)-2-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-1-hydroxyprop-2-en-1-ylidene]-1-methyl-3,5-dioxopyrrolidin-2-yl}methyl)-2-hydroxy-3-methylbutanoic acid)

3D Structure for NP0195232 (2-({4-[(2e)-3-[(1s,2s,4ar,8as)-2-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-1-hydroxyprop-2-en-1-ylidene]-1-methyl-3,5-dioxopyrrolidin-2-yl}methyl)-2-hydroxy-3-methylbutanoic acid)