NP-MRD: Showing NP-Card for (2r,3r,4as,5s,8ar)-5-[(5r)-5-hydroxyoctyl]-2-methyl-decahydroquinolin-3-yl (2e,4e)-octa-2,4-dienoate (NP0164710)

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Record Information

Version

2.0

Created at

2022-09-02 23:38:34 UTC

Updated at

2022-09-02 23:38:34 UTC

NP-MRD ID

NP0164710

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r,4as,5s,8ar)-5-[(5r)-5-hydroxyoctyl]-2-methyl-decahydroquinolin-3-yl (2e,4e)-octa-2,4-dienoate

Description

(+)-Lepadin G belongs to the class of organic compounds known as quinolidines. These are organic compounds containing a quinolidine or decahydroquinoline moiety, which is a bicyclic skeleton consisting of a piperidine fused to a cyclohexane ring. (2r,3r,4as,5s,8ar)-5-[(5r)-5-hydroxyoctyl]-2-methyl-decahydroquinolin-3-yl (2e,4e)-octa-2,4-dienoate was first documented in 2009 (PMID: 19775165). Based on a literature review very few articles have been published on (+)-Lepadin G.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032201382D          

 30 31  0  0  1  0            999 V2000
    3.3362    5.3562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7961    4.7325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9860    4.8885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4459    4.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6358    4.4207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0957    3.7971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.9530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2546    3.3293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0647    3.4853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9845    2.5498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5246    1.9262    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2546    1.1466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7946    0.5230    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5246   -0.2566    0.0000 C   0  0  1  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
   -0.4444   -1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3657   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9058   -0.7243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7159   -0.8802    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9860   -1.6598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0662   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6062    0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 27 28  1  1  0  0  0
 28 29  1  0  0  0  0
 11 29  1  0  0  0  0
 29 30  1  6  0  0  0
M  END

     RDKit          3D

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   -6.2541    0.0654   -0.8611 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -7.1173    2.2508    0.0128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8760    2.8263    1.2009 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5127   -0.0599    2.0333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1935    0.1006    2.7537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0050    0.2448    1.8682 C   0  0  1  0  0  0  0  0  0  0  0  0
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    1.1561   -1.7828    2.3164 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1521   -2.5083    3.1857 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.3409   -1.3349   -1.6948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6522    0.2478   -2.0343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6701    1.1798   -2.7233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5504   -0.4645   -3.3788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7689   -0.0553   -3.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2960   -1.3065   -1.7933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9205    1.6646   -1.4670 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.1537   -0.9982   -0.5725 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309032201382D          

 30 31  0  0  1  0            999 V2000
    3.3362    5.3562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2546    3.3293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9845    2.5498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5246    1.9262    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.4444   -1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3657   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9058   -0.7243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7159   -0.8802    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9860   -1.6598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2560   -0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0662   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6062    0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 29 30  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0164710

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC\C=C\C=C\C(=O)O[C@@H]1C[C@H]2[C@@H](CCCC[C@H](O)CCC)CCC[C@H]2N[C@@H]1C

> <INCHI_IDENTIFIER>
InChI=1S/C26H45NO3/c1-4-6-7-8-9-18-26(29)30-25-19-23-21(14-10-11-16-22(28)13-5-2)15-12-17-24(23)27-20(25)3/h7-9,18,20-25,27-28H,4-6,10-17,19H2,1-3H3/b8-7+,18-9+/t20-,21+,22-,23+,24-,25-/m1/s1

> <INCHI_KEY>
RLTXIRPCJHXWEP-WHZAVNHLSA-N

> <FORMULA>
C26H45NO3

> <MOLECULAR_WEIGHT>
419.65

> <EXACT_MASS>
419.339944313

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
52.63697657864984

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4aS,5S,8aR)-5-[(5R)-5-hydroxyoctyl]-2-methyl-decahydroquinolin-3-yl (2E,4E)-octa-2,4-dienoate

> <ALOGPS_LOGP>
6.25

> <JCHEM_LOGP>
6.530093059

> <ALOGPS_LOGS>
-6.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.516277260233043

> <JCHEM_PKA_STRONGEST_BASIC>
9.721874677306781

> <JCHEM_POLAR_SURFACE_AREA>
58.56

> <JCHEM_REFRACTIVITY>
126.2473

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.85e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4aS,5S,8aR)-5-[(5R)-5-hydroxyoctyl]-2-methyl-decahydroquinolin-3-yl (2E,4E)-octa-2,4-dienoate

> <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       6.228   9.998   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.219   8.834   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.707   9.125   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.699   7.961   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.187   8.252   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.179   7.088   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   7.379   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.342   6.215   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.854   6.506   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -1.838   4.760   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.846   3.595   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.342   2.140   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.350   0.976   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.846  -0.479   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.830  -2.225   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.683  -2.516   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.691  -1.352   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.203  -1.643   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.707  -3.098   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.211  -0.479   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.723  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.732   0.394   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.854  -1.643   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.366  -1.352   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -5.870   0.103   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.862   1.267   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0      -5.366   2.722   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0      -4.358   3.887   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -4.862   5.342   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   29                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   27                                                  
CONECT   14   13   15   24                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   14   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   13   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   11   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₄₅NO₃

Average Mass

419.6500 Da

Monoisotopic Mass

419.33994 Da

IUPAC Name

(2R,3R,4aS,5S,8aR)-5-[(5R)-5-hydroxyoctyl]-2-methyl-decahydroquinolin-3-yl (2E,4E)-octa-2,4-dienoate

Traditional Name

(2R,3R,4aS,5S,8aR)-5-[(5R)-5-hydroxyoctyl]-2-methyl-decahydroquinolin-3-yl (2E,4E)-octa-2,4-dienoate

CAS Registry Number

Not Available

SMILES

CCC\C=C\C=C\C(=O)O[C@@H]1C[C@H]2[C@@H](CCCC[C@H](O)CCC)CCC[C@H]2N[C@@H]1C

InChI Identifier

InChI=1S/C26H45NO3/c1-4-6-7-8-9-18-26(29)30-25-19-23-21(14-10-11-16-22(28)13-5-2)15-12-17-24(23)27-20(25)3/h7-9,18,20-25,27-28H,4-6,10-17,19H2,1-3H3/b8-7+,18-9+/t20-,21+,22-,23+,24-,25-/m1/s1

InChI Key

RLTXIRPCJHXWEP-WHZAVNHLSA-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 quinolidines. These are organic compounds containing a quinolidine or decahydroquinoline moiety, which is a bicyclic skeleton consisting of a piperidine fused to a cyclohexane ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolidines

Sub Class

Not Available

Direct Parent

Quinolidines

Alternative Parents

Substituents

Quinolidine
Fatty acid ester
Piperidine
Fatty acyl
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Amino acid or derivatives
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Azacycle
Secondary aliphatic amine
Monocarboxylic acid or derivatives
Secondary amine
Organonitrogen compound
Hydrocarbon derivative
Organic nitrogen compound
Amine
Organic oxide
Organopnictogen compound
Organooxygen compound
Alcohol
Carbonyl group
Organic oxygen 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	6.25	ALOGPS
logP	6.53	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	18.52	ChemAxon
pKa (Strongest Basic)	9.72	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.56 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	126.25 m³·mol⁻¹	ChemAxon
Polarizability	52.64 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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

553749

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

638193

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li G, Hsung RP: Assignment of the C5' relative stereochemistry in (+)-lepadin F and (+)-lepadin G and absolute configuration of (+)-lepadin G. Org Lett. 2009 Oct 15;11(20):4616-9. doi: 10.1021/ol9018997. [PubMed:19775165 ]
LOTUS database [Link]

Showing NP-Card for (2r,3r,4as,5s,8ar)-5-[(5r)-5-hydroxyoctyl]-2-methyl-decahydroquinolin-3-yl (2e,4e)-octa-2,4-dienoate (NP0164710)

MOL for NP0164710 ((2r,3r,4as,5s,8ar)-5-[(5r)-5-hydroxyoctyl]-2-methyl-decahydroquinolin-3-yl (2e,4e)-octa-2,4-dienoate)

3D MOL for NP0164710 ((2r,3r,4as,5s,8ar)-5-[(5r)-5-hydroxyoctyl]-2-methyl-decahydroquinolin-3-yl (2e,4e)-octa-2,4-dienoate)

3D SDF for NP0164710 ((2r,3r,4as,5s,8ar)-5-[(5r)-5-hydroxyoctyl]-2-methyl-decahydroquinolin-3-yl (2e,4e)-octa-2,4-dienoate)

3D-SDF for NP0164710 ((2r,3r,4as,5s,8ar)-5-[(5r)-5-hydroxyoctyl]-2-methyl-decahydroquinolin-3-yl (2e,4e)-octa-2,4-dienoate)

PDB for NP0164710 ((2r,3r,4as,5s,8ar)-5-[(5r)-5-hydroxyoctyl]-2-methyl-decahydroquinolin-3-yl (2e,4e)-octa-2,4-dienoate)

3D PDB for NP0164710 ((2r,3r,4as,5s,8ar)-5-[(5r)-5-hydroxyoctyl]-2-methyl-decahydroquinolin-3-yl (2e,4e)-octa-2,4-dienoate)

SMILES for NP0164710 ((2r,3r,4as,5s,8ar)-5-[(5r)-5-hydroxyoctyl]-2-methyl-decahydroquinolin-3-yl (2e,4e)-octa-2,4-dienoate)

INCHI for NP0164710 ((2r,3r,4as,5s,8ar)-5-[(5r)-5-hydroxyoctyl]-2-methyl-decahydroquinolin-3-yl (2e,4e)-octa-2,4-dienoate)

Structure for NP0164710 ((2r,3r,4as,5s,8ar)-5-[(5r)-5-hydroxyoctyl]-2-methyl-decahydroquinolin-3-yl (2e,4e)-octa-2,4-dienoate)

3D Structure for NP0164710 ((2r,3r,4as,5s,8ar)-5-[(5r)-5-hydroxyoctyl]-2-methyl-decahydroquinolin-3-yl (2e,4e)-octa-2,4-dienoate)