NP-MRD: Showing NP-Card for methyl 5-[4-hydroxy-5-(hydroxymethyl)-1,4a-dimethyl-2-{[(2-phenylacetyl)oxy]methyl}-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-methylpent-2-enoate (NP0196198)

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Record Information

Version

1.0

Created at

2022-09-04 14:14:11 UTC

Updated at

2022-09-04 14:14:11 UTC

NP-MRD ID

NP0196198

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 5-[4-hydroxy-5-(hydroxymethyl)-1,4a-dimethyl-2-{[(2-phenylacetyl)oxy]methyl}-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-methylpent-2-enoate

Description

Methyl 5-[4-hydroxy-5-(hydroxymethyl)-1,4a-dimethyl-2-{[(2-phenylacetyl)oxy]methyl}-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl]-3-methylpent-2-enoate belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations. methyl 5-[4-hydroxy-5-(hydroxymethyl)-1,4a-dimethyl-2-{[(2-phenylacetyl)oxy]methyl}-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-methylpent-2-enoate is found in Moquiniastrum paniculatum. Methyl 5-[4-hydroxy-5-(hydroxymethyl)-1,4a-dimethyl-2-{[(2-phenylacetyl)oxy]methyl}-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl]-3-methylpent-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171517192D          

 35 37  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004171517192D          

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  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 12 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 10 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 27 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0196198

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C=C(C)CCC1(C)C(COC(=O)CC2=CC=CC=C2)CC(O)C2(C)C1CCC=C2CO

> <INCHI_IDENTIFIER>
InChI=1S/C29H40O6/c1-20(15-26(32)34-4)13-14-28(2)23(19-35-27(33)16-21-9-6-5-7-10-21)17-25(31)29(3)22(18-30)11-8-12-24(28)29/h5-7,9-11,15,23-25,30-31H,8,12-14,16-19H2,1-4H3

> <INCHI_KEY>
ULEQWUMXYWDQSB-UHFFFAOYSA-N

> <FORMULA>
C29H40O6

> <MOLECULAR_WEIGHT>
484.633

> <EXACT_MASS>
484.282489008

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
53.98629761635764

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 5-[4-hydroxy-5-(hydroxymethyl)-1,4a-dimethyl-2-{[(2-phenylacetyl)oxy]methyl}-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl]-3-methylpent-2-enoate

> <ALOGPS_LOGP>
4.33

> <JCHEM_LOGP>
4.206036823

> <ALOGPS_LOGS>
-5.26

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.261336083988006

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.50737816248305

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7368231579447464

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
136.77810000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.65e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 5-[4-hydroxy-5-(hydroxymethyl)-1,4a-dimethyl-2-{[(2-phenylacetyl)oxy]methyl}-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-methylpent-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0     -10.370   1.699   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -8.853   1.967   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -7.863   0.787   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -8.390  -0.660   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -6.347   1.055   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.357  -0.125   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.883  -1.572   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.840   0.142   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.850  -1.037   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.860   0.677   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   29                                             
CONECT   11   10                                                            
CONECT   12   10   13   24                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   18                                                       
CONECT   24   12   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29   33                                             
CONECT   28   27                                                            
CONECT   29   27   10   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   27   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

View in JSmol

Synonyms

Value	Source
Methyl 5-[4-hydroxy-5-(hydroxymethyl)-1,4a-dimethyl-2-{[(2-phenylacetyl)oxy]methyl}-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl]-3-methylpent-2-enoic acid	Generator

Chemical Formula

C₂₉H₄₀O₆

Average Mass

484.6330 Da

Monoisotopic Mass

484.28249 Da

IUPAC Name

methyl 5-[4-hydroxy-5-(hydroxymethyl)-1,4a-dimethyl-2-{[(2-phenylacetyl)oxy]methyl}-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl]-3-methylpent-2-enoate

Traditional Name

methyl 5-[4-hydroxy-5-(hydroxymethyl)-1,4a-dimethyl-2-{[(2-phenylacetyl)oxy]methyl}-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-methylpent-2-enoate

CAS Registry Number

Not Available

SMILES

COC(=O)C=C(C)CCC1(C)C(COC(=O)CC2=CC=CC=C2)CC(O)C2(C)C1CCC=C2CO

InChI Identifier

InChI=1S/C29H40O6/c1-20(15-26(32)34-4)13-14-28(2)23(19-35-27(33)16-21-9-6-5-7-10-21)17-25(31)29(3)22(18-30)11-8-12-24(28)29/h5-7,9-11,15,23-25,30-31H,8,12-14,16-19H2,1-4H3

InChI Key

ULEQWUMXYWDQSB-UHFFFAOYSA-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
Gochnatia paniculata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Colensane and clerodane diterpenoids

Alternative Parents

Substituents

Clerodane diterpenoid
Fatty acid ester
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Fatty acyl
Benzenoid
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
Primary alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic 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	4.33	ALOGPS
logP	4.21	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	14.51	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	136.78 m³·mol⁻¹	ChemAxon
Polarizability	53.99 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 5-[4-hydroxy-5-(hydroxymethyl)-1,4a-dimethyl-2-{[(2-phenylacetyl)oxy]methyl}-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-methylpent-2-enoate (NP0196198)

MOL for NP0196198 (methyl 5-[4-hydroxy-5-(hydroxymethyl)-1,4a-dimethyl-2-{[(2-phenylacetyl)oxy]methyl}-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-methylpent-2-enoate)

3D MOL for NP0196198 (methyl 5-[4-hydroxy-5-(hydroxymethyl)-1,4a-dimethyl-2-{[(2-phenylacetyl)oxy]methyl}-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-methylpent-2-enoate)

3D SDF for NP0196198 (methyl 5-[4-hydroxy-5-(hydroxymethyl)-1,4a-dimethyl-2-{[(2-phenylacetyl)oxy]methyl}-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-methylpent-2-enoate)

3D-SDF for NP0196198 (methyl 5-[4-hydroxy-5-(hydroxymethyl)-1,4a-dimethyl-2-{[(2-phenylacetyl)oxy]methyl}-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-methylpent-2-enoate)

PDB for NP0196198 (methyl 5-[4-hydroxy-5-(hydroxymethyl)-1,4a-dimethyl-2-{[(2-phenylacetyl)oxy]methyl}-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-methylpent-2-enoate)

3D PDB for NP0196198 (methyl 5-[4-hydroxy-5-(hydroxymethyl)-1,4a-dimethyl-2-{[(2-phenylacetyl)oxy]methyl}-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-methylpent-2-enoate)

SMILES for NP0196198 (methyl 5-[4-hydroxy-5-(hydroxymethyl)-1,4a-dimethyl-2-{[(2-phenylacetyl)oxy]methyl}-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-methylpent-2-enoate)

INCHI for NP0196198 (methyl 5-[4-hydroxy-5-(hydroxymethyl)-1,4a-dimethyl-2-{[(2-phenylacetyl)oxy]methyl}-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-methylpent-2-enoate)

Structure for NP0196198 (methyl 5-[4-hydroxy-5-(hydroxymethyl)-1,4a-dimethyl-2-{[(2-phenylacetyl)oxy]methyl}-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-methylpent-2-enoate)

3D Structure for NP0196198 (methyl 5-[4-hydroxy-5-(hydroxymethyl)-1,4a-dimethyl-2-{[(2-phenylacetyl)oxy]methyl}-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-methylpent-2-enoate)