NP-MRD: Showing NP-Card for 1-(3-hydroxy-4-methylpent-4-en-1-yl)-5-[(4-hydroxy-5,6-dimethyl-2-oxopyran-3-yl)methyl]-1,4a-dimethyl-6-methylidene-hexahydro-2h-naphthalen-2-yl acetate (NP0269751)

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Record Information

Version

2.0

Created at

2022-09-08 15:20:52 UTC

Updated at

2022-09-08 15:20:52 UTC

NP-MRD ID

NP0269751

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-(3-hydroxy-4-methylpent-4-en-1-yl)-5-[(4-hydroxy-5,6-dimethyl-2-oxopyran-3-yl)methyl]-1,4a-dimethyl-6-methylidene-hexahydro-2h-naphthalen-2-yl acetate

Description

SCHEMBL14579972 belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. Based on a literature review very few articles have been published on SCHEMBL14579972.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082217202D          

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M  END

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M  END


  Mrv1652309082217202D          

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 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 21 29  1  0  0  0  0
 29 30  2  0  0  0  0
 19 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
  8 35  1  0  0  0  0
 17 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0269751

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1CCC2(C)C(CC3=C(O)C(C)=C(C)OC3=O)C(=C)CCC2C1(C)CCC(O)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C29H42O6/c1-16(2)23(31)11-13-29(8)24-10-9-17(3)22(28(24,7)14-12-25(29)35-20(6)30)15-21-26(32)18(4)19(5)34-27(21)33/h22-25,31-32H,1,3,9-15H2,2,4-8H3

> <INCHI_KEY>
UCNIKIQFSZAFQI-UHFFFAOYSA-N

> <FORMULA>
C29H42O6

> <MOLECULAR_WEIGHT>
486.649

> <EXACT_MASS>
486.298139072

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
55.03995548805791

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-(3-hydroxy-4-methylpent-4-en-1-yl)-5-[(4-hydroxy-5,6-dimethyl-2-oxo-2H-pyran-3-yl)methyl]-1,4a-dimethyl-6-methylidene-decahydronaphthalen-2-yl acetate

> <JCHEM_LOGP>
4.75721739266667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.96287027454507

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.6508930922807

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5028380628849578

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
137.43189999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
1-(3-hydroxy-4-methylpent-4-en-1-yl)-5-[(4-hydroxy-5,6-dimethyl-2-oxopyran-3-yl)methyl]-1,4a-dimethyl-6-methylidene-hexahydro-2H-naphthalen-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       5.357  -0.125   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.690  -0.895   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.690  -2.435   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.024  -0.125   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       8.024   1.415   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       9.358  -0.895   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.691  -0.125   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.025  -0.895   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.035  -2.075   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.552   0.552   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      11.562   1.732   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      12.089   3.179   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.099   4.359   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      13.605   3.446   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      14.068   0.819   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.058  -0.360   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.532  -1.807   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.048  -1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.522  -2.987   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      17.038  -2.720   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      18.028  -3.899   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      19.545  -3.632   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      20.071  -2.185   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      20.535  -4.812   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      22.051  -4.544   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      20.008  -6.259   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      20.998  -7.439   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      18.491  -6.526   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      17.501  -5.347   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      15.985  -5.614   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      14.995  -4.434   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      15.102  -5.971   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      13.478  -4.702   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      12.488  -3.522   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      13.015  -2.075   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   35                                             
CONECT    9    8                                                            
CONECT   10    8   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   10   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19   35                                             
CONECT   18   17                                                            
CONECT   19   17   20   31                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   29                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   21   30                                                  
CONECT   30   29                                                            
CONECT   31   19   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34    8   17                                                  
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₄₂O₆

Average Mass

486.6490 Da

Monoisotopic Mass

486.29814 Da

IUPAC Name

1-(3-hydroxy-4-methylpent-4-en-1-yl)-5-[(4-hydroxy-5,6-dimethyl-2-oxo-2H-pyran-3-yl)methyl]-1,4a-dimethyl-6-methylidene-decahydronaphthalen-2-yl acetate

Traditional Name

1-(3-hydroxy-4-methylpent-4-en-1-yl)-5-[(4-hydroxy-5,6-dimethyl-2-oxopyran-3-yl)methyl]-1,4a-dimethyl-6-methylidene-hexahydro-2H-naphthalen-2-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1CCC2(C)C(CC3=C(O)C(C)=C(C)OC3=O)C(=C)CCC2C1(C)CCC(O)C(C)=C

InChI Identifier

InChI=1S/C29H42O6/c1-16(2)23(31)11-13-29(8)24-10-9-17(3)22(28(24,7)14-12-25(29)35-20(6)30)15-21-26(32)18(4)19(5)34-27(21)33/h22-25,31-32H,1,3,9-15H2,2,4-8H3

InChI Key

UCNIKIQFSZAFQI-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Pyranone
Pyran
Heteroaromatic compound
Vinylogous acid
Carboxylic acid ester
Lactone
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Alcohol
Organooxygen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	4.76	ChemAxon
pKa (Strongest Acidic)	7.65	ChemAxon
pKa (Strongest Basic)	-1.5	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	8	ChemAxon
Refractivity	137.43 m³·mol⁻¹	ChemAxon
Polarizability	55.04 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

58810690

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-(3-hydroxy-4-methylpent-4-en-1-yl)-5-[(4-hydroxy-5,6-dimethyl-2-oxopyran-3-yl)methyl]-1,4a-dimethyl-6-methylidene-hexahydro-2h-naphthalen-2-yl acetate (NP0269751)

MOL for NP0269751 (1-(3-hydroxy-4-methylpent-4-en-1-yl)-5-[(4-hydroxy-5,6-dimethyl-2-oxopyran-3-yl)methyl]-1,4a-dimethyl-6-methylidene-hexahydro-2h-naphthalen-2-yl acetate)

3D MOL for NP0269751 (1-(3-hydroxy-4-methylpent-4-en-1-yl)-5-[(4-hydroxy-5,6-dimethyl-2-oxopyran-3-yl)methyl]-1,4a-dimethyl-6-methylidene-hexahydro-2h-naphthalen-2-yl acetate)

3D SDF for NP0269751 (1-(3-hydroxy-4-methylpent-4-en-1-yl)-5-[(4-hydroxy-5,6-dimethyl-2-oxopyran-3-yl)methyl]-1,4a-dimethyl-6-methylidene-hexahydro-2h-naphthalen-2-yl acetate)

3D-SDF for NP0269751 (1-(3-hydroxy-4-methylpent-4-en-1-yl)-5-[(4-hydroxy-5,6-dimethyl-2-oxopyran-3-yl)methyl]-1,4a-dimethyl-6-methylidene-hexahydro-2h-naphthalen-2-yl acetate)

PDB for NP0269751 (1-(3-hydroxy-4-methylpent-4-en-1-yl)-5-[(4-hydroxy-5,6-dimethyl-2-oxopyran-3-yl)methyl]-1,4a-dimethyl-6-methylidene-hexahydro-2h-naphthalen-2-yl acetate)

3D PDB for NP0269751 (1-(3-hydroxy-4-methylpent-4-en-1-yl)-5-[(4-hydroxy-5,6-dimethyl-2-oxopyran-3-yl)methyl]-1,4a-dimethyl-6-methylidene-hexahydro-2h-naphthalen-2-yl acetate)

SMILES for NP0269751 (1-(3-hydroxy-4-methylpent-4-en-1-yl)-5-[(4-hydroxy-5,6-dimethyl-2-oxopyran-3-yl)methyl]-1,4a-dimethyl-6-methylidene-hexahydro-2h-naphthalen-2-yl acetate)

INCHI for NP0269751 (1-(3-hydroxy-4-methylpent-4-en-1-yl)-5-[(4-hydroxy-5,6-dimethyl-2-oxopyran-3-yl)methyl]-1,4a-dimethyl-6-methylidene-hexahydro-2h-naphthalen-2-yl acetate)

Structure for NP0269751 (1-(3-hydroxy-4-methylpent-4-en-1-yl)-5-[(4-hydroxy-5,6-dimethyl-2-oxopyran-3-yl)methyl]-1,4a-dimethyl-6-methylidene-hexahydro-2h-naphthalen-2-yl acetate)

3D Structure for NP0269751 (1-(3-hydroxy-4-methylpent-4-en-1-yl)-5-[(4-hydroxy-5,6-dimethyl-2-oxopyran-3-yl)methyl]-1,4a-dimethyl-6-methylidene-hexahydro-2h-naphthalen-2-yl acetate)