NP-MRD: Showing NP-Card for 2-[4-(acetyloxy)-8-(benzoyloxy)-1-(cyanomethyl)-6-ethenyl-4a-hydroxy-1,6-dimethyl-5-oxo-hexahydronaphthalen-2-yl]-2-methylpropanoic acid (NP0175081)

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Record Information

Version

2.0

Created at

2022-09-03 12:27:46 UTC

Updated at

2022-09-03 12:27:46 UTC

NP-MRD ID

NP0175081

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[4-(acetyloxy)-8-(benzoyloxy)-1-(cyanomethyl)-6-ethenyl-4a-hydroxy-1,6-dimethyl-5-oxo-hexahydronaphthalen-2-yl]-2-methylpropanoic acid

Description

2-[4-(Acetyloxy)-8-(benzoyloxy)-1-(cyanomethyl)-6-ethenyl-4a-hydroxy-1,6-dimethyl-5-oxo-decahydronaphthalen-2-yl]-2-methylpropanoic acid belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. 2-[4-(acetyloxy)-8-(benzoyloxy)-1-(cyanomethyl)-6-ethenyl-4a-hydroxy-1,6-dimethyl-5-oxo-hexahydronaphthalen-2-yl]-2-methylpropanoic acid is found in Orthosiphon aristatus. 2-[4-(Acetyloxy)-8-(benzoyloxy)-1-(cyanomethyl)-6-ethenyl-4a-hydroxy-1,6-dimethyl-5-oxo-decahydronaphthalen-2-yl]-2-methylpropanoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241502202D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004241502202D          

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  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  7 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  3  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 22 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
  5 28  1  0  0  0  0
 19 28  1  0  0  0  0
 28 29  1  0  0  0  0
 20 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 33 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0175081

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1CC(C(C)(C)C(O)=O)C(C)(CC#N)C2C(CC(C)(C=C)C(=O)C12O)OC(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H35NO8/c1-7-27(5)16-19(38-23(32)18-11-9-8-10-12-18)22-28(6,13-14-30)20(26(3,4)25(34)35)15-21(37-17(2)31)29(22,36)24(27)33/h7-12,19-22,36H,1,13,15-16H2,2-6H3,(H,34,35)

> <INCHI_KEY>
MPPSSZWVJZPPHO-UHFFFAOYSA-N

> <FORMULA>
C29H35NO8

> <MOLECULAR_WEIGHT>
525.598

> <EXACT_MASS>
525.236267091

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
54.42920375194976

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[4-(acetyloxy)-8-(benzoyloxy)-1-(cyanomethyl)-6-ethenyl-4a-hydroxy-1,6-dimethyl-5-oxo-decahydronaphthalen-2-yl]-2-methylpropanoic acid

> <ALOGPS_LOGP>
2.80

> <JCHEM_LOGP>
3.953861884333331

> <ALOGPS_LOGS>
-4.31

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.820808025648745

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.6126802102383144

> <JCHEM_PKA_STRONGEST_BASIC>
-4.18941599932785

> <JCHEM_POLAR_SURFACE_AREA>
150.99

> <JCHEM_REFRACTIVITY>
136.03349999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.57e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[4-(acetyloxy)-8-(benzoyloxy)-1-(cyanomethyl)-6-ethenyl-4a-hydroxy-1,6-dimethyl-5-oxo-hexahydronaphthalen-2-yl]-2-methylpropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.770   1.334   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.657   1.180   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.677   1.180   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.204   2.627   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       2.731   4.074   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.185  -2.043   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.195  -3.757   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.712  -4.025   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.001  -3.850   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   28                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   14                                                  
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    7   15   16   19                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   14   20   28                                                  
CONECT   20   19   21   30                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24   26                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24                                                            
CONECT   26   22   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26    5   19   29                                             
CONECT   29   28                                                            
CONECT   30   20   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   38                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   33                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   80    0
END

View in JSmol

Synonyms

Value	Source
2-[4-(Acetyloxy)-8-(benzoyloxy)-1-(cyanomethyl)-6-ethenyl-4a-hydroxy-1,6-dimethyl-5-oxo-decahydronaphthalen-2-yl]-2-methylpropanoate	Generator

Chemical Formula

C₂₉H₃₅NO₈

Average Mass

525.5980 Da

Monoisotopic Mass

525.23627 Da

IUPAC Name

2-[4-(acetyloxy)-8-(benzoyloxy)-1-(cyanomethyl)-6-ethenyl-4a-hydroxy-1,6-dimethyl-5-oxo-decahydronaphthalen-2-yl]-2-methylpropanoic acid

Traditional Name

2-[4-(acetyloxy)-8-(benzoyloxy)-1-(cyanomethyl)-6-ethenyl-4a-hydroxy-1,6-dimethyl-5-oxo-hexahydronaphthalen-2-yl]-2-methylpropanoic acid

CAS Registry Number

Not Available

SMILES

CC(=O)OC1CC(C(C)(C)C(O)=O)C(C)(CC#N)C2C(CC(C)(C=C)C(=O)C12O)OC(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C29H35NO8/c1-7-27(5)16-19(38-23(32)18-11-9-8-10-12-18)22-28(6,13-14-30)20(26(3,4)25(34)35)15-21(37-17(2)31)29(22,36)24(27)33/h7-12,19-22,36H,1,13,15-16H2,2-6H3,(H,34,35)

InChI Key

MPPSSZWVJZPPHO-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
Orthosiphon aristatus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acid esters

Alternative Parents

Substituents

Benzoate ester
Tricarboxylic acid or derivatives
Benzoyl
Cyclic alcohol
Tertiary alcohol
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Carboxylic acid
Carbonitrile
Nitrile
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Alcohol
Carbonyl group
Organic nitrogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
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	2.8	ALOGPS
logP	3.95	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	2.61	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	150.99 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	136.03 m³·mol⁻¹	ChemAxon
Polarizability	54.43 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

73198144

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-(acetyloxy)-8-(benzoyloxy)-1-(cyanomethyl)-6-ethenyl-4a-hydroxy-1,6-dimethyl-5-oxo-hexahydronaphthalen-2-yl]-2-methylpropanoic acid (NP0175081)

MOL for NP0175081 (2-[4-(acetyloxy)-8-(benzoyloxy)-1-(cyanomethyl)-6-ethenyl-4a-hydroxy-1,6-dimethyl-5-oxo-hexahydronaphthalen-2-yl]-2-methylpropanoic acid)

3D MOL for NP0175081 (2-[4-(acetyloxy)-8-(benzoyloxy)-1-(cyanomethyl)-6-ethenyl-4a-hydroxy-1,6-dimethyl-5-oxo-hexahydronaphthalen-2-yl]-2-methylpropanoic acid)

3D SDF for NP0175081 (2-[4-(acetyloxy)-8-(benzoyloxy)-1-(cyanomethyl)-6-ethenyl-4a-hydroxy-1,6-dimethyl-5-oxo-hexahydronaphthalen-2-yl]-2-methylpropanoic acid)

3D-SDF for NP0175081 (2-[4-(acetyloxy)-8-(benzoyloxy)-1-(cyanomethyl)-6-ethenyl-4a-hydroxy-1,6-dimethyl-5-oxo-hexahydronaphthalen-2-yl]-2-methylpropanoic acid)

PDB for NP0175081 (2-[4-(acetyloxy)-8-(benzoyloxy)-1-(cyanomethyl)-6-ethenyl-4a-hydroxy-1,6-dimethyl-5-oxo-hexahydronaphthalen-2-yl]-2-methylpropanoic acid)

3D PDB for NP0175081 (2-[4-(acetyloxy)-8-(benzoyloxy)-1-(cyanomethyl)-6-ethenyl-4a-hydroxy-1,6-dimethyl-5-oxo-hexahydronaphthalen-2-yl]-2-methylpropanoic acid)

SMILES for NP0175081 (2-[4-(acetyloxy)-8-(benzoyloxy)-1-(cyanomethyl)-6-ethenyl-4a-hydroxy-1,6-dimethyl-5-oxo-hexahydronaphthalen-2-yl]-2-methylpropanoic acid)

INCHI for NP0175081 (2-[4-(acetyloxy)-8-(benzoyloxy)-1-(cyanomethyl)-6-ethenyl-4a-hydroxy-1,6-dimethyl-5-oxo-hexahydronaphthalen-2-yl]-2-methylpropanoic acid)

Structure for NP0175081 (2-[4-(acetyloxy)-8-(benzoyloxy)-1-(cyanomethyl)-6-ethenyl-4a-hydroxy-1,6-dimethyl-5-oxo-hexahydronaphthalen-2-yl]-2-methylpropanoic acid)

3D Structure for NP0175081 (2-[4-(acetyloxy)-8-(benzoyloxy)-1-(cyanomethyl)-6-ethenyl-4a-hydroxy-1,6-dimethyl-5-oxo-hexahydronaphthalen-2-yl]-2-methylpropanoic acid)