NP-MRD: Showing NP-Card for 7,8-diformyl-5-hydroxy-4,4,8a-trimethyl-1,2,3,4a,5,8-hexahydronaphthalen-1-yl 3-(4-methoxyphenyl)prop-2-enoate (NP0255558)

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Record Information

Version

2.0

Created at

2022-09-07 20:06:08 UTC

Updated at

2022-09-07 20:06:08 UTC

NP-MRD ID

NP0255558

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7,8-diformyl-5-hydroxy-4,4,8a-trimethyl-1,2,3,4a,5,8-hexahydronaphthalen-1-yl 3-(4-methoxyphenyl)prop-2-enoate

Description

7,8-Diformyl-5-hydroxy-4,4,8a-trimethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalen-1-yl 3-(4-methoxyphenyl)prop-2-enoate belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid. 7,8-diformyl-5-hydroxy-4,4,8a-trimethyl-1,2,3,4a,5,8-hexahydronaphthalen-1-yl 3-(4-methoxyphenyl)prop-2-enoate is found in Zygogynum acsmithii. 7,8-Diformyl-5-hydroxy-4,4,8a-trimethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalen-1-yl 3-(4-methoxyphenyl)prop-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004171522182D          

 31 33  0  0  0  0            999 V2000
    0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    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
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8986    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9592    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  7  6  1  4  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 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  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 25 28  1  0  0  0  0
 12 28  1  0  0  0  0
 18 28  1  0  0  0  0
 28 29  1  0  0  0  0
  6 30  1  0  0  0  0
 30 31  2  0  0  0  0
  3 31  1  0  0  0  0
M  END


  Mrv1533004171522182D          

 31 33  0  0  0  0            999 V2000
    0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    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
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8986    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9592    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  7  6  1  4  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 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  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 25 28  1  0  0  0  0
 12 28  1  0  0  0  0
 18 28  1  0  0  0  0
 28 29  1  0  0  0  0
  6 30  1  0  0  0  0
 30 31  2  0  0  0  0
  3 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0255558

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=CC(=O)OC2CCC(C)(C)C3C(O)C=C(C=O)C(C=O)C23C)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C25H30O6/c1-24(2)12-11-21(25(3)19(15-27)17(14-26)13-20(28)23(24)25)31-22(29)10-7-16-5-8-18(30-4)9-6-16/h5-10,13-15,19-21,23,28H,11-12H2,1-4H3

> <INCHI_KEY>
YWTPSTGVICXAEK-UHFFFAOYSA-N

> <FORMULA>
C25H30O6

> <MOLECULAR_WEIGHT>
426.509

> <EXACT_MASS>
426.204238686

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
46.217619012174296

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7,8-diformyl-5-hydroxy-4,4,8a-trimethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalen-1-yl 3-(4-methoxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
3.41

> <JCHEM_LOGP>
3.025170217333333

> <ALOGPS_LOGS>
-4.98

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.660637474427574

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.246352243782894

> <JCHEM_PKA_STRONGEST_BASIC>
-3.02525936123925

> <JCHEM_POLAR_SURFACE_AREA>
89.9

> <JCHEM_REFRACTIVITY>
118.09160000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.46e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7,8-diformyl-5-hydroxy-4,4,8a-trimethyl-1,2,3,4a,5,8-hexahydronaphthalen-1-yl 3-(4-methoxyphenyl)prop-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       1.334 -14.630   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000 -13.860   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -0.770   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       1.677   1.180   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.657   1.180   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+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       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.001  -5.390   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  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   31                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   30                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   28                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15   19   28                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   25   12   18   29                                             
CONECT   29   28                                                            
CONECT   30    6   31                                                       
CONECT   31   30    3                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Value	Source
7,8-Diformyl-5-hydroxy-4,4,8a-trimethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalen-1-yl 3-(4-methoxyphenyl)prop-2-enoic acid	Generator

Chemical Formula

C₂₅H₃₀O₆

Average Mass

426.5090 Da

Monoisotopic Mass

426.20424 Da

IUPAC Name

7,8-diformyl-5-hydroxy-4,4,8a-trimethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalen-1-yl 3-(4-methoxyphenyl)prop-2-enoate

Traditional Name

7,8-diformyl-5-hydroxy-4,4,8a-trimethyl-1,2,3,4a,5,8-hexahydronaphthalen-1-yl 3-(4-methoxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=CC(=O)OC2CCC(C)(C)C3C(O)C=C(C=O)C(C=O)C23C)C=C1

InChI Identifier

InChI=1S/C25H30O6/c1-24(2)12-11-21(25(3)19(15-27)17(14-26)13-20(28)23(24)25)31-22(29)10-7-16-5-8-18(30-4)9-6-16/h5-10,13-15,19-21,23,28H,11-12H2,1-4H3

InChI Key

YWTPSTGVICXAEK-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Zygogynum acsmithii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Cinnamic acid esters

Direct Parent

Cinnamic acid esters

Alternative Parents

Substituents

Cinnamic acid ester
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Styrene
Alkyl aryl ether
Fatty acid ester
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Aldehyde
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Alcohol
Organic oxide
Organic oxygen 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	3.41	ALOGPS
logP	3.03	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	13.25	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	89.9 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	118.09 m³·mol⁻¹	ChemAxon
Polarizability	46.22 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

74317559

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 7,8-diformyl-5-hydroxy-4,4,8a-trimethyl-1,2,3,4a,5,8-hexahydronaphthalen-1-yl 3-(4-methoxyphenyl)prop-2-enoate (NP0255558)

MOL for NP0255558 (7,8-diformyl-5-hydroxy-4,4,8a-trimethyl-1,2,3,4a,5,8-hexahydronaphthalen-1-yl 3-(4-methoxyphenyl)prop-2-enoate)

3D MOL for NP0255558 (7,8-diformyl-5-hydroxy-4,4,8a-trimethyl-1,2,3,4a,5,8-hexahydronaphthalen-1-yl 3-(4-methoxyphenyl)prop-2-enoate)

3D SDF for NP0255558 (7,8-diformyl-5-hydroxy-4,4,8a-trimethyl-1,2,3,4a,5,8-hexahydronaphthalen-1-yl 3-(4-methoxyphenyl)prop-2-enoate)

3D-SDF for NP0255558 (7,8-diformyl-5-hydroxy-4,4,8a-trimethyl-1,2,3,4a,5,8-hexahydronaphthalen-1-yl 3-(4-methoxyphenyl)prop-2-enoate)

PDB for NP0255558 (7,8-diformyl-5-hydroxy-4,4,8a-trimethyl-1,2,3,4a,5,8-hexahydronaphthalen-1-yl 3-(4-methoxyphenyl)prop-2-enoate)

3D PDB for NP0255558 (7,8-diformyl-5-hydroxy-4,4,8a-trimethyl-1,2,3,4a,5,8-hexahydronaphthalen-1-yl 3-(4-methoxyphenyl)prop-2-enoate)

SMILES for NP0255558 (7,8-diformyl-5-hydroxy-4,4,8a-trimethyl-1,2,3,4a,5,8-hexahydronaphthalen-1-yl 3-(4-methoxyphenyl)prop-2-enoate)

INCHI for NP0255558 (7,8-diformyl-5-hydroxy-4,4,8a-trimethyl-1,2,3,4a,5,8-hexahydronaphthalen-1-yl 3-(4-methoxyphenyl)prop-2-enoate)

Structure for NP0255558 (7,8-diformyl-5-hydroxy-4,4,8a-trimethyl-1,2,3,4a,5,8-hexahydronaphthalen-1-yl 3-(4-methoxyphenyl)prop-2-enoate)

3D Structure for NP0255558 (7,8-diformyl-5-hydroxy-4,4,8a-trimethyl-1,2,3,4a,5,8-hexahydronaphthalen-1-yl 3-(4-methoxyphenyl)prop-2-enoate)