NP-MRD: Showing NP-Card for methyl (2e)-3-(8-hydroxy-4a,8-dimethyl-octahydronaphthalen-2-yl)prop-2-enoate (NP0301057)

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Record Information

Version

2.0

Created at

2022-09-10 13:47:44 UTC

Updated at

2022-09-10 13:47:44 UTC

NP-MRD ID

NP0301057

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (2e)-3-(8-hydroxy-4a,8-dimethyl-octahydronaphthalen-2-yl)prop-2-enoate

Description

methyl (2e)-3-(8-hydroxy-4a,8-dimethyl-octahydronaphthalen-2-yl)prop-2-enoate is found in Tithonia diversifolia.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 45 46  0  0  0  0  0  0  0  0999 V2000
    7.0683   -1.2352    0.0122 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7622   -1.0810   -0.5114 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7674   -0.4802    0.2448 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0833   -0.0901    1.3929 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4131   -0.3185   -0.2939 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4447    0.2506    0.4048 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0898    0.4098   -0.1403 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6607    1.8574   -0.2556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5844    1.8936   -1.1114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7095    1.1664   -0.3816 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0256    1.9414    0.8609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9458    1.1099   -1.2341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2760   -0.2855   -1.6955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4033   -1.2579   -0.5603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3705   -1.0064    0.5189 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9170   -2.3497    1.0475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9441   -0.3156    1.5696 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2484   -0.2306   -0.1166 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0319   -0.2972    0.6831 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2472   -2.3065    0.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7804   -0.8179   -0.7267 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1764   -0.6243    0.9304 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2073   -0.6749   -1.2861 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7298    0.5889    1.4080 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0600   -0.0204   -1.1448 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4469    2.4926   -0.6927 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4363    2.2849    0.7496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3659    1.4352   -2.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8520    2.9807   -1.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5537    1.5732    1.7691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7486    3.0174    0.7268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1372    1.9587    1.0521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7655    1.7171   -2.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8469    1.5201   -0.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5519   -0.5761   -2.4552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2709   -0.2174   -2.2120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2413   -2.2873   -0.9857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4391   -1.2723   -0.1290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3606   -2.9345    0.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8395   -2.9108    1.3128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2864   -2.2480    1.9419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9230   -0.5111    1.5368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0350   -0.7064   -1.0968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0321    0.2136    1.6508 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2684   -1.3556    0.8597 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  1
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  1
 15 18  1  0
 18 19  1  0
 19  7  1  0
 18 10  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  5 23  1  0
  6 24  1  0
  7 25  1  6
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 16 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 18 43  1  6
 19 44  1  0
 19 45  1  0
M  END


  Mrv1652309102215472D          

 19 20  0  0  0  0            999 V2000
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   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
   -1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -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
    2.1434   -0.4125    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
    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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3276   -2.2820    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
    1.4289   -1.6500    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
  3  5  1  0  0  0  0
  5  6  2  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
  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  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  0  0  0  0
  7 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0301057

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)\C=C\C1CCC2(C)CCCC(C)(O)C2C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H26O3/c1-15-8-4-9-16(2,18)13(15)11-12(7-10-15)5-6-14(17)19-3/h5-6,12-13,18H,4,7-11H2,1-3H3/b6-5+

> <INCHI_KEY>
NZLOBLLOXJHWHM-AATRIKPKSA-N

> <FORMULA>
C16H26O3

> <MOLECULAR_WEIGHT>
266.381

> <EXACT_MASS>
266.188194697

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
31.14736775354477

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2E)-3-(8-hydroxy-4a,8-dimethyl-decahydronaphthalen-2-yl)prop-2-enoate

> <JCHEM_LOGP>
3.171686141666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-0.4615409372659477

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
76.08720000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2E)-3-(8-hydroxy-4a,8-dimethyl-octahydronaphthalen-2-yl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.325  -4.260   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.345  -4.260   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   19                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   18                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15   10   19                                                  
CONECT   19   18    7                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₆O₃

Average Mass

266.3810 Da

Monoisotopic Mass

266.18819 Da

IUPAC Name

methyl (2E)-3-(8-hydroxy-4a,8-dimethyl-decahydronaphthalen-2-yl)prop-2-enoate

Traditional Name

methyl (2E)-3-(8-hydroxy-4a,8-dimethyl-octahydronaphthalen-2-yl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

COC(=O)\C=C\C1CCC2(C)CCCC(C)(O)C2C1

InChI Identifier

InChI=1S/C16H26O3/c1-15-8-4-9-16(2,18)13(15)11-12(7-10-15)5-6-14(17)19-3/h5-6,12-13,18H,4,7-11H2,1-3H3/b6-5+

InChI Key

NZLOBLLOXJHWHM-AATRIKPKSA-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
Tithonia diversifolia	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

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	3.17	ChemAxon
pKa (Strongest Basic)	-0.46	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	76.09 m³·mol⁻¹	ChemAxon
Polarizability	31.15 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (2e)-3-(8-hydroxy-4a,8-dimethyl-octahydronaphthalen-2-yl)prop-2-enoate (NP0301057)

MOL for NP0301057 (methyl (2e)-3-(8-hydroxy-4a,8-dimethyl-octahydronaphthalen-2-yl)prop-2-enoate)

3D MOL for NP0301057 (methyl (2e)-3-(8-hydroxy-4a,8-dimethyl-octahydronaphthalen-2-yl)prop-2-enoate)

3D SDF for NP0301057 (methyl (2e)-3-(8-hydroxy-4a,8-dimethyl-octahydronaphthalen-2-yl)prop-2-enoate)

3D-SDF for NP0301057 (methyl (2e)-3-(8-hydroxy-4a,8-dimethyl-octahydronaphthalen-2-yl)prop-2-enoate)

PDB for NP0301057 (methyl (2e)-3-(8-hydroxy-4a,8-dimethyl-octahydronaphthalen-2-yl)prop-2-enoate)

3D PDB for NP0301057 (methyl (2e)-3-(8-hydroxy-4a,8-dimethyl-octahydronaphthalen-2-yl)prop-2-enoate)

SMILES for NP0301057 (methyl (2e)-3-(8-hydroxy-4a,8-dimethyl-octahydronaphthalen-2-yl)prop-2-enoate)

INCHI for NP0301057 (methyl (2e)-3-(8-hydroxy-4a,8-dimethyl-octahydronaphthalen-2-yl)prop-2-enoate)

Structure for NP0301057 (methyl (2e)-3-(8-hydroxy-4a,8-dimethyl-octahydronaphthalen-2-yl)prop-2-enoate)

3D Structure for NP0301057 (methyl (2e)-3-(8-hydroxy-4a,8-dimethyl-octahydronaphthalen-2-yl)prop-2-enoate)