NP-MRD: Showing NP-Card for 2,4,11-trihydroxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0³,⁷.0¹⁰,¹³]pentadecan-7-yl benzoate (NP0277214)

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Record Information

Version

2.0

Created at

2022-09-09 01:44:56 UTC

Updated at

2022-09-09 01:44:57 UTC

NP-MRD ID

NP0277214

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,4,11-trihydroxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0³,⁷.0¹⁰,¹³]pentadecan-7-yl benzoate

Description

2,4,11-Trihydroxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0³,⁷.0¹⁰,¹³]Pentadecan-7-yl benzoate belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. 2,4,11-trihydroxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0³,⁷.0¹⁰,¹³]pentadecan-7-yl benzoate is found in Euphorbia micractina. 2,4,11-Trihydroxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0³,⁷.0¹⁰,¹³]Pentadecan-7-yl benzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161505332D          

 33 37  0  0  0  0            999 V2000
    0.6069   -2.3715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3975   -2.1359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0529   -2.6370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7320   -2.1686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8837   -2.9795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2573   -3.5164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4791   -3.2423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4090   -4.3273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1871   -4.6014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3388   -5.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7124   -5.9492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9342   -5.6751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7825   -4.8642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4963   -1.3780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6716   -1.3578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2032   -0.6786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0632   -0.7786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8276    0.0121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8658   -0.9698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.2352   -0.5617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4708   -1.3523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9039   -1.9517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5033   -2.5186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5263   -3.3433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7702   -3.1505    0.0000 O   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
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  6  7  2  0  0  0  0
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  9 10  1  0  0  0  0
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  8 13  1  0  0  0  0
  4 14  1  0  0  0  0
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 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
  4 32  1  0  0  0  0
 32 33  2  0  0  0  0
M  END

     RDKit          3D

 69 73  0  0  0  0  0  0  0  0999 V2000
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    4.7468    2.8110    0.3263 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0762    0.2717    0.5940 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2628    1.4880    0.6979 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2970   -0.2070    0.8512 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -2.4350    1.9278   -0.0722 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -3.9556    1.7953    0.1105 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.7406    1.6802   -1.1459 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004161505332D          

 33 37  0  0  0  0            999 V2000
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 32 33  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0277214

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CC2(OC(=O)C3=CC=CC=C3)C(C1O)C(O)C1(C)CCC3C(C(O)C3(C)C)C1(C)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H36O6/c1-14-13-27(33-22(31)15-9-7-6-8-10-15)18(19(14)28)21(30)25(4)12-11-16-17(20(29)24(16,2)3)26(25,5)23(27)32/h6-10,14,16-21,28-30H,11-13H2,1-5H3

> <INCHI_KEY>
BQWBELRGLGGKOD-UHFFFAOYSA-N

> <FORMULA>
C27H36O6

> <MOLECULAR_WEIGHT>
456.579

> <EXACT_MASS>
456.251188879

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
49.61109142172121

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,4,11-trihydroxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0³,⁷.0¹⁰,¹³]pentadecan-7-yl benzoate

> <ALOGPS_LOGP>
2.63

> <JCHEM_LOGP>
3.6750419009999984

> <ALOGPS_LOGS>
-4.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.487285560480348

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.950588838458486

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9902780989091777

> <JCHEM_POLAR_SURFACE_AREA>
104.06

> <JCHEM_REFRACTIVITY>
121.92149999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.47e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,4,11-trihydroxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0³,⁷.0¹⁰,¹³]pentadecan-7-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       1.133  -4.427   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.609  -3.987   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.832  -4.922   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.100  -4.048   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.383  -5.562   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.214  -6.564   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.761  -6.052   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.497  -8.078   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.949  -8.589   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.232 -10.103   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.063 -11.105   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.611 -10.593   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.327  -9.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.660  -2.572   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.120  -2.534   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.246  -1.267   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.718  -1.453   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.278   0.023   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       7.216  -1.810   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.776  -0.334   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.274  -0.691   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.772  -1.048   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.212  -2.524   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.154  -3.643   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.273  -4.701   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      10.316  -6.241   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      11.331  -3.582   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.666  -4.350   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.621  -2.742   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.656  -3.286   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.096  -4.762   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.598  -4.405   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       7.038  -5.881   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   14   32                                             
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14    4   15   17                                                  
CONECT   15   14    2   16                                                  
CONECT   16   15                                                            
CONECT   17   14   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21   30                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   27                                                  
CONECT   24   23   25   30                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   23   28   29                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   24   19   31   32                                             
CONECT   31   30                                                            
CONECT   32   30    4   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Value	Source
2,4,11-Trihydroxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0,.0,]pentadecan-7-yl benzoic acid	Generator
2,4,11-Trihydroxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0³,⁷.0¹⁰,¹³]pentadecan-7-yl benzoic acid	Generator

Chemical Formula

C₂₇H₃₆O₆

Average Mass

456.5790 Da

Monoisotopic Mass

456.25119 Da

IUPAC Name

2,4,11-trihydroxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0³,⁷.0¹⁰,¹³]pentadecan-7-yl benzoate

Traditional Name

2,4,11-trihydroxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0³,⁷.0¹⁰,¹³]pentadecan-7-yl benzoate

CAS Registry Number

Not Available

SMILES

CC1CC2(OC(=O)C3=CC=CC=C3)C(C1O)C(O)C1(C)CCC3C(C(O)C3(C)C)C1(C)C2=O

InChI Identifier

InChI=1S/C27H36O6/c1-14-13-27(33-22(31)15-9-7-6-8-10-15)18(19(14)28)21(30)25(4)12-11-16-17(20(29)24(16,2)3)26(25,5)23(27)32/h6-10,14,16-21,28-30H,11-13H2,1-5H3

InChI Key

BQWBELRGLGGKOD-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
Euphorbia micractina	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
Benzoyl
Cyclic alcohol
Carboxylic acid ester
Secondary alcohol
Cyclobutanol
Ketone
Carboxylic acid derivative
Polyol
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxide
Organooxygen compound
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	2.63	ALOGPS
logP	3.68	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	13.95	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	121.92 m³·mol⁻¹	ChemAxon
Polarizability	49.61 Å³	ChemAxon
Number of Rings	5	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

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 2,4,11-trihydroxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0³,⁷.0¹⁰,¹³]pentadecan-7-yl benzoate (NP0277214)

MOL for NP0277214 (2,4,11-trihydroxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0³,⁷.0¹⁰,¹³]pentadecan-7-yl benzoate)

3D MOL for NP0277214 (2,4,11-trihydroxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0³,⁷.0¹⁰,¹³]pentadecan-7-yl benzoate)

3D SDF for NP0277214 (2,4,11-trihydroxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0³,⁷.0¹⁰,¹³]pentadecan-7-yl benzoate)

3D-SDF for NP0277214 (2,4,11-trihydroxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0³,⁷.0¹⁰,¹³]pentadecan-7-yl benzoate)

PDB for NP0277214 (2,4,11-trihydroxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0³,⁷.0¹⁰,¹³]pentadecan-7-yl benzoate)

3D PDB for NP0277214 (2,4,11-trihydroxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0³,⁷.0¹⁰,¹³]pentadecan-7-yl benzoate)

SMILES for NP0277214 (2,4,11-trihydroxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0³,⁷.0¹⁰,¹³]pentadecan-7-yl benzoate)

INCHI for NP0277214 (2,4,11-trihydroxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0³,⁷.0¹⁰,¹³]pentadecan-7-yl benzoate)

Structure for NP0277214 (2,4,11-trihydroxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0³,⁷.0¹⁰,¹³]pentadecan-7-yl benzoate)

3D Structure for NP0277214 (2,4,11-trihydroxy-1,5,9,12,12-pentamethyl-8-oxotetracyclo[7.6.0.0³,⁷.0¹⁰,¹³]pentadecan-7-yl benzoate)