NP-MRD: Showing NP-Card for 13-(acetyloxy)-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-16-yl benzoate (NP0190219)

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Record Information

Version

2.0

Created at

2022-09-04 06:51:24 UTC

Updated at

2022-09-04 06:51:24 UTC

NP-MRD ID

NP0190219

Secondary Accession Numbers

None

Natural Product Identification

Common Name

13-(acetyloxy)-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-16-yl benzoate

Description

13-(Acetyloxy)-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]Hexadec-10-en-16-yl benzoate belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 13-(acetyloxy)-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-16-yl benzoate is found in Euphorbia characias. Based on a literature review very few articles have been published on 13-(acetyloxy)-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]Hexadec-10-en-16-yl benzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042208512D          

 35 39  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309042208512D          

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 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 28 27  1  4  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
  5 31  1  0  0  0  0
 31 32  2  0  0  0  0
 27 33  1  0  0  0  0
 26 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0190219

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CC2(OC(C)=O)C(C3OC3(C)CCC3C(C=C(C)C2=O)C3(C)C)C1OC(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H36O6/c1-16-14-21-20(27(21,4)5)12-13-28(6)25(35-28)22-23(33-26(32)19-10-8-7-9-11-19)17(2)15-29(22,24(16)31)34-18(3)30/h7-11,14,17,20-23,25H,12-13,15H2,1-6H3

> <INCHI_KEY>
LDPYFVODKJALRT-UHFFFAOYSA-N

> <FORMULA>
C29H36O6

> <MOLECULAR_WEIGHT>
480.601

> <EXACT_MASS>
480.251188879

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
52.46451307385637

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
13-(acetyloxy)-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.0^{2,4}.0^{7,9}]hexadec-10-en-16-yl benzoate

> <JCHEM_LOGP>
5.540664237000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.208435184283774

> <JCHEM_POLAR_SURFACE_AREA>
82.19999999999999

> <JCHEM_REFRACTIVITY>
130.6335

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
13-(acetyloxy)-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.0^{2,4}.0^{7,9}]hexadec-10-en-16-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      14.028   3.202   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.888   4.236   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      13.213   5.742   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      11.421   3.766   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      11.096   2.261   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.486   2.922   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.545   1.803   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.072   2.003   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.809   0.451   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      13.470  -0.940   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      15.005  -1.062   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      15.879   0.206   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      15.666  -2.453   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.201  -2.576   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      17.863  -3.967   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.989  -5.235   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      15.454  -5.112   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.793  -3.721   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.295   0.733   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.637  -0.659   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      10.690  -2.198   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       9.330  -1.474   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.948  -2.966   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.791  -1.454   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.506  -0.605   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.885   0.804   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.124   2.326   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.147   3.476   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.631   3.891   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.651   5.431   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.102   3.437   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      10.952   4.722   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       4.687   1.772   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.578   2.841   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.303   1.095   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   19   31                                             
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   19                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
CONECT   19    9    5   20                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20   22                                                       
CONECT   22   21   20   23   24                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   33                                                  
CONECT   27   26   28   33                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29    5   32                                                  
CONECT   32   31                                                            
CONECT   33   27   26   34   35                                             
CONECT   34   33                                                            
CONECT   35   33                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Value	Source
13-(Acetyloxy)-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.0,.0,]hexadec-10-en-16-yl benzoic acid	Generator

Chemical Formula

C₂₉H₃₆O₆

Average Mass

480.6010 Da

Monoisotopic Mass

480.25119 Da

IUPAC Name

13-(acetyloxy)-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.0^{2,4}.0^{7,9}]hexadec-10-en-16-yl benzoate

Traditional Name

13-(acetyloxy)-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.0^{2,4}.0^{7,9}]hexadec-10-en-16-yl benzoate

CAS Registry Number

Not Available

SMILES

CC1CC2(OC(C)=O)C(C3OC3(C)CCC3C(C=C(C)C2=O)C3(C)C)C1OC(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C29H36O6/c1-16-14-21-20(27(21,4)5)12-13-28(6)25(35-28)22-23(33-26(32)19-10-8-7-9-11-19)17(2)15-29(22,24(16)31)34-18(3)30/h7-11,14,17,20-23,25H,12-13,15H2,1-6H3

InChI Key

LDPYFVODKJALRT-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 characias	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Lathyrane diterpenoid
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Alpha-acyloxy ketone
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Carboxylic acid ester
Ketone
Ether
Oxirane
Organoheterocyclic compound
Oxacycle
Dialkyl ether
Carboxylic acid derivative
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
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	5.54	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	82.2 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	130.63 m³·mol⁻¹	ChemAxon
Polarizability	52.46 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

162944235

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 13-(acetyloxy)-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-16-yl benzoate (NP0190219)

MOL for NP0190219 (13-(acetyloxy)-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-16-yl benzoate)

3D MOL for NP0190219 (13-(acetyloxy)-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-16-yl benzoate)

3D SDF for NP0190219 (13-(acetyloxy)-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-16-yl benzoate)

3D-SDF for NP0190219 (13-(acetyloxy)-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-16-yl benzoate)

PDB for NP0190219 (13-(acetyloxy)-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-16-yl benzoate)

3D PDB for NP0190219 (13-(acetyloxy)-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-16-yl benzoate)

SMILES for NP0190219 (13-(acetyloxy)-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-16-yl benzoate)

INCHI for NP0190219 (13-(acetyloxy)-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-16-yl benzoate)

Structure for NP0190219 (13-(acetyloxy)-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-16-yl benzoate)

3D Structure for NP0190219 (13-(acetyloxy)-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.0²,⁴.0⁷,⁹]hexadec-10-en-16-yl benzoate)