NP-MRD: Showing NP-Card for 13-(acetyloxy)-4,8,8,11,15-pentamethyl-7,12-dioxo-3-oxatricyclo[11.3.0.0²,⁴]hexadec-10-en-16-yl 2-methylbut-2-enoate (NP0144495)

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Record Information

Version

2.0

Created at

2022-09-01 23:28:57 UTC

Updated at

2022-09-01 23:28:57 UTC

NP-MRD ID

NP0144495

Secondary Accession Numbers

None

Natural Product Identification

Common Name

13-(acetyloxy)-4,8,8,11,15-pentamethyl-7,12-dioxo-3-oxatricyclo[11.3.0.0²,⁴]hexadec-10-en-16-yl 2-methylbut-2-enoate

Description

13-(Acetyloxy)-4,8,8,11,15-pentamethyl-7,12-dioxo-3-oxatricyclo[11.3.0.0²,⁴]Hexadec-10-en-16-yl 2-methylbut-2-enoate belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. 13-(acetyloxy)-4,8,8,11,15-pentamethyl-7,12-dioxo-3-oxatricyclo[11.3.0.0²,⁴]hexadec-10-en-16-yl 2-methylbut-2-enoate is found in Euphorbia characias. 13-(Acetyloxy)-4,8,8,11,15-pentamethyl-7,12-dioxo-3-oxatricyclo[11.3.0.0²,⁴]Hexadec-10-en-16-yl 2-methylbut-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241508332D          

 34 36  0  0  0  0            999 V2000
    4.8833   -3.3934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 33 34  2  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1533004241508332D          

 34 36  0  0  0  0            999 V2000
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 26 29  1  0  0  0  0
 30 29  1  4  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 12 33  1  0  0  0  0
 33 34  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0144495

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC=C(C)C(=O)OC1C(C)CC2(OC(C)=O)C1C1OC1(C)CCC(=O)C(C)(C)CC=C(C)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H38O7/c1-9-15(2)24(31)32-21-17(4)14-27(33-18(5)28)20(21)23-26(8,34-23)13-11-19(29)25(6,7)12-10-16(3)22(27)30/h9-10,17,20-21,23H,11-14H2,1-8H3

> <INCHI_KEY>
GCVVCMZQTGIKSX-UHFFFAOYSA-N

> <FORMULA>
C27H38O7

> <MOLECULAR_WEIGHT>
474.594

> <EXACT_MASS>
474.261753564

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
51.11197562661101

> <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-7,12-dioxo-3-oxatricyclo[11.3.0.0²,⁴]hexadec-10-en-16-yl 2-methylbut-2-enoate

> <ALOGPS_LOGP>
3.68

> <JCHEM_LOGP>
5.369843301666665

> <ALOGPS_LOGS>
-5.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.31054149400327

> <JCHEM_PKA_STRONGEST_BASIC>
-4.204313832787767

> <JCHEM_POLAR_SURFACE_AREA>
99.26999999999998

> <JCHEM_REFRACTIVITY>
127.24149999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.62e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13-(acetyloxy)-4,8,8,11,15-pentamethyl-7,12-dioxo-3-oxatricyclo[11.3.0.0²,⁴]hexadec-10-en-16-yl 2-methylbut-2-enoate

> <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       9.116  -6.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.640  -4.870   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.670  -3.725   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.176  -4.046   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.194  -2.261   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      10.225  -1.116   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       7.688  -1.941   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       7.212  -0.476   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.117   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.657   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.212   2.016   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.747   1.540   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.299   2.978   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       7.820   3.219   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.372   4.656   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.789   2.022   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.747   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.977  -1.334   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.977  -2.874   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.644  -2.104   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.245  -3.591   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.104  -2.104   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -1.488  -0.399   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.447   1.013   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.990   2.720   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.770   2.874   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.104   3.644   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.644   3.644   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.042   5.131   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.977   2.874   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       6.066   3.963   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   17                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   17   33                                             
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   12    8   18                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   20                                                       
CONECT   20   19   18   21   22                                             
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28   29                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   26   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   12   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Value	Source
13-(Acetyloxy)-4,8,8,11,15-pentamethyl-7,12-dioxo-3-oxatricyclo[11.3.0.0,]hexadec-10-en-16-yl 2-methylbut-2-enoic acid	Generator
13-(Acetyloxy)-4,8,8,11,15-pentamethyl-7,12-dioxo-3-oxatricyclo[11.3.0.0²,⁴]hexadec-10-en-16-yl 2-methylbut-2-enoic acid	Generator

Chemical Formula

C₂₇H₃₈O₇

Average Mass

474.5940 Da

Monoisotopic Mass

474.26175 Da

IUPAC Name

13-(acetyloxy)-4,8,8,11,15-pentamethyl-7,12-dioxo-3-oxatricyclo[11.3.0.0²,⁴]hexadec-10-en-16-yl 2-methylbut-2-enoate

Traditional Name

13-(acetyloxy)-4,8,8,11,15-pentamethyl-7,12-dioxo-3-oxatricyclo[11.3.0.0²,⁴]hexadec-10-en-16-yl 2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

CC=C(C)C(=O)OC1C(C)CC2(OC(C)=O)C1C1OC1(C)CCC(=O)C(C)(C)CC=C(C)C2=O

InChI Identifier

InChI=1S/C27H38O7/c1-9-15(2)24(31)32-21-17(4)14-27(33-18(5)28)20(21)23-26(8,34-23)13-11-19(29)25(6,7)12-10-16(3)22(27)30/h9-10,17,20-21,23H,11-14H2,1-8H3

InChI Key

GCVVCMZQTGIKSX-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 fatty acid esters. These are carboxylic ester derivatives of a fatty acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Fatty acid esters

Alternative Parents

Substituents

Fatty acid ester
Alpha-acyloxy ketone
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Ketone
Cyclic ketone
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	3.68	ALOGPS
logP	5.37	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	18.31	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	99.27 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	127.24 m³·mol⁻¹	ChemAxon
Polarizability	51.11 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	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 13-(acetyloxy)-4,8,8,11,15-pentamethyl-7,12-dioxo-3-oxatricyclo[11.3.0.0²,⁴]hexadec-10-en-16-yl 2-methylbut-2-enoate (NP0144495)

MOL for NP0144495 (13-(acetyloxy)-4,8,8,11,15-pentamethyl-7,12-dioxo-3-oxatricyclo[11.3.0.0²,⁴]hexadec-10-en-16-yl 2-methylbut-2-enoate)

3D MOL for NP0144495 (13-(acetyloxy)-4,8,8,11,15-pentamethyl-7,12-dioxo-3-oxatricyclo[11.3.0.0²,⁴]hexadec-10-en-16-yl 2-methylbut-2-enoate)

3D SDF for NP0144495 (13-(acetyloxy)-4,8,8,11,15-pentamethyl-7,12-dioxo-3-oxatricyclo[11.3.0.0²,⁴]hexadec-10-en-16-yl 2-methylbut-2-enoate)

3D-SDF for NP0144495 (13-(acetyloxy)-4,8,8,11,15-pentamethyl-7,12-dioxo-3-oxatricyclo[11.3.0.0²,⁴]hexadec-10-en-16-yl 2-methylbut-2-enoate)

PDB for NP0144495 (13-(acetyloxy)-4,8,8,11,15-pentamethyl-7,12-dioxo-3-oxatricyclo[11.3.0.0²,⁴]hexadec-10-en-16-yl 2-methylbut-2-enoate)

3D PDB for NP0144495 (13-(acetyloxy)-4,8,8,11,15-pentamethyl-7,12-dioxo-3-oxatricyclo[11.3.0.0²,⁴]hexadec-10-en-16-yl 2-methylbut-2-enoate)

SMILES for NP0144495 (13-(acetyloxy)-4,8,8,11,15-pentamethyl-7,12-dioxo-3-oxatricyclo[11.3.0.0²,⁴]hexadec-10-en-16-yl 2-methylbut-2-enoate)

INCHI for NP0144495 (13-(acetyloxy)-4,8,8,11,15-pentamethyl-7,12-dioxo-3-oxatricyclo[11.3.0.0²,⁴]hexadec-10-en-16-yl 2-methylbut-2-enoate)

Structure for NP0144495 (13-(acetyloxy)-4,8,8,11,15-pentamethyl-7,12-dioxo-3-oxatricyclo[11.3.0.0²,⁴]hexadec-10-en-16-yl 2-methylbut-2-enoate)

3D Structure for NP0144495 (13-(acetyloxy)-4,8,8,11,15-pentamethyl-7,12-dioxo-3-oxatricyclo[11.3.0.0²,⁴]hexadec-10-en-16-yl 2-methylbut-2-enoate)