NP-MRD: Showing NP-Card for methyl 14-(acetyloxy)-5,9-dimethyl-2-[(2-methylbut-2-enoyl)oxy]-13-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate (NP0243526)

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Record Information

Version

2.0

Created at

2022-09-07 04:05:39 UTC

Updated at

2022-09-07 04:05:39 UTC

NP-MRD ID

NP0243526

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 14-(acetyloxy)-5,9-dimethyl-2-[(2-methylbut-2-enoyl)oxy]-13-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate

Description

Methyl 14-(acetyloxy)-5,9-dimethyl-2-[(2-methylbut-2-enoyl)oxy]-13-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]Hexadecane-5-carboxylate belongs to the class of organic compounds known as atisane diterpenoids. These are diterpenoids with a structure based on the atisane skeleton, which is a tetracyclic compound containing the [2,2,2]bicyc1ic ring system with the C15-C16 bridge attached at C12. Methyl 14-(acetyloxy)-5,9-dimethyl-2-[(2-methylbut-2-enoyl)oxy]-13-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]Hexadecane-5-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241513342D          

 34 37  0  0  0  0            999 V2000
    5.9786   -2.6489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0675   -1.8287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6469   -1.6746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4907   -0.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2830   -0.7514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8548    0.2189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004241513342D          

 34 37  0  0  0  0            999 V2000
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 22 23  1  0  0  0  0
 23 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
 10 27  1  0  0  0  0
 22 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 22 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0243526

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1(C)CCCC2(C)C1CC(OC(=O)C(C)=CC)C13CCC(CC21)C(=C)C3OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H40O6/c1-8-16(2)24(30)34-22-15-20-26(5,11-9-12-27(20,6)25(31)32-7)21-14-19-10-13-28(21,22)23(17(19)3)33-18(4)29/h8,19-23H,3,9-15H2,1-2,4-7H3

> <INCHI_KEY>
PNNPMBCSJHYXLP-UHFFFAOYSA-N

> <FORMULA>
C28H40O6

> <MOLECULAR_WEIGHT>
472.622

> <EXACT_MASS>
472.282489008

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
52.032724989729786

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 14-(acetyloxy)-5,9-dimethyl-2-[(2-methylbut-2-enoyl)oxy]-13-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate

> <ALOGPS_LOGP>
5.41

> <JCHEM_LOGP>
5.302072791333334

> <ALOGPS_LOGS>
-6.18

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.499754678704489

> <JCHEM_POLAR_SURFACE_AREA>
78.9

> <JCHEM_REFRACTIVITY>
127.99099999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.11e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 14-(acetyloxy)-5,9-dimethyl-2-[(2-methylbut-2-enoyl)oxy]-13-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate

> <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      11.160  -4.945   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      11.326  -3.414   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      10.083  -2.504   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.674  -3.126   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      10.249  -0.973   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.728  -1.403   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.929   0.409   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.072   1.688   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.536   1.586   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.856   0.204   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.076   1.532   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.713  -1.075   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.935  -2.479   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.389  -2.390   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.708  -3.771   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.563  -5.052   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.100  -4.951   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.882  -6.433   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.737  -7.714   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.274  -7.613   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.345  -6.533   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.339  -1.172   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.353  -0.156   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.711   1.148   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.927   2.217   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.651   1.901   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.266   0.287   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.044   0.720   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.513   0.891   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.572  -0.919   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.580  -2.097   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       3.103  -3.545   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.619  -3.816   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       2.110  -4.722   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    7   12                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   27                                             
CONECT   11   10                                                            
CONECT   12   10    5   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   22                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18                                                            
CONECT   22   14   23   27   30                                             
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26   10   22                                                  
CONECT   28   25   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   22   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
Methyl 14-(acetyloxy)-5,9-dimethyl-2-[(2-methylbut-2-enoyl)oxy]-13-methylidenetetracyclo[10.2.2.0,.0,]hexadecane-5-carboxylic acid	Generator
Methyl 14-(acetyloxy)-5,9-dimethyl-2-[(2-methylbut-2-enoyl)oxy]-13-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid	Generator

Chemical Formula

C₂₈H₄₀O₆

Average Mass

472.6220 Da

Monoisotopic Mass

472.28249 Da

IUPAC Name

methyl 14-(acetyloxy)-5,9-dimethyl-2-[(2-methylbut-2-enoyl)oxy]-13-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate

Traditional Name

methyl 14-(acetyloxy)-5,9-dimethyl-2-[(2-methylbut-2-enoyl)oxy]-13-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1(C)CCCC2(C)C1CC(OC(=O)C(C)=CC)C13CCC(CC21)C(=C)C3OC(C)=O

InChI Identifier

InChI=1S/C28H40O6/c1-8-16(2)24(30)34-22-15-20-26(5,11-9-12-27(20,6)25(31)32-7)21-14-19-10-13-28(21,22)23(17(19)3)33-18(4)29/h8,19-23H,3,9-15H2,1-2,4-7H3

InChI Key

PNNPMBCSJHYXLP-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as atisane diterpenoids. These are diterpenoids with a structure based on the atisane skeleton, which is a tetracyclic compound containing the [2,2,2]bicyc1ic ring system with the C15-C16 bridge attached at C12.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Atisane diterpenoids

Alternative Parents

Substituents

Atisane diterpenoid
Tricarboxylic acid or derivatives
Alkaloid or derivatives
Fatty acid ester
Fatty acyl
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic 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	5.41	ALOGPS
logP	5.3	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Basic)	-6.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	78.9 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	127.99 m³·mol⁻¹	ChemAxon
Polarizability	52.03 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

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 methyl 14-(acetyloxy)-5,9-dimethyl-2-[(2-methylbut-2-enoyl)oxy]-13-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate (NP0243526)

MOL for NP0243526 (methyl 14-(acetyloxy)-5,9-dimethyl-2-[(2-methylbut-2-enoyl)oxy]-13-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate)

3D MOL for NP0243526 (methyl 14-(acetyloxy)-5,9-dimethyl-2-[(2-methylbut-2-enoyl)oxy]-13-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate)

3D SDF for NP0243526 (methyl 14-(acetyloxy)-5,9-dimethyl-2-[(2-methylbut-2-enoyl)oxy]-13-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate)

3D-SDF for NP0243526 (methyl 14-(acetyloxy)-5,9-dimethyl-2-[(2-methylbut-2-enoyl)oxy]-13-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate)

PDB for NP0243526 (methyl 14-(acetyloxy)-5,9-dimethyl-2-[(2-methylbut-2-enoyl)oxy]-13-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate)

3D PDB for NP0243526 (methyl 14-(acetyloxy)-5,9-dimethyl-2-[(2-methylbut-2-enoyl)oxy]-13-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate)

SMILES for NP0243526 (methyl 14-(acetyloxy)-5,9-dimethyl-2-[(2-methylbut-2-enoyl)oxy]-13-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate)

INCHI for NP0243526 (methyl 14-(acetyloxy)-5,9-dimethyl-2-[(2-methylbut-2-enoyl)oxy]-13-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate)

Structure for NP0243526 (methyl 14-(acetyloxy)-5,9-dimethyl-2-[(2-methylbut-2-enoyl)oxy]-13-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate)

3D Structure for NP0243526 (methyl 14-(acetyloxy)-5,9-dimethyl-2-[(2-methylbut-2-enoyl)oxy]-13-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate)