NP-MRD: Showing NP-Card for methyl 2-[10,13-bis(acetyloxy)-1,14-dihydroxy-4,15-dimethyl-8-oxo-3,7,17-trioxatetracyclo[12.2.1.1⁶,⁹.0²,⁴]octadeca-9(18),15-dien-12-yl]prop-2-enoate (NP0298002)

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Record Information

Version

2.0

Created at

2022-09-10 08:51:55 UTC

Updated at

2022-09-10 08:51:55 UTC

NP-MRD ID

NP0298002

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 2-[10,13-bis(acetyloxy)-1,14-dihydroxy-4,15-dimethyl-8-oxo-3,7,17-trioxatetracyclo[12.2.1.1⁶,⁹.0²,⁴]octadeca-9(18),15-dien-12-yl]prop-2-enoate

Description

Methyl 2-[10,13-bis(acetyloxy)-1,14-dihydroxy-4,15-dimethyl-8-oxo-3,7,17-trioxatetracyclo[12.2.1.1⁶,⁹.0²,⁴]Octadeca-9(18),15-dien-12-yl]prop-2-enoate belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Methyl 2-[10,13-bis(acetyloxy)-1,14-dihydroxy-4,15-dimethyl-8-oxo-3,7,17-trioxatetracyclo[12.2.1.1⁶,⁹.0²,⁴]Octadeca-9(18),15-dien-12-yl]prop-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251508592D          

 37 40  0  0  0  0            999 V2000
    2.8005    3.8855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3671    3.2858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1697    3.4766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4058    4.2672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7363    2.8770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5389    3.0678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5002    2.0865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0668    1.4868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8694    1.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1055    2.4681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9081    2.6589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1442    3.4494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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 16 35  1  0  0  0  0
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 36 37  2  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1533004251508592D          

 37 40  0  0  0  0            999 V2000
    2.8005    3.8855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  7 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 25 32  1  0  0  0  0
 32 33  2  0  0  0  0
 22 33  1  0  0  0  0
 32 34  1  0  0  0  0
 16 35  1  0  0  0  0
 35 36  1  0  0  0  0
 14 36  1  0  0  0  0
 36 37  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0298002

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C(=C)C1CC(OC(C)=O)C2=CC(CC3(C)OC3C3(O)OC(O)(C1OC(C)=O)C(C)=C3)OC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H30O12/c1-11-9-24(30)22-23(5,36-22)10-15-7-17(21(29)35-15)18(33-13(3)26)8-16(12(2)20(28)32-6)19(34-14(4)27)25(11,31)37-24/h7,9,15-16,18-19,22,30-31H,2,8,10H2,1,3-6H3

> <INCHI_KEY>
XXCSCQVYTNDURK-UHFFFAOYSA-N

> <FORMULA>
C25H30O12

> <MOLECULAR_WEIGHT>
522.503

> <EXACT_MASS>
522.173726406

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
50.687300145622636

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 2-[10,13-bis(acetyloxy)-1,14-dihydroxy-4,15-dimethyl-8-oxo-3,7,17-trioxatetracyclo[12.2.1.1⁶,⁹.0²,⁴]octadeca-9(18),15-dien-12-yl]prop-2-enoate

> <ALOGPS_LOGP>
0.57

> <JCHEM_LOGP>
1.2822898173333335

> <ALOGPS_LOGS>
-2.91

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.873234996793304

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.194592176956409

> <JCHEM_PKA_STRONGEST_BASIC>
-4.110779376140964

> <JCHEM_POLAR_SURFACE_AREA>
167.42

> <JCHEM_REFRACTIVITY>
122.27969999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.43e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2-[10,13-bis(acetyloxy)-1,14-dihydroxy-4,15-dimethyl-8-oxo-3,7,17-trioxatetracyclo[12.2.1.1⁶,⁹.0²,⁴]octadeca-9(18),15-dien-12-yl]prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       5.228   7.253   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.285   6.134   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.783   6.490   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.224   7.965   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       8.841   5.370   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.339   5.727   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.400   3.895   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.458   2.775   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.956   3.131   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      11.397   4.607   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      12.895   4.963   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      13.336   6.439   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      13.953   3.844   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.014   2.012   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.602   0.378   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.262  -1.014   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.143  -2.071   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.791  -1.333   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.346  -2.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.287  -2.788   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.279  -1.624   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.078  -0.532   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.465  -1.945   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       7.519   0.943   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.462   2.063   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.194   2.938   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.902   3.539   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.845   4.658   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.346   4.302   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       3.906   2.826   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       3.289   5.421   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.187   1.090   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.544  -0.408   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.737   1.608   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      13.638   0.123   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      13.512   1.658   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      14.680   2.662   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   27                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    9   15   36                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   35                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   18   22                                                  
CONECT   22   21   23   24   33                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27   32                                             
CONECT   26   25                                                            
CONECT   27   25    7   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   25   33   34                                                  
CONECT   33   32   22                                                       
CONECT   34   32                                                            
CONECT   35   16   36                                                       
CONECT   36   35   14   37                                                  
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
Methyl 2-[10,13-bis(acetyloxy)-1,14-dihydroxy-4,15-dimethyl-8-oxo-3,7,17-trioxatetracyclo[12.2.1.1,.0,]octadeca-9(18),15-dien-12-yl]prop-2-enoic acid	Generator
Methyl 2-[10,13-bis(acetyloxy)-1,14-dihydroxy-4,15-dimethyl-8-oxo-3,7,17-trioxatetracyclo[12.2.1.1⁶,⁹.0²,⁴]octadeca-9(18),15-dien-12-yl]prop-2-enoic acid	Generator

Chemical Formula

C₂₅H₃₀O₁₂

Average Mass

522.5030 Da

Monoisotopic Mass

522.17373 Da

IUPAC Name

methyl 2-[10,13-bis(acetyloxy)-1,14-dihydroxy-4,15-dimethyl-8-oxo-3,7,17-trioxatetracyclo[12.2.1.1⁶,⁹.0²,⁴]octadeca-9(18),15-dien-12-yl]prop-2-enoate

Traditional Name

methyl 2-[10,13-bis(acetyloxy)-1,14-dihydroxy-4,15-dimethyl-8-oxo-3,7,17-trioxatetracyclo[12.2.1.1⁶,⁹.0²,⁴]octadeca-9(18),15-dien-12-yl]prop-2-enoate

CAS Registry Number

Not Available

SMILES

COC(=O)C(=C)C1CC(OC(C)=O)C2=CC(CC3(C)OC3C3(O)OC(O)(C1OC(C)=O)C(C)=C3)OC2=O

InChI Identifier

InChI=1S/C25H30O12/c1-11-9-24(30)22-23(5,36-22)10-15-7-17(21(29)35-15)18(33-13(3)26)8-16(12(2)20(28)32-6)19(34-14(4)27)25(11,31)37-24/h7,9,15-16,18-19,22,30-31H,2,8,10H2,1,3-6H3

InChI Key

XXCSCQVYTNDURK-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 terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Sesquiterpenoid
Macrolide
Tetracarboxylic acid or derivatives
2-furanone
Dihydrofuran
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Hemiacetal
Carboxylic acid ester
Oxacycle
Ether
Oxirane
Dialkyl ether
Organoheterocyclic compound
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
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	0.57	ALOGPS
logP	1.28	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	10.19	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	167.42 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	122.28 m³·mol⁻¹	ChemAxon
Polarizability	50.69 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

74258283

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 2-[10,13-bis(acetyloxy)-1,14-dihydroxy-4,15-dimethyl-8-oxo-3,7,17-trioxatetracyclo[12.2.1.1⁶,⁹.0²,⁴]octadeca-9(18),15-dien-12-yl]prop-2-enoate (NP0298002)

MOL for NP0298002 (methyl 2-[10,13-bis(acetyloxy)-1,14-dihydroxy-4,15-dimethyl-8-oxo-3,7,17-trioxatetracyclo[12.2.1.1⁶,⁹.0²,⁴]octadeca-9(18),15-dien-12-yl]prop-2-enoate)

3D MOL for NP0298002 (methyl 2-[10,13-bis(acetyloxy)-1,14-dihydroxy-4,15-dimethyl-8-oxo-3,7,17-trioxatetracyclo[12.2.1.1⁶,⁹.0²,⁴]octadeca-9(18),15-dien-12-yl]prop-2-enoate)

3D SDF for NP0298002 (methyl 2-[10,13-bis(acetyloxy)-1,14-dihydroxy-4,15-dimethyl-8-oxo-3,7,17-trioxatetracyclo[12.2.1.1⁶,⁹.0²,⁴]octadeca-9(18),15-dien-12-yl]prop-2-enoate)

3D-SDF for NP0298002 (methyl 2-[10,13-bis(acetyloxy)-1,14-dihydroxy-4,15-dimethyl-8-oxo-3,7,17-trioxatetracyclo[12.2.1.1⁶,⁹.0²,⁴]octadeca-9(18),15-dien-12-yl]prop-2-enoate)

PDB for NP0298002 (methyl 2-[10,13-bis(acetyloxy)-1,14-dihydroxy-4,15-dimethyl-8-oxo-3,7,17-trioxatetracyclo[12.2.1.1⁶,⁹.0²,⁴]octadeca-9(18),15-dien-12-yl]prop-2-enoate)

3D PDB for NP0298002 (methyl 2-[10,13-bis(acetyloxy)-1,14-dihydroxy-4,15-dimethyl-8-oxo-3,7,17-trioxatetracyclo[12.2.1.1⁶,⁹.0²,⁴]octadeca-9(18),15-dien-12-yl]prop-2-enoate)

SMILES for NP0298002 (methyl 2-[10,13-bis(acetyloxy)-1,14-dihydroxy-4,15-dimethyl-8-oxo-3,7,17-trioxatetracyclo[12.2.1.1⁶,⁹.0²,⁴]octadeca-9(18),15-dien-12-yl]prop-2-enoate)

INCHI for NP0298002 (methyl 2-[10,13-bis(acetyloxy)-1,14-dihydroxy-4,15-dimethyl-8-oxo-3,7,17-trioxatetracyclo[12.2.1.1⁶,⁹.0²,⁴]octadeca-9(18),15-dien-12-yl]prop-2-enoate)

Structure for NP0298002 (methyl 2-[10,13-bis(acetyloxy)-1,14-dihydroxy-4,15-dimethyl-8-oxo-3,7,17-trioxatetracyclo[12.2.1.1⁶,⁹.0²,⁴]octadeca-9(18),15-dien-12-yl]prop-2-enoate)

3D Structure for NP0298002 (methyl 2-[10,13-bis(acetyloxy)-1,14-dihydroxy-4,15-dimethyl-8-oxo-3,7,17-trioxatetracyclo[12.2.1.1⁶,⁹.0²,⁴]octadeca-9(18),15-dien-12-yl]prop-2-enoate)