NP-MRD: Showing NP-Card for 19-(acetyloxy)-16-(furan-3-yl)-8,8,12,17-tetramethyl-4,11-dioxo-7-oxapentacyclo[10.7.0.0²,⁶.0²,⁹.0¹³,¹⁷]nonadec-13-en-18-yl acetate (NP0203016)

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Record Information

Version

2.0

Created at

2022-09-04 22:22:30 UTC

Updated at

2022-09-04 22:22:31 UTC

NP-MRD ID

NP0203016

Secondary Accession Numbers

None

Natural Product Identification

Common Name

19-(acetyloxy)-16-(furan-3-yl)-8,8,12,17-tetramethyl-4,11-dioxo-7-oxapentacyclo[10.7.0.0²,⁶.0²,⁹.0¹³,¹⁷]nonadec-13-en-18-yl acetate

Description

18-(Acetyloxy)-16-(furan-3-yl)-8,8,12,17-tetramethyl-4,11-dioxo-7-oxapentacyclo[10.7.0.0²,⁶.0²,⁹.0¹³,¹⁷]Nonadec-13-en-19-yl acetate belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. 19-(acetyloxy)-16-(furan-3-yl)-8,8,12,17-tetramethyl-4,11-dioxo-7-oxapentacyclo[10.7.0.0²,⁶.0²,⁹.0¹³,¹⁷]nonadec-13-en-18-yl acetate is found in Croton jatrophoides and Turraea wakefieldii. 18-(Acetyloxy)-16-(furan-3-yl)-8,8,12,17-tetramethyl-4,11-dioxo-7-oxapentacyclo[10.7.0.0²,⁶.0²,⁹.0¹³,¹⁷]Nonadec-13-en-19-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161520222D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004161520222D          

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    2.2902    1.5035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4241    2.3765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0266   -0.7794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8507   -0.7409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1420   -1.5128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4979   -2.0283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8086   -1.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
  5 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 27 30  1  0  0  0  0
 20 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 17 32  1  0  0  0  0
 32 33  2  0  0  0  0
 13 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 34 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0203016

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1C(OC(C)=O)C2(C)C(CC=C2C2(C)C1C13CC(=O)CC1OC(C)(C)C3CC2=O)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H36O8/c1-15(31)36-24-25-29(6,22(34)12-21-27(3,4)38-23-11-18(33)13-30(21,23)25)20-8-7-19(17-9-10-35-14-17)28(20,5)26(24)37-16(2)32/h8-10,14,19,21,23-26H,7,11-13H2,1-6H3

> <INCHI_KEY>
KSEPBLBDIIHMMF-UHFFFAOYSA-N

> <FORMULA>
C30H36O8

> <MOLECULAR_WEIGHT>
524.61

> <EXACT_MASS>
524.241018119

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
53.92539700387671

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
19-(acetyloxy)-16-(furan-3-yl)-8,8,12,17-tetramethyl-4,11-dioxo-7-oxapentacyclo[10.7.0.0²,⁶.0²,⁹.0¹³,¹⁷]nonadec-13-en-18-yl acetate

> <ALOGPS_LOGP>
4.03

> <JCHEM_LOGP>
2.5100382146666673

> <ALOGPS_LOGS>
-4.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.2419727355821

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.543841229931104

> <JCHEM_PKA_STRONGEST_BASIC>
-2.85708233983522

> <JCHEM_POLAR_SURFACE_AREA>
109.11

> <JCHEM_REFRACTIVITY>
135.12599999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.32e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
19-(acetyloxy)-16-(furan-3-yl)-8,8,12,17-tetramethyl-4,11-dioxo-7-oxapentacyclo[10.7.0.0²,⁶.0²,⁹.0¹³,¹⁷]nonadec-13-en-18-yl acetate

> <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       2.802  -6.357   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.676  -4.918   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.868  -6.011   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.645  -2.931   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.387  -1.266   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.906  -1.516   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.971  -3.279   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.723  -4.995   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.844  -6.870   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.412  -4.114   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.882  -0.325   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.731  -1.533   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.421  -0.253   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.828   1.233   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.541   2.079   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.338   1.116   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.819   1.366   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.775   2.727   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.843   0.174   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.323   0.424   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.610  -0.422   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.203  -1.907   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.994  -3.175   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.665  -1.979   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.121  -0.539   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.166   0.307   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.241   1.793   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.366   2.075   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.022   3.405   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.779   1.865   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.755   3.056   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.275   2.806   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.525   4.436   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       9.383  -1.455   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      10.921  -1.383   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      11.465  -2.824   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      10.263  -3.786   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.976  -2.940   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                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    6   12   13   16                                             
CONECT   12   11                                                            
CONECT   13   11   14   34                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11   17                                                  
CONECT   17   16   18   19   32                                             
CONECT   18   17                                                            
CONECT   19   17    5   20                                                  
CONECT   20   19   21   25   30                                             
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   20   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   27   20   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   17   33                                                  
CONECT   33   32                                                            
CONECT   34   13   35   38                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   34                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   86    0
END

View in JSmol

Synonyms

Value	Source
18-(Acetyloxy)-16-(furan-3-yl)-8,8,12,17-tetramethyl-4,11-dioxo-7-oxapentacyclo[10.7.0.0,.0,.0,]nonadec-13-en-19-yl acetic acid	Generator
18-(Acetyloxy)-16-(furan-3-yl)-8,8,12,17-tetramethyl-4,11-dioxo-7-oxapentacyclo[10.7.0.0²,⁶.0²,⁹.0¹³,¹⁷]nonadec-13-en-19-yl acetic acid	Generator

Chemical Formula

C₃₀H₃₆O₈

Average Mass

524.6100 Da

Monoisotopic Mass

524.24102 Da

IUPAC Name

19-(acetyloxy)-16-(furan-3-yl)-8,8,12,17-tetramethyl-4,11-dioxo-7-oxapentacyclo[10.7.0.0²,⁶.0²,⁹.0¹³,¹⁷]nonadec-13-en-18-yl acetate

Traditional Name

19-(acetyloxy)-16-(furan-3-yl)-8,8,12,17-tetramethyl-4,11-dioxo-7-oxapentacyclo[10.7.0.0²,⁶.0²,⁹.0¹³,¹⁷]nonadec-13-en-18-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1C(OC(C)=O)C2(C)C(CC=C2C2(C)C1C13CC(=O)CC1OC(C)(C)C3CC2=O)C1=COC=C1

InChI Identifier

InChI=1S/C30H36O8/c1-15(31)36-24-25-29(6,22(34)12-21-27(3,4)38-23-11-18(33)13-30(21,23)25)20-8-7-19(17-9-10-35-14-17)28(20,5)26(24)37-16(2)32/h8-10,14,19,21,23-26H,7,11-13H2,1-6H3

InChI Key

KSEPBLBDIIHMMF-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
Croton jatrophoides	LOTUS Database	35616633
Turraea wakefieldii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Dicarboxylic acids and derivatives

Direct Parent

Dicarboxylic acids and derivatives

Alternative Parents

Substituents

Dicarboxylic acid or derivatives
Furan
Heteroaromatic compound
Tetrahydrofuran
Carboxylic acid ester
Ketone
Cyclic ketone
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organooxygen 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	4.03	ALOGPS
logP	2.51	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	17.54	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	109.11 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	135.13 m³·mol⁻¹	ChemAxon
Polarizability	53.93 Å³	ChemAxon
Number of Rings	6	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

78201085

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 19-(acetyloxy)-16-(furan-3-yl)-8,8,12,17-tetramethyl-4,11-dioxo-7-oxapentacyclo[10.7.0.0²,⁶.0²,⁹.0¹³,¹⁷]nonadec-13-en-18-yl acetate (NP0203016)

MOL for NP0203016 (19-(acetyloxy)-16-(furan-3-yl)-8,8,12,17-tetramethyl-4,11-dioxo-7-oxapentacyclo[10.7.0.0²,⁶.0²,⁹.0¹³,¹⁷]nonadec-13-en-18-yl acetate)

3D MOL for NP0203016 (19-(acetyloxy)-16-(furan-3-yl)-8,8,12,17-tetramethyl-4,11-dioxo-7-oxapentacyclo[10.7.0.0²,⁶.0²,⁹.0¹³,¹⁷]nonadec-13-en-18-yl acetate)

3D SDF for NP0203016 (19-(acetyloxy)-16-(furan-3-yl)-8,8,12,17-tetramethyl-4,11-dioxo-7-oxapentacyclo[10.7.0.0²,⁶.0²,⁹.0¹³,¹⁷]nonadec-13-en-18-yl acetate)

3D-SDF for NP0203016 (19-(acetyloxy)-16-(furan-3-yl)-8,8,12,17-tetramethyl-4,11-dioxo-7-oxapentacyclo[10.7.0.0²,⁶.0²,⁹.0¹³,¹⁷]nonadec-13-en-18-yl acetate)

PDB for NP0203016 (19-(acetyloxy)-16-(furan-3-yl)-8,8,12,17-tetramethyl-4,11-dioxo-7-oxapentacyclo[10.7.0.0²,⁶.0²,⁹.0¹³,¹⁷]nonadec-13-en-18-yl acetate)

3D PDB for NP0203016 (19-(acetyloxy)-16-(furan-3-yl)-8,8,12,17-tetramethyl-4,11-dioxo-7-oxapentacyclo[10.7.0.0²,⁶.0²,⁹.0¹³,¹⁷]nonadec-13-en-18-yl acetate)

SMILES for NP0203016 (19-(acetyloxy)-16-(furan-3-yl)-8,8,12,17-tetramethyl-4,11-dioxo-7-oxapentacyclo[10.7.0.0²,⁶.0²,⁹.0¹³,¹⁷]nonadec-13-en-18-yl acetate)

INCHI for NP0203016 (19-(acetyloxy)-16-(furan-3-yl)-8,8,12,17-tetramethyl-4,11-dioxo-7-oxapentacyclo[10.7.0.0²,⁶.0²,⁹.0¹³,¹⁷]nonadec-13-en-18-yl acetate)

Structure for NP0203016 (19-(acetyloxy)-16-(furan-3-yl)-8,8,12,17-tetramethyl-4,11-dioxo-7-oxapentacyclo[10.7.0.0²,⁶.0²,⁹.0¹³,¹⁷]nonadec-13-en-18-yl acetate)

3D Structure for NP0203016 (19-(acetyloxy)-16-(furan-3-yl)-8,8,12,17-tetramethyl-4,11-dioxo-7-oxapentacyclo[10.7.0.0²,⁶.0²,⁹.0¹³,¹⁷]nonadec-13-en-18-yl acetate)