NP-MRD: Showing NP-Card for 7-(acetyloxy)-1,6-dimethyl-8-[(3-methylbut-2-enoyl)oxy]-9-(prop-1-en-2-yl)-5,12-dioxatricyclo[9.1.0.0⁴,⁶]dodecan-2-yl 2-methylbut-2-enoate (NP0261384)

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Record Information

Version

2.0

Created at

2022-09-08 03:49:05 UTC

Updated at

2022-09-08 03:49:06 UTC

NP-MRD ID

NP0261384

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-(acetyloxy)-1,6-dimethyl-8-[(3-methylbut-2-enoyl)oxy]-9-(prop-1-en-2-yl)-5,12-dioxatricyclo[9.1.0.0⁴,⁶]dodecan-2-yl 2-methylbut-2-enoate

Description

7-(Acetyloxy)-1,6-dimethyl-8-[(3-methylbut-2-enoyl)oxy]-9-(prop-1-en-2-yl)-5,12-dioxatricyclo[9.1.0.0⁴,⁶]Dodecan-2-yl 2-methylbut-2-enoate belongs to the class of organic compounds known as germacrane sesquiterpenoids. These are sesquiterpenoids having the germacrane skeleton, with a structure characterized by a cyclodecane ring substituted with an isopropyl and two methyl groups. 7-(acetyloxy)-1,6-dimethyl-8-[(3-methylbut-2-enoyl)oxy]-9-(prop-1-en-2-yl)-5,12-dioxatricyclo[9.1.0.0⁴,⁶]dodecan-2-yl 2-methylbut-2-enoate is found in Kleinia galpinii. 7-(Acetyloxy)-1,6-dimethyl-8-[(3-methylbut-2-enoyl)oxy]-9-(prop-1-en-2-yl)-5,12-dioxatricyclo[9.1.0.0⁴,⁶]Dodecan-2-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


  Mrv1533004241516032D          

 35 37  0  0  0  0            999 V2000
    4.0497    3.7019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3364    2.7153    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


  Mrv1533004241516032D          

 35 37  0  0  0  0            999 V2000
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 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 19 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
  8 31  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 27 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0261384

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC=C(C)C(=O)OC1CC2OC2(C)C(OC(C)=O)C(OC(=O)C=C(C)C)C(CC2OC12C)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C27H38O8/c1-10-16(6)25(30)32-19-13-21-27(9,35-21)24(31-17(7)28)23(33-22(29)11-14(2)3)18(15(4)5)12-20-26(19,8)34-20/h10-11,18-21,23-24H,4,12-13H2,1-3,5-9H3

> <INCHI_KEY>
QWLSMSQXVXQQJI-UHFFFAOYSA-N

> <FORMULA>
C27H38O8

> <MOLECULAR_WEIGHT>
490.593

> <EXACT_MASS>
490.256668184

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
52.2065944838576

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7-(acetyloxy)-1,6-dimethyl-2-[(2-methylbut-2-enoyl)oxy]-9-(prop-1-en-2-yl)-5,12-dioxatricyclo[9.1.0.0⁴,⁶]dodecan-8-yl 3-methylbut-2-enoate

> <ALOGPS_LOGP>
4.33

> <JCHEM_LOGP>
4.573223475000001

> <ALOGPS_LOGS>
-5.17

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.941870939748655

> <JCHEM_POLAR_SURFACE_AREA>
103.96000000000001

> <JCHEM_REFRACTIVITY>
128.5038

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.34e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-(acetyloxy)-1,6-dimethyl-2-[(2-methylbut-2-enoyl)oxy]-9-(prop-1-en-2-yl)-5,12-dioxatricyclo[9.1.0.0⁴,⁶]dodecan-8-yl 3-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       7.560   6.910   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.339   5.582   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.547   4.188   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.228   5.069   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.067   2.568   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       9.535   3.389   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       7.238   0.985   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       7.239  -0.893   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.307   0.216   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.802  -0.154   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      11.297  -0.523   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      10.229  -1.633   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.792  -1.571   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.161  -2.743   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      10.698  -3.740   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      12.204  -4.609   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      13.797  -4.629   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      13.180  -5.997   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.666  -2.373   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.039  -3.993   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.205  -5.350   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.522  -4.628   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.865  -6.991   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.715  -8.397   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.259  -9.838   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.195  -8.148   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.599  -3.483   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.104  -3.113   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.677  -1.633   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       4.249  -0.154   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       5.744  -0.523   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.047   0.973   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.122  -5.434   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.064  -6.697   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.533  -7.096   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                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   31                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10   12                                                       
CONECT   12   11   10   13   14                                             
CONECT   13   12                                                            
CONECT   14   12   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   14   20   27                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   19   28   33                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29   31                                                       
CONECT   31   30    8   29   32                                             
CONECT   32   31                                                            
CONECT   33   27   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

View in JSmol

Synonyms

Value	Source
7-(Acetyloxy)-1,6-dimethyl-8-[(3-methylbut-2-enoyl)oxy]-9-(prop-1-en-2-yl)-5,12-dioxatricyclo[9.1.0.0,]dodecan-2-yl 2-methylbut-2-enoic acid	Generator
7-(Acetyloxy)-1,6-dimethyl-8-[(3-methylbut-2-enoyl)oxy]-9-(prop-1-en-2-yl)-5,12-dioxatricyclo[9.1.0.0⁴,⁶]dodecan-2-yl 2-methylbut-2-enoic acid	Generator

Chemical Formula

C₂₇H₃₈O₈

Average Mass

490.5930 Da

Monoisotopic Mass

490.25667 Da

IUPAC Name

7-(acetyloxy)-1,6-dimethyl-2-[(2-methylbut-2-enoyl)oxy]-9-(prop-1-en-2-yl)-5,12-dioxatricyclo[9.1.0.0⁴,⁶]dodecan-8-yl 3-methylbut-2-enoate

Traditional Name

7-(acetyloxy)-1,6-dimethyl-2-[(2-methylbut-2-enoyl)oxy]-9-(prop-1-en-2-yl)-5,12-dioxatricyclo[9.1.0.0⁴,⁶]dodecan-8-yl 3-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

CC=C(C)C(=O)OC1CC2OC2(C)C(OC(C)=O)C(OC(=O)C=C(C)C)C(CC2OC12C)C(C)=C

InChI Identifier

InChI=1S/C27H38O8/c1-10-16(6)25(30)32-19-13-21-27(9,35-21)24(31-17(7)28)23(33-22(29)11-14(2)3)18(15(4)5)12-20-26(19,8)34-20/h10-11,18-21,23-24H,4,12-13H2,1-3,5-9H3

InChI Key

QWLSMSQXVXQQJI-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
Kleinia galpinii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as germacrane sesquiterpenoids. These are sesquiterpenoids having the germacrane skeleton, with a structure characterized by a cyclodecane ring substituted with an isopropyl and two methyl groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Germacrane sesquiterpenoids

Alternative Parents

Substituents

Germacrane sesquiterpenoid
Tricarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen 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	4.33	ALOGPS
logP	4.57	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	103.96 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	128.5 m³·mol⁻¹	ChemAxon
Polarizability	52.21 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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 7-(acetyloxy)-1,6-dimethyl-8-[(3-methylbut-2-enoyl)oxy]-9-(prop-1-en-2-yl)-5,12-dioxatricyclo[9.1.0.0⁴,⁶]dodecan-2-yl 2-methylbut-2-enoate (NP0261384)

MOL for NP0261384 (7-(acetyloxy)-1,6-dimethyl-8-[(3-methylbut-2-enoyl)oxy]-9-(prop-1-en-2-yl)-5,12-dioxatricyclo[9.1.0.0⁴,⁶]dodecan-2-yl 2-methylbut-2-enoate)

3D MOL for NP0261384 (7-(acetyloxy)-1,6-dimethyl-8-[(3-methylbut-2-enoyl)oxy]-9-(prop-1-en-2-yl)-5,12-dioxatricyclo[9.1.0.0⁴,⁶]dodecan-2-yl 2-methylbut-2-enoate)

3D SDF for NP0261384 (7-(acetyloxy)-1,6-dimethyl-8-[(3-methylbut-2-enoyl)oxy]-9-(prop-1-en-2-yl)-5,12-dioxatricyclo[9.1.0.0⁴,⁶]dodecan-2-yl 2-methylbut-2-enoate)

3D-SDF for NP0261384 (7-(acetyloxy)-1,6-dimethyl-8-[(3-methylbut-2-enoyl)oxy]-9-(prop-1-en-2-yl)-5,12-dioxatricyclo[9.1.0.0⁴,⁶]dodecan-2-yl 2-methylbut-2-enoate)

PDB for NP0261384 (7-(acetyloxy)-1,6-dimethyl-8-[(3-methylbut-2-enoyl)oxy]-9-(prop-1-en-2-yl)-5,12-dioxatricyclo[9.1.0.0⁴,⁶]dodecan-2-yl 2-methylbut-2-enoate)

3D PDB for NP0261384 (7-(acetyloxy)-1,6-dimethyl-8-[(3-methylbut-2-enoyl)oxy]-9-(prop-1-en-2-yl)-5,12-dioxatricyclo[9.1.0.0⁴,⁶]dodecan-2-yl 2-methylbut-2-enoate)

SMILES for NP0261384 (7-(acetyloxy)-1,6-dimethyl-8-[(3-methylbut-2-enoyl)oxy]-9-(prop-1-en-2-yl)-5,12-dioxatricyclo[9.1.0.0⁴,⁶]dodecan-2-yl 2-methylbut-2-enoate)

INCHI for NP0261384 (7-(acetyloxy)-1,6-dimethyl-8-[(3-methylbut-2-enoyl)oxy]-9-(prop-1-en-2-yl)-5,12-dioxatricyclo[9.1.0.0⁴,⁶]dodecan-2-yl 2-methylbut-2-enoate)

Structure for NP0261384 (7-(acetyloxy)-1,6-dimethyl-8-[(3-methylbut-2-enoyl)oxy]-9-(prop-1-en-2-yl)-5,12-dioxatricyclo[9.1.0.0⁴,⁶]dodecan-2-yl 2-methylbut-2-enoate)

3D Structure for NP0261384 (7-(acetyloxy)-1,6-dimethyl-8-[(3-methylbut-2-enoyl)oxy]-9-(prop-1-en-2-yl)-5,12-dioxatricyclo[9.1.0.0⁴,⁶]dodecan-2-yl 2-methylbut-2-enoate)