NP-MRD: Showing NP-Card for 1,8-bis(acetyloxy)-3-hydroxy-3-isopropyl-6,8a-dimethyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-methoxybenzoate (NP0219596)

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Record Information

Version

2.0

Created at

2022-09-05 20:38:52 UTC

Updated at

2022-09-05 20:38:52 UTC

NP-MRD ID

NP0219596

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,8-bis(acetyloxy)-3-hydroxy-3-isopropyl-6,8a-dimethyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-methoxybenzoate

Description

1,8-Bis(acetyloxy)-3-hydroxy-6,8a-dimethyl-3-(propan-2-yl)-1,2,3,3a,4,5,8,8a-octahydroazulen-4-yl 4-methoxybenzoate belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 1,8-bis(acetyloxy)-3-hydroxy-3-isopropyl-6,8a-dimethyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-methoxybenzoate is found in Ferula communis. Based on a literature review very few articles have been published on 1,8-bis(acetyloxy)-3-hydroxy-6,8a-dimethyl-3-(propan-2-yl)-1,2,3,3a,4,5,8,8a-octahydroazulen-4-yl 4-methoxybenzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052222382D          

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M  END

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  Mrv1652309052222382D          

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 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 28 33  1  0  0  0  0
 10 33  1  0  0  0  0
 20 33  1  0  0  0  0
  6 34  1  0  0  0  0
 34 35  2  0  0  0  0
  3 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0219596

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1)C(=O)OC1CC(C)=CC(OC(C)=O)C2(C)C(CC(O)(C(C)C)C12)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H36O8/c1-15(2)27(31)14-23(34-18(5)29)26(6)22(33-17(4)28)13-16(3)12-21(24(26)27)35-25(30)19-8-10-20(32-7)11-9-19/h8-11,13,15,21-24,31H,12,14H2,1-7H3

> <INCHI_KEY>
WAKHBUXWLXNILQ-UHFFFAOYSA-N

> <FORMULA>
C27H36O8

> <MOLECULAR_WEIGHT>
488.577

> <EXACT_MASS>
488.241018119

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
52.771864000376475

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,8-bis(acetyloxy)-3-hydroxy-6,8a-dimethyl-3-(propan-2-yl)-1,2,3,3a,4,5,8,8a-octahydroazulen-4-yl 4-methoxybenzoate

> <JCHEM_LOGP>
3.203864361333334

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.174288289583671

> <JCHEM_PKA_STRONGEST_BASIC>
-3.159966302136101

> <JCHEM_POLAR_SURFACE_AREA>
108.36

> <JCHEM_REFRACTIVITY>
128.1953

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
1,8-bis(acetyloxy)-3-hydroxy-3-isopropyl-6,8a-dimethyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-methoxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       1.602   9.761   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.073   9.307   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.416   7.806   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.887   7.352   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.230   5.851   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.101   4.803   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.444   3.302   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.315   2.254   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       5.916   2.848   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.258   1.347   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.760   1.004   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.428  -0.384   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.968  -0.384   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.760  -1.771   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.258  -2.114   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.916  -3.615   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       7.044  -4.663   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.516  -4.209   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.702  -6.164   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.054  -1.154   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.779  -2.669   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.590  -1.629   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.114  -3.094   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.607  -3.414   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.131  -4.879   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.577  -2.270   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.684  -0.384   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.590   0.862   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.216   2.269   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.256   1.632   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.256   3.172   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.922   0.862   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.054   0.386   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.630   5.257   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.287   6.759   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   35                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   34                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   33                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   15   21   22   33                                             
CONECT   21   20                                                            
CONECT   22   20   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   22   28                                                       
CONECT   28   27   29   30   33                                             
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   28   10   20                                                  
CONECT   34    6   35                                                       
CONECT   35   34    3                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

View in JSmol

Synonyms

Value	Source
1,8-Bis(acetyloxy)-3-hydroxy-6,8a-dimethyl-3-(propan-2-yl)-1,2,3,3a,4,5,8,8a-octahydroazulen-4-yl 4-methoxybenzoic acid	Generator

Chemical Formula

C₂₇H₃₆O₈

Average Mass

488.5770 Da

Monoisotopic Mass

488.24102 Da

IUPAC Name

1,8-bis(acetyloxy)-3-hydroxy-6,8a-dimethyl-3-(propan-2-yl)-1,2,3,3a,4,5,8,8a-octahydroazulen-4-yl 4-methoxybenzoate

Traditional Name

1,8-bis(acetyloxy)-3-hydroxy-3-isopropyl-6,8a-dimethyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-methoxybenzoate

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1)C(=O)OC1CC(C)=CC(OC(C)=O)C2(C)C(CC(O)(C(C)C)C12)OC(C)=O

InChI Identifier

InChI=1S/C27H36O8/c1-15(2)27(31)14-23(34-18(5)29)26(6)22(33-17(4)28)13-16(3)12-21(24(26)27)35-25(30)19-8-10-20(32-7)11-9-19/h8-11,13,15,21-24,31H,12,14H2,1-7H3

InChI Key

WAKHBUXWLXNILQ-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
Ferula communis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Daucane sesquiterpenoid
P-methoxybenzoic acid or derivatives
Benzoate ester
Benzoic acid or derivatives
Tricarboxylic acid or derivatives
Methoxybenzene
Phenol ether
Anisole
Phenoxy compound
Benzoyl
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Tertiary alcohol
Cyclic alcohol
Carboxylic acid ester
Ether
Carboxylic acid derivative
Carbonyl group
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organic oxygen compound
Organic oxide
Aromatic homopolycyclic compound

Molecular Framework

Aromatic 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	3.2	ChemAxon
pKa (Strongest Acidic)	14.17	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	108.36 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	128.2 m³·mol⁻¹	ChemAxon
Polarizability	52.77 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

14039825

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1,8-bis(acetyloxy)-3-hydroxy-3-isopropyl-6,8a-dimethyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-methoxybenzoate (NP0219596)

MOL for NP0219596 (1,8-bis(acetyloxy)-3-hydroxy-3-isopropyl-6,8a-dimethyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-methoxybenzoate)

3D MOL for NP0219596 (1,8-bis(acetyloxy)-3-hydroxy-3-isopropyl-6,8a-dimethyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-methoxybenzoate)

3D SDF for NP0219596 (1,8-bis(acetyloxy)-3-hydroxy-3-isopropyl-6,8a-dimethyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-methoxybenzoate)

3D-SDF for NP0219596 (1,8-bis(acetyloxy)-3-hydroxy-3-isopropyl-6,8a-dimethyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-methoxybenzoate)

PDB for NP0219596 (1,8-bis(acetyloxy)-3-hydroxy-3-isopropyl-6,8a-dimethyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-methoxybenzoate)

3D PDB for NP0219596 (1,8-bis(acetyloxy)-3-hydroxy-3-isopropyl-6,8a-dimethyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-methoxybenzoate)

SMILES for NP0219596 (1,8-bis(acetyloxy)-3-hydroxy-3-isopropyl-6,8a-dimethyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-methoxybenzoate)

INCHI for NP0219596 (1,8-bis(acetyloxy)-3-hydroxy-3-isopropyl-6,8a-dimethyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-methoxybenzoate)

Structure for NP0219596 (1,8-bis(acetyloxy)-3-hydroxy-3-isopropyl-6,8a-dimethyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-methoxybenzoate)

3D Structure for NP0219596 (1,8-bis(acetyloxy)-3-hydroxy-3-isopropyl-6,8a-dimethyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-methoxybenzoate)