NP-MRD: Showing NP-Card for 1-hydroxy-1-isopropyl-3a,6-dimethyl-8-[(2-methylbut-2-enoyl)oxy]-2,3,4,7,8,8a-hexahydroazulen-4-yl 4-methoxybenzoate (NP0199478)

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Record Information

Version

2.0

Created at

2022-09-04 18:07:52 UTC

Updated at

2022-09-04 18:07:52 UTC

NP-MRD ID

NP0199478

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-hydroxy-1-isopropyl-3a,6-dimethyl-8-[(2-methylbut-2-enoyl)oxy]-2,3,4,7,8,8a-hexahydroazulen-4-yl 4-methoxybenzoate

Description

1-Hydroxy-3a,6-dimethyl-8-[(2-methylbut-2-enoyl)oxy]-1-(propan-2-yl)-1,2,3,3a,4,7,8,8a-octahydroazulen-4-yl 4-methoxybenzoate belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 1-hydroxy-1-isopropyl-3a,6-dimethyl-8-[(2-methylbut-2-enoyl)oxy]-2,3,4,7,8,8a-hexahydroazulen-4-yl 4-methoxybenzoate is found in Ferula communis. 1-Hydroxy-3a,6-dimethyl-8-[(2-methylbut-2-enoyl)oxy]-1-(propan-2-yl)-1,2,3,3a,4,7,8,8a-octahydroazulen-4-yl 4-methoxybenzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241515112D          

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M  END

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M  END


  Mrv1533004241515112D          

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 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 25 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0199478

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1)C(=O)OC1C=C(C)CC(OC(=O)C(C)=CC)C2C1(C)CCC2(O)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C28H38O6/c1-8-19(5)25(29)33-22-15-18(4)16-23(27(6)13-14-28(31,17(2)3)24(22)27)34-26(30)20-9-11-21(32-7)12-10-20/h8-12,16-17,22-24,31H,13-15H2,1-7H3

> <INCHI_KEY>
LNAAKNMTRWAGLK-UHFFFAOYSA-N

> <FORMULA>
C28H38O6

> <MOLECULAR_WEIGHT>
470.606

> <EXACT_MASS>
470.266838944

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
52.91813264734303

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-hydroxy-3a,6-dimethyl-8-[(2-methylbut-2-enoyl)oxy]-1-(propan-2-yl)-1,2,3,3a,4,7,8,8a-octahydroazulen-4-yl 4-methoxybenzoate

> <ALOGPS_LOGP>
5.05

> <JCHEM_LOGP>
5.838155848333335

> <ALOGPS_LOGS>
-5.30

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.264520919240873

> <JCHEM_PKA_STRONGEST_BASIC>
-3.120498549924041

> <JCHEM_POLAR_SURFACE_AREA>
82.06

> <JCHEM_REFRACTIVITY>
132.2502

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.38e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-hydroxy-1-isopropyl-3a,6-dimethyl-8-[(2-methylbut-2-enoyl)oxy]-2,3,4,7,8,8a-hexahydroazulen-4-yl 4-methoxybenzoate

> <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       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       2.630   5.257   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.287   6.759   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.444   3.302   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.315   2.254   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       5.916   2.848   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.258   1.347   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.760   1.004   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.428  -0.384   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.968  -0.384   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.760  -1.771   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.258  -2.114   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.916  -3.615   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       7.044  -4.663   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.702  -6.164   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.516  -4.209   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.645  -5.256   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.116  -4.802   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.859  -2.707   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.054  -1.154   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.054   0.386   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.779   1.902   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  C   UNK     0       2.684  -0.384   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.590  -1.629   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.894  -3.139   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       2.456  -2.672   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.792  -4.175   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.986  -2.211   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3                                                       
CONECT    9    6   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   26                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   25                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21                                                            
CONECT   25   17   26   30                                                  
CONECT   26   25   12   27   28                                             
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   25   31   32                                             
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Value	Source
1-Hydroxy-3a,6-dimethyl-8-[(2-methylbut-2-enoyl)oxy]-1-(propan-2-yl)-1,2,3,3a,4,7,8,8a-octahydroazulen-4-yl 4-methoxybenzoic acid	Generator

Chemical Formula

C₂₈H₃₈O₆

Average Mass

470.6060 Da

Monoisotopic Mass

470.26684 Da

IUPAC Name

1-hydroxy-3a,6-dimethyl-8-[(2-methylbut-2-enoyl)oxy]-1-(propan-2-yl)-1,2,3,3a,4,7,8,8a-octahydroazulen-4-yl 4-methoxybenzoate

Traditional Name

1-hydroxy-1-isopropyl-3a,6-dimethyl-8-[(2-methylbut-2-enoyl)oxy]-2,3,4,7,8,8a-hexahydroazulen-4-yl 4-methoxybenzoate

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1)C(=O)OC1C=C(C)CC(OC(=O)C(C)=CC)C2C1(C)CCC2(O)C(C)C

InChI Identifier

InChI=1S/C28H38O6/c1-8-19(5)25(29)33-22-15-18(4)16-23(27(6)13-14-28(31,17(2)3)24(22)27)34-26(30)20-9-11-21(32-7)12-10-20/h8-12,16-17,22-24,31H,13-15H2,1-7H3

InChI Key

LNAAKNMTRWAGLK-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

Daucane sesquiterpenoid
Sesquiterpenoid
P-methoxybenzoic acid or derivatives
Benzoate ester
Benzoic acid or derivatives
Phenoxy compound
Anisole
Methoxybenzene
Benzoyl
Phenol ether
Alkyl aryl ether
Fatty acid ester
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Cyclic alcohol
Carboxylic acid ester
Carboxylic acid derivative
Ether
Carbonyl group
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
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	5.05	ALOGPS
logP	5.84	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	14.26	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	82.06 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	132.25 m³·mol⁻¹	ChemAxon
Polarizability	52.92 Å³	ChemAxon
Number of Rings	3	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 1-hydroxy-1-isopropyl-3a,6-dimethyl-8-[(2-methylbut-2-enoyl)oxy]-2,3,4,7,8,8a-hexahydroazulen-4-yl 4-methoxybenzoate (NP0199478)

MOL for NP0199478 (1-hydroxy-1-isopropyl-3a,6-dimethyl-8-[(2-methylbut-2-enoyl)oxy]-2,3,4,7,8,8a-hexahydroazulen-4-yl 4-methoxybenzoate)

3D MOL for NP0199478 (1-hydroxy-1-isopropyl-3a,6-dimethyl-8-[(2-methylbut-2-enoyl)oxy]-2,3,4,7,8,8a-hexahydroazulen-4-yl 4-methoxybenzoate)

3D SDF for NP0199478 (1-hydroxy-1-isopropyl-3a,6-dimethyl-8-[(2-methylbut-2-enoyl)oxy]-2,3,4,7,8,8a-hexahydroazulen-4-yl 4-methoxybenzoate)

3D-SDF for NP0199478 (1-hydroxy-1-isopropyl-3a,6-dimethyl-8-[(2-methylbut-2-enoyl)oxy]-2,3,4,7,8,8a-hexahydroazulen-4-yl 4-methoxybenzoate)

PDB for NP0199478 (1-hydroxy-1-isopropyl-3a,6-dimethyl-8-[(2-methylbut-2-enoyl)oxy]-2,3,4,7,8,8a-hexahydroazulen-4-yl 4-methoxybenzoate)

3D PDB for NP0199478 (1-hydroxy-1-isopropyl-3a,6-dimethyl-8-[(2-methylbut-2-enoyl)oxy]-2,3,4,7,8,8a-hexahydroazulen-4-yl 4-methoxybenzoate)

SMILES for NP0199478 (1-hydroxy-1-isopropyl-3a,6-dimethyl-8-[(2-methylbut-2-enoyl)oxy]-2,3,4,7,8,8a-hexahydroazulen-4-yl 4-methoxybenzoate)

INCHI for NP0199478 (1-hydroxy-1-isopropyl-3a,6-dimethyl-8-[(2-methylbut-2-enoyl)oxy]-2,3,4,7,8,8a-hexahydroazulen-4-yl 4-methoxybenzoate)

Structure for NP0199478 (1-hydroxy-1-isopropyl-3a,6-dimethyl-8-[(2-methylbut-2-enoyl)oxy]-2,3,4,7,8,8a-hexahydroazulen-4-yl 4-methoxybenzoate)

3D Structure for NP0199478 (1-hydroxy-1-isopropyl-3a,6-dimethyl-8-[(2-methylbut-2-enoyl)oxy]-2,3,4,7,8,8a-hexahydroazulen-4-yl 4-methoxybenzoate)