NP-MRD: Showing NP-Card for 3-(acetyloxy)-2,5-dihydroxy-5-isopropyl-2a,7a-dimethyl-hexahydro-1ah-azuleno[5,6-b]oxiren-6-yl 3,4-dimethoxybenzoate (NP0199006)

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Record Information

Version

2.0

Created at

2022-09-04 17:34:00 UTC

Updated at

2022-09-04 17:34:00 UTC

NP-MRD ID

NP0199006

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(acetyloxy)-2,5-dihydroxy-5-isopropyl-2a,7a-dimethyl-hexahydro-1ah-azuleno[5,6-b]oxiren-6-yl 3,4-dimethoxybenzoate

Description

3-(Acetyloxy)-2,5-dihydroxy-2a,7a-dimethyl-5-(propan-2-yl)-decahydroazuleno[5,6-b]oxiren-6-yl 3,4-dimethoxybenzoate belongs to the class of organic compounds known as p-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 4 of the benzene ring is replaced by a methoxy group. 3-(acetyloxy)-2,5-dihydroxy-5-isopropyl-2a,7a-dimethyl-hexahydro-1ah-azuleno[5,6-b]oxiren-6-yl 3,4-dimethoxybenzoate is found in Ferula lapidosa. 3-(Acetyloxy)-2,5-dihydroxy-2a,7a-dimethyl-5-(propan-2-yl)-decahydroazuleno[5,6-b]oxiren-6-yl 3,4-dimethoxybenzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161509172D          

 35 38  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004161509172D          

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 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 26 31  1  0  0  0  0
 14 31  1  0  0  0  0
 22 31  1  0  0  0  0
 24 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0199006

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1OC)C(=O)OC1CC2(C)OC2C(O)C2(C)C(CC(O)(C(C)C)C12)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H36O9/c1-13(2)26(30)12-19(33-14(3)27)25(5)20(26)18(11-24(4)22(35-24)21(25)28)34-23(29)15-8-9-16(31-6)17(10-15)32-7/h8-10,13,18-22,28,30H,11-12H2,1-7H3

> <INCHI_KEY>
IBEZMJKOIASRKO-UHFFFAOYSA-N

> <FORMULA>
C26H36O9

> <MOLECULAR_WEIGHT>
492.565

> <EXACT_MASS>
492.235932739

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
52.26262508454718

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(acetyloxy)-2,5-dihydroxy-2a,7a-dimethyl-5-(propan-2-yl)-decahydroazuleno[5,6-b]oxiren-6-yl 3,4-dimethoxybenzoate

> <ALOGPS_LOGP>
2.77

> <JCHEM_LOGP>
1.7873996309999995

> <ALOGPS_LOGS>
-3.78

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.278270806991298

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.475471728563999

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1595612024812816

> <JCHEM_POLAR_SURFACE_AREA>
124.05000000000001

> <JCHEM_REFRACTIVITY>
124.0699

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.14e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(acetyloxy)-2,5-dihydroxy-5-isopropyl-2a,7a-dimethyl-hexahydro-1aH-azuleno[5,6-b]oxiren-6-yl 3,4-dimethoxybenzoate

> <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       2.122  10.193   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.217   8.947   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.844   7.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.938   6.294   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.565   4.887   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.097   4.726   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.002   5.972   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.375   7.379   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.280   8.625   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.654  10.032   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.723   3.319   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.818   2.073   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       5.255   3.158   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.881   1.752   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.420   1.706   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.344   0.473   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.504   1.487   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.441  -0.607   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       7.957  -1.017   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.550  -1.643   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.504  -3.183   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.183  -0.934   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.206  -2.474   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.838  -1.684   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.709  -0.637   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.356   0.761   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.699   2.262   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.899   1.258   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.601   2.769   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.739   0.245   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.885   0.577   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       3.654  -3.213   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.238  -3.819   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       2.054  -5.348   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       1.006  -2.895   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   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    6   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   31                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   16   20                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24   31                                             
CONECT   23   22                                                            
CONECT   24   22   25   32                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28   31                                             
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   26   14   22                                                  
CONECT   32   24   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
3-(Acetyloxy)-2,5-dihydroxy-2a,7a-dimethyl-5-(propan-2-yl)-decahydroazuleno[5,6-b]oxiren-6-yl 3,4-dimethoxybenzoic acid	Generator

Chemical Formula

C₂₆H₃₆O₉

Average Mass

492.5650 Da

Monoisotopic Mass

492.23593 Da

IUPAC Name

3-(acetyloxy)-2,5-dihydroxy-2a,7a-dimethyl-5-(propan-2-yl)-decahydroazuleno[5,6-b]oxiren-6-yl 3,4-dimethoxybenzoate

Traditional Name

3-(acetyloxy)-2,5-dihydroxy-5-isopropyl-2a,7a-dimethyl-hexahydro-1aH-azuleno[5,6-b]oxiren-6-yl 3,4-dimethoxybenzoate

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1OC)C(=O)OC1CC2(C)OC2C(O)C2(C)C(CC(O)(C(C)C)C12)OC(C)=O

InChI Identifier

InChI=1S/C26H36O9/c1-13(2)26(30)12-19(33-14(3)27)25(5)20(26)18(11-24(4)22(35-24)21(25)28)34-23(29)15-8-9-16(31-6)17(10-15)32-7/h8-10,13,18-22,28,30H,11-12H2,1-7H3

InChI Key

IBEZMJKOIASRKO-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 lapidosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as p-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 4 of the benzene ring is replaced by a methoxy group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

P-methoxybenzoic acids and derivatives

Alternative Parents

Substituents

M-methoxybenzoic acid or derivatives
P-methoxybenzoic acid or derivatives
Benzoate ester
Dimethoxybenzene
O-dimethoxybenzene
Methoxybenzene
Anisole
Benzoyl
Phenol ether
Phenoxy compound
Alkyl aryl ether
Dicarboxylic acid or derivatives
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Dialkyl ether
Ether
Oxirane
Carbonyl group
Organic oxide
Organic oxygen compound
Organooxygen compound
Alcohol
Hydrocarbon derivative
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	2.77	ALOGPS
logP	1.79	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	13.48	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	124.05 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	124.07 m³·mol⁻¹	ChemAxon
Polarizability	52.26 Å³	ChemAxon
Number of Rings	4	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

45934331

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-(acetyloxy)-2,5-dihydroxy-5-isopropyl-2a,7a-dimethyl-hexahydro-1ah-azuleno[5,6-b]oxiren-6-yl 3,4-dimethoxybenzoate (NP0199006)

MOL for NP0199006 (3-(acetyloxy)-2,5-dihydroxy-5-isopropyl-2a,7a-dimethyl-hexahydro-1ah-azuleno[5,6-b]oxiren-6-yl 3,4-dimethoxybenzoate)

3D MOL for NP0199006 (3-(acetyloxy)-2,5-dihydroxy-5-isopropyl-2a,7a-dimethyl-hexahydro-1ah-azuleno[5,6-b]oxiren-6-yl 3,4-dimethoxybenzoate)

3D SDF for NP0199006 (3-(acetyloxy)-2,5-dihydroxy-5-isopropyl-2a,7a-dimethyl-hexahydro-1ah-azuleno[5,6-b]oxiren-6-yl 3,4-dimethoxybenzoate)

3D-SDF for NP0199006 (3-(acetyloxy)-2,5-dihydroxy-5-isopropyl-2a,7a-dimethyl-hexahydro-1ah-azuleno[5,6-b]oxiren-6-yl 3,4-dimethoxybenzoate)

PDB for NP0199006 (3-(acetyloxy)-2,5-dihydroxy-5-isopropyl-2a,7a-dimethyl-hexahydro-1ah-azuleno[5,6-b]oxiren-6-yl 3,4-dimethoxybenzoate)

3D PDB for NP0199006 (3-(acetyloxy)-2,5-dihydroxy-5-isopropyl-2a,7a-dimethyl-hexahydro-1ah-azuleno[5,6-b]oxiren-6-yl 3,4-dimethoxybenzoate)

SMILES for NP0199006 (3-(acetyloxy)-2,5-dihydroxy-5-isopropyl-2a,7a-dimethyl-hexahydro-1ah-azuleno[5,6-b]oxiren-6-yl 3,4-dimethoxybenzoate)

INCHI for NP0199006 (3-(acetyloxy)-2,5-dihydroxy-5-isopropyl-2a,7a-dimethyl-hexahydro-1ah-azuleno[5,6-b]oxiren-6-yl 3,4-dimethoxybenzoate)

Structure for NP0199006 (3-(acetyloxy)-2,5-dihydroxy-5-isopropyl-2a,7a-dimethyl-hexahydro-1ah-azuleno[5,6-b]oxiren-6-yl 3,4-dimethoxybenzoate)

3D Structure for NP0199006 (3-(acetyloxy)-2,5-dihydroxy-5-isopropyl-2a,7a-dimethyl-hexahydro-1ah-azuleno[5,6-b]oxiren-6-yl 3,4-dimethoxybenzoate)