NP-MRD: Showing NP-Card for 6-formyl-3-hydroxy-3-isopropyl-8a-methyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-hydroxybenzoate (NP0226708)

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Record Information

Version

2.0

Created at

2022-09-06 05:50:07 UTC

Updated at

2022-09-06 05:50:07 UTC

NP-MRD ID

NP0226708

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-formyl-3-hydroxy-3-isopropyl-8a-methyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-hydroxybenzoate

Description

6-Formyl-3-hydroxy-8a-methyl-3-(propan-2-yl)-1,2,3,3a,4,5,8,8a-octahydroazulen-4-yl 4-hydroxybenzoate belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 6-formyl-3-hydroxy-3-isopropyl-8a-methyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-hydroxybenzoate is found in Ferula kuhistanica. 6-Formyl-3-hydroxy-8a-methyl-3-(propan-2-yl)-1,2,3,3a,4,5,8,8a-octahydroazulen-4-yl 4-hydroxybenzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004251523402D          

 27 29  0  0  0  0            999 V2000
   -0.4723   -1.6436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2422   -2.0561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2422   -2.8811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9566   -1.6436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2922   -2.3972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4717   -0.9761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9566   -0.3087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413   -0.5636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5940    0.2481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3863   -0.0492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1906   -0.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5485   -0.9761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1906   -1.7194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3863   -1.9030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2027   -2.7073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -3.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5958   -3.0253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6239   -4.0728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2287   -4.6339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0451   -5.4382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2567   -5.6814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0731   -6.4857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6520   -5.1203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8355   -4.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413   -1.3886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3735   -0.9761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7860   -1.6906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 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
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 18 24  1  0  0  0  0
 14 25  1  0  0  0  0
  4 25  1  0  0  0  0
  8 25  1  0  0  0  0
 12 26  1  0  0  0  0
 26 27  2  0  0  0  0
M  END


  Mrv1533004251523402D          

 27 29  0  0  0  0            999 V2000
   -0.4723   -1.6436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2422   -2.0561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2422   -2.8811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9566   -1.6436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2922   -2.3972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4717   -0.9761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9566   -0.3087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413   -0.5636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5940    0.2481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3863   -0.0492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1906   -0.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5485   -0.9761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1906   -1.7194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3863   -1.9030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2027   -2.7073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -3.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5958   -3.0253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6239   -4.0728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2287   -4.6339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0451   -5.4382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2567   -5.6814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0731   -6.4857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6520   -5.1203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8355   -4.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413   -1.3886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3735   -0.9761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7860   -1.6906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 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
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 18 24  1  0  0  0  0
 14 25  1  0  0  0  0
  4 25  1  0  0  0  0
  8 25  1  0  0  0  0
 12 26  1  0  0  0  0
 26 27  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0226708

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1(O)CCC2(C)CC=C(CC(OC(=O)C3=CC=C(O)C=C3)C12)C=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H28O5/c1-14(2)22(26)11-10-21(3)9-8-15(13-23)12-18(19(21)22)27-20(25)16-4-6-17(24)7-5-16/h4-8,13-14,18-19,24,26H,9-12H2,1-3H3

> <INCHI_KEY>
JENQPAWXVQJHSO-UHFFFAOYSA-N

> <FORMULA>
C22H28O5

> <MOLECULAR_WEIGHT>
372.461

> <EXACT_MASS>
372.193674002

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
40.61102069987416

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-formyl-3-hydroxy-8a-methyl-3-(propan-2-yl)-1,2,3,3a,4,5,8,8a-octahydroazulen-4-yl 4-hydroxybenzoate

> <ALOGPS_LOGP>
3.59

> <JCHEM_LOGP>
3.5873045113333326

> <ALOGPS_LOGS>
-4.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.269310396823652

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.496311677188437

> <JCHEM_PKA_STRONGEST_BASIC>
-3.118403952809463

> <JCHEM_POLAR_SURFACE_AREA>
83.83000000000001

> <JCHEM_REFRACTIVITY>
103.3684

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.88e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-formyl-3-hydroxy-3-isopropyl-8a-methyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-hydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      -0.882  -3.068   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.452  -3.838   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.452  -5.378   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.786  -3.068   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.412  -4.475   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.881  -1.822   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.786  -0.576   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.250  -1.052   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.975   0.463   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.454  -0.092   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.956  -0.435   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.624  -1.822   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.956  -3.210   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.454  -3.552   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.112  -5.054   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.241  -6.101   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.712  -5.647   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.898  -7.602   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.027  -8.650   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.684 -10.151   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.213 -10.605   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.870 -12.107   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.084  -9.558   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.426  -8.056   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.250  -2.592   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.164  -1.822   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       8.934  -3.156   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6   25                                             
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   25                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   26                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   25                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   18                                                       
CONECT   25   14    4    8                                                  
CONECT   26   12   27                                                       
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Value	Source
6-Formyl-3-hydroxy-8a-methyl-3-(propan-2-yl)-1,2,3,3a,4,5,8,8a-octahydroazulen-4-yl 4-hydroxybenzoic acid	Generator

Chemical Formula

C₂₂H₂₈O₅

Average Mass

372.4610 Da

Monoisotopic Mass

372.19367 Da

IUPAC Name

6-formyl-3-hydroxy-8a-methyl-3-(propan-2-yl)-1,2,3,3a,4,5,8,8a-octahydroazulen-4-yl 4-hydroxybenzoate

Traditional Name

6-formyl-3-hydroxy-3-isopropyl-8a-methyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-hydroxybenzoate

CAS Registry Number

Not Available

SMILES

CC(C)C1(O)CCC2(C)CC=C(CC(OC(=O)C3=CC=C(O)C=C3)C12)C=O

InChI Identifier

InChI=1S/C22H28O5/c1-14(2)22(26)11-10-21(3)9-8-15(13-23)12-18(19(21)22)27-20(25)16-4-6-17(24)7-5-16/h4-8,13-14,18-19,24,26H,9-12H2,1-3H3

InChI Key

JENQPAWXVQJHSO-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ferula kuhistanica	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-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
Benzoate ester
Benzoic acid or derivatives
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Tertiary alcohol
Cyclic alcohol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Alcohol
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aldehyde
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	3.59	ALOGPS
logP	3.59	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	8.5	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	103.37 m³·mol⁻¹	ChemAxon
Polarizability	40.61 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

85428860

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-formyl-3-hydroxy-3-isopropyl-8a-methyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-hydroxybenzoate (NP0226708)

MOL for NP0226708 (6-formyl-3-hydroxy-3-isopropyl-8a-methyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-hydroxybenzoate)

3D MOL for NP0226708 (6-formyl-3-hydroxy-3-isopropyl-8a-methyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-hydroxybenzoate)

3D SDF for NP0226708 (6-formyl-3-hydroxy-3-isopropyl-8a-methyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-hydroxybenzoate)

3D-SDF for NP0226708 (6-formyl-3-hydroxy-3-isopropyl-8a-methyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-hydroxybenzoate)

PDB for NP0226708 (6-formyl-3-hydroxy-3-isopropyl-8a-methyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-hydroxybenzoate)

3D PDB for NP0226708 (6-formyl-3-hydroxy-3-isopropyl-8a-methyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-hydroxybenzoate)

SMILES for NP0226708 (6-formyl-3-hydroxy-3-isopropyl-8a-methyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-hydroxybenzoate)

INCHI for NP0226708 (6-formyl-3-hydroxy-3-isopropyl-8a-methyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-hydroxybenzoate)

Structure for NP0226708 (6-formyl-3-hydroxy-3-isopropyl-8a-methyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-hydroxybenzoate)

3D Structure for NP0226708 (6-formyl-3-hydroxy-3-isopropyl-8a-methyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-hydroxybenzoate)