NP-MRD: Showing NP-Card for 2-[(5r,8r,8ar)-3,8-dimethyl-2-oxo-4,5,6,7,8,8a-hexahydro-1h-azulen-5-yl]prop-2-en-1-yl 3-hydroxy-3-methylbutanoate (NP0233611)

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Record Information

Version

2.0

Created at

2022-09-06 15:16:39 UTC

Updated at

2022-09-06 15:16:39 UTC

NP-MRD ID

NP0233611

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(5r,8r,8ar)-3,8-dimethyl-2-oxo-4,5,6,7,8,8a-hexahydro-1h-azulen-5-yl]prop-2-en-1-yl 3-hydroxy-3-methylbutanoate

Description

2-[(5R,8R,8aR)-3,8-dimethyl-2-oxo-1,2,4,5,6,7,8,8a-octahydroazulen-5-yl]prop-2-en-1-yl 3-hydroxy-3-methylbutanoate belongs to the class of organic compounds known as guaianes. These are sesquiterpenoids with a structure based on the guaiane skeleton. Guaiane is a bicyclic compound consisting of a decahydroazulene moiety, substituted with two methyl groups and a 1-methylethyl group at the 1-, 4-, and 7-position, respectively. 2-[(5r,8r,8ar)-3,8-dimethyl-2-oxo-4,5,6,7,8,8a-hexahydro-1h-azulen-5-yl]prop-2-en-1-yl 3-hydroxy-3-methylbutanoate is found in Moscharia pinnatifida. Based on a literature review very few articles have been published on 2-[(5R,8R,8aR)-3,8-dimethyl-2-oxo-1,2,4,5,6,7,8,8a-octahydroazulen-5-yl]prop-2-en-1-yl 3-hydroxy-3-methylbutanoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062217162D          

 24 25  0  0  1  0            999 V2000
    4.3699    3.1868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6713    2.4188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4871    2.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0015    2.9409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8172    2.8179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1187    2.0499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3316    3.4629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1474    3.3399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9632    3.2170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2704    4.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0245    2.5242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569    1.7738    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5149    1.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569    0.2872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526    0.1036    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1690   -0.7007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076    0.6180    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9230    0.3631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4380    1.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6130    1.0305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230    1.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6680    2.4826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076    1.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526    1.9574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  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
  8 11  1  0  0  0  0
 12  2  1  6  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  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  0  0  0  0
 12 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0233611

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC[C@H](CC2=C(C)C(=O)C[C@H]12)C(=C)COC(=O)CC(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O4/c1-12-6-7-15(8-17-14(3)18(21)9-16(12)17)13(2)11-24-19(22)10-20(4,5)23/h12,15-16,23H,2,6-11H2,1,3-5H3/t12-,15-,16-/m1/s1

> <INCHI_KEY>
GIJMOEIBTVWHCV-DAXOMENPSA-N

> <FORMULA>
C20H30O4

> <MOLECULAR_WEIGHT>
334.456

> <EXACT_MASS>
334.214409446

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
37.78144617951837

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(5R,8R,8aR)-3,8-dimethyl-2-oxo-1,2,4,5,6,7,8,8a-octahydroazulen-5-yl]prop-2-en-1-yl 3-hydroxy-3-methylbutanoate

> <JCHEM_LOGP>
3.0726108189999994

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.129615382066667

> <JCHEM_PKA_STRONGEST_BASIC>
-2.742106231884039

> <JCHEM_POLAR_SURFACE_AREA>
63.6

> <JCHEM_REFRACTIVITY>
94.33729999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-[(5R,8R,8aR)-3,8-dimethyl-2-oxo-4,5,6,7,8,8a-hexahydro-1H-azulen-5-yl]prop-2-en-1-yl 3-hydroxy-3-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       8.157   5.949   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.720   4.515   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.243   4.286   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      11.203   5.490   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      12.726   5.260   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      13.288   3.827   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      13.686   6.464   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.209   6.235   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.731   6.005   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      15.438   7.757   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      14.979   4.712   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.760   3.311   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.428   1.924   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.760   0.536   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.258   0.193   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.916  -1.308   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.054   1.154   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.590   0.678   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.684   1.924   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.144   1.924   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.590   3.169   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.114   4.634   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.054   2.694   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.258   3.654   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8                                                            
CONECT   12    2   13   24                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   17   24                                                  
CONECT   24   23   12                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

View in JSmol

Synonyms

Value	Source
2-[(5R,8R,8AR)-3,8-dimethyl-2-oxo-1,2,4,5,6,7,8,8a-octahydroazulen-5-yl]prop-2-en-1-yl 3-hydroxy-3-methylbutanoic acid	Generator

Chemical Formula

C₂₀H₃₀O₄

Average Mass

334.4560 Da

Monoisotopic Mass

334.21441 Da

IUPAC Name

2-[(5R,8R,8aR)-3,8-dimethyl-2-oxo-1,2,4,5,6,7,8,8a-octahydroazulen-5-yl]prop-2-en-1-yl 3-hydroxy-3-methylbutanoate

Traditional Name

2-[(5R,8R,8aR)-3,8-dimethyl-2-oxo-4,5,6,7,8,8a-hexahydro-1H-azulen-5-yl]prop-2-en-1-yl 3-hydroxy-3-methylbutanoate

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC[C@H](CC2=C(C)C(=O)C[C@H]12)C(=C)COC(=O)CC(C)(C)O

InChI Identifier

InChI=1S/C20H30O4/c1-12-6-7-15(8-17-14(3)18(21)9-16(12)17)13(2)11-24-19(22)10-20(4,5)23/h12,15-16,23H,2,6-11H2,1,3-5H3/t12-,15-,16-/m1/s1

InChI Key

GIJMOEIBTVWHCV-DAXOMENPSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Moscharia pinnatifida	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianes. These are sesquiterpenoids with a structure based on the guaiane skeleton. Guaiane is a bicyclic compound consisting of a decahydroazulene moiety, substituted with two methyl groups and a 1-methylethyl group at the 1-, 4-, and 7-position, respectively.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Guaianes

Alternative Parents

Substituents

Guaiane sesquiterpenoid
Fatty acid ester
Fatty acyl
Tertiary alcohol
Carboxylic acid ester
Ketone
Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxide
Organic oxygen compound
Alcohol
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic 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	3.07	ChemAxon
pKa (Strongest Acidic)	15.13	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	94.34 m³·mol⁻¹	ChemAxon
Polarizability	37.78 Å³	ChemAxon
Number of Rings	2	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

15143877

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-[(5r,8r,8ar)-3,8-dimethyl-2-oxo-4,5,6,7,8,8a-hexahydro-1h-azulen-5-yl]prop-2-en-1-yl 3-hydroxy-3-methylbutanoate (NP0233611)

MOL for NP0233611 (2-[(5r,8r,8ar)-3,8-dimethyl-2-oxo-4,5,6,7,8,8a-hexahydro-1h-azulen-5-yl]prop-2-en-1-yl 3-hydroxy-3-methylbutanoate)

3D MOL for NP0233611 (2-[(5r,8r,8ar)-3,8-dimethyl-2-oxo-4,5,6,7,8,8a-hexahydro-1h-azulen-5-yl]prop-2-en-1-yl 3-hydroxy-3-methylbutanoate)

3D SDF for NP0233611 (2-[(5r,8r,8ar)-3,8-dimethyl-2-oxo-4,5,6,7,8,8a-hexahydro-1h-azulen-5-yl]prop-2-en-1-yl 3-hydroxy-3-methylbutanoate)

3D-SDF for NP0233611 (2-[(5r,8r,8ar)-3,8-dimethyl-2-oxo-4,5,6,7,8,8a-hexahydro-1h-azulen-5-yl]prop-2-en-1-yl 3-hydroxy-3-methylbutanoate)

PDB for NP0233611 (2-[(5r,8r,8ar)-3,8-dimethyl-2-oxo-4,5,6,7,8,8a-hexahydro-1h-azulen-5-yl]prop-2-en-1-yl 3-hydroxy-3-methylbutanoate)

3D PDB for NP0233611 (2-[(5r,8r,8ar)-3,8-dimethyl-2-oxo-4,5,6,7,8,8a-hexahydro-1h-azulen-5-yl]prop-2-en-1-yl 3-hydroxy-3-methylbutanoate)

SMILES for NP0233611 (2-[(5r,8r,8ar)-3,8-dimethyl-2-oxo-4,5,6,7,8,8a-hexahydro-1h-azulen-5-yl]prop-2-en-1-yl 3-hydroxy-3-methylbutanoate)

INCHI for NP0233611 (2-[(5r,8r,8ar)-3,8-dimethyl-2-oxo-4,5,6,7,8,8a-hexahydro-1h-azulen-5-yl]prop-2-en-1-yl 3-hydroxy-3-methylbutanoate)

Structure for NP0233611 (2-[(5r,8r,8ar)-3,8-dimethyl-2-oxo-4,5,6,7,8,8a-hexahydro-1h-azulen-5-yl]prop-2-en-1-yl 3-hydroxy-3-methylbutanoate)

3D Structure for NP0233611 (2-[(5r,8r,8ar)-3,8-dimethyl-2-oxo-4,5,6,7,8,8a-hexahydro-1h-azulen-5-yl]prop-2-en-1-yl 3-hydroxy-3-methylbutanoate)