NP-MRD: Showing NP-Card for (3r,3ar,4s,8as)-3-hydroxy-3-isopropyl-6,8a-dimethyl-8-oxo-2,3a,4,5-tetrahydro-1h-azulen-4-yl (2z)-2-methylbut-2-enoate (NP0254032)

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Record Information

Version

2.0

Created at

2022-09-07 18:04:44 UTC

Updated at

2022-09-07 18:04:44 UTC

NP-MRD ID

NP0254032

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r,3ar,4s,8as)-3-hydroxy-3-isopropyl-6,8a-dimethyl-8-oxo-2,3a,4,5-tetrahydro-1h-azulen-4-yl (2z)-2-methylbut-2-enoate

Description

(3R,3aR,4S,8aS)-3-hydroxy-6,8a-dimethyl-8-oxo-3-(propan-2-yl)-1,2,3,3a,4,5,8,8a-octahydroazulen-4-yl (2Z)-2-methylbut-2-enoate belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (3r,3ar,4s,8as)-3-hydroxy-3-isopropyl-6,8a-dimethyl-8-oxo-2,3a,4,5-tetrahydro-1h-azulen-4-yl (2z)-2-methylbut-2-enoate is found in Ferula communis. Based on a literature review very few articles have been published on (3R,3aR,4S,8aS)-3-hydroxy-6,8a-dimethyl-8-oxo-3-(propan-2-yl)-1,2,3,3a,4,5,8,8a-octahydroazulen-4-yl (2Z)-2-methylbut-2-enoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309072220042D          

 24 25  0  0  1  0            999 V2000
    4.9833    3.2091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1950    3.4523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5902    2.8912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8019    3.1343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7738    2.0868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5621    1.8437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1690    1.5257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526    0.7214    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1569    0.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5149   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3399   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569   -0.9488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526   -1.1324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1690   -1.9367    0.0000 O   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
    2.5603   -1.4297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230   -0.8729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4380   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230    0.4619    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2585    1.2156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2085    0.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2085    1.6994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4940    0.4619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076    0.2070    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  1  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 24 19  1  1  0  0  0
  8 24  1  0  0  0  0
 15 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0254032

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(\C)C(=O)O[C@H]1CC(C)=CC(=O)[C@@]2(C)CC[C@@](O)(C(C)C)[C@@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O4/c1-7-14(5)18(22)24-15-10-13(4)11-16(21)19(6)8-9-20(23,12(2)3)17(15)19/h7,11-12,15,17,23H,8-10H2,1-6H3/b14-7-/t15-,17-,19+,20+/m0/s1

> <INCHI_KEY>
YMWBTMBPEHUMBA-AUQFSEFCSA-N

> <FORMULA>
C20H30O4

> <MOLECULAR_WEIGHT>
334.456

> <EXACT_MASS>
334.214409446

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
37.01931471402464

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,3aR,4S,8aS)-3-hydroxy-6,8a-dimethyl-8-oxo-3-(propan-2-yl)-1,2,3,3a,4,5,8,8a-octahydroazulen-4-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_LOGP>
4.267892657333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.38795747095582

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.251297947469165

> <JCHEM_PKA_STRONGEST_BASIC>
-3.125959385798284

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
95.27340000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3R,3aR,4S,8aS)-3-hydroxy-3-isopropyl-6,8a-dimethyl-8-oxo-2,3a,4,5-tetrahydro-1H-azulen-4-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       9.302   5.990   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.831   6.444   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.702   5.397   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.230   5.851   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.044   3.895   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       8.516   3.442   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       5.916   2.848   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.258   1.347   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.760   1.004   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.428  -0.384   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.968  -0.384   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.760  -1.771   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.258  -2.114   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.916  -3.615   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.054  -1.154   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.779  -2.669   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.590  -1.629   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.684  -0.384   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.590   0.862   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.216   2.269   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.256   1.632   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.256   3.172   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.922   0.862   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.054   0.386   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   24                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17   24                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21   24                                             
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   19    8   15                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

View in JSmol

Synonyms

Value	Source
(3R,3AR,4S,8as)-3-hydroxy-6,8a-dimethyl-8-oxo-3-(propan-2-yl)-1,2,3,3a,4,5,8,8a-octahydroazulen-4-yl (2Z)-2-methylbut-2-enoic acid	Generator

Chemical Formula

C₂₀H₃₀O₄

Average Mass

334.4560 Da

Monoisotopic Mass

334.21441 Da

IUPAC Name

(3R,3aR,4S,8aS)-3-hydroxy-6,8a-dimethyl-8-oxo-3-(propan-2-yl)-1,2,3,3a,4,5,8,8a-octahydroazulen-4-yl (2Z)-2-methylbut-2-enoate

Traditional Name

(3R,3aR,4S,8aS)-3-hydroxy-3-isopropyl-6,8a-dimethyl-8-oxo-2,3a,4,5-tetrahydro-1H-azulen-4-yl (2Z)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

C\C=C(\C)C(=O)O[C@H]1CC(C)=CC(=O)[C@@]2(C)CC[C@@](O)(C(C)C)[C@@H]12

InChI Identifier

InChI=1S/C20H30O4/c1-7-14(5)18(22)24-15-10-13(4)11-16(21)19(6)8-9-20(23,12(2)3)17(15)19/h7,11-12,15,17,23H,8-10H2,1-6H3/b14-7-/t15-,17-,19+,20+/m0/s1

InChI Key

YMWBTMBPEHUMBA-AUQFSEFCSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

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
Fatty acid ester
Fatty acyl
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Carboxylic acid ester
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
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	4.27	ChemAxon
pKa (Strongest Acidic)	14.25	ChemAxon
pKa (Strongest Basic)	-3.1	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	4	ChemAxon
Refractivity	95.27 m³·mol⁻¹	ChemAxon
Polarizability	37.02 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

162968469

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3r,3ar,4s,8as)-3-hydroxy-3-isopropyl-6,8a-dimethyl-8-oxo-2,3a,4,5-tetrahydro-1h-azulen-4-yl (2z)-2-methylbut-2-enoate (NP0254032)

MOL for NP0254032 ((3r,3ar,4s,8as)-3-hydroxy-3-isopropyl-6,8a-dimethyl-8-oxo-2,3a,4,5-tetrahydro-1h-azulen-4-yl (2z)-2-methylbut-2-enoate)

3D MOL for NP0254032 ((3r,3ar,4s,8as)-3-hydroxy-3-isopropyl-6,8a-dimethyl-8-oxo-2,3a,4,5-tetrahydro-1h-azulen-4-yl (2z)-2-methylbut-2-enoate)

3D SDF for NP0254032 ((3r,3ar,4s,8as)-3-hydroxy-3-isopropyl-6,8a-dimethyl-8-oxo-2,3a,4,5-tetrahydro-1h-azulen-4-yl (2z)-2-methylbut-2-enoate)

3D-SDF for NP0254032 ((3r,3ar,4s,8as)-3-hydroxy-3-isopropyl-6,8a-dimethyl-8-oxo-2,3a,4,5-tetrahydro-1h-azulen-4-yl (2z)-2-methylbut-2-enoate)

PDB for NP0254032 ((3r,3ar,4s,8as)-3-hydroxy-3-isopropyl-6,8a-dimethyl-8-oxo-2,3a,4,5-tetrahydro-1h-azulen-4-yl (2z)-2-methylbut-2-enoate)

3D PDB for NP0254032 ((3r,3ar,4s,8as)-3-hydroxy-3-isopropyl-6,8a-dimethyl-8-oxo-2,3a,4,5-tetrahydro-1h-azulen-4-yl (2z)-2-methylbut-2-enoate)

SMILES for NP0254032 ((3r,3ar,4s,8as)-3-hydroxy-3-isopropyl-6,8a-dimethyl-8-oxo-2,3a,4,5-tetrahydro-1h-azulen-4-yl (2z)-2-methylbut-2-enoate)

INCHI for NP0254032 ((3r,3ar,4s,8as)-3-hydroxy-3-isopropyl-6,8a-dimethyl-8-oxo-2,3a,4,5-tetrahydro-1h-azulen-4-yl (2z)-2-methylbut-2-enoate)

Structure for NP0254032 ((3r,3ar,4s,8as)-3-hydroxy-3-isopropyl-6,8a-dimethyl-8-oxo-2,3a,4,5-tetrahydro-1h-azulen-4-yl (2z)-2-methylbut-2-enoate)

3D Structure for NP0254032 ((3r,3ar,4s,8as)-3-hydroxy-3-isopropyl-6,8a-dimethyl-8-oxo-2,3a,4,5-tetrahydro-1h-azulen-4-yl (2z)-2-methylbut-2-enoate)