NP-MRD: Showing NP-Card for (3as,5r,8s,8as)-8a-hydroxy-5-isopropyl-8-methyl-3-methylidene-hexahydro-1h-azulen-4-one (NP0225945)

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Record Information

Version

2.0

Created at

2022-09-06 04:49:32 UTC

Updated at

2022-09-06 04:49:32 UTC

NP-MRD ID

NP0225945

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3as,5r,8s,8as)-8a-hydroxy-5-isopropyl-8-methyl-3-methylidene-hexahydro-1h-azulen-4-one

Description

(3AS,5R,8S,8aS)-8a-hydroxy-8-methyl-3-methylidene-5-(propan-2-yl)-decahydroazulen-4-one 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. (3as,5r,8s,8as)-8a-hydroxy-5-isopropyl-8-methyl-3-methylidene-hexahydro-1h-azulen-4-one is found in Porella swartziana. Based on a literature review very few articles have been published on (3aS,5R,8S,8aS)-8a-hydroxy-8-methyl-3-methylidene-5-(propan-2-yl)-decahydroazulen-4-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062206492D          

 17 18  0  0  1  0            999 V2000
    0.7017   -2.4282    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
    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  2  0  0  0  0  0  0  0  0  0
    1.5940    0.2481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3863   -0.0492    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2027    0.7551    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  2  0  0  0  0  0  0  0  0  0
    3.7050   -2.3644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5208   -2.2415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4036   -3.1324    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
    1.7413   -1.3886    0.0000 C   0  0  1  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  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17  2  1  1  0  0  0
  5 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0225945

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@H]1CC[C@H](C)[C@@]2(O)CCC(=C)[C@@H]2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O2/c1-9(2)12-6-5-11(4)15(17)8-7-10(3)13(15)14(12)16/h9,11-13,17H,3,5-8H2,1-2,4H3/t11-,12+,13+,15-/m0/s1

> <INCHI_KEY>
YFBDNDYPTKETGA-JLNYLFASSA-N

> <FORMULA>
C15H24O2

> <MOLECULAR_WEIGHT>
236.355

> <EXACT_MASS>
236.177630013

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
27.505980703731417

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aS,5R,8S,8aS)-8a-hydroxy-8-methyl-3-methylidene-5-(propan-2-yl)-decahydroazulen-4-one

> <JCHEM_LOGP>
3.1632314530000003

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.740615815354829

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.735463911208306

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1964815874566463

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
68.8202

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3aS,5R,8S,8aS)-8a-hydroxy-5-isopropyl-8-methyl-3-methylidene-hexahydro-1H-azulen-4-one

> <JCHEM_VEBER_RULE>
1

$$$$

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       1.310  -4.533   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.786  -3.068   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.881  -1.822   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.786  -0.576   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.250  -1.052   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.975   0.463   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.454  -0.092   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.112   1.409   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.956  -0.435   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.624  -1.822   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.956  -3.210   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.916  -4.414   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.439  -4.184   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.353  -5.847   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.454  -3.552   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.112  -5.054   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.250  -2.592   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7   17                                             
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   11   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    2    5                                                  
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₄O₂

Average Mass

236.3550 Da

Monoisotopic Mass

236.17763 Da

IUPAC Name

(3aS,5R,8S,8aS)-8a-hydroxy-8-methyl-3-methylidene-5-(propan-2-yl)-decahydroazulen-4-one

Traditional Name

(3aS,5R,8S,8aS)-8a-hydroxy-5-isopropyl-8-methyl-3-methylidene-hexahydro-1H-azulen-4-one

CAS Registry Number

Not Available

SMILES

CC(C)[C@H]1CC[C@H](C)[C@@]2(O)CCC(=C)[C@@H]2C1=O

InChI Identifier

InChI=1S/C15H24O2/c1-9(2)12-6-5-11(4)15(17)8-7-10(3)13(15)14(12)16/h9,11-13,17H,3,5-8H2,1-2,4H3/t11-,12+,13+,15-/m0/s1

InChI Key

YFBDNDYPTKETGA-JLNYLFASSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Porella swartziana	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
Tertiary alcohol
Cyclic alcohol
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	3.16	ChemAxon
pKa (Strongest Acidic)	13.74	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	68.82 m³·mol⁻¹	ChemAxon
Polarizability	27.51 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

162868542

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3as,5r,8s,8as)-8a-hydroxy-5-isopropyl-8-methyl-3-methylidene-hexahydro-1h-azulen-4-one (NP0225945)

MOL for NP0225945 ((3as,5r,8s,8as)-8a-hydroxy-5-isopropyl-8-methyl-3-methylidene-hexahydro-1h-azulen-4-one)

3D MOL for NP0225945 ((3as,5r,8s,8as)-8a-hydroxy-5-isopropyl-8-methyl-3-methylidene-hexahydro-1h-azulen-4-one)

3D SDF for NP0225945 ((3as,5r,8s,8as)-8a-hydroxy-5-isopropyl-8-methyl-3-methylidene-hexahydro-1h-azulen-4-one)

3D-SDF for NP0225945 ((3as,5r,8s,8as)-8a-hydroxy-5-isopropyl-8-methyl-3-methylidene-hexahydro-1h-azulen-4-one)

PDB for NP0225945 ((3as,5r,8s,8as)-8a-hydroxy-5-isopropyl-8-methyl-3-methylidene-hexahydro-1h-azulen-4-one)

3D PDB for NP0225945 ((3as,5r,8s,8as)-8a-hydroxy-5-isopropyl-8-methyl-3-methylidene-hexahydro-1h-azulen-4-one)

SMILES for NP0225945 ((3as,5r,8s,8as)-8a-hydroxy-5-isopropyl-8-methyl-3-methylidene-hexahydro-1h-azulen-4-one)

INCHI for NP0225945 ((3as,5r,8s,8as)-8a-hydroxy-5-isopropyl-8-methyl-3-methylidene-hexahydro-1h-azulen-4-one)

Structure for NP0225945 ((3as,5r,8s,8as)-8a-hydroxy-5-isopropyl-8-methyl-3-methylidene-hexahydro-1h-azulen-4-one)

3D Structure for NP0225945 ((3as,5r,8s,8as)-8a-hydroxy-5-isopropyl-8-methyl-3-methylidene-hexahydro-1h-azulen-4-one)