NP-MRD: Showing NP-Card for (4s,4ar)-4a-hydroxy-1,1,4,7-tetramethyl-1ah,2h,3h,4h,5h,7bh-cyclopropa[e]azulen-6-one (NP0251434)

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Record Information

Version

2.0

Created at

2022-09-07 14:37:51 UTC

Updated at

2022-09-07 14:37:51 UTC

NP-MRD ID

NP0251434

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4s,4ar)-4a-hydroxy-1,1,4,7-tetramethyl-1ah,2h,3h,4h,5h,7bh-cyclopropa[e]azulen-6-one

Description

(4S,4aR)-4a-hydroxy-1,1,4,7-tetramethyl-1a,2,3,4,5,7b-hexahydrocyclopropa[e]azulen-6-one belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton. Based on a literature review very few articles have been published on (4S,4aR)-4a-hydroxy-1,1,4,7-tetramethyl-1a,2,3,4,5,7b-hexahydrocyclopropa[e]azulen-6-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309072216372D          

 17 19  0  0  1  0            999 V2000
    1.5587    0.5013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3506   -0.2970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8741   -0.9347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6946   -0.8490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2732   -1.4372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1740   -2.2562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4719   -2.6894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6955   -2.4105    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1073   -2.9890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4294   -1.6296    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8678   -2.2339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6311   -1.4214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5824   -0.5979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1125   -0.1532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4932   -0.6421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3069   -0.5055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6432    0.1692    0.0000 C   0  0  0  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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
  2 13  1  0  0  0  0
 13 14  2  0  0  0  0
  5 15  1  0  0  0  0
  4 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0251434

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CCC2C(C3=C(C)C(=O)C[C@@]13O)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O2/c1-8-5-6-10-13(14(10,3)4)12-9(2)11(16)7-15(8,12)17/h8,10,13,17H,5-7H2,1-4H3/t8-,10?,13?,15+/m0/s1

> <INCHI_KEY>
ZBZKCPGSZOLGGP-QAJPGIAFSA-N

> <FORMULA>
C15H22O2

> <MOLECULAR_WEIGHT>
234.339

> <EXACT_MASS>
234.161979948

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
26.862555342041123

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4aR,5S)-4a-hydroxy-1,1,2,5-tetramethyl-1H,1aH,3H,4H,4aH,5H,6H,7H,7aH-cyclopropa[e]azulen-3-one

> <JCHEM_LOGP>
2.451750401666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.987231077014357

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.745691558040214

> <JCHEM_PKA_STRONGEST_BASIC>
-3.347168642703674

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
67.49159999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4aR,5S)-4a-hydroxy-1,1,2,5-tetramethyl-1aH,4H,5H,6H,7H,7aH-cyclopropa[e]azulen-3-one

> <JCHEM_VEBER_RULE>
1

$$$$

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       2.910   0.936   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.521  -0.554   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.498  -1.745   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.030  -1.585   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.110  -2.683   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.925  -4.212   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.614  -5.020   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.165  -4.500   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.067  -5.580   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.668  -3.042   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.620  -4.170   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.178  -2.653   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.087  -1.116   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.210  -0.286   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.521  -1.199   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.039  -0.944   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.801   0.316   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5   15                                                  
CONECT    5    4    6   15                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    3   11   12                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12    2   14                                                  
CONECT   14   13                                                            
CONECT   15    5    4   16   17                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₂O₂

Average Mass

234.3390 Da

Monoisotopic Mass

234.16198 Da

IUPAC Name

(4aR,5S)-4a-hydroxy-1,1,2,5-tetramethyl-1H,1aH,3H,4H,4aH,5H,6H,7H,7aH-cyclopropa[e]azulen-3-one

Traditional Name

(4aR,5S)-4a-hydroxy-1,1,2,5-tetramethyl-1aH,4H,5H,6H,7H,7aH-cyclopropa[e]azulen-3-one

CAS Registry Number

Not Available

SMILES

C[C@H]1CCC2C(C3=C(C)C(=O)C[C@@]13O)C2(C)C

InChI Identifier

InChI=1S/C15H22O2/c1-8-5-6-10-13(14(10,3)4)12-9(2)11(16)7-15(8,12)17/h8,10,13,17H,5-7H2,1-4H3/t8-,10?,13?,15+/m0/s1

InChI Key

ZBZKCPGSZOLGGP-QAJPGIAFSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

5,10-cycloaromadendrane sesquiterpenoids

Alternative Parents

Substituents

5,10-cycloaromadendrane sesquiterpenoid
Tertiary alcohol
Cyclic alcohol
Cyclic ketone
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	2.45	ChemAxon
pKa (Strongest Acidic)	13.75	ChemAxon
pKa (Strongest Basic)	-3.3	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	0	ChemAxon
Refractivity	67.49 m³·mol⁻¹	ChemAxon
Polarizability	26.86 Å³	ChemAxon
Number of Rings	3	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

4438280

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5273907

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4s,4ar)-4a-hydroxy-1,1,4,7-tetramethyl-1ah,2h,3h,4h,5h,7bh-cyclopropa[e]azulen-6-one (NP0251434)

MOL for NP0251434 ((4s,4ar)-4a-hydroxy-1,1,4,7-tetramethyl-1ah,2h,3h,4h,5h,7bh-cyclopropa[e]azulen-6-one)

3D MOL for NP0251434 ((4s,4ar)-4a-hydroxy-1,1,4,7-tetramethyl-1ah,2h,3h,4h,5h,7bh-cyclopropa[e]azulen-6-one)

3D SDF for NP0251434 ((4s,4ar)-4a-hydroxy-1,1,4,7-tetramethyl-1ah,2h,3h,4h,5h,7bh-cyclopropa[e]azulen-6-one)

3D-SDF for NP0251434 ((4s,4ar)-4a-hydroxy-1,1,4,7-tetramethyl-1ah,2h,3h,4h,5h,7bh-cyclopropa[e]azulen-6-one)

PDB for NP0251434 ((4s,4ar)-4a-hydroxy-1,1,4,7-tetramethyl-1ah,2h,3h,4h,5h,7bh-cyclopropa[e]azulen-6-one)

3D PDB for NP0251434 ((4s,4ar)-4a-hydroxy-1,1,4,7-tetramethyl-1ah,2h,3h,4h,5h,7bh-cyclopropa[e]azulen-6-one)

SMILES for NP0251434 ((4s,4ar)-4a-hydroxy-1,1,4,7-tetramethyl-1ah,2h,3h,4h,5h,7bh-cyclopropa[e]azulen-6-one)

INCHI for NP0251434 ((4s,4ar)-4a-hydroxy-1,1,4,7-tetramethyl-1ah,2h,3h,4h,5h,7bh-cyclopropa[e]azulen-6-one)

Structure for NP0251434 ((4s,4ar)-4a-hydroxy-1,1,4,7-tetramethyl-1ah,2h,3h,4h,5h,7bh-cyclopropa[e]azulen-6-one)

3D Structure for NP0251434 ((4s,4ar)-4a-hydroxy-1,1,4,7-tetramethyl-1ah,2h,3h,4h,5h,7bh-cyclopropa[e]azulen-6-one)