NP-MRD: Showing NP-Card for 1',3',4',6'-tetrahydroxy-2',2',4',6'-tetramethyl-1',3'-dihydrospiro[cyclopropane-1,5'-inden]-7'-one (NP0322321)

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Record Information

Version

2.0

Created at

2022-09-12 01:01:43 UTC

Updated at

2022-09-12 01:01:43 UTC

NP-MRD ID

NP0322321

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1',3',4',6'-tetrahydroxy-2',2',4',6'-tetramethyl-1',3'-dihydrospiro[cyclopropane-1,5'-inden]-7'-one

Description

1',3',4',6'-Tetrahydroxy-2',2',4',6'-tetramethyl-1',2',3',4',6',7'-hexahydrospiro[cyclopropane-1,5'-indene]-7'-one belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. 1',3',4',6'-tetrahydroxy-2',2',4',6'-tetramethyl-1',3'-dihydrospiro[cyclopropane-1,5'-inden]-7'-one is found in Omphalotus illudens and Omphalotus nidiformis. 1',3',4',6'-Tetrahydroxy-2',2',4',6'-tetramethyl-1',2',3',4',6',7'-hexahydrospiro[cyclopropane-1,5'-indene]-7'-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004171514012D          

 20 22  0  0  0  0            999 V2000
    4.6233    1.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8875    1.5308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3355    0.8380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5934    2.3016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0441    2.9926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7694    2.2601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5543    1.4636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2453    1.0129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2869    0.1890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7570    1.2517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1042    0.5033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0803    0.7798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1748    1.8362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5903    1.2540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3783    2.0513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3899    2.6326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5682    2.7062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3196    3.4546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1872    2.8446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4023    3.6411    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  2  0  0  0  0
  7  8  1  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
  6 19  1  0  0  0  0
 19 20  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0322321

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)C(O)C2=C(C1O)C(C)(O)C1(CC1)C(C)(O)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O5/c1-12(2)9(16)7-8(11(12)18)13(3,19)15(5-6-15)14(4,20)10(7)17/h9,11,16,18-20H,5-6H2,1-4H3

> <INCHI_KEY>
MVHBMSFOLKLQJQ-UHFFFAOYSA-N

> <FORMULA>
C15H22O5

> <MOLECULAR_WEIGHT>
282.336

> <EXACT_MASS>
282.146723808

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
29.51002502201053

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1',3',4',6'-tetrahydroxy-2',2',4',6'-tetramethyl-1',2',3',4',6',7'-hexahydrospiro[cyclopropane-1,5'-indene]-7'-one

> <ALOGPS_LOGP>
0.15

> <JCHEM_LOGP>
-0.4103479196666665

> <ALOGPS_LOGS>
-1.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.457396676487434

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.644125088468822

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2721787100270916

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
71.79799999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.63e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1',3',4',6'-tetrahydroxy-2',2',4',6'-tetramethyl-1',3'-dihydrospiro[cyclopropane-1,5'-indene]-7'-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       8.630   3.554   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.257   2.858   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.093   1.564   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.708   4.296   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       7.549   5.586   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.170   4.219   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.768   2.732   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.058   1.891   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.135   0.353   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.280   2.336   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.928   0.939   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.017   1.456   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.193   3.428   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.102   2.341   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.706   3.829   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.594   4.914   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.061   5.052   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.463   6.449   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.083   5.310   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.484   6.797   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    8                                             
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   19                                                  
CONECT    7    6    8   10                                                  
CONECT    8    7    2    9                                                  
CONECT    9    8                                                            
CONECT   10    7   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10   14   15   16                                             
CONECT   14   13   15                                                       
CONECT   15   14   13                                                       
CONECT   16   13   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16    6   20                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₂O₅

Average Mass

282.3360 Da

Monoisotopic Mass

282.14672 Da

IUPAC Name

1',3',4',6'-tetrahydroxy-2',2',4',6'-tetramethyl-1',2',3',4',6',7'-hexahydrospiro[cyclopropane-1,5'-indene]-7'-one

Traditional Name

1',3',4',6'-tetrahydroxy-2',2',4',6'-tetramethyl-1',3'-dihydrospiro[cyclopropane-1,5'-indene]-7'-one

CAS Registry Number

Not Available

SMILES

CC1(C)C(O)C2=C(C1O)C(C)(O)C1(CC1)C(C)(O)C2=O

InChI Identifier

InChI=1S/C15H22O5/c1-12(2)9(16)7-8(11(12)18)13(3,19)15(5-6-15)14(4,20)10(7)17/h9,11,16,18-20H,5-6H2,1-4H3

InChI Key

MVHBMSFOLKLQJQ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Omphalotus illudens	LOTUS Database	35616633
Omphalotus nidiformis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclohexenones

Alternative Parents

Substituents

Cyclohexenone
Acyloin
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Polyol
Organic oxide
Hydrocarbon derivative
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	0.15	ALOGPS
logP	-0.41	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	12.64	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	71.8 m³·mol⁻¹	ChemAxon
Polarizability	29.51 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

14864082

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1',3',4',6'-tetrahydroxy-2',2',4',6'-tetramethyl-1',3'-dihydrospiro[cyclopropane-1,5'-inden]-7'-one (NP0322321)

MOL for NP0322321 (1',3',4',6'-tetrahydroxy-2',2',4',6'-tetramethyl-1',3'-dihydrospiro[cyclopropane-1,5'-inden]-7'-one)

3D MOL for NP0322321 (1',3',4',6'-tetrahydroxy-2',2',4',6'-tetramethyl-1',3'-dihydrospiro[cyclopropane-1,5'-inden]-7'-one)

3D SDF for NP0322321 (1',3',4',6'-tetrahydroxy-2',2',4',6'-tetramethyl-1',3'-dihydrospiro[cyclopropane-1,5'-inden]-7'-one)

3D-SDF for NP0322321 (1',3',4',6'-tetrahydroxy-2',2',4',6'-tetramethyl-1',3'-dihydrospiro[cyclopropane-1,5'-inden]-7'-one)

PDB for NP0322321 (1',3',4',6'-tetrahydroxy-2',2',4',6'-tetramethyl-1',3'-dihydrospiro[cyclopropane-1,5'-inden]-7'-one)

3D PDB for NP0322321 (1',3',4',6'-tetrahydroxy-2',2',4',6'-tetramethyl-1',3'-dihydrospiro[cyclopropane-1,5'-inden]-7'-one)

SMILES for NP0322321 (1',3',4',6'-tetrahydroxy-2',2',4',6'-tetramethyl-1',3'-dihydrospiro[cyclopropane-1,5'-inden]-7'-one)

INCHI for NP0322321 (1',3',4',6'-tetrahydroxy-2',2',4',6'-tetramethyl-1',3'-dihydrospiro[cyclopropane-1,5'-inden]-7'-one)

Structure for NP0322321 (1',3',4',6'-tetrahydroxy-2',2',4',6'-tetramethyl-1',3'-dihydrospiro[cyclopropane-1,5'-inden]-7'-one)

3D Structure for NP0322321 (1',3',4',6'-tetrahydroxy-2',2',4',6'-tetramethyl-1',3'-dihydrospiro[cyclopropane-1,5'-inden]-7'-one)