NP-MRD: Showing NP-Card for 2',2',4',6'-tetramethyl-3',7'-dihydrospiro[cyclopropane-1,5'-indene]-3',6',7'-triol (NP0322639)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-12 01:31:27 UTC

Updated at

2022-09-12 01:31:27 UTC

NP-MRD ID

NP0322639

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

2',2',4',6'-Tetramethyl-2',3',6',7'-tetrahydrospiro[cyclopropane-1,5'-indene]-3',6',7'-triol belongs to the class of organic compounds known as illudanes and illudins. These are sesquiterpenoids containing either the illudane moiety (based on a 3,6,6,7b-tetramethyl-decahydro-1H-cyclobuta[e]indene ring system), the illudin moiety (2',2',4',6'-tetramethyl-octahydrospiro[cyclopropane-1,5'-indene]), or a derivative thereof. 2',2',4',6'-tetramethyl-3',7'-dihydrospiro[cyclopropane-1,5'-indene]-3',6',7'-triol is found in Granulobasidium vellereum and Omphalotus illudens. 2',2',4',6'-Tetramethyl-2',3',6',7'-tetrahydrospiro[cyclopropane-1,5'-indene]-3',6',7'-triol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004231521252D          

 18 20  0  0  0  0            999 V2000
    2.6689    1.0205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8840    0.2240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6813    0.0120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3723    0.4627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4138    1.2867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0145   -0.0552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4624    0.6376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7503   -0.4283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7203   -0.8260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8964   -0.7844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3142   -1.3689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5293   -2.1654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5169   -1.1570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4466   -1.9790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6952   -1.2305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3018   -0.3605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5053   -0.5756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7173    0.2217    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
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 13 16  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0322639

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C2C(O)C(C)(C)C=C2C(O)C(C)(O)C11CC1

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O3/c1-8-10-9(7-13(2,3)12(10)17)11(16)14(4,18)15(8)5-6-15/h7,11-12,16-18H,5-6H2,1-4H3

> <INCHI_KEY>
MBTBAQPUVNSQEB-UHFFFAOYSA-N

> <FORMULA>
C15H22O3

> <MOLECULAR_WEIGHT>
250.338

> <EXACT_MASS>
250.156894568

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
28.01968120582805

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2',2',4',6'-tetramethyl-2',3',6',7'-tetrahydrospiro[cyclopropane-1,5'-indene]-3',6',7'-triol

> <ALOGPS_LOGP>
1.15

> <JCHEM_LOGP>
0.4207676313333327

> <ALOGPS_LOGS>
-1.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.961326991127553

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.071498692324436

> <JCHEM_PKA_STRONGEST_BASIC>
-3.226411518967974

> <JCHEM_POLAR_SURFACE_AREA>
60.69

> <JCHEM_REFRACTIVITY>
70.4519

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.73e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0       4.982   1.905   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.383   0.418   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.872   0.022   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.162   0.864   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       8.239   2.402   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       9.360  -0.103   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.197   1.190   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.734  -0.799   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.811  -1.542   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.273  -1.464   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.186  -2.555   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.588  -4.042   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.698  -2.160   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.567  -3.694   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.164  -2.297   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.297  -0.673   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.810  -1.075   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.206   0.414   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6   10                                                       
CONECT   10    9    3   11                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13    2   17   18                                             
CONECT   17   16   18                                                       
CONECT   18   17   16                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₂O₃

Average Mass

250.3380 Da

Monoisotopic Mass

250.15689 Da

IUPAC Name

2',2',4',6'-tetramethyl-2',3',6',7'-tetrahydrospiro[cyclopropane-1,5'-indene]-3',6',7'-triol

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC1=C2C(O)C(C)(C)C=C2C(O)C(C)(O)C11CC1

InChI Identifier

InChI=1S/C15H22O3/c1-8-10-9(7-13(2,3)12(10)17)11(16)14(4,18)15(8)5-6-15/h7,11-12,16-18H,5-6H2,1-4H3

InChI Key

MBTBAQPUVNSQEB-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Granulobasidium vellereum	LOTUS Database	35616633
Omphalotus illudens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as illudanes and illudins. These are sesquiterpenoids containing either the illudane moiety (based on a 3,6,6,7b-tetramethyl-decahydro-1H-cyclobuta[e]indene ring system), the illudin moiety (2',2',4',6'-tetramethyl-octahydrospiro[cyclopropane-1,5'-indene]), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Illudanes and illudins

Alternative Parents

Substituents

Illudine sesquiterpenoid
Tertiary alcohol
Secondary alcohol
Polyol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
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	1.15	ALOGPS
logP	0.42	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	13.07	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	60.69 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	70.45 m³·mol⁻¹	ChemAxon
Polarizability	28.02 Å³	ChemAxon
Number of Rings	3	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

254355

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2',2',4',6'-tetramethyl-3',7'-dihydrospiro[cyclopropane-1,5'-indene]-3',6',7'-triol (NP0322639)

MOL for NP0322639 (2',2',4',6'-tetramethyl-3',7'-dihydrospiro[cyclopropane-1,5'-indene]-3',6',7'-triol)

3D MOL for NP0322639 (2',2',4',6'-tetramethyl-3',7'-dihydrospiro[cyclopropane-1,5'-indene]-3',6',7'-triol)

3D SDF for NP0322639 (2',2',4',6'-tetramethyl-3',7'-dihydrospiro[cyclopropane-1,5'-indene]-3',6',7'-triol)

3D-SDF for NP0322639 (2',2',4',6'-tetramethyl-3',7'-dihydrospiro[cyclopropane-1,5'-indene]-3',6',7'-triol)

PDB for NP0322639 (2',2',4',6'-tetramethyl-3',7'-dihydrospiro[cyclopropane-1,5'-indene]-3',6',7'-triol)

3D PDB for NP0322639 (2',2',4',6'-tetramethyl-3',7'-dihydrospiro[cyclopropane-1,5'-indene]-3',6',7'-triol)

SMILES for NP0322639 (2',2',4',6'-tetramethyl-3',7'-dihydrospiro[cyclopropane-1,5'-indene]-3',6',7'-triol)

INCHI for NP0322639 (2',2',4',6'-tetramethyl-3',7'-dihydrospiro[cyclopropane-1,5'-indene]-3',6',7'-triol)

Structure for NP0322639 (2',2',4',6'-tetramethyl-3',7'-dihydrospiro[cyclopropane-1,5'-indene]-3',6',7'-triol)

3D Structure for NP0322639 (2',2',4',6'-tetramethyl-3',7'-dihydrospiro[cyclopropane-1,5'-indene]-3',6',7'-triol)