NP-MRD: Showing NP-Card for {2,2a,4a,7-tetrahydroxy-6,6,7b-trimethyl-1h,2h,5h,7h,7ah-cyclobuta[e]inden-3-yl}methyl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate (NP0166702)

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Record Information

Version

1.0

Created at

2022-09-03 02:07:47 UTC

Updated at

2022-09-03 02:07:48 UTC

NP-MRD ID

NP0166702

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{2,2a,4a,7-tetrahydroxy-6,6,7b-trimethyl-1h,2h,5h,7h,7ah-cyclobuta[e]inden-3-yl}methyl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate

Description

{2,2A,4a,7-tetrahydroxy-6,6,7b-trimethyl-1H,2H,2aH,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-3-yl}methyl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate 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. {2,2a,4a,7-tetrahydroxy-6,6,7b-trimethyl-1h,2h,5h,7h,7ah-cyclobuta[e]inden-3-yl}methyl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate is found in Armillaria novae-zelandiae. {2,2A,4a,7-tetrahydroxy-6,6,7b-trimethyl-1H,2H,2aH,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-3-yl}methyl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004261504322D          

 33 36  0  0  0  0            999 V2000
   -3.0283    2.2251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6427    2.9544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8183    2.9851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4326    3.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6082    3.7451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2225    4.4744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1694    3.0465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6550    3.0771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0407    3.8064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0938    2.3785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9182    2.4092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3570    1.7105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1815    1.7412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6202    1.0426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0800    1.7276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4330    0.9012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7651    1.5572    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
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 32 33  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1533004261504322D          

 33 36  0  0  0  0            999 V2000
   -3.0283    2.2251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0166702

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C(C(=O)OCC2=CC3(O)CC(C)(C)C(O)C3C3(C)CC(O)C23O)C(C)=C1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C24H31ClO8/c1-11-16(13(26)6-14(32-5)17(11)25)20(29)33-9-12-7-23(30)10-21(2,3)19(28)18(23)22(4)8-15(27)24(12,22)31/h6-7,15,18-19,26-28,30-31H,8-10H2,1-5H3

> <INCHI_KEY>
RFGVTAUBLVGNQH-UHFFFAOYSA-N

> <FORMULA>
C24H31ClO8

> <MOLECULAR_WEIGHT>
482.95

> <EXACT_MASS>
482.1707457

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
49.22292682491074

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{2,2a,4a,7-tetrahydroxy-6,6,7b-trimethyl-1H,2H,2aH,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-3-yl}methyl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate

> <ALOGPS_LOGP>
1.73

> <JCHEM_LOGP>
2.273020069666667

> <ALOGPS_LOGS>
-3.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.86683087730827

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.327166476638508

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0722334222982175

> <JCHEM_POLAR_SURFACE_AREA>
136.68

> <JCHEM_REFRACTIVITY>
121.18459999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.57e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{2,2a,4a,7-tetrahydroxy-6,6,7b-trimethyl-1H,2H,5H,7H,7aH-cyclobuta[e]inden-3-yl}methyl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0      -5.653   4.154   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.933   5.515   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -3.394   5.572   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.674   6.934   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.135   6.991   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.415   8.352   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.316   5.687   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.223   5.744   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.943   7.105   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       2.042   4.440   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.581   4.497   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.400   3.193   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.939   3.250   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.758   1.946   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.616   3.225   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.275   1.682   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.493   0.158   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.986   0.534   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.023  -1.288   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.110  -0.521   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.846  -2.038   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.038   0.585   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.499   0.527   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.953  -0.944   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.195  -0.292   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.376   1.013   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.874   1.356   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       3.680   1.832   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.551   2.879   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -1.036   4.325   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.217   3.021   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.575   4.268   0.000  0.00  0.00           C+0
HETATM   33 Cl   UNK     0      -3.295   2.907   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   32                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   30                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   28                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16   22                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   17   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   14   23                                                  
CONECT   23   22   24   25   28                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   12   23   29                                             
CONECT   29   28                                                            
CONECT   30    7   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30    3   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
{2,2a,4a,7-tetrahydroxy-6,6,7b-trimethyl-1H,2H,2ah,4ah,5H,6H,7H,7ah,7BH-cyclobuta[e]inden-3-yl}methyl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoic acid	Generator

Chemical Formula

C₂₄H₃₁ClO₈

Average Mass

482.9500 Da

Monoisotopic Mass

482.17075 Da

IUPAC Name

{2,2a,4a,7-tetrahydroxy-6,6,7b-trimethyl-1H,2H,2aH,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-3-yl}methyl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate

Traditional Name

{2,2a,4a,7-tetrahydroxy-6,6,7b-trimethyl-1H,2H,5H,7H,7aH-cyclobuta[e]inden-3-yl}methyl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C(C(=O)OCC2=CC3(O)CC(C)(C)C(O)C3C3(C)CC(O)C23O)C(C)=C1Cl

InChI Identifier

InChI=1S/C24H31ClO8/c1-11-16(13(26)6-14(32-5)17(11)25)20(29)33-9-12-7-23(30)10-21(2,3)19(28)18(23)22(4)8-15(27)24(12,22)31/h6-7,15,18-19,26-28,30-31H,8-10H2,1-5H3

InChI Key

RFGVTAUBLVGNQH-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Armillaria novae-zelandiae	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

Illudane sesquiterpenoid
O-hydroxybenzoic acid ester
P-methoxybenzoic acid or derivatives
Methoxyphenol
Benzoate ester
Salicylic acid or derivatives
3-halobenzoic acid or derivatives
Halobenzoic acid or derivatives
Benzoic acid or derivatives
4-halophenol
Phenoxy compound
M-cresol
Benzoyl
Anisole
4-chlorophenol
Phenol ether
Methoxybenzene
Chlorobenzene
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Halobenzene
Toluene
Aryl chloride
Monocyclic benzene moiety
Aryl halide
Benzenoid
Cyclic alcohol
Tertiary alcohol
Vinylogous acid
Secondary alcohol
Carboxylic acid ester
Cyclobutanol
Carboxylic acid derivative
Polyol
Monocarboxylic acid or derivatives
Ether
Organic oxygen compound
Organohalogen compound
Organochloride
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Aromatic homopolycyclic compound

Molecular Framework

Aromatic 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	1.73	ALOGPS
logP	2.27	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	9.33	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	136.68 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	121.18 m³·mol⁻¹	ChemAxon
Polarizability	49.22 Å³	ChemAxon
Number of Rings	4	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

76152749

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for {2,2a,4a,7-tetrahydroxy-6,6,7b-trimethyl-1h,2h,5h,7h,7ah-cyclobuta[e]inden-3-yl}methyl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate (NP0166702)

MOL for NP0166702 ({2,2a,4a,7-tetrahydroxy-6,6,7b-trimethyl-1h,2h,5h,7h,7ah-cyclobuta[e]inden-3-yl}methyl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate)

3D MOL for NP0166702 ({2,2a,4a,7-tetrahydroxy-6,6,7b-trimethyl-1h,2h,5h,7h,7ah-cyclobuta[e]inden-3-yl}methyl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate)

3D SDF for NP0166702 ({2,2a,4a,7-tetrahydroxy-6,6,7b-trimethyl-1h,2h,5h,7h,7ah-cyclobuta[e]inden-3-yl}methyl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate)

3D-SDF for NP0166702 ({2,2a,4a,7-tetrahydroxy-6,6,7b-trimethyl-1h,2h,5h,7h,7ah-cyclobuta[e]inden-3-yl}methyl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate)

PDB for NP0166702 ({2,2a,4a,7-tetrahydroxy-6,6,7b-trimethyl-1h,2h,5h,7h,7ah-cyclobuta[e]inden-3-yl}methyl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate)

3D PDB for NP0166702 ({2,2a,4a,7-tetrahydroxy-6,6,7b-trimethyl-1h,2h,5h,7h,7ah-cyclobuta[e]inden-3-yl}methyl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate)

SMILES for NP0166702 ({2,2a,4a,7-tetrahydroxy-6,6,7b-trimethyl-1h,2h,5h,7h,7ah-cyclobuta[e]inden-3-yl}methyl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate)

INCHI for NP0166702 ({2,2a,4a,7-tetrahydroxy-6,6,7b-trimethyl-1h,2h,5h,7h,7ah-cyclobuta[e]inden-3-yl}methyl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate)

Structure for NP0166702 ({2,2a,4a,7-tetrahydroxy-6,6,7b-trimethyl-1h,2h,5h,7h,7ah-cyclobuta[e]inden-3-yl}methyl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate)

3D Structure for NP0166702 ({2,2a,4a,7-tetrahydroxy-6,6,7b-trimethyl-1h,2h,5h,7h,7ah-cyclobuta[e]inden-3-yl}methyl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate)