NP-MRD: Showing NP-Card for 2a,4-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-octahydrocyclobuta[e]inden-2-yl 3-chloro-4,6-dihydroxy-2-methylbenzoate (NP0286366)

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Record Information

Version

2.0

Created at

2022-09-09 14:54:34 UTC

Updated at

2022-09-09 14:54:34 UTC

NP-MRD ID

NP0286366

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2a,4-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-octahydrocyclobuta[e]inden-2-yl 3-chloro-4,6-dihydroxy-2-methylbenzoate

Description

2A,4-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-decahydro-1H-cyclobuta[e]inden-2-yl 3-chloro-4,6-dihydroxy-2-methylbenzoate belongs to the class of organic compounds known as melleolides and analogues. Melleolides and analogues are compounds with a structure characterized by the presence of a 2-hydroxy-4-methoxy-6-methylbenzoic acid derivative linked to a 3,6,6,7b-tetramethyl-cyclobuta[e]indene moiety. Based on a literature review very few articles have been published on 2a,4-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-decahydro-1H-cyclobuta[e]inden-2-yl 3-chloro-4,6-dihydroxy-2-methylbenzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092216542D          

 31 34  0  0  0  0            999 V2000
   -1.1423   -1.8493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7036   -1.2447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5079   -1.4284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7509   -2.2168    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.0691   -0.8238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8734   -1.0075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8261   -0.0354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0218    0.1484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7788    0.9368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4606   -0.4563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6563   -0.2725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4133    0.5159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0950   -0.8772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7092   -0.6934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1480    0.0052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8467   -0.4336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0897    0.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2455    0.1279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9862   -0.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.7863   -0.4368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8032   -1.6935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309092216542D          

 31 34  0  0  0  0            999 V2000
   -1.1423   -1.8493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7036   -1.2447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5079   -1.4284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7509   -2.2168    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0286366

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(Cl)C(O)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C(O)C(CO)C12O

> <INCHI_IDENTIFIER>
InChI=1S/C23H31ClO7/c1-10-17(14(26)5-15(27)18(10)24)20(29)31-16-8-22(4)12-7-21(2,3)6-11(12)19(28)13(9-25)23(16,22)30/h5,11-13,16,19,25-28,30H,6-9H2,1-4H3

> <INCHI_KEY>
DEMXZQWBLZZLIK-UHFFFAOYSA-N

> <FORMULA>
C23H31ClO7

> <MOLECULAR_WEIGHT>
454.94

> <EXACT_MASS>
454.175831

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
47.61951327077575

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2a,4-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-decahydro-1H-cyclobuta[e]inden-2-yl 3-chloro-4,6-dihydroxy-2-methylbenzoate

> <JCHEM_LOGP>
3.5633157609999992

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.025567515359626

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.20897582401605

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6705950385499326

> <JCHEM_POLAR_SURFACE_AREA>
127.45000000000002

> <JCHEM_REFRACTIVITY>
114.34839999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2a,4-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-octahydrocyclobuta[e]inden-2-yl 3-chloro-4,6-dihydroxy-2-methylbenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.132  -3.452   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.180  -2.323   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.681  -2.666   0.000  0.00  0.00           C+0
HETATM    4 Cl   UNK     0      -5.135  -4.138   0.000  0.00  0.00          Cl+0
HETATM    5  C   UNK     0      -5.729  -1.538   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -7.230  -1.881   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -5.275  -0.066   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.774   0.277   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.321   1.749   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.726  -0.852   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.225  -0.509   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.771   0.963   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -0.177  -1.637   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.324  -1.294   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.143   0.010   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.447  -0.809   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.901   0.662   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.986  -0.867   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.058   0.239   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.441  -0.439   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.971   1.006   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.934  -0.815   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.223  -1.964   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.706  -2.228   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.887  -3.532   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.607  -4.893   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.348  -3.475   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.529  -4.779   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       0.990  -4.722   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.628  -2.113   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.499  -3.161   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    2   11                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   30                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18   30                                             
CONECT   17   16                                                            
CONECT   18   16   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20   24                                                       
CONECT   24   23   18   25                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   27   14   16   31                                             
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Value	Source
2a,4-Dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-decahydro-1H-cyclobuta[e]inden-2-yl 3-chloro-4,6-dihydroxy-2-methylbenzoic acid	Generator

Chemical Formula

C₂₃H₃₁ClO₇

Average Mass

454.9400 Da

Monoisotopic Mass

454.17583 Da

IUPAC Name

2a,4-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-decahydro-1H-cyclobuta[e]inden-2-yl 3-chloro-4,6-dihydroxy-2-methylbenzoate

Traditional Name

2a,4-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-octahydrocyclobuta[e]inden-2-yl 3-chloro-4,6-dihydroxy-2-methylbenzoate

CAS Registry Number

Not Available

SMILES

CC1=C(Cl)C(O)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C(O)C(CO)C12O

InChI Identifier

InChI=1S/C23H31ClO7/c1-10-17(14(26)5-15(27)18(10)24)20(29)31-16-8-22(4)12-7-21(2,3)6-11(12)19(28)13(9-25)23(16,22)30/h5,11-13,16,19,25-28,30H,6-9H2,1-4H3

InChI Key

DEMXZQWBLZZLIK-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as melleolides and analogues. Melleolides and analogues are compounds with a structure characterized by the presence of a 2-hydroxy-4-methoxy-6-methylbenzoic acid derivative linked to a 3,6,6,7b-tetramethyl-cyclobuta[e]indene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Melleolides and analogues

Alternative Parents

Substituents

Melleolide-skeleton
Diterpenoid
P-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
O-hydroxybenzoic acid ester
Dihydroxybenzoic acid
Halobenzoic acid or derivatives
3-halobenzoic acid or derivatives
Salicylic acid or derivatives
Benzoate ester
Benzoic acid or derivatives
Resorcinol
4-chlorophenol
2-chlorophenol
M-cresol
2-halophenol
4-halophenol
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Toluene
Phenol
Halobenzene
Chlorobenzene
Benzenoid
Monocyclic benzene moiety
Aryl halide
Aryl chloride
Vinylogous acid
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Cyclobutanol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organochloride
Organohalogen compound
Alcohol
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	3.56	ChemAxon
pKa (Strongest Acidic)	7.21	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	127.45 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	114.35 m³·mol⁻¹	ChemAxon
Polarizability	47.62 Å³	ChemAxon
Number of Rings	4	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

76799406

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2a,4-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-octahydrocyclobuta[e]inden-2-yl 3-chloro-4,6-dihydroxy-2-methylbenzoate (NP0286366)

MOL for NP0286366 (2a,4-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-octahydrocyclobuta[e]inden-2-yl 3-chloro-4,6-dihydroxy-2-methylbenzoate)

3D MOL for NP0286366 (2a,4-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-octahydrocyclobuta[e]inden-2-yl 3-chloro-4,6-dihydroxy-2-methylbenzoate)

3D SDF for NP0286366 (2a,4-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-octahydrocyclobuta[e]inden-2-yl 3-chloro-4,6-dihydroxy-2-methylbenzoate)

3D-SDF for NP0286366 (2a,4-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-octahydrocyclobuta[e]inden-2-yl 3-chloro-4,6-dihydroxy-2-methylbenzoate)

PDB for NP0286366 (2a,4-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-octahydrocyclobuta[e]inden-2-yl 3-chloro-4,6-dihydroxy-2-methylbenzoate)

3D PDB for NP0286366 (2a,4-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-octahydrocyclobuta[e]inden-2-yl 3-chloro-4,6-dihydroxy-2-methylbenzoate)

SMILES for NP0286366 (2a,4-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-octahydrocyclobuta[e]inden-2-yl 3-chloro-4,6-dihydroxy-2-methylbenzoate)

INCHI for NP0286366 (2a,4-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-octahydrocyclobuta[e]inden-2-yl 3-chloro-4,6-dihydroxy-2-methylbenzoate)

Structure for NP0286366 (2a,4-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-octahydrocyclobuta[e]inden-2-yl 3-chloro-4,6-dihydroxy-2-methylbenzoate)

3D Structure for NP0286366 (2a,4-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-octahydrocyclobuta[e]inden-2-yl 3-chloro-4,6-dihydroxy-2-methylbenzoate)