NP-MRD: Showing NP-Card for {2,2a,4-trihydroxy-6,6,7b-trimethyl-octahydrocyclobuta[e]inden-3-yl}methyl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate (NP0315765)

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Record Information

Version

1.0

Created at

2022-09-11 14:33:35 UTC

Updated at

2022-09-11 14:33:35 UTC

NP-MRD ID

NP0315765

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{2,2a,4-trihydroxy-6,6,7b-trimethyl-octahydrocyclobuta[e]inden-3-yl}methyl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate

Description

{2,2A,4-trihydroxy-6,6,7b-trimethyl-decahydro-1H-cyclobuta[e]inden-3-yl}methyl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Based on a literature review very few articles have been published on {2,2a,4-trihydroxy-6,6,7b-trimethyl-decahydro-1H-cyclobuta[e]inden-3-yl}methyl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112216332D          

 32 35  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
    3.5671    2.4705    0.0000 O   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
    4.4330    0.9012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5497    0.0844    0.0000 C   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


  Mrv1652309112216332D          

 32 35  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>
NP0315765

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C(C(=O)OCC2C(O)C3CC(C)(C)CC3C3(C)CC(O)C23O)C(C)=C1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C24H33ClO7/c1-11-18(15(26)6-16(31-5)19(11)25)21(29)32-10-14-20(28)12-7-22(2,3)8-13(12)23(4)9-17(27)24(14,23)30/h6,12-14,17,20,26-28,30H,7-10H2,1-5H3

> <INCHI_KEY>
QDXBMSKCOMLNLC-UHFFFAOYSA-N

> <FORMULA>
C24H33ClO7

> <MOLECULAR_WEIGHT>
468.97

> <EXACT_MASS>
468.1914811

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
49.91873225962736

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
3.709209816999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.150441698666814

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.331055116573726

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0110289564792483

> <JCHEM_POLAR_SURFACE_AREA>
116.45000000000002

> <JCHEM_REFRACTIVITY>
118.83069999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
{2,2a,4-trihydroxy-6,6,7b-trimethyl-octahydrocyclobuta[e]inden-3-yl}methyl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         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  O   UNK     0       6.659   4.612   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.758   1.946   0.000  0.00  0.00           C+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  C   UNK     0       6.038   0.585   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.499   0.527   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.953  -0.944   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.195  -0.292   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.376   1.013   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.874   1.356   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.680   1.832   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.551   2.879   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -1.036   4.325   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.217   3.021   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.575   4.268   0.000  0.00  0.00           C+0
HETATM   32 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   31                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   29                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   27                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   17   21                                                       
CONECT   21   20   15   22                                                  
CONECT   22   21   23   24   27                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   12   22   28                                             
CONECT   28   27                                                            
CONECT   29    7   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29    3   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

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

Chemical Formula

C₂₄H₃₃ClO₇

Average Mass

468.9700 Da

Monoisotopic Mass

468.19148 Da

IUPAC Name

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

Traditional Name

{2,2a,4-trihydroxy-6,6,7b-trimethyl-octahydrocyclobuta[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)OCC2C(O)C3CC(C)(C)CC3C3(C)CC(O)C23O)C(C)=C1Cl

InChI Identifier

InChI=1S/C24H33ClO7/c1-11-18(15(26)6-16(31-5)19(11)25)21(29)32-10-14-20(28)12-7-22(2,3)8-13(12)23(4)9-17(27)24(14,23)30/h6,12-14,17,20,26-28,30H,7-10H2,1-5H3

InChI Key

QDXBMSKCOMLNLC-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 diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
O-hydroxybenzoic acid ester
P-methoxybenzoic acid or derivatives
Halobenzoic acid or derivatives
3-halobenzoic acid or derivatives
Salicylic acid or derivatives
Methoxyphenol
Benzoate ester
Benzoic acid or derivatives
Phenoxy compound
Methoxybenzene
Phenol ether
4-chlorophenol
M-cresol
4-halophenol
Benzoyl
Anisole
1-hydroxy-2-unsubstituted benzenoid
Toluene
Phenol
Halobenzene
Chlorobenzene
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Aryl halide
Aryl chloride
Vinylogous acid
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Cyclobutanol
Carboxylic acid ester
Polyol
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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	3.71	ChemAxon
pKa (Strongest Acidic)	9.33	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.45 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	118.83 m³·mol⁻¹	ChemAxon
Polarizability	49.92 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

163010407

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,4-trihydroxy-6,6,7b-trimethyl-octahydrocyclobuta[e]inden-3-yl}methyl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate (NP0315765)

MOL for NP0315765 ({2,2a,4-trihydroxy-6,6,7b-trimethyl-octahydrocyclobuta[e]inden-3-yl}methyl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate)

3D MOL for NP0315765 ({2,2a,4-trihydroxy-6,6,7b-trimethyl-octahydrocyclobuta[e]inden-3-yl}methyl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate)

3D SDF for NP0315765 ({2,2a,4-trihydroxy-6,6,7b-trimethyl-octahydrocyclobuta[e]inden-3-yl}methyl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate)

3D-SDF for NP0315765 ({2,2a,4-trihydroxy-6,6,7b-trimethyl-octahydrocyclobuta[e]inden-3-yl}methyl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate)

PDB for NP0315765 ({2,2a,4-trihydroxy-6,6,7b-trimethyl-octahydrocyclobuta[e]inden-3-yl}methyl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate)

3D PDB for NP0315765 ({2,2a,4-trihydroxy-6,6,7b-trimethyl-octahydrocyclobuta[e]inden-3-yl}methyl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate)

SMILES for NP0315765 ({2,2a,4-trihydroxy-6,6,7b-trimethyl-octahydrocyclobuta[e]inden-3-yl}methyl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate)

INCHI for NP0315765 ({2,2a,4-trihydroxy-6,6,7b-trimethyl-octahydrocyclobuta[e]inden-3-yl}methyl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate)

Structure for NP0315765 ({2,2a,4-trihydroxy-6,6,7b-trimethyl-octahydrocyclobuta[e]inden-3-yl}methyl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate)

3D Structure for NP0315765 ({2,2a,4-trihydroxy-6,6,7b-trimethyl-octahydrocyclobuta[e]inden-3-yl}methyl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate)