NP-MRD: Showing NP-Card for (2r,2as,7r,7as,7br)-2a,7-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate (NP0272969)

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Record Information

Version

2.0

Created at

2022-09-08 19:49:37 UTC

Updated at

2022-09-08 19:49:37 UTC

NP-MRD ID

NP0272969

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,2as,7r,7as,7br)-2a,7-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate

Description

(2R,2aS,7R,7aS,7bR)-2a,7-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1H,2H,2aH,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-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. (2r,2as,7r,7as,7br)-2a,7-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate is found in Armillaria. Based on a literature review very few articles have been published on (2R,2aS,7R,7aS,7bR)-2a,7-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1H,2H,2aH,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082221492D          

 32 35  0  0  1  0            999 V2000
   -4.1164   -1.7959    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
   -3.0691   -0.8238    0.0000 C   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  2  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  2  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
    2.6711   -0.4642    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0567   -1.1935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3548   -2.5601    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
    4.2702    0.5392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -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

     RDKit          3D

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M  END


  Mrv1652309082221492D          

 32 35  0  0  1  0            999 V2000
   -4.1164   -1.7959    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
   -3.0691   -0.8238    0.0000 C   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
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M  END
> <DATABASE_ID>
NP0272969

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C(C(=O)O[C@@H]2C[C@]3(C)[C@H]4[C@@H](O)C(C)(C)CC4C=C(CO)[C@]23O)C(C)=C1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C24H31ClO7/c1-11-17(14(27)7-15(31-5)19(11)25)21(29)32-16-9-23(4)18-12(8-22(2,3)20(18)28)6-13(10-26)24(16,23)30/h6-7,12,16,18,20,26-28,30H,8-10H2,1-5H3/t12?,16-,18-,20-,23-,24+/m1/s1

> <INCHI_KEY>
UMEBHTBMSZKYQM-NKKOJTMQSA-N

> <FORMULA>
C24H31ClO7

> <MOLECULAR_WEIGHT>
466.96

> <EXACT_MASS>
466.175831

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
48.208549320233814

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,2aS,7R,7aS,7bR)-2a,7-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1H,2H,2aH,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate

> <JCHEM_LOGP>
3.3907631076666664

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.917911414372899

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.32542111921384

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7659471047328115

> <JCHEM_POLAR_SURFACE_AREA>
116.45000000000002

> <JCHEM_REFRACTIVITY>
119.75529999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,2aS,7R,7aS,7bR)-2a,7-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1H,2H,4aH,5H,7H,7aH-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -7.684  -3.352   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -7.230  -1.881   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -5.729  -1.538   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.275  -0.066   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.774   0.277   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -3.321   1.749   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -2.726  -0.852   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.225  -0.509   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.771   0.963   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -0.177  -1.637   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.324  -1.294   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.143   0.010   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.447  -0.809   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.901   0.662   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.986  -0.867   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.706  -2.228   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.887  -3.532   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.348  -3.475   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.529  -4.779   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.990  -4.722   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.628  -2.113   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.499  -3.161   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.223  -1.964   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.441  -0.439   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.934  -0.815   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.971   1.006   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.058   0.239   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.794   1.756   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -3.180  -2.323   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.132  -3.452   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -4.681  -2.666   0.000  0.00  0.00           C+0
HETATM   32 Cl   UNK     0      -5.135  -4.138   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   21                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15   21                                             
CONECT   14   13                                                            
CONECT   15   13   16   27                                                  
CONECT   16   15   17   23                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   11   13   22                                             
CONECT   22   21                                                            
CONECT   23   16   24                                                       
CONECT   24   23   25   26   27                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   24   15   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
(2R,2AS,7R,7as,7BR)-2a,7-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1H,2H,2ah,4ah,5H,6H,7H,7ah,7BH-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoic acid	Generator

Chemical Formula

C₂₄H₃₁ClO₇

Average Mass

466.9600 Da

Monoisotopic Mass

466.17583 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C(C(=O)O[C@@H]2C[C@]3(C)[C@H]4[C@@H](O)C(C)(C)CC4C=C(CO)[C@]23O)C(C)=C1Cl

InChI Identifier

InChI=1S/C24H31ClO7/c1-11-17(14(27)7-15(31-5)19(11)25)21(29)32-16-9-23(4)18-12(8-22(2,3)20(18)28)6-13(10-26)24(16,23)30/h6-7,12,16,18,20,26-28,30H,8-10H2,1-5H3/t12?,16-,18-,20-,23-,24+/m1/s1

InChI Key

UMEBHTBMSZKYQM-NKKOJTMQSA-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	LOTUS Database	35616633

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
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
Monocarboxylic acid or derivatives
Ether
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

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

145720607

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,2as,7r,7as,7br)-2a,7-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate (NP0272969)

MOL for NP0272969 ((2r,2as,7r,7as,7br)-2a,7-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate)

3D MOL for NP0272969 ((2r,2as,7r,7as,7br)-2a,7-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate)

3D SDF for NP0272969 ((2r,2as,7r,7as,7br)-2a,7-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate)

3D-SDF for NP0272969 ((2r,2as,7r,7as,7br)-2a,7-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate)

PDB for NP0272969 ((2r,2as,7r,7as,7br)-2a,7-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate)

3D PDB for NP0272969 ((2r,2as,7r,7as,7br)-2a,7-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate)

SMILES for NP0272969 ((2r,2as,7r,7as,7br)-2a,7-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate)

INCHI for NP0272969 ((2r,2as,7r,7as,7br)-2a,7-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate)

Structure for NP0272969 ((2r,2as,7r,7as,7br)-2a,7-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate)

3D Structure for NP0272969 ((2r,2as,7r,7as,7br)-2a,7-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate)