MiMeDB: Showing metabocard for Judeol (MMDBc0015756)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 06:31:52 UTC

Update Date

2022-12-15 22:51:45 UTC

Metabolite ID

MMDBc0015756

Metabolite Identification

Common Name

Judeol

Description

4-hydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1H,2H,4H,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-2-yl 2,3,4-trihydroxy-6-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. 4-hydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1H,2H,4H,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-2-yl 2,3,4-trihydroxy-6-methylbenzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152108312D          

 30 33  0  0  0  0            999 V2000
   -0.2606   -2.2664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3497    0.5391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8336    1.5152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6532    1.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6261   -1.8455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4330   -0.0762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8090    1.1039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7115    0.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9182   -1.5842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8218   -1.6617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6202   -0.2176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3570   -0.8855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2346    0.5118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1874   -1.2408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2727    0.2826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5788   -0.8733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9714   -0.1562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1815   -0.9162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9444   -0.4524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1401   -0.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2254   -0.6896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5497    0.7406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4102    0.5424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3039   -2.3135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9917   -1.4246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5671   -1.6455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5056    0.1522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8971    0.5197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7867   -1.2942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4685    0.0988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10  1  1  0  0  0  0
 10  5  2  0  0  0  0
 11  6  1  0  0  0  0
 12  9  1  0  0  0  0
 13  7  1  0  0  0  0
 13 11  1  0  0  0  0
 14  5  1  0  0  0  0
 15  8  1  0  0  0  0
 16 10  1  0  0  0  0
 17 12  2  0  0  0  0
 17 15  1  0  0  0  0
 18 11  1  0  0  0  0
 18 12  1  0  0  0  0
 19 14  2  0  0  0  0
 20 16  2  0  0  0  0
 20 19  1  0  0  0  0
 21 16  1  0  0  0  0
 22  2  1  0  0  0  0
 22  3  1  0  0  0  0
 22  6  1  0  0  0  0
 22  7  1  0  0  0  0
 23  4  1  0  0  0  0
 23  8  1  0  0  0  0
 23 13  1  0  0  0  0
 23 17  1  0  0  0  0
 24  9  1  0  0  0  0
 25 14  1  0  0  0  0
 26 18  1  0  0  0  0
 27 19  1  0  0  0  0
 28 20  1  0  0  0  0
 29 21  2  0  0  0  0
 30 15  1  0  0  0  0
 30 21  1  0  0  0  0
M  END


  Mrv1652305152108312D          

 30 33  0  0  0  0            999 V2000
   -0.2606   -2.2664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3497    0.5391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8336    1.5152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6532    1.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6261   -1.8455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4330   -0.0762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8090    1.1039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7115    0.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9182   -1.5842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8218   -1.6617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6202   -0.2176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3570   -0.8855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2346    0.5118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1874   -1.2408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2727    0.2826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5788   -0.8733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9714   -0.1562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1815   -0.9162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9444   -0.4524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1401   -0.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2254   -0.6896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5497    0.7406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4102    0.5424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3039   -2.3135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9917   -1.4246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5671   -1.6455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5056    0.1522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8971    0.5197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7867   -1.2942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4685    0.0988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10  1  1  0  0  0  0
 10  5  2  0  0  0  0
 11  6  1  0  0  0  0
 12  9  1  0  0  0  0
 13  7  1  0  0  0  0
 13 11  1  0  0  0  0
 14  5  1  0  0  0  0
 15  8  1  0  0  0  0
 16 10  1  0  0  0  0
 17 12  2  0  0  0  0
 17 15  1  0  0  0  0
 18 11  1  0  0  0  0
 18 12  1  0  0  0  0
 19 14  2  0  0  0  0
 20 16  2  0  0  0  0
 20 19  1  0  0  0  0
 21 16  1  0  0  0  0
 22  2  1  0  0  0  0
 22  3  1  0  0  0  0
 22  6  1  0  0  0  0
 22  7  1  0  0  0  0
 23  4  1  0  0  0  0
 23  8  1  0  0  0  0
 23 13  1  0  0  0  0
 23 17  1  0  0  0  0
 24  9  1  0  0  0  0
 25 14  1  0  0  0  0
 26 18  1  0  0  0  0
 27 19  1  0  0  0  0
 28 20  1  0  0  0  0
 29 21  2  0  0  0  0
 30 15  1  0  0  0  0
 30 21  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0015756

> <DATABASE_NAME>
MIME

> <SMILES>
CC1=CC(O)=C(O)C(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C(O)C(CO)=C12

> <INCHI_IDENTIFIER>
InChI=1S/C23H30O7/c1-10-5-14(25)19(27)20(28)16(10)21(29)30-15-8-23(4)13-7-22(2,3)6-11(13)18(26)12(9-24)17(15)23/h5,11,13,15,18,24-28H,6-9H2,1-4H3

> <INCHI_KEY>
PTVABGVMGJFKGM-UHFFFAOYSA-N

> <FORMULA>
C23H30O7

> <MOLECULAR_WEIGHT>
418.486

> <EXACT_MASS>
418.199153306

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
45.22875397439228

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1H,2H,4H,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-2-yl 2,3,4-trihydroxy-6-methylbenzoate

> <ALOGPS_LOGP>
2.32

> <JCHEM_LOGP>
3.1410860739999995

> <ALOGPS_LOGS>
-4.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.726804465795912

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.77853428740405

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7730707526503604

> <JCHEM_POLAR_SURFACE_AREA>
127.45

> <JCHEM_REFRACTIVITY>
110.96239999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.17e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1H,2H,4H,4aH,5H,7H,7aH-cyclobuta[e]inden-2-yl 2,3,4-trihydroxy-6-methylbenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0      -0.486  -4.231   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.986   1.006   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.023   2.828   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.953   2.484   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.035  -3.445   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.275  -0.142   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.110   2.061   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.195   1.832   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.581  -2.957   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.534  -3.102   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.758  -0.406   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.400  -1.653   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.038   0.955   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.083  -2.316   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.376   0.527   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.080  -1.630   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.680  -0.292   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.939  -1.710   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.630  -0.845   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.128  -0.502   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.421  -1.287   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.493   1.382   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.499   1.013   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.301  -4.318   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -5.584  -2.659   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       6.659  -3.072   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -4.677   0.284   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -1.675   0.970   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       1.469  -2.416   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       0.874   0.184   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   22                                                            
CONECT    3   22                                                            
CONECT    4   23                                                            
CONECT    5   10   14                                                       
CONECT    6   11   22                                                       
CONECT    7   13   22                                                       
CONECT    8   15   23                                                       
CONECT    9   12   24                                                       
CONECT   10    1    5   16                                                  
CONECT   11    6   13   18                                                  
CONECT   12    9   17   18                                                  
CONECT   13    7   11   23                                                  
CONECT   14    5   19   25                                                  
CONECT   15    8   17   30                                                  
CONECT   16   10   20   21                                                  
CONECT   17   12   15   23                                                  
CONECT   18   11   12   26                                                  
CONECT   19   14   20   27                                                  
CONECT   20   16   19   28                                                  
CONECT   21   16   29   30                                                  
CONECT   22    2    3    6    7                                             
CONECT   23    4    8   13   17                                             
CONECT   24    9                                                            
CONECT   25   14                                                            
CONECT   26   18                                                            
CONECT   27   19                                                            
CONECT   28   20                                                            
CONECT   29   21                                                            
CONECT   30   15   21                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

Synonyms

Value	Source
4-Hydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1H,2H,4H,4ah,5H,6H,7H,7ah,7BH-cyclobuta[e]inden-2-yl 2,3,4-trihydroxy-6-methylbenzoic acid	Generator

Molecular Formula

C₂₃H₃₀O₇

Average Mass

418.486

Monoisotopic Mass

418.199153306

IUPAC Name

4-hydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1H,2H,4H,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-2-yl 2,3,4-trihydroxy-6-methylbenzoate

Traditional Name

4-hydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1H,2H,4H,4aH,5H,7H,7aH-cyclobuta[e]inden-2-yl 2,3,4-trihydroxy-6-methylbenzoate

CAS Registry Number

Not Available

SMILES

CC1=CC(O)=C(O)C(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C(O)C(CO)=C12

InChI Identifier

InChI=1S/C23H30O7/c1-10-5-14(25)19(27)20(28)16(10)21(29)30-15-8-23(4)13-7-22(2,3)6-11(13)18(26)12(9-24)17(15)23/h5,11,13,15,18,24-28H,6-9H2,1-4H3

InChI Key

PTVABGVMGJFKGM-UHFFFAOYSA-N

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
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
O-hydroxybenzoic acid ester
Benzoate ester
Salicylic acid or derivatives
Benzenetriol
Benzoic acid or derivatives
Pyrogallol derivative
M-cresol
Benzoyl
P-cresol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Toluene
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Polyol
Alcohol
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.042 g/L	ALOGPS
logP	2.32	ALOGPS
logP	3.14	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	8.78	ChemAxon
pKa (Strongest Basic)	-2.8	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	110.96 m³·mol⁻¹	ChemAxon
Polarizability	45.23 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

Spectra

Not Available

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Basidiomycota	3	Human feces	Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78443842

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

78173191

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for Judeol (MMDBc0015756)

MOL for #<Metabolite:0x00007fecd87fe488>

3D MOL for #<Metabolite:0x00007fecd87fe488>

3D SDF for #<Metabolite:0x00007fecd87fe488>

3D-SDF for #<Metabolite:0x00007fecd87fe488>

PDB for #<Metabolite:0x00007fecd87fe488>

3D PDB for #<Metabolite:0x00007fecd87fe488>

SMILES for #<Metabolite:0x00007fecd87fe488>

INCHI for #<Metabolite:0x00007fecd87fe488>

Structure for #<Metabolite:0x00007fecd87fe488>

3D Structure for #<Metabolite:0x00007fecd87fe488>