MiMeDB: Showing metabocard for Aculeatusquinone B (MMDBc0015027)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 05:56:09 UTC

Update Date

2022-08-31 06:38:39 UTC

Metabolite ID

MMDBc0015027

Metabolite Identification

Common Name

Aculeatusquinone B

Description

Aculeatusquinone B belongs to the class of organic compounds known as p-xylenols. These are aromatic compounds that contain a p-xylenol moiety, which is a monocyclic benzene carrying exactly two methyl groups at the 1- and 4-positions, and at least one hydroxyl group. Based on a literature review a significant number of articles have been published on Aculeatusquinone B.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152107562D          

 24 25  0  0  1  0            999 V2000
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7111    1.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5236   -0.0935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2414    0.6817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  0  0  0  0
  8  6  2  0  0  0  0
  8  7  1  0  0  0  0
  9  2  1  0  0  0  0
 10  3  1  0  0  0  0
 11  6  1  0  0  0  0
 11  9  2  0  0  0  0
 12  7  2  0  0  0  0
 12  9  1  0  0  0  0
 13 10  2  0  0  0  0
 14 10  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  1  0  0  0  0
 17  4  1  1  0  0  0
 17 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 11  1  0  0  0  0
 19 13  1  0  0  0  0
 20 14  2  0  0  0  0
 21 15  2  0  0  0  0
 22  5  1  0  0  0  0
 17 22  1  6  0  0  0
 23 12  1  0  0  0  0
 16 23  1  1  0  0  0
 16 24  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0015027

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]1(OC2=CC(C)=CC(O)=C2C)C(=O)C(C)=C(O)C(=O)[C@@]1(C)OC

> <INCHI_IDENTIFIER>
InChI=1S/C17H20O6/c1-8-6-11(18)9(2)12(7-8)23-16-14(20)10(3)13(19)15(21)17(16,4)22-5/h6-7,16,18-19H,1-5H3/t16-,17-/m1/s1

> <INCHI_KEY>
NRPVNOLWZYAELE-IAGOWNOFSA-N

> <FORMULA>
C17H20O6

> <MOLECULAR_WEIGHT>
320.341

> <EXACT_MASS>
320.125988364

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
32.41781321267986

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S,6S)-3-hydroxy-6-(3-hydroxy-2,5-dimethylphenoxy)-5-methoxy-2,5-dimethylcyclohex-2-ene-1,4-dione

> <ALOGPS_LOGP>
1.92

> <JCHEM_LOGP>
3.246442527666666

> <ALOGPS_LOGS>
-2.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.997355727495325

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.678302008346818

> <JCHEM_PKA_STRONGEST_BASIC>
-4.14077950560757

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
84.7474

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.76e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5S,6S)-3-hydroxy-6-(3-hydroxy-2,5-dimethylphenoxy)-5-methoxy-2,5-dimethylcyclohex-2-ene-1,4-dione

> <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       4.001   8.470   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.194   2.987   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.711  -0.175   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.184   1.273   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   24  H   UNK     0       2.667   3.080   0.000  0.00  0.00           H+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4   17                                                            
CONECT    5   22                                                            
CONECT    6    8   11                                                       
CONECT    7    8   12                                                       
CONECT    8    1    6    7                                                  
CONECT    9    2   11   12                                                  
CONECT   10    3   13   14                                                  
CONECT   11    6    9   18                                                  
CONECT   12    7    9   23                                                  
CONECT   13   10   15   19                                                  
CONECT   14   10   16   20                                                  
CONECT   15   13   17   21                                                  
CONECT   16   14   17   23   24                                             
CONECT   17    4   15   16   22                                             
CONECT   18   11                                                            
CONECT   19   13                                                            
CONECT   20   14                                                            
CONECT   21   15                                                            
CONECT   22    5   17                                                       
CONECT   23   12   16                                                       
CONECT   24   16                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

Synonyms

Not Available

Molecular Formula

C₁₇H₂₀O₆

Average Mass

320.341

Monoisotopic Mass

320.125988364

IUPAC Name

(5S,6S)-3-hydroxy-6-(3-hydroxy-2,5-dimethylphenoxy)-5-methoxy-2,5-dimethylcyclohex-2-ene-1,4-dione

Traditional Name

(5S,6S)-3-hydroxy-6-(3-hydroxy-2,5-dimethylphenoxy)-5-methoxy-2,5-dimethylcyclohex-2-ene-1,4-dione

CAS Registry Number

Not Available

SMILES

[H][C@@]1(OC2=CC(C)=CC(O)=C2C)C(=O)C(C)=C(O)C(=O)[C@@]1(C)OC

InChI Identifier

InChI=1S/C17H20O6/c1-8-6-11(18)9(2)12(7-8)23-16-14(20)10(3)13(19)15(21)17(16,4)22-5/h6-7,16,18-19H,1-5H3/t16-,17-/m1/s1

InChI Key

NRPVNOLWZYAELE-IAGOWNOFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as p-xylenols. These are aromatic compounds that contain a p-xylenol moiety, which is a monocyclic benzene carrying exactly two methyl groups at the 1- and 4-positions, and at least one hydroxyl group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Xylenes

Direct Parent

p-Xylenols

Alternative Parents

Substituents

P-xylenol
Phenoxy compound
M-cresol
O-cresol
Phenol ether
P-xylene
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Cyclohexenone
Vinylogous acid
Ketone
Cyclic ketone
Dialkyl ether
Ether
Enol
Organic oxygen compound
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.48 g/L	ALOGPS
logP	1.92	ALOGPS
logP	3.25	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	4.68	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	84.75 m³·mol⁻¹	ChemAxon
Polarizability	32.42 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Biological Properties

Cellular Locations

Not Available

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

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

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	Ascomycota	1	Human feces	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	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

29215666

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71606915

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

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 Aculeatusquinone B (MMDBc0015027)

MOL for #<Metabolite:0x00007f12200230a8>

3D MOL for #<Metabolite:0x00007f12200230a8>

3D SDF for #<Metabolite:0x00007f12200230a8>

3D-SDF for #<Metabolite:0x00007f12200230a8>

PDB for #<Metabolite:0x00007f12200230a8>

3D PDB for #<Metabolite:0x00007f12200230a8>

SMILES for #<Metabolite:0x00007f12200230a8>

INCHI for #<Metabolite:0x00007f12200230a8>

Structure for #<Metabolite:0x00007f12200230a8>

3D Structure for #<Metabolite:0x00007f12200230a8>