MiMeDB: Showing metabocard for Pheofungin B (MMDBc0001178)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-14 19:31:12 UTC

Update Date

2022-08-31 06:17:43 UTC

Metabolite ID

MMDBc0001178

Metabolite Identification

Common Name

Pheofungin B

Description

Pheofungin B belongs to the class of organic compounds known as 7,8-dihydroxycoumarins. These are coumarins bearing two hydroxyl groups at the C7- and C8-positions of the coumarin skeleton, respectively. Based on a literature review a significant number of articles have been published on Pheofungin B.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305142121312D          

 24 27  0  0  0  0            999 V2000
   -1.7946    1.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9860    1.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5246    3.0434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4444    2.1079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3362    2.1079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2546    2.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5261    2.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9845    3.6671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8763    2.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0957    2.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2560    3.0434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1744    3.5111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1758    3.9789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6062    3.5111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7961    3.6671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4459    3.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7159    4.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3657    4.1348    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2546    4.4466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6864    2.5757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1463    4.1348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4459    5.3821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5261    4.4466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9058    2.5757    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  6  3  2  0  0  0  0
  6  4  1  0  0  0  0
  7  2  1  0  0  0  0
  7  5  2  0  0  0  0
  8  3  1  0  0  0  0
  9  5  1  0  0  0  0
 10  4  2  0  0  0  0
 11  7  1  0  0  0  0
 12  8  2  0  0  0  0
 12 10  1  0  0  0  0
 14  9  2  0  0  0  0
 15 11  2  0  0  0  0
 15 14  1  0  0  0  0
 16 11  1  0  0  0  0
 16 13  2  0  0  0  0
 17 13  1  0  0  0  0
 18 12  1  0  0  0  0
 18 13  1  0  0  0  0
 19  8  1  0  0  0  0
 20  9  1  0  0  0  0
 21 14  1  0  0  0  0
 22 17  2  0  0  0  0
 23 15  1  0  0  0  0
 23 17  1  0  0  0  0
 24 10  1  0  0  0  0
 24 16  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0001178

> <DATABASE_NAME>
MIME

> <SMILES>
CC1=CC(O)=C2NC3=C(SC2=C1)C1=C(OC3=O)C(O)=C(O)C=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C17H13NO5S/c1-6-3-8(19)12-10(4-6)24-16-11-7(2)5-9(20)14(21)15(11)23-17(22)13(16)18-12/h3-5,18-21H,1-2H3

> <INCHI_KEY>
OUSUUNRYQRUYFB-UHFFFAOYSA-N

> <FORMULA>
C17H13NO5S

> <MOLECULAR_WEIGHT>
343.35

> <EXACT_MASS>
343.051443697

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
34.888029679973705

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,4,8-trihydroxy-1,10-dimethyl-6,7-dihydro-5-oxa-12-thia-7-azatetraphen-6-one

> <ALOGPS_LOGP>
3.01

> <JCHEM_LOGP>
3.2885982793333337

> <ALOGPS_LOGS>
-3.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.817468290330936

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.831698928389441

> <JCHEM_PKA_STRONGEST_BASIC>
-4.642056819844137

> <JCHEM_POLAR_SURFACE_AREA>
99.02000000000001

> <JCHEM_REFRACTIVITY>
94.06909999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.71e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4,8-trihydroxy-1,10-dimethyl-7H-5-oxa-12-thia-7-azatetraphen-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 14-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-MAY-21         0                                  
HETATM    1  C   UNK     0      -3.350   3.062   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.707   3.062   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.846   5.681   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.830   3.935   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.228   3.935   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.342   4.226   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.715   4.226   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.838   6.845   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.236   5.099   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.179   5.099   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.211   5.681   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.326   6.554   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.195   7.427   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.732   6.554   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.219   6.845   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.699   5.972   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.203   8.591   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       0.683   7.718   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0      -2.342   8.300   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       8.748   4.808   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       7.740   7.718   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.699  10.047   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.715   8.300   0.000  0.00  0.00           O+0
HETATM   24  S   UNK     0       1.691   4.808   0.000  0.00  0.00           S+0
CONECT    1    6                                                            
CONECT    2    7                                                            
CONECT    3    6    8                                                       
CONECT    4    6   10                                                       
CONECT    5    7    9                                                       
CONECT    6    1    3    4                                                  
CONECT    7    2    5   11                                                  
CONECT    8    3   12   19                                                  
CONECT    9    5   14   20                                                  
CONECT   10    4   12   24                                                  
CONECT   11    7   15   16                                                  
CONECT   12    8   10   18                                                  
CONECT   13   16   17   18                                                  
CONECT   14    9   15   21                                                  
CONECT   15   11   14   23                                                  
CONECT   16   11   13   24                                                  
CONECT   17   13   22   23                                                  
CONECT   18   12   13                                                       
CONECT   19    8                                                            
CONECT   20    9                                                            
CONECT   21   14                                                            
CONECT   22   17                                                            
CONECT   23   15   17                                                       
CONECT   24   10   16                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

Synonyms

Not Available

Molecular Formula

C₁₇H₁₃NO₅S

Average Mass

343.35

Monoisotopic Mass

343.051443697

IUPAC Name

3,4,8-trihydroxy-1,10-dimethyl-6,7-dihydro-5-oxa-12-thia-7-azatetraphen-6-one

Traditional Name

3,4,8-trihydroxy-1,10-dimethyl-7H-5-oxa-12-thia-7-azatetraphen-6-one

CAS Registry Number

Not Available

SMILES

CC1=CC(O)=C2NC3=C(SC2=C1)C1=C(OC3=O)C(O)=C(O)C=C1C

InChI Identifier

InChI=1S/C17H13NO5S/c1-6-3-8(19)12-10(4-6)24-16-11-7(2)5-9(20)14(21)15(11)23-17(22)13(16)18-12/h3-5,18-21H,1-2H3

InChI Key

OUSUUNRYQRUYFB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7,8-dihydroxycoumarins. These are coumarins bearing two hydroxyl groups at the C7- and C8-positions of the coumarin skeleton, respectively.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Hydroxycoumarins

Direct Parent

7,8-dihydroxycoumarins

Alternative Parents

Substituents

7,8-dihydroxycoumarin
Diarylthioether
Benzopyran
Benzothiazine
1-benzopyran
Aryl thioether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
1-hydroxy-4-unsubstituted benzenoid
Para-thiazine
Vinylogous thioester
Primary aromatic amine
Pyran
Benzenoid
Heteroaromatic compound
Lactone
Oxacycle
Azacycle
Polyol
Organoheterocyclic compound
Thioether
Secondary amine
Organonitrogen compound
Organic nitrogen compound
Organooxygen compound
Organic oxygen compound
Amine
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.17 g/L	ALOGPS
logP	3.01	ALOGPS
logP	3.29	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	7.83	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	99.02 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	94.07 m³·mol⁻¹	ChemAxon
Polarizability	34.89 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

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

Metabolic Reactions

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

78434603

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

56641606

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 Pheofungin B (MMDBc0001178)

MOL for #<Metabolite:0x00005645c9ada8f8>

3D MOL for #<Metabolite:0x00005645c9ada8f8>

3D SDF for #<Metabolite:0x00005645c9ada8f8>

3D-SDF for #<Metabolite:0x00005645c9ada8f8>

PDB for #<Metabolite:0x00005645c9ada8f8>

3D PDB for #<Metabolite:0x00005645c9ada8f8>

SMILES for #<Metabolite:0x00005645c9ada8f8>

INCHI for #<Metabolite:0x00005645c9ada8f8>

Structure for #<Metabolite:0x00005645c9ada8f8>

3D Structure for #<Metabolite:0x00005645c9ada8f8>