MiMeDB: Showing metabocard for (4S,8R)-2,13,16,20-tetrahydroxy-7,9-dioxapentacyclo[10.8.0.0(3,10).0(4,8).0(14,19)]icosa-1(12),2,5,10,13,16,19-heptaen-18-one (MMDBc0054960)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:38:39 UTC

Update Date

2022-08-12 20:09:10 UTC

Metabolite ID

MMDBc0054960

Metabolite Identification

Common Name

(4S,8R)-2,13,16,20-tetrahydroxy-7,9-dioxapentacyclo[10.8.0.0(3,10).0(4,8).0(14,19)]icosa-1(12),2,5,10,13,16,19-heptaen-18-one

Description

(4S,8R)-2,13,16,20-tetrahydroxy-7,9-dioxapentacyclo[10.8.0.0³,¹⁰.0⁴,⁸.0¹⁴,¹⁹]icosa-1,3(10),5,11,13,16,19-heptaen-18-one belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. Based on a literature review very few articles have been published on (4S,8R)-2,13,16,20-tetrahydroxy-7,9-dioxapentacyclo[10.8.0.0³,¹⁰.0⁴,⁸.0¹⁴,¹⁹]icosa-1,3(10),5,11,13,16,19-heptaen-18-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172221382D          

 27 31  0  0  1  0            999 V2000
    3.2351    3.9124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4906    3.5570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3179    2.4044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8644    3.7247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4846    2.0306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9723    2.9068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8032    3.3141    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5556    2.7199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1390    2.5330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1021    4.0402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7223    2.3461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4477    3.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6144    3.1640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0311    3.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9013    2.2175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6854    3.8533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2688    3.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4097    2.5890    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.7346    2.5913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9942    4.8581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0092    1.3996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5775    4.6712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1608    4.4843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5985    2.7391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9778    1.9907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1966    4.0392    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0163    1.8638    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  6  3  1  0  0  0  0
  6  4  2  0  0  0  0
  7  1  1  0  0  0  0
  8  3  1  0  0  0  0
  9  5  2  0  0  0  0
 10  4  1  0  0  0  0
 11  5  1  0  0  0  0
 12  8  1  0  0  0  0
 12 10  1  0  0  0  0
 13  7  1  0  0  0  0
 13 11  2  0  0  0  0
 14  9  1  0  0  0  0
 15  8  2  0  0  0  0
 15  9  1  0  0  0  0
 16 12  2  0  0  0  0
 16 14  1  0  0  0  0
 17 13  1  0  0  0  0
 17 14  2  0  0  0  0
 18  7  1  0  0  0  0
 19  6  1  0  0  0  0
 20 10  2  0  0  0  0
 21 15  1  0  0  0  0
 22 16  1  0  0  0  0
 23 17  1  0  0  0  0
 24  2  1  0  0  0  0
 24 18  1  0  0  0  0
 25 11  1  0  0  0  0
 25 18  1  0  0  0  0
  7 26  1  6  0  0  0
 18 27  1  6  0  0  0
M  END


  Mrv1652306172221382D          

 27 31  0  0  1  0            999 V2000
    3.2351    3.9124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4906    3.5570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3179    2.4044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8644    3.7247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4846    2.0306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9723    2.9068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8032    3.3141    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5556    2.7199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1390    2.5330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1021    4.0402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7223    2.3461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4477    3.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6144    3.1640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0311    3.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9013    2.2175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6854    3.8533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2688    3.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4097    2.5890    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.7346    2.5913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9942    4.8581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0092    1.3996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5775    4.6712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1608    4.4843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5985    2.7391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9778    1.9907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1966    4.0392    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0163    1.8638    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  6  3  1  0  0  0  0
  6  4  2  0  0  0  0
  7  1  1  0  0  0  0
  8  3  1  0  0  0  0
  9  5  2  0  0  0  0
 10  4  1  0  0  0  0
 11  5  1  0  0  0  0
 12  8  1  0  0  0  0
 12 10  1  0  0  0  0
 13  7  1  0  0  0  0
 13 11  2  0  0  0  0
 14  9  1  0  0  0  0
 15  8  2  0  0  0  0
 15  9  1  0  0  0  0
 16 12  2  0  0  0  0
 16 14  1  0  0  0  0
 17 13  1  0  0  0  0
 17 14  2  0  0  0  0
 18  7  1  0  0  0  0
 19  6  1  0  0  0  0
 20 10  2  0  0  0  0
 21 15  1  0  0  0  0
 22 16  1  0  0  0  0
 23 17  1  0  0  0  0
 24  2  1  0  0  0  0
 24 18  1  0  0  0  0
 25 11  1  0  0  0  0
 25 18  1  0  0  0  0
  7 26  1  6  0  0  0
 18 27  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0054960

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@]12OC=C[C@@]1([H])C1=C(O2)C=C2C(O)=C3CC(O)=CC(=O)C3=C(O)C2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C18H12O7/c19-6-3-8-12(10(20)4-6)16(22)14-9(15(8)21)5-11-13(17(14)23)7-1-2-24-18(7)25-11/h1-2,4-5,7,18-19,21-23H,3H2/t7-,18+/m0/s1

> <INCHI_KEY>
DWIQZFOGDHNQGC-ULCDLSAGSA-N

> <FORMULA>
C18H12O7

> <MOLECULAR_WEIGHT>
340.287

> <EXACT_MASS>
340.058302726

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
32.707491629578755

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S,8R)-2,13,16,20-tetrahydroxy-7,9-dioxapentacyclo[10.8.0.0^{3,10}.0^{4,8}.0^{14,19}]icosa-1(12),2,5,10,13,16,19-heptaen-18-one

> <JCHEM_LOGP>
2.131162648666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.785653194509834

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.852545449537371

> <JCHEM_PKA_STRONGEST_BASIC>
-4.878869124789545

> <JCHEM_POLAR_SURFACE_AREA>
116.45000000000002

> <JCHEM_REFRACTIVITY>
88.3014

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4S,8R)-2,13,16,20-tetrahydroxy-7,9-dioxapentacyclo[10.8.0.0^{3,10}.0^{4,8}.0^{14,19}]icosa-1(12),2,5,10,13,16,19-heptaen-18-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0       6.039   7.303   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.649   6.640   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.527   4.488   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.547   6.953   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.238   3.790   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.748   5.426   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.099   6.186   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.104   5.077   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.459   4.728   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      15.124   7.542   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.815   4.379   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.902   6.604   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.614   5.906   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.258   6.255   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.882   4.139   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.479   7.193   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.835   6.844   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.365   4.833   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      18.171   4.837   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      14.922   9.068   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      13.084   2.613   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      12.278   8.720   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       9.634   8.371   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       4.850   5.113   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       7.425   3.716   0.000  0.00  0.00           O+0
HETATM   26  H   UNK     0       7.834   7.540   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0       5.630   3.479   0.000  0.00  0.00           H+0
CONECT    1    2    7                                                       
CONECT    2    1   24                                                       
CONECT    3    6    8                                                       
CONECT    4    6   10                                                       
CONECT    5    9   11                                                       
CONECT    6    3    4   19                                                  
CONECT    7    1   13   18   26                                             
CONECT    8    3   12   15                                                  
CONECT    9    5   14   15                                                  
CONECT   10    4   12   20                                                  
CONECT   11    5   13   25                                                  
CONECT   12    8   10   16                                                  
CONECT   13    7   11   17                                                  
CONECT   14    9   16   17                                                  
CONECT   15    8    9   21                                                  
CONECT   16   12   14   22                                                  
CONECT   17   13   14   23                                                  
CONECT   18    7   24   25   27                                             
CONECT   19    6                                                            
CONECT   20   10                                                            
CONECT   21   15                                                            
CONECT   22   16                                                            
CONECT   23   17                                                            
CONECT   24    2   18                                                       
CONECT   25   11   18                                                       
CONECT   26    7                                                            
CONECT   27   18                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

Synonyms

Not Available

Molecular Formula

C₁₈H₁₂O₇

Average Mass

340.287

Monoisotopic Mass

340.058302726

IUPAC Name

(4S,8R)-2,13,16,20-tetrahydroxy-7,9-dioxapentacyclo[10.8.0.0^{3,10}.0^{4,8}.0^{14,19}]icosa-1(12),2,5,10,13,16,19-heptaen-18-one

Traditional Name

(4S,8R)-2,13,16,20-tetrahydroxy-7,9-dioxapentacyclo[10.8.0.0^{3,10}.0^{4,8}.0^{14,19}]icosa-1(12),2,5,10,13,16,19-heptaen-18-one

CAS Registry Number

Not Available

SMILES

[H][C@]12OC=C[C@@]1([H])C1=C(O2)C=C2C(O)=C3CC(O)=CC(=O)C3=C(O)C2=C1O

InChI Identifier

InChI=1S/C18H12O7/c19-6-3-8-12(10(20)4-6)16(22)14-9(15(8)21)5-11-13(17(14)23)7-1-2-24-18(7)25-11/h1-2,4-5,7,18-19,21-23H,3H2/t7-,18+/m0/s1

InChI Key

DWIQZFOGDHNQGC-ULCDLSAGSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthofurans

Sub Class

Not Available

Direct Parent

Naphthofurans

Alternative Parents

Substituents

Naphthofuran
1-naphthol
Naphthalene
Coumaran
Aryl ketone
Hydroquinone
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Vinylogous acid
Dihydrofuran
Ketone
Oxacycle
Polyol
Enol
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
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
logP	2.13	ChemAxon
pKa (Strongest Acidic)	4.85	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.45 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	88.3 m³·mol⁻¹	ChemAxon
Polarizability	32.71 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-10	View Spectrum

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	2

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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for (4S,8R)-2,13,16,20-tetrahydroxy-7,9-dioxapentacyclo[10.8.0.0(3,10).0(4,8).0(14,19)]icosa-1(12),2,5,10,13,16,19-heptaen-18-one (MMDBc0054960)

MOL for #<Metabolite:0x00007fecd91047d0>

3D MOL for #<Metabolite:0x00007fecd91047d0>

3D SDF for #<Metabolite:0x00007fecd91047d0>

3D-SDF for #<Metabolite:0x00007fecd91047d0>

PDB for #<Metabolite:0x00007fecd91047d0>

3D PDB for #<Metabolite:0x00007fecd91047d0>

SMILES for #<Metabolite:0x00007fecd91047d0>

INCHI for #<Metabolite:0x00007fecd91047d0>

Structure for #<Metabolite:0x00007fecd91047d0>

3D Structure for #<Metabolite:0x00007fecd91047d0>