MiMeDB: Showing metabocard for (3S,4R)-3,4-dihydrophenanthrene-3,4-diol (MMDBc0054916)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:37:47 UTC

Update Date

2022-08-12 20:09:08 UTC

Metabolite ID

MMDBc0054916

Metabolite Identification

Common Name

(3S,4R)-3,4-dihydrophenanthrene-3,4-diol

Description

cis-3,4-Dihydroxy-3,4-dihydrophenanthrene belongs to the class of organic compounds known as phenanthrols. Phenanthrols are compounds containing a phenanthrene (or its hydrogenated derivative) to which a hydroxyl group is attached. cis-3,4-Dihydroxy-3,4-dihydrophenanthrene is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on cis-3,4-Dihydroxy-3,4-dihydrophenanthrene.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172221372D          

 18 20  0  0  1  0            999 V2000
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1105   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5230   -0.3020    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.0164    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  5  2  0  0  0  0
  8  7  2  0  0  0  0
  9  3  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  4  2  0  0  0  0
 11  9  1  0  0  0  0
 12  8  1  0  0  0  0
 13 10  2  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 14 13  1  0  0  0  0
 12 15  1  1  0  0  0
 14 16  1  1  0  0  0
 12 17  1  6  0  0  0
 14 18  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0054916

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@]1(O)C=CC2=C(C3=CC=CC=C3C=C2)[C@@]1([H])O

> <INCHI_IDENTIFIER>
InChI=1S/C14H12O2/c15-12-8-7-10-6-5-9-3-1-2-4-11(9)13(10)14(12)16/h1-8,12,14-16H/t12-,14-/m0/s1

> <INCHI_KEY>
FOTICWSJABVKPW-JSGCOSHPSA-N

> <FORMULA>
C14H12O2

> <MOLECULAR_WEIGHT>
212.248

> <EXACT_MASS>
212.083729626

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
22.625765865965096

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,4R)-3,4-dihydrophenanthrene-3,4-diol

> <JCHEM_LOGP>
1.985947908

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.735291918372496

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.245289167123271

> <JCHEM_PKA_STRONGEST_BASIC>
-3.377312454002446

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
63.830000000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4R)-3,4-dihydrophenanthrene-3,4-diol

> <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       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.206  -1.897   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       2.874  -1.897   0.000  0.00  0.00           O+0
HETATM   17  H   UNK     0      -0.976  -0.564   0.000  0.00  0.00           H+0
HETATM   18  H   UNK     0       1.334  -1.897   0.000  0.00  0.00           H+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    9                                                       
CONECT    4    2   11                                                       
CONECT    5    6    9                                                       
CONECT    6    5   10                                                       
CONECT    7    8   10                                                       
CONECT    8    7   12                                                       
CONECT    9    3    5   11                                                  
CONECT   10    6    7   13                                                  
CONECT   11    4    9   13                                                  
CONECT   12    8   14   15   17                                             
CONECT   13   10   11   14                                                  
CONECT   14   12   13   16   18                                             
CONECT   15   12                                                            
CONECT   16   14                                                            
CONECT   17   12                                                            
CONECT   18   14                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

Synonyms

Value	Source
(+)-cis-3,4-Dihydrophenanthrene-3,4-diol	ChEBI

Molecular Formula

C₁₄H₁₂O₂

Average Mass

212.248

Monoisotopic Mass

212.083729626

IUPAC Name

(3S,4R)-3,4-dihydrophenanthrene-3,4-diol

Traditional Name

(3S,4R)-3,4-dihydrophenanthrene-3,4-diol

CAS Registry Number

Not Available

SMILES

[H][C@]1(O)C=CC2=C(C3=CC=CC=C3C=C2)[C@@]1([H])O

InChI Identifier

InChI=1S/C14H12O2/c15-12-8-7-10-6-5-9-3-1-2-4-11(9)13(10)14(12)16/h1-8,12,14-16H/t12-,14-/m0/s1

InChI Key

FOTICWSJABVKPW-JSGCOSHPSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthrols. Phenanthrols are compounds containing a phenanthrene (or its hydrogenated derivative) to which a hydroxyl group is attached.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Phenanthrols

Direct Parent

Phenanthrols

Alternative Parents

Substituents

Phenanthrol
Hydrophenanthrene
Naphthalene
Secondary alcohol
1,2-diol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

cis-3,4-dihydrophenanthrene-3,4-diol (CHEBI:15386 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	1.99	ChemAxon
pKa (Strongest Acidic)	13.25	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	63.83 m³·mol⁻¹	ChemAxon
Polarizability	22.63 Å³	ChemAxon
Number of Rings	3	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_1_2) - 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
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	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
Bacteria	Proteobacteria	1	Human

Exposure Sources

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

389315

KEGG Compound ID

C04468

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440351

PDB ID

Not Available

ChEBI ID

15386

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 (3S,4R)-3,4-dihydrophenanthrene-3,4-diol (MMDBc0054916)

MOL for #<Metabolite:0x00007fdb066a2028>

3D MOL for #<Metabolite:0x00007fdb066a2028>

3D SDF for #<Metabolite:0x00007fdb066a2028>

3D-SDF for #<Metabolite:0x00007fdb066a2028>

PDB for #<Metabolite:0x00007fdb066a2028>

3D PDB for #<Metabolite:0x00007fdb066a2028>

SMILES for #<Metabolite:0x00007fdb066a2028>

INCHI for #<Metabolite:0x00007fdb066a2028>

Structure for #<Metabolite:0x00007fdb066a2028>

3D Structure for #<Metabolite:0x00007fdb066a2028>