MiMeDB: Showing metabocard for Psoracorylifol C (MMDBc0001910)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-14 20:24:35 UTC

Update Date

2025-10-07 16:04:32 UTC

Metabolite ID

MMDBc0001910

Metabolite Identification

Common Name

Psoracorylifol C

Description

Psoracorylifol C is a member of the 6,8-dihydroxy-1,2-benzodioxole chemical class. This metabolite has garnered attention for its potential biological activities, although literature on its specific effects and applications remains limited. Notably, recent studies have focused on the total syntheses of related compounds, including the 6,8-DOBCO framework found in psoracorylifol B and ent-psoracorylifol C, highlighting their antimicrobial properties and synthetic accessibility. The first asymmetric total syntheses of these compounds demonstrated promising yields, with ent-Psoracorylifol C being synthesized with a 4.3% yield in 16 steps (PMID:24819702 ). Furthermore, a synopsis of various synthetic approaches has been provided, detailing the methodologies employed to access these complex natural products (PMID:26954099 ). Despite the progress in synthetic chemistry, further exploration of Psoracorylifol C's biological functions and therapeutic potentials is warranted, as current knowledge remains sparse.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305142122242D          

 23 25  0  0  1  0            999 V2000
    1.2522    2.8059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1905   -1.1493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5836   -1.4672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7710    1.7520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9667    2.3934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2876    2.4183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9076    1.1308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0309    2.7762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6509    1.4888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3247    0.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9667    0.0818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9788   -0.9061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2259    1.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7125    2.3115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5174    1.2376    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1624    1.7520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9667    1.5684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1624   -0.1018    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4558    2.6694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5174    0.4126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3941    0.8251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4250    2.0574    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4129    2.5380    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  2  0  0  0  0
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 11 10  1  0  0  0  0
 12  2  1  0  0  0  0
 12  3  1  0  0  0  0
 13  6  2  0  0  0  0
 13  7  1  0  0  0  0
 14  8  2  0  0  0  0
 14  9  1  0  0  0  0
 15 13  1  1  0  0  0
 16 15  1  0  0  0  0
 17  4  1  1  0  0  0
 17  5  1  6  0  0  0
 17 10  1  0  0  0  0
 17 16  1  0  0  0  0
 18 11  1  0  0  0  0
 18 12  1  1  0  0  0
 19 14  1  0  0  0  0
 20 15  1  0  0  0  0
 20 18  1  0  0  0  0
 21 16  1  0  0  0  0
 21 18  1  0  0  0  0
 15 22  1  6  0  0  0
 16 23  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0001910

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@]1(O[C@]2(CC[C@@](C)(C=C)[C@]1([H])O2)C(C)C)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H24O3/c1-5-17(4)10-11-18(12(2)3)20-15(16(17)21-18)13-6-8-14(19)9-7-13/h5-9,12,15-16,19H,1,10-11H2,2-4H3/t15-,16+,17+,18-/m0/s1

> <INCHI_KEY>
BPUKUJAZQKFJAN-MLHJIOFPSA-N

> <FORMULA>
C18H24O3

> <MOLECULAR_WEIGHT>
288.387

> <EXACT_MASS>
288.172544633

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
32.618379668962746

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(1S,2S,5R,7S)-2-ethenyl-2-methyl-5-(propan-2-yl)-6,8-dioxabicyclo[3.2.1]octan-7-yl]phenol

> <ALOGPS_LOGP>
3.55

> <JCHEM_LOGP>
4.641847423000001

> <ALOGPS_LOGS>
-4.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.470163692664862

> <JCHEM_PKA_STRONGEST_BASIC>
-4.096531871661098

> <JCHEM_POLAR_SURFACE_AREA>
38.69

> <JCHEM_REFRACTIVITY>
82.4327

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.64e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[(1S,2S,5R,7S)-2-ethenyl-5-isopropyl-2-methyl-6,8-dioxabicyclo[3.2.1]octan-7-yl]phenol

> <JCHEM_VEBER_RULE>
1

$$$$

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       2.338   5.238   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.356  -2.145   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.956  -2.739   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.173   3.270   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.671   4.468   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.537   4.514   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.694   2.111   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.924   5.182   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.082   2.779   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.339   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.671   0.153   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.827  -1.691   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.422   2.978   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.197   4.315   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.966   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.170   3.270   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.671   2.928   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.170  -0.190   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.584   4.983   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.966   0.770   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.602   1.540   0.000  0.00  0.00           O+0
HETATM   22  H   UNK     0       0.793   3.841   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0       2.637   4.738   0.000  0.00  0.00           H+0
CONECT    1    5                                                            
CONECT    2   12                                                            
CONECT    3   12                                                            
CONECT    4   17                                                            
CONECT    5    1   17                                                       
CONECT    6    8   13                                                       
CONECT    7    9   13                                                       
CONECT    8    6   14                                                       
CONECT    9    7   14                                                       
CONECT   10   11   17                                                       
CONECT   11   10   18                                                       
CONECT   12    2    3   18                                                  
CONECT   13    6    7   15                                                  
CONECT   14    8    9   19                                                  
CONECT   15   13   16   20   22                                             
CONECT   16   15   17   21   23                                             
CONECT   17    4    5   10   16                                             
CONECT   18   11   12   20   21                                             
CONECT   19   14                                                            
CONECT   20   15   18                                                       
CONECT   21   16   18                                                       
CONECT   22   15                                                            
CONECT   23   16                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

Synonyms

Not Available

Molecular Formula

C₁₈H₂₄O₃

Average Mass

288.387

Monoisotopic Mass

288.172544633

IUPAC Name

4-[(1S,2S,5R,7S)-2-ethenyl-2-methyl-5-(propan-2-yl)-6,8-dioxabicyclo[3.2.1]octan-7-yl]phenol

Traditional Name

4-[(1S,2S,5R,7S)-2-ethenyl-5-isopropyl-2-methyl-6,8-dioxabicyclo[3.2.1]octan-7-yl]phenol

CAS Registry Number

Not Available

SMILES

[H][C@]1(O[C@]2(CC[C@@](C)(C=C)[C@]1([H])O2)C(C)C)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C18H24O3/c1-5-17(4)10-11-18(12(2)3)20-15(16(17)21-18)13-6-8-14(19)9-7-13/h5-9,12,15-16,19H,1,10-11H2,2-4H3/t15-,16+,17+,18-/m0/s1

InChI Key

BPUKUJAZQKFJAN-MLHJIOFPSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxepanes

Sub Class

Not Available

Direct Parent

Oxepanes

Alternative Parents

Substituents

1-hydroxy-2-unsubstituted benzenoid
Ketal
Phenol
Oxepane
Benzenoid
Oxane
Monocyclic benzene moiety
Meta-dioxolane
Oxacycle
Acetal
Organic oxygen compound
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
Water Solubility	0.016 g/L	ALOGPS
logP	3.55	ALOGPS
logP	4.64	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	9.47	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.69 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	82.43 m³·mol⁻¹	ChemAxon
Polarizability	32.62 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (void)	2025-10-23	381.2
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	27.6
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	580.4
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	876.1
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	904.8
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-23	559.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	2726.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	78.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	395.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	678.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	402.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	292.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	228.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (void)	2025-10-23	8.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	432.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	386.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	477.6
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	1731.2
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	1584.7

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	Psoracorylifol C_TMS_1	C=C[C@]1(C)CC[C@]2(C(C)C)O[C@@H](C3=CC=C(O[Si](C)(C)C)C=C3)[C@H]1O2	standard non polar	2025-10-23	1357.79
Gas Chromatography	Psoracorylifol C_TMS_1	C=C[C@]1(C)CC[C@]2(C(C)C)O[C@@H](C3=CC=C(O[Si](C)(C)C)C=C3)[C@H]1O2	standard polar	2025-10-23	1563.47

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
Bacteria/Eubacteria	Proteobacteria	1	Human ; 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

9876711

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11701986

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 Psoracorylifol C (MMDBc0001910)

MOL for #<Metabolite:0x00007f9ad0dffa80>

3D MOL for #<Metabolite:0x00007f9ad0dffa80>

3D SDF for #<Metabolite:0x00007f9ad0dffa80>

3D-SDF for #<Metabolite:0x00007f9ad0dffa80>

PDB for #<Metabolite:0x00007f9ad0dffa80>

3D PDB for #<Metabolite:0x00007f9ad0dffa80>

SMILES for #<Metabolite:0x00007f9ad0dffa80>

INCHI for #<Metabolite:0x00007f9ad0dffa80>

Structure for #<Metabolite:0x00007f9ad0dffa80>

3D Structure for #<Metabolite:0x00007f9ad0dffa80>