MiMeDB: Showing metabocard for Pestaloficiol E (MMDBc0018451)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 08:38:35 UTC

Update Date

2022-08-31 06:43:51 UTC

Metabolite ID

MMDBc0018451

Metabolite Identification

Common Name

Pestaloficiol E

Description

Pestaloficiol E belongs to the class of organic compounds known as benzopyrans. These are organic compounds containing a benzene ring fused to a pyran ring. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds. Pestaloficiol E is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152110382D          

 25 27  0  0  1  0            999 V2000
    5.0238    0.4866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0132    0.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7525    0.2234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3246    0.7244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5950   -0.4882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5751    3.2859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8821    1.5377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6781    1.8155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8256    2.4999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7691    3.4620    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6316    2.3238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2880    1.2600    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2136    2.8520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2701    1.8899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3266    0.9278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5385    0.4739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4641    2.0660    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5186    4.2480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1871    2.9337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4076    3.0281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7890   -0.3121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5206    1.1038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9631    3.6381    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1121    1.2985    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6581    2.2421    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  6  1  0  0  0  0
 10  6  1  0  0  0  0
 11  7  1  0  0  0  0
 11  9  1  0  0  0  0
 12  8  1  0  0  0  0
 13 10  1  0  0  0  0
 14  9  2  0  0  0  0
 15  1  1  0  0  0  0
 15  2  1  0  0  0  0
 15  7  1  0  0  0  0
 16  3  1  0  0  0  0
 16  4  1  0  0  0  0
 12 16  1  6  0  0  0
 17  8  1  1  0  0  0
 17 12  1  0  0  0  0
 17 13  1  0  0  0  0
 17 14  1  0  0  0  0
 10 18  1  1  0  0  0
 19 11  2  0  0  0  0
 13 20  1  1  0  0  0
 21  5  1  0  0  0  0
 21 16  1  0  0  0  0
 22 14  1  0  0  0  0
 22 15  1  0  0  0  0
 10 23  1  6  0  0  0
 12 24  1  1  0  0  0
 13 25  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0018451

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@]1(C[C@@]11C2=C(C[C@]([H])(O)[C@]1([H])O)C(=O)CC(C)(C)O2)C(C)(C)OC

> <INCHI_IDENTIFIER>
InChI=1S/C17H26O5/c1-15(2)7-11(19)9-6-10(18)13(20)17(14(9)22-15)8-12(17)16(3,4)21-5/h10,12-13,18,20H,6-8H2,1-5H3/t10-,12-,13-,17+/m0/s1

> <INCHI_KEY>
PTEAJHVZALZNSN-HTWFXAOOSA-N

> <FORMULA>
C17H26O5

> <MOLECULAR_WEIGHT>
310.39

> <EXACT_MASS>
310.178023937

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
33.3072692287287

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3'R,6S,7R,8R)-6,7-dihydroxy-3'-(2-methoxypropan-2-yl)-2,2-dimethyl-2,3,4,5,6,7-hexahydrospiro[1-benzopyran-8,1'-cyclopropane]-4-one

> <ALOGPS_LOGP>
1.16

> <JCHEM_LOGP>
0.23384171499999906

> <ALOGPS_LOGS>
-2.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.043021857536974

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.47709484940263

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1984415306331107

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
82.4207

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.03e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3'R,6S,7R,8R)-6,7-dihydroxy-3'-(2-methoxypropan-2-yl)-2,2-dimethyl-3,5,6,7-tetrahydrospiro[1-benzopyran-8,1'-cyclopropane]-4-one

> <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       9.378   0.908   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.491   0.307   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.271   0.417   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.206   1.352   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.711  -0.911   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.674   6.134   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.113   2.870   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.132   3.389   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.141   4.666   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.169   6.462   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.646   4.338   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.271   2.352   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.132   5.324   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.104   3.528   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.076   1.732   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.739   0.885   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.600   3.856   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.701   7.930   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       9.683   5.476   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.628   5.652   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.206  -0.583   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.572   2.061   0.000  0.00  0.00           O+0
HETATM   23  H   UNK     0       3.664   6.791   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0       5.809   2.424   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0       3.095   4.185   0.000  0.00  0.00           H+0
CONECT    1   15                                                            
CONECT    2   15                                                            
CONECT    3   16                                                            
CONECT    4   16                                                            
CONECT    5   21                                                            
CONECT    6    9   10                                                       
CONECT    7   11   15                                                       
CONECT    8   12   17                                                       
CONECT    9    6   11   14                                                  
CONECT   10    6   13   18   23                                             
CONECT   11    7    9   19                                                  
CONECT   12    8   16   17   24                                             
CONECT   13   10   17   20   25                                             
CONECT   14    9   17   22                                                  
CONECT   15    1    2    7   22                                             
CONECT   16    3    4   12   21                                             
CONECT   17    8   12   13   14                                             
CONECT   18   10                                                            
CONECT   19   11                                                            
CONECT   20   13                                                            
CONECT   21    5   16                                                       
CONECT   22   14   15                                                       
CONECT   23   10                                                            
CONECT   24   12                                                            
CONECT   25   13                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

Synonyms

Not Available

Molecular Formula

C₁₇H₂₆O₅

Average Mass

310.39

Monoisotopic Mass

310.178023937

IUPAC Name

(3'R,6S,7R,8R)-6,7-dihydroxy-3'-(2-methoxypropan-2-yl)-2,2-dimethyl-2,3,4,5,6,7-hexahydrospiro[1-benzopyran-8,1'-cyclopropane]-4-one

Traditional Name

(3'R,6S,7R,8R)-6,7-dihydroxy-3'-(2-methoxypropan-2-yl)-2,2-dimethyl-3,5,6,7-tetrahydrospiro[1-benzopyran-8,1'-cyclopropane]-4-one

CAS Registry Number

Not Available

SMILES

[H][C@]1(C[C@@]11C2=C(C[C@]([H])(O)[C@]1([H])O)C(=O)CC(C)(C)O2)C(C)(C)OC

InChI Identifier

InChI=1S/C17H26O5/c1-15(2)7-11(19)9-6-10(18)13(20)17(14(9)22-15)8-12(17)16(3,4)21-5/h10,12-13,18,20H,6-8H2,1-5H3/t10-,12-,13-,17+/m0/s1

InChI Key

PTEAJHVZALZNSN-HTWFXAOOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzopyrans. These are organic compounds containing a benzene ring fused to a pyran ring. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

Not Available

Direct Parent

Benzopyrans

Alternative Parents

Substituents

Benzopyran
Dihydropyranone
Vinylogous ester
1,2-diol
Ketone
Secondary alcohol
Dialkyl ether
Ether
Oxacycle
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
Alcohol
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	3.03 g/L	ALOGPS
logP	1.16	ALOGPS
logP	0.23	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	13.48	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	82.42 m³·mol⁻¹	ChemAxon
Polarizability	33.31 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
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	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

Not Available

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

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

24700817

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44586462

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 Pestaloficiol E (MMDBc0018451)

MOL for #<Metabolite:0x00005634c2839120>

3D MOL for #<Metabolite:0x00005634c2839120>

3D SDF for #<Metabolite:0x00005634c2839120>

3D-SDF for #<Metabolite:0x00005634c2839120>

PDB for #<Metabolite:0x00005634c2839120>

3D PDB for #<Metabolite:0x00005634c2839120>

SMILES for #<Metabolite:0x00005634c2839120>

INCHI for #<Metabolite:0x00005634c2839120>

Structure for #<Metabolite:0x00005634c2839120>

3D Structure for #<Metabolite:0x00005634c2839120>