NP-MRD: Showing NP-Card for Oudemansin A (NP0049531)

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Record Information

Version

2.0

Created at

2022-03-17 21:14:00 UTC

Updated at

2022-03-17 21:14:00 UTC

NP-MRD ID

NP0049531

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Oudemansin A

Description

Oudemansin A belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety. Oudemansin A is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Oudemansin A has been detected, but not quantified in, mushrooms. This could make oudemansin a a potential biomarker for the consumption of these foods. Oudemansin A is found in Favolaschia tonkinensis, Mucidula mucida, Oudemansiella mucida and Xerula pudens. Oudemansin A is an antibiotic made by Collybia mushrooms.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061311312D          

 21 21  0  0  0  0            999 V2000
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 11 10  2  0  0  0  0
 13  1  1  0  0  0  0
 14  8  2  0  0  0  0
 14  9  1  0  0  0  0
 14 10  1  0  0  0  0
 15 12  2  0  0  0  0
 15 13  1  0  0  0  0
 16 11  1  0  0  0  0
 16 13  1  0  0  0  0
 17 15  1  0  0  0  0
 18 17  2  0  0  0  0
 19  2  1  0  0  0  0
 19 12  1  0  0  0  0
 20  3  1  0  0  0  0
 20 16  1  0  0  0  0
 21  4  1  0  0  0  0
 21 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049531

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO\C=C(\C(C)C(OC)\C=C/C1=CC=CC=C1)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C17H22O4/c1-13(15(12-19-2)17(18)21-4)16(20-3)11-10-14-8-6-5-7-9-14/h5-13,16H,1-4H3/b11-10-,15-12-

> <INCHI_KEY>
COBDENJOXQSLKO-MRZBGHJPSA-N

> <FORMULA>
C17H22O4

> <MOLECULAR_WEIGHT>
290.3542

> <EXACT_MASS>
290.151809192

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
31.610383927270966

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2Z,5Z)-4-methoxy-2-(methoxymethylidene)-3-methyl-6-phenylhex-5-enoate

> <ALOGPS_LOGP>
3.52

> <JCHEM_LOGP>
3.240285328666665

> <ALOGPS_LOGS>
-4.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.058167519794534

> <JCHEM_POLAR_SURFACE_AREA>
44.760000000000005

> <JCHEM_REFRACTIVITY>
83.50040000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.92e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
oudemansin A

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -6.668   3.850   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -5.335   1.540   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -5.335   6.160   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2   19                                                            
CONECT    3   20                                                            
CONECT    4   21                                                            
CONECT    5    6    7                                                       
CONECT    6    5    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   14                                                       
CONECT    9    7   14                                                       
CONECT   10   11   14                                                       
CONECT   11   10   16                                                       
CONECT   12   15   19                                                       
CONECT   13    1   15   16                                                  
CONECT   14    8    9   10                                                  
CONECT   15   12   13   17                                                  
CONECT   16   11   13   20                                                  
CONECT   17   15   18   21                                                  
CONECT   18   17                                                            
CONECT   19    2   12                                                       
CONECT   20    3   16                                                       
CONECT   21    4   17                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

View in JSmol

Synonyms

Value	Source
(-)-Odemasin a	HMDB
(-)-Oudemansin a	HMDB
Methyl 4-methoxy-2-(methoxymethylene)-3-methyl-6-phenyl-5-hexenoate, 9ci	HMDB
Oudemansin	HMDB
Oudemansin b	HMDB
Methyl (5Z)-4-methoxy-2-(methoxymethylidene)-3-methyl-6-phenylhex-5-enoic acid	Generator

Chemical Formula

C₁₇H₂₂O₄

Average Mass

290.3542 Da

Monoisotopic Mass

290.15181 Da

IUPAC Name

methyl (2Z,5Z)-4-methoxy-2-(methoxymethylidene)-3-methyl-6-phenylhex-5-enoate

Traditional Name

oudemansin A

CAS Registry Number

73341-71-6

SMILES

CO\C=C(\C(C)C(OC)\C=C/C1=CC=CC=C1)C(=O)OC

InChI Identifier

InChI=1S/C17H22O4/c1-13(15(12-19-2)17(18)21-4)16(20-3)11-10-14-8-6-5-7-9-14/h5-13,16H,1-4H3/b11-10-,15-12-

InChI Key

COBDENJOXQSLKO-MRZBGHJPSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Agaricus bisporus	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Favolaschia tonkinensis	LOTUS Database	35616633
Mucidula mucida	LOTUS Database	35616633
Oudemansiella mucida	Fungi	KNApSAcK
Pleurotus ostreatus	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Xerula pudens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Styrenes

Direct Parent

Styrenes

Alternative Parents

Substituents

Styrene
Fatty acid ester
Fatty acyl
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.52	ALOGPS
logP	3.24	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	44.76 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	83.5 m³·mol⁻¹	ChemAxon
Polarizability	31.61 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0039949

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB019611

KNApSAcK ID

C00018254

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Oudemansin A

METLIN ID

Not Available

PubChem Compound

131752766

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Oudemansin A (NP0049531)

MOL for NP0049531 (Oudemansin A)

3D MOL for NP0049531 (Oudemansin A)

3D SDF for NP0049531 (Oudemansin A)

3D-SDF for NP0049531 (Oudemansin A)

PDB for NP0049531 (Oudemansin A)

3D PDB for NP0049531 (Oudemansin A)

SMILES for NP0049531 (Oudemansin A)

INCHI for NP0049531 (Oudemansin A)

Structure for NP0049531 (Oudemansin A)

3D Structure for NP0049531 (Oudemansin A)