NP-MRD: Showing NP-Card for Naematolone (NP0048322)

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Record Information

Version

2.0

Created at

2022-03-17 20:54:37 UTC

Updated at

2022-03-17 20:54:37 UTC

NP-MRD ID

NP0048322

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Naematolone

Description

Naematolone belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Naematolone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Naematolone has been detected, but not quantified in, mushrooms. Naematolone is found in Hypholoma capnoides , Hypholoma elongatipes and Hypholoma sublateritium . This could make naematolone a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061308422D          

 22 23  0  0  0  0            999 V2000
    5.6877    2.2468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1162   -0.8178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0949   -0.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3484    1.3537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1734    2.1787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3378    0.9412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1734    0.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0557    1.7165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5287   -0.1033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4629   -0.0822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9984    0.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0557    0.1660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9984    1.3537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3412    2.1290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3412   -0.2465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5287    1.9857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1734    1.3537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6062    0.7303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4845    2.9414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4845   -1.0590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1162    2.7002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6877   -0.3643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  0  0  0  0
  8  6  2  0  0  0  0
  9  2  2  0  0  0  0
 10  3  1  0  0  0  0
 11  7  1  0  0  0  0
 11  9  1  0  0  0  0
 12  6  1  0  0  0  0
 13 11  1  0  0  0  0
 14  8  1  0  0  0  0
 15  9  1  0  0  0  0
 15 12  1  0  0  0  0
 16 13  1  0  0  0  0
 16 14  1  0  0  0  0
 17  4  1  0  0  0  0
 17  5  1  0  0  0  0
 17  7  1  0  0  0  0
 17 13  1  0  0  0  0
 18 10  2  0  0  0  0
 19 14  2  0  0  0  0
 20 15  2  0  0  0  0
 21 16  1  0  0  0  0
 22 10  1  0  0  0  0
 22 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048322

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1\C=C(C)/C(=O)C(O)C2C(CC2(C)C)C(=C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H22O5/c1-8-6-12(22-10(3)18)15(20)9(2)11-7-17(4,5)13(11)16(21)14(8)19/h6,11-13,16,21H,2,7H2,1,3-5H3/b8-6-

> <INCHI_KEY>
BBRNVDBLOTVLMB-VURMDHGXSA-N

> <FORMULA>
C17H22O5

> <MOLECULAR_WEIGHT>
306.3536

> <EXACT_MASS>
306.146723814

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
31.862549872218484

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z)-8-hydroxy-6,10,10-trimethyl-2-methylidene-3,7-dioxobicyclo[7.2.0]undec-5-en-4-yl acetate

> <ALOGPS_LOGP>
1.57

> <JCHEM_LOGP>
2.1175974280000007

> <ALOGPS_LOGS>
-2.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.132163808134994

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.02014183744414

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6213034274082148

> <JCHEM_POLAR_SURFACE_AREA>
80.67

> <JCHEM_REFRACTIVITY>
80.74369999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.27e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5Z)-8-hydroxy-6,10,10-trimethyl-2-methylidene-3,7-dioxobicyclo[7.2.0]undec-5-en-4-yl acetate

> <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      10.617   4.194   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.817  -1.527   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.244  -1.143   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.517   2.527   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.057   4.067   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.964   1.757   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.057   0.987   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.437   3.204   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.587  -0.193   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.064  -0.153   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.597   0.987   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.437   0.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.597   2.527   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.104   3.974   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.104  -0.460   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.587   3.707   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.057   2.527   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      12.332   1.363   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       8.371   5.491   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       8.371  -1.977   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.817   5.040   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      10.617  -0.680   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4   17                                                            
CONECT    5   17                                                            
CONECT    6    8   12                                                       
CONECT    7   11   17                                                       
CONECT    8    1    6   14                                                  
CONECT    9    2   11   15                                                  
CONECT   10    3   18   22                                                  
CONECT   11    7    9   13                                                  
CONECT   12    6   15   22                                                  
CONECT   13   11   16   17                                                  
CONECT   14    8   16   19                                                  
CONECT   15    9   12   20                                                  
CONECT   16   13   14   21                                                  
CONECT   17    4    5    7   13                                             
CONECT   18   10                                                            
CONECT   19   14                                                            
CONECT   20   15                                                            
CONECT   21   16                                                            
CONECT   22   10   12                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Value	Source
Naematolon	HMDB
Nematolone	HMDB
(5Z)-8-Hydroxy-6,10,10-trimethyl-2-methylidene-3,7-dioxobicyclo[7.2.0]undec-5-en-4-yl acetic acid	Generator
4-Acetyloxy-8-hydroxy-2-methylene-6,10,10-trimethyl-bicyclo(7.2.0)undec-5-ene-3,7-dione	MeSH

Chemical Formula

C₁₇H₂₂O₅

Average Mass

306.3536 Da

Monoisotopic Mass

306.14672 Da

IUPAC Name

(5Z)-8-hydroxy-6,10,10-trimethyl-2-methylidene-3,7-dioxobicyclo[7.2.0]undec-5-en-4-yl acetate

Traditional Name

(5Z)-8-hydroxy-6,10,10-trimethyl-2-methylidene-3,7-dioxobicyclo[7.2.0]undec-5-en-4-yl acetate

CAS Registry Number

92121-62-5

SMILES

CC(=O)OC1\C=C(C)/C(=O)C(O)C2C(CC2(C)C)C(=C)C1=O

InChI Identifier

InChI=1S/C17H22O5/c1-8-6-12(22-10(3)18)15(20)9(2)11-7-17(4,5)13(11)16(21)14(8)19/h6,11-13,16,21H,2,7H2,1,3-5H3/b8-6-

InChI Key

BBRNVDBLOTVLMB-VURMDHGXSA-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...
Hypholoma capnoides	Fungi	KNApSAcK
Hypholoma elongatipes	Fungi	KNApSAcK
Hypholoma sublateritium	Fungi	KNApSAcK
Pleurotus ostreatus	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Caryophyllane sesquiterpenoid
Alpha-acyloxy ketone
Carboxylic acid ester
Ketone
Secondary alcohol
Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Carbonyl group
Organooxygen compound
Alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	1.57	ALOGPS
logP	2.12	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	11.02	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.67 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	80.74 m³·mol⁻¹	ChemAxon
Polarizability	31.86 Å³	ChemAxon
Number of Rings	2	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

HMDB0035781

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014528

KNApSAcK ID

C00012495

Chemspider ID

20145021

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

20839779

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Naematolone (NP0048322)

MOL for NP0048322 (Naematolone)

3D MOL for NP0048322 (Naematolone)

3D SDF for NP0048322 (Naematolone)

3D-SDF for NP0048322 (Naematolone)

PDB for NP0048322 (Naematolone)

3D PDB for NP0048322 (Naematolone)

SMILES for NP0048322 (Naematolone)

INCHI for NP0048322 (Naematolone)

Structure for NP0048322 (Naematolone)

3D Structure for NP0048322 (Naematolone)