NP-MRD: Showing NP-Card for Mellitoxin (NP0051928)

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Record Information

Version

2.0

Created at

2022-04-27 23:07:56 UTC

Updated at

2022-04-27 23:07:56 UTC

NP-MRD ID

NP0051928

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Mellitoxin

Description

(1'R,2R,2'R,3'S,5'R,7'R,8'S,9'S,12'S)-2',8',12'-trihydroxy-7'-methyl-12'-(prop-1-en-2-yl)-4',10'-dioxaspiro[oxirane-2,6'-tetracyclo[7.2.1.0²,⁷.0³,⁵]Dodecane]-11'-one belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Mellitoxin is found in Coriaria arborea, Scolypopa australis and Toxicodendron globosum. Based on a literature review very few articles have been published on (1'R,2R,2'R,3'S,5'R,7'R,8'S,9'S,12'S)-2',8',12'-trihydroxy-7'-methyl-12'-(prop-1-en-2-yl)-4',10'-dioxaspiro[oxirane-2,6'-tetracyclo[7.2.1.0²,⁷.0³,⁵]Dodecane]-11'-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282201072D          

 22 26  0  0  1  0            999 V2000
    0.3188    0.4705    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1036    0.2160    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4169    1.1186    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2686    2.0624    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4512    1.9512    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0285    1.2427    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7760    1.4257    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8504    2.2474    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0920    2.5721    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7525    3.0665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0421    0.6448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5853    1.2658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5458    0.4855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7523    2.8195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8653    1.4927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6622    1.8211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7919    0.6709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8563    0.5336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0372   -0.4291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5315    1.1848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8495    1.6810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0038   -0.3510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  6  0  0  0
  8 10  1  6  0  0  0
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
  7 12  1  6  0  0  0
  6 13  1  6  0  0  0
  5 14  1  6  0  0  0
  4 15  1  6  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  2 17  1  1  0  0  0
  3 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
  3 21  1  6  0  0  0
  1 22  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0051928

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)[C@]1(O)[C@H]2OC(=O)[C@H]1[C@]1(O)[C@H]3O[C@H]3[C@]3(CO3)[C@]1(C)[C@@H]2O

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O7/c1-5(2)14(18)6-11(17)22-8(14)7(16)12(3)13(4-20-13)9-10(21-9)15(6,12)19/h6-10,16,18-19H,1,4H2,2-3H3/t6-,7-,8+,9-,10+,12+,13-,14-,15+/m1/s1

> <INCHI_KEY>
DWCJGLPGZULWPZ-JSACTSDDSA-N

> <FORMULA>
C15H18O7

> <MOLECULAR_WEIGHT>
310.302

> <EXACT_MASS>
310.10525292

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
49.402283646827186

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1'R,2R,2'R,3'S,5'R,7'R,8'S,9'S,12'S)-2',8',12'-trihydroxy-7'-methyl-12'-(prop-1-en-2-yl)-4',10'-dioxaspiro[oxirane-2,6'-tetracyclo[7.2.1.0^{2,7}.0^{3,5}]dodecane]-11'-one

> <ALOGPS_LOGP>
-0.24

> <JCHEM_LOGP>
-1.4318971290000002

> <ALOGPS_LOGS>
-0.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.980009582737598

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.334109592218752

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4793967492237874

> <JCHEM_POLAR_SURFACE_AREA>
112.05000000000001

> <JCHEM_REFRACTIVITY>
68.60990000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.82e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1'R,2R,2'R,3'S,5'R,7'R,8'S,9'S,12'S)-2',8',12'-trihydroxy-7'-methyl-12'-(prop-1-en-2-yl)-4',10'-dioxaspiro[oxirane-2,6'-tetracyclo[7.2.1.0^{2,7}.0^{3,5}]dodecane]-11'-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       0.595   0.878   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.060   0.403   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.645   2.088   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.368   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.842   3.642   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.053   2.320   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.448   2.661   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.587   4.195   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.172   4.801   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.405   5.724   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.945   1.204   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.959   2.363   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.019   0.906   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.404   5.263   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.482   2.786   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.969   3.399   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       3.345   1.252   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.598   0.996   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.936  -0.801   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.992   2.212   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.586   3.138   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.007  -0.655   0.000  0.00  0.00           O+0
CONECT    1    2    6   22                                                  
CONECT    2    1    3   17                                                  
CONECT    3    2    4   18   21                                             
CONECT    4    3    5   15                                                  
CONECT    5    4    6    9   14                                             
CONECT    6    5    1    7   13                                             
CONECT    7    6    8   11   12                                             
CONECT    8    7    9   10                                                  
CONECT    9    8    5   10                                                  
CONECT   10    9    8                                                       
CONECT   11    7   12                                                       
CONECT   12   11    7                                                       
CONECT   13    6                                                            
CONECT   14    5                                                            
CONECT   15    4   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    2                                                       
CONECT   18    3   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21    3                                                            
CONECT   22    1                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₈O₇

Average Mass

310.3020 Da

Monoisotopic Mass

310.10525 Da

IUPAC Name

(1'R,2R,2'R,3'S,5'R,7'R,8'S,9'S,12'S)-2',8',12'-trihydroxy-7'-methyl-12'-(prop-1-en-2-yl)-4',10'-dioxaspiro[oxirane-2,6'-tetracyclo[7.2.1.0^{2,7}.0^{3,5}]dodecane]-11'-one

Traditional Name

(1'R,2R,2'R,3'S,5'R,7'R,8'S,9'S,12'S)-2',8',12'-trihydroxy-7'-methyl-12'-(prop-1-en-2-yl)-4',10'-dioxaspiro[oxirane-2,6'-tetracyclo[7.2.1.0^{2,7}.0^{3,5}]dodecane]-11'-one

CAS Registry Number

Not Available

SMILES

CC(=C)[C@]1(O)[C@H]2OC(=O)[C@H]1[C@]1(O)[C@H]3O[C@H]3[C@]3(CO3)[C@]1(C)[C@@H]2O

InChI Identifier

InChI=1S/C15H18O7/c1-5(2)14(18)6-11(17)22-8(14)7(16)12(3)13(4-20-13)9-10(21-9)15(6,12)19/h6-10,16,18-19H,1,4H2,2-3H3/t6-,7-,8+,9-,10+,12+,13-,14-,15+/m1/s1

InChI Key

DWCJGLPGZULWPZ-JSACTSDDSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Coriaria arborea	Plant	KNApSAcK
Scolypopa australis	-	KNApSAcK
Toxicodendron globosum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Oxepane
Oxane
Gamma butyrolactone
Tetrahydrofuran
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Oxacycle
Polyol
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	-0.24	ALOGPS
logP	-1.4	ChemAxon
logS	-0.81	ALOGPS
pKa (Strongest Acidic)	12.33	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	112.05 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	68.61 m³·mol⁻¹	ChemAxon
Polarizability	49.4 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163080707

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Mellitoxin (NP0051928)

MOL for NP0051928 (Mellitoxin)

3D MOL for NP0051928 (Mellitoxin)

3D SDF for NP0051928 (Mellitoxin)

3D-SDF for NP0051928 (Mellitoxin)

PDB for NP0051928 (Mellitoxin)

3D PDB for NP0051928 (Mellitoxin)

SMILES for NP0051928 (Mellitoxin)

INCHI for NP0051928 (Mellitoxin)

Structure for NP0051928 (Mellitoxin)

3D Structure for NP0051928 (Mellitoxin)