NP-MRD: Showing NP-Card for Apotrichothecene (NP0337679)

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Record Information

Version

2.0

Created at

2024-09-11 11:54:17 UTC

Updated at

2024-09-11 11:54:17 UTC

NP-MRD ID

NP0337679

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Apotrichothecene

Description

Apotrichothecene belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen. Apotrichothecene was first documented in 1991 (PMID: 2034260). Based on a literature review very few articles have been published on Apotrichothecene (PMID: 10552458).

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05262314262D          

 17 19  0  0  0  0            999 V2000
   -1.4163    0.7651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7274    0.3059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4929    0.0769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7991   -0.6892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2633   -1.3015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5694   -2.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7274    1.5311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1152    0.9182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1152    1.7608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6503    2.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1095    1.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6503    0.6885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4157    0.5355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7991   -0.2293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4978   -1.1485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2676   -0.3059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4972   -0.1528    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
  2  8  1  0  0  0  0
  2 16  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
  5 15  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 12  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 17  1  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0337679

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC2OC3(CO)CCCC3(C)C2(C)CC1

> <INCHI_IDENTIFIER>
InChI=1/C15H24O2/c1-11-5-8-13(2)12(9-11)17-15(10-16)7-4-6-14(13,15)3/h9,12,16H,4-8,10H2,1-3H3

> <INCHI_KEY>
JFZZTCKYMWJCGK-UHFFFAOYNA-N

> <FORMULA>
C15H24O2

> <MOLECULAR_WEIGHT>
236.355

> <EXACT_MASS>
236.177630013

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
27.74094722148596

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{1,2,10-trimethyl-7-oxatricyclo[6.4.0.0^{2,6}]dodec-9-en-6-yl}methanol

> <JCHEM_LOGP>
2.6826197300000003

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.347724369950885

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0841053605834823

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
68.6016

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
{1,2,10-trimethyl-7-oxatricyclo[6.4.0.0^{2,6}]dodec-9-en-6-yl}methanol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0      -2.644   1.428   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.358   0.571   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.787   0.144   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.358  -1.287   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.358  -2.429   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.930  -3.858   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.358   2.858   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.215   1.714   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.215   3.287   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.214   3.858   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.071   2.571   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.214   1.285   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.643   1.000   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.358  -0.428   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.929  -2.144   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.500  -0.571   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.928  -0.285   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8   16                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   15                                                  
CONECT    6    5                                                            
CONECT    7    8                                                            
CONECT    8    2    7    9   12                                             
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12    8   11   13   17                                             
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15    5   16                                                       
CONECT   16    2   15   17                                                  
CONECT   17   12   16                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₄O₂

Average Mass

236.3550 Da

Monoisotopic Mass

236.17763 Da

IUPAC Name

{1,2,10-trimethyl-7-oxatricyclo[6.4.0.0^{2,6}]dodec-9-en-6-yl}methanol

Traditional Name

{1,2,10-trimethyl-7-oxatricyclo[6.4.0.0^{2,6}]dodec-9-en-6-yl}methanol

CAS Registry Number

Not Available

SMILES

CC1=CC2OC3(CO)CCCC3(C)C2(C)CC1

InChI Identifier

InChI=1/C15H24O2/c1-11-5-8-13(2)12(9-11)17-15(10-16)7-4-6-14(13,15)3/h9,12,16H,4-8,10H2,1-3H3

InChI Key

JFZZTCKYMWJCGK-UHFFFAOYNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrahydrofurans

Sub Class

Not Available

Direct Parent

Tetrahydrofurans

Alternative Parents

Substituents

Tetrahydrofuran
Oxacycle
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
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	2.68	ChemAxon
pKa (Strongest Acidic)	14.35	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.46 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	68.6 m³·mol⁻¹	ChemAxon
Polarizability	27.74 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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Senter LH, Sanson DR, Corley DG, Tempesta MS, Rottinghaus AA, Rottinghaus GE: Cytotoxicity of trichothecene mycotoxins isolated from Fusarium sporotrichioides (MC-72083) and Fusarium sambucinum in baby hamster kidney (BHK-21) cells. Mycopathologia. 1991 Feb;113(2):127-31. doi: 10.1007/BF00442425. [PubMed:2034260 ]
Zamir LO, Nikolakakis A, Sauriol F, Mamer O: Biosynthesis of trichothecenes and apotrichothecenes. J Agric Food Chem. 1999 May;47(5):1823-35. doi: 10.1021/jf980808r. [PubMed:10552458 ]

Showing NP-Card for Apotrichothecene (NP0337679)

MOL for NP0337679 (Apotrichothecene)

3D MOL for NP0337679 (Apotrichothecene)

3D SDF for NP0337679 (Apotrichothecene)

3D-SDF for NP0337679 (Apotrichothecene)

PDB for NP0337679 (Apotrichothecene)

3D PDB for NP0337679 (Apotrichothecene)

SMILES for NP0337679 (Apotrichothecene)

INCHI for NP0337679 (Apotrichothecene)

Structure for NP0337679 (Apotrichothecene)

3D Structure for NP0337679 (Apotrichothecene)