NP-MRD: Showing NP-Card for (3alpha,4beta,7alpha)12,13-Epoxy-trichothec-9-ene-3,4,7,15-tetrol 4,15-diacetate (NP0059141)

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Record Information

Version

2.0

Created at

2022-04-28 04:24:58 UTC

Updated at

2022-04-28 04:24:58 UTC

NP-MRD ID

NP0059141

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3alpha,4beta,7alpha)12,13-Epoxy-trichothec-9-ene-3,4,7,15-tetrol 4,15-diacetate

Description

[(1'R,2S,2'R,3'R,7'R,9'R,10'R,11'S)-11'-(acetyloxy)-3',10'-dihydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]Dodecan]-5'-en-2'-yl]methyl acetate belongs to the class of organic compounds known as trichothecenes. These are sesquiterpene mycotoxins structurally characterized by the presence of an epoxide ring and a benzopyran derivative with a variant number of hydroxyl, acetyl, or other substituents. The most important structural features causing the biological activities of trichothecenes are the 12,13-epoxy ring, the presence of hydroxyl or acetyl groups at appropriate positions on the trichothecene nucleus and the structure and position of the side-chain. (3alpha,4beta,7alpha)12,13-Epoxy-trichothec-9-ene-3,4,7,15-tetrol 4,15-diacetate is found in Fusarium spp. Based on a literature review very few articles have been published on [(1'R,2S,2'R,3'R,7'R,9'R,10'R,11'S)-11'-(acetyloxy)-3',10'-dihydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]Dodecan]-5'-en-2'-yl]methyl acetate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282206242D          

 27 30  0  0  1  0            999 V2000
    3.3584    0.4952    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7212    1.0193    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8566    1.8331    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6290    2.1229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2661    1.5988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1308    0.7849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0386    1.8885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3047    2.4463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4811    2.3972    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5184    1.4425    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0006    0.6177    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2373    0.9307    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0061    1.7227    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1923    1.8580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6241    0.3788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7954   -0.4282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5800   -0.6833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1822   -0.9801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0498   -0.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9482    0.8463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7170    1.6383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6471    0.1976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3216   -0.2774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2475   -1.0990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9220   -1.5741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4989   -1.4457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7273   -0.2427    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  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  3  8  1  6  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  1  0  0  0
 12 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 11 19  1  1  0  0  0
 10 20  1  1  0  0  0
 20 21  1  0  0  0  0
 10 21  1  0  0  0  0
  2 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
  1 27  1  1  0  0  0
M  END


  Mrv1652304282206242D          

 27 30  0  0  1  0            999 V2000
    3.3584    0.4952    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7212    1.0193    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8566    1.8331    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6290    2.1229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2661    1.5988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1308    0.7849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0386    1.8885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3047    2.4463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4811    2.3972    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5184    1.4425    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0006    0.6177    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2373    0.9307    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0061    1.7227    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1923    1.8580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6241    0.3788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7954   -0.4282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5800   -0.6833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1822   -0.9801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0498   -0.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9482    0.8463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7170    1.6383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6471    0.1976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3216   -0.2774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2475   -1.0990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9220   -1.5741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4989   -1.4457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7273   -0.2427    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  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  3  8  1  6  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  1  0  0  0
 12 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 11 19  1  1  0  0  0
 10 20  1  1  0  0  0
 20 21  1  0  0  0  0
 10 21  1  0  0  0  0
  2 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
  1 27  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0059141

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC[C@]12[C@H](O)CC(C)=C[C@H]1O[C@@H]1[C@H](O)[C@@H](OC(C)=O)[C@]2(C)[C@]11CO1

> <INCHI_IDENTIFIER>
InChI=1S/C19H26O8/c1-9-5-12(22)18(7-24-10(2)20)13(6-9)27-16-14(23)15(26-11(3)21)17(18,4)19(16)8-25-19/h6,12-16,22-23H,5,7-8H2,1-4H3/t12-,13-,14-,15-,16-,17+,18+,19+/m1/s1

> <INCHI_KEY>
DXOMWDQITCLYBJ-AVNVQCJHSA-N

> <FORMULA>
C19H26O8

> <MOLECULAR_WEIGHT>
382.409

> <EXACT_MASS>
382.162767797

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
38.417650069346266

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1'R,2S,2'R,3'R,7'R,9'R,10'R,11'S)-11'-(acetyloxy)-3',10'-dihydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-2'-yl]methyl acetate

> <ALOGPS_LOGP>
0.45

> <JCHEM_LOGP>
-0.8538114616666654

> <ALOGPS_LOGS>
-2.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.4626181905249

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.054111351366576

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0418348061085405

> <JCHEM_POLAR_SURFACE_AREA>
114.82000000000001

> <JCHEM_REFRACTIVITY>
90.61519999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.85e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1'R,2S,2'R,3'R,7'R,9'R,10'R,11'S)-11'-(acetyloxy)-3',10'-dihydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-2'-ylmethyl acetate

> <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       6.269   0.924   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.080   1.903   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.332   3.422   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.774   3.963   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.963   2.984   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.711   1.465   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.405   3.525   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.302   4.567   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.765   4.475   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.834   2.693   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.734   1.153   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.310   1.737   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.878   3.216   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.359   3.468   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       1.165   0.707   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.485  -0.799   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.949  -1.275   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.340  -1.830   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.826  -0.384   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.770   1.580   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.338   3.058   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.941   0.369   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.200  -0.518   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.062  -2.052   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       7.321  -2.938   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.665  -2.699   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.958  -0.453   0.000  0.00  0.00           O+0
CONECT    1    2    6   27                                                  
CONECT    2    1    3   11   22                                             
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5                                                            
CONECT    8    3    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11   20   21                                             
CONECT   11   10    2   12   19                                             
CONECT   12   11   13   15                                                  
CONECT   13   12    9   14                                                  
CONECT   14   13                                                            
CONECT   15   12   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   11                                                            
CONECT   20   10   21                                                       
CONECT   21   20   10                                                       
CONECT   22    2   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27    1                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

View in JSmol

Synonyms

Value	Source
[(1'r,2S,2'r,3'r,7'r,9'r,10'r,11's)-11'-(Acetyloxy)-3',10'-dihydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0,]dodecan]-5'-en-2'-yl]methyl acetic acid	Generator

Chemical Formula

C₁₉H₂₆O₈

Average Mass

382.4090 Da

Monoisotopic Mass

382.16277 Da

IUPAC Name

[(1'R,2S,2'R,3'R,7'R,9'R,10'R,11'S)-11'-(acetyloxy)-3',10'-dihydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-2'-yl]methyl acetate

Traditional Name

(1'R,2S,2'R,3'R,7'R,9'R,10'R,11'S)-11'-(acetyloxy)-3',10'-dihydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-2'-ylmethyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC[C@]12[C@H](O)CC(C)=C[C@H]1O[C@@H]1[C@H](O)[C@@H](OC(C)=O)[C@]2(C)[C@]11CO1

InChI Identifier

InChI=1S/C19H26O8/c1-9-5-12(22)18(7-24-10(2)20)13(6-9)27-16-14(23)15(26-11(3)21)17(18,4)19(16)8-25-19/h6,12-16,22-23H,5,7-8H2,1-4H3/t12-,13-,14-,15-,16-,17+,18+,19+/m1/s1

InChI Key

DXOMWDQITCLYBJ-AVNVQCJHSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Fusarium spp.	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as trichothecenes. These are sesquiterpene mycotoxins structurally characterized by the presence of an epoxide ring and a benzopyran derivative with a variant number of hydroxyl, acetyl, or other substituents. The most important structural features causing the biological activities of trichothecenes are the 12,13-epoxy ring, the presence of hydroxyl or acetyl groups at appropriate positions on the trichothecene nucleus and the structure and position of the side-chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Trichothecenes

Alternative Parents

Substituents

Trichothecene skeleton
Oxepane
Oxane
Dicarboxylic acid or derivatives
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
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	0.45	ALOGPS
logP	-0.85	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	13.05	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	114.82 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	90.62 m³·mol⁻¹	ChemAxon
Polarizability	38.42 Å³	ChemAxon
Number of Rings	4	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

163045360

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (3alpha,4beta,7alpha)12,13-Epoxy-trichothec-9-ene-3,4,7,15-tetrol 4,15-diacetate (NP0059141)

MOL for NP0059141 ((3alpha,4beta,7alpha)12,13-Epoxy-trichothec-9-ene-3,4,7,15-tetrol 4,15-diacetate)

3D MOL for NP0059141 ((3alpha,4beta,7alpha)12,13-Epoxy-trichothec-9-ene-3,4,7,15-tetrol 4,15-diacetate)

3D SDF for NP0059141 ((3alpha,4beta,7alpha)12,13-Epoxy-trichothec-9-ene-3,4,7,15-tetrol 4,15-diacetate)

3D-SDF for NP0059141 ((3alpha,4beta,7alpha)12,13-Epoxy-trichothec-9-ene-3,4,7,15-tetrol 4,15-diacetate)

PDB for NP0059141 ((3alpha,4beta,7alpha)12,13-Epoxy-trichothec-9-ene-3,4,7,15-tetrol 4,15-diacetate)

3D PDB for NP0059141 ((3alpha,4beta,7alpha)12,13-Epoxy-trichothec-9-ene-3,4,7,15-tetrol 4,15-diacetate)

SMILES for NP0059141 ((3alpha,4beta,7alpha)12,13-Epoxy-trichothec-9-ene-3,4,7,15-tetrol 4,15-diacetate)

INCHI for NP0059141 ((3alpha,4beta,7alpha)12,13-Epoxy-trichothec-9-ene-3,4,7,15-tetrol 4,15-diacetate)

Structure for NP0059141 ((3alpha,4beta,7alpha)12,13-Epoxy-trichothec-9-ene-3,4,7,15-tetrol 4,15-diacetate)

3D Structure for NP0059141 ((3alpha,4beta,7alpha)12,13-Epoxy-trichothec-9-ene-3,4,7,15-tetrol 4,15-diacetate)