NP-MRD: Showing NP-Card for 8-Propanoylneosolaniol (NP0337805)

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Record Information

Version

2.0

Created at

2024-09-11 12:33:06 UTC

Updated at

2024-09-11 12:33:06 UTC

NP-MRD ID

NP0337805

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-Propanoylneosolaniol

Description

8-Propanoylneosolaniol 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. Based on a literature review very few articles have been published on 8-Propanoylneosolaniol.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05262315052D          

 31 34  0  0  0  0            999 V2000
    0.6689   -3.7075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0456   -4.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0456   -4.9450    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6689   -5.3575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3834   -4.9450    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3834   -4.1200    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0978   -3.7075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0978   -5.3575    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8123   -4.9450    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8123   -4.1200    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7600   -3.7075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7600   -5.3575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3834   -5.7700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0978   -6.1825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6373   -4.9450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2248   -5.6594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9383   -6.6873    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8232   -5.2789    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6239   -5.0800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0958   -7.4971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4745   -4.9450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1890   -5.3575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9034   -4.9450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4745   -4.1200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6689   -7.0075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0456   -7.4200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6689   -6.1825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3834   -7.4200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0958   -8.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3814   -8.7346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8103   -8.7346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  5  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10  7  1  6  0  0  0
  2 11  1  0  0  0  0
  3 12  1  6  0  0  0
  5 13  1  6  0  0  0
  8 14  1  1  0  0  0
  9 16  1  1  0  0  0
 16 15  1  0  0  0  0
  8 17  1  0  0  0  0
 10 18  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 17 20  1  1  0  0  0
 12 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21 24  2  0  0  0  0
 13 27  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
 29 20  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
  9 15  1  6  0  0  0
M  END


  Mrv2104 05262315052D          

 31 34  0  0  0  0            999 V2000
    0.6689   -3.7075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0456   -4.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0456   -4.9450    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6689   -5.3575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3834   -4.9450    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3834   -4.1200    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0978   -3.7075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0978   -5.3575    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8123   -4.9450    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8123   -4.1200    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7600   -3.7075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7600   -5.3575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3834   -5.7700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0978   -6.1825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6373   -4.9450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2248   -5.6594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9383   -6.6873    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8232   -5.2789    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6239   -5.0800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0958   -7.4971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4745   -4.9450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1890   -5.3575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9034   -4.9450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4745   -4.1200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6689   -7.0075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0456   -7.4200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6689   -6.1825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3834   -7.4200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0958   -8.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3814   -8.7346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8103   -8.7346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  5  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10  7  1  6  0  0  0
  2 11  1  0  0  0  0
  3 12  1  6  0  0  0
  5 13  1  6  0  0  0
  8 14  1  1  0  0  0
  9 16  1  1  0  0  0
 16 15  1  0  0  0  0
  8 17  1  0  0  0  0
 10 18  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 17 20  1  1  0  0  0
 12 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21 24  2  0  0  0  0
 13 27  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
 29 20  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
  9 15  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0337805

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(=O)O[C@H]1C[C@@]2(COC(C)=O)[C@H](O[C@@H]3[C@H](O)[C@@H](OC(C)=O)[C@@]2(C)[C@]32CO2)C=C1C

> <INCHI_IDENTIFIER>
InChI=1/C22H30O9/c1-6-16(25)30-14-8-21(9-27-12(3)23)15(7-11(14)2)31-19-17(26)18(29-13(4)24)20(21,5)22(19)10-28-22/h7,14-15,17-19,26H,6,8-10H2,1-5H3/t14-,15+,17+,18+,19+,20+,21+,22-/s2

> <INCHI_KEY>
ZSGWJLBSFZRJAT-PMYCIFIANA-N

> <FORMULA>
C22H30O9

> <MOLECULAR_WEIGHT>
438.473

> <EXACT_MASS>
438.188982546

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
44.430377204204184

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1'S,2S,2'R,4'S,7'R,9'R,10'R,11'S)-11'-(acetyloxy)-2'-[(acetyloxy)methyl]-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-4'-yl propanoate

> <JCHEM_LOGP>
0.28784979566666713

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.072305054496203

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6419737691633602

> <JCHEM_POLAR_SURFACE_AREA>
120.89000000000001

> <JCHEM_REFRACTIVITY>
104.39359999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1'S,2S,2'R,4'S,7'R,9'R,10'R,11'S)-11'-(acetyloxy)-2'-[(acetyloxy)methyl]-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-4'-yl propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

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       1.249  -6.921   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.085  -7.691   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.085  -9.231   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.249 -10.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.582  -9.231   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.582  -7.691   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.916  -6.921   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.916 -10.001   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.250  -9.231   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.250  -7.691   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.419  -6.921   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.419 -10.001   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.582 -10.771   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.916 -11.541   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.790  -9.231   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.020 -10.564   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.351 -12.483   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.003  -9.854   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.498  -9.483   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       7.645 -13.995   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.752  -9.231   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.086 -10.001   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.420  -9.231   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.752  -7.691   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.249 -13.081   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.085 -13.851   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       1.249 -11.541   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.582 -13.851   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.645 -15.535   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       6.312 -16.305   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       8.979 -16.305   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   11                                                  
CONECT    3    2    4   12                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8   13                                             
CONECT    6    1    7    5                                                  
CONECT    7    6   10                                                       
CONECT    8    5    9   14   17                                             
CONECT    9    8   10   16   15                                             
CONECT   10    9    7   18                                                  
CONECT   11    2                                                            
CONECT   12    3   21                                                       
CONECT   13    5   27                                                       
CONECT   14    8                                                            
CONECT   15   16    9                                                       
CONECT   16    9   15                                                       
CONECT   17    8   18   20                                                  
CONECT   18   10   17   19                                                  
CONECT   19   18                                                            
CONECT   20   17   29                                                       
CONECT   21   12   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21                                                            
CONECT   25   26   27   28                                                  
CONECT   26   25                                                            
CONECT   27   13   25                                                       
CONECT   28   25                                                            
CONECT   29   20   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₀O₉

Average Mass

438.4730 Da

Monoisotopic Mass

438.18898 Da

IUPAC Name

(1'S,2S,2'R,4'S,7'R,9'R,10'R,11'S)-11'-(acetyloxy)-2'-[(acetyloxy)methyl]-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-4'-yl propanoate

Traditional Name

(1'S,2S,2'R,4'S,7'R,9'R,10'R,11'S)-11'-(acetyloxy)-2'-[(acetyloxy)methyl]-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-4'-yl propanoate

CAS Registry Number

Not Available

SMILES

CCC(=O)O[C@H]1C[C@@]2(COC(C)=O)[C@H](O[C@@H]3[C@H](O)[C@@H](OC(C)=O)[C@@]2(C)[C@]32CO2)C=C1C

InChI Identifier

InChI=1/C22H30O9/c1-6-16(25)30-14-8-21(9-27-12(3)23)15(7-11(14)2)31-19-17(26)18(29-13(4)24)20(21,5)22(19)10-28-22/h7,14-15,17-19,26H,6,8-10H2,1-5H3/t14-,15+,17+,18+,19+,20+,21+,22-/s2

InChI Key

ZSGWJLBSFZRJAT-PMYCIFIANA-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 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
Tricarboxylic acid or derivatives
Oxepane
Oxane
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Alcohol
Carbonyl group
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	0.29	ChemAxon
pKa (Strongest Acidic)	13.07	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	120.89 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	104.39 m³·mol⁻¹	ChemAxon
Polarizability	44.43 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

Not Available

Showing NP-Card for 8-Propanoylneosolaniol (NP0337805)

MOL for NP0337805 (8-Propanoylneosolaniol)

3D MOL for NP0337805 (8-Propanoylneosolaniol)

3D SDF for NP0337805 (8-Propanoylneosolaniol)

3D-SDF for NP0337805 (8-Propanoylneosolaniol)

PDB for NP0337805 (8-Propanoylneosolaniol)

3D PDB for NP0337805 (8-Propanoylneosolaniol)

SMILES for NP0337805 (8-Propanoylneosolaniol)

INCHI for NP0337805 (8-Propanoylneosolaniol)

Structure for NP0337805 (8-Propanoylneosolaniol)

3D Structure for NP0337805 (8-Propanoylneosolaniol)