NP-MRD: Showing NP-Card for 4-(1-chloroethyl)-4,7-dihydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione (NP0319362)

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Record Information

Version

2.0

Created at

2022-09-11 20:21:06 UTC

Updated at

2022-09-11 20:21:06 UTC

NP-MRD ID

NP0319362

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-(1-chloroethyl)-4,7-dihydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione

Description

4-(1-Chloroethyl)-4,7-dihydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]Heptadec-11-ene-3,8-dione belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. 4-(1-chloroethyl)-4,7-dihydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione is found in Senecio selloi. Based on a literature review very few articles have been published on 4-(1-chloroethyl)-4,7-dihydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]Heptadec-11-ene-3,8-dione.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309112222212D          

 27 29  0  0  0  0            999 V2000
    7.2162    2.2373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4562    2.5583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3542    3.3769    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.7982    2.0606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    2.7950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4026    1.4990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2184    0.6948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4299    0.4522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8228    0.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2709    0.8260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5828   -0.1877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2408    0.3100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6386   -0.6709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2430   -1.2325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8501   -0.9135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2458   -0.3520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4572   -0.5946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9619   -1.2543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1814   -0.9871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1943   -0.1622    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7199    0.5127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2152    1.1725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0370    0.7712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8255    1.0138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0097    1.8180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4053    2.3796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8529   -0.0330    0.0000 C   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  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  4 25  1  0  0  0  0
 25 26  2  0  0  0  0
 23 27  1  0  0  0  0
 17 27  1  0  0  0  0
 20 27  1  0  0  0  0
M  END


  Mrv1652309112222212D          

 27 29  0  0  0  0            999 V2000
    7.2162    2.2373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4562    2.5583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3542    3.3769    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.7982    2.0606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    2.7950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4026    1.4990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2184    0.6948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4299    0.4522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8228    0.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2709    0.8260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5828   -0.1877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2408    0.3100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6386   -0.6709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2430   -1.2325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8501   -0.9135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2458   -0.3520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4572   -0.5946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9619   -1.2543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1814   -0.9871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1943   -0.1622    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7199    0.5127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2152    1.1725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0370    0.7712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8255    1.0138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0097    1.8180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4053    2.3796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8529   -0.0330    0.0000 C   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  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  4 25  1  0  0  0  0
 25 26  2  0  0  0  0
 23 27  1  0  0  0  0
 17 27  1  0  0  0  0
 20 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0319362

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(Cl)C1(O)CC(C)C(O)(CO)C(=O)OCC2=CCN3CCC(OC1=O)C23

> <INCHI_IDENTIFIER>
InChI=1S/C18H26ClNO7/c1-10-7-17(24,11(2)19)16(23)27-13-4-6-20-5-3-12(14(13)20)8-26-15(22)18(10,25)9-21/h3,10-11,13-14,21,24-25H,4-9H2,1-2H3

> <INCHI_KEY>
CGCFGXYYCACKOW-UHFFFAOYSA-N

> <FORMULA>
C18H26ClNO7

> <MOLECULAR_WEIGHT>
403.86

> <EXACT_MASS>
403.1397799

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
39.479401417393234

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(1-chloroethyl)-4,7-dihydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0^{14,17}]heptadec-11-ene-3,8-dione

> <JCHEM_LOGP>
-0.1883664493333338

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
11.774434642312517

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.165455853580292

> <JCHEM_PKA_STRONGEST_BASIC>
6.922769382375687

> <JCHEM_POLAR_SURFACE_AREA>
116.53

> <JCHEM_REFRACTIVITY>
96.11789999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4-(1-chloroethyl)-4,7-dihydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0^{14,17}]heptadec-11-ene-3,8-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      13.470   4.176   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.052   4.775   0.000  0.00  0.00           C+0
HETATM    3 Cl   UNK     0      11.861   6.304   0.000  0.00  0.00          Cl+0
HETATM    4  C   UNK     0      10.823   3.846   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      10.122   5.217   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      11.951   2.798   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.608   1.297   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.136   0.844   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.736   0.249   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      13.572   1.542   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      14.155  -0.350   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      15.383   0.579   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      12.392  -1.252   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      13.520  -2.301   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      10.920  -1.705   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       9.792  -0.657   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.320  -1.110   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.396  -2.341   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.939  -1.843   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       5.963  -0.303   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       5.077   0.957   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.002   2.189   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.536   1.440   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       9.008   1.892   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       9.351   3.394   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.223   4.442   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       7.192  -0.062   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6   25                                             
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11   13                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11                                                            
CONECT   13    9   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   27                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   27                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   27                                                  
CONECT   24   23   25                                                       
CONECT   25   24    4   26                                                  
CONECT   26   25                                                            
CONECT   27   23   17   20                                                  
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₂₆ClNO₇

Average Mass

403.8600 Da

Monoisotopic Mass

403.13978 Da

IUPAC Name

4-(1-chloroethyl)-4,7-dihydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0^{14,17}]heptadec-11-ene-3,8-dione

Traditional Name

4-(1-chloroethyl)-4,7-dihydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0^{14,17}]heptadec-11-ene-3,8-dione

CAS Registry Number

Not Available

SMILES

CC(Cl)C1(O)CC(C)C(O)(CO)C(=O)OCC2=CCN3CCC(OC1=O)C23

InChI Identifier

InChI=1S/C18H26ClNO7/c1-10-7-17(24,11(2)19)16(23)27-13-4-6-20-5-3-12(14(13)20)8-26-15(22)18(10,25)9-21/h3,10-11,13-14,21,24-25H,4-9H2,1-2H3

InChI Key

CGCFGXYYCACKOW-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Senecio selloi	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Not Available

Direct Parent

Macrolides and analogues

Alternative Parents

Substituents

Senecionan-skeleton
Macrolide
Alkaloid or derivatives
Pyrrolizine
Dicarboxylic acid or derivatives
N-alkylpyrrolidine
Tertiary alcohol
Pyrroline
Pyrrolidine
Amino acid or derivatives
Carboxylic acid ester
Chlorohydrin
Halohydrin
Lactone
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid derivative
Oxacycle
Azacycle
Organoheterocyclic compound
Organohalogen compound
Alkyl chloride
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Alcohol
Carbonyl group
Organic oxygen compound
Amine
Alkyl halide
Organochloride
Organonitrogen compound
Organooxygen compound
Primary 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	-0.19	ChemAxon
pKa (Strongest Acidic)	11.17	ChemAxon
pKa (Strongest Basic)	6.92	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	116.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	96.12 m³·mol⁻¹	ChemAxon
Polarizability	39.48 Å³	ChemAxon
Number of Rings	3	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

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

152771922

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-(1-chloroethyl)-4,7-dihydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione (NP0319362)

MOL for NP0319362 (4-(1-chloroethyl)-4,7-dihydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione)

3D MOL for NP0319362 (4-(1-chloroethyl)-4,7-dihydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione)

3D SDF for NP0319362 (4-(1-chloroethyl)-4,7-dihydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione)

3D-SDF for NP0319362 (4-(1-chloroethyl)-4,7-dihydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione)

PDB for NP0319362 (4-(1-chloroethyl)-4,7-dihydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione)

3D PDB for NP0319362 (4-(1-chloroethyl)-4,7-dihydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione)

SMILES for NP0319362 (4-(1-chloroethyl)-4,7-dihydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione)

INCHI for NP0319362 (4-(1-chloroethyl)-4,7-dihydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione)

Structure for NP0319362 (4-(1-chloroethyl)-4,7-dihydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione)

3D Structure for NP0319362 (4-(1-chloroethyl)-4,7-dihydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione)