NP-MRD: Showing NP-Card for intergerrimine (NP0323412)

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Record Information

Version

2.0

Created at

2022-09-12 02:49:16 UTC

Updated at

2022-09-12 02:49:17 UTC

NP-MRD ID

NP0323412

Secondary Accession Numbers

None

Natural Product Identification

Common Name

intergerrimine

Description

SCHEMBL18952968 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. intergerrimine is found in Senecio magnificus, Jacobaea subalpina and Senecio vulgaris. Based on a literature review very few articles have been published on SCHEMBL18952968.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309122204492D          

 24 26  0  0  1  0            999 V2000
    5.3780    3.4264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9824    2.8648    0.0000 C   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
    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  1  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  2  0  0  0  0  0  0  0  0  0
    7.2709    0.8260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5828   -0.1877    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  1  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  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  6  0  0  0
  7 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 19  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  3 22  1  0  0  0  0
 22 23  2  0  0  0  0
 20 24  1  0  0  0  0
 14 24  1  0  0  0  0
 24 17  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0323412

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C1\C[C@@H](C)[C@](C)(O)C(=O)OCC2=CCN3CC[C@@H](OC1=O)[C@@H]23

> <INCHI_IDENTIFIER>
InChI=1S/C18H25NO5/c1-4-12-9-11(2)18(3,22)17(21)23-10-13-5-7-19-8-6-14(15(13)19)24-16(12)20/h4-5,11,14-15,22H,6-10H2,1-3H3/b12-4-/t11-,14-,15-,18+/m1/s1

> <INCHI_KEY>
HKODIGSRFALUTA-VMMLDVGYSA-N

> <FORMULA>
C18H25NO5

> <MOLECULAR_WEIGHT>
335.4

> <EXACT_MASS>
335.173272909

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
35.11435141294727

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4Z,6R,7S,17R)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0^{14,17}]heptadec-11-ene-3,8-dione

> <JCHEM_LOGP>
1.6438626153333336

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.370863309435826

> <JCHEM_PKA_STRONGEST_BASIC>
7.136068783494923

> <JCHEM_POLAR_SURFACE_AREA>
76.07

> <JCHEM_REFRACTIVITY>
89.40659999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4Z,6R,7S,17R)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0^{14,17}]heptadec-11-ene-3,8-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      10.039   6.396   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.167   5.348   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.823   3.846   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.951   2.798   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.608   1.297   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.136   0.844   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.736   0.249   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.572   1.542   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      14.155  -0.350   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      12.392  -1.252   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      13.520  -2.301   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      10.920  -1.705   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       9.792  -0.657   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.320  -1.110   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.396  -2.341   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.939  -1.843   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       5.963  -0.303   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       5.077   0.957   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.002   2.189   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.536   1.440   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.008   1.892   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       9.351   3.394   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       8.223   4.442   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       7.192  -0.062   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   22                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   24                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   24                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   24                                                  
CONECT   21   20   22                                                       
CONECT   22   21    3   23                                                  
CONECT   23   22                                                            
CONECT   24   20   14   17                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₂₅NO₅

Average Mass

335.4000 Da

Monoisotopic Mass

335.17327 Da

IUPAC Name

(1R,4Z,6R,7S,17R)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0^{14,17}]heptadec-11-ene-3,8-dione

Traditional Name

(1R,4Z,6R,7S,17R)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0^{14,17}]heptadec-11-ene-3,8-dione

CAS Registry Number

Not Available

SMILES

C\C=C1\C[C@@H](C)[C@](C)(O)C(=O)OCC2=CCN3CC[C@@H](OC1=O)[C@@H]23

InChI Identifier

InChI=1S/C18H25NO5/c1-4-12-9-11(2)18(3,22)17(21)23-10-13-5-7-19-8-6-14(15(13)19)24-16(12)20/h4-5,11,14-15,22H,6-10H2,1-3H3/b12-4-/t11-,14-,15-,18+/m1/s1

InChI Key

HKODIGSRFALUTA-VMMLDVGYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Senecio magnificus	LOTUS Database	35616633
Senecio subalpinus	LOTUS Database	35616633
Senecio vulgaris	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
Pyrrolidine
Pyrroline
Tertiary alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Amino acid or derivatives
Carboxylic acid ester
Lactone
Tertiary amine
Tertiary aliphatic amine
Carboxylic acid derivative
Oxacycle
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic nitrogen compound
Organic oxygen compound
Carbonyl group
Amine
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	1.64	ChemAxon
pKa (Strongest Acidic)	12.37	ChemAxon
pKa (Strongest Basic)	7.14	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	76.07 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	89.41 m³·mol⁻¹	ChemAxon
Polarizability	35.11 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

16739574

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12299896

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for intergerrimine (NP0323412)

MOL for NP0323412 (intergerrimine)

3D MOL for NP0323412 (intergerrimine)

3D SDF for NP0323412 (intergerrimine)

3D-SDF for NP0323412 (intergerrimine)

PDB for NP0323412 (intergerrimine)

3D PDB for NP0323412 (intergerrimine)

SMILES for NP0323412 (intergerrimine)

INCHI for NP0323412 (intergerrimine)

Structure for NP0323412 (intergerrimine)

3D Structure for NP0323412 (intergerrimine)