integerrimine

ID: ALA488203

Cas Number: 480-79-5

PubChem CID: 5281733

Max Phase: Preclinical

Molecular Formula: C18H25NO5

Molecular Weight: 335.40

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Integerrimine | Integerrimine|Squalidine|Squalidin|480-79-5|(-)-Integerrimine|Inegerrimine|Intergerrimine|NSC 79540|UNII-3179A6U4PN|(15E)-12-Hydroxysenecionan-11,16-dione|3179A6U4PN|Senecionan-11,16-dione, 12-hydroxy-, (15E)-|CHEBI:5935|DTXSID601016480|NSC-79540|(1R,4E,6R,7R,17R)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione|(1,6)DIOXACYCLODODECINO(2,3,4-GH)PYRROLIZINE-2,7-DIONE, 3-ETHYLIDENE-3,4,5,6,9,11,13,14,14A,14B-DECAHYDRO-6-HYDROXY-5,6Show More⌵

Canonical SMILES:  C/C=C1\C[C@@H](C)[C@@](C)(O)C(=O)OCC2=CCN3CC[C@@H](OC1=O)[C@@H]23

Standard InChI:  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

Standard InChI Key:  HKODIGSRFALUTA-IKZAEVNJSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    4.7959   -3.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7810   -1.8836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3031   -2.5561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5659   -2.1303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5751   -2.9535    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3599   -3.2003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8381   -2.5278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3451   -1.8662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3819   -2.7084    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4336   -1.0469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1810   -0.7162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5191   -1.1001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8099   -0.6774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0932   -1.0780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8224    0.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1138    0.5682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5438    0.5465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2478    0.1239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9691    0.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2301    0.1063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9638    0.4747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2352   -0.6992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5483    1.1132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5520    1.2441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1263    1.3914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7919   -1.7365    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2 12  1  0
  2  3  1  0
 12 13  1  0
  3  1  1  0
 13 14  2  0
  5  6  1  0
 13 15  1  0
  6  7  1  0
 15 16  2  0
  7  8  2  0
 15 17  1  0
  8  4  1  0
 17 18  1  0
  4  5  1  0
 18 19  1  0
  4  9  1  6
 11 20  1  0
  1  5  1  0
 20 21  2  0
 19 20  1  0
  8 10  1  0
 18 22  1  6
 19 23  1  6
 10 11  1  0
 19 24  1  0
  4  2  1  0
 16 25  1  0
  2 26  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA488203

   INTEGERRIMINE

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 335.40

Molecular Weight (Monoisotopic): 335.1733

AlogP: 1.19

#Rotatable Bonds: ┄

Polar Surface Area: 76.07

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.37

CX Basic pKa: 8.14

CX LogP: 1.64

CX LogD: 0.84

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.41

Np Likeness Score: 2.96

References

1. Zalkow LH, Asibal CF, Glinski JA, Bonetti SJ, Gelbaum LT, VanDerveer D, Powis G..  (1988)  Macrocyclic pyrrolizidine alkaloids from Senecio anonymus. Separation of a complex alkaloid extract using droplet counter-current chromatography.,  51  (4): [PMID:3210016] [10.1021/np50058a005]

2.  (2008)  36  (3): [10.1016/jbse.2007.08.015]

Source

Source(1):

• Scientific Literature