8,9-Dihydroxy-7,8,9-trimethyl-2a-oxy-2,3,4,4a,8,9,12,12b-octahydro-7H-5,11-dioxa-2a-aza-cycloundeca[cd]pentalene-6,10-dione

ID: ALA469442

Chembl Id: CHEMBL469442

Cas Number: 35337-98-5

PubChem CID: 21586627

Max Phase: Preclinical

Molecular Formula: C16H23NO7

Molecular Weight: 341.36

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Monocrotaline N-Oxide | Monocrotaline N-oxide|Monocrotaline oxide|2LCP0RBK6G|35337-98-5|Monocrotaline, N-oxide|(1R,4R,5R,6R,16R)-5,6-dihydroxy-4,5,6-trimethyl-13-oxido-2,8-dioxa-13-azoniatricyclo[8.5.1.013,16]hexadec-10-ene-3,7-dione|UNII-2LCP0RBK6G|CHEMBL469442|14,19-Dihydro-12,13-dihydroxy-20-norcrotalanan-11,15-dione 4-oxide (13-alpha,14-alpha)-|20-Norcrotalanan-11,15-dione, 14,19-dihydro-12,13-dihydroxy-, 4-oxide, (13-alpha,14-alpha)-|20-Norcrotalanan-11,15-dione, 14,19-dihydro-12,13-dihydroShow More⌵

Canonical SMILES:  C[C@H]1C(=O)O[C@@H]2CC[N+]3([O-])CC=C(COC(=O)[C@](C)(O)[C@]1(C)O)[C@H]23

Standard InChI:  InChI=1S/C16H23NO7/c1-9-13(18)24-11-5-7-17(22)6-4-10(12(11)17)8-23-14(19)16(3,21)15(9,2)20/h4,9,11-12,20-21H,5-8H2,1-3H3/t9-,11+,12+,15+,16-,17?/m0/s1

Standard InChI Key:  LHVAZUAALQTANZ-ANYXPJNNSA-N

Alternative Forms

1. Parent:

   

   ALA469442

   MONOCROTALINE N-OXIDE

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: 341.36

Molecular Weight (Monoisotopic): 341.1475

AlogP: -0.38

#Rotatable Bonds: 0

Polar Surface Area: 116.12

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 11.49

CX Basic pKa: 2.82

CX LogP: -1.46

CX LogD: -1.46

Aromatic Rings: 0

Heavy Atoms: 24

QED Weighted: 0.27

Np Likeness Score: 3.09

References

1. Zalkow LH, Glinski JA, Gelbaum LT, Moore D, Melder D, Powis G..  (1988)  Semisynthetic pyrrolizidine alkaloid N-oxide antitumor agents. Esters of heliotridine.,  31  (8): [PMID:3397989] [10.1021/jm00403a008]

2. 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]

3. Thoden TC, Boppré M, Hallmann J..  (2009)  Effects of pyrrolizidine alkaloids on the performance of plant-parasitic and free-living nematodes.,  65  (7): [PMID:19378265] [10.1002/ps.1764]

Source

Source(1):

• Scientific Literature