picropodophyllin   Click here for help

GtoPdb Ligand ID: 7873

Synonyms: AXL1717
Compound class: Synthetic organic
Comment: Picropodophyllin is a lignan extract from podophyllin resin produced in the roots of podophyllum plants. It is an epimer of picropodophyllotoxin. Picropodophyllin has been suggested to act as a selective inhibitor of the insulin-like growth factor 1 receptor (IGF1R) and has potential antineoplastic activity [1-2]. Its effect via IGF1R have been questioned [3].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 92.68
Molecular weight 414.13
XLogP 1.64
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES COc1cc(cc(c1OC)OC)C1C2C(=O)OCC2C(c2c1cc1OCOc1c2)O
Isomeric SMILES COc1cc(cc(c1OC)OC)[C@H]1[C@@H]2C(=O)OC[C@@H]2[C@H](c2c1cc1OCOc1c2)O
InChI InChI=1S/C22H22O8/c1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h4-7,13,18-20,23H,8-9H2,1-3H3/t13-,18+,19+,20-/m0/s1
InChI Key YJGVMLPVUAXIQN-HAEOHBJNSA-N
References
1. Ekman S, Frödin JE, Harmenberg J, Bergman A, Hedlund A, Dahg P, Alvfors C, Ståhl B, Bergström S, Bergqvist M. (2011)
Clinical Phase I study with an Insulin-like Growth Factor-1 receptor inhibitor: experiences in patients with squamous non-small cell lung carcinoma.
Acta Oncol, 50 (3): 441-7. [PMID:20698809]
2. Girnita A, Girnita L, del Prete F, Bartolazzi A, Larsson O, Axelson M. (2004)
Cyclolignans as inhibitors of the insulin-like growth factor-1 receptor and malignant cell growth.
Cancer Res, 64 (1): 236-42. [PMID:14729630]
3. Linder S, Shoshan MC, Gupta RS. (2007)
Picropodophyllotoxin or podophyllotoxin does not induce cell death via insulin-like growth factor-I receptor.
Cancer Res, 67 (6): 2899; author reply 2899-900. [PMID:17363615]