ID: ALA47037

Max Phase: Preclinical

Molecular Formula: C17H16O5

Molecular Weight: 300.31

Molecule Type: Small molecule

Representations

Synonyms (1): Combretastatin A-2
Synonyms from Alternative Forms(1):

Canonical SMILES:  COc1ccc(/C=C\c2cc(OC)c3c(c2)OCO3)cc1O

Standard InChI:  InChI=1S/C17H16O5/c1-19-14-6-5-11(7-13(14)18)3-4-12-8-15(20-2)17-16(9-12)21-10-22-17/h3-9,18H,10H2,1-2H3/b4-3-

Standard InChI Key:  YTVCXBVFGQEBAL-ARJAWSKDSA-N

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

Properties

Molecular Weight: 300.31

Molecular Weight (Monoisotopic): 300.0998

AlogP: 3.31

#Rotatable Bonds: 4

Polar Surface Area: 57.15

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 9.84

CX Basic pKa:

CX LogP: 3.32

CX LogD: 3.32

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.88

Np Likeness Score: 0.83

References

1. Pettit GR, Singh SB, Boyd MR, Hamel E, Pettit RK, Schmidt JM, Hogan F..  (1995)  Antineoplastic agents. 291. Isolation and synthesis of combretastatins A-4, A-5, and A-6(1a),  38  (10): [PMID:7752190] [10.1021/jm00010a011]

2. Pettit GR, Anderson CR, Herald DL, Jung MK, Lee DJ, Hamel E, Pettit RK..  (2003)  Antineoplastic agents. 487. Synthesis and biological evaluation of the antineoplastic agent 3,4-methylenedioxy-5,4'-dimethoxy-3'-amino-Z-stilbene and derived amino acid amides.,  46  (4): [PMID:12570374] [10.1021/jm020204l]

3. Simoni D, Romagnoli R, Baruchello R, Rondanin R, Grisolia G, Eleopra M, Rizzi M, Tolomeo M, Giannini G, Alloatti D, Castorina M, Marcellini M, Pisano C..  (2008)  Novel A-ring and B-ring modified combretastatin A-4 (CA-4) analogues endowed with interesting cytotoxic activity.,  51  (19): [PMID:18783207] [10.1021/jm8005004]

4. Messaoudi S, Tréguier B, Hamze A, Provot O, Peyrat JF, De Losada JR, Liu JM, Bignon J, Wdzieczak-Bakala J, Thoret S, Dubois J, Brion JD, Alami M..  (2009)  Isocombretastatins a versus combretastatins a: the forgotten isoCA-4 isomer as a highly promising cytotoxic and antitubulin agent.,  52  (14): [PMID:19530698] [10.1021/jm900321u]

5. Pettit GR, Thornhill A, Melody N, Knight JC..  (2009)  Antineoplastic agents. 578. Synthesis of stilstatins 1 and 2 and their water-soluble prodrugs.,  72  (3): [PMID:19228038] [10.1021/np800608c]

6. Kiselyov AS, Semenova MN, Chernyshova NB, Leitao A, Samet AV, Kislyi KA, Raihstat MM, Oprea T, Lemcke H, Lantow M, Weiss DG, Ikizalp NN, Kuznetsov SA, Semenov VV..  (2010)  Novel derivatives of 1,3,4-oxadiazoles are potent mitostatic agents featuring strong microtubule depolymerizing activity in the sea urchin embryo and cell culture assays.,  45  (5): [PMID:20110137] [10.1016/j.ejmech.2009.12.072]

7. Semenov VV, Kiselyov AS, Titov IY, Sagamanova IK, Ikizalp NN, Chernysheva NB, Tsyganov DV, Konyushkin LD, Firgang SI, Semenov RV, Karmanova IB, Raihstat MM, Semenova MN..  (2010)  Synthesis of antimitotic polyalkoxyphenyl derivatives of combretastatin using plant allylpolyalkoxybenzenes.,  73  (11): [PMID:21049975] [10.1021/np1004278]

8. Titov IY, Sagamanova IK, Gritsenko RT, Karmanova IB, Atamanenko OP, Semenova MN, Semenov VV..  (2011)  Application of plant allylpolyalkoxybenzenes in synthesis of antimitotic phenstatin analogues.,  21  (6): [PMID:21345676] [10.1016/j.bmcl.2011.01.124]

9. Demchuk DV, Samet AV, Chernysheva NB, Ushkarov VI, Stashina GA, Konyushkin LD, Raihstat MM, Firgang SI, Philchenkov AA, Zavelevich MP, Kuiava LM, Chekhun VF, Blokhin DY, Kiselyov AS, Semenova MN, Semenov VV..  (2014)  Synthesis and antiproliferative activity of conformationally restricted 1,2,3-triazole analogues of combretastatins in the sea urchin embryo model and against human cancer cell lines.,  22  (2): [PMID:24387982] [10.1016/j.bmc.2013.12.015]

10. Tsyganov DV, Khrustalev VN, Konyushkin LD, Raihstat MM, Firgang SI, Semenov RV, Kiselyov AS, Semenova MN, Semenov VV..  (2014)  3-(5-)-Amino-o-diarylisoxazoles: regioselective synthesis and antitubulin activity.,  73  [PMID:24388833] [10.1016/j.ejmech.2013.12.006]

Source

Source(1):

• Scientific Literature