ID: ALA519243

Max Phase: Preclinical

Molecular Formula: C22H28O9

Molecular Weight: 436.46

Molecule Type: Small molecule

Representations

Synonyms (2): Holacanthone | Holocanthone
Synonyms from Alternative Forms(2):

Canonical SMILES:  CC(=O)O[C@H]1C(=O)O[C@@H]2C[C@H]3C(C)=CC(=O)[C@@H](O)[C@]3(C)[C@H]3[C@]4(O)OC[C@]32[C@@H]1[C@@H](C)[C@H]4O

Standard InChI:  InChI=1S/C22H28O9/c1-8-5-12(24)17(26)20(4)11(8)6-13-21-7-29-22(28,19(20)21)16(25)9(2)14(21)15(18(27)31-13)30-10(3)23/h5,9,11,13-17,19,25-26,28H,6-7H2,1-4H3/t9-,11+,13-,14-,15-,16-,17-,19-,20-,21+,22-/m1/s1

Standard InChI Key:  OFHVBIQKCNMHKC-ISEFROCLSA-N

Molecule Features

Natural Product: Yes

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: 436.46

Molecular Weight (Monoisotopic): 436.1733

AlogP: -0.29

#Rotatable Bonds: 1

Polar Surface Area: 139.59

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 10.89

CX Basic pKa:

CX LogP: -0.34

CX LogD: -0.34

Aromatic Rings: 0

Heavy Atoms: 31

QED Weighted: 0.47

Np Likeness Score: 4.08

References

1. Van Tri M, Polonsky J, Merienne C, Sevenet T..  (1981)  Soularubinone, a new antileukemic quassionoid from Soulamea tomentosa.,  44  (3): [PMID:7264678] [10.1021/np50015a007]

2. Handa SS, Kinghorn AD, Cordell GA, Farnsworth NR..  (1983)  Plant anticancer agents XXV. Constituents of Soulamea soulameoides.,  46  (3): [PMID:6619884] [10.1021/np50027a011]

3. Perdue RE..  (1982)  KB cell culture I. Role in discovery of antitumor agents from higher plants.,  45  (4): [PMID:7130986] [10.1021/np50022a010]

4. Santana L, González-Díaz H, Quezada E, Uriarte E, Yáñez M, Viña D, Orallo F..  (2008)  Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.,  51  (21): [PMID:18834112] [10.1021/jm800656v]

5. Mata-Greenwood E, Daeuble JF, Grieco PA, Dou J, McChesney JD, Mehta RG, Kinghorn AD, Pezzuto JM..  (2001)  Novel esters of glaucarubolone as inducers of terminal differentiation of promyelocytic HL-60 cells and inhibitors of 7,12-dimethylbenz[a]anthracene-induced preneoplastic lesion formation in mouse mammary organ culture.,  64  (12): [PMID:11754601] [10.1021/np010212p]

6. Dou J, McChesney JD, Sindelar RD, Goins DK, Walker LA..  (1996)  A new quassinoid from Castela texana.,  59  (1): [PMID:8984156] [10.1021/np960013j]

7. Hamburger MO, Cordell GA..  (1987)  A direct bioautographic tlc assay for compounds possessing antibacterial activity.,  50  (1): [PMID:3110376] [10.1021/np50049a003]

8. Beutler JA, Kang MI, Robert F, Clement JA, Pelletier J, Colburn NH, McKee TC, Goncharova E, McMahon JB, Henrich CJ..  (2009)  Quassinoid inhibition of AP-1 function does not correlate with cytotoxicity or protein synthesis inhibition.,  72  (3): [PMID:19199792] [10.1021/np800732n]

9. Ramirez-Galicia G, Martinez-Pacheco H, Garduno-Juarez R, Deeb O.  (2012)  Exploring QSAR of antiamoebic agents of isolated natural products by MLR, ANN, and RTO,  21  (9): [10.1007/s00044-011-9767-1]

10. Gutierrez C, Gonzalez-Coloma A, Hoffmann JJ.  (1999)  Antifeedant properties of natural products from Parthenium argentatum, P. argentatumP. tomentosum (Asteraceae) and Castela emoryi (Simaroubeaceae) against Reticulitermes flavipes,  10  (1): [10.1016/S0926-6690(99)00003-5]

Source

Source(1):

• Scientific Literature