calactin

ID: ALA502127

Chembl Id: CHEMBL502127

Cas Number: 20304-47-6

PubChem CID: 441849

Max Phase: Preclinical

Molecular Formula: C29H40O9

Molecular Weight: 532.63

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Calactin | Calactin|Pecilocerin B|Pekilocerin B|Poekilocerin B|Pokilocerin B|20304-47-6|6299V7SZXG|CHEBI:3299|(1S,3R,5S,7R,9R,10S,12R,14R,15S,18R,19R,22S,23R)-9,10,22-trihydroxy-7,18-dimethyl-19-(5-oxo-2H-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.03,12.05,10.015,23.018,22]pentacosane-14-carbaldehyde|UNII-6299V7SZXG|HSDB 3467|CHEMBL502127|SCHEMBL24394828|DTXSID80174192|Card-20(22)-enolide, 3-((4,6-dideoxy-beta-D-erythro-hexopyranos-2-ulos-1-yl)oxy)-2,14-dihydroxy-19-oxo-, (2alpha,3beta,5alpha)-|Show More⌵

Canonical SMILES:  C[C@@H]1C[C@@H](O)[C@]2(O)O[C@@H]3C[C@@]4(C=O)[C@@H](CC[C@@H]5[C@@H]4CC[C@]4(C)[C@@H](C6=CC(=O)OC6)CC[C@]54O)C[C@H]3O[C@@H]2O1

Standard InChI:  InChI=1S/C29H40O9/c1-15-9-23(31)29(34)25(36-15)37-21-11-17-3-4-20-19(27(17,14-30)12-22(21)38-29)5-7-26(2)18(6-8-28(20,26)33)16-10-24(32)35-13-16/h10,14-15,17-23,25,31,33-34H,3-9,11-13H2,1-2H3/t15-,17+,18-,19+,20-,21-,22-,23-,25+,26-,27-,28+,29+/m1/s1

Standard InChI Key:  OWPWFVVPBYFKBG-SXDHXEJRSA-N

Alternative Forms

1. Parent:

   

   ALA502127

   CALACTIN

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

Calculated Properties

Molecular Weight: 532.63

Molecular Weight (Monoisotopic): 532.2672

AlogP: 2.00

#Rotatable Bonds: 2

Polar Surface Area: 131.75

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.18

CX Basic pKa: 0.27

CX LogP: 1.96

CX LogD: 1.54

Aromatic Rings: ┄

Heavy Atoms: 38

QED Weighted: 0.28

Np Likeness Score: 3.57

References

1. Hamed AI, Plaza A, Balestrieri ML, Mahalel UA, Springuel IV, Oleszek W, Pizza C, Piacente S..  (2006)  Cardenolide glycosides from Pergularia tomentosa and their proapoptotic activity in Kaposi's sarcoma cells.,  69  (9): [PMID:16989527] [10.1021/np060228l]

2. Lhinhatrakool T, Sutthivaiyakit S..  (2006)  19-Nor- and 18,20-epoxy-cardenolides from the leaves of Calotropis gigantea.,  69  (8): [PMID:16933890] [10.1021/np060249f]

3. Roy MC, Chang FR, Huang HC, Chiang MY, Wu YC..  (2005)  Cytotoxic principles from the formosan milkweed, Asclepias curassavica.,  68  (10): [PMID:16252914] [10.1021/np0501740]

4. Piacente S, Masullo M, De Nève N, Dewelle J, Hamed A, Kiss R, Mijatovic T..  (2009)  Cardenolides from Pergularia tomentosa display cytotoxic activity resulting from their potent inhibition of Na+/K+-ATPase.,  72  (6): [PMID:19555122] [10.1021/np800810f]

5. PubChem BioAssay data set, 

6. Mohamed NH, Liu M, Abdel-Mageed WM, Alwahibi LH, Dai H, Ismail MA, Badr G, Quinn RJ, Liu X, Zhang L, Shoreit AA..  (2015)  Cytotoxic cardenolides from the latex of Calotropis procera.,  25  (20): [PMID:26323871] [10.1016/j.bmcl.2015.08.044]

7. Hosseini SH, Masullo M, Cerulli A, Martucciello S, Ayyari M, Pizza C, Piacente S..  (2019)  Antiproliferative Cardenolides from the Aerial Parts of Pergularia tomentosa.,  82  (1): [PMID:30629433] [10.1021/acs.jnatprod.8b00630]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays