strebloside

ID: ALA449686

Chembl Id: CHEMBL449686

Cas Number: 59015-79-1

PubChem CID: 21123718

Max Phase: Preclinical

Molecular Formula: C31H46O10

Molecular Weight: 578.70

Molecule Type: Small molecule

Names and Identifiers

Synonyms: strebloside | Strebloside|59015-79-1|CHEMBL449686|NSC 382876|Card-20(22)-enolide, 3-((6-deoxy-2,3-di-O-methyl-beta-D-galactopyranosyl)oxy)-5,14-dihydroxy-19-oxo-, (3beta,5beta)-|(3S,5S,8R,9S,10S,13R,14S,17R)-5,14-dihydroxy-3-[(2R,3R,4S,5S,6R)-5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl]oxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde

Canonical SMILES:  CO[C@H]1[C@H](O[C@H]2CC[C@]3(C=O)[C@H]4CC[C@]5(C)[C@@H](C6=CC(=O)OC6)CC[C@]5(O)[C@@H]4CC[C@]3(O)C2)O[C@H](C)[C@H](O)[C@@H]1OC

Standard InChI:  InChI=1S/C31H46O10/c1-17-24(34)25(37-3)26(38-4)27(40-17)41-19-5-10-29(16-32)21-6-9-28(2)20(18-13-23(33)39-15-18)8-12-31(28,36)22(21)7-11-30(29,35)14-19/h13,16-17,19-22,24-27,34-36H,5-12,14-15H2,1-4H3/t17-,19+,20-,21+,22-,24+,25+,26-,27+,28-,29+,30+,31+/m1/s1

Standard InChI Key:  BGGIZHKHJBQRTI-HJKWRMQUSA-N

Alternative Forms

1. Parent:

   

   ALA449686

   STREBLOSIDE

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: 578.70

Molecular Weight (Monoisotopic): 578.3091

AlogP: 2.06

#Rotatable Bonds: 6

Polar Surface Area: 140.98

Molecular Species: NEUTRAL

HBA: 10

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.88

CX Basic pKa: 0.27

CX LogP: 1.43

CX LogD: 1.43

Aromatic Rings: ┄

Heavy Atoms: 41

QED Weighted: 0.24

Np Likeness Score: 3.02

References

1. Fiebig M, Duh CY, Pezzuto JM, Kinghorn AD, Farnsworth NR..  (1985)  Plant anticancer agents, XLI. Cardiac glycosides from Streblus asper.,  48  (6): [PMID:4093781] [10.1021/np50042a019]

2. Pezzuto JM, Che CT, McPherson DD, Zhu JP, Topcu G, Erdelmeier CA, Cordell GA..  (1991)  DNA as an affinity probe useful in the detection and isolation of biologically active natural products.,  54  (6): [PMID:1812211] [10.1021/np50078a006]

3. Ren Y, Chen WL, Lantvit DD, Sass EJ, Shriwas P, Ninh TN, Chai HB, Zhang X, Soejarto DD, Chen X, Lucas DM, Swanson SM, Burdette JE, Kinghorn AD..  (2017)  Cardiac Glycoside Constituents of Streblus asper with Potential Antineoplastic Activity.,  80  (3): [PMID:27983842] [10.1021/acs.jnatprod.6b00924]

4. Chen WL, Ren Y, Ren J, Erxleben C, Johnson ME, Gentile S, Kinghorn AD, Swanson SM, Burdette JE..  (2017)  (+)-Strebloside-Induced Cytotoxicity in Ovarian Cancer Cells Is Mediated through Cardiac Glycoside Signaling Networks.,  80  (3): [PMID:28234008] [10.1021/acs.jnatprod.6b01150]

5. Ren Y, Tan Q, Heath K, Wu S, Wilson JR, Ren J, Shriwas P, Yuan C, Ngoc Ninh T, Chai HB, Chen X, Soejarto DD, Johnson ME, Cheng X, Burdette JE, Kinghorn AD..  (2020)  Cytotoxic and non-cytotoxic cardiac glycosides isolated from the combined flowers, leaves, and twigs of Streblus asper.,  28  (4): [PMID:31953129] [10.1016/j.bmc.2019.115301]

6. Aldrich LN, Burdette JE, Carcache de Blanco E, Coss CC, Eustaquio AS, Fuchs JR, Kinghorn AD, MacFarlane A, Mize BK, Oberlies NH, Orjala J, Pearce CJ, Phelps MA, Rakotondraibe LH, Ren Y, Soejarto DD, Stockwell BR, Yalowich JC, Zhang X..  (2022)  Discovery of Anticancer Agents of Diverse Natural Origin.,  85  (3.0): [PMID:35213158] [10.1021/acs.jnatprod.2c00036]

Source

Source(1):

• Scientific Literature