ID: ALA382330

Max Phase: Preclinical

Molecular Formula: C22H27NO4

Molecular Weight: 369.46

Molecule Type: Small molecule

Representations

Synonyms (1): (+)-Madindoline A
Synonyms from Alternative Forms(1):

Canonical SMILES:  CCCCC1=C(C)C(=O)[C@@](C)(CN2c3ccccc3[C@]3(O)CCO[C@H]23)C1=O

Standard InChI:  InChI=1S/C22H27NO4/c1-4-5-8-15-14(2)18(24)21(3,19(15)25)13-23-17-10-7-6-9-16(17)22(26)11-12-27-20(22)23/h6-7,9-10,20,26H,4-5,8,11-13H2,1-3H3/t20-,21+,22+/m0/s1

Standard InChI Key:  XPVQXXLKOCZMGG-BHDDXSALSA-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: 369.46

Molecular Weight (Monoisotopic): 369.1940

AlogP: 3.11

#Rotatable Bonds: 5

Polar Surface Area: 66.84

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 12.65

CX Basic pKa:

CX LogP: 4.49

CX LogD: 4.49

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.81

Np Likeness Score: 1.17

References

1. Yamamoto D, Sunazuka T, Hirose T, Kojima N, Kaji E, Omura S..  (2006)  Design, synthesis, and biological activities of madindoline analogues.,  16  (10): [PMID:16481161] [10.1016/j.bmcl.2006.01.107]

2. Singh S, Gajulapati V, Gajulapati K, Goo JI, Park YH, Jung HY, Lee SY, Choi JH, Kim YK, Lee K, Heo TH, Choi Y..  (2016)  Structure-activity relationship study of a series of novel oxazolidinone derivatives as IL-6 signaling blockers.,  26  (4): [PMID:26810262] [10.1016/j.bmcl.2016.01.016]

3. Zheng J, Chen D, Xu J, Ding X, Wu Y, Shen HC, Tan X..  (2021)  Small molecule approaches to treat autoimmune and inflammatory diseases (Part III): Targeting cytokines and cytokine receptor complexes.,  48  [PMID:34214508] [10.1016/j.bmcl.2021.128229]

Source

Source(1):

• Scientific Literature