rohitukine

ID: ALA1077604

Chembl Id: CHEMBL1077604

Cas Number: 71294-60-5

PubChem CID: 13422573

Max Phase: Preclinical

Molecular Formula: C16H19NO5

Molecular Weight: 305.33

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Rohitukine | Rohitukine|71294-60-5|5,7-dihydroxy-8-[(3S,4R)-3-hydroxy-1-methylpiperidin-4-yl]-2-methylchromen-4-one|5,7-Dihydroxy-8-[(3R,4S)-3-hydroxy-1-methylpiperidin-4-yl]-2-methylchromen-4-one|5,7-Dihydroxy-8-[(3S,4R)-3-hydroxy-1-methylpiperidin-4-yl]-2-methyl-4H-1-benzopyran-4-one|NSC623611|5,7-Dihydroxy-8-((3S,4R)-3-hydroxy-1-methylpiperidin-4-yl)-2-methyl-4H-chromen-4-one|5,7-dihydroxy-8-[(3S,4R)-3-hydroxy-1-methylpiperidin-4-yl]-2-methyl-4H-chromen-4-one|CHEMBL1077604|SCHEMBL23718142|DTXShow More⌵

Canonical SMILES:  Cc1cc(=O)c2c(O)cc(O)c([C@H]3CCN(C)C[C@H]3O)c2o1

Standard InChI:  InChI=1S/C16H19NO5/c1-8-5-10(18)15-12(20)6-11(19)14(16(15)22-8)9-3-4-17(2)7-13(9)21/h5-6,9,13,19-21H,3-4,7H2,1-2H3/t9-,13+/m0/s1

Standard InChI Key:  MOCVYVBNJQIVOV-TVQRCGJNSA-N

Alternative Forms

1. Parent:

   

   ALA1077604

   ROHITUKINE

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: 305.33

Molecular Weight (Monoisotopic): 305.1263

AlogP: 1.29

#Rotatable Bonds: 1

Polar Surface Area: 94.14

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.68

CX Basic pKa: 7.32

CX LogP: 0.74

CX LogD: 0.65

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.73

Np Likeness Score: 1.48

References

1. Ismail IS, Nagakura Y, Hirasawa Y, Hosoya T, Lazim MI, Lajis NH, Shiro M, Morita H..  (2009)  Chrotacumines A-D, chromone alkaloids from Dysoxylum acutangulum.,  72  (10): [PMID:19757855] [10.1021/np9003849]

2. Baell JB..  (2016)  Feeling Nature's PAINS: Natural Products, Natural Product Drugs, and Pan Assay Interference Compounds (PAINS).,  79  (3): [PMID:26900761] [10.1021/acs.jnatprod.5b00947]

3. Kumar V, Guru SK, Jain SK, Joshi P, Gandhi SG, Bharate SB, Bhushan S, Bharate SS, Vishwakarma RA..  (2016)  A chromatography-free isolation of rohitukine from leaves of Dysoxylum binectariferum: Evaluation for in vitro cytotoxicity, Cdk inhibition and physicochemical properties.,  26  (15): [PMID:27363938] [10.1016/j.bmcl.2016.06.046]

4. Bharate SB, Kumar V, Jain SK, Mintoo MJ, Guru SK, Nuthakki VK, Sharma M, Bharate SS, Gandhi SG, Mondhe DM, Bhushan S, Vishwakarma RA..  (2018)  Discovery and Preclinical Development of IIIM-290, an Orally Active Potent Cyclin-Dependent Kinase Inhibitor.,  61  (4): [PMID:29370702] [10.1021/acs.jmedchem.7b01765]

5. Zhao L, Yuan X, Wang J, Feng Y, Ji F, Li Z, Bian J..  (2019)  A review on flavones targeting serine/threonine protein kinases for potential anticancer drugs.,  27  (5): [PMID:30733087] [10.1016/j.bmc.2019.01.027]

Source

Source(1):

• Scientific Literature