ID: ALA448297

Max Phase: Preclinical

Molecular Formula: C16H14O5

Molecular Weight: 286.28

Molecule Type: Small molecule

Representations

Synonyms (3): 7-O-Methylnaringenin | Naringenin 7-Methyl Ether | Sakuranetin
Synonyms from Alternative Forms(3):

Canonical SMILES:  COc1cc(O)c2c(c1)O[C@H](c1ccc(O)cc1)CC2=O

Standard InChI:  InChI=1S/C16H14O5/c1-20-11-6-12(18)16-13(19)8-14(21-15(16)7-11)9-2-4-10(17)5-3-9/h2-7,14,17-18H,8H2,1H3/t14-/m0/s1

Standard InChI Key:  DJOJDHGQRNZXQQ-AWEZNQCLSA-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: 286.28

Molecular Weight (Monoisotopic): 286.0841

AlogP: 2.81

#Rotatable Bonds: 2

Polar Surface Area: 75.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 8.62

CX Basic pKa:

CX LogP: 2.98

CX LogD: 2.96

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.89

Np Likeness Score: 1.50

References

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9. Zhang LB, Ji J, Lei C, Wang HY, Zhao QS, Hou AJ..  (2012)  Isoprenylated flavonoid and adipogenesis-promoting constituents of Dodonaea viscosa.,  75  (4): [PMID:22512738] [10.1021/np2009797]

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11. Wesołowska O, Wiśniewski J, Sroda-Pomianek K, Bielawska-Pohl A, Paprocka M, Duś D, Duarte N, Ferreira MJ, Michalak K..  (2012)  Multidrug resistance reversal and apoptosis induction in human colon cancer cells by some flavonoids present in citrus plants.,  75  (11): [PMID:23137376] [10.1021/np3003468]

12. Wubshet SG, Tahtah Y, Heskes AM, Kongstad KT, Pateraki I, Hamberger B, Møller BL, Staerk D..  (2016)  Identification of PTP1B and α-Glucosidase Inhibitory Serrulatanes from Eremophila spp. by Combined use of Dual High-Resolution PTP1B and α-Glucosidase Inhibition Profiling and HPLC-HRMS-SPE-NMR.,  79  (4): [PMID:26960032] [10.1021/acs.jnatprod.5b01128]

13. Park I, Byun HS, Hur GM, Na M..  (2021)  Tulipiferamide A, an Alkamide from Liriodendron tulipifera, Exhibits an Anti-Inflammatory Effect via Targeting IKKβ Phosphorylation.,  84  (5.0): [PMID:33939429] [10.1021/acs.jnatprod.1c00146]

14. Ferreira RJ, Gajdács M, Kincses A, Spengler G, Dos Santos DJVA, Ferreira MU..  (2020)  Nitrogen-containing naringenin derivatives for reversing multidrug resistance in cancer.,  28  (23.0): [PMID:33038666] [10.1016/j.bmc.2020.115798]

Source

Source(1):

• Scientific Literature