ID: ALA464997

Max Phase: Preclinical

Molecular Formula: C14H16O3

Molecular Weight: 232.28

Molecule Type: Small molecule

Representations

Synonyms (1): Drupanin
Synonyms from Alternative Forms(1):

Canonical SMILES:  CC(C)=CCc1cc(/C=C/C(=O)O)ccc1O

Standard InChI:  InChI=1S/C14H16O3/c1-10(2)3-6-12-9-11(4-7-13(12)15)5-8-14(16)17/h3-5,7-9,15H,6H2,1-2H3,(H,16,17)/b8-5+

Standard InChI Key:  HZKNHDLUFBYIQN-VMPITWQZSA-N

Molecule Features

Natural Product: No

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: 232.28

Molecular Weight (Monoisotopic): 232.1099

AlogP: 3.00

#Rotatable Bonds: 4

Polar Surface Area: 57.53

Molecular Species: ACID

HBA: 2

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 3.77

CX Basic pKa:

CX LogP: 3.56

CX LogD: 0.28

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.62

Np Likeness Score: 1.68

References

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2. Carrizo R, Sosa ME, Favier LS, Penna F, Guerreiro E, Giordano OS, Tonn CE..  (1998)  Growth-inhibitory activities of benzofuran and chromene derivatives toward Tenebrio molitor.,  61  (10): [PMID:9784153] [10.1021/np9800248]

3. Tani H, Hasumi K, Tatefuji T, Hashimoto K, Koshino H, Takahashi S..  (2010)  Inhibitory activity of Brazilian green propolis components and their derivatives on the release of cys-leukotrienes.,  18  (1): [PMID:19942440] [10.1016/j.bmc.2009.11.007]

4. Hattori H, Okuda K, Murase T, Shigetsura Y, Narise K, Semenza GL, Nagasawa H..  (2011)  Isolation, identification, and biological evaluation of HIF-1-modulating compounds from Brazilian green propolis.,  19  (18): [PMID:21865046] [10.1016/j.bmc.2011.07.060]

5. Soda M, Hu D, Endo S, Takemura M, Li J, Wada R, Ifuku S, Zhao HT, El-Kabbani O, Ohta S, Yamamura K, Toyooka N, Hara A, Matsunaga T..  (2012)  Design, synthesis and evaluation of caffeic acid phenethyl ester-based inhibitors targeting a selectivity pocket in the active site of human aldo-keto reductase 1B10.,  48  [PMID:22236472] [10.1016/j.ejmech.2011.12.034]

6. Endo S, Matsunaga T, Kanamori A, Otsuji Y, Nagai H, Sundaram K, El-Kabbani O, Toyooka N, Ohta S, Hara A..  (2012)  Selective inhibition of human type-5 17β-hydroxysteroid dehydrogenase (AKR1C3) by baccharin, a component of Brazilian propolis.,  75  (4): [PMID:22506594] [10.1021/np201002x]

7. Faini F, Labbe C, Salgado I, Coll J.  (1997)  Chemistry, toxicity and antifeedant activity of the resin of Flourensia thurifera,  25  (3): [10.1016/S0305-1978(96)00100-7]

8. Faini F, Labbe C, Coll J.  (1999)  Seasonal changes in chemical composition of epicuticular waxes from the leaves of Baccharis linearis,  27  (7): [10.1016/S0305-1978(98)00131-8]

9. Verma K, Zang T, Penning TM, Trippier PC..  (2019)  Potent and Highly Selective Aldo-Keto Reductase 1C3 (AKR1C3) Inhibitors Act as Chemotherapeutic Potentiators in Acute Myeloid Leukemia and T-Cell Acute Lymphoblastic Leukemia.,  62  (7): [PMID:30836001] [10.1021/acs.jmedchem.9b00090]

10. Verma K, Zang T, Gupta N, Penning TM, Trippier PC..  (2016)  Selective AKR1C3 Inhibitors Potentiate Chemotherapeutic Activity in Multiple Acute Myeloid Leukemia (AML) Cell Lines.,  7  (8): [PMID:27563402] [10.1021/acsmedchemlett.6b00163]

11. Rodrigues DM, Portapilla GB, Silva GM, Duarte A, Rotta CG, da Silva CHTP, de Albuquerque S, Bastos JK, Campo VL..  (2021)  Synthesis, antitumor activity and in silico analyses of amino acid derivatives of artepillin C, drupanin and baccharin from green propolis.,  47  [PMID:34454129] [10.1016/j.bmc.2021.116372]

Source

Source(1):

• Scientific Literature