pinostrobin

ID: ALA254613

Chembl Id: CHEMBL254613

Cas Number: 480-37-5

PubChem CID: 73201

Max Phase: Preclinical

Molecular Formula: C16H14O4

Molecular Weight: 270.28

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Pinostrombin | Pinostrobin|480-37-5|Pinostrombin|dihydrotectochrysin|(-)-pinostrobin|(2S)-pinostrobin|Pinocembrin-7-methylether|5-hydroxy-7-methoxy-2-phenylchroman-4-one|SZD9LZS694|CHEMBL254613|5-Hydroxy-7-methoxy-2-phenyl-2,3-dihydro-4H-chromen-4-one|CHEBI:80491|(2s)-5-hydroxy-7-methoxyflavanone|4H-1-Benzopyran-4-one, 2,3-dihydro-5-hydroxy-7-methoxy-2-phenyl-, (S)-|pinocembrin-7-methyl ether|(S)-2,3-Dihydro-5-hydroxy-7-methoxy-2-phenyl-4-benzopyrone|7-METHYLPINOCEMBRIN|UNII-SZD9LZS694|(2S)-5-hyShow More⌵

Canonical SMILES:  COc1cc(O)c2c(c1)O[C@H](c1ccccc1)CC2=O

Standard InChI:  InChI=1S/C16H14O4/c1-19-11-7-12(17)16-13(18)9-14(20-15(16)8-11)10-5-3-2-4-6-10/h2-8,14,17H,9H2,1H3/t14-/m0/s1

Standard InChI Key:  ORJDDOBAOGKRJV-AWEZNQCLSA-N

Alternative Forms

1. Parent:

   

   ALA254613

   PINOSTROBIN

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: 270.28

Molecular Weight (Monoisotopic): 270.0892

AlogP: 3.11

#Rotatable Bonds: 2

Polar Surface Area: 55.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.69

CX Basic pKa: ┄

CX LogP: 3.28

CX LogD: 3.26

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.91

Np Likeness Score: 1.33

References

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2. Win NN, Awale S, Esumi H, Tezuka Y, Kadota S..  (2007)  Bioactive secondary metabolites from Boesenbergia pandurata of Myanmar and their preferential cytotoxicity against human pancreatic cancer PANC-1 cell line in nutrient-deprived medium.,  70  (10): [PMID:17896818] [10.1021/np070286m]

3. Usia T, Banskota AH, Tezuka Y, Midorikawa K, Matsushige K, Kadota S..  (2002)  Constituents of Chinese propolis and their antiproliferative activities.,  65  (5): [PMID:12027739] [10.1021/np010486c]

4. Gu JQ, Park EJ, Vigo JS, Graham JG, Fong HH, Pezzuto JM, Kinghorn AD..  (2002)  Activity-guided isolation of constituents of Renealmia nicolaioides with the potential to induce the phase II enzyme quinone reductase.,  65  (11): [PMID:12444686] [10.1021/np020249p]

5. Lee S, Woo Y, Shin SY, Lee YH, Lim Y..  (2009)  Relationships between the structures of flavanone derivatives and their effects in enhancing early growth response-1 gene expression.,  19  (8): [PMID:19307119] [10.1016/j.bmcl.2009.03.017]

6. Poerwono H, Sasaki S, Hattori Y, Higashiyama K..  (2010)  Efficient microwave-assisted prenylation of pinostrobin and biological evaluation of its derivatives as antitumor agents.,  20  (7): [PMID:20219370] [10.1016/j.bmcl.2010.02.068]

7. Li F, Awale S, Tezuka Y, Esumi H, Kadota S..  (2010)  Study on the constituents of Mexican propolis and their cytotoxic activity against PANC-1 human pancreatic cancer cells.,  73  (4): [PMID:20307087] [10.1021/np900772m]

8. Yenjai C, Wanich S..  (2010)  Cytotoxicity against KB and NCI-H187 cell lines of modified flavonoids from Kaempferia parviflora.,  20  (9): [PMID:20362442] [10.1016/j.bmcl.2010.03.054]

9. Kaur K, Jain M, Kaur T, Jain R..  (2009)  Antimalarials from nature.,  17  (9): [PMID:19299148] [10.1016/j.bmc.2009.02.050]

10. Chou TH, Chen JJ, Lee SJ, Chiang MY, Yang CW, Chen IS..  (2010)  Cytotoxic flavonoids from the leaves of Cryptocarya chinensis.,  73  (9): [PMID:20704331] [10.1021/np100014j]

11. Pick A, Müller H, Mayer R, Haenisch B, Pajeva IK, Weigt M, Bönisch H, Müller CE, Wiese M..  (2011)  Structure-activity relationships of flavonoids as inhibitors of breast cancer resistance protein (BCRP).,  19  (6): [PMID:21354800] [10.1016/j.bmc.2010.12.043]

12. Ramirez-Galicia G, Martinez-Pacheco H, Garduno-Juarez R, Deeb O.  (2012)  Exploring QSAR of antiamoebic agents of isolated natural products by MLR, ANN, and RTO,  21  (9): [10.1007/s00044-011-9767-1]

13. Lee C, Lee JW, Jin Q, Jang DS, Lee SJ, Lee D, Hong JT, Kim Y, Lee MK, Hwang BY..  (2013)  Inhibitory constituents of the heartwood of Dalbergia odorifera on nitric oxide production in RAW 264.7 macrophages.,  23  (14): [PMID:23743282] [10.1016/j.bmcl.2013.04.032]

14. Kumar G, Kiran Tudu A..  (2023)  Tackling multidrug-resistant Staphylococcus aureus by natural products and their analogues acting as NorA efflux pump inhibitors.,  80  [PMID:36731248] [10.1016/j.bmc.2023.117187]

Source

Source(1):

• Scientific Literature