ID: ALA15972

Max Phase: Unknown

Molecular Formula: C7H6O

Molecular Weight: 106.12

Molecule Type: Small molecule

Representations

Synonyms (7): Benzaldehyde | Benzaldehyde spirit | Benzoic acid aldehyde | Benzoic aldehyde | Nci-c56133 | FEMA NO. 2127 | NSC-7917
Synonyms from Alternative Forms(7):

Canonical SMILES:  O=Cc1ccccc1

Standard InChI:  InChI=1S/C7H6O/c8-6-7-4-2-1-3-5-7/h1-6H

Standard InChI Key:  HUMNYLRZRPPJDN-UHFFFAOYSA-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: Yes

Availability: No

Prodrug: No

Properties

Molecular Weight: 106.12

Molecular Weight (Monoisotopic): 106.0419

AlogP: 1.50

#Rotatable Bonds: 1

Polar Surface Area: 17.07

Molecular Species:

HBA: 1

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 1

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 1.69

CX LogD: 1.69

Aromatic Rings: 1

Heavy Atoms: 8

QED Weighted: 0.50

Np Likeness Score: 0.11

References

1. Jorgensen WL, Duffy EM..  (2000)  Prediction of drug solubility from Monte Carlo simulations.,  10  (11): [PMID:10866370] [10.1016/s0960-894x(00)00172-4]

2. Fernandez JP, Robbe Y, Chapat JP, Chanal JL, Genin M, Sentenac-Roumanou H, Fatome M..  (1983)  Relationship between metabolism and radioprotective activity of 2-phenylthiazolidine and its m-bromo derivative.,  26  (9): [PMID:6887207] [10.1021/jm00363a018]

3. Nihei K, Yamagiwa Y, Kamikawa T, Kubo I..  (2004)  2-hydroxy-4-isopropylbenzaldehyde, a potent partial tyrosinase inhibitor.,  14  (3): [PMID:14741268] [10.1016/j.bmcl.2003.11.033]

4. Caron G, Ermondi G..  (2005)  Calculating virtual log P in the alkane/water system (log P(N)(alk)) and its derived parameters deltalog P(N)(oct-alk) and log D(pH)(alk).,  48  (9): [PMID:15857133] [10.1021/jm048980b]

5. Rahnasto M, Raunio H, Poso A, Wittekindt C, Juvonen RO..  (2005)  Quantitative structure-activity relationship analysis of inhibitors of the nicotine metabolizing CYP2A6 enzyme.,  48  (2): [PMID:15658857] [10.1021/jm049536b]

6. Xue CB, Zhang L, Luo WC, Xie XY, Jiang L, Xiao T..  (2007)  3D-QSAR and molecular docking studies of benzaldehyde thiosemicarbazone, benzaldehyde, benzoic acid, and their derivatives as phenoloxidase inhibitors.,  15  (5): [PMID:17258462] [10.1016/j.bmc.2006.12.038]

7. Gu K, Bi L, Zhao M, Wang C, Ju J, Peng S..  (2007)  Toward the development of chemoprevention agents. Part 1: Design, synthesis, and anti-inflammatory activities of a new class of 2,5-disubstituted-dioxacycloalkanes.,  15  (14): [PMID:17512740] [10.1016/j.bmc.2007.05.013]

8. Pérez-Garrido A, Morales Helguera A, Abellán Guillén A, Cordeiro MN, Garrido Escudero A..  (2009)  Convenient QSAR model for predicting the complexation of structurally diverse compounds with beta-cyclodextrins.,  17  (2): [PMID:19056282] [10.1016/j.bmc.2008.11.040]

9. PubChem BioAssay data set, 

10. PubChem BioAssay data set, 

11. Liu L, Ma H, Tang Y, Chen W, Lu Y, Guo J, Duan JA..  (2012)  Discovery of estrogen receptor α modulators from natural compounds in Si-Wu-Tang series decoctions using estrogen-responsive MCF-7 breast cancer cells.,  22  (1): [PMID:22137340] [10.1016/j.bmcl.2011.11.041]

12. Vieira RP, Lessa JA, Ferreira WC, Costa FB, Bastos LF, Rocha WR, Coelho MM, Beraldo H..  (2012)  Influence of susceptibility to hydrolysis and hydrophobicity of arylsemicarbazones on their anti-nociceptive and anti-inflammatory activities.,  50  [PMID:22357114] [10.1016/j.ejmech.2012.01.048]

13. Williams DE, Steinø A, de Voogd NJ, Mauk AG, Andersen RJ..  (2012)  Halicloic acids A and B isolated from the marine sponge Haliclona sp. collected in the Philippines inhibit indoleamine 2,3-dioxygenase.,  75  (8): [PMID:22873824] [10.1021/np300345j]

14. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

15. Ford KA, Gulevich AG, Swenson TL, Casida JE..  (2011)  Neonicotinoid insecticides: oxidative stress in planta and metallo-oxidase inhibition.,  59  (9): [PMID:21476569] [10.1021/jf200485k]

16. Kim J, Seo SM, Lee SG, Shin SC, Park IK..  (2008)  Nematicidal activity of plant essential oils and components from coriander (Coriandrum sativum), Oriental sweetgum (Liquidambar orientalis), and valerian (Valeriana wallichii) essential oils against pine wood nematode (Bursaphelenchus xylophilus).,  56  (16): [PMID:18605734] [10.1021/jf800780f]

17. Teulon DA, Davidson MM, Hedderley DI, James DE, Fletcher CD, Larsen L, Green VC, Perry NB..  (2007)  4-pyridyl carbonyl and related compounds as thrips lures: effectiveness for onion thrips and new zealand flower thrips in field experiments.,  55  (15): [PMID:17602496] [10.1021/jf070389a]

18. Caboni P, Aissani N, Cabras T, Falqui A, Marotta R, Liori B, Ntalli N, Sarais G, Sasanelli N, Tocco G..  (2013)  Potent nematicidal activity of phthalaldehyde, salicylaldehyde, and cinnamic aldehyde against Meloidogyne incognita.,  61  (8): [PMID:23379671] [10.1021/jf305164m]

19. PubChem BioAssay data set, 

20. PubChem BioAssay data set, 

21. PubChem BioAssay data set, 

22. Fontaine F, Hequet A, Voisin-Chiret AS, Bouillon A, Lesnard A, Cresteil T, Jolivalt C, Rault S..  (2014)  First identification of boronic species as novel potential inhibitors of the Staphylococcus aureus NorA efflux pump.,  57  (6): [PMID:24499135] [10.1021/jm401808n]

23. Fujita T, Nishioka T, Nakajima M..  (1977)  Hydrogen-bonding parameter and its significance in quantitative structure--activity studies.,  20  (8): [PMID:894678] [10.1021/jm00218a017]

24. Loeffler LJ, Sajadi Z, Hall IH..  (1977)  Antineoplastic agents. 1. N-Protected vinyl, 1,2-dihaloethyl, and cyanomethyl esters of phenylalanine.,  20  (12): [PMID:592322] [10.1021/jm00222a008]

25. Loeffler LJ, Sajadi Z, Hall IH..  (1977)  Antineoplastic agents. 2. Structure-activity studies on N-protected vinyl, 1,2-dibromoethyl, and cyanomethyl esters of several amino acids.,  20  (12): [PMID:592323] [10.1021/jm00222a009]

26. Alam MI, Alam MA, Alam O, Nargotra A, Taneja SC, Koul S..  (2016)  Molecular modeling and snake venom phospholipase A2 inhibition by phenolic compounds: Structure-activity relationship.,  114  [PMID:26986086] [10.1016/j.ejmech.2016.03.008]

27. Soubhye J, Gelbcke M, Van Antwerpen P, Dufrasne F, Boufadi MY, Nève J, Furtmüller PG, Obinger C, Zouaoui Boudjeltia K, Meyer F..  (2017)  From Dynamic Combinatorial Chemistry to in Vivo Evaluation of Reversible and Irreversible Myeloperoxidase Inhibitors.,  8  (2): [PMID:28197313] [10.1021/acsmedchemlett.6b00417]

28. Harrell WA, Vieira RC, Ensel SM, Montgomery V, Guernieri R, Eccard VS, Campbell Y, Roxas-Duncan V, Cardellina JH, Webb RP, Smith LA..  (2017)  A matrix-focused structure-activity and binding site flexibility study of quinolinol inhibitors of botulinum neurotoxin serotype A.,  27  (3): [PMID:28043798] [10.1016/j.bmcl.2016.11.019]

29. Yang HH, Oh KE, Jo YH, Ahn JH, Liu Q, Turk A, Jang JY, Hwang BY, Lee KY, Lee MK..  (2018)  Characterization of tyrosinase inhibitory constituents from the aerial parts of Humulus japonicus using LC-MS/MS coupled online assay.,  26  (2): [PMID:29254897] [10.1016/j.bmc.2017.12.011]

30. Huber SK, Höfner G, Wanner KT..  (2019)  Application of the concept of oxime library screening by mass spectrometry (MS) binding assays to pyrrolidine-3-carboxylic acid derivatives as potential inhibitors of γ-aminobutyric acid transporter 1 (GAT1).,  27  (13): [PMID:31097402] [10.1016/j.bmc.2019.05.001]

31. Kern F, Wanner KT..  (2019)  Screening oxime libraries by means of mass spectrometry (MS) binding assays: Identification of new highly potent inhibitors to optimized inhibitors γ-aminobutyric acid transporter 1.,  27  (7): [PMID:30777661] [10.1016/j.bmc.2019.02.015]

32. Nainwal LM, Tasneem S, Akhtar W, Verma G, Khan MF, Parvez S, Shaquiquzzaman M, Akhter M, Alam MM..  (2019)  Green recipes to quinoline: A review.,  164  [PMID:30594028] [10.1016/j.ejmech.2018.11.026]

33. Nakaya T, Aizawa K, Taguchi Y, Tsuji K, Sekine S, Murakami K, Kasai M, Nakano H, Kondoh Y, Dan S, Yoshimori A, Kouji H, Takehara D, Suzuki T, Osada H, Murata M, Tanaka A, Nagai R..  (2022)  Development of Low-Molecular-Weight Compounds Targeting the Cancer-Associated KLF5 Transcription Factor.,  13  (4.0): [PMID:35450365] [10.1021/acsmedchemlett.1c00721]

Source

Source(3):

• Scientific Literature
• PubChem BioAssays
• USP Dictionary of USAN and International Drug Names