ID: ALA449062

Max Phase: Phase

Molecular Formula: C10H16

Molecular Weight: 136.24

Molecule Type: Small molecule

Representations

Synonyms (18): (d)-limonene | Cajeputene | Cinene | D-limonene | Dipenten | Dipentene | Dipentene no. 122 | Eulimen | Kautschin | Limonene | Limonene, d- | Limonene, dl- | Nesol | Orange x | FEMA NO. 2633 | NSC-21446 | NSC-757069 | NSC-844
Synonyms from Alternative Forms(18):

Canonical SMILES:  C=C(C)[C@H]1CC=C(C)CC1

Standard InChI:  InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,10H,1,5-7H2,2-3H3/t10-/m0/s1

Standard InChI Key:  XMGQYMWWDOXHJM-JTQLQIEISA-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: 136.24

Molecular Weight (Monoisotopic): 136.1252

AlogP: 3.31

#Rotatable Bonds: 1

Polar Surface Area: 0.00

Molecular Species:

HBA: 0

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 0

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 3.22

CX LogD: 3.22

Aromatic Rings: 0

Heavy Atoms: 10

QED Weighted: 0.49

Np Likeness Score: 2.36

References

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6. Himejima M, Kubo I..  (1992)  Antimicrobial agents from Licaria puchuri-major and their synergistic effect with polygodial.,  55  (5): [PMID:1517735] [10.1021/np50083a010]

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8. Graebin CS, Madeira Mde F, Yokoyama-Yasunaka JK, Miguel DC, Uliana SR, Benitez D, Cerecetto H, González M, Rosa RG, Eifler-Lima VL..  (2010)  Synthesis and in vitro activity of limonene derivatives against Leishmania and Trypanosoma.,  45  (4): [PMID:20116908] [10.1016/j.ejmech.2009.12.061]

9. Greene N, Fisk L, Naven RT, Note RR, Patel ML, Pelletier DJ..  (2010)  Developing structure-activity relationships for the prediction of hepatotoxicity.,  23  (7): [PMID:20553011] [10.1021/tx1000865]

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11. Duelund L, Amiot A, Fillon A, Mouritsen OG..  (2012)  Influence of the active compounds of Perilla frutescens leaves on lipid membranes.,  75  (2): [PMID:22272932] [10.1021/np200713q]

12. Furneri PM, Mondello L, Mandalari G, Paolino D, Dugo P, Garozzo A, Bisignano G..  (2012)  In vitro antimycoplasmal activity of Citrus bergamia essential oil and its major components.,  52  [PMID:22465092] [10.1016/j.ejmech.2012.03.005]

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

14. Zhang JS, Zhao NN, Liu QZ, Liu ZL, Du SS, Zhou L, Deng ZW..  (2011)  Repellent constituents of essential oil of Cymbopogon distans aerial parts against two stored-product insects.,  59  (18): [PMID:21819085] [10.1021/jf202266n]

15. Ntalli NG, Ferrari F, Giannakou I, Menkissoglu-Spiroudi U..  (2010)  Phytochemistry and nematicidal activity of the essential oils from 8 Greek Lamiaceae aromatic plants and 13 terpene components.,  58  (13): [PMID:20527965] [10.1021/jf100797m]

16. Kordali S, Kesdek M, Çakir A..  (2007)  Toxicity of monoterpenes against larvae and adults of Colorado potato beetle, Leptinotarsa decemlineata Say (Coleoptera: Chrysomelidae),  26  (3): [10.1016/j.indcrop.2007.03.009]

17. Han J, Kim SI, Choi BR, Lee SG, Ahn YJ..  (2011)  Fumigant toxicity of lemon eucalyptus oil constituents to acaricide-susceptible and acaricide-resistant Tetranychus urticae.,  67  (12): [PMID:21674753] [10.1002/ps.2216]

18. Tong F, Coats JR..  (2012)  Quantitative structure-activity relationships of monoterpenoid binding activities to the housefly GABA receptor.,  68  (8): [PMID:22461383] [10.1002/ps.3280]

19. PubChem BioAssay data set, 

20. Vandresen F, Falzirolli H, Almeida Batista SA, da Silva-Giardini AP, de Oliveira DN, Catharino RR, Ruiz AL, de Carvalho JE, Foglio MA, da Silva CC..  (2014)  Novel R-(+)-limonene-based thiosemicarbazones and their antitumor activity against human tumor cell lines.,  79  [PMID:24727464] [10.1016/j.ejmech.2014.03.086]

21. Bibi H, Reany O, Waisman D, Keinan E..  (2015)  Prophylactic treatment of asthma by an ozone scavenger in a mouse model.,  25  (2): [PMID:25499435] [10.1016/j.bmcl.2014.11.035]

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23. Durço AO, de Souza DS, Heimfarth L, Miguel-Dos-Santos R, Rabelo TK, Oliveira Barreto T, Rhana P, Santos Santana MN, Braga WF, Santos Cruz JD, Lauton-Santos S, Santana-Filho VJ, Barreto RSS, Guimarães AG, Alvarez-Leite JI, Quintans Júnior LJ, Vasconcelos CML, Santos MRVD, Barreto AS..  (2019)  d-Limonene Ameliorates Myocardial Infarction Injury by Reducing Reactive Oxygen Species and Cell Apoptosis in a Murine Model.,  82  (11): [PMID:31710486] [10.1021/acs.jnatprod.9b00523]

24. Unpublished dataset, 

Source

Source(5):

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