Details of Natural Product (NP)

General Information of Natural Product (ID: NP0935)
  Natural Product Name
Toluene
  Synonyms
toluene; methylbenzene; toluol; 108-88-3; Benzene, methyl-; Phenylmethane; methacide; methylbenzol; antisal 1a; Toluen; tolu-sol; monomethyl benzene; Methane, phenyl-; Tolueen; Toluolo; phenyl methane; methyl-Benzene; p-toluene; RCRA waste number U220; NCI-C07272; 4-methylbenzene; Benzene, methyl; CP 25; UNII-3FPU23BG52; NSC 406333; UN 1294; PHME; CHEMBL9113; 3FPU23BG52; CHEBI:17578; Toluene, anhydrous; MFCD00008512; NSC-406333; NCGC00090939-02; DSSTox_CID_1360; Tolueen [Dutch]; Toluen [Czech]; Toluene, analytical standard; DSSTox_RID_76107; DSSTox_GSID_21360; Tolueno [Spanish]; Toluolo [Italian]; 22904-44-5; Caswell No. 859; Tolueno; methyl benzene; para-toluene; Toluene, ACS reagent, >=99.5%; 1-Methylbenzene; Toluene 1000 microg/mL in Methanol; CAS-108-88-3; CCRIS 2366; HSDB 131; EINECS 203-625-9; UN1294; RCRA waste no. U220; EPA Pesticide Chemical Code 080601; Dracyl; phenyl-methane; toluene solvent; 2-methylbenzene; toluene solution; toluene-; AI3-02261; MePh; Titration Solvent; 2-methyl benzene; 4-methyl-benzene; Benzylidyne radical; Toluene ACS Grade; Toluene HPLC grade; Methylbenzene, 9CI; Toluene (Technical); Toluene, for HPLC; PhCH3; Toluene, ACS reagent; Toluene, HPLC Grade; 4i7k; Toluene, 99.5%; OTOLINE (9CI); Toluene Reagent Grade ACS; EC 203-625-9; Toluene, Environmental Grade; Toluene, Semiconductor Grade; Toluene, LR, >=99%; C6H5CH3; WLN: 1R; BIDD:ER0288; Toluene, anhydrous, 99.8%; Toluene, ASTM, 99.5%; Toluene, p.a., 99.5%; GTPL5481; DTXSID7021360; Toluene, AR, >=99.5%; Toluene, for HPLC, 99.9%; Toluene, LR, rectified, 99%; DTXSID00184990; Toluene GC, for residue analysis; Toluene, HPLC grade, 99.8%; Toluene, Spectrophotometric Grade; Toluene 10 microg/mL in Methanol; Toluene, LR, sulfur free, 99%; ZINC967534; Toluene, AR, rectified, 99.5%; Toluene, technical grade, 95.0%; BCP16202; Toluene, for HPLC, >=99.8%; Toluene, for HPLC, >=99.9%; Toluene, histology grade, practical; Toluene, PRA grade, >=99.8%; Toluene 100 microg/mL in Methanol; Tox21_111042; Tox21_201224; BDBM50008558; NSC406333; Toluene, purification grade, 99.8%; AKOS015840411; ZINC100116646; DB11558; MCULE-4817136027; Toluene, puriss., >=99.5% (GC); Toluene, SAJ first grade, >=99.0%; NCGC00090939-01; NCGC00090939-03; NCGC00258776-01; Toluene [UN1294] [Flammable liquid]; Toluene, JIS special grade, >=99.5%; Toluene, Laboratory Reagent, >=99.3%; 50643-04-4; Toluene, for HPLC, >=99.7% (GC); Toluene, UV HPLC spectroscopic, 99.5%; Toluene, anhydrous, ZerO2(TM), 99.8%; FT-0688208; T0260; Toluene, suitable for determination of dioxins; C01455; Q15779; Toluene, suitable for scintillation, >=99.7%; Toluene liquid density, NIST(R) SRM(R) 211d; Toluene, for residue analysis, >=99.8% (GC); A801937; SR-01000944565; Toluene, ACS spectrophotometric grade, >=99.5%; SR-01000944565-1; Toluene, p.a., ACS reagent, reag. ISO, 99.5%; Toluene, suitable for 5000 per JIS, for residue analysis; Toluene, HPLC Plus, for HPLC, GC, and residue analysis, >=99.9%; Toluene, p.a., ACS reagent, reag. ISO, reag. Ph. Eur., 99.5%; Toluene, suitable for 300 per JIS, for residue analysis, >=99.8%; Toluene, absolute, over molecular sieve (H2O <=0.005%), >=99.7% (GC); Toluene, Pharmaceutical Secondary Standard; Certified Reference Material; Toluene, suitable for 1000 per JIS, for residue analysis, >=99.8%; Residual Solvent - Toluene, Pharmaceutical Secondary Standard; Certified Reference Material; Toluene, puriss. p.a., ACS reagent, reag. ISO, reag. Ph. Eur., >=99.7% (GC)
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  Formula C7H8
  Weight 92.14
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C7H8/c1-7-5-3-2-4-6-7/h2-6H,1H3
  InChI Key YXFVVABEGXRONW-UHFFFAOYSA-N
  Isomeric SMILES CC1=CC=CC=C1
  Canonical SMILES CC1=CC=CC=C1
  External Links PubChem ID 1140
CAS ID 108-88-3
NPASS ID NPC277704
HIT ID C0450
CHEMBL ID CHEMBL9113
  NP Activity Charts   Click to show/hide
  Activity Info  

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: phaseolorum sp. PR4
  Factor Name: PDB medium [1]
              Species Info Factor Info
               Experiment Detail
PR4 was isolated as an endophyte from the rhizome of Picrorhiza kurroa. Picrorhiza kurroa Royle ex. Benth (Plantaginaceae) is a perennial herb endemic to the north western alpine Himalayas. The endophyte PR4 was grown on PDA and in PDB at 26 ℃ for 15 days with constant shaking at 200 rpm in the latter case.
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               Mechanism
The two candidate NR-PKSs (PKS_3671 and PKS_4063) show differences in their domain organizations. PKS_3671 possesses two ACP-domains. Apart from that, only PKS_3671 contains a SAT-domain . These domains provide the first building block in the polyketide assembly, which usually is different from the extender unit malonyl-CoA (also known as the 'starter unit effect'). The ACA-synthesis however is believed to involve merely malonyl-CoA molecules. Even though the ACA-producing PKSs MdpG, ACAS, EncA, AptA and ClaG contain SAT-domains, an amino acid sequence alignment of these domains revealed that they all lack the active-site cysteine in the GXCXG motif and therefore most likely have no acyl transferase activity. Instead, all malonate building blocks are assumed to be loaded by the MAT. Under this aspect, the SAT-domain of PKS_3671 (that includes the correct GXCXG motif) likely incorporates a starter unit different from malonyl-CoA indicating that this enzyme is not involved in the biosynthesis of ACA. Therefore, the ACA-synthesizing PKS in C. asteris would rather be PKS_4063 that misses the SAT-domain .In the monodictyphenone and cladofulvin pathways, the cluster-encoded gene products MdpH and ClaH are crucial enzymes pushing the biosynthesis towards emodin. These EthD-domain-containing enzymes are suggested to catalyze the decarboxylation of ACA (3) into atrochrysone (4). Surprisingly, no such EthD-domain is encoded in the whole C. asteris genome. On the other hand, four genes directly attached to the putative ACA-synthase-coding gene pks_4063 show high similarity to genes of non-investigated PKS clusters in other fungi , which indicates an involvement in tailoring reactions of the respective polyketide pathways. According to InterProScan and BLASTp analyses, the genes sky_4060-62 encode a dehydratase and two dehydrogenases potentially catalyzing the multistep conversion of ACA (3) into emodin (1). Gene sky_4059 codes for a monooxygenase that putatively can connect two emodin molecules to the final product skyrin (2) in the style of the monooxygenase ClaM involved in the dimerization of the bisanthraquinone cladofulvin. Thus, the presence of these genes in the gene cluster gives further support to the hypothesis that PKS_4063 is the ACA-synthase in C. asteris. Mutational studies will be done in order to confirm these assumptions after a gene transfer system for this strain has been developed.
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               Factor Part Location NP Content
 
PDB medium (26℃ + 4 days)
 Rhizomes Himalayas
NP Content: 0.75 % Relative area
      Species Name: Vitis vinifera cv. Pinot noir
  Factor Name: Drought Stress Treatment [2]
              Species Info Factor Info
               Experiment Detail
3-year old single shoot V. vinifera plants (cultivar Pinot noir 18 Gm grafted on Kober 5BB, 51 plants) potted in 3L pots in a sandy loam soil were used. All plants were well watered (200 mL per day) at the beginning of the experiment (04.06.2010; DAY 0; 5 plants) and water was supplied to all control plants once every day (250 mL per day), whereas water supply of stressed plants was stopped. Physiological measurements and sampling of leaves took place on 07.06.2010 (DAY 3; 5 control, 5 stressed plants), 10.06.2010 (DAY 6; 5 control, 5 stressed plants) and 12.06.2010 (DAY 8; 5 control, 10 stressed plants). Due to very hot weather conditions in June 2010 the experiment was stopped after 8 days and 12 available control plants were used to restart the drought treatment with 6 control and 6 stressed plants on 11.06.2010 and all plants were measured on 15.06.2010 (DAY 5). The mean leaf temperatures at midday were: 25 ℃ (04.06.2010; DAY 0), 31.9 ℃ (07.06.2010; DAY 3), 30.8 ℃ (15.06.2010; DAY 5), 35.8 ℃ (10.06.2010; DAY 6) and 35.7 ℃ (12.06.2010; DAY 8). The mean PAR radiation per day (measured from 6:00 am till 7:00 pm) was 144.1 µmol m-2 s-1. Each plant was used only once for physiological measurements and sampling of leaves.On every day of the experiment (day 0, 3, 5, 6, 8) the pot weight and the volumetric soil moisture content (ThetaProbe ML2x and handheld data logger Moisture Meter HH2, Delta-T Devices, Cambridge, United Kingdom) was recorded. The water potential (PWSC Model 3000, Soilmoisture Equipment Corporation, Santa Barbara, USA) was determined for the 6th leaf (representing the insertion level of the shoot from the basis) of every plant and measurement day. Chlorophyll fluorescence and gas exchange parameters of light adapted leaves were determined with the 4th and 5th leaf, whereas dark adaptation was performed only with the 5th leaf. Immediately after these non-invasive measurements, the 5th leaf was harvested, frozen in liquid nitrogen and further used for the measurement of polyphenols, selected primary metabolites and volatiles (VOCs).
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               Factor Function
The content of different groups of primary and secondary metabolites is significantly influenced by severe drought stress in grapevine leaves. The content of the majority of the metabolites (around 60% of primary metabolites, around 85% of polyphenols and about 40% of the detected and identified VOCs) increased upon drought stress treatment. Among these especially the primary metabolites citric acid and glyceric acid were strongly influenced by the short as well as the prolonged drought stress treatment, whereas all polyphenols were only induced upon the prolonged drought stress treatment.
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               Factor Part Location NP Content
 
Normal condition
 Leaves Vienna, Austria
NP Content: 12053.5 ± 28459.9 peak areas
 
Dry 3-5 days
 Leaves Vienna, Austria
NP Content: 16106.7 ± 37421.1 peak areas
 
Dry 6-8 days
 Leaves Vienna, Austria
NP Content: 101634.8 ± 125103.4 peak areas
References
1 An endophyte of Picrorhiza kurroa Royle ex. Benth, producing menthol, phenylethyl alcohol and 3-hydroxypropionic acid, and other volatile organic compounds
2 Severe drought stress is affecting selected primary metabolites, polyphenols, and volatile metabolites in grapevine leaves (Vitis vinifera cv. Pinot noir)