 Chemical Structure.png)
Physicochemical Properties
| Molecular Formula | C123H212N44O35S.C2HF3O2 |
| Molecular Weight | 3013.36 |
| Related CAS # | Orexin B, human;205640-91-1 |
| Sequence | Arg-Ser-Gly-Pro-Pro-Gly-Leu-Gln-Gly-Arg-Leu-Gln-Arg-Leu-Leu-Gln-Ala-Ser-Gly-Asn-His-Ala-Ala-Gly-Ile-Leu-Thr-Met-NH2 |
| SequenceShortening | RSGPPGLQGRLQRLLQASGNHAAGILTM-NH2 |
| Appearance | White to off-white solid powder |
| LogP | -11.5 |
| SMILES | CC[C@H](C)[C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCSC)C(=O)N)NC(=O)CNC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC1=CNC=N1)NC(=O)[C@H](CC(=O)N)NC(=O)CNC(=O)[C@H](CO)NC(=O)[C@H](C)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(=N)N)NC(=O)CNC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@@H]2CCCN2C(=O)[C@@H]3CCCN3C(=O)CNC(=O)[C@H](CO)NC(=O)[C@H](CCCNC(=N)N)N |
| InChi Key | DHBREICAXZPFDD-WMQZXSDYSA-N |
| InChi Code | InChI=1S/C123H212N44O35S/c1-18-63(12)96(118(200)161-80(46-62(10)11)116(198)165-97(67(16)170)119(201)152-70(98(129)180)35-41-203-17)164-94(178)53-140-99(181)64(13)146-100(182)65(14)148-110(192)81(47-68-49-136-57-145-68)160-115(197)82(48-90(128)174)151-92(176)51-142-104(186)83(55-168)162-101(183)66(15)147-106(188)74(30-33-88(126)172)155-113(195)78(44-60(6)7)159-114(196)79(45-61(8)9)158-108(190)72(26-21-38-139-123(134)135)153-109(191)75(31-34-89(127)173)156-112(194)77(43-59(4)5)157-107(189)71(25-20-37-138-122(132)133)149-91(175)50-141-103(185)73(29-32-87(125)171)154-111(193)76(42-58(2)3)150-93(177)52-143-117(199)85-27-22-40-167(85)120(202)86-28-23-39-166(86)95(179)54-144-105(187)84(56-169)163-102(184)69(124)24-19-36-137-121(130)131/h49,57-67,69-86,96-97,168-170H,18-48,50-56,124H2,1-17H3,(H2,125,171)(H2,126,172)(H2,127,173)(H2,128,174)(H2,129,180)(H,136,145)(H,140,181)(H,141,185)(H,142,186)(H,143,199)(H,144,187)(H,146,182)(H,147,188)(H,148,192)(H,149,175)(H,150,177)(H,151,176)(H,152,201)(H,153,191)(H,154,193)(H,155,195)(H,156,194)(H,157,189)(H,158,190)(H,159,196)(H,160,197)(H,161,200)(H,162,183)(H,163,184)(H,164,178)(H,165,198)(H4,130,131,137)(H4,132,133,138)(H4,134,135,139)/t63-,64-,65-,66-,67+,69-,70-,71-,72-,73-,74-,75-,76-,77-,78-,79-,80-,81-,82-,83-,84-,85-,86-,96-,97-/m0/s1 |
| Chemical Name | (2S)-N-[2-[[(2S)-1-[[(2S)-1-[[(2S)-5-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-5-amino-1-[[(2S)-1-[[(2S)-1-[[2-[[(2S)-4-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[2-[[(2S,3S)-1-[[(2S)-1-[[(2S,3R)-1-[[(2S)-1-amino-4-methylsulfanyl-1-oxobutan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-2-oxoethyl]amino]-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-(1H-imidazol-4-yl)-1-oxopropan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-2-oxoethyl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-2-oxoethyl]-2-[[(2S)-2-[[2-[[(2S)-1-[(2S)-1-[2-[[(2S)-2-[[(2S)-2-amino-5-carbamimidamidopentanoyl]amino]-3-hydroxypropanoyl]amino]acetyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl]amino]acetyl]amino]-4-methylpentanoyl]amino]pentanediamide |
| Synonyms | Orexin B (human); 205640-91-1; Orexin B, human TFA; Human orexin B TFA; (Met-28 = C-terminal amide); RSGPPGLQGRLQRLLQASGNHAAGILTM; C123H212N44O35S; HB5323; |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets | Ki: 420 nM (OX1), 36 nM (OX2)[1]. |
| ln Vitro | Orexin B is produced by prepro-orexin, a precursor of proteolytic amino acids that is encoded by a gene found on human chromosome 17q21. Orexin B has been shown to have a greater affinity for the OX2 receptor in radioligand binding studies[1]. When comparing the human orexin B sequence to the rat sequence, two amino acid substitutions are present. With an EC50 of 60 nM in the [Ca2+]i transient experiment and an IC50 of 36 nM in the binding assay, the OX2 receptor is in fact a high-affinity receptor for human orexin B. The computed IC50 in the competitive binding test and the EC50 in the [Ca2+]i transient experiment for human orexin-B are 420 nM and 2500 nM, respectively[2]. This indicates that human Orexin B has a much lower affinity for human OX1. |
| ln Vivo | Human orexin B dramatically increases food intake; at the 2-hour mark, 3 nM and 30 nM of orexin-B, respectively, were shown to stimulate food consumption 5- and 12-fold, respectively[2]. |
| Animal Protocol |
Animal/Disease Models: Male Wistar rats (180 -200 g)[2]. Doses: 3 nM and 30 nM. Route of Administration: Administered in a 5 mL bolus through a catheter placed in the left lateral ventricle in early light phase. Experimental Results: Dramatically augmented food intake. |
| References |
[1]. Orexins: a new family of neuropeptides. Br J Anaesth. 1999 Nov;83(5):695-7. [2]. Orexins and orexin receptors: a family of hypothalamic neuropeptides and G protein-coupled receptors that regulate feeding behavior. Cell. 1998 Feb 20;92(4):573-85. |
| Additional Infomation | The hypothalamus plays a central role in the integrated control of feeding and energy homeostasis. We have identified two novel neuropeptides, both derived from the same precursor by proteolytic processing, that bind and activate two closely related (previously) orphan G protein-coupled receptors. These peptides, termed orexin-A and -B, have no significant structural similarities to known families of regulatory peptides. prepro-orexin mRNA and immunoreactive orexin-A are localized in neurons within and around the lateral and posterior hypothalamus in the adult rat brain. When administered centrally to rats, these peptides stimulate food consumption. prepro-orexin mRNA level is up-regulated upon fasting, suggesting a physiological role for the peptides as mediators in the central feedback mechanism that regulates feeding behavior.[2] |
Solubility Data
| Solubility (In Vitro) | May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples |
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 0.3319 mL | 1.6593 mL | 3.3186 mL | |
| 5 mM | 0.0664 mL | 0.3319 mL | 0.6637 mL | |
| 10 mM | 0.0332 mL | 0.1659 mL | 0.3319 mL |