(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-{2-[(2S)-2-[(2S)-2-(2-{[(2S)-1-[(2S)-1-{2-[(2S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]-3-hydroxypropanamido]acetyl}pyrrolidine-2-carbonyl]pyrrolidin-2-yl]formamido}acetamido)-4-methylpentanamido]-4-carbamoylbutanamido]acetamido}-5-carbamimidamidopentanamido]propanamido]-4-carbamoylbutanamido]-5-carbamimidamidopentanamido]-4-methylpentanamido]-4-methylpentanamido]-N-[(1S)-1-{[(1S)-1-[({[(1S)-2-carbamoyl-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-[({[(1S,2S)-1-{[(1S)-1-{[(1S,2R)-1-{[(1S)-1-carbamoyl-3-(methylsulfanyl)propyl]carbamoyl}-2-hydroxypropyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-methylbutyl]carbamoyl}methyl)carbamoyl]ethyl]carbamoyl}ethyl]carbamoyl}-2-(1H-imidazol-5-yl)ethyl]carbamoyl}ethyl]carbamoyl}methyl)carbamoyl]-2-hydroxyethyl]carbamoyl}ethyl]pentanediamide

• ChemBase ID: 153901
• Molecular Formular: C120H206N44O35S
• Molecular Mass: 2857.25844
• Monoisotopic Mass: 2855.54129551
• 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](Cc1cnc[nH]1)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](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]1CCCN1C(=O)[C@@H]1CCCN1C(=O)CNC(=O)[C@H](CO)NC(=O)[C@H](CCCNC(=N)N)N
• Canonical SMILES: CSCC[C@@H](C(=O)N)NC(=O)[C@H]([C@H](O)C)NC(=O)[C@@H](NC(=O)[C@H]([C@H](CC)C)NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CC(=O)N)NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CNC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CCCN1C(=O)CNC(=O)[C@@H](NC(=O)[C@H](CCCNC(=N)N)N)CO)CC(C)C)CCC(=O)N)CCCNC(=N)N)C)CCC(=O)N)CCCNC(=N)N)CC(C)C)CC(C)C)CCC(=O)N)C)CO)Cc1[nH]cnc1)C)C)CC(C)C
• InChI: InChI=1S/C120H206N44O35S/c1-17-60(10)93(115(197)158-77(44-59(8)9)113(195)162-94(65(15)167)116(198)150-68(95(126)177)34-40-200-16)161-91(175)51-137-96(178)61(11)143-97(179)62(12)146-108(190)78(45-66-47-133-55-142-66)157-112(194)79(46-87(125)171)149-89(173)49-139-102(184)80(53-165)159-99(181)64(14)145-105(187)72(29-32-85(123)169)154-110(192)75(42-57(4)5)156-111(193)76(43-58(6)7)155-106(188)70(25-20-37-136-120(131)132)152-107(189)73(30-33-86(124)170)151-98(180)63(13)144-104(186)69(24-19-36-135-119(129)130)147-88(172)48-138-101(183)71(28-31-84(122)168)153-109(191)74(41-56(2)3)148-90(174)50-140-114(196)82-26-21-39-164(82)117(199)83-27-22-38-163(83)92(176)52-141-103(185)81(54-166)160-100(182)67(121)23-18-35-134-118(127)128/h47,55-65,67-83,93-94,165-167H,17-46,48-54,121H2,1-16H3,(H2,122,168)(H2,123,169)(H2,124,170)(H2,125,171)(H2,126,177)(H,133,142)(H,137,178)(H,138,183)(H,139,184)(H,140,196)(H,141,185)(H,143,179)(H,144,186)(H,145,187)(H,146,190)(H,147,172)(H,148,174)(H,149,173)(H,150,198)(H,151,180)(H,152,189)(H,153,191)(H,154,192)(H,155,188)(H,156,193)(H,157,194)(H,158,197)(H,159,181)(H,160,182)(H,161,175)(H,162,195)(H4,127,128,134)(H4,129,130,135)(H4,131,132,136)/t60-,61-,62-,63-,64-,65+,67-,68-,69-,70-,71-,72-,73-,74-,75-,76-,77-,78-,79-,80-,81-,82-,83-,93-,94-/m0/s1
• InChIKey: SURUUKNICBOUOQ-JNZZMZGCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-{2-[(2S)-2-[(2S)-2-(2-{[(2S)-1-[(2S)-1-{2-[(2S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]-3-hydroxypropanamido]acetyl}pyrrolidine-2-carbonyl]pyrrolidin-2-yl]formamido}acetamido)-4-methylpentanamido]-4-carbamoylbutanamido]acetamido}-5-carbamimidamidopentanamido]propanamido]-4-carbamoylbutanamido]-5-carbamimidamidopentanamido]-4-methylpentanamido]-4-methylpentanamido]-N-[(1S)-1-{[(1S)-1-[({[(1S)-2-carbamoyl-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-[({[(1S,2S)-1-{[(1S)-1-{[(1S,2R)-1-{[(1S)-1-carbamoyl-3-(methylsulfanyl)propyl]carbamoyl}-2-hydroxypropyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-methylbutyl]carbamoyl}methyl)carbamoyl]ethyl]carbamoyl}ethyl]carbamoyl}-2-(1H-imidazol-5-yl)ethyl]carbamoyl}ethyl]carbamoyl}methyl)carbamoyl]-2-hydroxyethyl]carbamoyl}ethyl]pentanediamide
• IUPAC Traditional name: (2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-{2-[(2S)-2-[(2S)-2-(2-{[(2S)-1-[(2S)-1-{2-[(2S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]-3-hydroxypropanamido]acetyl}pyrrolidine-2-carbonyl]pyrrolidin-2-yl]formamido}acetamido)-4-methylpentanamido]-4-carbamoylbutanamido]acetamido}-5-carbamimidamidopentanamido]propanamido]-4-carbamoylbutanamido]-5-carbamimidamidopentanamido]-4-methylpentanamido]-4-methylpentanamido]-N-[(1S)-1-{[(1S)-1-[({[(1S)-2-carbamoyl-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-[({[(1S,2S)-1-{[(1S)-1-{[(1S,2R)-1-{[(1S)-1-carbamoyl-3-(methylsulfanyl)propyl]carbamoyl}-2-hydroxypropyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-methylbutyl]carbamoyl}methyl)carbamoyl]ethyl]carbamoyl}ethyl]carbamoyl}-2-(3H-imidazol-4-yl)ethyl]carbamoyl}ethyl]carbamoyl}methyl)carbamoyl]-2-hydroxyethyl]carbamoyl}ethyl]pentanediamide
• Synonyms: SB-668875

Database IDs

• CAS Number: 274252-40-3
• PubChem SID: 162248040
• PubChem CID: 16201464

CALCULATED PROPERTIES

• H Acceptors: 46
• H Donor: 44
• LogD (pH = 5.5): -32.30044
• LogD (pH = 7.4): -30.14707
• Log P: -22.324978
• Molar Refractivity: 740.2221 cm^3
• Polarizability: 276.61447 Å^3
• Polar Surface Area: 1284.66 Å^2
• Rotatable Bonds: 94
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥95% (HPLC)
• Empirical Formula (Hill Notation): C120H206N44O35S

DETAILS

Sigma Aldrich - S0946

Amino Acid Sequence
Arg-Ser-Gly-Pro-Pro-Gly-Leu-Gln-Gly-Arg-Ala-Gln-Arg-Leu-Leu-Gln-Ala-Ser-Gly-Asn-His-Ala-Ala-Gly-Ile-Leu-Thr-Met-NH2
Biochem/physiol Actions
SB-668875 is a novel, selective peptide agonist at OX2 orexin receptors. SB-668875 possesses advantages over Orexins A and B which are equipotent at OX2 orexin receptors. The orexins can cause direct and reversible depolarisation of the postsynaptic membrane. The rank order of potencies of orexin receptor agonists to excite serotonergic DRN neurones is orexin-A = orexin-B > SB-668875-DM. In contrast, the rank order of potency of these agonists to excite noradrenergic locus coreleus (LC) neurones is orexin-A > orexin-B > SB-668875-DM.