CAS 86168-78-7|sermorelin|Growth Hormone Releasing Factor Fragment 1-29 amide human|Sermorelin|growth hormone-releasing hormone (1-29)|(3S)-3-{[(1S)-1-{[(1S,2S)-1-{[(1S)-1-{[(1S,2R)-1-{[(1S)-1-{[(1S...

General Information

Structure

Molecular Formula

C₁₄₉H₂₄₆N₄₄O₄₂S

Molecular Mass

3357.88214

Exact Mass

3355.81869913

Charge

InChI

InChI=1S/C149H246N44O42S/c1-20-77(13)116(191-122(211)81(17)168-132(221)104(66-113(204)205)178-121(210)79(15)167-123(212)88(152)62-84-39-43-86(198)44-40-84)145(234)185-102(63-83-32-23-22-24-33-83)138(227)193-118(82(18)197)146(235)186-103(65-111(155)202)137(226)189-108(71-196)142(231)182-101(64-85-41-45-87(199)46-42-85)136(225)175-93(38-31-56-165-149(161)162)126(215)174-91(35-26-28-53-151)131(220)190-115(76(11)12)143(232)184-97(58-72(3)4)124(213)166-68-112(203)170-94(47-49-109(153)200)128(217)180-100(61-75(9)10)135(224)188-106(69-194)140(229)169-80(16)120(209)172-92(37-30-55-164-148(159)160)125(214)173-90(34-25-27-52-150)127(216)179-99(60-74(7)8)134(223)181-98(59-73(5)6)133(222)176-95(48-50-110(154)201)129(218)183-105(67-114(206)207)139(228)192-117(78(14)21-2)144(233)177-96(51-57-236-19)130(219)187-107(70-195)141(230)171-89(119(156)208)36-29-54-163-147(157)158/h22-24,32-33,39-46,72-82,88-108,115-118,194-199H,20-21,25-31,34-38,47-71,150-152H2,1-19H3,(H2,153,200)(H2,154,201)(H2,155,202)(H2,156,208)(H,166,213)(H,167,212)(H,168,221)(H,169,229)(H,170,203)(H,171,230)(H,172,209)(H,173,214)(H,174,215)(H,175,225)(H,176,222)(H,177,233)(H,178,210)(H,179,216)(H,180,217)(H,181,223)(H,182,231)(H,183,218)(H,184,232)(H,185,234)(H,186,235)(H,187,219)(H,188,224)(H,189,226)(H,190,220)(H,191,211)(H,192,228)(H,193,227)(H,204,205)(H,206,207)(H4,157,158,163)(H4,159,160,164)(H4,161,162,165)/t77-,78-,79-,80-,81-,82+,88-,89-,90-,91-,92-,93-,94-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,115-,116-,117-,118-/m0/s1

InChIKey

WGWPRVFKDLAUQJ-MITYVQBRSA-N

Canonic Smiles

NCCCC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N)CCCNC(=N)N)CO)CCSC)[C@H](CC)C)CC(=O)O)CCC(=O)N)CC(C)C)CC(C)C)CCCCN)CCCNC(=N)N)C)CO)CC(C)C)CCC(=O)N)CC(C)C)C(C)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]([C@H](O)C)NC(=O)[C@@H](NC(=O)[C@H]([C@H](CC)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](Cc1ccc(cc1)O)N)C)CC(=O)O)C)Cc1ccccc1)CC(=O)N)CO)Cc1ccc(cc1)O)CCCNC(=N)N

Isomeric Smiles

CC[C@H](C)[C@@H](C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H](CO)C(=O)N[C@@H](Cc1ccc(cc1)O)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N)NC(=O)[C@H](C)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](C)NC(=O)[C@H](Cc1ccc(cc1)O)N

Calculated Properties

JChem

LogD (pH = 7.4)

-26.44

LogD (pH = 5.5)

-28.88

Log P

-18.96

Rotatable Bonds

115

H Donor

H Acceptors

Lipinski's Rule of Five

false

Acid pKa

12.44

Polar Surface Area

1,446.90

Polarizability

349.84

Molar Refractivity

878.59

LOG S

45.43

Data Source

Commercial Catalog

Academic Data

Data Source

Names and Identifiers

Synonyms

Growth Hormone Releasing Factor Fragment 1-29 amide humanSermorelinGHRH(1-29)growth hormone-releasing factor (1-29)growth hormone-releasing hormone (1-29)sermorelinGHRH(1-29)-NH2L-Tyr-L-Ala-L-Asp-L-Ala-L-Ile-L-Phe-L-Thr-L-Asn-L-Ser-L-Tyr-L-Arg-L-Lys-L-Val-L-Leu-Gly-L-Gln-L-Leu-L-Ser-L-Ala-L-Arg-L-Lys-L-Leu-L-Leu-L-Gln-L-Asp-L-Ile-L-Met-L-Ser-L-ArgH-Tyr-Ala-Asp-Ala-Ile-Phe-Thr-Asn-Ser-Tyr-Arg-Lys-Val-Leu-Gly-Gln-Leu-Ser-Ala-Arg-Lys-Leu-Leu-Gln-Asp-Ile-Met-Ser-Arg-NH2YADAIFTNSYRKVLGQLSARKLLQDIMSR

IUPAC Traditional name

sermorelin

IUPAC name

(3S)-3-{[(1S)-1-{[(1S,2S)-1-{[(1S)-1-{[(1S,2R)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-[({[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S,2S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-4-carbamimidamido-1-carbamoylbutyl]carbamoyl}-2-hydroxyethyl]carbamoyl}-3-(methylsulfanyl)propyl]carbamoyl}-2-methylbutyl]carbamoyl}-2-carboxyethyl]carbamoyl}-3-carbamoylpropyl]carbamoyl}-3-methylbutyl]carbamoyl}-3-methylbutyl]carbamoyl}pentyl]carbamoyl}-4-carbamimidamidobutyl]carbamoyl}ethyl]carbamoyl}-2-hydroxyethyl]carbamoyl}-3-methylbutyl]carbamoyl}-3-carbamoylpropyl]carbamoyl}methyl)carbamoyl]-3-methylbutyl]carbamoyl}-2-methylpropyl]carbamoyl}pentyl]carbamoyl}-4-carbamimidamidobutyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl]carbamoyl}-2-hydroxyethyl]carbamoyl}-2-carbamoylethyl]carbamoyl}-2-hydroxypropyl]carbamoyl}-2-phenylethyl]carbamoyl}-2-methylbutyl]carbamoyl}ethyl]carbamoyl}-3-[(2S)-2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]propanamido]propanoic acid

International Nonproprietary Name (INN)

sermorelinesermorelinumsermorelinasermorelin

Names and Identifiers

Registration numbers

CHEMBL

DrugBank ID

PubChem CID

ATC CODE

KEGG ID

Wikipedia Title

Unique Ingredient Identifier

CAS Number

MDL Number

PubChem SID

SureChEMBL Database

PubMed Citation Links

26382721288303171803117326879649144997077553739322578551804690826456392329714742143200

CHEBI ID

CHEBI:80299CHEBI:9118

BindingDB Database

50004966

Drug Central Database

KEGG DRUG Database

Chemspider ID

CompTox Database

Registration numbers

Properties

Pharmacology Properties

Gene Information

human ... GHRH(2691), GHRHR(2692)

Safety Information

Storage Temperature

-20°C

German water hazard class

Personal Protective Equipment

Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

Purity

≥97% (HPLC)

Properties

Related Proteins

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Molecular Spectra

No Data Available

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Molecule Details

Sigma Aldrich

G6771

Amino Acid Sequence
Tyr-Ala-Asp-Ala-Ile-Phe-Thr-Asn-Ser-Tyr-Arg-Lys-Val-Leu-Gly-Gln-Leu-Ser-Ala-Arg-Lys-Leu-Leu-Gln-Asp-Ile-Met-Ser-Arg-NH2
Biochem/physiol Actions
Amidated GRF fragment that is equipotent to GRF in releasing somatotropin from anterior pituitary.

A 29 amino acid polypeptide that is used to treat growth problems (usually in children) due to growth hormone deficiency. It is the biologically active fragment of human growth hormone-releasing factor (GHRH).

Molecule Details

References

PubChem Literature

No Data Available

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References

Bioactivity

PubChem BioAssay

Bioactivity

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General Information

Calculated Properties