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6918-09-8 molecular structure
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N-(1-{2-[(carbamoylmethyl)carbamoyl]pyrrolidin-1-yl}-5-[(diaminomethylidene)amino]-1-oxopentan-2-yl)-2-{2-[2-(3-hydroxy-2-{2-[3-(1H-imidazol-5-yl)-2-[(5-oxopyrrolidin-2-yl)formamido]propanamido]-3-(1H-indol-3-yl)propanamido}propanamido)-3-(4-hydroxyphenyl)propanamido]acetamido}-4-methylpentanamide

ChemBase ID: 526
Molecular Formular: C55H75N17O13
Molecular Mass: 1182.2901
Monoisotopic Mass: 1181.57302555
SMILES and InChIs

SMILES:
O=C(N1C(CCC1)C(=O)NCC(=O)N)C(NC(=O)C(NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C1NC(=O)CC1)Cc1[nH]cnc1)Cc1c2c([nH]c1)cccc2)CO)Cc1ccc(O)cc1)CC(C)C)CCCN=C(N)N
Canonical SMILES:
OCC(C(=O)NC(C(=O)NCC(=O)NC(C(=O)NC(C(=O)N1CCCC1C(=O)NCC(=O)N)CCCN=C(N)N)CC(C)C)Cc1ccc(cc1)O)NC(=O)C(Cc1c[nH]c2c1cccc2)NC(=O)C(NC(=O)C1CCC(=O)N1)Cc1[nH]cnc1
InChI:
InChI=1S/C55H75N17O13/c1-29(2)19-38(49(80)67-37(9-5-17-60-55(57)58)54(85)72-18-6-10-43(72)53(84)62-25-44(56)75)66-46(77)26-63-47(78)39(20-30-11-13-33(74)14-12-30)68-52(83)42(27-73)71-50(81)40(21-31-23-61-35-8-4-3-7-34(31)35)69-51(82)41(22-32-24-59-28-64-32)70-48(79)36-15-16-45(76)65-36/h3-4,7-8,11-14,23-24,28-29,36-43,61,73-74H,5-6,9-10,15-22,25-27H2,1-2H3,(H2,56,75)(H,59,64)(H,62,84)(H,63,78)(H,65,76)(H,66,77)(H,67,80)(H,68,83)(H,69,82)(H,70,79)(H,71,81)(H4,57,58,60)
InChIKey:
XLXSAKCOAKORKW-UHFFFAOYSA-N

Cite this record

CBID:526 http://www.chembase.cn/molecule-526.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
N-(1-{2-[(carbamoylmethyl)carbamoyl]pyrrolidin-1-yl}-5-[(diaminomethylidene)amino]-1-oxopentan-2-yl)-2-{2-[2-(3-hydroxy-2-{2-[3-(1H-imidazol-5-yl)-2-[(5-oxopyrrolidin-2-yl)formamido]propanamido]-3-(1H-indol-3-yl)propanamido}propanamido)-3-(4-hydroxyphenyl)propanamido]acetamido}-4-methylpentanamide
IUPAC Traditional name
gonadorelin
Brand Name
Dirigestran
Dirigestran Spofa
Factrel
Fertagyl
Gonadorelina [INN-Spanish]
Gonadorelinum [INN-Latin]
Gonadotropin releasing hormone
Gonadotropin-releasing factor
Gonadotropin-releasing hormone
Human LH-RH
Hypocrine
Luforan
Lutal
Lutamin
Lutrefact
Lutrepulse
Lutrepulse KIT
Mammalian GnRH
Mammalian LH-RH
Ovine LH-RH
Porchine LH-RH
Porcine LH-releasing factor
Relefact
Relisorm
Relisorm L
Synthetic Gn-RH
Synthetic LH-FSH releasing hormone
Synthetic LH-RF
Synthetic LH-RH
Synthetic LH-releasing factor
Synthetic LH-releasing hormone
Synthetic LRF
Synthetic decapeptide FSH/LH-RH
Synthetic gonadoliberin
Synonyms
Gonadorelin
CAS Number
6918-09-8
PubChem SID
160963989
46506144
PubChem CID
36523

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
DrugBank DB00644 external link
PubChem 36523 external link
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Lipinski's Rule of Five false  Acid pKa 9.470687 
H Acceptors 17  H Donor 16 
LogD (pH = 5.5) -8.74699  LogD (pH = 7.4) -7.980599 
Log P -6.3192887  Molar Refractivity 302.5053 cm3
Polarizability 117.86165 Å3 Polar Surface Area 474.63 Å2
Rotatable Bonds 31 
Solubility (Water) 5.88e-02 g/l  Log P -0.09 
LOG S -4.3 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Solubility
1 mg/mL expand Show data source
Hydrophobicity(logP)
-3.6 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00644 external link
Item Information
Drug Groups approved
Description Gonadorelin is another name for gonadotropin-releasing hormone (GnRH). It is a synthetic decapeptide prepared using solid phase peptide synthesis. GnRH is responsible for the release of follicle stimulating hormone and leutinizing hormone from the anterior pitutitary.
Indication For evaluating the functional capacity and response of the gonadotropes of the anterior pituitary also for evaluating residual gonadotropic function of the pituitary following removal of a pituitary tumor by surgery and/or irradiation.
Pharmacology Gonadorelin is responsible for the release of follicle stimulating hormone and leutinizing hormone from the anterior pitutitary. In the pituitary GnRH stimulates synthesis and release of FSH and LH, a process that is controlled by the frequency and amplitude of GnRH pulses, as well as the feedback of androgens and estrogens. The pulsatility of GnRH secretion has been seen in all vertebrates, and it is necessary to ensure a correct reproductive function. Thus a single hormone, GnRH, controls a complex process of follicular growth, ovulation, and corpus luteum maintenance in the female, and spermatogenesis in the male. Its short half life requires infusion pumps for its clinical use
Toxicity LD50>3000 mg/kg (rat, oral)
Affected Organisms
Humans and other mammals
Biotransformation Rapidly hydrolyzed to inactive peptide components
Absorption Rapidly absorbed when injected
Half Life Very short, initial, 2 to 10 minutes; terminal, 10 to 40 minutes
References
Dungan HM, Clifton DK, Steiner RA: Minireview: kisspeptin neurons as central processors in the regulation of gonadotropin-releasing hormone secretion. Endocrinology. 2006 Mar;147(3):1154-8. Epub 2005 Dec 22. [Pubmed]
Franceschini I, Lomet D, Cateau M, Delsol G, Tillet Y, Caraty A: Kisspeptin immunoreactive cells of the ovine preoptic area and arcuate nucleus co-express estrogen receptor alpha. Neurosci Lett. 2006 Jul 3;401(3):225-30. Epub 2006 Apr 18. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com

REFERENCES

REFERENCES

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  • • Dungan HM, Clifton DK, Steiner RA: Minireview: kisspeptin neurons as central processors in the regulation of gonadotropin-releasing hormone secretion. Endocrinology. 2006 Mar;147(3):1154-8. Epub 2005 Dec 22. Pubmed
  • • Franceschini I, Lomet D, Cateau M, Delsol G, Tillet Y, Caraty A: Kisspeptin immunoreactive cells of the ovine preoptic area and arcuate nucleus co-express estrogen receptor alpha. Neurosci Lett. 2006 Jul 3;401(3):225-30. Epub 2006 Apr 18. Pubmed
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PATENTS

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