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Chemistry

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Also known as: 59004-96-5, 61512-76-3, Endorphin, alpha, Lipotropin 61-76, A-endorphin, Alpha -endorphin
Molecular Formula
C77H120N18O26S
Molecular Weight
1745.9  g/mol
InChI Key
NXSIJWJXMWBCBX-NWKQFZAZSA-N

Alpha-Endorphin
An endogenous opioid peptide derived from BETA-LIPOTROPIN of the pro-opiomelanocortin (POMC) system. It is the 16-amino acid sequence of the N-terminal of BETA-ENDORPHIN and differs from GAMMA-ENDORPHIN by one amino acid (beta-endorphin 1-17).
1 2D Structure

Alpha-Endorphin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(4S)-5-[[(2S)-6-amino-1-[[(2S)-1-[[(2S)-5-amino-1-[[(2S,3R)-1-[(2S)-2-[[(2S)-1-[[(2S)-1-[[(1S,2R)-1-carboxy-2-hydroxypropyl]amino]-3-methyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamoyl]pyrrolidin-1-yl]-3-hydroxy-1-oxobutan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-1-oxohexan-2-yl]amino]-4-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2S)-2-[[2-[[2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylsulfanylbutanoyl]amino]-3-hydroxybutanoyl]amino]-3-hydroxypropanoyl]amino]-5-oxopentanoic acid
2.1.2 InChI
InChI=1S/C77H120N18O26S/c1-38(2)31-51(70(113)91-60(39(3)4)74(117)94-63(42(7)100)77(120)121)88-73(116)55-18-14-29-95(55)76(119)62(41(6)99)93-67(110)48(23-25-56(80)102)85-71(114)53(36-96)89-65(108)47(17-12-13-28-78)84-66(109)49(24-26-59(105)106)86-72(115)54(37-97)90-75(118)61(40(5)98)92-68(111)50(27-30-122-8)87-69(112)52(33-43-15-10-9-11-16-43)83-58(104)35-81-57(103)34-82-64(107)46(79)32-44-19-21-45(101)22-20-44/h9-11,15-16,19-22,38-42,46-55,60-63,96-101H,12-14,17-18,23-37,78-79H2,1-8H3,(H2,80,102)(H,81,103)(H,82,107)(H,83,104)(H,84,109)(H,85,114)(H,86,115)(H,87,112)(H,88,116)(H,89,108)(H,90,118)(H,91,113)(H,92,111)(H,93,110)(H,94,117)(H,105,106)(H,120,121)/t40-,41-,42-,46+,47+,48+,49+,50+,51+,52+,53+,54+,55+,60+,61+,62+,63+/m1/s1
2.1.3 InChI Key
NXSIJWJXMWBCBX-NWKQFZAZSA-N
2.1.4 Canonical SMILES
CC(C)CC(C(=O)NC(C(C)C)C(=O)NC(C(C)O)C(=O)O)NC(=O)C1CCCN1C(=O)C(C(C)O)NC(=O)C(CCC(=O)N)NC(=O)C(CO)NC(=O)C(CCCCN)NC(=O)C(CCC(=O)O)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C(CCSC)NC(=O)C(CC2=CC=CC=C2)NC(=O)CNC(=O)CNC(=O)C(CC3=CC=C(C=C3)O)N
2.1.5 Isomeric SMILES
C[C@H]([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H]([C@@H](C)O)C(=O)O)NC(=O)[C@H](CCSC)NC(=O)[C@H](CC2=CC=CC=C2)NC(=O)CNC(=O)CNC(=O)[C@H](CC3=CC=C(C=C3)O)N)O
2.2 Synonyms
2.2.1 MeSH Synonyms

1. Alpha Endorphin

2. Beta-endorphin (1-16)

3. Endorphin, Alpha

2.2.2 Depositor-Supplied Synonyms

1. 59004-96-5

2. 61512-76-3

3. Endorphin, Alpha

4. Lipotropin 61-76

5. A-endorphin

6. Alpha -endorphin

7. Alpha-endorphin, Human

8. Chembl255300

9. Mfcd00076381

10. Akos037645059

11. Lph(61-76)

12. Alpha-endorphin Human, >=97% (hplc)

13. As-56652

14. Q4734927

15. H-tyr-gly-gly-phe-met-thr-ser-glu-lys-ser-gln-thr-pro-leu-val-thr-oh

2.3 Create Date
2007-07-04
3 Chemical and Physical Properties
Molecular Weight 1745.9 g/mol
Molecular Formula C77H120N18O26S
XLogP3-9.7
Hydrogen Bond Donor Count25
Hydrogen Bond Acceptor Count29
Rotatable Bond Count55
Exact Mass1744.83418718 g/mol
Monoisotopic Mass1744.83418718 g/mol
Topological Polar Surface Area744 Ų
Heavy Atom Count122
Formal Charge0
Complexity3520
Isotope Atom Count0
Defined Atom Stereocenter Count17
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Neurotransmitter Agents

Substances used for their pharmacological actions on any aspect of neurotransmitter systems. Neurotransmitter agents include agonists, antagonists, degradation inhibitors, uptake inhibitors, depleters, precursors, and modulators of receptor function. (See all compounds classified as Neurotransmitter Agents.)


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