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Alpha Endorphin

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Synopsis

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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

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 Formula	C₇₇H₁₂₀N₁₈O₂₆S
Molecular Weight	1745.9 g/mol
XLogP3	-9.7
Hydrogen Bond Donor Count	25
Hydrogen Bond Acceptor Count	29
Rotatable Bond Count	55
Exact Mass	1744.83418718 g/mol
Monoisotopic Mass	1744.83418718 g/mol
Topological Polar Surface Area	744 Å²
Heavy Atom Count	122
Formal Charge	0
Complexity	3520
Isotope Atom Count	0
Defined Atom Stereocenter Count	17
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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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