Deltorphin II

ID: ALA20226

Chembl Id: CHEMBL20226

Cas Number: 122752-16-3

PubChem CID: 10033203

Max Phase: Preclinical

Molecular Formula: C38H54N8O10

Molecular Weight: 782.90

Molecule Type: Protein

Names and Identifiers

Synonyms: Deltorphin II | Deltorphin II|122752-16-3|Deltorphin 2|Deltorphin B|[D-Ala2]-Deltorphin II|CHEMBL20226|Deltorphin-II|CHEBI:81498|Glycinamide, L-tyrosyl-D-alanyl-L-phenylalanyl-L-alpha-glutamyl-L-valyl-L-valyl-|MFCD00080072|Tyr-D-Ala-Phe-Glu-Val-Val-Gly amide|Tyr-D-Ala-Phe-Glu-Val-Val-Gly-NH2|(4S)-4-[[(2S)-2-[[(2R)-2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]propanoyl]amino]-3-phenylpropanoyl]amino]-5-[[(2S)-1-[[(2S)-1-[(2-amino-2-oxoethyl)amino]-3-methyl-1-oxobutan-2-yl]amino]-3-methyl-1Show More⌵

Canonical SMILES:  CC(C)[C@H](NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@@H](C)NC(=O)[C@@H](N)Cc1ccc(O)cc1)C(=O)N[C@H](C(=O)NCC(N)=O)C(C)C

Standard InChI:  InChI=1S/C38H54N8O10/c1-20(2)31(37(55)41-19-29(40)48)46-38(56)32(21(3)4)45-35(53)27(15-16-30(49)50)43-36(54)28(18-23-9-7-6-8-10-23)44-33(51)22(5)42-34(52)26(39)17-24-11-13-25(47)14-12-24/h6-14,20-22,26-28,31-32,47H,15-19,39H2,1-5H3,(H2,40,48)(H,41,55)(H,42,52)(H,43,54)(H,44,51)(H,45,53)(H,46,56)(H,49,50)/t22-,26+,27+,28+,31+,32+/m1/s1

Standard InChI Key:  NUNBRHVOPFWRRG-RCEFDBTISA-N

Alternative Forms

1. Parent:

   

   ALA20226

   DELTORPHIN II

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Protein

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 782.90

Molecular Weight (Monoisotopic): 782.3963

AlogP: -1.27

#Rotatable Bonds: 22

Polar Surface Area: 301.24

Molecular Species: ACID

HBA: 10

HBD: 10

#RO5 Violations: 2

HBA (Lipinski): 18

HBD (Lipinski): 12

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 4.07

CX Basic pKa: 7.73

CX LogP: -3.01

CX LogD: -3.15

Aromatic Rings: 2

Heavy Atoms: 56

QED Weighted: 0.07

Np Likeness Score: 0.03

References

1. Gao B, Hagenbuch B, Kullak-Ublick GA, Benke D, Aguzzi A, Meier PJ..  (2000)  Organic anion-transporting polypeptides mediate transport of opioid peptides across blood-brain barrier.,  294  (1): [PMID:10871297]

2. Kullak-Ublick GA, Ismair MG, Stieger B, Landmann L, Huber R, Pizzagalli F, Fattinger K, Meier PJ, Hagenbuch B..  (2001)  Organic anion-transporting polypeptide B (OATP-B) and its functional comparison with three other OATPs of human liver.,  120  (1): [PMID:11159893] [10.1053/gast.2001.21176]

3. Pizzagalli F, Hagenbuch B, Stieger B, Klenk U, Folkers G, Meier PJ..  (2002)  Identification of a novel human organic anion transporting polypeptide as a high affinity thyroxine transporter.,  16  (1): [PMID:12351693] [10.1210/me.2001-0309]

4. Cattori V, van Montfoort JE, Stieger B, Landmann L, Meijer DK, Winterhalter KH, Meier PJ, Hagenbuch B..  (2001)  Localization of organic anion transporting polypeptide 4 (Oatp4) in rat liver and comparison of its substrate specificity with Oatp1, Oatp2 and Oatp3.,  443  (1): [PMID:11713643] [10.1007/s004240100697]

5. Petrov RR, Lee YS, Vardanyan RS, Liu L, Ma SW, Davis P, Lai J, Porreca F, Vanderah TW, Hruby VJ..  (2013)  Effect of anchoring 4-anilidopiperidines to opioid peptides.,  23  (11): [PMID:23623418] [10.1016/j.bmcl.2013.03.065]

6. Kutsumura N, Nakajima R, Koyama Y, Miyata Y, Saitoh T, Yamamoto N, Iwata S, Fujii H, Nagase H..  (2015)  Investigation of 7-benzylidenenaltrexone derivatives as a novel structural antitrichomonal lead compound.,  25  (21): [PMID:26099536] [10.1016/j.bmcl.2015.06.002]

7. Faouzi A,Uprety R,Gomes I,Massaly N,Keresztes AI,Le Rouzic V,Gupta A,Zhang T,Yoon HJ,Ansonoff M,Allaoa A,Pan YX,Pintar J,Morón JA,Streicher JM,Devi LA,Majumdar S.  (2020)  Synthesis and Pharmacology of a Novel μ-δ Opioid Receptor Heteromer-Selective Agonist Based on the Carfentanyl Template.,  63  (22): [PMID:33170687] [10.1021/acs.jmedchem.0c00901]

Source

Source(2):

• Scientific Literature
• TP-search Transporter Database