Cyclosporin H

Details

• Internal ID: 5044d43f-202e-4caa-a333-f342799444cd
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Peptoid-peptide hybrids > Cyclosporins
• IUPAC Name: (3R,6S,9S,12R,15S,18S,21S,24S,30S,33S)-30-ethyl-33-[(E,1R,2R)-1-hydroxy-2-methylhex-4-enyl]-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18,24-tetrakis(2-methylpropyl)-3,21-di(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone
• SMILES (Canonical): CCC1C(=O)N(CC(=O)N(C(C(=O)NC(C(=O)N(C(C(=O)NC(C(=O)NC(C(=O)N(C(C(=O)N(C(C(=O)N(C(C(=O)N(C(C(=O)N1)C(C(C)CC=CC)O)C)C(C)C)C)CC(C)C)C)CC(C)C)C)C)C)CC(C)C)C)C(C)C)CC(C)C)C)C
• SMILES (Isomeric): CC[C@H]1C(=O)N(CC(=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)N1)[C@@H]([C@H](C)C/C=C/C)O)C)C(C)C)C)CC(C)C)C)CC(C)C)C)C)C)CC(C)C)C)C(C)C)CC(C)C)C)C
• InChI: InChI=1S/C62H111N11O12/c1-25-27-28-40(15)52(75)51-56(79)65-43(26-2)58(81)67(18)33-48(74)68(19)44(29-34(3)4)55(78)66-49(38(11)12)61(84)69(20)45(30-35(5)6)54(77)63-41(16)53(76)64-42(17)57(80)70(21)46(31-36(7)8)59(82)71(22)47(32-37(9)10)60(83)72(23)50(39(13)14)62(85)73(51)24/h25,27,34-47,49-52,75H,26,28-33H2,1-24H3,(H,63,77)(H,64,76)(H,65,79)(H,66,78)/b27-25+/t40-,41+,42-,43+,44+,45+,46+,47+,49+,50-,51+,52-/m1/s1
• InChI Key: PMATZTZNYRCHOR-JLPRAAIDSA-N
• Popularity: 48 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆₂H₁₁₁N₁₁O₁₂
• Molecular Weight: 1202.60 g/mol
• Exact Mass: 1201.84136802 g/mol
• Topological Polar Surface Area (TPSA): 279.00 Ų
• XlogP: 7.50

Synonyms

• 83602-39-5
• Cyclosporine H
• FUO6O3NDNH
• (3R,6S,9S,12R,15S,18S,21S,24S,30S,33S)-30-ethyl-33-((1R,2R,E)-1-hydroxy-2-methylhex-4-en-1-yl)-6,9,18,24-tetraisobutyl-3,21-diisopropyl-1,4,7,10,12,15,19,25,28-nonamethyl-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontan-2,5,8,11,14,17,20,23,26,29,32-undecaone
• Cyclosporin A, 5-(N-methyl-D-valine)-
• Csh cyclosporin
• (3R,6S,9S,12R,15S,18S,21S,24S,30S,33S)-30-ethyl-33-[(E,1R,2R)-1-hydroxy-2-methylhex-4-enyl]-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18,24-tetrakis(2-methylpropyl)-3,21-di(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone
• MFCD04039488
• 5-(N-Methyl-D-valine)cyclosporine A
• UNII-FUO6O3NDNH
• [D-MeVal]11-CsA
• CYCLOSPORIN H, (-)-
• CHEMBL4448165
• SANDOZ-37-839
• PMATZTZNYRCHOR-JLPRAAIDSA-N
• DTXSID801017527
• EX-A2225
• HY-P1122
• 5-(N-Methyl-D-valine)cyclosporin A
• NCGC00386167-01
• CS-0027967
• D83129
• Q27278214
• (3R,6S,9S,12R,15S,18S,21S,24S,30S,33S)-30-ethyl-33-[(E,1R,2R)-1-hydroxy-2-methyl-hex-4-enyl]-6,9,18,24-tetraisobutyl-3,21-diisopropyl-1,4,7,10,12,15,19,25,28-nonamethyl-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone
• 12-((4E)(1R,2R)-1-hydroxy-2-methylhex-4-enyl)(6S,12S,15S,21S,24S,27S,30S,3R,9R,33R)-9,24-bis(methylethyl)-15-ethyl-2,5,8,11,17,20,26,30,33-nonamethyl-3,6,21,27-tetrakis(2-methylpropyl)-2,5,8,11,14,17,20,23,26,29,32-undecaazacyclotritriacontane-1,4,7,10,13,16,19,22,25,28,31-undecaone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL6020	O95342	Bile salt export pump	500 nM	IC50	via Super-PRED
CHEMBL1949	P62937	Cyclophilin A	11 nM; 9.7 nM; 6.7 nM	Kd; IC50; Ki	via Super-PRED; via Super-PRED; via Super-PRED
CHEMBL2075	P23284	Cyclophilin B	9.8 nM	Kd	via Super-PRED
CHEMBL1697657	Q08752	Peptidyl-prolyl cis-trans isomerase D	2.58 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.56%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.45%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.49%	96.09%
CHEMBL1937	Q92769	Histone deacetylase 2	91.53%	94.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.40%	95.56%
CHEMBL5103	Q969S8	Histone deacetylase 10	90.32%	90.08%
CHEMBL4072	P07858	Cathepsin B	89.74%	93.67%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	88.94%	90.71%
CHEMBL321	P14780	Matrix metalloproteinase 9	88.77%	92.12%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.34%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.24%	85.14%
CHEMBL218	P21554	Cannabinoid CB1 receptor	86.46%	96.61%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	85.14%	95.71%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	84.93%	90.93%
CHEMBL255	P29275	Adenosine A2b receptor	84.88%	98.59%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.71%	99.23%
CHEMBL333	P08253	Matrix metalloproteinase-2	84.37%	96.31%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.21%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.03%	89.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	82.86%	96.47%
CHEMBL4208	P20618	Proteasome component C5	82.86%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.54%	94.45%
CHEMBL226	P30542	Adenosine A1 receptor	81.49%	95.93%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 6476564
• LOTUS: LTS0075391
• wikiData: Q27278214