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Cyclosporin; Cyclosporin H

AlkaPlorer ID: AK293825

Synonym: 5-(N-Methyl-D-valine)cyclosporin A 

IUPAC Name: 30-ethyl-33-[(E)-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

Structure

SMILES: C/C=C/CC(C)C(O)C1C(O)=NC(CC)C(=O)N(C)CC(=O)N(C)C(CC(C)C)C(O)=NC(C(C)C)C(=O)N(C)C(CC(C)C)C(O)=NC(C)C(O)=NC(C)C(=O)N(C)C(CC(C)C)C(=O)N(C)C(CC(C)C)C(=O)N(C)C(C(C)C)C(=O)N1C

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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+

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InChIKey: PMATZTZNYRCHOR-IMVLJIQESA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain

Properties Information

Molecule Weight: 1202.634999999999

TPSA？: 292.76

MolLogP？: 6.630200000000022

Number of H-Donors: 5

Number of H-Acceptors: 12

RingCount: 1

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Bacillus subtilis (strain 168) DNA polymerase III Potency 15003.0 nM None
Equus caballus Ferritin light chain Potency 2818.4 nM None
Equus caballus Ferritin light chain Potency 56234.1 nM None
Escherichia coli K-12 Endonuclease 4 Potency 10000.0 nM None
Homo sapiens 786-0 GI50 12764.39 nM None
Homo sapiens 78 kDa glucose-regulated protein Potency 1648.2 nM None
Homo sapiens A498 GI50 4954.5 nM None
Homo sapiens A549 GI50 5248.07 nM None
Homo sapiens ACHN GI50 5495.41 nM None
Homo sapiens Amyloid-beta A4 protein Potency 4610.9 nM None
Homo sapiens Ataxin-2 Potency 4466.8 nM None
Homo sapiens Ataxin-2 Potency 5011.9 nM None
Homo sapiens ATPase family AAA domain-containing protein 5 Potency 5802.4 nM None
Homo sapiens ATPase family AAA domain-containing protein 5 Potency 6510.4 nM None
Homo sapiens Beta-glucocerebrosidase Potency 17782.8 nM None
Homo sapiens Bile salt export pump IC50 460.0 nM None
Homo sapiens Bloom syndrome protein Potency 12589.3 nM None
Homo sapiens CAKI-1 GI50 6982.32 nM None
Homo sapiens Canalicular multispecific organic anion transporter 1 IC50 3100.0 nM None
Homo sapiens Canalicular multispecific organic anion transporter 1 IC50 4100.0 nM None
Homo sapiens CCRF-CEM GI50 3076.1 nM None
Homo sapiens Cerebroside-sulfatase Potency 425.6 nM None
Homo sapiens Chromobox protein homolog 1 Potency 63095.7 nM None
Homo sapiens COLO 205 GI50 1770.11 nM None
Homo sapiens Cyclophilin A IC50 9.7 nM None
Homo sapiens DLD-1 GI50 5321.08 nM None
Homo sapiens DMS-114 GI50 3698.28 nM None
Homo sapiens DMS-273 GI50 4698.94 nM None
Homo sapiens DNA-(apurinic or apyrimidinic site) lyase Potency 8912.5 nM None
Homo sapiens DNA-(apurinic or apyrimidinic site) lyase Potency 11220.2 nM None
Homo sapiens DNA polymerase beta Potency 12589.3 nM None
Homo sapiens DNA polymerase iota Potency 14125.4 nM None
Homo sapiens DNA polymerase kappa Potency 10621.3 nM None
Homo sapiens EKVX GI50 10375.28 nM None
Homo sapiens Geminin Potency 7943.3 nM None
Homo sapiens Geminin Potency 8199.5 nM None
Homo sapiens HCC 2998 GI50 2152.78 nM None
Homo sapiens HCT-116 GI50 4852.89 nM None
Homo sapiens HCT-15 GI50 4477.13 nM None
Homo sapiens HEK293 Potency 11220.2 nM None
Homo sapiens HEK293 Potency 23099.9 nM None
Homo sapiens Histone acetyltransferase GCN5 Potency 28183.8 nM None
Homo sapiens Histone deacetylase 6 Inhibition -3.9 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition 10.4 % 10.6019/CHEMBL4808148
Homo sapiens Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Potency 79432.8 nM None
Homo sapiens HL-60 GI50 2249.05 nM None
Homo sapiens HOP-18 GI50 11066.24 nM None
Homo sapiens HOP-62 GI50 3908.41 nM None
Homo sapiens HOP-92 GI50 4645.15 nM None
Homo sapiens HT-29 GI50 2285.6 nM None
Homo sapiens IGROV-1 GI50 5236.0 nM None
Homo sapiens K562 GI50 3990.25 nM None
Homo sapiens KM12 GI50 5942.92 nM None
Homo sapiens KM-20L2 GI50 2971.67 nM None
Homo sapiens LOX IMVI GI50 2432.2 nM None
Homo sapiens LXFL 529 GI50 6886.52 nM None
Homo sapiens M14 GI50 2606.15 nM None
Homo sapiens M19-MEL GI50 2365.92 nM None
Homo sapiens Malme-3M GI50 7447.32 nM None
Homo sapiens Menin/Histone-lysine N-methyltransferase MLL Potency 2511.9 nM None
Homo sapiens Microtubule-associated protein tau Potency 8912.5 nM None
Homo sapiens MOLT-4 GI50 2978.52 nM None
Homo sapiens NCI-H226 GI50 4385.31 nM None
Homo sapiens NCI-H23 GI50 5370.32 nM None
Homo sapiens NCI-H322M GI50 3732.5 nM None
Homo sapiens NCI-H460 GI50 3872.58 nM None
Homo sapiens NCI-H522 GI50 5482.77 nM None
Homo sapiens Neuropeptide S receptor Potency 1000.0 nM None
Homo sapiens Nuclear factor erythroid 2-related factor 2 Potency 9200.0 nM None
Homo sapiens OVCAR-3 GI50 3801.89 nM None
Homo sapiens OVCAR-4 GI50 4178.3 nM None
Homo sapiens OVCAR-5 GI50 6934.26 nM None
Homo sapiens OVCAR-8 GI50 12218.0 nM None
Homo sapiens Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 Potency 13459.1 nM None
Homo sapiens Peripheral myelin protein 22 Potency 3793.3 nM None
Homo sapiens P-glycoprotein 1 IC50 730.0 nM None
Homo sapiens Prelamin-A/C Potency 7079.5 nM None
Homo sapiens RPMI-8226 GI50 2483.13 nM None
Homo sapiens RXF 393 GI50 7447.32 nM None
Homo sapiens RXF 631 GI50 1981.53 nM None
Homo sapiens Serine/threonine-protein kinase mTOR Potency 4645.1 nM None
Homo sapiens Serine/threonine-protein kinase mTOR Potency 10399.2 nM None
Homo sapiens SF-268 GI50 7261.06 nM None
Homo sapiens SF-295 GI50 2792.54 nM None
Homo sapiens SF-539 GI50 4295.36 nM None
Homo sapiens SH-SY5Y Potency 5011.9 nM None
Homo sapiens SK-MEL-2 GI50 3169.57 nM None
Homo sapiens SK-MEL-28 GI50 5675.45 nM None
Homo sapiens SK-MEL-5 GI50 3784.43 nM None
Homo sapiens SK-OV-3 GI50 12941.96 nM None
Homo sapiens SN12C GI50 3953.67 nM None
Homo sapiens SNB-19 GI50 10471.29 nM None
Homo sapiens SNB-75 GI50 7211.07 nM None
Homo sapiens SNB-78 GI50 4977.37 nM None
Homo sapiens Solute carrier organic anion transporter family member 1B1 IC50 850.0 nM None
Homo sapiens Solute carrier organic anion transporter family member 1B3 IC50 130.0 nM None
Homo sapiens SR GI50 1472.31 nM None
Homo sapiens Survival motor neuron protein Potency 14125.4 nM None
Homo sapiens SW-620 GI50 11194.38 nM None
Homo sapiens TK-10 GI50 7816.28 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 1018.3 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 1282.0 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 2818.4 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 4466.8 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 29092.9 nM None
Homo sapiens U-251 GI50 7655.97 nM None
Homo sapiens UACC-257 GI50 2051.16 nM None
Homo sapiens UACC-62 GI50 3854.78 nM None
Homo sapiens Ubiquitin carboxyl-terminal hydrolase 1 Potency 14125.4 nM None
Homo sapiens Ubiquitin carboxyl-terminal hydrolase 1 Potency 50118.7 nM None
Homo sapiens Ubiquitin carboxyl-terminal hydrolase 2 Potency 10000.0 nM None
Homo sapiens UO-31 GI50 3258.37 nM None
Homo sapiens XF498 GI50 3962.78 nM None
Influenza A virus Nonstructural protein 1 Potency 1412.5 nM None
Plasmodium falciparum Plasmodium falciparum Potency 585.8 nM None
Plasmodium falciparum Plasmodium falciparum Potency 827.5 nM None
Rattus norvegicus Thioredoxin reductase 1, cytoplasmic Potency 631.0 nM None
Rattus norvegicus Thioredoxin reductase 1, cytoplasmic Potency 8436.8 nM None
Rattus norvegicus Thioredoxin reductase 1, cytoplasmic Potency 10621.3 nM None
Rattus norvegicus Thioredoxin reductase 1, cytoplasmic Potency 18887.6 nM None
Rattus norvegicus Thioredoxin reductase 1, cytoplasmic Potency 21192.3 nM None
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 14.61 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition -0.21 % 10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 100.07 % 10.21203/rs.3.rs-23951/v1
Trypanosoma brucei 6-phospho-1-fructokinase Potency 9.5 nM None
Trypanosoma cruzi Cruzipain Potency 1584.9 nM None
Trypanosoma cruzi Cruzipain Potency 15848.9 nM None
None NON-PROTEIN TARGET Potency 446.7 nM None
None NON-PROTEIN TARGET Potency 562.3 nM None
None NON-PROTEIN TARGET Potency 794.3 nM None
None NON-PROTEIN TARGET Potency 891.3 nM None
None NON-PROTEIN TARGET Potency 1412.5 nM None
None Unchecked Potency 1258.9 nM None
None Unchecked Potency 4685.9 nM None
None Unchecked Potency 6309.6 nM None
None Unchecked Potency 8196.1 nM None
None Unchecked Potency 11220.2 nM None
None Unchecked Potency 15848.9 nM None
None Unchecked Potency 17782.8 nM None
None Unchecked Potency 25118.9 nM None
None Unchecked Potency 28183.8 nM None

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT001484 C/C=C/CC(C)C(O)C1C(=O)NC(CC)C(=O)N(C)CC(=O)N(C)C(CC(C)C)C(=O)NC(C(C)C)C(=O)N(C)C(CC(C)C)C(=O)NC(C)C(=O)NC(C)C(=O)N(C)C(CC(C)C)C(=O)N(C)C(CC(C)C)C(=O)N(C)C(C(C)C)C(=O)N1C>>C/C=C/CC(C)C(O)C1C(=O)NC(CC)C(=O)N(C)CC(=O)N(C)C(CC(C)C)C(=O)NC(C(C)C)C(=O)N(C)C(CC(C)C)C(=O)NC(C)C(=O)NC(C)C(=O)N(C)C(CC(C)(C)O)C(=O)N(C)C(CC(C)C)C(=O)N(C)C(C(C)C)C(=O)N1C MNXR154634
AKRT001485 C/C=C/CC(C)C(O)C1C(=O)NC(CC)C(=O)N(C)CC(=O)N(C)C(CC(C)C)C(=O)NC(C(C)C)C(=O)N(C)C(CC(C)C)C(=O)NC(C)C(=O)NC(C)C(=O)N(C)C(CC(C)C)C(=O)N(C)C(CC(C)C)C(=O)N(C)C(C(C)C)C(=O)N1C>>CCC1NC(=O)C(C(O)C(C)C/C=C/CO)N(C)C(=O)C(C(C)C)N(C)C(=O)C(CC(C)C)N(C)C(=O)C(CC(C)C)N(C)C(=O)C(C)NC(=O)C(C)NC(=O)C(CC(C)C)N(C)C(=O)C(C(C)C)NC(=O)C(CC(C)C)N(C)C(=O)CN(C)C1=O MNXR154625
AKRT001486 C/C=C/CC(C)C(O)C1C(=O)NC(CC)C(=O)N(C)CC(=O)N(C)C(CC(C)C)C(=O)NC(C(C)C)C(=O)N(C)C(CC(C)C)C(=O)NC(C)C(=O)NC(C)C(=O)N(C)C(CC(C)C)C(=O)N(C)C(CC(C)C)C(=O)N(C)C(C(C)C)C(=O)N1C>>CCC1NC(=O)C(C2OC(CCO)CC2C)N(C)C(=O)C(C(C)C)N(C)C(=O)C(CC(C)C)N(C)C(=O)C(CC(C)C)N(C)C(=O)C(C)NC(=O)C(C)NC(=O)C(CC(C)C)N(C)C(=O)C(C(C)C)NC(=O)C(CC(C)C)N(C)C(=O)CN(C)C1=O MNXR154619
AKRT001487 C/C=C/CC(C)C(O)C1C(=O)NC(CC)C(=O)N(C)CC(=O)NC(CC(C)C)C(=O)NC(C(C)C)C(=O)N(C)C(CC(C)C)C(=O)NC(C)C(=O)NC(C)C(=O)N(C)C(CC(C)C)C(=O)N(C)C(CC(C)C)C(=O)N(C)C(C(C)C)C(=O)N1C.C[SAH]>>C/C=C/CC(C)C(O)C1C(=O)NC(CC)C(=O)N(C)CC(=O)N(C)C(CC(C)C)C(=O)NC(C(C)C)C(=O)N(C)C(CC(C)C)C(=O)NC(C)C(=O)NC(C)C(=O)N(C)C(CC(C)C)C(=O)N(C)C(CC(C)C)C(=O)N(C)C(C(C)C)C(=O)N1C MNXR154631
AKRT001489 C/C=C/CC(C)C(OS(=O)(=O)O)C1C(=O)NC(CC)C(=O)N(C)CC(=O)N(C)C(CC(C)C)C(=O)NC(C(C)C)C(=O)N(C)C(CC(C)C)C(=O)NC(C)C(=O)NC(C)C(=O)N(C)C(CC(C)C)C(=O)N(C)C(CC(C)C)C(=O)N(C)C(C(C)C)C(=O)N1C>>C/C=C/CC(C)C(O)C1C(=O)NC(CC)C(=O)N(C)CC(=O)N(C)C(CC(C)C)C(=O)NC(C(C)C)C(=O)N(C)C(CC(C)C)C(=O)NC(C)C(=O)NC(C)C(=O)N(C)C(CC(C)C)C(=O)N(C)C(CC(C)C)C(=O)N(C)C(C(C)C)C(=O)N1C MNXR155387