Cyclosporin C

Details

• Internal ID: 9204e9b0-dd14-48e6-aa37-4b442ee24838
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Peptoid-peptide hybrids > Cyclosporins
• IUPAC Name: (3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-30-[(1R)-1-hydroxyethyl]-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
• InChI: InChI=1S/C62H111N11O13/c1-25-26-27-39(14)52(76)51-56(80)66-49(42(17)74)60(84)67(18)32-47(75)68(19)43(28-33(2)3)55(79)65-48(37(10)11)61(85)69(20)44(29-34(4)5)54(78)63-40(15)53(77)64-41(16)57(81)70(21)45(30-35(6)7)58(82)71(22)46(31-36(8)9)59(83)72(23)50(38(12)13)62(86)73(51)24/h25-26,33-46,48-52,74,76H,27-32H2,1-24H3,(H,63,78)(H,64,77)(H,65,79)(H,66,80)/b26-25+/t39-,40+,41-,42-,43+,44+,45+,46+,48+,49+,50+,51+,52-/m1/s1
• InChI Key: JTOKYIBTLUQVQV-QRVTZXGZSA-N
• Popularity: 32 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆₂H₁₁₁N₁₁O₁₃
• Molecular Weight: 1218.60 g/mol
• Exact Mass: 1217.83628264 g/mol
• Topological Polar Surface Area (TPSA): 299.00 Ų
• XlogP: 6.90
• Atomic LogP (AlogP): 2.24
• H-Bond Acceptor: 13
• H-Bond Donor: 6
• Rotatable Bonds: 15

Synonyms

• 59787-61-0
• 6S744L5508
• 7-Threonine-cyclosporin A
• (3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-30-[(1R)-1-Hydroxyethyl]-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-undecazacyclotri-triacontane-2,5,8,11,14,17,20,23,26,29,32-undecone
• Thr2-cyclosporine
• UNII-6S744L5508
• (3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-30-[(1R)-1-hydroxyethyl]-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
• (3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-33-((1R,2R,E)-1-Hydroxy-2-methylhex-4-en-1-yl)-30-((R)-1-hydroxyethyl)-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
• [Thr2]CsA
• 7-L-Threoninecyclosporin A
• CYCLOSPORIN C [MI]
• CHEMBL2370014
• SCHEMBL22032784
• JTOKYIBTLUQVQV-QRVTZXGZSA-N
• DTXSID501017530
• EX-A2529
• HY-N6027
• HB3859
• AKOS037748855
• CYCLOSPORIN A, 7-L-THREONINE-
• BS-17695
• CS-0032194
• D83121
• SR-01000872584
• Q-100690
• SR-01000872584-1
• Cyclosporin C, Antibiotic for Culture Media Use Only
• Q27265421
• CYCLO(L-ALANYL-D-ALANYL-N-METHYL-L-LEUCYL-N-METHYL-L-LEUCYL-N-METHYL-L-VALYL-(3R,4R,6E)-6,7-DIDEHYDRO-3-HYDROXY-N,4-DIMETHYL-L-2-AMINOOCTANOYL-L-THREONYL-N-METHYLGLYCYL-N-METHYL-L-LEUCYL-L-VALYL-N-METHYL-L-LEUCYL)
• Cyclo[[(E)-(2S,3R,4R)-3-hydroxy-4-methyl-2-(methylamino)-6-octenoyl]-L-threonine-N-methylglycyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl-L-alanyl-D-alanyl-N-methyl-L-leucyl-N-methyl-L-leucyl-N-methyl-L-valyl]

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6133	61.33%
Caco-2	-	0.8587	85.87%
Blood Brain Barrier	-	0.9250	92.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.6659	66.59%
OATP2B1 inhibitior	-	0.8564	85.64%
OATP1B1 inhibitior	-	0.5697	56.97%
OATP1B3 inhibitior	-	0.4004	40.04%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9495	94.95%
P-glycoprotein inhibitior	+	0.7399	73.99%
P-glycoprotein substrate	+	0.7735	77.35%
CYP3A4 substrate	+	0.7534	75.34%
CYP2C9 substrate	-	0.8284	82.84%
CYP2D6 substrate	-	0.8475	84.75%
CYP3A4 inhibition	-	0.7882	78.82%
CYP2C9 inhibition	-	0.9323	93.23%
CYP2C19 inhibition	-	0.9017	90.17%
CYP2D6 inhibition	-	0.9352	93.52%
CYP1A2 inhibition	-	0.9263	92.63%
CYP2C8 inhibition	+	0.5296	52.96%
CYP inhibitory promiscuity	-	0.9964	99.64%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.7900	79.00%
Carcinogenicity (trinary)	Non-required	0.6011	60.11%
Eye corrosion	-	0.9840	98.40%
Eye irritation	-	0.8986	89.86%
Skin irritation	-	0.7537	75.37%
Skin corrosion	-	0.9184	91.84%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3677	36.77%
Micronuclear	+	0.7600	76.00%
Hepatotoxicity	+	0.8625	86.25%
skin sensitisation	-	0.8782	87.82%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.6800	68.00%
Acute Oral Toxicity (c)	III	0.7384	73.84%
Estrogen receptor binding	+	0.7735	77.35%
Androgen receptor binding	+	0.7275	72.75%
Thyroid receptor binding	+	0.6482	64.82%
Glucocorticoid receptor binding	+	0.7203	72.03%
Aromatase binding	+	0.5895	58.95%
PPAR gamma	+	0.7971	79.71%
Honey bee toxicity	-	0.7856	78.56%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7400	74.00%
Fish aquatic toxicity	-	0.6078	60.78%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1949	P62937	Cyclophilin A	99.09%	98.57%
CHEMBL2581	P07339	Cathepsin D	98.89%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.95%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.31%	97.25%
CHEMBL5103	Q969S8	Histone deacetylase 10	93.51%	90.08%
CHEMBL1937	Q92769	Histone deacetylase 2	92.02%	94.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.20%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.03%	85.14%
CHEMBL4072	P07858	Cathepsin B	90.63%	93.67%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	88.23%	90.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.94%	97.09%
CHEMBL321	P14780	Matrix metalloproteinase 9	87.53%	92.12%
CHEMBL4208	P20618	Proteasome component C5	86.96%	90.00%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	85.57%	90.93%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.64%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.13%	89.00%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	82.89%	89.67%
CHEMBL255	P29275	Adenosine A2b receptor	82.75%	98.59%
CHEMBL3310	Q96DB2	Histone deacetylase 11	82.68%	88.56%
CHEMBL332	P03956	Matrix metalloproteinase-1	82.51%	94.50%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	82.41%	91.11%
CHEMBL333	P08253	Matrix metalloproteinase-2	81.20%	96.31%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	80.54%	95.71%
CHEMBL4588	P22894	Matrix metalloproteinase 8	80.36%	94.66%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.36%	93.00%
CHEMBL2730	P21980	Protein-glutamine gamma-glutamyltransferase	80.35%	92.38%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.22%	99.17%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 5287817
• LOTUS: LTS0129283
• wikiData: Q27265421