Cyclosporin L

Details

• Internal ID: 83758db0-22a3-44f6-af2d-1b6fab98dd54
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Peptides > Oligopeptides
• IUPAC Name: (3S,6S,9R,12S,15S,18S,21S,27S,30S,33S)-27-ethyl-30-[(E,1R,2R)-1-hydroxy-2-methylhex-4-enyl]-1,4,7,9,12,16,22,25-octamethyl-3,6,15,21-tetrakis(2-methylpropyl)-18,33-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/C61H109N11O12/c1-24-26-27-39(15)51(74)49-55(78)64-42(25-2)58(81)67(18)32-47(73)68(19)43(28-33(3)4)54(77)65-48(37(11)12)61(84)69(20)44(29-34(5)6)53(76)62-40(16)52(75)63-41(17)57(80)70(21)45(30-35(7)8)59(82)71(22)46(31-36(9)10)60(83)72(23)50(38(13)14)56(79)66-49/h24,26,33-46,48-51,74H,25,27-32H2,1-23H3,(H,62,76)(H,63,75)(H,64,78)(H,65,77)(H,66,79)/b26-24+/t39-,40+,41-,42+,43+,44+,45+,46+,48+,49+,50+,51-/m1/s1
• InChI Key: ZSNYYEIGOZADKA-WKHWYDSQSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆₁H₁₀₉N₁₁O₁₂
• Molecular Weight: 1188.60 g/mol
• Exact Mass: 1187.82571795 g/mol
• Topological Polar Surface Area (TPSA): 288.00 Ų
• XlogP: 7.30
• Atomic LogP (AlogP): 2.93
• H-Bond Acceptor: 12
• H-Bond Donor: 6
• Rotatable Bonds: 15

Synonyms

• 108027-39-0
• (3R,4R)-3-Hydroxy-5-[(E)-1-propenyl]cyclo[L-Leu-L-Abu-Sar-N-methyl-L-Leu-L-Val-N-methyl-L-Leu-L-Ala-D-Ala-N-methyl-L-Leu-N-methyl-L-Leu-N-methyl-L-Val-]
• (3S,6S,9R,12S,15S,18S,21S,27S,30S,33S)-27-ethyl-30-[(E,1R,2R)-1-hydroxy-2-methylhex-4-enyl]-1,4,7,9,12,16,22,25-octamethyl-3,6,15,21-tetrakis(2-methylpropyl)-18,33-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
• GLXC-23061
• FC174904
• cyclo[Abu-Sar-N(Me)Leu-Val-N(Me)Leu-Ala-D-Ala-N(Me)Leu-N(Me)Leu-N(Me)Val-Bmt(E)]
• (3R,4R)-3-Hydroxy-5-[(E)-1-propenyl]cyclo[L-Leu-L-Abu-Sar-N-methyl-L-Leu-L-Val-N-methyl-L-Leu-L-Ala-
• (3S,6S,9R,12S,15S,18S,21S,27S,30S,33S)-27-ethyl-30-((1R,2R,E)-1-hydroxy-2-methylhex-4-en-1-yl)-3,6,15,21-tetraisobutyl-18,33-diisopropyl-1,4,7,9,12,16,22,25-octamethyl-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontan-2,5,8,11,14,17,20,23,26,29,32-undecaone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6464	64.64%
Caco-2	-	0.8583	85.83%
Blood Brain Barrier	-	0.9250	92.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.5714	57.14%
OATP2B1 inhibitior	-	0.8555	85.55%
OATP1B1 inhibitior	-	0.6399	63.99%
OATP1B3 inhibitior	-	0.5699	56.99%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9637	96.37%
P-glycoprotein inhibitior	+	0.7432	74.32%
P-glycoprotein substrate	+	0.8076	80.76%
CYP3A4 substrate	+	0.7600	76.00%
CYP2C9 substrate	-	0.8284	82.84%
CYP2D6 substrate	-	0.8475	84.75%
CYP3A4 inhibition	-	0.6112	61.12%
CYP2C9 inhibition	-	0.9230	92.30%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	-	0.9265	92.65%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	+	0.5773	57.73%
CYP inhibitory promiscuity	-	0.9968	99.68%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.7700	77.00%
Carcinogenicity (trinary)	Non-required	0.5869	58.69%
Eye corrosion	-	0.9848	98.48%
Eye irritation	-	0.8990	89.90%
Skin irritation	-	0.7606	76.06%
Skin corrosion	-	0.9104	91.04%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3797	37.97%
Micronuclear	+	0.7400	74.00%
Hepatotoxicity	+	0.8182	81.82%
skin sensitisation	-	0.8771	87.71%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.8112	81.12%
Acute Oral Toxicity (c)	III	0.7726	77.26%
Estrogen receptor binding	+	0.7821	78.21%
Androgen receptor binding	+	0.7313	73.13%
Thyroid receptor binding	+	0.6401	64.01%
Glucocorticoid receptor binding	+	0.7167	71.67%
Aromatase binding	+	0.6192	61.92%
PPAR gamma	+	0.8012	80.12%
Honey bee toxicity	-	0.7706	77.06%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	-	0.5926	59.26%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1949	P62937	Cyclophilin A	99.46%	98.57%
CHEMBL2581	P07339	Cathepsin D	98.62%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.95%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.79%	97.25%
CHEMBL1937	Q92769	Histone deacetylase 2	93.03%	94.75%
CHEMBL5103	Q969S8	Histone deacetylase 10	90.91%	90.08%
CHEMBL321	P14780	Matrix metalloproteinase 9	90.77%	92.12%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.51%	95.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	89.91%	90.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.25%	97.09%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	87.07%	95.71%
CHEMBL333	P08253	Matrix metalloproteinase-2	86.63%	96.31%
CHEMBL226	P30542	Adenosine A1 receptor	86.56%	95.93%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	85.08%	96.47%
CHEMBL218	P21554	Cannabinoid CB1 receptor	84.31%	96.61%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	84.01%	90.93%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.89%	85.14%
CHEMBL4208	P20618	Proteasome component C5	83.77%	90.00%
CHEMBL228	P31645	Serotonin transporter	83.70%	95.51%
CHEMBL2996	Q05655	Protein kinase C delta	83.63%	97.79%
CHEMBL4072	P07858	Cathepsin B	83.41%	93.67%
CHEMBL255	P29275	Adenosine A2b receptor	83.05%	98.59%
CHEMBL4588	P22894	Matrix metalloproteinase 8	81.66%	94.66%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	81.40%	97.47%
CHEMBL299	P17252	Protein kinase C alpha	81.32%	98.03%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.57%	93.56%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.57%	100.00%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	80.27%	97.21%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.21%	99.23%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 101609649
• LOTUS: LTS0181050
• wikiData: Q105382603