(3S,6R,9R,12R,15R,18S,24S,30S,33R)-30-ethyl-33-[(E,1S)-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

Details

• Internal ID: 09d8dcb6-1f7b-4a48-8ccc-5058fb31cd46
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Peptoid-peptide hybrids > Cyclosporins
• IUPAC Name: (3S,6R,9R,12R,15R,18S,24S,30S,33R)-30-ethyl-33-[(E,1S)-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)NC(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(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-WIUPBDCUSA-N
• Popularity: 5 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
• Atomic LogP (AlogP): 3.27
• H-Bond Acceptor: 12
• H-Bond Donor: 5
• Rotatable Bonds: 15

Synonyms

• AS-13319

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6464	64.64%
Caco-2	-	0.8576	85.76%
Blood Brain Barrier	-	0.9250	92.50%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.5714	57.14%
OATP2B1 inhibitior	-	0.8558	85.58%
OATP1B1 inhibitior	-	0.7738	77.38%
OATP1B3 inhibitior	-	0.5699	56.99%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9652	96.52%
P-glycoprotein inhibitior	+	0.7432	74.32%
P-glycoprotein substrate	+	0.7957	79.57%
CYP3A4 substrate	+	0.7849	78.49%
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	+	0.5675	56.75%
CYP inhibitory promiscuity	-	0.9968	99.68%
UGT catelyzed	-	0.6000	60.00%
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	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3876	38.76%
Micronuclear	+	0.7400	74.00%
Hepatotoxicity	+	0.8682	86.82%
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	-	0.7217	72.17%
Acute Oral Toxicity (c)	III	0.7726	77.26%
Estrogen receptor binding	+	0.7745	77.45%
Androgen receptor binding	+	0.7266	72.66%
Thyroid receptor binding	+	0.6466	64.66%
Glucocorticoid receptor binding	+	0.7233	72.33%
Aromatase binding	+	0.6014	60.14%
PPAR gamma	+	0.8019	80.19%
Honey bee toxicity	-	0.7737	77.37%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	-	0.5926	59.26%

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: 132274082
• LOTUS: LTS0174767
• wikiData: Q104403628