Microcystin WR

Details

• Internal ID: 35ae511c-ac93-443f-9e34-31804a0810e4
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Hybrid peptides
• IUPAC Name: (5R,8S,11R,12S,15S,18S,19S,22R)-15-[3-(diaminomethylideneamino)propyl]-8-(1H-indol-3-ylmethyl)-18-[(1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dienyl]-1,5,12,19-tetramethyl-2-methylidene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptazacyclopentacosane-11,22-dicarboxylic acid
• InChI: InChI=1S/C54H73N11O12/c1-29(25-30(2)43(77-8)26-35-15-10-9-11-16-35)20-21-38-31(3)46(67)62-41(52(73)74)22-23-44(66)65(7)34(6)49(70)59-33(5)48(69)63-42(27-36-28-58-39-18-13-12-17-37(36)39)51(72)64-45(53(75)76)32(4)47(68)61-40(50(71)60-38)19-14-24-57-54(55)56/h9-13,15-18,20-21,25,28,30-33,38,40-43,45,58H,6,14,19,22-24,26-27H2,1-5,7-8H3,(H,59,70)(H,60,71)(H,61,68)(H,62,67)(H,63,69)(H,64,72)(H,73,74)(H,75,76)(H4,55,56,57)/b21-20+,29-25+/t30-,31-,32-,33+,38-,40-,41+,42-,43-,45+/m0/s1
• InChI Key: UGNOHFGJSOFQHC-ZISXDMAXSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₄H₇₃N₁₁O₁₂
• Molecular Weight: 1068.20 g/mol
• Exact Mass: 1067.54401681 g/mol
• Topological Polar Surface Area (TPSA): 359.00 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 1.30
• H-Bond Acceptor: 11
• H-Bond Donor: 11
• Rotatable Bonds: 15

Synonyms

• Microcystin-WR
• 138234-58-9
• 3-L-Tryptophan-5-L-argininecyanoginosin La
• (5R,8S,11R,12S,15S,18S,19S,22R)-15-[3-(diaminomethylideneamino)propyl]-8-(1H-indol-3-ylmethyl)-18-[(1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dienyl]-1,5,12,19-tetramethyl-2-methylidene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptazacyclopentacosane-11,22-dicarboxylic acid
• MC-WR
• DTXSID101016178
• HY-N11681
• CS-0693712

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5745	57.45%
Caco-2	-	0.8648	86.48%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.5156	51.56%
OATP2B1 inhibitior	-	0.8546	85.46%
OATP1B1 inhibitior	+	0.8226	82.26%
OATP1B3 inhibitior	+	0.9260	92.60%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9291	92.91%
P-glycoprotein inhibitior	+	0.7467	74.67%
P-glycoprotein substrate	+	0.8601	86.01%
CYP3A4 substrate	+	0.7542	75.42%
CYP2C9 substrate	-	0.8060	80.60%
CYP2D6 substrate	-	0.8573	85.73%
CYP3A4 inhibition	-	0.6763	67.63%
CYP2C9 inhibition	-	0.7126	71.26%
CYP2C19 inhibition	-	0.6966	69.66%
CYP2D6 inhibition	-	0.8617	86.17%
CYP1A2 inhibition	-	0.6872	68.72%
CYP2C8 inhibition	+	0.7876	78.76%
CYP inhibitory promiscuity	-	0.7029	70.29%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.5587	55.87%
Eye corrosion	-	0.9832	98.32%
Eye irritation	-	0.8995	89.95%
Skin irritation	-	0.7667	76.67%
Skin corrosion	-	0.9227	92.27%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7486	74.86%
Micronuclear	+	0.8200	82.00%
Hepatotoxicity	-	0.5038	50.38%
skin sensitisation	-	0.8416	84.16%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	-	0.7933	79.33%
Acute Oral Toxicity (c)	I	0.3470	34.70%
Estrogen receptor binding	+	0.7191	71.91%
Androgen receptor binding	+	0.7229	72.29%
Thyroid receptor binding	+	0.6856	68.56%
Glucocorticoid receptor binding	+	0.6986	69.86%
Aromatase binding	+	0.6535	65.35%
PPAR gamma	+	0.7845	78.45%
Honey bee toxicity	-	0.6576	65.76%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.8799	87.99%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	100.00%	83.82%
CHEMBL2581	P07339	Cathepsin D	99.71%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.55%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.27%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	99.06%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.71%	95.56%
CHEMBL3837	P07711	Cathepsin L	96.87%	96.61%
CHEMBL4644	P41968	Melanocortin receptor 3	96.51%	99.52%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.46%	94.45%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	96.42%	97.64%
CHEMBL4072	P07858	Cathepsin B	95.06%	93.67%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	93.92%	91.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	93.50%	95.89%
CHEMBL3310	Q96DB2	Histone deacetylase 11	92.50%	88.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.15%	86.33%
CHEMBL5103	Q969S8	Histone deacetylase 10	90.46%	90.08%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.38%	99.17%
CHEMBL1255126	O15151	Protein Mdm4	88.83%	90.20%
CHEMBL2535	P11166	Glucose transporter	88.32%	98.75%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.24%	97.09%
CHEMBL1937	Q92769	Histone deacetylase 2	86.91%	94.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.94%	89.00%
CHEMBL255	P29275	Adenosine A2b receptor	85.35%	98.59%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	83.06%	96.47%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.31%	99.23%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.24%	85.14%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	82.19%	100.00%
CHEMBL2959	Q08881	Tyrosine-protein kinase ITK/TSK	82.13%	95.00%
CHEMBL3891	P07384	Calpain 1	82.05%	93.04%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.18%	95.50%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 101619976
• LOTUS: LTS0181061
• wikiData: Q104246711