[D-Asp3,(Z)-Dhb7]Microcystin-LR

Details

• Internal ID: 383efb33-87c6-4906-b9d7-7169eb47e092
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Hybrid peptides
• IUPAC Name: (2Z,5R,8S,11R,15S,18S,19S,22R)-15-[3-(diaminomethylideneamino)propyl]-2-ethylidene-18-[(1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dienyl]-5,19-dimethyl-8-(3-methylbutyl)-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptazacyclopentacosane-11,22-dicarboxylic acid
• SMILES (Canonical): CC=C1C(=O)NC(C(=O)NC(C(=O)NC(CC(=O)NC(C(=O)NC(C(C(=O)NC(CCC(=O)N1)C(=O)O)C)C=CC(=CC(C)C(CC2=CC=CC=C2)OC)C)CCCN=C(N)N)C(=O)O)CCC(C)C)C
• SMILES (Isomeric): C/C=C\1/C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H](CC(=O)N[C@H](C(=O)N[C@H]([C@@H](C(=O)N[C@H](CCC(=O)N1)C(=O)O)C)/C=C/C(=C/[C@H](C)[C@H](CC2=CC=CC=C2)OC)/C)CCCN=C(N)N)C(=O)O)CCC(C)C)C
• InChI: InChI=1S/C49H74N10O12/c1-9-33-44(64)53-31(7)43(63)57-36(19-17-27(2)3)46(66)59-38(48(69)70)26-41(61)55-35(16-13-23-52-49(50)51)45(65)56-34(30(6)42(62)58-37(47(67)68)21-22-40(60)54-33)20-18-28(4)24-29(5)39(71-8)25-32-14-11-10-12-15-32/h9-12,14-15,18,20,24,27,29-31,34-39H,13,16-17,19,21-23,25-26H2,1-8H3,(H,53,64)(H,54,60)(H,55,61)(H,56,65)(H,57,63)(H,58,62)(H,59,66)(H,67,68)(H,69,70)(H4,50,51,52)/b20-18+,28-24+,33-9-/t29-,30-,31+,34-,35-,36-,37+,38+,39-/m0/s1
• InChI Key: UJXOFCVEZJEEPR-BCCFPGDPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₉H₇₄N₁₀O₁₂
• Molecular Weight: 995.20 g/mol
• Exact Mass: 994.54876783 g/mol
• Topological Polar Surface Area (TPSA): 352.00 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 0.81
• H-Bond Acceptor: 11
• H-Bond Donor: 11
• Rotatable Bonds: 16

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7883	78.83%
Caco-2	-	0.8667	86.67%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7817	78.17%
OATP2B1 inhibitior	-	0.7170	71.70%
OATP1B1 inhibitior	+	0.8082	80.82%
OATP1B3 inhibitior	+	0.9271	92.71%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9251	92.51%
P-glycoprotein inhibitior	+	0.7500	75.00%
P-glycoprotein substrate	+	0.8655	86.55%
CYP3A4 substrate	+	0.7397	73.97%
CYP2C9 substrate	-	0.5747	57.47%
CYP2D6 substrate	-	0.8803	88.03%
CYP3A4 inhibition	-	0.9205	92.05%
CYP2C9 inhibition	-	0.7967	79.67%
CYP2C19 inhibition	-	0.7515	75.15%
CYP2D6 inhibition	-	0.9061	90.61%
CYP1A2 inhibition	-	0.8213	82.13%
CYP2C8 inhibition	+	0.7677	76.77%
CYP inhibitory promiscuity	-	0.9422	94.22%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.6293	62.93%
Eye corrosion	-	0.9838	98.38%
Eye irritation	-	0.9022	90.22%
Skin irritation	-	0.7667	76.67%
Skin corrosion	-	0.9237	92.37%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7301	73.01%
Micronuclear	+	0.7000	70.00%
Hepatotoxicity	-	0.6038	60.38%
skin sensitisation	-	0.8257	82.57%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.6616	66.16%
Acute Oral Toxicity (c)	III	0.3746	37.46%
Estrogen receptor binding	+	0.7848	78.48%
Androgen receptor binding	+	0.7186	71.86%
Thyroid receptor binding	+	0.6118	61.18%
Glucocorticoid receptor binding	+	0.6699	66.99%
Aromatase binding	+	0.6556	65.56%
PPAR gamma	+	0.8025	80.25%
Honey bee toxicity	-	0.6714	67.14%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.7741	77.41%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.58%	96.09%
CHEMBL2581	P07339	Cathepsin D	99.53%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	98.13%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.02%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.06%	94.45%
CHEMBL3837	P07711	Cathepsin L	95.72%	96.61%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.36%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	93.83%	95.89%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	93.75%	97.64%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.59%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.49%	99.17%
CHEMBL2179	P04062	Beta-glucocerebrosidase	93.47%	85.31%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.15%	97.09%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	91.79%	91.71%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	91.74%	82.69%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	91.45%	90.71%
CHEMBL1937	Q92769	Histone deacetylase 2	90.76%	94.75%
CHEMBL5103	Q969S8	Histone deacetylase 10	87.90%	90.08%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.81%	95.89%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.75%	95.50%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	87.42%	96.47%
CHEMBL1255126	O15151	Protein Mdm4	87.28%	90.20%
CHEMBL2535	P11166	Glucose transporter	86.87%	98.75%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	84.65%	93.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.78%	100.00%
CHEMBL1902	P62942	FK506-binding protein 1A	82.99%	97.05%
CHEMBL4072	P07858	Cathepsin B	82.51%	93.67%
CHEMBL3310	Q96DB2	Histone deacetylase 11	81.48%	88.56%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.12%	97.14%
CHEMBL226	P30542	Adenosine A1 receptor	80.62%	95.93%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	80.59%	92.88%
CHEMBL340	P08684	Cytochrome P450 3A4	80.55%	91.19%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	80.51%	89.67%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.10%	85.14%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 102120571
• LOTUS: LTS0037980
• wikiData: Q75057808