[D-Asp3, Dhb7]microcystin-LR

Details

• Internal ID: 3459d089-14d7-4424-8fbf-5a146451559a
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Hybrid peptides
• IUPAC Name: (2E,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-(2-methylpropyl)-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)CC(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)CC(C)C)C
• InChI: InChI=1S/C48H72N10O12/c1-9-32-43(63)52-30(7)42(62)57-36(22-26(2)3)45(65)58-37(47(68)69)25-40(60)54-34(16-13-21-51-48(49)50)44(64)55-33(29(6)41(61)56-35(46(66)67)19-20-39(59)53-32)18-17-27(4)23-28(5)38(70-8)24-31-14-11-10-12-15-31/h9-12,14-15,17-18,23,26,28-30,33-38H,13,16,19-22,24-25H2,1-8H3,(H,52,63)(H,53,59)(H,54,60)(H,55,64)(H,56,61)(H,57,62)(H,58,65)(H,66,67)(H,68,69)(H4,49,50,51)/b18-17+,27-23+,32-9+/t28-,29-,30+,33-,34-,35+,36-,37+,38-/m0/s1
• InChI Key: VDTOBYMILGRBLM-ZUCGMWCSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₈H₇₂N₁₀O₁₂
• Molecular Weight: 981.10 g/mol
• Exact Mass: 980.53311777 g/mol
• Topological Polar Surface Area (TPSA): 352.00 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 0.42
• H-Bond Acceptor: 11
• H-Bond Donor: 11
• Rotatable Bonds: 15

Synonyms

• [D-Asp3, Dhb7]microcystin-LR

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7883	78.83%
Caco-2	-	0.8663	86.63%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7817	78.17%
OATP2B1 inhibitior	-	0.7164	71.64%
OATP1B1 inhibitior	+	0.8064	80.64%
OATP1B3 inhibitior	+	0.9271	92.71%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9419	94.19%
P-glycoprotein inhibitior	+	0.7499	74.99%
P-glycoprotein substrate	+	0.8653	86.53%
CYP3A4 substrate	+	0.7359	73.59%
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	+	0.7808	78.08%
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	-	0.9026	90.26%
Skin irritation	-	0.7667	76.67%
Skin corrosion	-	0.9237	92.37%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7485	74.85%
Micronuclear	+	0.7000	70.00%
Hepatotoxicity	-	0.5932	59.32%
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	-	0.6096	60.96%
Acute Oral Toxicity (c)	III	0.3746	37.46%
Estrogen receptor binding	+	0.7858	78.58%
Androgen receptor binding	+	0.7262	72.62%
Thyroid receptor binding	+	0.6276	62.76%
Glucocorticoid receptor binding	+	0.6584	65.84%
Aromatase binding	+	0.6446	64.46%
PPAR gamma	+	0.8025	80.25%
Honey bee toxicity	-	0.6541	65.41%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
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
CHEMBL4040	P28482	MAP kinase ERK2	99.69%	83.82%
CHEMBL2581	P07339	Cathepsin D	99.65%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.48%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.29%	91.11%
CHEMBL3837	P07711	Cathepsin L	96.65%	96.61%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.27%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.49%	95.56%
CHEMBL2179	P04062	Beta-glucocerebrosidase	95.16%	85.31%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.25%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.48%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.05%	97.09%
CHEMBL1937	Q92769	Histone deacetylase 2	92.87%	94.75%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	92.85%	91.71%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	92.52%	97.64%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.85%	95.89%
CHEMBL1255126	O15151	Protein Mdm4	91.20%	90.20%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	91.12%	82.69%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	88.97%	95.89%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	88.53%	90.71%
CHEMBL2535	P11166	Glucose transporter	87.84%	98.75%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	87.56%	89.67%
CHEMBL5103	Q969S8	Histone deacetylase 10	87.02%	90.08%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	86.88%	96.47%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.81%	95.50%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.66%	93.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.42%	97.14%
CHEMBL1902	P62942	FK506-binding protein 1A	82.28%	97.05%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.13%	100.00%
CHEMBL3524	P56524	Histone deacetylase 4	81.58%	92.97%
CHEMBL4072	P07858	Cathepsin B	81.26%	93.67%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.07%	100.00%

Plants that contains it

• Elsholtzia bodinieri
• Ipomoea purpurea

Cross-Links

• PubChem: 21637043
• NPASS: NPC29679
• LOTUS: LTS0116456
• wikiData: Q77377792