(5R,8S,11R,15S,18S,19S,22R)-18-[(1E,3E,5S,6S)-6-acetyloxy-3,5-dimethyl-7-phenylhepta-1,3-dienyl]-15-[4-(diaminomethylideneamino)butyl]-1,5,19-trimethyl-2-methylidene-8-(2-methylpropyl)-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptazacyclopentacosane-11,22-dicarboxylic acid

Details

• Internal ID: a9707465-7606-429d-b9b9-6440a668ba0d
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Hybrid peptides
• IUPAC Name: (5R,8S,11R,15S,18S,19S,22R)-18-[(1E,3E,5S,6S)-6-acetyloxy-3,5-dimethyl-7-phenylhepta-1,3-dienyl]-15-[4-(diaminomethylideneamino)butyl]-1,5,19-trimethyl-2-methylidene-8-(2-methylpropyl)-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptazacyclopentacosane-11,22-dicarboxylic acid
• InChI: InChI=1S/C50H74N10O13/c1-27(2)23-38-47(68)59-39(49(71)72)26-41(62)55-36(17-13-14-22-53-50(51)52)46(67)56-35(19-18-28(3)24-29(4)40(73-33(8)61)25-34-15-11-10-12-16-34)30(5)43(64)57-37(48(69)70)20-21-42(63)60(9)32(7)45(66)54-31(6)44(65)58-38/h10-12,15-16,18-19,24,27,29-31,35-40H,7,13-14,17,20-23,25-26H2,1-6,8-9H3,(H,54,66)(H,55,62)(H,56,67)(H,57,64)(H,58,65)(H,59,68)(H,69,70)(H,71,72)(H4,51,52,53)/b19-18+,28-24+/t29-,30-,31+,35-,36-,37+,38-,39+,40-/m0/s1
• InChI Key: WJEBNDAWEAQNLR-KDMHZOGOSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₀H₇₄N₁₀O₁₃
• Molecular Weight: 1023.20 g/mol
• Exact Mass: 1022.54368245 g/mol
• Topological Polar Surface Area (TPSA): 360.00 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 0.68
• H-Bond Acceptor: 12
• H-Bond Donor: 10
• Rotatable Bonds: 16

Synonyms

• (Asp(3)-admaadda(5))microcystin-lhar
• 141663-36-7
• [D-Asp3,ADMAdda5]MC-LHar
• (5R,8S,11R,15S,18S,19S,22R)-18-[(1E,3E,5S,6S)-6-acetyloxy-3,5-dimethyl-7-phenylhepta-1,3-dienyl]-15-[4-(diaminomethylideneamino)butyl]-1,5,19-trimethyl-2-methylidene-8-(2-methylpropyl)-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptazacyclopentacosane-11,22-dicarboxylic acid
• DTXSID401046168
• 4-D-beta-Aspartic acid-5-(N6-(aminoiminomethyl)-L-lysin)-6-((2S,4E,6E,8S,9S)-9-(acetyloxy)-4,5,6,7-tetradehydro-2,6,8-trimethyl-10-phenyl-L-3-aminodecanoic acid)cyanoginosin LA
• Cyanoginosin LA, 4-D-beta-aspartic acid-5-(N6-(aminoiminomethyl)-L-lysin)-6-((2S,4E,6E,8S,9S)-9-(acetyloxy)-4,5,6,7-tetradehydro-2,6,8-trimethyl-10-phenyl-L-3-aminodecanoic acid)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5552	55.52%
Caco-2	-	0.8640	86.40%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7074	70.74%
OATP2B1 inhibitior	-	0.8549	85.49%
OATP1B1 inhibitior	+	0.8119	81.19%
OATP1B3 inhibitior	+	0.9206	92.06%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9081	90.81%
P-glycoprotein inhibitior	+	0.7457	74.57%
P-glycoprotein substrate	+	0.8750	87.50%
CYP3A4 substrate	+	0.7423	74.23%
CYP2C9 substrate	-	0.6215	62.15%
CYP2D6 substrate	-	0.8724	87.24%
CYP3A4 inhibition	-	0.8186	81.86%
CYP2C9 inhibition	-	0.7291	72.91%
CYP2C19 inhibition	-	0.7268	72.68%
CYP2D6 inhibition	-	0.8896	88.96%
CYP1A2 inhibition	-	0.7517	75.17%
CYP2C8 inhibition	+	0.7804	78.04%
CYP inhibitory promiscuity	-	0.9527	95.27%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.6064	60.64%
Eye corrosion	-	0.9823	98.23%
Eye irritation	-	0.9002	90.02%
Skin irritation	-	0.7584	75.84%
Skin corrosion	-	0.9180	91.80%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7176	71.76%
Micronuclear	+	0.8000	80.00%
Hepatotoxicity	+	0.6014	60.14%
skin sensitisation	-	0.8339	83.39%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.6501	65.01%
Acute Oral Toxicity (c)	I	0.6806	68.06%
Estrogen receptor binding	+	0.7564	75.64%
Androgen receptor binding	+	0.7389	73.89%
Thyroid receptor binding	+	0.6472	64.72%
Glucocorticoid receptor binding	+	0.6432	64.32%
Aromatase binding	+	0.6542	65.42%
PPAR gamma	+	0.7845	78.45%
Honey bee toxicity	-	0.6547	65.47%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9571	95.71%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.92%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	99.92%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.34%	96.09%
CHEMBL3837	P07711	Cathepsin L	98.31%	96.61%
CHEMBL4072	P07858	Cathepsin B	97.14%	93.67%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.66%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.85%	86.33%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	95.70%	97.64%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.59%	99.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.13%	91.11%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	90.70%	91.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.52%	94.45%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	90.33%	95.89%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.23%	95.89%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	88.95%	90.71%
CHEMBL1937	Q92769	Histone deacetylase 2	87.80%	94.75%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	87.44%	93.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.96%	97.09%
CHEMBL5103	Q969S8	Histone deacetylase 10	86.02%	90.08%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	85.41%	97.33%
CHEMBL2535	P11166	Glucose transporter	83.83%	98.75%
CHEMBL1255126	O15151	Protein Mdm4	83.09%	90.20%
CHEMBL217	P14416	Dopamine D2 receptor	82.93%	95.62%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.83%	93.56%
CHEMBL4644	P41968	Melanocortin receptor 3	82.40%	99.52%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.97%	82.69%
CHEMBL2327	P21452	Neurokinin 2 receptor	80.36%	98.89%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 6441259
• LOTUS: LTS0099501
• wikiData: Q105306707