Phallacidin

Details

• Internal ID: 7ef70535-abf9-4ca0-8147-4b594430580e
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Peptides > Oligopeptides
• IUPAC Name: 2-[28-(2,3-dihydroxy-2-methylpropyl)-18-hydroxy-23-methyl-15,21,24,26,29,32,35-heptaoxo-31-propan-2-yl-12-thia-10,16,22,25,27,30,33,36-octazapentacyclo[12.11.11.03,11.04,9.016,20]hexatriaconta-3(11),4,6,8-tetraen-34-yl]-2-hydroxyacetic acid
• SMILES (Canonical): CC1C(=O)NC2CC3=C(NC4=CC=CC=C34)SCC(C(=O)N5CC(CC5C(=O)N1)O)NC(=O)C(NC(=O)C(NC(=O)C(NC2=O)CC(C)(CO)O)C(C)C)C(C(=O)O)O
• SMILES (Isomeric): CC1C(=O)NC2CC3=C(NC4=CC=CC=C34)SCC(C(=O)N5CC(CC5C(=O)N1)O)NC(=O)C(NC(=O)C(NC(=O)C(NC2=O)CC(C)(CO)O)C(C)C)C(C(=O)O)O
• InChI: InChI=1S/C37H50N8O13S/c1-15(2)25-32(53)44-26(27(48)36(56)57)33(54)41-23-13-59-34-19(18-7-5-6-8-20(18)42-34)10-21(29(50)40-22(30(51)43-25)11-37(4,58)14-46)39-28(49)16(3)38-31(52)24-9-17(47)12-45(24)35(23)55/h5-8,15-17,21-27,42,46-48,58H,9-14H2,1-4H3,(H,38,52)(H,39,49)(H,40,50)(H,41,54)(H,43,51)(H,44,53)(H,56,57)
• InChI Key: KUBDTFZQCYLLGC-UHFFFAOYSA-N
• Popularity: 47 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₅₀N₈O₁₃S
• Molecular Weight: 846.90 g/mol
• Exact Mass: 846.32180485 g/mol
• Topological Polar Surface Area (TPSA): 354.00 Ų
• XlogP: -1.50
• Atomic LogP (AlogP): -4.04
• H-Bond Acceptor: 13
• H-Bond Donor: 12
• Rotatable Bonds: 6

Synonyms

• 26645-35-2
• cyclic(L-Alanyl-2-mercapto-L-tryptophyl-4,5-dihydroxy-L-leucyl-L-valyl-erythro-3-hydroxy-D-alpha-aspartyl-L-cysteinyl-cis-4-hydroxy-L-prolyl) cyclic (2-6)-sulfide
• BRN 0604129
• SCHEMBL3507281
• DTXSID001046316
• Phallacidin from Amanita phalloides, >=85%
• J-016505

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6438	64.38%
Caco-2	-	0.8767	87.67%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.4445	44.45%
OATP2B1 inhibitior	+	0.5144	51.44%
OATP1B1 inhibitior	+	0.8016	80.16%
OATP1B3 inhibitior	+	0.9320	93.20%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.8877	88.77%
P-glycoprotein inhibitior	+	0.7223	72.23%
P-glycoprotein substrate	+	0.8164	81.64%
CYP3A4 substrate	+	0.7245	72.45%
CYP2C9 substrate	-	0.6082	60.82%
CYP2D6 substrate	-	0.8367	83.67%
CYP3A4 inhibition	-	0.8564	85.64%
CYP2C9 inhibition	-	0.7738	77.38%
CYP2C19 inhibition	-	0.6556	65.56%
CYP2D6 inhibition	-	0.8765	87.65%
CYP1A2 inhibition	-	0.7573	75.73%
CYP2C8 inhibition	+	0.7078	70.78%
CYP inhibitory promiscuity	-	0.6376	63.76%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7900	79.00%
Carcinogenicity (trinary)	Non-required	0.5687	56.87%
Eye corrosion	-	0.9864	98.64%
Eye irritation	-	0.9117	91.17%
Skin irritation	-	0.7624	76.24%
Skin corrosion	-	0.9253	92.53%
Ames mutagenesis	-	0.6408	64.08%
Human Ether-a-go-go-Related Gene inhibition	-	0.3638	36.38%
Micronuclear	+	0.8000	80.00%
Hepatotoxicity	+	0.7375	73.75%
skin sensitisation	-	0.8362	83.62%
Respiratory toxicity	+	0.9000	90.00%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.8060	80.60%
Acute Oral Toxicity (c)	III	0.5592	55.92%
Estrogen receptor binding	+	0.8056	80.56%
Androgen receptor binding	+	0.7238	72.38%
Thyroid receptor binding	+	0.5844	58.44%
Glucocorticoid receptor binding	+	0.6294	62.94%
Aromatase binding	+	0.6290	62.90%
PPAR gamma	+	0.7861	78.61%
Honey bee toxicity	-	0.7321	73.21%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9044	90.44%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.81%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.85%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.28%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.66%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	96.47%	83.82%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.47%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.28%	97.25%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	95.82%	94.23%
CHEMBL5103	Q969S8	Histone deacetylase 10	94.46%	90.08%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.20%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.41%	97.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	92.56%	97.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.50%	99.23%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	92.33%	96.47%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	92.30%	94.62%
CHEMBL1914	P06276	Butyrylcholinesterase	90.86%	95.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.64%	89.00%
CHEMBL1902	P62942	FK506-binding protein 1A	90.58%	97.05%
CHEMBL213	P08588	Beta-1 adrenergic receptor	90.40%	95.56%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	89.92%	91.71%
CHEMBL3310	Q96DB2	Histone deacetylase 11	89.25%	88.56%
CHEMBL3359	P21462	Formyl peptide receptor 1	88.41%	93.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.47%	99.17%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	87.45%	94.08%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	83.97%	97.64%
CHEMBL221	P23219	Cyclooxygenase-1	83.82%	90.17%
CHEMBL1949	P62937	Cyclophilin A	83.52%	98.57%
CHEMBL2535	P11166	Glucose transporter	81.05%	98.75%
CHEMBL2959	Q08881	Tyrosine-protein kinase ITK/TSK	80.20%	95.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 3034055
• LOTUS: LTS0011232
• wikiData: Q105146052