Cytochalasin Z4

Details

• Internal ID: f96a4906-e706-4c99-8ddf-7f6a75d78bd3
• Taxonomy: Alkaloids and derivatives > Cytochalasans > Cytochalasins
• IUPAC Name: (1S,4E,6R,10R,12E,14S,15S,17S,18S,19S)-6,15-dihydroxy-19-[(2-hydroxyphenyl)methyl]-10,17-dimethyl-16-methylidene-2-oxa-20-azatricyclo[12.7.0.01,18]henicosa-4,12-diene-3,21-dione
• SMILES (Canonical): CC1CCCC(C=CC(=O)OC23C(C=CC1)C(C(=C)C(C2C(NC3=O)CC4=CC=CC=C4O)C)O)O
• SMILES (Isomeric): C[C@@H]1CCC[C@H](/C=C/C(=O)O[C@]23[C@@H](/C=C/C1)[C@@H](C(=C)[C@H]([C@H]2[C@@H](NC3=O)CC4=CC=CC=C4O)C)O)O
• InChI: InChI=1S/C29H37NO6/c1-17-8-6-11-21(31)14-15-25(33)36-29-22(12-7-9-17)27(34)19(3)18(2)26(29)23(30-28(29)35)16-20-10-4-5-13-24(20)32/h4-5,7,10,12-15,17-18,21-23,26-27,31-32,34H,3,6,8-9,11,16H2,1-2H3,(H,30,35)/b12-7+,15-14+/t17-,18-,21-,22+,23+,26+,27-,29-/m1/s1
• InChI Key: MCTQEULMNSKBJK-YKQYRMHISA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₇NO₆
• Molecular Weight: 495.60 g/mol
• Exact Mass: 495.26208790 g/mol
• Topological Polar Surface Area (TPSA): 116.00 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 3.20
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 2

Synonyms

• CHEMBL467209
• (1S,4E,6R,10R,12E,14S,15S,17S,18S,19S)-6,15-dihydroxy-19-[(2-hydroxyphenyl)methyl]-10,17-dimethyl-16-methylidene-2-oxa-20-azatricyclo[12.7.0.01,18]henicosa-4,12-diene-3,21-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9830	98.30%
Caco-2	-	0.8197	81.97%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6697	66.97%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8071	80.71%
OATP1B3 inhibitior	+	0.8994	89.94%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.7822	78.22%
BSEP inhibitior	+	0.7529	75.29%
P-glycoprotein inhibitior	-	0.7130	71.30%
P-glycoprotein substrate	+	0.6532	65.32%
CYP3A4 substrate	+	0.6862	68.62%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8672	86.72%
CYP3A4 inhibition	-	0.7594	75.94%
CYP2C9 inhibition	-	0.7959	79.59%
CYP2C19 inhibition	-	0.7230	72.30%
CYP2D6 inhibition	-	0.9166	91.66%
CYP1A2 inhibition	-	0.7434	74.34%
CYP2C8 inhibition	+	0.6448	64.48%
CYP inhibitory promiscuity	-	0.6327	63.27%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Danger	0.4579	45.79%
Eye corrosion	-	0.9905	99.05%
Eye irritation	-	0.9624	96.24%
Skin irritation	-	0.7258	72.58%
Skin corrosion	-	0.9257	92.57%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6588	65.88%
Micronuclear	+	0.7300	73.00%
Hepatotoxicity	+	0.6460	64.60%
skin sensitisation	-	0.8148	81.48%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	+	0.5918	59.18%
Acute Oral Toxicity (c)	III	0.4777	47.77%
Estrogen receptor binding	+	0.7624	76.24%
Androgen receptor binding	+	0.6719	67.19%
Thyroid receptor binding	-	0.4890	48.90%
Glucocorticoid receptor binding	+	0.7899	78.99%
Aromatase binding	+	0.5977	59.77%
PPAR gamma	+	0.6706	67.06%
Honey bee toxicity	-	0.7684	76.84%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.9913	99.13%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.71%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.59%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.87%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.74%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.82%	96.09%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	90.98%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.01%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.75%	86.33%
CHEMBL1937	Q92769	Histone deacetylase 2	86.56%	94.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.33%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.12%	95.89%
CHEMBL3192	Q9BY41	Histone deacetylase 8	83.12%	93.99%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.08%	97.25%
CHEMBL4530	P00488	Coagulation factor XIII	82.25%	96.00%
CHEMBL4208	P20618	Proteasome component C5	81.82%	90.00%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	81.03%	92.88%

Plants that contains it

• Aconitum brevicalcaratum
• Ammodendron conollyi
• Cirsium dipsacolepis
• Cocculus diversifolius
• Crinum kirkii
• Cytisus scoparius
• Heliomeris longifolia var. annua
• Hypericum triquetrifolium
• Isodon japonicus
• Knightia deplanchei
• Mallotus rhamnifolius
• Malva sylvestris
• Mesembryanthemum emarcidum
• Nerium oleander
• Plantago lanceolata
• Ptilidium ciliare
• Scutellaria seleriana
• Solanum pimpinellifolium
• Teucrium pestalozzae
• Trichotosia subsessilis
• Trifolium apertum
• Tripodanthus acutifolius
• Veronica pectinata

Cross-Links

• PubChem: 21574191
• NPASS: NPC223865
• LOTUS: LTS0253839
• wikiData: Q75067250