Isocyclamin

Details

• Internal ID: 4730fa6a-3e7c-4064-9601-d16bbb85de1c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (1S,2R,4S,5R,8R,10S,13R,14R,17S,18R,20S)-10-[(2S,3R,4S,5S)-5-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-4-hydroxy-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-hydroxy-4,5,9,9,13,20-hexamethyl-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracosane-20-carbaldehyde
• SMILES (Canonical): CC1(C2CCC3(C(C2(CCC1OC4C(C(C(CO4)OC5C(C(C(C(O5)COC6C(C(C(C(O6)CO)O)O)O)O)O)OC7C(C(C(CO7)O)O)O)O)OC8C(C(C(C(O8)CO)O)O)O)C)CCC91C3(CC(C2(C9CC(CC2)(C)C=O)CO1)O)C)C)C
• SMILES (Isomeric): C[C@@]1(CC[C@@]23CO[C@]4([C@@H]2C1)CC[C@@H]5[C@]6(CC[C@@H](C([C@@H]6CC[C@]5([C@@]4(C[C@H]3O)C)C)(C)C)O[C@H]7[C@@H]([C@H]([C@H](CO7)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O)O)O)O[C@H]1[C@@H]([C@H]([C@H](CO1)O)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)C)C=O
• InChI: InChI=1S/C58H94O27/c1-52(2)29-7-11-55(5)30(8-12-58-31-15-53(3,22-61)13-14-57(31,23-78-58)32(63)16-56(55,58)6)54(29,4)10-9-33(52)83-50-45(85-49-44(74)40(70)36(66)26(18-60)80-49)38(68)28(21-77-50)82-51-46(84-48-42(72)34(64)24(62)19-75-48)41(71)37(67)27(81-51)20-76-47-43(73)39(69)35(65)25(17-59)79-47/h22,24-51,59-60,62-74H,7-21,23H2,1-6H3/t24-,25+,26+,27+,28-,29-,30+,31+,32+,33-,34-,35+,36+,37+,38-,39-,40-,41-,42+,43+,44+,45+,46+,47+,48-,49-,50-,51-,53-,54-,55+,56-,57+,58-/m0/s1
• InChI Key: OPQUPAIXWBVUBV-KNVVNGEPSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₈H₉₄O₂₇
• Molecular Weight: 1223.30 g/mol
• Exact Mass: 1222.59824772 g/mol
• Topological Polar Surface Area (TPSA): 422.00 Ų
• XlogP: -3.20
• Atomic LogP (AlogP): -4.07
• H-Bond Acceptor: 27
• H-Bond Donor: 15
• Rotatable Bonds: 14

Synonyms

• CHEMBL449272

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6397	63.97%
Caco-2	-	0.8753	87.53%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7227	72.27%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8038	80.38%
OATP1B3 inhibitior	+	0.9276	92.76%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	+	0.8751	87.51%
P-glycoprotein inhibitior	+	0.7431	74.31%
P-glycoprotein substrate	+	0.5915	59.15%
CYP3A4 substrate	+	0.7505	75.05%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8272	82.72%
CYP3A4 inhibition	-	0.9228	92.28%
CYP2C9 inhibition	-	0.8526	85.26%
CYP2C19 inhibition	-	0.8627	86.27%
CYP2D6 inhibition	-	0.9523	95.23%
CYP1A2 inhibition	-	0.9157	91.57%
CYP2C8 inhibition	+	0.7412	74.12%
CYP inhibitory promiscuity	-	0.9693	96.93%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6545	65.45%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.8997	89.97%
Skin irritation	-	0.6766	67.66%
Skin corrosion	-	0.9455	94.55%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7951	79.51%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.9229	92.29%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.6663	66.63%
Acute Oral Toxicity (c)	I	0.6300	63.00%
Estrogen receptor binding	+	0.7925	79.25%
Androgen receptor binding	+	0.7539	75.39%
Thyroid receptor binding	+	0.5532	55.32%
Glucocorticoid receptor binding	+	0.7177	71.77%
Aromatase binding	+	0.6283	62.83%
PPAR gamma	+	0.7872	78.72%
Honey bee toxicity	-	0.5771	57.71%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5655	56.55%
Fish aquatic toxicity	+	0.8764	87.64%

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	95.38%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	95.26%	95.93%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.00%	91.11%
CHEMBL2581	P07339	Cathepsin D	90.09%	98.95%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	90.08%	91.24%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	90.01%	95.50%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.37%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.64%	97.09%
CHEMBL1871	P10275	Androgen Receptor	88.55%	96.43%
CHEMBL233	P35372	Mu opioid receptor	88.45%	97.93%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.97%	100.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	86.94%	96.61%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.69%	95.89%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	86.25%	94.33%
CHEMBL3922	P50579	Methionine aminopeptidase 2	86.18%	97.28%
CHEMBL5957	P21589	5'-nucleotidase	86.07%	97.78%
CHEMBL1937	Q92769	Histone deacetylase 2	84.50%	94.75%
CHEMBL5255	O00206	Toll-like receptor 4	83.73%	92.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.32%	95.89%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	82.91%	100.00%
CHEMBL221	P23219	Cyclooxygenase-1	82.90%	90.17%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.73%	96.21%
CHEMBL5028	O14672	ADAM10	81.89%	97.50%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	81.59%	82.38%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.26%	96.77%
CHEMBL4302	P08183	P-glycoprotein 1	81.19%	92.98%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	81.18%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.51%	92.62%

Plants that contains it

• Artemisia cana
• Cyclamen hederifolium
• Cyclamen mirabile
• Cyclamen repandum

Cross-Links

• PubChem: 44566609
• LOTUS: LTS0008685
• wikiData: Q105347639