Cyclamin

Details

• Internal ID: 9e1bbb78-ae1e-4c4c-a89f-3dfeb6439d3d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (1S,2R,4S,5R,8R,10S,13R,14R,17S,18R,20S)-2-hydroxy-10-[(2S,3R,4S,5S)-4-hydroxy-5-[(2S,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-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)CO)O)OC6C(C(C(C(O6)CO)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)O)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)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(3,22-62)13-14-57(31,23-77-58)32(64)16-56(55,58)6)54(29,4)10-9-33(52)82-50-45(84-49-43(74)40(71)36(67)26(18-60)79-49)38(69)28(21-76-50)81-51-46(85-47-41(72)34(65)24(63)20-75-47)44(37(68)27(19-61)80-51)83-48-42(73)39(70)35(66)25(17-59)78-48/h22,24-51,59-61,63-74H,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+/m1/s1
• InChI Key: JPEQATLMKATGAQ-JOONIPAFSA-N
• Popularity: 5 references 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: -2.70
• Atomic LogP (AlogP): -4.07
• H-Bond Acceptor: 27
• H-Bond Donor: 15
• Rotatable Bonds: 14

Synonyms

• CHEBI:3987
• 23643-76-7
• C08938
• CHEMBL373379
• C58H94O27
• C58-H94-O27
• DTXSID301318584
• Oleanan-29-al, 13,28-epoxy-3-[(O-.beta.-D-glucopyranosyl-(1.fwdarw.3)-O-[.beta.-D-xylopyranosyl-(1.fwdarw.2)]-O-.beta.-D-glucopyranosyl-(1.fwdarw.4)-O-[.beta.-D-glucopyranosyl-(1.fwdarw.2)]-.alpha.-L-arabinopyranosyl)oxy]-16-hydroxy-, (3.beta.,16.alpha.,20.beta.)-
• Q27106281

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6397	63.97%
Caco-2	-	0.8752	87.52%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7227	72.27%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7969	79.69%
OATP1B3 inhibitior	+	0.9276	92.76%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	+	0.9064	90.64%
P-glycoprotein inhibitior	+	0.7438	74.38%
P-glycoprotein substrate	+	0.5620	56.20%
CYP3A4 substrate	+	0.7488	74.88%
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	+	0.7232	72.32%
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	-	0.8998	89.98%
Skin irritation	-	0.6766	67.66%
Skin corrosion	-	0.9455	94.55%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7926	79.26%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	-	0.8000	80.00%
skin sensitisation	-	0.9229	92.29%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.6866	68.66%
Acute Oral Toxicity (c)	I	0.6300	63.00%
Estrogen receptor binding	+	0.7897	78.97%
Androgen receptor binding	+	0.7555	75.55%
Thyroid receptor binding	+	0.5448	54.48%
Glucocorticoid receptor binding	+	0.7123	71.23%
Aromatase binding	+	0.6313	63.13%
PPAR gamma	+	0.7821	78.21%
Honey bee toxicity	-	0.5709	57.09%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5355	53.55%
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	95.36%	96.09%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	94.12%	91.24%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.63%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	91.83%	95.93%
CHEMBL2581	P07339	Cathepsin D	90.68%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.90%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.97%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.19%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.15%	95.89%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	86.64%	95.50%
CHEMBL233	P35372	Mu opioid receptor	86.60%	97.93%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	86.05%	94.33%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	85.86%	96.21%
CHEMBL3922	P50579	Methionine aminopeptidase 2	85.58%	97.28%
CHEMBL4302	P08183	P-glycoprotein 1	85.36%	92.98%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.83%	96.77%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	83.68%	91.03%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.32%	95.89%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	82.74%	92.88%
CHEMBL5255	O00206	Toll-like receptor 4	82.00%	92.50%
CHEMBL1937	Q92769	Histone deacetylase 2	81.91%	94.75%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.82%	100.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	80.39%	96.61%
CHEMBL259	P32245	Melanocortin receptor 4	80.02%	95.38%

Plants that contains it

• Ardisia japonica
• Cycas revoluta
• Cyclamen mirabile
• Cyclamen purpurascens

Cross-Links

• PubChem: 441916
• NPASS: NPC262567
• ChEMBL: CHEMBL373379
• LOTUS: LTS0194481
• wikiData: Q27106281