(2S,3R,4S,5S)-2-[[(3S,3aS,4S,5aR,5bR,7S,7aR,9S,11aR,11bR,13aR,13bR)-9-[(2S,3R,4S,5S)-3,5-dihydroxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-7-hydroxy-3-(2-hydroxypropan-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-1,2,3,3a,4,5,6,7,7a,9,10,11,11b,12,13,13a-hexadecahydrocyclopenta[a]chrysen-4-yl]oxy]oxane-3,4,5-triol

Details

• Internal ID: ccb69bf7-3482-4d12-befe-0b3b5216a09a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Hopanoids
• IUPAC Name: (2S,3R,4S,5S)-2-[[(3S,3aS,4S,5aR,5bR,7S,7aR,9S,11aR,11bR,13aR,13bR)-9-[(2S,3R,4S,5S)-3,5-dihydroxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-7-hydroxy-3-(2-hydroxypropan-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-1,2,3,3a,4,5,6,7,7a,9,10,11,11b,12,13,13a-hexadecahydrocyclopenta[a]chrysen-4-yl]oxy]oxane-3,4,5-triol
• SMILES (Canonical): CC1(C(CCC2(C1C(CC3(C2CCC4C3(CC(C5C4(CCC5C(C)(C)O)C)OC6C(C(C(CO6)O)O)O)C)C)O)C)OC7C(C(C(CO7)O)OC8C(C(C(CO8)O)O)O)O)C
• SMILES (Isomeric): C[C@]12CC[C@@H]([C@@H]1[C@H](C[C@@]3([C@@H]2CC[C@H]4[C@]3(C[C@@H]([C@@H]5[C@@]4(CC[C@@H](C5(C)C)O[C@H]6[C@@H]([C@H]([C@H](CO6)O)O[C@H]7[C@@H]([C@H]([C@@H](CO7)O)O)O)O)C)O)C)C)O[C@H]8[C@@H]([C@H]([C@H](CO8)O)O)O)C(C)(C)O
• InChI: InChI=1S/C45H76O16/c1-40(2)28(60-39-34(54)35(24(49)19-58-39)61-38-33(53)31(51)23(48)18-57-38)12-14-43(6)27-10-9-26-42(5)13-11-20(41(3,4)55)29(42)25(59-37-32(52)30(50)22(47)17-56-37)16-45(26,8)44(27,7)15-21(46)36(40)43/h20-39,46-55H,9-19H2,1-8H3/t20-,21-,22-,23+,24-,25-,26+,27+,28-,29+,30-,31-,32+,33+,34+,35-,36-,37-,38-,39-,42+,43+,44+,45+/m0/s1
• InChI Key: XLPWHCKLGKFHCL-GSHBARKISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₅H₇₆O₁₆
• Molecular Weight: 873.10 g/mol
• Exact Mass: 872.51333633 g/mol
• Topological Polar Surface Area (TPSA): 258.00 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 0.55
• H-Bond Acceptor: 16
• H-Bond Donor: 10
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5910	59.10%
Caco-2	-	0.8821	88.21%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6634	66.34%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8841	88.41%
OATP1B3 inhibitior	+	0.9056	90.56%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	-	0.6365	63.65%
P-glycoprotein inhibitior	+	0.7520	75.20%
P-glycoprotein substrate	-	0.5684	56.84%
CYP3A4 substrate	+	0.7168	71.68%
CYP2C9 substrate	-	0.7981	79.81%
CYP2D6 substrate	-	0.8283	82.83%
CYP3A4 inhibition	-	0.9691	96.91%
CYP2C9 inhibition	-	0.9021	90.21%
CYP2C19 inhibition	-	0.8903	89.03%
CYP2D6 inhibition	-	0.9560	95.60%
CYP1A2 inhibition	-	0.9021	90.21%
CYP2C8 inhibition	+	0.5989	59.89%
CYP inhibitory promiscuity	-	0.9822	98.22%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6337	63.37%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9062	90.62%
Skin irritation	-	0.7062	70.62%
Skin corrosion	-	0.9456	94.56%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7429	74.29%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.9138	91.38%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.9213	92.13%
Acute Oral Toxicity (c)	I	0.4989	49.89%
Estrogen receptor binding	+	0.7343	73.43%
Androgen receptor binding	+	0.7312	73.12%
Thyroid receptor binding	-	0.5765	57.65%
Glucocorticoid receptor binding	+	0.5920	59.20%
Aromatase binding	+	0.6579	65.79%
PPAR gamma	+	0.7407	74.07%
Honey bee toxicity	-	0.6208	62.08%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.8551	85.51%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.49%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.02%	91.11%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	93.72%	92.88%
CHEMBL241	Q14432	Phosphodiesterase 3A	93.19%	92.94%
CHEMBL1937	Q92769	Histone deacetylase 2	91.95%	94.75%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.51%	95.89%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.96%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.71%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.43%	94.45%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.53%	96.77%
CHEMBL3922	P50579	Methionine aminopeptidase 2	87.32%	97.28%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.19%	97.14%
CHEMBL2581	P07339	Cathepsin D	86.50%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.03%	100.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.00%	94.00%
CHEMBL2179	P04062	Beta-glucocerebrosidase	83.98%	85.31%
CHEMBL325	Q13547	Histone deacetylase 1	83.67%	95.92%
CHEMBL2815	P04629	Nerve growth factor receptor Trk-A	83.29%	87.16%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.39%	89.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.30%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.15%	85.14%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.67%	82.69%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.54%	86.33%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	80.27%	94.78%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	80.22%	100.00%
CHEMBL1974	P36888	Tyrosine-protein kinase receptor FLT3	80.05%	91.83%

Plants that contains it

• Polycarpon succulentum
• Polypodium vulgare

Cross-Links

• PubChem: 102438588
• LOTUS: LTS0187454
• wikiData: Q105278871