Bacteriohopanetetrol glucosamine

Details

• Internal ID: 157173ea-d41f-441f-9f13-2634a4b3ea50
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Hopanoids > Bacteriohopanoids
• IUPAC Name: (2S,3R,4R,7R)-7-[(3R,3aS,5aR,5bR,7aS,11aS,11bR,13aR,13bS)-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-3-yl]-1-[(2R,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctane-2,3,4-triol
• SMILES (Canonical): CC(CCC(C(C(COC1C(C(C(C(O1)CO)O)O)N)O)O)O)C2CCC3(C2CCC4(C3CCC5C4(CCC6C5(CCCC6(C)C)C)C)C)C
• SMILES (Isomeric): C[C@H](CC[C@H]([C@H]([C@H](CO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)N)O)O)O)[C@H]2CC[C@]3([C@H]2CC[C@@]4([C@@H]3CC[C@H]5[C@]4(CC[C@@H]6[C@@]5(CCCC6(C)C)C)C)C)C
• InChI: InChI=1S/C41H73NO8/c1-23(9-10-26(44)33(46)27(45)22-49-36-32(42)35(48)34(47)28(21-43)50-36)24-13-18-38(4)25(24)14-19-40(6)30(38)11-12-31-39(5)17-8-16-37(2,3)29(39)15-20-41(31,40)7/h23-36,43-48H,8-22,42H2,1-7H3/t23-,24-,25+,26-,27+,28-,29+,30-,31-,32-,33-,34-,35-,36-,38+,39+,40-,41-/m1/s1
• InChI Key: BDUDNTRWKFDSBE-GAXZCFOGSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₁H₇₃NO₈
• Molecular Weight: 708.00 g/mol
• Exact Mass: 707.53361829 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: 7.30
• Atomic LogP (AlogP): 4.76
• H-Bond Acceptor: 9
• H-Bond Donor: 7
• Rotatable Bonds: 10

Synonyms

• Bacteriohopanetetrol-glucosamine
• Tetrahydroxybacteriohopane-glucosamine
• CHEMBL505546
• CHEBI:132143
• tetrahydroxybacteriohopane glucosamine
• C21121
• Q27225440
• bacteriohopane-32,33,34,35-tetrol 35-beta-D-glucosaminide
• 35-O-(beta-D-glucosaminyl) bacteriohopane-32,33,34,35-tetrol
• (2S,3R,4R,7R)-7-[(3R,3aS,5aR,5bR,7aS,11aS,11bR,13aR,13bS)-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-3-yl]-1-[(2R,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctane-2,3,4-triol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7668	76.68%
Caco-2	-	0.8699	86.99%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Lysosomes	0.6226	62.26%
OATP2B1 inhibitior	-	0.7221	72.21%
OATP1B1 inhibitior	+	0.8615	86.15%
OATP1B3 inhibitior	+	0.9270	92.70%
MATE1 inhibitior	-	0.9212	92.12%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	-	0.9404	94.04%
P-glycoprotein inhibitior	+	0.7020	70.20%
P-glycoprotein substrate	-	0.6381	63.81%
CYP3A4 substrate	+	0.6954	69.54%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7785	77.85%
CYP3A4 inhibition	-	0.9485	94.85%
CYP2C9 inhibition	-	0.9112	91.12%
CYP2C19 inhibition	-	0.8282	82.82%
CYP2D6 inhibition	-	0.9396	93.96%
CYP1A2 inhibition	-	0.9231	92.31%
CYP2C8 inhibition	+	0.5490	54.90%
CYP inhibitory promiscuity	-	0.9056	90.56%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6304	63.04%
Eye corrosion	-	0.9872	98.72%
Eye irritation	-	0.9151	91.51%
Skin irritation	-	0.7362	73.62%
Skin corrosion	-	0.9280	92.80%
Ames mutagenesis	-	0.7343	73.43%
Human Ether-a-go-go-Related Gene inhibition	+	0.6828	68.28%
Micronuclear	+	0.5600	56.00%
Hepatotoxicity	-	0.7053	70.53%
skin sensitisation	-	0.8731	87.31%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.9103	91.03%
Acute Oral Toxicity (c)	III	0.5879	58.79%
Estrogen receptor binding	+	0.7269	72.69%
Androgen receptor binding	+	0.7517	75.17%
Thyroid receptor binding	-	0.5655	56.55%
Glucocorticoid receptor binding	+	0.5784	57.84%
Aromatase binding	+	0.6847	68.47%
PPAR gamma	+	0.6814	68.14%
Honey bee toxicity	-	0.7061	70.61%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7500	75.00%
Fish aquatic toxicity	-	0.3933	39.33%

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	98.78%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	97.70%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.51%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.82%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.66%	94.45%
CHEMBL226	P30542	Adenosine A1 receptor	94.15%	95.93%
CHEMBL218	P21554	Cannabinoid CB1 receptor	93.91%	96.61%
CHEMBL2581	P07339	Cathepsin D	92.22%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.66%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.32%	100.00%
CHEMBL1937	Q92769	Histone deacetylase 2	87.70%	94.75%
CHEMBL4227	P25090	Lipoxin A4 receptor	87.25%	100.00%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	87.13%	97.29%
CHEMBL237	P41145	Kappa opioid receptor	86.90%	98.10%
CHEMBL4581	P52732	Kinesin-like protein 1	84.90%	93.18%
CHEMBL2094135	Q96BI3	Gamma-secretase	84.30%	98.05%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.37%	100.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.94%	93.56%
CHEMBL3401	O75469	Pregnane X receptor	82.83%	94.73%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.65%	96.21%
CHEMBL344	Q99705	Melanin-concentrating hormone receptor 1	82.59%	92.50%
CHEMBL5103	Q969S8	Histone deacetylase 10	82.43%	90.08%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.92%	95.50%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	81.48%	91.03%
CHEMBL2360	P00492	Hypoxanthine-guanine phosphoribosyltransferase	80.11%	87.38%
CHEMBL2514	O95665	Neurotensin receptor 2	80.08%	100.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 11204813
• LOTUS: LTS0170655
• wikiData: Q27225440