Pfafforside B

Details

• Internal ID: 9e02dcab-ade1-4b3b-b0c4-abc5f9e3fc8e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: [1-[16-[5-[4-[3,5-dihydroxy-6-(hydroxymethyl)-4-methoxyoxan-2-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[5-[4-[3,5-dihydroxy-6-(hydroxymethyl)-4-methoxyoxan-2-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydroxyoxan-2-yl]oxy-4-hydroxyoxan-2-yl]oxy-2,6,13,17,17-pentamethyl-8-oxo-7-oxapentacyclo[10.8.0.02,9.05,9.013,18]icos-1(20)-en-6-yl]-4-methylpentan-2-yl] acetate
• SMILES (Canonical): CC(C)CC(CC1(C2CCC3(C2(CCC4C3=CCC5C4(CCC(C5(C)C)OC6C(C(C(CO6)OC7C(C(C(C(O7)CO)O)OC8C(C(C(C(O8)CO)O)OC)O)O)O)OC9C(C(C(CO9)OC2C(C(C(C(O2)CO)O)OC2C(C(C(C(O2)CO)O)OC)O)O)O)O)C)C(=O)O1)C)C)OC(=O)C
• SMILES (Isomeric): CC(C)CC(CC1(C2CCC3(C2(CCC4C3=CCC5C4(CCC(C5(C)C)OC6C(C(C(CO6)OC7C(C(C(C(O7)CO)O)OC8C(C(C(C(O8)CO)O)OC)O)O)O)OC9C(C(C(CO9)OC2C(C(C(C(O2)CO)O)OC2C(C(C(C(O2)CO)O)OC)O)O)O)O)C)C(=O)O1)C)C)OC(=O)C
• InChI: InChI=1S/C68H110O33/c1-27(2)19-29(90-28(3)73)20-67(8)39-14-17-66(7)31-11-12-38-64(4,5)40(15-16-65(38,6)30(31)13-18-68(39,66)63(85)101-67)97-62-56(46(79)37(26-89-62)96-59-51(84)55(45(78)35(24-72)92-59)99-61-49(82)53(87-10)43(76)33(22-70)94-61)100-57-47(80)41(74)36(25-88-57)95-58-50(83)54(44(77)34(23-71)91-58)98-60-48(81)52(86-9)42(75)32(21-69)93-60/h11,27,29-30,32-62,69-72,74-84H,12-26H2,1-10H3
• InChI Key: UTTMVFMTWNLRGZ-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆₈H₁₁₀O₃₃
• Molecular Weight: 1455.60 g/mol
• Exact Mass: 1454.6929359 g/mol
• Topological Polar Surface Area (TPSA): 485.00 Ų
• XlogP: -1.80
• Atomic LogP (AlogP): -3.85
• H-Bond Acceptor: 33
• H-Bond Donor: 15
• Rotatable Bonds: 23

Synonyms

• Pfafforside B
• Stichloroside A
• Pfaffoside B
• Lanost-7-en-18-oic acid, 23-(acetyloxy)-20-hydroxy-3-((O-3-O-methyl-beta-D-glucopyranosyl-(1->3)-O-beta-D-glucopyranosyl-(1->4)-O-(O-3-O-methyl-beta-D-glucopyranosyl-(1->3)-O-beta-D-glucopyranosyl-(1->4)-beta-D-xylopyranosyl-(1->2))-beta-D-xylopyranosyl)oxy)-, gamma-lactone, (3beta,9beta,23S)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8036	80.36%
Caco-2	-	0.8630	86.30%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.8743	87.43%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8103	81.03%
OATP1B3 inhibitior	+	0.8514	85.14%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	+	0.9501	95.01%
P-glycoprotein inhibitior	+	0.7438	74.38%
P-glycoprotein substrate	+	0.6775	67.75%
CYP3A4 substrate	+	0.7486	74.86%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8868	88.68%
CYP3A4 inhibition	-	0.8952	89.52%
CYP2C9 inhibition	-	0.8464	84.64%
CYP2C19 inhibition	-	0.8975	89.75%
CYP2D6 inhibition	-	0.9411	94.11%
CYP1A2 inhibition	-	0.8952	89.52%
CYP2C8 inhibition	+	0.7527	75.27%
CYP inhibitory promiscuity	-	0.9266	92.66%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4843	48.43%
Eye corrosion	-	0.9880	98.80%
Eye irritation	-	0.8970	89.70%
Skin irritation	-	0.6018	60.18%
Skin corrosion	-	0.9376	93.76%
Ames mutagenesis	-	0.5934	59.34%
Human Ether-a-go-go-Related Gene inhibition	+	0.7816	78.16%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.6342	63.42%
skin sensitisation	-	0.9041	90.41%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	+	0.5783	57.83%
Acute Oral Toxicity (c)	III	0.6253	62.53%
Estrogen receptor binding	+	0.7055	70.55%
Androgen receptor binding	+	0.7652	76.52%
Thyroid receptor binding	+	0.6673	66.73%
Glucocorticoid receptor binding	+	0.8008	80.08%
Aromatase binding	+	0.6800	68.00%
PPAR gamma	+	0.8175	81.75%
Honey bee toxicity	-	0.6042	60.42%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9617	96.17%

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	98.77%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.29%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.69%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.61%	94.45%
CHEMBL1937	Q92769	Histone deacetylase 2	92.27%	94.75%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.19%	97.25%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	91.37%	96.77%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.17%	89.00%
CHEMBL221	P23219	Cyclooxygenase-1	89.68%	90.17%
CHEMBL332	P03956	Matrix metalloproteinase-1	89.37%	94.50%
CHEMBL5255	O00206	Toll-like receptor 4	88.10%	92.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.64%	97.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.98%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.89%	95.56%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	86.71%	94.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.36%	92.62%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	86.20%	95.71%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	85.86%	95.71%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.62%	100.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	85.51%	97.36%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.50%	97.09%
CHEMBL3922	P50579	Methionine aminopeptidase 2	84.37%	97.28%
CHEMBL5028	O14672	ADAM10	83.76%	97.50%
CHEMBL5103	Q969S8	Histone deacetylase 10	82.77%	90.08%
CHEMBL340	P08684	Cytochrome P450 3A4	82.57%	91.19%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.78%	100.00%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	80.74%	95.36%
CHEMBL4581	P52732	Kinesin-like protein 1	80.49%	93.18%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.42%	93.56%

Plants that contains it

• Hebanthe eriantha

Cross-Links

• PubChem: 157178
• LOTUS: LTS0237485
• wikiData: Q105279087