beta-Hederin

Details

• Internal ID: 9719e330-3690-4d56-a6fb-d449b1b891a3
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(COC2OC3CCC4(C(C3(C)C)CCC5(C4CC=C6C5(CCC7(C6CC(CC7)(C)C)C(=O)O)C)C)C)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@H](CO[C@H]2O[C@H]3CC[C@]4([C@H](C3(C)C)CC[C@@]5([C@@H]4CC=C6[C@]5(CC[C@@]7([C@H]6CC(CC7)(C)C)C(=O)O)C)C)C)O)O)O)O)O
• InChI: InChI=1S/C41H66O11/c1-21-28(43)30(45)31(46)33(50-21)52-32-29(44)24(42)20-49-34(32)51-27-12-13-38(6)25(37(27,4)5)11-14-40(8)26(38)10-9-22-23-19-36(2,3)15-17-41(23,35(47)48)18-16-39(22,40)7/h9,21,23-34,42-46H,10-20H2,1-8H3,(H,47,48)/t21-,23-,24-,25-,26+,27-,28-,29-,30+,31+,32+,33-,34-,38-,39+,40+,41-/m0/s1
• InChI Key: IBAJNOZMACNWJD-HVUPOBLPSA-N
• Popularity: 88 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₁H₆₆O₁₁
• Molecular Weight: 735.00 g/mol
• Exact Mass: 734.46051292 g/mol
• Topological Polar Surface Area (TPSA): 175.00 Ų
• XlogP: 4.90
• Atomic LogP (AlogP): 4.55
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

• 35790-95-5
• (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• CHEBI:10419
• .beta.-Hederin
• C08955
• CHEMBL502407
• SCHEMBL22761642
• DTXSID90331673
• (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• HY-N7489
• AKOS037514570
• CS-0129980
• Q27108632
• Olean-12-en-28-oic acid, 3-[[2-O-(6-deoxy-.alpha.-L-mannopyranosyl)-.alpha.-L-arabinopyranosyl]oxy]-, (3.beta.)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8956	89.56%
Caco-2	-	0.8717	87.17%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8672	86.72%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.6841	68.41%
OATP1B3 inhibitior	-	0.2786	27.86%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6526	65.26%
BSEP inhibitior	-	0.5559	55.59%
P-glycoprotein inhibitior	+	0.7676	76.76%
P-glycoprotein substrate	-	0.7150	71.50%
CYP3A4 substrate	+	0.7178	71.78%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8798	87.98%
CYP3A4 inhibition	-	0.9290	92.90%
CYP2C9 inhibition	-	0.8742	87.42%
CYP2C19 inhibition	-	0.9193	91.93%
CYP2D6 inhibition	-	0.9330	93.30%
CYP1A2 inhibition	-	0.8587	85.87%
CYP2C8 inhibition	+	0.6450	64.50%
CYP inhibitory promiscuity	-	0.9661	96.61%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6143	61.43%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9160	91.60%
Skin irritation	-	0.5408	54.08%
Skin corrosion	-	0.9417	94.17%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3879	38.79%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.8875	88.75%
skin sensitisation	-	0.8585	85.85%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.8699	86.99%
Acute Oral Toxicity (c)	III	0.6425	64.25%
Estrogen receptor binding	+	0.6971	69.71%
Androgen receptor binding	+	0.7073	70.73%
Thyroid receptor binding	-	0.6165	61.65%
Glucocorticoid receptor binding	+	0.6384	63.84%
Aromatase binding	+	0.6607	66.07%
PPAR gamma	+	0.6996	69.96%
Honey bee toxicity	-	0.7223	72.23%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5105	51.05%
Fish aquatic toxicity	+	0.9724	97.24%

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	96.04%	91.11%
CHEMBL3714130	P46095	G-protein coupled receptor 6	94.50%	97.36%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.53%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	91.26%	96.77%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	89.56%	95.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.86%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.72%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.01%	97.09%
CHEMBL221	P23219	Cyclooxygenase-1	86.59%	90.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.88%	89.00%
CHEMBL2581	P07339	Cathepsin D	83.76%	98.95%
CHEMBL2179	P04062	Beta-glucocerebrosidase	83.42%	85.31%
CHEMBL5028	O14672	ADAM10	82.70%	97.50%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.63%	92.94%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.23%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.64%	95.89%

Plants that contains it

• Akebia quinata
• Anemoclema glaucifolium
• Anemone coronaria
• Clematis tangutica
• Eleutherococcus senticosus
• Hedera canariensis
• Hedera caucasigena
• Hedera helix
• Hedera nepalensis
• Kalopanax septemlobus
• Polyscias fulva
• Pulsatilla chinensis

Cross-Links

• PubChem: 441929
• NPASS: NPC56713
• ChEMBL: CHEMBL502407
• LOTUS: LTS0195425
• wikiData: Q27108632