10-[4,5-Dihydroxy-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid

Details

• Internal ID: b3a329a3-11cf-4770-a1ef-c1c31a341884
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: 10-[4,5-dihydroxy-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-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)CO)CCC5(C4CC=C6C5(CCC7(C6CC(CC7)(C)C)C(=O)O)C)C)C)O)O)O)O)O
• SMILES (Isomeric): CC1C(C(C(C(O1)OC2C(C(COC2OC3CCC4(C(C3(C)CO)CCC5(C4CC=C6C5(CCC7(C6CC(CC7)(C)C)C(=O)O)C)C)C)O)O)O)O)O
• InChI: InChI=1S/C41H66O12/c1-21-28(44)30(46)31(47)33(51-21)53-32-29(45)24(43)19-50-34(32)52-27-11-12-37(4)25(38(27,5)20-42)10-13-40(7)26(37)9-8-22-23-18-36(2,3)14-16-41(23,35(48)49)17-15-39(22,40)6/h8,21,23-34,42-47H,9-20H2,1-7H3,(H,48,49)
• InChI Key: KEOITPILCOILGM-UHFFFAOYSA-N
• Popularity: 14 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₁H₆₆O₁₂
• Molecular Weight: 751.00 g/mol
• Exact Mass: 750.45542754 g/mol
• Topological Polar Surface Area (TPSA): 196.00 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 3.52
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 6

Synonyms

• 27013-91-8
• 10-[4,5-dihydroxy-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• helixin (the saponin)
• 3-[[2-O-(alpha-L-Rhamnopyranosyl)-alpha-L-arabinopyranosyl]oxy]-23-hydroxyolean-12-en-28-oic acid
• NSC106553
• NSC-106553
• 3-{[2-o-(6-deoxyhexopyranosyl)pentopyranosyl]oxy}-23-hydroxyolean-12-en-28-oic acid
• CHEMBL1980760
• DTXSID20949785
• Olean-12-en-28-oic acid, 3-[[2-O-(6-deoxy-.alpha.-L-mannopyranosyl)-.alpha.-L-arabinopyranosyl]oxy]-23-hydroxy-, (3.beta.,4.alpha.)-
• STL454351
• NCI60_000155
• FT-0626874
• Olean-12-en-28-oic acid, (3.beta.,4.alpha.)-
• B0005-177593
• 3-{[2-O-(6-Deoxyhexopyranosyl)pentopyranosyl]oxy}-23-hydroxyolean-12-en-28-oato
• (3|A,4|A)-3-[[2-O-(6-Deoxy-|A-L-mannopyranosyl)-|A-L-arabinopyranosyl]oxy]-23-hydroxyolean-12-en-28-oic acid
• Olean-12-en-28-oic acid, 3-[[2-O-(6-deoxy-.alpha.-L-mannopyranosyl)-.alpha.-L-arabinopyranosyl]oxy]-23-hydroxy-, (3.beta.)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7891	78.91%
Caco-2	-	0.8761	87.61%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.8567	85.67%
OATP2B1 inhibitior	-	0.8731	87.31%
OATP1B1 inhibitior	+	0.8340	83.40%
OATP1B3 inhibitior	-	0.5700	57.00%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6276	62.76%
BSEP inhibitior	+	0.5643	56.43%
P-glycoprotein inhibitior	+	0.7597	75.97%
P-glycoprotein substrate	-	0.6154	61.54%
CYP3A4 substrate	+	0.7201	72.01%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8798	87.98%
CYP3A4 inhibition	-	0.9300	93.00%
CYP2C9 inhibition	-	0.8838	88.38%
CYP2C19 inhibition	-	0.9101	91.01%
CYP2D6 inhibition	-	0.9422	94.22%
CYP1A2 inhibition	-	0.8933	89.33%
CYP2C8 inhibition	+	0.6699	66.99%
CYP inhibitory promiscuity	-	0.9668	96.68%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6254	62.54%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9159	91.59%
Skin irritation	-	0.6103	61.03%
Skin corrosion	-	0.9480	94.80%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6802	68.02%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.9125	91.25%
skin sensitisation	-	0.8917	89.17%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.7625	76.25%
Nephrotoxicity	-	0.7505	75.05%
Acute Oral Toxicity (c)	III	0.7945	79.45%
Estrogen receptor binding	+	0.7143	71.43%
Androgen receptor binding	+	0.7217	72.17%
Thyroid receptor binding	-	0.6191	61.91%
Glucocorticoid receptor binding	+	0.6180	61.80%
Aromatase binding	+	0.6543	65.43%
PPAR gamma	+	0.7009	70.09%
Honey bee toxicity	-	0.7556	75.56%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5850	58.50%
Fish aquatic toxicity	+	0.9411	94.11%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	96.05%	95.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.47%	91.11%
CHEMBL3714130	P46095	G-protein coupled receptor 6	95.25%	97.36%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.88%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.42%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.34%	86.33%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	88.17%	96.77%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.56%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.38%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.44%	94.45%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.69%	91.07%
CHEMBL5028	O14672	ADAM10	83.27%	97.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.48%	95.89%

Plants that contains it

• Akebia quinata
• Anemoclema glaucifolium
• Anemone coronaria
• Clematis chinensis
• Clematis orientalis
• Clematis tibetana
• Elattostachys apetala
• Eleutherococcus sieboldianus
• Gliricidia sepium
• Hedera canariensis
• Hedera caucasigena
• Hedera colchica
• Hedera helix
• Hedera nepalensis
• Hedera rhombea
• Hedera taurica
• Kalopanax septemlobus
• Lepisanthes rubiginosa
• Lonicera japonica
• Medicago polymorpha
• Nigella sativa
• Patrinia scabiosifolia
• Pulsatilla cernua
• Pulsatilla chinensis
• Pulsatilla dahurica
• Sapindus delavayi
• Sapindus mukorossi

Cross-Links

• PubChem: 267360
• NPASS: NPC279554
• LOTUS: LTS0107537
• wikiData: Q105140097