(4aS,6aR,6aR,6bR,8aR,10S,12aR,14bS)-6a-[[16-[[(4aS,6aR,6aR,6bR,8aR,10S,12aR,14bS)-4a-carboxy-10-hydroxy-2,2,6b,9,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicen-6a-yl]methoxycarbonyl]-4,5,10-trihydroxy-8-oxatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2,4,6,9,11,13,15-octaene-15-carbonyl]oxymethyl]-10-hydroxy-2,2,6b,9,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid

Details

• Internal ID: 6ead2180-5bad-4069-8c70-b7c1508afcdb
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (4aS,6aR,6aR,6bR,8aR,10S,12aR,14bS)-6a-[[16-[[(4aS,6aR,6aR,6bR,8aR,10S,12aR,14bS)-4a-carboxy-10-hydroxy-2,2,6b,9,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicen-6a-yl]methoxycarbonyl]-4,5,10-trihydroxy-8-oxatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2,4,6,9,11,13,15-octaene-15-carbonyl]oxymethyl]-10-hydroxy-2,2,6b,9,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• SMILES (Canonical): CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)O)C)C)C2C1)COC(=O)C6=C(C7=C8C(=C6)C=CC(=C8OC9=CC(=C(C=C97)O)O)O)C(=O)OCC12CCC3(CCC(CC3C1=CCC1C2(CCC2C1(CCC(C2(C)C)O)C)C)(C)C)C(=O)O)C(=O)O)C
• SMILES (Isomeric): C[C@]12CC[C@@H](C([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(CC[C@@]5([C@H]4CC(CC5)(C)C)C(=O)O)COC(=O)C6=C(C7=C8C(=C6)C=CC(=C8OC9=CC(=C(C=C97)O)O)O)C(=O)OC[C@@]12CC[C@]3(CCC(C[C@H]3C1=CC[C@H]1[C@]2(CC[C@@H]2[C@@]1(CC[C@@H](C2(C)C)O)C)C)(C)C)C(=O)O)C)(C)C)O
• InChI: InChI=1S/C78H102O14/c1-67(2)27-29-75(65(86)87)31-33-77(45(47(75)38-67)14-17-55-71(9)23-21-57(82)69(5,6)53(71)19-25-73(55,77)11)40-90-63(84)44-35-42-13-16-49(79)62-59(42)60(43-36-50(80)51(81)37-52(43)92-62)61(44)64(85)91-41-78-34-32-76(66(88)89)30-28-68(3,4)39-48(76)46(78)15-18-56-72(10)24-22-58(83)70(7,8)54(72)20-26-74(56,78)12/h13-16,35-37,47-48,53-58,79-83H,17-34,38-41H2,1-12H3,(H,86,87)(H,88,89)/t47-,48-,53-,54-,55+,56+,57-,58-,71-,72-,73+,74+,75-,76-,77-,78-/m0/s1
• InChI Key: GTXOHZIHSXRHCH-SXEUNUEYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₇₈H₁₀₂O₁₄
• Molecular Weight: 1263.60 g/mol
• Exact Mass: 1262.72695792 g/mol
• Topological Polar Surface Area (TPSA): 238.00 Ų
• XlogP: 16.10
• Atomic LogP (AlogP): 16.62
• H-Bond Acceptor: 12
• H-Bond Donor: 7
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9397	93.97%
Caco-2	-	0.8543	85.43%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.8854	88.54%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8327	83.27%
OATP1B3 inhibitior	+	0.7893	78.93%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8026	80.26%
BSEP inhibitior	+	0.9901	99.01%
P-glycoprotein inhibitior	+	0.7476	74.76%
P-glycoprotein substrate	+	0.6332	63.32%
CYP3A4 substrate	+	0.7252	72.52%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8567	85.67%
CYP3A4 inhibition	-	0.7459	74.59%
CYP2C9 inhibition	-	0.6991	69.91%
CYP2C19 inhibition	-	0.6192	61.92%
CYP2D6 inhibition	-	0.9009	90.09%
CYP1A2 inhibition	+	0.6878	68.78%
CYP2C8 inhibition	+	0.8332	83.32%
CYP inhibitory promiscuity	-	0.9283	92.83%
UGT catelyzed	+	0.5362	53.62%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.6622	66.22%
Eye corrosion	-	0.9913	99.13%
Eye irritation	-	0.8978	89.78%
Skin irritation	-	0.7306	73.06%
Skin corrosion	-	0.9483	94.83%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6771	67.71%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	-	0.6726	67.26%
skin sensitisation	-	0.8686	86.86%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.9400	94.00%
Acute Oral Toxicity (c)	III	0.5074	50.74%
Estrogen receptor binding	+	0.6451	64.51%
Androgen receptor binding	+	0.7806	78.06%
Thyroid receptor binding	+	0.6638	66.38%
Glucocorticoid receptor binding	+	0.7765	77.65%
Aromatase binding	+	0.6831	68.31%
PPAR gamma	+	0.8094	80.94%
Honey bee toxicity	-	0.7076	70.76%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5471	54.71%
Fish aquatic toxicity	+	1.0000	100.00%

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	99.30%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.51%	94.45%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	96.00%	95.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.85%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.03%	97.09%
CHEMBL221	P23219	Cyclooxygenase-1	92.99%	90.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.07%	99.23%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.30%	99.15%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.10%	95.56%
CHEMBL2581	P07339	Cathepsin D	87.80%	98.95%
CHEMBL2179	P04062	Beta-glucocerebrosidase	87.21%	85.31%
CHEMBL1914	P06276	Butyrylcholinesterase	86.58%	95.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.26%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.04%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.72%	95.89%
CHEMBL5028	O14672	ADAM10	83.36%	97.50%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.33%	96.21%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.29%	96.09%

Plants that contains it

• Rhoiptelea chiliantha

Cross-Links

• PubChem: 101998883
• LOTUS: LTS0122766
• wikiData: Q105019601