[(3S,4R,5R,6S)-4,5-dihydroxy-6-[[(3S,6R,8S,11R,12S,15S,16R,19R,21R)-19-hydroxy-3,7,7,11,16,20,20-heptamethyl-8-pentacyclo[13.8.0.03,12.06,11.016,21]tricos-1(23)-enyl]oxy]oxan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate

Details

• Internal ID: a94de87c-4553-42f3-ad7f-fdfa2f9057ec
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: [(3S,4R,5R,6S)-4,5-dihydroxy-6-[[(3S,6R,8S,11R,12S,15S,16R,19R,21R)-19-hydroxy-3,7,7,11,16,20,20-heptamethyl-8-pentacyclo[13.8.0.03,12.06,11.016,21]tricos-1(23)-enyl]oxy]oxan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1(C2CCC3(CC4=CCC5C(C(CCC5(C4CCC3C2(CCC1OC6C(C(C(CO6)OC(=O)C=CC7=CC=C(C=C7)O)O)O)C)C)O)(C)C)C)C
• SMILES (Isomeric): C[C@@]12CC[C@@H]3[C@@]([C@H]1CC[C@H]4C(=CC[C@@H]5[C@@]4(CC[C@H](C5(C)C)O)C)C2)(CC[C@@H](C3(C)C)O[C@H]6[C@@H]([C@H]([C@H](CO6)OC(=O)/C=C/C7=CC=C(C=C7)O)O)O)C
• InChI: InChI=1S/C44H64O8/c1-40(2)31-15-11-27-24-42(5)21-18-32-41(3,4)35(20-23-44(32,7)33(42)16-14-29(27)43(31,6)22-19-34(40)46)52-39-38(49)37(48)30(25-50-39)51-36(47)17-10-26-8-12-28(45)13-9-26/h8-13,17,29-35,37-39,45-46,48-49H,14-16,18-25H2,1-7H3/b17-10+/t29-,30-,31-,32-,33-,34+,35-,37-,38+,39-,42-,43+,44-/m0/s1
• InChI Key: YZQIFKLWKKIFBP-MOBCCOSKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₄H₆₄O₈
• Molecular Weight: 721.00 g/mol
• Exact Mass: 720.46011900 g/mol
• Topological Polar Surface Area (TPSA): 126.00 Ų
• XlogP: 8.30
• Atomic LogP (AlogP): 7.57
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9730	97.30%
Caco-2	-	0.8580	85.80%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.8566	85.66%
OATP2B1 inhibitior	-	0.8629	86.29%
OATP1B1 inhibitior	+	0.8440	84.40%
OATP1B3 inhibitior	+	0.8429	84.29%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7818	78.18%
BSEP inhibitior	+	0.8494	84.94%
P-glycoprotein inhibitior	+	0.7455	74.55%
P-glycoprotein substrate	+	0.5431	54.31%
CYP3A4 substrate	+	0.7374	73.74%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8758	87.58%
CYP3A4 inhibition	-	0.7825	78.25%
CYP2C9 inhibition	-	0.6141	61.41%
CYP2C19 inhibition	-	0.5305	53.05%
CYP2D6 inhibition	-	0.8885	88.85%
CYP1A2 inhibition	+	0.7126	71.26%
CYP2C8 inhibition	+	0.8190	81.90%
CYP inhibitory promiscuity	-	0.9338	93.38%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.6362	63.62%
Eye corrosion	-	0.9914	99.14%
Eye irritation	-	0.9139	91.39%
Skin irritation	-	0.6419	64.19%
Skin corrosion	-	0.9437	94.37%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7711	77.11%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.6360	63.60%
skin sensitisation	-	0.8348	83.48%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.8907	89.07%
Acute Oral Toxicity (c)	III	0.4090	40.90%
Estrogen receptor binding	+	0.7695	76.95%
Androgen receptor binding	+	0.7373	73.73%
Thyroid receptor binding	+	0.5191	51.91%
Glucocorticoid receptor binding	+	0.7035	70.35%
Aromatase binding	+	0.6308	63.08%
PPAR gamma	+	0.7255	72.55%
Honey bee toxicity	-	0.6339	63.39%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	+	0.9953	99.53%

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	98.15%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.24%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.64%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.57%	96.09%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	92.84%	89.67%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.32%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.85%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.67%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.52%	95.56%
CHEMBL221	P23219	Cyclooxygenase-1	89.13%	90.17%
CHEMBL325	Q13547	Histone deacetylase 1	87.63%	95.92%
CHEMBL2581	P07339	Cathepsin D	86.90%	98.95%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	86.51%	97.33%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	85.33%	89.44%
CHEMBL3922	P50579	Methionine aminopeptidase 2	83.20%	97.28%
CHEMBL3192	Q9BY41	Histone deacetylase 8	83.03%	93.99%
CHEMBL2179	P04062	Beta-glucocerebrosidase	82.90%	85.31%
CHEMBL242	Q92731	Estrogen receptor beta	82.38%	98.35%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.22%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.20%	100.00%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	81.40%	85.49%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.26%	92.94%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.64%	99.17%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	80.49%	83.57%
CHEMBL1937	Q92769	Histone deacetylase 2	80.05%	94.75%

Plants that contains it

• Lycopodiella inundata

Cross-Links

• PubChem: 163186072
• LOTUS: LTS0196543
• wikiData: Q105369400