[(2S,3S,4S,5R)-4-[(S)-[(2R,3S)-8-[(S)-[(2R,3S,4S,5S)-4-(2,4-dihydroxybenzoyl)-2-(2,4-dihydroxyphenyl)-5-(4-hydroxyphenyl)oxolan-3-yl]-phenylmethyl]-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromen-6-yl]-phenylmethyl]-5-(2,4-dihydroxyphenyl)-2-(4-hydroxyphenyl)oxolan-3-yl]-(2,4-dihydroxyphenyl)methanone

Details

• Internal ID: edd26f1c-cef7-4ba9-a9a0-7fde8d39786c
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > 6-prenylated flavans
• IUPAC Name: [(2S,3S,4S,5R)-4-[(S)-[(2R,3S)-8-[(S)-[(2R,3S,4S,5S)-4-(2,4-dihydroxybenzoyl)-2-(2,4-dihydroxyphenyl)-5-(4-hydroxyphenyl)oxolan-3-yl]-phenylmethyl]-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromen-6-yl]-phenylmethyl]-5-(2,4-dihydroxyphenyl)-2-(4-hydroxyphenyl)oxolan-3-yl]-(2,4-dihydroxyphenyl)methanone
• SMILES (Canonical): C1C(C(OC2=C(C(=C(C(=C21)O)C(C3C(C(OC3C4=C(C=C(C=C4)O)O)C5=CC=C(C=C5)O)C(=O)C6=C(C=C(C=C6)O)O)C7=CC=CC=C7)O)C(C8C(C(OC8C9=C(C=C(C=C9)O)O)C1=CC=C(C=C1)O)C(=O)C1=C(C=C(C=C1)O)O)C1=CC=CC=C1)C1=CC=C(C=C1)O)O
• SMILES (Isomeric): C1[C@@H]([C@H](OC2=C(C(=C(C(=C21)O)[C@@H]([C@H]3[C@@H]([C@H](O[C@H]3C4=C(C=C(C=C4)O)O)C5=CC=C(C=C5)O)C(=O)C6=C(C=C(C=C6)O)O)C7=CC=CC=C7)O)[C@@H]([C@H]8[C@@H]([C@H](O[C@H]8C9=C(C=C(C=C9)O)O)C1=CC=C(C=C1)O)C(=O)C1=C(C=C(C=C1)O)O)C1=CC=CC=C1)C1=CC=C(C=C1)O)O
• InChI: InChI=1S/C75H62O19/c76-41-17-11-38(12-18-41)70-57(87)35-52-68(90)62(58(36-7-3-1-4-8-36)60-64(66(88)48-27-23-44(79)31-53(48)83)71(39-13-19-42(77)20-14-39)93-73(60)50-29-25-46(81)33-55(50)85)69(91)63(75(52)92-70)59(37-9-5-2-6-10-37)61-65(67(89)49-28-24-45(80)32-54(49)84)72(40-15-21-43(78)22-16-40)94-74(61)51-30-26-47(82)34-56(51)86/h1-34,57-61,64-65,70-74,76-87,90-91H,35H2/t57-,58+,59+,60-,61-,64+,65+,70+,71+,72+,73-,74-/m0/s1
• InChI Key: IQNKMQHDYQAEFN-ONFVCGNHSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₇₅H₆₂O₁₉
• Molecular Weight: 1267.30 g/mol
• Exact Mass: 1266.38852974 g/mol
• Topological Polar Surface Area (TPSA): 345.00 Ų
• XlogP: 11.30
• Atomic LogP (AlogP): 12.42
• H-Bond Acceptor: 19
• H-Bond Donor: 14
• Rotatable Bonds: 15

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9566	95.66%
Caco-2	-	0.8861	88.61%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6594	65.94%
OATP2B1 inhibitior	-	0.8479	84.79%
OATP1B1 inhibitior	+	0.7840	78.40%
OATP1B3 inhibitior	+	0.8039	80.39%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.8387	83.87%
P-glycoprotein inhibitior	+	0.7341	73.41%
P-glycoprotein substrate	+	0.5793	57.93%
CYP3A4 substrate	+	0.6689	66.89%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7550	75.50%
CYP3A4 inhibition	-	0.7228	72.28%
CYP2C9 inhibition	-	0.5902	59.02%
CYP2C19 inhibition	-	0.7714	77.14%
CYP2D6 inhibition	-	0.8996	89.96%
CYP1A2 inhibition	-	0.7456	74.56%
CYP2C8 inhibition	+	0.5599	55.99%
CYP inhibitory promiscuity	-	0.8188	81.88%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5447	54.47%
Eye corrosion	-	0.9913	99.13%
Eye irritation	-	0.8899	88.99%
Skin irritation	-	0.6401	64.01%
Skin corrosion	-	0.9379	93.79%
Ames mutagenesis	-	0.6454	64.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.6860	68.60%
Micronuclear	+	0.8859	88.59%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.8187	81.87%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.7730	77.30%
Acute Oral Toxicity (c)	III	0.3457	34.57%
Estrogen receptor binding	+	0.7486	74.86%
Androgen receptor binding	+	0.7740	77.40%
Thyroid receptor binding	+	0.5554	55.54%
Glucocorticoid receptor binding	-	0.5555	55.55%
Aromatase binding	-	0.5414	54.14%
PPAR gamma	+	0.6988	69.88%
Honey bee toxicity	-	0.7595	75.95%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.8298	82.98%

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	98.82%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.05%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.84%	96.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.37%	99.15%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.46%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.11%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	88.95%	94.73%
CHEMBL2535	P11166	Glucose transporter	87.55%	98.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.42%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.20%	99.23%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.15%	95.89%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.49%	90.71%
CHEMBL3227	P41594	Metabotropic glutamate receptor 5	86.30%	96.42%
CHEMBL3359	P21462	Formyl peptide receptor 1	86.19%	93.56%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.12%	95.50%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	84.74%	85.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.52%	97.09%
CHEMBL217	P14416	Dopamine D2 receptor	83.71%	95.62%
CHEMBL3714130	P46095	G-protein coupled receptor 6	83.32%	97.36%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	82.54%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.82%	85.14%
CHEMBL340	P08684	Cytochrome P450 3A4	81.11%	91.19%
CHEMBL3192	Q9BY41	Histone deacetylase 8	80.40%	93.99%

Plants that contains it

• Ochna calodendron

Cross-Links

• PubChem: 101128133
• LOTUS: LTS0256566
• wikiData: Q105118046