(1R,8S,9R,16R,18S,27S)-9-(3,4-dihydroxyphenyl)-5,8,16,21,23-pentahydroxy-2,10,17,26-tetraoxaheptacyclo[14.11.1.01,13.03,12.06,11.018,27.020,25]octacosa-3(12),4,6(11),13,20,22,24-heptaen-15-one

Details

• Internal ID: ef50f41f-69f7-4395-983f-3ffd9f27a8d4
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Catechins
• IUPAC Name: (1R,8S,9R,16R,18S,27S)-9-(3,4-dihydroxyphenyl)-5,8,16,21,23-pentahydroxy-2,10,17,26-tetraoxaheptacyclo[14.11.1.01,13.03,12.06,11.018,27.020,25]octacosa-3(12),4,6(11),13,20,22,24-heptaen-15-one
• SMILES (Canonical): C1C(C(OC2=C1C(=CC3=C2C4=CC(=O)C5(CC4(O3)C6C(O5)CC7=C(C=C(C=C7O6)O)O)O)O)C8=CC(=C(C=C8)O)O)O
• SMILES (Isomeric): C1[C@@H]([C@H](OC2=C1C(=CC3=C2C4=CC(=O)[C@]5(C[C@]4(O3)[C@@H]6[C@@H](O5)CC7=C(C=C(C=C7O6)O)O)O)O)C8=CC(=C(C=C8)O)O)O
• InChI: InChI=1S/C30H24O12/c31-12-4-17(33)13-7-23-28(39-21(13)5-12)29-10-30(38,42-23)24(37)8-15(29)25-22(41-29)9-18(34)14-6-20(36)26(40-27(14)25)11-1-2-16(32)19(35)3-11/h1-5,8-9,20,23,26,28,31-36,38H,6-7,10H2/t20-,23-,26+,28-,29+,30+/m0/s1
• InChI Key: XNGZKGIFXTWBFN-LTVJOWCOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₂₄O₁₂
• Molecular Weight: 576.50 g/mol
• Exact Mass: 576.12677620 g/mol
• Topological Polar Surface Area (TPSA): 196.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 1.83
• H-Bond Acceptor: 12
• H-Bond Donor: 7
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9502	95.02%
Caco-2	-	0.9038	90.38%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7352	73.52%
OATP2B1 inhibitior	-	0.7095	70.95%
OATP1B1 inhibitior	+	0.8592	85.92%
OATP1B3 inhibitior	+	0.9225	92.25%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9289	92.89%
P-glycoprotein inhibitior	+	0.7095	70.95%
P-glycoprotein substrate	-	0.5058	50.58%
CYP3A4 substrate	+	0.6811	68.11%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8171	81.71%
CYP3A4 inhibition	-	0.7522	75.22%
CYP2C9 inhibition	-	0.5689	56.89%
CYP2C19 inhibition	-	0.6210	62.10%
CYP2D6 inhibition	-	0.8052	80.52%
CYP1A2 inhibition	-	0.8467	84.67%
CYP2C8 inhibition	+	0.6928	69.28%
CYP inhibitory promiscuity	-	0.8038	80.38%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4410	44.10%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.8679	86.79%
Skin irritation	-	0.6898	68.98%
Skin corrosion	-	0.9310	93.10%
Ames mutagenesis	+	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7366	73.66%
Micronuclear	+	0.7200	72.00%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.7658	76.58%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.7472	74.72%
Acute Oral Toxicity (c)	I	0.4287	42.87%
Estrogen receptor binding	+	0.8402	84.02%
Androgen receptor binding	+	0.7729	77.29%
Thyroid receptor binding	+	0.5570	55.70%
Glucocorticoid receptor binding	+	0.7063	70.63%
Aromatase binding	+	0.5856	58.56%
PPAR gamma	+	0.7221	72.21%
Honey bee toxicity	-	0.7002	70.02%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9812	98.12%

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	99.75%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	99.49%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.43%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.01%	94.45%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	94.00%	93.40%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.60%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.34%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.11%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.07%	97.09%
CHEMBL2581	P07339	Cathepsin D	90.00%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.39%	99.15%
CHEMBL2535	P11166	Glucose transporter	85.60%	98.75%
CHEMBL3401	O75469	Pregnane X receptor	84.37%	94.73%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.65%	85.14%
CHEMBL1929	P47989	Xanthine dehydrogenase	83.54%	96.12%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.31%	86.33%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	82.48%	85.11%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.31%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.77%	100.00%
CHEMBL4208	P20618	Proteasome component C5	80.47%	90.00%

Plants that contains it

• Aglaia elaeagnoidea
• Aldama linearis
• Artemisia absinthium
• Bryum argenteum
• Callicarpa japonica
• Coniogramme japonica
• Coprosma areolata
• Elephantopus hirtiflorus
• Entada phaseoloides
• Euonymus alatus
• Euphorbia amygdaloides
• Gmelina asiatica
• Helichrysum cephaloideum
• Hesperis matronalis
• Hypericum balearicum
• Jackiella javanica
• Jatropha macrorhiza
• Ligularia cymbulifera
• Lilium philadelphicum
• Magnolia montana
• Nematolepis phebalioides
• Pangium edule
• Phyllanthus emblica
• Platyosprion platycarpum
• Quercus ilex
• Searsia pyroides
• Sedum yvesi
• Senecio adenophyllus
• Solidago flexicaulis
• Sterculia foetida
• Trollius chinensis
• Vigna mungo

Cross-Links

• PubChem: 101925531
• NPASS: NPC3862
• LOTUS: LTS0240906
• wikiData: Q105331656