(1R,5R,6R,7S,13R,21R)-5,13-bis(3,4-dihydroxyphenyl)-16-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-7-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]-4,12,14-trioxapentacyclo[11.7.1.02,11.03,8.015,20]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol

Details

• Internal ID: 13a252c7-d1e9-4d02-a162-5ce0a1337560
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Biflavonoids and polyflavonoids
• IUPAC Name: (1R,5R,6R,7S,13R,21R)-5,13-bis(3,4-dihydroxyphenyl)-16-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-7-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]-4,12,14-trioxapentacyclo[11.7.1.02,11.03,8.015,20]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol
• SMILES (Canonical): C1C(C(OC2=C1C(=CC(=C2C3C(C(OC4=C3C(=CC5=C4C6C(C(O5)(OC7=C(C(=CC(=C67)O)O)C8C(C(OC9=C(C(=CC(=C89)O)O)C1C(C(OC2=CC(=CC(=C12)O)O)C1=CC(=C(C=C1)O)O)O)C1=CC(=C(C=C1)O)O)O)C1=CC(=C(C=C1)O)O)O)O)C1=CC(=C(C=C1)O)O)O)O)O)C1=CC(=C(C=C1)O)O)O
• SMILES (Isomeric): C1[C@H]([C@H](OC2=C1C(=CC(=C2[C@@H]3[C@H]([C@H](OC4=C3C(=CC5=C4[C@@H]6[C@H]([C@](O5)(OC7=C(C(=CC(=C67)O)O)[C@@H]8[C@H]([C@H](OC9=C(C(=CC(=C89)O)O)[C@@H]1[C@H]([C@H](OC2=CC(=CC(=C12)O)O)C1=CC(=C(C=C1)O)O)O)C1=CC(=C(C=C1)O)O)O)C1=CC(=C(C=C1)O)O)O)O)C1=CC(=C(C=C1)O)O)O)O)O)C1=CC(=C(C=C1)O)O)O
• InChI: InChI=1S/C75H60O30/c76-28-16-41(88)51-49(17-28)100-67(24-2-7-31(78)37(84)12-24)63(96)59(51)53-43(90)20-44(91)54-61(65(98)68(102-71(53)54)25-3-8-32(79)38(85)13-25)56-45(92)21-46(93)57-62-58-50(104-75(74(62)99,105-73(56)57)27-5-10-34(81)40(87)15-27)22-47(94)55-60(64(97)69(103-72(55)58)26-4-9-33(80)39(86)14-26)52-42(89)19-35(82)29-18-48(95)66(101-70(29)52)23-1-6-30(77)36(83)11-23/h1-17,19-22,48,59-69,74,76-99H,18H2/t48-,59-,60+,61-,62-,63-,64-,65-,66-,67-,68-,69-,74-,75-/m1/s1
• InChI Key: ODHOTFAKXJWQIS-XXSLXZJWSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₇₅H₆₀O₃₀
• Molecular Weight: 1441.30 g/mol
• Exact Mass: 1440.31694049 g/mol
• Topological Polar Surface Area (TPSA): 541.00 Ų
• XlogP: 5.20
• Atomic LogP (AlogP): 7.14
• H-Bond Acceptor: 30
• H-Bond Donor: 24
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7002	70.02%
Caco-2	-	0.8609	86.09%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.5149	51.49%
OATP2B1 inhibitior	-	0.8592	85.92%
OATP1B1 inhibitior	+	0.9010	90.10%
OATP1B3 inhibitior	+	0.8374	83.74%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9367	93.67%
P-glycoprotein inhibitior	+	0.7390	73.90%
P-glycoprotein substrate	-	0.5308	53.08%
CYP3A4 substrate	+	0.6721	67.21%
CYP2C9 substrate	-	0.7965	79.65%
CYP2D6 substrate	+	0.3672	36.72%
CYP3A4 inhibition	-	0.9095	90.95%
CYP2C9 inhibition	-	0.8939	89.39%
CYP2C19 inhibition	-	0.8571	85.71%
CYP2D6 inhibition	-	0.9488	94.88%
CYP1A2 inhibition	-	0.9758	97.58%
CYP2C8 inhibition	+	0.7921	79.21%
CYP inhibitory promiscuity	-	0.9554	95.54%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6019	60.19%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.8963	89.63%
Skin irritation	-	0.6303	63.03%
Skin corrosion	-	0.9314	93.14%
Ames mutagenesis	+	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7851	78.51%
Micronuclear	+	0.7759	77.59%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.8144	81.44%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	+	0.5243	52.43%
Acute Oral Toxicity (c)	IV	0.5178	51.78%
Estrogen receptor binding	+	0.7238	72.38%
Androgen receptor binding	+	0.7808	78.08%
Thyroid receptor binding	+	0.5840	58.40%
Glucocorticoid receptor binding	+	0.6128	61.28%
Aromatase binding	+	0.6003	60.03%
PPAR gamma	+	0.7422	74.22%
Honey bee toxicity	-	0.6340	63.40%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.6600	66.00%
Fish aquatic toxicity	+	0.7943	79.43%

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	99.72%	91.11%
CHEMBL233	P35372	Mu opioid receptor	95.86%	97.93%
CHEMBL4040	P28482	MAP kinase ERK2	95.60%	83.82%
CHEMBL236	P41143	Delta opioid receptor	94.52%	99.35%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.96%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.75%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.12%	89.00%
CHEMBL2581	P07339	Cathepsin D	89.51%	98.95%
CHEMBL2535	P11166	Glucose transporter	88.74%	98.75%
CHEMBL1929	P47989	Xanthine dehydrogenase	88.23%	96.12%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.59%	94.45%
CHEMBL1951	P21397	Monoamine oxidase A	87.44%	91.49%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.53%	99.15%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.69%	95.56%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	82.17%	96.37%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.49%	99.23%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	81.40%	94.62%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	80.29%	85.11%

Plants that contains it

• Cinnamomum burmanni
• Dicranopteris pedata
• Pavetta owariensis

Cross-Links

• PubChem: 16165471
• LOTUS: LTS0181362
• wikiData: Q105189855