Trifolirhizin

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	e9924613-6c8f-4c8d-b022-f1bba68afdf7
Taxonomy	Phenylpropanoids and polyketides > Isoflavonoids > Furanoisoflavonoids > Pterocarpans
IUPAC Name	(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[[(1R,12R)-5,7,11,19-tetraoxapentacyclo[10.8.0.02,10.04,8.013,18]icosa-2,4(8),9,13(18),14,16-hexaen-16-yl]oxy]oxane-3,4,5-triol
SMILES (Canonical)	C1C2C(C3=C(O1)C=C(C=C3)OC4C(C(C(C(O4)CO)O)O)O)OC5=CC6=C(C=C25)OCO6
SMILES (Isomeric)	C1[C@@H]2[C@H](C3=C(O1)C=C(C=C3)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)OC5=CC6=C(C=C25)OCO6
InChI	InChI=1S/C22H22O10/c23-6-17-18(24)19(25)20(26)22(32-17)30-9-1-2-10-13(3-9)27-7-12-11-4-15-16(29-8-28-15)5-14(11)31-21(10)12/h1-5,12,17-26H,6-8H2/t12-,17+,18+,19-,20+,21-,22+/m0/s1
InChI Key	VGSYCWGXBYZLLE-QEEQPWONSA-N
Popularity	97 references in papers

Physical and Chemical Properties

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Molecular Formula	C₂₂H₂₂O₁₀
Molecular Weight	446.40 g/mol
Exact Mass	446.12129689 g/mol
Topological Polar Surface Area (TPSA)	136.00 Å²
XlogP	0.60
Atomic LogP (AlogP)	0.20
H-Bond Acceptor	10
H-Bond Donor	4
Rotatable Bonds	3

Synonyms

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6807-83-6

Sophojaponicin B2

(-)-maackiain-3-O-glucoside

CHEBI:9714

trifolrhizin

(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[[(1R,12R)-5,7,11,19-tetraoxapentacyclo[10.8.0.02,10.04,8.013,18]icosa-2,4(8),9,13(18),14,16-hexaen-16-yl]oxy]oxane-3,4,5-triol

(-)-Maackiain 3-O-glucoside

beta-D-Glucopyranoside, 6a,12a-dihydro-6H-(1,3)dioxolo(5,6)benzofuro(3,2-c)(1)benzopyran-3-yl, (6aR-cis)-

CHEMBL454878

MFCD00238700

There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5863	58.63%
Caco-2	-	0.8618	86.18%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.5300	53.00%
OATP2B1 inhibitior	-	0.8582	85.82%
OATP1B1 inhibitior	+	0.9134	91.34%
OATP1B3 inhibitior	+	0.9590	95.90%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.6963	69.63%
P-glycoprotein inhibitior	-	0.6328	63.28%
P-glycoprotein substrate	-	0.8422	84.22%
CYP3A4 substrate	+	0.5803	58.03%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7727	77.27%
CYP3A4 inhibition	-	0.7256	72.56%
CYP2C9 inhibition	-	0.8922	89.22%
CYP2C19 inhibition	-	0.6642	66.42%
CYP2D6 inhibition	-	0.7229	72.29%
CYP1A2 inhibition	-	0.8626	86.26%
CYP2C8 inhibition	+	0.4659	46.59%
CYP inhibitory promiscuity	-	0.5097	50.97%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5121	51.21%
Eye corrosion	-	0.9924	99.24%
Eye irritation	-	0.9128	91.28%
Skin irritation	-	0.8012	80.12%
Skin corrosion	-	0.9534	95.34%
Ames mutagenesis	+	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3666	36.66%
Micronuclear	+	0.6059	60.59%
Hepatotoxicity	-	0.8302	83.02%
skin sensitisation	-	0.8555	85.55%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.7316	73.16%
Acute Oral Toxicity (c)	III	0.5505	55.05%
Estrogen receptor binding	+	0.6592	65.92%
Androgen receptor binding	+	0.5600	56.00%
Thyroid receptor binding	+	0.5339	53.39%
Glucocorticoid receptor binding	-	0.6121	61.21%
Aromatase binding	+	0.5332	53.32%
PPAR gamma	+	0.7878	78.78%
Honey bee toxicity	-	0.7831	78.31%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.7293	72.93%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
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	98.91%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.52%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	96.42%	95.93%
CHEMBL2039	P27338	Monoamine oxidase B	95.00%	92.51%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.30%	96.09%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	90.65%	94.80%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.78%	86.33%
CHEMBL2581	P07339	Cathepsin D	88.13%	98.95%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	88.00%	92.62%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.34%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.99%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.40%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	84.67%	94.73%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.56%	86.92%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.44%	89.00%
CHEMBL220	P22303	Acetylcholinesterase	83.22%	94.45%
CHEMBL4208	P20618	Proteasome component C5	82.03%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.45%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.92%	100.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.52%	94.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.47%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.28%	96.00%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.

Asimina parviflora

Atraphaxis spinosa

Baccharis neglecta

Centaurea cuneifolia subsp. cuneifolia

Chondrodendron tomentosum