Rhoeadine

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	e8300637-80cf-49ae-bec2-429d0c795dbb
Taxonomy	Alkaloids and derivatives > Rhoeadine alkaloids
IUPAC Name	(1R,14R,24S)-24-methoxy-13-methyl-5,7,19,21,25-pentaoxa-13-azahexacyclo[12.11.0.02,10.04,8.015,23.018,22]pentacosa-2,4(8),9,15(23),16,18(22)-hexaene
SMILES (Canonical)	CN1CCC2=CC3=C(C=C2C4C1C5=C(C(O4)OC)C6=C(C=C5)OCO6)OCO3
SMILES (Isomeric)	CN1CCC2=CC3=C(C=C2[C@@H]4[C@H]1C5=C([C@H](O4)OC)C6=C(C=C5)OCO6)OCO3
InChI	InChI=1S/C21H21NO6/c1-22-6-5-11-7-15-16(26-9-25-15)8-13(11)19-18(22)12-3-4-14-20(27-10-24-14)17(12)21(23-2)28-19/h3-4,7-8,18-19,21H,5-6,9-10H2,1-2H3/t18-,19-,21+/m1/s1
InChI Key	XRBIHOLQAKITPP-SBHAEUEKSA-N
Popularity	90 references in papers

Physical and Chemical Properties

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Molecular Formula	C₂₁H₂₁NO₆
Molecular Weight	383.40 g/mol
Exact Mass	383.13688739 g/mol
Topological Polar Surface Area (TPSA)	58.60 Å²
XlogP	2.40
Atomic LogP (AlogP)	3.09
H-Bond Acceptor	7
H-Bond Donor	0
Rotatable Bonds	1

Synonyms

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2718-25-4

Rhoeadin

Rheadine

BRN 0098745

UNII-9Q9C65WH3B

9Q9C65WH3B

8-beta-Methoxy-16-methyl-2,3:10,11-bis(methylenebis(oxy))rheadan

(1R,14R,24S)-24-methoxy-13-methyl-5,7,19,21,25-pentaoxa-13-azahexacyclo[12.11.0.02,10.04,8.015,23.018,22]pentacosa-2,4(8),9,15(23),16,18(22)-hexaene

4-27-00-06897 (Beilstein Handbook Reference)

Rheadan, 8-methoxy-16-methyl-2,3:10,11-bis(methylenebis(oxy))-, (8-beta)-

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	+	0.9297	92.97%
Caco-2	+	0.8677	86.77%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Lysosomes	0.6346	63.46%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9221	92.21%
OATP1B3 inhibitior	+	0.9491	94.91%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.9022	90.22%
P-glycoprotein inhibitior	+	0.6672	66.72%
P-glycoprotein substrate	-	0.6543	65.43%
CYP3A4 substrate	+	0.6245	62.45%
CYP2C9 substrate	+	0.5774	57.74%
CYP2D6 substrate	+	0.7008	70.08%
CYP3A4 inhibition	-	0.5804	58.04%
CYP2C9 inhibition	-	0.6193	61.93%
CYP2C19 inhibition	+	0.5465	54.65%
CYP2D6 inhibition	+	0.5566	55.66%
CYP1A2 inhibition	-	0.5077	50.77%
CYP2C8 inhibition	-	0.7763	77.63%
CYP inhibitory promiscuity	-	0.5201	52.01%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5998	59.98%
Eye corrosion	-	0.9877	98.77%
Eye irritation	-	0.9793	97.93%
Skin irritation	-	0.7835	78.35%
Skin corrosion	-	0.9394	93.94%
Ames mutagenesis	+	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7265	72.65%
Micronuclear	+	0.5300	53.00%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.8493	84.93%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.6823	68.23%
Acute Oral Toxicity (c)	III	0.7122	71.22%
Estrogen receptor binding	+	0.7210	72.10%
Androgen receptor binding	+	0.7203	72.03%
Thyroid receptor binding	+	0.5455	54.55%
Glucocorticoid receptor binding	+	0.8689	86.89%
Aromatase binding	-	0.5682	56.82%
PPAR gamma	+	0.7570	75.70%
Honey bee toxicity	-	0.8279	82.79%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	-	0.3631	36.31%

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
CHEMBL5697	Q9GZT9	Egl nine homolog 1	97.74%	93.40%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.51%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	94.99%	96.77%
CHEMBL2581	P07339	Cathepsin D	93.60%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.86%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.45%	86.33%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	89.53%	100.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.24%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.98%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.66%	95.89%
CHEMBL2056	P21728	Dopamine D1 receptor	87.61%	91.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.17%	92.62%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	85.00%	90.95%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	84.79%	82.67%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.08%	95.89%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	83.80%	96.39%
CHEMBL3192	Q9BY41	Histone deacetylase 8	82.27%	93.99%
CHEMBL3227	P41594	Metabotropic glutamate receptor 5	81.54%	96.42%
CHEMBL3401	O75469	Pregnane X receptor	81.47%	94.73%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	81.40%	100.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.87%	89.62%

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.

Papaver somniferum subsp. setigerum