Sikkimotoxin

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	5f42bec8-fb74-42e1-b577-0a493a5cd214
Taxonomy	Lignans, neolignans and related compounds > Lignan lactones
IUPAC Name	(3aR,4R,9R,9aR)-4-hydroxy-6,7-dimethoxy-9-(3,4,5-trimethoxyphenyl)-3a,4,9,9a-tetrahydro-3H-benzo[f][2]benzofuran-1-one
SMILES (Canonical)	COC1=CC(=CC(=C1OC)OC)C2C3C(COC3=O)C(C4=CC(=C(C=C24)OC)OC)O
SMILES (Isomeric)	COC1=CC(=CC(=C1OC)OC)[C@H]2[C@@H]3[C@H](COC3=O)[C@H](C4=CC(=C(C=C24)OC)OC)O
InChI	InChI=1S/C23H26O8/c1-26-15-8-12-13(9-16(15)27-2)21(24)14-10-31-23(25)20(14)19(12)11-6-17(28-3)22(30-5)18(7-11)29-4/h6-9,14,19-21,24H,10H2,1-5H3/t14-,19+,20-,21-/m0/s1
InChI Key	JQNGRAVMNACCCG-MGNXDGSBSA-N
Popularity	4 references in papers

Physical and Chemical Properties

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Molecular Formula	C₂₃H₂₆O₈
Molecular Weight	430.40 g/mol
Exact Mass	430.16276778 g/mol
Topological Polar Surface Area (TPSA)	92.70 Å²
XlogP	2.10
Atomic LogP (AlogP)	2.70
H-Bond Acceptor	8
H-Bond Donor	1
Rotatable Bonds	6

Synonyms

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Sikkimotoxin [MI]

UNII-P32T3N2QMR

P32T3N2QMR

18651-67-7

Naphtho(2,3-C)furan-1(3H)-one, 3a,4,9,9a-tetrahydro-4-hydroxy-6,7-dimethoxy-9-(3,4,5-trimethoxyphenyl)-, (3aR,4R,9R,9aR)-

Naphtho(2,3-C)furan-1(3H)-one, 3a,4,9,9a-tetrahydro-4-hydroxy-6,7-dimethoxy-9-(3,4,5-trimethoxyphenyl)-, (3ar-(3aalpha,4alpha,9alpha,9abeta))-

NAPHTHO(2,3-C)FURAN-1(3H)-ONE, 3A,4,9,9A-TETRAHYDRO-4-HYDROXY-6,7-DIMETHOXY-9-(3,4,5-TRIMETHOXYPHENYL)-, (3AR-(3A.ALPHA.,4.ALPHA.,9.ALPHA.,9A.BETA.))-

Naphtho[2,3-c]furan-1(3H)-one, 3a,4,9,9a-tetrahydro-4-hydroxy-6,7-dimethoxy-9-(3,4,5-trimethoxyphenyl)-, (3aR,4R,9R,9aR)-

Naphtho[2,3-c]furan-1(3H)-one, 3a,4,9,9a-tetrahydro-4-hydroxy-6,7-dimethoxy-9-(3,4,5-trimethoxyphenyl)-, [3aR-(3a.alpha.,4.alpha.,9.alpha.,9a.beta.)]-

CHEMBL2288931

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	+	0.9922	99.22%
Caco-2	+	0.7086	70.86%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7974	79.74%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8176	81.76%
OATP1B3 inhibitior	+	0.8854	88.54%
MATE1 inhibitior	-	0.6200	62.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.8708	87.08%
P-glycoprotein inhibitior	+	0.6131	61.31%
P-glycoprotein substrate	-	0.9035	90.35%
CYP3A4 substrate	+	0.5715	57.15%
CYP2C9 substrate	-	0.6054	60.54%
CYP2D6 substrate	-	0.7249	72.49%
CYP3A4 inhibition	-	0.5796	57.96%
CYP2C9 inhibition	+	0.8606	86.06%
CYP2C19 inhibition	+	0.6694	66.94%
CYP2D6 inhibition	-	0.9591	95.91%
CYP1A2 inhibition	-	0.5094	50.94%
CYP2C8 inhibition	-	0.6765	67.65%
CYP inhibitory promiscuity	+	0.6430	64.30%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5015	50.15%
Eye corrosion	-	0.9867	98.67%
Eye irritation	-	0.9114	91.14%
Skin irritation	-	0.8171	81.71%
Skin corrosion	-	0.9807	98.07%
Ames mutagenesis	-	0.7637	76.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.4849	48.49%
Micronuclear	+	0.8133	81.33%
Hepatotoxicity	-	0.5125	51.25%
skin sensitisation	-	0.8769	87.69%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	+	0.6899	68.99%
Acute Oral Toxicity (c)	III	0.4620	46.20%
Estrogen receptor binding	+	0.8953	89.53%
Androgen receptor binding	+	0.8299	82.99%
Thyroid receptor binding	+	0.8358	83.58%
Glucocorticoid receptor binding	+	0.8528	85.28%
Aromatase binding	-	0.7404	74.04%
PPAR gamma	+	0.5979	59.79%
Honey bee toxicity	-	0.7327	73.27%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9741	97.41%

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
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.92%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.38%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	94.96%	83.82%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.93%	89.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.35%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.89%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.16%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.85%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.79%	97.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.11%	94.00%
CHEMBL2535	P11166	Glucose transporter	83.65%	98.75%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.95%	92.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.66%	99.17%
CHEMBL2581	P07339	Cathepsin D	82.38%	98.95%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.09%	97.14%

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.

Dimorphotheca sinuata

Heptapleurum capitatum

Podophyllum hexandrum

Roldana mexicana