(13aS,14S)-3,7-dimethoxy-9,11,12,13,13a,14-hexahydrophenanthro[10,9-f]indolizine-6,14-diol

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	96277678-c60e-458a-813a-6ff1f52ea471
Taxonomy	Benzenoids > Phenanthrenes and derivatives > Phenanthroindolizidines
IUPAC Name	3,7-dimethoxy-9,11,12,13,13a,14-hexahydrophenanthro[10,9-f]indolizine-6,14-diol
SMILES (Canonical)	COC1=CC2=C(C=C1)C3=C(CN4CCCC4C3O)C5=CC(=C(C=C52)O)OC
SMILES (Isomeric)	COC1=CC2=C(C=C1)C3=C(CN4CCCC4C3O)C5=CC(=C(C=C52)O)OC
InChI	InChI=1S/C22H23NO4/c1-26-12-5-6-13-14(8-12)15-9-19(24)20(27-2)10-16(15)17-11-23-7-3-4-18(23)22(25)21(13)17/h5-6,8-10,18,22,24-25H,3-4,7,11H2,1-2H3
InChI Key	CMFIDYCYVJWPPL-UHFFFAOYSA-N
Popularity	8 references in papers

Physical and Chemical Properties

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Molecular Formula	C₂₂H₂₃NO₄
Molecular Weight	365.40 g/mol
Exact Mass	365.16270821 g/mol
Topological Polar Surface Area (TPSA)	62.20 Å²
XlogP	3.30
Atomic LogP (AlogP)	3.73
H-Bond Acceptor	5
H-Bond Donor	2
Rotatable Bonds	2

Synonyms

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32523-69-6

D0C1UM

TYLOPHORIDICINE A,98+%

(13aS,14S)-3,7-dimethoxy-9,11,12,13,13a,14-hexahydrophenanthro[10,9-f]indolizine-6,14-diol

3,7-Dimethoxy-6,14-dihydroxy-9,11,12,13,13a,14-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinoline

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	+	0.9126	91.26%
Caco-2	+	0.7735	77.35%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7877	78.77%
OATP2B1 inhibitior	-	0.8560	85.60%
OATP1B1 inhibitior	+	0.9265	92.65%
OATP1B3 inhibitior	+	0.9424	94.24%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	+	0.9012	90.12%
P-glycoprotein inhibitior	+	0.7100	71.00%
P-glycoprotein substrate	+	0.5989	59.89%
CYP3A4 substrate	+	0.5737	57.37%
CYP2C9 substrate	-	0.6075	60.75%
CYP2D6 substrate	+	0.8055	80.55%
CYP3A4 inhibition	-	0.8350	83.50%
CYP2C9 inhibition	-	0.8924	89.24%
CYP2C19 inhibition	+	0.5794	57.94%
CYP2D6 inhibition	+	0.8361	83.61%
CYP1A2 inhibition	+	0.7649	76.49%
CYP2C8 inhibition	-	0.6189	61.89%
CYP inhibitory promiscuity	-	0.6018	60.18%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6594	65.94%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.9618	96.18%
Skin irritation	-	0.7398	73.98%
Skin corrosion	-	0.9341	93.41%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6731	67.31%
Micronuclear	+	0.5900	59.00%
Hepatotoxicity	+	0.6500	65.00%
skin sensitisation	-	0.8800	88.00%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.7954	79.54%
Acute Oral Toxicity (c)	II	0.5349	53.49%
Estrogen receptor binding	+	0.7267	72.67%
Androgen receptor binding	+	0.6690	66.90%
Thyroid receptor binding	+	0.6470	64.70%
Glucocorticoid receptor binding	+	0.6634	66.34%
Aromatase binding	+	0.5985	59.85%
PPAR gamma	+	0.5725	57.25%
Honey bee toxicity	-	0.8816	88.16%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	+	0.6751	67.51%
Fish aquatic toxicity	+	0.6405	64.05%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4977	P05412	Proto-oncogene c-JUN	65 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.65%	91.11%
CHEMBL241	Q14432	Phosphodiesterase 3A	95.39%	92.94%
CHEMBL5608	Q16288	NT-3 growth factor receptor	95.34%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.88%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.21%	96.09%
CHEMBL3438	Q05513	Protein kinase C zeta	93.52%	88.48%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	90.66%	91.79%
CHEMBL2535	P11166	Glucose transporter	90.42%	98.75%
CHEMBL4208	P20618	Proteasome component C5	90.40%	90.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	89.44%	89.62%
CHEMBL4040	P28482	MAP kinase ERK2	89.22%	83.82%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.75%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.20%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.29%	94.00%
CHEMBL5203	P33316	dUTP pyrophosphatase	87.26%	99.18%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.50%	99.15%
CHEMBL3192	Q9BY41	Histone deacetylase 8	86.33%	93.99%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	86.28%	91.03%
CHEMBL2581	P07339	Cathepsin D	85.87%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.26%	86.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.10%	92.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.30%	89.00%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	81.21%	100.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	80.15%	93.40%

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.

Ficus septica

Vincetoxicum hirsutum

Vincetoxicum hirundinaria

Vincetoxicum indicum var. indicum