Tylophorinine

Details

• Internal ID: 0b17f8de-ed20-4d85-8506-f5ae1f7dccad
• Taxonomy: Benzenoids > Phenanthrenes and derivatives > Phenanthroindolizidines
• IUPAC Name: (13aS,14R)-3,6,7-trimethoxy-9,11,12,13,13a,14-hexahydrophenanthro[9,10-f]indolizin-14-ol
• SMILES (Canonical): COC1=CC2=C(C=C1)C3=C(CN4CCCC4C3O)C5=CC(=C(C=C52)OC)OC
• SMILES (Isomeric): COC1=CC2=C(C=C1)C3=C(CN4CCC[C@H]4[C@@H]3O)C5=CC(=C(C=C52)OC)OC
• InChI: InChI=1S/C23H25NO4/c1-26-13-6-7-14-15(9-13)16-10-20(27-2)21(28-3)11-17(16)18-12-24-8-4-5-19(24)23(25)22(14)18/h6-7,9-11,19,23,25H,4-5,8,12H2,1-3H3/t19-,23-/m0/s1
• InChI Key: LAWAARLALKUFQQ-CVDCTZTESA-N
• Popularity: 13 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₅NO₄
• Molecular Weight: 379.40 g/mol
• Exact Mass: 379.17835828 g/mol
• Topological Polar Surface Area (TPSA): 51.20 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 4.03
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• (13aS,14R)-3,6,7-trimethoxy-9,11,12,13,13a,14-hexahydrophenanthro[9,10-f]indolizin-14-ol
• (13aS,14R)-3,6,7-trimethoxy-9,11,12,13,13a,14-hexahydrophenanthro(9,10-f)indolizin-14-ol
• RefChem:192630
• Pergularinine
• 571-70-0
• CHEMBL398325
• (13as,14r)-3,6,7-trimethoxy-9,11,12,13,13a,14-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinolin-14-ol
• NSC100055
• SCHEMBL30112928
• SCHEMBL31237779
• DTXSID90972565
• Dibenzo(f,h)pyrrolo(1,2-b)isoquinolin-14-ol, 9,11,12,13,13a,14-hexahydro-3,6,7-trimethoxy-, (13aS-cis)-
• BDBM50213934
• NSC-100055
• (12As,13r)-3,6,7-trimethoxy-13-hydroxy-9,10,11,12,12a,13-hexahydro-9a-aza-9ah-cyclopenta[b]triphenylene
• 62181-70-8
• NCI60_000003
• 3,6,7-Trimethoxy-9,11,12,13,13a,14-hexahydrodibenzo[f,H]pyrrolo[1,2-b]isoquinolin-14-ol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9333	93.33%
Caco-2	+	0.8819	88.19%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7509	75.09%
OATP2B1 inhibitior	-	0.8597	85.97%
OATP1B1 inhibitior	+	0.9345	93.45%
OATP1B3 inhibitior	+	0.9356	93.56%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	+	0.6250	62.50%
BSEP inhibitior	+	0.9680	96.80%
P-glycoprotein inhibitior	+	0.8298	82.98%
P-glycoprotein substrate	+	0.6191	61.91%
CYP3A4 substrate	+	0.5486	54.86%
CYP2C9 substrate	-	0.6092	60.92%
CYP2D6 substrate	+	0.8461	84.61%
CYP3A4 inhibition	-	0.7609	76.09%
CYP2C9 inhibition	-	0.8706	87.06%
CYP2C19 inhibition	-	0.6350	63.50%
CYP2D6 inhibition	+	0.8084	80.84%
CYP1A2 inhibition	+	0.7016	70.16%
CYP2C8 inhibition	-	0.7275	72.75%
CYP inhibitory promiscuity	-	0.6904	69.04%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6586	65.86%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.9689	96.89%
Skin irritation	-	0.7488	74.88%
Skin corrosion	-	0.9371	93.71%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7237	72.37%
Micronuclear	+	0.5300	53.00%
Hepatotoxicity	+	0.6625	66.25%
skin sensitisation	-	0.8888	88.88%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.7894	78.94%
Acute Oral Toxicity (c)	II	0.6029	60.29%
Estrogen receptor binding	+	0.7050	70.50%
Androgen receptor binding	+	0.6549	65.49%
Thyroid receptor binding	+	0.6956	69.56%
Glucocorticoid receptor binding	+	0.7045	70.45%
Aromatase binding	-	0.4893	48.93%
PPAR gamma	-	0.5660	56.60%
Honey bee toxicity	-	0.8948	89.48%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.6851	68.51%
Fish aquatic toxicity	-	0.3825	38.25%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4977	P05412	Proto-oncogene c-JUN	110 nM; 110 nM	IC50; IC50	via Super-PRED; PMID: 17531481

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL241	Q14432	Phosphodiesterase 3A	95.81%	92.94%
CHEMBL5608	Q16288	NT-3 growth factor receptor	95.08%	95.89%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.30%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	93.30%	83.82%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.22%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.33%	91.11%
CHEMBL2535	P11166	Glucose transporter	90.57%	98.75%
CHEMBL4208	P20618	Proteasome component C5	89.78%	90.00%
CHEMBL3438	Q05513	Protein kinase C zeta	89.52%	88.48%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.75%	97.09%
CHEMBL5203	P33316	dUTP pyrophosphatase	88.13%	99.18%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	86.50%	89.62%
CHEMBL1871	P10275	Androgen Receptor	86.03%	96.43%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.17%	86.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.36%	92.62%
CHEMBL3192	Q9BY41	Histone deacetylase 8	84.14%	93.99%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	83.60%	91.03%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.52%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.38%	94.45%
CHEMBL2581	P07339	Cathepsin D	83.37%	98.95%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	81.85%	90.95%
CHEMBL264	Q9Y5N1	Histamine H3 receptor	81.60%	91.43%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	81.41%	91.79%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	81.05%	100.00%
CHEMBL5747	Q92793	CREB-binding protein	80.90%	95.12%

Plants that contains it

• Vincetoxicum hirsutum
• Vincetoxicum indicum var. indicum

Cross-Links

• PubChem: 264751
• NPASS: NPC233650
• ChEMBL: CHEMBL398325
• LOTUS: LTS0196674
• wikiData: Q82956350