Secaclavin

Details

• Internal ID: 9b31c061-f29f-4473-9faf-95dc0efca1b8
• Taxonomy: Alkaloids and derivatives > Ergoline and derivatives > Clavines and derivatives
• IUPAC Name: (E)-2-methyl-3-[4-(methylamino)-1,3,4,5-tetrahydrobenzo[cd]indol-5-yl]prop-2-en-1-ol
• SMILES (Canonical): CC(=CC1C(CC2=CNC3=CC=CC1=C23)NC)CO
• SMILES (Isomeric): C/C(=C\C1C(CC2=CNC3=CC=CC1=C23)NC)/CO
• InChI: InChI=1S/C16H20N2O/c1-10(9-19)6-13-12-4-3-5-14-16(12)11(8-18-14)7-15(13)17-2/h3-6,8,13,15,17-19H,7,9H2,1-2H3/b10-6+
• InChI Key: SAHHMCVYMGARBT-UXBLZVDNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₀N₂O
• Molecular Weight: 256.34 g/mol
• Exact Mass: 256.157563266 g/mol
• Topological Polar Surface Area (TPSA): 48.00 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.33
• H-Bond Acceptor: 2
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

• Secaclavine
• SCHEMBL10822246
• SAHHMCVYMGARBT-UXBLZVDNSA-N
• 2-Propen-1-ol, 2-methyl-3-[1,3,4,5-tetrahydro-4-(methylamino)benz[cd]indol-5-yl]-, [4R-[4.alpha.,5.beta.(E)]]-
• Benz[cd]indole, 2-propen-1-ol deriv.
• 2-Methyl-3-[4-(methylamino)-1,3,4,5-tetrahydrobenzo[cd]indol-5-yl]-2-propen-1-ol-, (4R-(4alpha,5beta (E)))-
• 2-Propen-1-ol, 2-methyl-3-[1,3,4,5-tetrahydro-4.beta.-(methylamino)benz[cd]indol-5.alpha.-yl]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9960	99.60%
Caco-2	+	0.6537	65.37%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Nucleus	0.3421	34.21%
OATP2B1 inhibitior	-	0.8579	85.79%
OATP1B1 inhibitior	+	0.9093	90.93%
OATP1B3 inhibitior	+	0.9441	94.41%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.6114	61.14%
P-glycoprotein inhibitior	-	0.9688	96.88%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.5992	59.92%
CYP2C9 substrate	-	0.6079	60.79%
CYP2D6 substrate	+	0.4918	49.18%
CYP3A4 inhibition	+	0.5414	54.14%
CYP2C9 inhibition	-	0.5523	55.23%
CYP2C19 inhibition	+	0.5594	55.94%
CYP2D6 inhibition	+	0.5779	57.79%
CYP1A2 inhibition	+	0.7582	75.82%
CYP2C8 inhibition	-	0.6290	62.90%
CYP inhibitory promiscuity	+	0.7792	77.92%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9410	94.10%
Carcinogenicity (trinary)	Non-required	0.6540	65.40%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.9976	99.76%
Skin irritation	-	0.7634	76.34%
Skin corrosion	-	0.8950	89.50%
Ames mutagenesis	+	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7980	79.80%
Micronuclear	+	0.6900	69.00%
Hepatotoxicity	-	0.7287	72.87%
skin sensitisation	-	0.8193	81.93%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	+	0.4912	49.12%
Acute Oral Toxicity (c)	III	0.5346	53.46%
Estrogen receptor binding	-	0.5070	50.70%
Androgen receptor binding	-	0.5820	58.20%
Thyroid receptor binding	+	0.5538	55.38%
Glucocorticoid receptor binding	+	0.5987	59.87%
Aromatase binding	+	0.6052	60.52%
PPAR gamma	+	0.5250	52.50%
Honey bee toxicity	-	0.8169	81.69%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9073	90.73%

Targets

Proven Targets:

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	97.15%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.05%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.85%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.73%	94.45%
CHEMBL2996	Q05655	Protein kinase C delta	90.65%	97.79%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	88.85%	91.79%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	88.84%	83.10%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	87.71%	96.39%
CHEMBL222	P23975	Norepinephrine transporter	87.07%	96.06%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.07%	95.89%
CHEMBL1951	P21397	Monoamine oxidase A	86.78%	91.49%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	85.21%	93.03%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.43%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.65%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.10%	100.00%
CHEMBL3227	P41594	Metabotropic glutamate receptor 5	82.62%	96.42%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	81.74%	89.62%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.70%	95.83%
CHEMBL3401	O75469	Pregnane X receptor	80.50%	94.73%

Plants that contains it

• Ipomoea nil

Cross-Links

• PubChem: 5374930
• NPASS: NPC91589