(1S,10S,12S,13Z,18S)-13-ethylidene-18-(hydroxymethyl)-8,15-diazapentacyclo[10.5.1.01,9.02,7.010,15]octadeca-2,4,6,8-tetraene-18-carboxylic acid

Details

• Internal ID: 4873b0ab-ae1f-4f95-b65e-d266ac546aca
• Taxonomy: Alkaloids and derivatives > Corynanthean-type alkaloids
• IUPAC Name: (1S,10S,12S,13Z,18S)-13-ethylidene-18-(hydroxymethyl)-8,15-diazapentacyclo[10.5.1.01,9.02,7.010,15]octadeca-2,4,6,8-tetraene-18-carboxylic acid
• SMILES (Canonical): CC=C1CN2CCC34C5=CC=CC=C5N=C3C2CC1C4(CO)C(=O)O
• SMILES (Isomeric): C/C=C/1\CN2CC[C@@]34C5=CC=CC=C5N=C3[C@@H]2C[C@@H]1[C@]4(CO)C(=O)O
• InChI: InChI=1S/C20H22N2O3/c1-2-12-10-22-8-7-19-13-5-3-4-6-15(13)21-17(19)16(22)9-14(12)20(19,11-23)18(24)25/h2-6,14,16,23H,7-11H2,1H3,(H,24,25)/b12-2+/t14-,16-,19+,20+/m0/s1
• InChI Key: FDYLWAVIWXASTK-GNSQTZGJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₂N₂O₃
• Molecular Weight: 338.40 g/mol
• Exact Mass: 338.16304257 g/mol
• Topological Polar Surface Area (TPSA): 73.10 Ų
• XlogP: -1.70
• Atomic LogP (AlogP): 2.13
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9038	90.38%
Caco-2	+	0.5492	54.92%
Blood Brain Barrier	+	0.6277	62.77%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6355	63.55%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8846	88.46%
OATP1B3 inhibitior	+	0.9370	93.70%
MATE1 inhibitior	-	0.9067	90.67%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.6515	65.15%
P-glycoprotein inhibitior	-	0.8591	85.91%
P-glycoprotein substrate	+	0.5146	51.46%
CYP3A4 substrate	+	0.6346	63.46%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7461	74.61%
CYP3A4 inhibition	-	0.9321	93.21%
CYP2C9 inhibition	-	0.8295	82.95%
CYP2C19 inhibition	-	0.8655	86.55%
CYP2D6 inhibition	-	0.7356	73.56%
CYP1A2 inhibition	-	0.6657	66.57%
CYP2C8 inhibition	-	0.5907	59.07%
CYP inhibitory promiscuity	-	0.9113	91.13%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.6572	65.72%
Eye corrosion	-	0.9841	98.41%
Eye irritation	-	0.9631	96.31%
Skin irritation	-	0.7443	74.43%
Skin corrosion	-	0.9106	91.06%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4551	45.51%
Micronuclear	+	0.5900	59.00%
Hepatotoxicity	+	0.5087	50.87%
skin sensitisation	-	0.8121	81.21%
Respiratory toxicity	+	0.9333	93.33%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	+	0.7131	71.31%
Acute Oral Toxicity (c)	III	0.6372	63.72%
Estrogen receptor binding	+	0.5826	58.26%
Androgen receptor binding	+	0.7310	73.10%
Thyroid receptor binding	+	0.5892	58.92%
Glucocorticoid receptor binding	+	0.6517	65.17%
Aromatase binding	-	0.6221	62.21%
PPAR gamma	-	0.5684	56.84%
Honey bee toxicity	-	0.9050	90.50%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9481	94.81%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.47%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.64%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.57%	86.33%
CHEMBL2581	P07339	Cathepsin D	86.00%	98.95%
CHEMBL5028	O14672	ADAM10	84.46%	97.50%
CHEMBL221	P23219	Cyclooxygenase-1	84.14%	90.17%
CHEMBL4208	P20618	Proteasome component C5	82.98%	90.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.75%	99.23%
CHEMBL3492	P49721	Proteasome Macropain subunit	82.56%	90.24%

Plants that contains it

• Catharanthus roseus
• Kopsia griffithii
• Kopsia teoi
• Rhazya stricta

Cross-Links

• PubChem: 101986486
• LOTUS: LTS0128010
• wikiData: Q104402114