(2S,3R)-2,3-dihydroxy-3-(9H-pyrido[3,4-b]indol-1-yl)propanoic acid

Details

• Internal ID: aeb3a8bc-5c42-46cd-ac48-f2bd3b51864a
• Taxonomy: Alkaloids and derivatives > Harmala alkaloids
• IUPAC Name: (2S,3R)-2,3-dihydroxy-3-(9H-pyrido[3,4-b]indol-1-yl)propanoic acid
• SMILES (Canonical): C1=CC=C2C(=C1)C3=C(N2)C(=NC=C3)C(C(C(=O)O)O)O
• SMILES (Isomeric): C1=CC=C2C(=C1)C3=C(N2)C(=NC=C3)[C@H]([C@@H](C(=O)O)O)O
• InChI: InChI=1S/C14H12N2O4/c17-12(13(18)14(19)20)11-10-8(5-6-15-11)7-3-1-2-4-9(7)16-10/h1-6,12-13,16-18H,(H,19,20)/t12-,13+/m1/s1
• InChI Key: ILYUVVMAFUMFKE-OLZOCXBDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₂N₂O₄
• Molecular Weight: 272.26 g/mol
• Exact Mass: 272.07970687 g/mol
• Topological Polar Surface Area (TPSA): 106.00 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): 1.19
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8895	88.95%
Caco-2	-	0.8014	80.14%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.5499	54.99%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9407	94.07%
OATP1B3 inhibitior	+	0.9455	94.55%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.6827	68.27%
P-glycoprotein inhibitior	-	0.9060	90.60%
P-glycoprotein substrate	-	0.8892	88.92%
CYP3A4 substrate	-	0.5114	51.14%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8332	83.32%
CYP3A4 inhibition	-	0.6732	67.32%
CYP2C9 inhibition	-	0.7832	78.32%
CYP2C19 inhibition	-	0.7387	73.87%
CYP2D6 inhibition	-	0.8642	86.42%
CYP1A2 inhibition	+	0.6933	69.33%
CYP2C8 inhibition	+	0.4754	47.54%
CYP inhibitory promiscuity	-	0.8078	80.78%
UGT catelyzed	+	0.7159	71.59%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.7223	72.23%
Eye corrosion	-	0.9937	99.37%
Eye irritation	-	0.6376	63.76%
Skin irritation	-	0.7650	76.50%
Skin corrosion	-	0.9725	97.25%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7799	77.99%
Micronuclear	+	0.7800	78.00%
Hepatotoxicity	+	0.5333	53.33%
skin sensitisation	-	0.9094	90.94%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.7870	78.70%
Acute Oral Toxicity (c)	III	0.5002	50.02%
Estrogen receptor binding	+	0.7378	73.78%
Androgen receptor binding	+	0.6470	64.70%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.5872	58.72%
Aromatase binding	+	0.7303	73.03%
PPAR gamma	+	0.8206	82.06%
Honey bee toxicity	-	0.9416	94.16%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	-	0.6569	65.69%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	96.15%	94.62%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.25%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.04%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.32%	91.11%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	89.44%	94.08%
CHEMBL2581	P07339	Cathepsin D	88.89%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.71%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.71%	95.56%
CHEMBL1781	P11387	DNA topoisomerase I	87.87%	97.00%
CHEMBL1868	P17948	Vascular endothelial growth factor receptor 1	87.87%	96.47%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.32%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.38%	94.45%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	83.53%	94.23%
CHEMBL213	P08588	Beta-1 adrenergic receptor	83.24%	95.56%

Plants that contains it

• Picrasma quassioides

Cross-Links

• PubChem: 163185547
• LOTUS: LTS0106702
• wikiData: Q105115552