3alpha-Hydroxyartemisinic acid

Details

• Internal ID: 68acff46-9db4-4b25-add9-268f4672d82c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (2R)-2-[(1S,4aR,6R,8aS)-6-hydroxy-4,7-dimethyl-1,2,4a,5,6,8a-hexahydronaphthalen-1-yl]propanoic acid
• SMILES (Canonical): CC1=CCC(C2C1CC(C(=C2)C)O)C(C)C(=O)O
• SMILES (Isomeric): CC1=CC[C@@H]([C@@H]2[C@H]1C[C@H](C(=C2)C)O)[C@@H](C)C(=O)O
• InChI: InChI=1S/C15H22O3/c1-8-4-5-11(10(3)15(17)18)13-6-9(2)14(16)7-12(8)13/h4,6,10-14,16H,5,7H2,1-3H3,(H,17,18)/t10-,11-,12+,13-,14-/m1/s1
• InChI Key: FHZJEKGROMUBDB-RKQHYHRCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₃
• Molecular Weight: 250.33 g/mol
• Exact Mass: 250.15689456 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 2.62
• H-Bond Acceptor: 2
• 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	+	0.9971	99.71%
Caco-2	+	0.6152	61.52%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7551	75.51%
OATP2B1 inhibitior	-	0.8529	85.29%
OATP1B1 inhibitior	+	0.9182	91.82%
OATP1B3 inhibitior	+	0.9620	96.20%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.8800	88.00%
P-glycoprotein inhibitior	-	0.9674	96.74%
P-glycoprotein substrate	-	0.8492	84.92%
CYP3A4 substrate	-	0.5543	55.43%
CYP2C9 substrate	-	0.6226	62.26%
CYP2D6 substrate	-	0.8423	84.23%
CYP3A4 inhibition	-	0.7878	78.78%
CYP2C9 inhibition	-	0.9323	93.23%
CYP2C19 inhibition	-	0.8800	88.00%
CYP2D6 inhibition	-	0.8583	85.83%
CYP1A2 inhibition	-	0.8783	87.83%
CYP2C8 inhibition	-	0.9395	93.95%
CYP inhibitory promiscuity	-	0.8073	80.73%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8913	89.13%
Carcinogenicity (trinary)	Non-required	0.6149	61.49%
Eye corrosion	-	0.9880	98.80%
Eye irritation	-	0.7891	78.91%
Skin irritation	+	0.5329	53.29%
Skin corrosion	-	0.9496	94.96%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7935	79.35%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	+	0.7125	71.25%
skin sensitisation	+	0.5000	50.00%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.6650	66.50%
Acute Oral Toxicity (c)	III	0.6993	69.93%
Estrogen receptor binding	-	0.7146	71.46%
Androgen receptor binding	-	0.6293	62.93%
Thyroid receptor binding	-	0.6278	62.78%
Glucocorticoid receptor binding	-	0.5546	55.46%
Aromatase binding	-	0.8275	82.75%
PPAR gamma	+	0.5294	52.94%
Honey bee toxicity	-	0.9210	92.10%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9746	97.46%

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	92.82%	96.09%
CHEMBL3359	P21462	Formyl peptide receptor 1	91.48%	93.56%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.00%	95.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.82%	90.71%
CHEMBL2581	P07339	Cathepsin D	83.42%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.20%	97.09%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	82.98%	97.21%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.24%	94.45%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 139585780
• LOTUS: LTS0235146
• wikiData: Q77491518