Artemisinic acid

Details

• Internal ID: 82e5b0d7-7497-42d1-875d-9d4adc8e641d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: 2-[(1R,4R,4aS,8aR)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl]prop-2-enoic acid
• SMILES (Canonical): CC1CCC(C2C1CCC(=C2)C)C(=C)C(=O)O
• SMILES (Isomeric): C[C@@H]1CC[C@H]([C@@H]2[C@H]1CCC(=C2)C)C(=C)C(=O)O
• InChI: InChI=1S/C15H22O2/c1-9-4-6-12-10(2)5-7-13(14(12)8-9)11(3)15(16)17/h8,10,12-14H,3-7H2,1-2H3,(H,16,17)/t10-,12+,13+,14+/m1/s1
• InChI Key: PLQMEXSCSAIXGB-SAXRGWBVSA-N
• Popularity: 154 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₂
• Molecular Weight: 234.33 g/mol
• Exact Mass: 234.161979940 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 3.65
• H-Bond Acceptor: 1
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• Artemisic acid
• 80286-58-4
• (+)-artemisinic acid
• Arteannuic acid
• 2-[(1R,4R,4aS,8aR)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl]prop-2-enoic acid
• CHEBI:63749
• UNII-53N99527G7
• MFCD00238540
• 53N99527G7
• EC 617-040-5
• 2-((1r,4r,4as,8ar)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl)acrylic acid
• 2-((1R,4R,4aS,8aR)-4,7-Dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl)prop-2-enoic acid
• Artemisinicacid
• Artemisinic-acid
• QING HAO ACID
• QING HAU ACID
• Qing Hao acid; Artemisinic acid; Arteannuic acid
• ARTEMISININIC ACID
• SCHEMBL159983
• CHEMBL457385
• ARTEMISINIC ACID [INCI]
• SINGLEEX ARTEMISINIC ACID
• PLQMEXSCSAIXGB-SAXRGWBVSA-N
• HY-N1984
• s9135
• 4,11(13)-Cadinadien-12-oic acid
• AKOS017343176
• 4,11(13)-Amorphadien-12-oic acid
• CCG-266821
• LMPR0103190015
• AC-34595
• AS-78501
• CS-0018305
• C20309
• 4,11(13)-Cadinadien-12-oic acid;Artemisic acid
• A856098
• Q27132774
• 222F86B0-6F56-4D85-98B2-F1B0E146A747
• 1-NAPHTHALENEACETIC ACID, 1,2,3,4,4A,5,6,8A-OCTAHYDRO-4,7-DIMETHYL-.ALPHA.-METHYLENE-, (1R,4R,4AS,8AR)-
• 1-NAPHTHALENEACETIC ACID, 1,2,3,4,4A,5,6,8A-OCTAHYDRO-4,7-DIMETHYL-.ALPHA.-METHYLENE-, (1R-(1.ALPHA.,4.BETA.,4A.BETA.,8A.BETA.))-
• 1-Naphthaleneacetic acid, 1,2,3,4,4a,5,6,8a-octahydro-4,7-dimethyl-alpha-methylene-, (1R-(1alpha,4beta,4abeta,8abeta))-
• 2-[(1R,4R,4aS,8aR)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl]prop-2-enoicacid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9955	99.55%
Caco-2	+	0.8274	82.74%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Plasma membrane	0.5259	52.59%
OATP2B1 inhibitior	-	0.8533	85.33%
OATP1B1 inhibitior	+	0.9394	93.94%
OATP1B3 inhibitior	+	0.8224	82.24%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	+	0.5750	57.50%
BSEP inhibitior	-	0.9452	94.52%
P-glycoprotein inhibitior	-	0.9509	95.09%
P-glycoprotein substrate	-	0.8627	86.27%
CYP3A4 substrate	+	0.5158	51.58%
CYP2C9 substrate	+	0.6092	60.92%
CYP2D6 substrate	-	0.8904	89.04%
CYP3A4 inhibition	-	0.8118	81.18%
CYP2C9 inhibition	-	0.7354	73.54%
CYP2C19 inhibition	-	0.6889	68.89%
CYP2D6 inhibition	-	0.9213	92.13%
CYP1A2 inhibition	-	0.6675	66.75%
CYP2C8 inhibition	-	0.7617	76.17%
CYP inhibitory promiscuity	-	0.8606	86.06%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.6194	61.94%
Eye corrosion	-	0.8818	88.18%
Eye irritation	-	0.4776	47.76%
Skin irritation	-	0.6351	63.51%
Skin corrosion	-	0.9774	97.74%
Ames mutagenesis	-	0.6954	69.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.6286	62.86%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	+	0.7000	70.00%
skin sensitisation	+	0.7794	77.94%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.5308	53.08%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.6711	67.11%
Acute Oral Toxicity (c)	III	0.8299	82.99%
Estrogen receptor binding	-	0.8381	83.81%
Androgen receptor binding	+	0.5673	56.73%
Thyroid receptor binding	-	0.6473	64.73%
Glucocorticoid receptor binding	-	0.5360	53.60%
Aromatase binding	-	0.7515	75.15%
PPAR gamma	-	0.6223	62.23%
Honey bee toxicity	-	0.9374	93.74%
Biodegradation	+	0.5250	52.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	91.08%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.26%	95.56%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	86.03%	94.80%
CHEMBL2581	P07339	Cathepsin D	82.72%	98.95%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.95%	93.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.40%	97.09%

Plants that contains it

• Artemisia annua
• Artemisia carvifolia
• Solanum lycopersicum

Cross-Links

• PubChem: 10922465
• NPASS: NPC35656
• LOTUS: LTS0224622
• wikiData: Q27132774