(-)-Chrysanthenone

Details

• Internal ID: 8ae38c64-27fd-41a3-b78a-32c88312ee91
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Bicyclic monoterpenoids
• IUPAC Name: (1R,5S)-2,7,7-trimethylbicyclo[3.1.1]hept-2-en-6-one
• SMILES (Canonical): CC1=CCC2C(=O)C1C2(C)C
• SMILES (Isomeric): CC1=CC[C@@H]2C(=O)[C@H]1C2(C)C
• InChI: InChI=1S/C10H14O/c1-6-4-5-7-9(11)8(6)10(7,2)3/h4,7-8H,5H2,1-3H3/t7-,8+/m1/s1
• InChI Key: IECBDTGWSQNQID-SFYZADRCSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₄O
• Molecular Weight: 150.22 g/mol
• Exact Mass: 150.104465066 g/mol
• Topological Polar Surface Area (TPSA): 17.10 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 2.18
• H-Bond Acceptor: 1
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• Chrysanthenone, (-)-
• UNII-TW9X9FD433
• 58437-73-3
• TW9X9FD433
• Bicyclo(3.1.1)hept-2-en-6-one, 2,7,7-trimethyl-, (1R,5S)-
• (?)-Chrysanthenone
• DTXSID60486649
• Q27290462

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9974	99.74%
Caco-2	+	0.5547	55.47%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.8857	88.57%
Subcellular localzation	Mitochondria	0.5296	52.96%
OATP2B1 inhibitior	-	0.8608	86.08%
OATP1B1 inhibitior	+	0.9459	94.59%
OATP1B3 inhibitior	+	0.9494	94.94%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.8993	89.93%
P-glycoprotein inhibitior	-	0.9710	97.10%
P-glycoprotein substrate	-	0.9692	96.92%
CYP3A4 substrate	-	0.5731	57.31%
CYP2C9 substrate	-	0.7977	79.77%
CYP2D6 substrate	-	0.8166	81.66%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.7575	75.75%
CYP2C19 inhibition	+	0.5593	55.93%
CYP2D6 inhibition	-	0.8873	88.73%
CYP1A2 inhibition	-	0.7658	76.58%
CYP2C8 inhibition	-	0.9881	98.81%
CYP inhibitory promiscuity	-	0.5888	58.88%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7600	76.00%
Carcinogenicity (trinary)	Non-required	0.4705	47.05%
Eye corrosion	-	0.8825	88.25%
Eye irritation	+	0.9641	96.41%
Skin irritation	+	0.6041	60.41%
Skin corrosion	-	0.9286	92.86%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6216	62.16%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	+	0.7125	71.25%
skin sensitisation	+	0.8755	87.55%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	-	0.5667	56.67%
Mitochondrial toxicity	-	0.7750	77.50%
Nephrotoxicity	+	0.5736	57.36%
Acute Oral Toxicity (c)	III	0.7560	75.60%
Estrogen receptor binding	-	0.8994	89.94%
Androgen receptor binding	-	0.6616	66.16%
Thyroid receptor binding	-	0.8509	85.09%
Glucocorticoid receptor binding	-	0.9023	90.23%
Aromatase binding	-	0.9328	93.28%
PPAR gamma	-	0.8547	85.47%
Honey bee toxicity	-	0.8461	84.61%
Biodegradation	+	0.6000	60.00%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9476	94.76%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.82%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.30%	96.09%
CHEMBL2581	P07339	Cathepsin D	84.20%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.44%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.76%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	81.87%	91.11%

Plants that contains it

• Anthemis aciphylla
• Artemisia annua
• Artemisia argyi
• Artemisia capillaris
• Artemisia montana
• Artemisia princeps
• Aucklandia costus
• Chrysanthemum indicum
• Coreocarpus arizonicus
• Laggera tomentosa
• Tanacetum vulgare subsp. vulgare

Cross-Links

• PubChem: 12303211
• NPASS: NPC71613
• LOTUS: LTS0167937
• wikiData: Q105219678