Rupicolin A

Details

• Internal ID: 92e65640-391a-439f-8cd5-686513999c4c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3aR,4S,6aS,9aR,9bS)-4,6a-dihydroxy-6,9-dimethyl-3-methylidene-4,7,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-2-one
• SMILES (Canonical): CC1=CCC2(C1C3C(C(C=C2C)O)C(=C)C(=O)O3)O
• SMILES (Isomeric): CC1=CC[C@@]2([C@H]1[C@@H]3[C@@H]([C@H](C=C2C)O)C(=C)C(=O)O3)O
• InChI: InChI=1S/C15H18O4/c1-7-4-5-15(18)8(2)6-10(16)11-9(3)14(17)19-13(11)12(7)15/h4,6,10-13,16,18H,3,5H2,1-2H3/t10-,11+,12+,13-,15+/m0/s1
• InChI Key: ALNCFDHHBVHAKC-IHWVXMPCSA-N
• Popularity: 16 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₄
• Molecular Weight: 262.30 g/mol
• Exact Mass: 262.12050905 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): 1.10
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• 41653-82-1
• (3aR,4S,6aS,9aR,9bS)-4,6a-dihydroxy-6,9-dimethyl-3-methylidene-4,7,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-2-one
• Azuleno(4,5-b)furan-2(3H)-one, 3a,4,6a,7,9a,9b-hexahydro-4,6a-dihydroxy-6,9-dimethyl-3-methylene-, (3aR-(3aalpha,4alpha,6aalpha,9aalpha,9bbeta))-
• DTXSID40194472

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9867	98.67%
Caco-2	-	0.5817	58.17%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.4381	43.81%
OATP2B1 inhibitior	-	0.8596	85.96%
OATP1B1 inhibitior	+	0.9126	91.26%
OATP1B3 inhibitior	+	0.9377	93.77%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9520	95.20%
P-glycoprotein inhibitior	-	0.9224	92.24%
P-glycoprotein substrate	-	0.8522	85.22%
CYP3A4 substrate	+	0.5573	55.73%
CYP2C9 substrate	-	0.8097	80.97%
CYP2D6 substrate	-	0.8447	84.47%
CYP3A4 inhibition	-	0.7994	79.94%
CYP2C9 inhibition	-	0.9273	92.73%
CYP2C19 inhibition	-	0.8945	89.45%
CYP2D6 inhibition	-	0.9487	94.87%
CYP1A2 inhibition	-	0.7215	72.15%
CYP2C8 inhibition	-	0.8530	85.30%
CYP inhibitory promiscuity	-	0.9353	93.53%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9325	93.25%
Carcinogenicity (trinary)	Non-required	0.4775	47.75%
Eye corrosion	-	0.9688	96.88%
Eye irritation	-	0.8125	81.25%
Skin irritation	+	0.5067	50.67%
Skin corrosion	-	0.8008	80.08%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6876	68.76%
Micronuclear	-	0.5900	59.00%
Hepatotoxicity	+	0.8908	89.08%
skin sensitisation	-	0.6217	62.17%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.6200	62.00%
Acute Oral Toxicity (c)	III	0.3581	35.81%
Estrogen receptor binding	-	0.5145	51.45%
Androgen receptor binding	-	0.4811	48.11%
Thyroid receptor binding	-	0.5354	53.54%
Glucocorticoid receptor binding	+	0.5419	54.19%
Aromatase binding	-	0.6040	60.40%
PPAR gamma	-	0.5167	51.67%
Honey bee toxicity	-	0.7851	78.51%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.8986	89.86%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.45%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.73%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.93%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.39%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.27%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.77%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.73%	94.00%

Plants that contains it

• Achillea clavennae
• Achillea clypeolata
• Achillea crithmifolia
• Achillea setacea
• Artemisia gmelinii
• Artemisia sylvatica
• Artemisia tripartita
• Artemisia xerophytica
• Mimosa diplotricha
• Schistostephium rotundifolium
• Tanacetum santolina

Cross-Links

• PubChem: 3082541
• NPASS: NPC304211
• LOTUS: LTS0138391
• wikiData: Q83067224