Calamusin A

Details

• Internal ID: dd6e8c35-0a74-4b0d-a026-9478b16edbb3
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (3aS,4R,8S,8aS)-3a-hydroxy-2-(2-hydroxypropan-2-yl)-4,8-dimethyl-5,6,8,8a-tetrahydro-4H-azulene-1,7-dione
• SMILES (Canonical): CC1CCC(=O)C(C2C1(C=C(C2=O)C(C)(C)O)O)C
• SMILES (Isomeric): C[C@@H]1CCC(=O)[C@H]([C@H]2[C@]1(C=C(C2=O)C(C)(C)O)O)C
• InChI: InChI=1S/C15H22O4/c1-8-5-6-11(16)9(2)12-13(17)10(14(3,4)18)7-15(8,12)19/h7-9,12,18-19H,5-6H2,1-4H3/t8-,9-,12-,15-/m1/s1
• InChI Key: WTUUXOKSFWSVCT-YGDJUROISA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.33 g/mol
• Exact Mass: 266.15180918 g/mol
• Topological Polar Surface Area (TPSA): 74.60 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 1.25
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• RefChem:122694
• (3aS,4R,8S,8aS)-3a-hydroxy-2-(2-hydroxypropan-2-yl)-4,8-dimethyl-5,6,8,8a-tetrahydro-4H-azulene-1,7-dione
• CHEMBL2063009

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9865	98.65%
Caco-2	+	0.5306	53.06%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6641	66.41%
OATP2B1 inhibitior	-	0.8533	85.33%
OATP1B1 inhibitior	+	0.9507	95.07%
OATP1B3 inhibitior	+	0.8894	88.94%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6321	63.21%
BSEP inhibitior	-	0.9438	94.38%
P-glycoprotein inhibitior	-	0.8973	89.73%
P-glycoprotein substrate	-	0.8680	86.80%
CYP3A4 substrate	+	0.5428	54.28%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8608	86.08%
CYP3A4 inhibition	-	0.8443	84.43%
CYP2C9 inhibition	-	0.6901	69.01%
CYP2C19 inhibition	-	0.8412	84.12%
CYP2D6 inhibition	-	0.9244	92.44%
CYP1A2 inhibition	-	0.5848	58.48%
CYP2C8 inhibition	-	0.9260	92.60%
CYP inhibitory promiscuity	-	0.9057	90.57%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.5501	55.01%
Eye corrosion	-	0.9850	98.50%
Eye irritation	-	0.6809	68.09%
Skin irritation	+	0.5734	57.34%
Skin corrosion	-	0.8628	86.28%
Ames mutagenesis	-	0.7398	73.98%
Human Ether-a-go-go-Related Gene inhibition	-	0.6687	66.87%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	+	0.5731	57.31%
skin sensitisation	-	0.5790	57.90%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.5909	59.09%
Acute Oral Toxicity (c)	II	0.3928	39.28%
Estrogen receptor binding	-	0.6666	66.66%
Androgen receptor binding	+	0.5415	54.15%
Thyroid receptor binding	+	0.5888	58.88%
Glucocorticoid receptor binding	-	0.6704	67.04%
Aromatase binding	-	0.7078	70.78%
PPAR gamma	-	0.7469	74.69%
Honey bee toxicity	-	0.9326	93.26%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9537	95.37%

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	96.96%	97.25%
CHEMBL2581	P07339	Cathepsin D	92.39%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.69%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.46%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.33%	91.11%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	85.25%	93.04%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.20%	100.00%
CHEMBL1902	P62942	FK506-binding protein 1A	83.55%	97.05%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.45%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.63%	95.89%

Plants that contains it

• Acorus calamus

Cross-Links

• PubChem: 60156050
• NPASS: NPC171665