[(2S,3S,3aS,4S,5R,6S,8aS)-4,6-diacetyloxy-3-hydroxy-3-methyl-8-methylidene-5-propan-2-yl-1,2,3a,4,5,6,7,8a-octahydroazulen-2-yl] acetate

Details

• Internal ID: 27405eaf-0319-4919-a3a6-5526599d5a56
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Guaianes
• IUPAC Name: [(2S,3S,3aS,4S,5R,6S,8aS)-4,6-diacetyloxy-3-hydroxy-3-methyl-8-methylidene-5-propan-2-yl-1,2,3a,4,5,6,7,8a-octahydroazulen-2-yl] acetate
• InChI: InChI=1S/C21H32O7/c1-10(2)18-16(26-12(4)22)8-11(3)15-9-17(27-13(5)23)21(7,25)19(15)20(18)28-14(6)24/h10,15-20,25H,3,8-9H2,1-2,4-7H3/t15-,16+,17+,18-,19+,20+,21-/m1/s1
• InChI Key: BUGLHVRUBMRPRP-SRWWVFQWSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₂O₇
• Molecular Weight: 396.50 g/mol
• Exact Mass: 396.21480336 g/mol
• Topological Polar Surface Area (TPSA): 99.10 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.40
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9786	97.86%
Caco-2	-	0.5211	52.11%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.7461	74.61%
OATP2B1 inhibitior	-	0.8594	85.94%
OATP1B1 inhibitior	+	0.9066	90.66%
OATP1B3 inhibitior	+	0.8555	85.55%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7348	73.48%
P-glycoprotein inhibitior	-	0.5379	53.79%
P-glycoprotein substrate	-	0.7217	72.17%
CYP3A4 substrate	+	0.6483	64.83%
CYP2C9 substrate	-	0.7948	79.48%
CYP2D6 substrate	-	0.8666	86.66%
CYP3A4 inhibition	-	0.5748	57.48%
CYP2C9 inhibition	-	0.7565	75.65%
CYP2C19 inhibition	-	0.7429	74.29%
CYP2D6 inhibition	-	0.9407	94.07%
CYP1A2 inhibition	-	0.7322	73.22%
CYP2C8 inhibition	-	0.8834	88.34%
CYP inhibitory promiscuity	-	0.9528	95.28%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5970	59.70%
Eye corrosion	-	0.9749	97.49%
Eye irritation	-	0.8564	85.64%
Skin irritation	-	0.5469	54.69%
Skin corrosion	-	0.9286	92.86%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5496	54.96%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	-	0.5074	50.74%
skin sensitisation	-	0.6323	63.23%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.6432	64.32%
Acute Oral Toxicity (c)	II	0.3912	39.12%
Estrogen receptor binding	+	0.8623	86.23%
Androgen receptor binding	-	0.5265	52.65%
Thyroid receptor binding	+	0.5299	52.99%
Glucocorticoid receptor binding	+	0.7092	70.92%
Aromatase binding	-	0.4907	49.07%
PPAR gamma	+	0.5567	55.67%
Honey bee toxicity	-	0.6441	64.41%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5655	56.55%
Fish aquatic toxicity	+	0.9917	99.17%

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	97.87%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.94%	85.14%
CHEMBL340	P08684	Cytochrome P450 3A4	93.57%	91.19%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.13%	91.11%
CHEMBL2581	P07339	Cathepsin D	89.45%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.89%	94.45%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.81%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.96%	97.09%
CHEMBL2996	Q05655	Protein kinase C delta	81.74%	97.79%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.44%	95.56%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	80.83%	92.86%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.04%	95.89%

Plants that contains it

• Salvia roborowskii

Cross-Links

• PubChem: 102280052
• LOTUS: LTS0018956
• wikiData: Q104946081