(1R,9S,10S)-3,4-dihydroxy-8-methoxy-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[7.5.2.01,10.02,7]hexadeca-2,4,6-trien-15-one

Details

• Internal ID: 6ddf6f1c-78e4-452e-9680-d7537c97090e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: (1R,9S,10S)-3,4-dihydroxy-8-methoxy-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[7.5.2.01,10.02,7]hexadeca-2,4,6-trien-15-one
• SMILES (Canonical): CC(C)C1=C(C(=C2C(=C1)C(C3C4C2(CCCC4(C)C)C(=O)O3)OC)O)O
• SMILES (Isomeric): CC(C)C1=C(C(=C2C(=C1)C([C@@H]3[C@@H]4[C@@]2(CCCC4(C)C)C(=O)O3)OC)O)O
• InChI: InChI=1S/C21H28O5/c1-10(2)11-9-12-13(15(23)14(11)22)21-8-6-7-20(3,4)18(21)17(16(12)25-5)26-19(21)24/h9-10,16-18,22-23H,6-8H2,1-5H3/t16?,17-,18+,21+/m1/s1
• InChI Key: XNPVHIQPSAZTLC-CXOHFUFESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₈O₅
• Molecular Weight: 360.40 g/mol
• Exact Mass: 360.19367399 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 3.90
• Atomic LogP (AlogP): 3.91
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9598	95.98%
Caco-2	+	0.6951	69.51%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7379	73.79%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8465	84.65%
OATP1B3 inhibitior	+	0.9156	91.56%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.6875	68.75%
P-glycoprotein inhibitior	-	0.6965	69.65%
P-glycoprotein substrate	-	0.7075	70.75%
CYP3A4 substrate	+	0.6564	65.64%
CYP2C9 substrate	-	0.6048	60.48%
CYP2D6 substrate	-	0.7528	75.28%
CYP3A4 inhibition	-	0.5699	56.99%
CYP2C9 inhibition	-	0.6544	65.44%
CYP2C19 inhibition	-	0.5145	51.45%
CYP2D6 inhibition	-	0.8640	86.40%
CYP1A2 inhibition	+	0.6299	62.99%
CYP2C8 inhibition	-	0.6633	66.33%
CYP inhibitory promiscuity	-	0.7721	77.21%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.5478	54.78%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.8938	89.38%
Skin irritation	-	0.6946	69.46%
Skin corrosion	-	0.9162	91.62%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8364	83.64%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	+	0.6088	60.88%
skin sensitisation	-	0.8627	86.27%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.6916	69.16%
Acute Oral Toxicity (c)	III	0.4831	48.31%
Estrogen receptor binding	+	0.7705	77.05%
Androgen receptor binding	+	0.6712	67.12%
Thyroid receptor binding	+	0.7134	71.34%
Glucocorticoid receptor binding	+	0.8710	87.10%
Aromatase binding	+	0.5328	53.28%
PPAR gamma	+	0.7311	73.11%
Honey bee toxicity	-	0.7440	74.40%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9936	99.36%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.99%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.62%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.25%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.15%	96.09%
CHEMBL2581	P07339	Cathepsin D	92.22%	98.95%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	91.90%	90.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.43%	95.89%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.59%	99.15%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.16%	96.77%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.15%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.91%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.60%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.43%	89.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.02%	91.07%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.96%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.64%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	84.01%	94.73%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.84%	93.56%
CHEMBL3286	P00749	Urokinase-type plasminogen activator	82.38%	97.88%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.22%	92.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.17%	94.00%
CHEMBL213	P08588	Beta-1 adrenergic receptor	81.71%	95.56%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	81.16%	96.38%
CHEMBL340	P08684	Cytochrome P450 3A4	81.02%	91.19%
CHEMBL5203	P33316	dUTP pyrophosphatase	80.55%	99.18%

Plants that contains it

• Rosmarinus officinalis

Cross-Links

• PubChem: 137706557
• LOTUS: LTS0109376
• wikiData: Q105331881