(1R,2S,3R,3'R,5R,6S,7S,8S,9S,12R)-3',12-dihydroxy-3'-(1-hydroxyethyl)-8-methoxy-7-methyl-12-propan-2-ylspiro[4,10-dioxatetracyclo[7.2.1.02,7.03,5]dodecane-6,5'-oxolane]-2',11-dione

Details

• Internal ID: 21a48993-7899-4d39-bd1d-25e1aaae52c7
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (1R,2S,3R,3'R,5R,6S,7S,8S,9S,12R)-3',12-dihydroxy-3'-(1-hydroxyethyl)-8-methoxy-7-methyl-12-propan-2-ylspiro[4,10-dioxatetracyclo[7.2.1.02,7.03,5]dodecane-6,5'-oxolane]-2',11-dione
• SMILES (Canonical): CC(C)C1(C2C3C4C(O4)C5(C3(C(C1OC2=O)OC)C)CC(C(=O)O5)(C(C)O)O)O
• SMILES (Isomeric): CC(C)[C@]1([C@H]2[C@@H]3[C@@H]4[C@@H](O4)[C@@]5([C@@]3([C@@H]([C@@H]1OC2=O)OC)C)C[C@](C(=O)O5)(C(C)O)O)O
• InChI: InChI=1S/C20H28O9/c1-7(2)20(25)10-9-11-12(27-11)19(6-18(24,8(3)21)16(23)29-19)17(9,4)13(26-5)14(20)28-15(10)22/h7-14,21,24-25H,6H2,1-5H3/t8?,9-,10+,11-,12-,13-,14+,17+,18-,19-,20-/m1/s1
• InChI Key: ZQSCAIZLHQRUNM-UZELFPAQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₉
• Molecular Weight: 412.40 g/mol
• Exact Mass: 412.17333247 g/mol
• Topological Polar Surface Area (TPSA): 135.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -0.86
• H-Bond Acceptor: 9
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9259	92.59%
Caco-2	-	0.7026	70.26%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6135	61.35%
OATP2B1 inhibitior	-	0.8552	85.52%
OATP1B1 inhibitior	+	0.9062	90.62%
OATP1B3 inhibitior	+	0.9196	91.96%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.8873	88.73%
P-glycoprotein inhibitior	-	0.6796	67.96%
P-glycoprotein substrate	-	0.6160	61.60%
CYP3A4 substrate	+	0.6382	63.82%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8553	85.53%
CYP3A4 inhibition	-	0.7364	73.64%
CYP2C9 inhibition	-	0.9344	93.44%
CYP2C19 inhibition	-	0.8794	87.94%
CYP2D6 inhibition	-	0.9192	91.92%
CYP1A2 inhibition	-	0.9224	92.24%
CYP2C8 inhibition	-	0.7929	79.29%
CYP inhibitory promiscuity	-	0.9807	98.07%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5440	54.40%
Eye corrosion	-	0.9830	98.30%
Eye irritation	-	0.9373	93.73%
Skin irritation	-	0.7341	73.41%
Skin corrosion	-	0.8948	89.48%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5397	53.97%
Micronuclear	+	0.5059	50.59%
Hepatotoxicity	+	0.5576	55.76%
skin sensitisation	-	0.8274	82.74%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.9400	94.00%
Acute Oral Toxicity (c)	III	0.4881	48.81%
Estrogen receptor binding	+	0.7843	78.43%
Androgen receptor binding	+	0.6815	68.15%
Thyroid receptor binding	+	0.5853	58.53%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	+	0.5426	54.26%
PPAR gamma	+	0.6982	69.82%
Honey bee toxicity	-	0.7824	78.24%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.6955	69.55%

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	97.84%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.13%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.97%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.74%	91.11%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	89.51%	97.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.00%	94.45%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	87.78%	96.38%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.19%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.18%	95.89%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	87.18%	96.47%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.74%	95.56%
CHEMBL2581	P07339	Cathepsin D	86.26%	98.95%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	84.53%	92.88%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.36%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.31%	89.00%
CHEMBL1937	Q92769	Histone deacetylase 2	81.84%	94.75%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.45%	96.77%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.46%	94.00%

Plants that contains it

• Picrodendron baccatum

Cross-Links

• PubChem: 101630473
• LOTUS: LTS0165361
• wikiData: Q105381702