1,4-Anthracenedione, 5,6,7,8-tetrahydro-2-hydroxy-3-[(1R)-2-hydroxy-1-methylethyl]-5,5,9-trimethyl-

Details

• Internal ID: 018944c4-d7fe-4c77-8375-74f63f0f80bd
• Taxonomy: Benzenoids > Anthracenes > Anthraquinones
• IUPAC Name: 4-hydroxy-3-[(2R)-1-hydroxypropan-2-yl]-5,5,9-trimethyl-7,8-dihydro-6H-anthracene-1,2-dione
• SMILES (Canonical): CC1=C2C(=CC3=C1CCCC3(C)C)C(=C(C(=O)C2=O)C(C)CO)O
• SMILES (Isomeric): CC1=C2C(=CC3=C1CCCC3(C)C)C(=C(C(=O)C2=O)[C@@H](C)CO)O
• InChI: InChI=1S/C20H24O4/c1-10(9-21)15-17(22)13-8-14-12(6-5-7-20(14,3)4)11(2)16(13)19(24)18(15)23/h8,10,21-22H,5-7,9H2,1-4H3/t10-/m0/s1
• InChI Key: HPDJDMAPXQNONF-JTQLQIEISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄O₄
• Molecular Weight: 328.40 g/mol
• Exact Mass: 328.16745924 g/mol
• Topological Polar Surface Area (TPSA): 74.60 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 3.27
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• CHEMBL1993232
• NSC-686516
• NCI60_031206
• 1,4-Anthracenedione, 5,6,7,8-tetrahydro-2-hydroxy-3-[(1R)-2-hydroxy-1-methylethyl]-5,5,9-trimethyl-
• 3-hydroxy-2-[(1R)-2-hydroxy-1-methyl-ethyl]-8,8,10-trimethyl-6,7-dihydro-5H-anthracene-1,4-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9884	98.84%
Caco-2	+	0.8057	80.57%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.8320	83.20%
OATP2B1 inhibitior	-	0.7174	71.74%
OATP1B1 inhibitior	+	0.8370	83.70%
OATP1B3 inhibitior	+	0.8456	84.56%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.6223	62.23%
BSEP inhibitior	-	0.7844	78.44%
P-glycoprotein inhibitior	-	0.8806	88.06%
P-glycoprotein substrate	-	0.8008	80.08%
CYP3A4 substrate	+	0.5582	55.82%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8688	86.88%
CYP3A4 inhibition	-	0.7660	76.60%
CYP2C9 inhibition	+	0.5457	54.57%
CYP2C19 inhibition	-	0.6557	65.57%
CYP2D6 inhibition	-	0.8359	83.59%
CYP1A2 inhibition	+	0.6682	66.82%
CYP2C8 inhibition	-	0.7656	76.56%
CYP inhibitory promiscuity	-	0.5955	59.55%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.6865	68.65%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.7660	76.60%
Skin irritation	-	0.6164	61.64%
Skin corrosion	-	0.9533	95.33%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5675	56.75%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.5519	55.19%
skin sensitisation	-	0.7229	72.29%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.8207	82.07%
Acute Oral Toxicity (c)	III	0.7824	78.24%
Estrogen receptor binding	-	0.6522	65.22%
Androgen receptor binding	-	0.5192	51.92%
Thyroid receptor binding	-	0.5082	50.82%
Glucocorticoid receptor binding	+	0.7932	79.32%
Aromatase binding	-	0.5842	58.42%
PPAR gamma	+	0.8470	84.70%
Honey bee toxicity	-	0.9215	92.15%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.7800	78.00%
Fish aquatic toxicity	+	0.9957	99.57%

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	98.33%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.72%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.24%	95.56%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	91.00%	96.38%
CHEMBL1937	Q92769	Histone deacetylase 2	90.79%	94.75%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	90.12%	91.79%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	89.42%	93.40%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	89.28%	98.75%
CHEMBL2535	P11166	Glucose transporter	87.89%	98.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.10%	89.00%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	86.82%	96.09%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.62%	90.71%
CHEMBL4835	P00338	L-lactate dehydrogenase A chain	85.17%	95.34%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.18%	99.15%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.30%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.05%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.52%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.01%	100.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.51%	96.21%

Plants that contains it

• Salvia aegyptiaca

Cross-Links

• PubChem: 389887
• LOTUS: LTS0212857
• wikiData: Q105031652