Dihydrotanshinone

Details

• Internal ID: b7146aba-5957-4c99-9150-1670b4b19111
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Tanshinones, isotanshinones, and derivatives
• IUPAC Name: 1,6-dimethyl-1,2-dihydronaphtho[1,2-g][1]benzofuran-10,11-dione
• SMILES (Canonical): CC1COC2=C1C(=O)C(=O)C3=C2C=CC4=C(C=CC=C43)C
• SMILES (Isomeric): CC1COC2=C1C(=O)C(=O)C3=C2C=CC4=C(C=CC=C43)C
• InChI: InChI=1S/C18H14O3/c1-9-4-3-5-12-11(9)6-7-13-15(12)17(20)16(19)14-10(2)8-21-18(13)14/h3-7,10H,8H2,1-2H3
• InChI Key: HARGZZNYNSYSGJ-UHFFFAOYSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₄O₃
• Molecular Weight: 278.30 g/mol
• Exact Mass: 278.094294304 g/mol
• Topological Polar Surface Area (TPSA): 43.40 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 3.29
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• 125623-97-4
• CHEMBL1358724
• 1,6-dimethyl-1,2-dihydronaphtho[1,2-g][1]benzofuran-10,11-dione
• BSPBio_002470
• SPECTRUM1505825
• SCHEMBL5940466
• BDBM50391428
• AKOS015903073
• CCG-214427
• NCGC00095712-01
• NCGC00095712-02
• NCGC00095712-03
• AC-22922
• BS-43783
• FT-0686597
• A14563
• Dihydrotanshinone I; 15,16-Dihydrotanshinone I
• Q-100873
• 1,6-dimethyl-1,2-dihydrophenanthro[1,2-b]furan-10,11-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.9002	90.02%
Blood Brain Barrier	+	0.5678	56.78%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7877	78.77%
OATP2B1 inhibitior	-	0.8593	85.93%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9712	97.12%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.6963	69.63%
P-glycoprotein inhibitior	-	0.6313	63.13%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.5955	59.55%
CYP2C9 substrate	-	0.8134	81.34%
CYP2D6 substrate	-	0.8183	81.83%
CYP3A4 inhibition	-	0.8310	83.10%
CYP2C9 inhibition	+	0.8163	81.63%
CYP2C19 inhibition	+	0.7145	71.45%
CYP2D6 inhibition	-	0.7503	75.03%
CYP1A2 inhibition	+	0.9385	93.85%
CYP2C8 inhibition	-	0.8299	82.99%
CYP inhibitory promiscuity	+	0.8855	88.55%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9543	95.43%
Carcinogenicity (trinary)	Non-required	0.5280	52.80%
Eye corrosion	-	0.9764	97.64%
Eye irritation	-	0.8367	83.67%
Skin irritation	-	0.7065	70.65%
Skin corrosion	-	0.9539	95.39%
Ames mutagenesis	+	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5075	50.75%
Micronuclear	+	0.6600	66.00%
Hepatotoxicity	+	0.5524	55.24%
skin sensitisation	+	0.4773	47.73%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.7592	75.92%
Acute Oral Toxicity (c)	III	0.4254	42.54%
Estrogen receptor binding	+	0.8206	82.06%
Androgen receptor binding	+	0.7474	74.74%
Thyroid receptor binding	-	0.6119	61.19%
Glucocorticoid receptor binding	+	0.6995	69.95%
Aromatase binding	+	0.5324	53.24%
PPAR gamma	-	0.4882	48.82%
Honey bee toxicity	-	0.9242	92.42%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9956	99.56%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	17782.8 nM	Potency	via CMAUP
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	398 nM	Ki	via Super-PRED
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	17782.8 nM	Potency	via CMAUP
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	39810.7 nM	Potency	via CMAUP
CHEMBL1293237	P54132	Bloom syndrome protein	28183.8 nM	Potency	via CMAUP
CHEMBL3180	O00748	Carboxylesterase 2	118 nM	Ki	via Super-PRED
CHEMBL4096	P04637	Cellular tumor antigen p53	19952.6 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	12589.3 nM; 12589.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	19952.6 nM	Potency	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	35481.3 nM	Potency	via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	15848.9 nM; 31622.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	7943.3 nM; 10000 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	22387.2 nM	Potency	via CMAUP
CHEMBL1947	P10828	Thyroid hormone receptor beta-1	44668.4 nM	Potency	via CMAUP
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	39810.7 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.50%	95.56%
CHEMBL2581	P07339	Cathepsin D	97.49%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.10%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	94.11%	91.49%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	93.86%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.73%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	89.19%	94.73%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	88.79%	94.80%
CHEMBL1907	P15144	Aminopeptidase N	86.65%	93.31%
CHEMBL4302	P08183	P-glycoprotein 1	84.61%	92.98%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.26%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.14%	86.33%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	83.86%	96.00%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	83.30%	93.65%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.78%	97.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.85%	96.00%
CHEMBL4805	Q99572	P2X purinoceptor 7	80.58%	97.50%

Plants that contains it

• Aquilaria sinensis
• Salvia digitaloides
• Salvia glutinosa
• Salvia miltiorrhiza
• Salvia prionitis
• Salvia przewalskii
• Salvia trijuga
• Salvia yunnanensis
• Veronicastrum sibiricum

Cross-Links

• PubChem: 5316743
• NPASS: NPC289432
• ChEMBL: CHEMBL1358724
• LOTUS: LTS0109215
• wikiData: Q105025008