Dihydrotanshinone I

Details

• Internal ID: f27082a1-6671-437e-afcf-76ac6b64da55
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Tanshinones, isotanshinones, and derivatives
• IUPAC Name: (1R)-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): C[C@H]1COC2=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/t10-/m0/s1
• InChI Key: HARGZZNYNSYSGJ-JTQLQIEISA-N
• Popularity: 104 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

• 87205-99-0
• 15,16-dihydrotanshinone I
• DihydrotanshinoneI
• (-)-Dihydrotanshinone I
• Dihydrotanshinone-I
• Tanshinone I, dihydro-
• HSDB 8105
• UNII-562G9360V6
• 562G9360V6
• DTXSID20236187
• (1R)-1,6-dimethyl-1,2-dihydronaphtho[1,2-g][1]benzofuran-10,11-dione
• DIHYDROTANSHINONE I, (-)-
• DIHYDROTANSHINONE
• PHENANTHRO(1,2-B)FURAN-10,11-DIONE, 1,2-DIHYDRO-1,6-DIMETHYL-, (1R)-
• SR-05000002191
• 15,16-dihydrotanshinone-I
• DHTS
• 'Dihydrotanshinone I'
• 4m0e
• CHEMBL227075
• SCHEMBL13049977
• DTXCID20158678
• CHEBI:149872
• HARGZZNYNSYSGJ-JTQLQIEISA-N
• HY-N0360
• (1R)-1,6-Dimethyl-1,2-dihydrophenanthro(1,2-b)furan-10,11-dione
• BDBM50423877
• MFCD28016070
• s9020
• AKOS032962078
• CCG-208567
• Dihydrotanshinone I, >=98% (HPLC)
• NCGC00163651-01
• NCGC00163651-06
• D5379
• A862726
• SR-05000002191-2
• SR-05000002191-3
• Q21099654
• DIHYDROTANSHINONE (CONSTITUENT OF CHINESE SALVIA)
• DIHYDROTANSHINONE (CONSTITUENT OF CHINESE SALVIA) [DSC]
• (R)-1,6-dimethyl-1,2-dihydrophenanthro[1,2-b]furan-10,11-dione
• '(1R)-1,6-dimethyl-1,2-dihydrophenanthro[1,2-b]furan-10,11-dione'
• (-)-1,2-Dihydro-1,6-dimethylphenanthro[1,2-b]furan-10,11-dione;1,6-Dimethyl-1,2,10,11-tetrahydrophenanthro[1,2-b]furan-10,11-dione;4,17-Dimethyl-15-oxagona-1,3,5(10),6,8,13-hexene-11,12-dione;15,16-Dihydrotanshine I;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
CHEMBL220	P22303	Acetylcholinesterase	1000 nM	IC50	PMID: 24900610
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	398 nM; 398 nM	Ki; Ki	via Super-PRED; PMID: 23286284
CHEMBL3180	O00748	Carboxylesterase 2	118 nM; 118 nM; 1830 nM	Ki; Ki; Ki	via Super-PRED; PMID: 23286284; PMID: 23286284
CHEMBL1250379	Q15717	ELAV-like protein 1	50 nM	Ki	via Super-PRED
CHEMBL3166	P29350	Protein-tyrosine phosphatase 1C	3670 nM	IC50	PMID: 23957426
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	3940 nM	IC50	PMID: 23957426
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	10000 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

• Agathosma thymifolia
• Amentotaxus yunnanensis
• Artemisia siversiana
• Asphodeline tenuior
• Bothriocline longipes
• Deguelia hatschbachii
• Delphinium cyphoplectrum
• Dioscorea communis
• Euphorbia ampliphylla
• Euphorbia retusa
• Glycine falcata
• Glycyrrhiza triphylla
• Hemionitis artax
• Iris hoogiana
• Metzgeria pubescens
• Picradeniopsis pringlei
• Salvia aerea
• Salvia castanea
• Salvia digitaloides
• Salvia glutinosa
• Salvia miltiorrhiza
• Salvia nipponica
• Salvia prionitis
• Salvia przewalskii
• Salvia trijuga
• Salvia yunnanensis
• Senecio madagascariensis
• Stauntonia obovatifoliola
• Uvaria klaineana
• Veronicastrum sibiricum
• Vicia sativa

Cross-Links

• PubChem: 11425923
• NPASS: NPC988
• ChEMBL: CHEMBL227075
• LOTUS: LTS0074988
• wikiData: Q21099654