Oleoyl neocryptotanshinone

Details

• Internal ID: ba79e796-1565-4742-a7cf-16da8d33b3bd
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Tanshinones, isotanshinones, and derivatives
• IUPAC Name: 2-(1-hydroxy-8,8-dimethyl-3,4-dioxo-6,7-dihydro-5H-phenanthren-2-yl)propyl (Z)-octadec-9-enoate
• SMILES (Canonical): CCCCCCCCC=CCCCCCCCC(=O)OCC(C)C1=C(C2=C(C3=C(C=C2)C(CCC3)(C)C)C(=O)C1=O)O
• SMILES (Isomeric): CCCCCCCC/C=C\CCCCCCCC(=O)OCC(C)C1=C(C2=C(C3=C(C=C2)C(CCC3)(C)C)C(=O)C1=O)O
• InChI: InChI=1S/C37H54O5/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22-31(38)42-26-27(2)32-34(39)29-23-24-30-28(21-20-25-37(30,3)4)33(29)36(41)35(32)40/h12-13,23-24,27,39H,5-11,14-22,25-26H2,1-4H3/b13-12-
• InChI Key: UKWHJYIGJNETGA-SEYXRHQNSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₅₄O₅
• Molecular Weight: 578.80 g/mol
• Exact Mass: 578.39712482 g/mol
• Topological Polar Surface Area (TPSA): 80.70 Ų
• XlogP: 11.10
• Atomic LogP (AlogP): 9.55
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 18

Synonyms

• CHEBI:66820
• 2-(3-hydroxy-8,8-dimethyl-1,4-dioxo-1,4,5,6,7,8-hexahydrophenanthren-2-yl)propyl (9Z)-octadec-9-enoate
• CHEMBL445779
• 16-O-oleoyl neocryptotanshinone
• 2-(1-hydroxy-8,8-dimethyl-3,4-dioxo-6,7-dihydro-5H-phenanthren-2-yl)propyl (Z)-octadec-9-enoate
• Q27135453

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9928	99.28%
Caco-2	-	0.7348	73.48%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8864	88.64%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7454	74.54%
OATP1B3 inhibitior	+	0.8899	88.99%
MATE1 inhibitior	-	0.7000	70.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.9747	97.47%
P-glycoprotein inhibitior	+	0.7344	73.44%
P-glycoprotein substrate	+	0.5341	53.41%
CYP3A4 substrate	+	0.6588	65.88%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8969	89.69%
CYP3A4 inhibition	-	0.6665	66.65%
CYP2C9 inhibition	-	0.5570	55.70%
CYP2C19 inhibition	-	0.5581	55.81%
CYP2D6 inhibition	-	0.8629	86.29%
CYP1A2 inhibition	+	0.5621	56.21%
CYP2C8 inhibition	+	0.6224	62.24%
CYP inhibitory promiscuity	-	0.6400	64.00%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6176	61.76%
Eye corrosion	-	0.9944	99.44%
Eye irritation	-	0.8839	88.39%
Skin irritation	-	0.5915	59.15%
Skin corrosion	-	0.9753	97.53%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5248	52.48%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.5323	53.23%
skin sensitisation	-	0.8264	82.64%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.8947	89.47%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.9202	92.02%
Acute Oral Toxicity (c)	III	0.7374	73.74%
Estrogen receptor binding	+	0.8026	80.26%
Androgen receptor binding	+	0.6910	69.10%
Thyroid receptor binding	-	0.6151	61.51%
Glucocorticoid receptor binding	+	0.7115	71.15%
Aromatase binding	+	0.5241	52.41%
PPAR gamma	-	0.5666	56.66%
Honey bee toxicity	-	0.8863	88.63%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6578	65.78%
Fish aquatic toxicity	+	1.0000	100.00%

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	99.69%	91.11%
CHEMBL2581	P07339	Cathepsin D	99.58%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.27%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.72%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.61%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.04%	94.45%
CHEMBL299	P17252	Protein kinase C alpha	92.51%	98.03%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	92.03%	100.00%
CHEMBL221	P23219	Cyclooxygenase-1	90.68%	90.17%
CHEMBL3359	P21462	Formyl peptide receptor 1	89.53%	93.56%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	88.78%	85.94%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	88.03%	96.38%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.05%	99.23%
CHEMBL2535	P11166	Glucose transporter	86.65%	98.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.55%	89.00%
CHEMBL230	P35354	Cyclooxygenase-2	86.50%	89.63%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	85.84%	95.17%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.58%	90.71%
CHEMBL4227	P25090	Lipoxin A4 receptor	85.48%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.80%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.75%	96.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.50%	95.89%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	83.38%	91.81%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	82.82%	91.79%
CHEMBL2996	Q05655	Protein kinase C delta	82.62%	97.79%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	81.93%	92.86%
CHEMBL5255	O00206	Toll-like receptor 4	81.89%	92.50%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.71%	93.03%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	81.67%	95.71%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	81.07%	91.71%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.43%	94.33%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	80.25%	96.47%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	80.12%	98.75%
CHEMBL340	P08684	Cytochrome P450 3A4	80.03%	91.19%

Plants that contains it

• Salvia miltiorrhiza

Cross-Links

• PubChem: 10483308
• NPASS: NPC33574