(3S,betaR)-10alpha-Acetyloxy-beta-bromo-3,4,4aalpha,5,6,6abeta,7,8,9,10,11,11a-dodecahydro-5alpha-hydroxy-3,11aalpha-dimethyl-7-methylene-9beta-[(1-oxohexadecyl)oxy]-2H-cyclohepta[a]naphthalene-3alpha-ethanol

Details

• Internal ID: 49c2fb77-b12d-4d53-93a4-02e304b66f4c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Tanshinones, isotanshinones, and derivatives
• IUPAC Name: [(3S,4aR,5R,6aR,9R,10R,11aR)-10-acetyloxy-3-[(1R)-1-bromo-2-hydroxyethyl]-5-hydroxy-3,11a-dimethyl-7-methylidene-2,4,4a,5,6,6a,8,9,10,11-decahydrocyclohepta[a]naphthalen-9-yl] hexadecanoate
• SMILES (Canonical): CCCCCCCCCCCCCCCC(=O)OC1CC(=C)C2CC(C3CC(CC=C3C2(CC1OC(=O)C)C)(C)C(CO)Br)O
• SMILES (Isomeric): CCCCCCCCCCCCCCCC(=O)O[C@@H]1CC(=C)[C@H]2C[C@H]([C@@H]3C[C@@](CC=C3[C@@]2(C[C@H]1OC(=O)C)C)(C)[C@H](CO)Br)O
• InChI: InChI=1S/C38H63BrO6/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-36(43)45-33-22-27(2)31-23-32(42)29-24-37(4,35(39)26-40)21-20-30(29)38(31,5)25-34(33)44-28(3)41/h20,29,31-35,40,42H,2,6-19,21-26H2,1,3-5H3/t29-,31-,32-,33-,34-,35+,37+,38+/m1/s1
• InChI Key: KFROHBBVEXISDY-VPZGYXPTSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₈H₆₃BrO₆
• Molecular Weight: 695.80 g/mol
• Exact Mass: 694.38080 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 10.10
• Atomic LogP (AlogP): 9.15
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 18

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9904	99.04%
Caco-2	-	0.8040	80.40%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7916	79.16%
OATP2B1 inhibitior	-	0.5647	56.47%
OATP1B1 inhibitior	+	0.8298	82.98%
OATP1B3 inhibitior	+	0.7918	79.18%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.5776	57.76%
BSEP inhibitior	+	0.9806	98.06%
P-glycoprotein inhibitior	+	0.6990	69.90%
P-glycoprotein substrate	+	0.6647	66.47%
CYP3A4 substrate	+	0.6910	69.10%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8529	85.29%
CYP3A4 inhibition	+	0.6214	62.14%
CYP2C9 inhibition	-	0.7351	73.51%
CYP2C19 inhibition	-	0.8609	86.09%
CYP2D6 inhibition	-	0.8764	87.64%
CYP1A2 inhibition	-	0.8576	85.76%
CYP2C8 inhibition	+	0.6128	61.28%
CYP inhibitory promiscuity	-	0.8706	87.06%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9321	93.21%
Carcinogenicity (trinary)	Non-required	0.6683	66.83%
Eye corrosion	-	0.9875	98.75%
Eye irritation	-	0.9009	90.09%
Skin irritation	+	0.5520	55.20%
Skin corrosion	-	0.9420	94.20%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4029	40.29%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	+	0.5016	50.16%
skin sensitisation	-	0.8871	88.71%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.6584	65.84%
Acute Oral Toxicity (c)	III	0.6345	63.45%
Estrogen receptor binding	+	0.7488	74.88%
Androgen receptor binding	+	0.6490	64.90%
Thyroid receptor binding	-	0.6600	66.00%
Glucocorticoid receptor binding	+	0.6039	60.39%
Aromatase binding	+	0.5940	59.40%
PPAR gamma	+	0.5422	54.22%
Honey bee toxicity	-	0.7330	73.30%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.6845	68.45%
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
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.32%	96.09%
CHEMBL2996	Q05655	Protein kinase C delta	99.09%	97.79%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.00%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.67%	94.45%
CHEMBL299	P17252	Protein kinase C alpha	98.28%	98.03%
CHEMBL2581	P07339	Cathepsin D	96.81%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	96.00%	90.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.15%	97.09%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	94.83%	94.08%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.75%	97.25%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	92.68%	85.94%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.65%	99.17%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	91.55%	97.29%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	91.03%	91.24%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	89.56%	92.86%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	88.64%	96.95%
CHEMBL340	P08684	Cytochrome P450 3A4	88.63%	91.19%
CHEMBL4227	P25090	Lipoxin A4 receptor	88.63%	100.00%
CHEMBL5255	O00206	Toll-like receptor 4	86.44%	92.50%
CHEMBL3359	P21462	Formyl peptide receptor 1	85.09%	93.56%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	84.53%	94.97%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	83.91%	94.62%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.63%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.46%	95.89%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	82.74%	97.21%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.37%	95.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.24%	86.33%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.91%	95.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.61%	94.33%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.46%	95.89%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.16%	96.90%

Plants that contains it

• Anethum graveolens
• Cymbidium aloifolium
• Delphinium dictyocarpum
• Ladeania juncea
• Ligularia atroviolacea
• Scutellaria glabra
• Trifolium pannonicum

Cross-Links

• PubChem: 21773166
• NPASS: NPC34504
• LOTUS: LTS0098683
• wikiData: Q105140531