[(2R,4R,4aS,4bS,5R,6S,7S,8aS,10R,10aR)-6,7,10-triacetyloxy-5-benzoyloxy-2-ethenyl-10a-hydroxy-2,4b,8,8-tetramethyl-1-oxo-4,4a,5,6,7,8a,9,10-octahydro-3H-phenanthren-4-yl] benzoate

Details

• Internal ID: b01e31b7-9623-45a0-81d3-0fa43a3a2f20
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: [(2R,4R,4aS,4bS,5R,6S,7S,8aS,10R,10aR)-6,7,10-triacetyloxy-5-benzoyloxy-2-ethenyl-10a-hydroxy-2,4b,8,8-tetramethyl-1-oxo-4,4a,5,6,7,8a,9,10-octahydro-3H-phenanthren-4-yl] benzoate
• SMILES (Canonical): CC(=O)OC1CC2C(C(C(C(C2(C3C1(C(=O)C(CC3OC(=O)C4=CC=CC=C4)(C)C=C)O)C)OC(=O)C5=CC=CC=C5)OC(=O)C)OC(=O)C)(C)C
• SMILES (Isomeric): CC(=O)O[C@@H]1C[C@@H]2[C@@]([C@@H]3[C@@]1(C(=O)[C@@](C[C@H]3OC(=O)C4=CC=CC=C4)(C)C=C)O)([C@H]([C@H]([C@H](C2(C)C)OC(=O)C)OC(=O)C)OC(=O)C5=CC=CC=C5)C
• InChI: InChI=1S/C40H46O12/c1-9-38(7)21-27(51-34(44)25-16-12-10-13-17-25)31-39(8)28(20-29(48-22(2)41)40(31,47)36(38)46)37(5,6)32(50-24(4)43)30(49-23(3)42)33(39)52-35(45)26-18-14-11-15-19-26/h9-19,27-33,47H,1,20-21H2,2-8H3/t27-,28+,29-,30+,31-,32-,33+,38+,39+,40+/m1/s1
• InChI Key: MKJGZDLMXUGLBP-HZYAOAIPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₄₆O₁₂
• Molecular Weight: 718.80 g/mol
• Exact Mass: 718.29892690 g/mol
• Topological Polar Surface Area (TPSA): 169.00 Ų
• XlogP: 5.90
• Atomic LogP (AlogP): 4.81
• H-Bond Acceptor: 12
• H-Bond Donor: 1
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9870	98.70%
Caco-2	-	0.8142	81.42%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7216	72.16%
OATP2B1 inhibitior	-	0.8596	85.96%
OATP1B1 inhibitior	+	0.8708	87.08%
OATP1B3 inhibitior	+	0.8419	84.19%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9919	99.19%
P-glycoprotein inhibitior	+	0.8797	87.97%
P-glycoprotein substrate	-	0.5897	58.97%
CYP3A4 substrate	+	0.6802	68.02%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8798	87.98%
CYP3A4 inhibition	+	0.6594	65.94%
CYP2C9 inhibition	-	0.7904	79.04%
CYP2C19 inhibition	-	0.7975	79.75%
CYP2D6 inhibition	-	0.9370	93.70%
CYP1A2 inhibition	-	0.6569	65.69%
CYP2C8 inhibition	+	0.6547	65.47%
CYP inhibitory promiscuity	-	0.9225	92.25%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9743	97.43%
Carcinogenicity (trinary)	Non-required	0.5616	56.16%
Eye corrosion	-	0.9928	99.28%
Eye irritation	-	0.8939	89.39%
Skin irritation	-	0.6934	69.34%
Skin corrosion	-	0.9376	93.76%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6850	68.50%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.6596	65.96%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.4715	47.15%
Acute Oral Toxicity (c)	III	0.6264	62.64%
Estrogen receptor binding	+	0.7798	77.98%
Androgen receptor binding	+	0.6851	68.51%
Thyroid receptor binding	+	0.6515	65.15%
Glucocorticoid receptor binding	+	0.7628	76.28%
Aromatase binding	+	0.6296	62.96%
PPAR gamma	+	0.7451	74.51%
Honey bee toxicity	-	0.6725	67.25%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
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
CHEMBL221	P23219	Cyclooxygenase-1	97.93%	90.17%
CHEMBL1951	P21397	Monoamine oxidase A	97.62%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.95%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.50%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.82%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.68%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	92.68%	91.19%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.79%	96.09%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	90.78%	94.62%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	88.96%	94.08%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	88.39%	95.50%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	85.46%	82.69%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	85.35%	83.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.05%	96.95%
CHEMBL240	Q12809	HERG	83.77%	89.76%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.63%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.38%	100.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.09%	91.07%
CHEMBL5028	O14672	ADAM10	81.58%	97.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.97%	95.89%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.95%	85.14%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	80.86%	97.53%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.47%	93.00%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	80.04%	96.39%

Plants that contains it

• Angelica ursina
• Ardisia macrocarpa
• Asplenium nidus
• Astragalus laxmannii subsp. laxmannii
• Celmisia petriei
• Cenchrus americanus
• Chlorophytum malayense
• Cirsium helenioides
• Clausena indica
• Clusia torresii
• Empetrum nigrum
• Ephedra lomatolepis
• Euonymus maackii
• Ferula assa-foetida
• Gentiana olivieri
• Handroanthus guayacan
• Jateorhiza palmata
• Lindera umbellata
• Morus notabilis
• Nicotiana gossei
• Orthosiphon aristatus
• Orthosiphon aristatus var. aristatus
• Oryza sativa
• Picradeniopsis oppositifolia
• Pinus halepensis
• Pinus thunbergii
• Populus tremula
• Primula veris
• Pterocaulon rugosum
• Rauvolfia tetraphylla
• Salvia prionitis
• Satureja montana
• Saussurea triangulata
• Senecio grandiflorus
• Senecio integerrimus
• Stephania succifera
• Stevia salicifolia
• Tetraria capillaris
• Teucrium alyssifolium
• Ulmus laciniata
• Vernonanthura serratuloides
• Zephyranthes carinata

Cross-Links

• PubChem: 9987409
• NPASS: NPC154819
• LOTUS: LTS0073936
• wikiData: Q105166021