[(4aR,4bR,7R,8aR,9R,10aR)-3-acetyloxy-7-ethenyl-8a-hydroxy-1,1,4a,7-tetramethyl-2,5,8-trioxo-6,9,10,10a-tetrahydro-4bH-phenanthren-9-yl] acetate

Details

• Internal ID: e2c3fbfe-0a16-41c1-bea0-265ebab2940b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: [(4aR,4bR,7R,8aR,9R,10aR)-3-acetyloxy-7-ethenyl-8a-hydroxy-1,1,4a,7-tetramethyl-2,5,8-trioxo-6,9,10,10a-tetrahydro-4bH-phenanthren-9-yl] acetate
• SMILES (Canonical): CC(=O)OC1CC2C(C(=O)C(=CC2(C3C1(C(=O)C(CC3=O)(C)C=C)O)C)OC(=O)C)(C)C
• SMILES (Isomeric): CC(=O)O[C@@H]1C[C@@H]2[C@](C=C(C(=O)C2(C)C)OC(=O)C)([C@@H]3[C@@]1(C(=O)[C@@](CC3=O)(C)C=C)O)C
• InChI: InChI=1S/C24H30O8/c1-8-22(6)10-14(27)18-23(7)11-15(31-12(2)25)19(28)21(4,5)16(23)9-17(32-13(3)26)24(18,30)20(22)29/h8,11,16-18,30H,1,9-10H2,2-7H3/t16-,17+,18+,22-,23-,24-/m0/s1
• InChI Key: YBPSGTZBJNUQAI-HSGHKLBJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₀O₈
• Molecular Weight: 446.50 g/mol
• Exact Mass: 446.19406791 g/mol
• Topological Polar Surface Area (TPSA): 124.00 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 2.08
• H-Bond Acceptor: 8
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9884	98.84%
Caco-2	-	0.6445	64.45%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7644	76.44%
OATP2B1 inhibitior	-	0.8591	85.91%
OATP1B1 inhibitior	+	0.8678	86.78%
OATP1B3 inhibitior	+	0.8427	84.27%
MATE1 inhibitior	-	0.6600	66.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.7070	70.70%
P-glycoprotein inhibitior	+	0.6070	60.70%
P-glycoprotein substrate	-	0.7250	72.50%
CYP3A4 substrate	+	0.6459	64.59%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9020	90.20%
CYP3A4 inhibition	-	0.5061	50.61%
CYP2C9 inhibition	-	0.8640	86.40%
CYP2C19 inhibition	-	0.8369	83.69%
CYP2D6 inhibition	-	0.9426	94.26%
CYP1A2 inhibition	-	0.7740	77.40%
CYP2C8 inhibition	-	0.6209	62.09%
CYP inhibitory promiscuity	-	0.9234	92.34%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9643	96.43%
Carcinogenicity (trinary)	Non-required	0.5666	56.66%
Eye corrosion	-	0.9875	98.75%
Eye irritation	-	0.9110	91.10%
Skin irritation	-	0.5766	57.66%
Skin corrosion	-	0.9338	93.38%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5442	54.42%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	-	0.5625	56.25%
skin sensitisation	-	0.5635	56.35%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	+	0.7317	73.17%
Acute Oral Toxicity (c)	III	0.5812	58.12%
Estrogen receptor binding	+	0.7237	72.37%
Androgen receptor binding	+	0.6814	68.14%
Thyroid receptor binding	+	0.6126	61.26%
Glucocorticoid receptor binding	+	0.6393	63.93%
Aromatase binding	+	0.5811	58.11%
PPAR gamma	+	0.6302	63.02%
Honey bee toxicity	-	0.5745	57.45%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9961	99.61%

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	97.08%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.01%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.42%	96.09%
CHEMBL340	P08684	Cytochrome P450 3A4	92.44%	91.19%
CHEMBL2581	P07339	Cathepsin D	88.56%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.61%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.22%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.40%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.40%	97.09%
CHEMBL1951	P21397	Monoamine oxidase A	81.63%	91.49%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.45%	100.00%
CHEMBL1902	P62942	FK506-binding protein 1A	80.06%	97.05%

Plants that contains it

• Angelica ursina
• Ardisia macrocarpa
• Cenchrus americanus
• Chlorophytum malayense
• Clausena indica
• Empetrum nigrum
• Ephedra lomatolepis
• Euonymus maackii
• Gentiana olivieri
• Jateorhiza palmata
• Lindera umbellata
• Morus notabilis
• Nicotiana gossei
• Orthosiphon aristatus var. aristatus
• Picradeniopsis oppositifolia
• Pinus halepensis
• Pinus thunbergii
• Pterocaulon rugosum
• Rauvolfia tetraphylla
• Salvia prionitis
• Satureja montana
• Saussurea triangulata
• Senecio grandiflorus
• Stephania succifera
• Stevia salicifolia
• Tetraria capillaris
• Teucrium alyssifolium
• Vernonanthura serratuloides
• Zephyranthes carinata

Cross-Links

• PubChem: 10072248
• NPASS: NPC55887
• LOTUS: LTS0046111
• wikiData: Q104919821