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

Details

• Internal ID: 167ae7e6-269d-4d02-8578-dfbf544f2b05
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: [(2R,4R,4aS,4bS,5R,6S,7S,8aS,10R,10aR)-6,7-diacetyloxy-5-benzoyloxy-2-ethenyl-10,10a-dihydroxy-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)OC1C(C(C2CC(C3(C(C2(C1OC(=O)C4=CC=CC=C4)C)C(CC(C3=O)(C)C=C)OC(=O)C5=CC=CC=C5)O)O)(C)C)OC(=O)C
• SMILES (Isomeric): CC(=O)O[C@@H]1[C@@H]([C@]2([C@@H](C[C@H]([C@@]3([C@@H]2[C@@H](C[C@](C3=O)(C)C=C)OC(=O)C4=CC=CC=C4)O)O)C([C@@H]1OC(=O)C)(C)C)C)OC(=O)C5=CC=CC=C5
• InChI: InChI=1S/C38H44O11/c1-8-36(6)20-25(48-32(42)23-15-11-9-12-16-23)29-37(7)26(19-27(41)38(29,45)34(36)44)35(4,5)30(47-22(3)40)28(46-21(2)39)31(37)49-33(43)24-17-13-10-14-18-24/h8-18,25-31,41,45H,1,19-20H2,2-7H3/t25-,26+,27-,28+,29-,30-,31+,36+,37+,38+/m1/s1
• InChI Key: OTUCGRAKVNACNG-OFUWLHILSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₈H₄₄O₁₁
• Molecular Weight: 676.70 g/mol
• Exact Mass: 676.28836222 g/mol
• Topological Polar Surface Area (TPSA): 163.00 Ų
• XlogP: 5.30
• Atomic LogP (AlogP): 4.24
• H-Bond Acceptor: 11
• H-Bond Donor: 2
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9776	97.76%
Caco-2	-	0.8152	81.52%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.6899	68.99%
OATP2B1 inhibitior	-	0.7212	72.12%
OATP1B1 inhibitior	+	0.8717	87.17%
OATP1B3 inhibitior	+	0.8634	86.34%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9926	99.26%
P-glycoprotein inhibitior	+	0.8580	85.80%
P-glycoprotein substrate	-	0.5810	58.10%
CYP3A4 substrate	+	0.6768	67.68%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8702	87.02%
CYP3A4 inhibition	+	0.5986	59.86%
CYP2C9 inhibition	-	0.8744	87.44%
CYP2C19 inhibition	-	0.8367	83.67%
CYP2D6 inhibition	-	0.9330	93.30%
CYP1A2 inhibition	-	0.7153	71.53%
CYP2C8 inhibition	+	0.6196	61.96%
CYP inhibitory promiscuity	-	0.9605	96.05%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9443	94.43%
Carcinogenicity (trinary)	Non-required	0.5910	59.10%
Eye corrosion	-	0.9933	99.33%
Eye irritation	-	0.9020	90.20%
Skin irritation	-	0.6857	68.57%
Skin corrosion	-	0.9218	92.18%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8123	81.23%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	+	0.5125	51.25%
skin sensitisation	-	0.6931	69.31%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.6372	63.72%
Acute Oral Toxicity (c)	III	0.6083	60.83%
Estrogen receptor binding	+	0.7796	77.96%
Androgen receptor binding	+	0.6953	69.53%
Thyroid receptor binding	+	0.6449	64.49%
Glucocorticoid receptor binding	+	0.7536	75.36%
Aromatase binding	+	0.6119	61.19%
PPAR gamma	+	0.7134	71.34%
Honey bee toxicity	-	0.6657	66.57%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
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
CHEMBL1951	P21397	Monoamine oxidase A	99.05%	91.49%
CHEMBL221	P23219	Cyclooxygenase-1	98.87%	90.17%
CHEMBL2581	P07339	Cathepsin D	96.63%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.42%	86.33%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	94.40%	94.62%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.30%	91.11%
CHEMBL340	P08684	Cytochrome P450 3A4	93.22%	91.19%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.19%	95.56%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	91.53%	96.95%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	90.20%	94.08%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	88.73%	97.21%
CHEMBL240	Q12809	HERG	87.79%	89.76%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.23%	95.50%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	87.04%	82.69%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.08%	96.09%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	84.82%	83.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.69%	99.23%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.22%	91.07%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.62%	100.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.56%	93.00%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	82.33%	97.53%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.27%	95.89%

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: 10327179
• NPASS: NPC265395
• ChEMBL: CHEMBL509450
• LOTUS: LTS0002725
• wikiData: Q105199838