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

Details

• Internal ID: 258b48d2-b005-4e58-9d83-0355d0c1c90d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: [(2R,4R,4aS,4bS,5R,6S,7S,8aS,9S,10R,10aR)-6,10-diacetyloxy-5-benzoyloxy-2-ethenyl-7,9,10a-trihydroxy-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(C2C(C(C3(C(C2(C1OC(=O)C4=CC=CC=C4)C)C(CC(C3=O)(C)C=C)OC(=O)C5=CC=CC=C5)O)OC(=O)C)O)(C)C)O
• SMILES (Isomeric): CC(=O)O[C@@H]1[C@@H]([C@@]2([C@H]3[C@@H](C[C@](C(=O)[C@@]3([C@@H]([C@H]([C@H]2C([C@@H]1O)(C)C)O)OC(=O)C)O)(C)C=C)OC(=O)C4=CC=CC=C4)C)OC(=O)C5=CC=CC=C5
• InChI: InChI=1S/C38H44O12/c1-8-36(6)19-24(49-32(43)22-15-11-9-12-16-22)27-37(7)28(25(41)30(48-21(3)40)38(27,46)34(36)45)35(4,5)29(42)26(47-20(2)39)31(37)50-33(44)23-17-13-10-14-18-23/h8-18,24-31,41-42,46H,1,19H2,2-7H3/t24-,25+,26+,27-,28+,29-,30-,31+,36+,37-,38-/m1/s1
• InChI Key: TZYOKXQYQQXUCI-BUUZRMBISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₈H₄₄O₁₂
• Molecular Weight: 692.70 g/mol
• Exact Mass: 692.28327683 g/mol
• Topological Polar Surface Area (TPSA): 183.00 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 3.21
• H-Bond Acceptor: 12
• H-Bond Donor: 3
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9251	92.51%
Caco-2	-	0.8350	83.50%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.6579	65.79%
OATP2B1 inhibitior	-	0.7142	71.42%
OATP1B1 inhibitior	+	0.8816	88.16%
OATP1B3 inhibitior	+	0.8884	88.84%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9809	98.09%
P-glycoprotein inhibitior	+	0.8348	83.48%
P-glycoprotein substrate	-	0.6396	63.96%
CYP3A4 substrate	+	0.6492	64.92%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8699	86.99%
CYP3A4 inhibition	+	0.6575	65.75%
CYP2C9 inhibition	-	0.7494	74.94%
CYP2C19 inhibition	-	0.8416	84.16%
CYP2D6 inhibition	-	0.9076	90.76%
CYP1A2 inhibition	-	0.7829	78.29%
CYP2C8 inhibition	+	0.5338	53.38%
CYP inhibitory promiscuity	-	0.8204	82.04%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9686	96.86%
Carcinogenicity (trinary)	Non-required	0.5384	53.84%
Eye corrosion	-	0.9931	99.31%
Eye irritation	-	0.8938	89.38%
Skin irritation	-	0.7556	75.56%
Skin corrosion	-	0.9404	94.04%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6412	64.12%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.6481	64.81%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.6306	63.06%
Acute Oral Toxicity (c)	III	0.6265	62.65%
Estrogen receptor binding	+	0.7338	73.38%
Androgen receptor binding	+	0.6760	67.60%
Thyroid receptor binding	+	0.6361	63.61%
Glucocorticoid receptor binding	+	0.6930	69.30%
Aromatase binding	+	0.5546	55.46%
PPAR gamma	+	0.7090	70.90%
Honey bee toxicity	-	0.7194	71.94%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
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	98.16%	91.49%
CHEMBL2581	P07339	Cathepsin D	97.47%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	97.34%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.04%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.66%	86.33%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	92.99%	94.62%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.90%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.87%	95.56%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	90.51%	94.08%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.31%	99.23%
CHEMBL340	P08684	Cytochrome P450 3A4	88.01%	91.19%
CHEMBL4208	P20618	Proteasome component C5	85.13%	90.00%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	85.10%	83.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.63%	95.89%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	84.58%	93.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.72%	95.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.18%	100.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.95%	91.07%
CHEMBL2535	P11166	Glucose transporter	80.18%	98.75%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.13%	82.69%

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: 10101175
• NPASS: NPC37454
• LOTUS: LTS0198249
• wikiData: Q105268489