(4aS,4bR,5S,7S,8aS,10R,10aS)-7-ethenyl-5,10-dihydroxy-4b,7,10a-trimethyl-1-methylidene-5,6,8,8a,9,10-hexahydro-4aH-phenanthren-4-one

Details

• Internal ID: c50f432b-95f3-410d-bb16-efd777e60145
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (4aS,4bR,5S,7S,8aS,10R,10aS)-7-ethenyl-5,10-dihydroxy-4b,7,10a-trimethyl-1-methylidene-5,6,8,8a,9,10-hexahydro-4aH-phenanthren-4-one
• SMILES (Canonical): CC1(CC2CC(C3(C(C2(C(C1)O)C)C(=O)C=CC3=C)C)O)C=C
• SMILES (Isomeric): C[C@@]1(C[C@H]2C[C@H]([C@]3([C@H]([C@@]2([C@H](C1)O)C)C(=O)C=CC3=C)C)O)C=C
• InChI: InChI=1S/C20H28O3/c1-6-18(3)10-13-9-15(22)19(4)12(2)7-8-14(21)17(19)20(13,5)16(23)11-18/h6-8,13,15-17,22-23H,1-2,9-11H2,3-5H3/t13-,15-,16+,17-,18+,19+,20+/m1/s1
• InChI Key: HHAUGWNUDTZZRE-YMDNOQLFSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₃
• Molecular Weight: 316.40 g/mol
• Exact Mass: 316.20384475 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 3.04
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9972	99.72%
Caco-2	+	0.6724	67.24%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.5620	56.20%
OATP2B1 inhibitior	-	0.8591	85.91%
OATP1B1 inhibitior	+	0.8951	89.51%
OATP1B3 inhibitior	+	0.9403	94.03%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.9104	91.04%
P-glycoprotein inhibitior	-	0.8767	87.67%
P-glycoprotein substrate	-	0.7713	77.13%
CYP3A4 substrate	+	0.5998	59.98%
CYP2C9 substrate	-	0.8117	81.17%
CYP2D6 substrate	-	0.8662	86.62%
CYP3A4 inhibition	-	0.6022	60.22%
CYP2C9 inhibition	-	0.8791	87.91%
CYP2C19 inhibition	-	0.7966	79.66%
CYP2D6 inhibition	-	0.9297	92.97%
CYP1A2 inhibition	-	0.8563	85.63%
CYP2C8 inhibition	-	0.8326	83.26%
CYP inhibitory promiscuity	-	0.7884	78.84%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8813	88.13%
Carcinogenicity (trinary)	Non-required	0.5402	54.02%
Eye corrosion	-	0.9927	99.27%
Eye irritation	-	0.7698	76.98%
Skin irritation	+	0.5675	56.75%
Skin corrosion	-	0.9410	94.10%
Ames mutagenesis	-	0.7164	71.64%
Human Ether-a-go-go-Related Gene inhibition	+	0.7338	73.38%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	+	0.5676	56.76%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	+	0.6199	61.99%
Acute Oral Toxicity (c)	III	0.7273	72.73%
Estrogen receptor binding	+	0.5280	52.80%
Androgen receptor binding	+	0.5478	54.78%
Thyroid receptor binding	+	0.6866	68.66%
Glucocorticoid receptor binding	+	0.5483	54.83%
Aromatase binding	+	0.6008	60.08%
PPAR gamma	-	0.7061	70.61%
Honey bee toxicity	-	0.8021	80.21%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9899	98.99%

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	95.37%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.12%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.82%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.37%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.65%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.43%	97.09%
CHEMBL2581	P07339	Cathepsin D	83.85%	98.95%
CHEMBL2039	P27338	Monoamine oxidase B	83.19%	92.51%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.43%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.98%	89.00%

Plants that contains it

• Simira eliezeriana

Cross-Links

• PubChem: 162867561
• LOTUS: LTS0054185
• wikiData: Q105028134