(4aR,4bS,10bR,12R,12aR)-12,12a-dihydroxy-8-[(1S)-1-[(1S,2R,4R,6S)-2-hydroxy-1,6-dimethyl-3,7-dioxabicyclo[4.1.0]heptan-4-yl]ethyl]-4a-methyl-4b,5,6,10b,11,12-hexahydro-1H-chrysen-4-one

Details

• Internal ID: 55a26b7f-c77e-44f7-a674-1b2649ac1c42
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Hydroxysteroids > 12-hydroxysteroids > 12-beta-hydroxysteroids
• IUPAC Name: (4aR,4bS,10bR,12R,12aR)-12,12a-dihydroxy-8-[(1S)-1-[(1S,2R,4R,6S)-2-hydroxy-1,6-dimethyl-3,7-dioxabicyclo[4.1.0]heptan-4-yl]ethyl]-4a-methyl-4b,5,6,10b,11,12-hexahydro-1H-chrysen-4-one
• SMILES (Canonical): CC(C1CC2(C(O2)(C(O1)O)C)C)C3=CC4=C(C=C3)C5CC(C6(CC=CC(=O)C6(C5CC4)C)O)O
• SMILES (Isomeric): C[C@H]([C@H]1C[C@]2([C@](O2)([C@@H](O1)O)C)C)C3=CC4=C(C=C3)[C@@H]5C[C@H]([C@]6(CC=CC(=O)[C@@]6([C@H]5CC4)C)O)O
• InChI: InChI=1S/C28H36O6/c1-15(21-14-25(2)27(4,34-25)24(31)33-21)16-7-9-18-17(12-16)8-10-20-19(18)13-23(30)28(32)11-5-6-22(29)26(20,28)3/h5-7,9,12,15,19-21,23-24,30-32H,8,10-11,13-14H2,1-4H3/t15-,19-,20-,21+,23+,24+,25-,26-,27+,28-/m0/s1
• InChI Key: KGRNYSOJSLFYHU-YVVOXUABSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₆O₆
• Molecular Weight: 468.60 g/mol
• Exact Mass: 468.25118886 g/mol
• Topological Polar Surface Area (TPSA): 99.50 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 3.12
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9185	91.85%
Caco-2	-	0.7304	73.04%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6663	66.63%
OATP2B1 inhibitior	-	0.8573	85.73%
OATP1B1 inhibitior	+	0.8792	87.92%
OATP1B3 inhibitior	+	0.8242	82.42%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8071	80.71%
BSEP inhibitior	+	0.8573	85.73%
P-glycoprotein inhibitior	+	0.6483	64.83%
P-glycoprotein substrate	+	0.6347	63.47%
CYP3A4 substrate	+	0.6876	68.76%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8714	87.14%
CYP3A4 inhibition	-	0.8103	81.03%
CYP2C9 inhibition	-	0.8921	89.21%
CYP2C19 inhibition	-	0.8264	82.64%
CYP2D6 inhibition	-	0.9429	94.29%
CYP1A2 inhibition	-	0.5963	59.63%
CYP2C8 inhibition	+	0.6487	64.87%
CYP inhibitory promiscuity	-	0.9872	98.72%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6131	61.31%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.9666	96.66%
Skin irritation	-	0.5932	59.32%
Skin corrosion	-	0.9206	92.06%
Ames mutagenesis	-	0.5470	54.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.5902	59.02%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	-	0.8251	82.51%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.7760	77.60%
Acute Oral Toxicity (c)	III	0.4070	40.70%
Estrogen receptor binding	+	0.7841	78.41%
Androgen receptor binding	+	0.7751	77.51%
Thyroid receptor binding	+	0.6508	65.08%
Glucocorticoid receptor binding	+	0.7621	76.21%
Aromatase binding	+	0.6914	69.14%
PPAR gamma	+	0.5340	53.40%
Honey bee toxicity	-	0.7486	74.86%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9867	98.67%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.32%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.42%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.77%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.72%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.85%	95.56%
CHEMBL226	P30542	Adenosine A1 receptor	93.68%	95.93%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.34%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.23%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.45%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	91.74%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.68%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.31%	95.89%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	88.85%	96.77%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	88.67%	90.71%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	88.17%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.39%	95.89%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	86.79%	90.24%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	86.32%	85.11%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.95%	97.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.28%	86.33%
CHEMBL1907598	P05106	Integrin alpha-V/beta-3	84.51%	95.71%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.69%	92.62%
CHEMBL220	P22303	Acetylcholinesterase	83.53%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.13%	99.23%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	82.85%	93.40%
CHEMBL4208	P20618	Proteasome component C5	81.84%	90.00%
CHEMBL340	P08684	Cytochrome P450 3A4	80.78%	91.19%

Plants that contains it

• Salpichroa origanifolia

Cross-Links

• PubChem: 101915921
• LOTUS: LTS0001075
• wikiData: Q105140948