12a-Hydroxydalpanol

Details

• Internal ID: 4baad4bc-1142-461e-b38e-5fdd65fe1c35
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Rotenoids > Rotenones
• IUPAC Name: (1R,6R,13R)-13-hydroxy-6-(2-hydroxypropan-2-yl)-16,17-dimethoxy-2,7,20-trioxapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one
• SMILES (Canonical): CC(C)(C1CC2=C(O1)C=CC3=C2OC4COC5=CC(=C(C=C5C4(C3=O)O)OC)OC)O
• SMILES (Isomeric): CC(C)([C@H]1CC2=C(O1)C=CC3=C2O[C@@H]4COC5=CC(=C(C=C5[C@@]4(C3=O)O)OC)OC)O
• InChI: InChI=1S/C23H24O8/c1-22(2,25)18-7-12-14(30-18)6-5-11-20(12)31-19-10-29-15-9-17(28-4)16(27-3)8-13(15)23(19,26)21(11)24/h5-6,8-9,18-19,25-26H,7,10H2,1-4H3/t18-,19-,23-/m1/s1
• InChI Key: NSFCLBVWJYYZMR-DNVFCKCGSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₄O₈
• Molecular Weight: 428.40 g/mol
• Exact Mass: 428.14711772 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.00
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• 85042-77-9
• DH-2,6-OH-rotenone
• 1',2'-Dihydro-2',6-dihydroxyrotenone
• (1R,6R,13R)-13-hydroxy-6-(2-hydroxypropan-2-yl)-16,17-dimethoxy-2,7,20-trioxapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one
• NSC646924
• 12Abeta-Hydroxydalpanol
• CHEMBL515078
• DTXSID801005413
• AKOS040734243
• NSC-646924
• NCI60_016219
• NCGC00385138-01!
• (1)Benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(6aH)-one, 1,2,12,12a-tetrahydro-6a-hydroxy-2-(1-hydroxy-1-methylethyl)-8,9-dimethoxy-, (2R-(2alpha,6aalpha,12aalpha))-
• 6a-Hydroxy-2-(2-hydroxypropan-2-yl)-8,9-dimethoxy-1,2,12,12a-tetrahydrofuro[2',3':7,8][1]benzopyrano[2,3-c][1]benzopyran-6(6aH)-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9864	98.64%
Caco-2	+	0.5485	54.85%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8257	82.57%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8910	89.10%
OATP1B3 inhibitior	+	0.9386	93.86%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8248	82.48%
P-glycoprotein inhibitior	+	0.7409	74.09%
P-glycoprotein substrate	+	0.5207	52.07%
CYP3A4 substrate	+	0.6518	65.18%
CYP2C9 substrate	-	0.8027	80.27%
CYP2D6 substrate	-	0.6873	68.73%
CYP3A4 inhibition	-	0.7794	77.94%
CYP2C9 inhibition	-	0.7548	75.48%
CYP2C19 inhibition	-	0.5076	50.76%
CYP2D6 inhibition	-	0.7636	76.36%
CYP1A2 inhibition	+	0.6575	65.75%
CYP2C8 inhibition	+	0.5089	50.89%
CYP inhibitory promiscuity	-	0.7071	70.71%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5731	57.31%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.7979	79.79%
Skin irritation	-	0.8158	81.58%
Skin corrosion	-	0.9531	95.31%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8614	86.14%
Micronuclear	+	0.5659	56.59%
Hepatotoxicity	+	0.5074	50.74%
skin sensitisation	-	0.8108	81.08%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.5676	56.76%
Acute Oral Toxicity (c)	III	0.7496	74.96%
Estrogen receptor binding	+	0.8625	86.25%
Androgen receptor binding	+	0.6050	60.50%
Thyroid receptor binding	+	0.7559	75.59%
Glucocorticoid receptor binding	+	0.7741	77.41%
Aromatase binding	+	0.6740	67.40%
PPAR gamma	+	0.8476	84.76%
Honey bee toxicity	-	0.7355	73.55%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6751	67.51%
Fish aquatic toxicity	+	0.9037	90.37%

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	97.59%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.14%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.30%	86.33%
CHEMBL2581	P07339	Cathepsin D	93.87%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.81%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.66%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	89.44%	97.14%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	88.61%	96.86%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.56%	97.25%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.05%	94.00%
CHEMBL4040	P28482	MAP kinase ERK2	87.76%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.84%	96.09%
CHEMBL2535	P11166	Glucose transporter	86.76%	98.75%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.05%	92.62%
CHEMBL2413	P32246	C-C chemokine receptor type 1	85.84%	89.50%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.83%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.48%	89.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.47%	96.77%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	84.19%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.95%	97.09%
CHEMBL4208	P20618	Proteasome component C5	82.92%	90.00%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	82.68%	82.67%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.21%	100.00%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	81.93%	97.33%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	80.40%	95.78%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.27%	92.94%

Plants that contains it

• Amorpha fruticosa

Cross-Links

• PubChem: 134875
• NPASS: NPC242395
• LOTUS: LTS0042530
• wikiData: Q83000806