(16R,18R)-7-hydroxy-9-methoxy-16,18-dimethyl-13-oxa-17-azapentacyclo[12.8.0.02,11.03,8.015,20]docosa-1(14),2,4,6,8,10,15(20),21-octaen-12-one

Details

• Internal ID: bab8740d-ae2a-44fd-a402-652b129a30af
• Taxonomy: Organoheterocyclic compounds > Naphthopyrans
• IUPAC Name: (16R,18R)-7-hydroxy-9-methoxy-16,18-dimethyl-13-oxa-17-azapentacyclo[12.8.0.02,11.03,8.015,20]docosa-1(14),2,4,6,8,10,15(20),21-octaen-12-one
• SMILES (Canonical): CC1CC2=C(C(N1)C)C3=C(C=C2)C4=C5C=CC=C(C5=C(C=C4C(=O)O3)OC)O
• SMILES (Isomeric): C[C@@H]1CC2=C([C@H](N1)C)C3=C(C=C2)C4=C5C=CC=C(C5=C(C=C4C(=O)O3)OC)O
• InChI: InChI=1S/C23H21NO4/c1-11-9-13-7-8-15-20-14-5-4-6-17(25)21(14)18(27-3)10-16(20)23(26)28-22(15)19(13)12(2)24-11/h4-8,10-12,24-25H,9H2,1-3H3/t11-,12-/m1/s1
• InChI Key: JXIICUPAPXXMPH-VXGBXAGGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₁NO₄
• Molecular Weight: 375.40 g/mol
• Exact Mass: 375.14705815 g/mol
• Topological Polar Surface Area (TPSA): 67.80 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 4.41
• H-Bond Acceptor: 5
• 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	+	0.9380	93.80%
Caco-2	-	0.5150	51.50%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.4023	40.23%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9107	91.07%
OATP1B3 inhibitior	+	0.9350	93.50%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9095	90.95%
P-glycoprotein inhibitior	+	0.6338	63.38%
P-glycoprotein substrate	+	0.6725	67.25%
CYP3A4 substrate	+	0.6401	64.01%
CYP2C9 substrate	-	0.6141	61.41%
CYP2D6 substrate	-	0.6953	69.53%
CYP3A4 inhibition	-	0.9213	92.13%
CYP2C9 inhibition	-	0.8240	82.40%
CYP2C19 inhibition	-	0.8533	85.33%
CYP2D6 inhibition	-	0.7073	70.73%
CYP1A2 inhibition	-	0.6336	63.36%
CYP2C8 inhibition	+	0.5309	53.09%
CYP inhibitory promiscuity	-	0.7859	78.59%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.4698	46.98%
Eye corrosion	-	0.9924	99.24%
Eye irritation	-	0.9317	93.17%
Skin irritation	-	0.8278	82.78%
Skin corrosion	-	0.9536	95.36%
Ames mutagenesis	+	0.6163	61.63%
Human Ether-a-go-go-Related Gene inhibition	+	0.6670	66.70%
Micronuclear	+	0.6300	63.00%
Hepatotoxicity	-	0.5323	53.23%
skin sensitisation	-	0.9095	90.95%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.9193	91.93%
Acute Oral Toxicity (c)	III	0.4454	44.54%
Estrogen receptor binding	+	0.7938	79.38%
Androgen receptor binding	+	0.7384	73.84%
Thyroid receptor binding	+	0.5247	52.47%
Glucocorticoid receptor binding	+	0.8898	88.98%
Aromatase binding	+	0.6929	69.29%
PPAR gamma	+	0.8802	88.02%
Honey bee toxicity	-	0.7957	79.57%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5151	51.51%
Fish aquatic toxicity	+	0.6707	67.07%

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	99.38%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.31%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.42%	94.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	95.94%	93.99%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.23%	94.45%
CHEMBL4040	P28482	MAP kinase ERK2	93.46%	83.82%
CHEMBL2581	P07339	Cathepsin D	93.28%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.20%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.60%	86.33%
CHEMBL2535	P11166	Glucose transporter	91.26%	98.75%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.78%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.84%	97.09%
CHEMBL217	P14416	Dopamine D2 receptor	88.21%	95.62%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.05%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.64%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.46%	85.14%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	84.25%	94.03%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.19%	99.17%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.47%	92.62%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.28%	96.95%
CHEMBL213	P08588	Beta-1 adrenergic receptor	82.18%	95.56%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	81.85%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.49%	92.94%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	80.81%	96.00%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	80.38%	96.39%
CHEMBL1907	P15144	Aminopeptidase N	80.27%	93.31%

Plants that contains it

• Triphyophyllum peltatum

Cross-Links

• PubChem: 10362108
• LOTUS: LTS0052661
• wikiData: Q105136591