(4S)-10,11-dimethoxyspiro[5-azatricyclo[6.3.1.04,12]dodeca-1(12),8,10-triene-2,4'-cyclohexa-2,5-diene]-1'-one

Details

• Internal ID: f1a94775-59c8-4a1a-b9d3-64ff4b1a7890
• Taxonomy: Alkaloids and derivatives > Proaporphines
• IUPAC Name: (4S)-10,11-dimethoxyspiro[5-azatricyclo[6.3.1.04,12]dodeca-1(12),8,10-triene-2,4'-cyclohexa-2,5-diene]-1'-one
• SMILES (Canonical): COC1=C(C2=C3C(CC24C=CC(=O)C=C4)NCCC3=C1)OC
• SMILES (Isomeric): COC1=C(C2=C3[C@H](CC24C=CC(=O)C=C4)NCCC3=C1)OC
• InChI: InChI=1S/C18H19NO3/c1-21-14-9-11-5-8-19-13-10-18(6-3-12(20)4-7-18)16(15(11)13)17(14)22-2/h3-4,6-7,9,13,19H,5,8,10H2,1-2H3/t13-/m0/s1
• InChI Key: OGJKMZVUJJYWKO-ZDUSSCGKSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₉NO₃
• Molecular Weight: 297.30 g/mol
• Exact Mass: 297.13649347 g/mol
• Topological Polar Surface Area (TPSA): 47.60 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.23
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.6965	69.65%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7303	73.03%
OATP2B1 inhibitior	-	0.8600	86.00%
OATP1B1 inhibitior	+	0.9491	94.91%
OATP1B3 inhibitior	+	0.9616	96.16%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.6045	60.45%
P-glycoprotein inhibitior	-	0.7424	74.24%
P-glycoprotein substrate	-	0.5941	59.41%
CYP3A4 substrate	+	0.6469	64.69%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.3560	35.60%
CYP3A4 inhibition	+	0.5193	51.93%
CYP2C9 inhibition	-	0.6962	69.62%
CYP2C19 inhibition	-	0.6855	68.55%
CYP2D6 inhibition	+	0.5721	57.21%
CYP1A2 inhibition	-	0.6012	60.12%
CYP2C8 inhibition	-	0.6547	65.47%
CYP inhibitory promiscuity	+	0.5377	53.77%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6415	64.15%
Eye corrosion	-	0.9862	98.62%
Eye irritation	-	0.9749	97.49%
Skin irritation	-	0.6773	67.73%
Skin corrosion	-	0.9287	92.87%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8145	81.45%
Micronuclear	-	0.6300	63.00%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.8157	81.57%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.7370	73.70%
Acute Oral Toxicity (c)	III	0.4900	49.00%
Estrogen receptor binding	+	0.5319	53.19%
Androgen receptor binding	+	0.5992	59.92%
Thyroid receptor binding	+	0.5635	56.35%
Glucocorticoid receptor binding	-	0.5659	56.59%
Aromatase binding	+	0.5422	54.22%
PPAR gamma	-	0.6192	61.92%
Honey bee toxicity	-	0.7968	79.68%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.6515	65.15%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.44%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.75%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.48%	94.45%
CHEMBL4302	P08183	P-glycoprotein 1	93.10%	92.98%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.73%	91.11%
CHEMBL3192	Q9BY41	Histone deacetylase 8	91.30%	93.99%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.07%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.50%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.34%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.04%	94.00%
CHEMBL2535	P11166	Glucose transporter	87.11%	98.75%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.86%	97.25%
CHEMBL1937	Q92769	Histone deacetylase 2	86.22%	94.75%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.92%	95.89%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	85.87%	91.03%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.28%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.63%	92.62%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	83.55%	100.00%
CHEMBL213	P08588	Beta-1 adrenergic receptor	82.90%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.84%	92.94%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.07%	95.50%
CHEMBL1871	P10275	Androgen Receptor	80.19%	96.43%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	80.09%	94.03%

Plants that contains it

• Alstonia angustiloba
• Amphiachyris dracunculoides
• Annona cherimola
• Artabotrys hexapetalus
• Baccharis grandicapitulata
• Beesia calthifolia
• Boschniakia rossica
• Botrychium ternatum
• Bursera kerberi
• Caryomene olivascens
• Clerodendrum trichotomum
• Clinacanthus nutans
• Crotalaria stolzii
• Curcuma aeruginosa
• Delphinium giraldii
• Eucalyptus albens
• Euonymus fortunei
• Euploca racemosa
• Hedysarum gmelinii
• Helenium integrifolium
• Juniperus scopulorum
• Lasianthaea podocephala
• Legnephora moorei
• Lupinus cosentinii
• Melampodium leucanthum
• Myrica pensylvanica
• Neopallasia pectinata
• Papaver pseudocanescens
• Pellacalyx axillaris
• Peperomia filiformis
• Phlomis crinita
• Psidium acutangulum
• Pyrolirion flavum
• Renealmia alpinia
• Rhododendron mucronulatum
• Seseli libanotis
• Sideritis dasygnaphala
• Sinomenium acutum
• Stellaria media
• Stephania tetrandra
• Stephania viridiflavens
• Tephroseris kirilowii
• Tephroseris palustris
• Ziziphus jujuba

Cross-Links

• PubChem: 830726
• NPASS: NPC2770
• LOTUS: LTS0134128
• wikiData: Q105191656