Homolycorine

Details

• Internal ID: 94077cd7-d6d7-4c10-ae3d-ca0add872d15
• Taxonomy: Alkaloids and derivatives > Amaryllidaceae alkaloids > Homolycorine-type amaryllidaceae alkaloids
• IUPAC Name: (5aR,11bS,11cS)-9,10-dimethoxy-1-methyl-2,3,5,5a,11b,11c-hexahydroisochromeno[3,4-g]indol-7-one
• SMILES (Canonical): CN1CCC2=CCC3C(C21)C4=CC(=C(C=C4C(=O)O3)OC)OC
• SMILES (Isomeric): CN1CCC2=CC[C@@H]3[C@H]([C@@H]21)C4=CC(=C(C=C4C(=O)O3)OC)OC
• InChI: InChI=1S/C18H21NO4/c1-19-7-6-10-4-5-13-16(17(10)19)11-8-14(21-2)15(22-3)9-12(11)18(20)23-13/h4,8-9,13,16-17H,5-7H2,1-3H3/t13-,16-,17-/m1/s1
• InChI Key: WXZAKVLYZHWSNF-KBRIMQKVSA-N
• Popularity: 12 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₁NO₄
• Molecular Weight: 315.40 g/mol
• Exact Mass: 315.14705815 g/mol
• Topological Polar Surface Area (TPSA): 48.00 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 2.36
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• 477-20-3
• 9,10-Dimethoxy-1-methyllycorenan-7-one
• T95J9AUU63
• (5aR,11bS,11cS)-9,10-dimethoxy-1-methyl-2,3,5,5a,11b,11c-hexahydroisochromeno[3,4-g]indol-7-one
• Lycorenan-7-one, 9,10-dimethoxy-1-methyl-
• (+)-homolycorine
• NARCIPOETINE
• UNII-T95J9AUU63
• SCHEMBL4373999
• CHEMBL1221973
• DTXSID80963902
• Q18349931
• (1S,10R,17S)-4,5-dimethoxy-16-methyl-9-oxa-16-azatetracyclo[8.7.0.0{2,7}.0{13,17}]heptadeca-2,4,6,12-tetraen-8-one
• (2)BENZOPYRANO(3,4-G)INDOL-7(1H)-ONE, 2,3,5,5A,11B,11C-HEXAHYDRO-9,10-DIMETHOXY-1-METHYL-, (5AR-(5A.ALPHA.,11B.ALPHA.,11C.BETA.))-
• (5AR,11BS,11CS)-2,3,5,5A,11B,11C-HEXAHYDRO-9,10-DIMETHOXY-1-METHYL(2)BENZOPYRANO(3,4-G)INDOL-7(1H)-ONE
• [2]Benzopyrano[3,4-g]indol-7(1H)-one, 2,3,5,5a,11b,11c-hexahydro-9,10-dimethoxy-1-methyl-, (5aR,11bS,11cS)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9750	97.50%
Caco-2	+	0.9298	92.98%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6301	63.01%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9241	92.41%
OATP1B3 inhibitior	+	0.9320	93.20%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	+	0.6821	68.21%
P-glycoprotein inhibitior	-	0.6415	64.15%
P-glycoprotein substrate	-	0.5632	56.32%
CYP3A4 substrate	+	0.6287	62.87%
CYP2C9 substrate	-	0.6153	61.53%
CYP2D6 substrate	+	0.4509	45.09%
CYP3A4 inhibition	-	0.8335	83.35%
CYP2C9 inhibition	-	0.9338	93.38%
CYP2C19 inhibition	-	0.8240	82.40%
CYP2D6 inhibition	+	0.6788	67.88%
CYP1A2 inhibition	-	0.7599	75.99%
CYP2C8 inhibition	-	0.8451	84.51%
CYP inhibitory promiscuity	-	0.8311	83.11%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5183	51.83%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.9629	96.29%
Skin irritation	-	0.7823	78.23%
Skin corrosion	-	0.9394	93.94%
Ames mutagenesis	-	0.5137	51.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.7429	74.29%
Micronuclear	-	0.5500	55.00%
Hepatotoxicity	+	0.6375	63.75%
skin sensitisation	-	0.8498	84.98%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	+	0.6944	69.44%
Acute Oral Toxicity (c)	III	0.6434	64.34%
Estrogen receptor binding	-	0.5697	56.97%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	-	0.5407	54.07%
Glucocorticoid receptor binding	+	0.7814	78.14%
Aromatase binding	-	0.6637	66.37%
PPAR gamma	+	0.6139	61.39%
Honey bee toxicity	-	0.7174	71.74%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9721	97.21%

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	97.20%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.34%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.65%	85.14%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	94.35%	93.40%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.40%	86.33%
CHEMBL2535	P11166	Glucose transporter	89.62%	98.75%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.10%	95.89%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	87.70%	96.86%
CHEMBL2581	P07339	Cathepsin D	87.45%	98.95%
CHEMBL4208	P20618	Proteasome component C5	86.65%	90.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.50%	94.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.76%	97.25%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.16%	96.77%
CHEMBL2413	P32246	C-C chemokine receptor type 1	84.44%	89.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.09%	97.14%
CHEMBL2056	P21728	Dopamine D1 receptor	84.08%	91.00%
CHEMBL3820	P35557	Hexokinase type IV	83.48%	91.96%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	82.73%	91.11%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	80.52%	95.53%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.47%	99.23%

Plants that contains it

• Amaryllidaceae
• Crinum viviparum
• Ferula persica
• Hippeastrum vittatum
• Hymenocallis littoralis
• Hymenocallis rotata
• Leucojum vernum
• Ligularia przewalskii
• Lycoris aurea
• Lycoris radiata
• Narcissus × tortifolius
• Narcissus confusus
• Narcissus munozii-garmendiae
• Narcissus pallidiflorus
• Narcissus papyraceus
• Narcissus papyraceus subsp. panizzianus
• Narcissus poeticus
• Narcissus primigenius
• Narcissus pseudonarcissus
• Narcissus pseudonarcissus subsp. minor
• Narcissus tazetta
• Stachys aegyptiaca

Cross-Links

• PubChem: 160473
• NPASS: NPC35680
• ChEMBL: CHEMBL1221973
• LOTUS: LTS0185840
• wikiData: Q18349931