l-Stepholidine

Details

• Internal ID: 857c4d83-d74d-40ec-8c72-6fafa7ad1c20
• Taxonomy: Alkaloids and derivatives > Protoberberine alkaloids and derivatives
• IUPAC Name: (13aS)-3,9-dimethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline-2,10-diol
• SMILES (Canonical): COC1=C(C=C2C3CC4=C(CN3CCC2=C1)C(=C(C=C4)O)OC)O
• SMILES (Isomeric): COC1=C(C=C2[C@@H]3CC4=C(CN3CCC2=C1)C(=C(C=C4)O)OC)O
• InChI: InChI=1S/C19H21NO4/c1-23-18-8-12-5-6-20-10-14-11(3-4-16(21)19(14)24-2)7-15(20)13(12)9-17(18)22/h3-4,8-9,15,21-22H,5-7,10H2,1-2H3/t15-/m0/s1
• InChI Key: JKPISQIIWUONPB-HNNXBMFYSA-N
• Popularity: 115 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₁NO₄
• Molecular Weight: 327.40 g/mol
• Exact Mass: 327.14705815 g/mol
• Topological Polar Surface Area (TPSA): 62.20 Ų
• XlogP: 2.60

Synonyms

• 16562-13-3
• stepholidine
• (-)-Stepholidine
• (S)-3,9-Dimethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[3,2-a]isoquinoline-2,10-diol
• 6H-Dibenzo[a,g]quinolizine-2,10-diol, 5,8,13,13a-tetrahydro-3,9-dimethoxy-, (13aS)-
• 0UPX3E69W8
• (13aS)-3,9-dimethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline-2,10-diol
• 3,9-Dimethoxy-13a-alpha-berbine-2,10-diol
• l-2,10-Dihydroxy-3,9-dimethyloxytetrahydropseudoberberine
• S-Stepholidine
• (S)-3,9-dimethoxy-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinoline-2,10-diol
• 6H-dibenzo(A,G)quinolizine-2,10-diol, 5,8,13,13A-tetrahydro-3,9-dimethoxy-, (13AS)-
• 6H-Dibenzo(a,g)quinolizine-2,10-diol, 5,8,13,13a-tetrahydro-3,9-dimethoxy-, (S)-
• L-(S)-Stepholidine
• l-SPD
• 13a-alpha-BERBINE-2,10-DIOL, 3,9-DIMETHOXY-
• D0L7OM
• UNII-0UPX3E69W8
• STEPHOLIDINE [WHO-DD]
• STEPHOLIDINE, (-)-
• CHEMBL487387
• GTPL8370
• SCHEMBL10001966
• HY-N6960
• BDBM50378584
• MFCD00211195
• AKOS016843116
• CS-1253
• HY-17415
• Q-100198
• Q27088886
• 13A.ALPHA.-BERBINE-2,10-DIOL, 3,9-DIMETHOXY-
• (12bS)-4,10-dimethoxy-7,8,12b,13-tetrahydro-5H-6-azatetraphene-3,11-diol
• (13AS)-5,8,13,13A-TETRAHYDRO-3,9-DIMETHOXY-6H-DIBENZO(A,G)QUINOLIZINE-2,10-DIOL

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4081	P13726	Coagulation factor III	104.58 nM; 104.58 nM	IC50; IC50	via Super-PRED; PMID: 23199480
CHEMBL2056	P21728	Dopamine D1 receptor	3.4 nM; 12.29 nM; 5.6 nM; 135 nM	Ki; IC50; Ki; Ki	via Super-PRED; PMID: 22748706; via Super-PRED; via Super-PRED
CHEMBL217	P14416	Dopamine D2 receptor	4380 nM; 11 nM; 115.5 nM; 105.41 nM	IC50; Ki; Ki; IC50	PMID: 25308766; via Super-PRED; via Super-PRED; PMID: 22748706
CHEMBL234	P35462	Dopamine D3 receptor	90.02 nM; 30 nM; 30 nM; 101 nM	Ki; Ki; Ki; Ki	PMID: 25308766; PMID: 27032890; via Super-PRED; via Super-PRED
CHEMBL219	P21917	Dopamine D4 receptor	3748 nM	Ki	PMID: 19744859
CHEMBL1850	P21918	Dopamine D5 receptor	4.4 nM; 4.4 nM	Ki; Ki	PMID: 19744859; via Super-PRED
CHEMBL287	Q99720	Sigma opioid receptor	269 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.59%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.17%	91.11%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	95.82%	93.40%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	94.21%	91.79%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.01%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.76%	94.45%
CHEMBL2535	P11166	Glucose transporter	91.33%	98.75%
CHEMBL3438	Q05513	Protein kinase C zeta	90.53%	88.48%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	90.47%	89.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.90%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.95%	92.94%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.85%	95.89%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.59%	85.14%
CHEMBL5747	Q92793	CREB-binding protein	85.45%	95.12%
CHEMBL2581	P07339	Cathepsin D	85.19%	98.95%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	84.85%	91.03%
CHEMBL4208	P20618	Proteasome component C5	84.62%	90.00%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	84.32%	82.38%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.80%	99.17%
CHEMBL3192	Q9BY41	Histone deacetylase 8	82.62%	93.99%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.04%	95.89%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	81.10%	100.00%

Plants that contains it

• Achyrocline satureioides
• Agathosma bisulca
• Alphonsea lutea
• Annona cherimola
• Annona glabra
• Brickellia dentata
• Cocculus laurifolius
• Dactylicapnos torulosa
• Desmos cochinchinensis
• Fibraurea recisa
• Greenwayodendron oliveri
• Horsfieldia iryaghedhi
• Karwinskia subcordata
• Liriodendron tulipifera
• Maytenus orbicularis
• Meiogyne monosperma
• Meiogyne virgata
• Menispermum dauricum
• Monodora junodii
• Pachygone ovata
• Passiflora coccinea
• Sinomenium acutum
• Stephania delavayi
• Stephania rotunda
• Stephania suberosa
• Stephania yunnanensis
• Tetraneuris ivesiana
• Ziziphus jujuba

Cross-Links

• PubChem: 6917970
• NPASS: NPC189266
• ChEMBL: CHEMBL487387
• LOTUS: LTS0267492
• wikiData: Q27088886