Corynanthine

Details

• Internal ID: 6c82f70a-9d13-41ec-bed8-531e9dd42d3b
• Taxonomy: Alkaloids and derivatives > Yohimbine alkaloids
• IUPAC Name: methyl (1S,15R,18S,19S,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
• SMILES (Canonical): COC(=O)C1C(CCC2C1CC3C4=C(CCN3C2)C5=CC=CC=C5N4)O
• SMILES (Isomeric): COC(=O)[C@@H]1[C@H](CC[C@@H]2[C@@H]1C[C@H]3C4=C(CCN3C2)C5=CC=CC=C5N4)O
• InChI: InChI=1S/C21H26N2O3/c1-26-21(25)19-15-10-17-20-14(13-4-2-3-5-16(13)22-20)8-9-23(17)11-12(15)6-7-18(19)24/h2-5,12,15,17-19,22,24H,6-11H2,1H3/t12-,15-,17-,18-,19-/m0/s1
• InChI Key: BLGXFZZNTVWLAY-DKJBZYCGSA-N
• Popularity: 6,021 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₆N₂O₃
• Molecular Weight: 354.40 g/mol
• Exact Mass: 354.19434270 g/mol
• Topological Polar Surface Area (TPSA): 65.60 Ų
• XlogP: 2.90

Synonyms

• 483-10-3
• Rauhimbine
• Rauhimbin
• Corynanthin
• F5Z7C9RK8U
• CHEMBL31410
• Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16beta,17alpha)-
• SMR000857089
• methyl hydroxy[?]carboxylate
• UNII-F5Z7C9RK8U
• NSC-407306
• EINECS 207-590-0
• NSC 407306
• Lopac-R-104
• Prestwick0_000578
• Prestwick1_000578
• Prestwick2_000578
• Prestwick3_000578
• CORYNANTHINE [MI]
• Lopac-Y-3125
• BSPBio_000396
• MLS001332619
• MLS001332620
• CORYNANTHINE [WHO-DD]
• SCHEMBL178061
• SPBio_002615
• BPBio1_000436
• GTPL5345
• MEGxp0_001869
• ACon1_002064
• CHEBI:92122
• BLGXFZZNTVWLAY-DKJBZYCGSA-N
• Bio1_000472
• Bio1_000961
• Bio1_001450
• DTXSID401317915
• HMS2231N15
• Methyl (16beta,17alpha)-17-hydroxyyohimban-16-carboxylate
• BDBM50027058
• MFCD00069659
• AKOS024282584
• CCG-208620
• SMP1_000080
• NCGC00015878-01
• NCGC00015878-02
• NCGC00016294-06
• HY-118638
• CS-0067661
• Q5173746
• BRD-K06467078-003-03-7
• YOHIMBINE HYDROCHLORIDE IMPURITY C [EP IMPURITY]
• 17alpha-Hydroxyyohimban-16beta-carboxylic acid methyl ester
• Yohimban-16beta-carboxylic acid, 17alpha-hydroxy-, methyl ester
• METHYL (16.BETA.,17.ALPHA.)-17-HYDROXYYOHIMBAN-16-CARBOXYLATE
• Yohimban-16.beta.-carboxylic acid, 17.alpha.-hydroxy-, methyl ester
• Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16.beta.,17.alpha.)-
• (1S,2S,4aR,13bS,14aS)-2-Hydroxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2'''',3'''':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester
• (1S,2S,4aR,13bS,14aS)-2-Hydroxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2'',3'':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester
• 2-Hydroxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2'',3'':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester
• methyl (1S,15R,18S,19S,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
• methyl (1S,15R,18S,19S,20S)-18-hydroxy-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8-tetraene-19-carboxylate

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
CHEMBL229	P35348	Alpha-1a adrenergic receptor	29 nM	Ki	via Super-PRED
CHEMBL232	P35368	Alpha-1b adrenergic receptor	7.2 nM; 517 nM	Ki; Ki	via Super-PRED; via Super-PRED
CHEMBL223	P25100	Alpha-1d adrenergic receptor	1.6 nM; 253 nM; 3.5 nM	Ki; Ki; Ki	via Super-PRED; via Super-PRED; via Super-PRED
CHEMBL1867	P08913	Alpha-2a adrenergic receptor	0.42 nM	Ki	via Super-PRED
CHEMBL1942	P18089	Alpha-2b adrenergic receptor	1.16 nM	Ki	via Super-PRED
CHEMBL1916	P18825	Alpha-2c adrenergic receptor	16 nM; 0.5 nM	IC50; Ki	via Super-PRED; via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	89.1 nM	Potency	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	98.57%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.19%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.93%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.05%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.87%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.92%	97.09%
CHEMBL2581	P07339	Cathepsin D	91.35%	98.95%
CHEMBL1914	P06276	Butyrylcholinesterase	90.98%	95.00%
CHEMBL2535	P11166	Glucose transporter	88.62%	98.75%
CHEMBL228	P31645	Serotonin transporter	88.51%	95.51%
CHEMBL5028	O14672	ADAM10	86.11%	97.50%
CHEMBL4040	P28482	MAP kinase ERK2	84.35%	83.82%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.97%	99.23%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	80.04%	94.08%

Plants that contains it

• Corynanthe pachyceras
• Rauvolfia biauriculata
• Rauvolfia serpentina
• Rauvolfia tetraphylla

Cross-Links

• PubChem: 92766
• LOTUS: LTS0085184
• wikiData: Q5173746