Rauwolscine

Details

• Internal ID: 2563544a-f672-489f-8944-3e2907de1c91
• Taxonomy: Alkaloids and derivatives > Yohimbine alkaloids
• IUPAC Name: methyl (1S,15S,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+/m1/s1
• InChI Key: BLGXFZZNTVWLAY-DIRVCLHFSA-N
• Popularity: 6,460 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
• Atomic LogP (AlogP): 2.65
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• alpha-Yohimbine
• 131-03-3
• Corynanthidine
• Isoyohimbine
• Mesoyohimbine
• meso-Yohimbine
• .alpha.-Yohimbine
• Methyl (16beta,17alpha,20alpha)-17-hydroxyyohimban-16-carboxylate
• T4LJ7LU45W
• CHEMBL10347
• DTXSID2045608
• CHEBI:48562
• 17alpha-hydroxy-20alpha-yohimban-16beta-carboxylic acid methyl ester
• methyl (1S,15S,18S,19S,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
• NCGC00017260-05
• methyl 17alpha-hydroxy-20alpha-yohimban-16beta-carboxylate
• 17-alpha-Hydroxy-20-alpha-yohimban-16-beta-carboxylic acid methyl ester
• 20-alpha-Yohimban-16-beta-carboxylic acid, 17-alpha-hydroxy-, methyl ester
• [3H]rauwolscine
• (1S,2S,4aS,13bS,14aS)-Methyl 2-hydroxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydroindolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylate
• methyl hydroxy[?]carboxylate
• SR-01000075289
• UNII-T4LJ7LU45W
• yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16beta,17alpha,20alpha)-
• EINECS 205-006-9
• I+/--Yohimbin
• Spectrum_001458
• Prestwick0_000577
• Prestwick1_000577
• Prestwick2_000577
• Prestwick3_000577
• Spectrum2_000870
• Spectrum3_001761
• Spectrum4_000319
• Spectrum5_001121
• Rauwolscine (6CI,7CI)
• Rauwolscine;[3H]rauwolscine
• Lopac0_001093
• BSPBio_000394
• BSPBio_003221
• GTPL136
• GTPL223
• KBioGR_000938
• KBioSS_001938
• YOHIMBINE, .ALPHA.-
• DivK1c_000414
• SCHEMBL244514
• SPBio_000919
• SPBio_002613
• BPBio1_000434
• .ALPHA.-YOHIMBINE [MI]
• Benz[g]indolo[2,3-a]quinolizine, yohimban-16-carboxylic acid deriv.
• DTXCID0025608
• KBio1_000414
• KBio2_001938
• KBio2_004506
• KBio2_007074
• KBio3_002721
• NINDS_000414
• Tox21_110811
• BDBM50026636
• -Yohimbine;Corynanthidine;Isoyohimbine
• AKOS032948426
• CCG-205170
• SDCCGMLS-0066742.P001
• SDCCGSBI-0051063.P003
• IDI1_000414
• Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16beta,17alpha,20alpha)- (9CI)
• .ALPHA.-YOHIMBINE [EP IMPURITY]
• NCGC00017260-06
• CAS-131-03-3
• FS-10296
• AB00514662
• 5-AMINO-1-BENZOTHIOPHENE-2-CARBOXYLICACID
• Q7296272
• SR-01000075289-6
• SR-01000075289-7
• SR-01000075289-8
• BRD-K77474816-003-04-2
• BRD-K77474816-003-05-9
• BRD-K77474816-003-09-1
• YOHIMBINE HYDROCHLORIDE IMPURITY B [EP IMPURITY]
• METHYL 17.ALPHA.-HYDROXY-20.ALPHA.-YOHIMBAN-16.BETA.-CARBOXYLATE
• 20alpha-Yohimban-16beta-carboxylic acid, 17alpha-hydroxy-, methyl ester (8CI)
• Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16-beta,17-alpha,20-alpha)-
• Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (17alpha,20alpha)-
• 112350-93-3
• YOHIMBAN-16-CARBOXYLIC ACID, 17-HYDROXY-, METHYL ESTER, (16.BETA.,17.ALPHA.,20.ALPHA.)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9856	98.56%
Caco-2	+	0.9312	93.12%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.9000	90.00%
Subcellular localzation	Mitochondria	0.7506	75.06%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9368	93.68%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.9071	90.71%
P-glycoprotein inhibitior	-	0.7032	70.32%
P-glycoprotein substrate	+	0.9344	93.44%
CYP3A4 substrate	+	0.7976	79.76%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4913	49.13%
CYP3A4 inhibition	-	0.8333	83.33%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9094	90.94%
CYP2D6 inhibition	+	0.8931	89.31%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.5764	57.64%
CYP inhibitory promiscuity	-	0.8682	86.82%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6191	61.91%
Eye corrosion	-	0.9911	99.11%
Eye irritation	-	0.9861	98.61%
Skin irritation	-	0.7617	76.17%
Skin corrosion	-	0.9523	95.23%
Ames mutagenesis	-	0.6378	63.78%
Human Ether-a-go-go-Related Gene inhibition	+	0.8763	87.63%
Micronuclear	+	0.6100	61.00%
Hepatotoxicity	-	0.8500	85.00%
skin sensitisation	-	0.9054	90.54%
Respiratory toxicity	+	0.9778	97.78%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	+	0.7565	75.65%
Acute Oral Toxicity (c)	II	0.4961	49.61%
Estrogen receptor binding	+	0.6268	62.68%
Androgen receptor binding	+	0.7850	78.50%
Thyroid receptor binding	-	0.5760	57.60%
Glucocorticoid receptor binding	-	0.6381	63.81%
Aromatase binding	-	0.8514	85.14%
PPAR gamma	-	0.8545	85.45%
Honey bee toxicity	-	0.8352	83.52%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	-	0.5922	59.22%

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

• Alstonia constricta
• Corynanthe pachyceras
• Rauvolfia caffra
• Rauvolfia serpentina
• Rauvolfia tetraphylla
• Rauvolfia volkensii
• Uncaria callophylla

Cross-Links

• PubChem: 643606
• LOTUS: LTS0236098
• wikiData: Q7296272