Reserpic acid

Details

• Internal ID: 6ebfe2f9-0ec9-4d45-80fa-d01085a6f19d
• Taxonomy: Alkaloids and derivatives > Corynanthean-type alkaloids
• IUPAC Name: (1R,15S,17R,18R,19S,20S)-17-hydroxy-6,18-dimethoxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylic acid
• SMILES (Canonical): COC1C(CC2CN3CCC4=C(C3CC2C1C(=O)O)NC5=C4C=CC(=C5)OC)O
• SMILES (Isomeric): CO[C@H]1[C@@H](C[C@@H]2CN3CCC4=C([C@H]3C[C@@H]2[C@@H]1C(=O)O)NC5=C4C=CC(=C5)OC)O
• InChI: InChI=1S/C22H28N2O5/c1-28-12-3-4-13-14-5-6-24-10-11-7-18(25)21(29-2)19(22(26)27)15(11)9-17(24)20(14)23-16(13)8-12/h3-4,8,11,15,17-19,21,23,25H,5-7,9-10H2,1-2H3,(H,26,27)/t11-,15+,17-,18-,19+,21+/m1/s1
• InChI Key: JVHNBFFHWQQPLL-WOXROFTLSA-N
• Popularity: 17 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₈N₂O₅
• Molecular Weight: 400.50 g/mol
• Exact Mass: 400.19982200 g/mol
• Topological Polar Surface Area (TPSA): 95.00 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): 2.19
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

• Reserpinolic acid
• 83-60-3
• K6L9W0QP1W
• DTXSID50232112
• NSC-81463
• (1R,15S,17R,18R,19S,20S)-17-hydroxy-6,18-dimethoxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylic acid
• CHEBI:46690
• (3beta,16beta,17alpha,18beta,20alpha)-18-hydroxy-11,17-dimethoxyyohimban-16-carboxylic acid
• Yohimban-16-carboxylic acid, 18-hydroxy-11,17-dimethoxy-, (3beta,16beta,17alpha,18beta,20alpha)-
• RefChem:178893
• DTXCID50154603
• CHEMBL411716
• 18beta-hydroxy-11,17alpha-dimethoxy-3beta,20alpha-yohimban-16beta-carboxylic acid
• NSC81463
• UNII-K6L9W0QP1W
• Reserpinsaure
• NSC 81463
• Prestwick0_000984
• Prestwick1_000984
• Prestwick2_000984
• Prestwick3_000984
• RESERPIC ACID [MI]
• BSPBio_001047
• SCHEMBL571464
• SPBio_002948
• BPBio1_001153
• SCHEMBL30401625
• BDBM50374533
• FR65662
• NCI60_041786
• AB00514690
• Q1690907
• 3.beta., 18.beta.-hydroxy-11,17.alpha.-dimethoxy-
• BRD-K32755366-003-03-4
• 3beta,20alpha-Yohimban-16beta-carboxylic acid, 18beta-hydroxy-11,17alpha-dimethoxy-
• Yohimban-16-carboxylic acid, 18-hydroxy-11,17-dimethoxy-, (3.beta.,16.beta.,17.alpha.,18.beta.,20.alpha.)-
• Yohimban-16-carboxylic acid,17-dimethoxy-, (3.beta.,16.beta.,17.alpha.,18.beta.,20.alpha.)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9217	92.17%
Caco-2	+	0.6082	60.82%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.6422	64.22%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7962	79.62%
OATP1B3 inhibitior	+	0.8104	81.04%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.8849	88.49%
P-glycoprotein inhibitior	-	0.9166	91.66%
P-glycoprotein substrate	-	0.5585	55.85%
CYP3A4 substrate	+	0.6620	66.20%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4628	46.28%
CYP3A4 inhibition	-	0.8650	86.50%
CYP2C9 inhibition	-	0.9333	93.33%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.6407	64.07%
CYP inhibitory promiscuity	-	0.8139	81.39%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5864	58.64%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9894	98.94%
Skin irritation	-	0.7806	78.06%
Skin corrosion	-	0.9512	95.12%
Ames mutagenesis	-	0.6978	69.78%
Human Ether-a-go-go-Related Gene inhibition	-	0.4157	41.57%
Micronuclear	+	0.5300	53.00%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	-	0.8937	89.37%
Respiratory toxicity	+	0.9333	93.33%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	1.0000	100.00%
Nephrotoxicity	-	0.8348	83.48%
Acute Oral Toxicity (c)	II	0.6856	68.56%
Estrogen receptor binding	+	0.6747	67.47%
Androgen receptor binding	+	0.8357	83.57%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.5902	59.02%
Aromatase binding	-	0.6015	60.15%
PPAR gamma	-	0.6858	68.58%
Honey bee toxicity	-	0.8382	83.82%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	-	0.4487	44.87%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	794.3 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	99.11%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.91%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.30%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.10%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	94.88%	91.49%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.49%	97.09%
CHEMBL2581	P07339	Cathepsin D	88.58%	98.95%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	86.26%	94.08%
CHEMBL3192	Q9BY41	Histone deacetylase 8	85.61%	93.99%
CHEMBL4208	P20618	Proteasome component C5	85.50%	90.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.42%	95.89%
CHEMBL2535	P11166	Glucose transporter	84.86%	98.75%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.67%	92.94%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.36%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.55%	86.33%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.13%	93.00%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	80.26%	91.79%

Plants that contains it

• Rauvolfia vomitoria

Cross-Links

• PubChem: 65747
• LOTUS: LTS0146102
• wikiData: Q1690907