Reserpine

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	c8bfc55c-1336-401b-8dd6-930b3d8cf379
Taxonomy	Alkaloids and derivatives > Yohimbine alkaloids
IUPAC Name	methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-(3,4,5-trimethoxybenzoyl)oxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
SMILES (Canonical)	COC1C(CC2CN3CCC4=C(C3CC2C1C(=O)OC)NC5=C4C=CC(=C5)OC)OC(=O)C6=CC(=C(C(=C6)OC)OC)OC
SMILES (Isomeric)	CO[C@H]1[C@@H](C[C@@H]2CN3CCC4=C([C@H]3C[C@@H]2[C@@H]1C(=O)OC)NC5=C4C=CC(=C5)OC)OC(=O)C6=CC(=C(C(=C6)OC)OC)OC
InChI	InChI=1S/C33H40N2O9/c1-38-19-7-8-20-21-9-10-35-16-18-13-27(44-32(36)17-11-25(39-2)30(41-4)26(12-17)40-3)31(42-5)28(33(37)43-6)22(18)15-24(35)29(21)34-23(20)14-19/h7-8,11-12,14,18,22,24,27-28,31,34H,9-10,13,15-16H2,1-6H3/t18-,22+,24-,27-,28+,31+/m1/s1
InChI Key	QEVHRUUCFGRFIF-MDEJGZGSSA-N
Popularity	28,084 references in papers

Physical and Chemical Properties

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Molecular Formula	C₃₃H₄₀N₂O₉
Molecular Weight	608.70 g/mol
Exact Mass	608.27338086 g/mol
Topological Polar Surface Area (TPSA)	118.00 Å²
XlogP	4.00
Atomic LogP (AlogP)	4.17
H-Bond Acceptor	10
H-Bond Donor	1
Rotatable Bonds	8

Synonyms

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50-55-5

Serpalan

Serpasil

Apoplon

Serpivite

Alserin

Hypersil

Sandril

Deserpine

Elserpine

There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9136	91.36%
Caco-2	-	0.7212	72.12%
Blood Brain Barrier	+	1.0000	100.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.6614	66.14%
OATP2B1 inhibitior	+	1.0000	100.00%
OATP1B1 inhibitior	-	0.7738	77.38%
OATP1B3 inhibitior	-	0.5699	56.99%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.6389	63.89%
BSEP inhibitior	+	0.9859	98.59%
P-glycoprotein inhibitior	+	0.9026	90.26%
P-glycoprotein substrate	+	0.8392	83.92%
CYP3A4 substrate	+	0.6235	62.35%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4057	40.57%
CYP3A4 inhibition	-	0.8310	83.10%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9384	93.84%
CYP1A2 inhibition	+	0.8965	89.65%
CYP2C8 inhibition	+	0.7224	72.24%
CYP inhibitory promiscuity	-	0.7062	70.62%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5756	57.56%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9540	95.40%
Skin irritation	-	0.8037	80.37%
Skin corrosion	-	0.9538	95.38%
Ames mutagenesis	-	0.9500	95.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9354	93.54%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	-	0.9875	98.75%
skin sensitisation	-	0.9087	90.87%
Respiratory toxicity	+	0.9889	98.89%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	-	0.8250	82.50%
Acute Oral Toxicity (c)	II	0.7393	73.93%
Estrogen receptor binding	+	0.8906	89.06%
Androgen receptor binding	+	0.8697	86.97%
Thyroid receptor binding	+	0.6241	62.41%
Glucocorticoid receptor binding	+	0.8684	86.84%
Aromatase binding	+	0.8685	86.85%
PPAR gamma	+	0.8370	83.70%
Honey bee toxicity	-	0.7417	74.17%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5349	53.49%
Fish aquatic toxicity	+	0.7635	76.35%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	19952.6 nM 39810.7 nM	Potency Potency	via CMAUP via CMAUP
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	19952.6 nM	Potency	via CMAUP
CHEMBL5393	Q9UNQ0	ATP-binding cassette sub-family G member 2	26302.68 nM	IC50	PMID: 18678495
CHEMBL1293237	P54132	Bloom syndrome protein	17782.8 nM 17782.8 nM	Potency Potency	via CMAUP via CMAUP
CHEMBL4801	P29466	Caspase-1	7943.3 nM	Potency	via CMAUP
CHEMBL3468	P55210	Caspase-7	7943.3 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	3981.1 nM 3981.1 nM	Potency Potency	via CMAUP via CMAUP
CHEMBL2392	P06746	DNA polymerase beta	31622.8 nM	Potency	via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	25118.9 nM	Potency	via CMAUP
CHEMBL1293278	O75496	Geminin	11220.2 nM	Potency	via CMAUP
CHEMBL4331	P68871	Hemoglobin beta chain	31622.8 nM	Potency	via CMAUP
CHEMBL1293299	Q03164	Histone-lysine N-methyltransferase MLL	28183.8 nM	Potency	via CMAUP
CHEMBL1287622	Q9Y468	Lethal(3)malignant brain tumor-like protein 1	28183.8 nM	Potency	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	22387.2 nM	Potency	via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	7943.3 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	14125.4 nM 12589.3 nM	Potency Potency	via CMAUP via CMAUP
CHEMBL233	P35372	Mu opioid receptor	4152 nM	IC50	via CMAUP
CHEMBL5162	Q6W5P4	Neuropeptide S receptor	10000 nM	Potency	via CMAUP
CHEMBL4302	P08183	P-glycoprotein 1	2100 nM 500 nM 2100 nM 2600 nM 3900 nM 5300 nM 3235.94 nM 6100 nM 3019.95 nM 3235.94 nM	IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50	PMID: 11716514 PMID: 11716514 PMID: 11716514 PMID: 11716514 PMID: 11716514 PMID: 11716514 PMID: 18678495 PMID: 11716514 PMID: 17890094 PMID: 17890094
CHEMBL1293298	Q01453	Peripheral myelin protein 22	47754.8 nM	Potency	via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	17782.8 nM	Potency	via CMAUP
CHEMBL1893	Q05940	Synaptic vesicular amine transporter	5.26 nM	Ki	via Super-PRED
CHEMBL1293256	P40225	Thrombopoietin	31622.8 nM 31622.8 nM	Potency Potency	via CMAUP via CMAUP
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	15848.9 nM 15848.9 nM	Potency Potency	via CMAUP via CMAUP
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	44668.4 nM 56234.1 nM 10000 nM	Potency Potency Potency	via CMAUP via CMAUP via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4302	P08183	P-glycoprotein 1	98.78%	92.98%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.63%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.18%	91.11%
CHEMBL2535	P11166	Glucose transporter	96.14%	98.75%
CHEMBL5747	Q92793	CREB-binding protein	95.03%	95.12%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	93.89%	91.79%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.55%	95.56%
CHEMBL3192	Q9BY41	Histone deacetylase 8	91.39%	93.99%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.35%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.09%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.95%	97.09%
CHEMBL4208	P20618	Proteasome component C5	89.55%	90.00%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	88.36%	90.95%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	88.12%	93.40%
CHEMBL4630	O14757	Serine/threonine-protein kinase Chk1	86.00%	97.03%
CHEMBL340	P08684	Cytochrome P450 3A4	85.28%	91.19%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.67%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.86%	95.89%
CHEMBL213	P08588	Beta-1 adrenergic receptor	82.50%	95.56%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.88%	92.62%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.73%	99.23%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.70%	95.89%
CHEMBL1907	P15144	Aminopeptidase N	80.18%	93.31%
CHEMBL3922	P50579	Methionine aminopeptidase 2	80.13%	97.28%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.04%	94.45%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	80.01%	82.38%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.

Rauvolfia verticillata

Rauvolfia volkensii

Rauvolfia vomitoria

Vinca minor