Deserpidine

Details

• Internal ID: 68ea2a25-a6e5-43c8-bb0f-9e205312372f
• Taxonomy: Alkaloids and derivatives > Yohimbine alkaloids
• IUPAC Name: methyl (1R,15S,17R,18R,19S,20S)-18-methoxy-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=CC=CC=C45)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=CC=CC=C45)OC(=O)C6=CC(=C(C(=C6)OC)OC)OC
• InChI: InChI=1S/C32H38N2O8/c1-37-24-12-17(13-25(38-2)29(24)39-3)31(35)42-26-14-18-16-34-11-10-20-19-8-6-7-9-22(19)33-28(20)23(34)15-21(18)27(30(26)40-4)32(36)41-5/h6-9,12-13,18,21,23,26-27,30,33H,10-11,14-16H2,1-5H3/t18-,21+,23-,26-,27+,30+/m1/s1
• InChI Key: CVBMAZKKCSYWQR-WCGOZPBSSA-N
• Popularity: 253 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₃₈N₂O₈
• Molecular Weight: 578.70 g/mol
• Exact Mass: 578.26281617 g/mol
• Topological Polar Surface Area (TPSA): 109.00 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 4.16
• H-Bond Acceptor: 9
• H-Bond Donor: 1
• Rotatable Bonds: 7

Synonyms

• 131-01-1
• Harmonyl
• Raunormine
• Recanescin
• Deserpidin
• Recanescine
• Canescine
• Desepridine
• Raunormin
• Canescin
• Reserpidine
• Desmethoxyreserpine
• Tranquinil
• 11-Demethoxyreserpine
• 11-Desmethoxyreserpine
• Deserpidinum
• Deserpidina
• Halmonyl
• Deserpidinum [INN-Latin]
• Deserpidina [INN-Spanish]
• Lilly 22641
• Deserpidine, (-)-
• CHEBI:27478
• EINECS 205-004-8
• Deresperine
• NSC 72138
• NSC-72138
• Deserpidic acid, methyl ester, 3,4,5-trimethoxybenzoate
• Deserpidine (INN)
• BRN 0101820
• A-11025
• DTXSID8020383
• UNII-9016E3VB47
• NSC72138
• Methyl 18beta-hydroxy-17alpha-methoxy-3beta,20alpha-yohimban-16beta-carboxylate, 3,4,5-trimethoxybenzoate (ester)
• 9016E3VB47
• DTXCID80383
• Methyl 17alpha-methoxy-18beta-(3,4,5-trimethoxybenzoyloxy)-3beta,20alpha-yohimban-16beta-carboxylat
• 4-25-00-01282 (Beilstein Handbook Reference)
• ENDURONYL COMPONENT DESERPIDINE
• 3-beta,20-alpha-Yohimban-16-beta-carboxylic acid, 18-beta-hydroxy-17-alpha-methoxy-, methyl ester, 3,4,5-trimethoxybenzoate (ester)
• methyl (1R,15S,17R,18R,19S,20S)-18-methoxy-17-(3,4,5-trimethoxybenzoyl)oxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
• methyl (3beta,16beta,17alpha,18beta,20alpha)-17-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylate
• Methyl 17alpha-methoxy-18beta-((3,4,5-trimethoxybenzoyl)oxy)-3beta,20alpha-yohimban-16beta-carboxylate
• NCGC00168786-01
• NCGC00168786-02
• DESERPIDINE COMPONENT OF ENDURONYL
• ORETICYL FORTE COMPONENT DESERPIDINE
• DESERPIDINE [INN]
• DESERPIDINE COMPONENT OF ORETICYL FORTE
• Deserpidinum (INN-Latin)
• Deserpidina (INN-Spanish)
• Deserpidine [INN:BAN]
• DESERPIDINE (MART.)
• DESERPIDINE [MART.]
• (3beta,16beta,17alpha,18beta,20alpha)-17-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylic acid methyl ester
• methyl (3beta,16beta,17alpha,18beta,20alpha)-17-(methyloxy)-18-({[3,4,5-tris(methyloxy)phenyl]carbonyl}oxy)yohimban-16-carboxylate
• Yohimban-16-carboxylic acid,17-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester,(3b,16b,17a,18b,20a)-
• Halmonyl (TN)
• CAS-131-01-1
• (3beta,16beta,17alpha,18beta,20alpha)-17-methoxy-18-((3,4,5-trimethoxybenzoyl)oxy)yohimban-16-carboxylic acid methyl ester
• methyl (3beta,16beta,17alpha,18beta,20alpha)-17-methoxy-18-((3,4,5-trimethoxybenzoyl)oxy)yohimban-16-carboxylate
• MD-0232
• DESERPIDINE [MI]
• DESERPIDINE [VANDF]
• DESERPIDINE [WHO-DD]
• MLS006010113
• SCHEMBL259343
• GTPL7064
• CHEMBL1200515
• C02AA05
• DESERPIDINE [ORANGE BOOK]
• METHYL 17.ALPHA.-METHOXY-18.BETA.-((3,4,5-TRIMETHOXYBENZOYL)OXY)-3.BETA.,20.ALPHA.-YOHIMBAN-16.BETA.-CARBOXYLATE
• Tox21_112646
• Tox21_113102
• BDBM50480272
• AKOS015896464
• DB01089
• (1S,2R,3R,4aS,13bR,14aS)-Methyl 2-methoxy-3-((3,4,5-trimethoxybenzoyl)oxy)-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydroindolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylate
• 17.alpha.-Methoxy-18.beta.-[(3,4,5-trimethoxybenzoyl)oxy]-3.beta.,20.alpha.-yohimban-16.beta.-carboxylic acid methyl ester
• SMR004701248
• HY-107339
• CS-0028177
• C06541
• D08194
• F82150
• EN300-19736832
• J-005923
• Q5263885
• Benz[g]indolo[2, 1,2,3,4,4a,5,7,8,-13,13b,14,14a-dodecahydro-3-hydroxy-2-methoxy-, methyl ester, 3,4,5-trimethoxybenzoate
• methyl (1R,15S,17R,18R,19S,20S)-18-methoxy-17-(3,4,5-trimethoxybenzoyloxy)-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4(9),5,7-tetraene-19-carboxylate
• methyl (1R,15S,17R,18R,19S,20S)-18-methoxy-17-[(3,4,5-trimethoxyphenyl)carbonyloxy]-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8-tetraene-19-carboxylate
• Yohimban-16-carboxylic acid, 17-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3b,16b,17a,18b,20a)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9282	92.82%
Caco-2	-	0.6903	69.03%
Blood Brain Barrier	+	1.0000	100.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.6253	62.53%
OATP2B1 inhibitior	+	0.5233	52.33%
OATP1B1 inhibitior	-	0.4883	48.83%
OATP1B3 inhibitior	-	0.4730	47.30%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.6389	63.89%
BSEP inhibitior	+	0.9795	97.95%
P-glycoprotein inhibitior	+	0.9112	91.12%
P-glycoprotein substrate	+	0.8688	86.88%
CYP3A4 substrate	+	0.7033	70.33%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4057	40.57%
CYP3A4 inhibition	-	0.8353	83.53%
CYP2C9 inhibition	-	0.8701	87.01%
CYP2C19 inhibition	-	0.8954	89.54%
CYP2D6 inhibition	-	0.9064	90.64%
CYP1A2 inhibition	+	0.8392	83.92%
CYP2C8 inhibition	+	0.7574	75.74%
CYP inhibitory promiscuity	-	0.7081	70.81%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5932	59.32%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9562	95.62%
Skin irritation	-	0.7995	79.95%
Skin corrosion	-	0.9526	95.26%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9403	94.03%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	-	0.9500	95.00%
skin sensitisation	-	0.9057	90.57%
Respiratory toxicity	+	0.9556	95.56%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	-	0.7338	73.38%
Acute Oral Toxicity (c)	II	0.6805	68.05%
Estrogen receptor binding	+	0.8906	89.06%
Androgen receptor binding	+	0.8283	82.83%
Thyroid receptor binding	+	0.6075	60.75%
Glucocorticoid receptor binding	+	0.8442	84.42%
Aromatase binding	+	0.7731	77.31%
PPAR gamma	+	0.8708	87.08%
Honey bee toxicity	-	0.7379	73.79%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5351	53.51%
Fish aquatic toxicity	+	0.7743	77.43%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4302	P08183	P-glycoprotein 1	99.58%	92.98%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.44%	96.09%
CHEMBL2535	P11166	Glucose transporter	97.02%	98.75%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.68%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.84%	95.56%
CHEMBL1914	P06276	Butyrylcholinesterase	93.79%	95.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	91.65%	93.99%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.66%	85.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.46%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.68%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.64%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.52%	99.23%
CHEMBL5747	Q92793	CREB-binding protein	86.49%	95.12%
CHEMBL5028	O14672	ADAM10	84.92%	97.50%
CHEMBL2581	P07339	Cathepsin D	84.85%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.63%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.38%	89.00%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	84.01%	90.95%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	82.82%	82.38%
CHEMBL340	P08684	Cytochrome P450 3A4	81.98%	91.19%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.76%	92.62%
CHEMBL213	P08588	Beta-1 adrenergic receptor	81.57%	95.56%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	80.17%	94.08%

Plants that contains it

• Lithospermum canescens
• Rauvolfia serpentina
• Rauvolfia tetraphylla

Cross-Links

• PubChem: 8550
• LOTUS: LTS0014722
• wikiData: Q5263885