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),4,6,8-tetraene-19-carboxylate

• ChemBase ID: 960
• Molecular Formular: C32H38N2O8
• Molecular Mass: 578.65272
• Monoisotopic Mass: 578.26281619
• SMILES: O([C@@H]1[C@H]([C@@H]2[C@@H](CN3[C@H](C2)c2[nH]c4c(c2CC3)cccc4)C[C@H]1OC(=O)c1cc(OC)c(OC)c(OC)c1)C(=O)OC)C
• Canonical SMILES: COC(=O)[C@@H]1[C@@H](OC)[C@@H](C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c1[nH]c1c2cccc1)OC(=O)c1cc(OC)c(c(c1)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
• InChIKey: CVBMAZKKCSYWQR-WCGOZPBSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 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),4,6,8-tetraene-19-carboxylate; methyl (1R,15S,17R,18R,19S,20S)-18-methoxy-17-(3,4,5-trimethoxybenzoyloxy)-3,13-diazapentacyclo[11.8.0.0^2,^1^0.0^4,^9.0^1^5,^2^0]henicosa-2(10),4,6,8-tetraene-19-carboxylate
• IUPAC Traditional name: 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),4,6,8-tetraene-19-carboxylate; desmethoxyreserpine
• Brand Name: Aescin; Canescin; Canescine; Enduronyl; Harmonyl; Raunorine; Raunormin; Raunormine; Recanescin; Recanescine; Reserpidine; Tranquinil; beta-Escin
• Synonyms: Deserpidina [INN-Spanish]; Deserpidinum [INN-Latin]; Deserpidin; Desepridine; Deresperine; Deserpine; Desmethoxyreserpine; Deserpidine

Database IDs

• CAS Number: 131-01-1
• PubChem SID: 46505311; 160964423
• PubChem CID: 8550
• CHEBI ID: 27478
• ATC CODE: C02AA05
• CHEMBL: 1200515
• Chemspider ID: 8232
• DrugBank ID: DB01089
• KEGG ID: D08194
• Unique Ingredient Identifier: 9016E3VB47
• Wikipedia Title: Deserpidine

CALCULATED PROPERTIES

JChem

• Acid pKa: 16.37495
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): 1.771058
• LogD (pH = 7.4): 3.3759513
• Log P: 3.6891673
• Molar Refractivity: 154.9553 cm^3
• Polarizability: 61.769245 Å^3
• Polar Surface Area: 108.55 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 4.25
• LOG S: -4.72
• Solubility (Water): 1.11e-02 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 3.3

DETAILS

DrugBank - DB01089

• Drug Groups: approved
• Description: Deserpidine is an ester alkaloid drug isolated from Rauwolfia canescens (family Apocynaceae) with antipsychotic and antihypertensive properties that has been used for the control of high blood pressure and for the relief of psychotic behavior.
• Indication: For the treatment of hypertension.
• Pharmacology: Deserpidine, an alkaloid of Rauwolfia canescens, is used as an antihypertensive. Rauwolfia alkaloids work by controlling nerve impulses along certain nerve pathways. As a result, they act on the heart and blood vessels to lower blood pressure.
• Toxicity: Symptoms of overdose include dizziness or drowsiness (severe), flushing of skin, pinpoint pupils of eyes and slowed pulse.
• Affected Organisms: Humans and other mammals