Ajmalicine






Names

    • D08470
    • RAUBASINE [MART.]
    • methyl (1S,15R,16S,20S)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8,18-pentaene-19-carboxylate
    • Cristanyl
    • methyl (19alpha)-19-methyl-16,17-didehydrooxayohimban-16-carboxylate
    • PYTETRAHYDROSERPENTINE
    • HY-N1919R
    • NSC 72133
    • AKOS015895125
    • Hydrosarpan
    • SpecPlus_000425
    • methyl (4S,4aR,13bS,14aS)-4-methyl-4a,5,7,8,13,13b,14,14a-octahydro-4H-indolo[2,3-a]pyrano[3,4-g]quinolizine-1-carboxylate
    • Oxayohimban-16-carboxylic acid, 16,17-didehydro-19-methyl-, methylester, (19a)-
    • 4a,5,7,8,13,13b,14,14a-octahydro-4H-indolo
    • KBio2_001255
    • BDBM50030612
    • (4S,4aR,13bS,14aS)-methyl 4-methyl-
    • py-Tetrahydroserpentine
    • Tetrahydroserpentine
    • BPBio1_000512
    • UNII-4QJL8OX71Z
    • Methyl 16,17-didehydro-19alpha-methyl-18-oxayohimban-16-carboxylat
    • Oxayohimban-16-carboxylic acid, 16,17-didehydro-19-methyl-, methyl ester, (19-.alpha).-
    • W-106052
    • [2,3-a]pyrano[3,4-g]quinolizine-1-carboxylate
    • NCGC00016647-06
    • CAS-6474-90-4
    • KBioSS_001255
    • Lamuran (TN)
    • HY-N1919
    • DivK1c_006521
    • DTXSID60904151
    • AC-20175
    • Methyl (19-methyl-16,17-dehydro-18-oxa-3alpha,15alpha,19beta,20beta-yohimban-16-carboxylat)
    • Raubasine
    • GTPL8746
    • Isoarteril
    • MFCD00042748
    • Raubasine (DCF)
    • Prestwick3_000592
    • BRD-K83028735-003-03-8
    • Q412957
    • KBio1_001465
    • delta-Yohimbine
    • BRD-K83028735-001-01-6
    • EN300-7385816
    • 19b-methyl-16-methoxycarbonyl-16,17-didehydro-oxayohimbane
    • CHEMBL123325
    • NCGC00016647-02
    • Prestwick0_000592
    • RAUBASINE [WHO-DD]
    • C09024
    • 16,17-Didehydro-19-methyloxayohimban-16-carboxylic acid methyl ester
    • .delta.-Yohimbine
    • NSC-72133
    • CS-0018230
    • CAS-4373-34-6
    • 4QJL8OX71Z
    • Ajmalicin
    • DA-70706
    • EINECS 207-589-5
    • Circolene
    • 483-04-5
    • Prestwick1_000592
    • MEGxp0_001818
    • SCHEMBL309914
    • BSPBio_000464
    • Oxayohimban-16-carboxylic acid, 16,17-didehydro-19-methyl-, methyl ester, (19-alpha)-
    • methyl (1S,15R,16S,20S)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4(9),5,7,18-pentaene-19-carboxylate
    • NCGC00016647-03
    • Spectrum_000775
    • Lamuran
    • SPBio_002683
    • Substance II
    • CHEBI:2524
    • methyl (1S,15R,16S,20S)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,18-pentaene-19-carboxylate
    • (19.ALPHA.)-16,17-DIDEHYDRO-19-METHYLOXAYOHIMBAN-16-CARBOXYLIC ACID METHYL ESTER
    • Sarpan
    • Methyl (19alpha)-19-methyl-16,17-didehydro-18-oxayohimban-16-carboxylate
    • ACon1_001630
    • AS-35306
    • NCGC00016647-01
    • AJN
    • 8063-17-0
    • Ajmalicine (Standard)
    • (4S,4aR,13bS,14aS)-methyl 4-methyl-4a,5,7,8,13,13b,14,14a-octahydro-4H-indolo[2,3-a]pyrano[3,4-g]quinolizine-1-carboxylate
    • Ajmalicine
    • Rauvasan
    • (7aR,8S,11aS,12aS)-8-Methyl-5,6,7a,8,11a,12,12a,13-octahydro-7H-9-oxa-6a,13-diaza-indeno[2,1-a]anthracene-11-carboxylic acid methyl ester
    • BRN 0097268
    • Prestwick2_000592
    • Alkaloids, Rauwolfia
    • RAUBASINE [MI]
    • NS00009801
    • 4-27-00-07927 (Beilstein Handbook Reference)
    • Raubasine,(S)
    • (19alpha)-16,17-Didehydro-19-methyl-oxayohimban-16-carboxylic acid methyl ester
    • rauwolfia alkaloid
    • NCGC00016647-04
    • KBio2_003823
    • KBio2_006391

Attributes

  • Canonical SMILES

    C[C@H]1[C@H]2CN3CCC4=C([C@@H]3C[C@@H]2C(=CO1)C(=O)OC)NC5=CC=CC=C45

  • InChI

    InChI=1S/C21H24N2O3/c1-12-16-10-23-8-7-14-13-5-3-4-6-18(13)22-20(14)19(23)9-15(16)17(11-26-12)21(24)25-2/h3-6,11-12,15-16,19,22H,7-10H2,1-2H3/t12-,15-,16+,19-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 54.559999999999995
  • #RotBonds: 1
  • MW: 352.434
  • HBD: 1
  • HBA: 4
  • logP: 3.1788000000000016
  • Chemical Formula: C21H24N2O3


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. bufalina China 403123 Cai20170220

External Databases


References

  • Alkaloids isolated from Tabernaemontana bufalina display xanthine oxidase inhibitory activity. Phytochemistry, 2019 (PMID 31302343).

Compound-Protein Relationships

Compound Activities

    • Xanthine oxidase inhibitory

Predicted NMR Spectral Data


Predicted MS Fragmentation Pattern

    N.B.: It is recommended to zoom in on a specific area of an MS plot before hovering on a peak.


Predicted ADMET Properties

    Property Model Name Predicted Value

    Absorption Caco-2 (logPaap) -4.82
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.85
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.02

    Distribution Blood-Brain Barrier (Central Nervous System) -2.67
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.77
    Plasma Protein Binding 50.19
    Steady State Volume of Distribution 7.1

    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor Non-Inhibitor
    CYP 2C19 substrate Substrate
    CYP 2C9 Inhibitor Non-Inhibitor
    CYP 2C9 Substrate Substrate
    CYP 2D6 Inhibitor Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor

    Excretion Clearance 11.13
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs

    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.6
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.48
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 7.54
    Micronucleos Toxic
    NR-AhR Toxic
    NR-AR Safe
    NR-AR-LBD Safe
    NR-Aromatase Safe
    NR-ER Safe
    NR-ER-LBD Safe
    NR-GR Safe
    NR-PPAR-gamma Safe
    NR-TR Safe
    T. Pyriformis -10.36
    Rat (Acute) 2.85
    Rat (Chronic Oral) 1.85
    Fathead Minnow 4.02
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe

    General Properties Boiling Point 413.93
    Hydration Free Energy -5.44
    Log(D) at pH=7.4 3.38
    Log(P) 3.19
    Log S -3.34
    Log(Vapor Pressure) -8.03
    Melting Point 203.07
    pKa Acid 9.92
    pKa Basic 7.59