17-Demethoxy-hydroisorhynchophylline






Names

    • 7F4P99KHLJ
    • CORYNOXAN-16-CARBOXYLIC ACID, 16,17-DIDEHYDRO-17-METHOXY-2-OXO-, METHYL ESTER, (16E,20.ALPHA.)-
    • AKOS025402306
    • UNII-7F4P99KHLJ', "methyl (E)-2-[(3S,6'R,7'S,8'aS)-6'-ethyl-2-oxospiro[1H-indole-3,1'-3,5,6,7,8,8a-hexahydro-2H-indolizine]-7'-yl]-3-methoxyprop-2-enoate", '(16E,20-alpha)-16,17-Didehydro-17-methoxy-2-oxo-corynoxan-16-carboxylic acid
    • AC-7996
    • HY-N0766
    • MLS000728608
    • SCHEMBL23259272
    • 1ST159053
    • C22H28N2O4
    • CHEMBL480521
    • 17-Demethoxy-hydroisorhynchophylline
    • HMS3886F22
    • CHEBI:70071
    • Isorhychophylline
    • 6859-01-4
    • Q-100013', "ISORHYNCHOPHYLLINE (CONSTITUENT OF CAT'S CLAW)", 'Q27138409', "ISORHYNCHOPHYLLINE (CONSTITUENT OF CAT'S CLAW) [DSC]", '(16E\\,20-alpha)-16\\,17-Didehydro-17-methoxy-2-oxo-corynoxan-16-carboxylic acid
    • HMS2267O23
    • 7-Isorhyncophylline
    • DA-54453
    • Isorhynchophylline
    • CORYNOXAN-16-CARBOXYLIC ACID, 16,17-DIDEHYDRO-17-METHOXY-2-OXO-, METHYL ESTER, (16E,20alpha)-', "methyl (2E)-2-[(3S,6'R,7'S,8'aS)-6'-ethyl-2-oxo-1,2,3',5',6',7',8',8'a-octahydro-2'H-spiro[indole-3,1'-indolizin]-7'-yl]-3-methoxyprop-2-enoate", "SPIRO(3H-INDOLE-3,1'(5'H)-INDOLIZINE)-7'-ACETIC ACID, 6'-ETHYL-1,2,2',3',6',7',8',8'A-OCTAHYDRO-.ALPHA.-(METHOXYMETHYLENE)-2-OXO-, METHYL ESTER, (.ALPHA.E,1'S,6'R,7'S,8'AS)-", "SPIRO(3H-INDOLE-3,1'(5'H)-INDOLIZINE)-7'-ACETIC ACID, 6'-ETHYL-1,2,2',3',6',7',8',8'A-OCTAHYDRO-alpha-(METHOXYMETHYLENE)-2-OXO-, METHYL ESTER, (alphaE,1'S,6'R,7'S,8'AS)-"
    • CCG-268459
    • 39032-62-7', "Rel-methyl (E)-2-((3S,6'R,7'S,8a'S)-6'-ethyl-2-oxo-2',3',6',7',8',8a'-hexahydro-5'H-spiro[indoline-3,1'-indolizin]-7'-yl)-3-methoxyacrylate", 'Isorhynchophylline (Standard)
    • AS-75287
    • SMR000470794
    • s9310
    • Isorhyncophylline
    • CS-3805
    • BDBM50531282
    • HY-N0766R
    • Corynoxan-16-carboxylic acid, 16,17-didehydro-17-methoxy-2-oxo-, methyl ester, (16E,20-alpha)-
    • C16980

Attributes

  • Canonical SMILES

    CC[C@H]1CN2CC[C@]3(C4=CC=CC=C4NC3=O)[C@]2([H])C[C@@H]1/C(C(OC)=O)=C\OC

  • InChI

    InChI=1S/C22H28N2O4/c1-4-14-12-24-10-9-22(17-7-5-6-8-18(17)23-21(22)26)19(24)11-15(14)16(13-27-2)20(25)28-3/h5-8,13-15,19H,4,9-12H2,1-3H3,(H,23,26)/b16-13+/t14-,15-,19-,22-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 67.87
  • #RotBonds: 4
  • MW: 384.4760000000002
  • HBD: 1
  • HBA: 5
  • logP: 2.7002000000000006
  • Chemical Formula: C22H28N2O4


Species

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

External Databases


References

  • Chemical Constituents from Tabernaemontana bufalina Lour. Chem Biodivers, 2019 (PMID 30411487).

Compound-Protein Relationships


Compound Activities

    • Cytotoxicity

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) -4.74
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.82
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.77
    Distribution Blood-Brain Barrier (Central Nervous System) -2.6
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.81
    Plasma Protein Binding 58.01
    Steady State Volume of Distribution 3.17
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor Non-Inhibitor
    CYP 2C19 substrate Substrate
    CYP 2C9 Inhibitor Non-Inhibitor
    CYP 2C9 Substrate Non-Substrate
    CYP 2D6 Inhibitor Non-Inhibitor
    CYP 2D6 Substrate Non-Substrate
    CYP 3A4 Inhibitor Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 6.22
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.28
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.57
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 5.4
    Micronucleos Toxic
    NR-AhR Safe
    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 -18.15
    Rat (Acute) 3.41
    Rat (Chronic Oral) 2.2
    Fathead Minnow 4.18
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Toxic
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 436.78
    Hydration Free Energy -5.46
    Log(D) at pH=7.4 2.67
    Log(P) 2.18
    Log S -3.44
    Log(Vapor Pressure) -7.85
    Melting Point 176.56
    pKa Acid 8.03
    pKa Basic 6.86