Coronarine






Names

    • CHEBI:4653
    • NCI60_005689
    • Thymidine,6-dihydro-6-methoxy-
    • BRD-K86301799-001-37-1
    • NCGC00015385-05
    • KBio3_001144
    • Dipyridamole, >=98% (TLC), powder
    • MLS001333724
    • Tox21_110133
    • 4-26-00-03840 (Beilstein Handbook Reference)', "2,2',2'',2'''-((4,8-Dipiperidinopyrimido(5,4-d)pyrimidine-2,6-diyl)dinitrilo)tetraethanol", 'AGGRENOX COMPONENT DIPYRIDAMOLE', "2,2',2'',2'''-((4,8-di(piperidin-1-yl)pyrimido[5,4-d]pyrimidine-2,6-diyl)bis(azanetriyl))tetrakis(ethan-1-ol)", "Ethanol, 2,2',2'',2'''-((4,8-di-1-piperidinylpyrimido(5,4-d)pyrimidine-2,6-diyl)dinitrilo)tetrakis-", "Ethanol, 2,2',2'',2'''-[(4,8-di-1-piperidinylpyrimido[5,4-d]pyrimidine-2,6-diyl)dinitrilo]tetrakis-", "Ethanol,2,2',2'',2'''-[(4,8-di-1-piperidinylpyrimido[5,4-d]pyrimidine-2,6-diyl)dinitrilo]tetrakis-", 'CAS-58-32-2
    • Spectrum2_000972
    • 2-[[2-[bis(2-hydroxyethyl)amino]-4,8-di(piperidin-1-yl)pyrimido[5,4-d]pyrimidin-6-yl]-(2-hydroxyethyl)amino]ethanol
    • BSPBio_000244
    • DIPYRIDAMOLE (USP MONOGRAPH)
    • BCP26947
    • EN300-70723
    • DIPYRIDAMOLE (EP MONOGRAPH)
    • Coroxin
    • Spectrum_001004
    • Q419374
    • NSC-756743
    • W-105400
    • 2,6-Bis(diethanolamine)-4,8-dipiperidinopyrimido[5,4-d]pyrimidine
    • IZEKFCXSFNUWAM-UHFFFAOYSA-
    • Curantyl
    • cid_3108
    • HMS3371J03
    • BRD-K86301799-001-34-8
    • HMS1568M06
    • HMS1989N16
    • DTXSID6040668
    • SMP2_000208
    • NINDS_000696
    • AB00051974
    • Apricor
    • EINECS 200-374-7
    • MFCD00010555
    • BSPBio_001554
    • Spectrum5_000839
    • KBio2_004052
    • DIPYRIDAMOLE [USP-RS]
    • Dipyridamole [USAN:USP:INN:BAN:JAN]
    • SBI-0050449.P004
    • HMS1920I10
    • AC-18100
    • HY-B0312R
    • NCGC00023914-07
    • 2,8-dipiperidinopyrimido[5,4-d]pyrimidine
    • NCGC00023914-02
    • DIPYRIDAMOLE [EP MONOGRAPH]
    • Dipiridamol
    • CCG-40190
    • D 9766
    • Dipyridamolum', "2,2',2'',2'''-((4,8-Di(piperidin-1-yl)pyrimido[5,4-d]pyrimidine-2,6-diyl)bis(azanetriyl))tetraethanol", 'RA-8
    • Lopac0_000464
    • UPCMLD-DP072
    • NCGC00015385-03
    • NCGC00015385-10
    • NCGC00023914-09
    • AKOS000509426
    • Dypyridamole
    • Dipridacot
    • BBL027781
    • NCGC00023914-10
    • HMS2232E19
    • Curanty', "2,2',2'',2'''-((4,8-Di(piperidin-1-yl)pyrimido(5,4-d)pyrimidine-2,6-diyl)dinitrilo)tetraethanol", "2,2',2'',2'''-((4,8-dipiperidin-1-ylpyrimido(5,4-d)pyrimidine-2,6-diyl)dinitrilo)tetraethanol", "2,2',2'',2'''-[(4,8-dipiperidin-1-ylpyrimido[5,4-d]pyrimidine-2,6-diyl)dinitrilo]tetraethanol", "Dipyridamole; 2,2',2'',2'''-[[4,8-Di(piperidin-1-yl)pyrimido[5,4-d]pyrimidine-2,6-diyl]dinitrilo]tetraethanol", 'H9F
    • NCGC00023914-11
    • Pyrimido(5, 2,6-bis[bis(2-hydroxyethyl)amino]-4,8-diperidino-', "2,2'',2'''-[4,8-Dipiperidinopyrimido[5,4-d]pyrimidine-2,6-diyl]dinitrilotetraethanol", "2,2',2'',2'''-(4,8-Dipiperidinopyrimido(5,4-d)pyrimidine-2,6-diyl)dinitrilotetraethanol", '2-[[2-(bis(2-hydroxyethyl)amino)-4,8-di(piperidin-1-yl)pyrimido[6,5-e]pyrimidin-
    • Prestwick3_000142
    • Pyrimido(5,4-d)pyrimidine, 2,6-bis(bis(2-hydroxyethyl)amino)-4,8-dipiperidino-
    • KBio1_000696
    • Dipyridamole for peak identification, European Pharmacopoeia (EP) Reference Standard', "Ethanol,2',2'',2'''-(4,8-dipiperidinopyrimido[5,4-d]pyrimidine-2,6-diyldinitrilo)tetra-", 'WLN: T66 BN DN GN INJ CCN HCN E- AT6NTJ B2Q F2Q& J- AT6NTJ B2Q F2Q', "2,2',2'',2''''-((4,8-Dipiperidinopyrimido-(5,4-d)pyrimidine-2,6-diyl)dinitrilo)tetraethanol", "2,2',2'',2'''-(4,8-di(piperidin-1-yl)pyrimido[5,4-d]pyrimidine-2,6-diyl)bis(azanetriyl)tetraethanol", "2,2',2'',2'''-[(4,8-Dipiperidinylpyrimido[5,4-d]pyrimidine-2,6-diyl)dinitrilo]tetraethanol", "2,2',2'',2'''-[(4,8-Dipiperidinylpyrimido[5,4-d]pyrimidine-2,6-diyl)dinitrilo]tetrakisethanol", "Ethanol, 2,2',2'',2'''-(4,8-dipiperidinopyrimido(5,4-d)pyrimidine-2,6-diyldinitrilo)tetra-", "Ethanol, 2,2',2',2'''-((4,8-di-1-iperidinylpyrimido(5,4-d)pyrimidine-2,6-diyl)dinitrilo)tetrakis-", "Ethanol,2',2'',2'''-[(4,8-di-1-piperidinylpyrimido[5,4-d]pyrimidine-2,6-diyl)dinitrilo]tetrakis-", "Ethanol,2',2'',2'''-[(4,8-dipiperidinopyrimido[5,4-d]pyrimidine-2,6-diyl)dinitrilo]tetra-", 'InChI=1/C24H40N8O4/c33-15-11-31(12-16-34)23-26-20-19(21(27-23)29-7-3-1-4-8-29)25-24(32(13-17-35)14-18-36)28-22(20)30-9-5-2-6-10-30/h33-36H,1-18H2
    • Stenocardil
    • Spectrum3_000402
    • Dipyridamole (Persantine)
    • 58-32-2
    • NCGC00015385-04
    • AB00051974_21
    • Piroan
    • Dipyridamolum [INN-Latin]
    • MLS000028420
    • Dipiridamol (INN-Spanish)
    • BPBio1_000270
    • BCP9000613
    • NCGC00015385-18
    • Dipyridan
    • Dipiridamol [INN-Spanish]
    • UPCMLD-DP072:001
    • Opera_ID_494
    • NS00010369
    • BIM-0050449.0001
    • MLS002548866
    • NSC756743
    • EU-0100464
    • Agilease
    • Coribon
    • 2-({6-[bis(2-hydroxyethyl)amino]-4,8-bis(piperidin-1-yl)pyrimido[5,4-d][1,3]diazin-2-yl}(2-hydroxyethyl)amino)ethan-1-ol
    • KBioGR_001123
    • Pharmakon1600-01500259
    • NCGC00015385-14
    • NSC515776
    • BRD-K86301799-001-19-9
    • Z1137167676
    • Dipyridamole (USAN:USP:INN:BAN:JAN)
    • GTPL4807
    • HMS3712M06
    • B01AC07
    • SMR000058382
    • NCGC00023914-08
    • DIPYRIDAMOLE [INN]
    • Cardoxin
    • DIPYRIDAMOLE [JAN]
    • BSPBio_001924
    • Dipyridamol
    • Justpertin
    • AB00051974_20
    • Peridamol
    • Persantin
    • Dipyridamole, United States Pharmacopeia (USP) Reference Standard
    • NCGC00023914-05
    • Dipyridamole, European Pharmacopoeia (EP) Reference Standard
    • Persantine (TN)
    • 2-[[2-[bis(2-hydroxyethyl)amino]-4,8-bis(1-piperidyl)pyrimido[5,4-d]pyrimidin-6-yl]-(2-hydroxyethyl)amino]ethanol
    • DIPYRIDAMOLE [MART.]', "2,2',2'',2'''-{[4,8-di(piperidin-1-yl)pyrimido[5,4-d]pyrimidine-2,6-diyl]dinitrilo}tetraethanol", 'DIPYRIDAMOLE (USP-RS)
    • NSC 515776
    • NCGC00261149-01', "2,2',2'',2'''-((4,8-Di(piperidin-1-yl)pyrimido[5,4-d]-pyrimidine-2,6-diyl)bis(azanetriyl))tetraethanol", '2-({6-[bis(2-hydroxyethyl)amino]-4,8-bis(piperidin-1-yl)-[1,3]diazino[5,4-d]pyrimidin-2-yl}(2-hydroxyethyl)amino)ethan-1-ol
    • Tox21_110133_1
    • SPECTRUM1500259
    • Tocris-0691
    • Permiltin
    • Stimolcardio
    • HMS2095M06
    • HMS3675B03
    • DTXCID4020668
    • BRN 0068373
    • Cleridium 150
    • Dipyridamolum (INN-Latin)', "Ethanol, 2,2',2'',2'''-((4,8-dipiperidinopyrimido(5,4-d)pyrimidine-2,6-diyl)dinitrilo)tetra-", 'DIPYRIDAMOLE (MART.)
    • Usaf Ge-12
    • BCPP000256
    • DivK1c_000696
    • LP00464
    • RA 8
    • HMS3742O03
    • KBio2_001484
    • HMS3402N16
    • 64ALC7F90C
    • SR-01000003065-2
    • Dipyridamole (JP18/USP/INN)
    • Prandiol
    • Dipyramidole
    • Dipyridamole, British Pharmacopoeia (BP) Reference Standard
    • Cardoxil
    • SW196456-3
    • 2,6-Bis(diethanolamino)-4,8-dipiperidinopyrimido[5,4-d]pyrimidine
    • UNII-64ALC7F90C
    • BRD-K86301799-001-35-5
    • HMS3259C03
    • CHEMBL932
    • Coronarine
    • SR-01000003065-5
    • STL377790
    • BDBM23620
    • HMS3261M10
    • Corosan
    • SDCCGSBI-0050449.P005
    • Protangix
    • Prestwick0_000142
    • C24H40N8O4
    • Anginal
    • Dipyudamine
    • HS-0041
    • Cleridium
    • NCGC00015385-13
    • Cardioflux
    • Dipridamole
    • SCHEMBL16119
    • NCGC00015385-17
    • (3E)-3-[[(1S,4aS,8aS)-Decahydro-5,5,8a-trimethyl-2-methylene-1-naphthalenyl]methylene]dihydro-5-methoxy-2(3H)3-[(1E)-2-[(1S,4aS,8aS)-Decahydro-5,5,8a-trimethyl-2-methylene-1-naphthalenyl]ethenyl]furan; (+)-Coronarin E-furanone; Coronarin D methyl ethe
    • SR-01000003065-7
    • HMS502C18
    • Prestwick2_000142
    • DIPYRIDAMOLE [ORANGE BOOK]
    • HMS1791N16
    • NCGC00015385-16
    • HMS2091O18
    • dipyridamole
    • SR-01000003065
    • DIPYRIDAMOLE [MI]
    • Iv Persantine
    • Dipyridamine
    • MLS001076306
    • AB00051974-18
    • DIPYRIDAMOLE [USAN]
    • BRD-K86301799-001-24-9
    • D00302
    • NSC-515776
    • s1895
    • NCGC00015385-02
    • HY-B0312
    • HMS3655I20
    • NCGC00015385-06
    • Tox21_500464
    • NCGC00015385-11
    • NCGC00023914-06
    • KBio2_006620
    • Persantine
    • NC00448
    • SR-01000003065-4
    • AB00051974-19
    • Chilcolan
    • Gulliostin
    • Dipyridamole (Standard)
    • BRD-K86301799-001-04-1
    • DIPYRIDAMOLE COMPONENT OF AGGRENOX
    • Stenocardiol
    • 2,6-Bis(diethanolamino)-4,8-dipiperidinopyrimido(5,4-d)pyrimidine
    • HMS3411B03
    • DIPYRIDAMOLE [VANDF]
    • NCGC00015385-07
    • NCGC00023914-04
    • Prestwick_145
    • HMS2089N15
    • HMS3867F13
    • Coridil
    • O10551
    • Prandiol 75
    • Natyl
    • NSC-619103
    • Kurantil
    • KBioSS_001484
    • BRD-K86301799-001-36-3
    • HMS3266J17
    • DB00975
    • NCGC00015385-15
    • Prestwick1_000142
    • SPBio_002183
    • Dypyridamol
    • Permole
    • IDI1_000696
    • NCGC00015385-01
    • DIPYRIDAMOLE [USP MONOGRAPH]
    • DIPYRIDAMOLE [WHO-DD]
    • NCGC00015385-29
    • Lopac-D-9766
    • SPBio_001003
    • NCGC00015385-12
    • dipiridamolo
    • NCGC00015385-08
    • NCGC00015385-09
    • Spectrum4_000522
    • AC-30804

Attributes

  • Canonical SMILES

    C=C3CC2CC[C@@]1([H])[C@](C)(C)CCC[C@@](C)1C2C[C@H]3/C=C/C4=COC=C4

  • InChI

    InChI=1S/C24H34O/c1-17-14-20-8-9-22-23(2,3)11-5-12-24(22,4)21(20)15-19(17)7-6-18-10-13-25-16-18/h6-7,10,13,16,19-22H,1,5,8-9,11-12,14-15H2,2-4H3/b7-6+/t19-,20?,21?,22+,24-/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 13.14
  • #RotBonds: 2
  • MW: 338.535
  • HBD: 0
  • HBA: 1
  • logP: 7.117800000000007
  • Chemical Formula: C24H34O


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. corymbosa Malaysia, China 1679252 GK604

External Databases


References

  • Tabercarpamines A-J, apoptosis-inducing indole alkaloids from the leaves of Tabernaemontana corymbosa. J Nat Prod, 2014 (PMID 24773071).

Compound-Protein Relationships


Compound Activities

    • Growth 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) -4.81
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.48
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability -3.11
    Distribution Blood-Brain Barrier (Central Nervous System) -1.58
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.84
    Plasma Protein Binding 73.43
    Steady State Volume of Distribution 1.57
    Metabolism Breast Cancer Resistance Protein Inhibitor
    CYP 1A2 Inhibitor Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor Inhibitor
    CYP 2C19 substrate Non-Substrate
    CYP 2C9 Inhibitor Inhibitor
    CYP 2C9 Substrate Non-Substrate
    CYP 2D6 Inhibitor Non-Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 7.89
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 2.68
    Biodegradation Safe
    Carcinogenesis Toxic
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.3
    Liver Injury II Safe
    hERG Blockers Safe
    Daphnia Maga 6.98
    Micronucleos Safe
    NR-AhR Safe
    NR-AR Safe
    NR-AR-LBD Safe
    NR-Aromatase Safe
    NR-ER Safe
    NR-ER-LBD Safe
    NR-GR Toxic
    NR-PPAR-gamma Safe
    NR-TR Safe
    T. Pyriformis -0.31
    Rat (Acute) 2.93
    Rat (Chronic Oral) 2.21
    Fathead Minnow 4.65
    Respiratory Disease Toxic
    Skin Sensitisation Toxic
    SR-ATAD5 Safe
    SR-ARE Toxic
    SR-HSE Toxic
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 388.37
    Hydration Free Energy -2.91
    Log(D) at pH=7.4 5.86
    Log(P) 7.48
    Log S -6.29
    Log(Vapor Pressure) -6.89
    Melting Point 101.58
    pKa Acid 11.52
    pKa Basic 7.44