Monocrotaline
PubChem CID: 9415
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| Compound Synonyms | monocrotaline, Crotaline, 315-22-0, Monocrotalin, (-)-Monocrotaline, NCI-C56462, CCRIS 416, CHEBI:6980, HSDB 3513, A 6080, Retronecine cyclic 2,3-dihydroxy-2,3,4-trimethylglutarate, UNII-73077K8HYV, BRN 0048732, MLS002153902, DTXSID9020902, 73077K8HYV, (13-alpha,14-alpha)-14,19-Dihydro-12,13-dihydroxy-20-norcrotalanan-11,15-dione, MONOCROTALINE [MI], 14,19-Dihydro-12,13-dihydroxy-20-norcrotolanan-11,15-dione, MONOCROTALINE [HSDB], MONOCROTALINE [IARC], NSC 28693, DTXCID50902, 20-Norcrotalanan-11,15-dione, 14,19-dihydro-12,13-dihydroxy-, (13alpha,14alpha)-, (3R,4R,5R,13aR,13bR)-4,5-dihydroxy-3,4,5-trimethyl-4,5,8,10,12,13,13a,13b-octahydro-2H-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione, 4-27-00-06660 (Beilstein Handbook Reference), 12-beta,13-beta-Dihydroxy-12-alpha,13-alpha,14-alpha-trimethylcrotal-1-enine, NSC-28693, 14,19-Dihydro-12,13-dihydroxy(13-alpha,14-alpha)-20-norcrotalanan-11,15-dione, (2,3,4-gh)pyrrolizine-2,6(3H)-dione, (4,5,8,10,12,13,13a,13b)-octahydro-4,5-dihydroxy-3,4,5-trimethyl-2H-(1,6)dioxacycloundecino-, NCGC00164256-01, 20-Norcrotalanan-11,15-dione, 14,19-dihydro-12,13-dihydroxy-, (13-alpha,14-alpha)-, MONOCROTALINE (IARC), (1R,4R,5R,6R,16R)-5,6-dihydroxy-4,5,6-trimethyl-2,8-dioxa-13-azatricyclo[8.5.1.013,16]hexadec-10-ene-3,7-dione, 2H-(1,6)Dioxacycloundecino(2,3,4-gh)pyrrolizine-2,6(3H)-dione, 4,5,8,10,12,13,13a,13b-octahydro-4,5-dihydroxy-3,4,5-trimethyl-, (3R,4R,5R,13aR,13bR)-, 2H-[1,6]Dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione, 4,5,8,10,12,13,13a,13b-octahydro-4,5-dihydroxy-3,4,5-trimethyl-, (3R,4R,5R,13aR,13bR)-, 2H-(1,6)DIOXACYCLOUNDECINO(2,3,4-GH)PYRROLIZINE-2,6(3H)-DIONE, 4,5,8,10,12,13,13A,13B-OCTAHYDRO-4,5-DIHYDROXY-3,4,5-TRIMETHYL-, (3R-(3R*,4R*,5R*,13AR*,13BR*))-, 20-Norcrotalanan-11,15-dione, 14,19-dihydro-12,13-dihydroxy-, (13.alpha.,14.alpha.)-, SR-01000838886, (1R,4R,5R,6R,16R)-5,6-dihydroxy-4,5,6-trimethyl-2,8-dioxa-13-azatricyclo(8.5.1.013,16)hexadec-10-ene-3,7-dione, (3R,4R,5R,13aR,13bR)-4,5-dihydroxy-3,4,5-trimethyl-4,5,8,10,12,13,13a,13b-octahydro-2H-(1,6)dioxacycloundecino(2,3,4-gh)pyrrolizine-2,6(3H)-dione, 2H-(1,6)DIOXACYCLOUNDECINO(2,3,4-gh)PYRROLIZINE-2,6(3H)-DIONE, 4,5,8,10,12,13,13a,13b-OCTAHYDRO-4,5-DIHYDROXY-3,4,5-TRIMETHYL-,(3R,4R,5R,13aR,13bR)-, 2H-[1,6]DIOXACYCLOUNDECINO[2,3,4-gh]PYRROLIZINE-2,6(3H)-DIONE, 4,5,8,10,12,13,13a,13b-OCTAHYDRO-4,5-DIHYDROXY-3,4,5-TRIMETHYL-,(3R,4R,5R,13aR,13bR)-, CAS-315-22-0, Prestwick_338, MFCD00084656, Spectrum_001224, Prestwick0_000603, Prestwick1_000603, Prestwick2_000603, Prestwick3_000603, Spectrum2_000906, Spectrum3_000947, Spectrum4_001057, Spectrum5_001233, BSPBio_000506, KBioGR_001354, KBioSS_001704, DivK1c_000959, SCHEMBL164486, SPECTRUM1502252, SPBio_000752, SPBio_002725, BPBio1_000558, CHEMBL521035, MEGxp0_001899, ACon0_000305, ACon1_000179, HMS502P21, KBio1_000959, KBio2_001704, KBio2_004272, KBio2_006840, KBio3_002014, (13-.alpha.,14-.alpha.)-14,19-Dihydro-12,13-dihydroxy-20-norcrotalanan-11,15-dione, 12.beta.,13.beta.-Dihydroxy-12.alpha.,13.alpha.,14.alpha.-trimethylcrotal-1-enine, 14,19-Dihydro-12,13-dihydroxy(13.alpha.,14.alpha.)-20-norcrotalanan-11,15-dione, 2H-(1,6)Dioxacycloundecino(2,3,4-gh)pyrrolizine, 20-norcrotalanan-11,15-dione deriv., 2H-[1,6]Dioxacycloundecino[2,3,4-gh]pyrrolizine, 20-norcrotalanan-11,15-dione deriv., Monocrotaline, analytical standard, NINDS_000959, HMS1569J08, HMS1921P04, HMS2096J08, HMS2235J12, HY-N0750, Tox21_112094, Tox21_201509, Tox21_302874, BDBM50480309, CCG-39621, s3812, AKOS015969712, AKOS032962048, Tox21_112094_1, CS-6164, FM64904, FS-5652, SDCCGMLS-0066675.P001, IDI1_000959, NCGC00179538-01, NCGC00179538-02, NCGC00179538-03, NCGC00256518-01, NCGC00259060-01, NCGC00262539-03, 1ST14173, AC-34918, SMR001233251, JACS 72: 158 (1950), SR-01000838886-3, SR-01000838886-4, BRD-K65508953-001-05-5, BRD-K65508953-001-08-9, Q27107379, Retronecine cyclic 2,3dihydroxy2,3,4trimethylglutarate, 12beta,13betaDihydroxy12alpha,13alpha,14alphatrimethylcrotal1enine, (13alpha,14alpha)14,19Dihydro12,13dihydroxy20norcrotalanan11,15dione, 12beta,13beta-Dihydroxy-12alpha,13alpha,14alpha-trimethylcrotal-1-enine, 14,19Dihydro12,13dihydroxy(13alpha,14alpha)20norcrotalanan11,15dione, (13alpha, 14alpha)-14,19-Dihydro-12,13-dihydroxy-20-norcrotolanan-11,15-dione, 14,19-Dihydro-12,13-dihydroxy(13alpha,14alpha)-20-norcrotalanan-11,15-dione, 20Norcrotalanan11,15dione, 14,19dihydro12,13dihydroxy, (13alpha,14alpha), (1R,4R,5R,6R,16R)-5,6-dihydroxy-4,5,6-trimethyl-2,8-dioxa-13-azatricyclo[8.5.1.0??,??]hexadec-10-ene-3,7-dione, (2,3,4-GH)PYRROLIZINE-2,6(3H)-DIONE, (4,5,8,10,12,13,13A,13B-OCTAHYDRO-4,5-DIHYDROXY-3,4,5-TRIMETHYL-2H-(1,6)DIOXACYCLOUNDECINO-, (3R,4R,5R,8a1R,13aR)-4,5-Dihydroxy-3,4,5-trimethyl-4,5,8,8a1,10,12,13,13a-octahydro-2H-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione, (3R,4R,8a1R,13aR)-4,5-Dihydroxy-3,4,5-trimethyl-4,5,8,8a1,10,12,13,13a-octahydro-2H-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione, 109525-74-8, 20-Norcrotalanan-11,15-dione, 14,19-dihydro-12,13-dihydroxy-, (13-alpha,14-alpha)-(9CI), 628-506-2, rel-(3R,4R,5R,8a1R,13aR)-4,5-Dihydroxy-3,4,5-trimethyl-4,5,8,8a1,10,12,13,13a-octahydro-2H-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione |
|---|---|
| Ghose Rule | True |
| Classyfire Kingdom | Organic compounds |
| Topological Polar Surface Area | 96.3 |
| Hydrogen Bond Donor Count | 2.0 |
| Pfizer 3 75 Rule | True |
| Scaffold Graph Level | CC1CCCC(C)CC2CCC3CCC(CC1)C32 |
| Np Classifier Class | Pyrrolizidine alkaloids |
| Deep Smiles | O=CO[C@@H]CCN[C@@H]5C=CC5))COC=O)[C@][C@][C@H]%14C))C)O))C)O |
| Heavy Atom Count | 23.0 |
| Classyfire Class | Pyrrolizines |
| Scaffold Graph Node Level | OC1CCCC(O)OC2CCN3CCC(CO1)C23 |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 575.0 |
| Database Name | cmaup_ingredients;imppat_phytochem;npass_chem_all;pubchem |
| Defined Atom Stereocenter Count | 5.0 |
| Uniprot Id | Q72547, P00811, P10828, O75496, P04637, O42275, P81908, Q9NUW8, Q9Y6L6, Q9NPD5, n.a., P04792 |
| Iupac Name | (1R,4R,5R,6R,16R)-5,6-dihydroxy-4,5,6-trimethyl-2,8-dioxa-13-azatricyclo[8.5.1.013,16]hexadec-10-ene-3,7-dione |
| Prediction Hob | 1.0 |
| Veber Rule | True |
| Classyfire Superclass | Organoheterocyclic compounds |
| Xlogp | -0.7 |
| Gsk 4 400 Rule | True |
| Molecular Formula | C16H23NO6 |
| Scaffold Graph Node Bond Level | O=C1CCCC(=O)OC2CCN3CC=C(CO1)C23 |
| Prediction Swissadme | 0.0 |
| Inchi Key | QVCMHGGNRFRMAD-XFGHUUIASA-N |
| Silicos It Class | Soluble |
| Fcsp3 | 0.75 |
| Logs | -1.96 |
| Rotatable Bond Count | 0.0 |
| Logd | 0.907 |
| Synonyms | crotaline, monocrotaline, pyrrolizidine alkaloid |
| Esol Class | Very soluble |
| Functional Groups | CC=C(C)C, CN(C)C, CO, COC(C)=O |
| Compound Name | Monocrotaline |
| Prediction Hob Swissadme | 0.0 |
| Exact Mass | 325.153 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 325.153 |
| Hydrogen Bond Acceptor Count | 7.0 |
| Molecular Weight | 325.36 |
| Gi Absorption | True |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 5.0 |
| Total Bond Stereocenter Count | 0.0 |
| Lipinski Rule Of 5 | True |
| Esol | -1.3973382000000005 |
| Inchi | InChI=1S/C16H23NO6/c1-9-13(18)23-11-5-7-17-6-4-10(12(11)17)8-22-14(19)16(3,21)15(9,2)20/h4,9,11-12,20-21H,5-8H2,1-3H3/t9-,11+,12+,15+,16-/m0/s1 |
| Smiles | C[C@H]1C(=O)O[C@@H]2CCN3[C@@H]2C(=CC3)COC(=O)[C@]([C@]1(C)O)(C)O |
| Nring | 3.0 |
| Np Classifier Biosynthetic Pathway | Alkaloids |
| Defined Bond Stereocenter Count | 0.0 |
| Egan Rule | True |
| Np Classifier Superclass | Ornithine alkaloids |
- 1. Outgoing r'ship
FOUND_INto/from Caccinia Macranthera (Plant) Rel Props:Reference:ISBN:9780387706375 - 2. Outgoing r'ship
FOUND_INto/from Cordia Dichotoma (Plant) Rel Props:Reference:ISBN:9788172361150 - 3. Outgoing r'ship
FOUND_INto/from Crotalaria Assamica (Plant) Rel Props:Reference:ISBN:9788172360481; ISBN:9788172362133; ISBN:9788185042084; ISBN:9788185042114 - 4. Outgoing r'ship
FOUND_INto/from Crotalaria Barbata (Plant) Rel Props:Reference:ISBN:9770972795006 - 5. Outgoing r'ship
FOUND_INto/from Crotalaria Burhia (Plant) Rel Props:Reference:ISBN:9770972795006 - 6. Outgoing r'ship
FOUND_INto/from Crotalaria Calycina (Plant) Rel Props:Reference:ISBN:9788185042114 - 7. Outgoing r'ship
FOUND_INto/from Crotalaria Ferruginea (Plant) Rel Props:Reference:ISBN:9788185042114 - 8. Outgoing r'ship
FOUND_INto/from Crotalaria Grahamiana (Plant) Rel Props:Reference:ISBN:9788185042114 - 9. Outgoing r'ship
FOUND_INto/from Crotalaria Mysorensis (Plant) Rel Props:Reference:ISBN:9770972795006; ISBN:9788185042053 - 10. Outgoing r'ship
FOUND_INto/from Crotalaria Pallida (Plant) Rel Props:Reference:ISBN:9770972795006; ISBN:9788172362133 - 11. Outgoing r'ship
FOUND_INto/from Crotalaria Retusa (Plant) Rel Props:Reference:https://doi.org/10.15482/usda.adc/1239279 - 12. Outgoing r'ship
FOUND_INto/from Crotalaria Sessiliflora (Plant) Rel Props:Reference:ISBN:9788185042114 - 13. Outgoing r'ship
FOUND_INto/from Crotalaria Spectabilis (Plant) Rel Props:Reference:ISBN:9788172361266 - 14. Outgoing r'ship
FOUND_INto/from Crotalaria Stipularia (Plant) Rel Props:Reference:ISBN:9770972795006 - 15. Outgoing r'ship
FOUND_INto/from Crotalaria Umbellata (Plant) Rel Props:Reference:ISBN:9788185042084 - 16. Outgoing r'ship
FOUND_INto/from Heliotropium Zeylanicum (Plant) Rel Props:Reference:ISBN:9788172362300 - 17. Outgoing r'ship
FOUND_INto/from Parsonsia Alboflavescens (Plant) Rel Props:Reference:ISBN:9788185042145 - 18. Outgoing r'ship
FOUND_INto/from Senecio Scandens (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all