Monocrotaline

Details

• Internal ID: 478a1b0f-3619-4592-bd37-236abcbb1c90
• Taxonomy: Organoheterocyclic compounds > Pyrrolizines
• 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
• SMILES (Canonical): CC1C(=O)OC2CCN3C2C(=CC3)COC(=O)C(C1(C)O)(C)O
• SMILES (Isomeric): C[C@H]1C(=O)O[C@@H]2CCN3[C@@H]2C(=CC3)COC(=O)[C@]([C@]1(C)O)(C)O
• 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
• InChI Key: QVCMHGGNRFRMAD-XFGHUUIASA-N
• Popularity: 3,062 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₃NO₆
• Molecular Weight: 325.36 g/mol
• Exact Mass: 325.15253745 g/mol
• Topological Polar Surface Area (TPSA): 96.30 Ų
• XlogP: -0.70

Synonyms

• Crotaline
• 315-22-0
• Monocrotalin
• (-)-Monocrotaline
• NCI-C56462
• NSC 28693
• CCRIS 416
• CHEBI:6980
• HSDB 3513
• Retronecine cyclic 2,3-dihydroxy-2,3,4-trimethylglutarate
• A 6080
• BRN 0048732
• (13-alpha,14-alpha)-14,19-Dihydro-12,13-dihydroxy-20-norcrotalanan-11,15-dione
• UNII-73077K8HYV
• MLS002153902
• DTXSID9020902
• 14,19-Dihydro-12,13-dihydroxy-20-norcrotolanan-11,15-dione
• 73077K8HYV
• 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
• NCGC00164256-01
• 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
• (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-
• 4-27-00-06660 (Beilstein Handbook Reference)
• DTXCID50902
• 20-Norcrotalanan-11,15-dione, 14,19-dihydro-12,13-dihydroxy-, (13-alpha,14-alpha)-
• 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)-
• SR-01000838886
• NSC-28693
• 20-Norcrotalanan-11,15-dione, 14,19-dihydro-12,13-dihydroxy-, (13.alpha.,14.alpha.)-
• CAS-315-22-0
• Prestwick_338
• Spectrum_001224
• Prestwick0_000603
• Prestwick1_000603
• Prestwick2_000603
• Prestwick3_000603
• Spectrum2_000906
• Spectrum3_000947
• Spectrum4_001057
• Spectrum5_001233
• MONOCROTALINE [MI]
• D0G6AB
• MONOCROTALINE [HSDB]
• MONOCROTALINE [IARC]
• 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
• Monocrotaline, analytical standard
• NINDS_000959
• HMS1569J08
• HMS1921P04
• HMS2096J08
• HMS2235J12
• HY-N0750
• Tox21_112094
• Tox21_201509
• Tox21_302874
• BDBM50480309
• CCG-39621
• MFCD00084656
• s3812
• AKOS015969712
• AKOS032962048
• Tox21_112094_1
• CS-6164
• FS-5652
• LS-7530
• SDCCGMLS-0066675.P001
• IDI1_000959
• NCGC00179538-01
• NCGC00179538-02
• NCGC00179538-03
• NCGC00256518-01
• NCGC00259060-01
• NCGC00262539-03
• AC-34918
• SMR001233251
• JACS 72: 158 (1950)
• Q-100395
• SR-01000838886-3
• SR-01000838886-4
• BRD-K65508953-001-05-5
• BRD-K65508953-001-08-9
• Q27107379
• (13-alpha,14-alpha)-14,19-dihydro-12,13-dihydroxy-20-norcrotolanan-11,15-dione
• (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
• (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,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
• (3S,4S,5R,13aR)-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
• 109525-74-8
• 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*))-
• 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

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.44%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.36%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.29%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.93%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.47%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.94%	94.45%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.29%	92.94%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.80%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.31%	97.25%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	83.03%	93.40%
CHEMBL1871	P10275	Androgen Receptor	82.58%	96.43%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.98%	99.23%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.14%	97.14%

Plants that contains it

• Crotalaria aegyptiaca
• Crotalaria grahamiana
• Crotalaria nitens
• Crotalaria recta
• Crotalaria retusa
• Crotalaria sagittalis
• Crotalaria scassellatii
• Crotalaria sessiliflora
• Crotalaria spectabilis
• Petasites hybridus
• Senecio scandens

Cross-Links

• PubChem: 9415
• NPASS: NPC30911
• ChEMBL: CHEMBL521035
• LOTUS: LTS0048870
• wikiData: Q27107379