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Monocrotaline
- Family: Plantae - Leguminosae/Fabaceae
- Kingdom: Plantae
- Class: Alkaloid
| Canonical Smiles | O=C1O[C@@H]2CCN3[C@@H]2C(=CC3)COC(=O)[C@]([C@]([C@H]1C)(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 |
| InChIKey | QVCMHGGNRFRMAD-XFGHUUIASA-N |
| Formula | C16H23NO6 |
| HBA | 7 |
| HBD | 2 |
| MW | 325.36 |
| Rotatable Bonds | 0 |
| TPSA | 96.3 |
| LogP | -0.39 |
| Number Rings | 3 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 23 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.75 |
| Exact Mass | 325.15 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Crotalaria albicaulis | Leguminosae/Fabaceae | Plantae | 1132156 |
Showing of synonyms
Monocrotaline
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-
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.)-
(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)-
(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.
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)
(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-
20-Norcrotalanan-11,15-dione, 14,19-dihydro-12,13-dihydroxy-, (13-alpha,14-alpha)-(9CI)
628-506-2
Qvcmhggnrfrmad-uhfffaoysa-n
Qvcmhggnrfrmad-xfghuuiasa-n
Crotaline
NCGC00164256-01
SR-01000838886
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
Monocrotaline, analytical standard
NINDS_000959
HMS1569J08
HMS1921P04
HMS2096J08
HMS2235J12
HY-N0750
MSK14173
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
(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
(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
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
Pubchem:
9415
Cas:
315-22-0
Gnps:
CCMSLIB00005767777
Zinc:
ZINC000053195720
Kegg Ligand:
C10350
Chebi:
6980
Metabolights:
MTBLC6980
Chembl:
CHEMBL521035
Comptox:
DTXSID9020902
Bindingdb:
50480309
CPRiL:
2228
SMILES: C1CN2CCC(C2C=13)OC(=O)CCCC(=O)OC3
Level: 0
Mol. Weight: 325.36 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.9
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.89
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.42
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.36
- Plasma Protein Binding
- 21.16
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 2.71
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.33
- Biodegradation
- Toxic
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.54
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 7.37
- 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
- -2.73
- Rat (Acute)
- 3.94
- Rat (Chronic Oral)
- 1.87
- Fathead Minnow
- 3.65
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 375.46
- Hydration Free Energy
- -10.72
- Log(D) at pH=7.4
- 0.0
- Log(P)
- -0.59
- Log S
- -1.4
- Log(Vapor Pressure)
- -7.9
- Melting Point
- 211.24
- pKa Acid
- 6.16
- pKa Basic
- 7.03
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7865 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7865 |
| Steroid C26-monooxygenase | P9WPP1 | CP125_MYCTU | Mycobacterium tuberculosis | 3 | 0.7833 |
| Steroid C26-monooxygenase | P9WPP1 | CP125_MYCTU | Mycobacterium tuberculosis | 3 | 0.7833 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7569 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7569 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7419 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7419 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.7340 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.7340 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7336 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7336 |
| Vitamin D-binding protein | P02774 | VTDB_HUMAN | Homo sapiens | 2 | 0.7241 |
| Vitamin D-binding protein | P02774 | VTDB_HUMAN | Homo sapiens | 2 | 0.7241 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 3 | 0.7102 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 3 | 0.7102 |