Methylmonocrotaline - Compound Card

Methylmonocrotaline

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Methylmonocrotaline

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles O=C1O[C@H]2CCN3C2C(=CC3)COC(=O)[C@@]([C@@](C1(C)C)(C)O)(C)O
InChI InChI=1S/C17H25NO6/c1-15(2)13(19)24-11-6-8-18-7-5-10(12(11)18)9-23-14(20)16(3,21)17(15,4)22/h5,11-12,21-22H,6-9H2,1-4H3/t11-,12?,16+,17-/m0/s1
InChIKey NQHCYMOPENHUTC-VDXHGNKCSA-N
Formula C17H25NO6
HBA 7
HBD 2
MW 339.39
Rotatable Bonds 0
TPSA 96.3
LogP -0.0
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.76
Exact Mass 339.17
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Crotalaria fascicularis Leguminosae/Fabaceae Plantae 1132202

Showing of synonyms

  • Asres K, Sporer F, et al. (2004). Patterns of pyrrolizidine alkaloids in 12 Ethiopian Crotalaria species.. Biochemical systematics and ecology,2004,32(10),915-930. [View] [PubMed]
Pubchem: 91749692

No compound-protein relationship available.

Structure

SMILES: C1CN2CCC(C2C=13)OC(=O)CCCC(=O)OC3

Level: 0

Mol. Weight: 339.39 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.87
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.88
Human Oral Bioavailability 50%
Non-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)
0.42
Plasma Protein Binding
28.04
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
3.68
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.09
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.64
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.45
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
-2.99
Rat (Acute)
3.97
Rat (Chronic Oral)
1.87
Fathead Minnow
3.74
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
370.72
Hydration Free Energy
-9.96
Log(D) at pH=7.4
0.35
Log(P)
0.03
Log S
-1.79
Log(Vapor Pressure)
-7.37
Melting Point
204.95
pKa Acid
6.39
pKa Basic
7.0
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.9039
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.9039
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8880
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8880
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.8042
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.8042
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7656
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7656
Raucaffricine-O-beta-D-glucosidase Q9SPP9 RG1_RAUSE Rauvolfia serpentina 3 0.7391
Raucaffricine-O-beta-D-glucosidase Q9SPP9 RG1_RAUSE Rauvolfia serpentina 3 0.7391
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7175
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7175
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7171
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7171
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7094
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7094

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