Madurensine - Compound Card

Madurensine

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Madurensine

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles C/C=C/1\C[C@@H](C)[C@@](C)(O)C(=O)OCC2=CCN3C[C@@H](OC1=O)[C@@H](O)C23
InChI InChI=1S/C18H25NO6/c1-4-11-7-10(2)18(3,23)17(22)24-9-12-5-6-19-8-13(25-16(11)21)15(20)14(12)19/h4-5,10,13-15,20,23H,6-9H2,1-3H3/b11-4+/t10-,13-,14?,15-,18-/m1/s1
InChIKey QBXXZMDYXQHARQ-VREGACOESA-N
Formula C18H25NO6
HBA 7
HBD 2
MW 351.4
Rotatable Bonds 0
TPSA 96.3
LogP 0.16
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 351.17
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Crotalaria agatiflora Leguminosae/Fabaceae Plantae 1127378
2 Crotalaria laburnifolia Leguminosae/Fabaceae Plantae 992673

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: 5459074

No compound-protein relationship available.

Structure

SMILES: C1OC(=O)CCCC(=C)C(=O)OC(C2)CN(C2C1=3)CC3

Level: 0

Mol. Weight: 351.4 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.9
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.92
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.86

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.56
Plasma Protein Binding
24.96
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
4.62
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.84
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.11
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
9.3
Micronucleos
Toxic
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
-4.54
Rat (Acute)
3.7
Rat (Chronic Oral)
1.98
Fathead Minnow
4.01
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
394.69
Hydration Free Energy
-12.07
Log(D) at pH=7.4
0.63
Log(P)
0.73
Log S
-1.75
Log(Vapor Pressure)
-8.4
Melting Point
188.97
pKa Acid
6.31
pKa Basic
6.28
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8952
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8952
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8742
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8742
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8164
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8164
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7958
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7958
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7780
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7780
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7408
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7408
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7072
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7072
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7063
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7063

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