13-hydroxylupanine - Compound Card

13-hydroxylupanine

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13-hydroxylupanine

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Quinolizidine Alkaloid
Canonical Smiles OC1CCN2C(C1)C1CC(C2)C2N(C1)C(=O)CCC2
InChI InChI=1S/C15H24N2O2/c18-12-4-5-16-8-10-6-11(14(16)7-12)9-17-13(10)2-1-3-15(17)19/h10-14,18H,1-9H2
InChIKey JVYKIBAJVKEZSQ-UHFFFAOYSA-N
Formula C15H24N2O2
HBA 3
HBD 1
MW 264.37
Rotatable Bonds 0
TPSA 43.78
LogP 0.84
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.93
Exact Mass 264.18
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Lupinus digitatus Leguminosae/Fabaceae Plantae 53225
2 Lupinus tassilicus Leguminosae/Fabaceae Plantae 925616

Showing of synonyms

  • Ainouche A, Greinwald R, et al. (1996). Seed Alkaloid Composition of Lupinus tassilicus Maire (Fabaceae: Genisteae) and Comparison with its Related Rough Seeded Lupin Species. Biochemical Systematics and Ecology, 1996, 24(5), 405-414. [View]
Pubchem: 250873
Nmrshiftdb2: 60068195
CPRiL: 303002
Structure

SMILES: C1CCC(=O)N(C1C23)CC(C2)C4N(C3)CCCC4

Level: 0

Mol. Weight: 264.37 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.44
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.99
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.47

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.27
Plasma Protein Binding
27.35
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
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
9.1
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Toxic
Bee
Toxic
Bioconcentration Factor
-1.97
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.59
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.17
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
4.6
Rat (Acute)
2.19
Rat (Chronic Oral)
1.38
Fathead Minnow
3.58
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
369.06
Hydration Free Energy
-6.17
Log(D) at pH=7.4
-1.02
Log(P)
-0.2
Log S
-1.14
Log(Vapor Pressure)
-7.26
Melting Point
130.83
pKa Acid
9.0
pKa Basic
9.71
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.8500
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 3 0.8224
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8010
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7811
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7613
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7559
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7546
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7374
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7348
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7041
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7037

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