Leontogenin - Compound Card

Leontogenin

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Leontogenin

Structure
Zoomed Structure
  • Family: Plantae - Dioscoreaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Spirotane
Canonical Smiles O=C[C@@H]1[C@H]2[C@@H]3C[C@H]4[C@@H]([C@@]3(C)CC[C@@H]2[C@@]2([C@@]1(O)C[C@@H](O)CC2)C)[C@@H]([C@]1(O4)CC[C@H](CO1)C)C
InChI InChI=1S/C27H42O5/c1-15-5-10-27(31-14-15)16(2)23-21(32-27)11-19-22-18(7-8-24(19,23)3)25(4)9-6-17(29)12-26(25,30)20(22)13-28/h13,15-23,29-30H,5-12,14H2,1-4H3/t15-,16+,17+,18+,19+,20-,21+,22-,23+,24+,25-,26-,27-/m1/s1
InChIKey GKGKOBNJESCNOE-PHYFNPPMSA-N
Formula C27H42O5
HBA 5
HBD 2
MW 446.63
Rotatable Bonds 1
TPSA 75.99
LogP 3.94
Number Rings 6
Number Aromatic Rings 0
Heavy Atom Count 32
Formal Charge 0
Fraction CSP3 0.96
Exact Mass 446.3
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Tacca leontopetaloides Dioscoreaceae Plantae 72648

Showing of synonyms

  • Abdel-Aziz A, Brain K, et al. (1990). A B-ring contracted spirostane from Tacca leontopetaloides. Phytochemistry,1990,29(8),2623-2627. [View]
Pubchem: 102060705

No compound-protein relationship available.

Structure

SMILES: O1CCCCC12CC3C4C(CC3O2)C5C(CC4)C6C(C5)CCCC6

Level: 0

Mol. Weight: 446.63 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.93
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.680
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.64

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.820
Plasma Protein Binding
70.66
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
14.100
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.000
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.040
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.180
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-127.250
Rat (Acute)
2.950
Rat (Chronic Oral)
1.610
Fathead Minnow
3.760
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
453.800
Hydration Free Energy
-2.570
Log(D) at pH=7.4
4.420
Log(P)
3.88
Log S
-5.02
Log(Vapor Pressure)
-9.16
Melting Point
207.97
pKa Acid
7.82
pKa Basic
6.87
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9328
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9328
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8889
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8889
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.8050
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.8050
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7939
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7939
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7793
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7793
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7786
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7786
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7306
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7306
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7192
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7192
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7110
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7110

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