Lupinifolinol - Compound Card

Lupinifolinol

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Lupinifolinol

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavone
Canonical Smiles CC(=CCc1c2O[C@H](c3ccc(cc3)O)[C@H](C(=O)c2c(c2c1OC(C)(C)C=C2)O)O)C
InChI InChI=1S/C25H26O6/c1-13(2)5-10-17-23-16(11-12-25(3,4)31-23)19(27)18-20(28)21(29)22(30-24(17)18)14-6-8-15(26)9-7-14/h5-9,11-12,21-22,26-27,29H,10H2,1-4H3/t21-,22+/m0/s1
InChIKey VRUKIMJALJVJOM-FCHUYYIVSA-N
Formula C25H26O6
HBA 6
HBD 3
MW 422.48
Rotatable Bonds 3
TPSA 96.22
LogP 4.47
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.32
Exact Mass 422.17
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Mundulea sericea Leguminosae/Fabaceae Plantae 54460

Showing of synonyms

  • Chepkirui C, Ochieng PJ, et al. (2021). Antiplasmodial and antileishmanial flavonoids from Mundulea sericea. Fitoterapia,2021, 149(), 104796. [View] [PubMed]
Pubchem: 21721869
Nmrshiftdb2: 60074355

No compound-protein relationship available.

Structure

SMILES: O1CC=Cc(c2)c1cc(c23)OC(CC3=O)c4ccccc4

Level: 1

Mol. Weight: 422.48 g/mol

Structure

SMILES: O=C1CCOc(c12)cc3c(c2)C=CCO3

Level: 0

Mol. Weight: 422.48 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 422.48 g/mol

Anti-plasmodial
Cytotoxic

Absorption

Caco-2 (logPapp)
-5.05
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.82
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.26

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.17
Plasma Protein Binding
85.67
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
Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.39
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.91
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.73
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.13
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
-34.99
Rat (Acute)
2.73
Rat (Chronic Oral)
2.46
Fathead Minnow
4.88
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
489.55
Hydration Free Energy
-4.92
Log(D) at pH=7.4
3.96
Log(P)
5.0
Log S
-5.52
Log(Vapor Pressure)
-9.68
Melting Point
212.26
pKa Acid
6.94
pKa Basic
4.69
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9299
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.9094
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9013
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.9006
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8766
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 5 0.8447
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8332
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.8215
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8125
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7974
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7967
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7743
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.7743
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7706
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7490
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7486
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7466
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7383
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7371
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 4 0.7316
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7309
Cyclin-dependent kinase 6 Q00534 CDK6_HUMAN Homo sapiens 5 0.7294
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A Q13946 PDE7A_HUMAN Homo sapiens 3 0.7287
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7277
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7263
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7227
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7179
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7179
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7144
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 4 0.7123
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7121
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7092
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7090
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.7077
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.7070
23S rRNA (guanine(745)-N(1))-methyltransferase P36999 RLMA_ECOLI Escherichia coli 3 0.7027
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 4 0.7005

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