Lupinifolin - Compound Card

Lupinifolin

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Lupinifolin

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavanone
Canonical Smiles CC(=CCc1c2OC(CC(=O)c2c(c2c1OC(C)(C)C=C2)O)c1ccc(cc1)O)C
InChI InChI=1S/C25H26O5/c1-14(2)5-10-18-23-17(11-12-25(3,4)30-23)22(28)21-19(27)13-20(29-24(18)21)15-6-8-16(26)9-7-15/h5-9,11-12,20,26,28H,10,13H2,1-4H3
InChIKey PDTJZCUQXSFLDW-UHFFFAOYSA-N
Formula C25H26O5
HBA 5
HBD 2
MW 406.48
Rotatable Bonds 3
TPSA 75.99
LogP 5.5
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.32
Exact Mass 406.18
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Derris trifoliata Leguminosae/Fabaceae Plantae 185716

Showing of synonyms

  • Yenesew AB, Twinomuhwezi H, et al. (2009). Antiplasmodial and larvicidal flavonoids from Derris trifoliata.. Bulletin of the Chemical Society of Ethiopia,2009,23(3),409-414. [View] [PubMed]
Pubchem: 13846826
Nmrshiftdb2: 70017132

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 406.48 g/mol

Structure

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

Level: 0

Mol. Weight: 406.48 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 406.48 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.69
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.73
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.69

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.18
Plasma Protein Binding
55.38
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
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
5.7
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.04
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.25
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.64
Micronucleos
Toxic
NR-AhR
Toxic
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
Toxic
T. Pyriformis
-19.57
Rat (Acute)
2.38
Rat (Chronic Oral)
2.1
Fathead Minnow
5.13
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
485.02
Hydration Free Energy
-5.59
Log(D) at pH=7.4
4.3
Log(P)
5.79
Log S
-6.3
Log(Vapor Pressure)
-9.07
Melting Point
183.99
pKa Acid
8.38
pKa Basic
5.42
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.9397
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.9397
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9386
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9386
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.9323
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.9323
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.9047
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.9047
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8855
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8855
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8493
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8493
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8481
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8481
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.8429
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.8429
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.8358
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.8358
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8308
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8308
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.8243
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.8243
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8107
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8107
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8083
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.8083
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8083
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.8083
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8029
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8029
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7994
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7994
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7876
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7876
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7751
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7751
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7714
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7714
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.7661
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.7661
Apoptosis regulator Bcl-2 P10415 BCL2_HUMAN Homo sapiens 3 0.7569
Apoptosis regulator Bcl-2 P10415 BCL2_HUMAN Homo sapiens 3 0.7569
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A Q13946 PDE7A_HUMAN Homo sapiens 3 0.7534
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A Q13946 PDE7A_HUMAN Homo sapiens 3 0.7534
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7507
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7507
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7464
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7464
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7433
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7433
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7419
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7419
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7414
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7414
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7411
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7411
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.7399
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.7399
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 4 0.7396
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 4 0.7396
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7384
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7384
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7306
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7306
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7295
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7295
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7292
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7292
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7289
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7289
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7280
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7280
Threonine--tRNA ligase P0A8M3 SYT_ECOLI Escherichia coli 3 0.7272
Threonine--tRNA ligase P0A8M3 SYT_ECOLI Escherichia coli 3 0.7272
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7253
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7253
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7222
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7222
23S rRNA (guanine(745)-N(1))-methyltransferase P36999 RLMA_ECOLI Escherichia coli 3 0.7197
23S rRNA (guanine(745)-N(1))-methyltransferase P36999 RLMA_ECOLI Escherichia coli 3 0.7197
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7180
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7180
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7155
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7155
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7078
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7078
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7049
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7049
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.7035
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.7035

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