Dehydrolupinifolinol - Compound Card

Dehydrolupinifolinol

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Dehydrolupinifolinol

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavanol
Canonical Smiles CC(=CCc1c2OC(C)(C)C=Cc2c(c2c1oc(c1ccc(cc1)O)c(c2=O)O)O)C
InChI InChI=1S/C25H24O6/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/h5-9,11-12,26-27,29H,10H2,1-4H3
InChIKey GMVWMCZZGCSTMK-UHFFFAOYSA-N
Formula C25H24O6
HBA 6
HBD 3
MW 420.46
Rotatable Bonds 3
TPSA 100.13
LogP 5.27
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.24
Exact Mass 420.16
Number of Lipinski Rule Violations 1
# 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: 16215899
Nmrshiftdb2: 70024456

No compound-protein relationship available.

Structure

SMILES: O1CC=Cc(c2)c1cc(c23)oc(cc3=O)-c4ccccc4

Level: 1

Mol. Weight: 420.46 g/mol

Structure

SMILES: O=c1ccoc(c12)cc3c(c2)C=CCO3

Level: 0

Mol. Weight: 420.46 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 420.46 g/mol

Anti-leishmanial

Absorption

Caco-2 (logPapp)
-5.01
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.85
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.77

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.44
Plasma Protein Binding
86.4
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
4.57
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.25
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.78
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.42
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
Safe
T. Pyriformis
-33.52
Rat (Acute)
2.55
Rat (Chronic Oral)
2.49
Fathead Minnow
5.26
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
515.68
Hydration Free Energy
-4.87
Log(D) at pH=7.4
3.71
Log(P)
5.2
Log S
-5.88
Log(Vapor Pressure)
-9.69
Melting Point
230.97
pKa Acid
8.33
pKa Basic
6.36
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.9600
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9343
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9134
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8991
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8698
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.8615
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8511
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8500
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 5 0.8431
Cyclin-dependent kinase 5 Q00535 CDK5_HUMAN Homo sapiens 5 0.8217
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8197
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8080
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7878
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7852
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7826
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7825
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.7788
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 4 0.7688
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7656
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 2 0.7597
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7596
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7589
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7579
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 4 0.7570
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7518
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7510
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7505
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7476
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7444
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7395
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7375
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7357
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7294
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7292
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7288
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7276
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7260
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7255
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7221
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 3 0.7217
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7186
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase Q46381 BPHB_COMTE Comamonas testosteroni 3 0.7157
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7126
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7114
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7077
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7065
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7061
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7058
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7050
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7028
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7021
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7005
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7004

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