Pseudosemiglabrin - Compound Card

Pseudosemiglabrin

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Pseudosemiglabrin

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Prenylated Flavanone
Canonical Smiles CC(=O)O[C@@H]1[C@H]2[C@@H](OC1(C)C)Oc1c2c2oc(cc(=O)c2cc1)c1ccccc1
InChI InChI=1S/C23H20O6/c1-12(24)26-21-19-18-16(28-22(19)29-23(21,2)3)10-9-14-15(25)11-17(27-20(14)18)13-7-5-4-6-8-13/h4-11,19,21-22H,1-3H3/t19-,21+,22+/m0/s1
InChIKey XTIQPKJOGKMOSY-KSEOMHKRSA-N
Formula C23H20O6
HBA 6
HBD 0
MW 392.41
Rotatable Bonds 2
TPSA 74.97
LogP 4.0
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.3
Exact Mass 392.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Tephrosia apollinea Leguminosae/Fabaceae Plantae 1390541
2 Tephrosia purpurea Leguminosae/Fabaceae Plantae 228354

Showing of synonyms

  • Kassem M.E.S, Sharaf M, et al. (2006). Bioactive Flavonoids from Tephrosia purpurea. Natural product communications, 2006, 1(11),. [View]
  • Khalafallah A, Suleiman S, et al. (2009). Prenylated flavonoids from Tephrosia apollinea. Chinese Chemical Letters, 2009, 20(12), 1465-1468. [View]
Pubchem: 156341
Nmrshiftdb2: 60070783

No compound-protein relationship available.

Structure

SMILES: O1CCC2C1Oc(c23)ccc4c3oc(cc4=O)-c5ccccc5

Level: 1

Mol. Weight: 392.41 g/mol

Structure

SMILES: O1CCC2C1Oc(c23)ccc4c3occc4=O

Level: 0

Mol. Weight: 392.41 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 392.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.87
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.5
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.11

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.4
Plasma Protein Binding
95.15
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
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
7.25
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.76
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.39
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.88
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
-26.76
Rat (Acute)
3.43
Rat (Chronic Oral)
1.36
Fathead Minnow
5.06
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
481.04
Hydration Free Energy
-5.12
Log(D) at pH=7.4
3.68
Log(P)
3.94
Log S
-5.14
Log(Vapor Pressure)
-8.79
Melting Point
183.64
pKa Acid
8.89
pKa Basic
3.0
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.9372
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9149
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9065
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8891
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8381
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8308
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8179
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.8076
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8040
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7964
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7902
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 4 0.7749
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7739
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7709
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 2 0.7665
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7662
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7659
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7653
Phosphodiesterase Q53I60 Q53I60_TRYCR Trypanosoma cruzi 4 0.7640
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7635
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7599
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 3 0.7488
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7470
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7469
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7437
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7435
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7428
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7401
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7398
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7376
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7357
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7355
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7330
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7325
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7323
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7297
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7297
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7291
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7283
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7270
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7241
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7239
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7227
Orf1a polyprotein Q692E5 Q692E5_CVHSA SARS coronavirus TJF 2 0.7145
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7124
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7121
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7120
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 2 0.7111
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7100
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7097
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7061
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7055
Genome polyprotein O93077 O93077_9HEPC Hepacivirus hominis 3 0.7022
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7022
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 3 0.7016
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7010

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