Poinsettifolin B - Compound Card

Poinsettifolin B

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Poinsettifolin B

Structure
Zoomed Structure
  • Family: Plantae - Moraceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Geranylated Flavonoid
Canonical Smiles CC(=CCCC1(C)C=Cc2c(O1)c(O)ccc2/C=C/C(=O)c1ccc(c(c1O)CC=C(C)C)O)C
InChI InChI=1S/C30H34O5/c1-19(2)7-6-17-30(5)18-16-22-21(10-14-27(33)29(22)35-30)9-13-25(31)24-12-15-26(32)23(28(24)34)11-8-20(3)4/h7-10,12-16,18,32-34H,6,11,17H2,1-5H3/b13-9+
InChIKey MPFPWDKHTLSMIF-UKTHLTGXSA-N
Formula C30H34O5
HBA 5
HBD 3
MW 474.6
Rotatable Bonds 8
TPSA 86.99
LogP 7.12
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 35
Formal Charge 0
Fraction CSP3 0.3
Exact Mass 474.24
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Dorstenia poinsettiifolia Moraceae Plantae 2605000

Showing of synonyms

  • Ngadjui BT, Kapche GW, et al. (1999). Prenylated flavonoids and a dihydro-4-phenylcoumarinfrom Dorstenia poinsettifolia. Phytochemistry, 1999, 51(1), 119-123. [View]
Pubchem: 11798732

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)C=Cc2cccc(c23)OCC=C3

Level: 1

Mol. Weight: 474.6 g/mol

Structure

SMILES: C1=CCOc(c12)cccc2

Level: 0

Mol. Weight: 474.6 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 474.6 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.0
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.85
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.58

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.22
Plasma Protein Binding
59.55
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
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
Non-Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
4.53
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.9
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.61
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.3
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
-187.92
Rat (Acute)
2.11
Rat (Chronic Oral)
2.83
Fathead Minnow
5.87
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
518.36
Hydration Free Energy
-3.2
Log(D) at pH=7.4
4.9
Log(P)
8.55
Log S
-7.08
Log(Vapor Pressure)
-9.57
Melting Point
165.17
pKa Acid
8.87
pKa Basic
6.3
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9460
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.9236
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9134
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8967
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8918
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8908
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.8855
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8770
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8699
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8659
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8545
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8453
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8428
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 3 0.8425
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8369
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.8361
Isoliquiritigenin 2'-O-methyltransferase P93324 CHOMT_MEDSA Medicago sativa 4 0.8336
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8295
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 3 0.8217
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8184
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.8141
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.8092
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 3 0.8084
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8057
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7975
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7966
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7960
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7937
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 3 0.7884
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7878
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7867
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 4 0.7849
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7844
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7835
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.7812
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7780
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7777
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7773
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.7768
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7730
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7725
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7720
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7719
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7713
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7703
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7669
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7650
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 3 0.7647
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7576
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7548
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7543
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7535
DNA double-strand break repair protein Mre11 Q9X1X0 Q9X1X0_THEMA Thermotoga maritima MSB8 3 0.7526
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7522
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7485
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7481
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7477
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7476
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7476
Chloramphenicol acetyltransferase P62577 CAT_ECOLX Escherichia coli 2 0.7475
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 3 0.7465
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7459
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.7456
Acetylcholine-binding protein P58154 ACHP_LYMST Lymnaea stagnalis 3 0.7447
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7396
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 4 0.7381
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.7380
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7374
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7372
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7368
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.7359
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7354
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7339
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7321
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7318
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7307
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7302
3',5'-cyclic-AMP phosphodiesterase 4A P27815 PDE4A_HUMAN Homo sapiens 3 0.7292
Corticosteroid-binding globulin P31211 CBG_RAT Rattus norvegicus 3 0.7277
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7263
Japanin M1MR49 M1MR49_RHIAP Rhipicephalus appendiculatus 4 0.7260
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7258
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7254
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7245
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7221
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7220
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7208
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7206
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7197
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7197
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7187
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7187
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7182
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7179
Purine nucleoside phosphorylase DeoD-type Q5EEL8 DEOD_BACCE Bacillus cereus 3 0.7175
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7173
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.7173
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.7158
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 3 0.7157
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 3 0.7142
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7130
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7129
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 3 0.7128
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7124
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7119
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 3 0.7111
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7108
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7107
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7085
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7078
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7076
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7074
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 3 0.7072
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7072
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.7071
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.7068
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7068
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7061
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7060
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 2 0.7052
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7046
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7046
FKBP-type peptidyl-prolyl cis-trans isomerase FkpA P45523 FKBA_ECOLI Escherichia coli 4 0.7042
Casein kinase I isoform gamma-2 P78368 KC1G2_HUMAN Homo sapiens 3 0.7034
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7033
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.7017
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7014
3',5'-cyclic-AMP phosphodiesterase 4B Q07343 PDE4B_HUMAN Homo sapiens 3 0.7012
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7008
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7000

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