Seputhecarpan B - Compound Card

Seputhecarpan B

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Seputhecarpan B

Structure
Zoomed Structure
  • Family: Sapotaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Pterocarpan
Canonical Smiles OCC(=C)[C@@H]1Oc2c(C1)cc1c(c2)OC[C@H]2[C@@H]1Oc1c2ccc(c1)O
InChI InChI=1S/C20H18O5/c1-10(8-21)16-5-11-4-14-18(7-17(11)24-16)23-9-15-13-3-2-12(22)6-19(13)25-20(14)15/h2-4,6-7,15-16,20-22H,1,5,8-9H2/t15-,16-,20-/m1/s1
InChIKey ZLKIFMGEGVNRAI-JXXFODFXSA-N
Formula C20H18O5
HBA 5
HBD 2
MW 338.36
Rotatable Bonds 2
TPSA 68.15
LogP 2.85
Number Rings 5
Number Aromatic Rings 2
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.3
Exact Mass 338.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Synsepalum zenkeri Sapotaceae Plantae 233754

Showing of synonyms

  • Kuete V, Ngnintedo D, et al. (2018). Cytotoxicity of seputhecarpan D, thonningiol and 12 other phytochemicals from African flora towards human carcinoma cells.. BMC complementary and alternative medicine,2018, 18(1), 36. [View] [PubMed]
Pubchem: 132557132

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)OC3C2COc4c3cc5c(c4)OCC5

Level: 0

Mol. Weight: 266.3 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.87
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.530
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.01

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.990
Plasma Protein Binding
75.64
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
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
12.810
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.060
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.110
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.430
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
-3.970
Rat (Acute)
2.470
Rat (Chronic Oral)
1.800
Fathead Minnow
4.560
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
463.220
Hydration Free Energy
-7.940
Log(D) at pH=7.4
2.980
Log(P)
2.68
Log S
-4.09
Log(Vapor Pressure)
-10.3
Melting Point
202.84
pKa Acid
9.93
pKa Basic
6.1
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9696
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.9540
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9192
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.9152
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 3 0.9110
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8831
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8821
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.8800
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.8758
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8732
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8712
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8705
Beta-2-microglobulin P61769 B2MG_HUMAN Homo sapiens 3 0.8693
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8598
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8570
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8471
Amine oxidase [flavin-containing] B P27338 AOFB_HUMAN Homo sapiens 3 0.8458
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.8427
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.8390
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8388
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8367
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.8272
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8235
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8188
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8169
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8135
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.8126
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8093
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.8081
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.8055
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.8029
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.7997
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.7982
cAMP-activated global transcriptional regulator Vfr P55222 VFR_PSEAE Pseudomonas aeruginosa 4 0.7952
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7942
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7939
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7931
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 3 0.7913
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7872
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7863
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7848
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7790
Metapyrocatechase Q7WYF5 Q7WYF5_9PSED Pseudomonas alkylphenolica 3 0.7777
Dihydrofolate reductase P16184 DYR_PNECA Pneumocystis carinii 3 0.7760
Cholinesterase P06276 CHLE_HUMAN Homo sapiens 3 0.7751
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7733
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7732
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7702
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7696
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7678
Dihydrofolate reductase Q83AB2 Q83AB2_COXBU Coxiella burnetii 3 0.7662
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7631
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7609
Dihydrofolate reductase P16184 DYR_PNECA Pneumocystis carinii 3 0.7606
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7606
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7600
Dihydrofolate reductase O30463 O30463_MYCAV Mycobacterium avium 3 0.7592
cGMP-dependent protein kinase 1 P00516 KGP1_BOVIN Bos taurus 3 0.7587
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7585
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7578
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7578
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.7573
orotidine-5'-phosphate decarboxylase Q8T6J6 Q8T6J6_PLAFA Plasmodium falciparum 4 0.7559
Dihydrofolate reductase type 1 from Tn4003 P13955 DYRA_STAAU Staphylococcus aureus 3 0.7556
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7552
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 3 0.7549
E3 ubiquitin-protein ligase Mdm2 P56273 MDM2_XENLA Xenopus laevis 3 0.7528
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7521
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 3 0.7496
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7487
Glutamine synthetase P9WN39 GLN1B_MYCTU Mycobacterium tuberculosis 3 0.7485
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7473
Cytochrome P450 130 P9WPN5 CP130_MYCTU Mycobacterium tuberculosis 3 0.7469
Uridine phosphorylase Q5XA29 Q5XA29_STRP6 Streptococcus pyogenes serotype M6 3 0.7466
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 3 0.7465
Troponin C, slow skeletal and cardiac muscles P63316 TNNC1_HUMAN Homo sapiens 3 0.7464
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7458
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7445
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7441
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7441
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7434
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7424
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 3 0.7415
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7413
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7409
Putative N-acetyl glucosaminyl transferase Q6U8B0 Q6U8B0_RAOTE Raoultella terrigena 3 0.7392
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7376
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7367
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7355
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7352
Cyclin-dependent kinase 5 Q00535 CDK5_HUMAN Homo sapiens 3 0.7341
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7339
Dihydrofolate reductase P22906 DYR_CANAX Candida albicans 3 0.7337
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7335
Carbonic anhydrase 4 P22748 CAH4_HUMAN Homo sapiens 3 0.7324
Scytalone dehydratase P56221 SCYD_MAGO7 Pyricularia oryzae 3 0.7316
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.7307
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Q8RQP5 ISPF_THET8 Thermus thermophilus 3 0.7301
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7297
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.7296
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7280
Scytalone dehydratase P56221 SCYD_MAGO7 Pyricularia oryzae 3 0.7278
Dihydrofolate reductase Q81R22 Q81R22_BACAN Bacillus anthracis 3 0.7275
Dihydrofolate reductase Q81R22 Q81R22_BACAN Bacillus anthracis 3 0.7258
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7257
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7254
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7242
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7235
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7231
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 3 0.7220
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7206
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7198
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7197
Aldo-keto reductase family 1 member A1 P50578 AK1A1_PIG Sus scrofa 3 0.7193
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7186
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.7176
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 2 0.7169
Enoyl-ACP reductase Q9BH77 Q9BH77_PLAFA Plasmodium falciparum 3 0.7168
Dihydrofolate reductase Q81R22 Q81R22_BACAN Bacillus anthracis 3 0.7159
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7153
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7146
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.7134
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7131
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 3 0.7128
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 2 0.7126
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7123
Cytochrome P450 2C8 P10632 CP2C8_HUMAN Homo sapiens 3 0.7117
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7111
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7109
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7105
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7104
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 4 0.7103
Cytosolic heat shock protein 90 Q7XJ80 Q7XJ80_HORVU Hordeum vulgare 3 0.7103
Enoyl-[acyl-carrier-protein] reductase [NADH] Q5NGQ3 Q5NGQ3_FRATT Francisella tularensis subsp. tularensis 3 0.7097
Putative cytochrome P450 Q70AS3 Q70AS3_STRPE Streptomyces peucetius 4 0.7096
Transcriptional enhancer factor TEF-4 Q15562 TEAD2_HUMAN Homo sapiens 3 0.7086
Bis(5'-adenosyl)-triphosphatase P49789 FHIT_HUMAN Homo sapiens 2 0.7082
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7080
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7079
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7070
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.7066
Dihydrofolate reductase P0ABQ4 DYR_ECOLI Escherichia coli 4 0.7063
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7063
Genome polyprotein O93077 O93077_9HEPC Hepacivirus hominis 3 0.7062
Naphthalene 1,2-dioxygenase system, large oxygenase component P0A110 NDOB_PSEPU Pseudomonas putida 3 0.7057
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7056
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.7052
Aspartate carbamoyltransferase catalytic subunit P0A786 PYRB_ECOLI Escherichia coli 2 0.7052
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.7050
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 3 0.7047
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7033
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7028
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7028
Cyclic nucleotide-binding domain-containing protein E0RR11 E0RR11_SPITD Spirochaeta thermophila 3 0.7027
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7023
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7023
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7023
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7022
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7011
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7007
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7003
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7000

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