Seputhecarpan D - Compound Card

Seputhecarpan D

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Seputhecarpan D

Structure
Zoomed Structure
  • Family: Plantae - Sapotaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Pterocarpan
Canonical Smiles COc1ccc2c(c1)OC1C2COc2c1cc(c(c2)O)C(C=C)(C)C
InChI InChI=1S/C21H22O4/c1-5-21(2,3)16-9-14-18(10-17(16)22)24-11-15-13-7-6-12(23-4)8-19(13)25-20(14)15/h5-10,15,20,22H,1,11H2,2-4H3
InChIKey DQERMSYUZHYRMN-UHFFFAOYSA-N
Formula C21H22O4
HBA 4
HBD 1
MW 338.4
Rotatable Bonds 3
TPSA 47.92
LogP 4.47
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.33
Exact Mass 338.15
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]

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)OC3C2COc4c3cccc4

Level: 0

Mol. Weight: 338.4 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.85
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.490
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.88

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.100
Plasma Protein Binding
43.95
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
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
9.960
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.170
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.500
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.010
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
1.630
Rat (Acute)
2.190
Rat (Chronic Oral)
1.680
Fathead Minnow
4.960
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
424.670
Hydration Free Energy
-8.160
Log(D) at pH=7.4
4.090
Log(P)
4.38
Log S
-5.51
Log(Vapor Pressure)
-7.85
Melting Point
127.22
pKa Acid
10.63
pKa Basic
6.53
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9674
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9574
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.9505
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9366
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.9260
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.9203
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.9131
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.9014
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8938
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8911
Caspase-6 P55212 CASP6_HUMAN Homo sapiens 3 0.8812
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8784
Apoptosis regulator Bcl-2 P10415 BCL2_HUMAN Homo sapiens 3 0.8781
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.8760
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8621
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 3 0.8580
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8576
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.8572
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8552
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.8499
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.8497
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.8458
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.8445
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8348
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8338
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8257
Beta-2-microglobulin P61769 B2MG_HUMAN Homo sapiens 3 0.8218
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.8138
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8101
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8062
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8058
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8000
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7924
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7916
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 3 0.7864
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.7856
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7826
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7824
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7820
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7811
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7802
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 3 0.7801
Oxysterols receptor LXR-beta P55055 NR1H2_HUMAN Homo sapiens 3 0.7758
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7743
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7664
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7662
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7661
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7660
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7655
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7654
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7649
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7632
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7611
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7607
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7606
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7604
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7603
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7589
Enoyl-[acyl-carrier-protein] reductase [NADH] Q5NGQ3 Q5NGQ3_FRATT Francisella tularensis subsp. tularensis 3 0.7579
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7562
Lanosterol synthase P48449 ERG7_HUMAN Homo sapiens 3 0.7560
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7523
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7516
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7508
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7485
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7483
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 3 0.7480
Cellular retinol-binding protein type II Q8UVG6 Q8UVG6_DANRE Danio rerio 3 0.7470
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7469
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7462
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 3 0.7459
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7454
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7444
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 2 0.7436
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7425
Retinaldehyde-binding protein 1 P12271 RLBP1_HUMAN Homo sapiens 3 0.7414
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 3 0.7401
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7401
Thymidine phosphorylase P07650 TYPH_ECOLI Escherichia coli 4 0.7383
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7371
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7370
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7369
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7367
Acetylcholine-binding protein P58154 ACHP_LYMST Lymnaea stagnalis 3 0.7361
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7358
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7357
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7356
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7350
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7348
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7338
Prostaglandin E synthase 2 Q9N0A4 PGES2_MACFA Macaca fascicularis 3 0.7314
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7309
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7300
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7295
Tau-tubulin kinase 1 Q5TCY1 TTBK1_HUMAN Homo sapiens 4 0.7293
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7280
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7276
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7276
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7276
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7272
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7269
Serine/threonine-protein kinase Nek2 P51955 NEK2_HUMAN Homo sapiens 3 0.7261
orotidine-5'-phosphate decarboxylase Q8T6J6 Q8T6J6_PLAFA Plasmodium falciparum 4 0.7259
Enoyl-acyl carrier reductase Q6UCJ9 Q6UCJ9_TOXGO Toxoplasma gondii 4 0.7257
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7257
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7249
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7246
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7219
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7212
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7211
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7208
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7199
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 4 0.7193
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7192
Scytalone dehydratase P56221 SCYD_MAGO7 Pyricularia oryzae 3 0.7191
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 4 0.7173
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7169
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7160
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 2 0.7159
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7158
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7152
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7129
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7126
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7087
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7086
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7085
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7085
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7080
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7071
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7069
Uridine phosphorylase Q5XA29 Q5XA29_STRP6 Streptococcus pyogenes serotype M6 3 0.7067
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7067
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 2 0.7067
Bifunctional dihydrofolate reductase-thymidylate synthase Q27793 DRTS_TRYCR Trypanosoma cruzi 3 0.7059
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 2 0.7059
Glutamate racemase Q9ZLT0 MURI_HELPJ Helicobacter pylori 3 0.7054
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7052
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 2 0.7047
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7042
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7032
Sulfotransferase 1E1 P49888 ST1E1_HUMAN Homo sapiens 3 0.7031
Putative cytochrome P450 120 Q59990 CP120_SYNY3 Synechocystis sp 3 0.7029
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7019
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7018
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7011
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7008

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