Drimiopsin F - Compound Card

Drimiopsin F

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Drimiopsin F

Structure
Zoomed Structure
  • Family: Plantae - Hyacinthaceae
  • Kingdom: Plantae
  • Class: Xanthone
Canonical Smiles COc1cc(C)c2c(c1)oc1c(c2=O)c(O)c(c(c1)O)OC
InChI InChI=1S/C16H14O6/c1-7-4-8(20-2)5-10-12(7)14(18)13-11(22-10)6-9(17)16(21-3)15(13)19/h4-6,17,19H,1-3H3
InChIKey MSFILNYKSUAMKK-UHFFFAOYSA-N
Formula C16H14O6
HBA 6
HBD 2
MW 302.28
Rotatable Bonds 2
TPSA 89.13
LogP 2.68
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.19
Exact Mass 302.08
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Drimiopsis maculata Hyacinthaceae Plantae 81747

Showing of synonyms

  • Mulholland DA, Koorbanally C, et al. (2004). Xanthones from Drimiopsis maculata. Journal of natural products, 2004, 67(10), 1726–1728. [View]
Pubchem: 11231920
Nmrshiftdb2: 70105802

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)oc3c(c2=O)cccc3

Level: 0

Mol. Weight: 302.28 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.72
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.840
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.7

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.410
Plasma Protein Binding
74.78
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
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
3.100
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.210
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.680
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.800
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
4.240
Rat (Acute)
2.110
Rat (Chronic Oral)
2.690
Fathead Minnow
4.750
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
424.350
Hydration Free Energy
-10.240
Log(D) at pH=7.4
2.900
Log(P)
3.51
Log S
-4.9
Log(Vapor Pressure)
-7.09
Melting Point
232.75
pKa Acid
7.59
pKa Basic
3.66
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9202
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9168
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9160
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9096
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8955
11-beta-hydroxysteroid dehydrogenase 1 Q6QLL4 DHI1_CAVPO Cavia porcellus 3 0.8926
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8917
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8829
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8820
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.8813
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8773
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8715
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.8576
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8572
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8557
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.8544
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 4 0.8414
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8326
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8293
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8256
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8255
Nucleoside permease Q9KPL5 Q9KPL5_VIBCH Vibrio cholerae serotype O1 4 0.8250
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8240
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8229
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8196
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8191
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8187
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.8183
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.8181
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8174
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8166
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8162
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8155
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.8097
Dihydrofolate reductase P16184 DYR_PNECA Pneumocystis carinii 4 0.8092
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 4 0.8080
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 4 0.8074
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 4 0.8067
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8067
Dihydrofolate reductase O30463 O30463_MYCAV Mycobacterium avium 4 0.8041
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.8019
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.8012
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.7928
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7913
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7890
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7886
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7875
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.7866
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7847
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7813
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7788
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7781
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7778
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7748
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7718
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7715
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7708
Dihydroorotate dehydrogenase (quinone), mitochondrial Q02127 PYRD_HUMAN Homo sapiens 4 0.7708
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7690
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7656
Dodecin Q5SIE3 DODEC_THET8 Thermus thermophilus 4 0.7651
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7645
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7635
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7631
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7627
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7625
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7612
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7603
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7586
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7546
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 5 0.7527
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7506
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7505
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7500
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7499
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7481
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 4 0.7465
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7444
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7444
Glutamate receptor 2 P42262 GRIA2_HUMAN Homo sapiens 5 0.7440
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7432
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7423
Putative cytochrome P450 Q70AS3 Q70AS3_STRPE Streptomyces peucetius 4 0.7418
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7417
Oxygen-insensitive NAD(P)H nitroreductase P38489 NFSB_ECOLI Escherichia coli 3 0.7404
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7395
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 4 0.7393
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7369
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7344
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7335
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7331
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7313
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7304
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7300
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7297
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7287
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7279
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 3 0.7277
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7252
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7249
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7234
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7222
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7210
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7206
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7204
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7200
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7197
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 4 0.7193
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7190
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7185
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 5 0.7184
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 4 0.7182
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7175
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7165
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.7165
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7164
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7164
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7145
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7126
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7125
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7119
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7119
Diguanylate phosphodiesterase A6T8V8 A6T8V8_KLEP7 Klebsiella pneumoniae subsp. pneumoniae 4 0.7116
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7113
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7097
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7094
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7089
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7084
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 3 0.7084
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7083
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7047
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7036
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.7015
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7011
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7001

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