Drimiopsin E - Compound Card

Drimiopsin E

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Drimiopsin E

Structure
Zoomed Structure
  • Family: Plantae - Hyacinthaceae
  • Kingdom: Plantae
  • Class: Xanthone
Canonical Smiles COc1c(O)cc(c2c1oc1cc(O)cc(c1c2=O)C)O
InChI InChI=1S/C15H12O6/c1-6-3-7(16)4-10-11(6)13(19)12-8(17)5-9(18)14(20-2)15(12)21-10/h3-5,16-18H,1-2H3
InChIKey RXOAJJSKXAWTAP-UHFFFAOYSA-N
Formula C15H12O6
HBA 6
HBD 3
MW 288.25
Rotatable Bonds 1
TPSA 100.13
LogP 2.38
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 21
Formal Charge 0
Fraction CSP3 0.13
Exact Mass 288.06
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: 11437683
Nmrshiftdb2: 70105800

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 288.25 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.01
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.930
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.09

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.200
Plasma Protein Binding
72.91
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
4.370
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.890
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.720
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.730
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
4.460
Rat (Acute)
2.200
Rat (Chronic Oral)
2.910
Fathead Minnow
4.450
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
441.310
Hydration Free Energy
-9.450
Log(D) at pH=7.4
2.540
Log(P)
3.2
Log S
-4.44
Log(Vapor Pressure)
-6.97
Melting Point
279.68
pKa Acid
9.13
pKa Basic
4.85
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 0.9266
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9202
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9137
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9070
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.8918
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 4 0.8858
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8806
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8729
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.8674
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8662
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8572
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8566
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.8555
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8554
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 4 0.8497
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8468
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.8466
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8393
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.8288
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 4 0.8267
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8267
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8265
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 4 0.8253
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8249
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8188
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.8184
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.8183
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8176
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8175
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.8135
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.8135
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8132
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8129
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.8112
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8105
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8032
Dihydrofolate reductase P16184 DYR_PNECA Pneumocystis carinii 4 0.8027
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7999
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7968
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7910
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7909
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7906
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.7875
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7874
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7873
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7873
Dihydrofolate reductase O30463 O30463_MYCAV Mycobacterium avium 4 0.7840
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7825
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7796
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 2 0.7794
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7767
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.7748
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7731
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7716
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7714
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7709
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7704
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7681
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7675
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.7651
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.7649
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7639
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7633
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7631
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 4 0.7615
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7604
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.7581
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7555
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7550
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7537
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7532
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.7522
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7476
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7475
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7466
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7466
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7444
Dihydrofolate reductase Q83AB2 Q83AB2_COXBU Coxiella burnetii 4 0.7440
Putative cytochrome P450 Q70AS3 Q70AS3_STRPE Streptomyces peucetius 4 0.7431
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7418
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7416
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7414
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.7407
Riboflavin kinase Q969G6 RIFK_HUMAN Homo sapiens 4 0.7404
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7403
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7390
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7386
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7380
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7375
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7350
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7347
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7345
11-beta-hydroxysteroid dehydrogenase 1 Q6QLL4 DHI1_CAVPO Cavia porcellus 3 0.7342
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7342
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7328
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7326
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 4 0.7321
Dodecin Q5SIE3 DODEC_THET8 Thermus thermophilus 4 0.7302
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7281
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7273
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7265
Nucleoside diphosphate kinase A 2 P52175 NDKA2_BOVIN Bos taurus 3 0.7254
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7253
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 4 0.7235
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 4 0.7234
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7230
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7225
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 4 0.7220
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7220
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7219
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7218
mitogen-activated protein kinase kinase Q7YTF7 Q7YTF7_PLAF7 Plasmodium falciparum 4 0.7217
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7217
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7212
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7206
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7196
NADPH--cytochrome P450 reductase P00388 NCPR_RAT Rattus norvegicus 4 0.7176
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7176
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7175
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7168
Cyclin-dependent kinase 6 Q00534 CDK6_HUMAN Homo sapiens 3 0.7165
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 4 0.7158
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7158
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7149
Actin-related protein 3 P61157 ARP3_BOVIN Bos taurus 4 0.7143
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.7140
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7131
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7115
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7109
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7109
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7094
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.7086
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7085
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7053
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7050
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7047
Methyltransferase D0VX01 D0VX01_WSLV Wesselsbron virus 4 0.7031
NADPH--cytochrome P450 reductase P00388 NCPR_RAT Rattus norvegicus 4 0.7027
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7004

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