Drimiopsin C - Compound Card

Drimiopsin C

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Drimiopsin C

Structure
Zoomed Structure
  • Family: Plantae - Hyacinthaceae
  • Kingdom: Plantae
  • Class: Xanthone
Canonical Smiles COc1c(O)cc2c(c1O)c(=O)c1c(o2)cc(cc1C)O
InChI InChI=1S/C15H12O6/c1-6-3-7(16)4-9-11(6)13(18)12-10(21-9)5-8(17)15(20-2)14(12)19/h3-5,16-17,19H,1-2H3
InChIKey IMMSZLMLFUYPBT-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: 11254733
Nmrshiftdb2: 70105804

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)
-4.97
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.920
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.83

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.170
Plasma Protein Binding
73.06
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
5.050
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.410
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.160
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.940
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
4.470
Rat (Acute)
2.210
Rat (Chronic Oral)
3.000
Fathead Minnow
4.400
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
439.150
Hydration Free Energy
-10.720
Log(D) at pH=7.4
2.520
Log(P)
3.06
Log S
-4.56
Log(Vapor Pressure)
-7.19
Melting Point
276.25
pKa Acid
6.52
pKa Basic
5.19
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 0.9176
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9164
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9161
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9023
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8892
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8830
11-beta-hydroxysteroid dehydrogenase 1 Q6QLL4 DHI1_CAVPO Cavia porcellus 3 0.8762
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.8748
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8642
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8583
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8571
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8566
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.8544
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8531
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8525
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8489
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8474
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 4 0.8414
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.8319
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8319
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.8265
Nucleoside permease Q9KPL5 Q9KPL5_VIBCH Vibrio cholerae serotype O1 4 0.8224
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8210
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8203
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.8184
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8180
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.8159
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8120
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8079
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 4 0.8075
Dihydrofolate reductase P16184 DYR_PNECA Pneumocystis carinii 4 0.8072
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 4 0.8068
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8064
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8057
Dihydrofolate reductase O30463 O30463_MYCAV Mycobacterium avium 4 0.8031
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8005
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7999
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 4 0.7983
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7952
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7901
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7868
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7835
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7813
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.7803
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.7800
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7784
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7762
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7742
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7697
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7692
Oxygen-insensitive NAD(P)H nitroreductase P38489 NFSB_ECOLI Escherichia coli 3 0.7651
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7640
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7633
Dodecin Q5SIE3 DODEC_THET8 Thermus thermophilus 4 0.7626
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7625
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7614
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7614
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7612
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7612
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7592
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7589
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7566
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7553
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7522
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7506
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.7500
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.7496
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7490
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7482
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 4 0.7461
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7453
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7429
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7421
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7418
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7415
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7408
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7403
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7385
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7384
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 5 0.7353
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7353
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7353
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7324
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7321
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7307
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7305
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7293
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7250
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 4 0.7247
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7245
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7236
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7227
Glutamate receptor 2 P42262 GRIA2_HUMAN Homo sapiens 5 0.7224
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7220
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 3 0.7184
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 4 0.7152
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7142
Putative cytochrome P450 Q70AS3 Q70AS3_STRPE Streptomyces peucetius 4 0.7116
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7113
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7113
Diguanylate phosphodiesterase A6T8V8 A6T8V8_KLEP7 Klebsiella pneumoniae subsp. pneumoniae 4 0.7103
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7101
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7094
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7092
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7091
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7090
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.7071
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7030
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7008
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7004

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