Digitolutein - Compound Card

Digitolutein

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Digitolutein

Structure
Zoomed Structure
  • Family: Plantae - Rubiaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Anthraquinone
Canonical Smiles COc1c2C(=O)c3ccccc3C(=O)c2cc(c1O)C
InChI InChI=1S/C16H12O4/c1-8-7-11-12(16(20-2)13(8)17)15(19)10-6-4-3-5-9(10)14(11)18/h3-7,17H,1-2H3
InChIKey WCRMDMYSQWZTSF-UHFFFAOYSA-N
Formula C16H12O4
HBA 4
HBD 1
MW 268.27
Rotatable Bonds 1
TPSA 63.6
LogP 2.48
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.12
Exact Mass 268.07
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Morinda lucida Rubiaceae Plantae 339305

Showing of synonyms

  • Longue Ekon J, Zra T, et al. (2020). New anthraquinone derivatives from the stem barks of Morinda lucida Benth. Phytochemistry Letters, 2020, 39, 94-98. [View]
Pubchem: 160475
Nmrshiftdb2: 60081591

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)C(=O)c3c(C2=O)cccc3

Level: 0

Mol. Weight: 268.27 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.58
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.31
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.32

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.87
Plasma Protein Binding
60.87
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
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.17
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.47
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.09
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.37
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
4.31
Rat (Acute)
2.48
Rat (Chronic Oral)
2.44
Fathead Minnow
4.57
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
393.89
Hydration Free Energy
-6.62
Log(D) at pH=7.4
1.78
Log(P)
3.14
Log S
-5.43
Log(Vapor Pressure)
-6.76
Melting Point
195.24
pKa Acid
6.54
pKa Basic
3.36
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.9748
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.9735
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.9306
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9289
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.9135
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9021
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8857
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8791
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 3 0.8712
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.8706
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8628
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.8580
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8577
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.8456
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 4 0.8453
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8441
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.8408
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8352
Aklavinone 12-hydroxylase RdmE Q54530 DNRF_STREF Streptomyces purpurascens 4 0.8277
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.8247
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 3 0.8221
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.8146
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.8124
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8114
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.8080
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8070
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.8029
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.8027
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8025
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7999
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7976
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7940
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.7905
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.7895
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7865
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7863
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7812
Aldehyde dehydrogenase, dimeric NADP-preferring P30838 AL3A1_HUMAN Homo sapiens 3 0.7768
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7767
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7717
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7702
Scytalone dehydratase P56221 SCYD_MAGO7 Pyricularia oryzae 3 0.7683
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7678
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7647
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7633
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7631
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7629
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7624
Troponin C, slow skeletal and cardiac muscles P63316 TNNC1_HUMAN Homo sapiens 3 0.7599
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7595
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7593
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7578
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7550
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7542
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7535
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7517
Sulfotransferase 1E1 P49888 ST1E1_HUMAN Homo sapiens 3 0.7516
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7504
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 4 0.7498
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7460
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7458
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7457
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7434
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7409
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7407
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7407
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7405
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7404
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7403
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7397
cGMP-dependent protein kinase, putative A5K0N4 A5K0N4_PLAVS Plasmodium vivax 3 0.7397
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7394
Biphenyl dioxygenase subunit alpha P37333 BPHA_PARXL Paraburkholderia xenovorans 4 0.7383
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7382
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7381
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7344
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7341
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7336
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7328
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7322
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7322
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7307
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7305
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7283
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7258
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7227
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7222
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7222
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7222
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.7215
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7210
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7206
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7202
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7201
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7201
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 3 0.7193
Chymotrypsinogen A P00766 CTRA_BOVIN Bos taurus 3 0.7191
Troponin C, slow skeletal and cardiac muscles P63316 TNNC1_HUMAN Homo sapiens 3 0.7179
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7179
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7179
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7175
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7172
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7171
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7169
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7161
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7154
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7142
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7139
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7119
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7109
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7099
Bifunctional dihydrofolate reductase-thymidylate synthase Q27793 DRTS_TRYCR Trypanosoma cruzi 3 0.7097
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7087
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7084
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.7082
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7079
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7074
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7067
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7049
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7048
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7044
cAMP-dependent protein kinase catalytic subunit alpha P17612 KAPCA_HUMAN Homo sapiens 3 0.7036
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7026
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7020
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 3 0.7014
Nucleoprotein P33469 NCAP_CVHOC Human coronavirus OC43 3 0.7014
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7001

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