3-O-geranylemodin - Compound Card

3-O-geranylemodin

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3-O-geranylemodin

Structure
Zoomed Structure
  • Family: Plantae - Hypericaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Anthraquinone Derivative
Canonical Smiles c1(O)cc(O/C=C(\C)/CCC=C(C)C)cc2C(=O)c3cc(O)cc(O)c3C(=O)c12
InChI InChI=1S/C23H22O6/c1-12(2)5-4-6-13(3)11-29-15-9-17-21(19(26)10-15)23(28)20-16(22(17)27)7-14(24)8-18(20)25/h5,7-11,24-26H,4,6H2,1-3H3/b13-11+
InChIKey MYMFHFJDMCKSGP-ACCUITESSA-N
Formula C23H22O6
HBA 6
HBD 3
MW 394.42
Rotatable Bonds 5
TPSA 104.06
LogP 4.61
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.22
Exact Mass 394.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Hypericum lanceolatum Hypericaceae Plantae 55962

Showing of synonyms

  • Fobofou SA, Franke K, et al. (2016). Tricyclic Acylphloroglucinols from Hypericum lanceolatum and Regioselective Synthesis of Selancins A and B.. Journal of natural products,2016, 79(4), 743-753. [View] [PubMed]

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 394.42 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.16
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.84
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.79

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.06
Plasma Protein Binding
74.12
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
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
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.48
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.04
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.8
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.5
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
Safe
T. Pyriformis
-6.12
Rat (Acute)
2.3
Rat (Chronic Oral)
3.28
Fathead Minnow
5.31
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
497.19
Hydration Free Energy
-8.25
Log(D) at pH=7.4
3.63
Log(P)
6.43
Log S
-7.51
Log(Vapor Pressure)
-8.65
Melting Point
199.14
pKa Acid
7.36
pKa Basic
5.24
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.9532
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9414
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9356
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9355
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8995
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8974
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8959
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8917
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8910
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8898
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8725
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8717
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 4 0.8686
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8599
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.8584
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8570
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8533
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8520
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8469
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8449
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8430
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.8409
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8370
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8363
Dihydrofolate reductase Q83AB2 Q83AB2_COXBU Coxiella burnetii 4 0.8352
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8293
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8266
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 4 0.8177
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8177
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8132
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8125
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8089
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8067
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8064
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8057
Dihydrofolate reductase O30463 O30463_MYCAV Mycobacterium avium 4 0.8019
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8010
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.8006
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7997
Dihydrofolate reductase P00381 DYR_LACCA Lacticaseibacillus casei 4 0.7955
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7942
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 5 0.7932
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7920
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.7907
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.7871
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7865
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7863
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7852
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7733
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7726
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7701
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7685
Catalase-peroxidase 2 O59651 KATG2_HALMA Haloarcula marismortui 3 0.7672
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7672
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7664
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7663
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7648
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.7643
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7598
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7551
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 5 0.7550
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7530
Cytochrome b6 P83791 CYB6_MASLA Mastigocladus laminosus 3 0.7530
DNA double-strand break repair protein Mre11 Q9X1X0 Q9X1X0_THEMA Thermotoga maritima MSB8 4 0.7509
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7501
Dihydrofolate reductase P16184 DYR_PNECA Pneumocystis carinii 4 0.7490
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7485
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7474
Dihydrofolate reductase Q81R22 Q81R22_BACAN Bacillus anthracis 4 0.7474
Catalase-peroxidase Q3JNW6 KATG_BURP1 Burkholderia pseudomallei 3 0.7473
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 3 0.7460
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7458
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7453
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7452
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7448
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7441
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7436
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7435
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7435
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7433
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7424
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7422
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 5 0.7394
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7361
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.7336
Aclacinomycin 10-hydroxylase RdmB Q54527 RDMB_STREF Streptomyces purpurascens 3 0.7302
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7296
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7295
Dimethylsulfonioproprionate demethylase DmdA Q4FP21 DMDA_PELUB Pelagibacter ubique 4 0.7264
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7250
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7234
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7234
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7202
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7184
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7183
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7180
Cyclin-dependent kinase 6 Q00534 CDK6_HUMAN Homo sapiens 3 0.7175
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7165
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7164
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7164
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7157
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7152
Dihydrofolate reductase P16184 DYR_PNECA Pneumocystis carinii 4 0.7142
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7138
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7120
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7110
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7103
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7101
Orotidine 5'-phosphate decarboxylase Q9KQT7 PYRF_VIBCH Vibrio cholerae serotype O1 4 0.7098
Aklavinone 12-hydroxylase RdmE Q54530 DNRF_STREF Streptomyces purpurascens 4 0.7080
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7071
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7061
Nitric oxide synthase 3 P29474 NOS3_HUMAN Homo sapiens 5 0.7057
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7057
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7055
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7054
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7048
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7047
Isoflavone 4'-O-methyltransferase Q29U70 I4OMT_MEDTR Medicago truncatula 3 0.7036
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7033
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7030
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7029
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7018
Orotidine 5'-phosphate decarboxylase O58462 PYRF_PYRHO Pyrococcus horikoshii 3 0.7018
Acetyl-CoA carboxylase Q00955 ACAC_YEAST Saccharomyces cerevisiae 3 0.7013
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7002

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