8'-epi-cleomiscosin A - Compound Card

8'-epi-cleomiscosin A

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8'-epi-cleomiscosin A

Structure
Zoomed Structure
  • Family: Plantae - Sapindaceae
  • Kingdom: Plantae
  • Class: Coumarin
Canonical Smiles OC[C@@H]1Oc2c(O[C@@H]1c1ccc(c(c1)OC)O)c(OC)cc1c2oc(=O)cc1
InChI InChI=1S/C20H18O8/c1-24-13-7-10(3-5-12(13)22)17-15(9-21)26-20-18-11(4-6-16(23)27-18)8-14(25-2)19(20)28-17/h3-8,15,17,21-22H,9H2,1-2H3/t15-,17+/m0/s1
InChIKey OCBGWPJNUZMLCA-DOTOQJQBSA-N
Formula C20H18O8
HBA 8
HBD 2
MW 386.36
Rotatable Bonds 4
TPSA 107.59
LogP 2.39
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.25
Exact Mass 386.1
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pancovia pedicellaris Sapindaceae Plantae 1195016

Showing of synonyms

  • Soh R, Bankeu J, et al. (2009). Antibacterial Ellagic Acid Derivatives and Other Constituents from Pancovia pedicellaris. Zeitschrift für Naturforschung B. 2009, 64(9), 1070-1076. [View]
Pubchem: 11200016
Chebi: 65642
Nmrshiftdb2: 60065289
Metabolights: MTBLC65642

No compound-protein relationship available.

Structure

SMILES: O=c(o1)ccc2ccc(c3c12)OC(CO3)c4ccccc4

Level: 1

Mol. Weight: 386.36 g/mol

Structure

SMILES: O1CCOc(c1c23)ccc2ccc(=O)o3

Level: 0

Mol. Weight: 386.36 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 386.36 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.61
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.740
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.89

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.540
Plasma Protein Binding
88.15
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Non-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
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.190
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.610
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.240
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.790
Micronucleos
Toxic
NR-AhR
Safe
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
-12.000
Rat (Acute)
2.060
Rat (Chronic Oral)
2.160
Fathead Minnow
4.660
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
475.520
Hydration Free Energy
-7.830
Log(D) at pH=7.4
2.160
Log(P)
1.3
Log S
-4.35
Log(Vapor Pressure)
-8.67
Melting Point
194.62
pKa Acid
7.23
pKa Basic
0.97
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.9662
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.9487
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9230
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.9122
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9072
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9071
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.9000
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8868
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8800
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8613
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8439
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.8391
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8242
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.8220
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8207
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.8169
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8076
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8061
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7983
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7978
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7977
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7966
GTPase KRas P01116 RASK_HUMAN Homo sapiens 3 0.7905
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 4 0.7878
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7863
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7836
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7826
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7823
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7811
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7741
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7717
Acetolactate synthase catalytic subunit, mitochondrial P07342 ILVB_YEAST Saccharomyces cerevisiae 3 0.7683
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7639
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.7615
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7615
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7613
Ephrin type-A receptor 3 P29320 EPHA3_HUMAN Homo sapiens 4 0.7605
Pol protein Q000H7 Q000H7_9HIV1 Human immunodeficiency virus 1 3 0.7593
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7584
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7533
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7509
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7462
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7444
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7439
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7423
[LysW]-aminoadipate kinase O50147 LYSZ_THET2 Thermus thermophilus 3 0.7397
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7381
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7380
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7348
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7318
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7314
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7311
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7308
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7297
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7296
cGMP-dependent protein kinase 1 P00516 KGP1_BOVIN Bos taurus 3 0.7295
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 5 0.7293
Mu-type opioid receptor P42866 OPRM_MOUSE Mus musculus 3 0.7276
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7244
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 2 0.7234
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7183
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7183
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 4 0.7181
Deoxycytidylate deaminase H6WFU3 H6WFU3_9CAUD Cyanophage S-TIM5 4 0.7172
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7165
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7155
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7148
Interstitial collagenase P03956 MMP1_HUMAN Homo sapiens 3 0.7137
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7132
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7131
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7128
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7112
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7084
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7084
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7084
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7083
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7075
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7062
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7055
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 3 0.7053
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7052
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7044
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7033
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7030
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7021
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7018
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7013
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7007

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