Swertiaperennin - Compound Card

Swertiaperennin

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Swertiaperennin

Structure
Zoomed Structure
  • Family: Plantae - Loganiaceae
  • Kingdom: Plantae
  • Class: Xanthone
Canonical Smiles COc1cc(O)c2c(c1)oc1c(c2=O)c(O)c(cc1)OC
InChI InChI=1S/C15H12O6/c1-19-7-5-8(16)12-11(6-7)21-9-3-4-10(20-2)14(17)13(9)15(12)18/h3-6,16-17H,1-2H3
InChIKey PUECEVJMPDNNHT-UHFFFAOYSA-N
Formula C15H12O6
HBA 6
HBD 2
MW 288.25
Rotatable Bonds 2
TPSA 89.13
LogP 2.37
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 Anthocleista liebrechtsiana Loganiaceae Plantae 2708715

Showing of synonyms

  • Shammari LA, Mamun AA, et al. (2019). Alkaloid Profiling of Hippeastrum Cultivars by GC-MS, Isolation of Amaryllidaceae Alkaloids and Evaluation of Their Cytotoxicity. Records of Natural Products,2019, 14, 154-159. [View]
Pubchem: 5281653
Kegg Ligand: C10083
Chebi: 1228
Nmrshiftdb2: 60001980
Metabolights: MTBLC1228
Bindingdb: 174836

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)
-4.76
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.720
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.68

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.360
Plasma Protein Binding
69.31
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
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
4.390
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.230
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.630
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.210
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
4.070
Rat (Acute)
2.190
Rat (Chronic Oral)
2.740
Fathead Minnow
4.730
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
419.280
Hydration Free Energy
-9.760
Log(D) at pH=7.4
2.870
Log(P)
3.4
Log S
-5.08
Log(Vapor Pressure)
-7.19
Melting Point
214.9
pKa Acid
8.42
pKa Basic
3.65
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9568
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9410
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9396
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.9384
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9356
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.9303
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9251
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.9234
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.9141
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.9006
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8999
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8982
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8865
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8855
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8844
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8736
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8718
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8678
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8648
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8640
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8628
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 4 0.8624
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.8616
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8600
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8594
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8589
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8515
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.8477
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.8460
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8457
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.8450
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8427
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.8402
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8371
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.8351
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8348
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 4 0.8347
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8345
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.8274
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8257
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8242
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.8213
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.8210
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8209
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 3 0.8080
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8045
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.8039
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.8036
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8018
Oxygen-insensitive NAD(P)H nitroreductase P38489 NFSB_ECOLI Escherichia coli 3 0.7972
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7970
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7965
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7961
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7940
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 3 0.7903
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7872
Biphenyl dioxygenase subunit alpha P37333 BPHA_PARXL Paraburkholderia xenovorans 3 0.7871
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7808
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7807
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7803
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7793
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7750
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7746
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7732
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7708
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7662
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 3 0.7652
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7642
Glutamate receptor 3 P19492 GRIA3_RAT Rattus norvegicus 4 0.7617
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7615
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7573
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.7558
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7554
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.7547
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 4 0.7546
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7518
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7511
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7497
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7491
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7488
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7476
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7467
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 2 0.7463
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7461
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7459
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 4 0.7443
Reaction center protein L chain P0C0Y8 RCEL_RHOSH Rhodobacter sphaeroides 3 0.7443
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7436
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.7436
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7428
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7412
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7402
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7394
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7393
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7388
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7387
Cholinesterase P06276 CHLE_HUMAN Homo sapiens 2 0.7385
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7379
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.7375
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7363
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7357
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7339
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7339
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7317
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7315
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7311
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7310
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7289
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7287
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7284
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7284
Orotidine 5'-phosphate decarboxylase Q9KQT7 PYRF_VIBCH Vibrio cholerae serotype O1 4 0.7271
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7269
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7260
Catalase-peroxidase Q3JNW6 KATG_BURP1 Burkholderia pseudomallei 3 0.7229
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7214
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7210
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 5 0.7209
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7201
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7199
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7180
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.7178
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7171
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7162
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7159
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7159
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7156
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7149
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7149
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7144
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7139
Catalase-peroxidase 2 O59651 KATG2_HALMA Haloarcula marismortui 2 0.7110
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7103
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7100
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7066
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7066
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7062
GTPase IMAP family member 2 Q9UG22 GIMA2_HUMAN Homo sapiens 3 0.7045
Nitroreductase domain-containing protein Q8DW21 Q8DW21_STRMU Streptococcus mutans serotype c 3 0.7032
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7024
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7009
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7004

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