Swertianin - Compound Card

Swertianin

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Swertianin

Structure
Zoomed Structure
  • Family: Plantae - Loganiaceae
  • Kingdom: Plantae
  • Class: Xanthone
Canonical Smiles COc1cc(O)c2c(c1)oc1c(c2=O)c(O)c(cc1)O
InChI InChI=1S/C14H10O6/c1-19-6-4-8(16)11-10(5-6)20-9-3-2-7(15)13(17)12(9)14(11)18/h2-5,15-17H,1H3
InChIKey BDBVOZGRVBXANN-UHFFFAOYSA-N
Formula C14H10O6
HBA 6
HBD 3
MW 274.23
Rotatable Bonds 1
TPSA 100.13
LogP 2.07
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.07
Exact Mass 274.05
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: 5281661
Kegg Ligand: C10092
Chebi: 9371
Nmrshiftdb2: 60071114
Metabolights: MTBLC9371
Bindingdb: 50155435

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)oc3c(c2=O)cccc3

Level: 0

Mol. Weight: 274.23 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.34
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.930
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.21

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.130
Plasma Protein Binding
70.8
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
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.350
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.700
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.710
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.100
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
4.530
Rat (Acute)
2.270
Rat (Chronic Oral)
3.080
Fathead Minnow
4.370
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
434.990
Hydration Free Energy
-10.530
Log(D) at pH=7.4
2.160
Log(P)
2.87
Log S
-4.28
Log(Vapor Pressure)
-7.02
Melting Point
241.01
pKa Acid
9.11
pKa Basic
4.44
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9567
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9396
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9358
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.9334
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9245
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.9194
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.9182
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.9147
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.9044
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.9008
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8999
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.8934
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8835
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8821
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8677
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8666
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 4 0.8604
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8576
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8573
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8571
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8566
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8488
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8459
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.8457
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8427
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.8374
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8334
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8302
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.8300
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.8295
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8292
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8268
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8254
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 4 0.8212
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.8190
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.8129
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.8127
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.8117
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8051
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8038
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 3 0.8035
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8016
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7991
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7979
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7976
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7972
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7963
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7960
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7952
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.7948
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 3 0.7937
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7935
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7932
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7912
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7872
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7827
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7821
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 3 0.7797
Tyrosine 3-monooxygenase P04177 TY3H_RAT Rattus norvegicus 4 0.7797
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7767
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.7763
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7760
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7753
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7719
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7719
Oxygen-insensitive NAD(P)H nitroreductase P38489 NFSB_ECOLI Escherichia coli 3 0.7713
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7677
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7666
Biphenyl dioxygenase subunit alpha P37333 BPHA_PARXL Paraburkholderia xenovorans 3 0.7659
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 4 0.7655
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7608
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7603
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7602
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7598
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7598
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7555
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7528
NAD-dependent protein deacetylase Q9WYW0 NPD_THEMA Thermotoga maritima 3 0.7520
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7507
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7503
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.7501
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7495
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7493
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7474
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7453
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 4 0.7446
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.7443
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7439
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7435
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7428
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7418
Hexokinase-4 P35557 HXK4_HUMAN Homo sapiens 3 0.7406
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7391
Reaction center protein L chain P0C0Y8 RCEL_RHOSH Rhodobacter sphaeroides 3 0.7391
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7385
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7378
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7377
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7362
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7347
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7343
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7341
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7335
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.7333
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7333
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 4 0.7316
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7316
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7313
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7311
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7295
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7281
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7280
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7278
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7265
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.7247
Orotidine 5'-phosphate decarboxylase Q9KQT7 PYRF_VIBCH Vibrio cholerae serotype O1 4 0.7239
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7239
Glutamate receptor 3 P19492 GRIA3_RAT Rattus norvegicus 4 0.7239
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7238
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7235
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7231
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7211
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7210
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7206
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7201
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7194
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7189
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7189
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7176
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 3 0.7174
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7168
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7167
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7160
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7153
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7153
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 4 0.7137
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7135
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7133
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7122
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7092
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 5 0.7077
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7064
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7063
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7060
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7057
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7057
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7048
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7047
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 3 0.7046
GTPase IMAP family member 2 Q9UG22 GIMA2_HUMAN Homo sapiens 3 0.7043
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7041
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7020
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7014

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