(R)-scillascillin - Compound Card

(R)-scillascillin

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(R)-scillascillin

Structure
Zoomed Structure
  • Family: Plantae - Hyacinthaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Homoisoflavonoid
Canonical Smiles Oc1cc(O)c2c(c1)OC[C@@]1(C2=O)Cc2c1cc1c(c2)OCO1
InChI InChI=1S/C17H12O6/c18-9-2-11(19)15-14(3-9)21-6-17(16(15)20)5-8-1-12-13(4-10(8)17)23-7-22-12/h1-4,18-19H,5-7H2/t17-/m0/s1
InChIKey SAXOGBBWXWKZKR-KRWDZBQOSA-N
Formula C17H12O6
HBA 6
HBD 2
MW 312.28
Rotatable Bonds 0
TPSA 85.22
LogP 1.9
Number Rings 5
Number Aromatic Rings 2
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.24
Exact Mass 312.06
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Drimiopsis maculata, Eucomis schiffii, Urginea epigea, Drimia altissima Hyacinthaceae Plantae —

Showing of synonyms

  • Fusi F, Ferrara A, et al. (2008). Vascular myorelaxing activity of isolates from South African Hyacinthaceae partly mediated by activation of soluble guanylyl cyclase in rat aortic ring preparations. Journal of pharmacy and pharmacology, 2008, 60(4), 489–497. [View]
Pubchem: 75492722
Nmrshiftdb2: 70037280

No compound-protein relationship available.

Structure

SMILES: O1COc(c2)c1cc(C3)c2C34C(=O)c5c(OC4)cccc5

Level: 0

Mol. Weight: 312.28 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.69
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.68
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.88

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.01
Plasma Protein Binding
74.22
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
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
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
13.29
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.67
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.58
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.4
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
Toxic
T. Pyriformis
2.35
Rat (Acute)
1.98
Rat (Chronic Oral)
2.34
Fathead Minnow
4.44
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
431.49
Hydration Free Energy
-9.21
Log(D) at pH=7.4
2.37
Log(P)
2.78
Log S
-4.99
Log(Vapor Pressure)
-9.07
Melting Point
254.47
pKa Acid
7.46
pKa Basic
4.32
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.9600
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.9561
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.9554
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 4 0.9552
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9372
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 4 0.9342
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 4 0.9309
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9253
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9225
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.9206
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9189
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9040
Dihydrofolate reductase P22906 DYR_CANAX Candida albicans 4 0.9031
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8904
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8878
Transthyretin P02767 TTHY_RAT Rattus norvegicus 3 0.8835
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.8829
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.8808
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8782
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 4 0.8725
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8712
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8701
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8679
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 4 0.8646
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.8641
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8546
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.8518
Isoflavone 4'-O-methyltransferase Q29U70 I4OMT_MEDTR Medicago truncatula 4 0.8495
Dihydrofolate reductase Q81R22 Q81R22_BACAN Bacillus anthracis 4 0.8460
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8457
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.8453
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 4 0.8423
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8408
RNA polymerase sigma factor SigA Q5SKW1 Q5SKW1_THET8 Thermus thermophilus 3 0.8405
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8374
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.8368
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8359
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.8357
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8353
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8324
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8312
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8277
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8247
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.8226
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.8215
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8214
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8210
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8186
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.8179
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8179
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8178
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8110
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 3 0.8103
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.8045
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.8033
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 4 0.8024
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8023
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.8017
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.8016
Dihydrofolate reductase Q81R22 Q81R22_BACAN Bacillus anthracis 4 0.8011
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8010
Transthyretin P02766 TTHY_HUMAN Homo sapiens 4 0.7991
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7984
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7969
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7941
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7940
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 4 0.7929
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7912
Purine nucleoside phosphorylase DeoD-type Q5EEL8 DEOD_BACCE Bacillus cereus 3 0.7869
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7819
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7806
Tau-tubulin kinase 1 Q5TCY1 TTBK1_HUMAN Homo sapiens 3 0.7791
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7781
Dihydrofolate reductase P22906 DYR_CANAX Candida albicans 3 0.7756
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 4 0.7747
Putative cytochrome P450 Q70AS3 Q70AS3_STRPE Streptomyces peucetius 4 0.7741
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7719
Enoyl-ACP reductase Q9BH77 Q9BH77_PLAFA Plasmodium falciparum 3 0.7706
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7696
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7659
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7654
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7647
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7640
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7633
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7629
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7628
Ephrin type-A receptor 4 Q03137 EPHA4_MOUSE Mus musculus 4 0.7621
Beta-adrenergic receptor kinase 1 P25098 ARBK1_HUMAN Homo sapiens 3 0.7614
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 3 0.7598
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7598
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7596
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 4 0.7570
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7562
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7562
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7553
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7540
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7539
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7539
UDP-N-acetylmuramoyl-L-alanyl-D-glutamate--LD-lysine ligase Q9WY79 MURE_THEMA Thermotoga maritima 3 0.7513
Calmodulin-like domain protein kinase isoenzyme gamma, related F0V9W9 F0V9W9_NEOCL Neospora caninum 3 0.7512
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7508
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 2 0.7507
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7497
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7491
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7483
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7472
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7451
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7434
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.7431
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 4 0.7422
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.7414
Acetolactate synthase catalytic subunit, mitochondrial P07342 ILVB_YEAST Saccharomyces cerevisiae 3 0.7411
Pyridoxal kinase P82197 PDXK_SHEEP Ovis aries 3 0.7367
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7364
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7329
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7313
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7310
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7307
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7303
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7293
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7288
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.7287
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7268
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.7253
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7244
Caspase-6 P55212 CASP6_HUMAN Homo sapiens 3 0.7244
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7220
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7200
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7183
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.7178
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.7177
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7170
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7170
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 3 0.7163
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7150
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7139
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7128
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7116
Chalcone synthase 2 P30074 CHS2_MEDSA Medicago sativa 3 0.7099
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7095
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7093
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7086
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7068
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7065
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 3 0.7061
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7061
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7054
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.7028
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7025
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7010
Ribonuclease TTHA0252 Q5SLP1 RNSE_THET8 Thermus thermophilus 3 0.7010
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7007
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 4 0.7002

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