Vismione D - Compound Card

Vismione D

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Vismione D

Structure
Zoomed Structure
  • Family: Plantae - Hypericaceae
  • Kingdom: Plantae
  • Class: Anthraquinone
Canonical Smiles C/C(=C\COc1cc(O)c2c(c1)cc1c(c2O)C(=O)CC(C1)(C)O)/CCC=C(C)C
InChI InChI=1S/C25H30O5/c1-15(2)6-5-7-16(3)8-9-30-19-11-17-10-18-13-25(4,29)14-21(27)23(18)24(28)22(17)20(26)12-19/h6,8,10-12,26,28-29H,5,7,9,13-14H2,1-4H3/b16-8+
InChIKey KZPCPZBBGCTGCN-LZYBPNLTSA-N
Formula C25H30O5
HBA 5
HBD 3
MW 410.51
Rotatable Bonds 6
TPSA 86.99
LogP 5.2
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.4
Exact Mass 410.21
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Psorospermum aurantiacum Hypericaceae Plantae 999533

Showing of synonyms

  • Tiani G, Ahmed I, et al. (2013). Kenganthranol F, a new Anthranol from Psorospermum aurantiacum.. Natural Product Communications, 2013, 8(1), 103-104. [View] [PubMed]
Pubchem: 5281573
Kegg Ligand: C09977
Chebi: 10000
Nmrshiftdb2: 60071570

No compound-protein relationship available.

Structure

SMILES: O=C1CCCc(c12)cc3c(c2)cccc3

Level: 0

Mol. Weight: 410.51 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.86
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.81
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.94

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.06
Plasma Protein Binding
62.53
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
5.93
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.83
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.26
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.44
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
-10.97
Rat (Acute)
2.2
Rat (Chronic Oral)
2.73
Fathead Minnow
5.3
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
474.89
Hydration Free Energy
-6.32
Log(D) at pH=7.4
3.96
Log(P)
6.39
Log S
-6.07
Log(Vapor Pressure)
-8.39
Melting Point
138.65
pKa Acid
7.9
pKa Basic
5.57
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9463
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9420
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.9410
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.9332
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.9196
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9165
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.9086
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.9008
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8986
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8985
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.8977
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8892
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8842
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.8792
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8786
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8769
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.8633
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8605
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8604
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8593
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8578
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.8557
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.8552
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8530
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8526
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.8526
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8509
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8430
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8415
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 4 0.8377
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8361
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8337
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8307
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 3 0.8307
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8305
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8286
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8251
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 3 0.8205
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8200
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8199
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8145
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8051
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.8043
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8023
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8016
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.8001
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7998
Fumarate reductase subunit D P0A8Q3 FRDD_ECOLI Escherichia coli 3 0.7991
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.7986
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7979
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7943
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 3 0.7920
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7920
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7919
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7874
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7856
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7849
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7846
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7834
Putative polyketide cyclase P23154 CYPC_STRCO Streptomyces coelicolor / M145) 5 0.7803
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 3 0.7781
Purine nucleoside phosphorylase DeoD-type Q5EEL8 DEOD_BACCE Bacillus cereus 3 0.7764
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.7762
Ribosomal RNA small subunit methyltransferase E Q5SKI6 Q5SKI6_THET8 Thermus thermophilus 4 0.7747
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7740
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7724
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7720
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7687
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7683
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 4 0.7681
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7648
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7640
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7639
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7625
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7606
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7600
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7573
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7566
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7528
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7528
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.7528
Cholesterol side-chain cleavage enzyme, mitochondrial P00189 CP11A_BOVIN Bos taurus 4 0.7514
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7506
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7504
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7503
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7498
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7490
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7484
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7484
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7484
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 3 0.7464
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 2 0.7462
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7451
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7448
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7428
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7400
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7397
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7390
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 3 0.7390
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.7387
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7376
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7359
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7355
Rifampin ADP-ribosyl transferase A0QRS5 A0QRS5_MYCS2 Mycolicibacterium smegmatis155) 4 0.7311
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.7300
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7274
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7263
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7252
Nucleoside diphosphate kinase A 2 P52175 NDKA2_BOVIN Bos taurus 3 0.7252
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7252
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7250
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7248
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7245
DNA mismatch repair protein Msh2 P43246 MSH2_HUMAN Homo sapiens 3 0.7239
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7235
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7235
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 4 0.7226
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7214
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 3 0.7209
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 2 0.7205
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7201
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7198
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7196
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7182
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7171
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7166
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7159
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7158
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7118
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 2 0.7113
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7113
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7106
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7102
Aspartokinase 1, chloroplastic Q9LYU8 AK1_ARATH Arabidopsis thaliana 3 0.7102
SRSF protein kinase 1 Q96SB4 SRPK1_HUMAN Homo sapiens 3 0.7083
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7053
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7052
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7052
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7051
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7044
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7044
Tyrosine-protein kinase ABL1 P00519 ABL1_HUMAN Homo sapiens 3 0.7036
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7035
tRNA (adenine(9)-N1)-methyltransferase Q4J894 TRM10_SULAC Sulfolobus acidocaldarius 4 0.7033
DNA mismatch repair protein MutS P23909 MUTS_ECOLI Escherichia coli 3 0.7033
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7032
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7030
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7029
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7028
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 4 0.7028
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7027
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7025
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7020
Maltokinase A1TH50 MAK_MYCVP Mycolicibacterium vanbaalenii 3 0.7017
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7015
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7013
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7004
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 3 0.7002
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7002

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