Ferruginin B - Compound Card

Ferruginin B

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Ferruginin B

Structure
Zoomed Structure
  • Family: Plantae - Hypericaceae
  • Kingdom: Plantae
  • Class: Anthranol
Canonical Smiles CC(=CCC1(CC=C(C)C)C(=O)C(=C(c2c1cc1cc(C)cc(c1c2O)O)O)CC=C(C)C)C
InChI InChI=1S/C30H36O4/c1-17(2)8-9-22-27(32)26-23(16-21-14-20(7)15-24(31)25(21)28(26)33)30(29(22)34,12-10-18(3)4)13-11-19(5)6/h8,10-11,14-16,31-33H,9,12-13H2,1-7H3
InChIKey SAZNPNYLSKFIJG-UHFFFAOYSA-N
Formula C30H36O4
HBA 4
HBD 3
MW 460.61
Rotatable Bonds 6
TPSA 77.76
LogP 7.72
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 34
Formal Charge 0
Fraction CSP3 0.37
Exact Mass 460.26
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: 21680812
Nmrshiftdb2: 60052999

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)cc3c(c2)C=CC(=O)C3

Level: 0

Mol. Weight: 460.61 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.82
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.87
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.46

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.21
Plasma Protein Binding
60.93
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
Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.29
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.48
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.36
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.37
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-92.06
Rat (Acute)
2.09
Rat (Chronic Oral)
3.65
Fathead Minnow
5.79
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
472.06
Hydration Free Energy
-3.44
Log(D) at pH=7.4
5.2
Log(P)
8.78
Log S
-6.8
Log(Vapor Pressure)
-9.08
Melting Point
172.64
pKa Acid
8.68
pKa Basic
6.33
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.9003
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.8970
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8860
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8689
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8682
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 3 0.8465
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8387
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.8319
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7987
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7965
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 3 0.7920
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.7821
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.7802
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7726
Metallo-beta-lactamase type 2 P26918 BLAB_AERHY Aeromonas hydrophila 3 0.7659
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7659
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7634
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7604
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7475
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7468
Protein mono-ADP-ribosyltransferase PARP14 Q460N5 PAR14_HUMAN Homo sapiens 3 0.7435
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.7415
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7361
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7236
GTP 3',8-cyclase P69848 MOAA_STAA8 Staphylococcus aureus 3 0.7157
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7155
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7030
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7027
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7003
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7000

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