Rugulosin B - Compound Card

Rugulosin B

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Rugulosin B

Structure
Zoomed Structure
  • Family: Fungi - Trichocomaceae
  • Kingdom: Fungi
  • Class: Alkaloid
    • Subclass: Cyclic Peptide
Canonical Smiles OCc1cc(O)c2c(c1)C(=O)[C@]13C(=C2O)C(=O)[C@H]2[C@H]([C@@H]3[C@H]3[C@@H]([C@@H]1C(=O)C1=C(O)c4c(C(=O)[C@]231)cc(cc4O)C)O)O
InChI InChI=1S/C30H22O11/c1-7-2-9-13(11(32)3-7)21(34)17-25(38)20-23(36)15-16-24(37)19(29(15,17)27(9)40)26(39)18-22(35)14-10(28(41)30(16,18)20)4-8(6-31)5-12(14)33/h2-5,15-16,19-20,23-24,31-37H,6H2,1H3/t15-,16-,19+,20+,23-,24-,29+,30+/m0/s1
InChIKey ZPRZJORQEHCPCD-PUTAFCBNSA-N
Formula C30H22O11
HBA 11
HBD 7
MW 558.5
Rotatable Bonds 1
TPSA 209.89
LogP 0.88
Number Rings 8
Number Aromatic Rings 2
Heavy Atom Count 41
Formal Charge 0
Fraction CSP3 0.33
Exact Mass 558.12
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Talaromyces wortmannii Trichocomaceae Fungi 28567

Showing of synonyms

  • Bara R (2012). Natural Products from Endophytic Fungus Talaromyces wortmannii: Their Structure and mechanism of Actions. PhD Thesis, Institute for Pharmaceutical Biology and Biotechnology, University of Dusseldorf,2012, pp. 1-142.. [View]
Pubchem: 102162848

No compound-protein relationship available.

Structure

SMILES: c1cccc(C2=O)c1C=C(C(=O)C3C4)C2(C4C5C367)C(C5)C(=O)C6=Cc8c(C7=O)cccc8

Level: 0

Mol. Weight: 558.5 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.24
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.97
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
5.26

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.68
Plasma Protein Binding
83.14
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.53
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-3.95
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.82
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.59
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Toxic
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
-10719.02
Rat (Acute)
3.34
Rat (Chronic Oral)
5.14
Fathead Minnow
24.67
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
479.77
Hydration Free Energy
-2.94
Log(D) at pH=7.4
0.66
Log(P)
2.37
Log S
-4.37
Log(Vapor Pressure)
-11.24
Melting Point
297.96
pKa Acid
6.84
pKa Basic
0.01
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 3 0.8893
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 3 0.8893
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7403
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7403
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7182
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7182

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