Skyrin - Compound Card

Skyrin

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Skyrin

Structure
Zoomed Structure
  • Family: Fungi - Trichocomaceae
  • Kingdom: Fungi
  • Class: Alkaloid
    • Subclass: Cyclic Peptide
Canonical Smiles Cc1cc(O)c2c(c1)C(=O)c1c(C2=O)c(O)cc(c1c1c(O)cc(c2c1C(=O)c1cc(C)cc(c1C2=O)O)O)O
InChI InChI=1S/C30H18O10/c1-9-3-11-19(13(31)5-9)29(39)23-17(35)7-15(33)21(25(23)27(11)37)22-16(34)8-18(36)24-26(22)28(38)12-4-10(2)6-14(32)20(12)30(24)40/h3-8,31-36H,1-2H3
InChIKey MQSXZQXHIJMNAF-UHFFFAOYSA-N
Formula C30H18O10
HBA 10
HBD 6
MW 538.46
Rotatable Bonds 1
TPSA 189.66
LogP 3.75
Number Rings 6
Number Aromatic Rings 4
Heavy Atom Count 40
Formal Charge 0
Fraction CSP3 0.07
Exact Mass 538.09
Number of Lipinski Rule Violations 2
# 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: 73071
Chebi: 144311
Nmrshiftdb2: 60076434
Bindingdb: 50388868
CPRiL: 64003
Structure

SMILES: c1cccc(C2=O)c1C(=O)c(c23)cccc3-c4cccc(c45)C(=O)c6c(C5=O)cccc6

Level: 1

Mol. Weight: 538.46 g/mol

Structure

SMILES: c1cccc(c12)C(=O)c3c(C2=O)cccc3

Level: 0

Mol. Weight: 538.46 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.09
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.1
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
2.78

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.94
Plasma Protein Binding
80.43
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
8.81
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.13
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.92
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.77
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
-3531.5
Rat (Acute)
2.44
Rat (Chronic Oral)
4.46
Fathead Minnow
16.83
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
611.02
Hydration Free Energy
-3.13
Log(D) at pH=7.4
2.47
Log(P)
6.78
Log S
-7.35
Log(Vapor Pressure)
-8.13
Melting Point
368.22
pKa Acid
9.79
pKa Basic
1.34
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8391
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8391
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.8181
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.8181
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8170
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8170
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.8030
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.8030
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7893
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7893
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.7750
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.7750
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.7638
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.7638
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7581
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7581
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7363
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7363
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7244
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7244
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 4 0.7230
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 4 0.7230
3-hydroxy-3-methylglutaryl-coenzyme A reductase P04035 HMDH_HUMAN Homo sapiens 3 0.7181
3-hydroxy-3-methylglutaryl-coenzyme A reductase P04035 HMDH_HUMAN Homo sapiens 3 0.7181
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Q3JRA0 ISPF_BURP1 Burkholderia pseudomallei 4 0.7048
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Q3JRA0 ISPF_BURP1 Burkholderia pseudomallei 4 0.7048
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7022
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7022

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