Variecolorin O - Compound Card

Variecolorin O

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Variecolorin O

Structure
Zoomed Structure
  • Family: Fungi - Trichocomaceae
  • Kingdom: Fungi
  • Class: Alkaloid
    • Subclass: Indole Alkaloid
Canonical Smiles C=CC(c1[nH]c2c(c1/C=C/1\NC(=O)C(NC1=O)(C)O)cccc2)(C)C
InChI InChI=1S/C19H21N3O3/c1-5-18(2,3)15-12(11-8-6-7-9-13(11)20-15)10-14-16(23)22-19(4,25)17(24)21-14/h5-10,20,25H,1H2,2-4H3,(H,21,24)(H,22,23)/b14-10-
InChIKey KXDOFLWMYBNRGX-UVTDQMKNSA-N
Formula C19H21N3O3
HBA 3
HBD 4
MW 339.4
Rotatable Bonds 3
TPSA 94.22
LogP 1.93
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.26
Exact Mass 339.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Aspergillus amstelodami Trichocomaceae Fungi 5054

Showing of synonyms

  • Elsbaey M, Sallam A, et al. (2019). Melanogenesis Inhibitors from the Endophytic Fungus Aspergillus amstelodami. Chem Biodivers,2019,16(8),e1900237. [View] [PubMed]
Pubchem: 49831794

No compound-protein relationship available.

Structure

SMILES: N1C(=O)CNC(=O)C1=Cc2c[nH]c(c23)cccc3

Level: 1

Mol. Weight: 339.4 g/mol

Structure

SMILES: C=C1C(=O)NCC(=O)N1

Level: 0

Mol. Weight: 339.4 g/mol

Structure

SMILES: c1c[nH]c(c12)cccc2

Level: 0

Mol. Weight: 339.4 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.08
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.72
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.03

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.04
Plasma Protein Binding
36.88
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
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
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.1
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.1
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.04
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.65
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
Toxic
T. Pyriformis
-1.27
Rat (Acute)
2.76
Rat (Chronic Oral)
2.99
Fathead Minnow
4.17
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
467.72
Hydration Free Energy
-15.7
Log(D) at pH=7.4
2.46
Log(P)
2.57
Log S
-4.26
Log(Vapor Pressure)
-10.02
Melting Point
207.2
pKa Acid
7.68
pKa Basic
5.86
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.9267
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.8883
Adenosine kinase Q9TVW2 ADK_TOXGO Toxoplasma gondii 4 0.8784
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.8016
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7937
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7899
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7868
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7831
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7822
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7753
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7717
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7706
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 3 0.7660
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7613
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7507
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7503
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7461
Purine nucleoside phosphorylase Q8I3X4 Q8I3X4_PLAF7 Plasmodium falciparum 3 0.7433
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7432
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7403
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 2 0.7346
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7339
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7321
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.7317
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7312
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7312
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7291
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7290
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 3 0.7275
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7165
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7125
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7090
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7060
Nitroreductase domain-containing protein Q8DW21 Q8DW21_STRMU Streptococcus mutans serotype c 3 0.7037

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