18-metoxycytochalasin J - Compound Card

18-metoxycytochalasin J

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18-metoxycytochalasin J

Structure
Zoomed Structure
  • Family: Fungi - Valsaceae
  • Kingdom: Fungi
  • Class: Alkaloid
Canonical Smiles CO[C@@]1(C)/C=C/[C@@H](O)[C@@]23C(=O)N[C@H](C2[C@H](C)C(=C)[C@H]([C@H]3/C=C/C[C@@H](C1)C)O)Cc1ccccc1
InChI InChI=1S/C29H39NO4/c1-18-10-9-13-22-26(32)20(3)19(2)25-23(16-21-11-7-6-8-12-21)30-27(33)29(22,25)24(31)14-15-28(4,17-18)34-5/h6-9,11-15,18-19,22-26,31-32H,3,10,16-17H2,1-2,4-5H3,(H,30,33)/b13-9+,15-14+/t18-,19+,22+,23-,24+,25?,26+,28-,29+/m0/s1
InChIKey LIZLHKYMYYPMJW-DHSLCVIJSA-N
Formula C29H39NO4
HBA 4
HBD 3
MW 465.63
Rotatable Bonds 3
TPSA 78.79
LogP 3.82
Number Rings 4
Number Aromatic Rings 1
Heavy Atom Count 34
Formal Charge 0
Fraction CSP3 0.55
Exact Mass 465.29
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Phomopsis sp. Valsaceae Fungi —

Showing of synonyms

  • Jouda JB, Tamokou JD, et al. (2016). Antibacterial and cytotoxic cytochalasins from the endophytic fungus Phomopsis sp. harbored in Garcinia kola (Heckel) nut.. BMC complementary and alternative medicine,2016, 16(1), 462. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1ccccc1CC(NC2=O)C(C234)CC(=C)CC3C=CCCCCC=CC4

Level: 1

Mol. Weight: 465.63 g/mol

Structure

SMILES: O=C1NCC(C123)CC(=C)CC2C=CCCCCC=CC3

Level: 0

Mol. Weight: 465.63 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 465.63 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.85
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.850
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.96

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.270
Plasma Protein Binding
82.71
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
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
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.780
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.240
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.510
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.520
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
-202.420
Rat (Acute)
4.020
Rat (Chronic Oral)
2.510
Fathead Minnow
4.040
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
467.640
Hydration Free Energy
-3.160
Log(D) at pH=7.4
3.480
Log(P)
3.96
Log S
-4.77
Log(Vapor Pressure)
-9.47
Melting Point
179.01
pKa Acid
7.42
pKa Basic
5.14
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8513
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.8092
Protein LlR18A P52778 L18A_LUPLU Lupinus luteus 3 0.8087
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7856
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7856
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.7645
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7642
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7619
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7563
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7556
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7478
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7471
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7432
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.7410
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 2 0.7392
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7300
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7215
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7193
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 2 0.7109
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7101
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 2 0.7098
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7023
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7006

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