Cytochalasin H - Compound Card

Cytochalasin H

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Cytochalasin H

Structure
Zoomed Structure
  • Family: Fungi - Valsaceae
  • Kingdom: Fungi
  • Class: Alkaloid
Canonical Smiles CC(=O)O[C@@H]1/C=C\[C@](C)(O)C[C@H](C/C=C\[C@@H]2[C@]31C(=O)N[C@H]([C@@H]3[C@H](C)C(=C)[C@H]2O)Cc1ccccc1)C
InChI InChI=1S/C30H39NO5/c1-18-10-9-13-23-27(33)20(3)19(2)26-24(16-22-11-7-6-8-12-22)31-28(34)30(23,26)25(36-21(4)32)14-15-29(5,35)17-18/h6-9,11-15,18-19,23-27,33,35H,3,10,16-17H2,1-2,4-5H3,(H,31,34)/b13-9-,15-14-/t18-,19+,23-,24-,25+,26-,27+,29-,30+/m0/s1
InChIKey NAEWXXDGBKTIMN-LWYXIPTFSA-N
Formula C30H39NO5
HBA 5
HBD 3
MW 493.64
Rotatable Bonds 3
TPSA 95.86
LogP 3.74
Number Rings 4
Number Aromatic Rings 1
Heavy Atom Count 36
Formal Charge 0
Fraction CSP3 0.53
Exact Mass 493.28
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]
Pubchem: 101706637
Nmrshiftdb2: 70096453
CPRiL: 74582
Structure

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

Level: 1

Mol. Weight: 493.64 g/mol

Structure

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

Level: 0

Mol. Weight: 493.64 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 493.64 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.71
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.76
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.63

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.2
Plasma Protein Binding
86.27
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
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
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.83
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.01
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.07
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.65
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-413.66
Rat (Acute)
4.2
Rat (Chronic Oral)
2.24
Fathead Minnow
4.04
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
486.49
Hydration Free Energy
-3.11
Log(D) at pH=7.4
3.35
Log(P)
3.29
Log S
-4.67
Log(Vapor Pressure)
-9.78
Melting Point
168.44
pKa Acid
7.15
pKa Basic
4.55
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 4 0.8062
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.8048
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7819
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7596
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7539
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7528
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7306
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7299
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.7241
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7199
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7188
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7183
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.7182
Chymotrypsinogen A P00766 CTRA_BOVIN Bos taurus 3 0.7137
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 2 0.7112
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7030
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 2 0.7023
Large structural protein Q91L20 Q91L20_9MONO Human metapneumovirus 3 0.7005

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