Phomacin B - Compound Card

Phomacin B

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Phomacin B

Structure
Zoomed Structure
  • Family: Fungi - Sporormiaceae
  • Kingdom: Fungi
  • Class: Alkaloid
    • Subclass: Cytochalasan Alkaloid
Canonical Smiles OC[C@H]1C/C(=C/[C@H]2C=C(C)[C@H]([C@@H]3[C@@]2(OC(=O)/C=C\[C@H](C1)O)C(=O)N[C@H]3CC(C)C)C)/C
InChI InChI=1S/C25H37NO5/c1-14(2)8-21-23-17(5)16(4)11-19-10-15(3)9-18(13-27)12-20(28)6-7-22(29)31-25(19,23)24(30)26-21/h6-7,10-11,14,17-21,23,27-28H,8-9,12-13H2,1-5H3,(H,26,30)/b7-6-,15-10+/t17-,18+,19+,20-,21+,23+,25-/m1/s1
InChIKey IXONDWQZWWLZDF-ZCMVJGEESA-N
Formula C25H37NO5
HBA 5
HBD 3
MW 431.57
Rotatable Bonds 3
TPSA 95.86
LogP 2.91
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.68
Exact Mass 431.27
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Westerdykella nigra Sporormiaceae Fungi 325665

Showing of synonyms

  • Sallam A, Sabry M.A, et al. (2021). Westalsan: A new acetylcholine esterase inhibitor from the endophytic fungus Westerdykella nigra. Chemistry & biodiversity, 2021, 18(4), e2000957. [View] [PubMed]
Pubchem: 10622584
Chebi: 66747
Nmrshiftdb2: 80005362
Metabolights: MTBLC66747

No compound-protein relationship available.

Structure

SMILES: O=C1NCC(C123)CC=CC2C=CCCCCC=CC(=O)O3

Level: 0

Mol. Weight: 431.57 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.69
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.890
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.41

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.900
Plasma Protein Binding
64.24
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
Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.880
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.980
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.360
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.080
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
-31.860
Rat (Acute)
2.680
Rat (Chronic Oral)
2.290
Fathead Minnow
3.920
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
478.800
Hydration Free Energy
-3.700
Log(D) at pH=7.4
3.220
Log(P)
2.6
Log S
-4.4
Log(Vapor Pressure)
-8.69
Melting Point
169.32
pKa Acid
6.13
pKa Basic
6.26
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8236
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7814
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7697
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7536
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7180

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