Fusaproliferin - Compound Card

Fusaproliferin

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Fusaproliferin

Structure
Zoomed Structure
  • Family: Fungi - Nectriaceae
  • Kingdom: Fungi
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CC(=O)OC[C@H](C1=C(O)C(=O)[C@@]2([C@@H]1C/C=C(\C)/[C@@H](O)CC/C(=C/CC/C(=C/C2)/C)/C)C)C
InChI InChI=1S/C27H40O5/c1-17-8-7-9-18(2)14-15-27(6)22(12-11-19(3)23(29)13-10-17)24(25(30)26(27)31)20(4)16-32-21(5)28/h8,11,14,20,22-23,29-30H,7,9-10,12-13,15-16H2,1-6H3/b17-8+,18-14+,19-11+/t20-,22-,23+,27+/m1/s1
InChIKey VRGWBRLULZUWAJ-UEWDWXLZSA-N
Formula C27H40O5
HBA 5
HBD 2
MW 444.61
Rotatable Bonds 3
TPSA 83.83
LogP 5.76
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 32
Formal Charge 0
Fraction CSP3 0.63
Exact Mass 444.29
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Fusarium sp. Nectriaceae Fungi 29916

Showing of synonyms

  • Kongue Tatong M, Talontsi F, et al. (2014). Banchromene and other secondary metabolites from the endophytic fungus Fusarium sp. obtained from Piper guineense inhibit the motility of phytopathogenic Plasmopara viticola zoospores. Tetrahedron Letters, 2014, 55(30), 4057-4061. [View]
Pubchem: 6506535
Nmrshiftdb2: 70107227
CPRiL: 227027
Structure

SMILES: O=C1C=CC(C12)CC=CCCCC=CCCC=CC2

Level: 0

Mol. Weight: 444.61 g/mol

Cytotoxic
Motility-impairing

Absorption

Caco-2 (logPapp)
-4.55
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.77
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.77

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.94
Plasma Protein Binding
89.35
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
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
Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.29
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.65
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.63
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.66
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Toxic
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-35.81
Rat (Acute)
2.64
Rat (Chronic Oral)
2.28
Fathead Minnow
4.95
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
461.3
Hydration Free Energy
-3.83
Log(D) at pH=7.4
3.52
Log(P)
6.03
Log S
-5.08
Log(Vapor Pressure)
-7.52
Melting Point
142.36
pKa Acid
8.86
pKa Basic
3.55
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.9376
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.9168
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8852
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8697
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.8697
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8368
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7869
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7868
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7821
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7748
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7686
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7641
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7477
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7467
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7349
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7307
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7264
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7246
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7224
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7186
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 3 0.7179
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7146
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7126
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7113
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7084
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7012

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