Penialidin B - Compound Card

Penialidin B

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Penialidin B

Structure
Zoomed Structure
  • Family: Fungi - Trichocomaceae
  • Kingdom: Fungi, Plantae
  • Class: Chromone
    • Subclass: Polyketide
Canonical Smiles CO[C@]1(C)OCCc2c1oc1cc(O)c(c(c1c2=O)C(=O)O)O
InChI InChI=1S/C15H14O8/c1-15(21-2)13-6(3-4-22-15)11(17)9-8(23-13)5-7(16)12(18)10(9)14(19)20/h5,16,18H,3-4H2,1-2H3,(H,19,20)/t15-/m1/s1
InChIKey BBMNPWJIXCHDBW-OAHLLOKOSA-N
Formula C15H14O8
HBA 7
HBD 3
MW 322.27
Rotatable Bonds 2
TPSA 126.43
LogP 1.29
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.33
Exact Mass 322.07
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Garcinia nobilis Clusiaceae Plantae 469933
2 Penicillium sp. Trichocomaceae Fungi 5081
3 Penicillium sp. Trichocomaceae Fungi 5081
4 Penicillium sp. Trichocomaceae Fungi 5081

Showing of synonyms

  • Jouda JB, Mawabo IK, et al. (2016). Anti-mycobacterial activity of polyketides from Penicillium sp. endophyte isolated from Garcinia nobilis against Mycobacteriumsmegmatis.. International journal of mycobacteriology,2016, 5(2), 192-196. [View] [PubMed]
  • Jouda JB, Tamokou JD, et al. (2016). Anticancer and antibacterial secondary metabolites from the endophytic fungus Penicillium sp. CAM64 against multi-drug resistant Gram-negative bacteria.. African health sciences,2016, 16(3), 734-743. [View] [PubMed]
  • Jouda JB, Kusari S, et al. (2014). Penialidins A-C with strong antibacterial activities from Penicillium sp., an endophytic fungus harboring leaves of Garcinia nobilis.. Fitoterapia,2014, 98, 209-214. [View] [PubMed]
Pubchem: 139587010
Nmrshiftdb2: 80008054

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)oc3c(c2=O)CCOC3

Level: 0

Mol. Weight: 322.27 g/mol

Antibacterial
Anticancer

Absorption

Caco-2 (logPapp)
-5.97
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.480
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-4.01

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.750
Plasma Protein Binding
54.67
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
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
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
6.400
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.310
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.080
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.660
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
2.220
Rat (Acute)
2.130
Rat (Chronic Oral)
3.010
Fathead Minnow
3.960
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
430.160
Hydration Free Energy
-6.950
Log(D) at pH=7.4
-0.990
Log(P)
0.62
Log S
-2.7
Log(Vapor Pressure)
-10.32
Melting Point
255.76
pKa Acid
3.62
pKa Basic
5.36
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8823
Three-prime repair exonuclease 1 Q91XB0 TREX1_MOUSE Mus musculus 3 0.8741
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8428
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.8181
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8149
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8053
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.7912
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7774
3-hydroxybenzoate 4-monooxygenase Q6SSJ6 MOBA_COMTE Comamonas testosteroni 3 0.7438
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7436
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7407
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7262
Nitroreductase domain-containing protein Q8DW21 Q8DW21_STRMU Streptococcus mutans serotype c 3 0.7260
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7245
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7212
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7176
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.7103
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 4 0.7031
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7012

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