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Citromycetin
- Family: Fungi - Trichocomaceae
- Kingdom: Fungi, Plantae
-
Class: Chromone
- Subclass: Polyketide
| Canonical Smiles | Cc1cc(=O)c2c(o1)c1c(OC2)cc(c(c1C(=O)O)O)O |
|---|---|
| InChI | InChI=1S/C14H10O7/c1-5-2-7(15)6-4-20-9-3-8(16)12(17)11(14(18)19)10(9)13(6)21-5/h2-3,16-17H,4H2,1H3,(H,18,19) |
| InChIKey | PKEPGKZPVDAVKI-UHFFFAOYSA-N |
| Formula | C14H10O7 |
| HBA | 6 |
| HBD | 3 |
| MW | 290.23 |
| Rotatable Bonds | 1 |
| TPSA | 117.2 |
| LogP | 1.62 |
| Number Rings | 3 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 21 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.14 |
| Exact Mass | 290.04 |
| 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
Citromycetin
478-60-4
Frequentic acid
8,9-dihydroxy-2-methyl-4-oxo-5H-pyrano[3,2-c]chromene-10-carboxylic acid
UNII-6LQ9JP1YA7
6LQ9JP1YA7
NSC 53584
BRN 0330020
CITROMYCETIN [MI]
NSC-53584
DTXSID60197283
4-19-00-03953 (Beilstein Handbook Reference)
4H,5H-Pyrano(3,2-c)(1)benzopyran-10-carboxylic acid, 8,9-dihydroxy-2-methyl-4-oxo-
8,9-Dihydroxy-2-methyl-4-oxo-4H,5H-pyrano[3,2-c][1]benzopyran-10-carboxylic acid
8,9-DIHYDROXY-2-METHYL-4-OXO-4H,5H-PYRANO(3,2-C)(1)BENZOPYRAN-10-CARBOXYLIC ACID
8,9-Dihydroxy-2-methyl-4-oxo-4H,5H-pyrano(3,2-c)chromene-10-carboxylate
8,9-Dihydroxy-2-methyl-4-oxo-4H,5H-pyrano[3,2-c]chromene-10-carboxylate
8,9-dihydroxy-2-methyl-4-oxo-5H-pyrano(3,2-c)chromene-10-carboxylic acid
DTXCID70119774
NSC53584
8,9-Dihydroxy-2-methyl-4-oxo-4H,5H-pyrano[3,2-c]chromene-10-carboxylic acid
4H,5H-Pyrano[3,2-c][1]benzopyran-10-carboxylicacid, 8,9-dihydroxy-2-methyl-4-oxo-
Spectrum_000290
SpecPlus_000355
Spectrum5_000777
KBioSS_000770
DivK1c_006451
SCHEMBL2137852
ACon1_002335
KBio1_001395
KBio2_000770
KBio2_003338
KBio2_005906
CHEBI:201809
AKOS040748138
FC32531
NCGC00169943-01
DA-62352
HY-116479
CS-0065609
Q15410873
4H,2-c][1]benzopyran-10-carboxylic acid, 8,9-dihydroxy-2-methyl-4-oxo-
- 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]
No compound-protein relationship available.
SMILES: o1ccc(=O)c(c1c23)COc2cccc3
Level: 0
Mol. Weight: 290.23 g/mol
Antibacterial
Anticancer
Absorption
- Caco-2 (logPapp)
- -6.07
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.57
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -3.0
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 1.21
- Plasma Protein Binding
- 59.53
- 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
- 8.47
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- -0.15
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.45
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 3.41
- 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
- 5.54
- Rat (Acute)
- 2.34
- Rat (Chronic Oral)
- 3.5
- Fathead Minnow
- 3.93
- 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
- 461.91
- Hydration Free Energy
- -6.02
- Log(D) at pH=7.4
- -0.13
- Log(P)
- 0.87
- Log S
- -3.01
- Log(Vapor Pressure)
- -10.95
- Melting Point
- 318.58
- pKa Acid
- 3.89
- pKa Basic
- 6.0
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.9216 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.9146 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8871 |
| 11-beta-hydroxysteroid dehydrogenase 1 | Q6QLL4 | DHI1_CAVPO | Cavia porcellus | 3 | 0.8825 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 4 | 0.8637 |
| Anthranilate phosphoribosyltransferase | P9WFX5 | TRPD_MYCTU | Mycobacterium tuberculosis | 3 | 0.8582 |
| Gag-Pol polyprotein | P03366 | POL_HV1B1 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.8477 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.8406 |
| Gag-Pol polyprotein | P03366 | POL_HV1B1 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.8383 |
| Gag-Pol polyprotein | P04585 | POL_HV1H2 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.8351 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | P48736 | PK3CG_HUMAN | Homo sapiens | 3 | 0.8331 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.8305 |
| Fibroblast growth factor receptor 1 | P11362 | FGFR1_HUMAN | Homo sapiens | 3 | 0.8299 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 3 | 0.8248 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.8248 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8219 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 3 | 0.8204 |
| Bifunctional dihydrofolate reductase-thymidylate synthase | P13922 | DRTS_PLAFK | Plasmodium falciparum | 3 | 0.8066 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.8065 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.8041 |
| Serine/threonine-protein kinase PLK2 | Q9NYY3 | PLK2_HUMAN | Homo sapiens | 3 | 0.7967 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7967 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7915 |
| Catalase-peroxidase 2 | O59651 | KATG2_HALMA | Haloarcula marismortui | 3 | 0.7896 |
| Glycogen phosphorylase, muscle form | P00489 | PYGM_RABIT | Oryctolagus cuniculus | 3 | 0.7869 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7829 |
| Aminoglycoside 3'-phosphotransferase AphA1-IAB | B0VD92 | B0VD92_ACIBY | Acinetobacter baumannii | 4 | 0.7823 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7812 |
| Proto-oncogene tyrosine-protein kinase Src | P00523 | SRC_CHICK | Gallus gallus | 3 | 0.7753 |
| Gag-Pol polyprotein | P03367 | POL_HV1BR | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7741 |
| Protocatechuate 3,4-dioxygenase beta chain | P00437 | PCXB_PSEPU | Pseudomonas putida | 3 | 0.7734 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.7704 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 3 | 0.7700 |
| Gag-Pol polyprotein | P04585 | POL_HV1H2 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7693 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.7681 |
| Gag-Pol polyprotein | P04585 | POL_HV1H2 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7673 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7664 |
| Anthranilate phosphoribosyltransferase | P00500 | TRPD_ACIAD | Acinetobacter baylyi | 3 | 0.7663 |
| Riboflavin synthase | P0AFU8 | RISA_ECOLI | Escherichia coli | 3 | 0.7623 |
| cGMP-specific 3',5'-cyclic phosphodiesterase | O76074 | PDE5A_HUMAN | Homo sapiens | 4 | 0.7618 |
| MAP kinase-activated protein kinase 2 | P49137 | MAPK2_HUMAN | Homo sapiens | 3 | 0.7608 |
| Thermolysin | P00800 | THER_BACTH | Bacillus thermoproteolyticus | 3 | 0.7597 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 3 | 0.7596 |
| Gag-Pol polyprotein | P04585 | POL_HV1H2 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7510 |
| cGMP-specific 3',5'-cyclic phosphodiesterase | O76074 | PDE5A_HUMAN | Homo sapiens | 4 | 0.7492 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.7486 |
| Polymerase acidic protein | Q5EP34 | Q5EP34_9INFA | Influenza A virus | 3 | 0.7425 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7415 |
| LIM domain kinase 1 | P53667 | LIMK1_HUMAN | Homo sapiens | 2 | 0.7369 |
| UDP-galactopyranose mutase | Q48485 | GLF1_KLEPN | Klebsiella pneumoniae | 3 | 0.7358 |
| Protoporphyrinogen oxidase | P50336 | PPOX_HUMAN | Homo sapiens | 3 | 0.7357 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7355 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.7328 |
| Serine/threonine-protein kinase PLK2 | Q9NYY3 | PLK2_HUMAN | Homo sapiens | 3 | 0.7311 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.7310 |
| Aminoglycoside 3'-phosphotransferase AphA1-IAB | B0VD92 | B0VD92_ACIBY | Acinetobacter baumannii | 4 | 0.7296 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 4 | 0.7288 |
| Ribonuclease J | H9CZL7 | H9CZL7_DEIRD | Deinococcus radiodurans | 3 | 0.7284 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7281 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7276 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7258 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7248 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7241 |
| Methionine aminopeptidase 2 | P50579 | MAP2_HUMAN | Homo sapiens | 4 | 0.7236 |
| Nucleoprotein | P33469 | NCAP_CVHOC | Human coronavirus OC43 | 3 | 0.7227 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 4 | 0.7212 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7210 |
| Flavin-dependent thymidylate synthase | Q9WYT0 | THYX_THEMA | Thermotoga maritima | 3 | 0.7181 |
| Acetyl-CoA carboxylase | Q00955 | ACAC_YEAST | Saccharomyces cerevisiae | 3 | 0.7180 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 4 | 0.7171 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 2 | 0.7163 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7157 |
| Homoserine dehydrogenase | P31116 | DHOM_YEAST | Saccharomyces cerevisiae | 3 | 0.7147 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7124 |
| N-acetylhexosamine 1-kinase | E8MF12 | NAHK_BIFL2 | Bifidobacterium longum subsp. longum | 3 | 0.7085 |
| Cyclin-dependent kinase 5 | Q00535 | CDK5_HUMAN | Homo sapiens | 4 | 0.7082 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7074 |
| Histone-lysine N-methyltransferase SETD7 | Q8WTS6 | SETD7_HUMAN | Homo sapiens | 3 | 0.7068 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7064 |
| NAD(P)H dehydrogenase [quinone] 1 | P15559 | NQO1_HUMAN | Homo sapiens | 3 | 0.7037 |
| Tyrosine-protein kinase JAK3 | P52333 | JAK3_HUMAN | Homo sapiens | 3 | 0.7037 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7034 |
| Ephrin type-B receptor 2 | P54763 | EPHB2_MOUSE | Mus musculus | 2 | 0.7022 |
| Steroid C26-monooxygenase | P9WPP1 | CP125_MYCTU | Mycobacterium tuberculosis | 3 | 0.7014 |
| Actin-related protein 3 | P61157 | ARP3_BOVIN | Bos taurus | 3 | 0.7007 |
| Dihydroflavonol 4-reductase | P51110 | DFRA_VITVI | Vitis vinifera | 4 | 0.7003 |
| E3 ubiquitin-protein ligase Mdm2 | Q00987 | MDM2_HUMAN | Homo sapiens | 3 | 0.7002 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7002 |