Citriquinochroman - Compound Card

Citriquinochroman

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Citriquinochroman

Structure
Zoomed Structure
  • Family: Fungi - Trichocomaceae
  • Kingdom: Fungi
  • Class: Alkaloid
Canonical Smiles COc1cc(O)c(c2c1C(O[C@H](C2)C)c1ccc2n1c(=O)c1c2[nH]c2c(c1=O)cccc2)C
InChI InChI=1S/C26H22N2O5/c1-12-10-15-13(2)19(29)11-20(32-3)21(15)25(33-12)18-9-8-17-23-22(26(31)28(17)18)24(30)14-6-4-5-7-16(14)27-23/h4-9,11-12,25,29H,10H2,1-3H3,(H,27,30)/t12-,25?/m0/s1
InChIKey YMMHCLHJARLKFK-UNHBDAOFSA-N
Formula C26H22N2O5
HBA 6
HBD 2
MW 442.47
Rotatable Bonds 2
TPSA 93.55
LogP 4.07
Number Rings 6
Number Aromatic Rings 4
Heavy Atom Count 33
Formal Charge 0
Fraction CSP3 0.23
Exact Mass 442.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Penicillium citrinum Trichocomaceae Fungi 5077

Showing of synonyms

  • El-Neketi M, Ebrahim W, et al. (2013). Alkaloids and polyketides from Penicillium citrinum, an endophyte isolated from the Moroccan plant Ceratonia siliqua. Journal of Natural Products,2013,76(6),1099-1104. [View] [PubMed]
Pubchem: 102528165

No compound-protein relationship available.

Structure

SMILES: c1cccc(c2=O)c1[nH]c(c23)c4n(C3=O)c(cc4)C5OCCc(c56)cccc6

Level: 1

Mol. Weight: 442.47 g/mol

Structure

SMILES: c1ccn(C2=O)c1c(c23)[nH]c4c(c3=O)cccc4

Level: 0

Mol. Weight: 442.47 g/mol

Structure

SMILES: C1COCc(c12)cccc2

Level: 0

Mol. Weight: 442.47 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-5.44
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.880
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.43

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.460
Plasma Protein Binding
73.53
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-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
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.070
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.990
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.340
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.080
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
-310.710
Rat (Acute)
2.980
Rat (Chronic Oral)
1.630
Fathead Minnow
5.820
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
573.200
Hydration Free Energy
-3.450
Log(D) at pH=7.4
3.230
Log(P)
3.4
Log S
-5.74
Log(Vapor Pressure)
-10.73
Melting Point
297.17
pKa Acid
10.03
pKa Basic
6.87
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.9609
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.9609
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.9363
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.9363
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.9297
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.9297
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9057
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9057
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.9057
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.9057
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.8890
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.8890
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8696
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8696
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8648
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8648
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.8596
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.8596
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8265
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8265
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 3 0.8238
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 3 0.8238
Dipeptidyl peptidase 4 P14740 DPP4_RAT Rattus norvegicus 3 0.8230
Dipeptidyl peptidase 4 P14740 DPP4_RAT Rattus norvegicus 3 0.8230
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8227
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8227
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8166
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8166
Geranylgeranyl transferase type-2 subunit alpha Q08602 PGTA_RAT Rattus norvegicus 3 0.8098
Geranylgeranyl transferase type-2 subunit alpha Q08602 PGTA_RAT Rattus norvegicus 3 0.8098
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 3 0.8038
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8038
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8038
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 3 0.8038
Caspase-6 P55212 CASP6_HUMAN Homo sapiens 3 0.7954
Caspase-6 P55212 CASP6_HUMAN Homo sapiens 3 0.7954
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7909
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7909
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7888
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7888
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7806
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7806
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7805
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7805
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7784
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7784
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7757
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7757
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7754
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7754
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 4 0.7752
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 4 0.7752
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 3 0.7685
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 3 0.7685
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7680
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7680
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7660
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7660
UDP-N-acetylglucosamine 1-carboxyvinyltransferase P33038 MURA_ENTCC Enterobacter cloacae subsp. cloacae 3 0.7605
UDP-N-acetylglucosamine 1-carboxyvinyltransferase P33038 MURA_ENTCC Enterobacter cloacae subsp. cloacae 3 0.7605
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7602
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7602
Dihydrofolate reductase Q81R22 Q81R22_BACAN Bacillus anthracis 4 0.7600
Dihydrofolate reductase Q81R22 Q81R22_BACAN Bacillus anthracis 4 0.7600
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7579
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7579
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7525
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7525
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7517
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7517
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 2 0.7516
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 2 0.7516
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7465
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7465
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7437
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7437
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7433
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7433
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7420
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7420
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7405
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7405
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7398
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7398
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7398
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7398
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7372
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7372
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7348
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7348
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7314
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7314
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 3 0.7308
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 3 0.7308
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.7299
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.7299
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7272
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7272
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7268
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7268
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7261
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7261
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7246
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7246
L-lactate dehydrogenase Q27743 LDH_PLAFD Plasmodium falciparum 2 0.7223
L-lactate dehydrogenase Q27743 LDH_PLAFD Plasmodium falciparum 2 0.7223
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7198
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7198
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7166
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7166
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7156
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7156
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 2 0.7154
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 2 0.7154
Vanillate porin OpdK Q9HUR5 Q9HUR5_PSEAE Pseudomonas aeruginosa 2 0.7134
Vanillate porin OpdK Q9HUR5 Q9HUR5_PSEAE Pseudomonas aeruginosa 2 0.7134
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7132
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7132
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7131
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7131
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7090
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7090
Histone demethylase UTY O14607 UTY_HUMAN Homo sapiens 3 0.7078
Histone demethylase UTY O14607 UTY_HUMAN Homo sapiens 3 0.7078
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7059
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7059
Renin P00797 RENI_HUMAN Homo sapiens 3 0.7039
Renin P00797 RENI_HUMAN Homo sapiens 3 0.7039
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7031
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7031
Cholinesterase P06276 CHLE_HUMAN Homo sapiens 3 0.7028
Cholinesterase P06276 CHLE_HUMAN Homo sapiens 3 0.7028
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7017
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7017

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