Aegyptolidine B - Compound Card

Aegyptolidine B

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Aegyptolidine B

Structure
Zoomed Structure
  • Family: Fungi - Trichocomaceae
  • Kingdom: Fungi
  • Class: Alkaloid
    • Subclass: Pyrrolidine Alkaloid
Canonical Smiles OC[C@H]1NC(=O)[C@H]([C@H]1Oc1ccc(cc1)O)Cl
InChI InChI=1S/C11H12ClNO4/c12-9-10(8(5-14)13-11(9)16)17-7-3-1-6(15)2-4-7/h1-4,8-10,14-15H,5H2,(H,13,16)/t8-,9+,10+/m1/s1
InChIKey CVICVWIGLPZPJX-UTLUCORTSA-N
Formula C11H12ClNO4
HBA 4
HBD 3
MW 257.67
Rotatable Bonds 3
TPSA 78.79
LogP 0.24
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 17
Formal Charge 0
Fraction CSP3 0.36
Exact Mass 257.05
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Aspergillus aegyptiacus Trichocomaceae Fungi 5052

Showing of synonyms

  • Ibrahim S, Mohamed G, et al. (2015). Aegyptolidines A and B: New pyrrolidine alkaloids from the fungus Aspergillus aegyptiacus. Phytochemistry Letters,2015,12,90–93. [View]
Pubchem: 139585485
Nmrshiftdb2: 70103938

No compound-protein relationship available.

Structure

SMILES: O=C1CC(CN1)Oc2ccccc2

Level: 1

Mol. Weight: 257.67 g/mol

Structure

SMILES: O=C1CCCN1

Level: 0

Mol. Weight: 257.67 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 257.67 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.15
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.850
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.08

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.380
Plasma Protein Binding
33.85
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
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
9.070
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.330
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.130
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.980
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
1.010
Rat (Acute)
2.320
Rat (Chronic Oral)
2.300
Fathead Minnow
3.970
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
366.610
Hydration Free Energy
-15.970
Log(D) at pH=7.4
0.190
Log(P)
0.35
Log S
-2.17
Log(Vapor Pressure)
-7.52
Melting Point
177.29
pKa Acid
8.21
pKa Basic
4.2
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.9860
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.9267
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9084
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8881
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8863
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 4 0.8848
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 3 0.8824
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8723
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.8722
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.8652
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.8565
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 3 0.8562
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8541
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8531
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8517
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8503
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8475
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8420
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.8417
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8360
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8355
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8342
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8329
Threonine synthase 1, chloroplastic Q9S7B5 THRC1_ARATH Arabidopsis thaliana 3 0.8308
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8212
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8181
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8173
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8091
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8053
Protein UshA P07024 USHA_ECOLI Escherichia coli 3 0.8031
Ras-related protein Rap-1b P61224 RAP1B_HUMAN Homo sapiens 4 0.8028
Coniferyl alcohol 9-O-methyltransferase A6XNE6 A6XNE6_9ROSI Linum nodiflorum 3 0.8009
Cobalt-precorrin-4 C(11)-methyltransferase O87696 CBIF_BACME Priestia megaterium 3 0.7981
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 4 0.7970
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7938
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7905
Nucleoside 2-deoxyribosyltransferase Q8RLY5 Q8RLY5_LACHE Lactobacillus helveticus 3 0.7869
Type II methyltransferase M.RsrI P14751 MTR1_RHOSH Cereibacter sphaeroides 4 0.7868
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7801
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7792
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7717
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7657
Type II methyltransferase M.RsrI P14751 MTR1_RHOSH Cereibacter sphaeroides 4 0.7656
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 3 0.7614
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7600
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7597
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7574
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7556
Myosin heavy chain, striated muscle P24733 MYS_ARGIR Argopecten irradians 3 0.7532
NADPH-dependent 7-cyano-7-deazaguanine reductase Q9KTK0 QUEF_VIBCH Vibrio cholerae serotype O1 3 0.7529
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7516
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7515
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7511
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 2 0.7506
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7485
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7473
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7465
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7464
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7427
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7427
Type IV pilus retractation ATPase PilT P24559 PILT_PSEAE Pseudomonas aeruginosa 3 0.7425
Catalase-peroxidase Q3JNW6 KATG_BURP1 Burkholderia pseudomallei 3 0.7413
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7411
Branched-chain alpha-ketoacid dehydrogenase kinase Q00972 BCKD_RAT Rattus norvegicus 4 0.7409
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 3 0.7403
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7399
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7382
IAG-nucleoside hydrolase Q9GPQ4 Q9GPQ4_TRYVI Trypanosoma vivax 3 0.7381
Raucaffricine-O-beta-D-glucosidase Q9SPP9 RG1_RAUSE Rauvolfia serpentina 3 0.7371
Peroxidase C1A P00433 PER1A_ARMRU Armoracia rusticana 3 0.7362
Phosphoglycerate kinase Q83AU6 PGK_COXBU Coxiella burnetii 3 0.7359
Probable bifunctional SAT/APS kinase O67174 SATC_AQUAE Aquifex aeolicus 3 0.7358
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.7352
16S rRNA (guanine(1405)-N(7))-methyltransferase Q763K9 Q763K9_ECOLX Escherichia coli 3 0.7316
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7315
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7314
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7296
Petrobactin biosynthesis protein AsbB Q81RQ8 Q81RQ8_BACAN Bacillus anthracis 3 0.7294
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 2 0.7290
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7250
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.7223
RNA polymerase sigma factor SigA Q5SKW1 Q5SKW1_THET8 Thermus thermophilus 2 0.7201
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7197
Threonine--tRNA ligase P0A8M3 SYT_ECOLI Escherichia coli 3 0.7192
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7183
Glycoside Hydrolase Family 13 Q65MI2 Q65MI2_BACLD Bacillus licheniformis 2 0.7176
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7167
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7162
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 2 0.7155
rRNA methylase Q8DSS3 Q8DSS3_STRMU Streptococcus mutans serotype c 3 0.7154
cGMP-dependent protein kinase 1 P00516 KGP1_BOVIN Bos taurus 3 0.7151
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7140
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7127
Adenosine 5'-monophosphoramidase HINT1 P80912 HINT1_RABIT Oryctolagus cuniculus 3 0.7117
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7107
Nucleoside diphosphate kinase A 2 P52175 NDKA2_BOVIN Bos taurus 3 0.7096
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7090
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7089
Tyrosine-protein kinase receptor TYRO3 P55144 TYRO3_MOUSE Mus musculus 3 0.7081
Isoleucine--tRNA ligase P56690 SYI_THET8 Thermus thermophilus 3 0.7077
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 2 0.7075
Virulence sensor histidine kinase PhoQ P0DM80 PHOQ_SALTY Salmonella typhimurium 3 0.7067
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7058
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7049
Geranyl diphosphate 2-C-methyltransferase D3KYU3 GPPMT_STRLS Streptomyces lasalocidi 3 0.7047
AcsD Q93AT8 Q93AT8_DICCH Dickeya chrysanthemi 3 0.7047
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7043
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7039
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7026
Amine oxidase [flavin-containing] B P27338 AOFB_HUMAN Homo sapiens 3 0.7021
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Q8ZMF7 ISPF_SALTY Salmonella typhimurium 3 0.7003
Cytosine-specific methyltransferase Q8EVR5 Q8EVR5_MYCPE Mycoplasma penetrans 3 0.7002

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