11alpha-methoxycurvularin - Compound Card

11alpha-methoxycurvularin

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11alpha-methoxycurvularin

Structure
Zoomed Structure
  • Family: Fungi - Trichocomaceae
  • Kingdom: Fungi
  • Class: Lactone
    • Subclass: Macrolide
Canonical Smiles CO[C@H]1CCC[C@H](C)OC(=O)Cc2c(C(=O)C1)c(O)cc(c2)O
InChI InChI=1S/C17H22O6/c1-10-4-3-5-13(22-2)9-15(20)17-11(7-16(21)23-10)6-12(18)8-14(17)19/h6,8,10,13,18-19H,3-5,7,9H2,1-2H3/t10-,13-/m0/s1
InChIKey LBVPDFGFLMFDPI-GWCFXTLKSA-N
Formula C17H22O6
HBA 6
HBD 2
MW 322.36
Rotatable Bonds 1
TPSA 93.06
LogP 2.34
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.53
Exact Mass 322.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Penicillium species Trichocomaceae Fungi 5073

Showing of synonyms

  • Aly AH, Debbab A, et al. (2011). NF kappa B inhibitors and antitrypanosomal metabolites from endophytic fungus Penicillium sp. isolated from Limonium tubiflorum. Bioorganic and Medicinal Chemistry,2011,19(1),414-421. [View] [PubMed]
Pubchem: 14829838
Nmrshiftdb2: 70022238

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)CC(=O)OCCCCCCC2=O

Level: 0

Mol. Weight: 322.36 g/mol

Antitumor

Absorption

Caco-2 (logPapp)
-4.79
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.850
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.04

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.530
Plasma Protein Binding
38.85
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
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
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.240
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.100
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
-1.050
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.840
Micronucleos
Toxic
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
-1.490
Rat (Acute)
1.880
Rat (Chronic Oral)
2.240
Fathead Minnow
4.010
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
411.850
Hydration Free Energy
-10.460
Log(D) at pH=7.4
1.280
Log(P)
2.09
Log S
-3.24
Log(Vapor Pressure)
-7.05
Melting Point
183.58
pKa Acid
7.72
pKa Basic
6.36
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.9233
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.9233
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9087
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9087
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.9040
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.9040
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9029
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9029
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.9026
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.9026
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.9006
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.9006
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9003
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9003
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8887
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8887
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8821
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8821
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8794
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8794
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8771
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8771
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.8617
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.8617
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8597
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8597
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8581
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8581
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8545
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8545
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8452
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8452
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8438
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8438
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8396
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8396
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8386
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8386
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8285
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8285
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8273
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8273
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8222
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8222
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8002
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8002
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7998
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7998
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7996
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7996
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7951
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7951
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.7948
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.7948
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7896
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7896
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7875
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7875
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7855
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7855
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7804
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7804
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7792
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7792
Peptidoglycan recognition protein 1 Q9GK12 PGRP1_CAMDR Camelus dromedarius 3 0.7735
Peptidoglycan recognition protein 1 Q9GK12 PGRP1_CAMDR Camelus dromedarius 3 0.7735
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7684
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7684
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7612
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7612
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7596
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7596
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7596
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7596
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7560
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7560
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7532
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7532
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7531
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7531
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 3 0.7511
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 3 0.7511
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7506
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7506
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7481
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7481
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7467
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7467
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7399
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7399
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7394
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7394
orotidine-5'-phosphate decarboxylase Q8T6J6 Q8T6J6_PLAFA Plasmodium falciparum 4 0.7385
orotidine-5'-phosphate decarboxylase Q8T6J6 Q8T6J6_PLAFA Plasmodium falciparum 4 0.7385
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7382
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7382
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7364
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7364
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7336
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7336
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7322
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7322
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7319
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7319
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7307
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7307
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7269
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7269
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7256
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7256
Chymotrypsinogen A P00766 CTRA_BOVIN Bos taurus 3 0.7253
Chymotrypsinogen A P00766 CTRA_BOVIN Bos taurus 3 0.7253
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7247
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7247
D-mycarose 3-C-methyltransferase Q194Q4 Q194Q4_STRAA Streptomyces argillaceus 4 0.7241
D-mycarose 3-C-methyltransferase Q194Q4 Q194Q4_STRAA Streptomyces argillaceus 4 0.7241
4-hydroxyphenylacetate 3-monooxygenase, reductase component Q5SJP7 HPAC_THET8 Thermus thermophilus 3 0.7227
4-hydroxyphenylacetate 3-monooxygenase, reductase component Q5SJP7 HPAC_THET8 Thermus thermophilus 3 0.7227
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7221
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7221
Dihydrofolate reductase P0ABQ4 DYR_ECOLI Escherichia coli 3 0.7194
Dihydrofolate reductase P0ABQ4 DYR_ECOLI Escherichia coli 3 0.7194
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7159
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7159
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7147
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7147
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7144
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7144
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 4 0.7123
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 4 0.7123
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7113
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7113
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7111
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7111
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7096
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7096
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7092
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7092
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7064
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7064
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7054
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7054
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7038
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7038
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 2 0.7032
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 2 0.7032
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7029
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7029
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7022
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7022
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.7020
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.7020
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7006
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 2 0.7006
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 2 0.7006
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7006
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7002
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7002
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7002
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7002

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