Cytoglobosin C - Compound Card

Cytoglobosin C

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Cytoglobosin C

Structure
Zoomed Structure
  • Family: Fungi - Chaetomiaceae
  • Kingdom: Fungi
  • Class: Alkaloid
Canonical Smiles C[C@H]1C/C=C/[C@H]2[C@H](O)C(=C([C@@H]3[C@]2(C(=O)N[C@H]3Cc2c[nH]c3c2cccc3)C(=O)/C=C/[C@@H]([C@@H](/C(=C/1)/C)O)O)C)C
InChI InChI=1S/C32H38N2O5/c1-17-8-7-10-23-30(38)20(4)19(3)28-25(15-21-16-33-24-11-6-5-9-22(21)24)34-31(39)32(23,28)27(36)13-12-26(35)29(37)18(2)14-17/h5-7,9-14,16-17,23,25-26,28-30,33,35,37-38H,8,15H2,1-4H3,(H,34,39)/b10-7+,13-12+,18-14+/t17-,23-,25-,26-,28-,29+,30+,32+/m0/s1
InChIKey VWKVHGIGUCPWKR-HDCYGHGWSA-N
Formula C32H38N2O5
HBA 5
HBD 5
MW 530.67
Rotatable Bonds 2
TPSA 122.65
LogP 3.53
Number Rings 5
Number Aromatic Rings 2
Heavy Atom Count 39
Formal Charge 0
Fraction CSP3 0.44
Exact Mass 530.28
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Chaetomium sp. Chaetomiaceae Fungi 1769349

Showing of synonyms

  • Kabbaj FZ, Lu S, et al. (2015). Bioactive metabolites from Chaetomium aureum: Structure elucidation and inhibition of the Hsp90 machine chaperoning activity. Bioorganic and Medicinal Chemistry,2015,23(1),126-131. [View] [PubMed]
Pubchem: 44610809
Nmrshiftdb2: 70000338

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)[nH]cc2CC(NC3=O)C(C345)C=CCC4C=CCCC=CCCC=CC5=O

Level: 1

Mol. Weight: 530.67 g/mol

Structure

SMILES: O=C1NCC(C123)C=CCC2C=CCCC=CCCC=CC3=O

Level: 0

Mol. Weight: 530.67 g/mol

Structure

SMILES: c1c[nH]c(c12)cccc2

Level: 0

Mol. Weight: 530.67 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.54
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.07
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
0.18

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.23
Plasma Protein Binding
85.35
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
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.4
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.69
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.21
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.01
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
-3158.03
Rat (Acute)
4.36
Rat (Chronic Oral)
2.9
Fathead Minnow
13.45
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
520.68
Hydration Free Energy
-3.1
Log(D) at pH=7.4
3.61
Log(P)
3.07
Log S
-3.9
Log(Vapor Pressure)
-9.7
Melting Point
250.9
pKa Acid
6.23
pKa Basic
4.4
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8673
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.8531
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7921
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 3 0.7890
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7830
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7818
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7669
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7630
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.7626
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7539
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7534
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7530
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7515
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7463
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7417
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7394
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7364
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 2 0.7361
Genome polyprotein Q99AU2 Q99AU2_9HEPC Hepatitis C virus subtype 1b 4 0.7348
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.7324
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7306
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 2 0.7306
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7299
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7295
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7270
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7240
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7219
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 2 0.7179
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 2 0.7153
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 2 0.7146
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.7140
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7137
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7131
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7130
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7119
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7108
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7087
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7074
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7020
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7009
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7008
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7005
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7001

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