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Chetomin
- Family: Fungi - Chaetomiaceae
- Kingdom: Fungi
-
Class: Oxopiperazine
- Subclass: Epidithiodioxopiperazine
| Canonical Smiles | OC[C@@]12SS[C@@](C(=O)N1C)(N(C2=O)C)Cc1cn(c2c1cccc2)[C@@]12C[C@]34N([C@H]2Nc2c1cccc2)C(=O)[C@](SS3)(N(C4=O)C)CO |
|---|---|
| InChI | InChI=1S/C31H30N6O6S4/c1-33-25(42)30(15-38)34(2)23(40)28(33,44-46-30)12-17-13-36(21-11-7-4-8-18(17)21)27-14-29-24(41)35(3)31(16-39,47-45-29)26(43)37(29)22(27)32-20-10-6-5-9-19(20)27/h4-11,13,22,32,38-39H,12,14-16H2,1-3H3/t22-,27+,28+,29+,30+,31+/m1/s1 |
| InChIKey | ZRZWBWPDBOVIGQ-YWZWRZHGSA-N |
| Formula | C31H30N6O6S4 |
| HBA | 12 |
| HBD | 3 |
| MW | 710.89 |
| Rotatable Bonds | 5 |
| TPSA | 138.66 |
| LogP | 1.87 |
| Number Rings | 11 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 47 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.42 |
| Exact Mass | 710.11 |
| Number of Lipinski Rule Violations | 2 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Chaetomium sp. NF00761 | Chaetomiaceae | Fungi | 5149 |
Showing of synonyms
Chetomin
Chaetomin
1403-36-7
BKU7CX6USX
BRN 0077366
4-27-00-09496 (Beilstein Handbook Reference)
NSC-289491
NSC 289491
(1S,3S,11R,14S)-14-(hydroxymethyl)-3-[3-[[(1S,4S)-4-(hydroxymethyl)-5,7-dimethyl-6,8-dioxo-2,3-dithia-5,7-diazabicyclo[2.2.2]octan-1-yl]methyl]indol-1-yl]-18-methyl-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.01,12.03,11.04,9]octadeca-4,6,8-triene-13,17-dione
3,11a-Epidithio-11aH-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4-dione, 2,3,5a,6,10b,11-hexahydro-3-(hydroxymethyl)-10b-[(1S,4S)-3-[[4-(hydroxymethyl)-5,7-dimethyl-6,8-dioxo-2,3-dithia-5,7-diazabicyclo[2.2.2]oct-1-yl]methyl]-1H-indol-1-yl]-2-methyl-, (3S,5aR,10bS,11aS)-
(1S,3S,11R,14S)-14-(hydroxymethyl)-3-(3-(((1S,4S)-4-(hydroxymethyl)-5,7-dimethyl-6,8-dioxo-2,3-dithia-5,7-diazabicyclo(2.2.2)octan-1-yl)methyl)indol-1-yl)-18-methyl-15,16-dithia-10,12,18-triazapentacyclo(12.2.2.01,12.03,11.04,9)octadeca-4,6,8-triene-13,17-dione
3,11a-Epidithio-11aH-pyrazino(1',2':1,5)pyrrolo(2,3-b)indole-1,4-dione, 2,3,5a,6,10b,11-hexahydro-3-(hydroxymethyl)-10b-((1S,4S)-3-((4-(hydroxymethyl)-5,7-dimethyl-6,8-dioxo-2,3-dithia-5,7-diazabicyclo(2.2.2)oct-1-yl)methyl)-1H-indol-1-yl)-2-methyl-, (3S,5aR,10bS,11aS)-
(1s,3s,11r,14s)-14-(hydroxymethyl)-3-(3-(((1r,4s)-4-(hydroxymethyl)-5,7-dimethyl-6,8-dioxo-2,3-dithia-5,7-diazabicyclo(2.2.2)octan-1-yl)methyl)indol-1-yl)-18-methyl-15,16-dithia-10,12,18-triazapentacyclo(12.2.2.01,12.03,11.04,9)octadeca-4,6,8-triene-13,17-dione
(1s,3s,11r,14s)-14-(hydroxymethyl)-3-[3-[[(1r,4s)-4-(hydroxymethyl)-5,7-dimethyl-6,8-dioxo-2,3-dithia-5,7-diazabicyclo[2.2.2]octan-1-yl]methyl]indol-1-yl]-18-methyl-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.01,12.03,11.04,9]octadeca-4,6,8-triene-13,17-dione
CHEMBL499593
2,3S,5aR,6,10bS,11-hexahydro-3-(hydroxymethyl)-10b-[(1S,4S)-3-[[4-(hydroxymethyl)-5,7-dimethyl-6,8-dioxo-2,3-dithia-5,7-diazabicyclo[2.2.2]oct-1-yl]methyl]-1H-indol-1-yl]-2-methyl-3,11aS-epidithio-11aH-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4-dione
UNII-BKU7CX6USX
SCHEMBL1098248
ZRZWBWPDBOVIGQ-YWZWRZHGSA-N
GLXC-10588
BDBM50396027
AKOS040759040
DA-62263
MS-31200
HY-107553
CS-0028866
M04053
14-(Hydroxymethyl)-3-[3-[[4-(hydroxymethyl)-5,7-dimethyl-6,8-dioxo-2,3-dithia-5,7-diazabicyclo[2.2.2]octan-1-yl]methyl]indol-1-yl]-18-methyl-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.01,12.03,11.04,9]octadeca-4,6,8-triene-13,17-dione
Pubchem:
10417379
Cas:
1403-36-7
Zinc:
ZINC000049889095
Nmrshiftdb2:
60147243
Chembl:
CHEMBL499593
Bindingdb:
50396027
CPRiL:
84621
SMILES: N1C(=O)C(SS2)NC(=O)C12Cc3cn(c(c34)cccc4)C(C5)(c6c(N7)cccc6)C7N(C589)C(=O)C(SS9)NC8=O
Level: 2
Mol. Weight: 710.89 g/mol
SMILES: c1cccc(N2)c1C(C3)(C2N(C345)C(=O)C(SS5)NC4=O)n(cc6)c(c67)cccc7
Level: 1
Mol. Weight: 710.89 g/mol
SMILES: N1C(=O)C(SS2)NC(=O)C12Cc3c[nH]c(c34)cccc4
Level: 1
Mol. Weight: 710.89 g/mol
SMILES: c1cccc(N2)c1C(C3)C2N(C345)C(=O)C(SS5)NC4=O
Level: 0
Mol. Weight: 710.89 g/mol
SMILES: C12C(=O)NC(SS2)C(=O)N1
Level: 0
Mol. Weight: 710.89 g/mol
SMILES: c1c[nH]c(c12)cccc2
Level: 0
Mol. Weight: 710.89 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.66
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -3.71
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 232.1
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.83
- Plasma Protein Binding
- 83.92
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- 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
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 8.86
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Toxic
- Bee
- Toxic
- Bioconcentration Factor
- -3.72
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.25
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 3.19
- 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
- -416997.1
- Rat (Acute)
- 2.55
- Rat (Chronic Oral)
- 2.9
- Fathead Minnow
- 535.68
- 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
- 41474.68
- Hydration Free Energy
- -2.92
- Log(D) at pH=7.4
- 1.79
- Log(P)
- 1.67
- Log S
- -3.91
- Log(Vapor Pressure)
- -1375.82
- Melting Point
- 316.43
- pKa Acid
- 4.36
- pKa Basic
- 3.93
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.9085 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 4 | 0.8671 |
| Pyridoxal kinase | P82197 | PDXK_SHEEP | Ovis aries | 3 | 0.8356 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.8215 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8170 |
| cGMP-dependent protein kinase 1 | Q13976 | KGP1_HUMAN | Homo sapiens | 3 | 0.8128 |
| Protein LlR18A | P52778 | L18A_LUPLU | Lupinus luteus | 3 | 0.8111 |
| Bromodomain testis-specific protein | Q58F21 | BRDT_HUMAN | Homo sapiens | 3 | 0.8034 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7832 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7716 |
| Purine nucleoside phosphorylase DeoD-type | P0ABP9 | DEOD_ECO57 | Escherichia coli O157:H7 | 3 | 0.7712 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7630 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 3 | 0.7630 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7625 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.7599 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7580 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7565 |
| HTH-type transcriptional regulator QacR | P0A0N4 | QACR_STAAU | Staphylococcus aureus | 3 | 0.7549 |
| Lethal(3)malignant brain tumor-like protein 1 | Q9Y468 | LMBL1_HUMAN | Homo sapiens | 3 | 0.7515 |
| Glutathione S-transferase F2 | P46422 | GSTF2_ARATH | Arabidopsis thaliana | 3 | 0.7391 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7368 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7363 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.7338 |
| Ferrichrome outer membrane transporter/phage receptor | P06971 | FHUA_ECOLI | Escherichia coli | 3 | 0.7326 |
| Glutathione S-transferase P | P09211 | GSTP1_HUMAN | Homo sapiens | 2 | 0.7283 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7273 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7273 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 3 | 0.7266 |
| Bromodomain adjacent to zinc finger domain protein 2B | Q9UIF8 | BAZ2B_HUMAN | Homo sapiens | 3 | 0.7240 |
| Disks large homolog 1 | Q12959 | DLG1_HUMAN | Homo sapiens | 3 | 0.7186 |
| GCN5-related N-acetyltransferase | B1YEL6 | B1YEL6_EXIS2 | Exiguobacterium sibiricum | 3 | 0.7161 |
| Pantothenate kinase | P9WPA7 | COAA_MYCTU | Mycobacterium tuberculosis | 3 | 0.7158 |
| ABC-type polar amino acid transport system, ATPase component | Q8RCC2 | Q8RCC2_CALS4 | Caldanaerobacter subterraneus subsp. tengcongensis | 2 | 0.7131 |
| Peptidyl-prolyl cis-trans isomerase FKBP5 | Q13451 | FKBP5_HUMAN | Homo sapiens | 4 | 0.7064 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7057 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7017 |