(+)-sclerotiorin - Compound Card

(+)-sclerotiorin

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(+)-sclerotiorin

Structure
Zoomed Structure
  • Family: Fungi - Chaetomiaceae
  • Kingdom: Fungi
  • Class: Azaphilone
Canonical Smiles CC[C@@H](/C=C(/C=C/C1=CC2=C(Cl)C(=O)[C@](C(=O)C2=CO1)(C)OC(=O)C)\C)C
InChI InChI=1S/C21H23ClO5/c1-6-12(2)9-13(3)7-8-15-10-16-17(11-26-15)19(24)21(5,27-14(4)23)20(25)18(16)22/h7-12H,6H2,1-5H3/b8-7+,13-9+/t12-,21+/m0/s1
InChIKey SWJLTKXURNHVHE-UPWXJBBJSA-N
Formula C21H23ClO5
HBA 5
HBD 0
MW 390.86
Rotatable Bonds 5
TPSA 69.67
LogP 4.3
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.38
Exact Mass 390.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Chaetomium aureum Chaetomiaceae Fungi 79815

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]
CPRiL: 75369
Structure

SMILES: C1OC=CC(C=12)=CC(=O)CC2=O

Level: 0

Mol. Weight: 390.86 g/mol

Anticancer
Inhibition of the hsp90 machine chaperoning

Absorption

Caco-2 (logPapp)
-4.69
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.75
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.62

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.14
Plasma Protein Binding
65.79
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
3.0
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.93
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.47
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
8.14
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Toxic
NR-ER
Safe
NR-ER-LBD
Toxic
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-1.11
Rat (Acute)
1.97
Rat (Chronic Oral)
2.2
Fathead Minnow
5.39
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Toxic
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
388.33
Hydration Free Energy
-6.57
Log(D) at pH=7.4
3.55
Log(P)
4.19
Log S
-5.36
Log(Vapor Pressure)
-6.09
Melting Point
133.09
pKa Acid
5.57
pKa Basic
3.77
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8956
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8956
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8948
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8948
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8865
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8865
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8788
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8788
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8498
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8498
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8493
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8493
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8332
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8332
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.8317
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.8317
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.8293
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.8293
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8249
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8249
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8172
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8172
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8130
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8130
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8055
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8055
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7951
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7951
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7943
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7943
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7907
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7907
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7878
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7878
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7877
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7877
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7861
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7861
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7848
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7848
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7834
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7834
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7829
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7829
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7801
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7801
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7784
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7784
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7758
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7758
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7748
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7748
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7746
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7746
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7719
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7719
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7712
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7712
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7698
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7698
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7690
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7690
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7676
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7676
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7578
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7578
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 2 0.7573
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 2 0.7573
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7567
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7567
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7558
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7558
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7548
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7548
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7547
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7547
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7538
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7538
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7520
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7520
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7511
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7511
Steroid 17-alpha-hydroxylase/17,20 lyase P05093 CP17A_HUMAN Homo sapiens 2 0.7499
Steroid 17-alpha-hydroxylase/17,20 lyase P05093 CP17A_HUMAN Homo sapiens 2 0.7499
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7488
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7488
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7484
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7484
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7464
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7464
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 2 0.7452
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 2 0.7452
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7442
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7442
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7419
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7419
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7403
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7403
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 2 0.7401
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 2 0.7401
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7399
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7399
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7390
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7390
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7390
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7390
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 2 0.7383
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 2 0.7383
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7369
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7369
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7357
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7357
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7354
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7354
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7351
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7351
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7342
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7342
Aromatase P11511 CP19A_HUMAN Homo sapiens 2 0.7320
Aromatase P11511 CP19A_HUMAN Homo sapiens 2 0.7320
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7299
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7299
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7295
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7295
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7294
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7294
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7292
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7292
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7258
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7258
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7236
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7236
Epoxide hydrolase Q41415 Q41415_SOLTU Solanum tuberosum 2 0.7234
Epoxide hydrolase Q41415 Q41415_SOLTU Solanum tuberosum 2 0.7234
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7230
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7230
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7224
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7224
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7205
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7205
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7185
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7185
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7159
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7159
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7139
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7139
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7121
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7121
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7109
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7109
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7086
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7086
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7086
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7086
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7060
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7060
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7054
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7054
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7052
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7052
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7014
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7014
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7007
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7007
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7007
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7007

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