Chaetospirolactone - Compound Card

Chaetospirolactone

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Chaetospirolactone

Structure
Zoomed Structure
  • Family: Fungi - Chaetomiaceae
  • Kingdom: Fungi
  • Class: Lactone
    • Subclass: Spirolactone
Canonical Smiles C/C=C/C1=C(/C=C/C)C(=O)[C@@]2(C1)C[C@H](C(=O)O2)O
InChI InChI=1S/C14H16O4/c1-3-5-9-7-14(8-11(15)13(17)18-14)12(16)10(9)6-4-2/h3-6,11,15H,7-8H2,1-2H3/b5-3+,6-4+/t11-,14-/m1/s1
InChIKey XEMRXEYFLUVEGM-AIUSXAPHSA-N
Formula C14H16O4
HBA 4
HBD 1
MW 248.28
Rotatable Bonds 2
TPSA 63.6
LogP 1.45
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.43
Exact Mass 248.1
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Chaetomium sp. NF00754 Chaetomiaceae Fungi 5149

Showing of synonyms

  • Xu Q.L, Xiao Y.S, et al. (2018). Novel chaetospirolactone and orsellide F from an endophytic fungus Chaetomium sp.. Journal of Asian natural products research, 2018, 20(3), 234-241. [View] [PubMed]
Pubchem: 139591367
Nmrshiftdb2: 80016049

No compound-protein relationship available.

Structure

SMILES: C1C=CC(=O)C12CCC(=O)O2

Level: 0

Mol. Weight: 248.28 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.59
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.28
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.88

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.66
Plasma Protein Binding
50.43
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
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.22
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.02
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.76
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.44
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
1.27
Rat (Acute)
1.96
Rat (Chronic Oral)
2.09
Fathead Minnow
4.42
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
326.41
Hydration Free Energy
-9.01
Log(D) at pH=7.4
1.44
Log(P)
1.22
Log S
-2.27
Log(Vapor Pressure)
-5.74
Melting Point
145.15
pKa Acid
6.72
pKa Basic
3.67
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8103
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8049
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7625
Aromatase P11511 CP19A_HUMAN Homo sapiens 2 0.7519
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7493
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7381
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 2 0.7312
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 2 0.7293
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7113
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7069
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7018

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