Cissetin - Compound Card

Cissetin

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Cissetin

Structure
Zoomed Structure
  • Family: Fungi - Sporormiaceae
  • Kingdom: Fungi, Plantae
  • Class: Terpenoid
    • Subclass: Diterpene
Canonical Smiles C/C=C/[C@@H]1C=C[C@H]2[C@@H]([C@]1(C)/C(=C/1\C(=O)C(N(C1=O)C)C(O)C)/O)CC[C@@H](C2)C
InChI InChI=1S/C23H33NO4/c1-6-7-16-10-9-15-12-13(2)8-11-17(15)23(16,4)21(27)18-20(26)19(14(3)25)24(5)22(18)28/h6-7,9-10,13-17,19,25,27H,8,11-12H2,1-5H3/b7-6+,21-18-/t13-,14?,15+,16+,17-,19?,23+/m0/s1
InChIKey ALZYMNAJOKGMOH-BWURQPDZSA-N
Formula C23H33NO4
HBA 4
HBD 2
MW 387.52
Rotatable Bonds 3
TPSA 77.84
LogP 3.41
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.65
Exact Mass 387.24
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Enantia chlorantha Annonaceae Plantae 306909
2 Preussia sp. Sporormiaceae Fungi 1715257

Showing of synonyms

  • Talontsi FM, Lamshöft M, et al. (2014). Antiplasmodial and cytotoxic dibenzofurans from Preussia sp. harboured in Enantia chlorantha Oliv.. Fitoterapia,2014, 93, 233-238. [View] [PubMed]
Pubchem: 54693549

No compound-protein relationship available.

Structure

SMILES: O=C1NCC(=O)C1=CC(CC=C2)C(C23)CCCC3

Level: 1

Mol. Weight: 387.52 g/mol

Structure

SMILES: C1=CCCC(C12)CCCC2

Level: 0

Mol. Weight: 387.52 g/mol

Structure

SMILES: C=C1C(=O)CNC1=O

Level: 0

Mol. Weight: 387.52 g/mol

Anti-plasmodial
Cytotoxic

Absorption

Caco-2 (logPapp)
-4.7
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.73
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.75

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.08
Plasma Protein Binding
75.27
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
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.27
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.54
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.03
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
7.92
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
-7.42
Rat (Acute)
3.24
Rat (Chronic Oral)
2.33
Fathead Minnow
4.06
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
424.39
Hydration Free Energy
-8.31
Log(D) at pH=7.4
2.77
Log(P)
3.73
Log S
-3.61
Log(Vapor Pressure)
-8.68
Melting Point
119.16
pKa Acid
5.93
pKa Basic
5.28
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.9275
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.9183
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8795
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.8727
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.8644
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8510
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.8045
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.7748
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7638
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7604
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7508
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7467
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7398
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7361
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7352
Retinol-binding protein 2 P06768 RET2_RAT Rattus norvegicus 3 0.7206
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7176
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7107
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7075
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7024
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7017
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.7003

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