Schizozynine - Compound Card

Schizozynine

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Schizozynine

Structure
Zoomed Structure
  • Family: Plantae - Apocynaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Indoline Alkaloid
Canonical Smiles CCCC12CCC3(C2N(C)C)N(C(=O)C1)c1c(C3CC)cc2c(c1)OCO2
InChI InChI=1S/C22H30N2O3/c1-5-7-21-8-9-22(20(21)23(3)4)15(6-2)14-10-17-18(27-13-26-17)11-16(14)24(22)19(25)12-21/h10-11,15,20H,5-9,12-13H2,1-4H3
InChIKey UAUOPGDBAJNVOF-UHFFFAOYSA-N
Formula C22H30N2O3
HBA 4
HBD 0
MW 370.49
Rotatable Bonds 4
TPSA 42.01
LogP 3.91
Number Rings 5
Number Aromatic Rings 1
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.68
Exact Mass 370.23
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Schizozygia coffaeoides Apocynaceae Plantae 2896553

Showing of synonyms

  • Kariba RM, Houghton PJ, et al. (2002). Antimicrobial activities of a new schizozygane indoline alkaloid from Schizozygia coffaeoides and the revised structure of isoschizogaline.. Natural Product Letters,2002,65(4),566-569. [View] [PubMed]
Pubchem: 547445

No compound-protein relationship available.

Structure

SMILES: O1COc(c2)c1cc(C3)c2N(C345)C(=O)CC(C4)CC5

Level: 0

Mol. Weight: 370.49 g/mol

Antimicrobial

Absorption

Caco-2 (logPapp)
-4.61
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.76
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.41

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.81
Plasma Protein Binding
26.41
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
9.0
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.23
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.39
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
9.89
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
-9.08
Rat (Acute)
2.95
Rat (Chronic Oral)
0.87
Fathead Minnow
4.35
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
406.62
Hydration Free Energy
-6.89
Log(D) at pH=7.4
3.07
Log(P)
4.5
Log S
-2.95
Log(Vapor Pressure)
-7.84
Melting Point
151.15
pKa Acid
8.21
pKa Basic
7.51
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8330
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8330
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8027
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8027
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7812
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7812
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7799
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7799
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.7557
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.7557
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7440
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7440
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7404
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7404
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7395
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7395
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7319
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7319
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7097
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7097
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7032
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7032
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7022
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7022

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