6,7-dehydro-19beta-hydroxyschizozygin - Compound Card

6,7-dehydro-19beta-hydroxyschizozygin

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6,7-dehydro-19beta-hydroxyschizozygin

Structure
Zoomed Structure
  • Family: Plantae - Apocynaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Indoline Alkaloid
Canonical Smiles O=C1C[C@]23C=CCN4[C@@H]3[C@@]3(N1c1cc5OCOc5cc1C3=CC4)CC2
InChI InChI=1S/C20H18N2O3/c23-17-10-19-3-1-6-21-7-2-13-12-8-15-16(25-11-24-15)9-14(12)22(17)20(13,5-4-19)18(19)21/h1-3,8-9,18H,4-7,10-11H2/t18-,19-,20+/m0/s1
InChIKey HTBIKRALNBUMJM-SLFFLAALSA-N
Formula C20H18N2O3
HBA 4
HBD 0
MW 334.38
Rotatable Bonds 0
TPSA 42.01
LogP 2.32
Number Rings 7
Number Aromatic Rings 1
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.45
Exact Mass 334.13
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]

No compound-protein relationship available.

Structure

SMILES: O1COc(c2)c1cc(c2C=3C456)N6C(=O)CC7(CC5)C4N(CC3)CC=C7

Level: 0

Mol. Weight: 334.38 g/mol

Antimicrobial

Absorption

Caco-2 (logPapp)
-4.45
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.710
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.09

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.960
Plasma Protein Binding
54.11
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-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
12.190
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.450
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.210
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.050
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
-8.180
Rat (Acute)
2.820
Rat (Chronic Oral)
1.400
Fathead Minnow
4.040
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
486.880
Hydration Free Energy
-5.470
Log(D) at pH=7.4
2.000
Log(P)
2.48
Log S
-3.58
Log(Vapor Pressure)
-9.67
Melting Point
297.87
pKa Acid
9.13
pKa Basic
6.39
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.9217
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.9217
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8739
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8739
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8551
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8551
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8478
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8478
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8414
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8414
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.8112
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.8112
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8081
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8081
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7987
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7987
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7946
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7946
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7764
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7764
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7757
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7757
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7614
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7614
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7597
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7597
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7592
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7592
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7581
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7581
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7533
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7533
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7383
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7383
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7295
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7295
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7284
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7284
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A Q13946 PDE7A_HUMAN Homo sapiens 3 0.7145
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A Q13946 PDE7A_HUMAN Homo sapiens 3 0.7145
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7140
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7140
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 3 0.7130
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 3 0.7130
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7127
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7127
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7091
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7091
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7003
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7003

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