Jozibrevine B - Compound Card

Jozibrevine B

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Jozibrevine B

Structure
Zoomed Structure
  • Family: Plantae - Ancistrocladaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Naphthylisoquinoline Alkaloid
Canonical Smiles COc1cccc2c1c(O)c(c(c2c1ccc2c(c1O)[C@@H](C)N[C@@H](C2)C)C)c1c(C)c(c2ccc3c(c2O)[C@@H](C)NC(C3)C)c2c(c1O)c(OC)ccc2
InChI InChI=1S/C46H48N2O6/c1-21-19-27-15-17-31(43(49)39(27)25(5)47-21)35-23(3)37(45(51)41-29(35)11-9-13-33(41)53-7)38-24(4)36(30-12-10-14-34(54-8)42(30)46(38)52)32-18-16-28-20-22(2)48-26(6)40(28)44(32)50/h9-18,21-22,25-26,47-52H,19-20H2,1-8H3/t21-,22?,25-,26-/m1/s1
InChIKey RDYUUUNZMHSHKP-QNFUFWFBSA-N
Formula C46H48N2O6
HBA 8
HBD 6
MW 724.9
Rotatable Bonds 5
TPSA 123.44
LogP 9.64
Number Rings 8
Number Aromatic Rings 6
Heavy Atom Count 54
Formal Charge 0
Fraction CSP3 0.3
Exact Mass 724.35
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Ancistrocladus abbreviatus Ancistrocladaceae Plantae 122295

Showing of synonyms

  • Fayez S, Li Jun, et al. (2019). A near-complete series of four atropisomeric Jozimine A2‐Type naphthylisoquinoline dimers with antiplasmodial and cytotoxic activities and related alkaloids from Ancistrocladus abbreviatus. Journal of Natural Products,2019, 82(11). [View]

No compound-protein relationship available.

Structure

SMILES: C1NCCc(c12)ccc(c2)-c3cc(cc(c34)cccc4)-c(cc(c56)cccc6)cc5-c(c7)ccc(c78)CCNC8

Level: 3

Mol. Weight: 724.9 g/mol

Structure

SMILES: c1cccc(c12)ccc(c2)-c(cc(c34)cccc4)cc3-c(c5)ccc(c56)CCNC6

Level: 2

Mol. Weight: 724.9 g/mol

Structure

SMILES: c1cccc(c12)cccc2-c(c3)ccc(c34)CCNC4

Level: 1

Mol. Weight: 724.9 g/mol

Structure

SMILES: c1cccc(c12)ccc(c2)-c(c3)ccc(c34)cccc4

Level: 1

Mol. Weight: 724.9 g/mol

Structure

SMILES: C1CNCc(c12)cccc2

Level: 0

Mol. Weight: 724.9 g/mol

Structure

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 724.9 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.71
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
19.850
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
3354.23

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.440
Plasma Protein Binding
85.53
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
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
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
6.760
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Toxic
Bee
Toxic
Bioconcentration Factor
-79.720
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.760
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
8.250
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Toxic
NR-Aromatase
Toxic
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-6080422.140
Rat (Acute)
2.240
Rat (Chronic Oral)
2.170
Fathead Minnow
7680.040
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
678811.490
Hydration Free Energy
-2.920
Log(D) at pH=7.4
5.200
Log(P)
7.43
Log S
-7.27
Log(Vapor Pressure)
-22315.01
Melting Point
258.11
pKa Acid
-136.03
pKa Basic
10.56
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.9414
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.9085
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8811
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8350
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8202
Insulin-degrading enzyme P14735 IDE_HUMAN Homo sapiens 3 0.8191
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 3 0.8189
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8132
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8050
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7998
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7901
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7729
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7722
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.7710
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7575
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7562
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7527
GTPase KRas P01116 RASK_HUMAN Homo sapiens 3 0.7522
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.7478
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7475
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7420
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7221
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7214
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7189
Genome polyprotein A0EKU1 A0EKU1_9FLAV Meaban virus 3 0.7157
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7155
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7096
Nucleoside 2-deoxyribosyltransferase Q8RLY5 Q8RLY5_LACHE Lactobacillus helveticus 2 0.7029

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