Mbandakamine B2 - Compound Card

Mbandakamine B2

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Mbandakamine B2

Structure
Zoomed Structure
  • Family: Plantae - Ancistrocladaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Naphthylisoquinoline Alkaloid
Canonical Smiles COc1ccc(c2c1c(O)cc(c2c1cc(c2c(O)cc(c3c2C[C@H](C)N([C@@H]3C)C)OC)c2c(c1O)c(OC)cc(c2)C)C)c1c(O)cc(c2c1C[C@@H](C)N([C@@H]2C)C)OC
InChI InChI=1S/C50H56N2O8/c1-23-15-30-31(46-33-19-26(4)52(8)28(6)44(33)41(60-12)22-37(46)55)20-34(50(56)47(30)39(16-23)58-10)42-24(2)17-35(53)49-38(57-9)14-13-29(48(42)49)45-32-18-25(3)51(7)27(5)43(32)40(59-11)21-36(45)54/h13-17,20-22,25-28,53-56H,18-19H2,1-12H3/t25-,26+,27-,28-/m1/s1
InChIKey SGTVGGIXYKOMFX-JUDWXZBOSA-N
Formula C50H56N2O8
HBA 10
HBD 4
MW 813.0
Rotatable Bonds 7
TPSA 124.32
LogP 10.34
Number Rings 8
Number Aromatic Rings 6
Heavy Atom Count 60
Formal Charge 0
Fraction CSP3 0.36
Exact Mass 812.4
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Ancistrocladus liana Ancistrocladaceae Plantae 63071

Showing of synonyms

  • Lombe BK, Bruhn T, et al. (2017). Antiprotozoal spirombandakamines A1 and A2, fused naphthylisoquinoline dimers from a Congolese Ancistrocladus plant. Organic letters,2017, 19(24), 6740-6743. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: C1CNCc(c12)cccc2-c3cccc(c34)cccc4-c(cc(c56)cccc6)cc5-c7cccc(c78)CNCC8

Level: 3

Mol. Weight: 813.0 g/mol

Structure

SMILES: c1cccc(c12)cccc2-c(cc(c34)cccc4)cc3-c5cccc(c56)CNCC6

Level: 2

Mol. Weight: 813.0 g/mol

Structure

SMILES: c1cccc(c12)ccc(c2)-c3cccc(c34)cccc4-c5cccc(c56)CNCC6

Level: 2

Mol. Weight: 813.0 g/mol

Structure

SMILES: c1cccc(c12)cccc2-c3cccc(c34)CNCC4

Level: 1

Mol. Weight: 813.0 g/mol

Structure

SMILES: c1cccc(c12)cccc2-c(c3)ccc(c34)cccc4

Level: 1

Mol. Weight: 813.0 g/mol

Structure

SMILES: C1CNCc(c12)cccc2

Level: 0

Mol. Weight: 813.0 g/mol

Structure

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 813.0 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.72
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
332.130
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
44182.92

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.270
Plasma Protein Binding
71.84
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
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
7.450
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Toxic
Bee
Toxic
Bioconcentration Factor
-1026.890
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.240
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
4.320
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Safe
NR-Aromatase
Toxic
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-80184567.060
Rat (Acute)
2.410
Rat (Chronic Oral)
2.520
Fathead Minnow
101222.140
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
9013436.990
Hydration Free Energy
-2.920
Log(D) at pH=7.4
5.850
Log(P)
8.48
Log S
-7.3
Log(Vapor Pressure)
-296751.58
Melting Point
193.51
pKa Acid
-2120.15
pKa Basic
9.55
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8829
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8819
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.8698
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8619
Caspase-6 P55212 CASP6_HUMAN Homo sapiens 3 0.8244
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8194
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7952
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7687
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.7565
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7541
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.7534
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7465
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7251
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7224
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7187
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.7091
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7025

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