Mbandakamine D - Compound Card

Mbandakamine D

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Mbandakamine D

Structure
Zoomed Structure
  • Family: Ancistrocladaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Naphthylisoquinoline Alkaloid
Canonical Smiles COc1cc(O)c(c2c1[C@H](C)N[C@@H](C2)C)c1cc(c2c(C)cc(c3c2c(ccc3OC)c2c(O)cc(c3c2C[C@@H](C)N=C3C)OC)O)c(c2c1cc(C)cc2OC)O
InChI InChI=1S/C48H50N2O8/c1-21-13-28-29(44-31-17-24(4)50-26(6)42(31)39(58-10)20-35(44)53)18-32(48(54)45(28)37(14-21)56-8)40-22(2)15-33(51)47-36(55-7)12-11-27(46(40)47)43-30-16-23(3)49-25(5)41(30)38(57-9)19-34(43)52/h11-15,18-20,23-24,26,50-54H,16-17H2,1-10H3/t23-,24-,26+/m1/s1
InChIKey IUFTYFDUYNQGAW-MZKUHISZSA-N
Formula C48H50N2O8
HBA 10
HBD 5
MW 782.93
Rotatable Bonds 7
TPSA 142.23
LogP 9.82
Number Rings 8
Number Aromatic Rings 6
Heavy Atom Count 58
Formal Charge 0
Fraction CSP3 0.31
Exact Mass 782.36
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Ancistrocladus ealaensis Ancistrocladaceae Plantae 714098
2 Ancistrocladus liana Ancistrocladaceae Plantae 63071

Showing of synonyms

  • Tshitenge DT, Feineis D, et al. (2018). Mbandakamine-Type Naphthylisoquinoline Dimers and Related Alkaloids from the Central African Liana Ancistrocladus ealaensis with Antiparasitic and Antileukemic Activities.. Journal of natural products,2018, 81(4), 918-933. [View] [PubMed]
  • Lombe BK, Feineis D, et al. (2021). Spirombandakamine A3 and Cyclombandakamines A8 and A9, polycyclic naphthylisoquinoline dimers, with antiprotozoal activity, from a congolese ancistrocladus plant. Journal of natural products,2021, 84(4), 1335-1344. [View] [PubMed]
Pubchem: 145987248

No compound-protein relationship available.

Structure

SMILES: C1CN=Cc(c12)cccc2-c3cccc(c34)cccc4-c(cc(c56)cccc6)cc5-c7cccc(c78)CNCC8

Level: 3

Mol. Weight: 514.67 g/mol

Structure

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

Level: 2

Mol. Weight: 385.51 g/mol

Structure

SMILES: c1cccc(c12)ccc(c2)-c3cccc(c34)cccc4-c5cccc(c56)C=NCC6

Level: 2

Mol. Weight: 383.49 g/mol

Structure

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

Level: 1

Mol. Weight: 259.35 g/mol

Structure

SMILES: c1cccc(c12)cccc2-c3cccc(c34)C=NCC4

Level: 1

Mol. Weight: 257.34 g/mol

Structure

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

Level: 1

Mol. Weight: 254.33 g/mol

Structure

SMILES: C1CNCc(c12)cccc2

Level: 0

Mol. Weight: 133.19 g/mol

Structure

SMILES: C1=NCCc(c12)cccc2

Level: 0

Mol. Weight: 131.18 g/mol

Structure

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 128.17 g/mol

Antileukemia
Antiparasitic
Antiprotozoal

Absorption

Caco-2 (logPapp)
-5.78
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
134.020
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
18277.68

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.460
Plasma Protein Binding
80.14
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
8.410
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Toxic
Bee
Toxic
Bioconcentration Factor
-426.120
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.300
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
4.680
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Toxic
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
-33169334.270
Rat (Acute)
2.420
Rat (Chronic Oral)
3.160
Fathead Minnow
41878.250
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
3725442.200
Hydration Free Energy
-2.920
Log(D) at pH=7.4
5.870
Log(P)
8.75
Log S
-7.46
Log(Vapor Pressure)
-122633.43
Melting Point
259.11
pKa Acid
-853.21
pKa Basic
8.68
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.8579
Caspase-6 P55212 CASP6_HUMAN Homo sapiens 3 0.8535
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8531
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8426
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8286
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8183
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.7920
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7806
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7643
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7538
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.7233
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7190
Protease O38896 O38896_9HIV1 Human immunodeficiency virus 1 3 0.7154
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7087
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7081
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7019

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