Cyclombandakamine A8 - Compound Card

Cyclombandakamine A8

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Cyclombandakamine A8

Structure
Zoomed Structure
  • Family: Plantae - Ancistrocladaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Naphthylisoquinoline Alkaloid
Canonical Smiles COc1ccc2c3c1C(=O)C[C@]1([C@]3(Oc3c2c2C[C@@H](C)N[C@@H](c2c(c3)OC)C)c2cc(c3c(O)cc(c4c3C[C@H](C)N([C@@H]4C)C)OC)c3c(c2O1)c(OC)cc(c3)C)C
InChI InChI=1S/C49H52N2O8/c1-22-14-28-29(42-31-17-24(3)51(7)26(5)41(31)37(56-10)19-33(42)52)18-32-47(44(28)36(15-22)55-9)59-48(6)21-34(53)45-35(54-8)13-12-27-43-30-16-23(2)50-25(4)40(30)38(57-11)20-39(43)58-49(32,48)46(27)45/h12-15,18-20,23-26,50,52H,16-17,21H2,1-11H3/t23-,24+,25-,26-,48+,49+/m1/s1
InChIKey LVOSZNDYMKKAFL-QBODTSNLSA-N
Formula C49H52N2O8
HBA 10
HBD 2
MW 796.96
Rotatable Bonds 5
TPSA 107.95
LogP 9.13
Number Rings 10
Number Aromatic Rings 5
Heavy Atom Count 59
Formal Charge 0
Fraction CSP3 0.41
Exact Mass 796.37
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Ancistrocladus liana Ancistrocladaceae Plantae 63071

Showing of synonyms

  • 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: 164628379

No compound-protein relationship available.

Structure

SMILES: C1CNCc(c12)cccc2-c(c3)c(cccc4)c4c(c3C567)OC5CC(=O)c8c6c(ccc8)c9c1c(ccc9O7)CNCC1

Level: 1

Mol. Weight: 796.96 g/mol

Structure

SMILES: c1cccc(cc2)c1c(c2C345)OC3CC(=O)c6c4c(ccc6)c7c8c(ccc7O5)CNCC8

Level: 0

Mol. Weight: 796.96 g/mol

Structure

SMILES: C1CNCc(c12)cccc2

Level: 0

Mol. Weight: 796.96 g/mol

Antiprotozoal

Absorption

Caco-2 (logPapp)
-5.52
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
393.820
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
52180.48

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.160
Plasma Protein Binding
72.69
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
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
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
9.910
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Toxic
Bee
Toxic
Bioconcentration Factor
-1215.530
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.350
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
4.920
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-94704275.470
Rat (Acute)
3.000
Rat (Chronic Oral)
1.630
Fathead Minnow
119550.660
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
10647334.510
Hydration Free Energy
-2.920
Log(D) at pH=7.4
5.060
Log(P)
6.88
Log S
-6.14
Log(Vapor Pressure)
-350557.55
Melting Point
243.81
pKa Acid
-2500.15
pKa Basic
8.68
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8564
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.8526
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.8316
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8059
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7966
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7647
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7643
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7476
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7453
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7335
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7282
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7275
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7159
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7020

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