Cyclombandakamine A2 - Compound Card

Cyclombandakamine A2

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Cyclombandakamine A2

Structure
Zoomed Structure
  • Family: Plantae - Ancistrocladaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Naphthylisoquinoline Alkaloid
Canonical Smiles COc1cc2O[C@]34c5c(c2c2c1[C@@H](C)N(C)[C@@H](C2)C)ccc(c5C(=O)C[C@]4(C)Oc1c3cc(c2c(O)cc(c3c2C[C@H](C)N([C@@H]3C)C)OC)c2c1c(OC)cc(c2)C)OC
InChI InChI=1S/C50H54N2O8/c1-23-15-29-30(43-31-17-24(2)51(7)26(4)41(31)38(57-11)20-34(43)53)19-33-48(45(29)37(16-23)56-10)60-49(6)22-35(54)46-36(55-9)14-13-28-44-32-18-25(3)52(8)27(5)42(32)39(58-12)21-40(44)59-50(33,49)47(28)46/h13-16,19-21,24-27,53H,17-18,22H2,1-12H3/t24-,25+,26+,27+,49-,50-/m0/s1
InChIKey HNCYEGHHOCVPLZ-AAFKBUOQSA-N
Formula C50H54N2O8
HBA 10
HBD 1
MW 810.99
Rotatable Bonds 5
TPSA 99.16
LogP 9.47
Number Rings 10
Number Aromatic Rings 5
Heavy Atom Count 60
Formal Charge 0
Fraction CSP3 0.42
Exact Mass 810.39
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Ancistrocladus sp. Ancistrocladaceae Plantae 300538
2 Ancistrocladus liana Ancistrocladaceae Plantae 63071
3 Ancistrocladus liana Ancistrocladaceae Plantae 63071
4 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]
  • Lombe BK, Bruhn T, et al. (2017). Cyclombandakamines A1 and A2, oxygen-bridged naphthylisoquinoline dimers from a Congolese Ancistrocladus liana.. Organic letters,2017, 19(6), 1342-1345. [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: 132608472

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: 810.99 g/mol

Structure

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

Level: 0

Mol. Weight: 810.99 g/mol

Structure

SMILES: C1CNCc(c12)cccc2

Level: 0

Mol. Weight: 810.99 g/mol

Antimalarial
Antiprotozoal

Absorption

Caco-2 (logPapp)
-5.45
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
614.610
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
81032.72

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.120
Plasma Protein Binding
70.92
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
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
9.980
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Toxic
Bee
Toxic
Bioconcentration Factor
-1886.120
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.270
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
4.820
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
Toxic
T. Pyriformis
-147069184.420
Rat (Acute)
3.040
Rat (Chronic Oral)
1.640
Fathead Minnow
185650.330
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
16536942.740
Hydration Free Energy
-2.920
Log(D) at pH=7.4
4.350
Log(P)
7.1
Log S
-6.23
Log(Vapor Pressure)
-544498.83
Melting Point
226.81
pKa Acid
-3912.75
pKa Basic
1.81
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 0.8811
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8811
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.8437
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.8437
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.8221
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.8221
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8097
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8097
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7788
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7788
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7731
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7731
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7680
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7680
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7668
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7668
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7586
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7586
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7473
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7473
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7438
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7438
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7388
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7388
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7375
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7375
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7335
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7335
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7333
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7333
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7293
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7293
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7221
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7221
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7221
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7221
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7183
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7183
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7159
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7159

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