Cyclombandakamine A - Compound Card

Cyclombandakamine A

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Cyclombandakamine A

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)OC)c3c(c2O1)c(OC)cc(c3)C)C
InChI InChI=1S/C48H50N2O8/c1-21-13-27-28(41-29-15-22(2)49-24(4)39(29)36(55-9)18-32(41)51)17-31-46(43(27)35(14-21)54-8)58-47(6)20-33(52)44-34(53-7)12-11-26-42-30-16-23(3)50-25(5)40(30)37(56-10)19-38(42)57-48(31,47)45(26)44/h11-14,17-19,22-25,49-51H,15-16,20H2,1-10H3/t22-,23-,24-,25-,47+,48+/m1/s1
InChIKey YIBOSVQNPAMGPL-GVTUPBAYSA-N
Formula C48H50N2O8
HBA 10
HBD 3
MW 782.93
Rotatable Bonds 5
TPSA 116.74
LogP 8.79
Number Rings 10
Number Aromatic Rings 5
Heavy Atom Count 58
Formal Charge 0
Fraction CSP3 0.4
Exact Mass 782.36
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Ancistrocladus ealaensis Ancistrocladaceae Plantae 714098

Showing of synonyms

  • Tshitenge DT, Bruhn T, et al. (2019). An Unusually Broad Series of Seven Cyclombandakamines, Bridged Dimeric Naphthylisoquinoline Alkaloids from the Congolese Liana Ancistrocladus ealaensis.. Scientific reports,2019, 9(1), 9812. [View] [PubMed]

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: 782.93 g/mol

Structure

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

Level: 0

Mol. Weight: 782.93 g/mol

Structure

SMILES: C1CNCc(c12)cccc2

Level: 0

Mol. Weight: 782.93 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.59
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
251.460
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
33574.27

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.210
Plasma Protein Binding
73.78
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
9.620
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Toxic
Bee
Toxic
Bioconcentration Factor
-783.440
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.440
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.050
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Toxic
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-60935414.060
Rat (Acute)
2.900
Rat (Chronic Oral)
1.690
Fathead Minnow
76924.560
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
6849264.090
Hydration Free Energy
-2.920
Log(D) at pH=7.4
5.270
Log(P)
6.55
Log S
-6.07
Log(Vapor Pressure)
-225489.41
Melting Point
271.4
pKa Acid
-1590.7
pKa Basic
9.94
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 0.8260
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8118
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7941
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7798
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7753
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7551
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7496
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7481
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.7247
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7225
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7212
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7174
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7167
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7131
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7123

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