Spirombandakamine A3 - Compound Card

Spirombandakamine A3

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Spirombandakamine A3

Structure
Zoomed Structure
  • Family: Plantae - Ancistrocladaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Naphthylisoquinoline Alkaloid
Canonical Smiles COc1ccc2c3c1C(=O)C[C@@]13c3cc(c4c(O)cc(c5c4C[C@@H](C)N[C@@H]5C)OC)c4c(c3O[C@]1(C)Oc1c2c2C[C@@H](C)N([C@@H](c2c(c1)OC)C)C)c(OC)cc(c4)C
InChI InChI=1S/C49H52N2O8/c1-22-14-28-29(42-30-16-23(2)50-25(4)40(30)37(56-10)19-33(42)52)18-32-47(44(28)36(15-22)55-9)59-48(6)49(32)21-34(53)45-35(54-8)13-12-27(46(45)49)43-31-17-24(3)51(7)26(5)41(31)38(57-11)20-39(43)58-48/h12-15,18-20,23-26,50,52H,16-17,21H2,1-11H3/t23-,24-,25-,26-,48+,49+/m1/s1
InChIKey SBOFQONQPWYCKK-KUGNVKOJSA-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: 164628542

No compound-protein relationship available.

Structure

SMILES: C123c4c(C(=O)C3)cccc4c5c6c(CNCC6)ccc5OC2Oc7c1cc(c8c7cccc8)-c9cccc(c19)CNCC1

Level: 1

Mol. Weight: 796.96 g/mol

Structure

SMILES: C123c4c(C(=O)C3)cccc4c5c6c(CNCC6)ccc5OC2Oc7c1ccc8c7cccc8

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)
-5.55
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
411.860
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
54540.01

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.250
Plasma Protein Binding
74.7
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
9.700
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Toxic
Bee
Toxic
Bioconcentration Factor
-1270.430
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.360
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
Toxic
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-98986658.980
Rat (Acute)
3.000
Rat (Chronic Oral)
1.620
Fathead Minnow
124956.370
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
11129014.670
Hydration Free Energy
-2.920
Log(D) at pH=7.4
4.760
Log(P)
6.83
Log S
-6.18
Log(Vapor Pressure)
-366420.71
Melting Point
244.34
pKa Acid
-2616.47
pKa Basic
9.06
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9406
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.9173
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8880
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8750
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8528
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7240
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7172
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7168
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7119
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7117
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7005
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7003

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