1,2-didehydroancistrobertsonine D - Compound Card

1,2-didehydroancistrobertsonine D

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1,2-didehydroancistrobertsonine D

Structure
Zoomed Structure
  • Family: Plantae - Ancistrocladaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Naphthylisoquinoline Alkaloid
Canonical Smiles COC1=C(C(=O)C=C2C1=C(C)N[C@H](C2)C)c1c(C)cc(c2c1cccc2OC)OC
InChI InChI=1S/C25H27NO4/c1-13-10-20(29-5)23-17(8-7-9-19(23)28-4)21(13)24-18(27)12-16-11-14(2)26-15(3)22(16)25(24)30-6/h7-10,12,14,26H,11H2,1-6H3/t14-/m0/s1
InChIKey MQPWQLBUYQDOGW-AWEZNQCLSA-N
Formula C25H27NO4
HBA 5
HBD 1
MW 405.49
Rotatable Bonds 4
TPSA 56.79
LogP 4.69
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.32
Exact Mass 405.19
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Ancistrocladus robertsoniorum Ancistrocladaceae Plantae 714105

Showing of synonyms

  • Bringmann G, Teltschika F, et al. (1999). Ancistrobertsonines B, C, and D as well as 1,2-didehydroancistrobertsonine D from Ancistrocladus robertsoniorum. Phytochemistry,1999,52(2),321-332. [View] [PubMed]
Pubchem: 15489678

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)cccc2C(=C3)C(=O)C=C(C3=4)CCNC4

Level: 1

Mol. Weight: 405.49 g/mol

Structure

SMILES: C1NCCC(C=12)=CC(=O)C=C2

Level: 0

Mol. Weight: 405.49 g/mol

Structure

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 405.49 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.91
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.520
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.31

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.010
Plasma Protein Binding
50.07
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
4.920
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.090
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.040
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.800
Micronucleos
Safe
NR-AhR
Toxic
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
Safe
T. Pyriformis
-28.620
Rat (Acute)
2.760
Rat (Chronic Oral)
2.320
Fathead Minnow
5.240
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
495.790
Hydration Free Energy
-5.140
Log(D) at pH=7.4
3.390
Log(P)
3.36
Log S
-5.18
Log(Vapor Pressure)
-7.23
Melting Point
164.39
pKa Acid
9.81
pKa Basic
7.77
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7704
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7704
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7465
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7465
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7442
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7442
4-hydroxyphenylacetate 3-monooxygenase, reductase component Q5SJP7 HPAC_THET8 Thermus thermophilus 3 0.7388
4-hydroxyphenylacetate 3-monooxygenase, reductase component Q5SJP7 HPAC_THET8 Thermus thermophilus 3 0.7388
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7338
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7338
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7301
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7301
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7164
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7164
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 2 0.7157
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 2 0.7157
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7137
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7137

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