Ancistronaphthoic acid A - Compound Card

Ancistronaphthoic acid A

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Ancistronaphthoic acid A

Structure
Zoomed Structure
  • Family: Ancistrocladaceae
  • Kingdom: Plantae
  • Class: Naphthalene Derivative
Canonical Smiles COc1cc(cc2c1c(OC)ccc2)C(=O)O
InChI InChI=1S/C13H12O4/c1-16-10-5-3-4-8-6-9(13(14)15)7-11(17-2)12(8)10/h3-7H,1-2H3,(H,14,15)
InChIKey ALIUJDACFKDRMB-UHFFFAOYSA-N
Formula C13H12O4
HBA 3
HBD 1
MW 232.23
Rotatable Bonds 3
TPSA 55.76
LogP 2.56
Number Rings 2
Number Aromatic Rings 2
Heavy Atom Count 17
Formal Charge 0
Fraction CSP3 0.15
Exact Mass 232.07
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Ancistrocladus ealaensis Ancistrocladaceae Plantae 714098

Showing of synonyms

  • Bringmann G, Hamm A, et al. (2000). Ancistroealaines A and B, two new bioactive naphthylisoquinolines, and related naphthoic acids from Ancistrocladus ealaensis. Journal of natural products,2000, 63(11), 1465-1470. [View] [PubMed]
Pubchem: 21609766
Nmrshiftdb2: 20213088

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 128.17 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.62
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.540
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.67

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.200
Plasma Protein Binding
56.67
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-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
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.920
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.010
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.690
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.830
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
Safe
T. Pyriformis
2.150
Rat (Acute)
2.230
Rat (Chronic Oral)
2.780
Fathead Minnow
3.890
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
332.700
Hydration Free Energy
-10.420
Log(D) at pH=7.4
-0.120
Log(P)
3.27
Log S
-3.86
Log(Vapor Pressure)
-5.29
Melting Point
187.41
pKa Acid
5.16
pKa Basic
2.09
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9584
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9512
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9389
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 3 0.9360
4-chlorobenzoyl CoA ligase Q8GN86 Q8GN86_9BURK Alcaligenes sp. AL3007 3 0.9228
4-chlorobenzoyl CoA ligase Q8GN86 Q8GN86_9BURK Alcaligenes sp. AL3007 3 0.9018
Glutathione S-transferase A1 P08263 GSTA1_HUMAN Homo sapiens 3 0.8721
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 3 0.8578
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8543
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.8495
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8442
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8374
Dihydroorotate dehydrogenase (quinone), mitochondrial Q08210 PYRD_PLAF7 Plasmodium falciparum 3 0.8251
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.8217
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8060
4-chlorobenzoyl CoA ligase Q8GN86 Q8GN86_9BURK Alcaligenes sp. AL3007 3 0.8036
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7955
Aspartate aminotransferase, mitochondrial P00508 AATM_CHICK Gallus gallus 3 0.7870
Cysteine desulfurase IscS 2 O29689 ISCS2_ARCFU Archaeoglobus fulgidus 3 0.7769
Aldo-keto reductase family 1 member A1 P50578 AK1A1_PIG Sus scrofa 3 0.7766
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7741
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7705
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7641
Albumin P14639 ALBU_SHEEP Ovis aries 3 0.7606
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7576
Carbonic anhydrase Q39588 Q39588_CHLRE Chlamydomonas reinhardtii 3 0.7576
AGAP003309-PA A0A1U7F4W2 A0A1U7F4W2_ANOGA Anopheles gambiae 3 0.7564
L-lactate dehydrogenase (cytochrome) P00175 CYB2_YEAST Saccharomyces cerevisiae 3 0.7533
Aspartate aminotransferase, mitochondrial P00508 AATM_CHICK Gallus gallus 3 0.7515
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7488
Putative N-acetyl glucosaminyl transferase Q6U8B0 Q6U8B0_RAOTE Raoultella terrigena 3 0.7452
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.7419
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7412
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7335
Aspartate aminotransferase P00509 AAT_ECOLI Escherichia coli 3 0.7321
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7320
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7311
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7310
Poly [ADP-ribose] polymerase 1 P26446 PARP1_CHICK Gallus gallus 3 0.7295
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7292
Malate synthase G P9WK17 MASZ_MYCTU Mycobacterium tuberculosis 3 0.7286
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7271
Deoxycytidylate deaminase H6WFU3 H6WFU3_9CAUD Cyanophage S-TIM5 4 0.7227
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7194
Prostaglandin F2a synthase Q8I6L9 Q8I6L9_TRYCR Trypanosoma cruzi 2 0.7193
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Q8RQP5 ISPF_THET8 Thermus thermophilus 3 0.7165
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7154
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7149
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7081
Cytochrome P450 2A6 P11509 CP2A6_HUMAN Homo sapiens 3 0.7062
Dihydroorotate dehydrogenase (quinone), mitochondrial Q02127 PYRD_HUMAN Homo sapiens 3 0.7045
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7033
Cysteine desulfurase IscS 2 O29689 ISCS2_ARCFU Archaeoglobus fulgidus 3 0.7024

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