Ancistronaphthoic acid B - Compound Card

Ancistronaphthoic acid B

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Ancistronaphthoic acid B

Structure
Zoomed Structure
  • Family: Plantae - Ancistrocladaceae
  • Kingdom: Plantae
  • Class: Naphthoic Acid
Canonical Smiles COc1cc(cc2c1c(O)ccc2)C(=O)O
InChI InChI=1S/C12H10O4/c1-16-10-6-8(12(14)15)5-7-3-2-4-9(13)11(7)10/h2-6,13H,1H3,(H,14,15)
InChIKey GVGQCCXRDGHGTD-UHFFFAOYSA-N
Formula C12H10O4
HBA 3
HBD 2
MW 218.21
Rotatable Bonds 2
TPSA 66.76
LogP 2.25
Number Rings 2
Number Aromatic Rings 2
Heavy Atom Count 16
Formal Charge 0
Fraction CSP3 0.08
Exact Mass 218.06
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Ancistrocladus ealaensis Ancistrocladaceae Plantae 714098
2 Ancistrocladus likoko Ancistrocladaceae Plantae 714102

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]
  • Bringmann G, Saeb W, et al. (2003). Ancistrolikokine D, a 5,8'-coupled naphthylisoquinoline alkaloid, and related natural products from Ancistrocladus likoko. Phytochemistry,2003, 62(4), 631-636. [View] [PubMed]
Pubchem: 10751276
Nmrshiftdb2: 60030297

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 218.21 g/mol

Anti-leishmanial

Absorption

Caco-2 (logPapp)
-4.66
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.680
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.62

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.140
Plasma Protein Binding
51.71
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
9.640
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.030
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.360
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
1.780
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
3.840
Rat (Acute)
2.110
Rat (Chronic Oral)
3.390
Fathead Minnow
3.900
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
343.660
Hydration Free Energy
-9.760
Log(D) at pH=7.4
0.450
Log(P)
2.86
Log S
-3.39
Log(Vapor Pressure)
-6.01
Melting Point
210.77
pKa Acid
6.22
pKa Basic
2.74
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 0.9612
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9455
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 3 0.9341
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.9205
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9142
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.9140
4-chlorobenzoyl CoA ligase Q8GN86 Q8GN86_9BURK Alcaligenes sp. AL3007 3 0.9030
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 3 0.9004
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8988
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 3 0.8973
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8946
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8828
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8826
4-chlorobenzoyl CoA ligase Q8GN86 Q8GN86_9BURK Alcaligenes sp. AL3007 3 0.8821
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 3 0.8722
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 3 0.8701
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8611
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8591
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8584
Glutathione S-transferase A1 P08263 GSTA1_HUMAN Homo sapiens 3 0.8560
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.8542
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.8511
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8393
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.8224
Dihydroorotate dehydrogenase (quinone), mitochondrial Q08210 PYRD_PLAF7 Plasmodium falciparum 3 0.8212
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8167
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 3 0.8165
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8146
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 3 0.8137
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.8093
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.8016
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7999
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.7963
RIO-type serine/threonine-protein kinase Rio1 O28471 RIO1_ARCFU Archaeoglobus fulgidus 3 0.7943
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7927
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.7913
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7891
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7843
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7837
NAD-dependent protein deacetylase Q9WYW0 NPD_THEMA Thermotoga maritima 3 0.7789
Sepiapterin reductase Q64105 SPRE_MOUSE Mus musculus 4 0.7755
Dihydrofolate reductase P0ABQ4 DYR_ECOLI Escherichia coli 3 0.7729
Aldo-keto reductase family 1 member A1 P50578 AK1A1_PIG Sus scrofa 3 0.7703
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7675
DNA mismatch repair protein Msh2 P43246 MSH2_HUMAN Homo sapiens 3 0.7619
cAMP-dependent protein kinase catalytic subunit alpha P05132 KAPCA_MOUSE Mus musculus 3 0.7596
DNA mismatch repair protein MutS P23909 MUTS_ECOLI Escherichia coli 3 0.7592
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7590
Carbonic anhydrase Q39588 Q39588_CHLRE Chlamydomonas reinhardtii 3 0.7590
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7551
Aspartate aminotransferase, mitochondrial P00508 AATM_CHICK Gallus gallus 3 0.7543
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7518
SRSF protein kinase 1 Q96SB4 SRPK1_HUMAN Homo sapiens 3 0.7486
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7484
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7475
Cysteine desulfurase IscS 2 O29689 ISCS2_ARCFU Archaeoglobus fulgidus 3 0.7467
DNA-binding transcriptional dual regulator CRP P0ACJ8 CRP_ECOLI Escherichia coli 3 0.7464
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7453
DNA mismatch repair protein MutS P23909 MUTS_ECOLI Escherichia coli 3 0.7451
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.7423
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7388
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7372
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7370
4-chlorobenzoyl CoA ligase Q8GN86 Q8GN86_9BURK Alcaligenes sp. AL3007 3 0.7351
Aspartokinase 1, chloroplastic Q9LYU8 AK1_ARATH Arabidopsis thaliana 3 0.7333
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7330
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7316
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7295
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7282
tRNA (cytidine-2'-O-)-methyltransferase TrmJ Q4JB16 TRMJ_SULAC Sulfolobus acidocaldarius 4 0.7274
Tyrosine-protein kinase ABL1 P00519 ABL1_HUMAN Homo sapiens 3 0.7272
Shikimate dehydrogenase (NADP(+)) P56119 AROE_HELPY Helicobacter pylori 3 0.7271
Activated CDC42 kinase 1 Q07912 ACK1_HUMAN Homo sapiens 3 0.7270
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7267
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7266
Maltokinase A1TH50 MAK_MYCVP Mycolicibacterium vanbaalenii 3 0.7259
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7253
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.7247
Malate synthase G P9WK17 MASZ_MYCTU Mycobacterium tuberculosis 3 0.7241
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7231
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7231
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7223
tRNA (adenine(9)-N1)-methyltransferase Q4J894 TRM10_SULAC Sulfolobus acidocaldarius 3 0.7213
DNA-binding transcriptional dual regulator CRP P0ACJ8 CRP_ECOLI Escherichia coli 3 0.7210
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7209
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7208
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7196
Putative N-acetyl glucosaminyl transferase Q6U8B0 Q6U8B0_RAOTE Raoultella terrigena 3 0.7196
Rifampin ADP-ribosyl transferase A0QRS5 A0QRS5_MYCS2 Mycolicibacterium smegmatis155) 3 0.7194
Ribosomal protein S6 kinase alpha-1 Q15418 KS6A1_HUMAN Homo sapiens 3 0.7191
L-lactate dehydrogenase (cytochrome) P00175 CYB2_YEAST Saccharomyces cerevisiae 3 0.7190
Methyltransferase D0VX01 D0VX01_WSLV Wesselsbron virus 3 0.7189
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7181
ADP-ribose glycohydrolase AF_1521 O28751 Y1521_ARCFU Archaeoglobus fulgidus 4 0.7173
Genome polyprotein A0EKU1 A0EKU1_9FLAV Meaban virus 3 0.7170
Aspartate aminotransferase P00509 AAT_ECOLI Escherichia coli 3 0.7167
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7160
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7138
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7132
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7128
Dihydrofolate reductase P0ABQ4 DYR_ECOLI Escherichia coli 3 0.7124
Genome polyprotein P12823 POLG_DEN2P Dengue virus type 2 3 0.7117
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7115
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7107
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7073
Dihydroorotate dehydrogenase (quinone), mitochondrial Q02127 PYRD_HUMAN Homo sapiens 3 0.7054
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7050
DNA-binding transcriptional dual regulator CRP P0ACJ8 CRP_ECOLI Escherichia coli 3 0.7049
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7045
Mitogen-activated protein kinase kinase kinase 21 Q5TCX8 M3K21_HUMAN Homo sapiens 3 0.7025
DNA-binding transcriptional dual regulator CRP P0ACJ8 CRP_ECOLI Escherichia coli 3 0.7024
Deoxycytidylate deaminase H6WFU3 H6WFU3_9CAUD Cyanophage S-TIM5 4 0.7014
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7014
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7005
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7000

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