Structure

Physi-Chem Properties

Molecular Weight:  342.22
Volume:  388.427
LogP:  5.174
LogD:  4.101
LogS:  -2.856
# Rotatable Bonds:  13
TPSA:  57.53
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  1
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.339
Synthetic Accessibility Score:  2.708
Fsp3:  0.409
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.124
MDCK Permeability:  3.49836191162467e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.027
20% Bioavailability (F20%):  1.0
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.008
Plasma Protein Binding (PPB):  100.53140258789062%
Volume Distribution (VD):  0.134
Pgp-substrate:  0.3501322567462921%

ADMET: Metabolism

CYP1A2-inhibitor:  0.344
CYP1A2-substrate:  0.382
CYP2C19-inhibitor:  0.292
CYP2C19-substrate:  0.06
CYP2C9-inhibitor:  0.596
CYP2C9-substrate:  0.881
CYP2D6-inhibitor:  0.88
CYP2D6-substrate:  0.492
CYP3A4-inhibitor:  0.269
CYP3A4-substrate:  0.057

ADMET: Excretion

Clearance (CL):  2.123
Half-life (T1/2):  0.924

ADMET: Toxicity

hERG Blockers:  0.077
Human Hepatotoxicity (H-HT):  0.297
Drug-inuced Liver Injury (DILI):  0.439
AMES Toxicity:  0.682
Rat Oral Acute Toxicity:  0.013
Maximum Recommended Daily Dose:  0.076
Skin Sensitization:  0.923
Carcinogencity:  0.544
Eye Corrosion:  0.009
Eye Irritation:  0.678
Respiratory Toxicity:  0.946

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC184579

Natural Product ID:  NPC184579
Common Name*:   Anacardic Acid
IUPAC Name:   2-hydroxy-6-[(8Z,11Z)-pentadeca-8,11,14-trienyl]benzoic acid
Synonyms:   6-(Pentadecenyl)Salicylic Acid; 6-Pentadecylsalicylic Acid; Anacardic Acid
Standard InCHIKey:  QUVGEKPNSCFQIR-UTOQUPLUSA-N
Standard InCHI:  InChI=1S/C22H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19-17-15-18-20(23)21(19)22(24)25/h2,4-5,7-8,15,17-18,23H,1,3,6,9-14,16H2,(H,24,25)/b5-4-,8-7-
SMILES:  C=CC/C=CC/C=CCCCCCCCc1cccc(c1C(=O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL455368
PubChem CID:   9875131
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives
        • [CHEMONTID:0000176] Benzoic acids and derivatives
          • [CHEMONTID:0001248] Hydroxybenzoic acid derivatives
            • [CHEMONTID:0000487] Salicylic acid and derivatives
              • [CHEMONTID:0002514] Salicylic acids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO8896 Anacardium occidentale Species Anacardiaceae Eukaryota Fruits n.a. n.a. PMID[8021657]
NPO8896 Anacardium occidentale Species Anacardiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO8896 Anacardium occidentale Species Anacardiaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO8896 Anacardium occidentale Species Anacardiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO8896 Anacardium occidentale Species Anacardiaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO8896 Anacardium occidentale Species Anacardiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO8896 Anacardium occidentale Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8896 Anacardium occidentale Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3580 Rana amurensis Species Ranidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3469 Pteris dactylina Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8896 Anacardium occidentale Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3580 Rana amurensis Species Ranidae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8896 Anacardium occidentale Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13016 Viscaria viscosa Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11636 Ideopsis similis Species Nymphalidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3469 Pteris dactylina Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12510 Aronia arbutifolia Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13070 Clibadium mexiae Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1744 Discaria serratifolia Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9180 Pyrostegia venusta Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO998 Justicia hayatai Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3580 Rana amurensis Species Ranidae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT650 Individual Protein Beta-lactamase pse-1 Escherichia coli IC50 = 1100.0 ug.mL-1 PMID[504264]
NPT651 Individual Protein Beta-lactamase OXA-1 Escherichia coli IC50 = 25000.0 ug.mL-1 PMID[504264]
NPT652 Individual Protein Beta-lactamase TEM Escherichia coli IC50 = 800.0 ug.mL-1 PMID[504264]
NPT653 Individual Protein Beta-lactamase Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG12228) IC50 = 7200.0 ug.mL-1 PMID[504264]
NPT654 Individual Protein Beta-lactamase Enterobacter cloacae IC50 = 1400.0 ug.mL-1 PMID[504264]
NPT655 Individual Protein Beta-lactamase Proteus mirabilis IC50 = 31000.0 ug.mL-1 PMID[504264]
NPT466 Cell Line U-937 Homo sapiens Activity = 15.0 % PMID[504265]
NPT1432 Individual Protein Serine/threonine-protein kinase Aurora-A Homo sapiens Ka = 5.2 /uM PMID[504268]
NPT1432 Individual Protein Serine/threonine-protein kinase Aurora-A Homo sapiens Ka = 10.1 /uM PMID[504268]
NPT1432 Individual Protein Serine/threonine-protein kinase Aurora-A Homo sapiens Vmax = 62.5 mmol/min/mg PMID[504268]
NPT1432 Individual Protein Serine/threonine-protein kinase Aurora-A Homo sapiens Km = 40250000.0 nM PMID[504268]
NPT1432 Individual Protein Serine/threonine-protein kinase Aurora-A Homo sapiens Kcat = 281.5 /s PMID[504268]
NPT1432 Individual Protein Serine/threonine-protein kinase Aurora-A Homo sapiens Kcat/Km = 6.99 /s/mM PMID[504268]
NPT1079 Individual Protein Histone acetyltransferase p300 Homo sapiens IC50 = 5000.0 nM PMID[504273]
NPT43 Individual Protein Tyrosinase Agaricus bisporus Inhibition = 15.0 % PMID[504275]
NPT43 Individual Protein Tyrosinase Agaricus bisporus Inhibition = 45.0 % PMID[504276]
NPT43 Individual Protein Tyrosinase Agaricus bisporus ID50 = 4.2 mM PMID[504275]
NPT43 Individual Protein Tyrosinase Agaricus bisporus ID50 = 1.1 mM PMID[504276]
NPT4248 Individual Protein Histone acetyltransferase KAT5 Homo sapiens IC50 = 9000.0 nM PMID[504277]
NPT4248 Individual Protein Histone acetyltransferase KAT5 Homo sapiens IC50 = 374590.0 nM PMID[504277]
NPT1079 Individual Protein Histone acetyltransferase p300 Homo sapiens IC50 > 1000000.0 nM PMID[504277]
NPT1080 Individual Protein Histone acetyltransferase PCAF Homo sapiens IC50 = 667050.0 nM PMID[504277]
NPT1079 Individual Protein Histone acetyltransferase p300 Homo sapiens Activity = 53.1 % PMID[504278]
NPT1834 Individual Protein CREB-binding protein Homo sapiens Activity = 44.0 % PMID[504278]
NPT443 Individual Protein Histone acetyltransferase GCN5 Homo sapiens Activity = 112.6 % PMID[504278]
NPT1080 Individual Protein Histone acetyltransferase PCAF Homo sapiens Activity = 52.1 % PMID[504278]
NPT1080 Individual Protein Histone acetyltransferase PCAF Homo sapiens IC50 = 1000000.0 nM PMID[504279]
NPT1080 Individual Protein Histone acetyltransferase PCAF Homo sapiens Inhibition = 40.0 % PMID[504279]
NPT1489 Individual Protein Glyceraldehyde-3-phosphate dehydrogenase, glycosomal Trypanosoma cruzi IC50 = 28000.0 nM PMID[504280]
NPT1489 Individual Protein Glyceraldehyde-3-phosphate dehydrogenase, glycosomal Trypanosoma cruzi Ki = 4000.0 nM PMID[504280]
NPT1489 Individual Protein Glyceraldehyde-3-phosphate dehydrogenase, glycosomal Trypanosoma cruzi Ki = 6000.0 nM PMID[504280]
NPT1489 Individual Protein Glyceraldehyde-3-phosphate dehydrogenase, glycosomal Trypanosoma cruzi Ki = 2000.0 nM PMID[504280]
NPT1834 Individual Protein CREB-binding protein Homo sapiens Inhibition = 62.0 % PMID[504281]
NPT4248 Individual Protein Histone acetyltransferase KAT5 Homo sapiens Inhibition > 76.0 % PMID[504283]
NPT1080 Individual Protein Histone acetyltransferase PCAF Homo sapiens Inhibition <= 20.0 % PMID[504283]
NPT1079 Individual Protein Histone acetyltransferase p300 Homo sapiens Inhibition <= 20.0 % PMID[504283]
NPT4248 Individual Protein Histone acetyltransferase KAT5 Homo sapiens IC50 = 64000.0 nM PMID[504283]
NPT1080 Individual Protein Histone acetyltransferase PCAF Homo sapiens IC50 = 8500.0 nM PMID[504283]
NPT1079 Individual Protein Histone acetyltransferase p300 Homo sapiens IC50 = 5000.0 nM PMID[504283]
NPT1080 Individual Protein Histone acetyltransferase PCAF Homo sapiens Inhibition = 40.0 % PMID[504283]
NPT1079 Individual Protein Histone acetyltransferase p300 Homo sapiens Inhibition = 40.0 % PMID[504283]
NPT4248 Individual Protein Histone acetyltransferase KAT5 Homo sapiens Inhibition > 50.0 % PMID[504283]
NPT2653 Individual Protein Histone acetyltransferase KAT8 Homo sapiens IC50 = 43000.0 nM PMID[504283]
NPT2 Others Unspecified Activity = 62.0 % PMID[504269]
NPT878 Organism Streptococcus mutans Streptococcus mutans MIC = 1.56 ug.mL-1 PMID[504271]
NPT878 Organism Streptococcus mutans Streptococcus mutans MBC = 0.78 ug ml-1 PMID[504271]
NPT878 Organism Streptococcus mutans Streptococcus mutans MBC = 6.25 ug ml-1 PMID[504271]
NPT89 Individual Protein Seed lipoxygenase-1 Glycine max IC50 > 250000.0 nM PMID[504272]
NPT167 Organism Propionibacterium acnes Propionibacterium acnes MIC = 0.78 ug.mL-1 PMID[504274]
NPT2 Others Unspecified IC50 = 297230.0 nM PMID[504277]
NPT2 Others Unspecified Inhibition = 15.0 % PMID[504278]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

  Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

●  The left chart: Distribution of similarity level between NPC184579 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
1.0 High Similarity NPC233165
0.9823 High Similarity NPC301987
0.9823 High Similarity NPC244994
0.9823 High Similarity NPC292665
0.9823 High Similarity NPC179092
0.9823 High Similarity NPC159760
0.9823 High Similarity NPC115188
0.9823 High Similarity NPC35856
0.9823 High Similarity NPC178395
0.9823 High Similarity NPC26433
0.9823 High Similarity NPC272454
0.9823 High Similarity NPC222876
0.9652 High Similarity NPC244351
0.9643 High Similarity NPC125252
0.9407 High Similarity NPC167055
0.9407 High Similarity NPC240744
0.9381 High Similarity NPC477453
0.9316 High Similarity NPC283514
0.9231 High Similarity NPC198336
0.9024 High Similarity NPC247477
0.9024 High Similarity NPC17840
0.9 High Similarity NPC236189
0.9 High Similarity NPC265910
0.9 High Similarity NPC91475
0.8952 High Similarity NPC7012
0.8862 High Similarity NPC95537
0.8839 High Similarity NPC100551
0.8824 High Similarity NPC165197
0.8783 High Similarity NPC211421
0.878 High Similarity NPC181715
0.877 High Similarity NPC262671
0.877 High Similarity NPC201728
0.877 High Similarity NPC477454
0.876 High Similarity NPC477153
0.875 High Similarity NPC25168
0.873 High Similarity NPC470160
0.872 High Similarity NPC31539
0.8718 High Similarity NPC312800
0.8718 High Similarity NPC108288
0.8699 High Similarity NPC473691
0.8689 High Similarity NPC470163
0.8689 High Similarity NPC470162
0.8678 High Similarity NPC297193
0.8661 High Similarity NPC37299
0.8661 High Similarity NPC43627
0.8661 High Similarity NPC180261
0.8644 High Similarity NPC269414
0.8644 High Similarity NPC121259
0.8644 High Similarity NPC160199
0.864 High Similarity NPC92624
0.8632 High Similarity NPC161304
0.8629 High Similarity NPC209959
0.8607 High Similarity NPC275145
0.8605 High Similarity NPC118919
0.8594 High Similarity NPC474097
0.8583 High Similarity NPC216297
0.8583 High Similarity NPC7151
0.8583 High Similarity NPC473662
0.8583 High Similarity NPC285829
0.8583 High Similarity NPC206778
0.8571 High Similarity NPC259942
0.856 High Similarity NPC41263
0.8559 High Similarity NPC128825
0.8548 High Similarity NPC136342
0.8548 High Similarity NPC295202
0.8548 High Similarity NPC227741
0.8548 High Similarity NPC49647
0.8548 High Similarity NPC160499
0.8548 High Similarity NPC306765
0.8538 High Similarity NPC71256
0.8537 High Similarity NPC117794
0.8527 High Similarity NPC27407
0.8527 High Similarity NPC142027
0.8527 High Similarity NPC290803
0.8525 High Similarity NPC300274
0.8525 High Similarity NPC307174
0.8509 High Similarity NPC224584
0.8504 High Similarity NPC214702
0.8504 High Similarity NPC470831
0.85 High Similarity NPC328459
0.85 High Similarity NPC90522
0.85 High Similarity NPC195262
0.85 High Similarity NPC188814
0.8475 Intermediate Similarity NPC240163
0.8468 Intermediate Similarity NPC131799
0.8468 Intermediate Similarity NPC472592
0.8462 Intermediate Similarity NPC223004
0.8455 Intermediate Similarity NPC375356
0.845 Intermediate Similarity NPC474394
0.843 Intermediate Similarity NPC260837
0.843 Intermediate Similarity NPC72977
0.8417 Intermediate Similarity NPC94637
0.8417 Intermediate Similarity NPC41567
0.8413 Intermediate Similarity NPC48248
0.8397 Intermediate Similarity NPC149372
0.8397 Intermediate Similarity NPC474771
0.8397 Intermediate Similarity NPC178467
0.8397 Intermediate Similarity NPC194579
0.8397 Intermediate Similarity NPC65837
0.8397 Intermediate Similarity NPC62272
0.8397 Intermediate Similarity NPC474849
0.8397 Intermediate Similarity NPC70380
0.839 Intermediate Similarity NPC118288
0.839 Intermediate Similarity NPC276111
0.8387 Intermediate Similarity NPC173978
0.8387 Intermediate Similarity NPC74507
0.8387 Intermediate Similarity NPC234890
0.8385 Intermediate Similarity NPC72918
0.8385 Intermediate Similarity NPC161632
0.8374 Intermediate Similarity NPC46634
0.8372 Intermediate Similarity NPC48036
0.8359 Intermediate Similarity NPC219892
0.8359 Intermediate Similarity NPC189823
0.8347 Intermediate Similarity NPC232178
0.8346 Intermediate Similarity NPC474546
0.8333 Intermediate Similarity NPC94248
0.8333 Intermediate Similarity NPC478200
0.8333 Intermediate Similarity NPC212693
0.8333 Intermediate Similarity NPC472602
0.8333 Intermediate Similarity NPC187913
0.8333 Intermediate Similarity NPC191835
0.8333 Intermediate Similarity NPC9121
0.8333 Intermediate Similarity NPC33144
0.8333 Intermediate Similarity NPC471530
0.8333 Intermediate Similarity NPC475974
0.8333 Intermediate Similarity NPC177307
0.8333 Intermediate Similarity NPC4214
0.8321 Intermediate Similarity NPC291454
0.832 Intermediate Similarity NPC287473
0.832 Intermediate Similarity NPC103540
0.8308 Intermediate Similarity NPC282780
0.8308 Intermediate Similarity NPC166480
0.8293 Intermediate Similarity NPC196976
0.8291 Intermediate Similarity NPC228609
0.8284 Intermediate Similarity NPC313123
0.8284 Intermediate Similarity NPC478217
0.8279 Intermediate Similarity NPC233282
0.8271 Intermediate Similarity NPC295339
0.8264 Intermediate Similarity NPC474890
0.8264 Intermediate Similarity NPC161943
0.8264 Intermediate Similarity NPC273282
0.8261 Intermediate Similarity NPC34715
0.8258 Intermediate Similarity NPC261292
0.8258 Intermediate Similarity NPC301915
0.8254 Intermediate Similarity NPC3224
0.8254 Intermediate Similarity NPC96915
0.8254 Intermediate Similarity NPC473751
0.8254 Intermediate Similarity NPC231774
0.8244 Intermediate Similarity NPC204257
0.8244 Intermediate Similarity NPC254832
0.8244 Intermediate Similarity NPC278375
0.8244 Intermediate Similarity NPC229638
0.8244 Intermediate Similarity NPC29317
0.8244 Intermediate Similarity NPC176102
0.8244 Intermediate Similarity NPC71108
0.8244 Intermediate Similarity NPC267539
0.824 Intermediate Similarity NPC310540
0.824 Intermediate Similarity NPC152525
0.824 Intermediate Similarity NPC142956
0.824 Intermediate Similarity NPC68756
0.8231 Intermediate Similarity NPC153783
0.8231 Intermediate Similarity NPC200422
0.8231 Intermediate Similarity NPC157478
0.8231 Intermediate Similarity NPC289572
0.8231 Intermediate Similarity NPC295406
0.823 Intermediate Similarity NPC13426
0.8226 Intermediate Similarity NPC217756
0.8222 Intermediate Similarity NPC250755
0.822 Intermediate Similarity NPC231717
0.8217 Intermediate Similarity NPC85342
0.8211 Intermediate Similarity NPC149246
0.8211 Intermediate Similarity NPC190971
0.8211 Intermediate Similarity NPC241001
0.8209 Intermediate Similarity NPC168471
0.8209 Intermediate Similarity NPC158472
0.8203 Intermediate Similarity NPC34414
0.8203 Intermediate Similarity NPC109123
0.8203 Intermediate Similarity NPC146647
0.8195 Intermediate Similarity NPC61590
0.8195 Intermediate Similarity NPC472403
0.8189 Intermediate Similarity NPC71525
0.8182 Intermediate Similarity NPC223836
0.8182 Intermediate Similarity NPC158481
0.8182 Intermediate Similarity NPC472308
0.8174 Intermediate Similarity NPC317592
0.8168 Intermediate Similarity NPC12070
0.8168 Intermediate Similarity NPC288089
0.8168 Intermediate Similarity NPC175943
0.8162 Intermediate Similarity NPC478202
0.8154 Intermediate Similarity NPC246693
0.8154 Intermediate Similarity NPC110609
0.8154 Intermediate Similarity NPC242358
0.8148 Intermediate Similarity NPC478201
0.8148 Intermediate Similarity NPC53649
0.8148 Intermediate Similarity NPC475730
0.8148 Intermediate Similarity NPC1704
0.8148 Intermediate Similarity NPC257003
0.8148 Intermediate Similarity NPC67650
0.8148 Intermediate Similarity NPC472035
0.8148 Intermediate Similarity NPC158634

  Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC184579 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.8839 High Similarity NPD74 Approved
0.8839 High Similarity NPD9266 Approved
0.875 High Similarity NPD9267 Approved
0.875 High Similarity NPD9264 Approved
0.875 High Similarity NPD9263 Approved
0.8718 High Similarity NPD405 Clinical (unspecified phase)
0.8595 High Similarity NPD1201 Approved
0.8559 High Similarity NPD9493 Approved
0.8468 Intermediate Similarity NPD1164 Approved
0.8397 Intermediate Similarity NPD5404 Approved
0.8397 Intermediate Similarity NPD5406 Approved
0.8397 Intermediate Similarity NPD5405 Approved
0.8397 Intermediate Similarity NPD5408 Approved
0.8393 Intermediate Similarity NPD9261 Approved
0.832 Intermediate Similarity NPD1470 Approved
0.8235 Intermediate Similarity NPD9281 Approved
0.812 Intermediate Similarity NPD2935 Discontinued
0.7937 Intermediate Similarity NPD9717 Approved
0.7891 Intermediate Similarity NPD1203 Approved
0.7868 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7797 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7744 Intermediate Similarity NPD943 Approved
0.7727 Intermediate Similarity NPD411 Approved
0.7692 Intermediate Similarity NPD2798 Approved
0.7687 Intermediate Similarity NPD447 Suspended
0.7664 Intermediate Similarity NPD2346 Discontinued
0.7619 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7615 Intermediate Similarity NPD2797 Approved
0.7594 Intermediate Similarity NPD3764 Approved
0.7589 Intermediate Similarity NPD7390 Discontinued
0.7559 Intermediate Similarity NPD2932 Approved
0.7559 Intermediate Similarity NPD3019 Approved
0.7559 Intermediate Similarity NPD4626 Approved
0.7544 Intermediate Similarity NPD844 Approved
0.754 Intermediate Similarity NPD1759 Phase 1
0.7537 Intermediate Similarity NPD520 Approved
0.7535 Intermediate Similarity NPD2534 Approved
0.7535 Intermediate Similarity NPD2533 Approved
0.7535 Intermediate Similarity NPD2532 Approved
0.7518 Intermediate Similarity NPD3300 Phase 2
0.7518 Intermediate Similarity NPD2799 Discontinued
0.75 Intermediate Similarity NPD5951 Approved
0.75 Intermediate Similarity NPD3750 Approved
0.7478 Intermediate Similarity NPD288 Approved
0.7463 Intermediate Similarity NPD2313 Discontinued
0.746 Intermediate Similarity NPD1758 Phase 1
0.7444 Intermediate Similarity NPD6832 Phase 2
0.7438 Intermediate Similarity NPD6831 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD289 Clinical (unspecified phase)
0.7411 Intermediate Similarity NPD9256 Approved
0.7411 Intermediate Similarity NPD9258 Approved
0.7402 Intermediate Similarity NPD9545 Approved
0.7391 Intermediate Similarity NPD3299 Clinical (unspecified phase)
0.7385 Intermediate Similarity NPD9269 Phase 2
0.7377 Intermediate Similarity NPD4750 Phase 3
0.7376 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7365 Intermediate Similarity NPD7819 Suspended
0.7353 Intermediate Similarity NPD1240 Approved
0.7344 Intermediate Similarity NPD9268 Approved
0.7338 Intermediate Similarity NPD1551 Phase 2
0.7333 Intermediate Similarity NPD3268 Approved
0.7329 Intermediate Similarity NPD3226 Approved
0.7329 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7279 Intermediate Similarity NPD6663 Approved
0.7273 Intermediate Similarity NPD1283 Approved
0.7266 Intermediate Similarity NPD4308 Phase 3
0.7266 Intermediate Similarity NPD1510 Phase 2
0.7255 Intermediate Similarity NPD6232 Discontinued
0.7254 Intermediate Similarity NPD7003 Approved
0.7246 Intermediate Similarity NPD1607 Approved
0.7239 Intermediate Similarity NPD5736 Approved
0.7227 Intermediate Similarity NPD846 Approved
0.7227 Intermediate Similarity NPD940 Approved
0.7217 Intermediate Similarity NPD845 Approved
0.7213 Intermediate Similarity NPD2342 Discontinued
0.7209 Intermediate Similarity NPD5691 Approved
0.7203 Intermediate Similarity NPD3020 Approved
0.72 Intermediate Similarity NPD7635 Approved
0.7177 Intermediate Similarity NPD2181 Clinical (unspecified phase)
0.7172 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7167 Intermediate Similarity NPD1931 Clinical (unspecified phase)
0.7167 Intermediate Similarity NPD1929 Approved
0.7167 Intermediate Similarity NPD1930 Approved
0.7165 Intermediate Similarity NPD256 Approved
0.7165 Intermediate Similarity NPD255 Approved
0.7164 Intermediate Similarity NPD1019 Discontinued
0.7163 Intermediate Similarity NPD2344 Approved
0.7155 Intermediate Similarity NPD1432 Clinical (unspecified phase)
0.7154 Intermediate Similarity NPD7163 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD3748 Approved
0.7133 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7121 Intermediate Similarity NPD1608 Approved
0.7115 Intermediate Similarity NPD7473 Discontinued
0.7105 Intermediate Similarity NPD3749 Approved
0.7094 Intermediate Similarity NPD2859 Approved
0.7094 Intermediate Similarity NPD2860 Approved
0.7071 Intermediate Similarity NPD9279 Approved
0.7068 Intermediate Similarity NPD1755 Approved
0.7059 Intermediate Similarity NPD2066 Phase 3
0.7055 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7054 Intermediate Similarity NPD9259 Approved
0.7054 Intermediate Similarity NPD9257 Approved
0.705 Intermediate Similarity NPD230 Phase 1
0.7045 Intermediate Similarity NPD1281 Approved
0.7045 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7042 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7042 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD7768 Phase 2
0.7016 Intermediate Similarity NPD2182 Approved
0.7014 Intermediate Similarity NPD1196 Approved
0.7009 Intermediate Similarity NPD2933 Approved
0.7009 Intermediate Similarity NPD688 Clinical (unspecified phase)
0.7009 Intermediate Similarity NPD2934 Approved
0.6993 Remote Similarity NPD1549 Phase 2
0.6986 Remote Similarity NPD1511 Approved
0.6986 Remote Similarity NPD1543 Discontinued
0.6978 Remote Similarity NPD4307 Phase 2
0.6977 Remote Similarity NPD9568 Approved
0.6975 Remote Similarity NPD9495 Approved
0.697 Remote Similarity NPD3026 Approved
0.697 Remote Similarity NPD3023 Approved
0.697 Remote Similarity NPD3496 Discontinued
0.6967 Remote Similarity NPD164 Approved
0.6967 Remote Similarity NPD1237 Approved
0.6966 Remote Similarity NPD2309 Approved
0.6963 Remote Similarity NPD3266 Approved
0.6963 Remote Similarity NPD3267 Approved
0.696 Remote Similarity NPD3021 Approved
0.696 Remote Similarity NPD3022 Approved
0.6957 Remote Similarity NPD1086 Approved
0.6957 Remote Similarity NPD1090 Approved
0.6957 Remote Similarity NPD1089 Approved
0.6949 Remote Similarity NPD1809 Phase 2
0.6947 Remote Similarity NPD3024 Approved
0.6947 Remote Similarity NPD3025 Approved
0.6944 Remote Similarity NPD1195 Approved
0.6942 Remote Similarity NPD1932 Approved
0.6937 Remote Similarity NPD9491 Approved
0.6929 Remote Similarity NPD1933 Approved
0.6923 Remote Similarity NPD5122 Clinical (unspecified phase)
0.6923 Remote Similarity NPD1202 Approved
0.6912 Remote Similarity NPD257 Approved
0.6912 Remote Similarity NPD258 Approved
0.6908 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6897 Remote Similarity NPD3400 Discontinued
0.6897 Remote Similarity NPD8166 Discontinued
0.6894 Remote Similarity NPD17 Approved
0.6894 Remote Similarity NPD1778 Approved
0.6892 Remote Similarity NPD1512 Approved
0.6892 Remote Similarity NPD6273 Approved
0.6889 Remote Similarity NPD1876 Approved
0.6889 Remote Similarity NPD3225 Approved
0.6887 Remote Similarity NPD7411 Suspended
0.6883 Remote Similarity NPD7075 Discontinued
0.6875 Remote Similarity NPD75 Approved
0.6875 Remote Similarity NPD9277 Approved
0.6871 Remote Similarity NPD6799 Approved
0.687 Remote Similarity NPD800 Approved
0.6864 Remote Similarity NPD1693 Approved
0.6863 Remote Similarity NPD5402 Approved
0.6863 Remote Similarity NPD8438 Clinical (unspecified phase)
0.686 Remote Similarity NPD1242 Phase 1
0.6857 Remote Similarity NPD4060 Phase 1
0.6855 Remote Similarity NPD1444 Approved
0.6855 Remote Similarity NPD1445 Approved
0.6853 Remote Similarity NPD4477 Approved
0.6853 Remote Similarity NPD2796 Approved
0.6853 Remote Similarity NPD6100 Approved
0.6853 Remote Similarity NPD4476 Approved
0.6853 Remote Similarity NPD6099 Approved
0.6846 Remote Similarity NPD5403 Approved
0.6842 Remote Similarity NPD1934 Approved
0.6838 Remote Similarity NPD1088 Approved
0.6829 Remote Similarity NPD5909 Discontinued
0.6828 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6825 Remote Similarity NPD1792 Phase 2
0.6824 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6824 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6822 Remote Similarity NPD2629 Approved
0.6821 Remote Similarity NPD4380 Phase 2
0.6821 Remote Similarity NPD6599 Discontinued
0.6818 Remote Similarity NPD1651 Approved
0.6815 Remote Similarity NPD5711 Approved
0.6815 Remote Similarity NPD5710 Approved
0.6806 Remote Similarity NPD9278 Suspended
0.6806 Remote Similarity NPD9276 Approved
0.6806 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6806 Remote Similarity NPD9274 Approved
0.6806 Remote Similarity NPD9275 Approved
0.6797 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6797 Remote Similarity NPD5277 Phase 2
0.6797 Remote Similarity NPD2801 Approved
0.6791 Remote Similarity NPD422 Phase 1
0.6788 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6781 Remote Similarity NPD4628 Phase 3
0.6769 Remote Similarity NPD6671 Approved
0.6763 Remote Similarity NPD7008 Discontinued

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data