Structure

Physi-Chem Properties

Molecular Weight:  326.06
Volume:  296.881
LogP:  0.118
LogD:  0.529
LogS:  -1.172
# Rotatable Bonds:  4
TPSA:  161.59
# H-Bond Aceptor:  9
# H-Bond Donor:  5
# Rings:  2
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.372
Synthetic Accessibility Score:  3.747
Fsp3:  0.357
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.116
MDCK Permeability:  6.286783900577575e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.061
Human Intestinal Absorption (HIA):  0.337
20% Bioavailability (F20%):  0.967
30% Bioavailability (F30%):  0.911

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.242
Plasma Protein Binding (PPB):  72.89798736572266%
Volume Distribution (VD):  0.4
Pgp-substrate:  17.673999786376953%

ADMET: Metabolism

CYP1A2-inhibitor:  0.022
CYP1A2-substrate:  0.025
CYP2C19-inhibitor:  0.019
CYP2C19-substrate:  0.042
CYP2C9-inhibitor:  0.01
CYP2C9-substrate:  0.343
CYP2D6-inhibitor:  0.007
CYP2D6-substrate:  0.133
CYP3A4-inhibitor:  0.016
CYP3A4-substrate:  0.012

ADMET: Excretion

Clearance (CL):  14.374
Half-life (T1/2):  0.976

ADMET: Toxicity

hERG Blockers:  0.006
Human Hepatotoxicity (H-HT):  0.094
Drug-inuced Liver Injury (DILI):  0.477
AMES Toxicity:  0.02
Rat Oral Acute Toxicity:  0.009
Maximum Recommended Daily Dose:  0.005
Skin Sensitization:  0.104
Carcinogencity:  0.015
Eye Corrosion:  0.005
Eye Irritation:  0.389
Respiratory Toxicity:  0.039

Download Data

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  Natural Product: NPC239943

Natural Product ID:  NPC239943
Common Name*:   3-O-Galloylshikimic Acid
IUPAC Name:   (3R,4R,5R)-3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyl)oxycyclohexene-1-carboxylic acid
Synonyms:   3-O-Galloylshikimic Acid
Standard InCHIKey:  NTNQTAISNHFKRA-CKYFFXLPSA-N
Standard InCHI:  InChI=1S/C14H14O9/c15-7-2-6(3-8(16)11(7)18)14(22)23-10-4-5(13(20)21)1-9(17)12(10)19/h1-3,9-10,12,15-19H,4H2,(H,20,21)/t9-,10-,12-/m1/s1
SMILES:  O[C@@H]1C=C(C[C@H]([C@@H]1O)OC(=O)c1cc(O)c(c(c1)O)O)C(=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL289369
PubChem CID:   460897
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:0001251] Gallic acid and derivatives
              • [CHEMONTID:0003539] Galloyl esters

*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
NPO25715 Senna siamea Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[10757709]
NPO2130 Ehretia dicksonii Species Ehretiaceae Eukaryota n.a. leaf n.a. PMID[10830513]
NPO2130 Ehretia dicksonii Species Ehretiaceae Eukaryota n.a. twig n.a. PMID[10830513]
NPO2130 Ehretia dicksonii Species Ehretiaceae Eukaryota n.a. n.a. n.a. PMID[10830513]
NPO6774 Khaya senegalensis Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[12193039]
NPO10810 Acridocarpus vivy Species Malpighiaceae Eukaryota n.a. Madagascar rain forest n.a. PMID[15217279]
NPO25715 Senna siamea Species Fabaceae Eukaryota n.a. leaf n.a. PMID[17685627]
NPO1103 Dioscorea japonica Species Dioscoreaceae Eukaryota rhizomes n.a. n.a. PMID[21353549]
NPO13504 Lotus japonicus Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[21510636]
NPO25715 Senna siamea Species Fabaceae Eukaryota Stems n.a. n.a. PMID[23078294]
NPO6774 Khaya senegalensis Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[23210623]
NPO25715 Senna siamea Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[23513740]
NPO14089 Hypericum ascyron Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[30379546]
NPO14089 Hypericum ascyron Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[31596079]
NPO1103 Dioscorea japonica Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7690 Nyssa sinensis Species Nyssaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO995 Uncaria donisii Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14089 Hypericum ascyron Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13907 Senecio renardii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25774 Virola multinervia Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7690 Nyssa sinensis Species Nyssaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1103 Dioscorea japonica Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13907 Senecio renardii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO995 Uncaria donisii Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25715 Senna siamea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14089 Hypericum ascyron Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12475 Syneilesis palmata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25774 Virola multinervia Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3199 Balanophora involucrata Species Balanophoraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14089 Hypericum ascyron Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1103 Dioscorea japonica Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7169 Nama hispidum Species Namaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1496 Stevia porphyrea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7752 Beilschmiedia anacardioides Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7690 Nyssa sinensis Species Nyssaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25715 Senna siamea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12414 Penicillium paxilli Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9757 Cladonia macilenta Species Cladoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13701 Melaleuca rhaphiophylla Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12585 Craspidospermum verticillatum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10389 Larix cajanderi Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12069 Isaria felina Species Cordycipitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10865 Sextonia rubra Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1661 Bartramia pomiformis Species Bartramiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO995 Uncaria donisii Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11882 Cedrus libani Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10810 Acridocarpus vivy Species Malpighiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24896 Dinophysis acuminata Species Dinophysiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6179 Aframomum amaniense Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3458 Lupinus verbasciformis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2461 Perilla acuta Species Araneidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13907 Senecio renardii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14615 Streptomyces paulus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO12910 Ixeris stolonifera Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21498 Coccus ilicis Species Coccidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12234 Khaya ivorensis Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8313 Rhipocephalus phoenix Species Udoteaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21977 Psora corallina Species Psoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7292 Excoecaria kawakamii Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6774 Khaya senegalensis Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13504 Lotus japonicus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9669 Dictyopteris acrostichoides Species Dictyotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13076 Cephalaria grossheimii Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14200 Aristolochia zollingeriana Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2130 Ehretia dicksonii Species Ehretiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12475 Syneilesis palmata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14504 Alectoria divergens Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3199 Balanophora involucrata Species Balanophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12061 Justicia paniculata Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12765 Micromonospora inositola Species Micromonosporaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO25774 Virola multinervia Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8848 Colubrina elliptica Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12754 Cerinthe minor Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20026 Senecio callosus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14089 Hypericum ascyron Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7862 Faramea cyanea Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14289 Pieris napi Species Pieridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10012 Triaenophora rupestris Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22543 Cleome chrysantha Species Cleomaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1103 Dioscorea japonica Species Dioscoreaceae 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
NPT459 Individual Protein Human immunodeficiency virus type 1 reverse transcriptase Human immunodeficiency virus 1 Inhibition = 0.0 % PMID[508111]
NPT672 Cell Line TE-671 Homo sapiens ED50 > 10.0 ug ml-1 PMID[508113]
NPT180 Cell Line HCT-8 Homo sapiens ED50 > 10.0 ug ml-1 PMID[508113]
NPT81 Cell Line A549 Homo sapiens ED50 > 10.0 ug ml-1 PMID[508113]
NPT91 Cell Line KB Homo sapiens ED50 > 10.0 ug ml-1 PMID[508113]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 IC50 = 25000.0 nM PMID[508111]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 EC50 = 18000.0 nM PMID[508111]
NPT27 Others Unspecified Therapeutic index = 1.4 n.a. PMID[508111]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 Inhibition = 90.0 % PMID[508111]
NPT316 Protein Family Protein kinase C (PKC) Homo sapiens IC50 > 100000.0 nM PMID[508112]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 > 10.0 ug ml-1 PMID[508113]

☑ 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 NPC239943 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
0.9774 High Similarity NPC105525
0.9774 High Similarity NPC75763
0.9774 High Similarity NPC12218
0.9774 High Similarity NPC225036
0.9489 High Similarity NPC229036
0.9489 High Similarity NPC121573
0.9489 High Similarity NPC50221
0.9489 High Similarity NPC114242
0.9489 High Similarity NPC226738
0.9489 High Similarity NPC190587
0.9489 High Similarity NPC22176
0.947 High Similarity NPC304929
0.947 High Similarity NPC156124
0.947 High Similarity NPC1321
0.942 High Similarity NPC108455
0.9328 High Similarity NPC18646
0.9318 High Similarity NPC264145
0.9259 High Similarity NPC156892
0.922 High Similarity NPC120621
0.922 High Similarity NPC248257
0.922 High Similarity NPC142528
0.922 High Similarity NPC43123
0.9155 High Similarity NPC92117
0.9155 High Similarity NPC75945
0.9155 High Similarity NPC42464
0.9149 High Similarity NPC268366
0.9091 High Similarity NPC306343
0.9051 High Similarity NPC95679
0.9051 High Similarity NPC112068
0.9051 High Similarity NPC125417
0.9051 High Similarity NPC110899
0.9051 High Similarity NPC25305
0.9028 High Similarity NPC140151
0.9023 High Similarity NPC226855
0.8966 High Similarity NPC75695
0.8936 High Similarity NPC134975
0.8912 High Similarity NPC172920
0.8912 High Similarity NPC156624
0.8904 High Similarity NPC3746
0.8904 High Similarity NPC44260
0.8904 High Similarity NPC61152
0.8904 High Similarity NPC205037
0.8904 High Similarity NPC310661
0.8904 High Similarity NPC16024
0.8904 High Similarity NPC105827
0.8897 High Similarity NPC252979
0.8881 High Similarity NPC94810
0.8872 High Similarity NPC158654
0.8849 High Similarity NPC278068
0.8849 High Similarity NPC37250
0.8849 High Similarity NPC152942
0.8849 High Similarity NPC302857
0.8849 High Similarity NPC219428
0.8849 High Similarity NPC142703
0.8832 High Similarity NPC155098
0.8828 High Similarity NPC473091
0.8811 High Similarity NPC473867
0.8792 High Similarity NPC4747
0.8792 High Similarity NPC104275
0.8786 High Similarity NPC303683
0.8786 High Similarity NPC205751
0.8786 High Similarity NPC476820
0.8786 High Similarity NPC474875
0.8786 High Similarity NPC476819
0.8786 High Similarity NPC295492
0.8786 High Similarity NPC274891
0.8786 High Similarity NPC26241
0.8784 High Similarity NPC145425
0.8784 High Similarity NPC203757
0.8779 High Similarity NPC225710
0.8725 High Similarity NPC247629
0.8725 High Similarity NPC239019
0.8716 High Similarity NPC291510
0.8716 High Similarity NPC144801
0.8716 High Similarity NPC116850
0.8716 High Similarity NPC197188
0.8716 High Similarity NPC238672
0.8716 High Similarity NPC43872
0.8714 High Similarity NPC207516
0.8705 High Similarity NPC475111
0.8696 High Similarity NPC248150
0.869 High Similarity NPC472969
0.8681 High Similarity NPC262282
0.8667 High Similarity NPC1913
0.8667 High Similarity NPC49173
0.8667 High Similarity NPC238419
0.8667 High Similarity NPC472860
0.8667 High Similarity NPC172419
0.8662 High Similarity NPC224389
0.8662 High Similarity NPC477335
0.8662 High Similarity NPC13818
0.8662 High Similarity NPC35702
0.8662 High Similarity NPC471027
0.8662 High Similarity NPC297517
0.8662 High Similarity NPC206095
0.8652 High Similarity NPC471819
0.8652 High Similarity NPC4796
0.8633 High Similarity NPC274613
0.8633 High Similarity NPC208760
0.863 High Similarity NPC107636
0.8623 High Similarity NPC159418
0.8623 High Similarity NPC288743
0.8623 High Similarity NPC283823
0.8621 High Similarity NPC229264
0.8609 High Similarity NPC74319
0.8609 High Similarity NPC160780
0.8609 High Similarity NPC287872
0.8609 High Similarity NPC289811
0.8601 High Similarity NPC37331
0.8601 High Similarity NPC284948
0.8601 High Similarity NPC192831
0.8601 High Similarity NPC472016
0.8601 High Similarity NPC303090
0.8601 High Similarity NPC258469
0.8601 High Similarity NPC319628
0.8601 High Similarity NPC220664
0.8601 High Similarity NPC43158
0.8601 High Similarity NPC277315
0.86 High Similarity NPC88803
0.86 High Similarity NPC291948
0.86 High Similarity NPC250436
0.86 High Similarity NPC134925
0.86 High Similarity NPC104983
0.86 High Similarity NPC300845
0.8591 High Similarity NPC281477
0.8581 High Similarity NPC93498
0.8581 High Similarity NPC227485
0.8581 High Similarity NPC163883
0.8562 High Similarity NPC41009
0.8562 High Similarity NPC476463
0.8561 High Similarity NPC474895
0.8561 High Similarity NPC68517
0.8561 High Similarity NPC237330
0.8553 High Similarity NPC239966
0.8553 High Similarity NPC24164
0.8553 High Similarity NPC24627
0.8553 High Similarity NPC119125
0.8553 High Similarity NPC166277
0.8553 High Similarity NPC203020
0.8553 High Similarity NPC289346
0.8552 High Similarity NPC98356
0.8551 High Similarity NPC111888
0.8543 High Similarity NPC114179
0.8543 High Similarity NPC289322
0.8543 High Similarity NPC156818
0.8543 High Similarity NPC160512
0.8543 High Similarity NPC38779
0.8543 High Similarity NPC68324
0.8543 High Similarity NPC135222
0.8543 High Similarity NPC474010
0.854 High Similarity NPC299010
0.8533 High Similarity NPC82592
0.8533 High Similarity NPC16082
0.8523 High Similarity NPC146277
0.8523 High Similarity NPC19380
0.8521 High Similarity NPC247409
0.8514 High Similarity NPC96501
0.8503 High Similarity NPC98809
0.8503 High Similarity NPC476394
0.85 High Similarity NPC70680
0.85 High Similarity NPC233350
0.85 High Similarity NPC182217
0.8497 Intermediate Similarity NPC266365
0.8497 Intermediate Similarity NPC472859
0.8497 Intermediate Similarity NPC311803
0.8497 Intermediate Similarity NPC25389
0.8489 Intermediate Similarity NPC239855
0.8487 Intermediate Similarity NPC114791
0.8487 Intermediate Similarity NPC318826
0.8487 Intermediate Similarity NPC87317
0.8487 Intermediate Similarity NPC141331
0.8487 Intermediate Similarity NPC210501
0.8487 Intermediate Similarity NPC104222
0.8483 Intermediate Similarity NPC469683
0.8478 Intermediate Similarity NPC318799
0.8477 Intermediate Similarity NPC318432
0.8467 Intermediate Similarity NPC281703
0.8467 Intermediate Similarity NPC125487
0.8467 Intermediate Similarity NPC287504
0.8462 Intermediate Similarity NPC326065
0.8462 Intermediate Similarity NPC64664
0.8456 Intermediate Similarity NPC221249
0.8456 Intermediate Similarity NPC228662
0.8442 Intermediate Similarity NPC291957
0.8442 Intermediate Similarity NPC33298
0.8442 Intermediate Similarity NPC285108
0.8442 Intermediate Similarity NPC4013
0.8442 Intermediate Similarity NPC14030
0.8442 Intermediate Similarity NPC90905
0.844 Intermediate Similarity NPC156307
0.8435 Intermediate Similarity NPC471076
0.8435 Intermediate Similarity NPC192568
0.8435 Intermediate Similarity NPC81835
0.8431 Intermediate Similarity NPC53889
0.8431 Intermediate Similarity NPC476373
0.8429 Intermediate Similarity NPC106406
0.8421 Intermediate Similarity NPC84935
0.8421 Intermediate Similarity NPC190020
0.8421 Intermediate Similarity NPC77679
0.8414 Intermediate Similarity NPC473090

  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 NPC239943 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
0.947 High Similarity NPD230 Phase 1
0.8779 High Similarity NPD9269 Phase 2
0.8601 High Similarity NPD6190 Approved
0.86 High Similarity NPD4868 Clinical (unspecified phase)
0.8473 Intermediate Similarity NPD9268 Approved
0.812 Intermediate Similarity NPD9545 Approved
0.8105 Intermediate Similarity NPD1465 Phase 2
0.8075 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8039 Intermediate Similarity NPD1934 Approved
0.8028 Intermediate Similarity NPD943 Approved
0.8 Intermediate Similarity NPD3818 Discontinued
0.7987 Intermediate Similarity NPD1511 Approved
0.7929 Intermediate Similarity NPD9494 Approved
0.7891 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7885 Intermediate Similarity NPD3882 Suspended
0.7881 Intermediate Similarity NPD1512 Approved
0.7871 Intermediate Similarity NPD2801 Approved
0.7871 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7866 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7821 Intermediate Similarity NPD3817 Phase 2
0.7808 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7792 Intermediate Similarity NPD4380 Phase 2
0.7778 Intermediate Similarity NPD1653 Approved
0.7764 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7764 Intermediate Similarity NPD6166 Phase 2
0.7764 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.773 Intermediate Similarity NPD7054 Approved
0.7707 Intermediate Similarity NPD5353 Approved
0.7703 Intermediate Similarity NPD7266 Discontinued
0.7683 Intermediate Similarity NPD7472 Approved
0.7683 Intermediate Similarity NPD7074 Phase 3
0.7667 Intermediate Similarity NPD4628 Phase 3
0.764 Intermediate Similarity NPD6232 Discontinued
0.7636 Intermediate Similarity NPD6797 Phase 2
0.7622 Intermediate Similarity NPD5844 Phase 1
0.761 Intermediate Similarity NPD7075 Discontinued
0.761 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7603 Intermediate Similarity NPD447 Suspended
0.7597 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7595 Intermediate Similarity NPD5402 Approved
0.759 Intermediate Similarity NPD7251 Discontinued
0.759 Intermediate Similarity NPD7685 Pre-registration
0.7569 Intermediate Similarity NPD3027 Phase 3
0.7568 Intermediate Similarity NPD1510 Phase 2
0.7562 Intermediate Similarity NPD6234 Discontinued
0.7534 Intermediate Similarity NPD1613 Approved
0.7534 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7533 Intermediate Similarity NPD1549 Phase 2
0.7517 Intermediate Similarity NPD1551 Phase 2
0.7516 Intermediate Similarity NPD6799 Approved
0.75 Intermediate Similarity NPD7473 Discontinued
0.7468 Intermediate Similarity NPD6801 Discontinued
0.7468 Intermediate Similarity NPD2532 Approved
0.7468 Intermediate Similarity NPD37 Approved
0.7468 Intermediate Similarity NPD2534 Approved
0.7468 Intermediate Similarity NPD2533 Approved
0.7467 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7467 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.744 Intermediate Similarity NPD7808 Phase 3
0.7438 Intermediate Similarity NPD4966 Approved
0.7438 Intermediate Similarity NPD4967 Phase 2
0.7438 Intermediate Similarity NPD4965 Approved
0.7434 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7434 Intermediate Similarity NPD3750 Approved
0.7424 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7421 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7415 Intermediate Similarity NPD1240 Approved
0.7397 Intermediate Similarity NPD3764 Approved
0.7389 Intermediate Similarity NPD3455 Phase 2
0.7372 Intermediate Similarity NPD5403 Approved
0.7355 Intermediate Similarity NPD5401 Approved
0.7349 Intermediate Similarity NPD7228 Approved
0.7319 Intermediate Similarity NPD9493 Approved
0.7315 Intermediate Similarity NPD1607 Approved
0.7312 Intermediate Similarity NPD7819 Suspended
0.731 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.729 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7279 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD5242 Approved
0.726 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7239 Intermediate Similarity NPD919 Approved
0.7233 Intermediate Similarity NPD6599 Discontinued
0.7209 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7208 Intermediate Similarity NPD8166 Discontinued
0.7195 Intermediate Similarity NPD5494 Approved
0.7188 Intermediate Similarity NPD6385 Approved
0.7188 Intermediate Similarity NPD6386 Approved
0.7188 Intermediate Similarity NPD7411 Suspended
0.7176 Intermediate Similarity NPD6559 Discontinued
0.7171 Intermediate Similarity NPD2935 Discontinued
0.7153 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD7199 Phase 2
0.7134 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD3748 Approved
0.7105 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7069 Intermediate Similarity NPD8150 Discontinued
0.7059 Intermediate Similarity NPD2796 Approved
0.7059 Intermediate Similarity NPD9570 Approved
0.7055 Intermediate Similarity NPD1203 Approved
0.7048 Intermediate Similarity NPD1247 Approved
0.7044 Intermediate Similarity NPD920 Approved
0.7041 Intermediate Similarity NPD3751 Discontinued
0.7032 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7032 Intermediate Similarity NPD2800 Approved
0.7025 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7014 Intermediate Similarity NPD422 Phase 1
0.697 Remote Similarity NPD3749 Approved
0.6966 Remote Similarity NPD1608 Approved
0.6966 Remote Similarity NPD9717 Approved
0.6964 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6951 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6946 Remote Similarity NPD6959 Discontinued
0.6923 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6923 Remote Similarity NPD1243 Approved
0.6923 Remote Similarity NPD1652 Phase 2
0.6918 Remote Similarity NPD7410 Clinical (unspecified phase)
0.691 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6909 Remote Similarity NPD7768 Phase 2
0.6905 Remote Similarity NPD5710 Approved
0.6905 Remote Similarity NPD5711 Approved
0.6899 Remote Similarity NPD643 Clinical (unspecified phase)
0.6879 Remote Similarity NPD7240 Approved
0.6875 Remote Similarity NPD8434 Phase 2
0.6864 Remote Similarity NPD3926 Phase 2
0.6863 Remote Similarity NPD6651 Approved
0.6861 Remote Similarity NPD9266 Approved
0.6861 Remote Similarity NPD74 Approved
0.6855 Remote Similarity NPD4357 Discontinued
0.6842 Remote Similarity NPD826 Approved
0.6842 Remote Similarity NPD825 Approved
0.6835 Remote Similarity NPD228 Approved
0.6821 Remote Similarity NPD5953 Discontinued
0.6821 Remote Similarity NPD411 Approved
0.6813 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6813 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6797 Remote Similarity NPD555 Phase 2
0.6797 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6797 Remote Similarity NPD1933 Approved
0.6788 Remote Similarity NPD9267 Approved
0.6788 Remote Similarity NPD9264 Approved
0.6788 Remote Similarity NPD9263 Approved
0.6782 Remote Similarity NPD7038 Approved
0.6782 Remote Similarity NPD7039 Approved
0.6776 Remote Similarity NPD6233 Phase 2
0.6759 Remote Similarity NPD17 Approved
0.675 Remote Similarity NPD7390 Discontinued
0.6748 Remote Similarity NPD3226 Approved
0.6748 Remote Similarity NPD824 Approved
0.6746 Remote Similarity NPD8127 Discontinued
0.674 Remote Similarity NPD3473 Clinical (unspecified phase)
0.6738 Remote Similarity NPD1241 Discontinued
0.6735 Remote Similarity NPD1481 Phase 2
0.672 Remote Similarity NPD8151 Discontinued
0.6716 Remote Similarity NPD1242 Phase 1
0.6713 Remote Similarity NPD405 Clinical (unspecified phase)
0.6711 Remote Similarity NPD1164 Approved
0.6711 Remote Similarity NPD1296 Phase 2
0.6706 Remote Similarity NPD3787 Discontinued
0.6705 Remote Similarity NPD8313 Approved
0.6705 Remote Similarity NPD7286 Phase 2
0.6705 Remote Similarity NPD8312 Approved
0.6689 Remote Similarity NPD6832 Phase 2
0.6689 Remote Similarity NPD2982 Phase 2
0.6689 Remote Similarity NPD2983 Phase 2
0.6687 Remote Similarity NPD1006 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6667 Remote Similarity NPD520 Approved
0.6667 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6667 Remote Similarity NPD259 Phase 1
0.6667 Remote Similarity NPD258 Approved
0.6667 Remote Similarity NPD5536 Phase 2
0.6667 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4110 Phase 3
0.6667 Remote Similarity NPD1019 Discontinued
0.6667 Remote Similarity NPD1091 Approved
0.6667 Remote Similarity NPD1358 Approved
0.6667 Remote Similarity NPD257 Approved
0.6667 Remote Similarity NPD1535 Discovery
0.6647 Remote Similarity NPD4288 Approved
0.6646 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6645 Remote Similarity NPD6653 Approved
0.6644 Remote Similarity NPD1778 Approved
0.6644 Remote Similarity NPD3225 Approved
0.6642 Remote Similarity NPD1238 Approved
0.6625 Remote Similarity NPD2354 Approved
0.6624 Remote Similarity NPD6100 Approved
0.6624 Remote Similarity NPD5406 Approved
0.6624 Remote Similarity NPD6099 Approved
0.6624 Remote Similarity NPD5408 Approved
0.6624 Remote Similarity NPD5404 Approved
0.6624 Remote Similarity NPD5405 Approved
0.6623 Remote Similarity NPD9569 Approved
0.6623 Remote Similarity NPD3018 Phase 2
0.6622 Remote Similarity NPD2981 Phase 2
0.6621 Remote Similarity NPD1548 Phase 1
0.6605 Remote Similarity NPD3146 Approved
0.6605 Remote Similarity NPD3688 Clinical (unspecified phase)

  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