Structure

Physi-Chem Properties

Molecular Weight:  496.09
Volume:  445.438
LogP:  0.598
LogD:  0.409
LogS:  -1.593
# Rotatable Bonds:  7
TPSA:  251.74
# H-Bond Aceptor:  14
# H-Bond Donor:  9
# Rings:  3
# Heavy Atoms:  14

MedChem Properties

QED Drug-Likeness Score:  0.189
Synthetic Accessibility Score:  4.149
Fsp3:  0.286
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.705
MDCK Permeability:  1.2392303688102402e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.118
Human Intestinal Absorption (HIA):  0.895
20% Bioavailability (F20%):  1.0
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.054
Plasma Protein Binding (PPB):  88.4457778930664%
Volume Distribution (VD):  0.499
Pgp-substrate:  11.654974937438965%

ADMET: Metabolism

CYP1A2-inhibitor:  0.457
CYP1A2-substrate:  0.011
CYP2C19-inhibitor:  0.017
CYP2C19-substrate:  0.028
CYP2C9-inhibitor:  0.276
CYP2C9-substrate:  0.049
CYP2D6-inhibitor:  0.01
CYP2D6-substrate:  0.097
CYP3A4-inhibitor:  0.034
CYP3A4-substrate:  0.01

ADMET: Excretion

Clearance (CL):  3.735
Half-life (T1/2):  0.943

ADMET: Toxicity

hERG Blockers:  0.093
Human Hepatotoxicity (H-HT):  0.074
Drug-inuced Liver Injury (DILI):  0.941
AMES Toxicity:  0.029
Rat Oral Acute Toxicity:  0.0
Maximum Recommended Daily Dose:  0.003
Skin Sensitization:  0.893
Carcinogencity:  0.01
Eye Corrosion:  0.005
Eye Irritation:  0.874
Respiratory Toxicity:  0.013

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

  Natural Product: NPC43123

Natural Product ID:  NPC43123
Common Name*:   4,5-Di-O-Galloylquinic Acid
IUPAC Name:   (1R,3R,4S,5R)-1,3-dihydroxy-4,5-bis[(3,4,5-trihydroxybenzoyl)oxy]cyclohexane-1-carboxylic acid
Synonyms:  
Standard InCHIKey:  SKUCQDOSGKINGP-COESMTMPSA-N
Standard InCHI:  InChI=1S/C21H20O14/c22-9-1-7(2-10(23)15(9)27)18(29)34-14-6-21(33,20(31)32)5-13(26)17(14)35-19(30)8-3-11(24)16(28)12(25)4-8/h1-4,13-14,17,22-28,33H,5-6H2,(H,31,32)/t13-,14-,17+,21-/m1/s1
SMILES:  O[C@@H]1C[C@@](O)(C[C@H]([C@H]1OC(=O)c1cc(O)c(c(c1)O)O)OC(=O)c1cc(O)c(c(c1)O)O)C(=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL483230
PubChem CID:   13270012
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0000129] Alcohols and polyols
          • [CHEMONTID:0001292] Cyclic alcohols and derivatives
            • [CHEMONTID:0002509] Cyclitols and derivatives
              • [CHEMONTID:0002512] Quinic acids and derivatives

*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
NPO6039 Aglaia laxiflora Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[10785416]
NPO8621 Cylindrospermopsis raciborskii Species Aphanizomenonaceae Bacteria n.a. n.a. n.a. PMID[11223086]
NPO9973 Euphorbia turczaninowii Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[11520228]
NPO8621 Cylindrospermopsis raciborskii Species Aphanizomenonaceae Bacteria n.a. n.a. n.a. PMID[14559084]
NPO7381 Ircinia spinosula Species Irciniidae Eukaryota n.a. Bay of Naples, Italy n.a. PMID[7714539]
NPO5065 Cladonia fallax Species Cladoniaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9734 Vincetoxicum hirundinaria Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5065 Cladonia fallax Species Cladoniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9207 Styrax ferrugineus Species Styracaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9207 Styrax ferrugineus Species Styracaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9734 Vincetoxicum hirundinaria Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8909 Pteris radiata Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7625 Scopolia hladnikiana Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3119 Cephalaria uralensis Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO762 Digitalis isabelliana Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5065 Cladonia fallax Species Cladoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8437 Encyothalia cliftonii Species Sporochnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7381 Ircinia spinosula Species Irciniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2174 Polysiphonia elongata Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO550 Callicarpa maingayi Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7013 Dicoma capensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8621 Cylindrospermopsis raciborskii Species Aphanizomenonaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO5301 Haplophyllum ferganicum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15448 Chrysothamnus parryi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4073 Geranium sylvaticum Species Geraniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9973 Euphorbia turczaninowii Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3924 Penicillium alutaceum Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5541 Crotalaria aegyptiaca Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2723 Artemisia carvifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26170 Haliclona mucosa Species Chalinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8773 Sonchus ortunoi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6039 Aglaia laxiflora Species Meliaceae 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
NPT672 Cell Line TE-671 Homo sapiens ED50 > 10.0 ug ml-1 PMID[468345]
NPT180 Cell Line HCT-8 Homo sapiens ED50 > 10.0 ug ml-1 PMID[468345]
NPT81 Cell Line A549 Homo sapiens ED50 > 10.0 ug ml-1 PMID[468345]
NPT91 Cell Line KB Homo sapiens ED50 > 10.0 ug ml-1 PMID[468345]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 0.53 ug ml-1 PMID[468345]

☑ 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 NPC43123 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
0.9929 High Similarity NPC42464
0.9859 High Similarity NPC306343
0.9714 High Similarity NPC114242
0.9714 High Similarity NPC50221
0.9653 High Similarity NPC252979
0.9574 High Similarity NPC190587
0.9574 High Similarity NPC226738
0.9574 High Similarity NPC22176
0.9574 High Similarity NPC121573
0.9524 High Similarity NPC145425
0.9444 High Similarity NPC142528
0.9433 High Similarity NPC35702
0.9433 High Similarity NPC297517
0.9433 High Similarity NPC477335
0.9433 High Similarity NPC471027
0.9433 High Similarity NPC206095
0.9433 High Similarity NPC13818
0.9433 High Similarity NPC224389
0.9366 High Similarity NPC284948
0.9366 High Similarity NPC472016
0.9366 High Similarity NPC220664
0.9366 High Similarity NPC192831
0.9366 High Similarity NPC37331
0.9366 High Similarity NPC43158
0.9366 High Similarity NPC303090
0.9366 High Similarity NPC258469
0.9366 High Similarity NPC319628
0.9366 High Similarity NPC277315
0.9329 High Similarity NPC134925
0.932 High Similarity NPC93498
0.932 High Similarity NPC163883
0.931 High Similarity NPC120621
0.931 High Similarity NPC248257
0.9291 High Similarity NPC225036
0.9291 High Similarity NPC105525
0.9291 High Similarity NPC75763
0.9291 High Similarity NPC12218
0.9257 High Similarity NPC19380
0.9257 High Similarity NPC146277
0.9247 High Similarity NPC92117
0.9247 High Similarity NPC75945
0.922 High Similarity NPC302857
0.922 High Similarity NPC152942
0.922 High Similarity NPC37250
0.922 High Similarity NPC142703
0.922 High Similarity NPC239943
0.922 High Similarity NPC278068
0.922 High Similarity NPC219428
0.9178 High Similarity NPC192568
0.9178 High Similarity NPC471076
0.9155 High Similarity NPC274891
0.9155 High Similarity NPC476819
0.9155 High Similarity NPC474875
0.9155 High Similarity NPC26241
0.9155 High Similarity NPC476820
0.9155 High Similarity NPC303683
0.9155 High Similarity NPC295492
0.9155 High Similarity NPC205751
0.9133 High Similarity NPC203757
0.9128 High Similarity NPC61152
0.9128 High Similarity NPC205037
0.9128 High Similarity NPC44260
0.9128 High Similarity NPC16024
0.9128 High Similarity NPC3746
0.9122 High Similarity NPC140151
0.9103 High Similarity NPC477333
0.9085 High Similarity NPC24295
0.9085 High Similarity NPC283560
0.9034 High Similarity NPC229036
0.9007 High Similarity NPC18646
0.898 High Similarity NPC322660
0.898 High Similarity NPC229264
0.8973 High Similarity NPC108455
0.8947 High Similarity NPC247629
0.8947 High Similarity NPC239019
0.8944 High Similarity NPC156892
0.8936 High Similarity NPC68517
0.8933 High Similarity NPC75695
0.8912 High Similarity NPC98356
0.8889 High Similarity NPC238419
0.8889 High Similarity NPC172419
0.8873 High Similarity NPC70680
0.8873 High Similarity NPC182217
0.8873 High Similarity NPC233350
0.8865 High Similarity NPC1321
0.8865 High Similarity NPC304929
0.8865 High Similarity NPC156124
0.8831 High Similarity NPC287872
0.8831 High Similarity NPC74319
0.8824 High Similarity NPC88803
0.8824 High Similarity NPC300845
0.8824 High Similarity NPC250436
0.8824 High Similarity NPC104983
0.8824 High Similarity NPC291948
0.88 High Similarity NPC473091
0.8782 High Similarity NPC4013
0.8782 High Similarity NPC90905
0.8774 High Similarity NPC119125
0.8774 High Similarity NPC24164
0.8774 High Similarity NPC166277
0.8774 High Similarity NPC289346
0.8766 High Similarity NPC289322
0.8766 High Similarity NPC472860
0.8766 High Similarity NPC68324
0.8766 High Similarity NPC114179
0.8766 High Similarity NPC160512
0.8766 High Similarity NPC1913
0.8766 High Similarity NPC38779
0.8766 High Similarity NPC156818
0.8758 High Similarity NPC172920
0.8758 High Similarity NPC156624
0.8742 High Similarity NPC477334
0.8725 High Similarity NPC268366
0.8723 High Similarity NPC264145
0.8718 High Similarity NPC472859
0.8718 High Similarity NPC25389
0.8718 High Similarity NPC311803
0.871 High Similarity NPC318826
0.871 High Similarity NPC87317
0.871 High Similarity NPC210501
0.871 High Similarity NPC160780
0.871 High Similarity NPC114791
0.871 High Similarity NPC289811
0.871 High Similarity NPC141331
0.871 High Similarity NPC104222
0.8701 High Similarity NPC318432
0.8701 High Similarity NPC473275
0.8701 High Similarity NPC470896
0.8693 High Similarity NPC281703
0.8693 High Similarity NPC125487
0.8684 High Similarity NPC227485
0.8667 High Similarity NPC472969
0.8662 High Similarity NPC14030
0.8662 High Similarity NPC33298
0.8662 High Similarity NPC291957
0.8662 High Similarity NPC285108
0.8658 High Similarity NPC473867
0.8654 High Similarity NPC203020
0.8654 High Similarity NPC53889
0.8654 High Similarity NPC24627
0.8654 High Similarity NPC476373
0.8654 High Similarity NPC239966
0.8649 High Similarity NPC134975
0.8645 High Similarity NPC4747
0.8645 High Similarity NPC135222
0.8645 High Similarity NPC474010
0.8645 High Similarity NPC104275
0.8616 High Similarity NPC471823
0.8609 High Similarity NPC476394
0.8609 High Similarity NPC98809
0.8608 High Similarity NPC470898
0.8582 High Similarity NPC94810
0.8571 High Similarity NPC475058
0.8562 High Similarity NPC246566
0.8562 High Similarity NPC95498
0.8553 High Similarity NPC142614
0.8553 High Similarity NPC471788
0.8544 High Similarity NPC476371
0.8544 High Similarity NPC476372
0.8543 High Similarity NPC81835
0.8542 High Similarity NPC248150
0.8533 High Similarity NPC474465
0.8531 High Similarity NPC18074
0.8531 High Similarity NPC25581
0.8531 High Similarity NPC61
0.8531 High Similarity NPC5419
0.8523 High Similarity NPC474692
0.8509 High Similarity NPC476017
0.8509 High Similarity NPC198125
0.8509 High Similarity NPC95421
0.8506 High Similarity NPC105827
0.8506 High Similarity NPC474656
0.8506 High Similarity NPC310661
0.8503 High Similarity NPC156709
0.8503 High Similarity NPC179505
0.85 High Similarity NPC175793
0.8497 Intermediate Similarity NPC243891
0.8493 Intermediate Similarity NPC95679
0.8493 Intermediate Similarity NPC125417
0.8493 Intermediate Similarity NPC25305
0.8493 Intermediate Similarity NPC110899
0.8493 Intermediate Similarity NPC112068
0.8487 Intermediate Similarity NPC107636
0.8481 Intermediate Similarity NPC112418
0.8481 Intermediate Similarity NPC266365
0.8472 Intermediate Similarity NPC155209
0.8472 Intermediate Similarity NPC168799
0.8466 Intermediate Similarity NPC476374
0.8462 Intermediate Similarity NPC198388
0.8452 Intermediate Similarity NPC327032
0.8452 Intermediate Similarity NPC116850
0.8452 Intermediate Similarity NPC197188
0.8452 Intermediate Similarity NPC194095
0.8452 Intermediate Similarity NPC291510
0.8452 Intermediate Similarity NPC287504
0.8452 Intermediate Similarity NPC238672
0.8452 Intermediate Similarity NPC191046
0.8452 Intermediate Similarity NPC144801
0.8452 Intermediate Similarity NPC43872
0.8451 Intermediate Similarity NPC226855

  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 NPC43123 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
0.9366 High Similarity NPD6190 Approved
0.8865 High Similarity NPD230 Phase 1
0.8824 High Similarity NPD4868 Clinical (unspecified phase)
0.8519 High Similarity NPD7993 Clinical (unspecified phase)
0.8303 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8214 Intermediate Similarity NPD9269 Phase 2
0.821 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.821 Intermediate Similarity NPD6166 Phase 2
0.821 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8165 Intermediate Similarity NPD3817 Phase 2
0.8113 Intermediate Similarity NPD3882 Suspended
0.811 Intermediate Similarity NPD3818 Discontinued
0.8101 Intermediate Similarity NPD2801 Approved
0.805 Intermediate Similarity NPD5402 Approved
0.8038 Intermediate Similarity NPD1934 Approved
0.8 Intermediate Similarity NPD1512 Approved
0.7987 Intermediate Similarity NPD1465 Phase 2
0.7987 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7964 Intermediate Similarity NPD6797 Phase 2
0.7952 Intermediate Similarity NPD5844 Phase 1
0.795 Intermediate Similarity NPD7075 Discontinued
0.7929 Intermediate Similarity NPD9268 Approved
0.7917 Intermediate Similarity NPD7251 Discontinued
0.7911 Intermediate Similarity NPD4380 Phase 2
0.7871 Intermediate Similarity NPD1511 Approved
0.7866 Intermediate Similarity NPD6232 Discontinued
0.7844 Intermediate Similarity NPD7054 Approved
0.7836 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7834 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7829 Intermediate Similarity NPD7266 Discontinued
0.7812 Intermediate Similarity NPD6801 Discontinued
0.7811 Intermediate Similarity NPD7685 Pre-registration
0.7798 Intermediate Similarity NPD7074 Phase 3
0.7798 Intermediate Similarity NPD7472 Approved
0.7791 Intermediate Similarity NPD6234 Discontinued
0.7785 Intermediate Similarity NPD943 Approved
0.7765 Intermediate Similarity NPD7808 Phase 3
0.7764 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7756 Intermediate Similarity NPD6799 Approved
0.773 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7725 Intermediate Similarity NPD7473 Discontinued
0.7722 Intermediate Similarity NPD5403 Approved
0.7702 Intermediate Similarity NPD37 Approved
0.7677 Intermediate Similarity NPD4628 Phase 3
0.7673 Intermediate Similarity NPD1653 Approved
0.7669 Intermediate Similarity NPD4966 Approved
0.7669 Intermediate Similarity NPD4967 Phase 2
0.7669 Intermediate Similarity NPD4965 Approved
0.7651 Intermediate Similarity NPD3764 Approved
0.7606 Intermediate Similarity NPD9545 Approved
0.7595 Intermediate Similarity NPD5401 Approved
0.7586 Intermediate Similarity NPD8150 Discontinued
0.7584 Intermediate Similarity NPD3027 Phase 3
0.7582 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7574 Intermediate Similarity NPD7228 Approved
0.7532 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7514 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD5353 Approved
0.7484 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7471 Intermediate Similarity NPD3751 Discontinued
0.7469 Intermediate Similarity NPD6599 Discontinued
0.7468 Intermediate Similarity NPD1510 Phase 2
0.745 Intermediate Similarity NPD9494 Approved
0.7439 Intermediate Similarity NPD7819 Suspended
0.7436 Intermediate Similarity NPD1549 Phase 2
0.7436 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7434 Intermediate Similarity NPD1613 Approved
0.7434 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7427 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7425 Intermediate Similarity NPD5494 Approved
0.7423 Intermediate Similarity NPD7411 Suspended
0.7407 Intermediate Similarity NPD3455 Phase 2
0.7396 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7381 Intermediate Similarity NPD7199 Phase 2
0.7372 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7372 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD6233 Phase 2
0.7342 Intermediate Similarity NPD3750 Approved
0.7337 Intermediate Similarity NPD3787 Discontinued
0.7308 Intermediate Similarity NPD2935 Discontinued
0.7308 Intermediate Similarity NPD1551 Phase 2
0.7303 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7303 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD6559 Discontinued
0.7294 Intermediate Similarity NPD5242 Approved
0.7288 Intermediate Similarity NPD8434 Phase 2
0.7278 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD2534 Approved
0.7267 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD2532 Approved
0.7267 Intermediate Similarity NPD2533 Approved
0.7233 Intermediate Similarity NPD8166 Discontinued
0.7219 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7212 Intermediate Similarity NPD6386 Approved
0.7212 Intermediate Similarity NPD6385 Approved
0.7208 Intermediate Similarity NPD1240 Approved
0.7202 Intermediate Similarity NPD3749 Approved
0.7197 Intermediate Similarity NPD2796 Approved
0.7186 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7181 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD6959 Discontinued
0.7171 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7161 Intermediate Similarity NPD447 Suspended
0.716 Intermediate Similarity NPD919 Approved
0.7151 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD7768 Phase 2
0.7143 Intermediate Similarity NPD6534 Approved
0.7143 Intermediate Similarity NPD6535 Approved
0.7134 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7125 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD1607 Approved
0.7112 Intermediate Similarity NPD7435 Discontinued
0.7102 Intermediate Similarity NPD7240 Approved
0.7093 Intermediate Similarity NPD3926 Phase 2
0.7078 Intermediate Similarity NPD6798 Discontinued
0.7076 Intermediate Similarity NPD1247 Approved
0.7055 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7043 Intermediate Similarity NPD6777 Approved
0.7043 Intermediate Similarity NPD6779 Approved
0.7043 Intermediate Similarity NPD6776 Approved
0.7043 Intermediate Similarity NPD6780 Approved
0.7043 Intermediate Similarity NPD6778 Approved
0.7043 Intermediate Similarity NPD6781 Approved
0.7043 Intermediate Similarity NPD6782 Approved
0.7027 Intermediate Similarity NPD7699 Phase 2
0.7027 Intermediate Similarity NPD7700 Phase 2
0.7025 Intermediate Similarity NPD3748 Approved
0.7019 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD7039 Approved
0.7006 Intermediate Similarity NPD7038 Approved
0.6994 Remote Similarity NPD7390 Discontinued
0.6984 Remote Similarity NPD8320 Phase 1
0.6984 Remote Similarity NPD8319 Approved
0.6973 Remote Similarity NPD8090 Clinical (unspecified phase)
0.695 Remote Similarity NPD9265 Clinical (unspecified phase)
0.6927 Remote Similarity NPD8312 Approved
0.6927 Remote Similarity NPD8151 Discontinued
0.6927 Remote Similarity NPD8313 Approved
0.6903 Remote Similarity NPD7095 Approved
0.6891 Remote Similarity NPD7874 Approved
0.6891 Remote Similarity NPD7875 Clinical (unspecified phase)
0.689 Remote Similarity NPD4357 Discontinued
0.6889 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6886 Remote Similarity NPD3226 Approved
0.6886 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6879 Remote Similarity NPD8127 Discontinued
0.6875 Remote Similarity NPD5404 Approved
0.6875 Remote Similarity NPD5406 Approved
0.6875 Remote Similarity NPD5408 Approved
0.6875 Remote Similarity NPD5405 Approved
0.6871 Remote Similarity NPD9493 Approved
0.6871 Remote Similarity NPD3887 Approved
0.6871 Remote Similarity NPD2354 Approved
0.6863 Remote Similarity NPD1203 Approved
0.6854 Remote Similarity NPD5953 Discontinued
0.6842 Remote Similarity NPD7697 Approved
0.6842 Remote Similarity NPD7696 Phase 3
0.6842 Remote Similarity NPD7698 Approved
0.6835 Remote Similarity NPD6355 Discontinued
0.6835 Remote Similarity NPD1933 Approved
0.6824 Remote Similarity NPD8455 Phase 2
0.6815 Remote Similarity NPD4062 Phase 3
0.6813 Remote Similarity NPD7033 Discontinued
0.6809 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6807 Remote Similarity NPD6273 Approved
0.6806 Remote Similarity NPD7871 Phase 2
0.6806 Remote Similarity NPD7870 Phase 2
0.6802 Remote Similarity NPD6971 Discontinued
0.6788 Remote Similarity NPD7701 Phase 2
0.6786 Remote Similarity NPD7458 Discontinued
0.6776 Remote Similarity NPD1608 Approved
0.677 Remote Similarity NPD6099 Approved
0.677 Remote Similarity NPD6100 Approved
0.6766 Remote Similarity NPD920 Approved
0.6748 Remote Similarity NPD1652 Phase 2
0.6747 Remote Similarity NPD642 Clinical (unspecified phase)
0.6743 Remote Similarity NPD5710 Approved
0.6743 Remote Similarity NPD7229 Phase 3
0.6743 Remote Similarity NPD5711 Approved
0.6742 Remote Similarity NPD7286 Phase 2
0.6739 Remote Similarity NPD8360 Approved
0.6739 Remote Similarity NPD8361 Approved
0.6732 Remote Similarity NPD2983 Phase 2
0.6732 Remote Similarity NPD2982 Phase 2
0.6731 Remote Similarity NPD6832 Phase 2
0.673 Remote Similarity NPD1899 Clinical (unspecified phase)
0.673 Remote Similarity NPD4340 Discontinued
0.6727 Remote Similarity NPD7236 Approved
0.6727 Remote Similarity NPD7440 Discontinued
0.6722 Remote Similarity NPD8368 Discontinued
0.6711 Remote Similarity NPD5536 Phase 2
0.6708 Remote Similarity NPD4308 Phase 3
0.6706 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6688 Remote Similarity NPD3225 Approved
0.6685 Remote Similarity NPD7549 Discontinued
0.6684 Remote Similarity NPD7801 Approved
0.6684 Remote Similarity NPD7783 Phase 2
0.6684 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4060 Phase 1

  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