Structure

Physi-Chem Properties

Molecular Weight:  474.08
Volume:  445.8
LogP:  1.672
LogD:  3.427
LogS:  -3.503
# Rotatable Bonds:  11
TPSA:  208.12
# H-Bond Aceptor:  12
# H-Bond Donor:  6
# Rings:  2
# Heavy Atoms:  12

MedChem Properties

QED Drug-Likeness Score:  0.172
Synthetic Accessibility Score:  3.514
Fsp3:  0.091
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.45
MDCK Permeability:  1.0674276381905656e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.009
Human Intestinal Absorption (HIA):  0.59
20% Bioavailability (F20%):  0.527
30% Bioavailability (F30%):  0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.074
Plasma Protein Binding (PPB):  98.82763671875%
Volume Distribution (VD):  0.296
Pgp-substrate:  1.6545664072036743%

ADMET: Metabolism

CYP1A2-inhibitor:  0.057
CYP1A2-substrate:  0.01
CYP2C19-inhibitor:  0.07
CYP2C19-substrate:  0.029
CYP2C9-inhibitor:  0.402
CYP2C9-substrate:  0.925
CYP2D6-inhibitor:  0.01
CYP2D6-substrate:  0.122
CYP3A4-inhibitor:  0.066
CYP3A4-substrate:  0.007

ADMET: Excretion

Clearance (CL):  4.971
Half-life (T1/2):  0.974

ADMET: Toxicity

hERG Blockers:  0.01
Human Hepatotoxicity (H-HT):  0.176
Drug-inuced Liver Injury (DILI):  0.168
AMES Toxicity:  0.004
Rat Oral Acute Toxicity:  0.099
Maximum Recommended Daily Dose:  0.011
Skin Sensitization:  0.906
Carcinogencity:  0.127
Eye Corrosion:  0.003
Eye Irritation:  0.351
Respiratory Toxicity:  0.019

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

  Natural Product: NPC32626

Natural Product ID:  NPC32626
Common Name*:   (+)-Chicoricacid
IUPAC Name:   (2R,3S)-2,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]butanedioic acid
Synonyms:  
Standard InCHIKey:  YDDGKXBLOXEEMN-XAKUNQSDSA-N
Standard InCHI:  InChI=1S/C22H18O12/c23-13-5-1-11(9-15(13)25)3-7-17(27)33-19(21(29)30)20(22(31)32)34-18(28)8-4-12-2-6-14(24)16(26)10-12/h1-10,19-20,23-26H,(H,29,30)(H,31,32)/b7-3+,8-4+/t19-,20+
SMILES:  O=C(O[C@H]([C@@H](C(=O)O)OC(=O)/C=C/c1ccc(c(c1)O)O)C(=O)O)/C=C/c1ccc(c(c1)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL397730
PubChem CID:   6450976
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0000265] Carboxylic acids and derivatives
        • [CHEMONTID:0002966] Tetracarboxylic 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
NPO26361 Annona cherimolia Species Annonaceae Eukaryota Seeds n.a. n.a. PMID[11325235]
NPO26361 Annona cherimolia Species Annonaceae Eukaryota Seeds n.a. n.a. PMID[14575439]
NPO31082 Pulsatilla koreana Species Ranunculaceae Eukaryota n.a. root n.a. PMID[15473660]
NPO31082 Pulsatilla koreana Species Ranunculaceae Eukaryota Roots n.a. n.a. PMID[15730260]
NPO9865 Cichorium intybus Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[18341288]
NPO9865 Cichorium intybus Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[18460139]
NPO31082 Pulsatilla koreana Species Ranunculaceae Eukaryota Roots n.a. n.a. PMID[24360605]
NPO28626 Isodon rubescens Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[25590529]
NPO26622 Taraxacum officinale Species Asteraceae Eukaryota n.a. n.a. Database[FooDB]
NPO9865 Cichorium intybus Species Asteraceae Eukaryota Flower n.a. n.a. Database[FooDB]
NPO9865 Cichorium intybus Species Asteraceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO9865 Cichorium intybus Species Asteraceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO26622 Taraxacum officinale Species Asteraceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO26622 Taraxacum officinale Species Asteraceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO26622 Taraxacum officinale Species Asteraceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO26622 Taraxacum officinale Species Asteraceae Eukaryota n.a. n.a. Database[FooDB]
NPO9865 Cichorium intybus Species Asteraceae Eukaryota Roots n.a. Database[FooDB]
NPO9865 Cichorium intybus Species Asteraceae Eukaryota n.a. n.a. Database[FooDB]
NPO26785 Taraxacum mongolicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26622 Taraxacum officinale Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26361 Annona cherimolia Species Annonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9865 Cichorium intybus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9865 Cichorium intybus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[MetaboLights]
NPO26622 Taraxacum officinale Species Asteraceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO9865 Cichorium intybus Species Asteraceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO26785 Taraxacum mongolicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26622 Taraxacum officinale Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26361 Annona cherimolia Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28626 Isodon rubescens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9865 Cichorium intybus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26622 Taraxacum officinale Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26785 Taraxacum mongolicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9865 Cichorium intybus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28626 Isodon rubescens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9865 Cichorium intybus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO13668 Taraxacum platycarpum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO26785 Taraxacum mongolicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO23327 Taraxacum coreanum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16931 Cichorium glandulosum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO26622 Taraxacum officinale Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1596 Taraxacum borealisinense Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO26361 Annona cherimolia Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13123 Balanophora harlandii Species Balanophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO513 Agathosma scaberula Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1584 Tolypothrix tjipanasensis Species Tolypothrichaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO2161 Strychnos ledermannii Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO245 Euphorbia biglandulosa Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17549 Polemonium caeruleum Species Polemoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13668 Taraxacum platycarpum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9865 Cichorium intybus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16931 Cichorium glandulosum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4892 Viburnum davidii Species Adoxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26622 Taraxacum officinale Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23327 Taraxacum coreanum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28626 Isodon rubescens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29531 Lupinus cosentinii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26785 Taraxacum mongolicum Species Asteraceae 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
NPT12 Individual Protein Human immunodeficiency virus type 1 integrase Human immunodeficiency virus 1 IC50 = 15700.0 nM PMID[568790]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 CC50 = 42200.0 nM PMID[568790]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 EC50 = 7500.0 nM PMID[568790]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 TI = 5.6 n.a. PMID[568790]
NPT2 Others Unspecified IC50 = 60000.0 nM PMID[568791]

☑ 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 NPC32626 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 NPC237506
1.0 High Similarity NPC217052
1.0 High Similarity NPC329344
0.9593 High Similarity NPC132921
0.9516 High Similarity NPC168653
0.9516 High Similarity NPC251407
0.9462 High Similarity NPC279676
0.9462 High Similarity NPC67349
0.936 High Similarity NPC475695
0.9318 High Similarity NPC179505
0.9318 High Similarity NPC156709
0.9055 High Similarity NPC118584
0.9 High Similarity NPC108553
0.8978 High Similarity NPC53884
0.8978 High Similarity NPC258671
0.8976 High Similarity NPC67951
0.8968 High Similarity NPC285345
0.8931 High Similarity NPC18074
0.8931 High Similarity NPC61
0.8931 High Similarity NPC25581
0.8931 High Similarity NPC5419
0.8906 High Similarity NPC147192
0.8905 High Similarity NPC304956
0.8864 High Similarity NPC168799
0.8864 High Similarity NPC155209
0.8855 High Similarity NPC198388
0.8849 High Similarity NPC283081
0.8849 High Similarity NPC229264
0.8849 High Similarity NPC221383
0.8849 High Similarity NPC143892
0.8849 High Similarity NPC299090
0.8797 High Similarity NPC474895
0.8797 High Similarity NPC106406
0.873 High Similarity NPC470849
0.873 High Similarity NPC470848
0.872 High Similarity NPC263386
0.872 High Similarity NPC141791
0.8714 High Similarity NPC322660
0.8696 High Similarity NPC303090
0.8696 High Similarity NPC319628
0.8696 High Similarity NPC37331
0.8696 High Similarity NPC220664
0.8696 High Similarity NPC284948
0.8682 High Similarity NPC197832
0.8676 High Similarity NPC278068
0.8676 High Similarity NPC152942
0.8676 High Similarity NPC219428
0.8676 High Similarity NPC302857
0.8676 High Similarity NPC142703
0.8676 High Similarity NPC37250
0.8672 High Similarity NPC306100
0.8667 High Similarity NPC470572
0.8652 High Similarity NPC471076
0.8652 High Similarity NPC192568
0.864 High Similarity NPC275519
0.8629 High Similarity NPC281277
0.8626 High Similarity NPC110313
0.8623 High Similarity NPC471027
0.8623 High Similarity NPC477335
0.8623 High Similarity NPC13818
0.8623 High Similarity NPC206095
0.8623 High Similarity NPC297517
0.8623 High Similarity NPC35702
0.8623 High Similarity NPC224389
0.8613 High Similarity NPC274891
0.8613 High Similarity NPC476819
0.8613 High Similarity NPC26241
0.8613 High Similarity NPC303683
0.8613 High Similarity NPC474875
0.8613 High Similarity NPC476820
0.8613 High Similarity NPC205751
0.8613 High Similarity NPC295492
0.8561 High Similarity NPC43158
0.8561 High Similarity NPC277315
0.8561 High Similarity NPC472016
0.8561 High Similarity NPC192831
0.8561 High Similarity NPC258469
0.8548 High Similarity NPC233669
0.8542 High Similarity NPC246566
0.8542 High Similarity NPC95498
0.854 High Similarity NPC220942
0.8531 High Similarity NPC32197
0.8516 High Similarity NPC147654
0.85 High Similarity NPC474692
0.8492 Intermediate Similarity NPC309434
0.8478 Intermediate Similarity NPC288452
0.8478 Intermediate Similarity NPC289690
0.8478 Intermediate Similarity NPC471875
0.8468 Intermediate Similarity NPC217472
0.8468 Intermediate Similarity NPC261453
0.8468 Intermediate Similarity NPC328593
0.8468 Intermediate Similarity NPC33749
0.8462 Intermediate Similarity NPC246704
0.844 Intermediate Similarity NPC477333
0.8433 Intermediate Similarity NPC318799
0.8425 Intermediate Similarity NPC241634
0.8425 Intermediate Similarity NPC70084
0.8421 Intermediate Similarity NPC229784
0.8421 Intermediate Similarity NPC477300
0.8421 Intermediate Similarity NPC477293
0.8421 Intermediate Similarity NPC477294
0.8417 Intermediate Similarity NPC38473
0.8413 Intermediate Similarity NPC65791
0.8409 Intermediate Similarity NPC476873
0.8406 Intermediate Similarity NPC283560
0.8406 Intermediate Similarity NPC24295
0.8403 Intermediate Similarity NPC221091
0.8403 Intermediate Similarity NPC259576
0.84 Intermediate Similarity NPC474967
0.8397 Intermediate Similarity NPC289459
0.8387 Intermediate Similarity NPC95381
0.8385 Intermediate Similarity NPC224208
0.8385 Intermediate Similarity NPC474275
0.8382 Intermediate Similarity NPC287597
0.8382 Intermediate Similarity NPC135127
0.8382 Intermediate Similarity NPC886
0.8382 Intermediate Similarity NPC34293
0.8382 Intermediate Similarity NPC68517
0.8369 Intermediate Similarity NPC183824
0.8346 Intermediate Similarity NPC203124
0.8346 Intermediate Similarity NPC86198
0.8346 Intermediate Similarity NPC232880
0.8345 Intermediate Similarity NPC300329
0.8333 Intermediate Similarity NPC120225
0.8333 Intermediate Similarity NPC213552
0.8321 Intermediate Similarity NPC476870
0.8321 Intermediate Similarity NPC70680
0.8321 Intermediate Similarity NPC311742
0.8321 Intermediate Similarity NPC182217
0.8321 Intermediate Similarity NPC233350
0.8321 Intermediate Similarity NPC288945
0.8309 Intermediate Similarity NPC471749
0.8299 Intermediate Similarity NPC477299
0.8298 Intermediate Similarity NPC285550
0.8296 Intermediate Similarity NPC219677
0.8286 Intermediate Similarity NPC477279
0.8284 Intermediate Similarity NPC83062
0.8281 Intermediate Similarity NPC470215
0.8281 Intermediate Similarity NPC470214
0.8281 Intermediate Similarity NPC109371
0.8273 Intermediate Similarity NPC284409
0.8268 Intermediate Similarity NPC145023
0.8268 Intermediate Similarity NPC200988
0.8268 Intermediate Similarity NPC610
0.8268 Intermediate Similarity NPC175799
0.8252 Intermediate Similarity NPC98356
0.8244 Intermediate Similarity NPC212541
0.8239 Intermediate Similarity NPC160378
0.8235 Intermediate Similarity NPC473924
0.8235 Intermediate Similarity NPC473285
0.8227 Intermediate Similarity NPC477277
0.8227 Intermediate Similarity NPC477278
0.8226 Intermediate Similarity NPC226250
0.8219 Intermediate Similarity NPC477334
0.8207 Intermediate Similarity NPC42464
0.8201 Intermediate Similarity NPC78363
0.8201 Intermediate Similarity NPC308976
0.8201 Intermediate Similarity NPC260425
0.8188 Intermediate Similarity NPC477301
0.8175 Intermediate Similarity NPC254398
0.8175 Intermediate Similarity NPC475468
0.8168 Intermediate Similarity NPC86900
0.816 Intermediate Similarity NPC51698
0.816 Intermediate Similarity NPC131530
0.8156 Intermediate Similarity NPC9218
0.8154 Intermediate Similarity NPC471877
0.8154 Intermediate Similarity NPC204466
0.8151 Intermediate Similarity NPC306343
0.8146 Intermediate Similarity NPC44507
0.8143 Intermediate Similarity NPC321184
0.8143 Intermediate Similarity NPC171134
0.8143 Intermediate Similarity NPC197316
0.8143 Intermediate Similarity NPC68092
0.8143 Intermediate Similarity NPC64141
0.8143 Intermediate Similarity NPC321638
0.8143 Intermediate Similarity NPC89105
0.8143 Intermediate Similarity NPC328273
0.8143 Intermediate Similarity NPC472350
0.8143 Intermediate Similarity NPC205195
0.8143 Intermediate Similarity NPC476383
0.8143 Intermediate Similarity NPC81515
0.8138 Intermediate Similarity NPC473138
0.8138 Intermediate Similarity NPC43123
0.8138 Intermediate Similarity NPC1580
0.8138 Intermediate Similarity NPC28776
0.8133 Intermediate Similarity NPC223335
0.8133 Intermediate Similarity NPC40920
0.8129 Intermediate Similarity NPC90431
0.8129 Intermediate Similarity NPC471664
0.8129 Intermediate Similarity NPC471665
0.8116 Intermediate Similarity NPC471883
0.8112 Intermediate Similarity NPC50221
0.8112 Intermediate Similarity NPC226738
0.8112 Intermediate Similarity NPC190587
0.8112 Intermediate Similarity NPC121573
0.8112 Intermediate Similarity NPC114242
0.8112 Intermediate Similarity NPC22176
0.8112 Intermediate Similarity NPC470130
0.8108 Intermediate Similarity NPC475216
0.8108 Intermediate Similarity NPC475162

  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 NPC32626 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
0.8696 High Similarity NPD6190 Approved
0.8143 Intermediate Similarity NPD7266 Discontinued
0.8106 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.766 Intermediate Similarity NPD230 Phase 1
0.7576 Intermediate Similarity NPD5536 Phase 2
0.7518 Intermediate Similarity NPD6233 Phase 2
0.7484 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7484 Intermediate Similarity NPD3882 Suspended
0.7483 Intermediate Similarity NPD8166 Discontinued
0.7465 Intermediate Similarity NPD4060 Phase 1
0.7434 Intermediate Similarity NPD3455 Phase 2
0.7419 Intermediate Similarity NPD3817 Phase 2
0.7378 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7376 Intermediate Similarity NPD7095 Approved
0.7376 Intermediate Similarity NPD3027 Phase 3
0.7364 Intermediate Similarity NPD3022 Approved
0.7364 Intermediate Similarity NPD3021 Approved
0.7357 Intermediate Similarity NPD9494 Approved
0.7329 Intermediate Similarity NPD2935 Discontinued
0.7324 Intermediate Similarity NPD6798 Discontinued
0.7308 Intermediate Similarity NPD5402 Approved
0.7292 Intermediate Similarity NPD447 Suspended
0.7292 Intermediate Similarity NPD6355 Discontinued
0.7273 Intermediate Similarity NPD4062 Phase 3
0.7255 Intermediate Similarity NPD1653 Approved
0.7246 Intermediate Similarity NPD9269 Phase 2
0.7222 Intermediate Similarity NPD943 Approved
0.7215 Intermediate Similarity NPD7075 Discontinued
0.7209 Intermediate Similarity NPD1358 Approved
0.7179 Intermediate Similarity NPD1934 Approved
0.7178 Intermediate Similarity NPD3818 Discontinued
0.716 Intermediate Similarity NPD6166 Phase 2
0.716 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD6797 Phase 2
0.7134 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD2801 Approved
0.7124 Intermediate Similarity NPD1512 Approved
0.7121 Intermediate Similarity NPD228 Approved
0.7108 Intermediate Similarity NPD7251 Discontinued
0.7105 Intermediate Similarity NPD6799 Approved
0.7103 Intermediate Similarity NPD1613 Approved
0.7103 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7078 Intermediate Similarity NPD5403 Approved
0.7063 Intermediate Similarity NPD6234 Discontinued
0.7055 Intermediate Similarity NPD4340 Discontinued
0.7041 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD6232 Discontinued
0.7027 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.702 Intermediate Similarity NPD4628 Phase 3
0.7007 Intermediate Similarity NPD9545 Approved
0.7006 Intermediate Similarity NPD7685 Pre-registration
0.7 Intermediate Similarity NPD3134 Approved
0.6993 Remote Similarity NPD1511 Approved
0.6993 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6986 Remote Similarity NPD825 Approved
0.6986 Remote Similarity NPD826 Approved
0.6985 Remote Similarity NPD9493 Approved
0.698 Remote Similarity NPD6032 Approved
0.698 Remote Similarity NPD9570 Approved
0.6972 Remote Similarity NPD1203 Approved
0.6966 Remote Similarity NPD3764 Approved
0.6964 Remote Similarity NPD7808 Phase 3
0.6962 Remote Similarity NPD6801 Discontinued
0.6959 Remote Similarity NPD7097 Phase 1
0.6957 Remote Similarity NPD9268 Approved
0.6948 Remote Similarity NPD5401 Approved
0.6944 Remote Similarity NPD1529 Clinical (unspecified phase)
0.6943 Remote Similarity NPD4380 Phase 2
0.6928 Remote Similarity NPD7054 Approved
0.6912 Remote Similarity NPD4198 Discontinued
0.6909 Remote Similarity NPD7473 Discontinued
0.6908 Remote Similarity NPD4110 Phase 3
0.6908 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6892 Remote Similarity NPD6653 Approved
0.6889 Remote Similarity NPD5283 Phase 1
0.6887 Remote Similarity NPD5958 Discontinued
0.6887 Remote Similarity NPD4534 Discontinued
0.6886 Remote Similarity NPD7472 Approved
0.6886 Remote Similarity NPD7074 Phase 3
0.6883 Remote Similarity NPD4357 Discontinued
0.6875 Remote Similarity NPD5736 Approved
0.6875 Remote Similarity NPD1530 Clinical (unspecified phase)
0.6867 Remote Similarity NPD3751 Discontinued
0.6866 Remote Similarity NPD969 Suspended
0.6857 Remote Similarity NPD3496 Discontinued
0.6855 Remote Similarity NPD37 Approved
0.6842 Remote Similarity NPD2067 Discontinued
0.6839 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6838 Remote Similarity NPD2629 Approved
0.6835 Remote Similarity NPD1357 Approved
0.6835 Remote Similarity NPD5585 Approved
0.6835 Remote Similarity NPD6599 Discontinued
0.6832 Remote Similarity NPD4965 Approved
0.6832 Remote Similarity NPD4967 Phase 2
0.6832 Remote Similarity NPD4966 Approved
0.6828 Remote Similarity NPD6832 Phase 2
0.6824 Remote Similarity NPD1933 Approved
0.6824 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6824 Remote Similarity NPD555 Phase 2
0.6821 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6813 Remote Similarity NPD1465 Phase 2
0.6809 Remote Similarity NPD1535 Discovery
0.6806 Remote Similarity NPD5647 Approved
0.68 Remote Similarity NPD2799 Discontinued
0.679 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6766 Remote Similarity NPD7228 Approved
0.6763 Remote Similarity NPD1894 Discontinued
0.6761 Remote Similarity NPD1481 Phase 2
0.6757 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6755 Remote Similarity NPD2438 Suspended
0.6755 Remote Similarity NPD1501 Clinical (unspecified phase)
0.6755 Remote Similarity NPD1551 Phase 2
0.6746 Remote Similarity NPD2934 Approved
0.6746 Remote Similarity NPD2933 Approved
0.6744 Remote Similarity NPD1242 Phase 1
0.6743 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6738 Remote Similarity NPD3847 Discontinued
0.6736 Remote Similarity NPD1164 Approved
0.6735 Remote Similarity NPD2313 Discontinued
0.6713 Remote Similarity NPD2982 Phase 2
0.6713 Remote Similarity NPD2983 Phase 2
0.6711 Remote Similarity NPD5763 Approved
0.6711 Remote Similarity NPD5762 Approved
0.6711 Remote Similarity NPD2029 Clinical (unspecified phase)
0.6705 Remote Similarity NPD8150 Discontinued
0.6693 Remote Similarity NPD2860 Approved
0.6693 Remote Similarity NPD2859 Approved
0.669 Remote Similarity NPD257 Approved
0.669 Remote Similarity NPD258 Approved
0.6689 Remote Similarity NPD259 Phase 1
0.6689 Remote Similarity NPD6663 Approved
0.6687 Remote Similarity NPD6386 Approved
0.6687 Remote Similarity NPD6385 Approved
0.6687 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4626 Approved
0.6667 Remote Similarity NPD3225 Approved
0.6667 Remote Similarity NPD3020 Approved
0.6667 Remote Similarity NPD8127 Discontinued
0.6667 Remote Similarity NPD2424 Discontinued
0.6646 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6645 Remote Similarity NPD5404 Approved
0.6645 Remote Similarity NPD5405 Approved
0.6645 Remote Similarity NPD2354 Approved
0.6645 Remote Similarity NPD5406 Approved
0.6645 Remote Similarity NPD5408 Approved
0.6645 Remote Similarity NPD3887 Approved
0.6644 Remote Similarity NPD3620 Phase 2
0.6644 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6644 Remote Similarity NPD3059 Approved
0.6644 Remote Similarity NPD3062 Approved
0.6644 Remote Similarity NPD9569 Approved
0.6644 Remote Similarity NPD3061 Approved
0.6643 Remote Similarity NPD2981 Phase 2
0.6643 Remote Similarity NPD9717 Approved
0.6642 Remote Similarity NPD9266 Approved
0.6642 Remote Similarity NPD74 Approved
0.6627 Remote Similarity NPD3787 Discontinued
0.6627 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6627 Remote Similarity NPD5844 Phase 1
0.6624 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6624 Remote Similarity NPD3536 Discontinued
0.6622 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6621 Remote Similarity NPD1470 Approved
0.6621 Remote Similarity NPD2797 Approved
0.6619 Remote Similarity NPD405 Clinical (unspecified phase)
0.6617 Remote Similarity NPD968 Approved
0.6609 Remote Similarity NPD8434 Phase 2
0.6608 Remote Similarity NPD6559 Discontinued
0.6605 Remote Similarity NPD7819 Suspended
0.6601 Remote Similarity NPD2346 Discontinued
0.6597 Remote Similarity NPD4359 Approved
0.6596 Remote Similarity NPD5691 Approved
0.6594 Remote Similarity NPD690 Clinical (unspecified phase)
0.6581 Remote Similarity NPD3400 Discontinued
0.6581 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6579 Remote Similarity NPD1510 Phase 2
0.6579 Remote Similarity NPD7033 Discontinued
0.657 Remote Similarity NPD3936 Clinical (unspecified phase)
0.6569 Remote Similarity NPD7843 Approved
0.6569 Remote Similarity NPD5535 Approved
0.6567 Remote Similarity NPD9265 Clinical (unspecified phase)
0.6567 Remote Similarity NPD9264 Approved
0.6567 Remote Similarity NPD9263 Approved
0.6567 Remote Similarity NPD9267 Approved
0.6562 Remote Similarity NPD3226 Approved
0.6558 Remote Similarity NPD1549 Phase 2
0.6558 Remote Similarity NPD970 Clinical (unspecified phase)
0.6556 Remote Similarity NPD5314 Approved
0.6552 Remote Similarity NPD1283 Approved
0.6549 Remote Similarity NPD1778 Approved
0.6549 Remote Similarity NPD9381 Approved
0.6549 Remote Similarity NPD9384 Approved
0.6547 Remote Similarity NPD7157 Approved
0.6545 Remote Similarity NPD919 Approved
0.6544 Remote Similarity NPD9280 Clinical (unspecified phase)
0.6533 Remote Similarity NPD2979 Phase 3
0.6532 Remote Similarity NPD8313 Approved

  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