Structure

Physi-Chem Properties

Molecular Weight:  956.5
Volume:  929.417
LogP:  0.811
LogD:  1.601
LogS:  -2.779
# Rotatable Bonds:  11
TPSA:  312.05
# H-Bond Aceptor:  19
# H-Bond Donor:  11
# Rings:  8
# Heavy Atoms:  19

MedChem Properties

QED Drug-Likeness Score:  0.102
Synthetic Accessibility Score:  6.416
Fsp3:  0.917
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.216
MDCK Permeability:  0.00013517528714146465
Pgp-inhibitor:  0.018
Pgp-substrate:  0.231
Human Intestinal Absorption (HIA):  0.974
20% Bioavailability (F20%):  0.041
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.006
Plasma Protein Binding (PPB):  77.55896759033203%
Volume Distribution (VD):  0.436
Pgp-substrate:  11.37540340423584%

ADMET: Metabolism

CYP1A2-inhibitor:  0.002
CYP1A2-substrate:  0.519
CYP2C19-inhibitor:  0.001
CYP2C19-substrate:  0.306
CYP2C9-inhibitor:  0.001
CYP2C9-substrate:  0.024
CYP2D6-inhibitor:  0.004
CYP2D6-substrate:  0.064
CYP3A4-inhibitor:  0.034
CYP3A4-substrate:  0.005

ADMET: Excretion

Clearance (CL):  0.591
Half-life (T1/2):  0.641

ADMET: Toxicity

hERG Blockers:  0.318
Human Hepatotoxicity (H-HT):  0.223
Drug-inuced Liver Injury (DILI):  0.008
AMES Toxicity:  0.063
Rat Oral Acute Toxicity:  0.065
Maximum Recommended Daily Dose:  0.024
Skin Sensitization:  0.151
Carcinogencity:  0.008
Eye Corrosion:  0.003
Eye Irritation:  0.007
Respiratory Toxicity:  0.178

Download Data

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

  Natural Product: NPC146563

Natural Product ID:  NPC146563
Common Name*:   Acankoreoside A
IUPAC Name:   (1R,3aS,5aR,5bR,7aR,8S,9R,11aR,11bR,13aR,13bR)-3a-[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxycarbonyl-9-hydroxy-5a,5b,8,11a-tetramethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-8-carboxylic acid
Synonyms:   Acankoreoside A
Standard InCHIKey:  OSXJYFIVZQMFMF-ATHBPGJJSA-N
Standard InCHI:  InChI=1S/C48H76O19/c1-20(2)22-10-15-48(17-16-45(5)23(29(22)48)8-9-26-44(4)13-12-28(50)47(7,42(59)60)27(44)11-14-46(26,45)6)43(61)67-41-36(57)33(54)31(52)25(65-41)19-62-39-37(58)34(55)38(24(18-49)64-39)66-40-35(56)32(53)30(51)21(3)63-40/h21-41,49-58H,1,8-19H2,2-7H3,(H,59,60)/t21-,22-,23+,24+,25+,26+,27+,28+,29+,30-,31+,32+,33-,34+,35+,36+,37+,38+,39+,40-,41-,44+,45+,46+,47-,48-/m0/s1
SMILES:  OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](OC(=O)[C@@]34CC[C@H]([C@@H]4[C@@H]4[C@](CC3)(C)[C@]3(C)CC[C@@H]5[C@]([C@H]3CC4)(C)CC[C@H]([C@@]5(C)C(=O)O)O)C(=C)C)[C@@H]([C@H]([C@@H]2O)O)O)[C@@H]([C@H]([C@@H]1O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1269324
PubChem CID:   10795959
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0002049] Terpene glycosides
          • [CHEMONTID:0001580] Triterpene glycosides
            • [CHEMONTID:0002358] Triterpene saponins

*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
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0031-9422(00)89267-5]
NPO6003 Halorosellinia oceanica Species Xylariaceae Eukaryota n.a. n.a. n.a. PMID[11454459]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[12882150]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[15666542]
NPO10814 Ilex latifolia Species Aquifoliaceae Eukaryota n.a. stem n.a. PMID[16252920]
NPO12610 Diospyros dendo Species Ebenaceae Eukaryota n.a. n.a. n.a. PMID[16441080]
NPO3029 Daedalea dickinsii Species Coriolaceae Eukaryota n.a. mycelium n.a. PMID[17986791]
NPO6003 Halorosellinia oceanica Species Xylariaceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO17954 Narcissus tazetta Species Amaryllidaceae Eukaryota n.a. Turkey n.a. PMID[19299148]
NPO29834 Acanthopanax koreanum n.a. n.a. n.a. n.a. n.a. n.a. PMID[20621475]
NPO29834 Acanthopanax koreanum n.a. n.a. n.a. steamed leaves n.a. n.a. PMID[20932756]
NPO6003 Halorosellinia oceanica Species Xylariaceae Eukaryota n.a. n.a. n.a. PMID[21265556]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota n.a. trunk bark n.a. PMID[556731]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota n.a. n.a. Database[FooDB]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO22136 Hedysarum alpinum Species Fabaceae Eukaryota n.a. n.a. Database[FooDB]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota Tubers n.a. Database[FooDB]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota Tuber n.a. n.a. Database[FooDB]
NPO29834 Acanthopanax koreanum n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO29219 Primula veris Species Primulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5200 Diphylleia grayi Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17954 Narcissus tazetta Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10814 Ilex latifolia Species Aquifoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO10814 Ilex latifolia Species Aquifoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17954 Narcissus tazetta Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5200 Diphylleia grayi Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29219 Primula veris Species Primulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5200 Diphylleia grayi Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12610 Diospyros dendo Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3029 Daedalea dickinsii Species Coriolaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10670 Bidens frondosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15944 Primnoa resedaeformis Species Primnoidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22136 Hedysarum alpinum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12019 Orontium japonicum Species Araceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10814 Ilex latifolia Species Aquifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5200 Diphylleia grayi Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12781 Schefflera heptaphylla Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12836 Mentha javanica Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15495 Narcissus cantabricus Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29219 Primula veris Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13061 Balanocarpus zeylanicus n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO3568 Myristica dactyloides Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1349 Zanthoxylum zanthoxyloides Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6003 Halorosellinia oceanica Species Xylariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17954 Narcissus tazetta Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14426 Halictus sexcinctus Species Halictidae 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
NPT2 Others Unspecified Activity = 2.89 pg/ml PMID[524455]
NPT2 Others Unspecified Activity = 4.62 pg/ml PMID[524455]
NPT2 Others Unspecified Activity = 4.57 pg/ml PMID[524455]
NPT2 Others Unspecified Activity = 17.04 pg/ml PMID[524455]
NPT2 Others Unspecified Activity = 24.87 pg/ml PMID[524455]
NPT2 Others Unspecified Activity = 29.78 pg/ml PMID[524455]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition < 50.0 % PMID[524456]

☑ 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 NPC146563 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
0.9811 High Similarity NPC137414
0.9811 High Similarity NPC469820
0.9811 High Similarity NPC469823
0.9808 High Similarity NPC204392
0.9808 High Similarity NPC240734
0.9808 High Similarity NPC1876
0.9808 High Similarity NPC275668
0.9808 High Similarity NPC91838
0.9808 High Similarity NPC11035
0.9717 High Similarity NPC54395
0.963 High Similarity NPC469822
0.9615 High Similarity NPC51947
0.9615 High Similarity NPC473844
0.9537 High Similarity NPC156651
0.9533 High Similarity NPC469821
0.9528 High Similarity NPC470543
0.9519 High Similarity NPC88744
0.9429 High Similarity NPC240125
0.9429 High Similarity NPC91583
0.9423 High Similarity NPC287269
0.9369 High Similarity NPC470478
0.9252 High Similarity NPC272242
0.9231 High Similarity NPC469827
0.9174 High Similarity NPC475486
0.9174 High Similarity NPC164389
0.9167 High Similarity NPC243572
0.9099 High Similarity NPC232237
0.9099 High Similarity NPC105800
0.9091 High Similarity NPC288205
0.9091 High Similarity NPC37134
0.9091 High Similarity NPC51465
0.9091 High Similarity NPC291903
0.9091 High Similarity NPC476992
0.9091 High Similarity NPC26626
0.9091 High Similarity NPC75287
0.9091 High Similarity NPC305267
0.9083 High Similarity NPC102619
0.9083 High Similarity NPC73986
0.9043 High Similarity NPC273962
0.9038 High Similarity NPC94919
0.9018 High Similarity NPC207738
0.9009 High Similarity NPC470876
0.9009 High Similarity NPC323359
0.9009 High Similarity NPC33012
0.9009 High Similarity NPC286457
0.9009 High Similarity NPC123522
0.9009 High Similarity NPC85154
0.9009 High Similarity NPC220160
0.9009 High Similarity NPC475209
0.9009 High Similarity NPC104137
0.9009 High Similarity NPC473824
0.9009 High Similarity NPC300419
0.9009 High Similarity NPC69811
0.9009 High Similarity NPC8524
0.9009 High Similarity NPC475514
0.9009 High Similarity NPC475119
0.9009 High Similarity NPC309223
0.9009 High Similarity NPC473452
0.9009 High Similarity NPC102505
0.9009 High Similarity NPC191827
0.8991 High Similarity NPC276093
0.8991 High Similarity NPC471383
0.8991 High Similarity NPC139044
0.8991 High Similarity NPC109079
0.8991 High Similarity NPC475504
0.8991 High Similarity NPC79718
0.8991 High Similarity NPC469946
0.8991 High Similarity NPC104400
0.8991 High Similarity NPC104071
0.8991 High Similarity NPC475516
0.8991 High Similarity NPC10320
0.8991 High Similarity NPC101744
0.8991 High Similarity NPC1046
0.8991 High Similarity NPC324875
0.8991 High Similarity NPC80843
0.8991 High Similarity NPC102439
0.8991 High Similarity NPC473373
0.8991 High Similarity NPC292677
0.8991 High Similarity NPC257468
0.8972 High Similarity NPC224414
0.8972 High Similarity NPC469826
0.8938 High Similarity NPC110385
0.8938 High Similarity NPC144644
0.8938 High Similarity NPC37860
0.8938 High Similarity NPC267694
0.8938 High Similarity NPC142151
0.8938 High Similarity NPC473645
0.8938 High Similarity NPC153673
0.8929 High Similarity NPC473459
0.8929 High Similarity NPC237191
0.8919 High Similarity NPC472718
0.8909 High Similarity NPC163183
0.8909 High Similarity NPC238935
0.8909 High Similarity NPC475208
0.8909 High Similarity NPC219180
0.8909 High Similarity NPC174720
0.8909 High Similarity NPC258885
0.8909 High Similarity NPC96641
0.8909 High Similarity NPC151543
0.8909 High Similarity NPC309714
0.8909 High Similarity NPC251263
0.8909 High Similarity NPC114287
0.8909 High Similarity NPC473343
0.8909 High Similarity NPC241909
0.8909 High Similarity NPC166422
0.8909 High Similarity NPC295823
0.8909 High Similarity NPC155410
0.8909 High Similarity NPC73318
0.8909 High Similarity NPC475467
0.8909 High Similarity NPC134835
0.8909 High Similarity NPC473826
0.8909 High Similarity NPC46665
0.8909 High Similarity NPC192600
0.8909 High Similarity NPC475287
0.8909 High Similarity NPC323341
0.8909 High Similarity NPC150400
0.8909 High Similarity NPC124296
0.8909 High Similarity NPC133818
0.8909 High Similarity NPC114304
0.8899 High Similarity NPC31839
0.8899 High Similarity NPC164419
0.8899 High Similarity NPC274833
0.8889 High Similarity NPC469825
0.886 High Similarity NPC293031
0.886 High Similarity NPC51099
0.886 High Similarity NPC68767
0.886 High Similarity NPC275225
0.885 High Similarity NPC25663
0.885 High Similarity NPC471577
0.885 High Similarity NPC473386
0.885 High Similarity NPC51564
0.885 High Similarity NPC135849
0.8839 High Similarity NPC471580
0.8829 High Similarity NPC471385
0.8829 High Similarity NPC123199
0.8829 High Similarity NPC475160
0.8829 High Similarity NPC119592
0.8829 High Similarity NPC41061
0.8829 High Similarity NPC473714
0.8829 High Similarity NPC60557
0.8829 High Similarity NPC224381
0.8829 High Similarity NPC293330
0.8829 High Similarity NPC100639
0.8829 High Similarity NPC227551
0.8829 High Similarity NPC475140
0.8829 High Similarity NPC298034
0.8829 High Similarity NPC4328
0.8829 High Similarity NPC250247
0.8829 High Similarity NPC294453
0.8829 High Similarity NPC54636
0.8829 High Similarity NPC161717
0.8829 High Similarity NPC469782
0.8829 High Similarity NPC261506
0.8829 High Similarity NPC43550
0.8829 High Similarity NPC65105
0.8829 High Similarity NPC305981
0.8829 High Similarity NPC476068
0.8829 High Similarity NPC79643
0.8829 High Similarity NPC70809
0.8829 High Similarity NPC57484
0.8829 High Similarity NPC309907
0.8829 High Similarity NPC204414
0.8829 High Similarity NPC202828
0.8829 High Similarity NPC471550
0.8829 High Similarity NPC236638
0.8829 High Similarity NPC71065
0.8829 High Similarity NPC67857
0.8829 High Similarity NPC76972
0.8818 High Similarity NPC48249
0.8818 High Similarity NPC473383
0.8818 High Similarity NPC139894
0.8818 High Similarity NPC472719
0.8818 High Similarity NPC207845
0.8818 High Similarity NPC233003
0.8807 High Similarity NPC279554
0.8807 High Similarity NPC474589
0.8807 High Similarity NPC106760
0.8807 High Similarity NPC242611
0.8807 High Similarity NPC90856
0.8807 High Similarity NPC475296
0.8807 High Similarity NPC270667
0.8807 High Similarity NPC136877
0.8807 High Similarity NPC174679
0.8807 High Similarity NPC127056
0.8807 High Similarity NPC164194
0.8807 High Similarity NPC59804
0.8807 High Similarity NPC29069
0.8807 High Similarity NPC56713
0.8772 High Similarity NPC476991
0.8761 High Similarity NPC475899
0.8761 High Similarity NPC239293
0.875 High Similarity NPC58448
0.875 High Similarity NPC160415
0.875 High Similarity NPC471384
0.875 High Similarity NPC161674
0.8739 High Similarity NPC477074
0.8739 High Similarity NPC251309
0.8727 High Similarity NPC285410
0.8727 High Similarity NPC65167
0.8727 High Similarity NPC473481

  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 NPC146563 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
0.9083 High Similarity NPD8133 Approved
0.839 Intermediate Similarity NPD8328 Phase 3
0.8348 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.8053 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.8018 Intermediate Similarity NPD8170 Clinical (unspecified phase)
0.7983 Intermediate Similarity NPD8377 Approved
0.7983 Intermediate Similarity NPD8294 Approved
0.7917 Intermediate Similarity NPD8335 Approved
0.7917 Intermediate Similarity NPD8380 Approved
0.7917 Intermediate Similarity NPD8379 Approved
0.7917 Intermediate Similarity NPD8296 Approved
0.7917 Intermediate Similarity NPD8378 Approved
0.7903 Intermediate Similarity NPD7319 Approved
0.783 Intermediate Similarity NPD8035 Phase 2
0.783 Intermediate Similarity NPD8034 Phase 2
0.7805 Intermediate Similarity NPD7507 Approved
0.7769 Intermediate Similarity NPD8033 Approved
0.7719 Intermediate Similarity NPD6412 Phase 2
0.768 Intermediate Similarity NPD7736 Approved
0.7596 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7593 Intermediate Similarity NPD8171 Discontinued
0.7521 Intermediate Similarity NPD7328 Approved
0.7521 Intermediate Similarity NPD7327 Approved
0.75 Intermediate Similarity NPD6686 Approved
0.746 Intermediate Similarity NPD8293 Discontinued
0.7459 Intermediate Similarity NPD7516 Approved
0.7339 Intermediate Similarity NPD8515 Approved
0.7339 Intermediate Similarity NPD8517 Approved
0.7339 Intermediate Similarity NPD8513 Phase 3
0.7339 Intermediate Similarity NPD8516 Approved
0.728 Intermediate Similarity NPD6370 Approved
0.72 Intermediate Similarity NPD7503 Approved
0.7165 Intermediate Similarity NPD7492 Approved
0.712 Intermediate Similarity NPD6059 Approved
0.712 Intermediate Similarity NPD6054 Approved
0.712 Intermediate Similarity NPD6319 Approved
0.7109 Intermediate Similarity NPD6616 Approved
0.7059 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7054 Intermediate Similarity NPD7748 Approved
0.7054 Intermediate Similarity NPD7078 Approved
0.7018 Intermediate Similarity NPD7902 Approved
0.6967 Remote Similarity NPD6882 Approved
0.6967 Remote Similarity NPD8297 Approved
0.6957 Remote Similarity NPD7638 Approved
0.6935 Remote Similarity NPD6940 Discontinued
0.6929 Remote Similarity NPD6016 Approved
0.6929 Remote Similarity NPD6015 Approved
0.6923 Remote Similarity NPD6697 Approved
0.6923 Remote Similarity NPD6114 Approved
0.6923 Remote Similarity NPD6118 Approved
0.6923 Remote Similarity NPD6115 Approved
0.6897 Remote Similarity NPD7639 Approved
0.6897 Remote Similarity NPD7640 Approved
0.688 Remote Similarity NPD7115 Discovery
0.688 Remote Similarity NPD6009 Approved
0.6875 Remote Similarity NPD7515 Phase 2
0.6875 Remote Similarity NPD5988 Approved
0.6827 Remote Similarity NPD6116 Phase 1
0.6814 Remote Similarity NPD6399 Phase 3
0.6774 Remote Similarity NPD4632 Approved
0.6754 Remote Similarity NPD7900 Approved
0.6754 Remote Similarity NPD7901 Clinical (unspecified phase)
0.675 Remote Similarity NPD6675 Approved
0.675 Remote Similarity NPD6402 Approved
0.675 Remote Similarity NPD7128 Approved
0.675 Remote Similarity NPD5739 Approved
0.6748 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6731 Remote Similarity NPD6117 Approved
0.6721 Remote Similarity NPD6373 Approved
0.6721 Remote Similarity NPD6372 Approved
0.6692 Remote Similarity NPD6067 Discontinued
0.6639 Remote Similarity NPD6899 Approved
0.6639 Remote Similarity NPD6881 Approved
0.6639 Remote Similarity NPD7320 Approved
0.6617 Remote Similarity NPD6033 Approved
0.6613 Remote Similarity NPD6649 Approved
0.6613 Remote Similarity NPD6650 Approved
0.6613 Remote Similarity NPD8130 Phase 1
0.6585 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6557 Remote Similarity NPD5697 Approved
0.6557 Remote Similarity NPD5701 Approved
0.6538 Remote Similarity NPD6113 Clinical (unspecified phase)
0.6538 Remote Similarity NPD6921 Approved
0.6532 Remote Similarity NPD7102 Approved
0.6532 Remote Similarity NPD6883 Approved
0.6532 Remote Similarity NPD4634 Approved
0.6532 Remote Similarity NPD7290 Approved
0.65 Remote Similarity NPD7632 Discontinued
0.6496 Remote Similarity NPD8450 Suspended
0.6481 Remote Similarity NPD6928 Phase 2
0.648 Remote Similarity NPD6869 Approved
0.648 Remote Similarity NPD6617 Approved
0.648 Remote Similarity NPD6847 Approved
0.6455 Remote Similarity NPD3669 Approved
0.6455 Remote Similarity NPD3670 Clinical (unspecified phase)
0.6452 Remote Similarity NPD6013 Approved
0.6452 Remote Similarity NPD6014 Approved
0.6452 Remote Similarity NPD6012 Approved
0.6441 Remote Similarity NPD6084 Phase 2
0.6441 Remote Similarity NPD6083 Phase 2
0.6439 Remote Similarity NPD7604 Phase 2
0.6423 Remote Similarity NPD8449 Approved
0.6418 Remote Similarity NPD8074 Phase 3
0.6412 Remote Similarity NPD5983 Phase 2
0.6404 Remote Similarity NPD5328 Approved
0.64 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6396 Remote Similarity NPD4786 Approved
0.6387 Remote Similarity NPD4225 Approved
0.6371 Remote Similarity NPD6011 Approved
0.637 Remote Similarity NPD8337 Approved
0.637 Remote Similarity NPD8336 Approved
0.6349 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6343 Remote Similarity NPD6336 Discontinued
0.6341 Remote Similarity NPD6008 Approved
0.633 Remote Similarity NPD7525 Registered
0.6316 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6306 Remote Similarity NPD4788 Approved
0.6303 Remote Similarity NPD4755 Approved
0.6301 Remote Similarity NPD7625 Phase 1
0.6293 Remote Similarity NPD6411 Approved
0.6293 Remote Similarity NPD6079 Approved
0.6293 Remote Similarity NPD7637 Suspended
0.6283 Remote Similarity NPD3618 Phase 1
0.6273 Remote Similarity NPD1779 Approved
0.6273 Remote Similarity NPD1780 Approved
0.6239 Remote Similarity NPD7645 Phase 2
0.6239 Remote Similarity NPD4202 Approved
0.6231 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6216 Remote Similarity NPD3667 Approved
0.6198 Remote Similarity NPD5286 Approved
0.6198 Remote Similarity NPD4700 Approved
0.6198 Remote Similarity NPD5285 Approved
0.6198 Remote Similarity NPD4696 Approved
0.619 Remote Similarity NPD4808 Clinical (unspecified phase)
0.619 Remote Similarity NPD4809 Clinical (unspecified phase)
0.6187 Remote Similarity NPD8338 Approved
0.6174 Remote Similarity NPD6672 Approved
0.6174 Remote Similarity NPD5737 Approved
0.6168 Remote Similarity NPD3703 Phase 2
0.616 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6159 Remote Similarity NPD5956 Approved
0.6154 Remote Similarity NPD6274 Approved
0.6154 Remote Similarity NPD7983 Approved
0.614 Remote Similarity NPD5330 Approved
0.614 Remote Similarity NPD7334 Approved
0.614 Remote Similarity NPD7146 Approved
0.614 Remote Similarity NPD6409 Approved
0.614 Remote Similarity NPD7521 Approved
0.614 Remote Similarity NPD6684 Approved
0.6136 Remote Similarity NPD7100 Approved
0.6136 Remote Similarity NPD7101 Approved
0.6134 Remote Similarity NPD5695 Phase 3
0.6121 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6121 Remote Similarity NPD6101 Approved
0.6116 Remote Similarity NPD5696 Approved
0.6098 Remote Similarity NPD5226 Approved
0.6098 Remote Similarity NPD5225 Approved
0.6098 Remote Similarity NPD4633 Approved
0.6098 Remote Similarity NPD5211 Phase 2
0.6098 Remote Similarity NPD5224 Approved
0.6083 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6083 Remote Similarity NPD4697 Phase 3
0.6083 Remote Similarity NPD5221 Approved
0.6083 Remote Similarity NPD5222 Approved
0.608 Remote Similarity NPD4768 Approved
0.608 Remote Similarity NPD4767 Approved
0.6068 Remote Similarity NPD46 Approved
0.6068 Remote Similarity NPD6698 Approved
0.6061 Remote Similarity NPD6335 Approved
0.6048 Remote Similarity NPD5175 Approved
0.6048 Remote Similarity NPD5174 Approved
0.6045 Remote Similarity NPD8274 Clinical (unspecified phase)
0.6045 Remote Similarity NPD6908 Approved
0.6045 Remote Similarity NPD6909 Approved
0.6034 Remote Similarity NPD6903 Approved
0.6033 Remote Similarity NPD5173 Approved
0.6031 Remote Similarity NPD6868 Approved
0.6019 Remote Similarity NPD3702 Approved
0.6016 Remote Similarity NPD1700 Approved
0.6016 Remote Similarity NPD5223 Approved
0.6 Remote Similarity NPD3700 Clinical (unspecified phase)
0.6 Remote Similarity NPD3699 Clinical (unspecified phase)
0.6 Remote Similarity NPD4057 Clinical (unspecified phase)
0.6 Remote Similarity NPD4056 Clinical (unspecified phase)
0.6 Remote Similarity NPD5141 Approved
0.6 Remote Similarity NPD8080 Discontinued
0.6 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6 Remote Similarity NPD4267 Clinical (unspecified phase)
0.5985 Remote Similarity NPD6317 Approved
0.5984 Remote Similarity NPD4729 Approved
0.5984 Remote Similarity NPD4730 Approved
0.5983 Remote Similarity NPD4753 Phase 2
0.5968 Remote Similarity NPD8084 Approved
0.5968 Remote Similarity NPD8086 Approved
0.5968 Remote Similarity NPD8139 Approved
0.5968 Remote Similarity NPD8083 Approved
0.5968 Remote Similarity NPD8085 Approved
0.5968 Remote Similarity NPD8082 Approved
0.5968 Remote Similarity NPD8138 Approved
0.5966 Remote Similarity NPD5778 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