Structure

Physi-Chem Properties

Molecular Weight:  400.26
Volume:  443.185
LogP:  3.993
LogD:  3.715
LogS:  -4.62
# Rotatable Bonds:  7
TPSA:  59.06
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.219
Synthetic Accessibility Score:  5.375
Fsp3:  0.56
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.685
MDCK Permeability:  1.9184939446859062e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.197
Human Intestinal Absorption (HIA):  0.127
20% Bioavailability (F20%):  0.014
30% Bioavailability (F30%):  0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.914
Plasma Protein Binding (PPB):  78.54356384277344%
Volume Distribution (VD):  0.764
Pgp-substrate:  11.473857879638672%

ADMET: Metabolism

CYP1A2-inhibitor:  0.053
CYP1A2-substrate:  0.407
CYP2C19-inhibitor:  0.416
CYP2C19-substrate:  0.699
CYP2C9-inhibitor:  0.614
CYP2C9-substrate:  0.151
CYP2D6-inhibitor:  0.348
CYP2D6-substrate:  0.224
CYP3A4-inhibitor:  0.939
CYP3A4-substrate:  0.38

ADMET: Excretion

Clearance (CL):  2.773
Half-life (T1/2):  0.697

ADMET: Toxicity

hERG Blockers:  0.026
Human Hepatotoxicity (H-HT):  0.947
Drug-inuced Liver Injury (DILI):  0.045
AMES Toxicity:  0.017
Rat Oral Acute Toxicity:  0.066
Maximum Recommended Daily Dose:  0.991
Skin Sensitization:  0.945
Carcinogencity:  0.087
Eye Corrosion:  0.017
Eye Irritation:  0.119
Respiratory Toxicity:  0.967

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

  Natural Product: NPC61527

Natural Product ID:  NPC61527
Common Name*:   Vibsanin R
IUPAC Name:   [(1S,4E,7S,8E,10R,11R)-4-(hydroxymethyl)-7,11-dimethyl-7-[(2E)-4-methylpenta-2,4-dienyl]-12-oxabicyclo[9.1.0]dodeca-4,8-dien-10-yl] 3-methylbut-2-enoate
Synonyms:   Vibsanin R
Standard InCHIKey:  CZECWCCJJGKHQY-HFHNTLNYSA-N
Standard InCHI:  InChI=1S/C25H36O4/c1-18(2)8-7-13-24(5)14-11-20(17-26)9-10-22-25(6,29-22)21(12-15-24)28-23(27)16-19(3)4/h7-8,11-12,15-16,21-22,26H,1,9-10,13-14,17H2,2-6H3/b8-7+,15-12+,20-11+/t21-,22+,24+,25+/m1/s1
SMILES:  C=C(C)/C=C/C[C@@]1(C)C/C=C(CC[C@H]2[C@](C)([C@@H](/C=C/1)OC(=O)C=C(C)C)O2)/CO
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL511651
PubChem CID:   11258097
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0003909] Fatty Acyls
        • [CHEMONTID:0000324] Fatty acid 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
NPO6082 Centaurium pulchellum Species Gentianaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0031-9422(00)83457-3]
NPO8911 Aspergillus aculeatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[10075772]
NPO8404 Isodon xerophilus Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[10843567]
NPO6717 Viburnum awabuki Species Adoxaceae Eukaryota n.a. n.a. n.a. PMID[15043405]
NPO8911 Aspergillus aculeatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[16155971]
NPO4979 Elysia grandifolia Species Placobranchidae Eukaryota n.a. n.a. n.a. PMID[17125219]
NPO8404 Isodon xerophilus Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[17665952]
NPO8269 Isodon nervosus Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[18345641]
NPO8911 Aspergillus aculeatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[19824618]
NPO8911 Aspergillus aculeatus Species Aspergillaceae Eukaryota n.a. mycelium n.a. PMID[21667999]
NPO8911 Aspergillus aculeatus Species Aspergillaceae Eukaryota n.a. latex n.a. PMID[21854017]
NPO7935 Strychnos angustiflora Species Loganiaceae Eukaryota n.a. n.a. n.a. PMID[27592135]
NPO8911 Aspergillus aculeatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[324959]
NPO8404 Isodon xerophilus Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[33325237]
NPO6717 Viburnum awabuki Species Adoxaceae Eukaryota n.a. leaf n.a. Database[Article]
NPO8404 Isodon xerophilus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2476 Lonicera fulvotomentosa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7935 Strychnos angustiflora Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO149 Heliotropium europaeum Species Heliotropiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO149 Heliotropium europaeum Species Heliotropiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6717 Viburnum awabuki Species Adoxaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2476 Lonicera fulvotomentosa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7935 Strychnos angustiflora Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2637 Agave rigidissima Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8404 Isodon xerophilus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5144 Berberis japonica Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9228.1 Narcissus pseudonarcissus subsp. leonensis Subspecies Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2476 Lonicera fulvotomentosa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO149 Heliotropium europaeum Species Heliotropiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8911 Aspergillus aculeatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[Title]
NPO2476 Lonicera fulvotomentosa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7935 Strychnos angustiflora Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO149 Heliotropium europaeum Species Heliotropiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8269 Isodon nervosus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7766 Pericopsis schliebenii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4516 Fasciospongia rimosa Species Thorectidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9228.1 Narcissus pseudonarcissus subsp. leonensis Subspecies Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8103 Lecanora melanophthalma Species Lecanoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1355 Urechis caupo Species Urechidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8911 Aspergillus aculeatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9903 Engelhardia spicata Species Juglandaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8404 Isodon xerophilus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2304 Byssovorax cruenta Species Polyangiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO6717 Viburnum awabuki Species Adoxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25481 Lonchocarpus oaxacensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7060 Ficus ruficaulis Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2637 Agave rigidissima Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4979 Elysia grandifolia Species Placobranchidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO276 Miscanthus sacchariflorus Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5144 Berberis japonica Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15610 Citrus trifolia Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10806 Achillea roseoalba Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24370 Crassocephalum crepidioides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2476 Lonicera fulvotomentosa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6082 Centaurium pulchellum Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5319 Ulmus thomasii Species Ulmaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3830 Euplotes rariseta Species Euplotidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6310 Ruta bracteosa Species Rutaceae 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
NPT168 Cell Line P388 Mus musculus ED50 < 10.0 ug ml-1 PMID[516866]

☑ 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 NPC61527 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
0.975 High Similarity NPC186155
0.975 High Similarity NPC78673
0.975 High Similarity NPC160517
0.8889 High Similarity NPC471537
0.8642 High Similarity NPC84360
0.8519 High Similarity NPC188860
0.8506 High Similarity NPC199382
0.8488 Intermediate Similarity NPC471494
0.8452 Intermediate Similarity NPC184208
0.8452 Intermediate Similarity NPC8538
0.8452 Intermediate Similarity NPC315731
0.8452 Intermediate Similarity NPC474894
0.8427 Intermediate Similarity NPC3952
0.8415 Intermediate Similarity NPC233071
0.8415 Intermediate Similarity NPC477203
0.8293 Intermediate Similarity NPC477202
0.8276 Intermediate Similarity NPC11804
0.8256 Intermediate Similarity NPC474809
0.8256 Intermediate Similarity NPC161045
0.8214 Intermediate Similarity NPC139712
0.8191 Intermediate Similarity NPC475653
0.8182 Intermediate Similarity NPC311163
0.8172 Intermediate Similarity NPC57664
0.8172 Intermediate Similarity NPC255410
0.8163 Intermediate Similarity NPC469957
0.8163 Intermediate Similarity NPC472263
0.8163 Intermediate Similarity NPC469959
0.8163 Intermediate Similarity NPC108682
0.8152 Intermediate Similarity NPC469491
0.8148 Intermediate Similarity NPC329890
0.8148 Intermediate Similarity NPC329914
0.8148 Intermediate Similarity NPC477085
0.8111 Intermediate Similarity NPC83423
0.8105 Intermediate Similarity NPC475053
0.809 Intermediate Similarity NPC316138
0.809 Intermediate Similarity NPC313658
0.8085 Intermediate Similarity NPC205143
0.8085 Intermediate Similarity NPC120299
0.8072 Intermediate Similarity NPC469880
0.8072 Intermediate Similarity NPC301525
0.8065 Intermediate Similarity NPC300710
0.8061 Intermediate Similarity NPC93026
0.8061 Intermediate Similarity NPC265502
0.8061 Intermediate Similarity NPC29389
0.8061 Intermediate Similarity NPC469960
0.8046 Intermediate Similarity NPC231601
0.8025 Intermediate Similarity NPC477086
0.8025 Intermediate Similarity NPC477084
0.8025 Intermediate Similarity NPC477087
0.8023 Intermediate Similarity NPC475944
0.8 Intermediate Similarity NPC1180
0.8 Intermediate Similarity NPC65700
0.7978 Intermediate Similarity NPC122502
0.7938 Intermediate Similarity NPC473596
0.7935 Intermediate Similarity NPC158061
0.7912 Intermediate Similarity NPC133450
0.7907 Intermediate Similarity NPC474739
0.7901 Intermediate Similarity NPC476037
0.7901 Intermediate Similarity NPC473361
0.7901 Intermediate Similarity NPC476012
0.7901 Intermediate Similarity NPC329904
0.7901 Intermediate Similarity NPC4299
0.7882 Intermediate Similarity NPC209135
0.7882 Intermediate Similarity NPC474005
0.7882 Intermediate Similarity NPC248775
0.7882 Intermediate Similarity NPC474816
0.7849 Intermediate Similarity NPC109406
0.7831 Intermediate Similarity NPC477204
0.7831 Intermediate Similarity NPC315843
0.7831 Intermediate Similarity NPC107654
0.7826 Intermediate Similarity NPC177668
0.7816 Intermediate Similarity NPC112868
0.7812 Intermediate Similarity NPC203627
0.7812 Intermediate Similarity NPC475068
0.7812 Intermediate Similarity NPC161855
0.7805 Intermediate Similarity NPC316185
0.7791 Intermediate Similarity NPC470149
0.7791 Intermediate Similarity NPC180725
0.7791 Intermediate Similarity NPC470148
0.7791 Intermediate Similarity NPC86971
0.7789 Intermediate Similarity NPC173329
0.7789 Intermediate Similarity NPC476315
0.7789 Intermediate Similarity NPC473291
0.7789 Intermediate Similarity NPC288350
0.7789 Intermediate Similarity NPC279621
0.7778 Intermediate Similarity NPC269841
0.7778 Intermediate Similarity NPC101622
0.7778 Intermediate Similarity NPC164393
0.7766 Intermediate Similarity NPC472467
0.7765 Intermediate Similarity NPC262747
0.7755 Intermediate Similarity NPC11956
0.7742 Intermediate Similarity NPC114172
0.7742 Intermediate Similarity NPC206679
0.7742 Intermediate Similarity NPC476075
0.7742 Intermediate Similarity NPC476084
0.7742 Intermediate Similarity NPC471324
0.7732 Intermediate Similarity NPC79631
0.7732 Intermediate Similarity NPC98813
0.7732 Intermediate Similarity NPC13743
0.7711 Intermediate Similarity NPC185186
0.7711 Intermediate Similarity NPC327383
0.7708 Intermediate Similarity NPC475332
0.7708 Intermediate Similarity NPC120446
0.7701 Intermediate Similarity NPC470147
0.7701 Intermediate Similarity NPC133226
0.7684 Intermediate Similarity NPC272050
0.7684 Intermediate Similarity NPC14961
0.7684 Intermediate Similarity NPC107476
0.7684 Intermediate Similarity NPC270013
0.7684 Intermediate Similarity NPC220221
0.7683 Intermediate Similarity NPC469660
0.7677 Intermediate Similarity NPC23584
0.7674 Intermediate Similarity NPC279532
0.767 Intermediate Similarity NPC71680
0.766 Intermediate Similarity NPC238090
0.766 Intermediate Similarity NPC476049
0.766 Intermediate Similarity NPC472195
0.766 Intermediate Similarity NPC475838
0.766 Intermediate Similarity NPC228451
0.766 Intermediate Similarity NPC472196
0.766 Intermediate Similarity NPC159092
0.766 Intermediate Similarity NPC125674
0.7654 Intermediate Similarity NPC305698
0.764 Intermediate Similarity NPC170377
0.764 Intermediate Similarity NPC49208
0.764 Intermediate Similarity NPC23748
0.764 Intermediate Similarity NPC44261
0.7634 Intermediate Similarity NPC473448
0.7634 Intermediate Similarity NPC474761
0.7634 Intermediate Similarity NPC313670
0.7634 Intermediate Similarity NPC476004
0.7629 Intermediate Similarity NPC222303
0.7619 Intermediate Similarity NPC265290
0.7619 Intermediate Similarity NPC227814
0.7619 Intermediate Similarity NPC144995
0.7619 Intermediate Similarity NPC305044
0.7609 Intermediate Similarity NPC474471
0.7609 Intermediate Similarity NPC227379
0.7604 Intermediate Similarity NPC473333
0.7604 Intermediate Similarity NPC472995
0.7586 Intermediate Similarity NPC325869
0.7586 Intermediate Similarity NPC477088
0.7582 Intermediate Similarity NPC208473
0.7579 Intermediate Similarity NPC474035
0.7579 Intermediate Similarity NPC57405
0.7579 Intermediate Similarity NPC81386
0.7579 Intermediate Similarity NPC474247
0.7579 Intermediate Similarity NPC256368
0.7579 Intermediate Similarity NPC303942
0.7579 Intermediate Similarity NPC159698
0.7573 Intermediate Similarity NPC15551
0.7561 Intermediate Similarity NPC329656
0.7558 Intermediate Similarity NPC475711
0.7558 Intermediate Similarity NPC474026
0.7558 Intermediate Similarity NPC315394
0.7556 Intermediate Similarity NPC471301
0.7553 Intermediate Similarity NPC472468
0.7551 Intermediate Similarity NPC288876
0.7551 Intermediate Similarity NPC38855
0.7531 Intermediate Similarity NPC259299
0.7529 Intermediate Similarity NPC285840
0.7529 Intermediate Similarity NPC327041
0.7528 Intermediate Similarity NPC471298
0.7528 Intermediate Similarity NPC323251
0.7528 Intermediate Similarity NPC324170
0.7527 Intermediate Similarity NPC49783
0.7527 Intermediate Similarity NPC246028
0.7526 Intermediate Similarity NPC2666
0.7526 Intermediate Similarity NPC182811
0.7524 Intermediate Similarity NPC106395
0.7524 Intermediate Similarity NPC101400
0.7524 Intermediate Similarity NPC46269
0.7524 Intermediate Similarity NPC101965
0.7524 Intermediate Similarity NPC287075
0.75 Intermediate Similarity NPC240838
0.75 Intermediate Similarity NPC469583
0.75 Intermediate Similarity NPC474765
0.75 Intermediate Similarity NPC477959
0.75 Intermediate Similarity NPC36954
0.7475 Intermediate Similarity NPC472753
0.7474 Intermediate Similarity NPC212486
0.7474 Intermediate Similarity NPC475912
0.7473 Intermediate Similarity NPC137033
0.7473 Intermediate Similarity NPC99395
0.7473 Intermediate Similarity NPC197903
0.7471 Intermediate Similarity NPC477089
0.747 Intermediate Similarity NPC129630
0.7453 Intermediate Similarity NPC67290
0.7453 Intermediate Similarity NPC138303
0.7453 Intermediate Similarity NPC133677
0.7451 Intermediate Similarity NPC266514
0.7449 Intermediate Similarity NPC274458
0.7447 Intermediate Similarity NPC472466
0.7447 Intermediate Similarity NPC202886
0.7447 Intermediate Similarity NPC475855
0.7444 Intermediate Similarity NPC471297
0.7442 Intermediate Similarity NPC203277
0.7442 Intermediate Similarity NPC236228
0.7442 Intermediate Similarity NPC256720
0.7429 Intermediate Similarity NPC138757

  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 NPC61527 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
0.8636 High Similarity NPD7838 Discovery
0.8022 Intermediate Similarity NPD6698 Approved
0.8022 Intermediate Similarity NPD46 Approved
0.7917 Intermediate Similarity NPD6648 Approved
0.7835 Intermediate Similarity NPD5344 Discontinued
0.7812 Intermediate Similarity NPD8029 Clinical (unspecified phase)
0.7553 Intermediate Similarity NPD7983 Approved
0.75 Intermediate Similarity NPD2685 Clinical (unspecified phase)
0.7363 Intermediate Similarity NPD6400 Clinical (unspecified phase)
0.7238 Intermediate Similarity NPD6371 Approved
0.7188 Intermediate Similarity NPD7637 Suspended
0.6947 Remote Similarity NPD7524 Approved
0.6939 Remote Similarity NPD5779 Approved
0.6939 Remote Similarity NPD5778 Approved
0.6931 Remote Similarity NPD4225 Approved
0.6915 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6907 Remote Similarity NPD5785 Approved
0.6882 Remote Similarity NPD6695 Phase 3
0.6882 Remote Similarity NPD7154 Phase 3
0.6863 Remote Similarity NPD7639 Approved
0.6863 Remote Similarity NPD7640 Approved
0.6809 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6774 Remote Similarity NPD5209 Approved
0.6771 Remote Similarity NPD4250 Approved
0.6771 Remote Similarity NPD4251 Approved
0.6765 Remote Similarity NPD7638 Approved
0.6747 Remote Similarity NPD5325 Clinical (unspecified phase)
0.6742 Remote Similarity NPD8039 Approved
0.6739 Remote Similarity NPD7332 Phase 2
0.6739 Remote Similarity NPD4822 Approved
0.6739 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6739 Remote Similarity NPD7514 Phase 3
0.6739 Remote Similarity NPD4821 Approved
0.6739 Remote Similarity NPD4819 Approved
0.6739 Remote Similarity NPD4820 Approved
0.6733 Remote Similarity NPD7839 Suspended
0.6729 Remote Similarity NPD6686 Approved
0.6705 Remote Similarity NPD4732 Discontinued
0.6696 Remote Similarity NPD7115 Discovery
0.6667 Remote Similarity NPD4249 Approved
0.6667 Remote Similarity NPD6902 Approved
0.6636 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6609 Remote Similarity NPD7503 Approved
0.6598 Remote Similarity NPD7750 Discontinued
0.6559 Remote Similarity NPD6930 Phase 2
0.6559 Remote Similarity NPD6931 Approved
0.6545 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6526 Remote Similarity NPD5362 Discontinued
0.6522 Remote Similarity NPD4271 Approved
0.6522 Remote Similarity NPD7145 Approved
0.6522 Remote Similarity NPD4268 Approved
0.6522 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6514 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6512 Remote Similarity NPD4247 Clinical (unspecified phase)
0.6506 Remote Similarity NPD4193 Approved
0.6506 Remote Similarity NPD4194 Approved
0.6506 Remote Similarity NPD4192 Approved
0.6506 Remote Similarity NPD4191 Approved
0.65 Remote Similarity NPD6411 Approved
0.6471 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6452 Remote Similarity NPD6929 Approved
0.6413 Remote Similarity NPD6932 Approved
0.6413 Remote Similarity NPD6925 Approved
0.6413 Remote Similarity NPD5776 Phase 2
0.6392 Remote Similarity NPD5363 Approved
0.6392 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6387 Remote Similarity NPD8273 Phase 1
0.6386 Remote Similarity NPD4246 Clinical (unspecified phase)
0.6374 Remote Similarity NPD8264 Approved
0.6356 Remote Similarity NPD7830 Approved
0.6356 Remote Similarity NPD7829 Approved
0.6354 Remote Similarity NPD5332 Approved
0.6354 Remote Similarity NPD5331 Approved
0.6348 Remote Similarity NPD7327 Approved
0.6348 Remote Similarity NPD7328 Approved
0.6344 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6337 Remote Similarity NPD7087 Discontinued
0.6325 Remote Similarity NPD8516 Approved
0.6325 Remote Similarity NPD8515 Approved
0.6325 Remote Similarity NPD8517 Approved
0.6325 Remote Similarity NPD8033 Approved
0.6325 Remote Similarity NPD8513 Phase 3
0.6316 Remote Similarity NPD4790 Discontinued
0.6316 Remote Similarity NPD6898 Phase 1
0.6306 Remote Similarity NPD5955 Clinical (unspecified phase)
0.63 Remote Similarity NPD1695 Approved
0.63 Remote Similarity NPD6101 Approved
0.63 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6293 Remote Similarity NPD7516 Approved
0.6262 Remote Similarity NPD7632 Discontinued
0.6261 Remote Similarity NPD7505 Discontinued
0.625 Remote Similarity NPD4269 Approved
0.625 Remote Similarity NPD4792 Clinical (unspecified phase)
0.625 Remote Similarity NPD4270 Approved
0.6239 Remote Similarity NPD6640 Phase 3
0.6239 Remote Similarity NPD8294 Approved
0.6239 Remote Similarity NPD8377 Approved
0.6224 Remote Similarity NPD6893 Approved
0.6214 Remote Similarity NPD5282 Discontinued
0.6211 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6195 Remote Similarity NPD6053 Discontinued
0.6186 Remote Similarity NPD8296 Approved
0.6186 Remote Similarity NPD8335 Approved
0.6186 Remote Similarity NPD8380 Approved
0.6186 Remote Similarity NPD8379 Approved
0.6186 Remote Similarity NPD6110 Phase 1
0.6186 Remote Similarity NPD8378 Approved
0.6162 Remote Similarity NPD5786 Approved
0.6146 Remote Similarity NPD5369 Approved
0.6145 Remote Similarity NPD585 Clinical (unspecified phase)
0.6129 Remote Similarity NPD6933 Approved
0.6105 Remote Similarity NPD6683 Phase 2
0.6087 Remote Similarity NPD6924 Approved
0.6087 Remote Similarity NPD6926 Approved
0.6083 Remote Similarity NPD7642 Approved
0.6082 Remote Similarity NPD6435 Approved
0.6082 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6066 Remote Similarity NPD8074 Phase 3
0.6064 Remote Similarity NPD4756 Discovery
0.6061 Remote Similarity NPD1696 Phase 3
0.6042 Remote Similarity NPD4252 Approved
0.6036 Remote Similarity NPD5954 Clinical (unspecified phase)
0.5984 Remote Similarity NPD7507 Approved
0.5983 Remote Similarity NPD7500 Approved
0.598 Remote Similarity NPD6051 Approved
0.5965 Remote Similarity NPD7116 Clinical (unspecified phase)
0.5934 Remote Similarity NPD7144 Approved
0.5934 Remote Similarity NPD7143 Approved
0.5932 Remote Similarity NPD7641 Discontinued
0.5922 Remote Similarity NPD3168 Discontinued
0.5922 Remote Similarity NPD7136 Phase 2
0.5917 Remote Similarity NPD8444 Approved
0.5909 Remote Similarity NPD6647 Phase 2
0.5904 Remote Similarity NPD4219 Approved
0.59 Remote Similarity NPD1694 Approved
0.5893 Remote Similarity NPD6412 Phase 2
0.5888 Remote Similarity NPD6083 Phase 2
0.5888 Remote Similarity NPD6084 Phase 2
0.5877 Remote Similarity NPD6421 Discontinued
0.5876 Remote Similarity NPD5368 Approved
0.5873 Remote Similarity NPD7260 Phase 2
0.587 Remote Similarity NPD7152 Approved
0.587 Remote Similarity NPD7151 Approved
0.587 Remote Similarity NPD7150 Approved
0.5854 Remote Similarity NPD8451 Approved
0.5841 Remote Similarity NPD5345 Clinical (unspecified phase)
0.584 Remote Similarity NPD7319 Approved
0.5825 Remote Similarity NPD5370 Suspended
0.5824 Remote Similarity NPD6922 Approved
0.5824 Remote Similarity NPD6923 Approved
0.5806 Remote Similarity NPD8448 Approved
0.5804 Remote Similarity NPD4211 Phase 1
0.5804 Remote Similarity NPD5048 Discontinued
0.5795 Remote Similarity NPD3197 Phase 1
0.5776 Remote Similarity NPD8297 Approved
0.5772 Remote Similarity NPD8340 Approved
0.5772 Remote Similarity NPD8342 Approved
0.5772 Remote Similarity NPD8341 Approved
0.5772 Remote Similarity NPD8299 Approved
0.5755 Remote Similarity NPD7748 Approved
0.5747 Remote Similarity NPD368 Approved
0.5726 Remote Similarity NPD4632 Approved
0.5714 Remote Similarity NPD4198 Discontinued
0.5714 Remote Similarity NPD4810 Clinical (unspecified phase)
0.5714 Remote Similarity NPD7509 Discontinued
0.5714 Remote Similarity NPD7515 Phase 2
0.5702 Remote Similarity NPD6881 Approved
0.5702 Remote Similarity NPD7741 Discontinued
0.5702 Remote Similarity NPD6899 Approved
0.5702 Remote Similarity NPD6319 Approved
0.5701 Remote Similarity NPD5695 Phase 3
0.5691 Remote Similarity NPD7604 Phase 2
0.5676 Remote Similarity NPD3653 Clinical (unspecified phase)
0.5669 Remote Similarity NPD8391 Approved
0.5669 Remote Similarity NPD8392 Approved
0.5669 Remote Similarity NPD8390 Approved
0.5667 Remote Similarity NPD694 Clinical (unspecified phase)
0.5667 Remote Similarity NPD7331 Phase 2
0.5664 Remote Similarity NPD6402 Approved
0.5664 Remote Similarity NPD6675 Approved
0.5664 Remote Similarity NPD5739 Approved
0.5664 Remote Similarity NPD7128 Approved
0.5664 Remote Similarity NPD6008 Approved
0.566 Remote Similarity NPD6399 Phase 3
0.5649 Remote Similarity NPD7966 Clinical (unspecified phase)
0.5645 Remote Similarity NPD7492 Approved
0.5631 Remote Similarity NPD4751 Clinical (unspecified phase)
0.563 Remote Similarity NPD2629 Approved
0.5625 Remote Similarity NPD4220 Pre-registration
0.5614 Remote Similarity NPD6685 Approved
0.5614 Remote Similarity NPD5697 Approved
0.5603 Remote Similarity NPD6883 Approved
0.5603 Remote Similarity NPD7102 Approved
0.5603 Remote Similarity NPD7290 Approved
0.5603 Remote Similarity NPD2067 Discontinued
0.56 Remote Similarity NPD6616 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