Structure

Physi-Chem Properties

Molecular Weight:  416.26
Volume:  451.976
LogP:  3.602
LogD:  3.187
LogS:  -4.506
# Rotatable Bonds:  7
TPSA:  76.13
# H-Bond Aceptor:  5
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.225
Synthetic Accessibility Score:  5.464
Fsp3:  0.6
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.813
MDCK Permeability:  1.5275123587343842e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.395
Human Intestinal Absorption (HIA):  0.319
20% Bioavailability (F20%):  0.035
30% Bioavailability (F30%):  0.064

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.747
Plasma Protein Binding (PPB):  80.24529266357422%
Volume Distribution (VD):  1.183
Pgp-substrate:  7.934236526489258%

ADMET: Metabolism

CYP1A2-inhibitor:  0.027
CYP1A2-substrate:  0.36
CYP2C19-inhibitor:  0.425
CYP2C19-substrate:  0.644
CYP2C9-inhibitor:  0.578
CYP2C9-substrate:  0.202
CYP2D6-inhibitor:  0.223
CYP2D6-substrate:  0.133
CYP3A4-inhibitor:  0.916
CYP3A4-substrate:  0.351

ADMET: Excretion

Clearance (CL):  2.216
Half-life (T1/2):  0.696

ADMET: Toxicity

hERG Blockers:  0.021
Human Hepatotoxicity (H-HT):  0.931
Drug-inuced Liver Injury (DILI):  0.111
AMES Toxicity:  0.007
Rat Oral Acute Toxicity:  0.04
Maximum Recommended Daily Dose:  0.992
Skin Sensitization:  0.841
Carcinogencity:  0.176
Eye Corrosion:  0.012
Eye Irritation:  0.03
Respiratory Toxicity:  0.976

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

  Natural Product: NPC83423

Natural Product ID:  NPC83423
Common Name*:   Vibsanin T
IUPAC Name:   [(1S,4E,7S,8E,10R,11R)-4-formyl-7-[(E)-4-hydroxy-4-methylpent-2-enyl]-7,11-dimethyl-12-oxabicyclo[9.1.0]dodeca-4,8-dien-10-yl] 3-methylbut-2-enoate
Synonyms:   Vibsanin T
Standard InCHIKey:  ZCZKJKIOPWIFME-XWMBFTBISA-N
Standard InCHI:  InChI=1S/C25H36O5/c1-18(2)16-22(27)29-20-11-15-24(5,13-7-12-23(3,4)28)14-10-19(17-26)8-9-21-25(20,6)30-21/h7,10-12,15-17,20-21,28H,8-9,13-14H2,1-6H3/b12-7+,15-11+,19-10+/t20-,21+,24+,25+/m1/s1
SMILES:  O=C/C/1=C/C[C@](C)(C/C=C/C(O)(C)C)/C=C/[C@H]([C@]2([C@H](CC1)O2)C)OC(=O)C=C(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL471393
PubChem CID:   11441439
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]
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]
NPO8404 Isodon xerophilus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
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]
NPO9228.1 Narcissus pseudonarcissus subsp. leonensis Subspecies Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5144 Berberis japonica Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
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]
NPO149 Heliotropium europaeum Species Heliotropiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2476 Lonicera fulvotomentosa Species Caprifoliaceae 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]
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]
NPO24370 Crassocephalum crepidioides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10806 Achillea roseoalba Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6082 Centaurium pulchellum Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2476 Lonicera fulvotomentosa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3830 Euplotes rariseta Species Euplotidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5319 Ulmus thomasii Species Ulmaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6310 Ruta bracteosa Species Rutaceae 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]
NPO7935 Strychnos angustiflora Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4516 Fasciospongia rimosa Species Thorectidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7766 Pericopsis schliebenii Species Fabaceae 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]
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]
NPO8911 Aspergillus aculeatus Species Aspergillaceae 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[553283]

☑ 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 NPC83423 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
0.8353 Intermediate Similarity NPC136033
0.8295 Intermediate Similarity NPC160517
0.8295 Intermediate Similarity NPC186155
0.8295 Intermediate Similarity NPC78673
0.8111 Intermediate Similarity NPC61527
0.8111 Intermediate Similarity NPC122502
0.8105 Intermediate Similarity NPC476315
0.809 Intermediate Similarity NPC70424
0.809 Intermediate Similarity NPC243618
0.809 Intermediate Similarity NPC72464
0.8043 Intermediate Similarity NPC106040
0.8043 Intermediate Similarity NPC115179
0.8 Intermediate Similarity NPC11804
0.8 Intermediate Similarity NPC14961
0.8 Intermediate Similarity NPC270013
0.7978 Intermediate Similarity NPC170377
0.7978 Intermediate Similarity NPC161045
0.7957 Intermediate Similarity NPC474761
0.7957 Intermediate Similarity NPC476004
0.7957 Intermediate Similarity NPC475748
0.7935 Intermediate Similarity NPC227379
0.7935 Intermediate Similarity NPC474471
0.7931 Intermediate Similarity NPC471537
0.7912 Intermediate Similarity NPC198314
0.7895 Intermediate Similarity NPC57405
0.7895 Intermediate Similarity NPC474035
0.7895 Intermediate Similarity NPC81386
0.7895 Intermediate Similarity NPC303942
0.7889 Intermediate Similarity NPC474865
0.7889 Intermediate Similarity NPC9868
0.7865 Intermediate Similarity NPC85772
0.7857 Intermediate Similarity NPC475053
0.7857 Intermediate Similarity NPC288876
0.7841 Intermediate Similarity NPC233377
0.7831 Intermediate Similarity NPC469660
0.7826 Intermediate Similarity NPC471738
0.7826 Intermediate Similarity NPC231889
0.7826 Intermediate Similarity NPC72513
0.7812 Intermediate Similarity NPC36954
0.7812 Intermediate Similarity NPC475659
0.7802 Intermediate Similarity NPC137033
0.7802 Intermediate Similarity NPC197903
0.7802 Intermediate Similarity NPC99395
0.7802 Intermediate Similarity NPC474547
0.78 Intermediate Similarity NPC472755
0.7789 Intermediate Similarity NPC475912
0.7789 Intermediate Similarity NPC212486
0.7789 Intermediate Similarity NPC476300
0.7778 Intermediate Similarity NPC108045
0.7778 Intermediate Similarity NPC472753
0.7778 Intermediate Similarity NPC53867
0.7778 Intermediate Similarity NPC475622
0.7766 Intermediate Similarity NPC473448
0.7766 Intermediate Similarity NPC51004
0.7766 Intermediate Similarity NPC51653
0.7753 Intermediate Similarity NPC141810
0.7753 Intermediate Similarity NPC325031
0.7742 Intermediate Similarity NPC153805
0.7742 Intermediate Similarity NPC281516
0.7732 Intermediate Similarity NPC473859
0.7732 Intermediate Similarity NPC279621
0.7717 Intermediate Similarity NPC234038
0.7717 Intermediate Similarity NPC164393
0.7717 Intermediate Similarity NPC469483
0.7708 Intermediate Similarity NPC473316
0.7708 Intermediate Similarity NPC473330
0.77 Intermediate Similarity NPC472754
0.7692 Intermediate Similarity NPC14575
0.7692 Intermediate Similarity NPC196487
0.7692 Intermediate Similarity NPC31086
0.7684 Intermediate Similarity NPC30515
0.7684 Intermediate Similarity NPC184463
0.7684 Intermediate Similarity NPC303697
0.7684 Intermediate Similarity NPC261607
0.7684 Intermediate Similarity NPC300312
0.7684 Intermediate Similarity NPC111114
0.7667 Intermediate Similarity NPC474252
0.7667 Intermediate Similarity NPC474291
0.766 Intermediate Similarity NPC307411
0.766 Intermediate Similarity NPC166919
0.766 Intermediate Similarity NPC212598
0.766 Intermediate Similarity NPC474032
0.766 Intermediate Similarity NPC151770
0.7653 Intermediate Similarity NPC40812
0.7647 Intermediate Similarity NPC472751
0.7647 Intermediate Similarity NPC472749
0.764 Intermediate Similarity NPC474510
0.7634 Intermediate Similarity NPC248602
0.7634 Intermediate Similarity NPC475703
0.7634 Intermediate Similarity NPC474765
0.7629 Intermediate Similarity NPC477922
0.7624 Intermediate Similarity NPC472747
0.7624 Intermediate Similarity NPC472750
0.7614 Intermediate Similarity NPC267231
0.7614 Intermediate Similarity NPC93763
0.7614 Intermediate Similarity NPC108816
0.7609 Intermediate Similarity NPC38468
0.7609 Intermediate Similarity NPC21469
0.7609 Intermediate Similarity NPC261380
0.7609 Intermediate Similarity NPC319795
0.7609 Intermediate Similarity NPC50362
0.7604 Intermediate Similarity NPC475838
0.7604 Intermediate Similarity NPC295204
0.7604 Intermediate Similarity NPC273579
0.7604 Intermediate Similarity NPC125674
0.7604 Intermediate Similarity NPC288240
0.7604 Intermediate Similarity NPC228451
0.7604 Intermediate Similarity NPC162205
0.7586 Intermediate Similarity NPC271070
0.7582 Intermediate Similarity NPC52609
0.7582 Intermediate Similarity NPC1761
0.7582 Intermediate Similarity NPC474809
0.7582 Intermediate Similarity NPC11620
0.7582 Intermediate Similarity NPC475947
0.7579 Intermediate Similarity NPC49342
0.7579 Intermediate Similarity NPC166554
0.7579 Intermediate Similarity NPC265856
0.7579 Intermediate Similarity NPC251385
0.7579 Intermediate Similarity NPC469368
0.7576 Intermediate Similarity NPC261377
0.7576 Intermediate Similarity NPC473326
0.7576 Intermediate Similarity NPC255592
0.7576 Intermediate Similarity NPC141191
0.7576 Intermediate Similarity NPC187761
0.7576 Intermediate Similarity NPC83895
0.7576 Intermediate Similarity NPC308567
0.7576 Intermediate Similarity NPC474213
0.7556 Intermediate Similarity NPC286229
0.7556 Intermediate Similarity NPC471325
0.7556 Intermediate Similarity NPC475481
0.7556 Intermediate Similarity NPC79277
0.7553 Intermediate Similarity NPC475902
0.7553 Intermediate Similarity NPC472008
0.7553 Intermediate Similarity NPC476704
0.7551 Intermediate Similarity NPC477921
0.7549 Intermediate Similarity NPC472748
0.7549 Intermediate Similarity NPC474741
0.7528 Intermediate Similarity NPC469690
0.7528 Intermediate Similarity NPC617
0.7528 Intermediate Similarity NPC469617
0.7528 Intermediate Similarity NPC469620
0.7528 Intermediate Similarity NPC471740
0.7528 Intermediate Similarity NPC471299
0.7527 Intermediate Similarity NPC150755
0.7527 Intermediate Similarity NPC474045
0.7527 Intermediate Similarity NPC305475
0.7527 Intermediate Similarity NPC261253
0.7527 Intermediate Similarity NPC220478
0.7527 Intermediate Similarity NPC469676
0.7527 Intermediate Similarity NPC475461
0.7526 Intermediate Similarity NPC471147
0.7526 Intermediate Similarity NPC167219
0.7526 Intermediate Similarity NPC474247
0.7526 Intermediate Similarity NPC65829
0.7525 Intermediate Similarity NPC473596
0.75 Intermediate Similarity NPC474776
0.75 Intermediate Similarity NPC475441
0.75 Intermediate Similarity NPC174314
0.75 Intermediate Similarity NPC219874
0.75 Intermediate Similarity NPC473321
0.75 Intermediate Similarity NPC470373
0.75 Intermediate Similarity NPC261398
0.75 Intermediate Similarity NPC470379
0.7477 Intermediate Similarity NPC56448
0.7476 Intermediate Similarity NPC223450
0.7476 Intermediate Similarity NPC243998
0.7475 Intermediate Similarity NPC245521
0.7475 Intermediate Similarity NPC169205
0.7474 Intermediate Similarity NPC295312
0.7473 Intermediate Similarity NPC145963
0.7473 Intermediate Similarity NPC475690
0.7451 Intermediate Similarity NPC309398
0.7451 Intermediate Similarity NPC474581
0.7451 Intermediate Similarity NPC473624
0.7451 Intermediate Similarity NPC475367
0.7451 Intermediate Similarity NPC473816
0.7449 Intermediate Similarity NPC272050
0.7449 Intermediate Similarity NPC214694
0.7449 Intermediate Similarity NPC472469
0.7447 Intermediate Similarity NPC179659
0.7447 Intermediate Similarity NPC160138
0.7444 Intermediate Similarity NPC281132
0.7429 Intermediate Similarity NPC47951
0.7426 Intermediate Similarity NPC133907
0.7426 Intermediate Similarity NPC474742
0.7426 Intermediate Similarity NPC476270
0.7426 Intermediate Similarity NPC185141
0.7426 Intermediate Similarity NPC303559
0.7426 Intermediate Similarity NPC128733
0.7426 Intermediate Similarity NPC46998
0.7426 Intermediate Similarity NPC110443
0.7423 Intermediate Similarity NPC469692
0.7423 Intermediate Similarity NPC179746
0.7423 Intermediate Similarity NPC81419
0.7423 Intermediate Similarity NPC469645
0.7423 Intermediate Similarity NPC476049
0.7419 Intermediate Similarity NPC149725
0.7419 Intermediate Similarity NPC47958
0.7419 Intermediate Similarity NPC304509
0.7419 Intermediate Similarity NPC474369

  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 NPC83423 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
0.7766 Intermediate Similarity NPD46 Approved
0.7766 Intermediate Similarity NPD6698 Approved
0.7609 Intermediate Similarity NPD1733 Clinical (unspecified phase)
0.7396 Intermediate Similarity NPD5785 Approved
0.7396 Intermediate Similarity NPD7838 Discovery
0.732 Intermediate Similarity NPD7983 Approved
0.7273 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7229 Intermediate Similarity NPD2685 Clinical (unspecified phase)
0.7204 Intermediate Similarity NPD7154 Phase 3
0.7196 Intermediate Similarity NPD6371 Approved
0.7117 Intermediate Similarity NPD7115 Discovery
0.7079 Intermediate Similarity NPD8039 Approved
0.699 Remote Similarity NPD6648 Approved
0.6923 Remote Similarity NPD5344 Discontinued
0.6915 Remote Similarity NPD5209 Approved
0.6915 Remote Similarity NPD4752 Clinical (unspecified phase)
0.69 Remote Similarity NPD5778 Approved
0.69 Remote Similarity NPD5779 Approved
0.6893 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6893 Remote Similarity NPD4225 Approved
0.6875 Remote Similarity NPD5363 Approved
0.6848 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6842 Remote Similarity NPD5362 Discontinued
0.6804 Remote Similarity NPD5786 Approved
0.68 Remote Similarity NPD6411 Approved
0.6771 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6759 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6737 Remote Similarity NPD6435 Approved
0.6702 Remote Similarity NPD4820 Approved
0.6702 Remote Similarity NPD4821 Approved
0.6702 Remote Similarity NPD4822 Approved
0.6702 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6702 Remote Similarity NPD4819 Approved
0.6701 Remote Similarity NPD1694 Approved
0.6699 Remote Similarity NPD7839 Suspended
0.6697 Remote Similarity NPD6686 Approved
0.661 Remote Similarity NPD7642 Approved
0.66 Remote Similarity NPD1695 Approved
0.66 Remote Similarity NPD6101 Approved
0.66 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6562 Remote Similarity NPD4270 Approved
0.6562 Remote Similarity NPD4269 Approved
0.6552 Remote Similarity NPD7331 Phase 2
0.6526 Remote Similarity NPD5368 Approved
0.6489 Remote Similarity NPD4271 Approved
0.6489 Remote Similarity NPD4268 Approved
0.646 Remote Similarity NPD8297 Approved
0.6458 Remote Similarity NPD5369 Approved
0.6396 Remote Similarity NPD6881 Approved
0.6396 Remote Similarity NPD6899 Approved
0.6383 Remote Similarity NPD4756 Discovery
0.6372 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6364 Remote Similarity NPD7507 Approved
0.6355 Remote Similarity NPD7640 Approved
0.6355 Remote Similarity NPD7639 Approved
0.6354 Remote Similarity NPD4252 Approved
0.6339 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6333 Remote Similarity NPD7829 Approved
0.6333 Remote Similarity NPD7830 Approved
0.6327 Remote Similarity NPD5332 Approved
0.6327 Remote Similarity NPD5331 Approved
0.6316 Remote Similarity NPD6053 Discontinued
0.6311 Remote Similarity NPD7637 Suspended
0.6306 Remote Similarity NPD5697 Approved
0.63 Remote Similarity NPD6422 Discontinued
0.6292 Remote Similarity NPD4247 Clinical (unspecified phase)
0.6289 Remote Similarity NPD4790 Discontinued
0.6283 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6283 Remote Similarity NPD6883 Approved
0.6283 Remote Similarity NPD7290 Approved
0.6283 Remote Similarity NPD7102 Approved
0.6262 Remote Similarity NPD7638 Approved
0.6238 Remote Similarity NPD3573 Approved
0.6238 Remote Similarity NPD4250 Approved
0.6238 Remote Similarity NPD4251 Approved
0.6228 Remote Similarity NPD6649 Approved
0.6228 Remote Similarity NPD6869 Approved
0.6228 Remote Similarity NPD6617 Approved
0.6228 Remote Similarity NPD6650 Approved
0.6228 Remote Similarity NPD8130 Phase 1
0.6228 Remote Similarity NPD6847 Approved
0.6216 Remote Similarity NPD6675 Approved
0.6216 Remote Similarity NPD7128 Approved
0.6216 Remote Similarity NPD5739 Approved
0.6216 Remote Similarity NPD6402 Approved
0.621 Remote Similarity NPD7319 Approved
0.62 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6195 Remote Similarity NPD6014 Approved
0.6195 Remote Similarity NPD6013 Approved
0.6195 Remote Similarity NPD6012 Approved
0.619 Remote Similarity NPD7748 Approved
0.619 Remote Similarity NPD5282 Discontinued
0.6186 Remote Similarity NPD7641 Discontinued
0.6174 Remote Similarity NPD6882 Approved
0.6168 Remote Similarity NPD6084 Phase 2
0.6168 Remote Similarity NPD6083 Phase 2
0.6167 Remote Similarity NPD8513 Phase 3
0.6167 Remote Similarity NPD8516 Approved
0.6167 Remote Similarity NPD8517 Approved
0.6167 Remote Similarity NPD8515 Approved
0.6161 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6139 Remote Similarity NPD6684 Approved
0.6139 Remote Similarity NPD7521 Approved
0.6139 Remote Similarity NPD5330 Approved
0.6139 Remote Similarity NPD6409 Approved
0.6139 Remote Similarity NPD7334 Approved
0.6139 Remote Similarity NPD7146 Approved
0.6139 Remote Similarity NPD4249 Approved
0.6136 Remote Similarity NPD3197 Phase 1
0.6136 Remote Similarity NPD5325 Clinical (unspecified phase)
0.6132 Remote Similarity NPD5695 Phase 3
0.6106 Remote Similarity NPD6011 Approved
0.6106 Remote Similarity NPD7320 Approved
0.6095 Remote Similarity NPD6399 Phase 3
0.6091 Remote Similarity NPD5211 Phase 2
0.6087 Remote Similarity NPD7116 Clinical (unspecified phase)
0.6071 Remote Similarity NPD6008 Approved
0.6067 Remote Similarity NPD7341 Phase 2
0.6053 Remote Similarity NPD6372 Approved
0.6053 Remote Similarity NPD6373 Approved
0.604 Remote Similarity NPD1696 Phase 3
0.602 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6019 Remote Similarity NPD6903 Approved
0.6019 Remote Similarity NPD7902 Approved
0.6019 Remote Similarity NPD5737 Approved
0.6019 Remote Similarity NPD6672 Approved
0.6019 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6018 Remote Similarity NPD5701 Approved
0.6 Remote Similarity NPD6079 Approved
0.6 Remote Similarity NPD7515 Phase 2
0.6 Remote Similarity NPD5693 Phase 1
0.5984 Remote Similarity NPD7260 Phase 2
0.5983 Remote Similarity NPD4632 Approved
0.5982 Remote Similarity NPD5141 Approved
0.5977 Remote Similarity NPD4246 Clinical (unspecified phase)
0.5968 Remote Similarity NPD8451 Approved
0.5968 Remote Similarity NPD8273 Phase 1
0.5965 Remote Similarity NPD5345 Clinical (unspecified phase)
0.5963 Remote Similarity NPD5696 Approved
0.5962 Remote Similarity NPD5370 Suspended
0.595 Remote Similarity NPD6319 Approved
0.5935 Remote Similarity NPD7604 Phase 2
0.592 Remote Similarity NPD8448 Approved
0.592 Remote Similarity NPD8074 Phase 3
0.5909 Remote Similarity NPD5285 Approved
0.5909 Remote Similarity NPD4696 Approved
0.5909 Remote Similarity NPD4194 Approved
0.5909 Remote Similarity NPD4191 Approved
0.5909 Remote Similarity NPD4193 Approved
0.5909 Remote Similarity NPD4192 Approved
0.5909 Remote Similarity NPD5286 Approved
0.5888 Remote Similarity NPD7901 Clinical (unspecified phase)
0.5888 Remote Similarity NPD7900 Approved
0.5887 Remote Similarity NPD8342 Approved
0.5887 Remote Similarity NPD8340 Approved
0.5887 Remote Similarity NPD8341 Approved
0.5887 Remote Similarity NPD7492 Approved
0.5887 Remote Similarity NPD8299 Approved
0.5868 Remote Similarity NPD7101 Approved
0.5868 Remote Similarity NPD7100 Approved
0.5862 Remote Similarity NPD2067 Discontinued
0.5859 Remote Similarity NPD4695 Discontinued
0.5849 Remote Similarity NPD4810 Clinical (unspecified phase)
0.5842 Remote Similarity NPD6110 Phase 1
0.584 Remote Similarity NPD6616 Approved
0.5833 Remote Similarity NPD4266 Approved
0.5833 Remote Similarity NPD3196 Approved
0.5833 Remote Similarity NPD3194 Approved
0.5833 Remote Similarity NPD6009 Approved
0.5833 Remote Similarity NPD7500 Approved
0.5833 Remote Similarity NPD6356 Clinical (unspecified phase)
0.5833 Remote Similarity NPD3195 Phase 2
0.5825 Remote Similarity NPD4519 Discontinued
0.5825 Remote Similarity NPD4623 Approved
0.5824 Remote Similarity NPD6108 Clinical (unspecified phase)
0.582 Remote Similarity NPD6054 Approved
0.5812 Remote Similarity NPD6401 Clinical (unspecified phase)
0.581 Remote Similarity NPD6080 Approved
0.581 Remote Similarity NPD6904 Approved
0.581 Remote Similarity NPD5328 Approved
0.581 Remote Similarity NPD6673 Approved
0.581 Remote Similarity NPD6051 Approved
0.5804 Remote Similarity NPD5225 Approved
0.5804 Remote Similarity NPD7632 Discontinued
0.5804 Remote Similarity NPD5224 Approved
0.5804 Remote Similarity NPD4633 Approved
0.5804 Remote Similarity NPD5226 Approved
0.5794 Remote Similarity NPD7078 Approved
0.5785 Remote Similarity NPD6335 Approved
0.5781 Remote Similarity NPD8391 Approved
0.5781 Remote Similarity NPD8390 Approved
0.5781 Remote Similarity NPD8392 Approved
0.578 Remote Similarity NPD5222 Approved
0.578 Remote Similarity NPD5221 Approved
0.578 Remote Similarity NPD4697 Phase 3
0.578 Remote Similarity NPD4792 Clinical (unspecified phase)
0.578 Remote Similarity NPD5220 Clinical (unspecified phase)
0.5772 Remote Similarity NPD8444 Approved
0.5772 Remote Similarity NPD5983 Phase 2
0.5769 Remote Similarity NPD7524 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