Structure

Physi-Chem Properties

Molecular Weight:  260.1
Volume:  270.225
LogP:  3.172
LogD:  3.019
LogS:  -3.927
# Rotatable Bonds:  4
TPSA:  48.67
# H-Bond Aceptor:  4
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.626
Synthetic Accessibility Score:  2.282
Fsp3:  0.267
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.677
MDCK Permeability:  2.0651514205383137e-05
Pgp-inhibitor:  0.039
Pgp-substrate:  0.04
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.024
30% Bioavailability (F30%):  0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.062
Plasma Protein Binding (PPB):  80.85944366455078%
Volume Distribution (VD):  1.103
Pgp-substrate:  12.06779956817627%

ADMET: Metabolism

CYP1A2-inhibitor:  0.971
CYP1A2-substrate:  0.908
CYP2C19-inhibitor:  0.889
CYP2C19-substrate:  0.415
CYP2C9-inhibitor:  0.386
CYP2C9-substrate:  0.879
CYP2D6-inhibitor:  0.342
CYP2D6-substrate:  0.874
CYP3A4-inhibitor:  0.197
CYP3A4-substrate:  0.399

ADMET: Excretion

Clearance (CL):  13.676
Half-life (T1/2):  0.517

ADMET: Toxicity

hERG Blockers:  0.038
Human Hepatotoxicity (H-HT):  0.943
Drug-inuced Liver Injury (DILI):  0.863
AMES Toxicity:  0.086
Rat Oral Acute Toxicity:  0.031
Maximum Recommended Daily Dose:  0.046
Skin Sensitization:  0.238
Carcinogencity:  0.514
Eye Corrosion:  0.008
Eye Irritation:  0.451
Respiratory Toxicity:  0.127

Download Data

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

  Natural Product: NPC137669

Natural Product ID:  NPC137669
Common Name*:   Prenyletin 6-Methyl Ether
IUPAC Name:   6-methoxy-7-(3-methylbut-2-enoxy)chromen-2-one
Synonyms:  
Standard InCHIKey:  ZLPLFUBVEZVYDX-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C15H16O4/c1-10(2)6-7-18-14-9-12-11(8-13(14)17-3)4-5-15(16)19-12/h4-6,8-9H,7H2,1-3H3
SMILES:  COc1cc2ccc(=O)oc2cc1OCC=C(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL594886
PubChem CID:   1764914
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000145] Coumarins 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
NPO10763 Aralia dasyphylla Species Araliaceae Eukaryota root bark n.a. n.a. PMID[10425135]
NPO13854 Prunus serotina Species Rosaceae Eukaryota n.a. kernel n.a. PMID[16652960]
NPO10051 Phyla nodiflora Species Verbenaceae Eukaryota n.a. aerial part n.a. PMID[25140335]
NPO20798 Echinodorus grandiflorus Species Alismataceae Eukaryota n.a. leaf n.a. PMID[26692456]
NPO8366 Gersemia fruticosa Species Nephtheidae Eukaryota n.a. n.a. n.a. PMID[26894524]
NPO13854 Prunus serotina Species Rosaceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO13854 Prunus serotina Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14974.1 0stoc commune var. flagelliforme Varieties 0stocaceae Bacteria n.a. n.a. n.a. Database[MetaboLights]
NPO14974.1 0stoc commune var. flagelliforme Varieties 0stocaceae Bacteria n.a. n.a. n.a. Database[TCMID]
NPO10051 Phyla nodiflora Species Verbenaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13854 Prunus serotina Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13704 Endarachne binghamiae Species Scytosiphonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13854 Prunus serotina Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21606 Monocyclanthus vignei Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20798 Echinodorus grandiflorus Species Alismataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14974.1 0stoc commune var. flagelliforme Varieties 0stocaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO20919 Utetheisa ornatrix Species Erebidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4687 Gyromitra esculenta Species Discinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13854 Prunus serotina Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18959 Neolitsea buisanensis Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12674 Colchicum ritchii Species Colchicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21835 Buxus rugulosa Species Buxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19647 Palicourea crocea Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20118 Hormothamnion enteromorphoides n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO10763 Aralia dasyphylla Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15750 Thymus nummularius Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15830 Arachniodes maximowiczii Species Dryopteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9531 Premna latifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19458 Petunia axillaris Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17426 Vismia baccifera Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20725 Eysenhardtia adenostylis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20885 Duguetia furfuracea Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13704 Endarachne binghamiae Species Scytosiphonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17731 Endiandra baillonii Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10051 Phyla nodiflora Species Verbenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8366 Gersemia fruticosa Species Nephtheidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19133 Brickellia baccharidea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19215 Ormosia semicastrata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18367 Cassia grandis Species Fabaceae 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
NPT466 Cell Line U-937 Homo sapiens CC50 = 799000.0 nM PMID[565026]
NPT466 Cell Line U-937 Homo sapiens IC50 > 400000.0 nM PMID[565026]
NPT776 Organism Spodoptera littoralis Spodoptera littoralis FR50 = 0.43 n.a. PMID[565027]
NPT176 Organism Artemia salina Artemia salina LC50 = 17.6 ppm PMID[565027]

☑ 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 NPC137669 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
0.9921 High Similarity NPC241341
0.9921 High Similarity NPC36437
0.9921 High Similarity NPC233018
0.984 High Similarity NPC244799
0.984 High Similarity NPC240722
0.976 High Similarity NPC123127
0.976 High Similarity NPC27239
0.9688 High Similarity NPC309953
0.9685 High Similarity NPC319969
0.9683 High Similarity NPC19242
0.9542 High Similarity NPC164148
0.9542 High Similarity NPC43500
0.9466 High Similarity NPC20796
0.9398 High Similarity NPC300611
0.9394 High Similarity NPC270256
0.9394 High Similarity NPC13067
0.9389 High Similarity NPC167517
0.9389 High Similarity NPC286843
0.9318 High Similarity NPC76336
0.9318 High Similarity NPC20511
0.9318 High Similarity NPC139548
0.9318 High Similarity NPC52086
0.9318 High Similarity NPC148835
0.9318 High Similarity NPC95162
0.9313 High Similarity NPC240915
0.9313 High Similarity NPC234865
0.9308 High Similarity NPC472522
0.9259 High Similarity NPC138212
0.9242 High Similarity NPC82271
0.9242 High Similarity NPC126682
0.9237 High Similarity NPC474600
0.9237 High Similarity NPC7163
0.9219 High Similarity NPC474616
0.9213 High Similarity NPC127604
0.9167 High Similarity NPC73071
0.9141 High Similarity NPC474670
0.9141 High Similarity NPC194841
0.9091 High Similarity NPC92830
0.9091 High Similarity NPC147030
0.9084 High Similarity NPC123954
0.9077 High Similarity NPC476399
0.907 High Similarity NPC474651
0.907 High Similarity NPC474623
0.9058 High Similarity NPC205361
0.9048 High Similarity NPC194626
0.9048 High Similarity NPC288238
0.904 High Similarity NPC163200
0.9023 High Similarity NPC472521
0.9015 High Similarity NPC26673
0.8993 High Similarity NPC15577
0.8992 High Similarity NPC474821
0.8986 High Similarity NPC476450
0.896 High Similarity NPC222175
0.8939 High Similarity NPC137949
0.8939 High Similarity NPC5423
0.8929 High Similarity NPC96294
0.8923 High Similarity NPC210674
0.8915 High Similarity NPC474632
0.8889 High Similarity NPC235190
0.8889 High Similarity NPC180006
0.8881 High Similarity NPC224941
0.8881 High Similarity NPC311430
0.888 High Similarity NPC281356
0.888 High Similarity NPC298796
0.8872 High Similarity NPC277021
0.8865 High Similarity NPC30688
0.8865 High Similarity NPC176903
0.8864 High Similarity NPC73738
0.8841 High Similarity NPC34245
0.8841 High Similarity NPC91492
0.8841 High Similarity NPC236419
0.8841 High Similarity NPC7439
0.8841 High Similarity NPC256555
0.8841 High Similarity NPC110067
0.8837 High Similarity NPC27352
0.8832 High Similarity NPC472520
0.8832 High Similarity NPC279851
0.8828 High Similarity NPC108545
0.8803 High Similarity NPC294522
0.8803 High Similarity NPC114740
0.8803 High Similarity NPC205727
0.8803 High Similarity NPC21184
0.8803 High Similarity NPC120426
0.88 High Similarity NPC152306
0.88 High Similarity NPC265547
0.8797 High Similarity NPC245120
0.8788 High Similarity NPC79184
0.8788 High Similarity NPC307042
0.8788 High Similarity NPC474617
0.8779 High Similarity NPC474636
0.8777 High Similarity NPC471763
0.8769 High Similarity NPC101894
0.875 High Similarity NPC474521
0.875 High Similarity NPC474530
0.875 High Similarity NPC474540
0.8741 High Similarity NPC213197
0.874 High Similarity NPC267064
0.8732 High Similarity NPC313334
0.8732 High Similarity NPC206264
0.8732 High Similarity NPC212670
0.8731 High Similarity NPC167111
0.8731 High Similarity NPC471910
0.8731 High Similarity NPC318400
0.8731 High Similarity NPC133956
0.8731 High Similarity NPC296624
0.8731 High Similarity NPC207002
0.873 High Similarity NPC308217
0.8723 High Similarity NPC178129
0.8723 High Similarity NPC231149
0.8723 High Similarity NPC476347
0.872 High Similarity NPC304208
0.872 High Similarity NPC52464
0.8712 High Similarity NPC168710
0.8705 High Similarity NPC230157
0.8682 High Similarity NPC472518
0.8682 High Similarity NPC273772
0.8682 High Similarity NPC109675
0.8681 High Similarity NPC163598
0.8681 High Similarity NPC120774
0.8681 High Similarity NPC264875
0.8672 High Similarity NPC310373
0.8667 High Similarity NPC319859
0.8667 High Similarity NPC55149
0.8667 High Similarity NPC18804
0.8667 High Similarity NPC84894
0.8667 High Similarity NPC267412
0.8667 High Similarity NPC74655
0.8667 High Similarity NPC166672
0.8667 High Similarity NPC260265
0.8667 High Similarity NPC307412
0.8667 High Similarity NPC100986
0.8667 High Similarity NPC195343
0.8667 High Similarity NPC198381
0.8667 High Similarity NPC164269
0.8667 High Similarity NPC47163
0.8667 High Similarity NPC287182
0.8667 High Similarity NPC111635
0.8667 High Similarity NPC127888
0.8662 High Similarity NPC476348
0.8662 High Similarity NPC139839
0.8662 High Similarity NPC187398
0.8657 High Similarity NPC14248
0.8651 High Similarity NPC96705
0.8647 High Similarity NPC80170
0.864 High Similarity NPC128633
0.8636 High Similarity NPC109275
0.8636 High Similarity NPC199204
0.8633 High Similarity NPC469564
0.8615 High Similarity NPC201667
0.8615 High Similarity NPC27671
0.8615 High Similarity NPC73413
0.8613 High Similarity NPC38874
0.8613 High Similarity NPC476171
0.8605 High Similarity NPC96286
0.8605 High Similarity NPC270326
0.8605 High Similarity NPC248429
0.8603 High Similarity NPC469675
0.8603 High Similarity NPC472424
0.8603 High Similarity NPC471625
0.8603 High Similarity NPC281241
0.8603 High Similarity NPC471909
0.8603 High Similarity NPC86892
0.8593 High Similarity NPC7526
0.8593 High Similarity NPC474810
0.8593 High Similarity NPC222036
0.8592 High Similarity NPC41844
0.8592 High Similarity NPC52740
0.8582 High Similarity NPC29734
0.8571 High Similarity NPC153547
0.8571 High Similarity NPC48315
0.8562 High Similarity NPC186507
0.8561 High Similarity NPC224774
0.8561 High Similarity NPC258567
0.8561 High Similarity NPC121740
0.855 High Similarity NPC471828
0.855 High Similarity NPC471827
0.854 High Similarity NPC128529
0.854 High Similarity NPC149320
0.854 High Similarity NPC160727
0.854 High Similarity NPC471630
0.854 High Similarity NPC55615
0.854 High Similarity NPC476455
0.854 High Similarity NPC26954
0.854 High Similarity NPC177281
0.854 High Similarity NPC38099
0.854 High Similarity NPC283019
0.8538 High Similarity NPC279379
0.8531 High Similarity NPC93924
0.8531 High Similarity NPC48366
0.8529 High Similarity NPC62366
0.8529 High Similarity NPC326600
0.8529 High Similarity NPC204353
0.8529 High Similarity NPC309744
0.8529 High Similarity NPC50896
0.8527 High Similarity NPC144418
0.8511 High Similarity NPC185127
0.8507 High Similarity NPC113098
0.8496 Intermediate Similarity NPC469453
0.8496 Intermediate Similarity NPC185066
0.8496 Intermediate Similarity NPC472519

  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 NPC137669 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
0.8732 High Similarity NPD1653 Approved
0.8244 Intermediate Similarity NPD422 Phase 1
0.8082 Intermediate Similarity NPD1940 Clinical (unspecified phase)
0.8042 Intermediate Similarity NPD1652 Phase 2
0.8013 Intermediate Similarity NPD3817 Phase 2
0.7956 Intermediate Similarity NPD1008 Clinical (unspecified phase)
0.792 Intermediate Similarity NPD1358 Approved
0.7895 Intermediate Similarity NPD3496 Discontinued
0.7883 Intermediate Similarity NPD3018 Phase 2
0.7857 Intermediate Similarity NPD1613 Approved
0.7857 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7857 Intermediate Similarity NPD919 Approved
0.7829 Intermediate Similarity NPD2801 Approved
0.7826 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7801 Intermediate Similarity NPD447 Suspended
0.7799 Intermediate Similarity NPD5844 Phase 1
0.7778 Intermediate Similarity NPD2981 Phase 2
0.777 Intermediate Similarity NPD3027 Phase 3
0.776 Intermediate Similarity NPD9697 Approved
0.7754 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7727 Intermediate Similarity NPD5536 Phase 2
0.7721 Intermediate Similarity NPD2983 Phase 2
0.7721 Intermediate Similarity NPD2982 Phase 2
0.7716 Intermediate Similarity NPD7549 Discontinued
0.7714 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7714 Intermediate Similarity NPD1296 Phase 2
0.7692 Intermediate Similarity NPD5494 Approved
0.7676 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7676 Intermediate Similarity NPD5124 Phase 1
0.7643 Intermediate Similarity NPD1247 Approved
0.7613 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.76 Intermediate Similarity NPD7314 Clinical (unspecified phase)
0.7584 Intermediate Similarity NPD6799 Approved
0.7574 Intermediate Similarity NPD3705 Approved
0.7559 Intermediate Similarity NPD3134 Approved
0.7552 Intermediate Similarity NPD230 Phase 1
0.755 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7548 Intermediate Similarity NPD5402 Approved
0.7537 Intermediate Similarity NPD1548 Phase 1
0.7532 Intermediate Similarity NPD1934 Approved
0.7517 Intermediate Similarity NPD3748 Approved
0.75 Intermediate Similarity NPD3882 Suspended
0.7481 Intermediate Similarity NPD5691 Approved
0.7467 Intermediate Similarity NPD1511 Approved
0.7466 Intermediate Similarity NPD2796 Approved
0.7445 Intermediate Similarity NPD1611 Approved
0.7436 Intermediate Similarity NPD5353 Approved
0.7434 Intermediate Similarity NPD920 Approved
0.7431 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7431 Intermediate Similarity NPD1933 Approved
0.7426 Intermediate Similarity NPD1778 Approved
0.7424 Intermediate Similarity NPD5283 Phase 1
0.7394 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7372 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7372 Intermediate Similarity NPD1465 Phase 2
0.7368 Intermediate Similarity NPD1512 Approved
0.7365 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD5677 Discontinued
0.7348 Intermediate Similarity NPD5535 Approved
0.7347 Intermediate Similarity NPD3539 Phase 1
0.7347 Intermediate Similarity NPD1551 Phase 2
0.7338 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7324 Intermediate Similarity NPD6832 Phase 2
0.7324 Intermediate Similarity NPD4908 Phase 1
0.7319 Intermediate Similarity NPD1610 Phase 2
0.7319 Intermediate Similarity NPD1091 Approved
0.7315 Intermediate Similarity NPD1243 Approved
0.7312 Intermediate Similarity NPD7199 Phase 2
0.7305 Intermediate Similarity NPD1019 Discontinued
0.7303 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7301 Intermediate Similarity NPD3818 Discontinued
0.7297 Intermediate Similarity NPD3540 Phase 1
0.729 Intermediate Similarity NPD6599 Discontinued
0.7286 Intermediate Similarity NPD3225 Approved
0.7285 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD3750 Approved
0.7267 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7261 Intermediate Similarity NPD7819 Suspended
0.7261 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7256 Intermediate Similarity NPD7054 Approved
0.7241 Intermediate Similarity NPD4060 Phase 1
0.7237 Intermediate Similarity NPD4357 Discontinued
0.7237 Intermediate Similarity NPD5297 Approved
0.723 Intermediate Similarity NPD2935 Discontinued
0.7226 Intermediate Similarity NPD5585 Approved
0.7222 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD5242 Approved
0.7219 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7212 Intermediate Similarity NPD7472 Approved
0.7208 Intermediate Similarity NPD5403 Approved
0.7197 Intermediate Similarity NPD37 Approved
0.7197 Intermediate Similarity NPD6801 Discontinued
0.7192 Intermediate Similarity NPD4340 Discontinued
0.719 Intermediate Similarity NPD5401 Approved
0.7181 Intermediate Similarity NPD7266 Discontinued
0.7178 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7178 Intermediate Similarity NPD6166 Phase 2
0.7178 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7174 Intermediate Similarity NPD4626 Approved
0.7172 Intermediate Similarity NPD6233 Phase 2
0.717 Intermediate Similarity NPD4965 Approved
0.717 Intermediate Similarity NPD4967 Phase 2
0.717 Intermediate Similarity NPD4966 Approved
0.7164 Intermediate Similarity NPD1241 Discontinued
0.7161 Intermediate Similarity NPD3686 Approved
0.7161 Intermediate Similarity NPD3687 Approved
0.716 Intermediate Similarity NPD6232 Discontinued
0.7143 Intermediate Similarity NPD228 Approved
0.7143 Intermediate Similarity NPD9717 Approved
0.7143 Intermediate Similarity NPD2653 Approved
0.7134 Intermediate Similarity NPD6386 Approved
0.7134 Intermediate Similarity NPD6385 Approved
0.7133 Intermediate Similarity NPD2237 Approved
0.7133 Intermediate Similarity NPD2861 Phase 2
0.7125 Intermediate Similarity NPD7075 Discontinued
0.7124 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7117 Intermediate Similarity NPD3926 Phase 2
0.7113 Intermediate Similarity NPD3267 Approved
0.7113 Intermediate Similarity NPD2797 Approved
0.7113 Intermediate Similarity NPD3266 Approved
0.7108 Intermediate Similarity NPD7074 Phase 3
0.7105 Intermediate Similarity NPD6190 Approved
0.7099 Intermediate Similarity NPD290 Approved
0.7099 Intermediate Similarity NPD8127 Discontinued
0.7092 Intermediate Similarity NPD4749 Approved
0.7086 Intermediate Similarity NPD6621 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD7808 Phase 3
0.7081 Intermediate Similarity NPD6234 Discontinued
0.7078 Intermediate Similarity NPD3688 Clinical (unspecified phase)
0.7078 Intermediate Similarity NPD3146 Approved
0.7078 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.707 Intermediate Similarity NPD4675 Approved
0.707 Intermediate Similarity NPD4678 Approved
0.7067 Intermediate Similarity NPD1375 Discontinued
0.7066 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7066 Intermediate Similarity NPD6797 Phase 2
0.7059 Intermediate Similarity NPD6671 Approved
0.705 Intermediate Similarity NPD17 Approved
0.7047 Intermediate Similarity NPD1510 Phase 2
0.7045 Intermediate Similarity NPD2684 Approved
0.7039 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD4110 Phase 3
0.7039 Intermediate Similarity NPD4628 Phase 3
0.7039 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD7473 Discontinued
0.7025 Intermediate Similarity NPD5090 Approved
0.7025 Intermediate Similarity NPD5089 Approved
0.7025 Intermediate Similarity NPD7411 Suspended
0.7024 Intermediate Similarity NPD7251 Discontinued
0.702 Intermediate Similarity NPD1549 Phase 2
0.7019 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7007 Intermediate Similarity NPD4307 Phase 2
0.7006 Intermediate Similarity NPD6055 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD8158 Clinical (unspecified phase)
0.6993 Remote Similarity NPD1203 Approved
0.6993 Remote Similarity NPD2219 Phase 1
0.6986 Remote Similarity NPD6798 Discontinued
0.6986 Remote Similarity NPD411 Approved
0.6986 Remote Similarity NPD3268 Approved
0.6986 Remote Similarity NPD6410 Clinical (unspecified phase)
0.6978 Remote Similarity NPD1357 Approved
0.6974 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6972 Remote Similarity NPD4359 Approved
0.6966 Remote Similarity NPD5752 Clinical (unspecified phase)
0.6963 Remote Similarity NPD7843 Approved
0.6962 Remote Similarity NPD4380 Phase 2
0.6959 Remote Similarity NPD6355 Discontinued
0.6957 Remote Similarity NPD7768 Phase 2
0.6957 Remote Similarity NPD1408 Clinical (unspecified phase)
0.6954 Remote Similarity NPD5763 Approved
0.6954 Remote Similarity NPD5762 Approved
0.6954 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6954 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6939 Remote Similarity NPD1726 Clinical (unspecified phase)
0.6937 Remote Similarity NPD4585 Approved
0.6934 Remote Similarity NPD7157 Approved
0.6923 Remote Similarity NPD8651 Approved
0.6923 Remote Similarity NPD3647 Clinical (unspecified phase)
0.6918 Remote Similarity NPD7095 Approved
0.6918 Remote Similarity NPD4625 Phase 3
0.6908 Remote Similarity NPD2424 Discontinued
0.6903 Remote Similarity NPD7837 Clinical (unspecified phase)
0.6901 Remote Similarity NPD1608 Approved
0.6897 Remote Similarity NPD9494 Approved
0.6894 Remote Similarity NPD968 Approved
0.6892 Remote Similarity NPD1240 Approved
0.6887 Remote Similarity NPD6032 Approved
0.6871 Remote Similarity NPD1699 Clinical (unspecified phase)
0.6871 Remote Similarity NPD1048 Approved
0.6867 Remote Similarity NPD6111 Discontinued
0.6863 Remote Similarity NPD6674 Discontinued
0.6859 Remote Similarity NPD2533 Approved
0.6859 Remote Similarity NPD1424 Approved
0.6859 Remote Similarity NPD2532 Approved
0.6859 Remote Similarity NPD2534 Approved
0.6857 Remote Similarity NPD9268 Approved
0.6839 Remote Similarity NPD7124 Phase 2
0.6835 Remote Similarity NPD7644 Approved
0.6831 Remote Similarity NPD1535 Discovery

  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