Structure

Physi-Chem Properties

Molecular Weight:  360.14
Volume:  333.462
LogP:  -0.575
LogD:  -0.05
LogS:  -1.908
# Rotatable Bonds:  4
TPSA:  145.91
# H-Bond Aceptor:  9
# H-Bond Donor:  5
# Rings:  3
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.36
Synthetic Accessibility Score:  4.945
Fsp3:  0.812
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.988
MDCK Permeability:  9.658019553171471e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.147
Human Intestinal Absorption (HIA):  0.905
20% Bioavailability (F20%):  0.008
30% Bioavailability (F30%):  0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.186
Plasma Protein Binding (PPB):  28.063215255737305%
Volume Distribution (VD):  0.456
Pgp-substrate:  55.54209899902344%

ADMET: Metabolism

CYP1A2-inhibitor:  0.016
CYP1A2-substrate:  0.086
CYP2C19-inhibitor:  0.015
CYP2C19-substrate:  0.452
CYP2C9-inhibitor:  0.004
CYP2C9-substrate:  0.083
CYP2D6-inhibitor:  0.003
CYP2D6-substrate:  0.112
CYP3A4-inhibitor:  0.008
CYP3A4-substrate:  0.056

ADMET: Excretion

Clearance (CL):  1.066
Half-life (T1/2):  0.739

ADMET: Toxicity

hERG Blockers:  0.042
Human Hepatotoxicity (H-HT):  0.249
Drug-inuced Liver Injury (DILI):  0.072
AMES Toxicity:  0.204
Rat Oral Acute Toxicity:  0.03
Maximum Recommended Daily Dose:  0.007
Skin Sensitization:  0.289
Carcinogencity:  0.849
Eye Corrosion:  0.004
Eye Irritation:  0.187
Respiratory Toxicity:  0.812

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

  Natural Product: NPC304163

Natural Product ID:  NPC304163
Common Name*:   Plantarenaloside
IUPAC Name:   (1S,4aR,7R,7aR)-4a-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,6,7,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carbaldehyde
Synonyms:  
Standard InCHIKey:  QCCRICPXIMDIGF-FHZCTKOVSA-N
Standard InCHI:  InChI=1S/C16H24O9/c1-7-2-3-16(22)8(4-17)6-23-14(10(7)16)25-15-13(21)12(20)11(19)9(5-18)24-15/h4,6-7,9-15,18-22H,2-3,5H2,1H3/t7-,9-,10+,11-,12+,13-,14+,15+,16+/m1/s1
SMILES:  OC[C@H]1O[C@@H](O[C@@H]2OC=C([C@@]3([C@H]2[C@H](C)CC3)O)C=O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3622814
PubChem CID:   155882
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0002049] Terpene glycosides
          • [CHEMONTID:0004081] Iridoid O-glycosides

*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
NPO21324 Plantago major Species Plantaginaceae Eukaryota Entire plants the surroundings of Uppsala, Sweden 1998-SEP PMID[11421736]
NPO21324 Plantago major Species Plantaginaceae Eukaryota Whole Plant the surroundings of Uppsala, Sweden 1998-SEP PMID[11421736]
NPO14928 Huperzia serrata Species Lycopodiaceae Eukaryota n.a. n.a. n.a. PMID[12141864]
NPO16360 Gardenia carinata Species Rubiaceae Eukaryota Leaves; Twigs n.a. n.a. PMID[23550966]
NPO21324 Plantago major Species Plantaginaceae Eukaryota n.a. seed n.a. PMID[24895551]
NPO33113 castilleja tenuiflora Species Orobanchaceae Eukaryota n.a. n.a. n.a. PMID[26351040]
NPO33356 vitex mollis Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[26351040]
NPO20005 Penstemon barbatus Species Plantaginaceae Eukaryota n.a. n.a. n.a. PMID[26351040]
NPO33328 cresentia alata Species n.a. n.a. n.a. n.a. n.a. PMID[26351040]
NPO793 Pestalotiopsis microspora Species Sporocadaceae Eukaryota n.a. n.a. n.a. PMID[27556865]
NPO21324 Plantago major Species Plantaginaceae Eukaryota n.a. n.a. n.a. PMID[9784154]
NPO120 Tecoma stans Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17761 Ophiorrhiza japonica Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14928 Huperzia serrata Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16598 Helenium elegans Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21324 Plantago major Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12853 Leucocarpus perfoliatus Species Phrymaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4436 Trillium erectum Species Melanthiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2656 Phtheirospermum japonicum Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21324 Plantago major Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17761 Ophiorrhiza japonica Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2656 Phtheirospermum japonicum Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12853 Leucocarpus perfoliatus Species Phrymaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16598 Helenium elegans Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO120 Tecoma stans Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14928 Huperzia serrata Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4436 Trillium erectum Species Melanthiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO120 Tecoma stans Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16598 Helenium elegans Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21324 Plantago major Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14928 Huperzia serrata Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO27644 Machaerocereus eruca n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO11903 Alysicarpus bupleurifolius Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27798 Verticillium intertextum Species Plectosphaerellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26510 Gentianopsis ciliata Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20005 Penstemon barbatus Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4436 Trillium erectum Species Melanthiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21689 Titanotrichum oldhamii Species Gesneriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17761 Ophiorrhiza japonica Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO120 Tecoma stans Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16360 Gardenia carinata Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO793 Pestalotiopsis microspora Species Sporocadaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24674 Trichoderma album Species Hypocreaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28896 Astragalus centralpinus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28518 Solanum wendlandii Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21324 Plantago major Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12853 Leucocarpus perfoliatus Species Phrymaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29280 Argopsis megalospora n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO25748 Eugenia grandis Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15523 Euphorbia calycina Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16598 Helenium elegans Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14042 Rollinia dolabripetala Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28080 Pedicularis palustris Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8687 Chaerophyllum temulum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14928 Huperzia serrata Species Lycopodiaceae 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
NPT30 Individual Protein Cyclooxygenase-1 Homo sapiens Inhibition = 36.3 % PMID[516390]
NPT30 Individual Protein Cyclooxygenase-1 Homo sapiens Inhibition = 36.6 % PMID[516390]
NPT30 Individual Protein Cyclooxygenase-1 Homo sapiens Inhibition = 39.9 % PMID[516390]
NPT31 Individual Protein Cyclooxygenase-2 Homo sapiens Inhibition <= 30.0 % PMID[516390]

☑ 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 NPC304163 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
0.9255 High Similarity NPC63897
0.9082 High Similarity NPC287539
0.9082 High Similarity NPC3488
0.8922 High Similarity NPC110701
0.8911 High Similarity NPC127235
0.89 High Similarity NPC37240
0.8878 High Similarity NPC37866
0.88 High Similarity NPC35185
0.88 High Similarity NPC474730
0.88 High Similarity NPC4899
0.88 High Similarity NPC177013
0.8713 High Similarity NPC475928
0.8673 High Similarity NPC161293
0.8641 High Similarity NPC148270
0.8641 High Similarity NPC80338
0.8641 High Similarity NPC197813
0.8544 High Similarity NPC170432
0.8431 Intermediate Similarity NPC106668
0.8396 Intermediate Similarity NPC193741
0.835 Intermediate Similarity NPC27687
0.8241 Intermediate Similarity NPC475851
0.8241 Intermediate Similarity NPC475924
0.8119 Intermediate Similarity NPC170527
0.8081 Intermediate Similarity NPC235051
0.802 Intermediate Similarity NPC93869
0.802 Intermediate Similarity NPC6765
0.7921 Intermediate Similarity NPC274588
0.7879 Intermediate Similarity NPC93190
0.783 Intermediate Similarity NPC329704
0.781 Intermediate Similarity NPC216911
0.7767 Intermediate Similarity NPC284063
0.7767 Intermediate Similarity NPC241911
0.7767 Intermediate Similarity NPC474297
0.7736 Intermediate Similarity NPC80144
0.7723 Intermediate Similarity NPC274274
0.7723 Intermediate Similarity NPC294643
0.7723 Intermediate Similarity NPC473150
0.7714 Intermediate Similarity NPC476211
0.7714 Intermediate Similarity NPC476320
0.7714 Intermediate Similarity NPC255677
0.7714 Intermediate Similarity NPC22149
0.7714 Intermediate Similarity NPC306344
0.77 Intermediate Similarity NPC50464
0.7692 Intermediate Similarity NPC86843
0.7692 Intermediate Similarity NPC58267
0.7692 Intermediate Similarity NPC261372
0.7692 Intermediate Similarity NPC263674
0.767 Intermediate Similarity NPC101051
0.7664 Intermediate Similarity NPC329834
0.7642 Intermediate Similarity NPC27474
0.7642 Intermediate Similarity NPC298255
0.7642 Intermediate Similarity NPC67296
0.7642 Intermediate Similarity NPC28304
0.7642 Intermediate Similarity NPC476230
0.7624 Intermediate Similarity NPC120021
0.7624 Intermediate Similarity NPC65665
0.7624 Intermediate Similarity NPC231710
0.7624 Intermediate Similarity NPC216826
0.7624 Intermediate Similarity NPC470573
0.7624 Intermediate Similarity NPC270908
0.7619 Intermediate Similarity NPC49833
0.7619 Intermediate Similarity NPC249171
0.7593 Intermediate Similarity NPC86095
0.7576 Intermediate Similarity NPC149018
0.7576 Intermediate Similarity NPC171484
0.7576 Intermediate Similarity NPC470657
0.7568 Intermediate Similarity NPC106760
0.7565 Intermediate Similarity NPC13710
0.7551 Intermediate Similarity NPC98276
0.7551 Intermediate Similarity NPC259296
0.7542 Intermediate Similarity NPC1980
0.7542 Intermediate Similarity NPC238005
0.7542 Intermediate Similarity NPC141196
0.7524 Intermediate Similarity NPC472290
0.7524 Intermediate Similarity NPC304445
0.7524 Intermediate Similarity NPC236580
0.7523 Intermediate Similarity NPC41681
0.7521 Intermediate Similarity NPC473228
0.7521 Intermediate Similarity NPC470829
0.75 Intermediate Similarity NPC284929
0.75 Intermediate Similarity NPC31349
0.75 Intermediate Similarity NPC473148
0.75 Intermediate Similarity NPC118761
0.75 Intermediate Similarity NPC197541
0.75 Intermediate Similarity NPC234304
0.75 Intermediate Similarity NPC267869
0.7477 Intermediate Similarity NPC471401
0.7477 Intermediate Similarity NPC476228
0.7458 Intermediate Similarity NPC216866
0.7455 Intermediate Similarity NPC254538
0.7455 Intermediate Similarity NPC474285
0.7453 Intermediate Similarity NPC472015
0.7451 Intermediate Similarity NPC117596
0.7451 Intermediate Similarity NPC246173
0.744 Intermediate Similarity NPC289700
0.744 Intermediate Similarity NPC62172
0.7417 Intermediate Similarity NPC198714
0.7407 Intermediate Similarity NPC261117
0.7407 Intermediate Similarity NPC222062
0.7407 Intermediate Similarity NPC13171
0.7407 Intermediate Similarity NPC250545
0.7407 Intermediate Similarity NPC195510
0.7407 Intermediate Similarity NPC310804
0.7398 Intermediate Similarity NPC155529
0.7387 Intermediate Similarity NPC224414
0.7383 Intermediate Similarity NPC473146
0.7379 Intermediate Similarity NPC66504
0.7379 Intermediate Similarity NPC472125
0.7379 Intermediate Similarity NPC472124
0.7379 Intermediate Similarity NPC472126
0.7373 Intermediate Similarity NPC42675
0.7368 Intermediate Similarity NPC102619
0.7355 Intermediate Similarity NPC152091
0.7353 Intermediate Similarity NPC22918
0.7345 Intermediate Similarity NPC63244
0.7345 Intermediate Similarity NPC122339
0.7323 Intermediate Similarity NPC75616
0.7321 Intermediate Similarity NPC8431
0.7308 Intermediate Similarity NPC61201
0.7288 Intermediate Similarity NPC281840
0.7282 Intermediate Similarity NPC307699
0.7281 Intermediate Similarity NPC471244
0.7281 Intermediate Similarity NPC473303
0.7281 Intermediate Similarity NPC243572
0.7281 Intermediate Similarity NPC471245
0.7281 Intermediate Similarity NPC157929
0.7281 Intermediate Similarity NPC145625
0.7265 Intermediate Similarity NPC469822
0.7265 Intermediate Similarity NPC475309
0.7257 Intermediate Similarity NPC471476
0.7257 Intermediate Similarity NPC473324
0.7255 Intermediate Similarity NPC148534
0.7248 Intermediate Similarity NPC94919
0.7241 Intermediate Similarity NPC277583
0.7241 Intermediate Similarity NPC88945
0.7236 Intermediate Similarity NPC180079
0.7236 Intermediate Similarity NPC471361
0.7236 Intermediate Similarity NPC6108
0.7236 Intermediate Similarity NPC469752
0.7236 Intermediate Similarity NPC86159
0.7236 Intermediate Similarity NPC471352
0.7236 Intermediate Similarity NPC17896
0.7236 Intermediate Similarity NPC89514
0.7236 Intermediate Similarity NPC469754
0.7236 Intermediate Similarity NPC469751
0.7236 Intermediate Similarity NPC469753
0.7236 Intermediate Similarity NPC197707
0.7236 Intermediate Similarity NPC284406
0.7236 Intermediate Similarity NPC471359
0.7236 Intermediate Similarity NPC9499
0.7236 Intermediate Similarity NPC251866
0.7236 Intermediate Similarity NPC10823
0.7236 Intermediate Similarity NPC70542
0.7236 Intermediate Similarity NPC471358
0.7236 Intermediate Similarity NPC471360
0.7236 Intermediate Similarity NPC219085
0.7236 Intermediate Similarity NPC469755
0.7222 Intermediate Similarity NPC158350
0.7217 Intermediate Similarity NPC132668
0.7217 Intermediate Similarity NPC477944
0.7217 Intermediate Similarity NPC73986
0.7217 Intermediate Similarity NPC94141
0.7212 Intermediate Similarity NPC472199
0.7207 Intermediate Similarity NPC285927
0.72 Intermediate Similarity NPC3464
0.72 Intermediate Similarity NPC475963
0.72 Intermediate Similarity NPC151176
0.7196 Intermediate Similarity NPC470683
0.7196 Intermediate Similarity NPC474313
0.7196 Intermediate Similarity NPC470684
0.7193 Intermediate Similarity NPC272242
0.7193 Intermediate Similarity NPC274833
0.719 Intermediate Similarity NPC277191
0.719 Intermediate Similarity NPC190846
0.7179 Intermediate Similarity NPC473304
0.717 Intermediate Similarity NPC167893
0.7168 Intermediate Similarity NPC471400
0.7168 Intermediate Similarity NPC208307
0.7167 Intermediate Similarity NPC28532
0.7165 Intermediate Similarity NPC127656
0.7157 Intermediate Similarity NPC258501
0.7156 Intermediate Similarity NPC20673
0.7156 Intermediate Similarity NPC98859
0.7156 Intermediate Similarity NPC4637
0.7155 Intermediate Similarity NPC17165
0.7155 Intermediate Similarity NPC74727
0.7143 Intermediate Similarity NPC471461
0.7143 Intermediate Similarity NPC475788
0.7143 Intermediate Similarity NPC67745
0.7131 Intermediate Similarity NPC250556
0.7131 Intermediate Similarity NPC469750
0.7131 Intermediate Similarity NPC93368
0.713 Intermediate Similarity NPC207845
0.713 Intermediate Similarity NPC472719
0.7119 Intermediate Similarity NPC475632
0.7119 Intermediate Similarity NPC471249
0.7119 Intermediate Similarity NPC86020
0.7115 Intermediate Similarity NPC6414
0.7115 Intermediate Similarity NPC303451
0.7105 Intermediate Similarity NPC27551

  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 NPC304163 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
0.7236 Intermediate Similarity NPD7319 Approved
0.7143 Intermediate Similarity NPD6412 Phase 2
0.7131 Intermediate Similarity NPD7507 Approved
0.693 Remote Similarity NPD6686 Approved
0.6923 Remote Similarity NPD8133 Approved
0.6885 Remote Similarity NPD6370 Approved
0.6803 Remote Similarity NPD8513 Phase 3
0.6803 Remote Similarity NPD7503 Approved
0.6721 Remote Similarity NPD6054 Approved
0.6667 Remote Similarity NPD6016 Approved
0.6667 Remote Similarity NPD8516 Approved
0.6667 Remote Similarity NPD8517 Approved
0.6667 Remote Similarity NPD6015 Approved
0.6667 Remote Similarity NPD8515 Approved
0.6614 Remote Similarity NPD7736 Approved
0.6613 Remote Similarity NPD5988 Approved
0.6585 Remote Similarity NPD6319 Approved
0.6585 Remote Similarity NPD6059 Approved
0.6574 Remote Similarity NPD7983 Approved
0.6555 Remote Similarity NPD6053 Discontinued
0.6552 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6535 Remote Similarity NPD8293 Discontinued
0.6525 Remote Similarity NPD6371 Approved
0.6508 Remote Similarity NPD7492 Approved
0.6481 Remote Similarity NPD46 Approved
0.6481 Remote Similarity NPD6698 Approved
0.6475 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6471 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6457 Remote Similarity NPD6616 Approved
0.6423 Remote Similarity NPD7327 Approved
0.6423 Remote Similarity NPD7328 Approved
0.6415 Remote Similarity NPD4249 Approved
0.6406 Remote Similarity NPD7078 Approved
0.6379 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6379 Remote Similarity NPD4057 Clinical (unspecified phase)
0.6379 Remote Similarity NPD4056 Clinical (unspecified phase)
0.6378 Remote Similarity NPD8299 Approved
0.6378 Remote Similarity NPD8341 Approved
0.6378 Remote Similarity NPD8342 Approved
0.6378 Remote Similarity NPD8340 Approved
0.6372 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6371 Remote Similarity NPD7516 Approved
0.6355 Remote Similarity NPD4251 Approved
0.6355 Remote Similarity NPD4250 Approved
0.6349 Remote Similarity NPD8080 Discontinued
0.6341 Remote Similarity NPD6009 Approved
0.632 Remote Similarity NPD8377 Approved
0.632 Remote Similarity NPD8294 Approved
0.6306 Remote Similarity NPD5282 Discontinued
0.6299 Remote Similarity NPD7642 Approved
0.629 Remote Similarity NPD7641 Discontinued
0.6281 Remote Similarity NPD6882 Approved
0.627 Remote Similarity NPD8033 Approved
0.627 Remote Similarity NPD8296 Approved
0.627 Remote Similarity NPD8380 Approved
0.627 Remote Similarity NPD8335 Approved
0.627 Remote Similarity NPD8378 Approved
0.627 Remote Similarity NPD8274 Clinical (unspecified phase)
0.627 Remote Similarity NPD8379 Approved
0.625 Remote Similarity NPD4634 Approved
0.623 Remote Similarity NPD4632 Approved
0.6202 Remote Similarity NPD8451 Approved
0.6195 Remote Similarity NPD7839 Suspended
0.619 Remote Similarity NPD6435 Approved
0.6172 Remote Similarity NPD8328 Phase 3
0.6172 Remote Similarity NPD7830 Approved
0.6172 Remote Similarity NPD7829 Approved
0.6168 Remote Similarity NPD5363 Approved
0.6154 Remote Similarity NPD8448 Approved
0.6154 Remote Similarity NPD8074 Phase 3
0.6148 Remote Similarity NPD8297 Approved
0.6136 Remote Similarity NPD5956 Approved
0.6132 Remote Similarity NPD7154 Phase 3
0.6132 Remote Similarity NPD4788 Approved
0.6132 Remote Similarity NPD5362 Discontinued
0.6111 Remote Similarity NPD5786 Approved
0.6107 Remote Similarity NPD8337 Approved
0.6107 Remote Similarity NPD6033 Approved
0.6107 Remote Similarity NPD8336 Approved
0.6095 Remote Similarity NPD5369 Approved
0.608 Remote Similarity NPD7115 Discovery
0.608 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6071 Remote Similarity NPD5779 Approved
0.6071 Remote Similarity NPD5778 Approved
0.6068 Remote Similarity NPD5211 Phase 2
0.6038 Remote Similarity NPD4270 Approved
0.6038 Remote Similarity NPD4269 Approved
0.6036 Remote Similarity NPD5785 Approved
0.6033 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6015 Remote Similarity NPD8392 Approved
0.6015 Remote Similarity NPD8391 Approved
0.6015 Remote Similarity NPD8390 Approved
0.6 Remote Similarity NPD4821 Approved
0.6 Remote Similarity NPD5368 Approved
0.6 Remote Similarity NPD4822 Approved
0.6 Remote Similarity NPD4819 Approved
0.6 Remote Similarity NPD4820 Approved
0.6 Remote Similarity NPD5697 Approved
0.6 Remote Similarity NPD5790 Clinical (unspecified phase)
0.5982 Remote Similarity NPD7637 Suspended
0.5966 Remote Similarity NPD5141 Approved
0.5962 Remote Similarity NPD4802 Phase 2
0.5962 Remote Similarity NPD4238 Approved
0.595 Remote Similarity NPD5345 Clinical (unspecified phase)
0.595 Remote Similarity NPD6881 Approved
0.595 Remote Similarity NPD6899 Approved
0.5941 Remote Similarity NPD3181 Approved
0.5935 Remote Similarity NPD6649 Approved
0.5935 Remote Similarity NPD6650 Approved
0.5932 Remote Similarity NPD8083 Approved
0.5932 Remote Similarity NPD8139 Approved
0.5932 Remote Similarity NPD8085 Approved
0.5932 Remote Similarity NPD8084 Approved
0.5932 Remote Similarity NPD8138 Approved
0.5932 Remote Similarity NPD8086 Approved
0.5932 Remote Similarity NPD8082 Approved
0.5926 Remote Similarity NPD8338 Approved
0.5923 Remote Similarity NPD6067 Discontinued
0.5917 Remote Similarity NPD6402 Approved
0.5917 Remote Similarity NPD6675 Approved
0.5917 Remote Similarity NPD5739 Approved
0.5917 Remote Similarity NPD7128 Approved
0.5909 Remote Similarity NPD7524 Approved
0.5902 Remote Similarity NPD6372 Approved
0.5902 Remote Similarity NPD6012 Approved
0.5902 Remote Similarity NPD6013 Approved
0.5902 Remote Similarity NPD6014 Approved
0.5902 Remote Similarity NPD6373 Approved
0.5897 Remote Similarity NPD4696 Approved
0.5897 Remote Similarity NPD5285 Approved
0.5897 Remote Similarity NPD5286 Approved
0.5891 Remote Similarity NPD8444 Approved
0.5891 Remote Similarity NPD8266 Approved
0.5891 Remote Similarity NPD5983 Phase 2
0.5891 Remote Similarity NPD8267 Approved
0.5891 Remote Similarity NPD8268 Approved
0.5891 Remote Similarity NPD8269 Approved
0.5882 Remote Similarity NPD8275 Approved
0.5882 Remote Similarity NPD8276 Approved
0.587 Remote Similarity NPD7966 Clinical (unspecified phase)
0.5868 Remote Similarity NPD5701 Approved
0.5862 Remote Similarity NPD4755 Approved
0.5862 Remote Similarity NPD6084 Phase 2
0.5862 Remote Similarity NPD6083 Phase 2
0.5854 Remote Similarity NPD6883 Approved
0.5854 Remote Similarity NPD7102 Approved
0.5854 Remote Similarity NPD7290 Approved
0.5849 Remote Similarity NPD4252 Approved
0.5833 Remote Similarity NPD6110 Phase 1
0.5833 Remote Similarity NPD8081 Approved
0.5826 Remote Similarity NPD5695 Phase 3
0.582 Remote Similarity NPD6011 Approved
0.582 Remote Similarity NPD7320 Approved
0.5812 Remote Similarity NPD4225 Approved
0.581 Remote Similarity NPD4271 Approved
0.581 Remote Similarity NPD4268 Approved
0.5806 Remote Similarity NPD6617 Approved
0.5806 Remote Similarity NPD6847 Approved
0.5806 Remote Similarity NPD6869 Approved
0.5806 Remote Similarity NPD8130 Phase 1
0.5804 Remote Similarity NPD4753 Phase 2
0.5804 Remote Similarity NPD5764 Clinical (unspecified phase)
0.5804 Remote Similarity NPD6101 Approved
0.5804 Remote Similarity NPD1695 Approved
0.5802 Remote Similarity NPD7604 Phase 2
0.5798 Remote Similarity NPD5224 Approved
0.5798 Remote Similarity NPD5225 Approved
0.5798 Remote Similarity NPD5226 Approved
0.5798 Remote Similarity NPD4633 Approved
0.5789 Remote Similarity NPD8171 Discontinued
0.5785 Remote Similarity NPD8393 Approved
0.578 Remote Similarity NPD7338 Clinical (unspecified phase)
0.5763 Remote Similarity NPD4700 Approved
0.5763 Remote Similarity NPD7640 Approved
0.5763 Remote Similarity NPD7639 Approved
0.5752 Remote Similarity NPD7838 Discovery
0.575 Remote Similarity NPD5175 Approved
0.575 Remote Similarity NPD5174 Approved
0.5738 Remote Similarity NPD8140 Approved
0.5738 Remote Similarity NPD8307 Discontinued
0.5736 Remote Similarity NPD4522 Approved
0.5727 Remote Similarity NPD1733 Clinical (unspecified phase)
0.5727 Remote Similarity NPD6082 Clinical (unspecified phase)
0.5714 Remote Similarity NPD5223 Approved
0.5714 Remote Similarity NPD6336 Discontinued
0.5702 Remote Similarity NPD6411 Approved
0.5691 Remote Similarity NPD4729 Approved
0.5691 Remote Similarity NPD4730 Approved
0.569 Remote Similarity NPD4629 Approved
0.569 Remote Similarity NPD5210 Approved
0.569 Remote Similarity NPD1698 Clinical (unspecified phase)
0.5688 Remote Similarity NPD5332 Approved
0.5688 Remote Similarity NPD5331 Approved
0.5688 Remote Similarity NPD6695 Phase 3
0.5678 Remote Similarity NPD7638 Approved
0.5678 Remote Similarity NPD5696 Approved
0.566 Remote Similarity NPD5784 Clinical (unspecified phase)
0.5656 Remote Similarity NPD6008 Approved
0.5656 Remote Similarity NPD4767 Approved
0.5656 Remote Similarity NPD4768 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