Structure

Physi-Chem Properties

Molecular Weight:  524.13
Volume:  500.457
LogP:  3.695
LogD:  2.611
LogS:  -4.51
# Rotatable Bonds:  6
TPSA:  157.28
# H-Bond Aceptor:  11
# H-Bond Donor:  4
# Rings:  5
# Heavy Atoms:  11

MedChem Properties

QED Drug-Likeness Score:  0.293
Synthetic Accessibility Score:  3.714
Fsp3:  0.222
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.414
MDCK Permeability:  2.2249783796723932e-05
Pgp-inhibitor:  0.994
Pgp-substrate:  0.157
Human Intestinal Absorption (HIA):  0.328
20% Bioavailability (F20%):  0.01
30% Bioavailability (F30%):  0.273

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.002
Plasma Protein Binding (PPB):  84.98221588134766%
Volume Distribution (VD):  0.75
Pgp-substrate:  24.484474182128906%

ADMET: Metabolism

CYP1A2-inhibitor:  0.15
CYP1A2-substrate:  0.913
CYP2C19-inhibitor:  0.077
CYP2C19-substrate:  0.066
CYP2C9-inhibitor:  0.765
CYP2C9-substrate:  0.728
CYP2D6-inhibitor:  0.081
CYP2D6-substrate:  0.697
CYP3A4-inhibitor:  0.606
CYP3A4-substrate:  0.649

ADMET: Excretion

Clearance (CL):  2.973
Half-life (T1/2):  0.769

ADMET: Toxicity

hERG Blockers:  0.325
Human Hepatotoxicity (H-HT):  0.283
Drug-inuced Liver Injury (DILI):  0.8
AMES Toxicity:  0.175
Rat Oral Acute Toxicity:  0.093
Maximum Recommended Daily Dose:  0.868
Skin Sensitization:  0.826
Carcinogencity:  0.027
Eye Corrosion:  0.003
Eye Irritation:  0.339
Respiratory Toxicity:  0.072

Download Data

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

  Natural Product: NPC101731

Natural Product ID:  NPC101731
Common Name*:   Palstatin
IUPAC Name:   5,7-dihydroxy-2-[(2R,3R)-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-5-methoxy-2,3-dihydro-1,4-benzodioxin-7-yl]chromen-4-one
Synonyms:   Palstatin
Standard InCHIKey:  KIEFQALNZCXSHH-ZEQKJWHPSA-N
Standard InCHI:  InChI=1S/C27H24O11/c1-33-19-6-13(7-20(34-2)25(19)32)26-23(11-28)38-27-21(35-3)4-12(5-22(27)37-26)17-10-16(31)24-15(30)8-14(29)9-18(24)36-17/h4-10,23,26,28-30,32H,11H2,1-3H3/t23-,26-/m1/s1
SMILES:  COc1cc(cc(c1O)OC)[C@@H]1[C@@H](CO)Oc2c(cc(cc2O1)c1cc(=O)c2c(cc(cc2o1)O)O)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL523569
PubChem CID:   5323578
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0001392] Lignans, neolignans and related compounds
      • [CHEMONTID:0001844] Flavonolignans

*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
NPO19975 Pycnandra acuminata Species Sapotaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.phytochem.2007.07.001]
NPO40862 Hymeneae palustris Species n.a. n.a. n.a. n.a. n.a. PMID[12608861]
NPO5140 Dipteryx odorata Species Fabaceae Eukaryota seeds n.a. n.a. PMID[12762787]
NPO5140 Dipteryx odorata Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[12762809]
NPO6412 Echinacea pallida Species Asteraceae Eukaryota root n.a. n.a. PMID[15921428]
NPO633 Mesembryanthemum expansum Species Aizoaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20569 Psychotria serpens Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5140 Dipteryx odorata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO633 Mesembryanthemum expansum Species Aizoaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20569 Psychotria serpens Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6856.1 Artemisia ludoviciana subsp. mexicana Subspecies Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5140 Dipteryx odorata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20569 Psychotria serpens Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO6412 Echinacea pallida Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12118 Cleistopholis staudtii Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11339 Litsea salicifolia Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12602 Leuzea centauroides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO940 Vernonia anisochaetoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12828 Dysidea tupha Species Dysideidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4759 Helleborus multifidus Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10970 Osmorhiza aristata Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6861 Galium dasypodum Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8129 Inocybe geophylla Species Inocybaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO218 Acer carpinifolium Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7874 Helichrysum lepidissimum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11506 Stipa vaseyi Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4322 Scabiosa succisa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26095 Hypericum revolutum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20569 Psychotria serpens Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO633 Mesembryanthemum expansum Species Aizoaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5534 Alternaria kikuchiana Species Pleosporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6856.1 Artemisia ludoviciana subsp. mexicana Subspecies Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19975 Pycnandra acuminata Species Sapotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8609 Hopea utilis Species Dipterocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1695 Monascus pilosus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10010 Evernia vulpina Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5140 Dipteryx odorata 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
NPT90 Cell Line DU-145 Homo sapiens GI50 > 10.0 ug.mL-1 PMID[450692]
NPT575 Cell Line KM-20L2 Homo sapiens GI50 > 10.0 ug.mL-1 PMID[450692]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 = 5.9 ug.mL-1 PMID[450692]
NPT395 Cell Line SF-268 Homo sapiens GI50 > 10.0 ug.mL-1 PMID[450692]
NPT83 Cell Line MCF7 Homo sapiens GI50 = 3.6 ug.mL-1 PMID[450692]
NPT1081 Cell Line BXPC-3 Homo sapiens GI50 = 3.2 ug.mL-1 PMID[450692]
NPT168 Cell Line P388 Mus musculus GI50 = 8.5 ug.mL-1 PMID[450692]
NPT1522 Organism Neisseria gonorrhoeae Neisseria gonorrhoeae MIC = 1.0 ug.mL-1 PMID[450692]

☑ 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 NPC101731 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
0.9934 High Similarity NPC305987
0.9934 High Similarity NPC288131
0.9934 High Similarity NPC113163
0.9934 High Similarity NPC66618
0.9934 High Similarity NPC165970
0.9934 High Similarity NPC84324
0.9803 High Similarity NPC476410
0.9803 High Similarity NPC284127
0.9803 High Similarity NPC172202
0.9737 High Similarity NPC183851
0.9737 High Similarity NPC63454
0.9675 High Similarity NPC158188
0.9618 High Similarity NPC243877
0.9618 High Similarity NPC295082
0.9615 High Similarity NPC125039
0.9615 High Similarity NPC72787
0.9615 High Similarity NPC7688
0.9615 High Similarity NPC7154
0.9615 High Similarity NPC36916
0.9615 High Similarity NPC58223
0.9615 High Similarity NPC36
0.9613 High Similarity NPC219927
0.9557 High Similarity NPC475212
0.9548 High Similarity NPC142252
0.9548 High Similarity NPC26326
0.9494 High Similarity NPC14662
0.949 High Similarity NPC477840
0.9487 High Similarity NPC476247
0.9487 High Similarity NPC477841
0.9427 High Similarity NPC222936
0.9427 High Similarity NPC284960
0.9423 High Similarity NPC474038
0.9419 High Similarity NPC117418
0.9419 High Similarity NPC53545
0.9416 High Similarity NPC250922
0.9412 High Similarity NPC18727
0.9404 High Similarity NPC48479
0.9404 High Similarity NPC177298
0.9379 High Similarity NPC472993
0.9371 High Similarity NPC260266
0.9367 High Similarity NPC311830
0.9367 High Similarity NPC22832
0.9363 High Similarity NPC473043
0.9359 High Similarity NPC472631
0.9359 High Similarity NPC470326
0.9359 High Similarity NPC119209
0.9359 High Similarity NPC472630
0.9359 High Similarity NPC118256
0.9359 High Similarity NPC174953
0.9359 High Similarity NPC192686
0.9359 High Similarity NPC475784
0.9355 High Similarity NPC470402
0.9355 High Similarity NPC183
0.9355 High Similarity NPC112954
0.9355 High Similarity NPC474055
0.9355 High Similarity NPC472598
0.9351 High Similarity NPC477503
0.9351 High Similarity NPC45849
0.9351 High Similarity NPC470327
0.9351 High Similarity NPC200761
0.9346 High Similarity NPC302950
0.9346 High Similarity NPC219582
0.9346 High Similarity NPC236637
0.9342 High Similarity NPC338131
0.9338 High Similarity NPC120464
0.9313 High Similarity NPC209296
0.9313 High Similarity NPC188079
0.9313 High Similarity NPC195257
0.9308 High Similarity NPC210073
0.9308 High Similarity NPC115674
0.9304 High Similarity NPC472625
0.9304 High Similarity NPC88023
0.9304 High Similarity NPC191306
0.9304 High Similarity NPC19709
0.9304 High Similarity NPC270335
0.9304 High Similarity NPC272064
0.9304 High Similarity NPC309025
0.9304 High Similarity NPC243930
0.9299 High Similarity NPC472634
0.9299 High Similarity NPC472632
0.9299 High Similarity NPC471499
0.9299 High Similarity NPC471212
0.9299 High Similarity NPC289771
0.9299 High Similarity NPC471211
0.9295 High Similarity NPC473990
0.929 High Similarity NPC320825
0.929 High Similarity NPC278778
0.929 High Similarity NPC326037
0.929 High Similarity NPC470328
0.929 High Similarity NPC13858
0.929 High Similarity NPC291878
0.929 High Similarity NPC35038
0.929 High Similarity NPC209614
0.929 High Similarity NPC472626
0.929 High Similarity NPC195796
0.9286 High Similarity NPC250822
0.9286 High Similarity NPC75279
0.9286 High Similarity NPC162351
0.9286 High Similarity NPC58382
0.9286 High Similarity NPC276409
0.9281 High Similarity NPC50403
0.9281 High Similarity NPC133953
0.9281 High Similarity NPC28274
0.9276 High Similarity NPC183950
0.9276 High Similarity NPC223579
0.9276 High Similarity NPC137062
0.9276 High Similarity NPC52005
0.9276 High Similarity NPC287101
0.9272 High Similarity NPC62536
0.9272 High Similarity NPC33265
0.9255 High Similarity NPC102277
0.9255 High Similarity NPC51326
0.9255 High Similarity NPC476365
0.9255 High Similarity NPC279209
0.9255 High Similarity NPC231194
0.925 High Similarity NPC226304
0.925 High Similarity NPC325555
0.925 High Similarity NPC265530
0.925 High Similarity NPC229729
0.9241 High Similarity NPC189142
0.9241 High Similarity NPC474033
0.9241 High Similarity NPC77660
0.9241 High Similarity NPC474034
0.9241 High Similarity NPC472635
0.9236 High Similarity NPC282009
0.9236 High Similarity NPC287328
0.9236 High Similarity NPC110349
0.9231 High Similarity NPC156057
0.9231 High Similarity NPC475267
0.9231 High Similarity NPC474836
0.9231 High Similarity NPC27337
0.9231 High Similarity NPC48208
0.9231 High Similarity NPC473272
0.9231 High Similarity NPC474208
0.9231 High Similarity NPC291508
0.9231 High Similarity NPC52889
0.9231 High Similarity NPC471515
0.9231 High Similarity NPC162869
0.9231 High Similarity NPC284820
0.9231 High Similarity NPC52530
0.9231 High Similarity NPC223787
0.9231 High Similarity NPC471479
0.9226 High Similarity NPC138360
0.9226 High Similarity NPC280339
0.9226 High Similarity NPC92659
0.9226 High Similarity NPC208197
0.9226 High Similarity NPC213622
0.9226 High Similarity NPC321779
0.9226 High Similarity NPC201136
0.9226 High Similarity NPC196439
0.9226 High Similarity NPC146165
0.9226 High Similarity NPC50715
0.9226 High Similarity NPC183597
0.9226 High Similarity NPC227325
0.9226 High Similarity NPC167815
0.9226 High Similarity NPC163780
0.9226 High Similarity NPC4455
0.9226 High Similarity NPC2476
0.9226 High Similarity NPC128863
0.9221 High Similarity NPC471982
0.9221 High Similarity NPC106976
0.9221 High Similarity NPC472912
0.9221 High Similarity NPC19721
0.9221 High Similarity NPC257648
0.9221 High Similarity NPC60972
0.9221 High Similarity NPC123886
0.9221 High Similarity NPC477231
0.9221 High Similarity NPC39732
0.9216 High Similarity NPC219330
0.9211 High Similarity NPC119059
0.9211 High Similarity NPC195202
0.9207 High Similarity NPC217520
0.9207 High Similarity NPC139571
0.9198 High Similarity NPC256760
0.9193 High Similarity NPC45638
0.9193 High Similarity NPC226294
0.9193 High Similarity NPC201292
0.9193 High Similarity NPC105025
0.9193 High Similarity NPC225434
0.9193 High Similarity NPC475942
0.9193 High Similarity NPC223747
0.9193 High Similarity NPC227508
0.9193 High Similarity NPC93337
0.9193 High Similarity NPC203050
0.9193 High Similarity NPC120099
0.9193 High Similarity NPC219904
0.9193 High Similarity NPC58053
0.9193 High Similarity NPC186807
0.9193 High Similarity NPC469931
0.9193 High Similarity NPC86008
0.9187 High Similarity NPC207575
0.9187 High Similarity NPC5778
0.9187 High Similarity NPC8856
0.9187 High Similarity NPC113968
0.9187 High Similarity NPC21100
0.9187 High Similarity NPC277174
0.9187 High Similarity NPC73855
0.9187 High Similarity NPC13481
0.9187 High Similarity NPC197285
0.9187 High Similarity NPC171985

  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 NPC101731 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
0.9615 High Similarity NPD6167 Clinical (unspecified phase)
0.9615 High Similarity NPD6166 Phase 2
0.9615 High Similarity NPD6168 Clinical (unspecified phase)
0.9346 High Similarity NPD1934 Approved
0.9313 High Similarity NPD7054 Approved
0.9255 High Similarity NPD7472 Approved
0.9161 High Similarity NPD2393 Clinical (unspecified phase)
0.9161 High Similarity NPD2801 Approved
0.9136 High Similarity NPD7074 Phase 3
0.908 High Similarity NPD6797 Phase 2
0.9045 High Similarity NPD4868 Clinical (unspecified phase)
0.9024 High Similarity NPD7251 Discontinued
0.897 High Similarity NPD7808 Phase 3
0.8947 High Similarity NPD1511 Approved
0.8896 High Similarity NPD3818 Discontinued
0.8861 High Similarity NPD3817 Phase 2
0.8855 High Similarity NPD4338 Clinical (unspecified phase)
0.8846 High Similarity NPD4380 Phase 2
0.8831 High Similarity NPD1512 Approved
0.8805 High Similarity NPD3882 Suspended
0.875 High Similarity NPD4381 Clinical (unspecified phase)
0.8735 High Similarity NPD7993 Clinical (unspecified phase)
0.8589 High Similarity NPD6959 Discontinued
0.8509 High Similarity NPD8443 Clinical (unspecified phase)
0.8503 High Similarity NPD7804 Clinical (unspecified phase)
0.8431 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8431 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8415 Intermediate Similarity NPD5494 Approved
0.8408 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8408 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8405 Intermediate Similarity NPD7075 Discontinued
0.8393 Intermediate Similarity NPD5844 Phase 1
0.8377 Intermediate Similarity NPD1549 Phase 2
0.8323 Intermediate Similarity NPD7411 Suspended
0.8313 Intermediate Similarity NPD6232 Discontinued
0.8282 Intermediate Similarity NPD5402 Approved
0.8274 Intermediate Similarity NPD7473 Discontinued
0.8272 Intermediate Similarity NPD6801 Discontinued
0.8247 Intermediate Similarity NPD2796 Approved
0.8221 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8221 Intermediate Similarity NPD1465 Phase 2
0.8187 Intermediate Similarity NPD5403 Approved
0.8182 Intermediate Similarity NPD1510 Phase 2
0.814 Intermediate Similarity NPD6559 Discontinued
0.8113 Intermediate Similarity NPD6799 Approved
0.811 Intermediate Similarity NPD7819 Suspended
0.8107 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8063 Intermediate Similarity NPD5401 Approved
0.8039 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.8039 Intermediate Similarity NPD1613 Approved
0.7922 Intermediate Similarity NPD1240 Approved
0.7911 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7853 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7843 Intermediate Similarity NPD3027 Phase 3
0.7836 Intermediate Similarity NPD3926 Phase 2
0.7829 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7824 Intermediate Similarity NPD7199 Phase 2
0.7821 Intermediate Similarity NPD1607 Approved
0.7821 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7818 Intermediate Similarity NPD6599 Discontinued
0.7806 Intermediate Similarity NPD943 Approved
0.7805 Intermediate Similarity NPD1653 Approved
0.7803 Intermediate Similarity NPD7228 Approved
0.7803 Intermediate Similarity NPD3751 Discontinued
0.7798 Intermediate Similarity NPD7768 Phase 2
0.7778 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD3787 Discontinued
0.7756 Intermediate Similarity NPD230 Phase 1
0.7751 Intermediate Similarity NPD3749 Approved
0.7719 Intermediate Similarity NPD1247 Approved
0.7706 Intermediate Similarity NPD919 Approved
0.7706 Intermediate Similarity NPD6234 Discontinued
0.7702 Intermediate Similarity NPD3750 Approved
0.7669 Intermediate Similarity NPD7390 Discontinued
0.7654 Intermediate Similarity NPD6190 Approved
0.764 Intermediate Similarity NPD8313 Approved
0.764 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.764 Intermediate Similarity NPD8312 Approved
0.7637 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.763 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7627 Intermediate Similarity NPD7685 Pre-registration
0.7619 Intermediate Similarity NPD37 Approved
0.7593 Intermediate Similarity NPD4628 Phase 3
0.7588 Intermediate Similarity NPD4966 Approved
0.7588 Intermediate Similarity NPD4965 Approved
0.7588 Intermediate Similarity NPD4967 Phase 2
0.7568 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7564 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7562 Intermediate Similarity NPD1551 Phase 2
0.7561 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7556 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7548 Intermediate Similarity NPD4908 Phase 1
0.7532 Intermediate Similarity NPD447 Suspended
0.7531 Intermediate Similarity NPD2800 Approved
0.7515 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7515 Intermediate Similarity NPD2532 Approved
0.7515 Intermediate Similarity NPD2534 Approved
0.7515 Intermediate Similarity NPD2533 Approved
0.75 Intermediate Similarity NPD8151 Discontinued
0.7485 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7453 Intermediate Similarity NPD6100 Approved
0.7453 Intermediate Similarity NPD6099 Approved
0.7453 Intermediate Similarity NPD2935 Discontinued
0.7452 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7447 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7421 Intermediate Similarity NPD1933 Approved
0.741 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD3748 Approved
0.7389 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7375 Intermediate Similarity NPD6651 Approved
0.7372 Intermediate Similarity NPD9494 Approved
0.7368 Intermediate Similarity NPD8455 Phase 2
0.7366 Intermediate Similarity NPD4360 Phase 2
0.7366 Intermediate Similarity NPD4363 Phase 3
0.7354 Intermediate Similarity NPD6778 Approved
0.7354 Intermediate Similarity NPD6779 Approved
0.7354 Intermediate Similarity NPD6782 Approved
0.7354 Intermediate Similarity NPD6776 Approved
0.7354 Intermediate Similarity NPD6781 Approved
0.7354 Intermediate Similarity NPD6777 Approved
0.7354 Intermediate Similarity NPD6780 Approved
0.7338 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7337 Intermediate Similarity NPD3226 Approved
0.7333 Intermediate Similarity NPD7240 Approved
0.7322 Intermediate Similarity NPD8150 Discontinued
0.7321 Intermediate Similarity NPD920 Approved
0.7317 Intermediate Similarity NPD1243 Approved
0.731 Intermediate Similarity NPD6844 Discontinued
0.7306 Intermediate Similarity NPD7584 Approved
0.7301 Intermediate Similarity NPD7266 Discontinued
0.7301 Intermediate Similarity NPD2344 Approved
0.7284 Intermediate Similarity NPD7033 Discontinued
0.7284 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD5953 Discontinued
0.7245 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7245 Intermediate Similarity NPD7783 Phase 2
0.724 Intermediate Similarity NPD7435 Discontinued
0.7235 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7233 Intermediate Similarity NPD6798 Discontinued
0.7225 Intermediate Similarity NPD5353 Approved
0.7215 Intermediate Similarity NPD6832 Phase 2
0.7212 Intermediate Similarity NPD1652 Phase 2
0.7208 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7202 Intermediate Similarity NPD7870 Phase 2
0.7202 Intermediate Similarity NPD7871 Phase 2
0.7202 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7198 Intermediate Similarity NPD7549 Discontinued
0.7188 Intermediate Similarity NPD6233 Phase 2
0.7186 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7171 Intermediate Similarity NPD1548 Phase 1
0.7169 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7167 Intermediate Similarity NPD7286 Phase 2
0.715 Intermediate Similarity NPD7697 Approved
0.715 Intermediate Similarity NPD7696 Phase 3
0.715 Intermediate Similarity NPD7698 Approved
0.7143 Intermediate Similarity NPD7038 Approved
0.7143 Intermediate Similarity NPD7039 Approved
0.7135 Intermediate Similarity NPD8434 Phase 2
0.7134 Intermediate Similarity NPD1203 Approved
0.7126 Intermediate Similarity NPD2309 Approved
0.7125 Intermediate Similarity NPD2313 Discontinued
0.7119 Intermediate Similarity NPD8127 Discontinued
0.7099 Intermediate Similarity NPD5124 Phase 1
0.7099 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7099 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7098 Intermediate Similarity NPD6823 Phase 2
0.7097 Intermediate Similarity NPD1610 Phase 2
0.7095 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7092 Intermediate Similarity NPD7701 Phase 2
0.7091 Intermediate Similarity NPD2346 Discontinued
0.709 Intermediate Similarity NPD6534 Approved
0.709 Intermediate Similarity NPD6535 Approved
0.7079 Intermediate Similarity NPD5711 Approved
0.7079 Intermediate Similarity NPD5710 Approved
0.7073 Intermediate Similarity NPD2799 Discontinued
0.7051 Intermediate Similarity NPD9269 Phase 2
0.7044 Intermediate Similarity NPD3018 Phase 2
0.7041 Intermediate Similarity NPD7212 Phase 2
0.7041 Intermediate Similarity NPD7213 Phase 3
0.7039 Intermediate Similarity NPD5242 Approved
0.7035 Intermediate Similarity NPD7458 Discontinued
0.7031 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.702 Intermediate Similarity NPD7874 Approved
0.702 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD3268 Approved
0.7006 Intermediate Similarity NPD2654 Approved
0.7006 Intermediate Similarity NPD6674 Discontinued
0.7 Intermediate Similarity NPD7447 Phase 1
0.6987 Remote Similarity NPD422 Phase 1
0.6985 Remote Similarity NPD7801 Approved
0.6983 Remote Similarity NPD7229 Phase 3
0.6981 Remote Similarity NPD2798 Approved
0.6979 Remote Similarity NPD7700 Phase 2
0.6979 Remote Similarity NPD7699 Phase 2
0.6974 Remote Similarity NPD7680 Approved
0.6963 Remote Similarity NPD4362 Clinical (unspecified phase)
0.6963 Remote Similarity NPD4361 Phase 2
0.6962 Remote Similarity NPD3225 Approved
0.6954 Remote Similarity NPD6386 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