Structure

Physi-Chem Properties

Molecular Weight:  270.05
Volume:  265.186
LogP:  3.502
LogD:  2.512
LogS:  -4.062
# Rotatable Bonds:  0
TPSA:  94.83
# H-Bond Aceptor:  5
# H-Bond Donor:  3
# Rings:  3
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.503
Synthetic Accessibility Score:  2.903
Fsp3:  0.067
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  2

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.016
MDCK Permeability:  1.3369167390919756e-05
Pgp-inhibitor:  0.228
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.039
20% Bioavailability (F20%):  0.158
30% Bioavailability (F30%):  0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.012
Plasma Protein Binding (PPB):  100.34050750732422%
Volume Distribution (VD):  0.324
Pgp-substrate:  2.214876651763916%

ADMET: Metabolism

CYP1A2-inhibitor:  0.975
CYP1A2-substrate:  0.374
CYP2C19-inhibitor:  0.168
CYP2C19-substrate:  0.063
CYP2C9-inhibitor:  0.731
CYP2C9-substrate:  0.544
CYP2D6-inhibitor:  0.672
CYP2D6-substrate:  0.206
CYP3A4-inhibitor:  0.272
CYP3A4-substrate:  0.088

ADMET: Excretion

Clearance (CL):  5.269
Half-life (T1/2):  0.604

ADMET: Toxicity

hERG Blockers:  0.003
Human Hepatotoxicity (H-HT):  0.249
Drug-inuced Liver Injury (DILI):  0.952
AMES Toxicity:  0.814
Rat Oral Acute Toxicity:  0.612
Maximum Recommended Daily Dose:  0.914
Skin Sensitization:  0.921
Carcinogencity:  0.833
Eye Corrosion:  0.027
Eye Irritation:  0.952
Respiratory Toxicity:  0.118

Download Data

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

  Natural Product: NPC416

Natural Product ID:  NPC416
Common Name*:   2-Hydroxychrysophanol
IUPAC Name:   1,2,8-trihydroxy-3-methylanthracene-9,10-dione
Synonyms:   2-Hydroxychrysophanol
Standard InCHIKey:  CQNVSNFEXPKHGW-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C15H10O5/c1-6-5-8-11(15(20)12(6)17)14(19)10-7(13(8)18)3-2-4-9(10)16/h2-5,16-17,20H,1H3
SMILES:  Oc1cccc2c1C(=O)c1c(C2=O)cc(c(c1O)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL190245
PubChem CID:   442759
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000018] Anthracenes
        • [CHEMONTID:0000151] Anthraquinones
          • [CHEMONTID:0001598] Hydroxyanthraquinones

*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
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. stem wood n.a. DOI[10.1021/np100247r]
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[10395501]
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[10425140]
NPO6333 Annona glabra Species Annonaceae Eukaryota Fruits n.a. n.a. PMID[15568797]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota n.a. n.a. n.a. PMID[19919095]
NPO6333 Annona glabra Species Annonaceae Eukaryota stem Taipei Botanical Garden, Taipei, Taiwan, China 2006-MAR PMID[20828184]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota flower buds and leaves Khon Kaen province, Thailand 2010 PMID[23270663]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota Leaves n.a. n.a. PMID[23642481]
NPO6333 Annona glabra Species Annonaceae Eukaryota fruits n.a. n.a. PMID[25499882]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota Flowers n.a. n.a. PMID[26462418]
NPO23736 Myrsine africana Species Primulaceae Eukaryota root n.a. n.a. PMID[2778455]
NPO23736 Myrsine africana Species Primulaceae Eukaryota n.a. n.a. n.a. PMID[29300477]
NPO20412 Magnolia grandiflora Species Magnoliaceae Eukaryota Wood n.a. n.a. PMID[7119806]
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[9584397]
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[9599260]
NPO23736 Myrsine africana Species Primulaceae Eukaryota n.a. fruit n.a. Database[Article]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota n.a. n.a. Database[FooDB]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota Rhizome n.a. n.a. Database[FooDB]
NPO20412 Magnolia grandiflora Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23736 Myrsine africana Species Primulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23736 Myrsine africana Species Primulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2443 Nelumbo lutea Species Nelumbonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20412 Magnolia grandiflora Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20412 Magnolia grandiflora Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20412 Magnolia grandiflora Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23736 Myrsine africana Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2443 Nelumbo lutea Species Nelumbonaceae 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
NPT81 Cell Line A549 Homo sapiens ED50 = 3.1 ug ml-1 PMID[469632]
NPT139 Cell Line HT-29 Homo sapiens ED50 = 2.8 ug ml-1 PMID[469632]
NPT138 Organism Brugia malayi Brugia malayi Mortality = 5.0 % PMID[469631]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Mortality = 3.0 % PMID[469631]
NPT138 Organism Brugia malayi Brugia malayi Mortality = 2.0 day PMID[469631]
NPT138 Organism Brugia malayi Brugia malayi Mortality = 3.0 day PMID[469631]
NPT138 Organism Brugia malayi Brugia malayi Mortality = 4.0 day PMID[469631]
NPT138 Organism Brugia malayi Brugia malayi Mortality = 5.0 day PMID[469631]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 5.7 ug ml-1 PMID[469632]

☑ 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 NPC416 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
1.0 High Similarity NPC61398
0.9771 High Similarity NPC258502
0.9618 High Similarity NPC294226
0.9478 High Similarity NPC147418
0.9412 High Similarity NPC203063
0.9313 High Similarity NPC99731
0.9242 High Similarity NPC117609
0.9237 High Similarity NPC282923
0.9237 High Similarity NPC234175
0.9209 High Similarity NPC238629
0.9191 High Similarity NPC53414
0.9191 High Similarity NPC53206
0.9124 High Similarity NPC13715
0.9118 High Similarity NPC254847
0.9097 High Similarity NPC302783
0.9097 High Similarity NPC473201
0.9058 High Similarity NPC242994
0.9058 High Similarity NPC138099
0.9051 High Similarity NPC471905
0.9044 High Similarity NPC283088
0.9037 High Similarity NPC52407
0.903 High Similarity NPC205992
0.9021 High Similarity NPC471907
0.9008 High Similarity NPC103540
0.8993 High Similarity NPC181560
0.8993 High Similarity NPC169452
0.8971 High Similarity NPC50924
0.8971 High Similarity NPC44437
0.8963 High Similarity NPC70622
0.8944 High Similarity NPC160777
0.8944 High Similarity NPC73416
0.8931 High Similarity NPC142956
0.8931 High Similarity NPC173978
0.8921 High Similarity NPC143438
0.8913 High Similarity NPC290030
0.8905 High Similarity NPC80035
0.8905 High Similarity NPC153088
0.8897 High Similarity NPC225051
0.8897 High Similarity NPC267205
0.8897 High Similarity NPC115458
0.8897 High Similarity NPC280295
0.8897 High Similarity NPC111845
0.8873 High Similarity NPC244691
0.8865 High Similarity NPC193555
0.8865 High Similarity NPC239136
0.8865 High Similarity NPC19631
0.8857 High Similarity NPC471853
0.8855 High Similarity NPC375356
0.8849 High Similarity NPC230811
0.8849 High Similarity NPC141368
0.8849 High Similarity NPC4214
0.8844 High Similarity NPC107109
0.8841 High Similarity NPC315275
0.8841 High Similarity NPC264112
0.8841 High Similarity NPC194764
0.8841 High Similarity NPC65005
0.8836 High Similarity NPC35
0.8836 High Similarity NPC118427
0.8832 High Similarity NPC288089
0.8824 High Similarity NPC135801
0.8815 High Similarity NPC136588
0.8815 High Similarity NPC199253
0.8806 High Similarity NPC48248
0.8797 High Similarity NPC3224
0.8794 High Similarity NPC246638
0.8794 High Similarity NPC204045
0.8794 High Similarity NPC305845
0.8792 High Similarity NPC178976
0.8786 High Similarity NPC472903
0.8786 High Similarity NPC190457
0.8786 High Similarity NPC26924
0.8779 High Similarity NPC91478
0.8779 High Similarity NPC300274
0.8777 High Similarity NPC264022
0.8776 High Similarity NPC164912
0.8776 High Similarity NPC312338
0.8776 High Similarity NPC149889
0.8768 High Similarity NPC72918
0.8759 High Similarity NPC138472
0.8759 High Similarity NPC53896
0.8759 High Similarity NPC314048
0.875 High Similarity NPC474517
0.875 High Similarity NPC93015
0.875 High Similarity NPC469526
0.875 High Similarity NPC72669
0.875 High Similarity NPC244699
0.875 High Similarity NPC34070
0.8741 High Similarity NPC21599
0.8741 High Similarity NPC79627
0.8741 High Similarity NPC193703
0.8741 High Similarity NPC146647
0.8741 High Similarity NPC34414
0.8732 High Similarity NPC135524
0.8732 High Similarity NPC73061
0.8732 High Similarity NPC248068
0.8731 High Similarity NPC324209
0.8725 High Similarity NPC14561
0.8725 High Similarity NPC77807
0.8725 High Similarity NPC5379
0.8723 High Similarity NPC315578
0.8714 High Similarity NPC123714
0.8714 High Similarity NPC206207
0.8707 High Similarity NPC144283
0.8705 High Similarity NPC272268
0.8705 High Similarity NPC191976
0.8705 High Similarity NPC155211
0.8705 High Similarity NPC474813
0.8702 High Similarity NPC120545
0.8696 High Similarity NPC282780
0.8696 High Similarity NPC166480
0.8686 High Similarity NPC58685
0.8676 High Similarity NPC233056
0.8676 High Similarity NPC31799
0.8676 High Similarity NPC26697
0.8667 High Similarity NPC199463
0.8667 High Similarity NPC37543
0.8662 High Similarity NPC472904
0.8662 High Similarity NPC290550
0.8657 High Similarity NPC96915
0.8657 High Similarity NPC231774
0.8643 High Similarity NPC245923
0.8636 High Similarity NPC307174
0.8623 High Similarity NPC4170
0.8618 High Similarity NPC311740
0.8611 High Similarity NPC471906
0.8611 High Similarity NPC48762
0.8601 High Similarity NPC291078
0.8593 High Similarity NPC473787
0.8592 High Similarity NPC96421
0.8571 High Similarity NPC223836
0.8571 High Similarity NPC7464
0.8553 High Similarity NPC84571
0.8552 High Similarity NPC68441
0.8552 High Similarity NPC34482
0.8542 High Similarity NPC66593
0.8542 High Similarity NPC471682
0.854 High Similarity NPC55949
0.8531 High Similarity NPC84273
0.8529 High Similarity NPC247250
0.8529 High Similarity NPC96024
0.8529 High Similarity NPC767
0.8521 High Similarity NPC1268
0.8519 High Similarity NPC160499
0.8511 High Similarity NPC277559
0.8511 High Similarity NPC53001
0.8511 High Similarity NPC49911
0.85 High Similarity NPC161632
0.8493 Intermediate Similarity NPC470570
0.8478 Intermediate Similarity NPC41847
0.8472 Intermediate Similarity NPC257644
0.8472 Intermediate Similarity NPC314271
0.8472 Intermediate Similarity NPC474961
0.8467 Intermediate Similarity NPC93552
0.8467 Intermediate Similarity NPC276238
0.8467 Intermediate Similarity NPC278928
0.8456 Intermediate Similarity NPC107672
0.8456 Intermediate Similarity NPC176130
0.8456 Intermediate Similarity NPC78364
0.8456 Intermediate Similarity NPC69424
0.8456 Intermediate Similarity NPC84672
0.8452 Intermediate Similarity NPC26386
0.8451 Intermediate Similarity NPC51531
0.8451 Intermediate Similarity NPC46242
0.8451 Intermediate Similarity NPC149773
0.8451 Intermediate Similarity NPC469857
0.8451 Intermediate Similarity NPC23667
0.8451 Intermediate Similarity NPC473479
0.8451 Intermediate Similarity NPC157284
0.8451 Intermediate Similarity NPC87723
0.8451 Intermediate Similarity NPC473779
0.8451 Intermediate Similarity NPC165191
0.8451 Intermediate Similarity NPC114333
0.8451 Intermediate Similarity NPC289358
0.8451 Intermediate Similarity NPC42384
0.8451 Intermediate Similarity NPC5014
0.8451 Intermediate Similarity NPC50615
0.8451 Intermediate Similarity NPC28592
0.8451 Intermediate Similarity NPC297797
0.8451 Intermediate Similarity NPC477849
0.8451 Intermediate Similarity NPC91887
0.8451 Intermediate Similarity NPC245760
0.844 Intermediate Similarity NPC118919
0.844 Intermediate Similarity NPC141934
0.844 Intermediate Similarity NPC86524
0.8435 Intermediate Similarity NPC190648
0.8435 Intermediate Similarity NPC56433
0.8435 Intermediate Similarity NPC118027
0.8435 Intermediate Similarity NPC476821
0.8435 Intermediate Similarity NPC312929
0.8435 Intermediate Similarity NPC289042
0.8435 Intermediate Similarity NPC119767
0.8435 Intermediate Similarity NPC245584
0.8435 Intermediate Similarity NPC10842
0.8435 Intermediate Similarity NPC37709
0.8435 Intermediate Similarity NPC126767
0.8429 Intermediate Similarity NPC161964
0.8429 Intermediate Similarity NPC287604
0.8429 Intermediate Similarity NPC293454
0.8429 Intermediate Similarity NPC12070
0.8429 Intermediate Similarity NPC472262

  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 NPC416 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
0.9118 High Similarity NPD1509 Clinical (unspecified phase)
0.9008 High Similarity NPD1470 Approved
0.8824 High Similarity NPD943 Approved
0.8702 High Similarity NPD1201 Approved
0.8552 High Similarity NPD7422 Clinical (unspecified phase)
0.844 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.8252 Intermediate Similarity NPD5405 Approved
0.8252 Intermediate Similarity NPD5408 Approved
0.8252 Intermediate Similarity NPD5404 Approved
0.8252 Intermediate Similarity NPD5406 Approved
0.8231 Intermediate Similarity NPD7390 Discontinued
0.8106 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.8089 Intermediate Similarity NPD6232 Discontinued
0.805 Intermediate Similarity NPD7473 Discontinued
0.7961 Intermediate Similarity NPD3226 Approved
0.7871 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7867 Intermediate Similarity NPD1511 Approved
0.7763 Intermediate Similarity NPD1512 Approved
0.7703 Intermediate Similarity NPD2346 Discontinued
0.7692 Intermediate Similarity NPD1934 Approved
0.7682 Intermediate Similarity NPD3300 Phase 2
0.7671 Intermediate Similarity NPD1607 Approved
0.766 Intermediate Similarity NPD1164 Approved
0.7643 Intermediate Similarity NPD2801 Approved
0.7588 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7571 Intermediate Similarity NPD9269 Phase 2
0.7568 Intermediate Similarity NPD1510 Phase 2
0.7547 Intermediate Similarity NPD3882 Suspended
0.7534 Intermediate Similarity NPD1240 Approved
0.7517 Intermediate Similarity NPD3764 Approved
0.7482 Intermediate Similarity NPD3019 Approved
0.7467 Intermediate Similarity NPD2344 Approved
0.7434 Intermediate Similarity NPD8166 Discontinued
0.7421 Intermediate Similarity NPD7819 Suspended
0.741 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.74 Intermediate Similarity NPD2935 Discontinued
0.7365 Intermediate Similarity NPD230 Phase 1
0.7362 Intermediate Similarity NPD6959 Discontinued
0.7357 Intermediate Similarity NPD2932 Approved
0.7355 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7355 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7342 Intermediate Similarity NPD4380 Phase 2
0.7333 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD6166 Phase 2
0.7333 Intermediate Similarity NPD2799 Discontinued
0.7313 Intermediate Similarity NPD3022 Approved
0.7313 Intermediate Similarity NPD3021 Approved
0.7312 Intermediate Similarity NPD1465 Phase 2
0.731 Intermediate Similarity NPD9494 Approved
0.7305 Intermediate Similarity NPD5844 Phase 1
0.7303 Intermediate Similarity NPD1549 Phase 2
0.7303 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7286 Intermediate Similarity NPD9268 Approved
0.7273 Intermediate Similarity NPD2309 Approved
0.7267 Intermediate Similarity NPD8150 Discontinued
0.7255 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD3818 Discontinued
0.7244 Intermediate Similarity NPD2532 Approved
0.7244 Intermediate Similarity NPD2533 Approved
0.7244 Intermediate Similarity NPD2534 Approved
0.7237 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7237 Intermediate Similarity NPD1471 Phase 3
0.7237 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7208 Intermediate Similarity NPD7003 Approved
0.72 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7195 Intermediate Similarity NPD5494 Approved
0.7178 Intermediate Similarity NPD3749 Approved
0.7178 Intermediate Similarity NPD7075 Discontinued
0.7174 Intermediate Similarity NPD5951 Approved
0.717 Intermediate Similarity NPD7458 Discontinued
0.7164 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7164 Intermediate Similarity NPD2342 Discontinued
0.7162 Intermediate Similarity NPD2313 Discontinued
0.7161 Intermediate Similarity NPD6190 Approved
0.716 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7123 Intermediate Similarity NPD2798 Approved
0.7105 Intermediate Similarity NPD3299 Clinical (unspecified phase)
0.7103 Intermediate Similarity NPD1283 Approved
0.7099 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD4628 Phase 3
0.7097 Intermediate Similarity NPD3750 Approved
0.7081 Intermediate Similarity NPD7411 Suspended
0.7063 Intermediate Similarity NPD3023 Approved
0.7063 Intermediate Similarity NPD3026 Approved
0.7059 Intermediate Similarity NPD7074 Phase 3
0.7055 Intermediate Similarity NPD3817 Phase 2
0.7042 Intermediate Similarity NPD1651 Approved
0.7042 Intermediate Similarity NPD3024 Approved
0.7042 Intermediate Similarity NPD3025 Approved
0.7034 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7022 Intermediate Similarity NPD6534 Approved
0.7022 Intermediate Similarity NPD6535 Approved
0.702 Intermediate Similarity NPD447 Suspended
0.7019 Intermediate Similarity NPD6599 Discontinued
0.7 Intermediate Similarity NPD7054 Approved
0.6994 Remote Similarity NPD8313 Approved
0.6994 Remote Similarity NPD8312 Approved
0.6985 Remote Similarity NPD9266 Approved
0.6985 Remote Similarity NPD74 Approved
0.6972 Remote Similarity NPD9545 Approved
0.6966 Remote Similarity NPD3972 Approved
0.6962 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6959 Remote Similarity NPD7472 Approved
0.695 Remote Similarity NPD9493 Approved
0.6948 Remote Similarity NPD2796 Approved
0.6933 Remote Similarity NPD6801 Discontinued
0.6923 Remote Similarity NPD6779 Approved
0.6923 Remote Similarity NPD6776 Approved
0.6923 Remote Similarity NPD6781 Approved
0.6923 Remote Similarity NPD6778 Approved
0.6923 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6923 Remote Similarity NPD2800 Approved
0.6923 Remote Similarity NPD6782 Approved
0.6923 Remote Similarity NPD6780 Approved
0.6923 Remote Similarity NPD6777 Approved
0.6919 Remote Similarity NPD6797 Phase 2
0.6914 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6912 Remote Similarity NPD9263 Approved
0.6912 Remote Similarity NPD9264 Approved
0.6912 Remote Similarity NPD9267 Approved
0.6909 Remote Similarity NPD7768 Phase 2
0.6906 Remote Similarity NPD7699 Phase 2
0.6906 Remote Similarity NPD7700 Phase 2
0.6906 Remote Similarity NPD7635 Approved
0.6901 Remote Similarity NPD6020 Phase 2
0.6897 Remote Similarity NPD1281 Approved
0.6879 Remote Similarity NPD6559 Discontinued
0.6879 Remote Similarity NPD7251 Discontinued
0.6879 Remote Similarity NPD5029 Approved
0.6879 Remote Similarity NPD5031 Approved
0.6879 Remote Similarity NPD5027 Approved
0.6875 Remote Similarity NPD7163 Clinical (unspecified phase)
0.6872 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6872 Remote Similarity NPD6213 Phase 3
0.6872 Remote Similarity NPD6212 Phase 3
0.6871 Remote Similarity NPD1876 Approved
0.6867 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6864 Remote Similarity NPD3926 Phase 2
0.6855 Remote Similarity NPD6799 Approved
0.6852 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6845 Remote Similarity NPD1247 Approved
0.6839 Remote Similarity NPD4338 Clinical (unspecified phase)
0.6839 Remote Similarity NPD1551 Phase 2
0.6832 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6831 Remote Similarity NPD7501 Clinical (unspecified phase)
0.6826 Remote Similarity NPD6234 Discontinued
0.6826 Remote Similarity NPD919 Approved
0.6824 Remote Similarity NPD1203 Approved
0.6821 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6811 Remote Similarity NPD7435 Discontinued
0.6781 Remote Similarity NPD3092 Approved
0.6781 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6779 Remote Similarity NPD257 Approved
0.6779 Remote Similarity NPD258 Approved
0.6776 Remote Similarity NPD6663 Approved
0.6774 Remote Similarity NPD8319 Approved
0.6774 Remote Similarity NPD8320 Phase 1
0.6774 Remote Similarity NPD3748 Approved
0.6772 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6759 Remote Similarity NPD4626 Approved
0.6759 Remote Similarity NPD2286 Discontinued
0.6755 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6747 Remote Similarity NPD2296 Approved
0.6744 Remote Similarity NPD7177 Discontinued
0.6744 Remote Similarity NPD3751 Discontinued
0.6743 Remote Similarity NPD5026 Approved
0.6743 Remote Similarity NPD5028 Approved
0.6743 Remote Similarity NPD5034 Approved
0.6743 Remote Similarity NPD7808 Phase 3
0.6743 Remote Similarity NPD4955 Approved
0.6743 Remote Similarity NPD36 Approved
0.6743 Remote Similarity NPD4954 Approved
0.6742 Remote Similarity NPD288 Approved
0.6735 Remote Similarity NPD1608 Approved
0.6735 Remote Similarity NPD4878 Approved
0.6733 Remote Similarity NPD5736 Approved
0.6731 Remote Similarity NPD6099 Approved
0.6731 Remote Similarity NPD6100 Approved
0.6727 Remote Similarity NPD37 Approved
0.672 Remote Similarity NPD7697 Approved
0.672 Remote Similarity NPD7696 Phase 3
0.672 Remote Similarity NPD8151 Discontinued
0.672 Remote Similarity NPD7698 Approved
0.6714 Remote Similarity NPD1609 Clinical (unspecified phase)
0.6711 Remote Similarity NPD3094 Phase 2
0.6711 Remote Similarity NPD411 Approved
0.6709 Remote Similarity NPD1243 Approved
0.6706 Remote Similarity NPD5710 Approved
0.6706 Remote Similarity NPD5711 Approved
0.6705 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6705 Remote Similarity NPD1221 Approved
0.669 Remote Similarity NPD9281 Approved
0.6689 Remote Similarity NPD1529 Clinical (unspecified phase)
0.6686 Remote Similarity NPD5030 Phase 2
0.6685 Remote Similarity NPD5037 Approved
0.6685 Remote Similarity NPD5038 Approved
0.6684 Remote Similarity NPD7871 Phase 2
0.6684 Remote Similarity NPD7870 Phase 2

  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