Structure

Physi-Chem Properties

Molecular Weight:  388.15
Volume:  389.179
LogP:  1.619
LogD:  1.922
LogS:  -3.676
# Rotatable Bonds:  7
TPSA:  97.61
# H-Bond Aceptor:  7
# H-Bond Donor:  3
# Rings:  3
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.671
Synthetic Accessibility Score:  3.488
Fsp3:  0.333
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.828
MDCK Permeability:  1.3485041563399136e-05
Pgp-inhibitor:  0.833
Pgp-substrate:  0.148
Human Intestinal Absorption (HIA):  0.028
20% Bioavailability (F20%):  0.004
30% Bioavailability (F30%):  0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.676
Plasma Protein Binding (PPB):  72.29446411132812%
Volume Distribution (VD):  0.617
Pgp-substrate:  23.50409698486328%

ADMET: Metabolism

CYP1A2-inhibitor:  0.053
CYP1A2-substrate:  0.827
CYP2C19-inhibitor:  0.018
CYP2C19-substrate:  0.833
CYP2C9-inhibitor:  0.048
CYP2C9-substrate:  0.685
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.443
CYP3A4-inhibitor:  0.46
CYP3A4-substrate:  0.9

ADMET: Excretion

Clearance (CL):  9.097
Half-life (T1/2):  0.766

ADMET: Toxicity

hERG Blockers:  0.185
Human Hepatotoxicity (H-HT):  0.26
Drug-inuced Liver Injury (DILI):  0.45
AMES Toxicity:  0.116
Rat Oral Acute Toxicity:  0.129
Maximum Recommended Daily Dose:  0.25
Skin Sensitization:  0.93
Carcinogencity:  0.078
Eye Corrosion:  0.003
Eye Irritation:  0.035
Respiratory Toxicity:  0.241

Download Data

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

  Natural Product: NPC87725

Natural Product ID:  NPC87725
Common Name*:   (+)-Simulanol
IUPAC Name:   4-[(2S,3R)-3-(hydroxymethyl)-5-[(E)-3-hydroxyprop-1-enyl]-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2,6-dimethoxyphenol
Synonyms:   (+)-Simulanol
Standard InCHIKey:  SGRRPSBKBJVKJE-BMSLLPBFSA-N
Standard InCHI:  InChI=1S/C21H24O7/c1-25-16-9-13(10-17(26-2)19(16)24)20-15(11-23)14-7-12(5-4-6-22)8-18(27-3)21(14)28-20/h4-5,7-10,15,20,22-24H,6,11H2,1-3H3/b5-4+/t15-,20+/m0/s1
SMILES:  OC/C=C/c1cc2c(c(c1)OC)O[C@@H]([C@H]2CO)c1cc(OC)c(c(c1)OC)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1761711
PubChem CID:   52918181
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO26992 Sophora leachiana Species Fabaceae Eukaryota n.a. root n.a. DOI[10.1016/0031-9422(90)85209-X]
NPO26409 Plakortis simplex Species Plakinidae Eukaryota n.a. Caribbean n.a. PMID[10021943]
NPO26409 Plakortis simplex Species Plakinidae Eukaryota n.a. Taiwan n.a. PMID[11277748]
NPO26409 Plakortis simplex Species Plakinidae Eukaryota n.a. n.a. n.a. PMID[15921424]
NPO26203 Dysidea villosa Species Dysideidae Eukaryota n.a. Hainan, China n.a. PMID[19091557]
NPO29118 Euonymus alatus Species Celastraceae Eukaryota leaves and twigs n.a. n.a. PMID[21435874]
NPO26409 Plakortis simplex Species Plakinidae Eukaryota n.a. n.a. n.a. PMID[23806071]
NPO26409 Plakortis simplex Species Plakinidae Eukaryota n.a. China n.a. PMID[25115700]
NPO26298 Zanthoxylum simulans Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[26666037]
NPO25406 Celastrus monospermus Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[28006915]
NPO26298 Zanthoxylum simulans Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[7798955]
NPO19672 Hosta sieboldiana Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26298 Zanthoxylum simulans Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26992 Sophora leachiana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29118 Euonymus alatus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25122 Conium maculatum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24478 Morinda coreia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26298 Zanthoxylum simulans Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29118 Euonymus alatus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13313 Talipariti tiliaceum Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24478 Morinda coreia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26992 Sophora leachiana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25122 Conium maculatum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19672 Hosta sieboldiana Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26298 Zanthoxylum simulans Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19672 Hosta sieboldiana Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25122 Conium maculatum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29118 Euonymus alatus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29118 Euonymus alatus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO26789 Tephrosia bidwilli Species Geometridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25122 Conium maculatum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1267 Acronychia laurifolia Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26298 Zanthoxylum simulans Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13313 Talipariti tiliaceum Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19672 Hosta sieboldiana Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3005 Passiflora morifolia Species Passifloraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9324 0techis scutatus Species Elapidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26160 Thielavia terricola Species Chaetomiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25714 Solanum spirale Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26992 Sophora leachiana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26849 Parmelia zollingeri Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28636 Vernonia lilacina Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29118 Euonymus alatus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25358 Senecio gilliesi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25833 Asclepias subulata Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22264 Inula salsoloides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25406 Celastrus monospermus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26409 Plakortis simplex Species Plakinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24918 Jacobaea cannabifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25259 Schrebera swietenoides Species Oleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22890 Eutrochium purpureum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26690 Lactarius subpiperatus Species Lactariidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25201 Aglaia pyramidata Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24547 Xanthoria parietina Species Teloschistaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26203 Dysidea villosa Species Dysideidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24478 Morinda coreia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25802 Agave deserti Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3963 Hortonia floribunda Species Monimiaceae 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
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 11700.0 nM PMID[553324]

☑ 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 NPC87725 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 NPC263261
0.9774 High Similarity NPC477938
0.9699 High Similarity NPC263367
0.9699 High Similarity NPC209985
0.9699 High Similarity NPC29799
0.9699 High Similarity NPC177160
0.9699 High Similarity NPC477939
0.9699 High Similarity NPC54743
0.9699 High Similarity NPC10737
0.9699 High Similarity NPC156502
0.9638 High Similarity NPC260397
0.9635 High Similarity NPC280092
0.9635 High Similarity NPC12641
0.9635 High Similarity NPC45257
0.9635 High Similarity NPC93323
0.963 High Similarity NPC160283
0.963 High Similarity NPC254759
0.963 High Similarity NPC184797
0.963 High Similarity NPC309124
0.9562 High Similarity NPC47633
0.9562 High Similarity NPC85264
0.9562 High Similarity NPC477616
0.9562 High Similarity NPC102044
0.9559 High Similarity NPC311530
0.9556 High Similarity NPC236306
0.9556 High Similarity NPC70682
0.9556 High Similarity NPC473739
0.9556 High Similarity NPC292882
0.9556 High Similarity NPC232164
0.9556 High Similarity NPC260741
0.9549 High Similarity NPC187616
0.9549 High Similarity NPC49603
0.9549 High Similarity NPC287745
0.9549 High Similarity NPC193026
0.95 High Similarity NPC473408
0.9493 High Similarity NPC63879
0.9489 High Similarity NPC107161
0.9478 High Similarity NPC256262
0.9474 High Similarity NPC26394
0.9474 High Similarity NPC475840
0.9474 High Similarity NPC158331
0.9429 High Similarity NPC16269
0.9429 High Similarity NPC101376
0.9429 High Similarity NPC21776
0.9424 High Similarity NPC181615
0.9416 High Similarity NPC471389
0.9416 High Similarity NPC471414
0.9416 High Similarity NPC35216
0.9416 High Similarity NPC247291
0.9407 High Similarity NPC265433
0.9407 High Similarity NPC470802
0.9407 High Similarity NPC270456
0.9407 High Similarity NPC162659
0.9407 High Similarity NPC472334
0.9407 High Similarity NPC248727
0.9407 High Similarity NPC306441
0.9407 High Similarity NPC472336
0.9407 High Similarity NPC16435
0.9403 High Similarity NPC326095
0.9403 High Similarity NPC244983
0.9398 High Similarity NPC230219
0.9398 High Similarity NPC175067
0.9398 High Similarity NPC204215
0.9357 High Similarity NPC324492
0.9357 High Similarity NPC317053
0.9353 High Similarity NPC473108
0.9348 High Similarity NPC2613
0.9348 High Similarity NPC475891
0.9348 High Similarity NPC41782
0.9348 High Similarity NPC59841
0.9348 High Similarity NPC204347
0.9348 High Similarity NPC253878
0.9343 High Similarity NPC27495
0.9343 High Similarity NPC259519
0.9333 High Similarity NPC61946
0.9333 High Similarity NPC234333
0.9333 High Similarity NPC121812
0.9333 High Similarity NPC134968
0.9333 High Similarity NPC99572
0.9333 High Similarity NPC474206
0.9333 High Similarity NPC472337
0.9333 High Similarity NPC112939
0.9333 High Similarity NPC47398
0.9333 High Similarity NPC470356
0.9333 High Similarity NPC112246
0.9333 High Similarity NPC260898
0.9333 High Similarity NPC126409
0.9333 High Similarity NPC473413
0.9333 High Similarity NPC94750
0.9323 High Similarity NPC472597
0.9323 High Similarity NPC474017
0.9291 High Similarity NPC328567
0.9291 High Similarity NPC320671
0.9291 High Similarity NPC327412
0.9291 High Similarity NPC320970
0.9286 High Similarity NPC180953
0.9286 High Similarity NPC469557
0.9281 High Similarity NPC474104
0.927 High Similarity NPC245207
0.927 High Similarity NPC471388
0.927 High Similarity NPC32630
0.927 High Similarity NPC319647
0.927 High Similarity NPC25966
0.927 High Similarity NPC127218
0.9265 High Similarity NPC269091
0.9265 High Similarity NPC227503
0.9265 High Similarity NPC474639
0.9265 High Similarity NPC302701
0.9265 High Similarity NPC230734
0.9259 High Similarity NPC317380
0.9259 High Similarity NPC478085
0.9259 High Similarity NPC16485
0.9254 High Similarity NPC35932
0.9254 High Similarity NPC160991
0.9254 High Similarity NPC470752
0.9254 High Similarity NPC184447
0.9254 High Similarity NPC7903
0.9254 High Similarity NPC16208
0.9254 High Similarity NPC18842
0.9248 High Similarity NPC77040
0.9248 High Similarity NPC241522
0.9248 High Similarity NPC257582
0.9248 High Similarity NPC64201
0.9248 High Similarity NPC92164
0.9248 High Similarity NPC242807
0.9248 High Similarity NPC187998
0.9248 High Similarity NPC145305
0.9248 High Similarity NPC472338
0.9248 High Similarity NPC153739
0.9248 High Similarity NPC174495
0.9248 High Similarity NPC42300
0.9231 High Similarity NPC472709
0.9231 High Similarity NPC472710
0.9225 High Similarity NPC227516
0.9225 High Similarity NPC20757
0.9214 High Similarity NPC471415
0.9214 High Similarity NPC470097
0.9214 High Similarity NPC93433
0.9214 High Similarity NPC50250
0.9214 High Similarity NPC474444
0.9214 High Similarity NPC264706
0.9214 High Similarity NPC284881
0.9214 High Similarity NPC114119
0.9209 High Similarity NPC131971
0.9203 High Similarity NPC291101
0.9203 High Similarity NPC266197
0.9197 High Similarity NPC103976
0.9197 High Similarity NPC276490
0.9197 High Similarity NPC474282
0.9197 High Similarity NPC211549
0.9197 High Similarity NPC326797
0.9197 High Similarity NPC176051
0.9197 High Similarity NPC102904
0.9197 High Similarity NPC107551
0.9191 High Similarity NPC141765
0.9191 High Similarity NPC165155
0.9191 High Similarity NPC151224
0.9191 High Similarity NPC164787
0.9191 High Similarity NPC24490
0.9191 High Similarity NPC34103
0.9185 High Similarity NPC229442
0.9185 High Similarity NPC263064
0.9185 High Similarity NPC11060
0.9185 High Similarity NPC168059
0.9179 High Similarity NPC277804
0.9179 High Similarity NPC309787
0.9173 High Similarity NPC222004
0.9173 High Similarity NPC202582
0.9173 High Similarity NPC475875
0.9173 High Similarity NPC470258
0.9173 High Similarity NPC190629
0.9173 High Similarity NPC212015
0.9173 High Similarity NPC3439
0.9173 High Similarity NPC218856
0.9173 High Similarity NPC170844
0.9173 High Similarity NPC226788
0.9173 High Similarity NPC210623
0.9173 High Similarity NPC476968
0.9173 High Similarity NPC285339
0.9173 High Similarity NPC273295
0.9172 High Similarity NPC470769
0.9161 High Similarity NPC211561
0.9155 High Similarity NPC474397
0.9149 High Similarity NPC163898
0.9149 High Similarity NPC221318
0.9143 High Similarity NPC81638
0.9137 High Similarity NPC265075
0.9137 High Similarity NPC178054
0.913 High Similarity NPC22517
0.913 High Similarity NPC475836
0.913 High Similarity NPC184613
0.9124 High Similarity NPC234952
0.9124 High Similarity NPC327735
0.9124 High Similarity NPC173660
0.9124 High Similarity NPC78047
0.9124 High Similarity NPC126101
0.9118 High Similarity NPC117048
0.9118 High Similarity NPC124085
0.9118 High Similarity NPC170694
0.9118 High Similarity NPC310854

  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 NPC87725 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
0.9173 High Similarity NPD3027 Phase 3
0.9111 High Similarity NPD1612 Clinical (unspecified phase)
0.9111 High Similarity NPD1613 Approved
0.8815 High Similarity NPD1529 Clinical (unspecified phase)
0.8741 High Similarity NPD1530 Clinical (unspecified phase)
0.8551 High Similarity NPD4907 Clinical (unspecified phase)
0.8406 Intermediate Similarity NPD4908 Phase 1
0.8296 Intermediate Similarity NPD1610 Phase 2
0.8235 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8201 Intermediate Similarity NPD2861 Phase 2
0.817 Intermediate Similarity NPD1934 Approved
0.8141 Intermediate Similarity NPD6234 Discontinued
0.8085 Intermediate Similarity NPD4625 Phase 3
0.8052 Intermediate Similarity NPD37 Approved
0.8042 Intermediate Similarity NPD4060 Phase 1
0.8028 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.8013 Intermediate Similarity NPD3882 Suspended
0.8013 Intermediate Similarity NPD4967 Phase 2
0.8013 Intermediate Similarity NPD4966 Approved
0.8013 Intermediate Similarity NPD4965 Approved
0.8 Intermediate Similarity NPD1548 Phase 1
0.7973 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7973 Intermediate Similarity NPD6674 Discontinued
0.7943 Intermediate Similarity NPD3018 Phase 2
0.7925 Intermediate Similarity NPD7199 Phase 2
0.7917 Intermediate Similarity NPD3620 Phase 2
0.7917 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7914 Intermediate Similarity NPD4749 Approved
0.7908 Intermediate Similarity NPD1653 Approved
0.7901 Intermediate Similarity NPD7228 Approved
0.7901 Intermediate Similarity NPD3818 Discontinued
0.7895 Intermediate Similarity NPD5283 Phase 1
0.7888 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7888 Intermediate Similarity NPD6166 Phase 2
0.7888 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7885 Intermediate Similarity NPD2801 Approved
0.7862 Intermediate Similarity NPD5494 Approved
0.7786 Intermediate Similarity NPD2983 Phase 2
0.7786 Intermediate Similarity NPD2982 Phase 2
0.7785 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7746 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7744 Intermediate Similarity NPD228 Approved
0.7744 Intermediate Similarity NPD5844 Phase 1
0.773 Intermediate Similarity NPD8651 Approved
0.7716 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7714 Intermediate Similarity NPD2981 Phase 2
0.7703 Intermediate Similarity NPD5588 Approved
0.7697 Intermediate Similarity NPD7074 Phase 3
0.766 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD1511 Approved
0.7643 Intermediate Similarity NPD1091 Approved
0.7643 Intermediate Similarity NPD3705 Approved
0.7636 Intermediate Similarity NPD7054 Approved
0.7635 Intermediate Similarity NPD4538 Approved
0.7635 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7635 Intermediate Similarity NPD4536 Approved
0.7619 Intermediate Similarity NPD5124 Phase 1
0.7619 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.761 Intermediate Similarity NPD6374 Clinical (unspecified phase)
0.76 Intermediate Similarity NPD5762 Approved
0.76 Intermediate Similarity NPD5763 Approved
0.7594 Intermediate Similarity NPD3021 Approved
0.7594 Intermediate Similarity NPD3022 Approved
0.759 Intermediate Similarity NPD7472 Approved
0.7582 Intermediate Similarity NPD5058 Phase 3
0.758 Intermediate Similarity NPD4380 Phase 2
0.7566 Intermediate Similarity NPD3892 Phase 2
0.7566 Intermediate Similarity NPD6331 Phase 2
0.7551 Intermediate Similarity NPD1558 Phase 1
0.7548 Intermediate Similarity NPD1512 Approved
0.7535 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7534 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7519 Intermediate Similarity NPD2684 Approved
0.7518 Intermediate Similarity NPD7157 Approved
0.7516 Intermediate Similarity NPD6055 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6355 Discontinued
0.75 Intermediate Similarity NPD3817 Phase 2
0.75 Intermediate Similarity NPD6559 Discontinued
0.75 Intermediate Similarity NPD5735 Approved
0.7484 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7483 Intermediate Similarity NPD6696 Suspended
0.7468 Intermediate Similarity NPD4675 Approved
0.7468 Intermediate Similarity NPD4678 Approved
0.7467 Intermediate Similarity NPD5960 Phase 3
0.7455 Intermediate Similarity NPD2489 Approved
0.7455 Intermediate Similarity NPD27 Approved
0.7444 Intermediate Similarity NPD290 Approved
0.744 Intermediate Similarity NPD6797 Phase 2
0.7439 Intermediate Similarity NPD6232 Discontinued
0.7434 Intermediate Similarity NPD2424 Discontinued
0.7429 Intermediate Similarity NPD1357 Approved
0.7426 Intermediate Similarity NPD7843 Approved
0.741 Intermediate Similarity NPD7473 Discontinued
0.7407 Intermediate Similarity NPD7075 Discontinued
0.7403 Intermediate Similarity NPD2677 Approved
0.7396 Intermediate Similarity NPD7251 Discontinued
0.7396 Intermediate Similarity NPD7240 Approved
0.7394 Intermediate Similarity NPD2969 Approved
0.7394 Intermediate Similarity NPD422 Phase 1
0.7394 Intermediate Similarity NPD2970 Approved
0.7391 Intermediate Similarity NPD2563 Approved
0.7391 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD6671 Approved
0.7391 Intermediate Similarity NPD2560 Approved
0.7386 Intermediate Similarity NPD4236 Phase 3
0.7386 Intermediate Similarity NPD5177 Phase 3
0.7386 Intermediate Similarity NPD1652 Phase 2
0.7386 Intermediate Similarity NPD4237 Approved
0.7384 Intermediate Similarity NPD4663 Approved
0.7368 Intermediate Similarity NPD7266 Discontinued
0.7368 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD6005 Phase 3
0.7368 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD3540 Phase 1
0.7368 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD6002 Phase 3
0.7368 Intermediate Similarity NPD6004 Phase 3
0.7353 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7353 Intermediate Similarity NPD7808 Phase 3
0.7338 Intermediate Similarity NPD4110 Phase 3
0.7338 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7337 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD3051 Approved
0.7333 Intermediate Similarity NPD7229 Phase 3
0.7329 Intermediate Similarity NPD1465 Phase 2
0.7329 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7325 Intermediate Similarity NPD1940 Clinical (unspecified phase)
0.7325 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7315 Intermediate Similarity NPD2238 Phase 2
0.7312 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.731 Intermediate Similarity NPD7311 Approved
0.731 Intermediate Similarity NPD4577 Approved
0.731 Intermediate Similarity NPD7313 Approved
0.731 Intermediate Similarity NPD7310 Approved
0.731 Intermediate Similarity NPD7312 Approved
0.731 Intermediate Similarity NPD4578 Approved
0.7308 Intermediate Similarity NPD7212 Phase 2
0.7308 Intermediate Similarity NPD7213 Phase 3
0.7303 Intermediate Similarity NPD6100 Approved
0.7303 Intermediate Similarity NPD3539 Phase 1
0.7303 Intermediate Similarity NPD6099 Approved
0.7301 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7296 Intermediate Similarity NPD4005 Discontinued
0.7273 Intermediate Similarity NPD3060 Approved
0.7267 Intermediate Similarity NPD6801 Discontinued
0.7267 Intermediate Similarity NPD7309 Approved
0.7261 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7261 Intermediate Similarity NPD7447 Phase 1
0.7255 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7255 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7255 Intermediate Similarity NPD1375 Discontinued
0.7251 Intermediate Similarity NPD7549 Discontinued
0.7244 Intermediate Similarity NPD7124 Phase 2
0.7241 Intermediate Similarity NPD7906 Approved
0.7237 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7237 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD7466 Approved
0.7226 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD4628 Phase 3
0.7225 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD2977 Approved
0.7222 Intermediate Similarity NPD7819 Suspended
0.7222 Intermediate Similarity NPD2978 Approved
0.7219 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD6653 Approved
0.7208 Intermediate Similarity NPD1549 Phase 2
0.7206 Intermediate Similarity NPD4750 Phase 3
0.7205 Intermediate Similarity NPD6072 Discontinued
0.72 Intermediate Similarity NPD4140 Approved
0.7197 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD4357 Discontinued
0.7192 Intermediate Similarity NPD3094 Phase 2
0.719 Intermediate Similarity NPD2161 Phase 2
0.7181 Intermediate Similarity NPD6798 Discontinued
0.7172 Intermediate Similarity NPD5327 Phase 3
0.7169 Intermediate Similarity NPD6959 Discontinued
0.7169 Intermediate Similarity NPD8127 Discontinued
0.7169 Intermediate Similarity NPD1247 Approved
0.7168 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7168 Intermediate Similarity NPD8053 Approved
0.7168 Intermediate Similarity NPD8054 Approved
0.7161 Intermediate Similarity NPD4162 Approved
0.7152 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD4123 Phase 3
0.7152 Intermediate Similarity NPD2534 Approved
0.7152 Intermediate Similarity NPD919 Approved
0.7152 Intermediate Similarity NPD2532 Approved
0.7152 Intermediate Similarity NPD2533 Approved
0.7143 Intermediate Similarity NPD6584 Phase 3
0.7134 Intermediate Similarity NPD6666 Approved
0.7134 Intermediate Similarity NPD7768 Phase 2
0.7134 Intermediate Similarity NPD6667 Approved
0.7133 Intermediate Similarity NPD6516 Phase 2
0.7133 Intermediate Similarity NPD5846 Approved
0.7133 Intermediate Similarity NPD5125 Phase 3
0.7133 Intermediate Similarity NPD5126 Approved
0.7126 Intermediate Similarity NPD6071 Discontinued
0.7124 Intermediate Similarity NPD7033 Discontinued

  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