Structure

Physi-Chem Properties

Molecular Weight:  314.19
Volume:  341.995
LogP:  3.18
LogD:  2.777
LogS:  -4.353
# Rotatable Bonds:  2
TPSA:  54.37
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.907
Synthetic Accessibility Score:  3.74
Fsp3:  0.6
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.69
MDCK Permeability:  2.0899968149024062e-05
Pgp-inhibitor:  0.081
Pgp-substrate:  0.007
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.145
30% Bioavailability (F30%):  0.498

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.256
Plasma Protein Binding (PPB):  88.53215789794922%
Volume Distribution (VD):  0.469
Pgp-substrate:  11.99771499633789%

ADMET: Metabolism

CYP1A2-inhibitor:  0.115
CYP1A2-substrate:  0.841
CYP2C19-inhibitor:  0.294
CYP2C19-substrate:  0.884
CYP2C9-inhibitor:  0.178
CYP2C9-substrate:  0.159
CYP2D6-inhibitor:  0.062
CYP2D6-substrate:  0.119
CYP3A4-inhibitor:  0.558
CYP3A4-substrate:  0.674

ADMET: Excretion

Clearance (CL):  11.841
Half-life (T1/2):  0.426

ADMET: Toxicity

hERG Blockers:  0.028
Human Hepatotoxicity (H-HT):  0.314
Drug-inuced Liver Injury (DILI):  0.105
AMES Toxicity:  0.067
Rat Oral Acute Toxicity:  0.504
Maximum Recommended Daily Dose:  0.325
Skin Sensitization:  0.145
Carcinogencity:  0.748
Eye Corrosion:  0.004
Eye Irritation:  0.05
Respiratory Toxicity:  0.703

Download Data

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

  Natural Product: NPC215419

Natural Product ID:  NPC215419
Common Name*:   Triptobenzene N
IUPAC Name:   (1S,4aS,10aR)-1-(hydroxymethyl)-1,4a-dimethyl-7-propan-2-yl-3,4,10,10a-tetrahydrophenanthrene-2,9-dione
Synonyms:   triptobenzene N
Standard InCHIKey:  AILBGNUDAQUSML-MISYRCLQSA-N
Standard InCHI:  InChI=1S/C20H26O3/c1-12(2)13-5-6-15-14(9-13)16(22)10-17-19(15,3)8-7-18(23)20(17,4)11-21/h5-6,9,12,17,21H,7-8,10-11H2,1-4H3/t17-,19-,20-/m1/s1
SMILES:  OC[C@@]1(C)C(=O)CC[C@]2([C@H]1CC(=O)c1c2ccc(c1)C(C)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL444235
PubChem CID:   21672229
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001551] Diterpenoids

*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
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. DOI[10.1016/0031-9422(90)85349-K]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. DOI[10.1186/1471-2202-6-1]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[10579865]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. leaf n.a. PMID[10716597]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[10757718]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[11374948]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[11561442]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[12579877]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[1375626]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[1375626]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[1602302]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[1602302]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[16864458]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota roots n.a. n.a. PMID[16989518]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[17250858]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[17265278]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[1823717]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. leaf n.a. PMID[1823717]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[18554602]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. bark n.a. PMID[18996177]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota root n.a. n.a. PMID[21486005]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[21486005]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[21514608]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota dried roots purchased from Sichuan Neautus Traditional Chinese Medicine Co. Ltd. (Chengdu, P.R. China) n.a. PMID[22148431]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota leaves n.a. n.a. PMID[23268606]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[23852638]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[24549173]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[24963543]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[25237706]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. bark n.a. PMID[2534610]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[2816380]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota Leaves n.a. n.a. PMID[29355322]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota Leaves n.a. n.a. PMID[31556299]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[7102323]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[7304185]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[8699928]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[8722541]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. Database[Article]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13661 Tripterygium wilfordii Species Celastraceae 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
NPT927 Cell Line PBMC Homo sapiens Inhibition = 13.3 % PMID[451673]
NPT927 Cell Line PBMC Homo sapiens Inhibition = 15.4 % PMID[451673]
NPT927 Cell Line PBMC Homo sapiens Inhibition = 37.9 % PMID[451673]
NPT927 Cell Line PBMC Homo sapiens Inhibition = -52.2 % PMID[451673]
NPT927 Cell Line PBMC Homo sapiens Inhibition = 64.5 % PMID[451673]
NPT927 Cell Line PBMC Homo sapiens Inhibition = 42.3 % PMID[451673]
NPT1872 Cell Line Bcap37 Homo sapiens IC50 > 100000.0 nM PMID[451674]
NPT65 Cell Line HepG2 Homo sapiens IC50 = 43730.0 nM PMID[451674]
NPT380 Cell Line U-251 Homo sapiens IC50 > 100000.0 nM PMID[451674]
NPT83 Cell Line MCF7 Homo sapiens IC50 > 100000.0 nM PMID[451674]
NPT81 Cell Line A549 Homo sapiens IC50 = 32840.0 nM PMID[451674]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 100000.0 nM PMID[451674]

☑ 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 NPC215419 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
0.9623 High Similarity NPC265513
0.9266 High Similarity NPC93287
0.9091 High Similarity NPC470253
0.9009 High Similarity NPC471721
0.9 High Similarity NPC280789
0.8839 High Similarity NPC130591
0.8839 High Similarity NPC234637
0.8796 High Similarity NPC471186
0.875 High Similarity NPC471481
0.8707 High Similarity NPC202015
0.8707 High Similarity NPC476645
0.8696 High Similarity NPC80605
0.8696 High Similarity NPC323440
0.8696 High Similarity NPC222968
0.8661 High Similarity NPC218855
0.8611 High Similarity NPC247976
0.8584 High Similarity NPC143768
0.8559 High Similarity NPC476234
0.85 High Similarity NPC85511
0.8487 Intermediate Similarity NPC269923
0.8487 Intermediate Similarity NPC167323
0.8475 Intermediate Similarity NPC472680
0.8475 Intermediate Similarity NPC472679
0.8462 Intermediate Similarity NPC318173
0.8426 Intermediate Similarity NPC109514
0.8403 Intermediate Similarity NPC472981
0.8396 Intermediate Similarity NPC219573
0.8396 Intermediate Similarity NPC185208
0.8393 Intermediate Similarity NPC470252
0.8378 Intermediate Similarity NPC100767
0.8378 Intermediate Similarity NPC94751
0.8378 Intermediate Similarity NPC142326
0.8348 Intermediate Similarity NPC196673
0.8347 Intermediate Similarity NPC472681
0.8333 Intermediate Similarity NPC471188
0.8333 Intermediate Similarity NPC471189
0.8318 Intermediate Similarity NPC239185
0.8305 Intermediate Similarity NPC472698
0.8305 Intermediate Similarity NPC472697
0.8304 Intermediate Similarity NPC112903
0.8291 Intermediate Similarity NPC469843
0.8257 Intermediate Similarity NPC136810
0.8257 Intermediate Similarity NPC476993
0.8257 Intermediate Similarity NPC128248
0.8257 Intermediate Similarity NPC133809
0.8241 Intermediate Similarity NPC134882
0.8214 Intermediate Similarity NPC83409
0.8214 Intermediate Similarity NPC185763
0.8197 Intermediate Similarity NPC328107
0.819 Intermediate Similarity NPC326664
0.819 Intermediate Similarity NPC294458
0.8175 Intermediate Similarity NPC471334
0.8174 Intermediate Similarity NPC292834
0.8148 Intermediate Similarity NPC265220
0.8145 Intermediate Similarity NPC470648
0.8113 Intermediate Similarity NPC323420
0.8091 Intermediate Similarity NPC225079
0.808 Intermediate Similarity NPC316553
0.808 Intermediate Similarity NPC51448
0.808 Intermediate Similarity NPC472678
0.808 Intermediate Similarity NPC115797
0.808 Intermediate Similarity NPC478165
0.808 Intermediate Similarity NPC478162
0.8073 Intermediate Similarity NPC75724
0.8067 Intermediate Similarity NPC268930
0.8067 Intermediate Similarity NPC61651
0.8036 Intermediate Similarity NPC329282
0.8019 Intermediate Similarity NPC220596
0.8017 Intermediate Similarity NPC186128
0.8 Intermediate Similarity NPC474106
0.8 Intermediate Similarity NPC221825
0.8 Intermediate Similarity NPC54647
0.7984 Intermediate Similarity NPC472694
0.7984 Intermediate Similarity NPC472693
0.7983 Intermediate Similarity NPC158157
0.7965 Intermediate Similarity NPC172483
0.7963 Intermediate Similarity NPC260233
0.7946 Intermediate Similarity NPC472691
0.7946 Intermediate Similarity NPC471829
0.7946 Intermediate Similarity NPC474866
0.7946 Intermediate Similarity NPC475939
0.7946 Intermediate Similarity NPC329556
0.7944 Intermediate Similarity NPC153885
0.7944 Intermediate Similarity NPC59677
0.7931 Intermediate Similarity NPC474057
0.792 Intermediate Similarity NPC328997
0.792 Intermediate Similarity NPC294050
0.7909 Intermediate Similarity NPC49994
0.7903 Intermediate Similarity NPC318067
0.7899 Intermediate Similarity NPC260886
0.787 Intermediate Similarity NPC289883
0.787 Intermediate Similarity NPC238219
0.7857 Intermediate Similarity NPC146239
0.785 Intermediate Similarity NPC133461
0.7846 Intermediate Similarity NPC477139
0.784 Intermediate Similarity NPC478108
0.7833 Intermediate Similarity NPC212891
0.783 Intermediate Similarity NPC298115
0.7829 Intermediate Similarity NPC471851
0.7818 Intermediate Similarity NPC226041
0.7818 Intermediate Similarity NPC324602
0.7807 Intermediate Similarity NPC134120
0.7788 Intermediate Similarity NPC274443
0.7786 Intermediate Similarity NPC474659
0.7778 Intermediate Similarity NPC155232
0.7778 Intermediate Similarity NPC475002
0.7778 Intermediate Similarity NPC95126
0.776 Intermediate Similarity NPC325740
0.776 Intermediate Similarity NPC51079
0.7752 Intermediate Similarity NPC472692
0.7752 Intermediate Similarity NPC472682
0.775 Intermediate Similarity NPC9274
0.7744 Intermediate Similarity NPC475957
0.7739 Intermediate Similarity NPC37914
0.7739 Intermediate Similarity NPC244933
0.7739 Intermediate Similarity NPC85560
0.7739 Intermediate Similarity NPC472699
0.7739 Intermediate Similarity NPC472700
0.7731 Intermediate Similarity NPC67377
0.7724 Intermediate Similarity NPC238861
0.7724 Intermediate Similarity NPC77000
0.7724 Intermediate Similarity NPC133389
0.7724 Intermediate Similarity NPC476225
0.7724 Intermediate Similarity NPC183339
0.7724 Intermediate Similarity NPC234337
0.7712 Intermediate Similarity NPC66208
0.771 Intermediate Similarity NPC78307
0.7699 Intermediate Similarity NPC244427
0.7699 Intermediate Similarity NPC222390
0.7685 Intermediate Similarity NPC125226
0.7685 Intermediate Similarity NPC141607
0.7685 Intermediate Similarity NPC187725
0.7674 Intermediate Similarity NPC25736
0.7672 Intermediate Similarity NPC472701
0.7672 Intermediate Similarity NPC21929
0.7672 Intermediate Similarity NPC472683
0.7672 Intermediate Similarity NPC472696
0.7672 Intermediate Similarity NPC472695
0.7667 Intermediate Similarity NPC217111
0.7667 Intermediate Similarity NPC93181
0.7667 Intermediate Similarity NPC186933
0.7667 Intermediate Similarity NPC474095
0.7667 Intermediate Similarity NPC221275
0.7667 Intermediate Similarity NPC476357
0.7656 Intermediate Similarity NPC84672
0.7656 Intermediate Similarity NPC176130
0.7656 Intermediate Similarity NPC78364
0.7656 Intermediate Similarity NPC69424
0.7652 Intermediate Similarity NPC202225
0.7652 Intermediate Similarity NPC23894
0.7642 Intermediate Similarity NPC204784
0.7634 Intermediate Similarity NPC144257
0.7632 Intermediate Similarity NPC19856
0.7627 Intermediate Similarity NPC137315
0.7623 Intermediate Similarity NPC45794
0.7615 Intermediate Similarity NPC188844
0.7615 Intermediate Similarity NPC1682
0.7611 Intermediate Similarity NPC472879
0.7607 Intermediate Similarity NPC475006
0.76 Intermediate Similarity NPC293831
0.76 Intermediate Similarity NPC369
0.7593 Intermediate Similarity NPC173413
0.7593 Intermediate Similarity NPC19256
0.7593 Intermediate Similarity NPC277277
0.7589 Intermediate Similarity NPC329387
0.7589 Intermediate Similarity NPC317280
0.7586 Intermediate Similarity NPC25385
0.7586 Intermediate Similarity NPC193640
0.7586 Intermediate Similarity NPC475905
0.7581 Intermediate Similarity NPC133302
0.7578 Intermediate Similarity NPC71610
0.7576 Intermediate Similarity NPC115458
0.757 Intermediate Similarity NPC267262
0.7559 Intermediate Similarity NPC295664
0.7547 Intermediate Similarity NPC307
0.7547 Intermediate Similarity NPC160339
0.754 Intermediate Similarity NPC65627
0.7538 Intermediate Similarity NPC262819
0.7538 Intermediate Similarity NPC276238
0.7537 Intermediate Similarity NPC472308
0.7523 Intermediate Similarity NPC284475
0.7521 Intermediate Similarity NPC211439
0.7521 Intermediate Similarity NPC274839
0.7521 Intermediate Similarity NPC203732
0.7521 Intermediate Similarity NPC228936
0.7521 Intermediate Similarity NPC470007
0.752 Intermediate Similarity NPC144547
0.7519 Intermediate Similarity NPC72667
0.75 Intermediate Similarity NPC470765
0.75 Intermediate Similarity NPC478107
0.75 Intermediate Similarity NPC275576
0.75 Intermediate Similarity NPC477476
0.75 Intermediate Similarity NPC470649
0.75 Intermediate Similarity NPC477475
0.7481 Intermediate Similarity NPC31799
0.7481 Intermediate Similarity NPC199253
0.7481 Intermediate Similarity NPC108129
0.7481 Intermediate Similarity NPC136588
0.748 Intermediate Similarity NPC198014
0.7477 Intermediate Similarity NPC69057

  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 NPC215419 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
0.8571 High Similarity NPD4141 Clinical (unspecified phase)
0.8318 Intermediate Similarity NPD3495 Discontinued
0.812 Intermediate Similarity NPD5951 Approved
0.8067 Intermediate Similarity NPD7610 Discontinued
0.7946 Intermediate Similarity NPD1930 Approved
0.7946 Intermediate Similarity NPD1931 Clinical (unspecified phase)
0.7946 Intermediate Similarity NPD1929 Approved
0.7851 Intermediate Similarity NPD7009 Phase 2
0.7838 Intermediate Similarity NPD2066 Phase 3
0.7724 Intermediate Similarity NPD3412 Clinical (unspecified phase)
0.7724 Intermediate Similarity NPD7163 Clinical (unspecified phase)
0.7699 Intermediate Similarity NPD1932 Approved
0.7615 Intermediate Similarity NPD7631 Approved
0.7607 Intermediate Similarity NPD2329 Discontinued
0.7538 Intermediate Similarity NPD7008 Discontinued
0.7538 Intermediate Similarity NPD5952 Clinical (unspecified phase)
0.7523 Intermediate Similarity NPD7609 Phase 3
0.752 Intermediate Similarity NPD7457 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6858 Approved
0.75 Intermediate Similarity NPD7094 Approved
0.7459 Intermediate Similarity NPD3317 Approved
0.7424 Intermediate Similarity NPD7961 Discontinued
0.7387 Intermediate Similarity NPD5122 Clinical (unspecified phase)
0.7381 Intermediate Similarity NPD4879 Approved
0.7315 Intermediate Similarity NPD650 Approved
0.7311 Intermediate Similarity NPD6831 Clinical (unspecified phase)
0.7297 Intermediate Similarity NPD1088 Approved
0.7265 Intermediate Similarity NPD1237 Approved
0.7168 Intermediate Similarity NPD1693 Approved
0.7168 Intermediate Similarity NPD688 Clinical (unspecified phase)
0.7154 Intermediate Similarity NPD6010 Discontinued
0.7132 Intermediate Similarity NPD4878 Approved
0.7117 Intermediate Similarity NPD1089 Approved
0.7117 Intermediate Similarity NPD1090 Approved
0.7117 Intermediate Similarity NPD1086 Approved
0.7107 Intermediate Similarity NPD1317 Discontinued
0.7054 Intermediate Similarity NPD1201 Approved
0.7031 Intermediate Similarity NPD3019 Approved
0.7027 Intermediate Similarity NPD800 Approved
0.6991 Remote Similarity NPD1508 Approved
0.697 Remote Similarity NPD1470 Approved
0.696 Remote Similarity NPD2629 Approved
0.6957 Remote Similarity NPD1989 Approved
0.6923 Remote Similarity NPD7236 Approved
0.6916 Remote Similarity NPD942 Approved
0.6903 Remote Similarity NPD1239 Approved
0.6901 Remote Similarity NPD7003 Approved
0.6899 Remote Similarity NPD2932 Approved
0.6899 Remote Similarity NPD2345 Approved
0.6899 Remote Similarity NPD4199 Phase 3
0.6897 Remote Similarity NPD1564 Approved
0.6897 Remote Similarity NPD1566 Phase 3
0.6897 Remote Similarity NPD1565 Approved
0.6891 Remote Similarity NPD6647 Phase 2
0.6891 Remote Similarity NPD5700 Clinical (unspecified phase)
0.687 Remote Similarity NPD6048 Clinical (unspecified phase)
0.687 Remote Similarity NPD6049 Phase 2
0.6855 Remote Similarity NPD1609 Clinical (unspecified phase)
0.6847 Remote Similarity NPD1087 Approved
0.6833 Remote Similarity NPD5909 Discontinued
0.6822 Remote Similarity NPD4196 Clinical (unspecified phase)
0.681 Remote Similarity NPD1843 Approved
0.6803 Remote Similarity NPD7239 Suspended
0.6786 Remote Similarity NPD1509 Clinical (unspecified phase)
0.6777 Remote Similarity NPD5048 Discontinued
0.6774 Remote Similarity NPD2181 Clinical (unspecified phase)
0.6759 Remote Similarity NPD8165 Discontinued
0.6742 Remote Similarity NPD3972 Approved
0.6741 Remote Similarity NPD7084 Phase 3
0.6738 Remote Similarity NPD5405 Approved
0.6738 Remote Similarity NPD5406 Approved
0.6738 Remote Similarity NPD5408 Approved
0.6738 Remote Similarity NPD5404 Approved
0.6726 Remote Similarity NPD5347 Phase 2
0.6726 Remote Similarity NPD5346 Phase 2
0.6718 Remote Similarity NPD3026 Approved
0.6718 Remote Similarity NPD3023 Approved
0.6692 Remote Similarity NPD5157 Phase 1
0.6692 Remote Similarity NPD5159 Phase 2
0.6692 Remote Similarity NPD3024 Approved
0.6692 Remote Similarity NPD5158 Clinical (unspecified phase)
0.6692 Remote Similarity NPD3025 Approved
0.669 Remote Similarity NPD2346 Discontinued
0.6667 Remote Similarity NPD6273 Approved
0.6667 Remote Similarity NPD6287 Discontinued
0.6667 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6667 Remote Similarity NPD3673 Approved
0.6667 Remote Similarity NPD2798 Approved
0.6667 Remote Similarity NPD3672 Approved
0.6644 Remote Similarity NPD3226 Approved
0.6644 Remote Similarity NPD7458 Discontinued
0.6642 Remote Similarity NPD6330 Clinical (unspecified phase)
0.6641 Remote Similarity NPD5836 Discontinued
0.6638 Remote Similarity NPD1563 Approved
0.6613 Remote Similarity NPD2182 Approved
0.6606 Remote Similarity NPD226 Approved
0.6599 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6594 Remote Similarity NPD5422 Clinical (unspecified phase)
0.6589 Remote Similarity NPD405 Clinical (unspecified phase)
0.6573 Remote Similarity NPD7702 Clinical (unspecified phase)
0.6549 Remote Similarity NPD4793 Discontinued
0.6547 Remote Similarity NPD7714 Approved
0.6547 Remote Similarity NPD6663 Approved
0.6547 Remote Similarity NPD7713 Phase 3
0.6547 Remote Similarity NPD7715 Approved
0.6531 Remote Similarity NPD7390 Discontinued
0.6529 Remote Similarity NPD2193 Phase 2
0.6529 Remote Similarity NPD2648 Phase 3
0.6522 Remote Similarity NPD6966 Discovery
0.6514 Remote Similarity NPD1507 Clinical (unspecified phase)
0.6512 Remote Similarity NPD4198 Discontinued
0.6504 Remote Similarity NPD1018 Approved
0.65 Remote Similarity NPD7798 Approved
0.6496 Remote Similarity NPD5736 Approved
0.6489 Remote Similarity NPD3091 Approved
0.6486 Remote Similarity NPD9491 Approved
0.6484 Remote Similarity NPD2652 Approved
0.6484 Remote Similarity NPD4869 Clinical (unspecified phase)
0.6484 Remote Similarity NPD2650 Approved
0.6483 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6475 Remote Similarity NPD6766 Clinical (unspecified phase)
0.6475 Remote Similarity NPD5765 Approved
0.6452 Remote Similarity NPD6685 Approved
0.6449 Remote Similarity NPD7055 Discontinued
0.6446 Remote Similarity NPD3135 Clinical (unspecified phase)
0.6444 Remote Similarity NPD182 Clinical (unspecified phase)
0.6439 Remote Similarity NPD1245 Approved
0.6438 Remote Similarity NPD4628 Phase 3
0.6438 Remote Similarity NPD8166 Discontinued
0.6434 Remote Similarity NPD2799 Discontinued
0.6424 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6423 Remote Similarity NPD4980 Approved
0.6423 Remote Similarity NPD164 Approved
0.6418 Remote Similarity NPD5618 Discontinued
0.6412 Remote Similarity NPD6065 Approved
0.6408 Remote Similarity NPD6817 Clinical (unspecified phase)
0.6397 Remote Similarity NPD1283 Approved
0.6397 Remote Similarity NPD1876 Approved
0.6393 Remote Similarity NPD2196 Discontinued
0.6391 Remote Similarity NPD3095 Discontinued
0.6387 Remote Similarity NPD7057 Phase 3
0.6387 Remote Similarity NPD7058 Phase 2
0.6383 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6379 Remote Similarity NPD9258 Approved
0.6379 Remote Similarity NPD9256 Approved
0.6378 Remote Similarity NPD3643 Approved
0.6378 Remote Similarity NPD3644 Approved
0.6378 Remote Similarity NPD3642 Approved
0.6372 Remote Similarity NPD5734 Clinical (unspecified phase)
0.637 Remote Similarity NPD6637 Approved
0.6364 Remote Similarity NPD1238 Approved
0.6364 Remote Similarity NPD7741 Discontinued
0.6357 Remote Similarity NPD2313 Discontinued
0.6356 Remote Similarity NPD1202 Approved
0.6351 Remote Similarity NPD3300 Phase 2
0.635 Remote Similarity NPD1164 Approved
0.6339 Remote Similarity NPD3971 Phase 1
0.6335 Remote Similarity NPD7799 Discontinued
0.633 Remote Similarity NPD225 Approved
0.633 Remote Similarity NPD227 Approved
0.6325 Remote Similarity NPD6079 Approved
0.6323 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6319 Remote Similarity NPD3299 Clinical (unspecified phase)
0.6319 Remote Similarity NPD7305 Phase 1
0.6316 Remote Similarity NPD6591 Clinical (unspecified phase)
0.6316 Remote Similarity NPD1651 Approved
0.6308 Remote Similarity NPD1711 Phase 2
0.6308 Remote Similarity NPD4766 Approved
0.6308 Remote Similarity NPD1246 Approved
0.6304 Remote Similarity NPD6085 Phase 2
0.6304 Remote Similarity NPD5740 Clinical (unspecified phase)
0.6303 Remote Similarity NPD4629 Approved
0.6303 Remote Similarity NPD4814 Discontinued
0.6303 Remote Similarity NPD4094 Approved
0.6303 Remote Similarity NPD5210 Approved
0.6299 Remote Similarity NPD3646 Clinical (unspecified phase)
0.6296 Remote Similarity NPD3092 Approved
0.6296 Remote Similarity NPD4216 Approved
0.6296 Remote Similarity NPD4215 Approved
0.6296 Remote Similarity NPD3132 Approved
0.6296 Remote Similarity NPD2611 Approved
0.6296 Remote Similarity NPD3131 Approved
0.6296 Remote Similarity NPD2610 Approved
0.6296 Remote Similarity NPD2608 Approved
0.6296 Remote Similarity NPD4218 Approved
0.6296 Remote Similarity NPD2612 Approved
0.6296 Remote Similarity NPD2609 Approved
0.6296 Remote Similarity NPD4217 Approved
0.6294 Remote Similarity NPD3528 Clinical (unspecified phase)
0.6284 Remote Similarity NPD7295 Approved
0.6283 Remote Similarity NPD3665 Phase 1
0.6283 Remote Similarity NPD3666 Approved
0.6283 Remote Similarity NPD3133 Approved
0.6281 Remote Similarity NPD9495 Approved
0.6261 Remote Similarity NPD506 Clinical (unspecified phase)
0.6258 Remote Similarity NPD7819 Suspended
0.625 Remote Similarity NPD3880 Clinical (unspecified phase)
0.625 Remote Similarity NPD5206 Clinical (unspecified phase)
0.6241 Remote Similarity NPD2846 Clinical (unspecified phase)
0.6241 Remote Similarity NPD3764 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