Structure

Physi-Chem Properties

Molecular Weight:  532.3
Volume:  550.35
LogP:  2.311
LogD:  1.241
LogS:  -2.666
# Rotatable Bonds:  6
TPSA:  146.04
# H-Bond Aceptor:  8
# H-Bond Donor:  3
# Rings:  4
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.473
Synthetic Accessibility Score:  5.348
Fsp3:  0.833
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.4
MDCK Permeability:  3.263759208493866e-05
Pgp-inhibitor:  0.517
Pgp-substrate:  0.598
Human Intestinal Absorption (HIA):  0.017
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.103

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.493
Plasma Protein Binding (PPB):  55.87446594238281%
Volume Distribution (VD):  0.32
Pgp-substrate:  31.466276168823242%

ADMET: Metabolism

CYP1A2-inhibitor:  0.001
CYP1A2-substrate:  0.129
CYP2C19-inhibitor:  0.004
CYP2C19-substrate:  0.808
CYP2C9-inhibitor:  0.005
CYP2C9-substrate:  0.24
CYP2D6-inhibitor:  0.003
CYP2D6-substrate:  0.101
CYP3A4-inhibitor:  0.019
CYP3A4-substrate:  0.156

ADMET: Excretion

Clearance (CL):  6.931
Half-life (T1/2):  0.832

ADMET: Toxicity

hERG Blockers:  0.008
Human Hepatotoxicity (H-HT):  0.387
Drug-inuced Liver Injury (DILI):  0.541
AMES Toxicity:  0.01
Rat Oral Acute Toxicity:  0.954
Maximum Recommended Daily Dose:  0.94
Skin Sensitization:  0.139
Carcinogencity:  0.033
Eye Corrosion:  0.112
Eye Irritation:  0.019
Respiratory Toxicity:  0.953

Download Data

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

  Natural Product: NPC5145

Natural Product ID:  NPC5145
Common Name*:   Eudistomin W
IUPAC Name:   1-[(1S)-1-hydroxy-2-phenylethyl]-9H-pyrido[3,4-b]indol-6-ol
Synonyms:   Eudistomin W
Standard InCHIKey:  NSUYQRXJCOMIRZ-KRWDZBQOSA-N
Standard InCHI:  InChI=1S/C19H16N2O2/c22-13-6-7-16-15(11-13)14-8-9-20-19(18(14)21-16)17(23)10-12-4-2-1-3-5-12/h1-9,11,17,21-23H,10H2/t17-/m0/s1
SMILES:  c1ccc(cc1)C[C@@H](c1c2c(ccn1)c1cc(ccc1[nH]2)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL442853
PubChem CID:   5323580
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0001140] Harmala alkaloids

*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
NPO33386 Eudistoma sp. Species n.a. n.a. n.a. n.a. n.a. PMID[10346975]
NPO33386 Eudistoma sp. Species n.a. n.a. n.a. Far-Eastern n.a. PMID[11754612]
NPO33386 Eudistoma sp. Species n.a. n.a. n.a. n.a. n.a. PMID[12608864]
NPO33386 Eudistoma sp. Species n.a. n.a. n.a. Korean n.a. PMID[18247569]

☑ 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
NPT20 Organism Candida albicans Candida albicans IZ = 13.0 mm PMID[481354]

☑ 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 NPC5145 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
0.9316 High Similarity NPC475070
0.9316 High Similarity NPC470500
0.8901 High Similarity NPC192315
0.8854 High Similarity NPC476167
0.8836 High Similarity NPC324149
0.8836 High Similarity NPC99666
0.8806 High Similarity NPC476041
0.8806 High Similarity NPC304926
0.871 High Similarity NPC48938
0.8617 High Similarity NPC314002
0.8615 High Similarity NPC176538
0.8615 High Similarity NPC249040
0.861 High Similarity NPC220765
0.8592 High Similarity NPC470501
0.8579 High Similarity NPC223427
0.8571 High Similarity NPC171171
0.8564 High Similarity NPC204717
0.8557 High Similarity NPC77555
0.8544 High Similarity NPC470502
0.8537 High Similarity NPC213530
0.8537 High Similarity NPC193267
0.8517 High Similarity NPC6215
0.8462 Intermediate Similarity NPC470503
0.8457 Intermediate Similarity NPC314394
0.8442 Intermediate Similarity NPC470505
0.8434 Intermediate Similarity NPC211813
0.8396 Intermediate Similarity NPC184964
0.839 Intermediate Similarity NPC477110
0.839 Intermediate Similarity NPC470799
0.839 Intermediate Similarity NPC8022
0.8357 Intermediate Similarity NPC469554
0.8341 Intermediate Similarity NPC81175
0.8333 Intermediate Similarity NPC46580
0.8333 Intermediate Similarity NPC26679
0.8326 Intermediate Similarity NPC295228
0.8316 Intermediate Similarity NPC251090
0.83 Intermediate Similarity NPC245816
0.83 Intermediate Similarity NPC476138
0.8274 Intermediate Similarity NPC156704
0.8271 Intermediate Similarity NPC207686
0.8241 Intermediate Similarity NPC477549
0.8241 Intermediate Similarity NPC19872
0.8235 Intermediate Similarity NPC123976
0.8235 Intermediate Similarity NPC167860
0.8224 Intermediate Similarity NPC476451
0.8214 Intermediate Similarity NPC307963
0.8204 Intermediate Similarity NPC477610
0.82 Intermediate Similarity NPC232727
0.8195 Intermediate Similarity NPC208284
0.8186 Intermediate Similarity NPC185782
0.8177 Intermediate Similarity NPC284678
0.8177 Intermediate Similarity NPC88008
0.8165 Intermediate Similarity NPC41679
0.815 Intermediate Similarity NPC315491
0.815 Intermediate Similarity NPC45459
0.8137 Intermediate Similarity NPC477111
0.8128 Intermediate Similarity NPC477861
0.8122 Intermediate Similarity NPC60006
0.8116 Intermediate Similarity NPC266931
0.8104 Intermediate Similarity NPC310118
0.8102 Intermediate Similarity NPC101543
0.8098 Intermediate Similarity NPC476116
0.8084 Intermediate Similarity NPC110151
0.8081 Intermediate Similarity NPC326634
0.8079 Intermediate Similarity NPC285558
0.8075 Intermediate Similarity NPC245348
0.8063 Intermediate Similarity NPC88363
0.8061 Intermediate Similarity NPC76748
0.806 Intermediate Similarity NPC213308
0.8047 Intermediate Similarity NPC253580
0.8047 Intermediate Similarity NPC314954
0.8039 Intermediate Similarity NPC476124
0.8039 Intermediate Similarity NPC477113
0.8039 Intermediate Similarity NPC476121
0.803 Intermediate Similarity NPC476098
0.803 Intermediate Similarity NPC200836
0.803 Intermediate Similarity NPC53144
0.8028 Intermediate Similarity NPC130570
0.802 Intermediate Similarity NPC92111
0.801 Intermediate Similarity NPC32771
0.801 Intermediate Similarity NPC296527
0.8 Intermediate Similarity NPC470126
0.8 Intermediate Similarity NPC27041
0.7991 Intermediate Similarity NPC471891
0.7973 Intermediate Similarity NPC171393
0.7973 Intermediate Similarity NPC295452
0.7962 Intermediate Similarity NPC477609
0.7953 Intermediate Similarity NPC319232
0.7953 Intermediate Similarity NPC24370
0.795 Intermediate Similarity NPC242209
0.7949 Intermediate Similarity NPC15102
0.7946 Intermediate Similarity NPC178858
0.7943 Intermediate Similarity NPC469592
0.7943 Intermediate Similarity NPC471080
0.7943 Intermediate Similarity NPC476287
0.7934 Intermediate Similarity NPC60621
0.7919 Intermediate Similarity NPC128751
0.7919 Intermediate Similarity NPC246700
0.7917 Intermediate Similarity NPC96890
0.7914 Intermediate Similarity NPC102423
0.7902 Intermediate Similarity NPC470504
0.79 Intermediate Similarity NPC276517
0.7895 Intermediate Similarity NPC219087
0.7895 Intermediate Similarity NPC316981
0.7892 Intermediate Similarity NPC473312
0.7887 Intermediate Similarity NPC132642
0.7887 Intermediate Similarity NPC276657
0.7879 Intermediate Similarity NPC106833
0.7879 Intermediate Similarity NPC95783
0.7879 Intermediate Similarity NPC469497
0.7874 Intermediate Similarity NPC82548
0.7873 Intermediate Similarity NPC15801
0.7854 Intermediate Similarity NPC475774
0.7853 Intermediate Similarity NPC474409
0.7822 Intermediate Similarity NPC153042
0.7822 Intermediate Similarity NPC267928
0.7816 Intermediate Similarity NPC264166
0.7816 Intermediate Similarity NPC274291
0.7816 Intermediate Similarity NPC329708
0.7816 Intermediate Similarity NPC118832
0.7816 Intermediate Similarity NPC47059
0.7816 Intermediate Similarity NPC165349
0.7812 Intermediate Similarity NPC39092
0.781 Intermediate Similarity NPC294620
0.781 Intermediate Similarity NPC471603
0.7807 Intermediate Similarity NPC131718
0.7799 Intermediate Similarity NPC85273
0.7798 Intermediate Similarity NPC477608
0.7798 Intermediate Similarity NPC477607
0.7794 Intermediate Similarity NPC315957
0.7793 Intermediate Similarity NPC264285
0.7793 Intermediate Similarity NPC469594
0.7789 Intermediate Similarity NPC63751
0.7788 Intermediate Similarity NPC171787
0.7784 Intermediate Similarity NPC72980
0.7783 Intermediate Similarity NPC97902
0.7783 Intermediate Similarity NPC469928
0.7778 Intermediate Similarity NPC472111
0.7772 Intermediate Similarity NPC222018
0.7763 Intermediate Similarity NPC326363
0.7761 Intermediate Similarity NPC106937
0.7761 Intermediate Similarity NPC329541
0.776 Intermediate Similarity NPC313791
0.7754 Intermediate Similarity NPC230869
0.7749 Intermediate Similarity NPC314940
0.7749 Intermediate Similarity NPC473764
0.774 Intermediate Similarity NPC270918
0.7738 Intermediate Similarity NPC323752
0.7732 Intermediate Similarity NPC59269
0.7731 Intermediate Similarity NPC280272
0.7718 Intermediate Similarity NPC473761
0.7714 Intermediate Similarity NPC11464
0.7713 Intermediate Similarity NPC184225
0.7706 Intermediate Similarity NPC103687
0.7706 Intermediate Similarity NPC132631
0.7703 Intermediate Similarity NPC182222
0.7703 Intermediate Similarity NPC325976
0.7696 Intermediate Similarity NPC317430
0.7696 Intermediate Similarity NPC265576
0.7696 Intermediate Similarity NPC212213
0.7696 Intermediate Similarity NPC229893
0.7692 Intermediate Similarity NPC42979
0.7692 Intermediate Similarity NPC474145
0.7692 Intermediate Similarity NPC475841
0.7685 Intermediate Similarity NPC473317
0.768 Intermediate Similarity NPC203754
0.768 Intermediate Similarity NPC150048
0.768 Intermediate Similarity NPC224764
0.7677 Intermediate Similarity NPC94943
0.7674 Intermediate Similarity NPC292958
0.7671 Intermediate Similarity NPC473185
0.7665 Intermediate Similarity NPC176127
0.7659 Intermediate Similarity NPC128823
0.7656 Intermediate Similarity NPC166492
0.7656 Intermediate Similarity NPC473362
0.7653 Intermediate Similarity NPC478032
0.7644 Intermediate Similarity NPC54988
0.7642 Intermediate Similarity NPC94157
0.7642 Intermediate Similarity NPC63971
0.7642 Intermediate Similarity NPC91868
0.7638 Intermediate Similarity NPC62749
0.7633 Intermediate Similarity NPC470678
0.7632 Intermediate Similarity NPC311276
0.7626 Intermediate Similarity NPC214980
0.7626 Intermediate Similarity NPC190007
0.7621 Intermediate Similarity NPC470497
0.7621 Intermediate Similarity NPC329793
0.7617 Intermediate Similarity NPC170114
0.7617 Intermediate Similarity NPC251936
0.7617 Intermediate Similarity NPC252590
0.7607 Intermediate Similarity NPC74619
0.7606 Intermediate Similarity NPC478074
0.7606 Intermediate Similarity NPC469762
0.7604 Intermediate Similarity NPC471506
0.7596 Intermediate Similarity NPC165599
0.7591 Intermediate Similarity NPC476492
0.7583 Intermediate Similarity NPC469589
0.7581 Intermediate Similarity NPC469727
0.758 Intermediate Similarity NPC125597
0.7576 Intermediate Similarity NPC212535

  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 NPC5145 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
0.8789 High Similarity NPD5575 Clinical (unspecified phase)
0.8462 Intermediate Similarity NPD7948 Phase 1
0.8301 Intermediate Similarity NPD5612 Discontinued
0.8214 Intermediate Similarity NPD1038 Approved
0.8213 Intermediate Similarity NPD6803 Clinical (unspecified phase)
0.815 Intermediate Similarity NPD484 Approved
0.8122 Intermediate Similarity NPD7603 Discontinued
0.8063 Intermediate Similarity NPD5483 Clinical (unspecified phase)
0.803 Intermediate Similarity NPD1304 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD5065 Approved
0.7982 Intermediate Similarity NPD7558 Phase 2
0.7981 Intermediate Similarity NPD3330 Phase 1
0.7962 Intermediate Similarity NPD8405 Clinical (unspecified phase)
0.7949 Intermediate Similarity NPD6344 Clinical (unspecified phase)
0.7913 Intermediate Similarity NPD7222 Phase 2
0.7902 Intermediate Similarity NPD4795 Phase 2
0.788 Intermediate Similarity NPD5559 Phase 2
0.7874 Intermediate Similarity NPD5658 Approved
0.7833 Intermediate Similarity NPD2176 Approved
0.7833 Intermediate Similarity NPD2175 Phase 3
0.7833 Intermediate Similarity NPD2177 Approved
0.7818 Intermediate Similarity NPD5040 Clinical (unspecified phase)
0.7816 Intermediate Similarity NPD31 Approved
0.7816 Intermediate Similarity NPD4039 Approved
0.7816 Intermediate Similarity NPD4037 Approved
0.7816 Intermediate Similarity NPD4033 Approved
0.7816 Intermediate Similarity NPD4035 Approved
0.7816 Intermediate Similarity NPD4038 Approved
0.7816 Intermediate Similarity NPD4122 Approved
0.7816 Intermediate Similarity NPD4034 Approved
0.7816 Intermediate Similarity NPD32 Approved
0.7816 Intermediate Similarity NPD4036 Approved
0.7811 Intermediate Similarity NPD3324 Clinical (unspecified phase)
0.7794 Intermediate Similarity NPD1740 Approved
0.7794 Intermediate Similarity NPD1739 Approved
0.7783 Intermediate Similarity NPD7112 Discontinued
0.7762 Intermediate Similarity NPD5067 Phase 2
0.7762 Intermediate Similarity NPD5066 Phase 2
0.7762 Intermediate Similarity NPD5939 Approved
0.7762 Intermediate Similarity NPD5936 Approved
0.7761 Intermediate Similarity NPD802 Phase 2
0.7746 Intermediate Similarity NPD7823 Clinical (unspecified phase)
0.7745 Intermediate Similarity NPD3825 Phase 3
0.7745 Intermediate Similarity NPD4118 Clinical (unspecified phase)
0.7744 Intermediate Similarity NPD6595 Phase 3
0.774 Intermediate Similarity NPD7452 Approved
0.774 Intermediate Similarity NPD7453 Approved
0.774 Intermediate Similarity NPD1392 Approved
0.774 Intermediate Similarity NPD6290 Phase 2
0.7723 Intermediate Similarity NPD2921 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD3003 Approved
0.7688 Intermediate Similarity NPD2383 Phase 1
0.7674 Intermediate Similarity NPD7194 Discontinued
0.7644 Intermediate Similarity NPD424 Approved
0.7644 Intermediate Similarity NPD425 Approved
0.7641 Intermediate Similarity NPD6159 Phase 2
0.7629 Intermediate Similarity NPD8442 Discontinued
0.7628 Intermediate Similarity NPD8109 Clinical (unspecified phase)
0.7609 Intermediate Similarity NPD5482 Discontinued
0.7604 Intermediate Similarity NPD5069 Clinical (unspecified phase)
0.7594 Intermediate Similarity NPD4502 Phase 2
0.7588 Intermediate Similarity NPD6610 Clinical (unspecified phase)
0.7573 Intermediate Similarity NPD8396 Approved
0.7573 Intermediate Similarity NPD8395 Approved
0.757 Intermediate Similarity NPD5903 Approved
0.757 Intermediate Similarity NPD5902 Approved
0.7558 Intermediate Similarity NPD6242 Discontinued
0.7548 Intermediate Similarity NPD3928 Approved
0.7548 Intermediate Similarity NPD3931 Approved
0.7538 Intermediate Similarity NPD9690 Approved
0.7536 Intermediate Similarity NPD2189 Approved
0.7536 Intermediate Similarity NPD2187 Approved
0.7526 Intermediate Similarity NPD9705 Discontinued
0.7526 Intermediate Similarity NPD112 Approved
0.7524 Intermediate Similarity NPD5530 Phase 1
0.7521 Intermediate Similarity NPD3343 Phase 3
0.7512 Intermediate Similarity NPD4886 Phase 2
0.7512 Intermediate Similarity NPD6141 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6494 Phase 2
0.75 Intermediate Similarity NPD2762 Phase 2
0.75 Intermediate Similarity NPD9695 Approved
0.75 Intermediate Similarity NPD4511 Phase 1
0.7467 Intermediate Similarity NPD7068 Approved
0.7467 Intermediate Similarity NPD7067 Approved
0.7463 Intermediate Similarity NPD706 Phase 1
0.7451 Intermediate Similarity NPD6569 Phase 2
0.7451 Intermediate Similarity NPD3404 Approved
0.745 Intermediate Similarity NPD5083 Clinical (unspecified phase)
0.7444 Intermediate Similarity NPD8512 Phase 3
0.7443 Intermediate Similarity NPD7726 Phase 1
0.7442 Intermediate Similarity NPD1322 Clinical (unspecified phase)
0.7441 Intermediate Similarity NPD3932 Clinical (unspecified phase)
0.7424 Intermediate Similarity NPD6473 Phase 1
0.7419 Intermediate Similarity NPD5164 Discontinued
0.7418 Intermediate Similarity NPD2125 Clinical (unspecified phase)
0.7411 Intermediate Similarity NPD2380 Approved
0.7411 Intermediate Similarity NPD2382 Approved
0.7411 Intermediate Similarity NPD2381 Approved
0.7406 Intermediate Similarity NPD3930 Clinical (unspecified phase)
0.7404 Intermediate Similarity NPD1768 Approved
0.7402 Intermediate Similarity NPD5913 Phase 3
0.7402 Intermediate Similarity NPD5912 Clinical (unspecified phase)
0.74 Intermediate Similarity NPD5596 Phase 2
0.7385 Intermediate Similarity NPD1326 Approved
0.7385 Intermediate Similarity NPD6985 Discontinued
0.7385 Intermediate Similarity NPD1325 Approved
0.7385 Intermediate Similarity NPD4184 Clinical (unspecified phase)
0.7374 Intermediate Similarity NPD6203 Clinical (unspecified phase)
0.736 Intermediate Similarity NPD6492 Phase 2
0.7353 Intermediate Similarity NPD8063 Discontinued
0.7352 Intermediate Similarity NPD3402 Phase 1
0.7352 Intermediate Similarity NPD534 Phase 2
0.7352 Intermediate Similarity NPD537 Phase 2
0.7349 Intermediate Similarity NPD4131 Phase 3
0.7344 Intermediate Similarity NPD9398 Clinical (unspecified phase)
0.734 Intermediate Similarity NPD8431 Approved
0.7337 Intermediate Similarity NPD4076 Approved
0.7337 Intermediate Similarity NPD4079 Approved
0.7327 Intermediate Similarity NPD6140 Clinical (unspecified phase)
0.7325 Intermediate Similarity NPD4344 Clinical (unspecified phase)
0.7325 Intermediate Similarity NPD4343 Phase 1
0.7324 Intermediate Similarity NPD6838 Clinical (unspecified phase)
0.7321 Intermediate Similarity NPD3814 Phase 1
0.7313 Intermediate Similarity NPD5522 Clinical (unspecified phase)
0.7311 Intermediate Similarity NPD5426 Phase 3
0.7311 Intermediate Similarity NPD5901 Discontinued
0.7311 Intermediate Similarity NPD7712 Clinical (unspecified phase)
0.7304 Intermediate Similarity NPD8110 Clinical (unspecified phase)
0.7303 Intermediate Similarity NPD5450 Discontinued
0.7299 Intermediate Similarity NPD6975 Discontinued
0.7292 Intermediate Similarity NPD5255 Approved
0.729 Intermediate Similarity NPD4612 Discontinued
0.729 Intermediate Similarity NPD7947 Clinical (unspecified phase)
0.7286 Intermediate Similarity NPD3506 Approved
0.7286 Intermediate Similarity NPD3505 Approved
0.7282 Intermediate Similarity NPD3921 Approved
0.7282 Intermediate Similarity NPD3924 Approved
0.7282 Intermediate Similarity NPD3922 Approved
0.7282 Intermediate Similarity NPD3923 Approved
0.7281 Intermediate Similarity NPD4454 Phase 2
0.7277 Intermediate Similarity NPD6978 Phase 2
0.7277 Intermediate Similarity NPD6977 Clinical (unspecified phase)
0.7277 Intermediate Similarity NPD4845 Discontinued
0.7273 Intermediate Similarity NPD4555 Clinical (unspecified phase)
0.7268 Intermediate Similarity NPD3321 Discontinued
0.7265 Intermediate Similarity NPD6976 Clinical (unspecified phase)
0.7264 Intermediate Similarity NPD4203 Approved
0.7264 Intermediate Similarity NPD7414 Clinical (unspecified phase)
0.7264 Intermediate Similarity NPD4204 Approved
0.726 Intermediate Similarity NPD6449 Clinical (unspecified phase)
0.7252 Intermediate Similarity NPD1856 Discontinued
0.7245 Intermediate Similarity NPD2781 Approved
0.7243 Intermediate Similarity NPD8410 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD3082 Discontinued
0.7235 Intermediate Similarity NPD8093 Discontinued
0.7232 Intermediate Similarity NPD7675 Phase 3
0.7232 Intermediate Similarity NPD7674 Phase 3
0.7232 Intermediate Similarity NPD7676 Clinical (unspecified phase)
0.7232 Intermediate Similarity NPD7426 Phase 1
0.7231 Intermediate Similarity NPD2780 Approved
0.7231 Intermediate Similarity NPD925 Approved
0.7231 Intermediate Similarity NPD926 Approved
0.7231 Intermediate Similarity NPD2782 Approved
0.7225 Intermediate Similarity NPD2952 Discontinued
0.7225 Intermediate Similarity NPD1229 Phase 2
0.7225 Intermediate Similarity NPD5003 Discontinued
0.722 Intermediate Similarity NPD6965 Clinical (unspecified phase)
0.7215 Intermediate Similarity NPD6147 Clinical (unspecified phase)
0.7211 Intermediate Similarity NPD6158 Phase 2
0.7211 Intermediate Similarity NPD6476 Clinical (unspecified phase)
0.7211 Intermediate Similarity NPD2882 Phase 1
0.7209 Intermediate Similarity NPD2916 Discontinued
0.7202 Intermediate Similarity NPD2616 Phase 3
0.7202 Intermediate Similarity NPD8488 Clinical (unspecified phase)
0.7202 Intermediate Similarity NPD604 Clinical (unspecified phase)
0.7202 Intermediate Similarity NPD2615 Phase 3
0.7196 Intermediate Similarity NPD4862 Clinical (unspecified phase)
0.7196 Intermediate Similarity NPD7001 Phase 3
0.7191 Intermediate Similarity NPD5644 Phase 1
0.7191 Intermediate Similarity NPD4558 Phase 2
0.7189 Intermediate Similarity NPD7470 Discontinued
0.7189 Intermediate Similarity NPD949 Phase 1
0.7189 Intermediate Similarity NPD3570 Phase 2
0.7179 Intermediate Similarity NPD5140 Approved
0.7179 Intermediate Similarity NPD5138 Approved
0.7178 Intermediate Similarity NPD7867 Phase 1
0.7175 Intermediate Similarity NPD7221 Approved
0.7175 Intermediate Similarity NPD7219 Approved
0.7172 Intermediate Similarity NPD5934 Clinical (unspecified phase)
0.7169 Intermediate Similarity NPD4897 Phase 2
0.7167 Intermediate Similarity NPD4440 Clinical (unspecified phase)
0.7166 Intermediate Similarity NPD3813 Approved
0.7162 Intermediate Similarity NPD5930 Phase 3
0.7161 Intermediate Similarity NPD8101 Phase 3
0.7157 Intermediate Similarity NPD7424 Clinical (unspecified phase)
0.7156 Intermediate Similarity NPD8458 Clinical (unspecified phase)
0.7155 Intermediate Similarity NPD5911 Clinical (unspecified phase)
0.715 Intermediate Similarity NPD4699 Discontinued
0.715 Intermediate Similarity NPD9383 Approved
0.715 Intermediate Similarity NPD5100 Phase 3

  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