Structure

Physi-Chem Properties

Molecular Weight:  331.17
Volume:  355.599
LogP:  3.619
LogD:  3.426
LogS:  -3.071
# Rotatable Bonds:  4
TPSA:  52.15
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  4
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.587
Synthetic Accessibility Score:  2.909
Fsp3:  0.19
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:  -4.849
MDCK Permeability:  9.713766303320881e-06
Pgp-inhibitor:  0.089
Pgp-substrate:  0.038
Human Intestinal Absorption (HIA):  0.059
20% Bioavailability (F20%):  0.101
30% Bioavailability (F30%):  0.042

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.966
Plasma Protein Binding (PPB):  81.13831329345703%
Volume Distribution (VD):  2.162
Pgp-substrate:  12.549720764160156%

ADMET: Metabolism

CYP1A2-inhibitor:  0.956
CYP1A2-substrate:  0.957
CYP2C19-inhibitor:  0.769
CYP2C19-substrate:  0.783
CYP2C9-inhibitor:  0.298
CYP2C9-substrate:  0.852
CYP2D6-inhibitor:  0.97
CYP2D6-substrate:  0.928
CYP3A4-inhibitor:  0.382
CYP3A4-substrate:  0.908

ADMET: Excretion

Clearance (CL):  9.617
Half-life (T1/2):  0.642

ADMET: Toxicity

hERG Blockers:  0.71
Human Hepatotoxicity (H-HT):  0.626
Drug-inuced Liver Injury (DILI):  0.636
AMES Toxicity:  0.626
Rat Oral Acute Toxicity:  0.95
Maximum Recommended Daily Dose:  0.955
Skin Sensitization:  0.198
Carcinogencity:  0.159
Eye Corrosion:  0.004
Eye Irritation:  0.028
Respiratory Toxicity:  0.978

Download Data

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

  Natural Product: NPC475070

Natural Product ID:  NPC475070
Common Name*:   Eudistomin X
IUPAC Name:   1-[1-(dimethylamino)-2-phenylethyl]-9H-pyrido[3,4-b]indol-6-ol
Synonyms:   Eudistomin X
Standard InCHIKey:  RHWHMFSBROSYKE-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C21H21N3O/c1-24(2)19(12-14-6-4-3-5-7-14)21-20-16(10-11-22-21)17-13-15(25)8-9-18(17)23-20/h3-11,13,19,23,25H,12H2,1-2H3
SMILES:  CN(C(c1nccc2c1[nH]c1c2cc(cc1)O)Cc1ccccc1)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL495660
PubChem CID:   10246141
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
NPT79 Organism Bacillus subtilis Bacillus subtilis IZ = 17.0 mm PMID[500167]
NPT79 Organism Bacillus subtilis Bacillus subtilis IZ = 18.0 mm PMID[500167]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus IZ = 11.0 mm PMID[500167]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus IZ = 12.0 mm PMID[500167]
NPT19 Organism Escherichia coli Escherichia coli IZ = 15.0 mm PMID[500167]
NPT19 Organism Escherichia coli Escherichia coli IZ = 20.0 mm PMID[500167]
NPT20 Organism Candida albicans Candida albicans IZ = 17.0 mm PMID[500167]
NPT20 Organism Candida albicans Candida albicans IZ = 18.0 mm PMID[500167]

☑ 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 NPC475070 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
0.9326 High Similarity NPC476041
0.9326 High Similarity NPC304926
0.9316 High Similarity NPC5145
0.9076 High Similarity NPC324149
0.9011 High Similarity NPC171171
0.8973 High Similarity NPC99666
0.8901 High Similarity NPC204717
0.8889 High Similarity NPC476167
0.8852 High Similarity NPC314002
0.8846 High Similarity NPC220765
0.8842 High Similarity NPC176538
0.8836 High Similarity NPC192315
0.8783 High Similarity NPC77555
0.8725 High Similarity NPC6215
0.8705 High Similarity NPC223427
0.8676 High Similarity NPC60006
0.866 High Similarity NPC470500
0.8653 High Similarity NPC211813
0.8646 High Similarity NPC249040
0.8626 High Similarity NPC184964
0.8612 High Similarity NPC295228
0.8579 High Similarity NPC476116
0.8564 High Similarity NPC213530
0.8564 High Similarity NPC193267
0.8537 High Similarity NPC245348
0.85 High Similarity NPC477610
0.8426 Intermediate Similarity NPC476124
0.8426 Intermediate Similarity NPC476121
0.84 Intermediate Similarity NPC208284
0.8394 Intermediate Similarity NPC156704
0.8381 Intermediate Similarity NPC207686
0.8378 Intermediate Similarity NPC88363
0.836 Intermediate Similarity NPC46580
0.8357 Intermediate Similarity NPC41679
0.835 Intermediate Similarity NPC123976
0.835 Intermediate Similarity NPC167860
0.8333 Intermediate Similarity NPC476451
0.8333 Intermediate Similarity NPC307963
0.8325 Intermediate Similarity NPC92111
0.8316 Intermediate Similarity NPC232727
0.8316 Intermediate Similarity NPC32771
0.8279 Intermediate Similarity NPC81175
0.8272 Intermediate Similarity NPC76748
0.8265 Intermediate Similarity NPC315491
0.8265 Intermediate Similarity NPC45459
0.8247 Intermediate Similarity NPC251090
0.8245 Intermediate Similarity NPC48938
0.8241 Intermediate Similarity NPC39092
0.8233 Intermediate Similarity NPC477861
0.8232 Intermediate Similarity NPC245816
0.8232 Intermediate Similarity NPC476138
0.8227 Intermediate Similarity NPC266931
0.8221 Intermediate Similarity NPC130570
0.822 Intermediate Similarity NPC296527
0.822 Intermediate Similarity NPC128751
0.822 Intermediate Similarity NPC246700
0.8191 Intermediate Similarity NPC285558
0.8178 Intermediate Similarity NPC477549
0.8177 Intermediate Similarity NPC106833
0.8177 Intermediate Similarity NPC469497
0.8173 Intermediate Similarity NPC213308
0.8159 Intermediate Similarity NPC477111
0.8158 Intermediate Similarity NPC15102
0.8155 Intermediate Similarity NPC477609
0.8146 Intermediate Similarity NPC8022
0.8146 Intermediate Similarity NPC470799
0.8141 Intermediate Similarity NPC53144
0.8141 Intermediate Similarity NPC200836
0.8141 Intermediate Similarity NPC476098
0.8125 Intermediate Similarity NPC310118
0.8107 Intermediate Similarity NPC27041
0.8103 Intermediate Similarity NPC326634
0.8081 Intermediate Similarity NPC19872
0.8081 Intermediate Similarity NPC329793
0.8073 Intermediate Similarity NPC171393
0.8073 Intermediate Similarity NPC295452
0.8069 Intermediate Similarity NPC82548
0.8066 Intermediate Similarity NPC314954
0.8066 Intermediate Similarity NPC253580
0.8066 Intermediate Similarity NPC477608
0.8066 Intermediate Similarity NPC477607
0.8061 Intermediate Similarity NPC242209
0.806 Intermediate Similarity NPC477113
0.8058 Intermediate Similarity NPC469928
0.8051 Intermediate Similarity NPC329541
0.8045 Intermediate Similarity NPC178858
0.8032 Intermediate Similarity NPC96890
0.8019 Intermediate Similarity NPC470126
0.8 Intermediate Similarity NPC280272
0.8 Intermediate Similarity NPC471603
0.8 Intermediate Similarity NPC26679
0.8 Intermediate Similarity NPC470501
0.7991 Intermediate Similarity NPC473312
0.799 Intermediate Similarity NPC276657
0.799 Intermediate Similarity NPC315957
0.7989 Intermediate Similarity NPC72980
0.798 Intermediate Similarity NPC265576
0.7972 Intermediate Similarity NPC184225
0.797 Intermediate Similarity NPC222018
0.7968 Intermediate Similarity NPC474409
0.7963 Intermediate Similarity NPC97902
0.7959 Intermediate Similarity NPC106937
0.7953 Intermediate Similarity NPC469554
0.7952 Intermediate Similarity NPC470502
0.7952 Intermediate Similarity NPC60621
0.7941 Intermediate Similarity NPC185782
0.7934 Intermediate Similarity NPC110151
0.7931 Intermediate Similarity NPC473362
0.7931 Intermediate Similarity NPC166492
0.7931 Intermediate Similarity NPC88008
0.7929 Intermediate Similarity NPC153042
0.7928 Intermediate Similarity NPC471891
0.7923 Intermediate Similarity NPC131718
0.7921 Intermediate Similarity NPC470505
0.7917 Intermediate Similarity NPC284678
0.7913 Intermediate Similarity NPC316981
0.7903 Intermediate Similarity NPC63751
0.7902 Intermediate Similarity NPC85273
0.7897 Intermediate Similarity NPC95783
0.7887 Intermediate Similarity NPC214980
0.7885 Intermediate Similarity NPC183407
0.7885 Intermediate Similarity NPC477110
0.7882 Intermediate Similarity NPC474145
0.7882 Intermediate Similarity NPC475841
0.7877 Intermediate Similarity NPC470503
0.7876 Intermediate Similarity NPC94943
0.7874 Intermediate Similarity NPC476287
0.7874 Intermediate Similarity NPC478074
0.787 Intermediate Similarity NPC101543
0.7865 Intermediate Similarity NPC176127
0.786 Intermediate Similarity NPC326363
0.7843 Intermediate Similarity NPC270918
0.7842 Intermediate Similarity NPC59269
0.7828 Intermediate Similarity NPC276517
0.7826 Intermediate Similarity NPC294620
0.7824 Intermediate Similarity NPC190007
0.7816 Intermediate Similarity NPC471304
0.7812 Intermediate Similarity NPC314394
0.781 Intermediate Similarity NPC264285
0.7807 Intermediate Similarity NPC317430
0.7804 Intermediate Similarity NPC319232
0.7804 Intermediate Similarity NPC24370
0.7804 Intermediate Similarity NPC132631
0.7804 Intermediate Similarity NPC103687
0.7798 Intermediate Similarity NPC325976
0.7783 Intermediate Similarity NPC475774
0.7772 Intermediate Similarity NPC212535
0.7762 Intermediate Similarity NPC469727
0.7756 Intermediate Similarity NPC53344
0.7754 Intermediate Similarity NPC49954
0.7754 Intermediate Similarity NPC474561
0.7747 Intermediate Similarity NPC325903
0.7744 Intermediate Similarity NPC62749
0.7742 Intermediate Similarity NPC102423
0.774 Intermediate Similarity NPC219087
0.7734 Intermediate Similarity NPC470678
0.7729 Intermediate Similarity NPC11464
0.7727 Intermediate Similarity NPC15801
0.7723 Intermediate Similarity NPC329747
0.7723 Intermediate Similarity NPC121772
0.7718 Intermediate Similarity NPC476465
0.7718 Intermediate Similarity NPC171787
0.7707 Intermediate Similarity NPC475288
0.7707 Intermediate Similarity NPC472111
0.7703 Intermediate Similarity NPC471080
0.7703 Intermediate Similarity NPC469592
0.7701 Intermediate Similarity NPC471178
0.7688 Intermediate Similarity NPC282231
0.7688 Intermediate Similarity NPC471177
0.7688 Intermediate Similarity NPC124542
0.7688 Intermediate Similarity NPC59779
0.7684 Intermediate Similarity NPC313791
0.7676 Intermediate Similarity NPC92796
0.7676 Intermediate Similarity NPC135141
0.7676 Intermediate Similarity NPC230869
0.7672 Intermediate Similarity NPC314940
0.7672 Intermediate Similarity NPC473764
0.7667 Intermediate Similarity NPC250835
0.7667 Intermediate Similarity NPC470549
0.7662 Intermediate Similarity NPC474188
0.766 Intermediate Similarity NPC160105
0.7659 Intermediate Similarity NPC165349
0.7659 Intermediate Similarity NPC264166
0.7659 Intermediate Similarity NPC274291
0.7659 Intermediate Similarity NPC47059
0.7659 Intermediate Similarity NPC329708
0.7659 Intermediate Similarity NPC118832
0.7655 Intermediate Similarity NPC91868
0.7655 Intermediate Similarity NPC63971
0.7653 Intermediate Similarity NPC132642
0.765 Intermediate Similarity NPC195314
0.765 Intermediate Similarity NPC25008
0.765 Intermediate Similarity NPC469760
0.765 Intermediate Similarity NPC469765
0.765 Intermediate Similarity NPC73952
0.765 Intermediate Similarity NPC469786
0.765 Intermediate Similarity NPC469763
0.765 Intermediate Similarity NPC259644
0.7635 Intermediate Similarity NPC23420
0.7635 Intermediate Similarity NPC106771

  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 NPC475070 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
0.913 High Similarity NPD5575 Clinical (unspecified phase)
0.8586 High Similarity NPD7948 Phase 1
0.8516 High Similarity NPD5065 Approved
0.8416 Intermediate Similarity NPD6803 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD1038 Approved
0.8265 Intermediate Similarity NPD484 Approved
0.8254 Intermediate Similarity NPD6344 Clinical (unspecified phase)
0.8238 Intermediate Similarity NPD1304 Clinical (unspecified phase)
0.8235 Intermediate Similarity NPD7112 Discontinued
0.8214 Intermediate Similarity NPD4118 Clinical (unspecified phase)
0.8155 Intermediate Similarity NPD8405 Clinical (unspecified phase)
0.8146 Intermediate Similarity NPD5612 Discontinued
0.8143 Intermediate Similarity NPD7603 Discontinued
0.81 Intermediate Similarity NPD4795 Phase 2
0.8084 Intermediate Similarity NPD5040 Clinical (unspecified phase)
0.8063 Intermediate Similarity NPD6610 Clinical (unspecified phase)
0.799 Intermediate Similarity NPD1740 Approved
0.799 Intermediate Similarity NPD1739 Approved
0.798 Intermediate Similarity NPD5658 Approved
0.7959 Intermediate Similarity NPD802 Phase 2
0.795 Intermediate Similarity NPD4511 Phase 1
0.791 Intermediate Similarity NPD3931 Approved
0.791 Intermediate Similarity NPD3928 Approved
0.7871 Intermediate Similarity NPD4886 Phase 2
0.7847 Intermediate Similarity NPD7823 Clinical (unspecified phase)
0.7843 Intermediate Similarity NPD7222 Phase 2
0.7828 Intermediate Similarity NPD3324 Clinical (unspecified phase)
0.7826 Intermediate Similarity NPD3330 Phase 1
0.7794 Intermediate Similarity NPD3932 Clinical (unspecified phase)
0.7766 Intermediate Similarity NPD1325 Approved
0.7766 Intermediate Similarity NPD1326 Approved
0.7761 Intermediate Similarity NPD8396 Approved
0.7761 Intermediate Similarity NPD8395 Approved
0.7761 Intermediate Similarity NPD3825 Phase 3
0.7761 Intermediate Similarity NPD3814 Phase 1
0.776 Intermediate Similarity NPD6595 Phase 3
0.7758 Intermediate Similarity NPD5483 Clinical (unspecified phase)
0.7756 Intermediate Similarity NPD6838 Clinical (unspecified phase)
0.7754 Intermediate Similarity NPD424 Approved
0.7754 Intermediate Similarity NPD425 Approved
0.7736 Intermediate Similarity NPD6242 Discontinued
0.7731 Intermediate Similarity NPD5559 Phase 2
0.7725 Intermediate Similarity NPD5934 Clinical (unspecified phase)
0.7718 Intermediate Similarity NPD2187 Approved
0.7718 Intermediate Similarity NPD2189 Approved
0.7707 Intermediate Similarity NPD5530 Phase 1
0.768 Intermediate Similarity NPD5522 Clinical (unspecified phase)
0.767 Intermediate Similarity NPD7452 Approved
0.767 Intermediate Similarity NPD7453 Approved
0.767 Intermediate Similarity NPD3930 Clinical (unspecified phase)
0.7659 Intermediate Similarity NPD31 Approved
0.7659 Intermediate Similarity NPD32 Approved
0.7659 Intermediate Similarity NPD4034 Approved
0.7659 Intermediate Similarity NPD4036 Approved
0.7659 Intermediate Similarity NPD4035 Approved
0.7659 Intermediate Similarity NPD4122 Approved
0.7659 Intermediate Similarity NPD4033 Approved
0.7659 Intermediate Similarity NPD4038 Approved
0.7659 Intermediate Similarity NPD4037 Approved
0.7659 Intermediate Similarity NPD4039 Approved
0.7656 Intermediate Similarity NPD6159 Phase 2
0.7656 Intermediate Similarity NPD6203 Clinical (unspecified phase)
0.7638 Intermediate Similarity NPD3404 Approved
0.7602 Intermediate Similarity NPD2762 Phase 2
0.7596 Intermediate Similarity NPD6158 Phase 2
0.7596 Intermediate Similarity NPD6476 Clinical (unspecified phase)
0.7591 Intermediate Similarity NPD7558 Phase 2
0.7579 Intermediate Similarity NPD4184 Clinical (unspecified phase)
0.7561 Intermediate Similarity NPD6975 Discontinued
0.7552 Intermediate Similarity NPD6492 Phase 2
0.7536 Intermediate Similarity NPD1322 Clinical (unspecified phase)
0.7525 Intermediate Similarity NPD2383 Phase 1
0.7525 Intermediate Similarity NPD8431 Approved
0.7525 Intermediate Similarity NPD6141 Clinical (unspecified phase)
0.7513 Intermediate Similarity NPD925 Approved
0.7513 Intermediate Similarity NPD926 Approved
0.75 Intermediate Similarity NPD2175 Phase 3
0.75 Intermediate Similarity NPD2176 Approved
0.75 Intermediate Similarity NPD2177 Approved
0.75 Intermediate Similarity NPD2882 Phase 1
0.7488 Intermediate Similarity NPD5426 Phase 3
0.7488 Intermediate Similarity NPD5901 Discontinued
0.7487 Intermediate Similarity NPD5255 Approved
0.7478 Intermediate Similarity NPD7068 Approved
0.7478 Intermediate Similarity NPD7067 Approved
0.7461 Intermediate Similarity NPD9690 Approved
0.7453 Intermediate Similarity NPD8488 Clinical (unspecified phase)
0.7447 Intermediate Similarity NPD112 Approved
0.7447 Intermediate Similarity NPD9705 Discontinued
0.7443 Intermediate Similarity NPD4845 Discontinued
0.7441 Intermediate Similarity NPD5936 Approved
0.7441 Intermediate Similarity NPD5939 Approved
0.7431 Intermediate Similarity NPD4401 Phase 2
0.7431 Intermediate Similarity NPD4403 Phase 3
0.7429 Intermediate Similarity NPD6545 Clinical (unspecified phase)
0.7429 Intermediate Similarity NPD2125 Clinical (unspecified phase)
0.7426 Intermediate Similarity NPD9695 Approved
0.7423 Intermediate Similarity NPD6375 Clinical (unspecified phase)
0.7416 Intermediate Similarity NPD1392 Approved
0.7414 Intermediate Similarity NPD8442 Discontinued
0.7406 Intermediate Similarity NPD8458 Clinical (unspecified phase)
0.74 Intermediate Similarity NPD8110 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD604 Clinical (unspecified phase)
0.7389 Intermediate Similarity NPD4418 Discontinued
0.7387 Intermediate Similarity NPD706 Phase 1
0.7383 Intermediate Similarity NPD6958 Approved
0.7383 Intermediate Similarity NPD6957 Approved
0.7381 Intermediate Similarity NPD7666 Phase 3
0.7381 Intermediate Similarity NPD2916 Discontinued
0.7381 Intermediate Similarity NPD7665 Phase 2
0.7376 Intermediate Similarity NPD3921 Approved
0.7376 Intermediate Similarity NPD3922 Approved
0.7376 Intermediate Similarity NPD3924 Approved
0.7376 Intermediate Similarity NPD3923 Approved
0.7376 Intermediate Similarity NPD8512 Phase 3
0.7368 Intermediate Similarity NPD5138 Approved
0.7368 Intermediate Similarity NPD5140 Approved
0.7368 Intermediate Similarity NPD3003 Approved
0.7366 Intermediate Similarity NPD2837 Discontinued
0.7363 Intermediate Similarity NPD3813 Approved
0.7361 Intermediate Similarity NPD7194 Discontinued
0.736 Intermediate Similarity NPD7414 Clinical (unspecified phase)
0.736 Intermediate Similarity NPD4203 Approved
0.736 Intermediate Similarity NPD4204 Approved
0.7358 Intermediate Similarity NPD5067 Phase 2
0.7358 Intermediate Similarity NPD5066 Phase 2
0.7354 Intermediate Similarity NPD6494 Phase 2
0.7348 Intermediate Similarity NPD4558 Phase 2
0.7345 Intermediate Similarity NPD2921 Clinical (unspecified phase)
0.7344 Intermediate Similarity NPD2781 Approved
0.7344 Intermediate Similarity NPD5069 Clinical (unspecified phase)
0.7337 Intermediate Similarity NPD4702 Approved
0.7337 Intermediate Similarity NPD4703 Approved
0.7333 Intermediate Similarity NPD5100 Phase 3
0.733 Intermediate Similarity NPD7000 Clinical (unspecified phase)
0.733 Intermediate Similarity NPD2782 Approved
0.733 Intermediate Similarity NPD2780 Approved
0.733 Intermediate Similarity NPD6999 Discontinued
0.7327 Intermediate Similarity NPD5912 Clinical (unspecified phase)
0.7327 Intermediate Similarity NPD5913 Phase 3
0.7324 Intermediate Similarity NPD8093 Discontinued
0.7316 Intermediate Similarity NPD1684 Approved
0.7316 Intermediate Similarity NPD1685 Approved
0.7316 Intermediate Similarity NPD5482 Discontinued
0.7311 Intermediate Similarity NPD3013 Phase 3
0.7311 Intermediate Similarity NPD3014 Clinical (unspecified phase)
0.731 Intermediate Similarity NPD8464 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD5669 Clinical (unspecified phase)
0.7302 Intermediate Similarity NPD6711 Approved
0.7297 Intermediate Similarity NPD6968 Phase 2
0.7297 Intermediate Similarity NPD6969 Phase 2
0.7296 Intermediate Similarity NPD4181 Approved
0.7293 Intermediate Similarity NPD3962 Phase 2
0.7293 Intermediate Similarity NPD3959 Phase 2
0.729 Intermediate Similarity NPD2615 Phase 3
0.729 Intermediate Similarity NPD2616 Phase 3
0.7285 Intermediate Similarity NPD6164 Phase 2
0.7285 Intermediate Similarity NPD6165 Phase 2
0.7277 Intermediate Similarity NPD6281 Approved
0.7277 Intermediate Similarity NPD949 Phase 1
0.7277 Intermediate Similarity NPD4502 Phase 2
0.7273 Intermediate Similarity NPD7867 Phase 1
0.7273 Intermediate Similarity NPD4044 Discontinued
0.7269 Intermediate Similarity NPD7423 Phase 2
0.726 Intermediate Similarity NPD7219 Approved
0.726 Intermediate Similarity NPD7221 Approved
0.7259 Intermediate Similarity NPD4079 Approved
0.7259 Intermediate Similarity NPD4076 Approved
0.7256 Intermediate Similarity NPD6140 Clinical (unspecified phase)
0.7256 Intermediate Similarity NPD4897 Phase 2
0.7251 Intermediate Similarity NPD6290 Phase 2
0.7251 Intermediate Similarity NPD1197 Approved
0.7248 Intermediate Similarity NPD5930 Phase 3
0.7246 Intermediate Similarity NPD4548 Discontinued
0.7243 Intermediate Similarity NPD7594 Clinical (unspecified phase)
0.7243 Intermediate Similarity NPD2794 Discontinued
0.724 Intermediate Similarity NPD5744 Clinical (unspecified phase)
0.7236 Intermediate Similarity NPD5728 Clinical (unspecified phase)
0.7236 Intermediate Similarity NPD2094 Phase 2
0.7236 Intermediate Similarity NPD2092 Phase 2
0.7236 Intermediate Similarity NPD2095 Phase 2
0.7235 Intermediate Similarity NPD3354 Phase 2
0.7228 Intermediate Similarity NPD6965 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD6147 Clinical (unspecified phase)
0.7217 Intermediate Similarity NPD7947 Clinical (unspecified phase)
0.7217 Intermediate Similarity NPD6376 Discontinued
0.7215 Intermediate Similarity NPD7726 Phase 1
0.7215 Intermediate Similarity NPD6530 Approved
0.7215 Intermediate Similarity NPD6531 Approved
0.7213 Intermediate Similarity NPD4637 Clinical (unspecified phase)
0.7209 Intermediate Similarity NPD8094 Discontinued
0.7208 Intermediate Similarity NPD3505 Approved
0.7208 Intermediate Similarity NPD3506 Approved
0.7206 Intermediate Similarity NPD6569 Phase 2
0.7205 Intermediate Similarity NPD6473 Phase 1
0.7204 Intermediate Similarity NPD4862 Clinical (unspecified phase)
0.7202 Intermediate Similarity NPD3402 Phase 1
0.72 Intermediate Similarity NPD2091 Phase 2
0.72 Intermediate Similarity NPD2096 Phase 2
0.7198 Intermediate Similarity NPD5644 Phase 1

  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