Structure

Physi-Chem Properties

Molecular Weight:  325.12
Volume:  341.769
LogP:  4.465
LogD:  3.717
LogS:  -6.02
# Rotatable Bonds:  2
TPSA:  50.8
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.5
Synthetic Accessibility Score:  2.229
Fsp3:  0.048
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.038
MDCK Permeability:  1.5509422155446373e-05
Pgp-inhibitor:  0.129
Pgp-substrate:  0.515
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.863
30% Bioavailability (F30%):  0.481

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.621
Plasma Protein Binding (PPB):  97.27393341064453%
Volume Distribution (VD):  1.972
Pgp-substrate:  1.2397550344467163%

ADMET: Metabolism

CYP1A2-inhibitor:  0.989
CYP1A2-substrate:  0.779
CYP2C19-inhibitor:  0.861
CYP2C19-substrate:  0.126
CYP2C9-inhibitor:  0.64
CYP2C9-substrate:  0.93
CYP2D6-inhibitor:  0.884
CYP2D6-substrate:  0.933
CYP3A4-inhibitor:  0.88
CYP3A4-substrate:  0.181

ADMET: Excretion

Clearance (CL):  3.668
Half-life (T1/2):  0.123

ADMET: Toxicity

hERG Blockers:  0.458
Human Hepatotoxicity (H-HT):  0.969
Drug-inuced Liver Injury (DILI):  0.964
AMES Toxicity:  0.903
Rat Oral Acute Toxicity:  0.623
Maximum Recommended Daily Dose:  0.871
Skin Sensitization:  0.747
Carcinogencity:  0.398
Eye Corrosion:  0.004
Eye Irritation:  0.9
Respiratory Toxicity:  0.99

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

  Natural Product: NPC123976

Natural Product ID:  NPC123976
Common Name*:   Trigonostemonine D
IUPAC Name:   1-(7-methoxyquinolin-4-yl)-9H-pyrido[3,4-b]indole
Synonyms:   Trigonostemonine D
Standard InCHIKey:  LKOLZHSYTUIODN-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C21H15N3O/c1-25-13-6-7-15-16(8-10-22-19(15)12-13)20-21-17(9-11-23-20)14-4-2-3-5-18(14)24-21/h2-12,24H,1H3
SMILES:  COc1ccc2c(c1)nccc2c1nccc2c1[nH]c1c2cccc1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1957113
PubChem CID:   57400007
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
NPO503 Trigonostemon lii Species Euphorbiaceae Eukaryota leaves n.a. n.a. PMID[22342628]
NPO503 Trigonostemon lii Species Euphorbiaceae 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
NPT116 Cell Line HL-60 Homo sapiens IC50 > 40000.0 nM PMID[553270]
NPT659 Cell Line SMMC-7721 Homo sapiens IC50 > 40000.0 nM PMID[553270]
NPT81 Cell Line A549 Homo sapiens IC50 > 40000.0 nM PMID[553270]
NPT83 Cell Line MCF7 Homo sapiens IC50 > 40000.0 nM PMID[553270]
NPT660 Cell Line SW480 Homo sapiens IC50 > 40000.0 nM PMID[553270]

☑ 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 NPC123976 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 NPC167860
0.9588 High Similarity NPC213530
0.9588 High Similarity NPC193267
0.957 High Similarity NPC232727
0.9418 High Similarity NPC285558
0.9005 High Similarity NPC176538
0.8808 High Similarity NPC19872
0.8744 High Similarity NPC314954
0.8725 High Similarity NPC60621
0.8708 High Similarity NPC469554
0.8673 High Similarity NPC245816
0.8673 High Similarity NPC476138
0.8643 High Similarity NPC174758
0.8641 High Similarity NPC122436
0.8634 High Similarity NPC310118
0.8632 High Similarity NPC235685
0.8619 High Similarity NPC101543
0.8614 High Similarity NPC470549
0.8592 High Similarity NPC101350
0.8571 High Similarity NPC170114
0.8564 High Similarity NPC84478
0.8542 High Similarity NPC324149
0.852 High Similarity NPC121772
0.852 High Similarity NPC329747
0.8505 High Similarity NPC13880
0.8498 Intermediate Similarity NPC295228
0.8485 Intermediate Similarity NPC223427
0.8465 Intermediate Similarity NPC208284
0.8458 Intermediate Similarity NPC185782
0.8429 Intermediate Similarity NPC110151
0.8424 Intermediate Similarity NPC26679
0.8396 Intermediate Similarity NPC260434
0.839 Intermediate Similarity NPC274982
0.8385 Intermediate Similarity NPC296527
0.8366 Intermediate Similarity NPC174672
0.835 Intermediate Similarity NPC475070
0.835 Intermediate Similarity NPC470500
0.8342 Intermediate Similarity NPC76748
0.8333 Intermediate Similarity NPC315957
0.8317 Intermediate Similarity NPC475910
0.8299 Intermediate Similarity NPC92111
0.8293 Intermediate Similarity NPC471080
0.8293 Intermediate Similarity NPC469592
0.8281 Intermediate Similarity NPC91868
0.8281 Intermediate Similarity NPC63971
0.8274 Intermediate Similarity NPC267928
0.8272 Intermediate Similarity NPC284678
0.8261 Intermediate Similarity NPC304926
0.8261 Intermediate Similarity NPC476041
0.8235 Intermediate Similarity NPC5145
0.8235 Intermediate Similarity NPC11464
0.8214 Intermediate Similarity NPC307963
0.8213 Intermediate Similarity NPC8022
0.8213 Intermediate Similarity NPC470799
0.8204 Intermediate Similarity NPC476287
0.8173 Intermediate Similarity NPC305984
0.8144 Intermediate Similarity NPC46580
0.8141 Intermediate Similarity NPC72211
0.8137 Intermediate Similarity NPC82548
0.8134 Intermediate Similarity NPC469594
0.8131 Intermediate Similarity NPC251090
0.8131 Intermediate Similarity NPC70259
0.81 Intermediate Similarity NPC287437
0.809 Intermediate Similarity NPC70956
0.809 Intermediate Similarity NPC243834
0.8081 Intermediate Similarity NPC131017
0.8081 Intermediate Similarity NPC205934
0.8081 Intermediate Similarity NPC43787
0.8068 Intermediate Similarity NPC316981
0.806 Intermediate Similarity NPC329793
0.8045 Intermediate Similarity NPC477861
0.8031 Intermediate Similarity NPC176127
0.8029 Intermediate Similarity NPC266931
0.802 Intermediate Similarity NPC267423
0.801 Intermediate Similarity NPC476167
0.8009 Intermediate Similarity NPC292958
0.7991 Intermediate Similarity NPC21638
0.799 Intermediate Similarity NPC36229
0.799 Intermediate Similarity NPC16452
0.799 Intermediate Similarity NPC476581
0.7961 Intermediate Similarity NPC287208
0.796 Intermediate Similarity NPC192315
0.7952 Intermediate Similarity NPC152768
0.7952 Intermediate Similarity NPC148183
0.7941 Intermediate Similarity NPC53144
0.7941 Intermediate Similarity NPC162484
0.7931 Intermediate Similarity NPC476044
0.7923 Intermediate Similarity NPC469589
0.7921 Intermediate Similarity NPC476582
0.7921 Intermediate Similarity NPC476578
0.7921 Intermediate Similarity NPC4071
0.7917 Intermediate Similarity NPC96890
0.7904 Intermediate Similarity NPC53534
0.7897 Intermediate Similarity NPC280272
0.7895 Intermediate Similarity NPC202768
0.7895 Intermediate Similarity NPC53069
0.7895 Intermediate Similarity NPC264176
0.7895 Intermediate Similarity NPC296482
0.7892 Intermediate Similarity NPC291535
0.7892 Intermediate Similarity NPC475085
0.7892 Intermediate Similarity NPC475112
0.7889 Intermediate Similarity NPC99666
0.7887 Intermediate Similarity NPC477533
0.7882 Intermediate Similarity NPC234197
0.788 Intermediate Similarity NPC471762
0.7877 Intermediate Similarity NPC473041
0.7876 Intermediate Similarity NPC72980
0.787 Intermediate Similarity NPC227908
0.7864 Intermediate Similarity NPC323345
0.7864 Intermediate Similarity NPC470164
0.7846 Intermediate Similarity NPC48938
0.7843 Intermediate Similarity NPC31930
0.7842 Intermediate Similarity NPC476518
0.7841 Intermediate Similarity NPC26543
0.7834 Intermediate Similarity NPC473185
0.7826 Intermediate Similarity NPC313189
0.781 Intermediate Similarity NPC96405
0.781 Intermediate Similarity NPC171409
0.781 Intermediate Similarity NPC94157
0.7805 Intermediate Similarity NPC199277
0.7805 Intermediate Similarity NPC135887
0.7805 Intermediate Similarity NPC295898
0.7804 Intermediate Similarity NPC86078
0.7801 Intermediate Similarity NPC121658
0.7801 Intermediate Similarity NPC14651
0.78 Intermediate Similarity NPC133140
0.78 Intermediate Similarity NPC195268
0.7796 Intermediate Similarity NPC26850
0.7788 Intermediate Similarity NPC476465
0.7788 Intermediate Similarity NPC153467
0.7778 Intermediate Similarity NPC476106
0.7778 Intermediate Similarity NPC152620
0.7768 Intermediate Similarity NPC99891
0.7767 Intermediate Similarity NPC475774
0.7761 Intermediate Similarity NPC84853
0.7761 Intermediate Similarity NPC106937
0.776 Intermediate Similarity NPC111624
0.7757 Intermediate Similarity NPC473179
0.7751 Intermediate Similarity NPC201697
0.774 Intermediate Similarity NPC135549
0.774 Intermediate Similarity NPC193777
0.7738 Intermediate Similarity NPC180504
0.7731 Intermediate Similarity NPC470501
0.7727 Intermediate Similarity NPC475253
0.7725 Intermediate Similarity NPC202605
0.7725 Intermediate Similarity NPC112206
0.7721 Intermediate Similarity NPC323969
0.7717 Intermediate Similarity NPC66777
0.7716 Intermediate Similarity NPC204717
0.7714 Intermediate Similarity NPC290689
0.7714 Intermediate Similarity NPC85273
0.771 Intermediate Similarity NPC303658
0.7707 Intermediate Similarity NPC249040
0.7707 Intermediate Similarity NPC477019
0.7704 Intermediate Similarity NPC161887
0.77 Intermediate Similarity NPC134079
0.77 Intermediate Similarity NPC183407
0.7692 Intermediate Similarity NPC472111
0.7689 Intermediate Similarity NPC162530
0.7685 Intermediate Similarity NPC470502
0.7685 Intermediate Similarity NPC477532
0.7685 Intermediate Similarity NPC242209
0.7681 Intermediate Similarity NPC200836
0.7677 Intermediate Similarity NPC94943
0.7677 Intermediate Similarity NPC314002
0.7673 Intermediate Similarity NPC198673
0.7667 Intermediate Similarity NPC473181
0.7665 Intermediate Similarity NPC212535
0.7665 Intermediate Similarity NPC220765
0.7664 Intermediate Similarity NPC27041
0.7656 Intermediate Similarity NPC249583
0.7656 Intermediate Similarity NPC4687
0.7653 Intermediate Similarity NPC235076
0.765 Intermediate Similarity NPC242928
0.7642 Intermediate Similarity NPC294620
0.7638 Intermediate Similarity NPC171171
0.763 Intermediate Similarity NPC199667
0.763 Intermediate Similarity NPC471304
0.763 Intermediate Similarity NPC188420
0.7628 Intermediate Similarity NPC264285
0.7626 Intermediate Similarity NPC190007
0.7621 Intermediate Similarity NPC11017
0.7615 Intermediate Similarity NPC470503
0.761 Intermediate Similarity NPC168911
0.7606 Intermediate Similarity NPC234078
0.7606 Intermediate Similarity NPC221100
0.76 Intermediate Similarity NPC30540
0.7593 Intermediate Similarity NPC17565
0.7591 Intermediate Similarity NPC6215
0.7588 Intermediate Similarity NPC81939
0.7579 Intermediate Similarity NPC177404
0.7578 Intermediate Similarity NPC141053
0.7577 Intermediate Similarity NPC474409
0.7573 Intermediate Similarity NPC187558
0.7573 Intermediate Similarity NPC18487
0.7561 Intermediate Similarity NPC77555
0.756 Intermediate Similarity NPC470930
0.756 Intermediate Similarity NPC470505
0.7559 Intermediate Similarity NPC48353
0.7559 Intermediate Similarity NPC471603

  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 NPC123976 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
0.85 High Similarity NPD5658 Approved
0.8442 Intermediate Similarity NPD4795 Phase 2
0.8333 Intermediate Similarity NPD1739 Approved
0.8333 Intermediate Similarity NPD1740 Approved
0.8308 Intermediate Similarity NPD1304 Clinical (unspecified phase)
0.8261 Intermediate Similarity NPD7823 Clinical (unspecified phase)
0.8233 Intermediate Similarity NPD7558 Phase 2
0.8214 Intermediate Similarity NPD1038 Approved
0.8164 Intermediate Similarity NPD6140 Clinical (unspecified phase)
0.8045 Intermediate Similarity NPD2921 Clinical (unspecified phase)
0.801 Intermediate Similarity NPD3825 Phase 3
0.801 Intermediate Similarity NPD4118 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD5482 Discontinued
0.7913 Intermediate Similarity NPD1392 Approved
0.791 Intermediate Similarity NPD7948 Phase 1
0.7902 Intermediate Similarity NPD5483 Clinical (unspecified phase)
0.79 Intermediate Similarity NPD6861 Clinical (unspecified phase)
0.79 Intermediate Similarity NPD3324 Clinical (unspecified phase)
0.7895 Intermediate Similarity NPD3815 Phase 1
0.7895 Intermediate Similarity NPD3816 Phase 1
0.7889 Intermediate Similarity NPD6569 Phase 2
0.7867 Intermediate Similarity NPD5612 Discontinued
0.7864 Intermediate Similarity NPD3003 Approved
0.7857 Intermediate Similarity NPD4440 Clinical (unspecified phase)
0.7844 Intermediate Similarity NPD6968 Phase 2
0.7844 Intermediate Similarity NPD6969 Phase 2
0.784 Intermediate Similarity NPD7194 Discontinued
0.78 Intermediate Similarity NPD3924 Approved
0.78 Intermediate Similarity NPD3922 Approved
0.78 Intermediate Similarity NPD3923 Approved
0.78 Intermediate Similarity NPD3921 Approved
0.7795 Intermediate Similarity NPD7414 Clinical (unspecified phase)
0.7788 Intermediate Similarity NPD2189 Approved
0.7788 Intermediate Similarity NPD2187 Approved
0.7762 Intermediate Similarity NPD5067 Phase 2
0.7762 Intermediate Similarity NPD5066 Phase 2
0.7761 Intermediate Similarity NPD5575 Clinical (unspecified phase)
0.7761 Intermediate Similarity NPD802 Phase 2
0.7757 Intermediate Similarity NPD3402 Phase 1
0.7745 Intermediate Similarity NPD4548 Discontinued
0.7736 Intermediate Similarity NPD5902 Approved
0.7736 Intermediate Similarity NPD5903 Approved
0.7721 Intermediate Similarity NPD6242 Discontinued
0.7717 Intermediate Similarity NPD5559 Phase 2
0.7696 Intermediate Similarity NPD6306 Phase 2
0.7692 Intermediate Similarity NPD8403 Phase 1
0.7679 Intermediate Similarity NPD7729 Clinical (unspecified phase)
0.7658 Intermediate Similarity NPD6494 Phase 2
0.7656 Intermediate Similarity NPD7222 Phase 2
0.7655 Intermediate Similarity NPD6473 Phase 1
0.7626 Intermediate Similarity NPD7426 Phase 1
0.7626 Intermediate Similarity NPD7675 Phase 3
0.7626 Intermediate Similarity NPD7674 Phase 3
0.7626 Intermediate Similarity NPD7676 Clinical (unspecified phase)
0.7621 Intermediate Similarity NPD7068 Approved
0.7621 Intermediate Similarity NPD7067 Approved
0.7613 Intermediate Similarity NPD4885 Approved
0.7608 Intermediate Similarity NPD5530 Phase 1
0.7602 Intermediate Similarity NPD8512 Phase 3
0.7595 Intermediate Similarity NPD5450 Discontinued
0.7588 Intermediate Similarity NPD4889 Approved
0.7573 Intermediate Similarity NPD1768 Approved
0.7566 Intermediate Similarity NPD4858 Phase 2
0.756 Intermediate Similarity NPD3397 Phase 2
0.7558 Intermediate Similarity NPD5930 Phase 3
0.7545 Intermediate Similarity NPD6963 Approved
0.7545 Intermediate Similarity NPD6964 Approved
0.7544 Intermediate Similarity NPD5802 Phase 2
0.7544 Intermediate Similarity NPD6573 Phase 3
0.7544 Intermediate Similarity NPD6572 Phase 2
0.7538 Intermediate Similarity NPD5065 Approved
0.7536 Intermediate Similarity NPD5863 Clinical (unspecified phase)
0.7513 Intermediate Similarity NPD6872 Clinical (unspecified phase)
0.7512 Intermediate Similarity NPD3478 Clinical (unspecified phase)
0.7512 Intermediate Similarity NPD3477 Phase 2
0.7512 Intermediate Similarity NPD3763 Approved
0.7511 Intermediate Similarity NPD6230 Discontinued
0.75 Intermediate Similarity NPD2472 Approved
0.75 Intermediate Similarity NPD2471 Approved
0.7489 Intermediate Similarity NPD4558 Phase 2
0.7489 Intermediate Similarity NPD6131 Phase 1
0.7476 Intermediate Similarity NPD4034 Approved
0.7476 Intermediate Similarity NPD32 Approved
0.7476 Intermediate Similarity NPD4122 Approved
0.7476 Intermediate Similarity NPD4035 Approved
0.7476 Intermediate Similarity NPD4038 Approved
0.7476 Intermediate Similarity NPD4036 Approved
0.7476 Intermediate Similarity NPD4033 Approved
0.7476 Intermediate Similarity NPD4039 Approved
0.7476 Intermediate Similarity NPD4037 Approved
0.7476 Intermediate Similarity NPD31 Approved
0.7465 Intermediate Similarity NPD8405 Clinical (unspecified phase)
0.7465 Intermediate Similarity NPD6985 Discontinued
0.7463 Intermediate Similarity NPD4418 Discontinued
0.7451 Intermediate Similarity NPD4372 Phase 1
0.7442 Intermediate Similarity NPD1322 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD1078 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD4926 Clinical (unspecified phase)
0.7429 Intermediate Similarity NPD4886 Phase 2
0.7413 Intermediate Similarity NPD7424 Clinical (unspecified phase)
0.7409 Intermediate Similarity NPD1856 Discontinued
0.7406 Intermediate Similarity NPD7453 Approved
0.7406 Intermediate Similarity NPD7452 Approved
0.7404 Intermediate Similarity NPD8442 Discontinued
0.7402 Intermediate Similarity NPD5913 Phase 3
0.7402 Intermediate Similarity NPD5912 Clinical (unspecified phase)
0.7397 Intermediate Similarity NPD5070 Clinical (unspecified phase)
0.7395 Intermediate Similarity NPD3330 Phase 1
0.7391 Intermediate Similarity NPD6769 Clinical (unspecified phase)
0.7382 Intermediate Similarity NPD6525 Clinical (unspecified phase)
0.7382 Intermediate Similarity NPD6244 Phase 3
0.7382 Intermediate Similarity NPD6243 Phase 3
0.7376 Intermediate Similarity NPD4920 Clinical (unspecified phase)
0.7376 Intermediate Similarity NPD4921 Phase 3
0.7376 Intermediate Similarity NPD4919 Phase 3
0.7373 Intermediate Similarity NPD6961 Discontinued
0.735 Intermediate Similarity NPD4204 Approved
0.735 Intermediate Similarity NPD3386 Phase 2
0.735 Intermediate Similarity NPD4203 Approved
0.7342 Intermediate Similarity NPD6246 Approved
0.734 Intermediate Similarity NPD1033 Clinical (unspecified phase)
0.734 Intermediate Similarity NPD6257 Clinical (unspecified phase)
0.734 Intermediate Similarity NPD1034 Phase 3
0.7337 Intermediate Similarity NPD3920 Phase 2
0.7336 Intermediate Similarity NPD2125 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD2062 Phase 2
0.733 Intermediate Similarity NPD7219 Approved
0.733 Intermediate Similarity NPD7221 Approved
0.732 Intermediate Similarity NPD2782 Approved
0.732 Intermediate Similarity NPD2780 Approved
0.7309 Intermediate Similarity NPD7603 Discontinued
0.7306 Intermediate Similarity NPD5632 Approved
0.7304 Intermediate Similarity NPD6790 Phase 1
0.7304 Intermediate Similarity NPD4021 Phase 2
0.7295 Intermediate Similarity NPD6491 Clinical (unspecified phase)
0.7291 Intermediate Similarity NPD4375 Approved
0.7282 Intermediate Similarity NPD425 Approved
0.7282 Intermediate Similarity NPD424 Approved
0.7277 Intermediate Similarity NPD3932 Clinical (unspecified phase)
0.7277 Intermediate Similarity NPD6150 Discontinued
0.7277 Intermediate Similarity NPD5601 Phase 2
0.7273 Intermediate Similarity NPD6500 Approved
0.7273 Intermediate Similarity NPD6501 Approved
0.7269 Intermediate Similarity NPD3570 Phase 2
0.7269 Intermediate Similarity NPD4131 Phase 3
0.7269 Intermediate Similarity NPD8091 Phase 3
0.7265 Intermediate Similarity NPD1258 Discontinued
0.7252 Intermediate Similarity NPD1954 Phase 1
0.7252 Intermediate Similarity NPD6824 Clinical (unspecified phase)
0.7249 Intermediate Similarity NPD4958 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD7859 Phase 2
0.7245 Intermediate Similarity NPD2781 Approved
0.7243 Intermediate Similarity NPD3930 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD6610 Clinical (unspecified phase)
0.7238 Intermediate Similarity NPD7955 Approved
0.7238 Intermediate Similarity NPD7956 Approved
0.7237 Intermediate Similarity NPD2757 Phase 2
0.7235 Intermediate Similarity NPD7069 Discontinued
0.7235 Intermediate Similarity NPD6202 Discontinued
0.7231 Intermediate Similarity NPD3343 Phase 3
0.7231 Intermediate Similarity NPD8284 Discontinued
0.7215 Intermediate Similarity NPD7112 Discontinued
0.7215 Intermediate Similarity NPD6803 Clinical (unspecified phase)
0.7214 Intermediate Similarity NPD2599 Approved
0.7214 Intermediate Similarity NPD2601 Approved
0.7214 Intermediate Similarity NPD2600 Approved
0.7214 Intermediate Similarity NPD6595 Phase 3
0.7212 Intermediate Similarity NPD6251 Discontinued
0.7212 Intermediate Similarity NPD3395 Approved
0.7212 Intermediate Similarity NPD3396 Approved
0.7209 Intermediate Similarity NPD5528 Clinical (unspecified phase)
0.7209 Intermediate Similarity NPD5529 Phase 1
0.7207 Intermediate Similarity NPD4881 Clinical (unspecified phase)
0.7206 Intermediate Similarity NPD5256 Discontinued
0.7205 Intermediate Similarity NPD1259 Discontinued
0.7204 Intermediate Similarity NPD4396 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD4072 Approved
0.72 Intermediate Similarity NPD1032 Phase 2
0.72 Intermediate Similarity NPD4071 Approved
0.7198 Intermediate Similarity NPD4876 Phase 3
0.7198 Intermediate Similarity NPD4875 Phase 3
0.7191 Intermediate Similarity NPD5644 Phase 1
0.7189 Intermediate Similarity NPD4502 Phase 2
0.7189 Intermediate Similarity NPD6567 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD3938 Phase 1
0.7179 Intermediate Similarity NPD8100 Phase 3
0.7164 Intermediate Similarity NPD1620 Clinical (unspecified phase)
0.7162 Intermediate Similarity NPD6760 Discontinued
0.7157 Intermediate Similarity NPD6344 Clinical (unspecified phase)
0.7155 Intermediate Similarity NPD8049 Phase 2
0.715 Intermediate Similarity NPD2334 Discontinued
0.7149 Intermediate Similarity NPD7705 Clinical (unspecified phase)
0.7149 Intermediate Similarity NPD8358 Approved
0.7149 Intermediate Similarity NPD4429 Discontinued
0.7143 Intermediate Similarity NPD1622 Discontinued
0.7143 Intermediate Similarity NPD2952 Discontinued
0.7143 Intermediate Similarity NPD3255 Phase 1
0.7143 Intermediate Similarity NPD3254 Phase 1
0.7137 Intermediate Similarity NPD4350 Approved
0.7137 Intermediate Similarity NPD4349 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