Structure

Physi-Chem Properties

Molecular Weight:  327.14
Volume:  344.406
LogP:  4.142
LogD:  3.347
LogS:  -5.363
# Rotatable Bonds:  2
TPSA:  50.27
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.602
Synthetic Accessibility Score:  2.55
Fsp3:  0.143
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:  -5.43
MDCK Permeability:  1.7591666619409807e-05
Pgp-inhibitor:  0.92
Pgp-substrate:  0.99
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.01
30% Bioavailability (F30%):  0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.954
Plasma Protein Binding (PPB):  96.90557098388672%
Volume Distribution (VD):  1.892
Pgp-substrate:  1.284916877746582%

ADMET: Metabolism

CYP1A2-inhibitor:  0.94
CYP1A2-substrate:  0.975
CYP2C19-inhibitor:  0.566
CYP2C19-substrate:  0.619
CYP2C9-inhibitor:  0.412
CYP2C9-substrate:  0.905
CYP2D6-inhibitor:  0.62
CYP2D6-substrate:  0.453
CYP3A4-inhibitor:  0.514
CYP3A4-substrate:  0.939

ADMET: Excretion

Clearance (CL):  2.564
Half-life (T1/2):  0.042

ADMET: Toxicity

hERG Blockers:  0.692
Human Hepatotoxicity (H-HT):  0.496
Drug-inuced Liver Injury (DILI):  0.443
AMES Toxicity:  0.17
Rat Oral Acute Toxicity:  0.496
Maximum Recommended Daily Dose:  0.991
Skin Sensitization:  0.337
Carcinogencity:  0.048
Eye Corrosion:  0.003
Eye Irritation:  0.049
Respiratory Toxicity:  0.707

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Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC285558

Natural Product ID:  NPC285558
Common Name*:   Trigonostemonine E
IUPAC Name:   1-(7-methoxyquinolin-4-yl)-4,9-dihydro-3H-pyrido[3,4-b]indole
Synonyms:   Trigonostemonine E
Standard InCHIKey:  NLVZCPMCDXOEPT-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C21H17N3O/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/h2-8,10,12,24H,9,11H2,1H3
SMILES:  COc1ccc2c(c1)nccc2C1=NCCc2c1[nH]c1c2cccc1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1957114
PubChem CID:   57401814
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[493845]
NPT659 Cell Line SMMC-7721 Homo sapiens IC50 > 40000.0 nM PMID[493845]
NPT81 Cell Line A549 Homo sapiens IC50 > 40000.0 nM PMID[493845]
NPT83 Cell Line MCF7 Homo sapiens IC50 > 40000.0 nM PMID[493845]
NPT660 Cell Line SW480 Homo sapiens IC50 > 40000.0 nM PMID[493845]

☑ 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 NPC285558 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
0.9418 High Similarity NPC167860
0.9418 High Similarity NPC123976
0.9301 High Similarity NPC232727
0.9036 High Similarity NPC193267
0.9036 High Similarity NPC213530
0.9006 High Similarity NPC84478
0.8929 High Similarity NPC470549
0.8883 High Similarity NPC170114
0.8842 High Similarity NPC329747
0.8776 High Similarity NPC208284
0.8743 High Similarity NPC176538
0.873 High Similarity NPC13880
0.8663 High Similarity NPC76748
0.8617 High Similarity NPC92111
0.861 High Similarity NPC296527
0.8579 High Similarity NPC174758
0.8549 High Similarity NPC19872
0.8542 High Similarity NPC72211
0.8535 High Similarity NPC11464
0.8534 High Similarity NPC70259
0.8526 High Similarity NPC307963
0.8482 Intermediate Similarity NPC43787
0.8482 Intermediate Similarity NPC205934
0.848 Intermediate Similarity NPC310118
0.848 Intermediate Similarity NPC60621
0.8441 Intermediate Similarity NPC176127
0.8434 Intermediate Similarity NPC475910
0.8418 Intermediate Similarity NPC476138
0.8418 Intermediate Similarity NPC245816
0.8398 Intermediate Similarity NPC122436
0.8394 Intermediate Similarity NPC243834
0.8394 Intermediate Similarity NPC70956
0.836 Intermediate Similarity NPC46580
0.8359 Intermediate Similarity NPC121772
0.8358 Intermediate Similarity NPC316981
0.8357 Intermediate Similarity NPC101350
0.8342 Intermediate Similarity NPC251090
0.8325 Intermediate Similarity NPC162484
0.8325 Intermediate Similarity NPC274982
0.8325 Intermediate Similarity NPC223427
0.8325 Intermediate Similarity NPC314954
0.8317 Intermediate Similarity NPC266931
0.8316 Intermediate Similarity NPC267423
0.831 Intermediate Similarity NPC235685
0.83 Intermediate Similarity NPC174672
0.8294 Intermediate Similarity NPC469554
0.829 Intermediate Similarity NPC131017
0.8281 Intermediate Similarity NPC324149
0.828 Intermediate Similarity NPC72980
0.8278 Intermediate Similarity NPC110151
0.8274 Intermediate Similarity NPC475112
0.8274 Intermediate Similarity NPC291535
0.8274 Intermediate Similarity NPC475085
0.8267 Intermediate Similarity NPC26679
0.8265 Intermediate Similarity NPC315957
0.8252 Intermediate Similarity NPC477533
0.8227 Intermediate Similarity NPC469592
0.8227 Intermediate Similarity NPC471080
0.8223 Intermediate Similarity NPC476044
0.8209 Intermediate Similarity NPC185782
0.8208 Intermediate Similarity NPC101543
0.8191 Intermediate Similarity NPC475070
0.8187 Intermediate Similarity NPC99666
0.8178 Intermediate Similarity NPC295228
0.8173 Intermediate Similarity NPC329793
0.816 Intermediate Similarity NPC260434
0.8155 Intermediate Similarity NPC473041
0.815 Intermediate Similarity NPC476106
0.8128 Intermediate Similarity NPC96890
0.8122 Intermediate Similarity NPC287437
0.8119 Intermediate Similarity NPC201697
0.8107 Intermediate Similarity NPC305984
0.8104 Intermediate Similarity NPC473185
0.81 Intermediate Similarity NPC36229
0.81 Intermediate Similarity NPC476581
0.81 Intermediate Similarity NPC16452
0.81 Intermediate Similarity NPC470500
0.8093 Intermediate Similarity NPC195268
0.8093 Intermediate Similarity NPC133140
0.8088 Intermediate Similarity NPC94157
0.8081 Intermediate Similarity NPC234197
0.8079 Intermediate Similarity NPC5145
0.8075 Intermediate Similarity NPC475253
0.8069 Intermediate Similarity NPC82548
0.8069 Intermediate Similarity NPC476465
0.8068 Intermediate Similarity NPC469594
0.8066 Intermediate Similarity NPC471762
0.8061 Intermediate Similarity NPC242209
0.8051 Intermediate Similarity NPC106937
0.805 Intermediate Similarity NPC475774
0.8049 Intermediate Similarity NPC162530
0.8038 Intermediate Similarity NPC477532
0.803 Intermediate Similarity NPC4071
0.803 Intermediate Similarity NPC476582
0.803 Intermediate Similarity NPC476578
0.8029 Intermediate Similarity NPC473179
0.802 Intermediate Similarity NPC193777
0.802 Intermediate Similarity NPC267928
0.8011 Intermediate Similarity NPC26850
0.801 Intermediate Similarity NPC284678
0.8009 Intermediate Similarity NPC21638
0.8 Intermediate Similarity NPC53069
0.8 Intermediate Similarity NPC295898
0.8 Intermediate Similarity NPC296482
0.8 Intermediate Similarity NPC135887
0.8 Intermediate Similarity NPC199277
0.8 Intermediate Similarity NPC202768
0.7981 Intermediate Similarity NPC303658
0.7973 Intermediate Similarity NPC91868
0.7973 Intermediate Similarity NPC63971
0.7972 Intermediate Similarity NPC153467
0.7971 Intermediate Similarity NPC470799
0.7971 Intermediate Similarity NPC8022
0.7969 Intermediate Similarity NPC94943
0.7961 Intermediate Similarity NPC476287
0.795 Intermediate Similarity NPC31930
0.7941 Intermediate Similarity NPC473181
0.7931 Intermediate Similarity NPC313189
0.7927 Intermediate Similarity NPC171171
0.7921 Intermediate Similarity NPC470930
0.7917 Intermediate Similarity NPC204717
0.7917 Intermediate Similarity NPC180504
0.7917 Intermediate Similarity NPC190007
0.7913 Intermediate Similarity NPC48353
0.7913 Intermediate Similarity NPC264176
0.7902 Intermediate Similarity NPC199667
0.7902 Intermediate Similarity NPC471304
0.79 Intermediate Similarity NPC477019
0.7897 Intermediate Similarity NPC66777
0.7892 Intermediate Similarity NPC287208
0.7885 Intermediate Similarity NPC148183
0.7885 Intermediate Similarity NPC152768
0.7882 Intermediate Similarity NPC323345
0.7882 Intermediate Similarity NPC470164
0.7876 Intermediate Similarity NPC314002
0.7871 Intermediate Similarity NPC53144
0.7865 Intermediate Similarity NPC220765
0.7865 Intermediate Similarity NPC212535
0.7854 Intermediate Similarity NPC469589
0.7847 Intermediate Similarity NPC304926
0.7847 Intermediate Similarity NPC476041
0.7846 Intermediate Similarity NPC242928
0.7845 Intermediate Similarity NPC26872
0.7843 Intermediate Similarity NPC249583
0.7843 Intermediate Similarity NPC4687
0.7837 Intermediate Similarity NPC235076
0.783 Intermediate Similarity NPC280272
0.7826 Intermediate Similarity NPC96405
0.7826 Intermediate Similarity NPC171409
0.7826 Intermediate Similarity NPC112206
0.7826 Intermediate Similarity NPC202605
0.782 Intermediate Similarity NPC132642
0.7816 Intermediate Similarity NPC290689
0.7816 Intermediate Similarity NPC188420
0.7814 Intermediate Similarity NPC252251
0.7811 Intermediate Similarity NPC11017
0.781 Intermediate Similarity NPC23614
0.781 Intermediate Similarity NPC100079
0.781 Intermediate Similarity NPC264285
0.7808 Intermediate Similarity NPC473183
0.7798 Intermediate Similarity NPC473184
0.7788 Intermediate Similarity NPC478074
0.7788 Intermediate Similarity NPC149471
0.7788 Intermediate Similarity NPC271215
0.7784 Intermediate Similarity NPC177404
0.7778 Intermediate Similarity NPC474409
0.7778 Intermediate Similarity NPC26543
0.7773 Intermediate Similarity NPC11408
0.7773 Intermediate Similarity NPC292958
0.7761 Intermediate Similarity NPC476167
0.7756 Intermediate Similarity NPC135549
0.775 Intermediate Similarity NPC77555
0.7744 Intermediate Similarity NPC204385
0.7742 Intermediate Similarity NPC477531
0.774 Intermediate Similarity NPC251160
0.7739 Intermediate Similarity NPC326634
0.7737 Intermediate Similarity NPC312872
0.7729 Intermediate Similarity NPC470020
0.7725 Intermediate Similarity NPC96321
0.772 Intermediate Similarity NPC474798
0.7713 Intermediate Similarity NPC63751
0.7711 Intermediate Similarity NPC192315
0.7703 Intermediate Similarity NPC99891
0.7703 Intermediate Similarity NPC217554
0.77 Intermediate Similarity NPC194967
0.77 Intermediate Similarity NPC198503
0.7696 Intermediate Similarity NPC209174
0.7692 Intermediate Similarity NPC87413
0.7689 Intermediate Similarity NPC17565
0.7689 Intermediate Similarity NPC46451
0.7681 Intermediate Similarity NPC209769
0.7679 Intermediate Similarity NPC78609
0.7679 Intermediate Similarity NPC81939
0.7678 Intermediate Similarity NPC473513
0.7664 Intermediate Similarity NPC16352
0.7658 Intermediate Similarity NPC477861
0.7656 Intermediate Similarity NPC473180
0.7656 Intermediate Similarity NPC184964
0.7656 Intermediate Similarity NPC59269
0.7656 Intermediate Similarity NPC308137

  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 NPC285558 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
0.8824 High Similarity NPD1304 Clinical (unspecified phase)
0.8622 High Similarity NPD5658 Approved
0.8526 High Similarity NPD1038 Approved
0.8517 High Similarity NPD7558 Phase 2
0.8376 Intermediate Similarity NPD4795 Phase 2
0.8308 Intermediate Similarity NPD4118 Clinical (unspecified phase)
0.8308 Intermediate Similarity NPD3825 Phase 3
0.8265 Intermediate Similarity NPD1740 Approved
0.8265 Intermediate Similarity NPD1739 Approved
0.8238 Intermediate Similarity NPD5575 Clinical (unspecified phase)
0.8205 Intermediate Similarity NPD7948 Phase 1
0.82 Intermediate Similarity NPD1392 Approved
0.8195 Intermediate Similarity NPD7823 Clinical (unspecified phase)
0.8186 Intermediate Similarity NPD6140 Clinical (unspecified phase)
0.8164 Intermediate Similarity NPD6242 Discontinued
0.815 Intermediate Similarity NPD3003 Approved
0.8146 Intermediate Similarity NPD5612 Discontinued
0.8095 Intermediate Similarity NPD7414 Clinical (unspecified phase)
0.8093 Intermediate Similarity NPD3921 Approved
0.8093 Intermediate Similarity NPD3922 Approved
0.8093 Intermediate Similarity NPD3923 Approved
0.8093 Intermediate Similarity NPD3924 Approved
0.8069 Intermediate Similarity NPD2187 Approved
0.8069 Intermediate Similarity NPD2189 Approved
0.8051 Intermediate Similarity NPD802 Phase 2
0.8039 Intermediate Similarity NPD5066 Phase 2
0.8039 Intermediate Similarity NPD5067 Phase 2
0.801 Intermediate Similarity NPD3324 Clinical (unspecified phase)
0.801 Intermediate Similarity NPD6861 Clinical (unspecified phase)
0.801 Intermediate Similarity NPD5903 Approved
0.801 Intermediate Similarity NPD5902 Approved
0.8 Intermediate Similarity NPD3815 Phase 1
0.8 Intermediate Similarity NPD6569 Phase 2
0.8 Intermediate Similarity NPD3816 Phase 1
0.7943 Intermediate Similarity NPD7194 Discontinued
0.7931 Intermediate Similarity NPD7222 Phase 2
0.7917 Intermediate Similarity NPD6494 Phase 2
0.79 Intermediate Similarity NPD2921 Clinical (unspecified phase)
0.7882 Intermediate Similarity NPD8403 Phase 1
0.7876 Intermediate Similarity NPD4889 Approved
0.7857 Intermediate Similarity NPD3402 Phase 1
0.7857 Intermediate Similarity NPD5482 Discontinued
0.785 Intermediate Similarity NPD1768 Approved
0.785 Intermediate Similarity NPD4548 Discontinued
0.7833 Intermediate Similarity NPD3397 Phase 2
0.7831 Intermediate Similarity NPD5065 Approved
0.7814 Intermediate Similarity NPD5559 Phase 2
0.7812 Intermediate Similarity NPD3386 Phase 2
0.7807 Intermediate Similarity NPD6872 Clinical (unspecified phase)
0.7798 Intermediate Similarity NPD6963 Approved
0.7798 Intermediate Similarity NPD6964 Approved
0.7758 Intermediate Similarity NPD6230 Discontinued
0.7758 Intermediate Similarity NPD5483 Clinical (unspecified phase)
0.7739 Intermediate Similarity NPD4418 Discontinued
0.7725 Intermediate Similarity NPD1078 Clinical (unspecified phase)
0.7725 Intermediate Similarity NPD6985 Discontinued
0.7703 Intermediate Similarity NPD1322 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD7424 Clinical (unspecified phase)
0.7689 Intermediate Similarity NPD3763 Approved
0.7677 Intermediate Similarity NPD5912 Clinical (unspecified phase)
0.7677 Intermediate Similarity NPD5913 Phase 3
0.767 Intermediate Similarity NPD7452 Approved
0.767 Intermediate Similarity NPD7453 Approved
0.7634 Intermediate Similarity NPD7068 Approved
0.7634 Intermediate Similarity NPD7067 Approved
0.7621 Intermediate Similarity NPD6244 Phase 3
0.7621 Intermediate Similarity NPD6243 Phase 3
0.7617 Intermediate Similarity NPD3920 Phase 2
0.7615 Intermediate Similarity NPD6968 Phase 2
0.7615 Intermediate Similarity NPD6969 Phase 2
0.7614 Intermediate Similarity NPD6257 Clinical (unspecified phase)
0.7613 Intermediate Similarity NPD7729 Clinical (unspecified phase)
0.7612 Intermediate Similarity NPD3477 Phase 2
0.7612 Intermediate Similarity NPD3478 Clinical (unspecified phase)
0.7596 Intermediate Similarity NPD2125 Clinical (unspecified phase)
0.7578 Intermediate Similarity NPD4858 Phase 2
0.7573 Intermediate Similarity NPD4038 Approved
0.7573 Intermediate Similarity NPD4036 Approved
0.7573 Intermediate Similarity NPD4037 Approved
0.7573 Intermediate Similarity NPD4039 Approved
0.7573 Intermediate Similarity NPD31 Approved
0.7573 Intermediate Similarity NPD4034 Approved
0.7573 Intermediate Similarity NPD4033 Approved
0.7573 Intermediate Similarity NPD32 Approved
0.7573 Intermediate Similarity NPD4035 Approved
0.7573 Intermediate Similarity NPD4122 Approved
0.7563 Intermediate Similarity NPD4921 Phase 3
0.7563 Intermediate Similarity NPD4919 Phase 3
0.7563 Intermediate Similarity NPD4920 Clinical (unspecified phase)
0.7562 Intermediate Similarity NPD6491 Clinical (unspecified phase)
0.7559 Intermediate Similarity NPD5632 Approved
0.7559 Intermediate Similarity NPD8405 Clinical (unspecified phase)
0.7558 Intermediate Similarity NPD7674 Phase 3
0.7558 Intermediate Similarity NPD7426 Phase 1
0.7558 Intermediate Similarity NPD7676 Clinical (unspecified phase)
0.7558 Intermediate Similarity NPD7675 Phase 3
0.7546 Intermediate Similarity NPD6306 Phase 2
0.7545 Intermediate Similarity NPD4885 Approved
0.7545 Intermediate Similarity NPD6790 Phase 1
0.7536 Intermediate Similarity NPD3932 Clinical (unspecified phase)
0.7536 Intermediate Similarity NPD6150 Discontinued
0.7524 Intermediate Similarity NPD3570 Phase 2
0.7513 Intermediate Similarity NPD6610 Clinical (unspecified phase)
0.7513 Intermediate Similarity NPD2782 Approved
0.7513 Intermediate Similarity NPD2780 Approved
0.7512 Intermediate Similarity NPD4511 Phase 1
0.7511 Intermediate Similarity NPD6473 Phase 1
0.75 Intermediate Similarity NPD3814 Phase 1
0.75 Intermediate Similarity NPD3930 Clinical (unspecified phase)
0.7488 Intermediate Similarity NPD7069 Discontinued
0.7488 Intermediate Similarity NPD6769 Clinical (unspecified phase)
0.7488 Intermediate Similarity NPD5930 Phase 3
0.7488 Intermediate Similarity NPD3330 Phase 1
0.7488 Intermediate Similarity NPD5070 Clinical (unspecified phase)
0.7487 Intermediate Similarity NPD4021 Phase 2
0.7487 Intermediate Similarity NPD6595 Phase 3
0.7478 Intermediate Similarity NPD4440 Clinical (unspecified phase)
0.7475 Intermediate Similarity NPD5256 Discontinued
0.7475 Intermediate Similarity NPD3810 Clinical (unspecified phase)
0.7475 Intermediate Similarity NPD3395 Approved
0.7475 Intermediate Similarity NPD6251 Discontinued
0.7475 Intermediate Similarity NPD3396 Approved
0.7474 Intermediate Similarity NPD4072 Approved
0.7474 Intermediate Similarity NPD4071 Approved
0.7467 Intermediate Similarity NPD6525 Clinical (unspecified phase)
0.7465 Intermediate Similarity NPD6803 Clinical (unspecified phase)
0.7464 Intermediate Similarity NPD5863 Clinical (unspecified phase)
0.7464 Intermediate Similarity NPD5529 Phase 1
0.7464 Intermediate Similarity NPD5528 Clinical (unspecified phase)
0.7458 Intermediate Similarity NPD5450 Discontinued
0.7455 Intermediate Similarity NPD8512 Phase 3
0.7452 Intermediate Similarity NPD5530 Phase 1
0.7449 Intermediate Similarity NPD4203 Approved
0.7449 Intermediate Similarity NPD4204 Approved
0.7441 Intermediate Similarity NPD4502 Phase 2
0.7437 Intermediate Similarity NPD1034 Phase 3
0.7437 Intermediate Similarity NPD1033 Clinical (unspecified phase)
0.7435 Intermediate Similarity NPD2781 Approved
0.7434 Intermediate Similarity NPD4875 Phase 3
0.7434 Intermediate Similarity NPD4876 Phase 3
0.7429 Intermediate Similarity NPD4437 Phase 3
0.7424 Intermediate Similarity NPD6344 Clinical (unspecified phase)
0.7419 Intermediate Similarity NPD1954 Phase 1
0.7415 Intermediate Similarity NPD5999 Phase 2
0.7413 Intermediate Similarity NPD2334 Discontinued
0.7402 Intermediate Similarity NPD2952 Discontinued
0.7401 Intermediate Similarity NPD7413 Phase 3
0.7397 Intermediate Similarity NPD7603 Discontinued
0.7395 Intermediate Similarity NPD4429 Discontinued
0.7391 Intermediate Similarity NPD5669 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD6208 Discontinued
0.7387 Intermediate Similarity NPD4375 Approved
0.7382 Intermediate Similarity NPD6961 Discontinued
0.7376 Intermediate Similarity NPD4372 Phase 1
0.7371 Intermediate Similarity NPD4926 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD4349 Approved
0.7368 Intermediate Similarity NPD4862 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD4350 Approved
0.7363 Intermediate Similarity NPD6281 Approved
0.7356 Intermediate Similarity NPD6991 Approved
0.7354 Intermediate Similarity NPD2472 Approved
0.7354 Intermediate Similarity NPD2471 Approved
0.735 Intermediate Similarity NPD8091 Phase 3
0.7347 Intermediate Similarity NPD1620 Clinical (unspecified phase)
0.734 Intermediate Similarity NPD4551 Phase 2
0.7339 Intermediate Similarity NPD6824 Clinical (unspecified phase)
0.7336 Intermediate Similarity NPD5417 Clinical (unspecified phase)
0.733 Intermediate Similarity NPD7555 Discontinued
0.7328 Intermediate Similarity NPD7859 Phase 2
0.7325 Intermediate Similarity NPD5802 Phase 2
0.7318 Intermediate Similarity NPD7051 Phase 3
0.7318 Intermediate Similarity NPD7050 Clinical (unspecified phase)
0.7315 Intermediate Similarity NPD3354 Phase 2
0.731 Intermediate Similarity NPD2600 Approved
0.731 Intermediate Similarity NPD2601 Approved
0.731 Intermediate Similarity NPD2599 Approved
0.7306 Intermediate Similarity NPD1325 Approved
0.7306 Intermediate Similarity NPD1326 Approved
0.7304 Intermediate Similarity NPD6590 Discontinued
0.7297 Intermediate Similarity NPD4374 Clinical (unspecified phase)
0.7296 Intermediate Similarity NPD5751 Clinical (unspecified phase)
0.7296 Intermediate Similarity NPD1032 Phase 2
0.7295 Intermediate Similarity NPD484 Approved
0.7295 Intermediate Similarity NPD4396 Clinical (unspecified phase)
0.7291 Intermediate Similarity NPD3404 Approved
0.7286 Intermediate Similarity NPD5083 Clinical (unspecified phase)
0.7285 Intermediate Similarity NPD6553 Clinical (unspecified phase)
0.7282 Intermediate Similarity NPD1923 Clinical (unspecified phase)
0.7277 Intermediate Similarity NPD6220 Phase 3
0.7273 Intermediate Similarity NPD6246 Approved
0.7273 Intermediate Similarity NPD4558 Phase 2
0.7273 Intermediate Similarity NPD4890 Phase 2
0.7268 Intermediate Similarity NPD6550 Discontinued
0.7265 Intermediate Similarity NPD8442 Discontinued
0.7265 Intermediate Similarity NPD4996 Approved
0.7265 Intermediate Similarity NPD4995 Approved
0.7264 Intermediate Similarity NPD8431 Approved
0.7263 Intermediate Similarity NPD9705 Discontinued
0.7263 Intermediate Similarity NPD112 Approved
0.7249 Intermediate Similarity NPD6573 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