Structure

Physi-Chem Properties

Molecular Weight:  506.23
Volume:  504.957
LogP:  2.779
LogD:  2.804
LogS:  -4.279
# Rotatable Bonds:  9
TPSA:  131.41
# H-Bond Aceptor:  11
# H-Bond Donor:  3
# Rings:  4
# Heavy Atoms:  11

MedChem Properties

QED Drug-Likeness Score:  0.299
Synthetic Accessibility Score:  3.644
Fsp3:  0.269
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.927
MDCK Permeability:  1.0064503840112593e-05
Pgp-inhibitor:  0.126
Pgp-substrate:  0.993
Human Intestinal Absorption (HIA):  0.096
20% Bioavailability (F20%):  0.025
30% Bioavailability (F30%):  0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.003
Plasma Protein Binding (PPB):  91.41869354248047%
Volume Distribution (VD):  0.502
Pgp-substrate:  3.8864247798919678%

ADMET: Metabolism

CYP1A2-inhibitor:  0.04
CYP1A2-substrate:  0.943
CYP2C19-inhibitor:  0.259
CYP2C19-substrate:  0.661
CYP2C9-inhibitor:  0.118
CYP2C9-substrate:  0.602
CYP2D6-inhibitor:  0.252
CYP2D6-substrate:  0.858
CYP3A4-inhibitor:  0.547
CYP3A4-substrate:  0.937

ADMET: Excretion

Clearance (CL):  6.522
Half-life (T1/2):  0.591

ADMET: Toxicity

hERG Blockers:  0.02
Human Hepatotoxicity (H-HT):  0.709
Drug-inuced Liver Injury (DILI):  0.69
AMES Toxicity:  0.275
Rat Oral Acute Toxicity:  0.542
Maximum Recommended Daily Dose:  0.109
Skin Sensitization:  0.037
Carcinogencity:  0.807
Eye Corrosion:  0.003
Eye Irritation:  0.016
Respiratory Toxicity:  0.24

Download Data

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

  Natural Product: NPC237978

Natural Product ID:  NPC237978
Common Name*:   (2E, 9E)-Pyronaamidine 9-(N-Methylimine)
IUPAC Name:   5-[[5-[(2-hydroxy-3,4-dimethoxyphenyl)methyl]-4-[(4-methoxyphenyl)methyl]-1-methylimidazol-2-yl]amino]-3-methyl-2-methyliminoimidazol-4-one
Synonyms:  
Standard InCHIKey:  YEZDHZOESSUWCE-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C26H30N6O5/c1-27-25-29-23(24(34)32(25)3)30-26-28-18(13-15-7-10-17(35-4)11-8-15)19(31(26)2)14-16-9-12-20(36-5)22(37-6)21(16)33/h7-12,33H,13-14H2,1-6H3,(H,27,28,29,30)
SMILES:  CN=C1NC(=Nc2nc(Cc3ccc(cc3)OC)c(Cc3ccc(c(c3O)OC)OC)n2C)C(=O)N1C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL518089
PubChem CID:   10436230
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000134] Phenols
        • [CHEMONTID:0000190] Methoxyphenols

*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
NPO32509 Leucetta chagosensis Species Leucettidae Eukaryota n.a. northern Mariana islands n.a. PMID[9249976]

☑ 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
NPT81 Cell Line A549 Homo sapiens GI50 = 6.0 ug.mL-1 PMID[523444]
NPT83 Cell Line MCF7 Homo sapiens GI50 = 3.0 ug.mL-1 PMID[523444]
NPT139 Cell Line HT-29 Homo sapiens GI50 = 6.0 ug.mL-1 PMID[523444]

☑ 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 NPC237978 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
0.9851 High Similarity NPC35761
0.9559 High Similarity NPC46970
0.9412 High Similarity NPC136924
0.8632 High Similarity NPC467439
0.8333 Intermediate Similarity NPC280638
0.8174 Intermediate Similarity NPC17305
0.8165 Intermediate Similarity NPC308906
0.7991 Intermediate Similarity NPC12100
0.7844 Intermediate Similarity NPC242923
0.7627 Intermediate Similarity NPC477806
0.7627 Intermediate Similarity NPC477805
0.7627 Intermediate Similarity NPC477795
0.7627 Intermediate Similarity NPC477796
0.7203 Intermediate Similarity NPC160666
0.7113 Intermediate Similarity NPC208898
0.7087 Intermediate Similarity NPC247251
0.6976 Remote Similarity NPC51854
0.6975 Remote Similarity NPC476997
0.6946 Remote Similarity NPC476996
0.6946 Remote Similarity NPC476998
0.6935 Remote Similarity NPC9729
0.6933 Remote Similarity NPC323244
0.6923 Remote Similarity NPC250178
0.6916 Remote Similarity NPC261388
0.6908 Remote Similarity NPC472031
0.6908 Remote Similarity NPC472067
0.6908 Remote Similarity NPC472066
0.6904 Remote Similarity NPC476994
0.6898 Remote Similarity NPC217554
0.6883 Remote Similarity NPC284141
0.6872 Remote Similarity NPC210256
0.6844 Remote Similarity NPC476995
0.6827 Remote Similarity NPC472068
0.6818 Remote Similarity NPC328924
0.6816 Remote Similarity NPC11408
0.6809 Remote Similarity NPC473822
0.6765 Remote Similarity NPC122463
0.6742 Remote Similarity NPC29531
0.6709 Remote Similarity NPC266931
0.6708 Remote Similarity NPC201508
0.6696 Remote Similarity NPC471563
0.6696 Remote Similarity NPC25897
0.6681 Remote Similarity NPC54066
0.6681 Remote Similarity NPC174049
0.6653 Remote Similarity NPC255800
0.6653 Remote Similarity NPC96584
0.664 Remote Similarity NPC473183
0.6636 Remote Similarity NPC181905
0.6608 Remote Similarity NPC127085
0.6596 Remote Similarity NPC112206
0.6596 Remote Similarity NPC202605
0.6581 Remote Similarity NPC113369
0.6571 Remote Similarity NPC476999
0.6565 Remote Similarity NPC199277
0.6565 Remote Similarity NPC135887
0.6559 Remote Similarity NPC277351
0.6559 Remote Similarity NPC473184
0.6537 Remote Similarity NPC223427
0.6525 Remote Similarity NPC129897
0.6516 Remote Similarity NPC187145
0.6508 Remote Similarity NPC15406
0.65 Remote Similarity NPC148409
0.6498 Remote Similarity NPC474594
0.6492 Remote Similarity NPC223223
0.6491 Remote Similarity NPC473639
0.6488 Remote Similarity NPC280272
0.6486 Remote Similarity NPC138083
0.6484 Remote Similarity NPC67401
0.6475 Remote Similarity NPC215837
0.6468 Remote Similarity NPC295452
0.6468 Remote Similarity NPC171393
0.6466 Remote Similarity NPC295228
0.6453 Remote Similarity NPC16249
0.645 Remote Similarity NPC54537
0.6441 Remote Similarity NPC14390
0.6438 Remote Similarity NPC228040
0.642 Remote Similarity NPC77878
0.6397 Remote Similarity NPC115595
0.639 Remote Similarity NPC469594
0.6389 Remote Similarity NPC471614
0.6388 Remote Similarity NPC79213
0.6387 Remote Similarity NPC316981
0.638 Remote Similarity NPC32064
0.6374 Remote Similarity NPC41982
0.6368 Remote Similarity NPC137929
0.6368 Remote Similarity NPC164374
0.6357 Remote Similarity NPC183537
0.6355 Remote Similarity NPC329837
0.6352 Remote Similarity NPC66815
0.6348 Remote Similarity NPC224928
0.6348 Remote Similarity NPC281629
0.6346 Remote Similarity NPC303374
0.6339 Remote Similarity NPC39092
0.6336 Remote Similarity NPC478006
0.6335 Remote Similarity NPC272549
0.6331 Remote Similarity NPC469792
0.6329 Remote Similarity NPC469589
0.6325 Remote Similarity NPC469440
0.6322 Remote Similarity NPC303658
0.6321 Remote Similarity NPC292003
0.632 Remote Similarity NPC473182
0.6318 Remote Similarity NPC471603
0.6316 Remote Similarity NPC315467
0.6316 Remote Similarity NPC318805
0.6316 Remote Similarity NPC133140
0.6316 Remote Similarity NPC473185
0.6316 Remote Similarity NPC41122
0.6316 Remote Similarity NPC195268
0.631 Remote Similarity NPC184680
0.6309 Remote Similarity NPC31930
0.6308 Remote Similarity NPC235628
0.6308 Remote Similarity NPC314882
0.6299 Remote Similarity NPC49672
0.6298 Remote Similarity NPC476581
0.6298 Remote Similarity NPC36229
0.6298 Remote Similarity NPC16452
0.6293 Remote Similarity NPC18487
0.6292 Remote Similarity NPC471080
0.6292 Remote Similarity NPC478009
0.6292 Remote Similarity NPC478010
0.6292 Remote Similarity NPC469592
0.629 Remote Similarity NPC315822
0.6285 Remote Similarity NPC470784
0.6285 Remote Similarity NPC470785
0.6281 Remote Similarity NPC238945
0.6275 Remote Similarity NPC296898
0.6274 Remote Similarity NPC150447
0.6272 Remote Similarity NPC469390
0.6266 Remote Similarity NPC477019
0.6266 Remote Similarity NPC471031
0.6266 Remote Similarity NPC469689
0.6261 Remote Similarity NPC85381
0.626 Remote Similarity NPC130570
0.6255 Remote Similarity NPC26543
0.625 Remote Similarity NPC203168
0.625 Remote Similarity NPC89549
0.625 Remote Similarity NPC53069
0.625 Remote Similarity NPC171409
0.625 Remote Similarity NPC296482
0.625 Remote Similarity NPC96405
0.625 Remote Similarity NPC202768
0.625 Remote Similarity NPC110151
0.6245 Remote Similarity NPC280964
0.6245 Remote Similarity NPC114335
0.6245 Remote Similarity NPC474595
0.6245 Remote Similarity NPC141915
0.624 Remote Similarity NPC8022
0.624 Remote Similarity NPC470799
0.6239 Remote Similarity NPC61350
0.6239 Remote Similarity NPC276120
0.6234 Remote Similarity NPC197125
0.6234 Remote Similarity NPC219664
0.623 Remote Similarity NPC90875
0.6228 Remote Similarity NPC174122
0.6228 Remote Similarity NPC64140
0.6226 Remote Similarity NPC127402
0.6225 Remote Similarity NPC194740
0.6223 Remote Similarity NPC476582
0.6223 Remote Similarity NPC4071
0.6223 Remote Similarity NPC476578
0.622 Remote Similarity NPC82472
0.622 Remote Similarity NPC118121
0.622 Remote Similarity NPC474183
0.6217 Remote Similarity NPC314056
0.6215 Remote Similarity NPC233334
0.6214 Remote Similarity NPC305984
0.6212 Remote Similarity NPC284685
0.621 Remote Similarity NPC200888
0.621 Remote Similarity NPC13916
0.621 Remote Similarity NPC264850
0.6207 Remote Similarity NPC243834
0.6207 Remote Similarity NPC234318
0.6207 Remote Similarity NPC70956
0.6203 Remote Similarity NPC472111
0.6199 Remote Similarity NPC164608
0.6198 Remote Similarity NPC318068
0.6197 Remote Similarity NPC242728
0.6197 Remote Similarity NPC475654
0.619 Remote Similarity NPC220852
0.6189 Remote Similarity NPC204446
0.6189 Remote Similarity NPC191489
0.6185 Remote Similarity NPC157931
0.6184 Remote Similarity NPC234069
0.6181 Remote Similarity NPC28945
0.618 Remote Similarity NPC50548
0.6179 Remote Similarity NPC310118
0.6176 Remote Similarity NPC135549
0.6176 Remote Similarity NPC313189
0.6176 Remote Similarity NPC478012
0.6176 Remote Similarity NPC478011
0.6176 Remote Similarity NPC193777
0.6174 Remote Similarity NPC63109
0.6172 Remote Similarity NPC210296
0.6172 Remote Similarity NPC99891
0.6169 Remote Similarity NPC56271
0.6168 Remote Similarity NPC475557
0.6167 Remote Similarity NPC11464
0.6164 Remote Similarity NPC24465
0.6163 Remote Similarity NPC213530
0.6163 Remote Similarity NPC193267

  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 NPC237978 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
0.7803 Intermediate Similarity NPD3590 Clinical (unspecified phase)
0.7662 Intermediate Similarity NPD4080 Discontinued
0.7511 Intermediate Similarity NPD4132 Clinical (unspecified phase)
0.7477 Intermediate Similarity NPD4048 Approved
0.7412 Intermediate Similarity NPD6856 Discontinued
0.7359 Intermediate Similarity NPD3042 Approved
0.7359 Intermediate Similarity NPD3043 Approved
0.7281 Intermediate Similarity NPD7980 Clinical (unspecified phase)
0.721 Intermediate Similarity NPD5703 Discontinued
0.7114 Intermediate Similarity NPD7588 Discontinued
0.7017 Intermediate Similarity NPD6708 Discontinued
0.6992 Remote Similarity NPD7486 Phase 1
0.6987 Remote Similarity NPD949 Phase 1
0.695 Remote Similarity NPD7682 Approved
0.695 Remote Similarity NPD7684 Approved
0.692 Remote Similarity NPD6743 Phase 2
0.692 Remote Similarity NPD6742 Phase 2
0.6907 Remote Similarity NPD1954 Phase 1
0.6867 Remote Similarity NPD6643 Discontinued
0.6857 Remote Similarity NPD2929 Clinical (unspecified phase)
0.684 Remote Similarity NPD6243 Phase 3
0.684 Remote Similarity NPD6244 Phase 3
0.6831 Remote Similarity NPD3838 Phase 3
0.6798 Remote Similarity NPD8442 Discontinued
0.6792 Remote Similarity NPD8292 Phase 2
0.6787 Remote Similarity NPD459 Clinical (unspecified phase)
0.6766 Remote Similarity NPD2530 Phase 2
0.6743 Remote Similarity NPD5107 Clinical (unspecified phase)
0.674 Remote Similarity NPD7134 Clinical (unspecified phase)
0.6734 Remote Similarity NPD5833 Phase 1
0.6718 Remote Similarity NPD7689 Approved
0.6707 Remote Similarity NPD7620 Phase 2
0.6697 Remote Similarity NPD4157 Discontinued
0.6696 Remote Similarity NPD3602 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6473 Phase 1
0.6653 Remote Similarity NPD5905 Phase 1
0.6652 Remote Similarity NPD4052 Clinical (unspecified phase)
0.6628 Remote Similarity NPD6773 Clinical (unspecified phase)
0.6625 Remote Similarity NPD6036 Suspended
0.6624 Remote Similarity NPD2540 Clinical (unspecified phase)
0.6612 Remote Similarity NPD4885 Approved
0.6607 Remote Similarity NPD994 Phase 2
0.6607 Remote Similarity NPD996 Phase 2
0.6596 Remote Similarity NPD6202 Discontinued
0.6587 Remote Similarity NPD5118 Phase 2
0.6586 Remote Similarity NPD7117 Phase 2
0.6581 Remote Similarity NPD4741 Phase 3
0.6581 Remote Similarity NPD4742 Phase 3
0.6573 Remote Similarity NPD5920 Clinical (unspecified phase)
0.6552 Remote Similarity NPD2060 Approved
0.6549 Remote Similarity NPD978 Clinical (unspecified phase)
0.6544 Remote Similarity NPD8525 Approved
0.6542 Remote Similarity NPD5070 Clinical (unspecified phase)
0.6535 Remote Similarity NPD3886 Phase 1
0.6525 Remote Similarity NPD2794 Discontinued
0.6511 Remote Similarity NPD6745 Discontinued
0.6504 Remote Similarity NPD4995 Approved
0.6504 Remote Similarity NPD4996 Approved
0.6502 Remote Similarity NPD6023 Discontinued
0.6496 Remote Similarity NPD5658 Approved
0.6492 Remote Similarity NPD2757 Phase 2
0.6475 Remote Similarity NPD7051 Phase 3
0.6475 Remote Similarity NPD8524 Approved
0.6475 Remote Similarity NPD7050 Clinical (unspecified phase)
0.6471 Remote Similarity NPD4558 Phase 2
0.6466 Remote Similarity NPD5861 Clinical (unspecified phase)
0.6464 Remote Similarity NPD8310 Clinical (unspecified phase)
0.6463 Remote Similarity NPD4925 Approved
0.6454 Remote Similarity NPD5908 Clinical (unspecified phase)
0.6449 Remote Similarity NPD6326 Phase 2
0.6449 Remote Similarity NPD6327 Phase 1
0.6449 Remote Similarity NPD4984 Phase 2
0.6437 Remote Similarity NPD5116 Phase 1
0.6435 Remote Similarity NPD3541 Clinical (unspecified phase)
0.6434 Remote Similarity NPD3938 Phase 1
0.6432 Remote Similarity NPD8105 Discontinued
0.6431 Remote Similarity NPD7898 Clinical (unspecified phase)
0.6431 Remote Similarity NPD7897 Phase 3
0.6429 Remote Similarity NPD4457 Phase 2
0.6429 Remote Similarity NPD3872 Phase 3
0.642 Remote Similarity NPD6503 Clinical (unspecified phase)
0.6413 Remote Similarity NPD2762 Phase 2
0.6408 Remote Similarity NPD1273 Discontinued
0.6405 Remote Similarity NPD6634 Clinical (unspecified phase)
0.6405 Remote Similarity NPD6633 Phase 2
0.64 Remote Similarity NPD2152 Clinical (unspecified phase)
0.6397 Remote Similarity NPD1900 Clinical (unspecified phase)
0.6392 Remote Similarity NPD6460 Clinical (unspecified phase)
0.6389 Remote Similarity NPD6537 Approved
0.6389 Remote Similarity NPD6536 Approved
0.6386 Remote Similarity NPD6223 Clinical (unspecified phase)
0.6386 Remote Similarity NPD6186 Approved
0.6384 Remote Similarity NPD6814 Phase 3
0.6381 Remote Similarity NPD4916 Discontinued
0.6377 Remote Similarity NPD4442 Phase 2
0.6375 Remote Similarity NPD5805 Approved
0.637 Remote Similarity NPD6153 Approved
0.6368 Remote Similarity NPD1287 Phase 2
0.6367 Remote Similarity NPD4932 Clinical (unspecified phase)
0.6364 Remote Similarity NPD3514 Clinical (unspecified phase)
0.6364 Remote Similarity NPD5949 Phase 3
0.6364 Remote Similarity NPD3814 Phase 1
0.6364 Remote Similarity NPD4555 Clinical (unspecified phase)
0.636 Remote Similarity NPD2894 Phase 2
0.636 Remote Similarity NPD6760 Discontinued
0.6356 Remote Similarity NPD5528 Clinical (unspecified phase)
0.6356 Remote Similarity NPD5529 Phase 1
0.635 Remote Similarity NPD7706 Clinical (unspecified phase)
0.6349 Remote Similarity NPD2812 Clinical (unspecified phase)
0.6349 Remote Similarity NPD2813 Phase 3
0.6345 Remote Similarity NPD4206 Approved
0.6345 Remote Similarity NPD4131 Phase 3
0.6345 Remote Similarity NPD7705 Clinical (unspecified phase)
0.6342 Remote Similarity NPD5644 Phase 1
0.6339 Remote Similarity NPD6344 Clinical (unspecified phase)
0.6339 Remote Similarity NPD6517 Phase 3
0.6339 Remote Similarity NPD5051 Phase 1
0.6336 Remote Similarity NPD6612 Phase 2
0.6335 Remote Similarity NPD3920 Phase 2
0.6321 Remote Similarity NPD6558 Phase 1
0.632 Remote Similarity NPD4306 Phase 1
0.6316 Remote Similarity NPD3922 Approved
0.6316 Remote Similarity NPD3924 Approved
0.6316 Remote Similarity NPD3923 Approved
0.6316 Remote Similarity NPD3921 Approved
0.6316 Remote Similarity NPD1882 Phase 2
0.6314 Remote Similarity NPD7068 Approved
0.6314 Remote Similarity NPD7067 Approved
0.6314 Remote Similarity NPD7263 Phase 2
0.6312 Remote Similarity NPD6228 Discontinued
0.6311 Remote Similarity NPD4414 Discontinued
0.6307 Remote Similarity NPD5612 Discontinued
0.6306 Remote Similarity NPD5459 Phase 2
0.6304 Remote Similarity NPD2482 Clinical (unspecified phase)
0.6304 Remote Similarity NPD7996 Phase 2
0.6299 Remote Similarity NPD6848 Phase 1
0.6293 Remote Similarity NPD5665 Clinical (unspecified phase)
0.6292 Remote Similarity NPD7506 Discontinued
0.629 Remote Similarity NPD5014 Discontinued
0.6289 Remote Similarity NPD6230 Discontinued
0.6285 Remote Similarity NPD7729 Clinical (unspecified phase)
0.6283 Remote Similarity NPD5509 Phase 1
0.6279 Remote Similarity NPD5572 Phase 3
0.6278 Remote Similarity NPD3343 Phase 3
0.6278 Remote Similarity NPD6216 Approved
0.6278 Remote Similarity NPD7273 Clinical (unspecified phase)
0.6278 Remote Similarity NPD8287 Phase 1
0.6278 Remote Similarity NPD8288 Phase 2
0.627 Remote Similarity NPD5930 Phase 3
0.6269 Remote Similarity NPD3254 Phase 1
0.6269 Remote Similarity NPD3255 Phase 1
0.6268 Remote Similarity NPD8421 Discontinued
0.6266 Remote Similarity NPD6528 Phase 1
0.6266 Remote Similarity NPD4358 Clinical (unspecified phase)
0.6261 Remote Similarity NPD4418 Discontinued
0.626 Remote Similarity NPD8016 Phase 3
0.626 Remote Similarity NPD8017 Clinical (unspecified phase)
0.6255 Remote Similarity NPD6482 Phase 1
0.625 Remote Similarity NPD6572 Phase 2
0.625 Remote Similarity NPD5802 Phase 2
0.625 Remote Similarity NPD6573 Phase 3
0.625 Remote Similarity NPD3816 Phase 1
0.625 Remote Similarity NPD3815 Phase 1
0.6245 Remote Similarity NPD7222 Phase 2
0.6245 Remote Similarity NPD7453 Approved
0.6245 Remote Similarity NPD7452 Approved
0.6245 Remote Similarity NPD3634 Approved
0.6245 Remote Similarity NPD3633 Approved
0.6245 Remote Similarity NPD5539 Phase 2
0.624 Remote Similarity NPD5139 Phase 1
0.624 Remote Similarity NPD5573 Clinical (unspecified phase)
0.624 Remote Similarity NPD5571 Phase 3
0.624 Remote Similarity NPD6772 Clinical (unspecified phase)
0.6239 Remote Similarity NPD7758 Approved
0.6239 Remote Similarity NPD2917 Approved
0.6239 Remote Similarity NPD7757 Approved
0.6238 Remote Similarity NPD1349 Approved
0.6238 Remote Similarity NPD1351 Approved
0.6238 Remote Similarity NPD1350 Approved
0.6233 Remote Similarity NPD6996 Clinical (unspecified phase)
0.6232 Remote Similarity NPD8046 Discontinued
0.623 Remote Similarity NPD3875 Discontinued
0.622 Remote Similarity NPD6824 Clinical (unspecified phase)
0.622 Remote Similarity NPD7221 Approved
0.622 Remote Similarity NPD7219 Approved
0.6217 Remote Similarity NPD6046 Clinical (unspecified phase)
0.6216 Remote Similarity NPD5007 Approved
0.6215 Remote Similarity NPD4847 Phase 1
0.6212 Remote Similarity NPD7956 Approved
0.6212 Remote Similarity NPD7955 Approved
0.6207 Remote Similarity NPD8357 Approved
0.6203 Remote Similarity NPD5530 Phase 1
0.6202 Remote Similarity NPD2219 Phase 1
0.6199 Remote Similarity NPD5018 Phase 3
0.6199 Remote Similarity NPD1225 Phase 2
0.6199 Remote Similarity NPD1224 Phase 2
0.6198 Remote Similarity NPD5902 Approved
0.6198 Remote Similarity NPD5911 Clinical (unspecified phase)
0.6198 Remote Similarity NPD5903 Approved
0.6194 Remote Similarity NPD983 Clinical (unspecified phase)

  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