Structure

Physi-Chem Properties

Molecular Weight:  568.23
Volume:  585.928
LogP:  5.322
LogD:  3.842
LogS:  -4.859
# Rotatable Bonds:  14
TPSA:  133.13
# H-Bond Aceptor:  8
# H-Bond Donor:  3
# Rings:  2
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.147
Synthetic Accessibility Score:  4.327
Fsp3:  0.387
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.089
MDCK Permeability:  2.5066881789825857e-05
Pgp-inhibitor:  1.0
Pgp-substrate:  0.052
Human Intestinal Absorption (HIA):  0.019
20% Bioavailability (F20%):  0.01
30% Bioavailability (F30%):  0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.014
Plasma Protein Binding (PPB):  100.22425079345703%
Volume Distribution (VD):  0.51
Pgp-substrate:  0.7190396785736084%

ADMET: Metabolism

CYP1A2-inhibitor:  0.537
CYP1A2-substrate:  0.736
CYP2C19-inhibitor:  0.643
CYP2C19-substrate:  0.198
CYP2C9-inhibitor:  0.936
CYP2C9-substrate:  0.91
CYP2D6-inhibitor:  0.718
CYP2D6-substrate:  0.354
CYP3A4-inhibitor:  0.918
CYP3A4-substrate:  0.331

ADMET: Excretion

Clearance (CL):  0.415
Half-life (T1/2):  0.856

ADMET: Toxicity

hERG Blockers:  0.519
Human Hepatotoxicity (H-HT):  0.662
Drug-inuced Liver Injury (DILI):  0.916
AMES Toxicity:  0.036
Rat Oral Acute Toxicity:  0.157
Maximum Recommended Daily Dose:  0.957
Skin Sensitization:  0.958
Carcinogencity:  0.591
Eye Corrosion:  0.003
Eye Irritation:  0.01
Respiratory Toxicity:  0.753

Download Data

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

  Natural Product: NPC272375

Natural Product ID:  NPC272375
Common Name*:   Chinikomycin A
IUPAC Name:   (2E,4E,6R)-N-[3-chloro-2,5-dihydroxy-4-[(1E,3E,5E)-7-[(2-hydroxy-5-oxocyclopenten-1-yl)amino]-7-oxohepta-1,3,5-trienyl]phenyl]-2,4,6-trimethyldeca-2,4-dienamide
Synonyms:  
Standard InCHIKey:  ZFIDLGUORHJAKX-RWZZEPMSSA-N
Standard InCHI:  InChI=1S/C31H37ClN2O6/c1-5-6-11-19(2)16-20(3)17-21(4)31(40)33-23-18-26(37)22(28(32)30(23)39)12-9-7-8-10-13-27(38)34-29-24(35)14-15-25(29)36/h7-10,12-13,16-19,35,37,39H,5-6,11,14-15H2,1-4H3,(H,33,40)(H,34,38)/b8-7+,12-9+,13-10+,20-16+,21-17+/t19-/m1/s1
SMILES:  CCCC[C@H](/C=C(/C=C(/C(=Nc1cc(O)c(c(c1O)Cl)/C=C/C=C/C=C/C(=NC1=C(O)CCC1=O)O)O)C)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL475474
PubChem CID:   11273076
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives
        • [CHEMONTID:0000285] Anilides

*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
NPO41058 Streptomyces sp. isolate M045 Strain Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[15787434]

☑ 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
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 6.0 ug.mL-1 PMID[537293]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 2.41 ug.mL-1 PMID[537293]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 4.15 ug.mL-1 PMID[537293]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 4.02 ug.mL-1 PMID[537293]

☑ 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 NPC272375 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
0.7184 Intermediate Similarity NPC315829
0.6952 Remote Similarity NPC225381
0.6738 Remote Similarity NPC238430
0.6701 Remote Similarity NPC295287
0.6667 Remote Similarity NPC166667
0.6591 Remote Similarity NPC106688
0.6458 Remote Similarity NPC83241
0.6447 Remote Similarity NPC471785
0.6402 Remote Similarity NPC72291
0.6392 Remote Similarity NPC95412
0.6378 Remote Similarity NPC472331
0.6378 Remote Similarity NPC274002
0.6378 Remote Similarity NPC126515
0.6302 Remote Similarity NPC127362
0.6296 Remote Similarity NPC291359
0.6296 Remote Similarity NPC9336
0.6278 Remote Similarity NPC314113
0.6235 Remote Similarity NPC255721
0.623 Remote Similarity NPC133470
0.623 Remote Similarity NPC475983
0.623 Remote Similarity NPC191863
0.623 Remote Similarity NPC289776
0.6227 Remote Similarity NPC274268
0.6219 Remote Similarity NPC313886
0.6218 Remote Similarity NPC19555
0.6205 Remote Similarity NPC310894
0.6203 Remote Similarity NPC184161
0.6201 Remote Similarity NPC43218
0.6195 Remote Similarity NPC227033
0.6193 Remote Similarity NPC313466
0.6183 Remote Similarity NPC241392
0.6181 Remote Similarity NPC39822
0.6176 Remote Similarity NPC473050
0.6176 Remote Similarity NPC473051
0.6175 Remote Similarity NPC323798
0.6169 Remote Similarity NPC477392
0.6169 Remote Similarity NPC315934
0.6154 Remote Similarity NPC301702
0.6154 Remote Similarity NPC257354
0.6139 Remote Similarity NPC477391
0.6133 Remote Similarity NPC47986
0.6131 Remote Similarity NPC474815
0.6111 Remote Similarity NPC8467
0.608 Remote Similarity NPC9475
0.6061 Remote Similarity NPC227778
0.6051 Remote Similarity NPC314861
0.6042 Remote Similarity NPC103250
0.6038 Remote Similarity NPC472329
0.6038 Remote Similarity NPC472330
0.6034 Remote Similarity NPC205946
0.6032 Remote Similarity NPC219383
0.603 Remote Similarity NPC168153
0.6028 Remote Similarity NPC133156
0.6022 Remote Similarity NPC126637
0.6019 Remote Similarity NPC144381
0.601 Remote Similarity NPC231862
0.6 Remote Similarity NPC232872
0.5991 Remote Similarity NPC177056
0.599 Remote Similarity NPC92803
0.599 Remote Similarity NPC28510
0.598 Remote Similarity NPC132751
0.5972 Remote Similarity NPC39528
0.5971 Remote Similarity NPC18890
0.5952 Remote Similarity NPC170333
0.5951 Remote Similarity NPC288854
0.593 Remote Similarity NPC12890
0.5917 Remote Similarity NPC317254
0.5913 Remote Similarity NPC70340
0.5913 Remote Similarity NPC300114
0.5909 Remote Similarity NPC151030
0.5909 Remote Similarity NPC269383
0.5904 Remote Similarity NPC208229
0.5904 Remote Similarity NPC476444
0.5902 Remote Similarity NPC471201
0.5902 Remote Similarity NPC469828
0.5902 Remote Similarity NPC322526
0.5899 Remote Similarity NPC478147
0.5897 Remote Similarity NPC57105
0.5889 Remote Similarity NPC328070
0.5879 Remote Similarity NPC112336
0.5879 Remote Similarity NPC474814
0.5874 Remote Similarity NPC150308
0.587 Remote Similarity NPC181526
0.5869 Remote Similarity NPC317727
0.5867 Remote Similarity NPC204867
0.5867 Remote Similarity NPC139506
0.5867 Remote Similarity NPC292143
0.5862 Remote Similarity NPC271958
0.5862 Remote Similarity NPC98416
0.5862 Remote Similarity NPC474862
0.5862 Remote Similarity NPC45112
0.5862 Remote Similarity NPC134413
0.5862 Remote Similarity NPC263507
0.586 Remote Similarity NPC96730
0.5854 Remote Similarity NPC320394
0.5847 Remote Similarity NPC473052
0.5847 Remote Similarity NPC473055
0.5843 Remote Similarity NPC282855
0.5843 Remote Similarity NPC26576
0.5843 Remote Similarity NPC296712
0.5843 Remote Similarity NPC26013
0.5842 Remote Similarity NPC315631
0.5838 Remote Similarity NPC316202
0.5838 Remote Similarity NPC67791
0.5833 Remote Similarity NPC326966
0.5824 Remote Similarity NPC222982
0.582 Remote Similarity NPC254798
0.5818 Remote Similarity NPC76327
0.5818 Remote Similarity NPC474366
0.5806 Remote Similarity NPC473422
0.5806 Remote Similarity NPC163829
0.5801 Remote Similarity NPC244866
0.5799 Remote Similarity NPC296144
0.5799 Remote Similarity NPC28784
0.5795 Remote Similarity NPC301163
0.5792 Remote Similarity NPC159589
0.5792 Remote Similarity NPC122542
0.5792 Remote Similarity NPC6913
0.5789 Remote Similarity NPC51047
0.5789 Remote Similarity NPC174629
0.5784 Remote Similarity NPC478032
0.5784 Remote Similarity NPC314252
0.5783 Remote Similarity NPC279887
0.5783 Remote Similarity NPC68260
0.578 Remote Similarity NPC158551
0.578 Remote Similarity NPC283760
0.5779 Remote Similarity NPC33507
0.5775 Remote Similarity NPC314287
0.5775 Remote Similarity NPC316282
0.5774 Remote Similarity NPC228609
0.5774 Remote Similarity NPC163674
0.5773 Remote Similarity NPC477889
0.5771 Remote Similarity NPC73280
0.5771 Remote Similarity NPC49315
0.5769 Remote Similarity NPC297584
0.5765 Remote Similarity NPC474114
0.5765 Remote Similarity NPC474050
0.5765 Remote Similarity NPC473931
0.5763 Remote Similarity NPC33402
0.5759 Remote Similarity NPC471531
0.5756 Remote Similarity NPC270301
0.575 Remote Similarity NPC314693
0.575 Remote Similarity NPC471778
0.5749 Remote Similarity NPC474498
0.5749 Remote Similarity NPC94943
0.5746 Remote Similarity NPC48909
0.5745 Remote Similarity NPC473804
0.5738 Remote Similarity NPC317872
0.5728 Remote Similarity NPC215747
0.5728 Remote Similarity NPC192939
0.5728 Remote Similarity NPC86678
0.5721 Remote Similarity NPC314573
0.5721 Remote Similarity NPC126676
0.5721 Remote Similarity NPC469671
0.5714 Remote Similarity NPC119569
0.5714 Remote Similarity NPC316297
0.5714 Remote Similarity NPC66191
0.5714 Remote Similarity NPC471535
0.5714 Remote Similarity NPC314817
0.5714 Remote Similarity NPC474149
0.5708 Remote Similarity NPC230403
0.5708 Remote Similarity NPC203972
0.5707 Remote Similarity NPC6570
0.5707 Remote Similarity NPC166169
0.5702 Remote Similarity NPC7560
0.5701 Remote Similarity NPC153042
0.57 Remote Similarity NPC190007
0.57 Remote Similarity NPC302235
0.5699 Remote Similarity NPC472243
0.5694 Remote Similarity NPC469830
0.569 Remote Similarity NPC319950
0.5689 Remote Similarity NPC146096
0.5685 Remote Similarity NPC306366
0.5682 Remote Similarity NPC283117
0.5682 Remote Similarity NPC212123
0.568 Remote Similarity NPC291305
0.568 Remote Similarity NPC260118
0.5678 Remote Similarity NPC15506
0.5678 Remote Similarity NPC204179
0.5674 Remote Similarity NPC138615
0.5674 Remote Similarity NPC132874
0.5674 Remote Similarity NPC218733
0.5674 Remote Similarity NPC265642
0.5673 Remote Similarity NPC114918
0.5673 Remote Similarity NPC118202
0.5673 Remote Similarity NPC197513
0.5673 Remote Similarity NPC42591
0.5673 Remote Similarity NPC28425
0.567 Remote Similarity NPC123011
0.567 Remote Similarity NPC256689
0.567 Remote Similarity NPC250448
0.5667 Remote Similarity NPC477839
0.5665 Remote Similarity NPC269414
0.5664 Remote Similarity NPC293151
0.5663 Remote Similarity NPC469428
0.5661 Remote Similarity NPC218388
0.566 Remote Similarity NPC294244
0.5657 Remote Similarity NPC53596
0.5657 Remote Similarity NPC160120
0.5657 Remote Similarity NPC17388

  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 NPC272375 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
0.675 Remote Similarity NPD4931 Phase 2
0.6738 Remote Similarity NPD7129 Suspended
0.6576 Remote Similarity NPD3684 Discontinued
0.6531 Remote Similarity NPD2166 Phase 3
0.6503 Remote Similarity NPD711 Discontinued
0.65 Remote Similarity NPD7628 Phase 3
0.65 Remote Similarity NPD7630 Phase 3
0.65 Remote Similarity NPD7629 Clinical (unspecified phase)
0.6448 Remote Similarity NPD1159 Approved
0.6432 Remote Similarity NPD5565 Discontinued
0.6417 Remote Similarity NPD3812 Clinical (unspecified phase)
0.6387 Remote Similarity NPD1414 Approved
0.6387 Remote Similarity NPD1413 Approved
0.6378 Remote Similarity NPD2425 Phase 1
0.6345 Remote Similarity NPD2169 Clinical (unspecified phase)
0.6344 Remote Similarity NPD1162 Approved
0.6298 Remote Similarity NPD2339 Phase 3
0.6294 Remote Similarity NPD1716 Phase 3
0.6287 Remote Similarity NPD408 Approved
0.6281 Remote Similarity NPD4012 Approved
0.6263 Remote Similarity NPD2168 Clinical (unspecified phase)
0.6263 Remote Similarity NPD2167 Clinical (unspecified phase)
0.623 Remote Similarity NPD1835 Phase 1
0.6202 Remote Similarity NPD712 Clinical (unspecified phase)
0.62 Remote Similarity NPD1361 Discontinued
0.6195 Remote Similarity NPD8067 Phase 3
0.6181 Remote Similarity NPD1717 Clinical (unspecified phase)
0.6173 Remote Similarity NPD1220 Phase 1
0.6165 Remote Similarity NPD5984 Phase 2
0.6162 Remote Similarity NPD1221 Approved
0.6154 Remote Similarity NPD9277 Approved
0.6154 Remote Similarity NPD75 Approved
0.615 Remote Similarity NPD6905 Phase 2
0.615 Remote Similarity NPD6807 Phase 3
0.6143 Remote Similarity NPD7542 Phase 3
0.6124 Remote Similarity NPD1106 Discontinued
0.6119 Remote Similarity NPD1381 Clinical (unspecified phase)
0.6117 Remote Similarity NPD5937 Approved
0.6108 Remote Similarity NPD9342 Approved
0.6105 Remote Similarity NPD1187 Discontinued
0.6099 Remote Similarity NPD9276 Approved
0.6099 Remote Similarity NPD9278 Suspended
0.6099 Remote Similarity NPD9274 Approved
0.6099 Remote Similarity NPD9275 Approved
0.6087 Remote Similarity NPD4591 Clinical (unspecified phase)
0.6087 Remote Similarity NPD4590 Approved
0.6077 Remote Similarity NPD5650 Approved
0.6077 Remote Similarity NPD5652 Approved
0.6077 Remote Similarity NPD5651 Approved
0.6071 Remote Similarity NPD1293 Approved
0.6064 Remote Similarity NPD3277 Phase 3
0.6058 Remote Similarity NPD4771 Phase 2
0.6058 Remote Similarity NPD4523 Approved
0.6053 Remote Similarity NPD5617 Suspended
0.6053 Remote Similarity NPD1514 Discontinued
0.6049 Remote Similarity NPD5800 Discontinued
0.6049 Remote Similarity NPD4113 Discontinued
0.6031 Remote Similarity NPD3453 Discontinued
0.6029 Remote Similarity NPD8249 Clinical (unspecified phase)
0.6021 Remote Similarity NPD980 Clinical (unspecified phase)
0.6019 Remote Similarity NPD5544 Approved
0.6 Remote Similarity NPD4604 Approved
0.6 Remote Similarity NPD4605 Approved
0.6 Remote Similarity NPD3065 Discontinued
0.6 Remote Similarity NPD1615 Approved
0.6 Remote Similarity NPD4979 Clinical (unspecified phase)
0.599 Remote Similarity NPD6058 Phase 2
0.5978 Remote Similarity NPD5729 Clinical (unspecified phase)
0.5972 Remote Similarity NPD4975 Approved
0.5972 Remote Similarity NPD4974 Approved
0.5971 Remote Similarity NPD2792 Approved
0.5969 Remote Similarity NPD1850 Phase 3
0.596 Remote Similarity NPD3975 Discontinued
0.5959 Remote Similarity NPD4485 Approved
0.5943 Remote Similarity NPD9687 Approved
0.5943 Remote Similarity NPD9688 Approved
0.5939 Remote Similarity NPD2681 Approved
0.5939 Remote Similarity NPD2680 Approved
0.5939 Remote Similarity NPD2821 Approved
0.5938 Remote Similarity NPD2469 Approved
0.5938 Remote Similarity NPD6913 Approved
0.5938 Remote Similarity NPD2468 Approved
0.5938 Remote Similarity NPD2672 Discontinued
0.5926 Remote Similarity NPD3932 Clinical (unspecified phase)
0.5922 Remote Similarity NPD3119 Phase 1
0.5922 Remote Similarity NPD3120 Approved
0.5919 Remote Similarity NPD7293 Approved
0.5916 Remote Similarity NPD1634 Approved
0.5899 Remote Similarity NPD3930 Clinical (unspecified phase)
0.5885 Remote Similarity NPD3296 Phase 1
0.5882 Remote Similarity NPD2616 Phase 3
0.5882 Remote Similarity NPD2615 Phase 3
0.5882 Remote Similarity NPD2802 Phase 3
0.5869 Remote Similarity NPD5609 Approved
0.5869 Remote Similarity NPD5608 Approved
0.5865 Remote Similarity NPD5928 Phase 1
0.5864 Remote Similarity NPD1633 Approved
0.5862 Remote Similarity NPD5445 Approved
0.5862 Remote Similarity NPD7959 Clinical (unspecified phase)
0.586 Remote Similarity NPD4387 Approved
0.586 Remote Similarity NPD4386 Approved
0.5857 Remote Similarity NPD4539 Phase 1
0.5851 Remote Similarity NPD3278 Clinical (unspecified phase)
0.5849 Remote Similarity NPD6162 Approved
0.5849 Remote Similarity NPD6161 Approved
0.5848 Remote Similarity NPD7292 Approved
0.5842 Remote Similarity NPD3793 Phase 3
0.5841 Remote Similarity NPD4914 Approved
0.5833 Remote Similarity NPD8014 Clinical (unspecified phase)
0.5829 Remote Similarity NPD5819 Phase 2
0.5829 Remote Similarity NPD522 Approved
0.5824 Remote Similarity NPD2470 Clinical (unspecified phase)
0.5822 Remote Similarity NPD4668 Phase 2
0.582 Remote Similarity NPD1543 Discontinued
0.5818 Remote Similarity NPD9507 Approved
0.5813 Remote Similarity NPD1503 Clinical (unspecified phase)
0.581 Remote Similarity NPD9689 Approved
0.581 Remote Similarity NPD3601 Discontinued
0.5805 Remote Similarity NPD6461 Clinical (unspecified phase)
0.5803 Remote Similarity NPD1092 Approved
0.5803 Remote Similarity NPD1093 Approved
0.5799 Remote Similarity NPD5845 Phase 2
0.5795 Remote Similarity NPD6060 Clinical (unspecified phase)
0.5792 Remote Similarity NPD471 Approved
0.5787 Remote Similarity NPD955 Approved
0.5787 Remote Similarity NPD7071 Clinical (unspecified phase)
0.5782 Remote Similarity NPD5610 Approved
0.5779 Remote Similarity NPD2034 Discontinued
0.5778 Remote Similarity NPD2372 Approved
0.5778 Remote Similarity NPD3136 Phase 2
0.5775 Remote Similarity NPD2941 Discontinued
0.5771 Remote Similarity NPD5858 Discontinued
0.5769 Remote Similarity NPD6346 Approved
0.5764 Remote Similarity NPD3965 Phase 1
0.5762 Remote Similarity NPD6656 Clinical (unspecified phase)
0.5759 Remote Similarity NPD9509 Clinical (unspecified phase)
0.5758 Remote Similarity NPD3363 Clinical (unspecified phase)
0.5749 Remote Similarity NPD6045 Phase 3
0.5745 Remote Similarity NPD1196 Approved
0.5742 Remote Similarity NPD1339 Discontinued
0.5742 Remote Similarity NPD5620 Clinical (unspecified phase)
0.5735 Remote Similarity NPD2826 Approved
0.5735 Remote Similarity NPD5587 Approved
0.5735 Remote Similarity NPD2827 Approved
0.5735 Remote Similarity NPD2825 Approved
0.5733 Remote Similarity NPD5545 Phase 2
0.5729 Remote Similarity NPD1230 Approved
0.5729 Remote Similarity NPD1411 Approved
0.5728 Remote Similarity NPD2744 Phase 1
0.5721 Remote Similarity NPD2216 Approved
0.5721 Remote Similarity NPD2215 Approved
0.5714 Remote Similarity NPD6836 Approved
0.5714 Remote Similarity NPD2498 Approved
0.5714 Remote Similarity NPD6283 Phase 2
0.5708 Remote Similarity NPD7429 Clinical (unspecified phase)
0.5708 Remote Similarity NPD1467 Approved
0.5708 Remote Similarity NPD1466 Phase 3
0.5708 Remote Similarity NPD1505 Phase 2
0.5701 Remote Similarity NPD4388 Approved
0.5701 Remote Similarity NPD4423 Clinical (unspecified phase)
0.5701 Remote Similarity NPD5543 Approved
0.5699 Remote Similarity NPD950 Clinical (unspecified phase)
0.5695 Remote Similarity NPD7301 Phase 3
0.5693 Remote Similarity NPD2246 Approved
0.5693 Remote Similarity NPD2248 Approved
0.5692 Remote Similarity NPD2789 Approved
0.5692 Remote Similarity NPD2366 Approved
0.5691 Remote Similarity NPD1195 Approved
0.5688 Remote Similarity NPD6289 Clinical (unspecified phase)
0.5687 Remote Similarity NPD2327 Clinical (unspecified phase)
0.5686 Remote Similarity NPD1170 Approved
0.5683 Remote Similarity NPD5496 Approved
0.568 Remote Similarity NPD5031 Approved
0.568 Remote Similarity NPD5029 Approved
0.568 Remote Similarity NPD5027 Approved
0.5679 Remote Similarity NPD3986 Discontinued
0.5677 Remote Similarity NPD4186 Clinical (unspecified phase)
0.5676 Remote Similarity NPD6636 Phase 3
0.5676 Remote Similarity NPD648 Clinical (unspecified phase)
0.5674 Remote Similarity NPD2727 Phase 2
0.5674 Remote Similarity NPD6325 Discontinued
0.5668 Remote Similarity NPD7083 Clinical (unspecified phase)
0.5668 Remote Similarity NPD7978 Discontinued
0.5668 Remote Similarity NPD3416 Discontinued
0.5667 Remote Similarity NPD1898 Discontinued
0.5667 Remote Similarity NPD3398 Discontinued
0.5665 Remote Similarity NPD313 Approved
0.5659 Remote Similarity NPD2322 Discovery
0.5656 Remote Similarity NPD7300 Phase 3
0.5656 Remote Similarity NPD7302 Phase 3
0.5652 Remote Similarity NPD3253 Clinical (unspecified phase)
0.565 Remote Similarity NPD3779 Clinical (unspecified phase)
0.5648 Remote Similarity NPD7523 Phase 3
0.5647 Remote Similarity NPD3259 Approved
0.5647 Remote Similarity NPD181 Approved
0.5646 Remote Similarity NPD3154 Approved
0.5646 Remote Similarity NPD3153 Approved
0.5645 Remote Similarity NPD1169 Approved
0.5645 Remote Similarity NPD204 Clinical (unspecified phase)
0.5644 Remote Similarity NPD4083 Discontinued

  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