Structure

Physi-Chem Properties

Molecular Weight:  668.33
Volume:  656.837
LogP:  2.202
LogD:  2.633
LogS:  -4.126
# Rotatable Bonds:  9
TPSA:  163.31
# H-Bond Aceptor:  12
# H-Bond Donor:  5
# Rings:  8
# Heavy Atoms:  12

MedChem Properties

QED Drug-Likeness Score:  0.262
Synthetic Accessibility Score:  7.332
Fsp3:  0.694
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.055
MDCK Permeability:  2.277413477713708e-05
Pgp-inhibitor:  0.102
Pgp-substrate:  0.999
Human Intestinal Absorption (HIA):  0.961
20% Bioavailability (F20%):  0.119
30% Bioavailability (F30%):  0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.15
Plasma Protein Binding (PPB):  69.44315338134766%
Volume Distribution (VD):  0.763
Pgp-substrate:  31.752979278564453%

ADMET: Metabolism

CYP1A2-inhibitor:  0.008
CYP1A2-substrate:  0.959
CYP2C19-inhibitor:  0.005
CYP2C19-substrate:  0.321
CYP2C9-inhibitor:  0.006
CYP2C9-substrate:  0.055
CYP2D6-inhibitor:  0.016
CYP2D6-substrate:  0.2
CYP3A4-inhibitor:  0.283
CYP3A4-substrate:  0.668

ADMET: Excretion

Clearance (CL):  3.623
Half-life (T1/2):  0.462

ADMET: Toxicity

hERG Blockers:  0.213
Human Hepatotoxicity (H-HT):  0.344
Drug-inuced Liver Injury (DILI):  0.035
AMES Toxicity:  0.194
Rat Oral Acute Toxicity:  0.024
Maximum Recommended Daily Dose:  0.502
Skin Sensitization:  0.495
Carcinogencity:  0.045
Eye Corrosion:  0.003
Eye Irritation:  0.009
Respiratory Toxicity:  0.922

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

  Natural Product: NPC473486

Natural Product ID:  NPC473486
Common Name*:   GFWYSOWSJXKFFQ-FPHKUYHXSA-N
IUPAC Name:   n.a.
Synonyms:   14-Deacetylnudicauline
Standard InCHIKey:  GFWYSOWSJXKFFQ-FPHKUYHXSA-N
Standard InCHI:  InChI=1S/C36H48N2O10/c1-6-37-16-33(17-48-31(42)19-9-7-8-10-22(19)38-25(39)13-18(2)30(38)41)12-11-24(46-4)35-21-14-20-23(45-3)15-34(43,26(21)27(20)40)36(44,32(35)37)29(47-5)28(33)35/h7-10,18,20-21,23-24,26-29,32,40,43-44H,6,11-17H2,1-5H3/t18?,20-,21-,23+,24+,26-,27+,28-,29+,32?,33+,34-,35+,36-/m1/s1
SMILES:  CCN1CC2(CCC(C34C2C(C(C31)(C5(CC(C6CC4C5C6O)OC)O)O)OC)OC)COC(=O)C7=CC=CC=C7N8C(=O)CC(C8=O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL443248
PubChem CID:   14239958
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001551] Diterpenoids
          • [CHEMONTID:0003788] Aconitane-type diterpenoid 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
NPO32441 delphinium sp. Species Ranunculaceae Eukaryota n.a. n.a. n.a. PMID[9748371]

☑ 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
NPT32 Organism Mus musculus Mus musculus LD50 = 4.0 mg.kg-1 PMID[458391]
NPT32 Organism Mus musculus Mus musculus LD50 = 4.0 mg.kg-1 PMID[458392]

☑ 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 NPC473486 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 NPC475316
0.9951 High Similarity NPC473781
0.9951 High Similarity NPC470631
0.9951 High Similarity NPC35390
0.9183 High Similarity NPC223590
0.9052 High Similarity NPC106593
0.9009 High Similarity NPC473667
0.8868 High Similarity NPC140311
0.8815 High Similarity NPC473837
0.8252 Intermediate Similarity NPC205
0.8252 Intermediate Similarity NPC124690
0.8252 Intermediate Similarity NPC184195
0.8252 Intermediate Similarity NPC166521
0.8252 Intermediate Similarity NPC172769
0.8252 Intermediate Similarity NPC281470
0.8116 Intermediate Similarity NPC108276
0.8116 Intermediate Similarity NPC163578
0.8068 Intermediate Similarity NPC40539
0.7778 Intermediate Similarity NPC475223
0.7742 Intermediate Similarity NPC246983
0.7742 Intermediate Similarity NPC475448
0.7727 Intermediate Similarity NPC476496
0.7685 Intermediate Similarity NPC475489
0.7602 Intermediate Similarity NPC106840
0.7602 Intermediate Similarity NPC94687
0.7602 Intermediate Similarity NPC476495
0.7557 Intermediate Similarity NPC326895
0.75 Intermediate Similarity NPC473458
0.7489 Intermediate Similarity NPC471512
0.7404 Intermediate Similarity NPC475427
0.7373 Intermediate Similarity NPC221687
0.735 Intermediate Similarity NPC471513
0.7348 Intermediate Similarity NPC288110
0.7311 Intermediate Similarity NPC170751
0.73 Intermediate Similarity NPC30456
0.7294 Intermediate Similarity NPC198205
0.7294 Intermediate Similarity NPC21483
0.7273 Intermediate Similarity NPC311054
0.7273 Intermediate Similarity NPC112752
0.726 Intermediate Similarity NPC97100
0.726 Intermediate Similarity NPC473375
0.7257 Intermediate Similarity NPC475303
0.7257 Intermediate Similarity NPC475596
0.7252 Intermediate Similarity NPC176371
0.7252 Intermediate Similarity NPC136573
0.7246 Intermediate Similarity NPC471190
0.7246 Intermediate Similarity NPC471977
0.7246 Intermediate Similarity NPC470486
0.7246 Intermediate Similarity NPC475644
0.724 Intermediate Similarity NPC90358
0.724 Intermediate Similarity NPC107828
0.7238 Intermediate Similarity NPC160113
0.7238 Intermediate Similarity NPC476220
0.7234 Intermediate Similarity NPC476436
0.7227 Intermediate Similarity NPC198390
0.7227 Intermediate Similarity NPC476429
0.7222 Intermediate Similarity NPC471980
0.7215 Intermediate Similarity NPC477397
0.7203 Intermediate Similarity NPC475600
0.7203 Intermediate Similarity NPC476110
0.7203 Intermediate Similarity NPC87152
0.7203 Intermediate Similarity NPC475631
0.7191 Intermediate Similarity NPC475137
0.7191 Intermediate Similarity NPC475498
0.719 Intermediate Similarity NPC476258
0.719 Intermediate Similarity NPC304837
0.7185 Intermediate Similarity NPC316841
0.7179 Intermediate Similarity NPC127026
0.7179 Intermediate Similarity NPC127720
0.7167 Intermediate Similarity NPC475406
0.7167 Intermediate Similarity NPC327769
0.7161 Intermediate Similarity NPC473506
0.7149 Intermediate Similarity NPC76565
0.7149 Intermediate Similarity NPC473441
0.7149 Intermediate Similarity NPC131273
0.7137 Intermediate Similarity NPC327904
0.7137 Intermediate Similarity NPC38959
0.7131 Intermediate Similarity NPC477787
0.7131 Intermediate Similarity NPC328186
0.7131 Intermediate Similarity NPC228377
0.7131 Intermediate Similarity NPC122968
0.7125 Intermediate Similarity NPC237702
0.7124 Intermediate Similarity NPC301368
0.7124 Intermediate Similarity NPC84815
0.7119 Intermediate Similarity NPC471583
0.7119 Intermediate Similarity NPC477394
0.7119 Intermediate Similarity NPC473850
0.7119 Intermediate Similarity NPC471782
0.7113 Intermediate Similarity NPC473689
0.7113 Intermediate Similarity NPC292416
0.711 Intermediate Similarity NPC105055
0.711 Intermediate Similarity NPC22689
0.7101 Intermediate Similarity NPC475362
0.7083 Intermediate Similarity NPC319880
0.7083 Intermediate Similarity NPC320324
0.7083 Intermediate Similarity NPC322621
0.7083 Intermediate Similarity NPC244839
0.7082 Intermediate Similarity NPC294579
0.7082 Intermediate Similarity NPC144779
0.7078 Intermediate Similarity NPC278540
0.7076 Intermediate Similarity NPC250807
0.7076 Intermediate Similarity NPC57797
0.7072 Intermediate Similarity NPC36607
0.7066 Intermediate Similarity NPC17160
0.7066 Intermediate Similarity NPC154922
0.7066 Intermediate Similarity NPC313720
0.7061 Intermediate Similarity NPC113455
0.7059 Intermediate Similarity NPC146824
0.7059 Intermediate Similarity NPC211920
0.7051 Intermediate Similarity NPC222046
0.7048 Intermediate Similarity NPC476500
0.7046 Intermediate Similarity NPC477902
0.7045 Intermediate Similarity NPC120239
0.7039 Intermediate Similarity NPC471016
0.7039 Intermediate Similarity NPC475408
0.7039 Intermediate Similarity NPC471014
0.7039 Intermediate Similarity NPC6981
0.7016 Intermediate Similarity NPC477396
0.7009 Intermediate Similarity NPC473089
0.7009 Intermediate Similarity NPC62367
0.7009 Intermediate Similarity NPC75600
0.7009 Intermediate Similarity NPC473115
0.7009 Intermediate Similarity NPC212768
0.7009 Intermediate Similarity NPC6576
0.7009 Intermediate Similarity NPC158020
0.7005 Intermediate Similarity NPC73644
0.7004 Intermediate Similarity NPC329932
0.7004 Intermediate Similarity NPC311451
0.7004 Intermediate Similarity NPC477393
0.6996 Remote Similarity NPC475559
0.6996 Remote Similarity NPC234772
0.6996 Remote Similarity NPC470306
0.6995 Remote Similarity NPC129624
0.6992 Remote Similarity NPC477395
0.6992 Remote Similarity NPC469452
0.6987 Remote Similarity NPC124029
0.6979 Remote Similarity NPC216428
0.6975 Remote Similarity NPC328154
0.6967 Remote Similarity NPC30171
0.6964 Remote Similarity NPC475648
0.6962 Remote Similarity NPC477788
0.6955 Remote Similarity NPC475426
0.6953 Remote Similarity NPC4421
0.694 Remote Similarity NPC127996
0.693 Remote Similarity NPC321211
0.6923 Remote Similarity NPC469451
0.6923 Remote Similarity NPC477907
0.6923 Remote Similarity NPC477909
0.6923 Remote Similarity NPC42678
0.692 Remote Similarity NPC90967
0.692 Remote Similarity NPC302548
0.692 Remote Similarity NPC477912
0.6911 Remote Similarity NPC469450
0.6911 Remote Similarity NPC253482
0.6905 Remote Similarity NPC253738
0.6901 Remote Similarity NPC96801
0.6901 Remote Similarity NPC477906
0.6901 Remote Similarity NPC150698
0.6885 Remote Similarity NPC35208
0.6875 Remote Similarity NPC148860
0.687 Remote Similarity NPC473565
0.6867 Remote Similarity NPC472553
0.6867 Remote Similarity NPC476467
0.6849 Remote Similarity NPC477903
0.6847 Remote Similarity NPC25401
0.6837 Remote Similarity NPC476441
0.6835 Remote Similarity NPC472555
0.6833 Remote Similarity NPC477998
0.6825 Remote Similarity NPC472574
0.682 Remote Similarity NPC469312
0.682 Remote Similarity NPC41318
0.681 Remote Similarity NPC477160
0.6808 Remote Similarity NPC469915
0.6807 Remote Similarity NPC318525
0.6807 Remote Similarity NPC10653
0.6803 Remote Similarity NPC469748
0.6802 Remote Similarity NPC301501
0.6802 Remote Similarity NPC473298
0.6783 Remote Similarity NPC329833
0.678 Remote Similarity NPC477910
0.6777 Remote Similarity NPC475601
0.6777 Remote Similarity NPC313757
0.6776 Remote Similarity NPC238278
0.6774 Remote Similarity NPC475094
0.6773 Remote Similarity NPC52262
0.6763 Remote Similarity NPC477900
0.6763 Remote Similarity NPC477899
0.6758 Remote Similarity NPC477159
0.6757 Remote Similarity NPC327699
0.6751 Remote Similarity NPC206343
0.6751 Remote Similarity NPC477908
0.675 Remote Similarity NPC477911
0.675 Remote Similarity NPC235364
0.6745 Remote Similarity NPC472106
0.6744 Remote Similarity NPC476425
0.6738 Remote Similarity NPC472550
0.6738 Remote Similarity NPC48042
0.6738 Remote Similarity NPC304179
0.6737 Remote Similarity NPC319128
0.6737 Remote Similarity NPC264674

  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 NPC473486 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
0.75 Intermediate Similarity NPD7497 Discontinued
0.715 Intermediate Similarity NPD8658 Clinical (unspecified phase)
0.7106 Intermediate Similarity NPD6997 Phase 2
0.6773 Remote Similarity NPD8468 Phase 2
0.6696 Remote Similarity NPD7238 Clinical (unspecified phase)
0.6682 Remote Similarity NPD7962 Phase 2
0.6578 Remote Similarity NPD8435 Approved
0.6578 Remote Similarity NPD8361 Approved
0.6578 Remote Similarity NPD8360 Approved
0.6569 Remote Similarity NPD7047 Phase 3
0.6562 Remote Similarity NPD8424 Clinical (unspecified phase)
0.655 Remote Similarity NPD8485 Approved
0.6531 Remote Similarity NPD7186 Phase 3
0.6506 Remote Similarity NPD6625 Approved
0.65 Remote Similarity NPD8470 Clinical (unspecified phase)
0.6493 Remote Similarity NPD5742 Approved
0.6493 Remote Similarity NPD5741 Approved
0.6493 Remote Similarity NPD5743 Approved
0.6466 Remote Similarity NPD8486 Clinical (unspecified phase)
0.6461 Remote Similarity NPD7858 Clinical (unspecified phase)
0.6461 Remote Similarity NPD3437 Discontinued
0.6445 Remote Similarity NPD4121 Phase 3
0.6445 Remote Similarity NPD4120 Approved
0.6426 Remote Similarity NPD7688 Phase 1
0.6416 Remote Similarity NPD6891 Phase 2
0.6416 Remote Similarity NPD8103 Clinical (unspecified phase)
0.6404 Remote Similarity NPD6659 Phase 2
0.6395 Remote Similarity NPD6805 Discontinued
0.6382 Remote Similarity NPD3912 Discontinued
0.6376 Remote Similarity NPD8146 Phase 2
0.6376 Remote Similarity NPD7570 Approved
0.6376 Remote Similarity NPD7569 Approved
0.6375 Remote Similarity NPD6723 Discontinued
0.6364 Remote Similarity NPD7880 Clinical (unspecified phase)
0.6364 Remote Similarity NPD7048 Phase 3
0.636 Remote Similarity NPD5928 Phase 1
0.6352 Remote Similarity NPD6874 Approved
0.6347 Remote Similarity NPD7795 Phase 2
0.6341 Remote Similarity NPD6995 Phase 1
0.6332 Remote Similarity NPD3808 Clinical (unspecified phase)
0.6327 Remote Similarity NPD8407 Phase 2
0.6327 Remote Similarity NPD8459 Approved
0.6327 Remote Similarity NPD8460 Approved
0.6324 Remote Similarity NPD5891 Approved
0.632 Remote Similarity NPD8364 Approved
0.632 Remote Similarity NPD8363 Approved
0.6314 Remote Similarity NPD7597 Clinical (unspecified phase)
0.6314 Remote Similarity NPD7064 Clinical (unspecified phase)
0.63 Remote Similarity NPD8466 Approved
0.63 Remote Similarity NPD8467 Approved
0.63 Remote Similarity NPD8465 Approved
0.6296 Remote Similarity NPD8149 Discontinued
0.629 Remote Similarity NPD5997 Discontinued
0.6279 Remote Similarity NPD7921 Approved
0.6274 Remote Similarity NPD7606 Phase 3
0.6273 Remote Similarity NPD8365 Clinical (unspecified phase)
0.6269 Remote Similarity NPD7803 Approved
0.6268 Remote Similarity NPD7295 Approved
0.625 Remote Similarity NPD7560 Approved
0.6245 Remote Similarity NPD7205 Discontinued
0.6245 Remote Similarity NPD7906 Approved
0.6245 Remote Similarity NPD7922 Phase 1
0.6241 Remote Similarity NPD7708 Approved
0.6235 Remote Similarity NPD7805 Phase 3
0.6235 Remote Similarity NPD7907 Approved
0.623 Remote Similarity NPD5025 Approved
0.6223 Remote Similarity NPD5411 Discontinued
0.6223 Remote Similarity NPD7667 Clinical (unspecified phase)
0.622 Remote Similarity NPD2899 Discontinued
0.622 Remote Similarity NPD7488 Clinical (unspecified phase)
0.622 Remote Similarity NPD7487 Discontinued
0.6215 Remote Similarity NPD6591 Clinical (unspecified phase)
0.621 Remote Similarity NPD5430 Discontinued
0.6209 Remote Similarity NPD8426 Approved
0.6209 Remote Similarity NPD8425 Approved
0.6204 Remote Similarity NPD5715 Clinical (unspecified phase)
0.6203 Remote Similarity NPD7956 Approved
0.6203 Remote Similarity NPD7955 Approved
0.6202 Remote Similarity NPD6716 Phase 1
0.6197 Remote Similarity NPD2973 Approved
0.6197 Remote Similarity NPD2974 Approved
0.6197 Remote Similarity NPD2975 Approved
0.6195 Remote Similarity NPD8368 Discontinued
0.6192 Remote Similarity NPD7174 Clinical (unspecified phase)
0.6188 Remote Similarity NPD5919 Clinical (unspecified phase)
0.6186 Remote Similarity NPD4580 Approved
0.6182 Remote Similarity NPD8428 Approved
0.6182 Remote Similarity NPD8429 Approved
0.6182 Remote Similarity NPD8427 Approved
0.6179 Remote Similarity NPD7878 Phase 2
0.6173 Remote Similarity NPD8462 Phase 1
0.6172 Remote Similarity NPD4846 Phase 2
0.6172 Remote Similarity NPD2820 Phase 3
0.617 Remote Similarity NPD4668 Phase 2
0.6165 Remote Similarity NPD8461 Discontinued
0.6163 Remote Similarity NPD7417 Discontinued
0.6161 Remote Similarity NPD5603 Clinical (unspecified phase)
0.6161 Remote Similarity NPD7799 Discontinued
0.616 Remote Similarity NPD3452 Approved
0.616 Remote Similarity NPD2494 Approved
0.616 Remote Similarity NPD2493 Approved
0.616 Remote Similarity NPD7821 Clinical (unspecified phase)
0.616 Remote Similarity NPD3450 Approved
0.6157 Remote Similarity NPD4900 Clinical (unspecified phase)
0.6157 Remote Similarity NPD2836 Approved
0.6154 Remote Similarity NPD5582 Discontinued
0.6151 Remote Similarity NPD8319 Approved
0.6151 Remote Similarity NPD4583 Approved
0.6151 Remote Similarity NPD8320 Phase 1
0.6151 Remote Similarity NPD4582 Approved
0.6151 Remote Similarity NPD5102 Clinical (unspecified phase)
0.6144 Remote Similarity NPD5609 Approved
0.6144 Remote Similarity NPD5608 Approved
0.6143 Remote Similarity NPD7854 Phase 2
0.6141 Remote Similarity NPD7302 Phase 3
0.6141 Remote Similarity NPD7300 Phase 3
0.614 Remote Similarity NPD5086 Approved
0.6138 Remote Similarity NPD8404 Phase 2
0.6132 Remote Similarity NPD7478 Approved
0.6129 Remote Similarity NPD5433 Clinical (unspecified phase)
0.6125 Remote Similarity NPD8161 Suspended
0.6124 Remote Similarity NPD2365 Approved
0.6121 Remote Similarity NPD5525 Clinical (unspecified phase)
0.612 Remote Similarity NPD7820 Phase 3
0.6109 Remote Similarity NPD4002 Approved
0.6109 Remote Similarity NPD4004 Approved
0.6107 Remote Similarity NPD7225 Discontinued
0.6104 Remote Similarity NPD8155 Clinical (unspecified phase)
0.6103 Remote Similarity NPD7528 Approved
0.6102 Remote Similarity NPD5197 Approved
0.6102 Remote Similarity NPD5194 Approved
0.6102 Remote Similarity NPD5196 Approved
0.609 Remote Similarity NPD8492 Approved
0.6089 Remote Similarity NPD4111 Phase 1
0.6089 Remote Similarity NPD4665 Approved
0.6081 Remote Similarity NPD6457 Approved
0.6079 Remote Similarity NPD6293 Clinical (unspecified phase)
0.6077 Remote Similarity NPD7702 Clinical (unspecified phase)
0.6076 Remote Similarity NPD7810 Phase 3
0.6076 Remote Similarity NPD7811 Phase 3
0.6075 Remote Similarity NPD2737 Clinical (unspecified phase)
0.6073 Remote Similarity NPD7600 Phase 2
0.6068 Remote Similarity NPD5610 Approved
0.6067 Remote Similarity NPD5005 Approved
0.6067 Remote Similarity NPD5006 Approved
0.6066 Remote Similarity NPD5676 Approved
0.6066 Remote Similarity NPD1945 Phase 1
0.6063 Remote Similarity NPD4981 Phase 2
0.6061 Remote Similarity NPD4663 Approved
0.6058 Remote Similarity NPD4901 Clinical (unspecified phase)
0.6056 Remote Similarity NPD7278 Phase 2
0.6056 Remote Similarity NPD7279 Phase 2
0.6052 Remote Similarity NPD5042 Phase 1
0.6052 Remote Similarity NPD6656 Clinical (unspecified phase)
0.6043 Remote Similarity NPD6021 Clinical (unspecified phase)
0.6042 Remote Similarity NPD6445 Discontinued
0.6041 Remote Similarity NPD7301 Phase 3
0.6038 Remote Similarity NPD6503 Clinical (unspecified phase)
0.6034 Remote Similarity NPD6608 Clinical (unspecified phase)
0.6034 Remote Similarity NPD4420 Approved
0.6033 Remote Similarity NPD7583 Approved
0.6027 Remote Similarity NPD7599 Phase 2
0.6026 Remote Similarity NPD8281 Discontinued
0.6025 Remote Similarity NPD6238 Discontinued
0.6025 Remote Similarity NPD5860 Discontinued
0.6025 Remote Similarity NPD6321 Discontinued
0.6024 Remote Similarity NPD6770 Approved
0.6024 Remote Similarity NPD5496 Approved
0.6022 Remote Similarity NPD7181 Phase 3
0.6019 Remote Similarity NPD7082 Approved
0.601 Remote Similarity NPD2670 Approved
0.6009 Remote Similarity NPD6211 Clinical (unspecified phase)
0.6009 Remote Similarity NPD6496 Clinical (unspecified phase)
0.6008 Remote Similarity NPD3940 Clinical (unspecified phase)
0.6008 Remote Similarity NPD4082 Approved
0.6008 Remote Similarity NPD7585 Approved
0.6008 Remote Similarity NPD7701 Phase 2
0.6 Remote Similarity NPD5721 Clinical (unspecified phase)
0.6 Remote Similarity NPD3057 Approved
0.6 Remote Similarity NPD4577 Approved
0.6 Remote Similarity NPD4493 Discontinued
0.6 Remote Similarity NPD4578 Approved
0.5993 Remote Similarity NPD8463 Approved
0.5992 Remote Similarity NPD6621 Clinical (unspecified phase)
0.5992 Remote Similarity NPD4946 Phase 2
0.5992 Remote Similarity NPD5619 Clinical (unspecified phase)
0.5991 Remote Similarity NPD7683 Discontinued
0.5991 Remote Similarity NPD7259 Approved
0.5984 Remote Similarity NPD8059 Phase 3
0.5984 Remote Similarity NPD8058 Clinical (unspecified phase)
0.5983 Remote Similarity NPD4107 Approved
0.5982 Remote Similarity NPD5186 Approved
0.5982 Remote Similarity NPD5183 Approved
0.5981 Remote Similarity NPD8165 Discontinued
0.5981 Remote Similarity NPD7794 Clinical (unspecified phase)
0.5981 Remote Similarity NPD1802 Approved
0.5981 Remote Similarity NPD1801 Approved
0.5976 Remote Similarity NPD7827 Phase 1
0.5973 Remote Similarity NPD3422 Phase 3
0.5973 Remote Similarity NPD3423 Phase 2

  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