Structure

Physi-Chem Properties

Molecular Weight:  580.34
Volume:  603.47
LogP:  4.58
LogD:  3.462
LogS:  -3.552
# Rotatable Bonds:  1
TPSA:  84.85
# H-Bond Aceptor:  7
# H-Bond Donor:  3
# Rings:  9
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.301
Synthetic Accessibility Score:  7.357
Fsp3:  0.583
Lipinski Rule-of-5:  Accepted
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:  -5.237
MDCK Permeability:  1.8560533135314472e-05
Pgp-inhibitor:  0.301
Pgp-substrate:  0.991
Human Intestinal Absorption (HIA):  0.016
20% Bioavailability (F20%):  1.0
30% Bioavailability (F30%):  0.146

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.815
Plasma Protein Binding (PPB):  90.78382110595703%
Volume Distribution (VD):  4.505
Pgp-substrate:  7.802577972412109%

ADMET: Metabolism

CYP1A2-inhibitor:  0.05
CYP1A2-substrate:  0.816
CYP2C19-inhibitor:  0.121
CYP2C19-substrate:  0.587
CYP2C9-inhibitor:  0.136
CYP2C9-substrate:  0.296
CYP2D6-inhibitor:  0.911
CYP2D6-substrate:  0.916
CYP3A4-inhibitor:  0.977
CYP3A4-substrate:  0.916

ADMET: Excretion

Clearance (CL):  8.748
Half-life (T1/2):  0.186

ADMET: Toxicity

hERG Blockers:  0.922
Human Hepatotoxicity (H-HT):  0.974
Drug-inuced Liver Injury (DILI):  0.045
AMES Toxicity:  0.673
Rat Oral Acute Toxicity:  0.206
Maximum Recommended Daily Dose:  0.985
Skin Sensitization:  0.935
Carcinogencity:  0.626
Eye Corrosion:  0.003
Eye Irritation:  0.008
Respiratory Toxicity:  0.952

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

  Natural Product: NPC81175

Natural Product ID:  NPC81175
Common Name*:   Manzamine X
IUPAC Name:   n.a.
Synonyms:   Manzamine X
Standard InCHIKey:  YFLBQKLEXJGASL-SLQIETCISA-N
Standard InCHI:  InChI=1S/C36H44N4O3/c41-24-9-10-30-27(20-24)26-12-16-37-31(32(26)38-30)28-21-35(42)14-5-3-1-2-4-6-17-39-19-13-29(28)34(23-39)22-36-15-11-25(43-36)8-7-18-40(36)33(34)35/h1,3,9-10,12,16,20-21,25,29,33,38,41-42H,2,4-8,11,13-15,17-19,22-23H2/b3-1-/t25-,29+,33-,34+,35+,36+/m1/s1
SMILES:  C1=CCC[C@@]2(C=C([C@@H]3CCN(CCCC1)C[C@]13C[C@@]34CC[C@@H](CCCN3[C@@H]21)O4)c1c2c(ccn1)c1cc(ccc1[nH]2)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL506416
PubChem CID:   21674226
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
NPO32531 sponge sp. Species n.a. n.a. n.a. collected from vertical slopes between 33 and 40 m from Knife Cape, Manado Bay, Indonesia 2011-MAR PMID[12828469]
NPO33280 Acanthostrongylophora sp. Species Petrosiidae Eukaryota n.a. n.a. n.a. PMID[15332848]
NPO33280 Acanthostrongylophora sp. Species Petrosiidae Eukaryota n.a. collected from vertical slopes between 33 and 40 m from Knife Cape Manado, Indonesia n.a. PMID[16872140]
NPO33280 Acanthostrongylophora sp. Species Petrosiidae Eukaryota n.a. collected from vertical slopes between 33 and 40 m from Knife Cape Manado, Indonesia 2004-Mar PMID[16872140]
NPO33280 Acanthostrongylophora sp. Species Petrosiidae Eukaryota n.a. Indonesian n.a. PMID[16872140]
NPO33280 Acanthostrongylophora sp. Species Petrosiidae Eukaryota n.a. collected from vertical slopes between 33 and 40 m from Knife Cape Manado, Indonesia 2002-May PMID[16872140]
NPO33280 Acanthostrongylophora sp. Species Petrosiidae Eukaryota n.a. n.a. n.a. PMID[28452477]

☑ 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
NPT139 Cell Line HT-29 Homo sapiens IC50 = 0.5 ug.mL-1 PMID[529331]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 0.95 ug.mL-1 PMID[529331]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 2.0 ug.mL-1 PMID[529331]
NPT633 Organism Leishmania donovani Leishmania donovani IC50 = 5.7 ug.mL-1 PMID[529331]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 5.1 ug.mL-1 PMID[529331]
NPT27 Others Unspecified IC50 = 5.1 ug.mL-1 PMID[529331]
NPT633 Organism Leishmania donovani Leishmania donovani IC90 = 11.0 ug.mL-1 PMID[529331]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 0.95 ug.mL-1 PMID[529332]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 2.0 ug.mL-1 PMID[529332]
NPT633 Organism Leishmania donovani Leishmania donovani IC50 = 5.7 ug.mL-1 PMID[529332]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus IC50 = 1.0 ug.mL-1 PMID[529332]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus IC50 = 0.75 ug.mL-1 PMID[529332]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans IC50 = 3.0 ug.mL-1 PMID[529332]
NPT86 Organism Mycobacterium intracellulare Mycobacterium intracellulare IC50 = 1.5 ug.mL-1 PMID[529332]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 EC50 = 2300.0 nM PMID[529332]
NPT633 Organism Leishmania donovani Leishmania donovani IC90 = 11.0 ug.mL-1 PMID[529332]

☑ 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 NPC81175 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
0.9245 High Similarity NPC471506
0.9209 High Similarity NPC6215
0.8982 High Similarity NPC471891
0.8839 High Similarity NPC41679
0.8824 High Similarity NPC476451
0.8604 High Similarity NPC476492
0.8478 Intermediate Similarity NPC473312
0.8447 Intermediate Similarity NPC304926
0.8447 Intermediate Similarity NPC476041
0.8372 Intermediate Similarity NPC166492
0.8372 Intermediate Similarity NPC473362
0.8341 Intermediate Similarity NPC5145
0.8318 Intermediate Similarity NPC472027
0.8311 Intermediate Similarity NPC473757
0.8279 Intermediate Similarity NPC475070
0.8211 Intermediate Similarity NPC476116
0.819 Intermediate Similarity NPC250835
0.8169 Intermediate Similarity NPC265576
0.8143 Intermediate Similarity NPC471564
0.808 Intermediate Similarity NPC473310
0.8077 Intermediate Similarity NPC477861
0.8042 Intermediate Similarity NPC476493
0.8035 Intermediate Similarity NPC475258
0.8 Intermediate Similarity NPC253580
0.7991 Intermediate Similarity NPC475338
0.7991 Intermediate Similarity NPC909
0.7991 Intermediate Similarity NPC251936
0.7991 Intermediate Similarity NPC475288
0.7974 Intermediate Similarity NPC469554
0.7957 Intermediate Similarity NPC470126
0.7949 Intermediate Similarity NPC295228
0.7945 Intermediate Similarity NPC470500
0.7926 Intermediate Similarity NPC249040
0.7821 Intermediate Similarity NPC101543
0.7752 Intermediate Similarity NPC192315
0.7748 Intermediate Similarity NPC474145
0.7748 Intermediate Similarity NPC475841
0.7725 Intermediate Similarity NPC476491
0.7717 Intermediate Similarity NPC476167
0.7706 Intermediate Similarity NPC77555
0.7692 Intermediate Similarity NPC314954
0.7685 Intermediate Similarity NPC99666
0.7682 Intermediate Similarity NPC329793
0.7682 Intermediate Similarity NPC176538
0.7675 Intermediate Similarity NPC183407
0.7675 Intermediate Similarity NPC469928
0.7652 Intermediate Similarity NPC213530
0.7652 Intermediate Similarity NPC193267
0.7623 Intermediate Similarity NPC329708
0.7623 Intermediate Similarity NPC47059
0.7623 Intermediate Similarity NPC118832
0.7623 Intermediate Similarity NPC274291
0.7623 Intermediate Similarity NPC264166
0.7623 Intermediate Similarity NPC165349
0.7617 Intermediate Similarity NPC171171
0.7611 Intermediate Similarity NPC475422
0.7609 Intermediate Similarity NPC469594
0.7605 Intermediate Similarity NPC325976
0.7604 Intermediate Similarity NPC324149
0.7598 Intermediate Similarity NPC477110
0.7598 Intermediate Similarity NPC8022
0.7598 Intermediate Similarity NPC470799
0.7588 Intermediate Similarity NPC475602
0.7588 Intermediate Similarity NPC477610
0.7586 Intermediate Similarity NPC310118
0.7573 Intermediate Similarity NPC477549
0.757 Intermediate Similarity NPC314002
0.7564 Intermediate Similarity NPC313884
0.7564 Intermediate Similarity NPC98371
0.7562 Intermediate Similarity NPC171393
0.7562 Intermediate Similarity NPC295452
0.7559 Intermediate Similarity NPC220765
0.7554 Intermediate Similarity NPC162748
0.7544 Intermediate Similarity NPC26679
0.7534 Intermediate Similarity NPC211813
0.7532 Intermediate Similarity NPC24370
0.7532 Intermediate Similarity NPC319232
0.7523 Intermediate Similarity NPC204717
0.7522 Intermediate Similarity NPC477111
0.7522 Intermediate Similarity NPC87755
0.7511 Intermediate Similarity NPC471080
0.7511 Intermediate Similarity NPC469592
0.7511 Intermediate Similarity NPC326363
0.7511 Intermediate Similarity NPC472111
0.75 Intermediate Similarity NPC110151
0.75 Intermediate Similarity NPC223427
0.7479 Intermediate Similarity NPC280272
0.7468 Intermediate Similarity NPC477608
0.7466 Intermediate Similarity NPC232130
0.7458 Intermediate Similarity NPC60006
0.7456 Intermediate Similarity NPC126066
0.7448 Intermediate Similarity NPC207686
0.7448 Intermediate Similarity NPC474192
0.7448 Intermediate Similarity NPC475720
0.7445 Intermediate Similarity NPC475910
0.7435 Intermediate Similarity NPC478074
0.7434 Intermediate Similarity NPC477113
0.743 Intermediate Similarity NPC329982
0.7424 Intermediate Similarity NPC208284
0.7412 Intermediate Similarity NPC185782
0.7404 Intermediate Similarity NPC470501
0.74 Intermediate Similarity NPC478080
0.7395 Intermediate Similarity NPC48938
0.7395 Intermediate Similarity NPC477607
0.7382 Intermediate Similarity NPC477609
0.738 Intermediate Similarity NPC167860
0.738 Intermediate Similarity NPC123976
0.7373 Intermediate Similarity NPC130570
0.7371 Intermediate Similarity NPC184964
0.7362 Intermediate Similarity NPC470502
0.7347 Intermediate Similarity NPC39092
0.7345 Intermediate Similarity NPC476138
0.7345 Intermediate Similarity NPC245816
0.7344 Intermediate Similarity NPC323752
0.7344 Intermediate Similarity NPC315467
0.7342 Intermediate Similarity NPC245348
0.7342 Intermediate Similarity NPC251090
0.733 Intermediate Similarity NPC307963
0.7327 Intermediate Similarity NPC15102
0.7322 Intermediate Similarity NPC33949
0.7319 Intermediate Similarity NPC132642
0.7311 Intermediate Similarity NPC214980
0.7309 Intermediate Similarity NPC156704
0.7306 Intermediate Similarity NPC477066
0.7304 Intermediate Similarity NPC471304
0.73 Intermediate Similarity NPC470503
0.7298 Intermediate Similarity NPC17437
0.7296 Intermediate Similarity NPC330009
0.7293 Intermediate Similarity NPC314957
0.7289 Intermediate Similarity NPC315491
0.7289 Intermediate Similarity NPC45459
0.7276 Intermediate Similarity NPC477067
0.7276 Intermediate Similarity NPC478081
0.7276 Intermediate Similarity NPC478082
0.7265 Intermediate Similarity NPC475816
0.7261 Intermediate Similarity NPC469589
0.726 Intermediate Similarity NPC46580
0.7257 Intermediate Similarity NPC232727
0.7254 Intermediate Similarity NPC15801
0.7254 Intermediate Similarity NPC184225
0.7249 Intermediate Similarity NPC53344
0.7248 Intermediate Similarity NPC478009
0.7248 Intermediate Similarity NPC478010
0.7244 Intermediate Similarity NPC478006
0.7241 Intermediate Similarity NPC294620
0.724 Intermediate Similarity NPC26543
0.724 Intermediate Similarity NPC92111
0.7235 Intermediate Similarity NPC139291
0.7235 Intermediate Similarity NPC472108
0.7234 Intermediate Similarity NPC96321
0.7227 Intermediate Similarity NPC32771
0.7212 Intermediate Similarity NPC19872
0.721 Intermediate Similarity NPC266931
0.7206 Intermediate Similarity NPC473540
0.7205 Intermediate Similarity NPC476124
0.7205 Intermediate Similarity NPC476121
0.7202 Intermediate Similarity NPC472294
0.7202 Intermediate Similarity NPC473105
0.7198 Intermediate Similarity NPC152620
0.7195 Intermediate Similarity NPC76748
0.7195 Intermediate Similarity NPC95783
0.7193 Intermediate Similarity NPC476098
0.7191 Intermediate Similarity NPC469727
0.7189 Intermediate Similarity NPC178858
0.7189 Intermediate Similarity NPC469734
0.7189 Intermediate Similarity NPC314394
0.7183 Intermediate Similarity NPC153400
0.7176 Intermediate Similarity NPC88363
0.7174 Intermediate Similarity NPC88008
0.7167 Intermediate Similarity NPC132631
0.7167 Intermediate Similarity NPC103687
0.7167 Intermediate Similarity NPC94157
0.7165 Intermediate Similarity NPC53534
0.7163 Intermediate Similarity NPC203754
0.7163 Intermediate Similarity NPC150048
0.7154 Intermediate Similarity NPC11408
0.7149 Intermediate Similarity NPC296527
0.7149 Intermediate Similarity NPC246700
0.7149 Intermediate Similarity NPC193761
0.7143 Intermediate Similarity NPC82548
0.7143 Intermediate Similarity NPC133366
0.7137 Intermediate Similarity NPC473185
0.7137 Intermediate Similarity NPC476287
0.7137 Intermediate Similarity NPC329747
0.7137 Intermediate Similarity NPC213308
0.7132 Intermediate Similarity NPC45048
0.7131 Intermediate Similarity NPC180504
0.7125 Intermediate Similarity NPC125597
0.7123 Intermediate Similarity NPC284678
0.7118 Intermediate Similarity NPC475774
0.7118 Intermediate Similarity NPC200836
0.7118 Intermediate Similarity NPC53144
0.7117 Intermediate Similarity NPC106833
0.7117 Intermediate Similarity NPC469497
0.7114 Intermediate Similarity NPC28945
0.711 Intermediate Similarity NPC478012
0.711 Intermediate Similarity NPC478011
0.711 Intermediate Similarity NPC471303
0.7107 Intermediate Similarity NPC311906
0.7101 Intermediate Similarity NPC276657

  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 NPC81175 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
0.7731 Intermediate Similarity NPD5575 Clinical (unspecified phase)
0.7699 Intermediate Similarity NPD3330 Phase 1
0.7626 Intermediate Similarity NPD7948 Phase 1
0.7623 Intermediate Similarity NPD32 Approved
0.7623 Intermediate Similarity NPD31 Approved
0.7623 Intermediate Similarity NPD4122 Approved
0.7623 Intermediate Similarity NPD4036 Approved
0.7623 Intermediate Similarity NPD4033 Approved
0.7623 Intermediate Similarity NPD4039 Approved
0.7623 Intermediate Similarity NPD4038 Approved
0.7623 Intermediate Similarity NPD4037 Approved
0.7623 Intermediate Similarity NPD4034 Approved
0.7623 Intermediate Similarity NPD4035 Approved
0.7564 Intermediate Similarity NPD6976 Clinical (unspecified phase)
0.7557 Intermediate Similarity NPD4118 Clinical (unspecified phase)
0.7522 Intermediate Similarity NPD5612 Discontinued
0.7522 Intermediate Similarity NPD7112 Discontinued
0.75 Intermediate Similarity NPD6977 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6978 Phase 2
0.7489 Intermediate Similarity NPD7823 Clinical (unspecified phase)
0.7419 Intermediate Similarity NPD6503 Clinical (unspecified phase)
0.7417 Intermediate Similarity NPD7558 Phase 2
0.7382 Intermediate Similarity NPD8405 Clinical (unspecified phase)
0.7371 Intermediate Similarity NPD6803 Clinical (unspecified phase)
0.735 Intermediate Similarity NPD3402 Phase 1
0.733 Intermediate Similarity NPD1038 Approved
0.7327 Intermediate Similarity NPD6344 Clinical (unspecified phase)
0.7322 Intermediate Similarity NPD5559 Phase 2
0.7321 Intermediate Similarity NPD8396 Approved
0.7321 Intermediate Similarity NPD8395 Approved
0.7298 Intermediate Similarity NPD8358 Approved
0.7292 Intermediate Similarity NPD7824 Approved
0.7289 Intermediate Similarity NPD484 Approved
0.7269 Intermediate Similarity NPD4886 Phase 2
0.7253 Intermediate Similarity NPD7073 Clinical (unspecified phase)
0.7249 Intermediate Similarity NPD7222 Phase 2
0.7249 Intermediate Similarity NPD7452 Approved
0.7249 Intermediate Similarity NPD7453 Approved
0.7248 Intermediate Similarity NPD6610 Clinical (unspecified phase)
0.7238 Intermediate Similarity NPD7603 Discontinued
0.7234 Intermediate Similarity NPD8109 Clinical (unspecified phase)
0.7208 Intermediate Similarity NPD7730 Approved
0.7208 Intermediate Similarity NPD7731 Approved
0.7202 Intermediate Similarity NPD5040 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD7271 Approved
0.7196 Intermediate Similarity NPD5065 Approved
0.7194 Intermediate Similarity NPD8442 Discontinued
0.7175 Intermediate Similarity NPD1304 Clinical (unspecified phase)
0.7162 Intermediate Similarity NPD4795 Phase 2
0.7156 Intermediate Similarity NPD5522 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD7726 Phase 1
0.7143 Intermediate Similarity NPD6773 Clinical (unspecified phase)
0.7131 Intermediate Similarity NPD7950 Approved
0.7131 Intermediate Similarity NPD6455 Phase 3
0.7131 Intermediate Similarity NPD7789 Approved
0.7131 Intermediate Similarity NPD7951 Approved
0.7131 Intermediate Similarity NPD7790 Approved
0.7131 Intermediate Similarity NPD7952 Approved
0.7131 Intermediate Similarity NPD7791 Approved
0.7131 Intermediate Similarity NPD7953 Approved
0.7124 Intermediate Similarity NPD7889 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD6717 Clinical (unspecified phase)
0.7093 Intermediate Similarity NPD2175 Phase 3
0.7093 Intermediate Similarity NPD2176 Approved
0.7093 Intermediate Similarity NPD2177 Approved
0.708 Intermediate Similarity NPD5483 Clinical (unspecified phase)
0.7078 Intermediate Similarity NPD8512 Phase 3
0.7061 Intermediate Similarity NPD6494 Phase 2
0.7056 Intermediate Similarity NPD8016 Phase 3
0.7056 Intermediate Similarity NPD8017 Clinical (unspecified phase)
0.7051 Intermediate Similarity NPD5939 Approved
0.7051 Intermediate Similarity NPD7470 Discontinued
0.7051 Intermediate Similarity NPD5936 Approved
0.7042 Intermediate Similarity NPD7219 Approved
0.7042 Intermediate Similarity NPD7221 Approved
0.7039 Intermediate Similarity NPD2125 Clinical (unspecified phase)
0.7031 Intermediate Similarity NPD4511 Phase 1
0.7026 Intermediate Similarity NPD6838 Clinical (unspecified phase)
0.7026 Intermediate Similarity NPD6290 Phase 2
0.7004 Intermediate Similarity NPD7181 Phase 3
0.7 Intermediate Similarity NPD6456 Discontinued
0.6996 Remote Similarity NPD5658 Approved
0.6996 Remote Similarity NPD7947 Clinical (unspecified phase)
0.6992 Remote Similarity NPD8488 Clinical (unspecified phase)
0.6991 Remote Similarity NPD3324 Clinical (unspecified phase)
0.6987 Remote Similarity NPD1739 Approved
0.6987 Remote Similarity NPD1740 Approved
0.6987 Remote Similarity NPD7194 Discontinued
0.6986 Remote Similarity NPD6595 Phase 3
0.6983 Remote Similarity NPD5530 Phase 1
0.6973 Remote Similarity NPD3343 Phase 3
0.6972 Remote Similarity NPD6203 Clinical (unspecified phase)
0.6969 Remote Similarity NPD8101 Phase 3
0.6958 Remote Similarity NPD8364 Approved
0.6958 Remote Similarity NPD8363 Approved
0.6955 Remote Similarity NPD7674 Phase 3
0.6955 Remote Similarity NPD7676 Clinical (unspecified phase)
0.6955 Remote Similarity NPD7675 Phase 3
0.6953 Remote Similarity NPD1392 Approved
0.6949 Remote Similarity NPD8458 Clinical (unspecified phase)
0.6943 Remote Similarity NPD3825 Phase 3
0.6926 Remote Similarity NPD8246 Approved
0.6926 Remote Similarity NPD8247 Approved
0.6923 Remote Similarity NPD7666 Phase 3
0.6923 Remote Similarity NPD7665 Phase 2
0.692 Remote Similarity NPD2921 Clinical (unspecified phase)
0.6914 Remote Similarity NPD7859 Phase 2
0.6912 Remote Similarity NPD8525 Approved
0.6908 Remote Similarity NPD4343 Phase 1
0.6908 Remote Similarity NPD4344 Clinical (unspecified phase)
0.6907 Remote Similarity NPD4502 Phase 2
0.6906 Remote Similarity NPD8365 Clinical (unspecified phase)
0.6904 Remote Similarity NPD5164 Discontinued
0.6903 Remote Similarity NPD6569 Phase 2
0.6902 Remote Similarity NPD5482 Discontinued
0.6901 Remote Similarity NPD1856 Discontinued
0.6898 Remote Similarity NPD7781 Approved
0.6898 Remote Similarity NPD7780 Approved
0.6887 Remote Similarity NPD8370 Discontinued
0.6885 Remote Similarity NPD6530 Approved
0.6885 Remote Similarity NPD6531 Approved
0.6884 Remote Similarity NPD425 Approved
0.6884 Remote Similarity NPD424 Approved
0.688 Remote Similarity NPD7729 Clinical (unspecified phase)
0.6877 Remote Similarity NPD7921 Approved
0.6875 Remote Similarity NPD8431 Approved
0.6875 Remote Similarity NPD2383 Phase 1
0.6873 Remote Similarity NPD7169 Suspended
0.6872 Remote Similarity NPD802 Phase 2
0.6867 Remote Similarity NPD5426 Phase 3
0.6866 Remote Similarity NPD8467 Approved
0.6866 Remote Similarity NPD8465 Approved
0.6866 Remote Similarity NPD8466 Approved
0.686 Remote Similarity NPD4881 Clinical (unspecified phase)
0.6858 Remote Similarity NPD5912 Clinical (unspecified phase)
0.6858 Remote Similarity NPD5913 Phase 3
0.6851 Remote Similarity NPD2187 Approved
0.6851 Remote Similarity NPD2189 Approved
0.685 Remote Similarity NPD8100 Phase 3
0.6847 Remote Similarity NPD5596 Phase 2
0.6838 Remote Similarity NPD3003 Approved
0.6838 Remote Similarity NPD7958 Clinical (unspecified phase)
0.6838 Remote Similarity NPD7068 Approved
0.6838 Remote Similarity NPD7067 Approved
0.6838 Remote Similarity NPD4440 Clinical (unspecified phase)
0.6838 Remote Similarity NPD7957 Phase 1
0.6836 Remote Similarity NPD6243 Phase 3
0.6836 Remote Similarity NPD6244 Phase 3
0.6835 Remote Similarity NPD6220 Phase 3
0.6835 Remote Similarity NPD5066 Phase 2
0.6835 Remote Similarity NPD4131 Phase 3
0.6835 Remote Similarity NPD5067 Phase 2
0.6833 Remote Similarity NPD8464 Clinical (unspecified phase)
0.6831 Remote Similarity NPD6824 Clinical (unspecified phase)
0.6828 Remote Similarity NPD3404 Approved
0.682 Remote Similarity NPD6140 Clinical (unspecified phase)
0.6818 Remote Similarity NPD6242 Discontinued
0.6816 Remote Similarity NPD6352 Phase 2
0.6814 Remote Similarity NPD6281 Approved
0.6814 Remote Similarity NPD8063 Discontinued
0.6807 Remote Similarity NPD7594 Clinical (unspecified phase)
0.6807 Remote Similarity NPD8093 Discontinued
0.6802 Remote Similarity NPD6968 Phase 2
0.6802 Remote Similarity NPD6969 Phase 2
0.68 Remote Similarity NPD3006 Discontinued
0.6798 Remote Similarity NPD4551 Phase 2
0.6797 Remote Similarity NPD4558 Phase 2
0.6797 Remote Similarity NPD5644 Phase 1
0.6793 Remote Similarity NPD3014 Clinical (unspecified phase)
0.6793 Remote Similarity NPD3013 Phase 3
0.6793 Remote Similarity NPD8321 Discontinued
0.6789 Remote Similarity NPD8430 Approved
0.6786 Remote Similarity NPD3082 Discontinued
0.6781 Remote Similarity NPD6975 Discontinued
0.678 Remote Similarity NPD8284 Discontinued
0.6778 Remote Similarity NPD1322 Clinical (unspecified phase)
0.6777 Remote Similarity NPD537 Phase 2
0.6777 Remote Similarity NPD4555 Clinical (unspecified phase)
0.6777 Remote Similarity NPD534 Phase 2
0.6776 Remote Similarity NPD7586 Clinical (unspecified phase)
0.6773 Remote Similarity NPD2382 Approved
0.6773 Remote Similarity NPD2380 Approved
0.6773 Remote Similarity NPD2381 Approved
0.6767 Remote Similarity NPD4600 Approved
0.6767 Remote Similarity NPD4601 Approved
0.6766 Remote Similarity NPD5601 Phase 2
0.6766 Remote Similarity NPD7001 Phase 3
0.6766 Remote Similarity NPD8403 Phase 1
0.6765 Remote Similarity NPD8459 Approved
0.6765 Remote Similarity NPD8425 Approved
0.6765 Remote Similarity NPD8426 Approved
0.6765 Remote Similarity NPD949 Phase 1
0.6765 Remote Similarity NPD8460 Approved
0.6762 Remote Similarity NPD8356 Approved
0.6754 Remote Similarity NPD5018 Phase 3
0.6751 Remote Similarity NPD4437 Phase 3
0.675 Remote Similarity NPD4897 Phase 2
0.6749 Remote Similarity NPD6856 Discontinued
0.6748 Remote Similarity NPD7050 Clinical (unspecified phase)
0.6748 Remote Similarity NPD7051 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