Structure

Physi-Chem Properties

Molecular Weight:  705.39
Volume:  714.861
LogP:  2.972
LogD:  2.432
LogS:  -3.134
# Rotatable Bonds:  31
TPSA:  268.28
# H-Bond Aceptor:  15
# H-Bond Donor:  8
# Rings:  0
# Heavy Atoms:  15

MedChem Properties

QED Drug-Likeness Score:  0.043
Synthetic Accessibility Score:  5.008
Fsp3:  0.824
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  2
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.469
MDCK Permeability:  0.00012563643394969404
Pgp-inhibitor:  0.0
Pgp-substrate:  0.975
Human Intestinal Absorption (HIA):  0.994
20% Bioavailability (F20%):  0.852
30% Bioavailability (F30%):  0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.014
Plasma Protein Binding (PPB):  76.00572204589844%
Volume Distribution (VD):  0.533
Pgp-substrate:  10.801794052124023%

ADMET: Metabolism

CYP1A2-inhibitor:  0.002
CYP1A2-substrate:  0.004
CYP2C19-inhibitor:  0.013
CYP2C19-substrate:  0.037
CYP2C9-inhibitor:  0.001
CYP2C9-substrate:  0.965
CYP2D6-inhibitor:  0.11
CYP2D6-substrate:  0.049
CYP3A4-inhibitor:  0.016
CYP3A4-substrate:  0.002

ADMET: Excretion

Clearance (CL):  5.0
Half-life (T1/2):  0.889

ADMET: Toxicity

hERG Blockers:  0.004
Human Hepatotoxicity (H-HT):  0.7
Drug-inuced Liver Injury (DILI):  0.067
AMES Toxicity:  0.003
Rat Oral Acute Toxicity:  0.0
Maximum Recommended Daily Dose:  0.781
Skin Sensitization:  0.62
Carcinogencity:  0.403
Eye Corrosion:  0.958
Eye Irritation:  0.268
Respiratory Toxicity:  0.043

Download Data

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

  Natural Product: NPC320936

Natural Product ID:  NPC320936
Common Name*:   Fumonisin B2
IUPAC Name:   (2R)-2-[2-[(5R,6R,7S,9S,16R,18S,19S)-19-amino-6-[(3R)-3,4-dicarboxybutanoyl]oxy-16,18-dihydroxy-5,9-dimethylicosan-7-yl]oxy-2-oxoethyl]butanedioic acid
Synonyms:   Fumonisin B2
Standard InCHIKey:  UXDPXZQHTDAXOZ-STOIETHLSA-N
Standard InCHI:  InChI=1S/C34H59NO14/c1-5-6-12-21(3)32(49-31(43)18-24(34(46)47)16-29(40)41)27(48-30(42)17-23(33(44)45)15-28(38)39)14-20(2)11-9-7-8-10-13-25(36)19-26(37)22(4)35/h20-27,32,36-37H,5-19,35H2,1-4H3,(H,38,39)(H,40,41)(H,44,45)(H,46,47)/t20-,21+,22-,23+,24+,25+,26-,27-,32+/m0/s1
SMILES:  CCCC[C@H]([C@H]([C@@H](OC(=O)C[C@H](C(=O)O)CC(=O)O)C[C@H](CCCCCC[C@H](C[C@@H]([C@@H](N)C)O)O)C)OC(=O)C[C@H](C(=O)O)CC(=O)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1700939
PubChem CID:   2733489
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0000265] Carboxylic acids and derivatives
        • [CHEMONTID:0001792] Fumonisins

*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
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0040-4039(01)88611-1]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. DOI[10.1021/np058103o]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. DOI[10.1039/JR9620000040]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. DOI[10.1080/00021369.1966.10858561]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. DOI[10.1080/00021369.1972.10860562]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. DOI[10.1080/00021369.1985.10867263]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. mycelium n.a. PMID[10695672]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[12458767]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[12542363]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[15387655]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. sponge-derived n.a. PMID[15387655]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[15556711]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[15620260]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[17653510]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[17827758]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[20014861]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[20028011]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21176790]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21543515]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. mycelium n.a. PMID[21774474]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. latex n.a. PMID[21854017]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21854017]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[22921072]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[24684908]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[25044953]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[25062661]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[25293978]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[26040782]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[26132344]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[26414728]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[27245874]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[32159958]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[6073032]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. mycelium n.a. Database[Article]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
UNPD: Universal Natural Products Database [PMID: 23638153].
StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
MetaboLights: a metabolomics database [PMID: 27010336].
FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT443 Individual Protein Histone acetyltransferase GCN5 Homo sapiens Potency n.a. 39810.7 nM PMID[529678]
NPT66 Individual Protein Acetylcholinesterase Electrophorus electricus Inhibition = -8.37 % PMID[529679]
NPT888 Individual Protein 78 kDa glucose-regulated protein Homo sapiens Potency n.a. 44668.4 nM PMID[529678]
NPT67 Individual Protein Cholinesterase Equus caballus Inhibition = 15.12 % PMID[529679]

☑ 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 NPC320936 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
0.7582 Intermediate Similarity NPC477729
0.7292 Intermediate Similarity NPC160066
0.7222 Intermediate Similarity NPC227051
0.7174 Intermediate Similarity NPC470282
0.7143 Intermediate Similarity NPC83839
0.7111 Intermediate Similarity NPC145748
0.7111 Intermediate Similarity NPC95478
0.7111 Intermediate Similarity NPC155670
0.7033 Intermediate Similarity NPC253975
0.7033 Intermediate Similarity NPC192025
0.7033 Intermediate Similarity NPC125253
0.6932 Remote Similarity NPC473984
0.6813 Remote Similarity NPC47135
0.6765 Remote Similarity NPC227622
0.6742 Remote Similarity NPC475616
0.6735 Remote Similarity NPC470283
0.6702 Remote Similarity NPC477728
0.6667 Remote Similarity NPC86064
0.6629 Remote Similarity NPC474003
0.6593 Remote Similarity NPC314466
0.6556 Remote Similarity NPC315131
0.6556 Remote Similarity NPC478017
0.6556 Remote Similarity NPC315535
0.6552 Remote Similarity NPC474100
0.6552 Remote Similarity NPC475260
0.6552 Remote Similarity NPC51249
0.6552 Remote Similarity NPC475232
0.6552 Remote Similarity NPC43219
0.6552 Remote Similarity NPC473775
0.6552 Remote Similarity NPC473699
0.6548 Remote Similarity NPC286842
0.6531 Remote Similarity NPC270005
0.6531 Remote Similarity NPC208537
0.65 Remote Similarity NPC470363
0.6471 Remote Similarity NPC82315
0.646 Remote Similarity NPC477237
0.6456 Remote Similarity NPC190385
0.6452 Remote Similarity NPC477730
0.6444 Remote Similarity NPC316242
0.6404 Remote Similarity NPC228411
0.6392 Remote Similarity NPC470284
0.6355 Remote Similarity NPC137453
0.6353 Remote Similarity NPC469925
0.6348 Remote Similarity NPC477238
0.6341 Remote Similarity NPC17455
0.6329 Remote Similarity NPC8979
0.6316 Remote Similarity NPC314268
0.6316 Remote Similarity NPC477515
0.6316 Remote Similarity NPC473791
0.6316 Remote Similarity NPC476523
0.6316 Remote Similarity NPC313802
0.6316 Remote Similarity NPC67917
0.6304 Remote Similarity NPC474702
0.6265 Remote Similarity NPC106216
0.6265 Remote Similarity NPC88898
0.6262 Remote Similarity NPC471844
0.625 Remote Similarity NPC474403
0.6234 Remote Similarity NPC123814
0.6216 Remote Similarity NPC76660
0.6216 Remote Similarity NPC276995
0.6207 Remote Similarity NPC478256
0.6207 Remote Similarity NPC28526
0.619 Remote Similarity NPC316250
0.618 Remote Similarity NPC476248
0.6163 Remote Similarity NPC470110
0.6163 Remote Similarity NPC195165
0.6162 Remote Similarity NPC159369
0.6162 Remote Similarity NPC39290
0.6154 Remote Similarity NPC330017
0.6136 Remote Similarity NPC477200
0.6136 Remote Similarity NPC470268
0.6102 Remote Similarity NPC315783
0.6098 Remote Similarity NPC68974
0.6092 Remote Similarity NPC472579
0.6087 Remote Similarity NPC233108
0.6076 Remote Similarity NPC2801
0.6061 Remote Similarity NPC203170
0.6061 Remote Similarity NPC292345
0.6055 Remote Similarity NPC317534
0.6047 Remote Similarity NPC222327
0.6047 Remote Similarity NPC188231
0.6047 Remote Similarity NPC241949
0.6047 Remote Similarity NPC470109
0.6044 Remote Similarity NPC476324
0.6044 Remote Similarity NPC476130
0.6026 Remote Similarity NPC474322
0.6022 Remote Similarity NPC470014
0.6 Remote Similarity NPC308096
0.6 Remote Similarity NPC291228
0.6 Remote Similarity NPC208657
0.6 Remote Similarity NPC138435
0.5978 Remote Similarity NPC472594
0.5963 Remote Similarity NPC236644
0.596 Remote Similarity NPC314364
0.596 Remote Similarity NPC52533
0.5955 Remote Similarity NPC476696
0.5955 Remote Similarity NPC476695
0.5955 Remote Similarity NPC476694
0.5955 Remote Similarity NPC306973
0.593 Remote Similarity NPC470108
0.593 Remote Similarity NPC476330
0.5909 Remote Similarity NPC474299
0.5909 Remote Similarity NPC474298
0.5909 Remote Similarity NPC473985
0.5909 Remote Similarity NPC475808
0.5909 Remote Similarity NPC28348
0.5909 Remote Similarity NPC315531
0.5904 Remote Similarity NPC319131
0.59 Remote Similarity NPC322966
0.5893 Remote Similarity NPC477997
0.5889 Remote Similarity NPC185419
0.5889 Remote Similarity NPC184550
0.5889 Remote Similarity NPC141325
0.5888 Remote Similarity NPC42320
0.5888 Remote Similarity NPC188453
0.5882 Remote Similarity NPC235788
0.5875 Remote Similarity NPC469937
0.5875 Remote Similarity NPC53463
0.5875 Remote Similarity NPC320588
0.5875 Remote Similarity NPC23155
0.5872 Remote Similarity NPC74035
0.587 Remote Similarity NPC217725
0.587 Remote Similarity NPC477002
0.5862 Remote Similarity NPC209734
0.5859 Remote Similarity NPC476717
0.5859 Remote Similarity NPC258824
0.5856 Remote Similarity NPC70235
0.5854 Remote Similarity NPC322148
0.5851 Remote Similarity NPC191345
0.5851 Remote Similarity NPC252483
0.5849 Remote Similarity NPC220234
0.5843 Remote Similarity NPC211428
0.5843 Remote Similarity NPC476285
0.5843 Remote Similarity NPC476291
0.5841 Remote Similarity NPC34977
0.5841 Remote Similarity NPC246399
0.5833 Remote Similarity NPC302188
0.5833 Remote Similarity NPC116320
0.5833 Remote Similarity NPC211049
0.5833 Remote Similarity NPC119922
0.5818 Remote Similarity NPC475918
0.5816 Remote Similarity NPC151176
0.5816 Remote Similarity NPC475963
0.5816 Remote Similarity NPC3464
0.5814 Remote Similarity NPC314103
0.581 Remote Similarity NPC471843
0.58 Remote Similarity NPC51662
0.5795 Remote Similarity NPC477760
0.5795 Remote Similarity NPC477754
0.5795 Remote Similarity NPC206601
0.5795 Remote Similarity NPC477758
0.5795 Remote Similarity NPC477761
0.5795 Remote Similarity NPC477759
0.5789 Remote Similarity NPC22742
0.5789 Remote Similarity NPC294748
0.5789 Remote Similarity NPC85759
0.5789 Remote Similarity NPC318258
0.5789 Remote Similarity NPC261750
0.5789 Remote Similarity NPC158302
0.5789 Remote Similarity NPC477344
0.5789 Remote Similarity NPC146992
0.5789 Remote Similarity NPC477346
0.5789 Remote Similarity NPC1111
0.5784 Remote Similarity NPC65359
0.5784 Remote Similarity NPC470114
0.5784 Remote Similarity NPC476019
0.5783 Remote Similarity NPC179624
0.5778 Remote Similarity NPC33267
0.5778 Remote Similarity NPC114640
0.5778 Remote Similarity NPC126366
0.5778 Remote Similarity NPC169976
0.5778 Remote Similarity NPC170963
0.5778 Remote Similarity NPC324165
0.5772 Remote Similarity NPC477793
0.5772 Remote Similarity NPC329919
0.5765 Remote Similarity NPC469923
0.5761 Remote Similarity NPC472595
0.5758 Remote Similarity NPC475206
0.5758 Remote Similarity NPC476715
0.575 Remote Similarity NPC72722
0.5747 Remote Similarity NPC469926
0.5747 Remote Similarity NPC474402
0.5745 Remote Similarity NPC83108
0.5745 Remote Similarity NPC214030
0.5743 Remote Similarity NPC193386
0.5743 Remote Similarity NPC470009
0.573 Remote Similarity NPC50228
0.573 Remote Similarity NPC268922
0.573 Remote Similarity NPC224700
0.573 Remote Similarity NPC320663
0.573 Remote Similarity NPC97736
0.5729 Remote Similarity NPC207657
0.5728 Remote Similarity NPC472197
0.5726 Remote Similarity NPC6531
0.5714 Remote Similarity NPC121062
0.5714 Remote Similarity NPC96966
0.5714 Remote Similarity NPC15413
0.5714 Remote Similarity NPC29222
0.5714 Remote Similarity NPC474468
0.5702 Remote Similarity NPC314629

  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 NPC320936 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
0.7115 Intermediate Similarity NPD8087 Discontinued
0.6813 Remote Similarity NPD7345 Approved
0.6765 Remote Similarity NPD8139 Approved
0.6765 Remote Similarity NPD8086 Approved
0.6765 Remote Similarity NPD8084 Approved
0.6765 Remote Similarity NPD8085 Approved
0.6765 Remote Similarity NPD8083 Approved
0.6765 Remote Similarity NPD8138 Approved
0.6765 Remote Similarity NPD8082 Approved
0.6735 Remote Similarity NPD8394 Approved
0.6731 Remote Similarity NPD8393 Approved
0.6699 Remote Similarity NPD8275 Approved
0.6699 Remote Similarity NPD8276 Approved
0.6667 Remote Similarity NPD8307 Discontinued
0.6667 Remote Similarity NPD8140 Approved
0.6635 Remote Similarity NPD8081 Approved
0.6627 Remote Similarity NPD9421 Phase 1
0.6585 Remote Similarity NPD7909 Approved
0.6556 Remote Similarity NPD7917 Clinical (unspecified phase)
0.6556 Remote Similarity NPD7918 Clinical (unspecified phase)
0.6549 Remote Similarity NPD8346 Approved
0.6549 Remote Similarity NPD8345 Approved
0.6549 Remote Similarity NPD8347 Approved
0.6456 Remote Similarity NPD9023 Clinical (unspecified phase)
0.6392 Remote Similarity NPD4264 Clinical (unspecified phase)
0.6348 Remote Similarity NPD8444 Approved
0.6341 Remote Similarity NPD9676 Phase 3
0.6275 Remote Similarity NPD6428 Approved
0.625 Remote Similarity NPD6944 Clinical (unspecified phase)
0.6239 Remote Similarity NPD8305 Approved
0.6239 Remote Similarity NPD8306 Approved
0.6234 Remote Similarity NPD3215 Phase 1
0.6162 Remote Similarity NPD3716 Discontinued
0.6105 Remote Similarity NPD882 Phase 2
0.6105 Remote Similarity NPD883 Phase 2
0.6102 Remote Similarity NPD7830 Approved
0.6102 Remote Similarity NPD7829 Approved
0.6091 Remote Similarity NPD6941 Approved
0.6087 Remote Similarity NPD3160 Suspended
0.6068 Remote Similarity NPD8267 Approved
0.6068 Remote Similarity NPD8266 Approved
0.6068 Remote Similarity NPD8269 Approved
0.6068 Remote Similarity NPD8268 Approved
0.6067 Remote Similarity NPD6704 Discontinued
0.6061 Remote Similarity NPD618 Clinical (unspecified phase)
0.6 Remote Similarity NPD9454 Approved
0.6 Remote Similarity NPD1448 Clinical (unspecified phase)
0.5981 Remote Similarity NPD8301 Approved
0.5981 Remote Similarity NPD8300 Approved
0.5974 Remote Similarity NPD3214 Discontinued
0.5918 Remote Similarity NPD619 Phase 3
0.5905 Remote Similarity NPD881 Approved
0.5893 Remote Similarity NPD6421 Discontinued
0.5889 Remote Similarity NPD1147 Phase 2
0.5875 Remote Similarity NPD3730 Approved
0.5875 Remote Similarity NPD3728 Approved
0.587 Remote Similarity NPD11 Approved
0.587 Remote Similarity NPD376 Approved
0.587 Remote Similarity NPD2257 Approved
0.5862 Remote Similarity NPD8137 Clinical (unspecified phase)
0.5843 Remote Similarity NPD2696 Approved
0.5843 Remote Similarity NPD8277 Approved
0.5843 Remote Similarity NPD2697 Approved
0.5843 Remote Similarity NPD2694 Approved
0.5843 Remote Similarity NPD2695 Approved
0.5833 Remote Similarity NPD9656 Approved
0.5812 Remote Similarity NPD7641 Discontinued
0.5806 Remote Similarity NPD2689 Clinical (unspecified phase)
0.5773 Remote Similarity NPD7643 Phase 1
0.5761 Remote Similarity NPD632 Discontinued
0.573 Remote Similarity NPD8278 Approved
0.573 Remote Similarity NPD3724 Clinical (unspecified phase)
0.5728 Remote Similarity NPD7983 Approved
0.5714 Remote Similarity NPD3187 Discontinued
0.5699 Remote Similarity NPD1453 Phase 1
0.5698 Remote Similarity NPD1151 Approved
0.5684 Remote Similarity NPD3732 Approved
0.5682 Remote Similarity NPD2263 Discontinued
0.5682 Remote Similarity NPD375 Phase 2
0.5679 Remote Similarity NPD3729 Clinical (unspecified phase)
0.5673 Remote Similarity NPD1447 Phase 3
0.5673 Remote Similarity NPD1446 Phase 3
0.5667 Remote Similarity NPD8274 Clinical (unspecified phase)
0.5663 Remote Similarity NPD9439 Approved
0.5663 Remote Similarity NPD9438 Approved
0.5656 Remote Similarity NPD8341 Approved
0.5656 Remote Similarity NPD8340 Approved
0.5656 Remote Similarity NPD8299 Approved
0.5656 Remote Similarity NPD8342 Approved
0.5641 Remote Similarity NPD6940 Discontinued
0.5641 Remote Similarity NPD9018 Approved
0.5641 Remote Similarity NPD9017 Approved
0.5636 Remote Similarity NPD8045 Clinical (unspecified phase)
0.562 Remote Similarity NPD8080 Discontinued
0.5619 Remote Similarity NPD573 Clinical (unspecified phase)
0.561 Remote Similarity NPD8451 Approved
0.5607 Remote Similarity NPD3715 Approved
0.5607 Remote Similarity NPD8038 Phase 2
0.5607 Remote Similarity NPD3713 Approved
0.5607 Remote Similarity NPD3714 Approved
0.5604 Remote Similarity NPD7532 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