Structure

Physi-Chem Properties

Molecular Weight:  140.05
Volume:  139.533
LogP:  1.171
LogD:  1.507
LogS:  -1.182
# Rotatable Bonds:  3
TPSA:  39.44
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  1
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.582
Synthetic Accessibility Score:  1.963
Fsp3:  0.286
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.338
MDCK Permeability:  5.0350907258689404e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.004
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.004
30% Bioavailability (F30%):  0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.983
Plasma Protein Binding (PPB):  62.910335540771484%
Volume Distribution (VD):  1.927
Pgp-substrate:  62.61255645751953%

ADMET: Metabolism

CYP1A2-inhibitor:  0.9
CYP1A2-substrate:  0.111
CYP2C19-inhibitor:  0.492
CYP2C19-substrate:  0.314
CYP2C9-inhibitor:  0.032
CYP2C9-substrate:  0.112
CYP2D6-inhibitor:  0.011
CYP2D6-substrate:  0.313
CYP3A4-inhibitor:  0.01
CYP3A4-substrate:  0.324

ADMET: Excretion

Clearance (CL):  8.325
Half-life (T1/2):  0.901

ADMET: Toxicity

hERG Blockers:  0.239
Human Hepatotoxicity (H-HT):  0.135
Drug-inuced Liver Injury (DILI):  0.619
AMES Toxicity:  0.531
Rat Oral Acute Toxicity:  0.43
Maximum Recommended Daily Dose:  0.021
Skin Sensitization:  0.146
Carcinogencity:  0.687
Eye Corrosion:  0.834
Eye Irritation:  0.984
Respiratory Toxicity:  0.176

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

  Natural Product: NPC229387

Natural Product ID:  NPC229387
Common Name*:   Furan-2-Ylmethyl Acetate
IUPAC Name:   furan-2-ylmethyl acetate
Synonyms:  
Standard InCHIKey:  CKOYRRWBOKMNRG-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C7H8O3/c1-6(8)10-5-7-3-2-4-9-7/h2-4H,5H2,1H3
SMILES:  CC(=O)OCc1ccco1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1522321
PubChem CID:   12170
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0004144] Heteroaromatic compounds

*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
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. root n.a. PMID[11374978]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[15679317]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota roots purchased from Kiu Shun Trading Ltd., Vancouver, Canada 2000 PMID[16643021]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. root n.a. PMID[17997069]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. leaf n.a. PMID[18409045]
NPO29141 Panax ginseng Species Araliaceae Eukaryota flower buds n.a. n.a. PMID[19926279]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. root n.a. PMID[2092947]
NPO29141 Panax ginseng Species Araliaceae Eukaryota berry n.a. n.a. PMID[21216145]
NPO29141 Panax ginseng Species Araliaceae Eukaryota leaves n.a. n.a. PMID[24290061]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. PMID[24968750]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. PMID[25152999]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[25538068]
NPO29141 Panax ginseng Species Araliaceae Eukaryota stems-leaves n.a. n.a. PMID[26420067]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[27400088]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. stem n.a. PMID[27914541]
NPO29141 Panax ginseng Species Araliaceae Eukaryota Flower Buds n.a. n.a. PMID[28345906]
NPO1436 Houttuynia cordata Species Saururaceae Eukaryota n.a. n.a. n.a. PMID[29099182]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. PMID[32129622]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1436 Houttuynia cordata Species Saururaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. Database[MetaboLights]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1436 Houttuynia cordata Species Saururaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1436 Houttuynia cordata Species Saururaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1436 Houttuynia cordata Species Saururaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11438 Angelica gigas Species Apiaceae 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
NPT108 Individual Protein Estrogen receptor alpha Homo sapiens Potency n.a. 50118.7 nM PMID[464844]
NPT162 Individual Protein Heat shock protein beta-1 Homo sapiens Potency n.a. 61644.8 nM PubChem BioAssay data set
NPT94 Individual Protein Aldehyde dehydrogenase 1A1 Homo sapiens Potency = 22387.2 nM PMID[464844]
NPT99 Individual Protein Peroxisome proliferator-activated receptor gamma Homo sapiens Potency n.a. 50118.7 nM PMID[464844]
NPT2 Others Unspecified Potency n.a. 3466.5 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 12589.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 61644.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 27139.5 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 48966.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 27306 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 3889.5 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 76489.5 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 76958.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 34166.6 nM PubChem BioAssay data set

☑ 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 NPC229387 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
0.9167 High Similarity NPC311987
0.9029 High Similarity NPC217226
0.8796 High Similarity NPC209111
0.8785 High Similarity NPC219969
0.8725 High Similarity NPC146316
0.8621 High Similarity NPC272487
0.8571 High Similarity NPC156768
0.8421 Intermediate Similarity NPC328451
0.8362 Intermediate Similarity NPC244293
0.835 Intermediate Similarity NPC233791
0.8349 Intermediate Similarity NPC298087
0.8348 Intermediate Similarity NPC107482
0.8246 Intermediate Similarity NPC292036
0.8182 Intermediate Similarity NPC42471
0.8182 Intermediate Similarity NPC52035
0.8103 Intermediate Similarity NPC476014
0.8103 Intermediate Similarity NPC476031
0.7966 Intermediate Similarity NPC187547
0.7966 Intermediate Similarity NPC21831
0.7899 Intermediate Similarity NPC244862
0.7899 Intermediate Similarity NPC67345
0.7815 Intermediate Similarity NPC254958
0.7815 Intermediate Similarity NPC291619
0.7705 Intermediate Similarity NPC174915
0.7705 Intermediate Similarity NPC270807
0.7565 Intermediate Similarity NPC473356
0.7565 Intermediate Similarity NPC471521
0.7563 Intermediate Similarity NPC205523
0.7563 Intermediate Similarity NPC11821
0.75 Intermediate Similarity NPC474987
0.75 Intermediate Similarity NPC76844
0.7478 Intermediate Similarity NPC140688
0.7459 Intermediate Similarity NPC4898
0.7438 Intermediate Similarity NPC227660
0.7438 Intermediate Similarity NPC312525
0.7438 Intermediate Similarity NPC217180
0.7438 Intermediate Similarity NPC131801
0.7373 Intermediate Similarity NPC105249
0.7339 Intermediate Similarity NPC474136
0.7333 Intermediate Similarity NPC282973
0.7321 Intermediate Similarity NPC132725
0.7319 Intermediate Similarity NPC195920
0.7317 Intermediate Similarity NPC473969
0.7311 Intermediate Similarity NPC1811
0.7311 Intermediate Similarity NPC26157
0.7293 Intermediate Similarity NPC303217
0.728 Intermediate Similarity NPC289911
0.728 Intermediate Similarity NPC283284
0.7266 Intermediate Similarity NPC475864
0.7266 Intermediate Similarity NPC474830
0.7266 Intermediate Similarity NPC137570
0.7258 Intermediate Similarity NPC474817
0.7244 Intermediate Similarity NPC474829
0.7222 Intermediate Similarity NPC475818
0.7222 Intermediate Similarity NPC476351
0.719 Intermediate Similarity NPC252004
0.7176 Intermediate Similarity NPC475092
0.7174 Intermediate Similarity NPC110305
0.7174 Intermediate Similarity NPC22248
0.7174 Intermediate Similarity NPC27220
0.7167 Intermediate Similarity NPC22678
0.7165 Intermediate Similarity NPC188377
0.7165 Intermediate Similarity NPC118853
0.7165 Intermediate Similarity NPC65735
0.7163 Intermediate Similarity NPC474255
0.7163 Intermediate Similarity NPC471618
0.7163 Intermediate Similarity NPC474220
0.7155 Intermediate Similarity NPC17537
0.7153 Intermediate Similarity NPC248795
0.7132 Intermediate Similarity NPC107571
0.7132 Intermediate Similarity NPC471573
0.7132 Intermediate Similarity NPC184391
0.7132 Intermediate Similarity NPC473355
0.7132 Intermediate Similarity NPC471554
0.7132 Intermediate Similarity NPC471501
0.7122 Intermediate Similarity NPC307346
0.7122 Intermediate Similarity NPC218712
0.7122 Intermediate Similarity NPC267004
0.7122 Intermediate Similarity NPC261733
0.7113 Intermediate Similarity NPC475904
0.7113 Intermediate Similarity NPC474270
0.7111 Intermediate Similarity NPC215109
0.7111 Intermediate Similarity NPC170604
0.7109 Intermediate Similarity NPC471559
0.7109 Intermediate Similarity NPC75557
0.7109 Intermediate Similarity NPC71274
0.7097 Intermediate Similarity NPC206007
0.7087 Intermediate Similarity NPC69403
0.7087 Intermediate Similarity NPC291189
0.708 Intermediate Similarity NPC148374
0.7073 Intermediate Similarity NPC470860
0.7071 Intermediate Similarity NPC37488
0.7068 Intermediate Similarity NPC293253
0.7063 Intermediate Similarity NPC1848
0.7059 Intermediate Similarity NPC177331
0.7054 Intermediate Similarity NPC329922
0.7054 Intermediate Similarity NPC216810
0.7054 Intermediate Similarity NPC474260
0.7054 Intermediate Similarity NPC81912
0.7054 Intermediate Similarity NPC329694
0.704 Intermediate Similarity NPC137710
0.7016 Intermediate Similarity NPC144745
0.7016 Intermediate Similarity NPC208906
0.7015 Intermediate Similarity NPC288209
0.7 Intermediate Similarity NPC141059
0.6992 Remote Similarity NPC45358
0.6992 Remote Similarity NPC28054
0.6992 Remote Similarity NPC473982
0.6992 Remote Similarity NPC471817
0.6992 Remote Similarity NPC220540
0.6977 Remote Similarity NPC221798
0.6977 Remote Similarity NPC473885
0.6977 Remote Similarity NPC471074
0.6972 Remote Similarity NPC71821
0.6972 Remote Similarity NPC474317
0.6966 Remote Similarity NPC474219
0.6966 Remote Similarity NPC474378
0.6963 Remote Similarity NPC14650
0.6961 Remote Similarity NPC225539
0.6957 Remote Similarity NPC325857
0.6947 Remote Similarity NPC474279
0.6947 Remote Similarity NPC474438
0.6942 Remote Similarity NPC57879
0.6935 Remote Similarity NPC45536
0.6923 Remote Similarity NPC83301
0.6917 Remote Similarity NPC17681
0.6894 Remote Similarity NPC208389
0.6892 Remote Similarity NPC246841
0.6892 Remote Similarity NPC1408
0.6889 Remote Similarity NPC200718
0.6875 Remote Similarity NPC2063
0.687 Remote Similarity NPC476016
0.687 Remote Similarity NPC475236
0.6866 Remote Similarity NPC97740
0.6864 Remote Similarity NPC128730
0.6861 Remote Similarity NPC307401
0.6861 Remote Similarity NPC286130
0.6846 Remote Similarity NPC473368
0.6842 Remote Similarity NPC170546
0.6842 Remote Similarity NPC66246
0.6828 Remote Similarity NPC228842
0.6825 Remote Similarity NPC243704
0.6815 Remote Similarity NPC474426
0.6815 Remote Similarity NPC470859
0.6815 Remote Similarity NPC474425
0.6815 Remote Similarity NPC474407
0.6807 Remote Similarity NPC176971
0.6803 Remote Similarity NPC54626
0.68 Remote Similarity NPC79202
0.68 Remote Similarity NPC33320
0.68 Remote Similarity NPC59035
0.68 Remote Similarity NPC316062
0.6794 Remote Similarity NPC473626
0.6794 Remote Similarity NPC165556
0.6791 Remote Similarity NPC136340
0.6791 Remote Similarity NPC183348
0.6791 Remote Similarity NPC282230
0.6772 Remote Similarity NPC61779
0.6769 Remote Similarity NPC243269
0.6769 Remote Similarity NPC11799
0.6769 Remote Similarity NPC141252
0.6767 Remote Similarity NPC59502
0.6767 Remote Similarity NPC50583
0.6765 Remote Similarity NPC106247
0.6763 Remote Similarity NPC474615
0.6763 Remote Similarity NPC202260
0.6761 Remote Similarity NPC86935
0.6755 Remote Similarity NPC243509
0.675 Remote Similarity NPC157473
0.675 Remote Similarity NPC151530
0.6746 Remote Similarity NPC217423
0.6746 Remote Similarity NPC45104
0.6744 Remote Similarity NPC471549
0.6744 Remote Similarity NPC473379
0.6741 Remote Similarity NPC15083
0.6741 Remote Similarity NPC104854
0.6741 Remote Similarity NPC196979
0.6741 Remote Similarity NPC470976
0.6741 Remote Similarity NPC470977
0.6739 Remote Similarity NPC473268
0.6735 Remote Similarity NPC121615
0.6735 Remote Similarity NPC294511
0.6735 Remote Similarity NPC98028
0.6721 Remote Similarity NPC183648
0.6719 Remote Similarity NPC230951
0.6718 Remote Similarity NPC179354
0.6716 Remote Similarity NPC21460
0.6711 Remote Similarity NPC14499
0.6711 Remote Similarity NPC216092
0.6711 Remote Similarity NPC475039
0.6711 Remote Similarity NPC476035
0.6695 Remote Similarity NPC179686
0.6694 Remote Similarity NPC53953
0.6693 Remote Similarity NPC293424
0.6692 Remote Similarity NPC16922
0.669 Remote Similarity NPC254198
0.6667 Remote Similarity NPC23332
0.6667 Remote Similarity NPC477645
0.6667 Remote Similarity NPC261184
0.6667 Remote Similarity NPC97566

  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 NPC229387 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
0.8348 Intermediate Similarity NPD9092 Discovery
0.8182 Intermediate Similarity NPD1049 Clinical (unspecified phase)
0.6885 Remote Similarity NPD769 Approved
0.6829 Remote Similarity NPD9069 Phase 1
0.68 Remote Similarity NPD919 Approved
0.675 Remote Similarity NPD1358 Approved
0.6713 Remote Similarity NPD6799 Approved
0.6694 Remote Similarity NPD1241 Discontinued
0.6643 Remote Similarity NPD643 Clinical (unspecified phase)
0.6643 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6575 Remote Similarity NPD920 Approved
0.6573 Remote Similarity NPD3887 Approved
0.6562 Remote Similarity NPD9545 Approved
0.6552 Remote Similarity NPD642 Clinical (unspecified phase)
0.6549 Remote Similarity NPD9365 Approved
0.6529 Remote Similarity NPD3134 Approved
0.6525 Remote Similarity NPD2355 Clinical (unspecified phase)
0.6525 Remote Similarity NPD2353 Approved
0.6493 Remote Similarity NPD1019 Discontinued
0.6462 Remote Similarity NPD1778 Approved
0.6456 Remote Similarity NPD1212 Approved
0.6443 Remote Similarity NPD6599 Discontinued
0.6439 Remote Similarity NPD9717 Approved
0.6438 Remote Similarity NPD5401 Approved
0.6434 Remote Similarity NPD1243 Approved
0.6408 Remote Similarity NPD1471 Phase 3
0.6397 Remote Similarity NPD6832 Phase 2
0.6389 Remote Similarity NPD4628 Phase 3
0.6387 Remote Similarity NPD1247 Approved
0.6364 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6351 Remote Similarity NPD5403 Approved
0.6345 Remote Similarity NPD2354 Approved
0.6338 Remote Similarity NPD1551 Phase 2
0.6336 Remote Similarity NPD17 Approved
0.6335 Remote Similarity NPD6765 Approved
0.6335 Remote Similarity NPD6764 Approved
0.6324 Remote Similarity NPD9494 Approved
0.6319 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6316 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6311 Remote Similarity NPD9697 Approved
0.6309 Remote Similarity NPD957 Approved
0.6286 Remote Similarity NPD1933 Approved
0.6258 Remote Similarity NPD5537 Clinical (unspecified phase)
0.625 Remote Similarity NPD690 Clinical (unspecified phase)
0.625 Remote Similarity NPD5647 Approved
0.625 Remote Similarity NPD6801 Discontinued
0.6232 Remote Similarity NPD2598 Clinical (unspecified phase)
0.6198 Remote Similarity NPD291 Approved
0.6194 Remote Similarity NPD1608 Approved
0.6194 Remote Similarity NPD7075 Discontinued
0.6187 Remote Similarity NPD6798 Discontinued
0.6184 Remote Similarity NPD958 Approved
0.6182 Remote Similarity NPD6784 Approved
0.6182 Remote Similarity NPD6785 Approved
0.6176 Remote Similarity NPD1203 Approved
0.617 Remote Similarity NPD447 Suspended
0.617 Remote Similarity NPD1899 Clinical (unspecified phase)
0.617 Remote Similarity NPD6355 Discontinued
0.6169 Remote Similarity NPD3817 Phase 2
0.6164 Remote Similarity NPD1562 Clinical (unspecified phase)
0.6143 Remote Similarity NPD4062 Phase 3
0.6143 Remote Similarity NPD6233 Phase 2
0.6136 Remote Similarity NPD5585 Approved
0.6129 Remote Similarity NPD3882 Suspended
0.6111 Remote Similarity NPD2796 Approved
0.6103 Remote Similarity NPD3225 Approved
0.6099 Remote Similarity NPD3142 Approved
0.6099 Remote Similarity NPD3140 Approved
0.6074 Remote Similarity NPD3972 Approved
0.6069 Remote Similarity NPD2344 Approved
0.6065 Remote Similarity NPD5402 Approved
0.6063 Remote Similarity NPD2181 Clinical (unspecified phase)
0.6058 Remote Similarity NPD3267 Approved
0.6058 Remote Similarity NPD3266 Approved
0.6056 Remote Similarity NPD4340 Discontinued
0.6048 Remote Similarity NPD8434 Phase 2
0.6042 Remote Similarity NPD3748 Approved
0.6033 Remote Similarity NPD1238 Approved
0.6031 Remote Similarity NPD9493 Approved
0.6026 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6 Remote Similarity NPD3688 Clinical (unspecified phase)
0.6 Remote Similarity NPD3146 Approved
0.5988 Remote Similarity NPD2163 Approved
0.5986 Remote Similarity NPD4307 Phase 2
0.5985 Remote Similarity NPD5536 Phase 2
0.5985 Remote Similarity NPD1876 Approved
0.5984 Remote Similarity NPD2067 Discontinued
0.5984 Remote Similarity NPD556 Approved
0.5968 Remote Similarity NPD9501 Approved
0.5966 Remote Similarity NPD9296 Approved
0.596 Remote Similarity NPD5049 Phase 3
0.596 Remote Similarity NPD2186 Approved
0.5957 Remote Similarity NPD2313 Discontinued
0.5957 Remote Similarity NPD411 Approved
0.5957 Remote Similarity NPD6859 Clinical (unspecified phase)
0.5952 Remote Similarity NPD290 Approved
0.5948 Remote Similarity NPD9295 Approved
0.5942 Remote Similarity NPD987 Approved
0.5942 Remote Similarity NPD6362 Approved
0.594 Remote Similarity NPD1894 Discontinued
0.5931 Remote Similarity NPD2799 Discontinued
0.5926 Remote Similarity NPD3496 Discontinued
0.5918 Remote Similarity NPD2897 Discontinued
0.5918 Remote Similarity NPD1549 Phase 2
0.5912 Remote Similarity NPD4359 Approved
0.5906 Remote Similarity NPD2309 Approved
0.5906 Remote Similarity NPD2684 Approved
0.5901 Remote Similarity NPD3926 Phase 2
0.589 Remote Similarity NPD1501 Clinical (unspecified phase)
0.5887 Remote Similarity NPD7095 Approved
0.5882 Remote Similarity NPD422 Phase 1
0.5874 Remote Similarity NPD1240 Approved
0.5871 Remote Similarity NPD7411 Suspended
0.5864 Remote Similarity NPD7784 Clinical (unspecified phase)
0.5864 Remote Similarity NPD4575 Clinical (unspecified phase)
0.585 Remote Similarity NPD1550 Clinical (unspecified phase)
0.585 Remote Similarity NPD1552 Clinical (unspecified phase)
0.5846 Remote Similarity NPD5535 Approved
0.5845 Remote Similarity NPD1048 Approved
0.5845 Remote Similarity NPD3268 Approved
0.5843 Remote Similarity NPD6559 Discontinued
0.5839 Remote Similarity NPD3750 Approved
0.5839 Remote Similarity NPD1878 Clinical (unspecified phase)
0.5833 Remote Similarity NPD230 Phase 1
0.5828 Remote Similarity NPD6143 Clinical (unspecified phase)
0.5827 Remote Similarity NPD9265 Clinical (unspecified phase)
0.5827 Remote Similarity NPD2797 Approved
0.5827 Remote Similarity NPD9552 Approved
0.5822 Remote Similarity NPD4308 Phase 3
0.5822 Remote Similarity NPD7033 Discontinued
0.5811 Remote Similarity NPD4534 Discontinued
0.5811 Remote Similarity NPD5958 Discontinued
0.5796 Remote Similarity NPD1006 Clinical (unspecified phase)
0.5796 Remote Similarity NPD7819 Suspended
0.5793 Remote Similarity NPD1607 Approved
0.5793 Remote Similarity NPD6653 Approved
0.5793 Remote Similarity NPD7893 Clinical (unspecified phase)
0.5789 Remote Similarity NPD4378 Clinical (unspecified phase)
0.5786 Remote Similarity NPD3749 Approved
0.5786 Remote Similarity NPD2798 Approved
0.5781 Remote Similarity NPD2182 Approved
0.5778 Remote Similarity NPD5691 Approved
0.5769 Remote Similarity NPD6385 Approved
0.5769 Remote Similarity NPD6386 Approved
0.5764 Remote Similarity NPD4060 Phase 1
0.576 Remote Similarity NPD9261 Approved
0.5759 Remote Similarity NPD5616 Clinical (unspecified phase)
0.5752 Remote Similarity NPD6273 Approved
0.5746 Remote Similarity NPD1408 Clinical (unspecified phase)
0.5745 Remote Similarity NPD454 Approved
0.5743 Remote Similarity NPD2346 Discontinued
0.5743 Remote Similarity NPD5763 Approved
0.5743 Remote Similarity NPD5762 Approved
0.5742 Remote Similarity NPD3226 Approved
0.5741 Remote Similarity NPD6808 Phase 2
0.5734 Remote Similarity NPD3764 Approved
0.5734 Remote Similarity NPD1296 Phase 2
0.5732 Remote Similarity NPD6280 Approved
0.5732 Remote Similarity NPD6279 Approved
0.5725 Remote Similarity NPD7843 Approved
0.5725 Remote Similarity NPD1481 Phase 2
0.5714 Remote Similarity NPD1510 Phase 2
0.5714 Remote Similarity NPD3873 Phase 3
0.5714 Remote Similarity NPD3869 Phase 3
0.5714 Remote Similarity NPD164 Approved
0.5714 Remote Similarity NPD5494 Approved
0.5706 Remote Similarity NPD1880 Phase 3
0.5705 Remote Similarity NPD970 Clinical (unspecified phase)
0.5704 Remote Similarity NPD1008 Clinical (unspecified phase)
0.5704 Remote Similarity NPD7534 Approved
0.5704 Remote Similarity NPD7533 Approved
0.5686 Remote Similarity NPD4662 Approved
0.5686 Remote Similarity NPD4661 Approved
0.5683 Remote Similarity NPD4379 Clinical (unspecified phase)
0.5658 Remote Similarity NPD6652 Clinical (unspecified phase)
0.5658 Remote Similarity NPD7440 Discontinued
0.5652 Remote Similarity NPD1281 Approved
0.5652 Remote Similarity NPD1535 Discovery
0.5649 Remote Similarity NPD969 Suspended
0.5649 Remote Similarity NPD1609 Clinical (unspecified phase)
0.5649 Remote Similarity NPD1512 Approved
0.5646 Remote Similarity NPD743 Approved
0.5641 Remote Similarity NPD7458 Discontinued
0.5638 Remote Similarity NPD6002 Phase 3
0.5638 Remote Similarity NPD6003 Clinical (unspecified phase)
0.5638 Remote Similarity NPD6006 Clinical (unspecified phase)
0.5638 Remote Similarity NPD6005 Phase 3
0.5638 Remote Similarity NPD6004 Phase 3
0.5633 Remote Similarity NPD1934 Approved
0.5625 Remote Similarity NPD968 Approved
0.5625 Remote Similarity NPD5019 Clinical (unspecified phase)
0.5625 Remote Similarity NPD4868 Clinical (unspecified phase)
0.5616 Remote Similarity NPD4622 Approved
0.5616 Remote Similarity NPD4618 Approved
0.5614 Remote Similarity NPD1163 Approved
0.5608 Remote Similarity NPD2164 Clinical (unspecified phase)
0.5605 Remote Similarity NPD4972 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