Structure

Physi-Chem Properties

Molecular Weight:  244.07
Volume:  244.373
LogP:  2.431
LogD:  2.524
LogS:  -3.09
# Rotatable Bonds:  1
TPSA:  59.67
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.618
Synthetic Accessibility Score:  3.318
Fsp3:  0.214
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.729
MDCK Permeability:  2.3705901185167022e-05
Pgp-inhibitor:  0.006
Pgp-substrate:  0.066
Human Intestinal Absorption (HIA):  0.009
20% Bioavailability (F20%):  0.006
30% Bioavailability (F30%):  0.738

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.019
Plasma Protein Binding (PPB):  86.431396484375%
Volume Distribution (VD):  0.995
Pgp-substrate:  16.435461044311523%

ADMET: Metabolism

CYP1A2-inhibitor:  0.961
CYP1A2-substrate:  0.926
CYP2C19-inhibitor:  0.342
CYP2C19-substrate:  0.085
CYP2C9-inhibitor:  0.391
CYP2C9-substrate:  0.842
CYP2D6-inhibitor:  0.593
CYP2D6-substrate:  0.856
CYP3A4-inhibitor:  0.31
CYP3A4-substrate:  0.229

ADMET: Excretion

Clearance (CL):  14.148
Half-life (T1/2):  0.475

ADMET: Toxicity

hERG Blockers:  0.012
Human Hepatotoxicity (H-HT):  0.972
Drug-inuced Liver Injury (DILI):  0.949
AMES Toxicity:  0.395
Rat Oral Acute Toxicity:  0.794
Maximum Recommended Daily Dose:  0.507
Skin Sensitization:  0.518
Carcinogencity:  0.92
Eye Corrosion:  0.058
Eye Irritation:  0.583
Respiratory Toxicity:  0.964

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

  Natural Product: NPC163557

Natural Product ID:  NPC163557
Common Name*:   (S)-5-Hydroxy-8-Isopropenyl-8,9-Dihydro-Furo[2,3-H]Chromen-2-One
IUPAC Name:   (8S)-5-hydroxy-8-prop-1-en-2-yl-8,9-dihydrofuro[2,3-h]chromen-2-one
Synonyms:  
Standard InCHIKey:  ZKVAWHGWTAJAEK-NSHDSACASA-N
Standard InCHI:  InChI=1S/C14H12O4/c1-7(2)11-5-9-12(17-11)6-10(15)8-3-4-13(16)18-14(8)9/h3-4,6,11,15H,1,5H2,2H3/t11-/m0/s1
SMILES:  CC(=C)[C@@H]1Cc2c(O1)cc(c1c2oc(=O)cc1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL305510
PubChem CID:   44310181
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000145] Coumarins and derivatives
        • [CHEMONTID:0000358] Furanocoumarins
          • [CHEMONTID:0002568] Angular furanocoumarins

*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
NPO8511 Gentiana strictiflora Species Gentianaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0031-9422(00)84162-X]
NPO6026 Zanthoxylum chiloperone Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[16309303]
NPO616 Glinus oppositifolius Species Molluginaceae Eukaryota aerial parts n.a. n.a. PMID[19299148]
NPO4977 Streptomyces globisporus Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21250756]
NPO4130 Machilus zuihoensis Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12499 Psiadia anchusifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4977 Streptomyces globisporus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO19040 Takifugu rubripes Species Tetraodontidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12499 Psiadia anchusifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10659 Helminthosporium victoriae Species Massarinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO616 Glinus oppositifolius Species Molluginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11135 Sideritis perfoliata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12159 Jasione montana Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7104 Pilocarpus grandiflorus Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11293 Naja naja Species Elapidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6026 Zanthoxylum chiloperone Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10960 Machilus odoratissima Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6834 Jurinea maxima Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3053 Flavoparmelia caperata Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20534 Flueggea microcarpa Species Phyllanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12048 Streptomyces griseocarneus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO4130 Machilus zuihoensis Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5708 Streptomyces sulfonofaciens Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO9037 Ophiopholis aculeata Species Ophiactidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1273 Streptomyces tateyamensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO25050 Mycetia nutans Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8511 Gentiana strictiflora Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11465 Arachniodes mutica Species Dryopteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6426 0tonia grandiflora n.a. n.a. n.a. 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
NPT1224 Individual Protein Glyceraldehyde-3-phosphate dehydrogenase liver Homo sapiens IC50 = 190546.07 nM PMID[492404]

☑ 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 NPC163557 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
0.9764 High Similarity NPC194277
0.9538 High Similarity NPC33986
0.9535 High Similarity NPC31849
0.9462 High Similarity NPC326600
0.9462 High Similarity NPC253574
0.9462 High Similarity NPC98179
0.9462 High Similarity NPC50896
0.9462 High Similarity NPC204353
0.9444 High Similarity NPC188327
0.9444 High Similarity NPC234109
0.9375 High Similarity NPC168710
0.9365 High Similarity NPC244495
0.9365 High Similarity NPC93219
0.9318 High Similarity NPC26954
0.9318 High Similarity NPC38099
0.9313 High Similarity NPC62366
0.9297 High Similarity NPC185066
0.9297 High Similarity NPC199204
0.9248 High Similarity NPC294456
0.9248 High Similarity NPC212124
0.9248 High Similarity NPC281014
0.9248 High Similarity NPC184861
0.9248 High Similarity NPC225106
0.9219 High Similarity NPC243688
0.9179 High Similarity NPC279573
0.9179 High Similarity NPC151946
0.9173 High Similarity NPC188380
0.9173 High Similarity NPC78746
0.9173 High Similarity NPC224543
0.9167 High Similarity NPC213173
0.9167 High Similarity NPC55149
0.9167 High Similarity NPC224475
0.9167 High Similarity NPC180716
0.9167 High Similarity NPC307412
0.916 High Similarity NPC14248
0.9154 High Similarity NPC80170
0.9104 High Similarity NPC155963
0.9104 High Similarity NPC232246
0.9104 High Similarity NPC153818
0.9098 High Similarity NPC472525
0.9091 High Similarity NPC7526
0.9091 High Similarity NPC222036
0.907 High Similarity NPC121740
0.907 High Similarity NPC258567
0.907 High Similarity NPC224774
0.9055 High Similarity NPC472518
0.9048 High Similarity NPC187868
0.9048 High Similarity NPC52247
0.9044 High Similarity NPC152771
0.9044 High Similarity NPC195357
0.9037 High Similarity NPC211110
0.9008 High Similarity NPC32463
0.9 High Similarity NPC469453
0.8986 High Similarity NPC471824
0.8984 High Similarity NPC201667
0.8984 High Similarity NPC73413
0.8976 High Similarity NPC96286
0.8976 High Similarity NPC248429
0.8971 High Similarity NPC312881
0.8968 High Similarity NPC302107
0.8947 High Similarity NPC318400
0.8947 High Similarity NPC296624
0.8947 High Similarity NPC167111
0.8947 High Similarity NPC133956
0.8947 High Similarity NPC471910
0.8947 High Similarity NPC207002
0.8939 High Similarity NPC250727
0.8915 High Similarity NPC168259
0.8915 High Similarity NPC471828
0.8915 High Similarity NPC471827
0.8906 High Similarity NPC273772
0.8906 High Similarity NPC109675
0.8905 High Similarity NPC287286
0.8898 High Similarity NPC144418
0.8889 High Similarity NPC283331
0.8889 High Similarity NPC247553
0.8881 High Similarity NPC18804
0.8881 High Similarity NPC47163
0.8881 High Similarity NPC84894
0.8881 High Similarity NPC131950
0.8881 High Similarity NPC260265
0.8881 High Similarity NPC287182
0.8881 High Similarity NPC164269
0.8881 High Similarity NPC127888
0.8881 High Similarity NPC166672
0.8881 High Similarity NPC74655
0.8881 High Similarity NPC198381
0.8881 High Similarity NPC267412
0.8881 High Similarity NPC100986
0.8881 High Similarity NPC319859
0.8881 High Similarity NPC195343
0.8865 High Similarity NPC169510
0.8864 High Similarity NPC113098
0.8855 High Similarity NPC472519
0.8855 High Similarity NPC219923
0.8849 High Similarity NPC471763
0.8846 High Similarity NPC471826
0.8837 High Similarity NPC27671
0.8837 High Similarity NPC111347
0.8819 High Similarity NPC163200
0.8815 High Similarity NPC472424
0.8815 High Similarity NPC281241
0.8815 High Similarity NPC471909
0.8815 High Similarity NPC86892
0.8815 High Similarity NPC471625
0.8815 High Similarity NPC469675
0.881 High Similarity NPC281356
0.881 High Similarity NPC298796
0.8797 High Similarity NPC272650
0.8797 High Similarity NPC267336
0.8797 High Similarity NPC29734
0.8794 High Similarity NPC296377
0.8786 High Similarity NPC43716
0.8786 High Similarity NPC469701
0.8786 High Similarity NPC106126
0.8786 High Similarity NPC101255
0.8786 High Similarity NPC475719
0.8786 High Similarity NPC108994
0.8777 High Similarity NPC229916
0.8768 High Similarity NPC183642
0.8768 High Similarity NPC310370
0.876 High Similarity NPC154176
0.876 High Similarity NPC173350
0.876 High Similarity NPC290605
0.8759 High Similarity NPC221046
0.875 High Similarity NPC149320
0.875 High Similarity NPC128529
0.875 High Similarity NPC223616
0.875 High Similarity NPC160727
0.875 High Similarity NPC471630
0.875 High Similarity NPC55615
0.875 High Similarity NPC177281
0.875 High Similarity NPC283019
0.875 High Similarity NPC476455
0.8731 High Similarity NPC19157
0.873 High Similarity NPC152306
0.873 High Similarity NPC96705
0.873 High Similarity NPC265547
0.8686 High Similarity NPC14697
0.8686 High Similarity NPC131198
0.8682 High Similarity NPC257188
0.8682 High Similarity NPC13007
0.8672 High Similarity NPC235190
0.8672 High Similarity NPC180006
0.8667 High Similarity NPC241165
0.8667 High Similarity NPC205797
0.8667 High Similarity NPC1220
0.8667 High Similarity NPC291551
0.8667 High Similarity NPC469449
0.8667 High Similarity NPC141822
0.8667 High Similarity NPC2363
0.8667 High Similarity NPC142563
0.8667 High Similarity NPC469965
0.8657 High Similarity NPC129784
0.8657 High Similarity NPC37009
0.8657 High Similarity NPC207892
0.8657 High Similarity NPC228369
0.8657 High Similarity NPC66430
0.8657 High Similarity NPC476166
0.8657 High Similarity NPC268917
0.8657 High Similarity NPC206224
0.8657 High Similarity NPC129106
0.8657 High Similarity NPC236014
0.8657 High Similarity NPC164574
0.8657 High Similarity NPC12875
0.8657 High Similarity NPC118114
0.8657 High Similarity NPC196765
0.8657 High Similarity NPC150011
0.8657 High Similarity NPC17343
0.8657 High Similarity NPC280653
0.8657 High Similarity NPC300875
0.8652 High Similarity NPC85624
0.8652 High Similarity NPC295696
0.8652 High Similarity NPC71739
0.8647 High Similarity NPC474289
0.8633 High Similarity NPC138149
0.8626 High Similarity NPC202594
0.8626 High Similarity NPC232692
0.8623 High Similarity NPC47040
0.8623 High Similarity NPC37428
0.8623 High Similarity NPC13067
0.8623 High Similarity NPC332594
0.8623 High Similarity NPC144512
0.8623 High Similarity NPC35501
0.8623 High Similarity NPC137262
0.8623 High Similarity NPC278600
0.8615 High Similarity NPC315807
0.8603 High Similarity NPC115335
0.8603 High Similarity NPC97834
0.8603 High Similarity NPC223008
0.8603 High Similarity NPC198154
0.8603 High Similarity NPC92830
0.8603 High Similarity NPC296915
0.8603 High Similarity NPC225696
0.8593 High Similarity NPC175159
0.8593 High Similarity NPC13005
0.8582 High Similarity NPC27187
0.8582 High Similarity NPC470225
0.8571 High Similarity NPC93640
0.8571 High Similarity NPC128633

  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 NPC163557 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
0.9048 High Similarity NPD422 Phase 1
0.8667 High Similarity NPD5124 Phase 1
0.8667 High Similarity NPD5123 Clinical (unspecified phase)
0.8295 Intermediate Similarity NPD1548 Phase 1
0.8239 Intermediate Similarity NPD1652 Phase 2
0.8182 Intermediate Similarity NPD1610 Phase 2
0.8175 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.8095 Intermediate Similarity NPD920 Approved
0.8056 Intermediate Similarity NPD3750 Approved
0.8043 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.8041 Intermediate Similarity NPD1653 Approved
0.8029 Intermediate Similarity NPD4908 Phase 1
0.8029 Intermediate Similarity NPD1008 Clinical (unspecified phase)
0.7986 Intermediate Similarity NPD1243 Approved
0.7959 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7959 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7945 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7929 Intermediate Similarity NPD1613 Approved
0.7929 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7917 Intermediate Similarity NPD1549 Phase 2
0.7914 Intermediate Similarity NPD1296 Phase 2
0.7902 Intermediate Similarity NPD1551 Phase 2
0.7857 Intermediate Similarity NPD7075 Discontinued
0.7847 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7847 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7832 Intermediate Similarity NPD1510 Phase 2
0.7808 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7793 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7792 Intermediate Similarity NPD7768 Phase 2
0.7778 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.777 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7763 Intermediate Similarity NPD7411 Suspended
0.774 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7737 Intermediate Similarity NPD3225 Approved
0.7724 Intermediate Similarity NPD6002 Phase 3
0.7724 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7724 Intermediate Similarity NPD6004 Phase 3
0.7724 Intermediate Similarity NPD6005 Phase 3
0.7724 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7718 Intermediate Similarity NPD2534 Approved
0.7718 Intermediate Similarity NPD2532 Approved
0.7718 Intermediate Similarity NPD2533 Approved
0.7712 Intermediate Similarity NPD6801 Discontinued
0.7708 Intermediate Similarity NPD3748 Approved
0.7704 Intermediate Similarity NPD3496 Discontinued
0.7698 Intermediate Similarity NPD9697 Approved
0.7698 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7697 Intermediate Similarity NPD4380 Phase 2
0.7687 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7681 Intermediate Similarity NPD2797 Approved
0.7676 Intermediate Similarity NPD4060 Phase 1
0.7676 Intermediate Similarity NPD1240 Approved
0.7662 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7662 Intermediate Similarity NPD7819 Suspended
0.7655 Intermediate Similarity NPD2935 Discontinued
0.7655 Intermediate Similarity NPD2796 Approved
0.7647 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.763 Intermediate Similarity NPD4626 Approved
0.7619 Intermediate Similarity NPD2800 Approved
0.76 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7591 Intermediate Similarity NPD9717 Approved
0.7589 Intermediate Similarity NPD3027 Phase 3
0.7589 Intermediate Similarity NPD4625 Phase 3
0.7586 Intermediate Similarity NPD7033 Discontinued
0.758 Intermediate Similarity NPD919 Approved
0.7571 Intermediate Similarity NPD2861 Phase 2
0.7569 Intermediate Similarity NPD1607 Approved
0.7564 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7556 Intermediate Similarity NPD5691 Approved
0.7554 Intermediate Similarity NPD1203 Approved
0.7551 Intermediate Similarity NPD2424 Discontinued
0.7536 Intermediate Similarity NPD4749 Approved
0.7535 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7535 Intermediate Similarity NPD3268 Approved
0.7533 Intermediate Similarity NPD6799 Approved
0.7531 Intermediate Similarity NPD5844 Phase 1
0.7518 Intermediate Similarity NPD1091 Approved
0.7516 Intermediate Similarity NPD3749 Approved
0.7516 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6559 Discontinued
0.75 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7484 Intermediate Similarity NPD1934 Approved
0.7466 Intermediate Similarity NPD4308 Phase 3
0.7453 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.745 Intermediate Similarity NPD4628 Phase 3
0.7442 Intermediate Similarity NPD1358 Approved
0.7424 Intermediate Similarity NPD5535 Approved
0.7417 Intermediate Similarity NPD1511 Approved
0.7413 Intermediate Similarity NPD2313 Discontinued
0.7413 Intermediate Similarity NPD1699 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD1611 Approved
0.7386 Intermediate Similarity NPD5403 Approved
0.7379 Intermediate Similarity NPD6355 Discontinued
0.7379 Intermediate Similarity NPD230 Phase 1
0.7372 Intermediate Similarity NPD1778 Approved
0.7368 Intermediate Similarity NPD5401 Approved
0.7365 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7364 Intermediate Similarity NPD3134 Approved
0.7362 Intermediate Similarity NPD3818 Discontinued
0.7355 Intermediate Similarity NPD6599 Discontinued
0.7353 Intermediate Similarity NPD9545 Approved
0.7351 Intermediate Similarity NPD6666 Approved
0.7351 Intermediate Similarity NPD6667 Approved
0.7347 Intermediate Similarity NPD2799 Discontinued
0.7342 Intermediate Similarity NPD3882 Suspended
0.7329 Intermediate Similarity NPD7229 Phase 3
0.7323 Intermediate Similarity NPD846 Approved
0.7323 Intermediate Similarity NPD940 Approved
0.732 Intermediate Similarity NPD1512 Approved
0.7317 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.731 Intermediate Similarity NPD4140 Approved
0.7308 Intermediate Similarity NPD290 Approved
0.7305 Intermediate Similarity NPD3266 Approved
0.7305 Intermediate Similarity NPD3267 Approved
0.7303 Intermediate Similarity NPD7213 Phase 3
0.7303 Intermediate Similarity NPD7212 Phase 2
0.7292 Intermediate Similarity NPD6798 Discontinued
0.7278 Intermediate Similarity NPD3817 Phase 2
0.7278 Intermediate Similarity NPD5402 Approved
0.7273 Intermediate Similarity NPD6832 Phase 2
0.7266 Intermediate Similarity NPD1535 Discovery
0.7261 Intermediate Similarity NPD37 Approved
0.726 Intermediate Similarity NPD447 Suspended
0.726 Intermediate Similarity NPD4340 Discontinued
0.7259 Intermediate Similarity NPD6671 Approved
0.7255 Intermediate Similarity NPD7447 Phase 1
0.7254 Intermediate Similarity NPD1019 Discontinued
0.7254 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.725 Intermediate Similarity NPD6234 Discontinued
0.7248 Intermediate Similarity NPD5762 Approved
0.7248 Intermediate Similarity NPD5763 Approved
0.7239 Intermediate Similarity NPD1241 Discontinued
0.7234 Intermediate Similarity NPD6696 Suspended
0.7234 Intermediate Similarity NPD8651 Approved
0.7233 Intermediate Similarity NPD4965 Approved
0.7233 Intermediate Similarity NPD4966 Approved
0.7233 Intermediate Similarity NPD4967 Phase 2
0.7231 Intermediate Similarity NPD968 Approved
0.7229 Intermediate Similarity NPD5953 Discontinued
0.7215 Intermediate Similarity NPD2801 Approved
0.7215 Intermediate Similarity NPD1465 Phase 2
0.7214 Intermediate Similarity NPD1608 Approved
0.7214 Intermediate Similarity NPD1481 Phase 2
0.7212 Intermediate Similarity NPD7286 Phase 2
0.7208 Intermediate Similarity NPD7314 Clinical (unspecified phase)
0.7205 Intermediate Similarity NPD5494 Approved
0.7192 Intermediate Similarity NPD4307 Phase 2
0.7179 Intermediate Similarity NPD8158 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD3226 Approved
0.7172 Intermediate Similarity NPD3764 Approved
0.7172 Intermediate Similarity NPD411 Approved
0.717 Intermediate Similarity NPD4288 Approved
0.7162 Intermediate Similarity NPD7097 Phase 1
0.716 Intermediate Similarity NPD6959 Discontinued
0.716 Intermediate Similarity NPD1247 Approved
0.7152 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD7549 Discontinued
0.7143 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7124 Intermediate Similarity NPD5058 Phase 3
0.7123 Intermediate Similarity NPD6233 Phase 2
0.7121 Intermediate Similarity NPD2684 Approved
0.7117 Intermediate Similarity NPD6232 Discontinued
0.7117 Intermediate Similarity NPD5710 Approved
0.7117 Intermediate Similarity NPD5711 Approved
0.7114 Intermediate Similarity NPD5588 Approved
0.7101 Intermediate Similarity NPD1894 Discontinued
0.708 Intermediate Similarity NPD9493 Approved
0.707 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7067 Intermediate Similarity NPD6100 Approved
0.7067 Intermediate Similarity NPD4476 Approved
0.7067 Intermediate Similarity NPD6099 Approved
0.7067 Intermediate Similarity NPD4477 Approved
0.7055 Intermediate Similarity NPD7199 Phase 2
0.7055 Intermediate Similarity NPD1048 Approved
0.7047 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7047 Intermediate Similarity NPD4536 Approved
0.7047 Intermediate Similarity NPD4538 Approved
0.7042 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD7843 Approved
0.703 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD6166 Phase 2
0.703 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7024 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.702 Intermediate Similarity NPD2344 Approved
0.702 Intermediate Similarity NPD2346 Discontinued
0.702 Intermediate Similarity NPD7266 Discontinued
0.7014 Intermediate Similarity NPD3690 Phase 2
0.7014 Intermediate Similarity NPD3691 Phase 2
0.7007 Intermediate Similarity NPD7157 Approved
0.7006 Intermediate Similarity NPD7054 Approved
0.7 Intermediate Similarity NPD17 Approved
0.7 Intermediate Similarity NPD8455 Phase 2
0.6993 Remote Similarity NPD1283 Approved
0.6988 Remote Similarity NPD7473 Discontinued
0.6987 Remote Similarity NPD1940 Clinical (unspecified phase)
0.6987 Remote Similarity NPD6273 Approved
0.698 Remote Similarity NPD6651 Approved
0.698 Remote Similarity NPD6653 Approved

  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