Structure

Physi-Chem Properties

Molecular Weight:  176.05
Volume:  177.592
LogP:  1.76
LogD:  1.659
LogS:  -2.316
# Rotatable Bonds:  1
TPSA:  39.44
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.622
Synthetic Accessibility Score:  1.737
Fsp3:  0.1
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:  -4.625
MDCK Permeability:  2.298484650964383e-05
Pgp-inhibitor:  0.014
Pgp-substrate:  0.105
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.61
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.252
Plasma Protein Binding (PPB):  84.58246612548828%
Volume Distribution (VD):  0.804
Pgp-substrate:  15.743474960327148%

ADMET: Metabolism

CYP1A2-inhibitor:  0.985
CYP1A2-substrate:  0.957
CYP2C19-inhibitor:  0.548
CYP2C19-substrate:  0.187
CYP2C9-inhibitor:  0.055
CYP2C9-substrate:  0.891
CYP2D6-inhibitor:  0.727
CYP2D6-substrate:  0.906
CYP3A4-inhibitor:  0.442
CYP3A4-substrate:  0.427

ADMET: Excretion

Clearance (CL):  11.545
Half-life (T1/2):  0.676

ADMET: Toxicity

hERG Blockers:  0.234
Human Hepatotoxicity (H-HT):  0.351
Drug-inuced Liver Injury (DILI):  0.877
AMES Toxicity:  0.232
Rat Oral Acute Toxicity:  0.209
Maximum Recommended Daily Dose:  0.126
Skin Sensitization:  0.318
Carcinogencity:  0.888
Eye Corrosion:  0.583
Eye Irritation:  0.987
Respiratory Toxicity:  0.092

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

  Natural Product: NPC87563

Natural Product ID:  NPC87563
Common Name*:   6-Methoxycoumarin
IUPAC Name:   6-methoxychromen-2-one
Synonyms:   6-Methoxycoumarin
Standard InCHIKey:  VKVCJIMMVPXDQD-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C10H8O3/c1-12-8-3-4-9-7(6-8)2-5-10(11)13-9/h2-6H,1H3
SMILES:  COc1ccc2c(c1)ccc(=O)o2
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL496547
PubChem CID:   11240776
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000145] Coumarins and derivatives

*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]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[25538068]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[27400088]
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]
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[TCMID]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11438 Angelica gigas Species Apiaceae 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]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
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]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2921 Angelica acutiloba 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
NPT1897 Organism Oryzias latipes Oryzias latipes LC50 = 75.0 ppm PMID[486689]
NPT1897 Organism Oryzias latipes Oryzias latipes LC100 = 100.0 ppm PMID[486689]
NPT2 Others Unspecified Selectivity Index > 1.0 n.a. PMID[486689]
NPT176 Organism Artemia salina Artemia salina LC50 > 80.0 ppm PMID[486689]
NPT176 Organism Artemia salina Artemia salina LC100 > 80.0 ppm PMID[486689]
NPT593 Organism Bursaphelenchus xylophilus Bursaphelenchus xylophilus MED = 80.0 ug PMID[486689]
NPT2 Others Unspecified Selectivity Index = 0.94 n.a. PMID[486689]

☑ 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 NPC87563 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
0.9292 High Similarity NPC14177
0.9279 High Similarity NPC163398
0.9151 High Similarity NPC139891
0.8991 High Similarity NPC149545
0.887 High Similarity NPC98748
0.8814 High Similarity NPC248786
0.8772 High Similarity NPC128633
0.8718 High Similarity NPC322569
0.8644 High Similarity NPC476165
0.8624 High Similarity NPC128730
0.8624 High Similarity NPC288760
0.8624 High Similarity NPC227255
0.8621 High Similarity NPC265547
0.8618 High Similarity NPC240722
0.8618 High Similarity NPC244799
0.8584 High Similarity NPC266116
0.8584 High Similarity NPC280760
0.8571 High Similarity NPC141068
0.8547 High Similarity NPC298796
0.8547 High Similarity NPC281356
0.8545 High Similarity NPC176971
0.8537 High Similarity NPC123127
0.8537 High Similarity NPC27239
0.8532 High Similarity NPC109637
0.8525 High Similarity NPC142087
0.8525 High Similarity NPC95034
0.848 Intermediate Similarity NPC137669
0.8468 Intermediate Similarity NPC157473
0.8468 Intermediate Similarity NPC151530
0.8462 Intermediate Similarity NPC96705
0.8462 Intermediate Similarity NPC152306
0.8455 Intermediate Similarity NPC81261
0.8448 Intermediate Similarity NPC33717
0.844 Intermediate Similarity NPC179686
0.8426 Intermediate Similarity NPC107101
0.8421 Intermediate Similarity NPC474920
0.8417 Intermediate Similarity NPC473464
0.8417 Intermediate Similarity NPC476332
0.8413 Intermediate Similarity NPC233018
0.8413 Intermediate Similarity NPC241341
0.8413 Intermediate Similarity NPC36437
0.8403 Intermediate Similarity NPC163200
0.8403 Intermediate Similarity NPC180006
0.8403 Intermediate Similarity NPC307253
0.8403 Intermediate Similarity NPC235190
0.8364 Intermediate Similarity NPC283546
0.8349 Intermediate Similarity NPC307425
0.8349 Intermediate Similarity NPC84325
0.8348 Intermediate Similarity NPC303522
0.8348 Intermediate Similarity NPC90903
0.8346 Intermediate Similarity NPC309953
0.8333 Intermediate Similarity NPC329427
0.8333 Intermediate Similarity NPC317601
0.8333 Intermediate Similarity NPC245552
0.8319 Intermediate Similarity NPC31314
0.8319 Intermediate Similarity NPC193193
0.8305 Intermediate Similarity NPC124916
0.8293 Intermediate Similarity NPC329272
0.8291 Intermediate Similarity NPC290470
0.8291 Intermediate Similarity NPC154256
0.8288 Intermediate Similarity NPC473855
0.8264 Intermediate Similarity NPC96286
0.8264 Intermediate Similarity NPC248429
0.8264 Intermediate Similarity NPC302211
0.8246 Intermediate Similarity NPC473809
0.823 Intermediate Similarity NPC291837
0.8226 Intermediate Similarity NPC298884
0.822 Intermediate Similarity NPC183154
0.822 Intermediate Similarity NPC263754
0.8217 Intermediate Similarity NPC167517
0.8217 Intermediate Similarity NPC115861
0.8214 Intermediate Similarity NPC326447
0.8211 Intermediate Similarity NPC224657
0.8205 Intermediate Similarity NPC473718
0.8198 Intermediate Similarity NPC2518
0.8197 Intermediate Similarity NPC472518
0.8197 Intermediate Similarity NPC273772
0.8197 Intermediate Similarity NPC109675
0.8189 Intermediate Similarity NPC319969
0.8182 Intermediate Similarity NPC144418
0.8175 Intermediate Similarity NPC19242
0.8174 Intermediate Similarity NPC233238
0.8167 Intermediate Similarity NPC474874
0.8167 Intermediate Similarity NPC230951
0.816 Intermediate Similarity NPC474616
0.816 Intermediate Similarity NPC199204
0.8154 Intermediate Similarity NPC76336
0.8154 Intermediate Similarity NPC20796
0.8154 Intermediate Similarity NPC148835
0.8154 Intermediate Similarity NPC95162
0.8154 Intermediate Similarity NPC52086
0.8154 Intermediate Similarity NPC139548
0.8154 Intermediate Similarity NPC20511
0.8145 Intermediate Similarity NPC128321
0.8145 Intermediate Similarity NPC234109
0.8145 Intermediate Similarity NPC188327
0.8145 Intermediate Similarity NPC101894
0.8142 Intermediate Similarity NPC233320
0.814 Intermediate Similarity NPC240915
0.814 Intermediate Similarity NPC234865
0.813 Intermediate Similarity NPC147896
0.813 Intermediate Similarity NPC27671
0.813 Intermediate Similarity NPC201667
0.813 Intermediate Similarity NPC111347
0.813 Intermediate Similarity NPC73413
0.8125 Intermediate Similarity NPC473393
0.8115 Intermediate Similarity NPC257188
0.8115 Intermediate Similarity NPC13007
0.8103 Intermediate Similarity NPC199462
0.8095 Intermediate Similarity NPC168710
0.8092 Intermediate Similarity NPC43500
0.8092 Intermediate Similarity NPC270256
0.8092 Intermediate Similarity NPC164148
0.8092 Intermediate Similarity NPC13067
0.8087 Intermediate Similarity NPC88868
0.8087 Intermediate Similarity NPC231251
0.8087 Intermediate Similarity NPC25067
0.8083 Intermediate Similarity NPC234956
0.8083 Intermediate Similarity NPC37858
0.808 Intermediate Similarity NPC474670
0.8077 Intermediate Similarity NPC286843
0.8077 Intermediate Similarity NPC82271
0.8077 Intermediate Similarity NPC126682
0.8073 Intermediate Similarity NPC175298
0.807 Intermediate Similarity NPC241549
0.8067 Intermediate Similarity NPC240664
0.8067 Intermediate Similarity NPC45104
0.8065 Intermediate Similarity NPC471827
0.8065 Intermediate Similarity NPC471828
0.8062 Intermediate Similarity NPC7163
0.8053 Intermediate Similarity NPC30416
0.8051 Intermediate Similarity NPC301321
0.8049 Intermediate Similarity NPC315807
0.8049 Intermediate Similarity NPC290605
0.8049 Intermediate Similarity NPC154176
0.8049 Intermediate Similarity NPC173350
0.8047 Intermediate Similarity NPC137949
0.8036 Intermediate Similarity NPC93831
0.8033 Intermediate Similarity NPC52247
0.8031 Intermediate Similarity NPC80170
0.8018 Intermediate Similarity NPC94343
0.8017 Intermediate Similarity NPC247553
0.8016 Intermediate Similarity NPC185066
0.8016 Intermediate Similarity NPC176590
0.8 Intermediate Similarity NPC73071
0.8 Intermediate Similarity NPC283616
0.8 Intermediate Similarity NPC277460
0.8 Intermediate Similarity NPC161856
0.8 Intermediate Similarity NPC291119
0.8 Intermediate Similarity NPC471826
0.8 Intermediate Similarity NPC281169
0.8 Intermediate Similarity NPC259554
0.8 Intermediate Similarity NPC51087
0.7984 Intermediate Similarity NPC472524
0.7984 Intermediate Similarity NPC190086
0.7984 Intermediate Similarity NPC276962
0.7984 Intermediate Similarity NPC277021
0.7984 Intermediate Similarity NPC474237
0.7984 Intermediate Similarity NPC472522
0.797 Intermediate Similarity NPC300611
0.7966 Intermediate Similarity NPC294941
0.7966 Intermediate Similarity NPC41851
0.7965 Intermediate Similarity NPC238115
0.7951 Intermediate Similarity NPC267064
0.7951 Intermediate Similarity NPC302107
0.7951 Intermediate Similarity NPC319378
0.7951 Intermediate Similarity NPC212559
0.7937 Intermediate Similarity NPC224774
0.7937 Intermediate Similarity NPC474821
0.7937 Intermediate Similarity NPC121740
0.7937 Intermediate Similarity NPC71525
0.7937 Intermediate Similarity NPC156298
0.7937 Intermediate Similarity NPC258567
0.7934 Intermediate Similarity NPC471449
0.7928 Intermediate Similarity NPC13755
0.7923 Intermediate Similarity NPC92830
0.7923 Intermediate Similarity NPC474600
0.792 Intermediate Similarity NPC170749
0.792 Intermediate Similarity NPC93219
0.792 Intermediate Similarity NPC165556
0.792 Intermediate Similarity NPC244495
0.7917 Intermediate Similarity NPC471503
0.7917 Intermediate Similarity NPC217423
0.7917 Intermediate Similarity NPC471498
0.7909 Intermediate Similarity NPC95755
0.7907 Intermediate Similarity NPC123954
0.7907 Intermediate Similarity NPC19157
0.7907 Intermediate Similarity NPC472882
0.7907 Intermediate Similarity NPC194277
0.7899 Intermediate Similarity NPC188907
0.7886 Intermediate Similarity NPC187868
0.7874 Intermediate Similarity NPC472519
0.7874 Intermediate Similarity NPC201419
0.7874 Intermediate Similarity NPC469453
0.7869 Intermediate Similarity NPC471504
0.7869 Intermediate Similarity NPC473290
0.7869 Intermediate Similarity NPC2058
0.7863 Intermediate Similarity NPC275627
0.7857 Intermediate Similarity NPC474632
0.7852 Intermediate Similarity NPC138212

  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 NPC87563 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
0.9151 High Similarity NPD9697 Approved
0.8718 High Similarity NPD3496 Discontinued
0.8487 Intermediate Similarity NPD1611 Approved
0.8214 Intermediate Similarity NPD3134 Approved
0.8142 Intermediate Similarity NPD1358 Approved
0.8083 Intermediate Similarity NPD5691 Approved
0.8083 Intermediate Similarity NPD5585 Approved
0.8051 Intermediate Similarity NPD6671 Approved
0.8033 Intermediate Similarity NPD422 Phase 1
0.8017 Intermediate Similarity NPD1778 Approved
0.7984 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7949 Intermediate Similarity NPD5535 Approved
0.7937 Intermediate Similarity NPD2237 Approved
0.7895 Intermediate Similarity NPD968 Approved
0.7881 Intermediate Similarity NPD1241 Discontinued
0.7869 Intermediate Similarity NPD4626 Approved
0.7857 Intermediate Similarity NPD1019 Discontinued
0.7823 Intermediate Similarity NPD9717 Approved
0.7778 Intermediate Similarity NPD3267 Approved
0.7778 Intermediate Similarity NPD3266 Approved
0.7778 Intermediate Similarity NPD2797 Approved
0.7769 Intermediate Similarity NPD7644 Approved
0.776 Intermediate Similarity NPD4359 Approved
0.7734 Intermediate Similarity NPD6832 Phase 2
0.7724 Intermediate Similarity NPD17 Approved
0.771 Intermediate Similarity NPD447 Suspended
0.7698 Intermediate Similarity NPD3225 Approved
0.7672 Intermediate Similarity NPD290 Approved
0.7638 Intermediate Similarity NPD1203 Approved
0.7634 Intermediate Similarity NPD4307 Phase 2
0.7615 Intermediate Similarity NPD411 Approved
0.7597 Intermediate Similarity NPD1008 Clinical (unspecified phase)
0.754 Intermediate Similarity NPD1608 Approved
0.7481 Intermediate Similarity NPD2313 Discontinued
0.7481 Intermediate Similarity NPD2935 Discontinued
0.7481 Intermediate Similarity NPD3268 Approved
0.748 Intermediate Similarity NPD5536 Phase 2
0.746 Intermediate Similarity NPD1535 Discovery
0.746 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD4308 Phase 3
0.7402 Intermediate Similarity NPD1481 Phase 2
0.7394 Intermediate Similarity NPD1653 Approved
0.7368 Intermediate Similarity NPD4060 Phase 1
0.7348 Intermediate Similarity NPD1296 Phase 2
0.7323 Intermediate Similarity NPD1281 Approved
0.7317 Intermediate Similarity NPD709 Approved
0.7313 Intermediate Similarity NPD1933 Approved
0.7311 Intermediate Similarity NPD2684 Approved
0.7299 Intermediate Similarity NPD2346 Discontinued
0.7293 Intermediate Similarity NPD4870 Approved
0.728 Intermediate Similarity NPD1182 Approved
0.728 Intermediate Similarity NPD1894 Discontinued
0.7258 Intermediate Similarity NPD9493 Approved
0.7252 Intermediate Similarity NPD2861 Phase 2
0.7239 Intermediate Similarity NPD4140 Approved
0.7226 Intermediate Similarity NPD6032 Approved
0.7194 Intermediate Similarity NPD1652 Phase 2
0.7177 Intermediate Similarity NPD2557 Approved
0.7176 Intermediate Similarity NPD2798 Approved
0.7174 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7165 Intermediate Similarity NPD2423 Clinical (unspecified phase)
0.7164 Intermediate Similarity NPD6233 Phase 2
0.7164 Intermediate Similarity NPD8032 Phase 2
0.7156 Intermediate Similarity NPD1282 Approved
0.7155 Intermediate Similarity NPD289 Clinical (unspecified phase)
0.7154 Intermediate Similarity NPD1283 Approved
0.7154 Intermediate Similarity NPD5283 Phase 1
0.7154 Intermediate Similarity NPD1398 Phase 1
0.7153 Intermediate Similarity NPD2799 Discontinued
0.7153 Intermediate Similarity NPD3748 Approved
0.7143 Intermediate Similarity NPD1548 Phase 1
0.7143 Intermediate Similarity NPD7095 Approved
0.7131 Intermediate Similarity NPD228 Approved
0.7101 Intermediate Similarity NPD1551 Phase 2
0.709 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.709 Intermediate Similarity NPD6798 Discontinued
0.709 Intermediate Similarity NPD7985 Registered
0.7087 Intermediate Similarity NPD3444 Approved
0.7087 Intermediate Similarity NPD1651 Approved
0.7087 Intermediate Similarity NPD6382 Discontinued
0.7087 Intermediate Similarity NPD3443 Approved
0.7087 Intermediate Similarity NPD3445 Approved
0.7077 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD7843 Approved
0.7073 Intermediate Similarity NPD821 Approved
0.7071 Intermediate Similarity NPD1243 Approved
0.7063 Intermediate Similarity NPD1578 Phase 2
0.7059 Intermediate Similarity NPD4622 Approved
0.7059 Intermediate Similarity NPD5124 Phase 1
0.7059 Intermediate Similarity NPD9694 Discovery
0.7059 Intermediate Similarity NPD4618 Approved
0.7059 Intermediate Similarity NPD6355 Discontinued
0.7059 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7054 Intermediate Similarity NPD1091 Approved
0.705 Intermediate Similarity NPD5762 Approved
0.705 Intermediate Similarity NPD5763 Approved
0.704 Intermediate Similarity NPD7157 Approved
0.7027 Intermediate Similarity NPD9295 Approved
0.7023 Intermediate Similarity NPD6696 Suspended
0.7021 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7016 Intermediate Similarity NPD592 Approved
0.7016 Intermediate Similarity NPD594 Approved
0.7014 Intermediate Similarity NPD7314 Clinical (unspecified phase)
0.7014 Intermediate Similarity NPD1940 Clinical (unspecified phase)
0.7008 Intermediate Similarity NPD9545 Approved
0.7007 Intermediate Similarity NPD6653 Approved
0.7 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD2231 Phase 2
0.7 Intermediate Similarity NPD1840 Phase 2
0.7 Intermediate Similarity NPD2235 Phase 2
0.6992 Remote Similarity NPD1139 Approved
0.6992 Remote Similarity NPD1137 Approved
0.6986 Remote Similarity NPD3226 Approved
0.6985 Remote Similarity NPD2979 Phase 3
0.6984 Remote Similarity NPD7340 Approved
0.698 Remote Similarity NPD5402 Approved
0.6978 Remote Similarity NPD2796 Approved
0.6977 Remote Similarity NPD3847 Discontinued
0.697 Remote Similarity NPD987 Approved
0.6967 Remote Similarity NPD5451 Approved
0.6966 Remote Similarity NPD920 Approved
0.6963 Remote Similarity NPD1048 Approved
0.6963 Remote Similarity NPD1699 Clinical (unspecified phase)
0.6957 Remote Similarity NPD5689 Approved
0.6957 Remote Similarity NPD5688 Approved
0.6953 Remote Similarity NPD3049 Approved
0.695 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6947 Remote Similarity NPD5327 Phase 3
0.6947 Remote Similarity NPD4749 Approved
0.6944 Remote Similarity NPD642 Clinical (unspecified phase)
0.694 Remote Similarity NPD2614 Approved
0.6935 Remote Similarity NPD1138 Approved
0.6934 Remote Similarity NPD4340 Discontinued
0.6923 Remote Similarity NPD1610 Phase 2
0.6923 Remote Similarity NPD1238 Approved
0.6923 Remote Similarity NPD643 Clinical (unspecified phase)
0.6906 Remote Similarity NPD7033 Discontinued
0.6903 Remote Similarity NPD9365 Approved
0.6901 Remote Similarity NPD3750 Approved
0.6899 Remote Similarity NPD2554 Approved
0.6899 Remote Similarity NPD2107 Clinical (unspecified phase)
0.6899 Remote Similarity NPD2556 Approved
0.6897 Remote Similarity NPD6273 Approved
0.6897 Remote Similarity NPD2675 Approved
0.6897 Remote Similarity NPD2676 Approved
0.6894 Remote Similarity NPD1876 Approved
0.6891 Remote Similarity NPD9261 Approved
0.6889 Remote Similarity NPD5163 Phase 2
0.6884 Remote Similarity NPD2653 Approved
0.6875 Remote Similarity NPD2486 Discontinued
0.687 Remote Similarity NPD2230 Approved
0.687 Remote Similarity NPD1244 Clinical (unspecified phase)
0.687 Remote Similarity NPD2233 Approved
0.687 Remote Similarity NPD3972 Approved
0.687 Remote Similarity NPD2232 Approved
0.6866 Remote Similarity NPD1712 Approved
0.6857 Remote Similarity NPD4476 Approved
0.6857 Remote Similarity NPD4477 Approved
0.685 Remote Similarity NPD3596 Phase 2
0.6846 Remote Similarity NPD6844 Discontinued
0.6846 Remote Similarity NPD3447 Discontinued
0.6842 Remote Similarity NPD4098 Discontinued
0.6842 Remote Similarity NPD6362 Approved
0.6838 Remote Similarity NPD3374 Clinical (unspecified phase)
0.6835 Remote Similarity NPD7097 Phase 1
0.6818 Remote Similarity NPD1421 Approved
0.6818 Remote Similarity NPD1420 Approved
0.6818 Remote Similarity NPD3600 Clinical (unspecified phase)
0.6815 Remote Similarity NPD600 Approved
0.6815 Remote Similarity NPD596 Approved
0.6815 Remote Similarity NPD1529 Clinical (unspecified phase)
0.6812 Remote Similarity NPD1184 Approved
0.681 Remote Similarity NPD844 Approved
0.6809 Remote Similarity NPD6800 Clinical (unspecified phase)
0.6803 Remote Similarity NPD2370 Clinical (unspecified phase)
0.68 Remote Similarity NPD769 Approved
0.6794 Remote Similarity NPD3705 Approved
0.6794 Remote Similarity NPD776 Approved
0.6791 Remote Similarity NPD6584 Phase 3
0.6788 Remote Similarity NPD4062 Phase 3
0.6783 Remote Similarity NPD4628 Phase 3
0.6783 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6772 Remote Similarity NPD6387 Discontinued
0.6767 Remote Similarity NPD2922 Phase 1
0.6765 Remote Similarity NPD5746 Approved
0.6765 Remote Similarity NPD4625 Phase 3
0.6761 Remote Similarity NPD2424 Discontinued
0.6761 Remote Similarity NPD2897 Discontinued
0.6759 Remote Similarity NPD6799 Approved
0.6759 Remote Similarity NPD7837 Clinical (unspecified phase)
0.6757 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6755 Remote Similarity NPD3817 Phase 2
0.6752 Remote Similarity NPD288 Approved
0.6744 Remote Similarity NPD6580 Approved
0.6744 Remote Similarity NPD6581 Approved
0.6741 Remote Similarity NPD1530 Clinical (unspecified phase)
0.6741 Remote Similarity NPD454 Approved
0.6741 Remote Similarity NPD9494 Approved
0.6739 Remote Similarity NPD1613 Approved
0.6739 Remote Similarity NPD3142 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