Structure

Physi-Chem Properties

Molecular Weight:  134.04
Volume:  136.846
LogP:  1.627
LogD:  1.769
LogS:  -1.986
# Rotatable Bonds:  0
TPSA:  26.3
# H-Bond Aceptor:  2
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.501
Synthetic Accessibility Score:  1.879
Fsp3:  0.125
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:  -4.421
MDCK Permeability:  3.761439802474342e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.528

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.634
Plasma Protein Binding (PPB):  82.5340805053711%
Volume Distribution (VD):  2.203
Pgp-substrate:  15.29952621459961%

ADMET: Metabolism

CYP1A2-inhibitor:  0.963
CYP1A2-substrate:  0.455
CYP2C19-inhibitor:  0.793
CYP2C19-substrate:  0.123
CYP2C9-inhibitor:  0.15
CYP2C9-substrate:  0.387
CYP2D6-inhibitor:  0.087
CYP2D6-substrate:  0.526
CYP3A4-inhibitor:  0.023
CYP3A4-substrate:  0.194

ADMET: Excretion

Clearance (CL):  11.621
Half-life (T1/2):  0.8

ADMET: Toxicity

hERG Blockers:  0.047
Human Hepatotoxicity (H-HT):  0.062
Drug-inuced Liver Injury (DILI):  0.583
AMES Toxicity:  0.197
Rat Oral Acute Toxicity:  0.049
Maximum Recommended Daily Dose:  0.012
Skin Sensitization:  0.316
Carcinogencity:  0.665
Eye Corrosion:  0.244
Eye Irritation:  0.987
Respiratory Toxicity:  0.042

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

  Natural Product: NPC89886

Natural Product ID:  NPC89886
Common Name*:   Phthalide
IUPAC Name:   3H-2-benzofuran-1-one
Synonyms:  
Standard InCHIKey:  WNZQDUSMALZDQF-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C8H6O2/c9-8-7-4-2-1-3-6(7)5-10-8/h1-4H,5H2
SMILES:  c1ccc2c(c1)COC2=O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2391738
PubChem CID:   6885
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0004191] Isocoumarans
        • [CHEMONTID:0003409] Isobenzofuranones
          • [CHEMONTID:0001873] Phthalides

*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]
NPO20902 Atractylodes macrocephala Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[17432574]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. root n.a. PMID[17997069]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. rhizome n.a. PMID[18787781]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[21302967]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[25538068]
NPO18951 Ligusticum sinense Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[26521454]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[27228227]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[27400088]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[9544564]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20902 Atractylodes macrocephala Species Asteraceae 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]
NPO22033 Cnidium officinale Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18951 Ligusticum sinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18951 Ligusticum sinense 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]
NPO22033 Cnidium officinale Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20902 Atractylodes macrocephala Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20902 Atractylodes macrocephala Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18951 Ligusticum sinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16087 Atractylodes lancea Species Asteraceae 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]
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]
NPO18951 Ligusticum sinense 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]
NPO22033 Cnidium officinale Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20902 Atractylodes macrocephala Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20902 Atractylodes macrocephala Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
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]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18951 Ligusticum sinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16087 Atractylodes lancea Species Asteraceae 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
NPT582 Individual Protein Monoamine oxidase B Homo sapiens IC50 = 28600.0 nM PMID[537006]
NPT261 Individual Protein Monoamine oxidase A Homo sapiens IC50 = 44900.0 nM PMID[537006]
NPT2 Others Unspecified Ratio IC50 = 1.6 n.a. PMID[537006]

☑ 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 NPC89886 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
0.9688 High Similarity NPC45613
0.95 High Similarity NPC83628
0.95 High Similarity NPC265407
0.93 High Similarity NPC119271
0.93 High Similarity NPC37622
0.93 High Similarity NPC30594
0.9208 High Similarity NPC56493
0.9192 High Similarity NPC60679
0.9118 High Similarity NPC10251
0.9118 High Similarity NPC17417
0.91 High Similarity NPC31786
0.9072 High Similarity NPC276775
0.9072 High Similarity NPC92754
0.9072 High Similarity NPC249912
0.9048 High Similarity NPC237366
0.9048 High Similarity NPC307651
0.9029 High Similarity NPC93084
0.9029 High Similarity NPC196246
0.9029 High Similarity NPC214067
0.9029 High Similarity NPC251854
0.9029 High Similarity NPC174099
0.899 High Similarity NPC42211
0.898 High Similarity NPC225060
0.898 High Similarity NPC35448
0.898 High Similarity NPC78701
0.8942 High Similarity NPC1082
0.8942 High Similarity NPC260818
0.8942 High Similarity NPC305912
0.8911 High Similarity NPC114594
0.8889 High Similarity NPC118343
0.8889 High Similarity NPC146351
0.8879 High Similarity NPC149691
0.8866 High Similarity NPC130398
0.8857 High Similarity NPC82899
0.8857 High Similarity NPC270699
0.8857 High Similarity NPC321852
0.8824 High Similarity NPC209632
0.88 High Similarity NPC70624
0.8762 High Similarity NPC210089
0.8762 High Similarity NPC167504
0.8762 High Similarity NPC474157
0.875 High Similarity NPC85493
0.8692 High Similarity NPC153053
0.8679 High Similarity NPC79496
0.8627 High Similarity NPC474365
0.8627 High Similarity NPC301943
0.8598 High Similarity NPC272524
0.8571 High Similarity NPC269023
0.8571 High Similarity NPC99846
0.8529 High Similarity NPC188895
0.8519 High Similarity NPC308744
0.8515 High Similarity NPC325497
0.8515 High Similarity NPC203925
0.8462 Intermediate Similarity NPC269457
0.844 Intermediate Similarity NPC210092
0.844 Intermediate Similarity NPC306740
0.844 Intermediate Similarity NPC474685
0.8431 Intermediate Similarity NPC473325
0.8431 Intermediate Similarity NPC282895
0.8426 Intermediate Similarity NPC474176
0.8421 Intermediate Similarity NPC318107
0.8416 Intermediate Similarity NPC229242
0.8411 Intermediate Similarity NPC243355
0.8396 Intermediate Similarity NPC469636
0.8396 Intermediate Similarity NPC474364
0.8364 Intermediate Similarity NPC100353
0.8351 Intermediate Similarity NPC173443
0.8349 Intermediate Similarity NPC477411
0.8317 Intermediate Similarity NPC270654
0.8257 Intermediate Similarity NPC128368
0.8198 Intermediate Similarity NPC226093
0.8182 Intermediate Similarity NPC196075
0.8173 Intermediate Similarity NPC284477
0.8165 Intermediate Similarity NPC158282
0.8165 Intermediate Similarity NPC474314
0.8144 Intermediate Similarity NPC89377
0.812 Intermediate Similarity NPC246166
0.8095 Intermediate Similarity NPC255676
0.8091 Intermediate Similarity NPC161611
0.8081 Intermediate Similarity NPC62765
0.8073 Intermediate Similarity NPC476003
0.802 Intermediate Similarity NPC261181
0.8018 Intermediate Similarity NPC474363
0.8 Intermediate Similarity NPC212415
0.8 Intermediate Similarity NPC119631
0.798 Intermediate Similarity NPC220893
0.7963 Intermediate Similarity NPC470391
0.7938 Intermediate Similarity NPC58616
0.7938 Intermediate Similarity NPC294134
0.7931 Intermediate Similarity NPC50872
0.7928 Intermediate Similarity NPC13784
0.7895 Intermediate Similarity NPC228318
0.7879 Intermediate Similarity NPC304760
0.7876 Intermediate Similarity NPC135730
0.7864 Intermediate Similarity NPC61944
0.7845 Intermediate Similarity NPC473243
0.783 Intermediate Similarity NPC304873
0.781 Intermediate Similarity NPC217621
0.7798 Intermediate Similarity NPC211439
0.7797 Intermediate Similarity NPC223351
0.7788 Intermediate Similarity NPC228936
0.7788 Intermediate Similarity NPC474095
0.7788 Intermediate Similarity NPC253423
0.7778 Intermediate Similarity NPC144547
0.7757 Intermediate Similarity NPC234305
0.775 Intermediate Similarity NPC121272
0.775 Intermediate Similarity NPC476599
0.7732 Intermediate Similarity NPC288903
0.7727 Intermediate Similarity NPC318327
0.7723 Intermediate Similarity NPC240108
0.7723 Intermediate Similarity NPC213156
0.7692 Intermediate Similarity NPC289432
0.7692 Intermediate Similarity NPC988
0.7686 Intermediate Similarity NPC51292
0.7667 Intermediate Similarity NPC295664
0.7664 Intermediate Similarity NPC25458
0.7652 Intermediate Similarity NPC190298
0.7647 Intermediate Similarity NPC46634
0.7647 Intermediate Similarity NPC474283
0.7647 Intermediate Similarity NPC475692
0.7647 Intermediate Similarity NPC472703
0.7647 Intermediate Similarity NPC110704
0.7642 Intermediate Similarity NPC472318
0.7642 Intermediate Similarity NPC98911
0.7642 Intermediate Similarity NPC228435
0.7636 Intermediate Similarity NPC249811
0.7632 Intermediate Similarity NPC81808
0.7632 Intermediate Similarity NPC470764
0.7624 Intermediate Similarity NPC9822
0.7615 Intermediate Similarity NPC105899
0.7607 Intermediate Similarity NPC204784
0.7607 Intermediate Similarity NPC137710
0.7586 Intermediate Similarity NPC469574
0.7586 Intermediate Similarity NPC217423
0.7586 Intermediate Similarity NPC45104
0.7583 Intermediate Similarity NPC228739
0.7583 Intermediate Similarity NPC472704
0.7583 Intermediate Similarity NPC475691
0.7581 Intermediate Similarity NPC470278
0.7573 Intermediate Similarity NPC77273
0.7563 Intermediate Similarity NPC26285
0.7542 Intermediate Similarity NPC238861
0.7542 Intermediate Similarity NPC77000
0.7542 Intermediate Similarity NPC232958
0.7541 Intermediate Similarity NPC169913
0.7523 Intermediate Similarity NPC269644
0.7522 Intermediate Similarity NPC66208
0.7521 Intermediate Similarity NPC94298
0.7521 Intermediate Similarity NPC94637
0.7521 Intermediate Similarity NPC27633
0.752 Intermediate Similarity NPC7012
0.75 Intermediate Similarity NPC147561
0.7478 Intermediate Similarity NPC474408
0.7477 Intermediate Similarity NPC277788
0.7459 Intermediate Similarity NPC470765
0.7459 Intermediate Similarity NPC275576
0.7458 Intermediate Similarity NPC90522
0.7458 Intermediate Similarity NPC328459
0.7449 Intermediate Similarity NPC323103
0.7436 Intermediate Similarity NPC240664
0.7434 Intermediate Similarity NPC291799
0.7431 Intermediate Similarity NPC82426
0.7431 Intermediate Similarity NPC91820
0.7431 Intermediate Similarity NPC160382
0.7423 Intermediate Similarity NPC121800
0.7414 Intermediate Similarity NPC188907
0.7414 Intermediate Similarity NPC220540
0.7411 Intermediate Similarity NPC281604
0.7407 Intermediate Similarity NPC112552
0.7398 Intermediate Similarity NPC472706
0.7398 Intermediate Similarity NPC470753
0.7398 Intermediate Similarity NPC473220
0.7396 Intermediate Similarity NPC176228
0.7395 Intermediate Similarity NPC72977
0.7395 Intermediate Similarity NPC233282
0.7391 Intermediate Similarity NPC87069
0.7391 Intermediate Similarity NPC279916
0.7387 Intermediate Similarity NPC51174
0.7387 Intermediate Similarity NPC1065
0.7383 Intermediate Similarity NPC175852
0.7383 Intermediate Similarity NPC160548
0.7383 Intermediate Similarity NPC210529
0.7379 Intermediate Similarity NPC185501
0.7377 Intermediate Similarity NPC107846
0.7374 Intermediate Similarity NPC39600
0.7374 Intermediate Similarity NPC285773
0.7374 Intermediate Similarity NPC270507
0.7373 Intermediate Similarity NPC293424
0.7373 Intermediate Similarity NPC206007
0.7368 Intermediate Similarity NPC23332
0.7368 Intermediate Similarity NPC54626
0.7364 Intermediate Similarity NPC249067
0.7364 Intermediate Similarity NPC85977
0.736 Intermediate Similarity NPC42234
0.736 Intermediate Similarity NPC82712
0.736 Intermediate Similarity NPC475508
0.736 Intermediate Similarity NPC272946
0.7355 Intermediate Similarity NPC217756
0.735 Intermediate Similarity NPC470860
0.735 Intermediate Similarity NPC131192

  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 NPC89886 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
0.9314 High Similarity NPD2181 Clinical (unspecified phase)
0.9118 High Similarity NPD2182 Approved
0.91 High Similarity NPD164 Approved
0.8889 High Similarity NPD1238 Approved
0.8421 Intermediate Similarity NPD9259 Approved
0.8421 Intermediate Similarity NPD9257 Approved
0.8081 Intermediate Similarity NPD9256 Approved
0.8081 Intermediate Similarity NPD9258 Approved
0.802 Intermediate Similarity NPD1202 Approved
0.8 Intermediate Similarity NPD1609 Clinical (unspecified phase)
0.7767 Intermediate Similarity NPD9260 Approved
0.7712 Intermediate Similarity NPD518 Clinical (unspecified phase)
0.7684 Intermediate Similarity NPD9490 Approved
0.7642 Intermediate Similarity NPD5952 Clinical (unspecified phase)
0.7632 Intermediate Similarity NPD690 Clinical (unspecified phase)
0.7542 Intermediate Similarity NPD3412 Clinical (unspecified phase)
0.7521 Intermediate Similarity NPD9545 Approved
0.75 Intermediate Similarity NPD2067 Discontinued
0.744 Intermediate Similarity NPD3764 Approved
0.7411 Intermediate Similarity NPD6831 Clinical (unspecified phase)
0.7383 Intermediate Similarity NPD9495 Approved
0.7374 Intermediate Similarity NPD9491 Approved
0.7364 Intermediate Similarity NPD1237 Approved
0.7358 Intermediate Similarity NPD1989 Approved
0.735 Intermediate Similarity NPD9493 Approved
0.7328 Intermediate Similarity NPD5951 Approved
0.7273 Intermediate Similarity NPD6287 Discontinued
0.7273 Intermediate Similarity NPD9261 Approved
0.7255 Intermediate Similarity NPD1087 Approved
0.7241 Intermediate Similarity NPD1241 Discontinued
0.7222 Intermediate Similarity NPD7008 Discontinued
0.7216 Intermediate Similarity NPD227 Approved
0.7216 Intermediate Similarity NPD225 Approved
0.7212 Intermediate Similarity NPD3672 Approved
0.7212 Intermediate Similarity NPD3673 Approved
0.712 Intermediate Similarity NPD6007 Clinical (unspecified phase)
0.7117 Intermediate Similarity NPD1929 Approved
0.7117 Intermediate Similarity NPD1930 Approved
0.7117 Intermediate Similarity NPD1931 Clinical (unspecified phase)
0.7117 Intermediate Similarity NPD6647 Phase 2
0.7103 Intermediate Similarity NPD688 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD2199 Approved
0.7097 Intermediate Similarity NPD2198 Approved
0.7097 Intermediate Similarity NPD1876 Approved
0.7054 Intermediate Similarity NPD5909 Discontinued
0.7048 Intermediate Similarity NPD1089 Approved
0.7048 Intermediate Similarity NPD1086 Approved
0.7048 Intermediate Similarity NPD1090 Approved
0.704 Intermediate Similarity NPD552 Approved
0.704 Intermediate Similarity NPD9567 Approved
0.704 Intermediate Similarity NPD553 Approved
0.7027 Intermediate Similarity NPD1932 Approved
0.7018 Intermediate Similarity NPD9267 Approved
0.7018 Intermediate Similarity NPD9263 Approved
0.7018 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD9264 Approved
0.7008 Intermediate Similarity NPD6832 Phase 2
0.7 Intermediate Similarity NPD226 Approved
0.7 Intermediate Similarity NPD2066 Phase 3
0.7 Intermediate Similarity NPD2347 Approved
0.6992 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6992 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6984 Remote Similarity NPD1019 Discontinued
0.6981 Remote Similarity NPD1239 Approved
0.6967 Remote Similarity NPD7163 Clinical (unspecified phase)
0.6957 Remote Similarity NPD74 Approved
0.6957 Remote Similarity NPD9266 Approved
0.6952 Remote Similarity NPD800 Approved
0.6944 Remote Similarity NPD1693 Approved
0.6935 Remote Similarity NPD9717 Approved
0.693 Remote Similarity NPD3134 Approved
0.6923 Remote Similarity NPD650 Approved
0.6923 Remote Similarity NPD9508 Approved
0.6923 Remote Similarity NPD969 Suspended
0.6923 Remote Similarity NPD1282 Approved
0.6917 Remote Similarity NPD405 Clinical (unspecified phase)
0.6916 Remote Similarity NPD1088 Approved
0.6911 Remote Similarity NPD7457 Clinical (unspecified phase)
0.6894 Remote Similarity NPD2567 Approved
0.6894 Remote Similarity NPD2569 Approved
0.687 Remote Similarity NPD1358 Approved
0.6864 Remote Similarity NPD5277 Phase 2
0.6855 Remote Similarity NPD1281 Approved
0.6852 Remote Similarity NPD1563 Approved
0.6842 Remote Similarity NPD9697 Approved
0.6803 Remote Similarity NPD1894 Discontinued
0.68 Remote Similarity NPD3972 Approved
0.6794 Remote Similarity NPD3373 Approved
0.6792 Remote Similarity NPD689 Discontinued
0.6772 Remote Similarity NPD1203 Approved
0.6769 Remote Similarity NPD2313 Discontinued
0.6759 Remote Similarity NPD1508 Approved
0.6757 Remote Similarity NPD5926 Approved
0.6752 Remote Similarity NPD4233 Approved
0.6752 Remote Similarity NPD4234 Approved
0.675 Remote Similarity NPD2629 Approved
0.6748 Remote Similarity NPD5691 Approved
0.6746 Remote Similarity NPD182 Clinical (unspecified phase)
0.6741 Remote Similarity NPD2346 Discontinued
0.6716 Remote Similarity NPD3748 Approved
0.6697 Remote Similarity NPD5122 Clinical (unspecified phase)
0.6694 Remote Similarity NPD17 Approved
0.6693 Remote Similarity NPD5667 Approved
0.6693 Remote Similarity NPD1283 Approved
0.6692 Remote Similarity NPD1654 Clinical (unspecified phase)
0.669 Remote Similarity NPD6591 Clinical (unspecified phase)
0.6667 Remote Similarity NPD1564 Approved
0.6667 Remote Similarity NPD1565 Approved
0.6667 Remote Similarity NPD7609 Phase 3
0.6667 Remote Similarity NPD6637 Approved
0.6667 Remote Similarity NPD9250 Approved
0.6667 Remote Similarity NPD2329 Discontinued
0.6667 Remote Similarity NPD1566 Phase 3
0.6667 Remote Similarity NPD942 Approved
0.6619 Remote Similarity NPD7236 Approved
0.6618 Remote Similarity NPD1471 Phase 3
0.6618 Remote Similarity NPD7702 Clinical (unspecified phase)
0.6617 Remote Similarity NPD230 Phase 1
0.6617 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6612 Remote Similarity NPD4766 Approved
0.6612 Remote Similarity NPD1246 Approved
0.6612 Remote Similarity NPD9281 Approved
0.661 Remote Similarity NPD3646 Clinical (unspecified phase)
0.661 Remote Similarity NPD5235 Approved
0.661 Remote Similarity NPD5240 Approved
0.661 Remote Similarity NPD5237 Approved
0.661 Remote Similarity NPD1756 Approved
0.661 Remote Similarity NPD1752 Approved
0.661 Remote Similarity NPD5236 Approved
0.661 Remote Similarity NPD5239 Approved
0.6606 Remote Similarity NPD7631 Approved
0.6604 Remote Similarity NPD4793 Discontinued
0.6596 Remote Similarity NPD6273 Approved
0.6593 Remote Similarity NPD2799 Discontinued
0.6591 Remote Similarity NPD7713 Phase 3
0.6589 Remote Similarity NPD2798 Approved
0.6589 Remote Similarity NPD5740 Clinical (unspecified phase)
0.6589 Remote Similarity NPD6085 Phase 2
0.6583 Remote Similarity NPD7094 Approved
0.6583 Remote Similarity NPD6858 Approved
0.6577 Remote Similarity NPD1843 Approved
0.6567 Remote Similarity NPD3528 Clinical (unspecified phase)
0.6566 Remote Similarity NPD9716 Approved
0.6565 Remote Similarity NPD6039 Approved
0.656 Remote Similarity NPD5306 Approved
0.656 Remote Similarity NPD5305 Approved
0.6557 Remote Similarity NPD4198 Discontinued
0.6555 Remote Similarity NPD4141 Clinical (unspecified phase)
0.6555 Remote Similarity NPD2201 Approved
0.6549 Remote Similarity NPD7798 Approved
0.6541 Remote Similarity NPD2979 Phase 3
0.6541 Remote Similarity NPD4307 Phase 2
0.6538 Remote Similarity NPD3971 Phase 1
0.6535 Remote Similarity NPD1608 Approved
0.6535 Remote Similarity NPD1877 Discontinued
0.6535 Remote Similarity NPD4878 Approved
0.6529 Remote Similarity NPD2650 Approved
0.6529 Remote Similarity NPD2652 Approved
0.6525 Remote Similarity NPD642 Clinical (unspecified phase)
0.6522 Remote Similarity NPD5738 Clinical (unspecified phase)
0.6519 Remote Similarity NPD2670 Approved
0.6515 Remote Similarity NPD411 Approved
0.6512 Remote Similarity NPD3267 Approved
0.6512 Remote Similarity NPD2797 Approved
0.6512 Remote Similarity NPD3266 Approved
0.6508 Remote Similarity NPD4135 Approved
0.6508 Remote Similarity NPD4106 Approved
0.6508 Remote Similarity NPD4136 Approved
0.6504 Remote Similarity NPD694 Clinical (unspecified phase)
0.65 Remote Similarity NPD643 Clinical (unspecified phase)
0.6493 Remote Similarity NPD447 Suspended
0.6493 Remote Similarity NPD1933 Approved
0.6481 Remote Similarity NPD5346 Phase 2
0.6481 Remote Similarity NPD5347 Phase 2
0.648 Remote Similarity NPD5585 Approved
0.648 Remote Similarity NPD1245 Approved
0.648 Remote Similarity NPD1651 Approved
0.6475 Remote Similarity NPD7003 Approved
0.6475 Remote Similarity NPD4628 Phase 3
0.6475 Remote Similarity NPD3750 Approved
0.6471 Remote Similarity NPD1110 Approved
0.6471 Remote Similarity NPD3170 Approved
0.6471 Remote Similarity NPD1109 Approved
0.6471 Remote Similarity NPD1317 Discontinued
0.6466 Remote Similarity NPD3046 Approved
0.6466 Remote Similarity NPD3048 Approved
0.6466 Remote Similarity NPD3047 Approved
0.6457 Remote Similarity NPD4807 Approved
0.6457 Remote Similarity NPD4806 Approved
0.6452 Remote Similarity NPD6065 Approved
0.6449 Remote Similarity NPD970 Clinical (unspecified phase)
0.6446 Remote Similarity NPD2607 Approved
0.6446 Remote Similarity NPD1279 Clinical (unspecified phase)
0.6436 Remote Similarity NPD9294 Approved
0.6429 Remote Similarity NPD1104 Approved
0.6429 Remote Similarity NPD1362 Clinical (unspecified phase)
0.6429 Remote Similarity NPD4626 Approved
0.6423 Remote Similarity NPD1551 Phase 2
0.6418 Remote Similarity NPD3142 Approved
0.6418 Remote Similarity NPD3140 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