Structure

Physi-Chem Properties

Molecular Weight:  282.11
Volume:  281.703
LogP:  1.152
LogD:  1.304
LogS:  -2.04
# Rotatable Bonds:  10
TPSA:  71.06
# H-Bond Aceptor:  6
# H-Bond Donor:  0
# Rings:  1
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.528
Synthetic Accessibility Score:  1.867
Fsp3:  0.429
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:  -4.401
MDCK Permeability:  4.3462092435220256e-05
Pgp-inhibitor:  0.071
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.002
20% Bioavailability (F20%):  0.937
30% Bioavailability (F30%):  0.798

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.72
Plasma Protein Binding (PPB):  24.397850036621094%
Volume Distribution (VD):  0.656
Pgp-substrate:  35.48465347290039%

ADMET: Metabolism

CYP1A2-inhibitor:  0.799
CYP1A2-substrate:  0.855
CYP2C19-inhibitor:  0.603
CYP2C19-substrate:  0.088
CYP2C9-inhibitor:  0.247
CYP2C9-substrate:  0.084
CYP2D6-inhibitor:  0.015
CYP2D6-substrate:  0.166
CYP3A4-inhibitor:  0.05
CYP3A4-substrate:  0.278

ADMET: Excretion

Clearance (CL):  10.661
Half-life (T1/2):  0.418

ADMET: Toxicity

hERG Blockers:  0.407
Human Hepatotoxicity (H-HT):  0.006
Drug-inuced Liver Injury (DILI):  0.243
AMES Toxicity:  0.078
Rat Oral Acute Toxicity:  0.002
Maximum Recommended Daily Dose:  0.003
Skin Sensitization:  0.541
Carcinogencity:  0.031
Eye Corrosion:  0.02
Eye Irritation:  0.976
Respiratory Toxicity:  0.032

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

  Natural Product: NPC174099

Natural Product ID:  NPC174099
Common Name*:   Bis(2-Methoxyethyl) Benzene-1,2-Dicarboxylate
IUPAC Name:   bis(2-methoxyethyl) benzene-1,2-dicarboxylate
Synonyms:  
Standard InCHIKey:  HSUIVCLOAAJSRE-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C14H18O6/c1-17-7-9-19-13(15)11-5-3-4-6-12(11)14(16)20-10-8-18-2/h3-6H,7-10H2,1-2H3
SMILES:  COCCOC(=O)c1ccccc1C(=O)OCCOC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1302251
PubChem CID:   8344
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives
        • [CHEMONTID:0000176] Benzoic acids and derivatives
          • [CHEMONTID:0001350] Benzoic acid esters

*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
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. DOI[10.1002/elan.200403102]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. DOI[10.1016/j.foodchem.2012.02.124]
NPO10494 Alpinia katsumadai Species Staphylinidae Eukaryota n.a. n.a. n.a. PMID[10654416]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. PMID[11077184]
NPO10494 Alpinia katsumadai Species Staphylinidae Eukaryota n.a. seed n.a. PMID[14577694]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. PMID[17328234]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flower buds n.a. n.a. PMID[18321056]
NPO10494 Alpinia katsumadai Species Staphylinidae Eukaryota n.a. n.a. n.a. PMID[20014777]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. flower n.a. PMID[21804227]
NPO10494 Alpinia katsumadai Species Staphylinidae Eukaryota n.a. seed n.a. PMID[21942765]
NPO10494 Alpinia katsumadai Species Staphylinidae Eukaryota seeds n.a. n.a. PMID[21942765]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota flower buds Henan province, China 2005-MAY PMID[21942812]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. flower bud n.a. PMID[21942812]
NPO10494 Alpinia katsumadai Species Staphylinidae Eukaryota n.a. n.a. n.a. PMID[22459211]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. leaf n.a. PMID[23265495]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flower buds n.a. n.a. PMID[24279769]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10494 Alpinia katsumadai Species Staphylinidae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10494 Alpinia katsumadai Species Staphylinidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO10494 Alpinia katsumadai Species Staphylinidae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO10494 Alpinia katsumadai Species Staphylinidae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10494 Alpinia katsumadai Species Staphylinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1515 Lonicera japonica Species Caprifoliaceae 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
NPT210 Individual Protein Thyroid stimulating hormone receptor Homo sapiens Potency = 199.5 nM PMID[478698]
NPT49 Individual Protein DNA-(apurinic or apyrimidinic site) lyase Homo sapiens Potency n.a. 1584.9 nM PMID[478698]
NPT610 Others Molecular identity unknown Potency n.a. 10000.0 nM PMID[478698]
NPT2 Others Unspecified Potency n.a. 21875.1 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 1.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 22003.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 62014.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 2169 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 6.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 2747.3 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 NPC174099 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
0.9802 High Similarity NPC56493
0.9706 High Similarity NPC10251
0.9706 High Similarity NPC17417
0.9703 High Similarity NPC119271
0.9612 High Similarity NPC196246
0.9612 High Similarity NPC93084
0.9612 High Similarity NPC251854
0.9612 High Similarity NPC214067
0.9519 High Similarity NPC305912
0.9519 High Similarity NPC1082
0.9505 High Similarity NPC31786
0.9429 High Similarity NPC82899
0.9429 High Similarity NPC321852
0.9429 High Similarity NPC270699
0.9333 High Similarity NPC260818
0.9252 High Similarity NPC153053
0.9143 High Similarity NPC85493
0.9074 High Similarity NPC307651
0.9029 High Similarity NPC89886
0.901 High Similarity NPC78701
0.901 High Similarity NPC35448
0.8962 High Similarity NPC83628
0.8962 High Similarity NPC265407
0.8932 High Similarity NPC45613
0.8922 High Similarity NPC146351
0.8911 High Similarity NPC249912
0.8911 High Similarity NPC276775
0.8911 High Similarity NPC92754
0.8857 High Similarity NPC269457
0.8846 High Similarity NPC474365
0.8846 High Similarity NPC301943
0.8824 High Similarity NPC225060
0.8796 High Similarity NPC474157
0.8774 High Similarity NPC30594
0.8774 High Similarity NPC37622
0.8727 High Similarity NPC308744
0.8713 High Similarity NPC130398
0.8679 High Similarity NPC209632
0.8667 High Similarity NPC60679
0.8654 High Similarity NPC70624
0.8654 High Similarity NPC42211
0.8649 High Similarity NPC210092
0.8624 High Similarity NPC210089
0.8611 High Similarity NPC474364
0.8611 High Similarity NPC469636
0.8585 High Similarity NPC114594
0.8571 High Similarity NPC149691
0.8559 High Similarity NPC474363
0.8558 High Similarity NPC118343
0.8558 High Similarity NPC203925
0.8558 High Similarity NPC325497
0.8476 Intermediate Similarity NPC282895
0.8475 Intermediate Similarity NPC246166
0.8468 Intermediate Similarity NPC272524
0.8455 Intermediate Similarity NPC167504
0.844 Intermediate Similarity NPC269023
0.844 Intermediate Similarity NPC99846
0.8396 Intermediate Similarity NPC188895
0.8393 Intermediate Similarity NPC237366
0.8378 Intermediate Similarity NPC79496
0.8319 Intermediate Similarity NPC474685
0.8304 Intermediate Similarity NPC128368
0.8304 Intermediate Similarity NPC474176
0.8286 Intermediate Similarity NPC229242
0.8218 Intermediate Similarity NPC173443
0.8214 Intermediate Similarity NPC158282
0.8214 Intermediate Similarity NPC474314
0.8158 Intermediate Similarity NPC306740
0.8142 Intermediate Similarity NPC161611
0.8125 Intermediate Similarity NPC476003
0.8103 Intermediate Similarity NPC469574
0.8087 Intermediate Similarity NPC100353
0.807 Intermediate Similarity NPC196075
0.807 Intermediate Similarity NPC477411
0.8056 Intermediate Similarity NPC284477
0.8051 Intermediate Similarity NPC473243
0.8039 Intermediate Similarity NPC220893
0.802 Intermediate Similarity NPC89377
0.8018 Intermediate Similarity NPC470391
0.8017 Intermediate Similarity NPC295664
0.7983 Intermediate Similarity NPC50872
0.7966 Intermediate Similarity NPC204784
0.7965 Intermediate Similarity NPC243355
0.7934 Intermediate Similarity NPC471466
0.7931 Intermediate Similarity NPC226093
0.7921 Intermediate Similarity NPC318107
0.7909 Intermediate Similarity NPC85977
0.7905 Intermediate Similarity NPC261181
0.7895 Intermediate Similarity NPC212415
0.7886 Intermediate Similarity NPC169913
0.7857 Intermediate Similarity NPC472394
0.7851 Intermediate Similarity NPC223351
0.785 Intermediate Similarity NPC270654
0.7845 Intermediate Similarity NPC474095
0.7845 Intermediate Similarity NPC228936
0.7826 Intermediate Similarity NPC13784
0.7822 Intermediate Similarity NPC58616
0.7822 Intermediate Similarity NPC294134
0.7818 Intermediate Similarity NPC234305
0.7818 Intermediate Similarity NPC255676
0.7812 Intermediate Similarity NPC311339
0.7805 Intermediate Similarity NPC476599
0.7805 Intermediate Similarity NPC121272
0.7805 Intermediate Similarity NPC275576
0.7798 Intermediate Similarity NPC473325
0.7778 Intermediate Similarity NPC135730
0.7768 Intermediate Similarity NPC472315
0.7768 Intermediate Similarity NPC475203
0.7768 Intermediate Similarity NPC474376
0.7768 Intermediate Similarity NPC472316
0.7767 Intermediate Similarity NPC304760
0.7742 Intermediate Similarity NPC51292
0.7727 Intermediate Similarity NPC304873
0.7724 Intermediate Similarity NPC125053
0.7714 Intermediate Similarity NPC119631
0.7706 Intermediate Similarity NPC217621
0.7706 Intermediate Similarity NPC472318
0.7706 Intermediate Similarity NPC98911
0.7705 Intermediate Similarity NPC46634
0.7705 Intermediate Similarity NPC472703
0.7698 Intermediate Similarity NPC27712
0.7698 Intermediate Similarity NPC475508
0.7692 Intermediate Similarity NPC81808
0.7685 Intermediate Similarity NPC253423
0.768 Intermediate Similarity NPC472707
0.768 Intermediate Similarity NPC115797
0.768 Intermediate Similarity NPC51448
0.7674 Intermediate Similarity NPC477893
0.7674 Intermediate Similarity NPC477896
0.7658 Intermediate Similarity NPC160382
0.7647 Intermediate Similarity NPC228318
0.7642 Intermediate Similarity NPC228739
0.7642 Intermediate Similarity NPC472704
0.7638 Intermediate Similarity NPC475478
0.7632 Intermediate Similarity NPC281604
0.7624 Intermediate Similarity NPC288903
0.7619 Intermediate Similarity NPC213156
0.7619 Intermediate Similarity NPC62765
0.7619 Intermediate Similarity NPC240108
0.7611 Intermediate Similarity NPC136962
0.7597 Intermediate Similarity NPC474608
0.7593 Intermediate Similarity NPC61944
0.7589 Intermediate Similarity NPC269644
0.7586 Intermediate Similarity NPC66208
0.7578 Intermediate Similarity NPC233860
0.7578 Intermediate Similarity NPC239358
0.7578 Intermediate Similarity NPC475569
0.7578 Intermediate Similarity NPC233692
0.7568 Intermediate Similarity NPC25458
0.7561 Intermediate Similarity NPC474283
0.7561 Intermediate Similarity NPC475692
0.7559 Intermediate Similarity NPC272946
0.7559 Intermediate Similarity NPC147561
0.7559 Intermediate Similarity NPC42234
0.7544 Intermediate Similarity NPC211439
0.7544 Intermediate Similarity NPC249811
0.7542 Intermediate Similarity NPC470764
0.7542 Intermediate Similarity NPC217111
0.7542 Intermediate Similarity NPC474408
0.7541 Intermediate Similarity NPC144547
0.7538 Intermediate Similarity NPC291638
0.7538 Intermediate Similarity NPC265459
0.7538 Intermediate Similarity NPC195647
0.7538 Intermediate Similarity NPC17877
0.7538 Intermediate Similarity NPC66761
0.7538 Intermediate Similarity NPC290833
0.7538 Intermediate Similarity NPC472577
0.7538 Intermediate Similarity NPC475262
0.7525 Intermediate Similarity NPC323103
0.7524 Intermediate Similarity NPC9822
0.7522 Intermediate Similarity NPC105899
0.7521 Intermediate Similarity NPC90522
0.7521 Intermediate Similarity NPC328459
0.752 Intermediate Similarity NPC470765
0.7519 Intermediate Similarity NPC472248
0.75 Intermediate Similarity NPC240664
0.75 Intermediate Similarity NPC472395
0.75 Intermediate Similarity NPC51079
0.75 Intermediate Similarity NPC472371
0.75 Intermediate Similarity NPC217423
0.75 Intermediate Similarity NPC475691
0.75 Intermediate Similarity NPC45104
0.75 Intermediate Similarity NPC470278
0.75 Intermediate Similarity NPC291799
0.7481 Intermediate Similarity NPC472374
0.7481 Intermediate Similarity NPC194769
0.7481 Intermediate Similarity NPC472372
0.7481 Intermediate Similarity NPC285221
0.748 Intermediate Similarity NPC301857
0.7478 Intermediate Similarity NPC318327
0.7477 Intermediate Similarity NPC112552
0.7477 Intermediate Similarity NPC77273
0.7462 Intermediate Similarity NPC134937
0.7462 Intermediate Similarity NPC311492
0.7462 Intermediate Similarity NPC38420
0.7462 Intermediate Similarity NPC136608
0.7462 Intermediate Similarity NPC472250
0.7462 Intermediate Similarity NPC153617
0.7462 Intermediate Similarity NPC329913
0.7462 Intermediate Similarity NPC298547

  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 NPC174099 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
0.9706 High Similarity NPD2182 Approved
0.9505 High Similarity NPD164 Approved
0.8972 High Similarity NPD2181 Clinical (unspecified phase)
0.8558 High Similarity NPD1238 Approved
0.8036 Intermediate Similarity NPD2067 Discontinued
0.7921 Intermediate Similarity NPD9257 Approved
0.7921 Intermediate Similarity NPD9259 Approved
0.7905 Intermediate Similarity NPD1202 Approved
0.7895 Intermediate Similarity NPD1609 Clinical (unspecified phase)
0.7845 Intermediate Similarity NPD690 Clinical (unspecified phase)
0.784 Intermediate Similarity NPD5952 Clinical (unspecified phase)
0.7769 Intermediate Similarity NPD518 Clinical (unspecified phase)
0.7632 Intermediate Similarity NPD6831 Clinical (unspecified phase)
0.7619 Intermediate Similarity NPD9256 Approved
0.7619 Intermediate Similarity NPD9258 Approved
0.748 Intermediate Similarity NPD6287 Discontinued
0.7459 Intermediate Similarity NPD3412 Clinical (unspecified phase)
0.7438 Intermediate Similarity NPD9545 Approved
0.7431 Intermediate Similarity NPD1989 Approved
0.7395 Intermediate Similarity NPD5951 Approved
0.7391 Intermediate Similarity NPD1358 Approved
0.7339 Intermediate Similarity NPD9260 Approved
0.7333 Intermediate Similarity NPD1087 Approved
0.7297 Intermediate Similarity NPD9495 Approved
0.729 Intermediate Similarity NPD3673 Approved
0.729 Intermediate Similarity NPD3672 Approved
0.7287 Intermediate Similarity NPD7008 Discontinued
0.7273 Intermediate Similarity NPD9493 Approved
0.7228 Intermediate Similarity NPD9490 Approved
0.7209 Intermediate Similarity NPD6832 Phase 2
0.7193 Intermediate Similarity NPD6647 Phase 2
0.7188 Intermediate Similarity NPD1019 Discontinued
0.7167 Intermediate Similarity NPD1241 Discontinued
0.7165 Intermediate Similarity NPD2199 Approved
0.7165 Intermediate Similarity NPD2198 Approved
0.713 Intermediate Similarity NPD1090 Approved
0.713 Intermediate Similarity NPD1089 Approved
0.713 Intermediate Similarity NPD5909 Discontinued
0.713 Intermediate Similarity NPD1237 Approved
0.713 Intermediate Similarity NPD1086 Approved
0.7115 Intermediate Similarity NPD9491 Approved
0.7107 Intermediate Similarity NPD2629 Approved
0.7099 Intermediate Similarity NPD3764 Approved
0.708 Intermediate Similarity NPD2066 Phase 3
0.7054 Intermediate Similarity NPD6007 Clinical (unspecified phase)
0.7049 Intermediate Similarity NPD4198 Discontinued
0.7043 Intermediate Similarity NPD1930 Approved
0.7043 Intermediate Similarity NPD1931 Clinical (unspecified phase)
0.7043 Intermediate Similarity NPD1929 Approved
0.704 Intermediate Similarity NPD7163 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD800 Approved
0.7031 Intermediate Similarity NPD1876 Approved
0.7031 Intermediate Similarity NPD5667 Approved
0.7009 Intermediate Similarity NPD3134 Approved
0.7009 Intermediate Similarity NPD650 Approved
0.7008 Intermediate Similarity NPD9717 Approved
0.7 Intermediate Similarity NPD1088 Approved
0.7 Intermediate Similarity NPD969 Suspended
0.6977 Remote Similarity NPD553 Approved
0.6977 Remote Similarity NPD9567 Approved
0.6977 Remote Similarity NPD552 Approved
0.6975 Remote Similarity NPD4233 Approved
0.6975 Remote Similarity NPD4234 Approved
0.6961 Remote Similarity NPD225 Approved
0.6961 Remote Similarity NPD227 Approved
0.6957 Remote Similarity NPD1932 Approved
0.6942 Remote Similarity NPD5277 Phase 2
0.694 Remote Similarity NPD447 Suspended
0.694 Remote Similarity NPD230 Phase 1
0.6937 Remote Similarity NPD5122 Clinical (unspecified phase)
0.6935 Remote Similarity NPD2347 Approved
0.6934 Remote Similarity NPD2346 Discontinued
0.6934 Remote Similarity NPD2343 Clinical (unspecified phase)
0.693 Remote Similarity NPD7798 Approved
0.6917 Remote Similarity NPD4141 Clinical (unspecified phase)
0.6909 Remote Similarity NPD7609 Phase 3
0.6906 Remote Similarity NPD4628 Phase 3
0.6905 Remote Similarity NPD5305 Approved
0.6905 Remote Similarity NPD5306 Approved
0.6897 Remote Similarity NPD9261 Approved
0.6875 Remote Similarity NPD1693 Approved
0.6875 Remote Similarity NPD3972 Approved
0.6875 Remote Similarity NPD688 Clinical (unspecified phase)
0.6875 Remote Similarity NPD6637 Approved
0.6866 Remote Similarity NPD3373 Approved
0.6866 Remote Similarity NPD2979 Phase 3
0.6852 Remote Similarity NPD1282 Approved
0.685 Remote Similarity NPD4136 Approved
0.685 Remote Similarity NPD4135 Approved
0.685 Remote Similarity NPD4106 Approved
0.6847 Remote Similarity NPD7631 Approved
0.6842 Remote Similarity NPD2313 Discontinued
0.6842 Remote Similarity NPD5926 Approved
0.6838 Remote Similarity NPD2569 Approved
0.6838 Remote Similarity NPD2567 Approved
0.6833 Remote Similarity NPD1317 Discontinued
0.6825 Remote Similarity NPD5691 Approved
0.6822 Remote Similarity NPD182 Clinical (unspecified phase)
0.6815 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6815 Remote Similarity NPD1933 Approved
0.6812 Remote Similarity NPD7702 Clinical (unspecified phase)
0.6809 Remote Similarity NPD7236 Approved
0.6797 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6797 Remote Similarity NPD1281 Approved
0.6797 Remote Similarity NPD4807 Approved
0.6797 Remote Similarity NPD4806 Approved
0.6788 Remote Similarity NPD2799 Discontinued
0.6786 Remote Similarity NPD1563 Approved
0.6762 Remote Similarity NPD226 Approved
0.6757 Remote Similarity NPD1239 Approved
0.675 Remote Similarity NPD2329 Discontinued
0.6741 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6739 Remote Similarity NPD2438 Suspended
0.6738 Remote Similarity NPD3887 Approved
0.6721 Remote Similarity NPD9508 Approved
0.672 Remote Similarity NPD405 Clinical (unspecified phase)
0.672 Remote Similarity NPD694 Clinical (unspecified phase)
0.6719 Remote Similarity NPD7457 Clinical (unspecified phase)
0.6718 Remote Similarity NPD1203 Approved
0.6694 Remote Similarity NPD5237 Approved
0.6694 Remote Similarity NPD1752 Approved
0.6694 Remote Similarity NPD1756 Approved
0.6694 Remote Similarity NPD5235 Approved
0.6694 Remote Similarity NPD5236 Approved
0.6694 Remote Similarity NPD5239 Approved
0.6694 Remote Similarity NPD5240 Approved
0.6693 Remote Similarity NPD4102 Approved
0.6693 Remote Similarity NPD5585 Approved
0.6693 Remote Similarity NPD4105 Approved
0.6667 Remote Similarity NPD3748 Approved
0.6667 Remote Similarity NPD9267 Approved
0.6667 Remote Similarity NPD5647 Approved
0.6667 Remote Similarity NPD5740 Clinical (unspecified phase)
0.6667 Remote Similarity NPD9265 Clinical (unspecified phase)
0.6667 Remote Similarity NPD9263 Approved
0.6667 Remote Similarity NPD2798 Approved
0.6667 Remote Similarity NPD7713 Phase 3
0.6667 Remote Similarity NPD6233 Phase 2
0.6667 Remote Similarity NPD6085 Phase 2
0.6667 Remote Similarity NPD9264 Approved
0.6644 Remote Similarity NPD6591 Clinical (unspecified phase)
0.6643 Remote Similarity NPD6799 Approved
0.6642 Remote Similarity NPD3528 Clinical (unspecified phase)
0.6642 Remote Similarity NPD6039 Approved
0.6641 Remote Similarity NPD17 Approved
0.6641 Remote Similarity NPD1283 Approved
0.6641 Remote Similarity NPD1104 Approved
0.6639 Remote Similarity NPD2201 Approved
0.6636 Remote Similarity NPD3971 Phase 1
0.6619 Remote Similarity NPD2935 Discontinued
0.6618 Remote Similarity NPD4307 Phase 2
0.6617 Remote Similarity NPD9494 Approved
0.6614 Remote Similarity NPD1894 Discontinued
0.6612 Remote Similarity NPD74 Approved
0.6612 Remote Similarity NPD9266 Approved
0.661 Remote Similarity NPD5738 Clinical (unspecified phase)
0.6609 Remote Similarity NPD1566 Phase 3
0.6609 Remote Similarity NPD1564 Approved
0.6609 Remote Similarity NPD1565 Approved
0.6596 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6594 Remote Similarity NPD2670 Approved
0.6593 Remote Similarity NPD6798 Discontinued
0.6591 Remote Similarity NPD2797 Approved
0.6591 Remote Similarity NPD3267 Approved
0.6591 Remote Similarity NPD3266 Approved
0.6589 Remote Similarity NPD3496 Discontinued
0.6577 Remote Similarity NPD5347 Phase 2
0.6577 Remote Similarity NPD5346 Phase 2
0.6575 Remote Similarity NPD7239 Suspended
0.6571 Remote Similarity NPD1471 Phase 3
0.6571 Remote Similarity NPD2355 Clinical (unspecified phase)
0.6571 Remote Similarity NPD2353 Approved
0.6569 Remote Similarity NPD6355 Discontinued
0.6569 Remote Similarity NPD4618 Approved
0.6569 Remote Similarity NPD4622 Approved
0.6562 Remote Similarity NPD1651 Approved
0.656 Remote Similarity NPD4766 Approved
0.6557 Remote Similarity NPD3646 Clinical (unspecified phase)
0.6555 Remote Similarity NPD3048 Approved
0.6555 Remote Similarity NPD3046 Approved
0.6555 Remote Similarity NPD3047 Approved
0.6554 Remote Similarity NPD6386 Approved
0.6554 Remote Similarity NPD6385 Approved
0.6552 Remote Similarity NPD6273 Approved
0.6549 Remote Similarity NPD1508 Approved
0.6549 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6549 Remote Similarity NPD7003 Approved
0.6547 Remote Similarity NPD1109 Approved
0.6547 Remote Similarity NPD3170 Approved
0.6547 Remote Similarity NPD1110 Approved
0.6545 Remote Similarity NPD4793 Discontinued
0.6544 Remote Similarity NPD7961 Discontinued
0.6544 Remote Similarity NPD4062 Phase 3
0.6532 Remote Similarity NPD7094 Approved
0.6532 Remote Similarity NPD6858 Approved
0.6532 Remote Similarity NPD2607 Approved
0.6531 Remote Similarity NPD3226 Approved
0.6525 Remote Similarity NPD970 Clinical (unspecified phase)
0.6525 Remote Similarity NPD2897 Discontinued
0.6522 Remote Similarity NPD1654 Clinical (unspecified phase)

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data