Structure

Physi-Chem Properties

Molecular Weight:  180.08
Volume:  188.785
LogP:  1.4
LogD:  1.158
LogS:  -1.565
# Rotatable Bonds:  4
TPSA:  46.53
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  1
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.713
Synthetic Accessibility Score:  2.122
Fsp3:  0.3
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:  -4.488
MDCK Permeability:  5.817433338961564e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.029
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.006
30% Bioavailability (F30%):  0.094

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.973
Plasma Protein Binding (PPB):  50.672630310058594%
Volume Distribution (VD):  0.894
Pgp-substrate:  56.43227005004883%

ADMET: Metabolism

CYP1A2-inhibitor:  0.368
CYP1A2-substrate:  0.304
CYP2C19-inhibitor:  0.159
CYP2C19-substrate:  0.64
CYP2C9-inhibitor:  0.037
CYP2C9-substrate:  0.534
CYP2D6-inhibitor:  0.01
CYP2D6-substrate:  0.4
CYP3A4-inhibitor:  0.011
CYP3A4-substrate:  0.351

ADMET: Excretion

Clearance (CL):  5.392
Half-life (T1/2):  0.697

ADMET: Toxicity

hERG Blockers:  0.03
Human Hepatotoxicity (H-HT):  0.016
Drug-inuced Liver Injury (DILI):  0.384
AMES Toxicity:  0.009
Rat Oral Acute Toxicity:  0.013
Maximum Recommended Daily Dose:  0.017
Skin Sensitization:  0.206
Carcinogencity:  0.02
Eye Corrosion:  0.017
Eye Irritation:  0.977
Respiratory Toxicity:  0.046

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

  Natural Product: NPC160382

Natural Product ID:  NPC160382
Common Name*:   Ethyl 2-Hydroxy-2-Phenylacetate
IUPAC Name:   ethyl 2-hydroxy-2-phenylacetate
Synonyms:   Hydroxy-Phenyl-Acetic Acid Ethyl Ester
Standard InCHIKey:  SAXHIDRUJXPDOD-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C10H12O3/c1-2-13-10(12)9(11)8-6-4-3-5-7-8/h3-7,9,11H,2H2,1H3
SMILES:  CCOC(=O)C(c1ccccc1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL165662
PubChem CID:   13050
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted 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
NPT1317 Cell Line CCRF S-180 Mus musculus Conversion rate = 21.2 % PMID[486123]
NPT2 Others Unspecified Ac50 n.a. 2.818 uM PMID[486124]
NPT2 Others Unspecified Ac50 n.a. 44.67 uM PMID[486124]
NPT2 Others Unspecified AC50 n.a. 2818.4 nM PMID[486124]
NPT2 Others Unspecified AC50 n.a. 44668.4 nM PMID[486124]
NPT2 Others Unspecified Potency n.a. 0.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 239.1 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 NPC160382 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
0.9579 High Similarity NPC175852
0.9579 High Similarity NPC160548
0.9579 High Similarity NPC210529
0.8947 High Similarity NPC317645
0.8679 High Similarity NPC158282
0.8598 High Similarity NPC48525
0.8491 Intermediate Similarity NPC326187
0.8349 Intermediate Similarity NPC474363
0.8333 Intermediate Similarity NPC474314
0.8316 Intermediate Similarity NPC294134
0.8286 Intermediate Similarity NPC472919
0.8241 Intermediate Similarity NPC476003
0.8208 Intermediate Similarity NPC136962
0.8198 Intermediate Similarity NPC210531
0.819 Intermediate Similarity NPC171831
0.819 Intermediate Similarity NPC249067
0.819 Intermediate Similarity NPC471466
0.819 Intermediate Similarity NPC280616
0.819 Intermediate Similarity NPC242913
0.8182 Intermediate Similarity NPC172525
0.8125 Intermediate Similarity NPC95965
0.8105 Intermediate Similarity NPC285773
0.8105 Intermediate Similarity NPC288903
0.8095 Intermediate Similarity NPC91820
0.8095 Intermediate Similarity NPC82426
0.8091 Intermediate Similarity NPC272524
0.8061 Intermediate Similarity NPC304760
0.8058 Intermediate Similarity NPC229242
0.8056 Intermediate Similarity NPC281604
0.8056 Intermediate Similarity NPC31274
0.8051 Intermediate Similarity NPC65310
0.8037 Intermediate Similarity NPC475203
0.8037 Intermediate Similarity NPC472315
0.8037 Intermediate Similarity NPC474376
0.8037 Intermediate Similarity NPC37115
0.8037 Intermediate Similarity NPC472316
0.8019 Intermediate Similarity NPC19136
0.8 Intermediate Similarity NPC87299
0.8 Intermediate Similarity NPC25458
0.8 Intermediate Similarity NPC103326
0.8 Intermediate Similarity NPC329319
0.8 Intermediate Similarity NPC99394
0.7981 Intermediate Similarity NPC217621
0.7966 Intermediate Similarity NPC57607
0.7963 Intermediate Similarity NPC156648
0.7961 Intermediate Similarity NPC249912
0.7961 Intermediate Similarity NPC253423
0.7961 Intermediate Similarity NPC92754
0.7961 Intermediate Similarity NPC276775
0.7959 Intermediate Similarity NPC89377
0.7959 Intermediate Similarity NPC322387
0.7944 Intermediate Similarity NPC13495
0.7909 Intermediate Similarity NPC260818
0.7905 Intermediate Similarity NPC469481
0.7905 Intermediate Similarity NPC52472
0.79 Intermediate Similarity NPC62765
0.7895 Intermediate Similarity NPC117180
0.789 Intermediate Similarity NPC474364
0.7885 Intermediate Similarity NPC78701
0.7885 Intermediate Similarity NPC35448
0.7885 Intermediate Similarity NPC225060
0.7879 Intermediate Similarity NPC329064
0.7857 Intermediate Similarity NPC87069
0.7838 Intermediate Similarity NPC321852
0.7835 Intermediate Similarity NPC304538
0.783 Intermediate Similarity NPC304873
0.7826 Intermediate Similarity NPC63126
0.7826 Intermediate Similarity NPC104514
0.7822 Intermediate Similarity NPC110704
0.7812 Intermediate Similarity NPC323103
0.781 Intermediate Similarity NPC245561
0.781 Intermediate Similarity NPC146351
0.78 Intermediate Similarity NPC9822
0.78 Intermediate Similarity NPC220893
0.7798 Intermediate Similarity NPC277788
0.7797 Intermediate Similarity NPC469927
0.7789 Intermediate Similarity NPC121800
0.7789 Intermediate Similarity NPC127343
0.7788 Intermediate Similarity NPC289201
0.7788 Intermediate Similarity NPC474685
0.7788 Intermediate Similarity NPC469509
0.7769 Intermediate Similarity NPC472707
0.7767 Intermediate Similarity NPC130398
0.7759 Intermediate Similarity NPC472708
0.7757 Intermediate Similarity NPC301943
0.7757 Intermediate Similarity NPC13426
0.7757 Intermediate Similarity NPC474365
0.7755 Intermediate Similarity NPC58616
0.7736 Intermediate Similarity NPC70624
0.7736 Intermediate Similarity NPC42211
0.7732 Intermediate Similarity NPC270507
0.7727 Intermediate Similarity NPC469636
0.7727 Intermediate Similarity NPC265407
0.7727 Intermediate Similarity NPC85493
0.7727 Intermediate Similarity NPC83628
0.7723 Intermediate Similarity NPC274455
0.7723 Intermediate Similarity NPC70940
0.7723 Intermediate Similarity NPC86670
0.7699 Intermediate Similarity NPC308744
0.7699 Intermediate Similarity NPC148969
0.7699 Intermediate Similarity NPC153053
0.7692 Intermediate Similarity NPC61944
0.7684 Intermediate Similarity NPC170484
0.7679 Intermediate Similarity NPC234376
0.7664 Intermediate Similarity NPC284477
0.7658 Intermediate Similarity NPC234639
0.7658 Intermediate Similarity NPC174099
0.7652 Intermediate Similarity NPC212891
0.7647 Intermediate Similarity NPC472319
0.7642 Intermediate Similarity NPC280869
0.7642 Intermediate Similarity NPC325497
0.7642 Intermediate Similarity NPC118343
0.7636 Intermediate Similarity NPC211439
0.7632 Intermediate Similarity NPC306740
0.7629 Intermediate Similarity NPC103387
0.7624 Intermediate Similarity NPC173443
0.7619 Intermediate Similarity NPC270654
0.7615 Intermediate Similarity NPC269457
0.7615 Intermediate Similarity NPC105899
0.7615 Intermediate Similarity NPC321670
0.7611 Intermediate Similarity NPC17693
0.7611 Intermediate Similarity NPC161611
0.7611 Intermediate Similarity NPC265002
0.7596 Intermediate Similarity NPC206764
0.7593 Intermediate Similarity NPC255676
0.7589 Intermediate Similarity NPC474157
0.7583 Intermediate Similarity NPC14141
0.7583 Intermediate Similarity NPC138798
0.757 Intermediate Similarity NPC282895
0.7568 Intermediate Similarity NPC475282
0.7568 Intermediate Similarity NPC317305
0.7561 Intermediate Similarity NPC301857
0.7551 Intermediate Similarity NPC172984
0.7551 Intermediate Similarity NPC44830
0.7547 Intermediate Similarity NPC260000
0.7545 Intermediate Similarity NPC317592
0.7545 Intermediate Similarity NPC119271
0.7544 Intermediate Similarity NPC11824
0.7544 Intermediate Similarity NPC237366
0.7522 Intermediate Similarity NPC212718
0.7522 Intermediate Similarity NPC185840
0.7521 Intermediate Similarity NPC471033
0.7521 Intermediate Similarity NPC246166
0.7521 Intermediate Similarity NPC311091
0.75 Intermediate Similarity NPC128249
0.75 Intermediate Similarity NPC188895
0.75 Intermediate Similarity NPC223351
0.75 Intermediate Similarity NPC108286
0.75 Intermediate Similarity NPC318107
0.7478 Intermediate Similarity NPC221870
0.7477 Intermediate Similarity NPC98911
0.7477 Intermediate Similarity NPC56493
0.7477 Intermediate Similarity NPC203925
0.7477 Intermediate Similarity NPC228435
0.7477 Intermediate Similarity NPC475465
0.7477 Intermediate Similarity NPC472314
0.7477 Intermediate Similarity NPC20485
0.7477 Intermediate Similarity NPC472318
0.7477 Intermediate Similarity NPC249811
0.7477 Intermediate Similarity NPC171843
0.7474 Intermediate Similarity NPC66655
0.7459 Intermediate Similarity NPC123704
0.7459 Intermediate Similarity NPC79608
0.7456 Intermediate Similarity NPC474176
0.7456 Intermediate Similarity NPC128368
0.7455 Intermediate Similarity NPC209632
0.7453 Intermediate Similarity NPC325499
0.7451 Intermediate Similarity NPC1793
0.7438 Intermediate Similarity NPC236981
0.7434 Intermediate Similarity NPC210089
0.7434 Intermediate Similarity NPC63345
0.7434 Intermediate Similarity NPC222084
0.7431 Intermediate Similarity NPC234305
0.7431 Intermediate Similarity NPC89886
0.7417 Intermediate Similarity NPC322332
0.7411 Intermediate Similarity NPC10251
0.7411 Intermediate Similarity NPC17417
0.7411 Intermediate Similarity NPC469511
0.7407 Intermediate Similarity NPC158623
0.7402 Intermediate Similarity NPC129889
0.7402 Intermediate Similarity NPC477281
0.7402 Intermediate Similarity NPC477280
0.7402 Intermediate Similarity NPC19719
0.7402 Intermediate Similarity NPC307006
0.7391 Intermediate Similarity NPC109241
0.7391 Intermediate Similarity NPC307651
0.7387 Intermediate Similarity NPC30594
0.7387 Intermediate Similarity NPC477251
0.7387 Intermediate Similarity NPC1065
0.7387 Intermediate Similarity NPC37622
0.7383 Intermediate Similarity NPC317280
0.7383 Intermediate Similarity NPC329387
0.7381 Intermediate Similarity NPC233692
0.7377 Intermediate Similarity NPC244454
0.7377 Intermediate Similarity NPC317163
0.7373 Intermediate Similarity NPC94298
0.7373 Intermediate Similarity NPC27633
0.7373 Intermediate Similarity NPC94637
0.7368 Intermediate Similarity NPC477250
0.7368 Intermediate Similarity NPC471188

  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 NPC160382 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
0.9579 High Similarity NPD9495 Approved
0.8962 High Similarity NPD2629 Approved
0.819 Intermediate Similarity NPD1237 Approved
0.8158 Intermediate Similarity NPD5306 Approved
0.8158 Intermediate Similarity NPD5305 Approved
0.8108 Intermediate Similarity NPD690 Clinical (unspecified phase)
0.8105 Intermediate Similarity NPD9491 Approved
0.8087 Intermediate Similarity NPD4135 Approved
0.8087 Intermediate Similarity NPD4136 Approved
0.8087 Intermediate Similarity NPD4106 Approved
0.8051 Intermediate Similarity NPD2626 Approved
0.8051 Intermediate Similarity NPD2625 Approved
0.8051 Intermediate Similarity NPD2627 Approved
0.8051 Intermediate Similarity NPD2160 Approved
0.8051 Intermediate Similarity NPD2628 Approved
0.8051 Intermediate Similarity NPD2159 Approved
0.8017 Intermediate Similarity NPD4806 Approved
0.8017 Intermediate Similarity NPD4807 Approved
0.7913 Intermediate Similarity NPD4105 Approved
0.7913 Intermediate Similarity NPD4102 Approved
0.79 Intermediate Similarity NPD9258 Approved
0.79 Intermediate Similarity NPD9256 Approved
0.7818 Intermediate Similarity NPD2067 Discontinued
0.78 Intermediate Similarity NPD800 Approved
0.7769 Intermediate Similarity NPD5204 Approved
0.7769 Intermediate Similarity NPD3664 Approved
0.7769 Intermediate Similarity NPD3662 Phase 3
0.7769 Intermediate Similarity NPD3663 Approved
0.7769 Intermediate Similarity NPD3661 Approved
0.7757 Intermediate Similarity NPD6647 Phase 2
0.7723 Intermediate Similarity NPD1089 Approved
0.7723 Intermediate Similarity NPD1086 Approved
0.7723 Intermediate Similarity NPD1090 Approved
0.7708 Intermediate Similarity NPD226 Approved
0.7705 Intermediate Similarity NPD4620 Approved
0.7705 Intermediate Similarity NPD5201 Approved
0.7705 Intermediate Similarity NPD5203 Approved
0.7705 Intermediate Similarity NPD4617 Approved
0.7684 Intermediate Similarity NPD9490 Approved
0.7642 Intermediate Similarity NPD1238 Approved
0.7596 Intermediate Similarity NPD1693 Approved
0.7589 Intermediate Similarity NPD2181 Clinical (unspecified phase)
0.7573 Intermediate Similarity NPD1088 Approved
0.7565 Intermediate Similarity NPD4198 Discontinued
0.7561 Intermediate Similarity NPD5202 Clinical (unspecified phase)
0.7524 Intermediate Similarity NPD1989 Approved
0.7522 Intermediate Similarity NPD969 Suspended
0.75 Intermediate Similarity NPD9257 Approved
0.75 Intermediate Similarity NPD9259 Approved
0.75 Intermediate Similarity NPD694 Clinical (unspecified phase)
0.7476 Intermediate Similarity NPD1239 Approved
0.7474 Intermediate Similarity NPD9294 Approved
0.746 Intermediate Similarity NPD5120 Approved
0.746 Intermediate Similarity NPD5119 Approved
0.746 Intermediate Similarity NPD5121 Approved
0.7455 Intermediate Similarity NPD5048 Discontinued
0.744 Intermediate Similarity NPD4621 Approved
0.744 Intermediate Similarity NPD4619 Approved
0.7431 Intermediate Similarity NPD5738 Clinical (unspecified phase)
0.7426 Intermediate Similarity NPD1087 Approved
0.7411 Intermediate Similarity NPD6831 Clinical (unspecified phase)
0.7411 Intermediate Similarity NPD2182 Approved
0.7396 Intermediate Similarity NPD225 Approved
0.7396 Intermediate Similarity NPD227 Approved
0.7379 Intermediate Similarity NPD3672 Approved
0.7379 Intermediate Similarity NPD3673 Approved
0.7373 Intermediate Similarity NPD9545 Approved
0.7364 Intermediate Similarity NPD164 Approved
0.7333 Intermediate Similarity NPD1202 Approved
0.7323 Intermediate Similarity NPD6311 Approved
0.7323 Intermediate Similarity NPD6310 Approved
0.7323 Intermediate Similarity NPD6309 Approved
0.7315 Intermediate Similarity NPD2066 Phase 3
0.7315 Intermediate Similarity NPD7798 Approved
0.7302 Intermediate Similarity NPD6798 Discontinued
0.729 Intermediate Similarity NPD1566 Phase 3
0.729 Intermediate Similarity NPD1565 Approved
0.729 Intermediate Similarity NPD1564 Approved
0.7282 Intermediate Similarity NPD5347 Phase 2
0.7282 Intermediate Similarity NPD5346 Phase 2
0.7264 Intermediate Similarity NPD688 Clinical (unspecified phase)
0.7255 Intermediate Similarity NPD4793 Discontinued
0.7244 Intermediate Similarity NPD4062 Phase 3
0.7244 Intermediate Similarity NPD6233 Phase 2
0.7236 Intermediate Similarity NPD5667 Approved
0.7207 Intermediate Similarity NPD5909 Discontinued
0.7203 Intermediate Similarity NPD9493 Approved
0.717 Intermediate Similarity NPD5122 Clinical (unspecified phase)
0.7168 Intermediate Similarity NPD9532 Phase 3
0.7132 Intermediate Similarity NPD6355 Discontinued
0.712 Intermediate Similarity NPD6007 Clinical (unspecified phase)
0.712 Intermediate Similarity NPD5647 Approved
0.7117 Intermediate Similarity NPD1929 Approved
0.7117 Intermediate Similarity NPD1930 Approved
0.7117 Intermediate Similarity NPD1931 Clinical (unspecified phase)
0.7094 Intermediate Similarity NPD2652 Approved
0.7094 Intermediate Similarity NPD2650 Approved
0.709 Intermediate Similarity NPD2575 Approved
0.7087 Intermediate Similarity NPD5952 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD1894 Discontinued
0.708 Intermediate Similarity NPD6685 Approved
0.7045 Intermediate Similarity NPD4173 Approved
0.7045 Intermediate Similarity NPD4172 Approved
0.7043 Intermediate Similarity NPD4233 Approved
0.7043 Intermediate Similarity NPD4234 Approved
0.7034 Intermediate Similarity NPD5951 Approved
0.7025 Intermediate Similarity NPD446 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD9267 Approved
0.7018 Intermediate Similarity NPD9263 Approved
0.7018 Intermediate Similarity NPD9264 Approved
0.7018 Intermediate Similarity NPD290 Approved
0.7018 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7009 Intermediate Similarity NPD1563 Approved
0.7009 Intermediate Similarity NPD5277 Phase 2
0.6984 Remote Similarity NPD5740 Clinical (unspecified phase)
0.6984 Remote Similarity NPD6085 Phase 2
0.6975 Remote Similarity NPD256 Approved
0.6975 Remote Similarity NPD255 Approved
0.6957 Remote Similarity NPD74 Approved
0.6957 Remote Similarity NPD9266 Approved
0.6952 Remote Similarity NPD689 Discontinued
0.6949 Remote Similarity NPD6010 Discontinued
0.6944 Remote Similarity NPD9260 Approved
0.6923 Remote Similarity NPD9508 Approved
0.6923 Remote Similarity NPD1282 Approved
0.6917 Remote Similarity NPD1501 Clinical (unspecified phase)
0.6909 Remote Similarity NPD9612 Approved
0.6909 Remote Similarity NPD9611 Approved
0.6909 Remote Similarity NPD9609 Approved
0.6855 Remote Similarity NPD4216 Approved
0.6855 Remote Similarity NPD2609 Approved
0.6855 Remote Similarity NPD2610 Approved
0.6855 Remote Similarity NPD2612 Approved
0.6855 Remote Similarity NPD4217 Approved
0.6855 Remote Similarity NPD4218 Approved
0.6855 Remote Similarity NPD4215 Approved
0.6855 Remote Similarity NPD3132 Approved
0.6855 Remote Similarity NPD2611 Approved
0.6855 Remote Similarity NPD2608 Approved
0.6855 Remote Similarity NPD3131 Approved
0.6852 Remote Similarity NPD1066 Discontinued
0.6838 Remote Similarity NPD4141 Clinical (unspecified phase)
0.6838 Remote Similarity NPD4628 Phase 3
0.6822 Remote Similarity NPD7008 Discontinued
0.6818 Remote Similarity NPD6653 Approved
0.6815 Remote Similarity NPD4534 Discontinued
0.6814 Remote Similarity NPD5765 Approved
0.681 Remote Similarity NPD2684 Approved
0.6807 Remote Similarity NPD1241 Discontinued
0.68 Remote Similarity NPD1481 Phase 2
0.68 Remote Similarity NPD9717 Approved
0.68 Remote Similarity NPD1608 Approved
0.6794 Remote Similarity NPD825 Approved
0.6794 Remote Similarity NPD826 Approved
0.6794 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6783 Remote Similarity NPD467 Phase 1
0.6777 Remote Similarity NPD9568 Approved
0.6752 Remote Similarity NPD1756 Approved
0.6752 Remote Similarity NPD1752 Approved
0.6746 Remote Similarity NPD5158 Clinical (unspecified phase)
0.6746 Remote Similarity NPD5157 Phase 1
0.6746 Remote Similarity NPD5159 Phase 2
0.6742 Remote Similarity NPD555 Phase 2
0.6735 Remote Similarity NPD9716 Approved
0.6727 Remote Similarity NPD5206 Clinical (unspecified phase)
0.6726 Remote Similarity NPD855 Approved
0.6726 Remote Similarity NPD854 Approved
0.6726 Remote Similarity NPD1932 Approved
0.6724 Remote Similarity NPD1358 Approved
0.6721 Remote Similarity NPD1758 Phase 1
0.672 Remote Similarity NPD1535 Discovery
0.6718 Remote Similarity NPD7714 Approved
0.6718 Remote Similarity NPD7715 Approved
0.6718 Remote Similarity NPD6663 Approved
0.6696 Remote Similarity NPD9712 Approved
0.6694 Remote Similarity NPD7163 Clinical (unspecified phase)
0.6694 Remote Similarity NPD1778 Approved
0.6693 Remote Similarity NPD1283 Approved
0.6692 Remote Similarity NPD4738 Phase 2
0.6692 Remote Similarity NPD3528 Clinical (unspecified phase)
0.6691 Remote Similarity NPD5958 Discontinued
0.6667 Remote Similarity NPD1759 Phase 1
0.6667 Remote Similarity NPD9261 Approved
0.6667 Remote Similarity NPD6190 Approved
0.6667 Remote Similarity NPD2240 Approved
0.6667 Remote Similarity NPD2239 Approved
0.6667 Remote Similarity NPD454 Approved
0.6667 Remote Similarity NPD5736 Approved
0.6667 Remote Similarity NPD9566 Approved
0.6667 Remote Similarity NPD5700 Clinical (unspecified phase)
0.6641 Remote Similarity NPD2797 Approved
0.6641 Remote Similarity NPD987 Approved
0.6639 Remote Similarity NPD6912 Phase 3
0.6639 Remote Similarity NPD4576 Approved
0.6639 Remote Similarity NPD4574 Approved
0.6639 Remote Similarity NPD1609 Clinical (unspecified phase)
0.6636 Remote Similarity NPD2934 Approved
0.6636 Remote Similarity NPD2933 Approved
0.6617 Remote Similarity NPD230 Phase 1
0.6612 Remote Similarity NPD9281 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