Structure

Physi-Chem Properties

Molecular Weight:  150.07
Volume:  162.698
LogP:  1.938
LogD:  1.898
LogS:  -2.238
# Rotatable Bonds:  3
TPSA:  26.3
# H-Bond Aceptor:  2
# H-Bond Donor:  0
# Rings:  1
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.596
Synthetic Accessibility Score:  1.293
Fsp3:  0.222
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:  -4.352
MDCK Permeability:  5.4859650845173746e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.006
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.002
30% Bioavailability (F30%):  0.761

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.976
Plasma Protein Binding (PPB):  45.523155212402344%
Volume Distribution (VD):  0.571
Pgp-substrate:  34.125755310058594%

ADMET: Metabolism

CYP1A2-inhibitor:  0.834
CYP1A2-substrate:  0.352
CYP2C19-inhibitor:  0.734
CYP2C19-substrate:  0.711
CYP2C9-inhibitor:  0.214
CYP2C9-substrate:  0.315
CYP2D6-inhibitor:  0.01
CYP2D6-substrate:  0.312
CYP3A4-inhibitor:  0.041
CYP3A4-substrate:  0.407

ADMET: Excretion

Clearance (CL):  12.557
Half-life (T1/2):  0.888

ADMET: Toxicity

hERG Blockers:  0.035
Human Hepatotoxicity (H-HT):  0.237
Drug-inuced Liver Injury (DILI):  0.804
AMES Toxicity:  0.075
Rat Oral Acute Toxicity:  0.054
Maximum Recommended Daily Dose:  0.013
Skin Sensitization:  0.449
Carcinogencity:  0.287
Eye Corrosion:  0.812
Eye Irritation:  0.958
Respiratory Toxicity:  0.07

Download Data

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  Natural Product: NPC288903

Natural Product ID:  NPC288903
Common Name*:   Methyl 2-Phenylacetate
IUPAC Name:   methyl 2-phenylacetate
Synonyms:  
Standard InCHIKey:  CRZQGDNQQAALAY-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C9H10O2/c1-11-9(10)7-8-5-3-2-4-6-8/h2-6H,7H2,1H3
SMILES:  COC(=O)Cc1ccccc1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3189123
PubChem CID:   7559
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
NPO15810 Zea mays Species Poaceae Eukaryota n.a. n.a. DOI[10.1021/jf00055a023]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. cone n.a. PMID[10336650]
NPO15810 Zea mays Species Poaceae Eukaryota n.a. seed n.a. PMID[11539687]
NPO15810 Zea mays Species Poaceae Eukaryota n.a. n.a. n.a. PMID[12713418]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. n.a. PMID[1402962]
NPO9290 Zanthoxylum piperitum Species Rutaceae Eukaryota n.a. leaf n.a. PMID[15388977]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[15679315]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[16252923]
NPO9290 Zanthoxylum piperitum Species Rutaceae Eukaryota n.a. stem n.a. PMID[17202689]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. cone n.a. PMID[17624889]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[18611049]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[18768384]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[19476340]
NPO9290 Zanthoxylum piperitum Species Rutaceae Eukaryota n.a. pericarp n.a. PMID[20628994]
NPO15810 Zea mays Species Poaceae Eukaryota n.a. n.a. n.a. PMID[21080643]
NPO15810 Zea mays Species Poaceae Eukaryota n.a. husk n.a. PMID[21574561]
NPO15810 Zea mays Species Poaceae Eukaryota n.a. leaf n.a. PMID[21574561]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[21912858]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. cone n.a. PMID[22111577]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. flower n.a. PMID[22166201]
NPO15810 Zea mays Species Poaceae Eukaryota n.a. seed n.a. PMID[23292602]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[23790907]
NPO5315 Zanthoxylum bungeanum Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[24175626]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[24948953]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[25564559]
NPO18951 Ligusticum sinense Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[26521454]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota Flower Buds n.a. n.a. PMID[26977531]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[29154541]
NPO15810 Zea mays Species Poaceae Eukaryota n.a. n.a. n.a. PMID[29762032]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. n.a. PMID[8904847]
NPO15810 Zea mays Species Poaceae Eukaryota n.a. pollen n.a. PMID[8987503]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota Stem n.a. n.a. Database[FooDB]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota Bark n.a. n.a. Database[FooDB]
NPO15810 Zea mays Species Poaceae Eukaryota Stem n.a. n.a. Database[FooDB]
NPO15810 Zea mays Species Poaceae Eukaryota Cob n.a. n.a. Database[FooDB]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. Database[FooDB]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota Essential Oil n.a. n.a. Database[FooDB]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. Database[FooDB]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO15810 Zea mays Species Poaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO15810 Zea mays Species Poaceae Eukaryota Husk Essent. Oil n.a. n.a. Database[FooDB]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO15810 Zea mays Species Poaceae Eukaryota Oil n.a. n.a. Database[FooDB]
NPO15810 Zea mays Species Poaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO15810 Zea mays Species Poaceae Eukaryota Pollen Or Spore n.a. n.a. Database[FooDB]
NPO15810 Zea mays Species Poaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO15810 Zea mays Species Poaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO15810 Zea mays Species Poaceae Eukaryota Seed Essent. Oil n.a. n.a. Database[FooDB]
NPO15810 Zea mays Species Poaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO15810 Zea mays Species Poaceae Eukaryota Silk Essent. Oil n.a. n.a. Database[FooDB]
NPO15810 Zea mays Species Poaceae Eukaryota Silk Stigma Style n.a. n.a. Database[FooDB]
NPO15810 Zea mays Species Poaceae Eukaryota n.a. n.a. Database[FooDB]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18951 Ligusticum sinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15810 Zea mays Species Poaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8698 Zanthoxylum schinifolium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO31073 Ligusticum chuanxiong Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5315 Zanthoxylum bungeanum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9290 Zanthoxylum piperitum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15810 Zea mays Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5315 Zanthoxylum bungeanum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9290 Zanthoxylum piperitum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18951 Ligusticum sinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8698 Zanthoxylum schinifolium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9290 Zanthoxylum piperitum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5315 Zanthoxylum bungeanum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15810 Zea mays Species Poaceae 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]
NPO31073 Ligusticum chuanxiong Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8698 Zanthoxylum schinifolium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5315 Zanthoxylum bungeanum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8698 Zanthoxylum schinifolium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15810 Zea mays Species Poaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO3987 Syzygium aromaticum Species Myrtaceae 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]
NPO9290 Zanthoxylum piperitum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8698 Zanthoxylum schinifolium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5315 Zanthoxylum bungeanum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9290 Zanthoxylum piperitum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18951 Ligusticum sinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15810 Zea mays Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3987 Syzygium aromaticum Species Myrtaceae 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
NPO15810 NPC288903 Raw Silk Essent. Oil 3500 3000 4000 mg/100g Database [DUKE]
NPO21556 NPC288903 n.a. Sclerotia 8.888 ± 2.103 n.a. n.a. % PMID[20527951]

☑ 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
NPT2 Others Unspecified Potency n.a. 49 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 48966.2 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 NPC288903 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
0.9747 High Similarity NPC294134
0.925 High Similarity NPC285773
0.9125 High Similarity NPC323103
0.9114 High Similarity NPC121800
0.9048 High Similarity NPC9822
0.9036 High Similarity NPC322387
0.9012 High Similarity NPC270507
0.8987 High Similarity NPC170484
0.8929 High Similarity NPC329064
0.8889 High Similarity NPC103387
0.8875 High Similarity NPC127343
0.8721 High Similarity NPC70940
0.8721 High Similarity NPC86670
0.8721 High Similarity NPC274455
0.8571 High Similarity NPC95965
0.8554 High Similarity NPC44830
0.8539 High Similarity NPC130398
0.8409 Intermediate Similarity NPC317645
0.8372 Intermediate Similarity NPC89377
0.8352 Intermediate Similarity NPC270654
0.8352 Intermediate Similarity NPC249912
0.8352 Intermediate Similarity NPC276775
0.8352 Intermediate Similarity NPC92754
0.8295 Intermediate Similarity NPC84288
0.8261 Intermediate Similarity NPC35448
0.8261 Intermediate Similarity NPC225060
0.8261 Intermediate Similarity NPC78701
0.8256 Intermediate Similarity NPC318107
0.8228 Intermediate Similarity NPC285679
0.8202 Intermediate Similarity NPC110704
0.8182 Intermediate Similarity NPC220893
0.8172 Intermediate Similarity NPC146351
0.8172 Intermediate Similarity NPC203925
0.814 Intermediate Similarity NPC58616
0.8132 Intermediate Similarity NPC172925
0.8125 Intermediate Similarity NPC208075
0.8105 Intermediate Similarity NPC160382
0.8101 Intermediate Similarity NPC74458
0.8085 Intermediate Similarity NPC42211
0.8085 Intermediate Similarity NPC473325
0.8085 Intermediate Similarity NPC70624
0.8068 Intermediate Similarity NPC304760
0.8065 Intermediate Similarity NPC229242
0.8065 Intermediate Similarity NPC210529
0.8065 Intermediate Similarity NPC160548
0.8065 Intermediate Similarity NPC175852
0.8022 Intermediate Similarity NPC261181
0.8021 Intermediate Similarity NPC31786
0.8 Intermediate Similarity NPC476484
0.8 Intermediate Similarity NPC271437
0.8 Intermediate Similarity NPC188895
0.7979 Intermediate Similarity NPC325497
0.7979 Intermediate Similarity NPC118343
0.7979 Intermediate Similarity NPC217621
0.7979 Intermediate Similarity NPC7435
0.7978 Intermediate Similarity NPC173443
0.7978 Intermediate Similarity NPC231591
0.7957 Intermediate Similarity NPC253423
0.7957 Intermediate Similarity NPC226041
0.7931 Intermediate Similarity NPC475710
0.7917 Intermediate Similarity NPC301943
0.7917 Intermediate Similarity NPC474365
0.7889 Intermediate Similarity NPC62765
0.7889 Intermediate Similarity NPC185501
0.7875 Intermediate Similarity NPC155429
0.7857 Intermediate Similarity NPC300205
0.7857 Intermediate Similarity NPC1065
0.7857 Intermediate Similarity NPC119271
0.7849 Intermediate Similarity NPC12695
0.7849 Intermediate Similarity NPC261947
0.7831 Intermediate Similarity NPC298023
0.7812 Intermediate Similarity NPC25458
0.7812 Intermediate Similarity NPC304873
0.7802 Intermediate Similarity NPC86987
0.7789 Intermediate Similarity NPC476042
0.7789 Intermediate Similarity NPC221825
0.7778 Intermediate Similarity NPC56493
0.7766 Intermediate Similarity NPC103048
0.7765 Intermediate Similarity NPC164086
0.7755 Intermediate Similarity NPC209632
0.7753 Intermediate Similarity NPC96625
0.7738 Intermediate Similarity NPC137847
0.7738 Intermediate Similarity NPC36342
0.7738 Intermediate Similarity NPC285470
0.7738 Intermediate Similarity NPC76455
0.7738 Intermediate Similarity NPC2785
0.7732 Intermediate Similarity NPC60679
0.7732 Intermediate Similarity NPC329556
0.7732 Intermediate Similarity NPC89886
0.7717 Intermediate Similarity NPC323164
0.7711 Intermediate Similarity NPC175393
0.7708 Intermediate Similarity NPC52472
0.7708 Intermediate Similarity NPC112552
0.77 Intermediate Similarity NPC83628
0.77 Intermediate Similarity NPC281604
0.77 Intermediate Similarity NPC17417
0.77 Intermediate Similarity NPC85493
0.77 Intermediate Similarity NPC10251
0.77 Intermediate Similarity NPC469636
0.77 Intermediate Similarity NPC265407
0.7692 Intermediate Similarity NPC213156
0.7692 Intermediate Similarity NPC240108
0.7684 Intermediate Similarity NPC271475
0.7683 Intermediate Similarity NPC108218
0.7677 Intermediate Similarity NPC30594
0.7677 Intermediate Similarity NPC37622
0.766 Intermediate Similarity NPC61944
0.7653 Intermediate Similarity NPC114594
0.7653 Intermediate Similarity NPC269644
0.7629 Intermediate Similarity NPC45613
0.7629 Intermediate Similarity NPC474112
0.7629 Intermediate Similarity NPC284477
0.7624 Intermediate Similarity NPC158854
0.7624 Intermediate Similarity NPC174099
0.7624 Intermediate Similarity NPC214067
0.7624 Intermediate Similarity NPC196246
0.7624 Intermediate Similarity NPC251854
0.7624 Intermediate Similarity NPC93084
0.7624 Intermediate Similarity NPC234639
0.7619 Intermediate Similarity NPC287790
0.7619 Intermediate Similarity NPC3672
0.7619 Intermediate Similarity NPC245966
0.7619 Intermediate Similarity NPC329318
0.7604 Intermediate Similarity NPC245561
0.759 Intermediate Similarity NPC189371
0.7579 Intermediate Similarity NPC477767
0.7576 Intermediate Similarity NPC476198
0.7576 Intermediate Similarity NPC105899
0.7576 Intermediate Similarity NPC269457
0.7558 Intermediate Similarity NPC190567
0.7558 Intermediate Similarity NPC157055
0.7551 Intermediate Similarity NPC255676
0.7551 Intermediate Similarity NPC13426
0.7549 Intermediate Similarity NPC1082
0.7549 Intermediate Similarity NPC210089
0.7549 Intermediate Similarity NPC260818
0.7549 Intermediate Similarity NPC474157
0.7549 Intermediate Similarity NPC305912
0.7529 Intermediate Similarity NPC103488
0.7529 Intermediate Similarity NPC224544
0.7527 Intermediate Similarity NPC77273
0.7526 Intermediate Similarity NPC282895
0.7525 Intermediate Similarity NPC474364
0.7525 Intermediate Similarity NPC99846
0.7525 Intermediate Similarity NPC269023
0.7525 Intermediate Similarity NPC31274
0.75 Intermediate Similarity NPC142326
0.75 Intermediate Similarity NPC197581
0.75 Intermediate Similarity NPC94751
0.75 Intermediate Similarity NPC145052
0.75 Intermediate Similarity NPC39600
0.75 Intermediate Similarity NPC322598
0.7476 Intermediate Similarity NPC321852
0.7476 Intermediate Similarity NPC270699
0.7476 Intermediate Similarity NPC82899
0.7475 Intermediate Similarity NPC19136
0.7475 Intermediate Similarity NPC38209
0.7473 Intermediate Similarity NPC477693
0.7473 Intermediate Similarity NPC477704
0.7471 Intermediate Similarity NPC73978
0.7471 Intermediate Similarity NPC145053
0.7471 Intermediate Similarity NPC100039
0.7447 Intermediate Similarity NPC23453
0.7447 Intermediate Similarity NPC34243
0.7442 Intermediate Similarity NPC272260
0.7442 Intermediate Similarity NPC78517
0.7442 Intermediate Similarity NPC167577
0.7439 Intermediate Similarity NPC208302
0.7426 Intermediate Similarity NPC156648
0.7426 Intermediate Similarity NPC249811
0.7423 Intermediate Similarity NPC280869
0.7423 Intermediate Similarity NPC12730
0.7423 Intermediate Similarity NPC228435
0.7419 Intermediate Similarity NPC141607
0.7419 Intermediate Similarity NPC187725
0.7419 Intermediate Similarity NPC119631
0.7412 Intermediate Similarity NPC9796
0.7404 Intermediate Similarity NPC272524
0.7404 Intermediate Similarity NPC128368
0.74 Intermediate Similarity NPC13495
0.7396 Intermediate Similarity NPC293628
0.7396 Intermediate Similarity NPC10781
0.7396 Intermediate Similarity NPC289201
0.7396 Intermediate Similarity NPC122493
0.7396 Intermediate Similarity NPC325499
0.7396 Intermediate Similarity NPC324569
0.7386 Intermediate Similarity NPC106313
0.7386 Intermediate Similarity NPC230068
0.7379 Intermediate Similarity NPC476003
0.7379 Intermediate Similarity NPC167504
0.7374 Intermediate Similarity NPC298224
0.7356 Intermediate Similarity NPC477703
0.7356 Intermediate Similarity NPC71664
0.7356 Intermediate Similarity NPC328178
0.7356 Intermediate Similarity NPC285716
0.7356 Intermediate Similarity NPC17408
0.7356 Intermediate Similarity NPC309279
0.7356 Intermediate Similarity NPC95868
0.7347 Intermediate Similarity NPC128248
0.7347 Intermediate Similarity NPC264728

  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 NPC288903 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
0.9481 High Similarity NPD9490 Approved
0.925 High Similarity NPD9491 Approved
0.9103 High Similarity NPD225 Approved
0.9103 High Similarity NPD227 Approved
0.9036 High Similarity NPD1087 Approved
0.8824 High Similarity NPD800 Approved
0.8765 High Similarity NPD226 Approved
0.8721 High Similarity NPD1089 Approved
0.8721 High Similarity NPD1086 Approved
0.8721 High Similarity NPD1090 Approved
0.8652 High Similarity NPD1989 Approved
0.8523 High Similarity NPD1088 Approved
0.8506 High Similarity NPD3672 Approved
0.8506 High Similarity NPD3673 Approved
0.8427 Intermediate Similarity NPD1563 Approved
0.8409 Intermediate Similarity NPD1239 Approved
0.8333 Intermediate Similarity NPD1693 Approved
0.8256 Intermediate Similarity NPD9259 Approved
0.8256 Intermediate Similarity NPD9257 Approved
0.8182 Intermediate Similarity NPD5347 Phase 2
0.8182 Intermediate Similarity NPD5346 Phase 2
0.8161 Intermediate Similarity NPD4793 Discontinued
0.8152 Intermediate Similarity NPD1566 Phase 3
0.8152 Intermediate Similarity NPD1564 Approved
0.8152 Intermediate Similarity NPD1565 Approved
0.8132 Intermediate Similarity NPD688 Clinical (unspecified phase)
0.8065 Intermediate Similarity NPD9495 Approved
0.8022 Intermediate Similarity NPD1202 Approved
0.8021 Intermediate Similarity NPD164 Approved
0.7979 Intermediate Similarity NPD1238 Approved
0.7979 Intermediate Similarity NPD2066 Phase 3
0.7889 Intermediate Similarity NPD9256 Approved
0.7889 Intermediate Similarity NPD9258 Approved
0.7826 Intermediate Similarity NPD5122 Clinical (unspecified phase)
0.7732 Intermediate Similarity NPD1930 Approved
0.7732 Intermediate Similarity NPD1931 Clinical (unspecified phase)
0.7732 Intermediate Similarity NPD1929 Approved
0.77 Intermediate Similarity NPD2182 Approved
0.7624 Intermediate Similarity NPD4234 Approved
0.7624 Intermediate Similarity NPD1756 Approved
0.7624 Intermediate Similarity NPD4233 Approved
0.7624 Intermediate Similarity NPD1752 Approved
0.7604 Intermediate Similarity NPD7798 Approved
0.7553 Intermediate Similarity NPD9260 Approved
0.7549 Intermediate Similarity NPD2181 Clinical (unspecified phase)
0.7474 Intermediate Similarity NPD5206 Clinical (unspecified phase)
0.7451 Intermediate Similarity NPD2067 Discontinued
0.7451 Intermediate Similarity NPD3646 Clinical (unspecified phase)
0.7447 Intermediate Similarity NPD1066 Discontinued
0.7404 Intermediate Similarity NPD1279 Clinical (unspecified phase)
0.7404 Intermediate Similarity NPD2607 Approved
0.7396 Intermediate Similarity NPD9566 Approved
0.7356 Intermediate Similarity NPD1507 Clinical (unspecified phase)
0.7353 Intermediate Similarity NPD6831 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD1371 Approved
0.7333 Intermediate Similarity NPD1373 Approved
0.7333 Intermediate Similarity NPD1370 Approved
0.7333 Intermediate Similarity NPD1374 Approved
0.7333 Intermediate Similarity NPD2650 Approved
0.7333 Intermediate Similarity NPD2652 Approved
0.732 Intermediate Similarity NPD253 Approved
0.73 Intermediate Similarity NPD5909 Discontinued
0.7273 Intermediate Similarity NPD1932 Approved
0.7273 Intermediate Similarity NPD942 Approved
0.7264 Intermediate Similarity NPD2629 Approved
0.7264 Intermediate Similarity NPD4766 Approved
0.7245 Intermediate Similarity NPD3097 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD6647 Phase 2
0.7176 Intermediate Similarity NPD9716 Approved
0.7174 Intermediate Similarity NPD650 Approved
0.7174 Intermediate Similarity NPD1282 Approved
0.713 Intermediate Similarity NPD4574 Approved
0.713 Intermediate Similarity NPD4576 Approved
0.7129 Intermediate Similarity NPD1237 Approved
0.7103 Intermediate Similarity NPD690 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD531 Approved
0.7075 Intermediate Similarity NPD181 Approved
0.7064 Intermediate Similarity NPD2347 Approved
0.7059 Intermediate Similarity NPD5048 Discontinued
0.703 Intermediate Similarity NPD5738 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD9261 Approved
0.7019 Intermediate Similarity NPD2329 Discontinued
0.7011 Intermediate Similarity NPD9294 Approved
0.7009 Intermediate Similarity NPD1280 Clinical (unspecified phase)
0.699 Remote Similarity NPD467 Phase 1
0.699 Remote Similarity NPD6685 Approved
0.6989 Remote Similarity NPD506 Clinical (unspecified phase)
0.6972 Remote Similarity NPD9493 Approved
0.697 Remote Similarity NPD5926 Approved
0.6952 Remote Similarity NPD1317 Discontinued
0.6944 Remote Similarity NPD5951 Approved
0.6944 Remote Similarity NPD1246 Approved
0.6923 Remote Similarity NPD3971 Phase 1
0.6916 Remote Similarity NPD7094 Approved
0.6916 Remote Similarity NPD5277 Phase 2
0.6916 Remote Similarity NPD6858 Approved
0.6893 Remote Similarity NPD1040 Phase 2
0.6875 Remote Similarity NPD7609 Phase 3
0.6875 Remote Similarity NPD5306 Approved
0.6875 Remote Similarity NPD5305 Approved
0.6863 Remote Similarity NPD5765 Approved
0.6852 Remote Similarity NPD1241 Discontinued
0.6847 Remote Similarity NPD9545 Approved
0.6827 Remote Similarity NPD5705 Approved
0.6827 Remote Similarity NPD5704 Approved
0.6827 Remote Similarity NPD5706 Approved
0.6822 Remote Similarity NPD1609 Clinical (unspecified phase)
0.6822 Remote Similarity NPD9508 Approved
0.6814 Remote Similarity NPD4106 Approved
0.6814 Remote Similarity NPD4136 Approved
0.6814 Remote Similarity NPD4135 Approved
0.6804 Remote Similarity NPD7631 Approved
0.6792 Remote Similarity NPD5278 Discontinued
0.6786 Remote Similarity NPD4105 Approved
0.6786 Remote Similarity NPD4102 Approved
0.6774 Remote Similarity NPD5734 Clinical (unspecified phase)
0.6762 Remote Similarity NPD9265 Clinical (unspecified phase)
0.6762 Remote Similarity NPD9267 Approved
0.6762 Remote Similarity NPD9264 Approved
0.6762 Remote Similarity NPD9263 Approved
0.6754 Remote Similarity NPD3131 Approved
0.6754 Remote Similarity NPD4807 Approved
0.6754 Remote Similarity NPD3132 Approved
0.6754 Remote Similarity NPD2608 Approved
0.6754 Remote Similarity NPD2610 Approved
0.6754 Remote Similarity NPD518 Clinical (unspecified phase)
0.6754 Remote Similarity NPD7436 Approved
0.6754 Remote Similarity NPD4217 Approved
0.6754 Remote Similarity NPD2611 Approved
0.6754 Remote Similarity NPD4218 Approved
0.6754 Remote Similarity NPD4806 Approved
0.6754 Remote Similarity NPD4215 Approved
0.6754 Remote Similarity NPD4216 Approved
0.6754 Remote Similarity NPD7437 Approved
0.6754 Remote Similarity NPD2612 Approved
0.6754 Remote Similarity NPD2609 Approved
0.6754 Remote Similarity NPD6287 Discontinued
0.6754 Remote Similarity NPD1281 Approved
0.6737 Remote Similarity NPD1101 Approved
0.6731 Remote Similarity NPD1018 Approved
0.6729 Remote Similarity NPD3643 Approved
0.6729 Remote Similarity NPD3642 Approved
0.6729 Remote Similarity NPD3644 Approved
0.6727 Remote Similarity NPD1348 Approved
0.6727 Remote Similarity NPD255 Approved
0.6727 Remote Similarity NPD256 Approved
0.6726 Remote Similarity NPD17 Approved
0.6703 Remote Similarity NPD9250 Approved
0.6698 Remote Similarity NPD74 Approved
0.6698 Remote Similarity NPD9266 Approved
0.6696 Remote Similarity NPD1894 Discontinued
0.6667 Remote Similarity NPD689 Discontinued
0.6667 Remote Similarity NPD3135 Clinical (unspecified phase)
0.6637 Remote Similarity NPD1245 Approved
0.6636 Remote Similarity NPD5235 Approved
0.6636 Remote Similarity NPD5236 Approved
0.6636 Remote Similarity NPD5239 Approved
0.6636 Remote Similarity NPD5240 Approved
0.6636 Remote Similarity NPD5237 Approved
0.6633 Remote Similarity NPD1508 Approved
0.6632 Remote Similarity NPD9538 Approved
0.6607 Remote Similarity NPD2116 Approved
0.6607 Remote Similarity NPD2115 Approved
0.6607 Remote Similarity NPD2117 Pre-registration
0.6607 Remote Similarity NPD6065 Approved
0.6581 Remote Similarity NPD5667 Approved
0.6581 Remote Similarity NPD1283 Approved
0.6579 Remote Similarity NPD7163 Clinical (unspecified phase)
0.6579 Remote Similarity NPD2345 Approved
0.6574 Remote Similarity NPD4141 Clinical (unspecified phase)
0.6574 Remote Similarity NPD2201 Approved
0.6574 Remote Similarity NPD189 Phase 3
0.6574 Remote Similarity NPD188 Approved
0.6569 Remote Similarity NPD1067 Discontinued
0.6569 Remote Similarity NPD9712 Approved
0.6566 Remote Similarity NPD719 Approved
0.6566 Remote Similarity NPD720 Approved
0.6552 Remote Similarity NPD1608 Approved
0.6549 Remote Similarity NPD2994 Approved
0.6549 Remote Similarity NPD2617 Discontinued
0.6549 Remote Similarity NPD4479 Discontinued
0.6545 Remote Similarity NPD6010 Discontinued
0.6542 Remote Similarity NPD476 Approved
0.6535 Remote Similarity NPD3495 Discontinued
0.6531 Remote Similarity NPD530 Approved
0.6525 Remote Similarity NPD2628 Approved
0.6525 Remote Similarity NPD2625 Approved
0.6525 Remote Similarity NPD2626 Approved
0.6525 Remote Similarity NPD2160 Approved
0.6525 Remote Similarity NPD2627 Approved
0.6525 Remote Similarity NPD2159 Approved
0.6518 Remote Similarity NPD3797 Approved
0.6518 Remote Similarity NPD9568 Approved
0.6514 Remote Similarity NPD6912 Phase 3
0.6509 Remote Similarity NPD3134 Approved
0.65 Remote Similarity NPD4094 Approved
0.6491 Remote Similarity NPD3032 Approved
0.6491 Remote Similarity NPD5981 Approved
0.6491 Remote Similarity NPD6993 Approved
0.6491 Remote Similarity NPD1855 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