Structure

Physi-Chem Properties

Molecular Weight:  222.09
Volume:  229.53
LogP:  2.633
LogD:  3.037
LogS:  -2.367
# Rotatable Bonds:  5
TPSA:  55.76
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  1
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.625
Synthetic Accessibility Score:  1.886
Fsp3:  0.25
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.549
MDCK Permeability:  2.4665712771820836e-05
Pgp-inhibitor:  0.02
Pgp-substrate:  0.011
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.718
30% Bioavailability (F30%):  0.905

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.81
Plasma Protein Binding (PPB):  94.43073272705078%
Volume Distribution (VD):  0.729
Pgp-substrate:  6.537950038909912%

ADMET: Metabolism

CYP1A2-inhibitor:  0.978
CYP1A2-substrate:  0.904
CYP2C19-inhibitor:  0.802
CYP2C19-substrate:  0.615
CYP2C9-inhibitor:  0.67
CYP2C9-substrate:  0.904
CYP2D6-inhibitor:  0.231
CYP2D6-substrate:  0.874
CYP3A4-inhibitor:  0.291
CYP3A4-substrate:  0.414

ADMET: Excretion

Clearance (CL):  12.472
Half-life (T1/2):  0.909

ADMET: Toxicity

hERG Blockers:  0.058
Human Hepatotoxicity (H-HT):  0.062
Drug-inuced Liver Injury (DILI):  0.072
AMES Toxicity:  0.185
Rat Oral Acute Toxicity:  0.455
Maximum Recommended Daily Dose:  0.181
Skin Sensitization:  0.931
Carcinogencity:  0.617
Eye Corrosion:  0.062
Eye Irritation:  0.788
Respiratory Toxicity:  0.436

Download Data

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

  Natural Product: NPC202474

Natural Product ID:  NPC202474
Common Name*:   Ethyl Ferulate
IUPAC Name:   ethyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Synonyms:   Ethyl Ferulate
Standard InCHIKey:  ATJVZXXHKSYELS-FNORWQNLSA-N
Standard InCHI:  InChI=1S/C12H14O4/c1-3-16-12(14)7-5-9-4-6-10(13)11(8-9)15-2/h4-8,13H,3H2,1-2H3/b7-5+
SMILES:  CCOC(=O)/C=C/c1ccc(c(c1)OC)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL286796
PubChem CID:   736681
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000476] Cinnamic acids and derivatives
        • [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives
          • [CHEMONTID:0000059] Coumaric acids and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO25518 Hedychium coronarium Species Zingiberaceae Eukaryota rhizomes n.a. n.a. PMID[21106458]
NPO1168 Euphorbia sikkimensis Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[23327832]
NPO4153 Illicium dunnianum Species Schisandraceae Eukaryota n.a. leaf n.a. PMID[2504190]
NPO4153 Illicium dunnianum Species Schisandraceae Eukaryota n.a. stem n.a. PMID[2504190]
NPO1168 Euphorbia sikkimensis Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[26756779]
NPO10316 Glechoma longituba Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8976 Agave americana Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25518 Hedychium coronarium Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3908 Eupatorium formosanum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10580 Herba glechomae n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO3908 Eupatorium formosanum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8291 Hyptis fasciculata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25518 Hedychium coronarium Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8976 Agave americana Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10316 Glechoma longituba Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25518 Hedychium coronarium Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8976 Agave americana Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO10316 Glechoma longituba Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3908 Eupatorium formosanum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO10316 Glechoma longituba Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25902 Glechoma grandis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8497 Pinus insularis Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9751 Korthalsella japonica Species Viscaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14829 Anemone patens Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1168 Euphorbia sikkimensis Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4153 Illicium dunnianum Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9932 Mantella viridis Species Mantellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2231 Arisaema tortuosum Species Araceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2036 Scopolia lurida Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8976 Agave americana Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10284 Micrandropsis scleroxylon Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5883 Nassauvia revoluta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25518 Hedychium coronarium Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9879 Artemisia anethifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3908 Eupatorium formosanum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO615 Lobelia exaltata Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10316 Glechoma longituba Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8291 Hyptis fasciculata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3662 Halokirschsteiniothelia maritima Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1720 Tyrophagus similis Species Acaridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9607 Tillandsia usneoides Species Bromeliaceae 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
NPO21556 NPC202474 n.a. Sclerotia 11.29 ± 1.433 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
NPT116 Cell Line HL-60 Homo sapiens Inhibition ~ 9.0 % PMID[528716]
NPT116 Cell Line HL-60 Homo sapiens Cell viability ~ 80.0 % PMID[528716]
NPT582 Individual Protein Monoamine oxidase B Homo sapiens IC50 = 6700.0 nM PMID[528718]
NPT81 Cell Line A549 Homo sapiens GI50 = 1200.0 nM PMID[528719]
NPT81 Cell Line A549 Homo sapiens LC50 = 5800.0 nM PMID[528719]
NPT136 Cell Line SK-N-SH Homo sapiens GI50 = 22300.0 nM PMID[528719]
NPT136 Cell Line SK-N-SH Homo sapiens LC50 = 31400.0 nM PMID[528719]
NPT83 Cell Line MCF7 Homo sapiens GI50 = 86300.0 nM PMID[528719]
NPT83 Cell Line MCF7 Homo sapiens LC50 > 100000.0 nM PMID[528719]
NPT165 Cell Line HeLa Homo sapiens GI50 = 52800.0 nM PMID[528719]
NPT165 Cell Line HeLa Homo sapiens LC50 = 67800.0 nM PMID[528719]
NPT1566 Individual Protein Glyoxalase I Homo sapiens Ki = 385000.0 nM PMID[528720]
NPT165 Cell Line HeLa Homo sapiens IC50 = 2130.0 nM PMID[528721]
NPT81 Cell Line A549 Homo sapiens IC50 = 12500.0 nM PMID[528721]
NPT1669 Cell Line NCI-H1792 Homo sapiens IC50 = 25600.0 nM PMID[528721]
NPT379 Cell Line HOP-62 Homo sapiens IC50 = 26800.0 nM PMID[528721]
NPT397 Cell Line NCI-H460 Homo sapiens IC50 = 29100.0 nM PMID[528721]
NPT1668 Cell Line NCI-H157 Homo sapiens IC50 = 32300.0 nM PMID[528721]
NPT2410 Cell Line NCI-H1299 Homo sapiens IC50 = 36800.0 nM PMID[528721]
NPT1307 Cell Line Calu-1 Homo sapiens IC50 > 50000.0 nM PMID[528721]
NPT390 Cell Line LOX IMVI Homo sapiens IC50 > 50000.0 nM PMID[528721]
NPT387 Cell Line M14 Homo sapiens IC50 > 50000.0 nM PMID[528721]
NPT25 Cell Line MT4 Homo sapiens CC50 > 10000.0 nM PMID[528726]
NPT591 Individual Protein Glycogen synthase kinase-3 beta Homo sapiens Inhibition = 21.38 % PMID[528728]
NPT35 Others n.a. Activity = 0.593 n.a. PMID[528717]
NPT35 Others n.a. Activity = 2.538 n.a. PMID[528717]
NPT35 Others n.a. LogP = 2.02 n.a. PMID[528717]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 24900.0 nM PMID[528721]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 28100.0 nM PMID[528721]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 32000.0 nM PMID[528721]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 33400.0 nM PMID[528721]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. TIME = 0.04167 hr PMID[528722]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 150020.0 nM PMID[528722]
NPT722 Organism Athelia rolfsii Athelia rolfsii GI = 43.0 % PMID[528723]
NPT723 Organism Pythium Pythium GI = 50.0 % PMID[528723]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 26.5 % PMID[528724]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 17.9 % PMID[528724]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 11.5 % PMID[528724]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 4.0 % PMID[528724]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 193200.0 nM PMID[528724]
NPT35 Others n.a. K = 0.013 /uM/s PMID[528725]
NPT35 Others n.a. Activity = 0.992 n.a. PMID[528725]
NPT35 Others n.a. Activity = 0.851 n.a. PMID[528725]
NPT35 Others n.a. Activity = 0.58 n.a. PMID[528725]
NPT35 Others n.a. Activity = 19.0 % PMID[528725]
NPT35 Others n.a. Activity = 29.0 % PMID[528725]
NPT35 Others n.a. Activity = 36.0 % PMID[528725]
NPT35 Others n.a. Activity = 42.0 % PMID[528725]
NPT35 Others n.a. K = 0.14 /min PMID[528725]
NPT35 Others n.a. K = 0.16 /min PMID[528725]
NPT35 Others n.a. K = 0.13 /min PMID[528725]
NPT35 Others n.a. Activity = 1.9 n.a. PMID[528725]
NPT35 Others n.a. Activity = 1.7 n.a. PMID[528725]
NPT35 Others n.a. Activity = 1.6 n.a. PMID[528725]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 EC50 > 10000.0 nM PMID[528726]
NPT2 Others Unspecified IC50 > 100000.0 nM PMID[528727]
NPT35 Others n.a. K = 4.6 10'3/M/s PMID[528728]

☑ 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 NPC202474 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
0.9912 High Similarity NPC204466
0.9825 High Similarity NPC70752
0.9821 High Similarity NPC164706
0.9821 High Similarity NPC137537
0.9821 High Similarity NPC272471
0.9821 High Similarity NPC107588
0.9821 High Similarity NPC70744
0.9649 High Similarity NPC2058
0.9573 High Similarity NPC20443
0.9573 High Similarity NPC60517
0.9573 High Similarity NPC146886
0.9573 High Similarity NPC246704
0.9492 High Similarity NPC289459
0.9464 High Similarity NPC294941
0.9412 High Similarity NPC120225
0.9412 High Similarity NPC213552
0.9391 High Similarity NPC37858
0.9386 High Similarity NPC39793
0.9375 High Similarity NPC95381
0.9304 High Similarity NPC124916
0.9292 High Similarity NPC217472
0.9292 High Similarity NPC328593
0.9292 High Similarity NPC261453
0.9292 High Similarity NPC33749
0.9256 High Similarity NPC110313
0.9256 High Similarity NPC109275
0.9217 High Similarity NPC65791
0.9211 High Similarity NPC474967
0.9211 High Similarity NPC233669
0.9196 High Similarity NPC226250
0.918 High Similarity NPC48315
0.918 High Similarity NPC83062
0.9167 High Similarity NPC58279
0.9167 High Similarity NPC300326
0.913 High Similarity NPC281277
0.9068 High Similarity NPC269843
0.9068 High Similarity NPC14007
0.9068 High Similarity NPC109083
0.9068 High Similarity NPC189844
0.9068 High Similarity NPC224814
0.9068 High Similarity NPC60962
0.9027 High Similarity NPC78918
0.9027 High Similarity NPC139617
0.9018 High Similarity NPC246358
0.9018 High Similarity NPC36108
0.9018 High Similarity NPC7097
0.9018 High Similarity NPC233731
0.9008 High Similarity NPC280767
0.8992 High Similarity NPC177291
0.8992 High Similarity NPC194416
0.8974 High Similarity NPC212743
0.8974 High Similarity NPC309434
0.8974 High Similarity NPC275519
0.8974 High Similarity NPC277460
0.8974 High Similarity NPC203124
0.8947 High Similarity NPC131530
0.8943 High Similarity NPC478215
0.8917 High Similarity NPC286573
0.8908 High Similarity NPC158949
0.8898 High Similarity NPC57501
0.8889 High Similarity NPC475468
0.886 High Similarity NPC156840
0.886 High Similarity NPC257124
0.886 High Similarity NPC8547
0.886 High Similarity NPC173746
0.8852 High Similarity NPC27352
0.8852 High Similarity NPC271985
0.8843 High Similarity NPC160900
0.8843 High Similarity NPC18984
0.8843 High Similarity NPC106659
0.8843 High Similarity NPC229084
0.8843 High Similarity NPC238810
0.8833 High Similarity NPC310373
0.8819 High Similarity NPC471110
0.8819 High Similarity NPC135127
0.8772 High Similarity NPC179309
0.876 High Similarity NPC114298
0.875 High Similarity NPC1075
0.875 High Similarity NPC470849
0.875 High Similarity NPC470848
0.875 High Similarity NPC1786
0.875 High Similarity NPC307253
0.875 High Similarity NPC294902
0.8739 High Similarity NPC141791
0.8739 High Similarity NPC241634
0.8739 High Similarity NPC263386
0.8729 High Similarity NPC212643
0.8729 High Similarity NPC199209
0.8729 High Similarity NPC280001
0.8699 High Similarity NPC87113
0.8696 High Similarity NPC245552
0.8689 High Similarity NPC257976
0.8689 High Similarity NPC242372
0.8689 High Similarity NPC4181
0.8689 High Similarity NPC164778
0.8682 High Similarity NPC90431
0.8682 High Similarity NPC157554
0.8682 High Similarity NPC120852
0.8678 High Similarity NPC114845
0.8673 High Similarity NPC227894
0.8672 High Similarity NPC92830
0.8672 High Similarity NPC111635
0.8661 High Similarity NPC111888
0.8661 High Similarity NPC288760
0.8655 High Similarity NPC205502
0.8655 High Similarity NPC255675
0.8644 High Similarity NPC221049
0.8629 High Similarity NPC276014
0.8618 High Similarity NPC312404
0.8618 High Similarity NPC273686
0.8615 High Similarity NPC126206
0.8607 High Similarity NPC288238
0.8594 High Similarity NPC283823
0.8594 High Similarity NPC159418
0.8583 High Similarity NPC299406
0.8583 High Similarity NPC181969
0.8583 High Similarity NPC311595
0.8583 High Similarity NPC320987
0.8583 High Similarity NPC69670
0.8583 High Similarity NPC24474
0.8571 High Similarity NPC164386
0.8571 High Similarity NPC2518
0.8571 High Similarity NPC241354
0.8571 High Similarity NPC293619
0.856 High Similarity NPC281020
0.856 High Similarity NPC203719
0.856 High Similarity NPC123722
0.856 High Similarity NPC151167
0.856 High Similarity NPC117237
0.856 High Similarity NPC276466
0.856 High Similarity NPC5018
0.856 High Similarity NPC123228
0.855 High Similarity NPC76032
0.855 High Similarity NPC100389
0.855 High Similarity NPC132723
0.855 High Similarity NPC13067
0.855 High Similarity NPC226005
0.855 High Similarity NPC284409
0.8547 High Similarity NPC264558
0.8547 High Similarity NPC303522
0.8538 High Similarity NPC186418
0.8538 High Similarity NPC471664
0.8538 High Similarity NPC471665
0.8537 High Similarity NPC474275
0.8537 High Similarity NPC224208
0.8534 High Similarity NPC195873
0.8534 High Similarity NPC55300
0.8525 High Similarity NPC193484
0.8525 High Similarity NPC147654
0.8525 High Similarity NPC470804
0.8516 High Similarity NPC245120
0.8512 High Similarity NPC229401
0.8512 High Similarity NPC222175
0.8512 High Similarity NPC177475
0.8512 High Similarity NPC148615
0.8512 High Similarity NPC35071
0.8504 High Similarity NPC298268
0.85 High Similarity NPC470626
0.85 High Similarity NPC159916
0.8485 Intermediate Similarity NPC288452
0.8485 Intermediate Similarity NPC106055
0.8485 Intermediate Similarity NPC110699
0.8485 Intermediate Similarity NPC289690
0.8482 Intermediate Similarity NPC304638
0.8482 Intermediate Similarity NPC179686
0.848 Intermediate Similarity NPC147192
0.848 Intermediate Similarity NPC303680
0.848 Intermediate Similarity NPC179777
0.848 Intermediate Similarity NPC90128
0.848 Intermediate Similarity NPC118584
0.848 Intermediate Similarity NPC84076
0.8473 Intermediate Similarity NPC139548
0.8473 Intermediate Similarity NPC95162
0.8473 Intermediate Similarity NPC20511
0.8473 Intermediate Similarity NPC52086
0.8473 Intermediate Similarity NPC76336
0.8473 Intermediate Similarity NPC148835
0.8462 Intermediate Similarity NPC165646
0.8462 Intermediate Similarity NPC477301
0.8455 Intermediate Similarity NPC209567
0.8448 Intermediate Similarity NPC137685
0.8443 Intermediate Similarity NPC471877
0.8443 Intermediate Similarity NPC207613
0.8438 Intermediate Similarity NPC73738
0.8425 Intermediate Similarity NPC304622
0.8421 Intermediate Similarity NPC19149
0.8417 Intermediate Similarity NPC259638
0.8413 Intermediate Similarity NPC32163
0.8413 Intermediate Similarity NPC16651
0.8407 Intermediate Similarity NPC52087
0.8407 Intermediate Similarity NPC79672
0.84 Intermediate Similarity NPC132921
0.84 Intermediate Similarity NPC67951
0.8397 Intermediate Similarity NPC126682
0.8397 Intermediate Similarity NPC37468
0.8397 Intermediate Similarity NPC82271
0.8393 Intermediate Similarity NPC12714
0.8393 Intermediate Similarity NPC310905
0.8393 Intermediate Similarity NPC94343
0.8387 Intermediate Similarity NPC21238

  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 NPC202474 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
0.886 High Similarity NPD228 Approved
0.8843 High Similarity NPD4379 Clinical (unspecified phase)
0.8673 High Similarity NPD1358 Approved
0.856 High Similarity NPD9494 Approved
0.8264 Intermediate Similarity NPD5536 Phase 2
0.8261 Intermediate Similarity NPD3134 Approved
0.813 Intermediate Similarity NPD1357 Approved
0.7895 Intermediate Similarity NPD447 Suspended
0.7895 Intermediate Similarity NPD230 Phase 1
0.7863 Intermediate Similarity NPD3027 Phase 3
0.7857 Intermediate Similarity NPD3496 Discontinued
0.7857 Intermediate Similarity NPD9296 Approved
0.782 Intermediate Similarity NPD4060 Phase 1
0.7817 Intermediate Similarity NPD1653 Approved
0.7787 Intermediate Similarity NPD5283 Phase 1
0.7778 Intermediate Similarity NPD4626 Approved
0.7737 Intermediate Similarity NPD7266 Discontinued
0.7698 Intermediate Similarity NPD5691 Approved
0.7667 Intermediate Similarity NPD2684 Approved
0.7619 Intermediate Similarity NPD9545 Approved
0.7607 Intermediate Similarity NPD291 Approved
0.7583 Intermediate Similarity NPD290 Approved
0.7561 Intermediate Similarity NPD7843 Approved
0.7556 Intermediate Similarity NPD1613 Approved
0.7556 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7537 Intermediate Similarity NPD3145 Approved
0.7537 Intermediate Similarity NPD3144 Approved
0.7535 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.752 Intermediate Similarity NPD7157 Approved
0.7519 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7519 Intermediate Similarity NPD422 Phase 1
0.7519 Intermediate Similarity NPD3705 Approved
0.75 Intermediate Similarity NPD1778 Approved
0.7481 Intermediate Similarity NPD2674 Phase 3
0.7463 Intermediate Similarity NPD7095 Approved
0.7459 Intermediate Similarity NPD3022 Approved
0.7459 Intermediate Similarity NPD3021 Approved
0.7447 Intermediate Similarity NPD4110 Phase 3
0.7447 Intermediate Similarity NPD8166 Discontinued
0.7447 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7444 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7426 Intermediate Similarity NPD1558 Phase 1
0.7426 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7426 Intermediate Similarity NPD3620 Phase 2
0.7417 Intermediate Similarity NPD9697 Approved
0.7394 Intermediate Similarity NPD6190 Approved
0.736 Intermediate Similarity NPD1241 Discontinued
0.7355 Intermediate Similarity NPD968 Approved
0.7353 Intermediate Similarity NPD1726 Clinical (unspecified phase)
0.7328 Intermediate Similarity NPD9717 Approved
0.7324 Intermediate Similarity NPD4628 Phase 3
0.7319 Intermediate Similarity NPD6653 Approved
0.7299 Intermediate Similarity NPD826 Approved
0.7299 Intermediate Similarity NPD825 Approved
0.7293 Intermediate Similarity NPD987 Approved
0.7286 Intermediate Similarity NPD2935 Discontinued
0.728 Intermediate Similarity NPD5535 Approved
0.7279 Intermediate Similarity NPD6798 Discontinued
0.7279 Intermediate Similarity NPD3111 Phase 1
0.7279 Intermediate Similarity NPD3455 Phase 2
0.7273 Intermediate Similarity NPD2983 Phase 2
0.7273 Intermediate Similarity NPD2982 Phase 2
0.7252 Intermediate Similarity NPD1535 Discovery
0.7248 Intermediate Similarity NPD1934 Approved
0.7246 Intermediate Similarity NPD555 Phase 2
0.7246 Intermediate Similarity NPD6355 Discontinued
0.7246 Intermediate Similarity NPD4340 Discontinued
0.7226 Intermediate Similarity NPD6233 Phase 2
0.7226 Intermediate Similarity NPD4062 Phase 3
0.7219 Intermediate Similarity NPD3882 Suspended
0.7219 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7218 Intermediate Similarity NPD1283 Approved
0.7211 Intermediate Similarity NPD3686 Approved
0.7211 Intermediate Similarity NPD3687 Approved
0.7209 Intermediate Similarity NPD1894 Discontinued
0.72 Intermediate Similarity NPD1006 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD9269 Phase 2
0.7197 Intermediate Similarity NPD2981 Phase 2
0.7197 Intermediate Similarity NPD1481 Phase 2
0.7194 Intermediate Similarity NPD2653 Approved
0.7188 Intermediate Similarity NPD9493 Approved
0.7177 Intermediate Similarity NPD556 Approved
0.7176 Intermediate Similarity NPD3847 Discontinued
0.7172 Intermediate Similarity NPD4357 Discontinued
0.7164 Intermediate Similarity NPD1203 Approved
0.7162 Intermediate Similarity NPD824 Approved
0.7154 Intermediate Similarity NPD5585 Approved
0.7153 Intermediate Similarity NPD411 Approved
0.7143 Intermediate Similarity NPD821 Approved
0.713 Intermediate Similarity NPD9365 Approved
0.7122 Intermediate Similarity NPD1933 Approved
0.7111 Intermediate Similarity NPD258 Approved
0.7111 Intermediate Similarity NPD257 Approved
0.7111 Intermediate Similarity NPD5647 Approved
0.7109 Intermediate Similarity NPD6671 Approved
0.7101 Intermediate Similarity NPD259 Phase 1
0.7086 Intermediate Similarity NPD2801 Approved
0.7071 Intermediate Similarity NPD2492 Phase 1
0.7068 Intermediate Similarity NPD1608 Approved
0.7063 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD3018 Phase 2
0.7055 Intermediate Similarity NPD1511 Approved
0.7054 Intermediate Similarity NPD111 Approved
0.705 Intermediate Similarity NPD4140 Approved
0.7047 Intermediate Similarity NPD3866 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD3817 Phase 2
0.7029 Intermediate Similarity NPD1048 Approved
0.7015 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7014 Intermediate Similarity NPD3060 Approved
0.7014 Intermediate Similarity NPD1652 Phase 2
0.7013 Intermediate Similarity NPD6234 Discontinued
0.7008 Intermediate Similarity NPD9377 Approved
0.7008 Intermediate Similarity NPD9379 Approved
0.7007 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.6993 Remote Similarity NPD5763 Approved
0.6993 Remote Similarity NPD1375 Discontinued
0.6993 Remote Similarity NPD5762 Approved
0.6992 Remote Similarity NPD1281 Approved
0.6992 Remote Similarity NPD1091 Approved
0.6985 Remote Similarity NPD6584 Phase 3
0.6984 Remote Similarity NPD9280 Clinical (unspecified phase)
0.6974 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6974 Remote Similarity NPD1465 Phase 2
0.6963 Remote Similarity NPD3225 Approved
0.6959 Remote Similarity NPD1512 Approved
0.6957 Remote Similarity NPD9295 Approved
0.6957 Remote Similarity NPD7685 Pre-registration
0.6954 Remote Similarity NPD6386 Approved
0.6954 Remote Similarity NPD6385 Approved
0.6947 Remote Similarity NPD1548 Phase 1
0.6934 Remote Similarity NPD9569 Approved
0.6929 Remote Similarity NPD969 Suspended
0.6923 Remote Similarity NPD694 Clinical (unspecified phase)
0.6923 Remote Similarity NPD6032 Approved
0.6923 Remote Similarity NPD2161 Phase 2
0.6923 Remote Similarity NPD1551 Phase 2
0.6923 Remote Similarity NPD8127 Discontinued
0.6913 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6912 Remote Similarity NPD2797 Approved
0.6906 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6901 Remote Similarity NPD7097 Phase 1
0.6899 Remote Similarity NPD9299 Approved
0.6899 Remote Similarity NPD690 Clinical (unspecified phase)
0.6897 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6897 Remote Similarity NPD4237 Approved
0.6897 Remote Similarity NPD4236 Phase 3
0.6897 Remote Similarity NPD4162 Approved
0.6894 Remote Similarity NPD9268 Approved
0.6892 Remote Similarity NPD3146 Approved
0.6892 Remote Similarity NPD3688 Clinical (unspecified phase)
0.6892 Remote Similarity NPD4739 Approved
0.6889 Remote Similarity NPD4359 Approved
0.688 Remote Similarity NPD9265 Clinical (unspecified phase)
0.6879 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6875 Remote Similarity NPD3656 Approved
0.6866 Remote Similarity NPD776 Approved
0.6866 Remote Similarity NPD1611 Approved
0.6866 Remote Similarity NPD1610 Phase 2
0.6863 Remote Similarity NPD5563 Clinical (unspecified phase)
0.6861 Remote Similarity NPD1019 Discontinued
0.6853 Remote Similarity NPD2799 Discontinued
0.6842 Remote Similarity NPD5846 Approved
0.6842 Remote Similarity NPD17 Approved
0.6842 Remote Similarity NPD9381 Approved
0.6842 Remote Similarity NPD6516 Phase 2
0.6842 Remote Similarity NPD9384 Approved
0.6838 Remote Similarity NPD2922 Phase 1
0.6835 Remote Similarity NPD5163 Phase 2
0.6828 Remote Similarity NPD4534 Discontinued
0.6828 Remote Similarity NPD7153 Discontinued
0.6828 Remote Similarity NPD2424 Discontinued
0.6824 Remote Similarity NPD6799 Approved
0.6818 Remote Similarity NPD1182 Approved
0.6815 Remote Similarity NPD2821 Approved
0.6813 Remote Similarity NPD3818 Discontinued
0.6812 Remote Similarity NPD2861 Phase 2
0.6812 Remote Similarity NPD454 Approved
0.6809 Remote Similarity NPD2979 Phase 3
0.6807 Remote Similarity NPD2933 Approved
0.6807 Remote Similarity NPD1432 Clinical (unspecified phase)
0.6807 Remote Similarity NPD2934 Approved
0.6806 Remote Similarity NPD2239 Approved
0.6806 Remote Similarity NPD2438 Suspended
0.6806 Remote Similarity NPD2240 Approved
0.6806 Remote Similarity NPD1501 Clinical (unspecified phase)
0.6803 Remote Similarity NPD2219 Phase 1
0.6803 Remote Similarity NPD1242 Phase 1
0.6803 Remote Similarity NPD2354 Approved
0.6797 Remote Similarity NPD37 Approved
0.6792 Remote Similarity NPD6166 Phase 2
0.6792 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6792 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6788 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6786 Remote Similarity NPD3764 Approved
0.6786 Remote Similarity NPD3268 Approved
0.6786 Remote Similarity NPD5110 Phase 2
0.6786 Remote Similarity NPD5111 Phase 2
0.6786 Remote Similarity NPD5109 Approved
0.6779 Remote Similarity NPD1754 Clinical (unspecified phase)
0.6779 Remote Similarity NPD3536 Discontinued

  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