Structure

Physi-Chem Properties

Molecular Weight:  283.12
Volume:  301.751
LogP:  2.64
LogD:  3.048
LogS:  -2.997
# Rotatable Bonds:  6
TPSA:  69.56
# H-Bond Aceptor:  4
# H-Bond Donor:  3
# Rings:  2
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.583
Synthetic Accessibility Score:  1.902
Fsp3:  0.118
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.922
MDCK Permeability:  1.5279501894838177e-05
Pgp-inhibitor:  0.015
Pgp-substrate:  0.011
Human Intestinal Absorption (HIA):  0.056
20% Bioavailability (F20%):  0.157
30% Bioavailability (F30%):  0.151

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.281
Plasma Protein Binding (PPB):  96.80609130859375%
Volume Distribution (VD):  0.566
Pgp-substrate:  2.2161853313446045%

ADMET: Metabolism

CYP1A2-inhibitor:  0.928
CYP1A2-substrate:  0.113
CYP2C19-inhibitor:  0.733
CYP2C19-substrate:  0.066
CYP2C9-inhibitor:  0.77
CYP2C9-substrate:  0.902
CYP2D6-inhibitor:  0.888
CYP2D6-substrate:  0.862
CYP3A4-inhibitor:  0.313
CYP3A4-substrate:  0.212

ADMET: Excretion

Clearance (CL):  13.443
Half-life (T1/2):  0.927

ADMET: Toxicity

hERG Blockers:  0.106
Human Hepatotoxicity (H-HT):  0.158
Drug-inuced Liver Injury (DILI):  0.05
AMES Toxicity:  0.547
Rat Oral Acute Toxicity:  0.207
Maximum Recommended Daily Dose:  0.757
Skin Sensitization:  0.949
Carcinogencity:  0.199
Eye Corrosion:  0.004
Eye Irritation:  0.191
Respiratory Toxicity:  0.341

Download Data

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

  Natural Product: NPC283468

Natural Product ID:  NPC283468
Common Name*:   Caffeic Acid Phenethyl Amide
IUPAC Name:   (E)-3-(3,4-dihydroxyphenyl)-N-(2-phenylethyl)prop-2-enamide
Synonyms:   Caffeic Acid Phenethyl Amide
Standard InCHIKey:  QOWABIXYAFJMQE-VQHVLOKHSA-N
Standard InCHI:  InChI=1S/C17H17NO3/c19-15-8-6-14(12-16(15)20)7-9-17(21)18-11-10-13-4-2-1-3-5-13/h1-9,12,19-20H,10-11H2,(H,18,21)/b9-7+
SMILES:  c1ccc(cc1)CCN=C(/C=C/c1ccc(c(c1)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL67498
PubChem CID:   11391937
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000476] Cinnamic acids and derivatives
        • [CHEMONTID:0001391] Hydroxycinnamic 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
NPO19242 Eucalyptus albens Species Myrtaceae Eukaryota flowers n.a. n.a. PMID[10075775]
NPO11164 Renealmia alpinia Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[10479331]
NPO19436 Annona cherimola Species Annonaceae Eukaryota Seeds n.a. n.a. PMID[15387664]
NPO19083 Alstonia angustiloba Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[18524603]
NPO17759 Rhododendron mucronulatum Species Ericaceae Eukaryota n.a. stem n.a. PMID[21443171]
NPO18602 Melampodium leucanthum Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[23501116]
NPO18602 Melampodium leucanthum Species Asteraceae Eukaryota leaves and branches San Antonio, Texas 2004-JUN PMID[25685941]
NPO18602 Melampodium leucanthum Species Asteraceae Eukaryota leaves and branches n.a. n.a. PMID[25685941]
NPO17296 Beesia calthifolia Species Ranunculaceae Eukaryota n.a. n.a. n.a. PMID[26238319]
NPO18676 Clerodendrum trichotomum Species Lamiaceae Eukaryota Roots n.a. n.a. PMID[29924604]
NPO11164 Renealmia alpinia Species Zingiberaceae Eukaryota n.a. Suriname rainforest n.a. PMID[9428162]
NPO19436 Annona cherimola Species Annonaceae Eukaryota n.a. n.a. Database[FooDB]
NPO19436 Annona cherimola Species Annonaceae Eukaryota n.a. n.a. Database[FooDB]
NPO19436 Annona cherimola Species Annonaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO19436 Annona cherimola Species Annonaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO18765 Juniperus scopulorum Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13737 Tephroseris kirilowii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1783 Euonymus fortunei Species Celastraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19769 Boschniakia rossica Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17759 Rhododendron mucronulatum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18676 Clerodendrum trichotomum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13358 Piper brachystachyum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17759 Rhododendron mucronulatum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19769 Boschniakia rossica Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13737 Tephroseris kirilowii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18765 Juniperus scopulorum Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1783 Euonymus fortunei Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11967 Delphinium giraldii Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14233 Ormosia dasycarpa Species Limoniidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17296 Beesia calthifolia Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24402.1 Coffea liberica var. dewevrei Varieties Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17759 Rhododendron mucronulatum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19769 Boschniakia rossica Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18765 Juniperus scopulorum Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1783 Euonymus fortunei Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19170 Lasianthaea podocephala Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24402.1 Coffea liberica var. dewevrei Varieties Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16325 Sideritis dasygnaphala Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29450 Streptomyces parvisporogenes Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO19083 Alstonia angustiloba Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19436 Annona cherimola Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12223 Stellaria media Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12870 Curcuma aeruginosa Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19572 Pellacalyx axillaris Species Rhizophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14233 Ormosia dasycarpa Species Limoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18765 Juniperus scopulorum Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11967 Delphinium giraldii Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18602 Melampodium leucanthum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16981 Gutierrezia dracunculoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18424 Selinum libanotis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11646 Morella pensylvanica Species Myricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15127 Senecio congestus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18927 Clinacanthus nutans Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12914 Sarcophyton flexuosum Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18262 Aspergillus microcysticus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18676 Clerodendrum trichotomum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29531 Lupinus cosentinii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17296 Beesia calthifolia Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13737 Tephroseris kirilowii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17354 Micromonospora echinospora Species Micromonosporaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO11081 Baccharis grandicapitulata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11164 Renealmia alpinia Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17759 Rhododendron mucronulatum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17230 Psidium acutangulum Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17499 Bursera kerberi Species Burseraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19709 Pseudocyphellaria australiensis Species Lobariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4679 Hedysarum gmelini Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19242 Eucalyptus albens Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13358 Piper brachystachyum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9906 Zephyranthes flava Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19371 Costasiella ocellifera Species Costasiellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18348 Crotalaria stolzii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17114 Streptomyces melanogenes Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO18048 Phlomis crinita Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8172 Emericellopsis minima Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16135 Pestalotiopsis oenotherae Species Sporocadaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17630 Helenium integrifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO968 Artemisia pectinata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18533 Delisea elegans Species Bonnemaisoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15802 Papaver pseudocanescens Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25370 Botrychium ternatum Species Ophioglossaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19769 Boschniakia rossica Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5455 Euploca racemosa Species Heliotropiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18169 Creosphaeria sassafras Species Xylariaceae 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
NPT737 Cell Line HUVEC Homo sapiens EC50 = 2000.0 nM PMID[451710]
NPT280 Individual Protein Matrix metalloproteinase 9 Homo sapiens IC50 = 7.28 nM PMID[451711]
NPT568 Individual Protein Matrix metalloproteinase-2 Homo sapiens IC50 = 8.2 nM PMID[451711]
NPT858 Cell Line LNCaP Homo sapiens IC50 > 100000.0 nM PMID[451712]
NPT2 Others Unspecified IC50 = 850.0 nM PMID[451708]
NPT2 Others Unspecified Ratio IC50 = 453.0 n.a. PMID[451711]
NPT22401 SELECTIVITY GROUP MMP-1/MMP-2 Homo sapiens Ratio IC50 = 403.0 n.a. PMID[451711]
NPT69 Individual Protein Matrix metalloproteinase-1 Homo sapiens IC50 = 3301.33 nM PMID[451711]
NPT1 Others Radical scavenging activity IC50 = 13800.0 nM PMID[451712]

☑ 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 NPC283468 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
0.9909 High Similarity NPC122009
0.9643 High Similarity NPC268572
0.9196 High Similarity NPC142599
0.9174 High Similarity NPC24101
0.9174 High Similarity NPC96224
0.9138 High Similarity NPC284078
0.9083 High Similarity NPC251571
0.9008 High Similarity NPC155838
0.8934 High Similarity NPC52029
0.8934 High Similarity NPC35961
0.8934 High Similarity NPC195749
0.879 High Similarity NPC214869
0.8739 High Similarity NPC142297
0.871 High Similarity NPC114102
0.8661 High Similarity NPC153690
0.8649 High Similarity NPC231705
0.8618 High Similarity NPC153990
0.8618 High Similarity NPC186898
0.8583 High Similarity NPC6913
0.8548 High Similarity NPC271808
0.8545 High Similarity NPC178902
0.8537 High Similarity NPC301713
0.8522 High Similarity NPC146422
0.845 Intermediate Similarity NPC312770
0.845 Intermediate Similarity NPC160607
0.845 Intermediate Similarity NPC204848
0.845 Intermediate Similarity NPC41473
0.845 Intermediate Similarity NPC14600
0.8421 Intermediate Similarity NPC258056
0.8417 Intermediate Similarity NPC252817
0.839 Intermediate Similarity NPC82963
0.8385 Intermediate Similarity NPC299583
0.8385 Intermediate Similarity NPC296898
0.8364 Intermediate Similarity NPC223393
0.8348 Intermediate Similarity NPC474149
0.832 Intermediate Similarity NPC477839
0.8319 Intermediate Similarity NPC38458
0.8319 Intermediate Similarity NPC311737
0.8306 Intermediate Similarity NPC318965
0.8304 Intermediate Similarity NPC471511
0.8261 Intermediate Similarity NPC62258
0.8261 Intermediate Similarity NPC228343
0.8261 Intermediate Similarity NPC254833
0.8261 Intermediate Similarity NPC55617
0.825 Intermediate Similarity NPC85276
0.823 Intermediate Similarity NPC239291
0.8214 Intermediate Similarity NPC196479
0.8203 Intermediate Similarity NPC93882
0.8203 Intermediate Similarity NPC130595
0.819 Intermediate Similarity NPC226401
0.819 Intermediate Similarity NPC120982
0.819 Intermediate Similarity NPC79793
0.819 Intermediate Similarity NPC174096
0.819 Intermediate Similarity NPC147634
0.8182 Intermediate Similarity NPC109955
0.8151 Intermediate Similarity NPC37302
0.814 Intermediate Similarity NPC313737
0.814 Intermediate Similarity NPC6854
0.814 Intermediate Similarity NPC285078
0.8125 Intermediate Similarity NPC255550
0.8125 Intermediate Similarity NPC308885
0.812 Intermediate Similarity NPC179002
0.812 Intermediate Similarity NPC187583
0.812 Intermediate Similarity NPC297657
0.812 Intermediate Similarity NPC257430
0.8077 Intermediate Similarity NPC218530
0.8067 Intermediate Similarity NPC118202
0.806 Intermediate Similarity NPC222039
0.806 Intermediate Similarity NPC100478
0.8033 Intermediate Similarity NPC43275
0.8017 Intermediate Similarity NPC233835
0.8015 Intermediate Similarity NPC5462
0.8 Intermediate Similarity NPC317254
0.8 Intermediate Similarity NPC477814
0.8 Intermediate Similarity NPC107522
0.7967 Intermediate Similarity NPC169207
0.7967 Intermediate Similarity NPC118522
0.7967 Intermediate Similarity NPC115627
0.7967 Intermediate Similarity NPC263835
0.7965 Intermediate Similarity NPC110764
0.7949 Intermediate Similarity NPC71266
0.7946 Intermediate Similarity NPC131587
0.7931 Intermediate Similarity NPC176527
0.7917 Intermediate Similarity NPC120280
0.7907 Intermediate Similarity NPC470706
0.7899 Intermediate Similarity NPC51698
0.7876 Intermediate Similarity NPC289381
0.7876 Intermediate Similarity NPC155847
0.7863 Intermediate Similarity NPC114392
0.7863 Intermediate Similarity NPC105727
0.7863 Intermediate Similarity NPC34864
0.7863 Intermediate Similarity NPC58427
0.7842 Intermediate Similarity NPC153644
0.7842 Intermediate Similarity NPC470935
0.7842 Intermediate Similarity NPC471032
0.7838 Intermediate Similarity NPC274678
0.7826 Intermediate Similarity NPC120719
0.7826 Intermediate Similarity NPC12278
0.7815 Intermediate Similarity NPC268032
0.7815 Intermediate Similarity NPC280382
0.7795 Intermediate Similarity NPC95733
0.7795 Intermediate Similarity NPC62101
0.7788 Intermediate Similarity NPC125732
0.7787 Intermediate Similarity NPC299252
0.7787 Intermediate Similarity NPC277394
0.7787 Intermediate Similarity NPC61062
0.7778 Intermediate Similarity NPC471315
0.7778 Intermediate Similarity NPC471314
0.777 Intermediate Similarity NPC115144
0.777 Intermediate Similarity NPC277857
0.7768 Intermediate Similarity NPC132271
0.7768 Intermediate Similarity NPC292730
0.7768 Intermediate Similarity NPC216520
0.7768 Intermediate Similarity NPC82664
0.7761 Intermediate Similarity NPC254610
0.776 Intermediate Similarity NPC83279
0.7748 Intermediate Similarity NPC76938
0.7748 Intermediate Similarity NPC151715
0.7742 Intermediate Similarity NPC283760
0.7739 Intermediate Similarity NPC68055
0.7724 Intermediate Similarity NPC145023
0.7724 Intermediate Similarity NPC200988
0.7724 Intermediate Similarity NPC175799
0.7724 Intermediate Similarity NPC86947
0.7724 Intermediate Similarity NPC610
0.7717 Intermediate Similarity NPC140359
0.7717 Intermediate Similarity NPC211218
0.7717 Intermediate Similarity NPC13020
0.771 Intermediate Similarity NPC473724
0.771 Intermediate Similarity NPC45191
0.7705 Intermediate Similarity NPC303370
0.7704 Intermediate Similarity NPC219233
0.7704 Intermediate Similarity NPC170170
0.7704 Intermediate Similarity NPC211468
0.7699 Intermediate Similarity NPC107619
0.7698 Intermediate Similarity NPC474862
0.7687 Intermediate Similarity NPC126637
0.7686 Intermediate Similarity NPC471485
0.7679 Intermediate Similarity NPC32714
0.7679 Intermediate Similarity NPC26244
0.7676 Intermediate Similarity NPC127402
0.7674 Intermediate Similarity NPC236347
0.7674 Intermediate Similarity NPC323775
0.7674 Intermediate Similarity NPC251466
0.7674 Intermediate Similarity NPC156944
0.7672 Intermediate Similarity NPC79672
0.7672 Intermediate Similarity NPC52087
0.7667 Intermediate Similarity NPC166837
0.7661 Intermediate Similarity NPC470626
0.7661 Intermediate Similarity NPC86198
0.7661 Intermediate Similarity NPC144343
0.7647 Intermediate Similarity NPC477837
0.7647 Intermediate Similarity NPC323123
0.7647 Intermediate Similarity NPC477838
0.7615 Intermediate Similarity NPC157740
0.7615 Intermediate Similarity NPC41331
0.7615 Intermediate Similarity NPC99798
0.7615 Intermediate Similarity NPC291449
0.7611 Intermediate Similarity NPC33168
0.7611 Intermediate Similarity NPC473388
0.76 Intermediate Similarity NPC109371
0.76 Intermediate Similarity NPC470215
0.76 Intermediate Similarity NPC263386
0.76 Intermediate Similarity NPC470214
0.76 Intermediate Similarity NPC281298
0.76 Intermediate Similarity NPC217174
0.76 Intermediate Similarity NPC70084
0.76 Intermediate Similarity NPC310338
0.76 Intermediate Similarity NPC141791
0.7597 Intermediate Similarity NPC170583
0.7597 Intermediate Similarity NPC71105
0.7597 Intermediate Similarity NPC182147
0.7597 Intermediate Similarity NPC152186
0.7597 Intermediate Similarity NPC246133
0.7597 Intermediate Similarity NPC29477
0.7597 Intermediate Similarity NPC207541
0.7586 Intermediate Similarity NPC477801
0.7586 Intermediate Similarity NPC477802
0.7581 Intermediate Similarity NPC278652
0.7581 Intermediate Similarity NPC293619
0.7581 Intermediate Similarity NPC277588
0.7578 Intermediate Similarity NPC318777
0.7568 Intermediate Similarity NPC45040
0.7565 Intermediate Similarity NPC294741
0.7557 Intermediate Similarity NPC469977
0.7557 Intermediate Similarity NPC147247
0.7557 Intermediate Similarity NPC325651
0.7557 Intermediate Similarity NPC246974
0.7552 Intermediate Similarity NPC52475
0.7544 Intermediate Similarity NPC32674
0.7542 Intermediate Similarity NPC294902
0.7542 Intermediate Similarity NPC1075
0.7542 Intermediate Similarity NPC19149
0.7542 Intermediate Similarity NPC1786
0.754 Intermediate Similarity NPC117780
0.754 Intermediate Similarity NPC475245
0.754 Intermediate Similarity NPC242885
0.754 Intermediate Similarity NPC17388
0.754 Intermediate Similarity NPC160120
0.754 Intermediate Similarity NPC34634

  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 NPC283468 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
0.8983 High Similarity NPD2337 Clinical (unspecified phase)
0.8525 High Similarity NPD5311 Approved
0.8525 High Similarity NPD5310 Approved
0.8522 High Similarity NPD9379 Approved
0.8522 High Similarity NPD9377 Approved
0.8455 Intermediate Similarity NPD3055 Approved
0.8455 Intermediate Similarity NPD3053 Approved
0.8261 Intermediate Similarity NPD3022 Approved
0.8261 Intermediate Similarity NPD3021 Approved
0.8203 Intermediate Similarity NPD2674 Phase 3
0.8125 Intermediate Similarity NPD3144 Approved
0.8125 Intermediate Similarity NPD2028 Clinical (unspecified phase)
0.8125 Intermediate Similarity NPD3145 Approved
0.8 Intermediate Similarity NPD3062 Approved
0.8 Intermediate Similarity NPD3059 Approved
0.8 Intermediate Similarity NPD3061 Approved
0.7983 Intermediate Similarity NPD2229 Approved
0.7983 Intermediate Similarity NPD2228 Approved
0.7983 Intermediate Similarity NPD2234 Approved
0.7967 Intermediate Similarity NPD9381 Approved
0.7967 Intermediate Similarity NPD9384 Approved
0.7886 Intermediate Similarity NPD4093 Discontinued
0.7881 Intermediate Similarity NPD9280 Clinical (unspecified phase)
0.7879 Intermediate Similarity NPD5314 Approved
0.7797 Intermediate Similarity NPD1792 Phase 2
0.7795 Intermediate Similarity NPD9634 Clinical (unspecified phase)
0.7748 Intermediate Similarity NPD2933 Approved
0.7748 Intermediate Similarity NPD2934 Approved
0.7717 Intermediate Similarity NPD9622 Approved
0.7717 Intermediate Similarity NPD1669 Approved
0.7692 Intermediate Similarity NPD1445 Approved
0.7692 Intermediate Similarity NPD1444 Approved
0.7679 Intermediate Similarity NPD2860 Approved
0.7679 Intermediate Similarity NPD2859 Approved
0.7674 Intermediate Similarity NPD9621 Approved
0.7674 Intermediate Similarity NPD7451 Discontinued
0.7674 Intermediate Similarity NPD9620 Approved
0.7674 Intermediate Similarity NPD9619 Approved
0.7632 Intermediate Similarity NPD3020 Approved
0.7619 Intermediate Similarity NPD3421 Phase 3
0.7576 Intermediate Similarity NPD597 Approved
0.7576 Intermediate Similarity NPD601 Approved
0.7576 Intermediate Similarity NPD598 Approved
0.7521 Intermediate Similarity NPD9610 Approved
0.7521 Intermediate Similarity NPD9608 Approved
0.752 Intermediate Similarity NPD2226 Clinical (unspecified phase)
0.7519 Intermediate Similarity NPD1130 Approved
0.7519 Intermediate Similarity NPD1132 Approved
0.7519 Intermediate Similarity NPD1136 Approved
0.7518 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7482 Intermediate Similarity NPD6331 Phase 2
0.7481 Intermediate Similarity NPD823 Approved
0.7481 Intermediate Similarity NPD9569 Approved
0.7481 Intermediate Similarity NPD817 Approved
0.7445 Intermediate Similarity NPD1632 Clinical (unspecified phase)
0.7414 Intermediate Similarity NPD1242 Phase 1
0.7402 Intermediate Similarity NPD5238 Clinical (unspecified phase)
0.7402 Intermediate Similarity NPD1751 Approved
0.7381 Intermediate Similarity NPD5303 Approved
0.7381 Intermediate Similarity NPD5304 Approved
0.7377 Intermediate Similarity NPD228 Approved
0.7376 Intermediate Similarity NPD2422 Clinical (unspecified phase)
0.7376 Intermediate Similarity NPD3845 Phase 1
0.7364 Intermediate Similarity NPD2561 Approved
0.7364 Intermediate Similarity NPD2562 Approved
0.7355 Intermediate Similarity NPD9380 Clinical (unspecified phase)
0.7344 Intermediate Similarity NPD1980 Approved
0.7344 Intermediate Similarity NPD1981 Approved
0.7344 Intermediate Similarity NPD1983 Approved
0.7339 Intermediate Similarity NPD1793 Approved
0.7339 Intermediate Similarity NPD1791 Approved
0.7333 Intermediate Similarity NPD1558 Phase 1
0.7333 Intermediate Similarity NPD6346 Approved
0.7324 Intermediate Similarity NPD2421 Approved
0.7324 Intermediate Similarity NPD2420 Approved
0.7319 Intermediate Similarity NPD2161 Phase 2
0.7308 Intermediate Similarity NPD3676 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD4659 Approved
0.7293 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7287 Intermediate Similarity NPD5351 Clinical (unspecified phase)
0.7287 Intermediate Similarity NPD5350 Clinical (unspecified phase)
0.7286 Intermediate Similarity NPD3060 Approved
0.7273 Intermediate Similarity NPD258 Approved
0.7273 Intermediate Similarity NPD4123 Phase 3
0.7273 Intermediate Similarity NPD257 Approved
0.7266 Intermediate Similarity NPD2667 Approved
0.7266 Intermediate Similarity NPD2668 Approved
0.7259 Intermediate Similarity NPD259 Phase 1
0.7252 Intermediate Similarity NPD2922 Phase 1
0.7244 Intermediate Similarity NPD1759 Phase 1
0.7239 Intermediate Similarity NPD5156 Approved
0.7239 Intermediate Similarity NPD9537 Phase 1
0.7239 Intermediate Similarity NPD5155 Approved
0.7239 Intermediate Similarity NPD9536 Phase 1
0.7234 Intermediate Similarity NPD6658 Clinical (unspecified phase)
0.7218 Intermediate Similarity NPD3635 Approved
0.7218 Intermediate Similarity NPD3636 Approved
0.7218 Intermediate Similarity NPD3637 Approved
0.7214 Intermediate Similarity NPD7153 Discontinued
0.72 Intermediate Similarity NPD9614 Approved
0.72 Intermediate Similarity NPD9618 Approved
0.7197 Intermediate Similarity NPD4104 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD4103 Phase 2
0.7185 Intermediate Similarity NPD5718 Phase 2
0.7176 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7165 Intermediate Similarity NPD16 Approved
0.7165 Intermediate Similarity NPD1758 Phase 1
0.7165 Intermediate Similarity NPD9616 Approved
0.7165 Intermediate Similarity NPD856 Approved
0.7165 Intermediate Similarity NPD9615 Approved
0.7165 Intermediate Similarity NPD9613 Approved
0.7164 Intermediate Similarity NPD2606 Approved
0.7164 Intermediate Similarity NPD3595 Approved
0.7164 Intermediate Similarity NPD3594 Approved
0.7164 Intermediate Similarity NPD2605 Approved
0.7153 Intermediate Similarity NPD555 Phase 2
0.7143 Intermediate Similarity NPD2194 Approved
0.7143 Intermediate Similarity NPD6584 Phase 3
0.7143 Intermediate Similarity NPD2195 Approved
0.713 Intermediate Similarity NPD1432 Clinical (unspecified phase)
0.7123 Intermediate Similarity NPD1972 Approved
0.7123 Intermediate Similarity NPD1973 Approved
0.7123 Intermediate Similarity NPD1969 Clinical (unspecified phase)
0.7122 Intermediate Similarity NPD6866 Clinical (unspecified phase)
0.7122 Intermediate Similarity NPD6867 Clinical (unspecified phase)
0.7111 Intermediate Similarity NPD3136 Phase 2
0.7111 Intermediate Similarity NPD2372 Approved
0.7109 Intermediate Similarity NPD316 Approved
0.7103 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD2568 Approved
0.7099 Intermediate Similarity NPD2232 Approved
0.7099 Intermediate Similarity NPD2233 Approved
0.7099 Intermediate Similarity NPD2230 Approved
0.7091 Intermediate Similarity NPD111 Approved
0.708 Intermediate Similarity NPD826 Approved
0.708 Intermediate Similarity NPD825 Approved
0.7071 Intermediate Similarity NPD7450 Phase 2
0.7069 Intermediate Similarity NPD844 Approved
0.7063 Intermediate Similarity NPD5241 Discontinued
0.705 Intermediate Similarity NPD3555 Approved
0.705 Intermediate Similarity NPD3552 Approved
0.705 Intermediate Similarity NPD3554 Approved
0.705 Intermediate Similarity NPD3553 Approved
0.7042 Intermediate Similarity NPD4162 Approved
0.7034 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.7031 Intermediate Similarity NPD318 Approved
0.7031 Intermediate Similarity NPD317 Approved
0.7027 Intermediate Similarity NPD4678 Approved
0.7027 Intermediate Similarity NPD4675 Approved
0.7021 Intermediate Similarity NPD6809 Clinical (unspecified phase)
0.7007 Intermediate Similarity NPD6407 Approved
0.7007 Intermediate Similarity NPD5729 Clinical (unspecified phase)
0.7007 Intermediate Similarity NPD6405 Approved
0.7 Intermediate Similarity NPD2286 Discontinued
0.6985 Remote Similarity NPD3027 Phase 3
0.6985 Remote Similarity NPD1024 Discontinued
0.6984 Remote Similarity NPD5283 Phase 1
0.697 Remote Similarity NPD2231 Phase 2
0.697 Remote Similarity NPD2235 Phase 2
0.6959 Remote Similarity NPD4005 Discontinued
0.6959 Remote Similarity NPD3455 Phase 2
0.6957 Remote Similarity NPD5837 Clinical (unspecified phase)
0.6953 Remote Similarity NPD9568 Approved
0.695 Remote Similarity NPD9570 Approved
0.6949 Remote Similarity NPD9273 Approved
0.6944 Remote Similarity NPD302 Approved
0.6934 Remote Similarity NPD5110 Phase 2
0.6934 Remote Similarity NPD5109 Approved
0.6934 Remote Similarity NPD5111 Phase 2
0.6933 Remote Similarity NPD7945 Clinical (unspecified phase)
0.6929 Remote Similarity NPD6896 Approved
0.6929 Remote Similarity NPD6895 Approved
0.6923 Remote Similarity NPD5177 Phase 3
0.6918 Remote Similarity NPD4739 Approved
0.6918 Remote Similarity NPD3645 Discontinued
0.6917 Remote Similarity NPD6583 Phase 3
0.6917 Remote Similarity NPD1755 Approved
0.6917 Remote Similarity NPD6582 Phase 2
0.6906 Remote Similarity NPD275 Approved
0.6906 Remote Similarity NPD274 Approved
0.6887 Remote Similarity NPD2978 Approved
0.6887 Remote Similarity NPD2977 Approved
0.6884 Remote Similarity NPD7477 Discontinued
0.6884 Remote Similarity NPD839 Approved
0.6884 Remote Similarity NPD840 Approved
0.6879 Remote Similarity NPD4108 Discontinued
0.6875 Remote Similarity NPD7066 Clinical (unspecified phase)
0.6875 Remote Similarity NPD709 Approved
0.6864 Remote Similarity NPD288 Approved
0.686 Remote Similarity NPD4658 Approved
0.686 Remote Similarity NPD4656 Approved
0.6857 Remote Similarity NPD2157 Approved
0.6849 Remote Similarity NPD4357 Discontinued
0.6838 Remote Similarity NPD4993 Discontinued
0.6838 Remote Similarity NPD1712 Approved
0.6833 Remote Similarity NPD289 Clinical (unspecified phase)
0.6833 Remote Similarity NPD3028 Approved
0.6824 Remote Similarity NPD2122 Discontinued
0.6822 Remote Similarity NPD7325 Clinical (unspecified phase)
0.6818 Remote Similarity NPD1671 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