Structure

Physi-Chem Properties

Molecular Weight:  232.11
Volume:  252.696
LogP:  3.765
LogD:  3.209
LogS:  -3.39
# Rotatable Bonds:  4
TPSA:  57.53
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  1
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.619
Synthetic Accessibility Score:  2.368
Fsp3:  0.214
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.907
MDCK Permeability:  1.7978880350710824e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.051
Human Intestinal Absorption (HIA):  0.012
20% Bioavailability (F20%):  0.016
30% Bioavailability (F30%):  0.026

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.106
Plasma Protein Binding (PPB):  98.0943603515625%
Volume Distribution (VD):  0.33
Pgp-substrate:  1.8590351343154907%

ADMET: Metabolism

CYP1A2-inhibitor:  0.192
CYP1A2-substrate:  0.101
CYP2C19-inhibitor:  0.063
CYP2C19-substrate:  0.057
CYP2C9-inhibitor:  0.421
CYP2C9-substrate:  0.444
CYP2D6-inhibitor:  0.13
CYP2D6-substrate:  0.158
CYP3A4-inhibitor:  0.043
CYP3A4-substrate:  0.093

ADMET: Excretion

Clearance (CL):  9.606
Half-life (T1/2):  0.913

ADMET: Toxicity

hERG Blockers:  0.023
Human Hepatotoxicity (H-HT):  0.822
Drug-inuced Liver Injury (DILI):  0.391
AMES Toxicity:  0.045
Rat Oral Acute Toxicity:  0.17
Maximum Recommended Daily Dose:  0.217
Skin Sensitization:  0.929
Carcinogencity:  0.313
Eye Corrosion:  0.046
Eye Irritation:  0.878
Respiratory Toxicity:  0.622

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  Natural Product: NPC303141

Natural Product ID:  NPC303141
Common Name*:   Drupanin
IUPAC Name:   (E)-3-[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]prop-2-enoic acid
Synonyms:   Drupanin
Standard InCHIKey:  HZKNHDLUFBYIQN-VMPITWQZSA-N
Standard InCHI:  InChI=1S/C14H16O3/c1-10(2)3-6-12-9-11(4-7-13(12)15)5-8-14(16)17/h3-5,7-9,15H,6H2,1-2H3,(H,16,17)/b8-5+
SMILES:  CC(=CCc1cc(/C=C/C(=O)O)ccc1O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL464997
PubChem CID:   6440361
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000476] Cinnamic acids and derivatives
        • [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives
          • [CHEMONTID:0002503] Hydroxycinnamic acids

*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
NPO11196 Impatiens balsamina Species Balsaminaceae Eukaryota n.a. aerial part n.a. PMID[12033510]
NPO12006 Apis mellifera Species Apidae Eukaryota n.a. n.a. n.a. PMID[17548953]
NPO13379 Schizanthus tricolor Species Solanaceae Eukaryota Aerial parts n.a. n.a. PMID[20166702]
NPO11266 Garcinia cambogia Species Clusiaceae Eukaryota n.a. exocarp n.a. PMID[21114277]
NPO13379 Schizanthus tricolor Species Solanaceae Eukaryota n.a. aerial part n.a. PMID[21171571]
NPO32851 brazilian green propolis Species n.a. n.a. n.a. Brazilian green propolis n.a. PMID[21865046]
NPO12006 Apis mellifera Species Apidae Eukaryota n.a. n.a. n.a. PMID[24675423]
NPO12006 Apis mellifera Species Apidae Eukaryota n.a. Bako, Ethiopia PMID[24926420]
NPO12006 Apis mellifera Species Apidae Eukaryota n.a. Enemore, Ethiopia PMID[24926420]
NPO12006 Apis mellifera Species Apidae Eukaryota n.a. Gedo, Ethiopia PMID[24926420]
NPO12006 Apis mellifera Species Apidae Eukaryota n.a. Holleta, Ethiopia PMID[24926420]
NPO11196 Impatiens balsamina Species Balsaminaceae Eukaryota n.a. n.a. n.a. PMID[28165740]
NPO3013 Clathria basilana Species Microcionidae Eukaryota n.a. n.a. n.a. PMID[29094598]
NPO11196 Impatiens balsamina Species Balsaminaceae Eukaryota Pericarp n.a. n.a. PMID[9748380]
NPO11266 Garcinia cambogia Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO506 Iris unguicularis Species Iridaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11196 Impatiens balsamina Species Balsaminaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13473 Anodendron affine Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12006 Apis mellifera Species Apidae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11842 Petasites laevigatus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21787 Betula pubescens Species Betulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7541 Ormosia hosiei Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7541 Ormosia hosiei Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11842 Petasites laevigatus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11266 Garcinia cambogia Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13473 Anodendron affine Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11196 Impatiens balsamina Species Balsaminaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21787 Betula pubescens Species Betulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO506 Iris unguicularis Species Iridaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7541 Ormosia hosiei Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12006 Apis mellifera Species Apidae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11196 Impatiens balsamina Species Balsaminaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11196 Impatiens balsamina Species Balsaminaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO13473 Anodendron affine Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9569 Licaria chrysophylla Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1571 Carissa ovata Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13379 Schizanthus tricolor Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11266 Garcinia cambogia Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5280 Rubia tetragona Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO506 Iris unguicularis Species Iridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12006 Apis mellifera Species Apidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14369 Pocillopora eydouxi Species Pocilloporidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4700 Pertusaria truncata Species Pertusariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12521 Sphaeranthus confertifolius Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7541 Ormosia hosiei Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3013 Clathria basilana Species Microcionidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13669 Hertia cheirifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11842 Petasites laevigatus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14470 Polypodium decumanum Species Polypodiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14169 Acrocarpia paniculata Species Sargassaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11196 Impatiens balsamina Species Balsaminaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13178 Ornithoglossum viride Species Colchicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21787 Betula pubescens Species Betulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13876 Cedrela salvadorensis Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9431 Baccharis sternbergiana Species Asteraceae 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
NPT165 Cell Line HeLa Homo sapiens IC50 = 10.3 ug.mL-1 PMID[528526]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 146.0 % PMID[528527]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 127.1 % PMID[528527]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 101.2 % PMID[528527]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 105.8 % PMID[528527]
NPT41 Individual Protein Aldose reductase Homo sapiens IC50 = 38000.0 nM PMID[528528]
NPT1270 Individual Protein Aldo-keto reductase family 1 member B10 Homo sapiens IC50 = 49000.0 nM PMID[528528]
NPT3504 Individual Protein Aldo-keto-reductase family 1 member C3 Homo sapiens Inhibition = 14.0 % PMID[528529]
NPT3507 Individual Protein Aldo-keto reductase family 1 member C2 Homo sapiens IC50 = 108000.0 nM PMID[528529]
NPT3504 Individual Protein Aldo-keto-reductase family 1 member C3 Homo sapiens IC50 = 15000.0 nM PMID[528529]
NPT3506 Individual Protein Aldo-keto reductase family 1 member C4 Homo sapiens Inhibition = 0.0 % PMID[528529]
NPT3505 Individual Protein Aldo-keto reductase family 1 member C1 Homo sapiens Inhibition = 30.0 % PMID[528529]
NPT3504 Individual Protein Aldo-keto-reductase family 1 member C3 Homo sapiens IC50 = 15000.0 nM PMID[528532]
NPT3507 Individual Protein Aldo-keto reductase family 1 member C2 Homo sapiens IC50 = 107000.0 nM PMID[528532]
NPT3504 Individual Protein Aldo-keto-reductase family 1 member C3 Homo sapiens IC50 = 15848.93 nM PMID[528533]
NPT3507 Individual Protein Aldo-keto reductase family 1 member C2 Homo sapiens IC50 = 125892.54 nM PMID[528533]
NPT454 Organism Tenebrio molitor Tenebrio molitor Activity = 63.0 % PMID[528524]
NPT454 Organism Tenebrio molitor Tenebrio molitor Activity = 13.0 day PMID[528524]
NPT566 Organism Salmonella typhimurium Salmonella enterica subsp. enterica serovar Typhimurium Inhibition = 0.3 % PMID[528525]
NPT566 Organism Salmonella typhimurium Salmonella enterica subsp. enterica serovar Typhimurium Inhibition = 0.6 % PMID[528525]
NPT566 Organism Salmonella typhimurium Salmonella enterica subsp. enterica serovar Typhimurium Inhibition = 12.0 % PMID[528525]
NPT2 Others Unspecified Ratio = 0.36 n.a. PMID[528527]
NPT2 Others Unspecified IC50 = 25600.0 nM PMID[528527]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 84.3 % PMID[528527]
NPT776 Organism Spodoptera littoralis Spodoptera littoralis FR50 = 78.0 n.a. PMID[528530]
NPT176 Organism Artemia salina Artemia salina LC50 = 104.3 ppm PMID[528530]
NPT2 Others Unspecified Ratio IC50 = 7.0 n.a. PMID[528532]
NPT2 Others Unspecified Ratio IC50 = 7.0 n.a. PMID[528533]

☑ 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 NPC303141 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
0.9796 High Similarity NPC243677
0.9794 High Similarity NPC470202
0.9604 High Similarity NPC75272
0.9604 High Similarity NPC471954
0.9505 High Similarity NPC470039
0.9175 High Similarity NPC246679
0.9072 High Similarity NPC32977
0.9072 High Similarity NPC81010
0.8962 High Similarity NPC199462
0.89 High Similarity NPC128723
0.8866 High Similarity NPC204210
0.8818 High Similarity NPC474890
0.8818 High Similarity NPC161943
0.8818 High Similarity NPC273282
0.8812 High Similarity NPC253746
0.88 High Similarity NPC77492
0.8788 High Similarity NPC8392
0.8776 High Similarity NPC181709
0.8713 High Similarity NPC252821
0.8713 High Similarity NPC122005
0.8704 High Similarity NPC242136
0.8667 High Similarity NPC228737
0.866 High Similarity NPC70436
0.866 High Similarity NPC242240
0.866 High Similarity NPC123273
0.866 High Similarity NPC318325
0.8641 High Similarity NPC304638
0.8636 High Similarity NPC83718
0.8627 High Similarity NPC225506
0.8624 High Similarity NPC114918
0.8611 High Similarity NPC228988
0.86 High Similarity NPC144682
0.86 High Similarity NPC257182
0.8598 High Similarity NPC473809
0.8558 High Similarity NPC93831
0.8557 High Similarity NPC25493
0.8557 High Similarity NPC113460
0.8529 High Similarity NPC245561
0.8519 High Similarity NPC139946
0.8519 High Similarity NPC228609
0.8515 High Similarity NPC283711
0.85 High Similarity NPC128062
0.85 High Similarity NPC289769
0.8476 Intermediate Similarity NPC138942
0.8469 Intermediate Similarity NPC177420
0.8469 Intermediate Similarity NPC258219
0.8469 Intermediate Similarity NPC280347
0.8462 Intermediate Similarity NPC135784
0.8462 Intermediate Similarity NPC168829
0.8455 Intermediate Similarity NPC41851
0.8454 Intermediate Similarity NPC307235
0.8454 Intermediate Similarity NPC407
0.8454 Intermediate Similarity NPC23167
0.8447 Intermediate Similarity NPC52472
0.8435 Intermediate Similarity NPC67300
0.8431 Intermediate Similarity NPC201967
0.8431 Intermediate Similarity NPC140619
0.8426 Intermediate Similarity NPC183700
0.8416 Intermediate Similarity NPC286006
0.8416 Intermediate Similarity NPC26244
0.8411 Intermediate Similarity NPC279887
0.8411 Intermediate Similarity NPC68260
0.8393 Intermediate Similarity NPC183154
0.8393 Intermediate Similarity NPC263754
0.8384 Intermediate Similarity NPC55561
0.8381 Intermediate Similarity NPC288411
0.8365 Intermediate Similarity NPC94343
0.8365 Intermediate Similarity NPC472585
0.8364 Intermediate Similarity NPC211421
0.8362 Intermediate Similarity NPC174991
0.8351 Intermediate Similarity NPC155393
0.8351 Intermediate Similarity NPC197783
0.835 Intermediate Similarity NPC130193
0.835 Intermediate Similarity NPC171843
0.8333 Intermediate Similarity NPC95172
0.8333 Intermediate Similarity NPC473388
0.8333 Intermediate Similarity NPC26013
0.8333 Intermediate Similarity NPC282855
0.8318 Intermediate Similarity NPC260952
0.8317 Intermediate Similarity NPC316301
0.8317 Intermediate Similarity NPC152415
0.8317 Intermediate Similarity NPC27323
0.8317 Intermediate Similarity NPC151715
0.8304 Intermediate Similarity NPC471936
0.8302 Intermediate Similarity NPC127676
0.8302 Intermediate Similarity NPC227255
0.83 Intermediate Similarity NPC304541
0.83 Intermediate Similarity NPC306074
0.83 Intermediate Similarity NPC45040
0.8291 Intermediate Similarity NPC184219
0.8288 Intermediate Similarity NPC197513
0.8286 Intermediate Similarity NPC13426
0.8286 Intermediate Similarity NPC108497
0.8265 Intermediate Similarity NPC184169
0.8257 Intermediate Similarity NPC63345
0.8257 Intermediate Similarity NPC208229
0.8252 Intermediate Similarity NPC260000
0.8247 Intermediate Similarity NPC248817
0.8247 Intermediate Similarity NPC175313
0.8247 Intermediate Similarity NPC286904
0.8246 Intermediate Similarity NPC473767
0.8241 Intermediate Similarity NPC61885
0.8241 Intermediate Similarity NPC206341
0.8241 Intermediate Similarity NPC31274
0.8241 Intermediate Similarity NPC63698
0.823 Intermediate Similarity NPC122117
0.823 Intermediate Similarity NPC160199
0.8224 Intermediate Similarity NPC69332
0.8224 Intermediate Similarity NPC1075
0.8224 Intermediate Similarity NPC95178
0.8224 Intermediate Similarity NPC1786
0.8224 Intermediate Similarity NPC29989
0.8224 Intermediate Similarity NPC294902
0.8224 Intermediate Similarity NPC271274
0.8218 Intermediate Similarity NPC325292
0.8218 Intermediate Similarity NPC138117
0.8208 Intermediate Similarity NPC2518
0.82 Intermediate Similarity NPC300017
0.8182 Intermediate Similarity NPC470355
0.8173 Intermediate Similarity NPC80027
0.8173 Intermediate Similarity NPC280869
0.8173 Intermediate Similarity NPC92730
0.8165 Intermediate Similarity NPC88141
0.8165 Intermediate Similarity NPC98392
0.8165 Intermediate Similarity NPC79543
0.8151 Intermediate Similarity NPC473751
0.8148 Intermediate Similarity NPC226699
0.8144 Intermediate Similarity NPC265146
0.8144 Intermediate Similarity NPC124436
0.8131 Intermediate Similarity NPC99557
0.8131 Intermediate Similarity NPC219286
0.8131 Intermediate Similarity NPC13495
0.812 Intermediate Similarity NPC475192
0.8119 Intermediate Similarity NPC155908
0.8119 Intermediate Similarity NPC270547
0.8113 Intermediate Similarity NPC269212
0.8113 Intermediate Similarity NPC68269
0.8108 Intermediate Similarity NPC17693
0.8108 Intermediate Similarity NPC26615
0.8108 Intermediate Similarity NPC286222
0.8103 Intermediate Similarity NPC131868
0.8103 Intermediate Similarity NPC241001
0.8103 Intermediate Similarity NPC164852
0.81 Intermediate Similarity NPC98772
0.8095 Intermediate Similarity NPC248396
0.8095 Intermediate Similarity NPC211885
0.8095 Intermediate Similarity NPC72729
0.8095 Intermediate Similarity NPC129373
0.8095 Intermediate Similarity NPC48730
0.8091 Intermediate Similarity NPC222905
0.8091 Intermediate Similarity NPC296683
0.8083 Intermediate Similarity NPC243688
0.8077 Intermediate Similarity NPC79241
0.8077 Intermediate Similarity NPC225464
0.8077 Intermediate Similarity NPC6597
0.8077 Intermediate Similarity NPC152097
0.8073 Intermediate Similarity NPC262365
0.8073 Intermediate Similarity NPC224584
0.807 Intermediate Similarity NPC278652
0.807 Intermediate Similarity NPC174087
0.8067 Intermediate Similarity NPC244495
0.8067 Intermediate Similarity NPC93219
0.8058 Intermediate Similarity NPC313650
0.8058 Intermediate Similarity NPC274678
0.8058 Intermediate Similarity NPC222146
0.8056 Intermediate Similarity NPC70843
0.8056 Intermediate Similarity NPC21594
0.8056 Intermediate Similarity NPC6984
0.8056 Intermediate Similarity NPC54765
0.8039 Intermediate Similarity NPC3358
0.8039 Intermediate Similarity NPC271440
0.8039 Intermediate Similarity NPC210497
0.8039 Intermediate Similarity NPC162314
0.8039 Intermediate Similarity NPC94139
0.8039 Intermediate Similarity NPC147284
0.8039 Intermediate Similarity NPC306884
0.8037 Intermediate Similarity NPC261573
0.8037 Intermediate Similarity NPC120693
0.8037 Intermediate Similarity NPC79672
0.8037 Intermediate Similarity NPC8931
0.8037 Intermediate Similarity NPC119860
0.8036 Intermediate Similarity NPC296144
0.8036 Intermediate Similarity NPC190212
0.8036 Intermediate Similarity NPC28784
0.8034 Intermediate Similarity NPC251259
0.802 Intermediate Similarity NPC192
0.8019 Intermediate Similarity NPC51015
0.8018 Intermediate Similarity NPC225679
0.8018 Intermediate Similarity NPC4493
0.8018 Intermediate Similarity NPC165770
0.8018 Intermediate Similarity NPC95716
0.8018 Intermediate Similarity NPC476632
0.8018 Intermediate Similarity NPC226250
0.8017 Intermediate Similarity NPC478121
0.8017 Intermediate Similarity NPC473744
0.8017 Intermediate Similarity NPC193203
0.8017 Intermediate Similarity NPC229894
0.8 Intermediate Similarity NPC299762
0.8 Intermediate Similarity NPC132078
0.8 Intermediate Similarity NPC184527

  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 NPC303141 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
0.86 High Similarity NPD1809 Phase 2
0.8586 High Similarity NPD845 Approved
0.8416 Intermediate Similarity NPD2860 Approved
0.8416 Intermediate Similarity NPD2859 Approved
0.8365 Intermediate Similarity NPD940 Approved
0.8365 Intermediate Similarity NPD846 Approved
0.8317 Intermediate Similarity NPD2933 Approved
0.8317 Intermediate Similarity NPD1432 Clinical (unspecified phase)
0.8317 Intermediate Similarity NPD2934 Approved
0.8235 Intermediate Similarity NPD844 Approved
0.8174 Intermediate Similarity NPD4626 Approved
0.8173 Intermediate Similarity NPD3020 Approved
0.8144 Intermediate Similarity NPD111 Approved
0.7982 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7981 Intermediate Similarity NPD288 Approved
0.7931 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7925 Intermediate Similarity NPD289 Clinical (unspecified phase)
0.7917 Intermediate Similarity NPD1164 Approved
0.7909 Intermediate Similarity NPD74 Approved
0.7909 Intermediate Similarity NPD9266 Approved
0.7826 Intermediate Similarity NPD9493 Approved
0.7818 Intermediate Similarity NPD9264 Approved
0.7818 Intermediate Similarity NPD9267 Approved
0.7818 Intermediate Similarity NPD9263 Approved
0.7778 Intermediate Similarity NPD5691 Approved
0.7739 Intermediate Similarity NPD256 Approved
0.7739 Intermediate Similarity NPD255 Approved
0.7731 Intermediate Similarity NPD422 Phase 1
0.7727 Intermediate Similarity NPD3134 Approved
0.7699 Intermediate Similarity NPD6124 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD9545 Approved
0.7658 Intermediate Similarity NPD1358 Approved
0.7565 Intermediate Similarity NPD7159 Clinical (unspecified phase)
0.7522 Intermediate Similarity NPD3022 Approved
0.7522 Intermediate Similarity NPD3021 Approved
0.7478 Intermediate Similarity NPD7635 Approved
0.7477 Intermediate Similarity NPD9697 Approved
0.7462 Intermediate Similarity NPD2935 Discontinued
0.7455 Intermediate Similarity NPD9261 Approved
0.7434 Intermediate Similarity NPD6831 Clinical (unspecified phase)
0.7395 Intermediate Similarity NPD5304 Approved
0.7395 Intermediate Similarity NPD5303 Approved
0.7395 Intermediate Similarity NPD1759 Phase 1
0.7387 Intermediate Similarity NPD9610 Approved
0.7387 Intermediate Similarity NPD9608 Approved
0.7373 Intermediate Similarity NPD9568 Approved
0.7368 Intermediate Similarity NPD4750 Phase 3
0.736 Intermediate Similarity NPD4208 Discontinued
0.736 Intermediate Similarity NPD4212 Discontinued
0.7355 Intermediate Similarity NPD3496 Discontinued
0.735 Intermediate Similarity NPD9281 Approved
0.7345 Intermediate Similarity NPD2342 Discontinued
0.7344 Intermediate Similarity NPD4060 Phase 1
0.7339 Intermediate Similarity NPD2797 Approved
0.7328 Intermediate Similarity NPD5535 Approved
0.7311 Intermediate Similarity NPD1758 Phase 1
0.7302 Intermediate Similarity NPD4207 Discontinued
0.7273 Intermediate Similarity NPD3019 Approved
0.7273 Intermediate Similarity NPD3028 Approved
0.7273 Intermediate Similarity NPD1242 Phase 1
0.7273 Intermediate Similarity NPD4589 Approved
0.7273 Intermediate Similarity NPD2932 Approved
0.7265 Intermediate Similarity NPD2228 Approved
0.7265 Intermediate Similarity NPD2229 Approved
0.7265 Intermediate Similarity NPD2234 Approved
0.7257 Intermediate Similarity NPD1444 Approved
0.7257 Intermediate Similarity NPD1445 Approved
0.7255 Intermediate Similarity NPD5734 Clinical (unspecified phase)
0.7252 Intermediate Similarity NPD2799 Discontinued
0.7248 Intermediate Similarity NPD9273 Approved
0.7238 Intermediate Similarity NPD9256 Approved
0.7238 Intermediate Similarity NPD9258 Approved
0.7236 Intermediate Similarity NPD9717 Approved
0.7227 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD5736 Approved
0.7213 Intermediate Similarity NPD3847 Discontinued
0.7197 Intermediate Similarity NPD5408 Approved
0.7197 Intermediate Similarity NPD5404 Approved
0.7197 Intermediate Similarity NPD5406 Approved
0.7197 Intermediate Similarity NPD5405 Approved
0.719 Intermediate Similarity NPD4235 Clinical (unspecified phase)
0.7177 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7164 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7154 Intermediate Similarity NPD1201 Approved
0.7143 Intermediate Similarity NPD6671 Approved
0.7143 Intermediate Similarity NPD9500 Approved
0.713 Intermediate Similarity NPD2684 Approved
0.712 Intermediate Similarity NPD1283 Approved
0.7113 Intermediate Similarity NPD9716 Approved
0.7111 Intermediate Similarity NPD7003 Approved
0.7107 Intermediate Similarity NPD3091 Approved
0.7094 Intermediate Similarity NPD228 Approved
0.7073 Intermediate Similarity NPD3143 Discontinued
0.7069 Intermediate Similarity NPD1792 Phase 2
0.7069 Intermediate Similarity NPD9380 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD1131 Approved
0.7063 Intermediate Similarity NPD1129 Approved
0.7063 Intermediate Similarity NPD1133 Approved
0.7063 Intermediate Similarity NPD1470 Approved
0.7063 Intermediate Similarity NPD1135 Approved
0.7063 Intermediate Similarity NPD1134 Approved
0.7063 Intermediate Similarity NPD1203 Approved
0.7059 Intermediate Similarity NPD5951 Approved
0.7054 Intermediate Similarity NPD3268 Approved
0.7054 Intermediate Similarity NPD3764 Approved
0.7034 Intermediate Similarity NPD1138 Approved
0.7027 Intermediate Similarity NPD2066 Phase 3
0.7023 Intermediate Similarity NPD5124 Phase 1
0.7023 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7016 Intermediate Similarity NPD1535 Discovery
0.701 Intermediate Similarity NPD9087 Approved
0.7008 Intermediate Similarity NPD257 Approved
0.7008 Intermediate Similarity NPD258 Approved
0.7 Intermediate Similarity NPD6663 Approved
0.6992 Remote Similarity NPD1778 Approved
0.6992 Remote Similarity NPD4059 Approved
0.6991 Remote Similarity NPD1931 Clinical (unspecified phase)
0.6991 Remote Similarity NPD1930 Approved
0.6991 Remote Similarity NPD1929 Approved
0.6981 Remote Similarity NPD800 Approved
0.6975 Remote Similarity NPD1241 Discontinued
0.6967 Remote Similarity NPD7330 Discontinued
0.696 Remote Similarity NPD1481 Phase 2
0.696 Remote Similarity NPD3070 Discontinued
0.6949 Remote Similarity NPD1139 Approved
0.6949 Remote Similarity NPD1137 Approved
0.6947 Remote Similarity NPD1240 Approved
0.6942 Remote Similarity NPD7325 Clinical (unspecified phase)
0.6937 Remote Similarity NPD9495 Approved
0.6935 Remote Similarity NPD2688 Clinical (unspecified phase)
0.6923 Remote Similarity NPD2313 Discontinued
0.6923 Remote Similarity NPD6798 Discontinued
0.6917 Remote Similarity NPD1476 Clinical (unspecified phase)
0.6916 Remote Similarity NPD1086 Approved
0.6916 Remote Similarity NPD1089 Approved
0.6916 Remote Similarity NPD1090 Approved
0.6911 Remote Similarity NPD4093 Discontinued
0.6905 Remote Similarity NPD4379 Clinical (unspecified phase)
0.69 Remote Similarity NPD9088 Approved
0.6897 Remote Similarity NPD290 Approved
0.6893 Remote Similarity NPD3971 Phase 1
0.6893 Remote Similarity NPD9491 Approved
0.6891 Remote Similarity NPD9379 Approved
0.6891 Remote Similarity NPD7843 Approved
0.6891 Remote Similarity NPD821 Approved
0.6891 Remote Similarity NPD9377 Approved
0.6885 Remote Similarity NPD856 Approved
0.6885 Remote Similarity NPD16 Approved
0.6881 Remote Similarity NPD5122 Clinical (unspecified phase)
0.688 Remote Similarity NPD1611 Approved
0.688 Remote Similarity NPD3092 Approved
0.688 Remote Similarity NPD1281 Approved
0.6875 Remote Similarity NPD2798 Approved
0.687 Remote Similarity NPD4248 Discontinued
0.6866 Remote Similarity NPD1509 Clinical (unspecified phase)
0.6861 Remote Similarity NPD8166 Discontinued
0.6857 Remote Similarity NPD9257 Approved
0.6857 Remote Similarity NPD9259 Approved
0.6855 Remote Similarity NPD2286 Discontinued
0.6855 Remote Similarity NPD1751 Approved
0.6855 Remote Similarity NPD5238 Clinical (unspecified phase)
0.685 Remote Similarity NPD3225 Approved
0.6846 Remote Similarity NPD3136 Phase 2
0.6842 Remote Similarity NPD1607 Approved
0.6842 Remote Similarity NPD6647 Phase 2
0.6829 Remote Similarity NPD1548 Phase 1
0.6829 Remote Similarity NPD1894 Discontinued
0.6825 Remote Similarity NPD9269 Phase 2
0.6818 Remote Similarity NPD1693 Approved
0.6818 Remote Similarity NPD943 Approved
0.6818 Remote Similarity NPD826 Approved
0.6818 Remote Similarity NPD825 Approved
0.6815 Remote Similarity NPD4476 Approved
0.6815 Remote Similarity NPD4477 Approved
0.681 Remote Similarity NPD968 Approved
0.6803 Remote Similarity NPD7636 Approved
0.68 Remote Similarity NPD9294 Approved
0.6797 Remote Similarity NPD987 Approved
0.6794 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6794 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6789 Remote Similarity NPD1088 Approved
0.6783 Remote Similarity NPD1237 Approved
0.6783 Remote Similarity NPD5909 Discontinued
0.678 Remote Similarity NPD5451 Approved
0.6777 Remote Similarity NPD475 Phase 2
0.6777 Remote Similarity NPD497 Approved
0.6777 Remote Similarity NPD1793 Approved
0.6777 Remote Similarity NPD690 Clinical (unspecified phase)
0.6777 Remote Similarity NPD1791 Approved
0.6774 Remote Similarity NPD9268 Approved
0.6774 Remote Similarity NPD1651 Approved
0.6767 Remote Similarity NPD6355 Discontinued
0.6765 Remote Similarity NPD7266 Discontinued
0.6748 Remote Similarity NPD318 Approved
0.6748 Remote Similarity NPD317 Approved
0.6746 Remote Similarity NPD1610 Phase 2
0.6744 Remote Similarity NPD3691 Phase 2
0.6744 Remote Similarity NPD3690 Phase 2
0.6742 Remote Similarity NPD520 Approved
0.6742 Remote Similarity NPD5729 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