Structure

Physi-Chem Properties

Molecular Weight:  270.05
Volume:  265.186
LogP:  2.991
LogD:  2.551
LogS:  -3.641
# Rotatable Bonds:  1
TPSA:  90.9
# H-Bond Aceptor:  5
# H-Bond Donor:  3
# Rings:  3
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.591
Synthetic Accessibility Score:  2.22
Fsp3:  0.0
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:  -4.824
MDCK Permeability:  1.2057118510711007e-05
Pgp-inhibitor:  0.004
Pgp-substrate:  0.866
Human Intestinal Absorption (HIA):  0.016
20% Bioavailability (F20%):  0.995
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.012
Plasma Protein Binding (PPB):  96.92609405517578%
Volume Distribution (VD):  0.443
Pgp-substrate:  4.070497512817383%

ADMET: Metabolism

CYP1A2-inhibitor:  0.971
CYP1A2-substrate:  0.161
CYP2C19-inhibitor:  0.314
CYP2C19-substrate:  0.052
CYP2C9-inhibitor:  0.396
CYP2C9-substrate:  0.868
CYP2D6-inhibitor:  0.63
CYP2D6-substrate:  0.877
CYP3A4-inhibitor:  0.766
CYP3A4-substrate:  0.162

ADMET: Excretion

Clearance (CL):  7.911
Half-life (T1/2):  0.868

ADMET: Toxicity

hERG Blockers:  0.026
Human Hepatotoxicity (H-HT):  0.082
Drug-inuced Liver Injury (DILI):  0.921
AMES Toxicity:  0.349
Rat Oral Acute Toxicity:  0.151
Maximum Recommended Daily Dose:  0.733
Skin Sensitization:  0.946
Carcinogencity:  0.396
Eye Corrosion:  0.006
Eye Irritation:  0.95
Respiratory Toxicity:  0.204

Download Data

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Structure MOL file  
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Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC7013

Natural Product ID:  NPC7013
Common Name*:   7-Hydroxy-3-(4-Hydroxyphenyl)-5-Methoxychromen-4-One
IUPAC Name:   7-hydroxy-3-(4-hydroxyphenyl)-5-methoxychromen-4-one
Synonyms:  
Standard InCHIKey:  YSINCDVRUMTOPK-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C16H12O5/c1-20-13-6-11(18)7-14-15(13)16(19)12(8-21-14)9-2-4-10(17)5-3-9/h2-8,17-18H,1H3
SMILES:  COc1cc(O)cc2c1c(=O)c(co2)c1ccc(cc1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1479463
PubChem CID:   5748551
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0002506] Isoflavonoids
        • [CHEMONTID:0002901] Isoflav-2-enes
          • [CHEMONTID:0000494] Isoflavones

*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
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/0003-9861(62)90112-1]
NPO5276 Zanthoxylum decaryi Species Rutaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/0031-9422(74)80113-5]
NPO22104 Trifolium pratense Species Fabaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0031-9422(00)94679-X]
NPO6775 Cistanche salsa Species Orobanchaceae Eukaryota n.a. whole plant n.a. PMID[10361686]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[11035032]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[12902239]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[13835567]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[14389294]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[1449509]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[14607989]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[15375647]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[15744050]
NPO11471 Garcinia oblongifolia Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[16724839]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[16850348]
NPO24639 Streptomyces filamentosus Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17284073]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[17439666]
NPO11471 Garcinia oblongifolia Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[19113969]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[22031445]
NPO546 Candida albicans Species Debaryomycetaceae Eukaryota n.a. n.a. n.a. PMID[23902158]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[2405251]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[24305546]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[24678285]
NPO11471 Garcinia oblongifolia Species Clusiaceae Eukaryota leaves Bobai, Guangxi Province, China 2005-Dec PMID[24679044]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[24733517]
NPO11471 Garcinia oblongifolia Species Clusiaceae Eukaryota Barks n.a. n.a. PMID[24754786]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[24831709]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[24981409]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[2687322]
NPO16444 Apios americana Species Fabaceae Eukaryota Tubers n.a. n.a. PMID[29932657]
NPO22104 Trifolium pratense Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[30199256]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[3289762]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[4266242]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[4616942]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[5764336]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[6306574]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[767332]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[7929110]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[8017107]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[8798704]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[8852895]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[8971708]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[9748245]
NPO1468 Crassostrea virginica Species Ostreidae Eukaryota n.a. n.a. Database[FooDB]
NPO5276 Zanthoxylum decaryi Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22104 Trifolium pratense Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6775 Cistanche salsa Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. Database[MetaboLights]
NPO5276 Zanthoxylum decaryi Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22104 Trifolium pratense Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6775 Cistanche salsa Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22104 Trifolium pratense Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1154 Neomeris annulata Species Dasycladaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11471 Garcinia oblongifolia Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9830 Arum maximum Species Araceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11127 Inulanthera calva Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26341 Trifolium resupinatum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2812 Lecanora kukunorensis Species Lecanoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22104 Trifolium pratense Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1077 Piper dilatatum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6948 Davidsoniella virescens Species Ceratocystidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1468 Crassostrea virginica Species Ostreidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26656 Heliotropium hirsutissimum Species Heliotropiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20657 Garuga pinnata Species Burseraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2419 Macrocentrus cingulum Species Braconidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO546 Candida albicans Species Debaryomycetaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24639 Streptomyces filamentosus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO2610 Chionodoxa gigantea n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO15242 Setosphaeria holmii Species Pleosporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14912 Linostoma pauciflorum n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO7011 Chamomilla recutita n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO6775 Cistanche salsa Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9298 Piper wightii Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6060 Amaranthus spinosus Species Amaranthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6679 Tephrosia watsoniana Species Geometridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16444 Apios americana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5276 Zanthoxylum decaryi Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10228 Ascochyta viciae Species Didymellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12152 Nicotiana raimondii Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4061 Trollius europaeus Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15875 Scolopia chinensis Species Salicaceae 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
NPT48 Individual Protein Lysine-specific demethylase 4D-like Homo sapiens Potency = 39810.7 nM PMID[549618]
NPT59 Individual Protein DNA polymerase beta Homo sapiens Potency = 70794.6 nM PMID[549618]
NPT64 Individual Protein ATPase family AAA domain-containing protein 5 Homo sapiens Potency n.a. 16353.5 nM PMID[549618]
NPT484 Individual Protein Luciferin 4-monooxygenase Photinus pyralis Potency n.a. 16944.1 nM PMID[549618]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 32642.7 nM PMID[549618]
NPT101 Individual Protein Glucagon-like peptide 1 receptor Homo sapiens Potency n.a. 3162.3 nM PMID[549618]
NPT113 Cell Line RAW264.7 Mus musculus IC50 > 1000.0 nM PMID[549620]
NPT2 Others Unspecified Potency n.a. 6309.6 nM PMID[549618]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 10417.9 nM PMID[549618]
NPT8 Individual Protein DNA polymerase iota Homo sapiens Potency n.a. 50118.7 nM PMID[549618]
NPT2 Others Unspecified Potency n.a. 11220.2 nM PMID[549618]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 13115.4 nM PMID[549618]
NPT2 Others Unspecified Potency n.a. 562.3 nM PMID[549618]
NPT35 Others n.a. LogD7.4 n.a. 2.0 n.a. PMID[549619]

☑ 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 NPC7013 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
1.0 High Similarity NPC303644
1.0 High Similarity NPC209560
1.0 High Similarity NPC294409
1.0 High Similarity NPC181124
1.0 High Similarity NPC116632
1.0 High Similarity NPC162680
0.9924 High Similarity NPC55162
0.9924 High Similarity NPC278323
0.9924 High Similarity NPC279668
0.9924 High Similarity NPC12175
0.9924 High Similarity NPC309154
0.9924 High Similarity NPC90665
0.985 High Similarity NPC295384
0.9847 High Similarity NPC39426
0.9847 High Similarity NPC234560
0.9776 High Similarity NPC144118
0.9776 High Similarity NPC219917
0.9776 High Similarity NPC215311
0.9776 High Similarity NPC48624
0.9776 High Similarity NPC80962
0.9776 High Similarity NPC101366
0.9776 High Similarity NPC259166
0.9776 High Similarity NPC326109
0.9776 High Similarity NPC213659
0.9776 High Similarity NPC172250
0.9776 High Similarity NPC204985
0.9773 High Similarity NPC87545
0.9773 High Similarity NPC235428
0.9704 High Similarity NPC26051
0.9704 High Similarity NPC469404
0.9704 High Similarity NPC55832
0.9704 High Similarity NPC268204
0.9704 High Similarity NPC52789
0.9701 High Similarity NPC283429
0.9699 High Similarity NPC212767
0.963 High Similarity NPC253822
0.9624 High Similarity NPC193792
0.9621 High Similarity NPC286336
0.9618 High Similarity NPC182428
0.9618 High Similarity NPC212631
0.9618 High Similarity NPC129132
0.9618 High Similarity NPC257756
0.9618 High Similarity NPC205468
0.9618 High Similarity NPC87231
0.9562 High Similarity NPC475705
0.9562 High Similarity NPC476178
0.9562 High Similarity NPC117836
0.9562 High Similarity NPC51887
0.9552 High Similarity NPC250266
0.9552 High Similarity NPC266597
0.9552 High Similarity NPC228661
0.9545 High Similarity NPC294593
0.9545 High Similarity NPC82225
0.9545 High Similarity NPC159623
0.9545 High Similarity NPC188646
0.9545 High Similarity NPC223354
0.9545 High Similarity NPC204960
0.9545 High Similarity NPC312318
0.9545 High Similarity NPC472365
0.9545 High Similarity NPC18877
0.9545 High Similarity NPC337373
0.9545 High Similarity NPC263670
0.9545 High Similarity NPC175098
0.9545 High Similarity NPC56031
0.9545 High Similarity NPC139813
0.9545 High Similarity NPC20560
0.9545 High Similarity NPC144051
0.9545 High Similarity NPC192304
0.9545 High Similarity NPC28753
0.9545 High Similarity NPC242294
0.9542 High Similarity NPC262359
0.9542 High Similarity NPC308037
0.9542 High Similarity NPC313618
0.9542 High Similarity NPC64359
0.9493 High Similarity NPC476055
0.9489 High Similarity NPC202981
0.9481 High Similarity NPC21350
0.9481 High Similarity NPC99333
0.9481 High Similarity NPC188947
0.9481 High Similarity NPC124269
0.9481 High Similarity NPC280284
0.9478 High Similarity NPC29353
0.9478 High Similarity NPC186838
0.9478 High Similarity NPC168105
0.9478 High Similarity NPC124784
0.9478 High Similarity NPC473391
0.9478 High Similarity NPC25287
0.9478 High Similarity NPC66349
0.9478 High Similarity NPC194281
0.9478 High Similarity NPC127447
0.9478 High Similarity NPC472364
0.9478 High Similarity NPC231772
0.9478 High Similarity NPC477242
0.9478 High Similarity NPC473887
0.9478 High Similarity NPC477244
0.9478 High Similarity NPC274109
0.9478 High Similarity NPC1486
0.9478 High Similarity NPC41461
0.9478 High Similarity NPC234133
0.9478 High Similarity NPC249606
0.9478 High Similarity NPC150399
0.9478 High Similarity NPC12165
0.9478 High Similarity NPC47815
0.9478 High Similarity NPC98115
0.9478 High Similarity NPC213603
0.9478 High Similarity NPC477243
0.9424 High Similarity NPC12377
0.9416 High Similarity NPC470087
0.9416 High Similarity NPC321980
0.9416 High Similarity NPC470089
0.9416 High Similarity NPC110969
0.9416 High Similarity NPC3188
0.9412 High Similarity NPC18260
0.9412 High Similarity NPC49242
0.9412 High Similarity NPC261234
0.9412 High Similarity NPC265871
0.9412 High Similarity NPC274784
0.9412 High Similarity NPC150648
0.9412 High Similarity NPC329203
0.9412 High Similarity NPC222342
0.9412 High Similarity NPC78913
0.9412 High Similarity NPC470211
0.9412 High Similarity NPC310135
0.9412 High Similarity NPC477956
0.9412 High Similarity NPC225153
0.9412 High Similarity NPC20709
0.9407 High Similarity NPC290291
0.9407 High Similarity NPC188879
0.9407 High Similarity NPC275055
0.9407 High Similarity NPC472419
0.9407 High Similarity NPC317119
0.9407 High Similarity NPC153979
0.9403 High Similarity NPC13575
0.9403 High Similarity NPC131039
0.9403 High Similarity NPC156092
0.9394 High Similarity NPC164236
0.9394 High Similarity NPC475008
0.9394 High Similarity NPC186097
0.9394 High Similarity NPC475009
0.9394 High Similarity NPC66384
0.9394 High Similarity NPC128348
0.9394 High Similarity NPC189106
0.9394 High Similarity NPC112192
0.9394 High Similarity NPC309717
0.9389 High Similarity NPC185497
0.9389 High Similarity NPC247779
0.9357 High Similarity NPC51070
0.9357 High Similarity NPC237635
0.9357 High Similarity NPC79469
0.9357 High Similarity NPC24673
0.9357 High Similarity NPC97716
0.9357 High Similarity NPC222298
0.9357 High Similarity NPC104406
0.9357 High Similarity NPC201731
0.9353 High Similarity NPC303185
0.9353 High Similarity NPC234629
0.9353 High Similarity NPC184649
0.9353 High Similarity NPC311741
0.9348 High Similarity NPC226636
0.9348 High Similarity NPC11561
0.9343 High Similarity NPC188243
0.9343 High Similarity NPC284550
0.9343 High Similarity NPC270883
0.9343 High Similarity NPC269652
0.9343 High Similarity NPC172986
0.9343 High Similarity NPC265178
0.9343 High Similarity NPC281207
0.9343 High Similarity NPC76445
0.9343 High Similarity NPC261227
0.9343 High Similarity NPC6407
0.9343 High Similarity NPC11056
0.9343 High Similarity NPC129853
0.9343 High Similarity NPC110228
0.9343 High Similarity NPC241100
0.9343 High Similarity NPC159275
0.9338 High Similarity NPC251681
0.9338 High Similarity NPC243528
0.9338 High Similarity NPC25427
0.9338 High Similarity NPC472460
0.9338 High Similarity NPC329225
0.9338 High Similarity NPC201395
0.9338 High Similarity NPC472368
0.9338 High Similarity NPC147686
0.9338 High Similarity NPC471620
0.9338 High Similarity NPC118813
0.9333 High Similarity NPC13408
0.9333 High Similarity NPC472367
0.9333 High Similarity NPC476333
0.9333 High Similarity NPC254741
0.9333 High Similarity NPC240593
0.9328 High Similarity NPC172262
0.9328 High Similarity NPC103842
0.9313 High Similarity NPC60558
0.9291 High Similarity NPC266572
0.9291 High Similarity NPC168085
0.9291 High Similarity NPC139364
0.9291 High Similarity NPC194653
0.9291 High Similarity NPC203747
0.9291 High Similarity NPC254702
0.9291 High Similarity NPC80710

  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 NPC7013 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
0.9847 High Similarity NPD1510 Phase 2
0.9542 High Similarity NPD1240 Approved
0.9398 High Similarity NPD1607 Approved
0.9338 High Similarity NPD1549 Phase 2
0.9265 High Similarity NPD1550 Clinical (unspecified phase)
0.9265 High Similarity NPD1552 Clinical (unspecified phase)
0.9214 High Similarity NPD4378 Clinical (unspecified phase)
0.9191 High Similarity NPD2796 Approved
0.9028 High Similarity NPD4380 Phase 2
0.8944 High Similarity NPD7410 Clinical (unspecified phase)
0.8776 High Similarity NPD1934 Approved
0.8741 High Similarity NPD1511 Approved
0.8716 High Similarity NPD2393 Clinical (unspecified phase)
0.8707 High Similarity NPD7411 Suspended
0.8667 High Similarity NPD4381 Clinical (unspecified phase)
0.8667 High Similarity NPD7075 Discontinued
0.8662 High Similarity NPD3750 Approved
0.8662 High Similarity NPD1878 Clinical (unspecified phase)
0.8658 High Similarity NPD8443 Clinical (unspecified phase)
0.8652 High Similarity NPD970 Clinical (unspecified phase)
0.8621 High Similarity NPD1512 Approved
0.8611 High Similarity NPD6799 Approved
0.8591 High Similarity NPD2801 Approved
0.8591 High Similarity NPD7819 Suspended
0.8591 High Similarity NPD7096 Clinical (unspecified phase)
0.8523 High Similarity NPD6801 Discontinued
0.8511 High Similarity NPD1551 Phase 2
0.8477 Intermediate Similarity NPD3882 Suspended
0.8389 Intermediate Similarity NPD6599 Discontinued
0.838 Intermediate Similarity NPD2935 Discontinued
0.8355 Intermediate Similarity NPD7768 Phase 2
0.8333 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.831 Intermediate Similarity NPD3748 Approved
0.8301 Intermediate Similarity NPD3749 Approved
0.8298 Intermediate Similarity NPD6651 Approved
0.8289 Intermediate Similarity NPD3817 Phase 2
0.8286 Intermediate Similarity NPD943 Approved
0.8273 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.8248 Intermediate Similarity NPD2798 Approved
0.8228 Intermediate Similarity NPD3818 Discontinued
0.8217 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8217 Intermediate Similarity NPD6166 Phase 2
0.8217 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8207 Intermediate Similarity NPD2800 Approved
0.8207 Intermediate Similarity NPD1243 Approved
0.8194 Intermediate Similarity NPD2344 Approved
0.8188 Intermediate Similarity NPD920 Approved
0.8188 Intermediate Similarity NPD5403 Approved
0.8182 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.8176 Intermediate Similarity NPD5401 Approved
0.8176 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8163 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.8141 Intermediate Similarity NPD6959 Discontinued
0.8089 Intermediate Similarity NPD6232 Discontinued
0.8063 Intermediate Similarity NPD7054 Approved
0.8054 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.8054 Intermediate Similarity NPD2532 Approved
0.8054 Intermediate Similarity NPD2534 Approved
0.8054 Intermediate Similarity NPD2533 Approved
0.805 Intermediate Similarity NPD7473 Discontinued
0.8043 Intermediate Similarity NPD1203 Approved
0.8015 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.8014 Intermediate Similarity NPD2313 Discontinued
0.8012 Intermediate Similarity NPD7074 Phase 3
0.8012 Intermediate Similarity NPD7472 Approved
0.8 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7985 Intermediate Similarity NPD1548 Phase 1
0.7975 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7973 Intermediate Similarity NPD2309 Approved
0.7963 Intermediate Similarity NPD5953 Discontinued
0.7963 Intermediate Similarity NPD6797 Phase 2
0.7962 Intermediate Similarity NPD5494 Approved
0.7935 Intermediate Similarity NPD5402 Approved
0.7931 Intermediate Similarity NPD2799 Discontinued
0.7914 Intermediate Similarity NPD7251 Discontinued
0.7905 Intermediate Similarity NPD4628 Phase 3
0.7883 Intermediate Similarity NPD1610 Phase 2
0.7872 Intermediate Similarity NPD6832 Phase 2
0.7872 Intermediate Similarity NPD4908 Phase 1
0.7866 Intermediate Similarity NPD7808 Phase 3
0.7852 Intermediate Similarity NPD9545 Approved
0.784 Intermediate Similarity NPD7286 Phase 2
0.7838 Intermediate Similarity NPD2654 Approved
0.7836 Intermediate Similarity NPD9493 Approved
0.7829 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7826 Intermediate Similarity NPD3972 Approved
0.7826 Intermediate Similarity NPD9717 Approved
0.7808 Intermediate Similarity NPD4308 Phase 3
0.7808 Intermediate Similarity NPD7033 Discontinued
0.7805 Intermediate Similarity NPD6559 Discontinued
0.7785 Intermediate Similarity NPD919 Approved
0.7762 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7762 Intermediate Similarity NPD3268 Approved
0.7758 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7755 Intermediate Similarity NPD6099 Approved
0.7755 Intermediate Similarity NPD6100 Approved
0.7754 Intermediate Similarity NPD422 Phase 1
0.7748 Intermediate Similarity NPD7390 Discontinued
0.7727 Intermediate Similarity NPD3226 Approved
0.7724 Intermediate Similarity NPD230 Phase 1
0.7688 Intermediate Similarity NPD1247 Approved
0.766 Intermediate Similarity NPD2797 Approved
0.766 Intermediate Similarity NPD1470 Approved
0.7639 Intermediate Similarity NPD3764 Approved
0.7626 Intermediate Similarity NPD1201 Approved
0.7622 Intermediate Similarity NPD5844 Phase 1
0.7613 Intermediate Similarity NPD7458 Discontinued
0.7603 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7595 Intermediate Similarity NPD4288 Approved
0.7593 Intermediate Similarity NPD3926 Phase 2
0.7589 Intermediate Similarity NPD3225 Approved
0.7589 Intermediate Similarity NPD1876 Approved
0.7584 Intermediate Similarity NPD2346 Discontinued
0.7568 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.755 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7535 Intermediate Similarity NPD3267 Approved
0.7535 Intermediate Similarity NPD1164 Approved
0.7535 Intermediate Similarity NPD3266 Approved
0.7534 Intermediate Similarity NPD4307 Phase 2
0.7532 Intermediate Similarity NPD1465 Phase 2
0.753 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7514 Intermediate Similarity NPD4363 Phase 3
0.7514 Intermediate Similarity NPD4360 Phase 2
0.7483 Intermediate Similarity NPD1933 Approved
0.7481 Intermediate Similarity NPD1241 Discontinued
0.7471 Intermediate Similarity NPD4361 Phase 2
0.7471 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7448 Intermediate Similarity NPD3027 Phase 3
0.7447 Intermediate Similarity NPD1608 Approved
0.7434 Intermediate Similarity NPD7003 Approved
0.7431 Intermediate Similarity NPD9494 Approved
0.7429 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7423 Intermediate Similarity NPD5711 Approved
0.7423 Intermediate Similarity NPD5710 Approved
0.7415 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7415 Intermediate Similarity NPD1613 Approved
0.7403 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.74 Intermediate Similarity NPD5404 Approved
0.74 Intermediate Similarity NPD5408 Approved
0.74 Intermediate Similarity NPD5406 Approved
0.74 Intermediate Similarity NPD5405 Approved
0.7397 Intermediate Similarity NPD411 Approved
0.7397 Intermediate Similarity NPD1296 Phase 2
0.7379 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7375 Intermediate Similarity NPD2296 Approved
0.7365 Intermediate Similarity NPD447 Suspended
0.7365 Intermediate Similarity NPD1729 Discontinued
0.7365 Intermediate Similarity NPD5124 Phase 1
0.7365 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7361 Intermediate Similarity NPD1019 Discontinued
0.7355 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.731 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7296 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7283 Intermediate Similarity NPD4287 Approved
0.7279 Intermediate Similarity NPD6798 Discontinued
0.7278 Intermediate Similarity NPD6104 Discontinued
0.7273 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.725 Intermediate Similarity NPD6844 Discontinued
0.7246 Intermediate Similarity NPD3751 Discontinued
0.7239 Intermediate Similarity NPD74 Approved
0.7239 Intermediate Similarity NPD9266 Approved
0.7237 Intermediate Similarity NPD1471 Phase 3
0.7237 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7234 Intermediate Similarity NPD17 Approved
0.7229 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7211 Intermediate Similarity NPD4625 Phase 3
0.7207 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7194 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD5890 Approved
0.7188 Intermediate Similarity NPD5889 Approved
0.717 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7164 Intermediate Similarity NPD9267 Approved
0.7164 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7164 Intermediate Similarity NPD9264 Approved
0.7164 Intermediate Similarity NPD9263 Approved
0.7163 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7161 Intermediate Similarity NPD2354 Approved
0.7158 Intermediate Similarity NPD7584 Approved
0.7153 Intermediate Similarity NPD4749 Approved
0.7152 Intermediate Similarity NPD7199 Phase 2
0.7143 Intermediate Similarity NPD6280 Approved
0.7143 Intermediate Similarity NPD37 Approved
0.7143 Intermediate Similarity NPD6279 Approved
0.7134 Intermediate Similarity NPD7447 Phase 1
0.7134 Intermediate Similarity NPD4661 Approved
0.7134 Intermediate Similarity NPD4662 Approved
0.7133 Intermediate Similarity NPD6355 Discontinued
0.7108 Intermediate Similarity NPD7229 Phase 3
0.7103 Intermediate Similarity NPD1283 Approved
0.7092 Intermediate Similarity NPD1894 Discontinued
0.7086 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD9269 Phase 2
0.7083 Intermediate Similarity NPD1481 Phase 2
0.7075 Intermediate Similarity NPD2861 Phase 2
0.7073 Intermediate Similarity NPD6971 Discontinued
0.707 Intermediate Similarity NPD7213 Phase 3
0.707 Intermediate Similarity NPD7212 Phase 2
0.7067 Intermediate Similarity NPD3140 Approved

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data