Structure

Physi-Chem Properties

Molecular Weight:  312.14
Volume:  328.216
LogP:  4.649
LogD:  3.678
LogS:  -3.757
# Rotatable Bonds:  2
TPSA:  59.67
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.668
Synthetic Accessibility Score:  3.351
Fsp3:  0.316
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.67
MDCK Permeability:  2.4323757315869443e-05
Pgp-inhibitor:  0.967
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.083
20% Bioavailability (F20%):  0.006
30% Bioavailability (F30%):  0.02

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.018
Plasma Protein Binding (PPB):  94.25752258300781%
Volume Distribution (VD):  1.104
Pgp-substrate:  6.6622772216796875%

ADMET: Metabolism

CYP1A2-inhibitor:  0.927
CYP1A2-substrate:  0.69
CYP2C19-inhibitor:  0.757
CYP2C19-substrate:  0.306
CYP2C9-inhibitor:  0.79
CYP2C9-substrate:  0.845
CYP2D6-inhibitor:  0.864
CYP2D6-substrate:  0.419
CYP3A4-inhibitor:  0.749
CYP3A4-substrate:  0.374

ADMET: Excretion

Clearance (CL):  1.675
Half-life (T1/2):  0.195

ADMET: Toxicity

hERG Blockers:  0.02
Human Hepatotoxicity (H-HT):  0.72
Drug-inuced Liver Injury (DILI):  0.689
AMES Toxicity:  0.015
Rat Oral Acute Toxicity:  0.963
Maximum Recommended Daily Dose:  0.614
Skin Sensitization:  0.56
Carcinogencity:  0.928
Eye Corrosion:  0.003
Eye Irritation:  0.114
Respiratory Toxicity:  0.863

Download Data

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Structure MOL file  
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  Natural Product: NPC37009

Natural Product ID:  NPC37009
Common Name*:   Nordentatin
IUPAC Name:   5-hydroxy-2,2-dimethyl-10-(2-methylbut-3-en-2-yl)pyrano[3,2-g]chromen-8-one
Synonyms:   Nordentatin
Standard InCHIKey:  WYMMNGQSPNWCIK-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C19H20O4/c1-6-18(2,3)14-16-11(7-8-13(20)22-16)15(21)12-9-10-19(4,5)23-17(12)14/h6-10,21H,1H2,2-5H3
SMILES:  C=CC(c1c2OC(C)(C)C=Cc2c(c2c1oc(=O)cc2)O)(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL158309
PubChem CID:   5495613
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000145] Coumarins and derivatives
        • [CHEMONTID:0003484] Pyranocoumarins
          • [CHEMONTID:0003486] Linear pyranocoumarins

*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
NPO19266 Clausena excavata Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[11000023]
NPO18265 Citrus tamurana Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[11999424]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[12628396]
NPO2236 Pyrola rotundifolia Species Ericaceae Eukaryota n.a. whole plant n.a. PMID[16079548]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota Hairy roots n.a. n.a. PMID[19271765]
NPO21978 Clausena harmandiana Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO5489 Cinnamomum tenuifolium Species Lauraceae Eukaryota stems n.a. n.a. PMID[19754130]
NPO21978 Clausena harmandiana Species Rutaceae Eukaryota n.a. root n.a. PMID[21302964]
NPO10906 Pinus koraiensis Species Pinaceae Eukaryota n.a. n.a. n.a. PMID[21953622]
NPO9537 Bauhinia racemosa Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[22348826]
NPO11021 Moringa oleifera Species Moringaceae Eukaryota n.a. leaf n.a. PMID[24024688]
NPO8528 Citrus junos Species Rutaceae Eukaryota n.a. fruit n.a. PMID[25522543]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[26285573]
NPO21978 Clausena harmandiana Species Rutaceae Eukaryota Root barks n.a. n.a. PMID[3236015]
NPO10906 Pinus koraiensis Species Pinaceae Eukaryota Twigs n.a. n.a. PMID[32520551]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[6619887]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[6631435]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[7264679]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[7264682]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[7320741]
NPO11021 Moringa oleifera Species Moringaceae Eukaryota n.a. n.a. n.a. PMID[7798960]
NPO11021 Moringa oleifera Species Moringaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO11021 Moringa oleifera Species Moringaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO11021 Moringa oleifera Species Moringaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO11021 Moringa oleifera Species Moringaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO11021 Moringa oleifera Species Moringaceae Eukaryota n.a. n.a. Database[FooDB]
NPO15730.1 Citrus medica var. etrog Varieties Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14773 Uncaria perrottetii Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18265 Citrus tamurana Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11785 Citrus hassaku Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2236 Pyrola rotundifolia Species Ericaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10906 Pinus koraiensis Species Pinaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9955 Citrus jambhiri Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8528 Citrus junos Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19266 Clausena excavata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7444 Clausena dentata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14773 Uncaria perrottetii Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18265 Citrus tamurana Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2236 Pyrola rotundifolia Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19266 Clausena excavata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15730.1 Citrus medica var. etrog Varieties Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11785 Citrus hassaku Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18677 Anagallis arvensis Species Primulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7444 Clausena dentata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10906 Pinus koraiensis Species Pinaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8528 Citrus junos Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9955 Citrus jambhiri Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19266 Clausena excavata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO10906 Pinus koraiensis Species Pinaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11107 Stevia alpina Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9537 Bauhinia racemosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7263 Phyllobates aurotaenia Species Dendrobatidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5904 Grindelia humilis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9919 Jaspis stellifera Species Ancorinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18265 Citrus tamurana Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9955 Citrus jambhiri Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2236 Pyrola rotundifolia Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5489 Cinnamomum tenuifolium Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21978 Clausena harmandiana Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29494 Stoeba extensa n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO2962 Curvularia spicifera Species Pleosporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14773 Uncaria perrottetii Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19266 Clausena excavata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11785 Citrus hassaku Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11978 Tanacetum argyrophyllum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7444 Clausena dentata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7003 Streptomyces violaceochromogenes Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17324 Pluchea dioscoridis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8528 Citrus junos Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12094 Cyclamen balearicum Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9765 Petriella guttulata Species Microascaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4311 Asterolasia squamuligera Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19014 Palythoa tuberculosa Species Sphenopidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10402 Strophanthus eminii Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10906 Pinus koraiensis Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24877 Maianthemum stellatum Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11021 Moringa oleifera Species Moringaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18677 Anagallis arvensis Species Primulaceae 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
NPT91 Cell Line KB Homo sapiens EC50 = 9.63 ug.mL-1 PMID[564008]
NPT83 Cell Line MCF7 Homo sapiens EC50 = 17.32 ug.mL-1 PMID[564008]
NPT81 Cell Line A549 Homo sapiens EC50 = 8.7 ug.mL-1 PMID[564008]
NPT639 Cell Line NCI-H187 Homo sapiens IC50 = 11810.0 nM PMID[564009]
NPT91 Cell Line KB Homo sapiens IC50 = 20620.0 nM PMID[564009]
NPT189 Cell Line Vero Chlorocebus aethiops IC50 = 56350.0 nM PMID[564009]
NPT32 Organism Mus musculus Mus musculus Inhibition = 91.2 % PMID[564006]
NPT963 Organism Hepatitis B virus Hepatitis B virus EC50 = 6380.0 nM PMID[564008]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. EC50 = 9.96 ug.mL-1 PMID[564008]

☑ 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 NPC37009 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 NPC66430
0.9841 High Similarity NPC83535
0.9597 High Similarity NPC163248
0.952 High Similarity NPC289316
0.936 High Similarity NPC232692
0.936 High Similarity NPC202594
0.912 High Similarity NPC150214
0.9062 High Similarity NPC243688
0.9048 High Similarity NPC50720
0.9048 High Similarity NPC143725
0.9015 High Similarity NPC131950
0.9 High Similarity NPC32463
0.8992 High Similarity NPC185066
0.8976 High Similarity NPC291899
0.8939 High Similarity NPC142563
0.8939 High Similarity NPC241165
0.8939 High Similarity NPC1220
0.8939 High Similarity NPC141822
0.8939 High Similarity NPC291551
0.8939 High Similarity NPC205797
0.8906 High Similarity NPC244495
0.8906 High Similarity NPC93219
0.8849 High Similarity NPC206212
0.8849 High Similarity NPC71184
0.8846 High Similarity NPC157212
0.8837 High Similarity NPC471826
0.8797 High Similarity NPC31849
0.8797 High Similarity NPC469965
0.8777 High Similarity NPC71739
0.876 High Similarity NPC471828
0.876 High Similarity NPC471827
0.875 High Similarity NPC290605
0.875 High Similarity NPC173350
0.875 High Similarity NPC154176
0.875 High Similarity NPC279573
0.8731 High Similarity NPC180716
0.8731 High Similarity NPC224475
0.8731 High Similarity NPC213173
0.8722 High Similarity NPC194277
0.8702 High Similarity NPC139595
0.8702 High Similarity NPC60704
0.8702 High Similarity NPC293642
0.8682 High Similarity NPC201667
0.8682 High Similarity NPC73413
0.8682 High Similarity NPC111347
0.8676 High Similarity NPC131198
0.8672 High Similarity NPC257188
0.8672 High Similarity NPC13007
0.8667 High Similarity NPC472525
0.8667 High Similarity NPC61499
0.8657 High Similarity NPC163557
0.8623 High Similarity NPC138149
0.8623 High Similarity NPC152771
0.8623 High Similarity NPC155552
0.8623 High Similarity NPC170812
0.8623 High Similarity NPC195357
0.8615 High Similarity NPC168259
0.8613 High Similarity NPC35501
0.8613 High Similarity NPC47040
0.8613 High Similarity NPC144512
0.8613 High Similarity NPC37428
0.8613 High Similarity NPC137262
0.8613 High Similarity NPC211110
0.8613 High Similarity NPC278600
0.8613 High Similarity NPC151946
0.8605 High Similarity NPC472518
0.8605 High Similarity NPC273772
0.8605 High Similarity NPC109675
0.8603 High Similarity NPC38099
0.8603 High Similarity NPC26954
0.8594 High Similarity NPC187868
0.8594 High Similarity NPC52247
0.8593 High Similarity NPC50896
0.8593 High Similarity NPC204353
0.8593 High Similarity NPC62366
0.8593 High Similarity NPC326600
0.8582 High Similarity NPC19157
0.8571 High Similarity NPC471824
0.8561 High Similarity NPC221173
0.8561 High Similarity NPC93640
0.8561 High Similarity NPC20631
0.8551 High Similarity NPC312881
0.8551 High Similarity NPC71903
0.854 High Similarity NPC153818
0.854 High Similarity NPC155963
0.854 High Similarity NPC281014
0.854 High Similarity NPC232246
0.854 High Similarity NPC294456
0.854 High Similarity NPC184861
0.854 High Similarity NPC212124
0.854 High Similarity NPC225106
0.8538 High Similarity NPC27671
0.8529 High Similarity NPC472521
0.8527 High Similarity NPC96286
0.8527 High Similarity NPC248429
0.8519 High Similarity NPC296624
0.8519 High Similarity NPC471910
0.8519 High Similarity NPC207002
0.8519 High Similarity NPC167111
0.8519 High Similarity NPC133956
0.8519 High Similarity NPC318400
0.8516 High Similarity NPC302107
0.8511 High Similarity NPC43716
0.8511 High Similarity NPC106126
0.8511 High Similarity NPC475719
0.8511 High Similarity NPC469701
0.8511 High Similarity NPC295696
0.8511 High Similarity NPC108994
0.8511 High Similarity NPC101255
0.85 High Similarity NPC470555
0.8496 Intermediate Similarity NPC168710
0.8496 Intermediate Similarity NPC474289
0.8489 Intermediate Similarity NPC310370
0.8489 Intermediate Similarity NPC472343
0.8489 Intermediate Similarity NPC287286
0.8489 Intermediate Similarity NPC183642
0.8485 Intermediate Similarity NPC121740
0.8485 Intermediate Similarity NPC258567
0.8485 Intermediate Similarity NPC224774
0.8478 Intermediate Similarity NPC221046
0.8467 Intermediate Similarity NPC224543
0.8467 Intermediate Similarity NPC78746
0.8467 Intermediate Similarity NPC283331
0.8467 Intermediate Similarity NPC188380
0.8456 Intermediate Similarity NPC100986
0.8456 Intermediate Similarity NPC18804
0.8456 Intermediate Similarity NPC84894
0.8456 Intermediate Similarity NPC260265
0.8456 Intermediate Similarity NPC267412
0.8456 Intermediate Similarity NPC287182
0.8456 Intermediate Similarity NPC166672
0.8456 Intermediate Similarity NPC74655
0.8456 Intermediate Similarity NPC98179
0.8456 Intermediate Similarity NPC253574
0.8456 Intermediate Similarity NPC147030
0.8456 Intermediate Similarity NPC198381
0.8456 Intermediate Similarity NPC195343
0.8456 Intermediate Similarity NPC319859
0.8456 Intermediate Similarity NPC164269
0.8456 Intermediate Similarity NPC127888
0.8456 Intermediate Similarity NPC47163
0.845 Intermediate Similarity NPC144418
0.8444 Intermediate Similarity NPC469956
0.8444 Intermediate Similarity NPC14248
0.844 Intermediate Similarity NPC36732
0.8438 Intermediate Similarity NPC247553
0.8433 Intermediate Similarity NPC80170
0.8433 Intermediate Similarity NPC113098
0.8421 Intermediate Similarity NPC472519
0.8421 Intermediate Similarity NPC469453
0.8406 Intermediate Similarity NPC14697
0.8406 Intermediate Similarity NPC306365
0.8394 Intermediate Similarity NPC86892
0.8394 Intermediate Similarity NPC33986
0.8394 Intermediate Similarity NPC471625
0.8394 Intermediate Similarity NPC471909
0.8394 Intermediate Similarity NPC281241
0.8394 Intermediate Similarity NPC472424
0.8382 Intermediate Similarity NPC222036
0.8382 Intermediate Similarity NPC469955
0.8382 Intermediate Similarity NPC7526
0.8382 Intermediate Similarity NPC469952
0.837 Intermediate Similarity NPC272650
0.837 Intermediate Similarity NPC29734
0.837 Intermediate Similarity NPC267336
0.8369 Intermediate Similarity NPC236419
0.8358 Intermediate Similarity NPC134360
0.8357 Intermediate Similarity NPC279851
0.8357 Intermediate Similarity NPC472520
0.8346 Intermediate Similarity NPC183154
0.8346 Intermediate Similarity NPC263754
0.8345 Intermediate Similarity NPC327612
0.8345 Intermediate Similarity NPC73078
0.8345 Intermediate Similarity NPC319870
0.8345 Intermediate Similarity NPC307883
0.8345 Intermediate Similarity NPC148738
0.8333 Intermediate Similarity NPC285748
0.8333 Intermediate Similarity NPC128529
0.8333 Intermediate Similarity NPC177281
0.8333 Intermediate Similarity NPC160727
0.8333 Intermediate Similarity NPC476455
0.8333 Intermediate Similarity NPC55615
0.8333 Intermediate Similarity NPC180477
0.8333 Intermediate Similarity NPC474108
0.8333 Intermediate Similarity NPC283019
0.8333 Intermediate Similarity NPC177995
0.8333 Intermediate Similarity NPC471630
0.8333 Intermediate Similarity NPC149320
0.8321 Intermediate Similarity NPC315807
0.8321 Intermediate Similarity NPC307412
0.8321 Intermediate Similarity NPC55149
0.831 Intermediate Similarity NPC471763
0.8309 Intermediate Similarity NPC281558
0.8309 Intermediate Similarity NPC123954
0.8286 Intermediate Similarity NPC199458
0.8286 Intermediate Similarity NPC183639
0.8284 Intermediate Similarity NPC199204
0.8281 Intermediate Similarity NPC152306
0.8276 Intermediate Similarity NPC208303
0.8276 Intermediate Similarity NPC161864

  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 NPC37009 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
0.8939 High Similarity NPD5123 Clinical (unspecified phase)
0.8939 High Similarity NPD5124 Phase 1
0.8594 High Similarity NPD422 Phase 1
0.8298 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.8042 Intermediate Similarity NPD3750 Approved
0.8029 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7883 Intermediate Similarity NPD4908 Phase 1
0.7847 Intermediate Similarity NPD2800 Approved
0.7826 Intermediate Similarity NPD4625 Phase 3
0.7823 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7794 Intermediate Similarity NPD2797 Approved
0.7778 Intermediate Similarity NPD4749 Approved
0.777 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7761 Intermediate Similarity NPD1610 Phase 2
0.7727 Intermediate Similarity NPD1548 Phase 1
0.7721 Intermediate Similarity NPD3225 Approved
0.7703 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD3748 Approved
0.7662 Intermediate Similarity NPD7768 Phase 2
0.7643 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7643 Intermediate Similarity NPD3268 Approved
0.7626 Intermediate Similarity NPD1008 Clinical (unspecified phase)
0.7603 Intermediate Similarity NPD1652 Phase 2
0.7532 Intermediate Similarity NPD7819 Suspended
0.7518 Intermediate Similarity NPD1296 Phase 2
0.7517 Intermediate Similarity NPD6099 Approved
0.7517 Intermediate Similarity NPD6100 Approved
0.7516 Intermediate Similarity NPD7411 Suspended
0.75 Intermediate Similarity NPD7075 Discontinued
0.7483 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7481 Intermediate Similarity NPD4626 Approved
0.7468 Intermediate Similarity NPD6801 Discontinued
0.7467 Intermediate Similarity NPD2532 Approved
0.7467 Intermediate Similarity NPD2534 Approved
0.7467 Intermediate Similarity NPD2533 Approved
0.7448 Intermediate Similarity NPD4308 Phase 3
0.7434 Intermediate Similarity NPD1653 Approved
0.7431 Intermediate Similarity NPD6651 Approved
0.7419 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7415 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7413 Intermediate Similarity NPD4060 Phase 1
0.7405 Intermediate Similarity NPD5535 Approved
0.7389 Intermediate Similarity NPD3749 Approved
0.7376 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7365 Intermediate Similarity NPD1243 Approved
0.7338 Intermediate Similarity NPD8651 Approved
0.7338 Intermediate Similarity NPD6696 Suspended
0.7338 Intermediate Similarity NPD6599 Discontinued
0.7329 Intermediate Similarity NPD1510 Phase 2
0.7329 Intermediate Similarity NPD2799 Discontinued
0.7329 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7324 Intermediate Similarity NPD7095 Approved
0.7315 Intermediate Similarity NPD4628 Phase 3
0.7305 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD3496 Discontinued
0.7297 Intermediate Similarity NPD1549 Phase 2
0.7286 Intermediate Similarity NPD3266 Approved
0.7286 Intermediate Similarity NPD3267 Approved
0.7279 Intermediate Similarity NPD2796 Approved
0.7279 Intermediate Similarity NPD2935 Discontinued
0.7279 Intermediate Similarity NPD1551 Phase 2
0.7279 Intermediate Similarity NPD5691 Approved
0.7273 Intermediate Similarity NPD2313 Discontinued
0.7266 Intermediate Similarity NPD9697 Approved
0.7261 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7255 Intermediate Similarity NPD920 Approved
0.7234 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.723 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.723 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD4380 Phase 2
0.7211 Intermediate Similarity NPD7033 Discontinued
0.72 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7195 Intermediate Similarity NPD5844 Phase 1
0.7194 Intermediate Similarity NPD9717 Approved
0.7179 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7172 Intermediate Similarity NPD4140 Approved
0.7172 Intermediate Similarity NPD4307 Phase 2
0.7172 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7172 Intermediate Similarity NPD1240 Approved
0.7172 Intermediate Similarity NPD1613 Approved
0.7171 Intermediate Similarity NPD6799 Approved
0.7163 Intermediate Similarity NPD1203 Approved
0.7152 Intermediate Similarity NPD4288 Approved
0.7143 Intermediate Similarity NPD5403 Approved
0.7132 Intermediate Similarity NPD7644 Approved
0.7114 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7114 Intermediate Similarity NPD6004 Phase 3
0.7114 Intermediate Similarity NPD6005 Phase 3
0.7114 Intermediate Similarity NPD6002 Phase 3
0.7114 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7111 Intermediate Similarity NPD6671 Approved
0.7107 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD6666 Approved
0.7105 Intermediate Similarity NPD6667 Approved
0.7105 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD1778 Approved
0.709 Intermediate Similarity NPD1398 Phase 1
0.7089 Intermediate Similarity NPD1465 Phase 2
0.7086 Intermediate Similarity NPD7003 Approved
0.7075 Intermediate Similarity NPD1607 Approved
0.7063 Intermediate Similarity NPD2861 Phase 2
0.7063 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD1511 Approved
0.7059 Intermediate Similarity NPD7340 Approved
0.7051 Intermediate Similarity NPD3226 Approved
0.7034 Intermediate Similarity NPD3764 Approved
0.7034 Intermediate Similarity NPD1699 Clinical (unspecified phase)
0.7031 Intermediate Similarity NPD940 Approved
0.7031 Intermediate Similarity NPD846 Approved
0.7024 Intermediate Similarity NPD7549 Discontinued
0.7013 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7013 Intermediate Similarity NPD5401 Approved
0.7013 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7013 Intermediate Similarity NPD7447 Phase 1
0.7007 Intermediate Similarity NPD4340 Discontinued
0.7 Intermediate Similarity NPD1611 Approved
0.7 Intermediate Similarity NPD2346 Discontinued
0.6994 Remote Similarity NPD6232 Discontinued
0.6985 Remote Similarity NPD7157 Approved
0.6981 Remote Similarity NPD2801 Approved
0.6968 Remote Similarity NPD1512 Approved
0.6966 Remote Similarity NPD3027 Phase 3
0.6954 Remote Similarity NPD2424 Discontinued
0.695 Remote Similarity NPD1608 Approved
0.6948 Remote Similarity NPD7213 Phase 3
0.6948 Remote Similarity NPD7837 Clinical (unspecified phase)
0.6948 Remote Similarity NPD7212 Phase 2
0.6947 Remote Similarity NPD3134 Approved
0.6943 Remote Similarity NPD8158 Clinical (unspecified phase)
0.6937 Remote Similarity NPD5402 Approved
0.6937 Remote Similarity NPD3817 Phase 2
0.6933 Remote Similarity NPD6959 Discontinued
0.6918 Remote Similarity NPD6798 Discontinued
0.6918 Remote Similarity NPD1934 Approved
0.6905 Remote Similarity NPD5953 Discontinued
0.6901 Remote Similarity NPD3600 Clinical (unspecified phase)
0.6897 Remote Similarity NPD6832 Phase 2
0.6894 Remote Similarity NPD1358 Approved
0.6892 Remote Similarity NPD6355 Discontinued
0.689 Remote Similarity NPD5711 Approved
0.689 Remote Similarity NPD7229 Phase 3
0.689 Remote Similarity NPD5710 Approved
0.6886 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6886 Remote Similarity NPD7286 Phase 2
0.6871 Remote Similarity NPD8032 Phase 2
0.6867 Remote Similarity NPD7473 Discontinued
0.6864 Remote Similarity NPD6559 Discontinued
0.6859 Remote Similarity NPD6273 Approved
0.6859 Remote Similarity NPD7314 Clinical (unspecified phase)
0.6835 Remote Similarity NPD7458 Discontinued
0.6835 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6821 Remote Similarity NPD4476 Approved
0.6821 Remote Similarity NPD4477 Approved
0.681 Remote Similarity NPD919 Approved
0.6803 Remote Similarity NPD411 Approved
0.6803 Remote Similarity NPD7985 Registered
0.68 Remote Similarity NPD7097 Phase 1
0.6797 Remote Similarity NPD5698 Clinical (unspecified phase)
0.6791 Remote Similarity NPD4750 Phase 3
0.679 Remote Similarity NPD3882 Suspended
0.6779 Remote Similarity NPD447 Suspended
0.6776 Remote Similarity NPD5763 Approved
0.6776 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6776 Remote Similarity NPD5762 Approved
0.6772 Remote Similarity NPD1809 Phase 2
0.6761 Remote Similarity NPD1091 Approved
0.6761 Remote Similarity NPD1535 Discovery
0.6759 Remote Similarity NPD2798 Approved
0.6753 Remote Similarity NPD7976 Clinical (unspecified phase)
0.6752 Remote Similarity NPD1940 Clinical (unspecified phase)
0.6752 Remote Similarity NPD5049 Phase 3
0.675 Remote Similarity NPD6072 Discontinued
0.6748 Remote Similarity NPD6971 Discontinued
0.6738 Remote Similarity NPD17 Approved
0.6733 Remote Similarity NPD4097 Suspended
0.6732 Remote Similarity NPD7974 Phase 3
0.6727 Remote Similarity NPD7199 Phase 2
0.6727 Remote Similarity NPD8127 Discontinued
0.6726 Remote Similarity NPD3818 Discontinued
0.6725 Remote Similarity NPD4419 Clinical (unspecified phase)
0.6716 Remote Similarity NPD2684 Approved
0.6714 Remote Similarity NPD9545 Approved
0.6714 Remote Similarity NPD1894 Discontinued
0.6713 Remote Similarity NPD1481 Phase 2
0.6711 Remote Similarity NPD5406 Approved
0.6711 Remote Similarity NPD5408 Approved
0.6711 Remote Similarity NPD5404 Approved
0.6711 Remote Similarity NPD5405 Approved
0.6708 Remote Similarity NPD37 Approved
0.6707 Remote Similarity NPD6234 Discontinued
0.669 Remote Similarity NPD987 Approved
0.669 Remote Similarity NPD3847 Discontinued
0.6688 Remote Similarity NPD6674 Discontinued
0.6687 Remote Similarity NPD4965 Approved
0.6687 Remote Similarity NPD4966 Approved
0.6687 Remote Similarity NPD4967 Phase 2
0.6667 Remote Similarity NPD5585 Approved
0.6667 Remote Similarity NPD8455 Phase 2
0.6667 Remote Similarity NPD230 Phase 1

  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