Structure

Physi-Chem Properties

Molecular Weight:  452.2
Volume:  435.208
LogP:  2.735
LogD:  2.761
LogS:  -4.496
# Rotatable Bonds:  2
TPSA:  93.06
# H-Bond Aceptor:  6
# H-Bond Donor:  2
# Rings:  5
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.669
Synthetic Accessibility Score:  5.226
Fsp3:  0.75
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
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:  -4.935
MDCK Permeability:  2.3558444809168577e-05
Pgp-inhibitor:  0.157
Pgp-substrate:  0.003
Human Intestinal Absorption (HIA):  0.051
20% Bioavailability (F20%):  0.909
30% Bioavailability (F30%):  0.087

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.996
Plasma Protein Binding (PPB):  68.33887481689453%
Volume Distribution (VD):  0.893
Pgp-substrate:  25.87775230407715%

ADMET: Metabolism

CYP1A2-inhibitor:  0.002
CYP1A2-substrate:  0.481
CYP2C19-inhibitor:  0.021
CYP2C19-substrate:  0.818
CYP2C9-inhibitor:  0.02
CYP2C9-substrate:  0.073
CYP2D6-inhibitor:  0.001
CYP2D6-substrate:  0.059
CYP3A4-inhibitor:  0.674
CYP3A4-substrate:  0.911

ADMET: Excretion

Clearance (CL):  10.067
Half-life (T1/2):  0.464

ADMET: Toxicity

hERG Blockers:  0.033
Human Hepatotoxicity (H-HT):  0.366
Drug-inuced Liver Injury (DILI):  0.41
AMES Toxicity:  0.248
Rat Oral Acute Toxicity:  0.61
Maximum Recommended Daily Dose:  0.898
Skin Sensitization:  0.098
Carcinogencity:  0.936
Eye Corrosion:  0.003
Eye Irritation:  0.009
Respiratory Toxicity:  0.98

Download Data

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

  Natural Product: NPC313528

Natural Product ID:  NPC313528
Common Name*:   FEBLZLNTKCEFIT-UHFFFAOYSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  FEBLZLNTKCEFIT-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C24H30F2O6/c1-20(2)31-19-9-13-14-8-16(25)15-7-12(28)5-6-21(15,3)23(14,26)17(29)10-22(13,4)24(19,32-20)18(30)11-27/h5-7,13-14,16-17,19,27,29H,8-11H2,1-4H3
SMILES:  CC1(OC2CC3C4CC(C5=CC(=O)C=CC5(C4(C(CC3(C2(O1)C(=O)CO)C)O)F)C)F)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1599911
PubChem CID:   3381
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0001295] Hydroxysteroids
          • [CHEMONTID:0003095] 21-hydroxysteroids

*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
NPO21072 Rhododendron dauricum Species Ericaceae Eukaryota n.a. whole plant n.a. DOI[10.1007/BF02329610]
NPO25089 Cinchona calisaya Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[11992775]
NPO21072 Rhododendron dauricum Species Ericaceae Eukaryota n.a. n.a. n.a. PMID[15270561]
NPO25870 Vaccinium vitis-idaea Species Ericaceae Eukaryota n.a. fruit n.a. PMID[16417304]
NPO25870 Vaccinium vitis-idaea Species Ericaceae Eukaryota n.a. n.a. Database[FooDB]
NPO4626 Pimpinella anisum Species Apiaceae Eukaryota Essential Oil n.a. n.a. Database[FooDB]
NPO366 Pyrus communis Species Rosaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO366 Pyrus communis Species Rosaceae Eukaryota Pericarp n.a. n.a. Database[FooDB]
NPO4626 Pimpinella anisum Species Apiaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO25870 Vaccinium vitis-idaea Species Ericaceae Eukaryota Fruits n.a. Database[FooDB]
NPO4626 Pimpinella anisum Species Apiaceae Eukaryota Tissue Culture n.a. n.a. Database[FooDB]
NPO366 Pyrus communis Species Rosaceae Eukaryota Fruits n.a. Database[FooDB]
NPO4626 Pimpinella anisum Species Apiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO4626 Pimpinella anisum Species Apiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO366 Pyrus communis Species Rosaceae Eukaryota n.a. n.a. Database[FooDB]
NPO21072 Rhododendron dauricum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16481 Xanthium canadense Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25870 Vaccinium vitis-idaea Species Ericaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19694 Senecio scandens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29385 Nidus vespae n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO23604 Fructus choerospondiatis n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO366 Pyrus communis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15565 Pinus resinosa Species Pinaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8886 Protea mellifera Species Proteaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11045 Paederia scandens Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4626 Pimpinella anisum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO366 Pyrus communis Species Rosaceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO366 Pyrus communis Species Rosaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO366 Pyrus communis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15565 Pinus resinosa Species Pinaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25089 Cinchona calisaya Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16481 Xanthium canadense Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25870 Vaccinium vitis-idaea Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21072 Rhododendron dauricum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29385 Nidus vespae n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO4626 Pimpinella anisum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19694 Senecio scandens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8886 Protea mellifera Species Proteaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23604 Fructus choerospondiatis n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO11045 Paederia scandens Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11045 Paederia scandens Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21072 Rhododendron dauricum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15565 Pinus resinosa Species Pinaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21072 Rhododendron dauricum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO19694 Senecio scandens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15565 Pinus resinosa Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19694 Senecio scandens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25089 Cinchona calisaya Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16481 Xanthium canadense Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25870 Vaccinium vitis-idaea Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4626 Pimpinella anisum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21072 Rhododendron dauricum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO366 Pyrus communis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11045 Paederia scandens Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8886 Protea mellifera Species Proteaceae 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
NPT483 Individual Protein Prelamin-A/C Homo sapiens Potency = 316.2 nM PMID[471362]
NPT64 Individual Protein ATPase family AAA domain-containing protein 5 Homo sapiens Potency n.a. 25918.5 nM PMID[471363]
NPT135 Individual Protein Chromobox protein homolog 1 Homo sapiens Potency n.a. 89125.1 nM PMID[471363]
NPT11 Individual Protein Guanine nucleotide-binding protein G(s), subunit alpha Homo sapiens Potency n.a. 7079.5 nM PMID[471363]
NPT536 Uncleic Acid microRNA 21 Homo sapiens Potency = 1.6 nM PMID[471363]
NPT2 Others Unspecified Potency n.a. 354.8 nM PMID[471363]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 13459.1 nM PMID[471362]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 5858.4 nM PMID[471363]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 10417.9 nM PMID[471363]
NPT2 Others Unspecified Potency n.a. 2818.4 nM PMID[471363]
NPT861 Individual Protein Isocitrate dehydrogenase [NADP] cytoplasmic Homo sapiens Potency n.a. 290.9 nM PMID[471363]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Potency n.a. 14950.2 nM PMID[471362]
NPT2 Others Unspecified Potency n.a. 22387.2 nM PMID[471363]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Potency n.a. 10583.9 nM PMID[471362]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Potency n.a. 9432.9 nM PMID[471362]

☑ 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 NPC313528 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
0.885 High Similarity NPC235077
0.8621 High Similarity NPC178981
0.8596 High Similarity NPC2766
0.8462 Intermediate Similarity NPC471627
0.8462 Intermediate Similarity NPC471173
0.8421 Intermediate Similarity NPC44063
0.8374 Intermediate Similarity NPC473255
0.8319 Intermediate Similarity NPC302471
0.825 Intermediate Similarity NPC218970
0.824 Intermediate Similarity NPC473265
0.824 Intermediate Similarity NPC305496
0.8235 Intermediate Similarity NPC471398
0.8214 Intermediate Similarity NPC144956
0.8205 Intermediate Similarity NPC163314
0.8182 Intermediate Similarity NPC297179
0.8175 Intermediate Similarity NPC473888
0.816 Intermediate Similarity NPC47113
0.816 Intermediate Similarity NPC174367
0.8151 Intermediate Similarity NPC52634
0.8151 Intermediate Similarity NPC194100
0.8145 Intermediate Similarity NPC238005
0.8145 Intermediate Similarity NPC1980
0.8145 Intermediate Similarity NPC141196
0.8136 Intermediate Similarity NPC207689
0.8136 Intermediate Similarity NPC471243
0.813 Intermediate Similarity NPC470921
0.8115 Intermediate Similarity NPC319570
0.8115 Intermediate Similarity NPC161065
0.8115 Intermediate Similarity NPC469488
0.811 Intermediate Similarity NPC470880
0.8099 Intermediate Similarity NPC477116
0.8099 Intermediate Similarity NPC27999
0.8095 Intermediate Similarity NPC473253
0.8095 Intermediate Similarity NPC287423
0.8095 Intermediate Similarity NPC470882
0.8095 Intermediate Similarity NPC42399
0.8083 Intermediate Similarity NPC243354
0.8083 Intermediate Similarity NPC326542
0.8083 Intermediate Similarity NPC477580
0.808 Intermediate Similarity NPC277191
0.808 Intermediate Similarity NPC190846
0.808 Intermediate Similarity NPC475194
0.8067 Intermediate Similarity NPC207251
0.8067 Intermediate Similarity NPC205534
0.8065 Intermediate Similarity NPC216866
0.8051 Intermediate Similarity NPC474567
0.8049 Intermediate Similarity NPC241192
0.8036 Intermediate Similarity NPC18509
0.8033 Intermediate Similarity NPC188667
0.8033 Intermediate Similarity NPC204552
0.8031 Intermediate Similarity NPC168899
0.8031 Intermediate Similarity NPC293623
0.8031 Intermediate Similarity NPC311534
0.8031 Intermediate Similarity NPC69273
0.8017 Intermediate Similarity NPC235539
0.8017 Intermediate Similarity NPC270958
0.8017 Intermediate Similarity NPC207217
0.8017 Intermediate Similarity NPC152199
0.8017 Intermediate Similarity NPC470309
0.8017 Intermediate Similarity NPC134869
0.8016 Intermediate Similarity NPC93368
0.8016 Intermediate Similarity NPC225049
0.8016 Intermediate Similarity NPC198714
0.8 Intermediate Similarity NPC471234
0.8 Intermediate Similarity NPC260665
0.7984 Intermediate Similarity NPC471855
0.7984 Intermediate Similarity NPC42675
0.7983 Intermediate Similarity NPC201992
0.7967 Intermediate Similarity NPC268958
0.7967 Intermediate Similarity NPC473203
0.7966 Intermediate Similarity NPC470257
0.7937 Intermediate Similarity NPC470922
0.7934 Intermediate Similarity NPC474906
0.7934 Intermediate Similarity NPC18547
0.7931 Intermediate Similarity NPC13149
0.7931 Intermediate Similarity NPC100955
0.7931 Intermediate Similarity NPC121566
0.7923 Intermediate Similarity NPC88668
0.792 Intermediate Similarity NPC28532
0.792 Intermediate Similarity NPC222688
0.7917 Intermediate Similarity NPC11252
0.7917 Intermediate Similarity NPC289312
0.7917 Intermediate Similarity NPC71348
0.7913 Intermediate Similarity NPC22388
0.7907 Intermediate Similarity NPC241008
0.7903 Intermediate Similarity NPC112038
0.7903 Intermediate Similarity NPC109973
0.7899 Intermediate Similarity NPC197428
0.7899 Intermediate Similarity NPC470065
0.7899 Intermediate Similarity NPC5284
0.7899 Intermediate Similarity NPC42776
0.7899 Intermediate Similarity NPC101450
0.7891 Intermediate Similarity NPC473620
0.7886 Intermediate Similarity NPC118638
0.7886 Intermediate Similarity NPC17772
0.7881 Intermediate Similarity NPC258323
0.7874 Intermediate Similarity NPC104427
0.7869 Intermediate Similarity NPC266728
0.7869 Intermediate Similarity NPC49492
0.7863 Intermediate Similarity NPC63023
0.7863 Intermediate Similarity NPC95243
0.7863 Intermediate Similarity NPC96377
0.7851 Intermediate Similarity NPC477944
0.7851 Intermediate Similarity NPC194273
0.7851 Intermediate Similarity NPC51978
0.7851 Intermediate Similarity NPC320118
0.7851 Intermediate Similarity NPC255017
0.7851 Intermediate Similarity NPC317210
0.7851 Intermediate Similarity NPC202889
0.7846 Intermediate Similarity NPC254614
0.7846 Intermediate Similarity NPC100390
0.7845 Intermediate Similarity NPC117185
0.7845 Intermediate Similarity NPC140723
0.784 Intermediate Similarity NPC46570
0.784 Intermediate Similarity NPC477046
0.784 Intermediate Similarity NPC102822
0.7833 Intermediate Similarity NPC231589
0.7833 Intermediate Similarity NPC118860
0.7833 Intermediate Similarity NPC474229
0.7833 Intermediate Similarity NPC214797
0.7829 Intermediate Similarity NPC264192
0.7829 Intermediate Similarity NPC471407
0.7829 Intermediate Similarity NPC473593
0.7829 Intermediate Similarity NPC231529
0.7823 Intermediate Similarity NPC470777
0.7823 Intermediate Similarity NPC9674
0.7823 Intermediate Similarity NPC19028
0.7815 Intermediate Similarity NPC474242
0.7812 Intermediate Similarity NPC298841
0.7812 Intermediate Similarity NPC152091
0.7812 Intermediate Similarity NPC2757
0.7812 Intermediate Similarity NPC469757
0.7812 Intermediate Similarity NPC146456
0.7812 Intermediate Similarity NPC471357
0.7812 Intermediate Similarity NPC292290
0.7812 Intermediate Similarity NPC117702
0.7805 Intermediate Similarity NPC470854
0.7805 Intermediate Similarity NPC239273
0.7805 Intermediate Similarity NPC97908
0.7805 Intermediate Similarity NPC122033
0.7805 Intermediate Similarity NPC287343
0.7805 Intermediate Similarity NPC474654
0.7797 Intermediate Similarity NPC144854
0.7797 Intermediate Similarity NPC3316
0.7797 Intermediate Similarity NPC58370
0.7797 Intermediate Similarity NPC43285
0.7797 Intermediate Similarity NPC220974
0.7795 Intermediate Similarity NPC30188
0.7795 Intermediate Similarity NPC241456
0.7795 Intermediate Similarity NPC473505
0.7795 Intermediate Similarity NPC8369
0.7795 Intermediate Similarity NPC177820
0.7795 Intermediate Similarity NPC32868
0.7787 Intermediate Similarity NPC300051
0.7787 Intermediate Similarity NPC473798
0.7786 Intermediate Similarity NPC475487
0.7778 Intermediate Similarity NPC255309
0.7778 Intermediate Similarity NPC107493
0.7778 Intermediate Similarity NPC471293
0.7778 Intermediate Similarity NPC137657
0.7778 Intermediate Similarity NPC29705
0.7778 Intermediate Similarity NPC131824
0.7769 Intermediate Similarity NPC130427
0.7769 Intermediate Similarity NPC234042
0.7769 Intermediate Similarity NPC170487
0.7769 Intermediate Similarity NPC474516
0.7769 Intermediate Similarity NPC280782
0.7769 Intermediate Similarity NPC173347
0.7769 Intermediate Similarity NPC152117
0.776 Intermediate Similarity NPC471406
0.776 Intermediate Similarity NPC79579
0.776 Intermediate Similarity NPC474585
0.776 Intermediate Similarity NPC107338
0.776 Intermediate Similarity NPC109607
0.776 Intermediate Similarity NPC472004
0.7744 Intermediate Similarity NPC243014
0.7742 Intermediate Similarity NPC86020
0.7742 Intermediate Similarity NPC475632
0.7734 Intermediate Similarity NPC285091
0.7731 Intermediate Similarity NPC55973
0.7731 Intermediate Similarity NPC189663
0.7731 Intermediate Similarity NPC154608
0.7731 Intermediate Similarity NPC89860
0.7731 Intermediate Similarity NPC94529
0.7731 Intermediate Similarity NPC192813
0.7731 Intermediate Similarity NPC277017
0.7731 Intermediate Similarity NPC472825
0.7727 Intermediate Similarity NPC478069
0.7727 Intermediate Similarity NPC198361
0.7724 Intermediate Similarity NPC243981
0.7724 Intermediate Similarity NPC328374
0.7724 Intermediate Similarity NPC138372
0.7724 Intermediate Similarity NPC40632
0.7724 Intermediate Similarity NPC298278
0.7724 Intermediate Similarity NPC96312
0.7724 Intermediate Similarity NPC106228
0.7724 Intermediate Similarity NPC251236
0.7717 Intermediate Similarity NPC120724
0.7717 Intermediate Similarity NPC473979
0.7717 Intermediate Similarity NPC469789

  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 NPC313528 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
1.0 High Similarity NPD5988 Approved
0.9911 High Similarity NPD6016 Approved
0.9911 High Similarity NPD6015 Approved
0.9739 High Similarity NPD6616 Approved
0.9652 High Similarity NPD7492 Approved
0.9646 High Similarity NPD6059 Approved
0.9646 High Similarity NPD6054 Approved
0.9487 High Similarity NPD7078 Approved
0.9478 High Similarity NPD6370 Approved
0.9322 High Similarity NPD8293 Discontinued
0.9138 High Similarity NPD6319 Approved
0.9083 High Similarity NPD7736 Approved
0.8926 High Similarity NPD6033 Approved
0.885 High Similarity NPD4634 Approved
0.8718 High Similarity NPD6009 Approved
0.8609 High Similarity NPD6617 Approved
0.8609 High Similarity NPD6847 Approved
0.8609 High Similarity NPD6869 Approved
0.8596 High Similarity NPD6014 Approved
0.8596 High Similarity NPD6012 Approved
0.8596 High Similarity NPD6013 Approved
0.8534 High Similarity NPD6882 Approved
0.8522 High Similarity NPD7102 Approved
0.8522 High Similarity NPD7290 Approved
0.8522 High Similarity NPD6883 Approved
0.8509 High Similarity NPD6011 Approved
0.8482 Intermediate Similarity NPD5175 Approved
0.8482 Intermediate Similarity NPD5174 Approved
0.848 Intermediate Similarity NPD5956 Approved
0.8448 Intermediate Similarity NPD8130 Phase 1
0.8443 Intermediate Similarity NPD7604 Phase 2
0.8421 Intermediate Similarity NPD5701 Approved
0.8421 Intermediate Similarity NPD5697 Approved
0.8393 Intermediate Similarity NPD5226 Approved
0.8393 Intermediate Similarity NPD4633 Approved
0.8393 Intermediate Similarity NPD5224 Approved
0.8393 Intermediate Similarity NPD5225 Approved
0.8376 Intermediate Similarity NPD8297 Approved
0.8348 Intermediate Similarity NPD6899 Approved
0.8348 Intermediate Similarity NPD6881 Approved
0.8305 Intermediate Similarity NPD4632 Approved
0.8304 Intermediate Similarity NPD5223 Approved
0.8246 Intermediate Similarity NPD5141 Approved
0.8214 Intermediate Similarity NPD5285 Approved
0.8214 Intermediate Similarity NPD4700 Approved
0.8214 Intermediate Similarity NPD5286 Approved
0.8214 Intermediate Similarity NPD4696 Approved
0.819 Intermediate Similarity NPD7320 Approved
0.8174 Intermediate Similarity NPD6675 Approved
0.8174 Intermediate Similarity NPD5739 Approved
0.8174 Intermediate Similarity NPD7128 Approved
0.8174 Intermediate Similarity NPD6402 Approved
0.8167 Intermediate Similarity NPD6274 Approved
0.816 Intermediate Similarity NPD6336 Discontinued
0.8136 Intermediate Similarity NPD6649 Approved
0.8136 Intermediate Similarity NPD6650 Approved
0.813 Intermediate Similarity NPD5983 Phase 2
0.8099 Intermediate Similarity NPD6317 Approved
0.807 Intermediate Similarity NPD5211 Phase 2
0.8036 Intermediate Similarity NPD5173 Approved
0.8036 Intermediate Similarity NPD4755 Approved
0.8034 Intermediate Similarity NPD5128 Approved
0.8033 Intermediate Similarity NPD6314 Approved
0.8033 Intermediate Similarity NPD6313 Approved
0.8 Intermediate Similarity NPD6067 Discontinued
0.7984 Intermediate Similarity NPD6291 Clinical (unspecified phase)
0.7966 Intermediate Similarity NPD6372 Approved
0.7966 Intermediate Similarity NPD6373 Approved
0.7946 Intermediate Similarity NPD5222 Approved
0.7946 Intermediate Similarity NPD5221 Approved
0.7946 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7899 Intermediate Similarity NPD5134 Clinical (unspecified phase)
0.7899 Intermediate Similarity NPD5249 Phase 3
0.7899 Intermediate Similarity NPD5248 Approved
0.7899 Intermediate Similarity NPD5251 Approved
0.7899 Intermediate Similarity NPD5247 Approved
0.7899 Intermediate Similarity NPD5135 Approved
0.7899 Intermediate Similarity NPD5250 Approved
0.7886 Intermediate Similarity NPD6335 Approved
0.7833 Intermediate Similarity NPD5127 Approved
0.7797 Intermediate Similarity NPD6412 Phase 2
0.775 Intermediate Similarity NPD5169 Approved
0.7731 Intermediate Similarity NPD4730 Approved
0.7731 Intermediate Similarity NPD4729 Approved
0.7712 Intermediate Similarity NPD6008 Approved
0.7692 Intermediate Similarity NPD7319 Approved
0.7686 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.768 Intermediate Similarity NPD7101 Approved
0.768 Intermediate Similarity NPD7100 Approved
0.7679 Intermediate Similarity NPD4202 Approved
0.7597 Intermediate Similarity NPD7507 Approved
0.7578 Intermediate Similarity NPD8328 Phase 3
0.7565 Intermediate Similarity NPD6083 Phase 2
0.7565 Intermediate Similarity NPD6084 Phase 2
0.7563 Intermediate Similarity NPD4767 Approved
0.7563 Intermediate Similarity NPD4768 Approved
0.7542 Intermediate Similarity NPD4754 Approved
0.7541 Intermediate Similarity NPD5217 Approved
0.7541 Intermediate Similarity NPD5216 Approved
0.7541 Intermediate Similarity NPD5215 Approved
0.754 Intermediate Similarity NPD4522 Approved
0.744 Intermediate Similarity NPD6868 Approved
0.7434 Intermediate Similarity NPD6079 Approved
0.7411 Intermediate Similarity NPD4753 Phase 2
0.7391 Intermediate Similarity NPD5210 Approved
0.7391 Intermediate Similarity NPD5695 Phase 3
0.7391 Intermediate Similarity NPD4629 Approved
0.735 Intermediate Similarity NPD5696 Approved
0.7328 Intermediate Similarity NPD4697 Phase 3
0.7295 Intermediate Similarity NPD5168 Approved
0.7287 Intermediate Similarity NPD6908 Approved
0.7287 Intermediate Similarity NPD6909 Approved
0.7257 Intermediate Similarity NPD5328 Approved
0.7246 Intermediate Similarity NPD6334 Approved
0.7246 Intermediate Similarity NPD6333 Approved
0.7244 Intermediate Similarity NPD7115 Discovery
0.7222 Intermediate Similarity NPD5167 Approved
0.7109 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7054 Intermediate Similarity NPD7328 Approved
0.7054 Intermediate Similarity NPD7327 Approved
0.7023 Intermediate Similarity NPD7503 Approved
0.7016 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD7516 Approved
0.6991 Remote Similarity NPD3618 Phase 1
0.6991 Remote Similarity NPD5690 Phase 2
0.6991 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6964 Remote Similarity NPD4197 Approved
0.6964 Remote Similarity NPD3665 Phase 1
0.6964 Remote Similarity NPD3133 Approved
0.6964 Remote Similarity NPD3666 Approved
0.6957 Remote Similarity NPD6673 Approved
0.6957 Remote Similarity NPD6904 Approved
0.6957 Remote Similarity NPD6080 Approved
0.6949 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6947 Remote Similarity NPD8294 Approved
0.6947 Remote Similarity NPD8377 Approved
0.6917 Remote Similarity NPD7638 Approved
0.6903 Remote Similarity NPD5329 Approved
0.6894 Remote Similarity NPD8296 Approved
0.6894 Remote Similarity NPD8379 Approved
0.6894 Remote Similarity NPD8378 Approved
0.6894 Remote Similarity NPD8033 Approved
0.6894 Remote Similarity NPD8335 Approved
0.6894 Remote Similarity NPD8380 Approved
0.688 Remote Similarity NPD6686 Approved
0.687 Remote Similarity NPD6672 Approved
0.687 Remote Similarity NPD5737 Approved
0.6864 Remote Similarity NPD5282 Discontinued
0.686 Remote Similarity NPD7639 Approved
0.686 Remote Similarity NPD7640 Approved
0.6838 Remote Similarity NPD5693 Phase 1
0.6838 Remote Similarity NPD5694 Approved
0.6813 Remote Similarity NPD7799 Discontinued
0.6797 Remote Similarity NPD6053 Discontinued
0.6786 Remote Similarity NPD4221 Approved
0.6786 Remote Similarity NPD4223 Phase 3
0.678 Remote Similarity NPD6399 Phase 3
0.6774 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6752 Remote Similarity NPD5692 Phase 3
0.6748 Remote Similarity NPD5091 Approved
0.6724 Remote Similarity NPD6903 Approved
0.6723 Remote Similarity NPD6001 Approved
0.6696 Remote Similarity NPD6409 Approved
0.6696 Remote Similarity NPD7334 Approved
0.6696 Remote Similarity NPD5280 Approved
0.6696 Remote Similarity NPD7146 Approved
0.6696 Remote Similarity NPD5330 Approved
0.6696 Remote Similarity NPD4694 Approved
0.6696 Remote Similarity NPD6684 Approved
0.6696 Remote Similarity NPD6098 Approved
0.6696 Remote Similarity NPD5279 Phase 3
0.6696 Remote Similarity NPD7521 Approved
0.6695 Remote Similarity NPD6050 Approved
0.6695 Remote Similarity NPD5281 Approved
0.6695 Remote Similarity NPD5284 Approved
0.6693 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6693 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6667 Remote Similarity NPD1700 Approved
0.6667 Remote Similarity NPD4786 Approved
0.6667 Remote Similarity NPD6614 Approved
0.6639 Remote Similarity NPD4225 Approved
0.6638 Remote Similarity NPD3573 Approved
0.6637 Remote Similarity NPD3667 Approved
0.6615 Remote Similarity NPD8133 Approved
0.661 Remote Similarity NPD5207 Approved
0.6583 Remote Similarity NPD7748 Approved
0.6581 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6557 Remote Similarity NPD7902 Approved
0.6555 Remote Similarity NPD7515 Phase 2
0.6552 Remote Similarity NPD5205 Approved
0.6552 Remote Similarity NPD4138 Approved
0.6552 Remote Similarity NPD4693 Phase 3
0.6552 Remote Similarity NPD4689 Approved
0.6552 Remote Similarity NPD4690 Approved
0.6552 Remote Similarity NPD4688 Approved
0.6535 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6533 Remote Similarity NPD7236 Approved
0.6519 Remote Similarity NPD8513 Phase 3
0.6519 Remote Similarity NPD8515 Approved
0.6519 Remote Similarity NPD8517 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