Structure

Physi-Chem Properties

Molecular Weight:  346.13
Volume:  322.086
LogP:  -0.681
LogD:  -0.881
LogS:  -0.729
# Rotatable Bonds:  6
TPSA:  138.07
# H-Bond Aceptor:  9
# H-Bond Donor:  5
# Rings:  2
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.411
Synthetic Accessibility Score:  3.522
Fsp3:  0.6
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.594
MDCK Permeability:  5.667160439770669e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.137
Human Intestinal Absorption (HIA):  0.475
20% Bioavailability (F20%):  0.009
30% Bioavailability (F30%):  0.276

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.317
Plasma Protein Binding (PPB):  23.4808349609375%
Volume Distribution (VD):  0.456
Pgp-substrate:  53.14067459106445%

ADMET: Metabolism

CYP1A2-inhibitor:  0.033
CYP1A2-substrate:  0.229
CYP2C19-inhibitor:  0.01
CYP2C19-substrate:  0.821
CYP2C9-inhibitor:  0.001
CYP2C9-substrate:  0.245
CYP2D6-inhibitor:  0.008
CYP2D6-substrate:  0.29
CYP3A4-inhibitor:  0.004
CYP3A4-substrate:  0.051

ADMET: Excretion

Clearance (CL):  2.492
Half-life (T1/2):  0.854

ADMET: Toxicity

hERG Blockers:  0.198
Human Hepatotoxicity (H-HT):  0.18
Drug-inuced Liver Injury (DILI):  0.05
AMES Toxicity:  0.092
Rat Oral Acute Toxicity:  0.004
Maximum Recommended Daily Dose:  0.006
Skin Sensitization:  0.322
Carcinogencity:  0.035
Eye Corrosion:  0.003
Eye Irritation:  0.032
Respiratory Toxicity:  0.011

Download Data

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

  Natural Product: NPC299144

Natural Product ID:  NPC299144
Common Name*:   Di-O-Methylcrenatin
IUPAC Name:   (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-(hydroxymethyl)-2,6-dimethoxyphenoxy]oxane-3,4,5-triol
Synonyms:   Di-O-Methylcrenatin
Standard InCHIKey:  RWIINOLFQCPJMH-VVSAWPALSA-N
Standard InCHI:  InChI=1S/C15H22O9/c1-21-8-3-7(5-16)4-9(22-2)14(8)24-15-13(20)12(19)11(18)10(6-17)23-15/h3-4,10-13,15-20H,5-6H2,1-2H3/t10-,11-,12+,13-,15+/m1/s1
SMILES:  COc1cc(cc(c1O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)OC)CO
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1923074
PubChem CID:   10736338
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates
          • [CHEMONTID:0002105] Glycosyl compounds
            • [CHEMONTID:0004165] Phenolic glycosides

*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
NPO6062 Acacia mearnsii Species Fabaceae Eukaryota n.a. bark n.a. PMID[21192716]
NPO14559 Acer saccharum Species Sapindaceae Eukaryota bark n.a. n.a. PMID[22032697]
NPO14559 Acer saccharum Species Sapindaceae Eukaryota n.a. bark n.a. PMID[22032697]
NPO13726 Agrobacterium tumefaciens Species Rhizobiaceae Bacteria n.a. n.a. n.a. PMID[22466953]
NPO22437 Eurya japonica Species Pentaphylacaceae Eukaryota n.a. n.a. n.a. PMID[23540981]
NPO13726 Agrobacterium tumefaciens Species Rhizobiaceae Bacteria n.a. n.a. n.a. PMID[24450804]
NPO41077 Xanthoceras sorbifolia Bunge Strain Sapindaceae Eukaryota Leaves n.a. n.a. PMID[27623545]
NPO22437 Eurya japonica Species Pentaphylacaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9357 Mitragyna inermis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6062 Acacia mearnsii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27620.1 Pteris cretica var. nervosa Varieties Pteridaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25181 Cyperus papyrus Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14381 Swertia pseudochinensis Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14559 Acer saccharum Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2340 Caulis spatholobi n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO6062 Acacia mearnsii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25181 Cyperus papyrus Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14381 Swertia pseudochinensis Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22798 Pseudofumaria lutea Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO277 Caulis millettiae n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO2340 Caulis spatholobi n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO9357 Mitragyna inermis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27620.1 Pteris cretica var. nervosa Varieties Pteridaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22437 Eurya japonica Species Pentaphylacaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14559 Acer saccharum Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25479 Sabal blackburniana Species Arecaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14381 Swertia pseudochinensis Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14381 Swertia pseudochinensis Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9017 Fagus grandifolia Species Fagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13685 Scrophularia umbrosa Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8628 Strychnos erichsonii Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12716 Stocksia brahuica n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO14559 Acer saccharum Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12564 Sinularia facile Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13987 Solanum sublobatum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22798 Pseudofumaria lutea Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12213 Perriera orientalis Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5383 Othonna dentata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27620.1 Pteris cretica var. nervosa Varieties Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22437 Eurya japonica Species Pentaphylacaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8181 Hypoxylon tinctor Species Xylariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14381 Swertia pseudochinensis Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12021 Artemisia incanescens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13600 Ichthyothere latifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10325 Boletus pini Species Boletaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3075 Dimorphotheca aurantiaca Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25181 Cyperus papyrus Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29152 Caloboletus calopus Species Boletaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6599 Neorautanenia ficifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9620 Rhodococcus fascians Species 0cardiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO9357 Mitragyna inermis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25479 Sabal blackburniana Species Arecaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13726 Agrobacterium tumefaciens Species Rhizobiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO13790 Abedus herberti Species Belostomatidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6062 Acacia mearnsii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14078 Paramecium tetraurelia Species Parameciidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26723 Lachnophyllum gossypinum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT393 Cell Line HCT-116 Homo sapiens IC50 < 5.0 ug.mL-1 PMID[528831]
NPT492 Cell Line Caco-2 Homo sapiens IC50 < 5.0 ug.mL-1 PMID[528831]
NPT27 Others Unspecified IC50 < 5.0 ug.mL-1 PMID[528831]
NPT1 Others Radical scavenging activity ED50 > 100.0 uM PMID[528832]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 91.12 % PMID[528833]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 100000.0 nM PMID[528833]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 94.7 % PMID[528833]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 90.71 % PMID[528833]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 87.01 % PMID[528833]

☑ 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 NPC299144 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
0.9843 High Similarity NPC48863
0.9843 High Similarity NPC251981
0.9843 High Similarity NPC13745
0.9764 High Similarity NPC215833
0.9764 High Similarity NPC49074
0.9764 High Similarity NPC69513
0.9685 High Similarity NPC162093
0.9685 High Similarity NPC470270
0.9603 High Similarity NPC166040
0.9538 High Similarity NPC164857
0.9535 High Similarity NPC107478
0.9462 High Similarity NPC470236
0.9457 High Similarity NPC132895
0.9449 High Similarity NPC248355
0.9394 High Similarity NPC212770
0.9394 High Similarity NPC98777
0.9389 High Similarity NPC104167
0.9375 High Similarity NPC472024
0.9375 High Similarity NPC80600
0.937 High Similarity NPC302378
0.9328 High Similarity NPC475084
0.9328 High Similarity NPC469559
0.9328 High Similarity NPC189115
0.9318 High Similarity NPC59324
0.9318 High Similarity NPC65530
0.9308 High Similarity NPC25821
0.9297 High Similarity NPC26653
0.9297 High Similarity NPC270849
0.9286 High Similarity NPC12308
0.9254 High Similarity NPC469661
0.9242 High Similarity NPC203230
0.9242 High Similarity NPC25695
0.9242 High Similarity NPC172818
0.9242 High Similarity NPC242028
0.9191 High Similarity NPC25292
0.9191 High Similarity NPC473045
0.9179 High Similarity NPC210478
0.9173 High Similarity NPC195196
0.916 High Similarity NPC115022
0.916 High Similarity NPC294166
0.9154 High Similarity NPC65942
0.9154 High Similarity NPC166168
0.9154 High Similarity NPC9912
0.9154 High Similarity NPC248307
0.9147 High Similarity NPC307110
0.9124 High Similarity NPC277867
0.9124 High Similarity NPC475096
0.9124 High Similarity NPC161700
0.9118 High Similarity NPC473044
0.9118 High Similarity NPC252169
0.9091 High Similarity NPC187194
0.9084 High Similarity NPC165686
0.9084 High Similarity NPC26080
0.9084 High Similarity NPC85799
0.9084 High Similarity NPC303422
0.9077 High Similarity NPC469612
0.9077 High Similarity NPC262606
0.9077 High Similarity NPC469614
0.9062 High Similarity NPC473960
0.9058 High Similarity NPC125755
0.9058 High Similarity NPC190714
0.9058 High Similarity NPC99515
0.9044 High Similarity NPC5262
0.9044 High Similarity NPC472714
0.903 High Similarity NPC470413
0.903 High Similarity NPC138738
0.9023 High Similarity NPC238243
0.9015 High Similarity NPC6836
0.9008 High Similarity NPC30043
0.9008 High Similarity NPC469698
0.9008 High Similarity NPC469625
0.9008 High Similarity NPC121376
0.9008 High Similarity NPC473412
0.9008 High Similarity NPC469613
0.9 High Similarity NPC273295
0.9 High Similarity NPC218856
0.9 High Similarity NPC222004
0.9 High Similarity NPC470258
0.9 High Similarity NPC190629
0.9 High Similarity NPC3439
0.9 High Similarity NPC226788
0.9 High Similarity NPC285339
0.9 High Similarity NPC210623
0.9 High Similarity NPC202582
0.8993 High Similarity NPC39657
0.8993 High Similarity NPC227902
0.8978 High Similarity NPC37793
0.8955 High Similarity NPC138350
0.8955 High Similarity NPC165482
0.8955 High Similarity NPC3293
0.8955 High Similarity NPC40664
0.8955 High Similarity NPC37468
0.8955 High Similarity NPC197723
0.8947 High Similarity NPC130496
0.8947 High Similarity NPC470881
0.8947 High Similarity NPC87696
0.8947 High Similarity NPC188555
0.8947 High Similarity NPC170694
0.8947 High Similarity NPC35731
0.8947 High Similarity NPC476411
0.8939 High Similarity NPC35932
0.8939 High Similarity NPC160991
0.8939 High Similarity NPC252833
0.8939 High Similarity NPC7903
0.8939 High Similarity NPC16208
0.8939 High Similarity NPC184447
0.8929 High Similarity NPC130449
0.8929 High Similarity NPC248132
0.8929 High Similarity NPC175976
0.8913 High Similarity NPC168579
0.8913 High Similarity NPC469313
0.8913 High Similarity NPC187774
0.8913 High Similarity NPC472713
0.8913 High Similarity NPC472712
0.8913 High Similarity NPC118385
0.8913 High Similarity NPC76176
0.8913 High Similarity NPC138227
0.8913 High Similarity NPC473046
0.8897 High Similarity NPC226547
0.8889 High Similarity NPC124149
0.8889 High Similarity NPC269242
0.8881 High Similarity NPC55040
0.8865 High Similarity NPC55158
0.8865 High Similarity NPC286235
0.8865 High Similarity NPC106138
0.8865 High Similarity NPC51328
0.8864 High Similarity NPC475067
0.8864 High Similarity NPC472597
0.8857 High Similarity NPC15538
0.8857 High Similarity NPC473480
0.8857 High Similarity NPC41844
0.8855 High Similarity NPC218003
0.8846 High Similarity NPC474119
0.8832 High Similarity NPC210192
0.8828 High Similarity NPC165375
0.8828 High Similarity NPC220598
0.8824 High Similarity NPC100389
0.8815 High Similarity NPC199459
0.8815 High Similarity NPC471719
0.8815 High Similarity NPC177035
0.8815 High Similarity NPC186418
0.8815 High Similarity NPC52277
0.8806 High Similarity NPC310854
0.8803 High Similarity NPC472710
0.8803 High Similarity NPC472709
0.8794 High Similarity NPC93924
0.8794 High Similarity NPC270751
0.8794 High Similarity NPC96294
0.8794 High Similarity NPC478237
0.8788 High Similarity NPC472338
0.8779 High Similarity NPC40377
0.8777 High Similarity NPC297342
0.8768 High Similarity NPC60249
0.8759 High Similarity NPC106944
0.875 High Similarity NPC152722
0.875 High Similarity NPC474039
0.875 High Similarity NPC304152
0.875 High Similarity NPC283949
0.8741 High Similarity NPC234333
0.8741 High Similarity NPC236522
0.8741 High Similarity NPC61946
0.8741 High Similarity NPC213197
0.8741 High Similarity NPC185778
0.8741 High Similarity NPC260898
0.8741 High Similarity NPC47398
0.874 High Similarity NPC276195
0.874 High Similarity NPC469412
0.874 High Similarity NPC199023
0.874 High Similarity NPC198734
0.8732 High Similarity NPC55715
0.8732 High Similarity NPC313334
0.8732 High Similarity NPC35877
0.8732 High Similarity NPC206264
0.8732 High Similarity NPC95392
0.8732 High Similarity NPC212670
0.8731 High Similarity NPC263064
0.8731 High Similarity NPC58585
0.8723 High Similarity NPC52740
0.8722 High Similarity NPC309787
0.8722 High Similarity NPC470095
0.8722 High Similarity NPC470096
0.8705 High Similarity NPC185307
0.8705 High Similarity NPC46092
0.8705 High Similarity NPC81638
0.8705 High Similarity NPC478239
0.8705 High Similarity NPC470950
0.8696 High Similarity NPC76871
0.8696 High Similarity NPC257095
0.8696 High Similarity NPC273932
0.8696 High Similarity NPC89686
0.8686 High Similarity NPC292487
0.8682 High Similarity NPC192810
0.8681 High Similarity NPC21902
0.8676 High Similarity NPC157554
0.8676 High Similarity NPC16435
0.8676 High Similarity NPC306441
0.8672 High Similarity NPC226712
0.8672 High Similarity NPC49341
0.8671 High Similarity NPC114740
0.8667 High Similarity NPC309744

  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 NPC299144 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
0.8732 High Similarity NPD1653 Approved
0.8672 High Similarity NPD1091 Approved
0.8571 High Similarity NPD3027 Phase 3
0.8519 High Similarity NPD1613 Approved
0.8519 High Similarity NPD1612 Clinical (unspecified phase)
0.8284 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.8222 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.8154 Intermediate Similarity NPD1357 Approved
0.8106 Intermediate Similarity NPD3705 Approved
0.8042 Intermediate Similarity NPD6674 Discontinued
0.7911 Intermediate Similarity NPD7054 Approved
0.7902 Intermediate Similarity NPD7266 Discontinued
0.7881 Intermediate Similarity NPD37 Approved
0.7862 Intermediate Similarity NPD7472 Approved
0.7862 Intermediate Similarity NPD7074 Phase 3
0.7852 Intermediate Similarity NPD2982 Phase 2
0.7852 Intermediate Similarity NPD2983 Phase 2
0.7843 Intermediate Similarity NPD4966 Approved
0.7843 Intermediate Similarity NPD4965 Approved
0.7843 Intermediate Similarity NPD4967 Phase 2
0.7778 Intermediate Similarity NPD2981 Phase 2
0.7754 Intermediate Similarity NPD3018 Phase 2
0.7742 Intermediate Similarity NPD6234 Discontinued
0.7736 Intermediate Similarity NPD7228 Approved
0.7736 Intermediate Similarity NPD3818 Discontinued
0.7716 Intermediate Similarity NPD7808 Phase 3
0.7702 Intermediate Similarity NPD6797 Phase 2
0.7674 Intermediate Similarity NPD228 Approved
0.7654 Intermediate Similarity NPD7251 Discontinued
0.7643 Intermediate Similarity NPD7199 Phase 2
0.7607 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7574 Intermediate Similarity NPD1610 Phase 2
0.7571 Intermediate Similarity NPD4908 Phase 1
0.7564 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7551 Intermediate Similarity NPD1652 Phase 2
0.7537 Intermediate Similarity NPD1548 Phase 1
0.7532 Intermediate Similarity NPD1934 Approved
0.75 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD290 Approved
0.7481 Intermediate Similarity NPD7843 Approved
0.7465 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7465 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7464 Intermediate Similarity NPD4749 Approved
0.7444 Intermediate Similarity NPD7157 Approved
0.7442 Intermediate Similarity NPD2684 Approved
0.7439 Intermediate Similarity NPD7240 Approved
0.7438 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7415 Intermediate Similarity NPD1375 Discontinued
0.7403 Intermediate Similarity NPD4675 Approved
0.7403 Intermediate Similarity NPD4678 Approved
0.74 Intermediate Similarity NPD5058 Phase 3
0.7391 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD6166 Phase 2
0.7381 Intermediate Similarity NPD6842 Approved
0.7381 Intermediate Similarity NPD6841 Approved
0.7381 Intermediate Similarity NPD6843 Phase 3
0.7381 Intermediate Similarity NPD291 Approved
0.7372 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7342 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD6559 Discontinued
0.7325 Intermediate Similarity NPD6374 Clinical (unspecified phase)
0.7325 Intermediate Similarity NPD3817 Phase 2
0.7319 Intermediate Similarity NPD422 Phase 1
0.731 Intermediate Similarity NPD230 Phase 1
0.7293 Intermediate Similarity NPD5283 Phase 1
0.7261 Intermediate Similarity NPD2801 Approved
0.7256 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7254 Intermediate Similarity NPD2861 Phase 2
0.7252 Intermediate Similarity NPD556 Approved
0.7241 Intermediate Similarity NPD1558 Phase 1
0.7237 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD6055 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD2219 Phase 1
0.7214 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7211 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7211 Intermediate Similarity NPD4536 Approved
0.7211 Intermediate Similarity NPD4538 Approved
0.7208 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7192 Intermediate Similarity NPD5124 Phase 1
0.7192 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7183 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7181 Intermediate Similarity NPD3540 Phase 1
0.7172 Intermediate Similarity NPD1726 Clinical (unspecified phase)
0.717 Intermediate Similarity NPD3882 Suspended
0.7161 Intermediate Similarity NPD3687 Approved
0.7161 Intermediate Similarity NPD3686 Approved
0.7153 Intermediate Similarity NPD4625 Phase 3
0.7152 Intermediate Similarity NPD5844 Phase 1
0.7152 Intermediate Similarity NPD2978 Approved
0.7152 Intermediate Similarity NPD2977 Approved
0.7152 Intermediate Similarity NPD8455 Phase 2
0.7126 Intermediate Similarity NPD7685 Pre-registration
0.7124 Intermediate Similarity NPD1511 Approved
0.7124 Intermediate Similarity NPD1774 Approved
0.7123 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7123 Intermediate Similarity NPD3620 Phase 2
0.7114 Intermediate Similarity NPD3539 Phase 1
0.7105 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD4237 Approved
0.7086 Intermediate Similarity NPD4236 Phase 3
0.7078 Intermediate Similarity NPD4123 Phase 3
0.7066 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD6671 Approved
0.7055 Intermediate Similarity NPD3787 Discontinued
0.7047 Intermediate Similarity NPD5588 Approved
0.7047 Intermediate Similarity NPD5960 Phase 3
0.7044 Intermediate Similarity NPD5773 Approved
0.7044 Intermediate Similarity NPD1465 Phase 2
0.7044 Intermediate Similarity NPD5772 Approved
0.7042 Intermediate Similarity NPD8651 Approved
0.7032 Intermediate Similarity NPD1512 Approved
0.7027 Intermediate Similarity NPD6653 Approved
0.7023 Intermediate Similarity NPD968 Approved
0.7013 Intermediate Similarity NPD4357 Discontinued
0.7007 Intermediate Similarity NPD4060 Phase 1
0.7006 Intermediate Similarity NPD4005 Discontinued
0.6993 Remote Similarity NPD6190 Approved
0.6993 Remote Similarity NPD2677 Approved
0.698 Remote Similarity NPD7097 Phase 1
0.6974 Remote Similarity NPD3060 Approved
0.6974 Remote Similarity NPD4162 Approved
0.6972 Remote Similarity NPD3685 Discontinued
0.6962 Remote Similarity NPD4380 Phase 2
0.6959 Remote Similarity NPD447 Suspended
0.6957 Remote Similarity NPD5536 Phase 2
0.6957 Remote Similarity NPD1408 Clinical (unspecified phase)
0.6939 Remote Similarity NPD6233 Phase 2
0.6929 Remote Similarity NPD1778 Approved
0.6928 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6928 Remote Similarity NPD4110 Phase 3
0.6928 Remote Similarity NPD4628 Phase 3
0.6923 Remote Similarity NPD1940 Clinical (unspecified phase)
0.6918 Remote Similarity NPD3179 Approved
0.6918 Remote Similarity NPD3180 Approved
0.6914 Remote Similarity NPD7075 Discontinued
0.691 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6908 Remote Similarity NPD2424 Discontinued
0.6901 Remote Similarity NPD2235 Phase 2
0.6901 Remote Similarity NPD2231 Phase 2
0.6899 Remote Similarity NPD1242 Phase 1
0.6894 Remote Similarity NPD5402 Approved
0.6894 Remote Similarity NPD5353 Approved
0.6886 Remote Similarity NPD3751 Discontinued
0.6879 Remote Similarity NPD3496 Discontinued
0.6879 Remote Similarity NPD2122 Discontinued
0.6867 Remote Similarity NPD6111 Discontinued
0.6863 Remote Similarity NPD5177 Phase 3
0.6849 Remote Similarity NPD5752 Clinical (unspecified phase)
0.6846 Remote Similarity NPD5735 Approved
0.6842 Remote Similarity NPD5763 Approved
0.6842 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6842 Remote Similarity NPD5762 Approved
0.6842 Remote Similarity NPD1358 Approved
0.6842 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6838 Remote Similarity NPD821 Approved
0.6832 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6831 Remote Similarity NPD776 Approved
0.6829 Remote Similarity NPD5494 Approved
0.6821 Remote Similarity NPD4108 Discontinued
0.6818 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6815 Remote Similarity NPD7527 Clinical (unspecified phase)
0.6815 Remote Similarity NPD52 Approved
0.6815 Remote Similarity NPD7526 Approved
0.6809 Remote Similarity NPD5846 Approved
0.6809 Remote Similarity NPD5125 Phase 3
0.6809 Remote Similarity NPD6516 Phase 2
0.6809 Remote Similarity NPD5126 Approved
0.6803 Remote Similarity NPD7095 Approved
0.6802 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6797 Remote Similarity NPD970 Clinical (unspecified phase)
0.6797 Remote Similarity NPD1549 Phase 2
0.6795 Remote Similarity NPD6799 Approved
0.6795 Remote Similarity NPD7212 Phase 2
0.6795 Remote Similarity NPD7213 Phase 3
0.679 Remote Similarity NPD2560 Approved
0.679 Remote Similarity NPD2563 Approved
0.6784 Remote Similarity NPD7549 Discontinued
0.6781 Remote Similarity NPD9494 Approved
0.6779 Remote Similarity NPD2238 Phase 2
0.6776 Remote Similarity NPD2161 Phase 2
0.6776 Remote Similarity NPD3454 Phase 3
0.6776 Remote Similarity NPD6100 Approved
0.6776 Remote Similarity NPD6099 Approved
0.6772 Remote Similarity NPD5403 Approved
0.677 Remote Similarity NPD3382 Approved
0.677 Remote Similarity NPD3383 Approved
0.677 Remote Similarity NPD6801 Discontinued
0.677 Remote Similarity NPD3384 Approved
0.6763 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6758 Remote Similarity NPD7680 Approved
0.6757 Remote Similarity NPD6798 Discontinued
0.6752 Remote Similarity NPD7447 Phase 1
0.6747 Remote Similarity NPD6232 Discontinued
0.6741 Remote Similarity NPD3021 Approved
0.6741 Remote Similarity NPD3022 Approved
0.6733 Remote Similarity NPD6355 Discontinued
0.6733 Remote Similarity NPD4340 Discontinued

  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