Structure

Physi-Chem Properties

Molecular Weight:  474.19
Volume:  467.387
LogP:  1.607
LogD:  2.057
LogS:  -4.246
# Rotatable Bonds:  7
TPSA:  127.07
# H-Bond Aceptor:  9
# H-Bond Donor:  4
# Rings:  4
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.467
Synthetic Accessibility Score:  4.003
Fsp3:  0.44
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:  -5.184
MDCK Permeability:  1.8915976397693157e-05
Pgp-inhibitor:  0.747
Pgp-substrate:  0.212
Human Intestinal Absorption (HIA):  0.578
20% Bioavailability (F20%):  0.004
30% Bioavailability (F30%):  0.318

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.207
Plasma Protein Binding (PPB):  73.0999526977539%
Volume Distribution (VD):  0.68
Pgp-substrate:  7.590222358703613%

ADMET: Metabolism

CYP1A2-inhibitor:  0.059
CYP1A2-substrate:  0.838
CYP2C19-inhibitor:  0.02
CYP2C19-substrate:  0.297
CYP2C9-inhibitor:  0.009
CYP2C9-substrate:  0.371
CYP2D6-inhibitor:  0.277
CYP2D6-substrate:  0.88
CYP3A4-inhibitor:  0.127
CYP3A4-substrate:  0.193

ADMET: Excretion

Clearance (CL):  5.891
Half-life (T1/2):  0.506

ADMET: Toxicity

hERG Blockers:  0.232
Human Hepatotoxicity (H-HT):  0.352
Drug-inuced Liver Injury (DILI):  0.119
AMES Toxicity:  0.657
Rat Oral Acute Toxicity:  0.034
Maximum Recommended Daily Dose:  0.74
Skin Sensitization:  0.694
Carcinogencity:  0.212
Eye Corrosion:  0.003
Eye Irritation:  0.013
Respiratory Toxicity:  0.041

Download Data

Data Type Select
General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC76871

Natural Product ID:  NPC76871
Common Name*:   Subavenoside E
IUPAC Name:   (2S,3R,4S,5S,6R)-2-[[3,9-dimethoxy-5-(methoxymethyl)-7H-dibenzo[1,3-d:3',4'-g][7]annulen-2-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:   Subavenoside E
Standard InCHIKey:  OZQFFZHCPIKJER-NHTNDUFYSA-N
Standard InCHI:  InChI=1S/C25H30O9/c1-30-12-14-5-4-13-8-15(31-2)6-7-16(13)18-10-20(19(32-3)9-17(14)18)33-25-24(29)23(28)22(27)21(11-26)34-25/h5-10,21-29H,4,11-12H2,1-3H3/t21-,22-,23+,24-,25-/m1/s1
SMILES:  COCC1=CCc2c(c3c1cc(OC)c(c3)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)ccc(c2)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2152484
PubChem CID:   71451248
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
NPO9305 Iotrochota purpurea Species Iotrochotidae Eukaryota n.a. n.a. n.a. PMID[10924179]
NPO8035 Tylophora tanakae Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[12350151]
NPO10900 Cinnamomum subavenium Species Lauraceae Eukaryota stems Wulai Hsiang, Taipei County, Taiwan 2005-MAY PMID[17253858]
NPO2298 Streptomyces platensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[19581087]
NPO2298 Streptomyces platensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[20299229]
NPO4138 Betula platyphylla Species Betulaceae Eukaryota bark n.a. n.a. PMID[20363129]
NPO2298 Streptomyces platensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21214253]
NPO10900 Cinnamomum subavenium Species Lauraceae Eukaryota Leaves n.a. n.a. PMID[23025417]
NPO9305 Iotrochota purpurea Species Iotrochotidae Eukaryota n.a. n.a. n.a. PMID[23131412]
NPO10900 Cinnamomum subavenium Species Lauraceae Eukaryota stem bark Laifeng, Hubei Province, China 2012-JUL PMID[26087384]
NPO11699 Ecballium elaterium Species Cucurbitaceae Eukaryota Fruit juice n.a. n.a. PMID[3404148]
NPO11699 Ecballium elaterium Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4138 Betula platyphylla Species Betulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4138 Betula platyphylla Species Betulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11699 Ecballium elaterium Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4138 Betula platyphylla Species Betulaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4138 Betula platyphylla Species Betulaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4493 Polygonum flaccidum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5008 Hubertia tomentosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15252 Clathria prolifera Species Microcionidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11811 Capparis ovata Species Capparaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8477 Myristica cagayanensis Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3378 Alstonia undulifolia Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1182 Croton montevidensis Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO761 Fagus fusca Species Fagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12888 Echinus microtuberculatus Species Echinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12308 Metridium senile Species Metridiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12436 Quercus imbricaria Species Fagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12669 Cassine papillosa Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6253 Conus pulicarius Species Conidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11699 Ecballium elaterium Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2298 Streptomyces platensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO5384 Ligustrum obtusifolium Species Oleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4138 Betula platyphylla Species Betulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20291 Phyllanthus oligospermus Species Phyllanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11256 Pseudowintera colorata Species Winteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12544 Dioscorea olfersiana Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10737 Asteriscus aquaticus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9305 Iotrochota purpurea Species Iotrochotidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5823 Helichrysum auriceps Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10900 Cinnamomum subavenium Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9922 Myelobia smerintha Species Crambidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11553 Phebalium dentatum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7709 Spiracantha cornifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3736 Scrophularia koelzii Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9672 Lotus ucrainicus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12188 Datisca glomerata Species Datiscaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7045 Viviparus japonicus Species Viviparidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2608 Solanum andigena Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8035 Tylophora tanakae Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10393 Ophidiaster ophidianus Species Ophidiasteridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9509 Charpentiera obovata Species Amaranthaceae 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
NPT2 Others Unspecified IC50 = 19000.0 nM PMID[517475]

☑ 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 NPC76871 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
0.9925 High Similarity NPC60249
0.9632 High Similarity NPC48309
0.9403 High Similarity NPC187194
0.9403 High Similarity NPC476411
0.9248 High Similarity NPC472024
0.9248 High Similarity NPC80600
0.9214 High Similarity NPC25292
0.9214 High Similarity NPC473045
0.9209 High Similarity NPC246947
0.9197 High Similarity NPC138738
0.9197 High Similarity NPC470413
0.9179 High Similarity NPC9912
0.9173 High Similarity NPC26653
0.9173 High Similarity NPC270849
0.9143 High Similarity NPC470950
0.9143 High Similarity NPC46092
0.9143 High Similarity NPC185307
0.9143 High Similarity NPC473044
0.9124 High Similarity NPC177035
0.9124 High Similarity NPC199459
0.9124 High Similarity NPC52277
0.9098 High Similarity NPC302378
0.9085 High Similarity NPC99515
0.9085 High Similarity NPC190714
0.9078 High Similarity NPC471063
0.9078 High Similarity NPC129417
0.9078 High Similarity NPC283995
0.9078 High Similarity NPC79429
0.9078 High Similarity NPC471667
0.9078 High Similarity NPC217635
0.9078 High Similarity NPC470235
0.9071 High Similarity NPC189115
0.9071 High Similarity NPC476356
0.9065 High Similarity NPC106944
0.903 High Similarity NPC248355
0.903 High Similarity NPC166040
0.9028 High Similarity NPC44452
0.9014 High Similarity NPC286245
0.9014 High Similarity NPC279298
0.9014 High Similarity NPC272619
0.9014 High Similarity NPC22150
0.9014 High Similarity NPC38041
0.9014 High Similarity NPC43508
0.9014 High Similarity NPC476301
0.9014 High Similarity NPC18979
0.9 High Similarity NPC469661
0.9 High Similarity NPC472711
0.8993 High Similarity NPC156376
0.8973 High Similarity NPC21902
0.8973 High Similarity NPC474442
0.8971 High Similarity NPC97316
0.8958 High Similarity NPC175976
0.8951 High Similarity NPC205796
0.8951 High Similarity NPC112861
0.8951 High Similarity NPC276753
0.8944 High Similarity NPC471065
0.8944 High Similarity NPC253015
0.8936 High Similarity NPC469559
0.8921 High Similarity NPC304152
0.8905 High Similarity NPC25821
0.8905 High Similarity NPC215833
0.8905 High Similarity NPC69513
0.8897 High Similarity NPC248307
0.8897 High Similarity NPC65942
0.8889 High Similarity NPC15956
0.8889 High Similarity NPC224674
0.8889 High Similarity NPC193473
0.8889 High Similarity NPC31325
0.8889 High Similarity NPC275284
0.8889 High Similarity NPC39657
0.8889 High Similarity NPC114505
0.8889 High Similarity NPC213074
0.8881 High Similarity NPC469586
0.8881 High Similarity NPC475096
0.8873 High Similarity NPC477898
0.8873 High Similarity NPC278961
0.8873 High Similarity NPC113680
0.8865 High Similarity NPC471908
0.8857 High Similarity NPC212770
0.8857 High Similarity NPC98777
0.8841 High Similarity NPC13745
0.8841 High Similarity NPC251981
0.8841 High Similarity NPC35731
0.8841 High Similarity NPC48863
0.8832 High Similarity NPC162093
0.8828 High Similarity NPC270751
0.8819 High Similarity NPC125755
0.8811 High Similarity NPC84181
0.8803 High Similarity NPC5262
0.8803 High Similarity NPC472714
0.8803 High Similarity NPC475084
0.8803 High Similarity NPC302506
0.8786 High Similarity NPC65530
0.8786 High Similarity NPC59324
0.8777 High Similarity NPC101624
0.8777 High Similarity NPC79957
0.8777 High Similarity NPC184938
0.8777 High Similarity NPC470236
0.8768 High Similarity NPC49074
0.8767 High Similarity NPC286235
0.8767 High Similarity NPC51328
0.8767 High Similarity NPC55158
0.8759 High Similarity NPC227902
0.875 High Similarity NPC161700
0.875 High Similarity NPC277867
0.875 High Similarity NPC307110
0.875 High Similarity NPC86030
0.875 High Similarity NPC5851
0.8741 High Similarity NPC478239
0.8714 High Similarity NPC164857
0.8714 High Similarity NPC25695
0.8714 High Similarity NPC203230
0.8714 High Similarity NPC242028
0.8714 High Similarity NPC172818
0.8707 High Similarity NPC475224
0.8707 High Similarity NPC158635
0.8707 High Similarity NPC98624
0.8707 High Similarity NPC229882
0.8705 High Similarity NPC470881
0.8699 High Similarity NPC248132
0.8699 High Similarity NPC130449
0.8696 High Similarity NPC299144
0.8681 High Similarity NPC118385
0.8681 High Similarity NPC76176
0.8681 High Similarity NPC472713
0.8681 High Similarity NPC472712
0.8681 High Similarity NPC138227
0.8681 High Similarity NPC164183
0.8681 High Similarity NPC187774
0.8681 High Similarity NPC168579
0.8681 High Similarity NPC179521
0.8681 High Similarity NPC469313
0.8681 High Similarity NPC473046
0.8676 High Similarity NPC252307
0.8676 High Similarity NPC72529
0.8676 High Similarity NPC245826
0.8676 High Similarity NPC474178
0.8671 High Similarity NPC253878
0.8671 High Similarity NPC140502
0.8671 High Similarity NPC157816
0.8662 High Similarity NPC226547
0.8658 High Similarity NPC78809
0.8657 High Similarity NPC94276
0.8657 High Similarity NPC109822
0.8647 High Similarity NPC71090
0.8643 High Similarity NPC55040
0.8639 High Similarity NPC95392
0.8639 High Similarity NPC35877
0.8639 High Similarity NPC55715
0.8633 High Similarity NPC6836
0.8633 High Similarity NPC263064
0.8633 High Similarity NPC294166
0.8633 High Similarity NPC115022
0.863 High Similarity NPC473480
0.863 High Similarity NPC15538
0.8623 High Similarity NPC475067
0.8623 High Similarity NPC469698
0.8623 High Similarity NPC473412
0.8611 High Similarity NPC252169
0.8611 High Similarity NPC37793
0.8603 High Similarity NPC106511
0.8603 High Similarity NPC118787
0.8603 High Similarity NPC111247
0.8603 High Similarity NPC163332
0.8603 High Similarity NPC41706
0.8603 High Similarity NPC292056
0.8603 High Similarity NPC147821
0.8603 High Similarity NPC183181
0.8603 High Similarity NPC319625
0.8601 High Similarity NPC210192
0.8601 High Similarity NPC471414
0.8601 High Similarity NPC186406
0.8592 High Similarity NPC22517
0.8591 High Similarity NPC302610
0.8582 High Similarity NPC37468
0.8581 High Similarity NPC472710
0.8581 High Similarity NPC469706
0.8581 High Similarity NPC145979
0.8581 High Similarity NPC182368
0.8581 High Similarity NPC183380
0.8581 High Similarity NPC218041
0.8581 High Similarity NPC225815
0.8581 High Similarity NPC260781
0.8581 High Similarity NPC185955
0.8581 High Similarity NPC469707
0.8581 High Similarity NPC9933
0.8581 High Similarity NPC214326
0.8581 High Similarity NPC472709
0.8581 High Similarity NPC238140
0.8571 High Similarity NPC478085
0.8571 High Similarity NPC93924
0.8571 High Similarity NPC87696
0.8571 High Similarity NPC170694
0.8571 High Similarity NPC107478
0.8571 High Similarity NPC116229
0.8571 High Similarity NPC47181
0.8562 High Similarity NPC241846
0.8562 High Similarity NPC93610
0.8562 High Similarity NPC199928
0.8561 High Similarity NPC254275

  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 NPC76871 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
0.8601 High Similarity NPD6674 Discontinued
0.8296 Intermediate Similarity NPD3705 Approved
0.8214 Intermediate Similarity NPD3027 Phase 3
0.8169 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.8169 Intermediate Similarity NPD1613 Approved
0.8082 Intermediate Similarity NPD7266 Discontinued
0.8029 Intermediate Similarity NPD1091 Approved
0.7973 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7935 Intermediate Similarity NPD37 Approved
0.7925 Intermediate Similarity NPD7199 Phase 2
0.7908 Intermediate Similarity NPD1653 Approved
0.7898 Intermediate Similarity NPD4966 Approved
0.7898 Intermediate Similarity NPD4967 Phase 2
0.7898 Intermediate Similarity NPD4965 Approved
0.7887 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7817 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7815 Intermediate Similarity NPD5058 Phase 3
0.7799 Intermediate Similarity NPD6234 Discontinued
0.7791 Intermediate Similarity NPD7228 Approved
0.7771 Intermediate Similarity NPD8455 Phase 2
0.7761 Intermediate Similarity NPD5283 Phase 1
0.7716 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7703 Intermediate Similarity NPD4108 Discontinued
0.7697 Intermediate Similarity NPD7074 Phase 3
0.7692 Intermediate Similarity NPD2861 Phase 2
0.7681 Intermediate Similarity NPD1357 Approved
0.7647 Intermediate Similarity NPD7157 Approved
0.7636 Intermediate Similarity NPD7054 Approved
0.7635 Intermediate Similarity NPD4538 Approved
0.7635 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7635 Intermediate Similarity NPD4536 Approved
0.7626 Intermediate Similarity NPD5125 Phase 3
0.7626 Intermediate Similarity NPD5126 Approved
0.7605 Intermediate Similarity NPD7240 Approved
0.759 Intermediate Similarity NPD7472 Approved
0.7576 Intermediate Similarity NPD3818 Discontinued
0.7556 Intermediate Similarity NPD7843 Approved
0.7551 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7551 Intermediate Similarity NPD4060 Phase 1
0.7551 Intermediate Similarity NPD3620 Phase 2
0.7532 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7519 Intermediate Similarity NPD2684 Approved
0.7517 Intermediate Similarity NPD4908 Phase 1
0.75 Intermediate Similarity NPD5735 Approved
0.7483 Intermediate Similarity NPD1375 Discontinued
0.7467 Intermediate Similarity NPD5588 Approved
0.7467 Intermediate Similarity NPD5960 Phase 3
0.7466 Intermediate Similarity NPD4625 Phase 3
0.7456 Intermediate Similarity NPD7808 Phase 3
0.7442 Intermediate Similarity NPD6842 Approved
0.7442 Intermediate Similarity NPD6841 Approved
0.7442 Intermediate Similarity NPD6843 Phase 3
0.744 Intermediate Similarity NPD6797 Phase 2
0.7439 Intermediate Similarity NPD3787 Discontinued
0.7425 Intermediate Similarity NPD5844 Phase 1
0.7415 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7413 Intermediate Similarity NPD2983 Phase 2
0.7413 Intermediate Similarity NPD2982 Phase 2
0.7407 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7403 Intermediate Similarity NPD2677 Approved
0.7396 Intermediate Similarity NPD7251 Discontinued
0.7394 Intermediate Similarity NPD1610 Phase 2
0.7375 Intermediate Similarity NPD1934 Approved
0.7368 Intermediate Similarity NPD5762 Approved
0.7368 Intermediate Similarity NPD5763 Approved
0.7361 Intermediate Similarity NPD8651 Approved
0.7353 Intermediate Similarity NPD228 Approved
0.7353 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7347 Intermediate Similarity NPD7095 Approved
0.7343 Intermediate Similarity NPD2981 Phase 2
0.7329 Intermediate Similarity NPD3018 Phase 2
0.7326 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7325 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7315 Intermediate Similarity NPD4140 Approved
0.7294 Intermediate Similarity NPD7685 Pre-registration
0.7294 Intermediate Similarity NPD6559 Discontinued
0.7285 Intermediate Similarity NPD7097 Phase 1
0.7255 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7254 Intermediate Similarity NPD6516 Phase 2
0.7254 Intermediate Similarity NPD5846 Approved
0.7248 Intermediate Similarity NPD6233 Phase 2
0.7246 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD6166 Phase 2
0.7239 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD4110 Phase 3
0.7226 Intermediate Similarity NPD6331 Phase 2
0.7226 Intermediate Similarity NPD6658 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD4628 Phase 3
0.7226 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD2977 Approved
0.7222 Intermediate Similarity NPD2978 Approved
0.72 Intermediate Similarity NPD5837 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD1558 Phase 1
0.7195 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD4005 Discontinued
0.7185 Intermediate Similarity NPD290 Approved
0.7181 Intermediate Similarity NPD6798 Discontinued
0.7181 Intermediate Similarity NPD5109 Approved
0.7181 Intermediate Similarity NPD5110 Phase 2
0.7181 Intermediate Similarity NPD5111 Phase 2
0.7178 Intermediate Similarity NPD3817 Phase 2
0.7178 Intermediate Similarity NPD2560 Approved
0.7178 Intermediate Similarity NPD2563 Approved
0.7172 Intermediate Similarity NPD3685 Discontinued
0.7172 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7172 Intermediate Similarity NPD5327 Phase 3
0.717 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7169 Intermediate Similarity NPD8127 Discontinued
0.7161 Intermediate Similarity NPD4162 Approved
0.7161 Intermediate Similarity NPD4237 Approved
0.7161 Intermediate Similarity NPD4236 Phase 3
0.716 Intermediate Similarity NPD3751 Discontinued
0.7152 Intermediate Similarity NPD6355 Discontinued
0.7126 Intermediate Similarity NPD3051 Approved
0.7126 Intermediate Similarity NPD6071 Discontinued
0.7124 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7124 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7118 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7117 Intermediate Similarity NPD1465 Phase 2
0.7115 Intermediate Similarity NPD4535 Phase 3
0.7113 Intermediate Similarity NPD1548 Phase 1
0.711 Intermediate Similarity NPD8312 Approved
0.711 Intermediate Similarity NPD8313 Approved
0.7107 Intermediate Similarity NPD1940 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD2969 Approved
0.7083 Intermediate Similarity NPD2970 Approved
0.708 Intermediate Similarity NPD3021 Approved
0.708 Intermediate Similarity NPD3022 Approved
0.7078 Intermediate Similarity NPD2438 Suspended
0.7073 Intermediate Similarity NPD6374 Clinical (unspecified phase)
0.707 Intermediate Similarity NPD5241 Discontinued
0.707 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7068 Intermediate Similarity NPD291 Approved
0.7067 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD4749 Approved
0.7051 Intermediate Similarity NPD1652 Phase 2
0.7051 Intermediate Similarity NPD3060 Approved
0.7051 Intermediate Similarity NPD5177 Phase 3
0.705 Intermediate Similarity NPD5535 Approved
0.7047 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7044 Intermediate Similarity NPD4123 Phase 3
0.7044 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7042 Intermediate Similarity NPD5536 Phase 2
0.7039 Intermediate Similarity NPD3657 Discovery
0.7035 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7027 Intermediate Similarity NPD6584 Phase 3
0.7025 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.7024 Intermediate Similarity NPD6232 Discontinued
0.7021 Intermediate Similarity NPD709 Approved
0.7021 Intermediate Similarity NPD6671 Approved
0.702 Intermediate Similarity NPD1726 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD3687 Approved
0.7019 Intermediate Similarity NPD3686 Approved
0.7013 Intermediate Similarity NPD2154 Approved
0.7013 Intermediate Similarity NPD2155 Approved
0.7013 Intermediate Similarity NPD2156 Approved
0.7012 Intermediate Similarity NPD2801 Approved
0.7012 Intermediate Similarity NPD7819 Suspended
0.7006 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD52 Approved
0.7 Intermediate Similarity NPD7527 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD7526 Approved
0.6993 Remote Similarity NPD6653 Approved
0.6993 Remote Similarity NPD6353 Approved
0.6986 Remote Similarity NPD1608 Approved
0.6981 Remote Similarity NPD1774 Approved
0.6978 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6975 Remote Similarity NPD6055 Clinical (unspecified phase)
0.6974 Remote Similarity NPD2238 Phase 2
0.6968 Remote Similarity NPD2161 Phase 2
0.6962 Remote Similarity NPD6190 Approved
0.6962 Remote Similarity NPD5084 Clinical (unspecified phase)
0.6959 Remote Similarity NPD3094 Phase 2
0.6957 Remote Similarity NPD556 Approved
0.6954 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6951 Remote Similarity NPD7945 Clinical (unspecified phase)
0.6941 Remote Similarity NPD27 Approved
0.6941 Remote Similarity NPD2489 Approved
0.6936 Remote Similarity NPD7007 Discovery
0.6933 Remote Similarity NPD4675 Approved
0.6933 Remote Similarity NPD7028 Phase 2
0.6933 Remote Similarity NPD4678 Approved
0.6928 Remote Similarity NPD4340 Discontinued
0.6919 Remote Similarity NPD7680 Approved
0.6918 Remote Similarity NPD1611 Approved
0.6909 Remote Similarity NPD5772 Approved
0.6909 Remote Similarity NPD5773 Approved
0.6909 Remote Similarity NPD6818 Clinical (unspecified phase)
0.6908 Remote Similarity NPD4062 Phase 3
0.6905 Remote Similarity NPD5494 Approved
0.6903 Remote Similarity NPD7033 Discontinued
0.6901 Remote Similarity NPD7473 Discontinued
0.6899 Remote Similarity NPD3892 Phase 2
0.6894 Remote Similarity NPD7314 Clinical (unspecified phase)
0.6892 Remote Similarity NPD1283 Approved
0.689 Remote Similarity NPD4773 Phase 2
0.689 Remote Similarity NPD4772 Phase 2

  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