Structure

Physi-Chem Properties

Molecular Weight:  742.27
Volume:  687.687
LogP:  -0.284
LogD:  0.122
LogS:  -3.359
# Rotatable Bonds:  12
TPSA:  254.14
# H-Bond Aceptor:  18
# H-Bond Donor:  8
# Rings:  6
# Heavy Atoms:  18

MedChem Properties

QED Drug-Likeness Score:  0.119
Synthetic Accessibility Score:  5.139
Fsp3:  0.647
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.454
MDCK Permeability:  9.085717465495691e-05
Pgp-inhibitor:  0.006
Pgp-substrate:  0.998
Human Intestinal Absorption (HIA):  0.909
20% Bioavailability (F20%):  0.001
30% Bioavailability (F30%):  0.955

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.14
Plasma Protein Binding (PPB):  34.8592529296875%
Volume Distribution (VD):  0.427
Pgp-substrate:  27.90294075012207%

ADMET: Metabolism

CYP1A2-inhibitor:  0.002
CYP1A2-substrate:  0.565
CYP2C19-inhibitor:  0.002
CYP2C19-substrate:  0.751
CYP2C9-inhibitor:  0.0
CYP2C9-substrate:  0.08
CYP2D6-inhibitor:  0.003
CYP2D6-substrate:  0.195
CYP3A4-inhibitor:  0.016
CYP3A4-substrate:  0.092

ADMET: Excretion

Clearance (CL):  1.436
Half-life (T1/2):  0.384

ADMET: Toxicity

hERG Blockers:  0.678
Human Hepatotoxicity (H-HT):  0.19
Drug-inuced Liver Injury (DILI):  0.135
AMES Toxicity:  0.082
Rat Oral Acute Toxicity:  0.011
Maximum Recommended Daily Dose:  0.034
Skin Sensitization:  0.732
Carcinogencity:  0.03
Eye Corrosion:  0.003
Eye Irritation:  0.007
Respiratory Toxicity:  0.019

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

  Natural Product: NPC35877

Natural Product ID:  NPC35877
Common Name*:   Eleutheroside E
IUPAC Name:   (2S,3R,4S,5S,6R)-2-[4-[(3R,3aS,6S,6aR)-6-[3,5-dimethoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2,6-dimethoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:  
Standard InCHIKey:  FFDULTAFAQRACT-JSGUJALWSA-N
Standard InCHI:  InChI=1S/C34H46O18/c1-43-17-5-13(6-18(44-2)31(17)51-33-27(41)25(39)23(37)21(9-35)49-33)29-15-11-48-30(16(15)12-47-29)14-7-19(45-3)32(20(8-14)46-4)52-34-28(42)26(40)24(38)22(10-36)50-34/h5-8,15-16,21-30,33-42H,9-12H2,1-4H3/t15-,16+,21-,22-,23-,24-,25+,26+,27-,28-,29+,30-,33+,34+/m1/s1
SMILES:  OC[C@H]1O[C@@H](Oc2c(OC)cc(cc2OC)[C@@H]2OC[C@H]3[C@H]2CO[C@@H]3c2cc(OC)c(c(c2)OC)O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2442731
PubChem CID:   71312557
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0001392] Lignans, neolignans and related compounds
      • [CHEMONTID:0001511] Lignan 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
NPO11872 Eleutherococcus senticosus Species Araliaceae Eukaryota n.a. leaf n.a. PMID[17125224]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. leaf n.a. PMID[18409045]
NPO29141 Panax ginseng Species Araliaceae Eukaryota flower buds n.a. n.a. PMID[19926279]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. root n.a. PMID[2092947]
NPO29141 Panax ginseng Species Araliaceae Eukaryota berry n.a. n.a. PMID[21216145]
NPO29141 Panax ginseng Species Araliaceae Eukaryota leaves n.a. n.a. PMID[24290061]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. PMID[24968750]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. PMID[25152999]
NPO29141 Panax ginseng Species Araliaceae Eukaryota stems-leaves n.a. n.a. PMID[26420067]
NPO11872 Eleutherococcus senticosus Species Araliaceae Eukaryota leaves n.a. n.a. PMID[27400231]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. stem n.a. PMID[27914541]
NPO29141 Panax ginseng Species Araliaceae Eukaryota Flower Buds n.a. n.a. PMID[28345906]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. PMID[32129622]
NPO8500 Acanthopanax gracilistylus Species Araliaceae Eukaryota n.a. n.a. n.a. PMID[32319765]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. Database[MetaboLights]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11872 Eleutherococcus senticosus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8500 Acanthopanax gracilistylus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO753 Acanthopanax sessiliflorum n.a. n.a. n.a. n.a. n.a. n.a. Database[TM-MC]
NPO11872 Eleutherococcus senticosus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8500 Acanthopanax gracilistylus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11872 Eleutherococcus senticosus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8500 Acanthopanax gracilistylus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29141 Panax ginseng Species Araliaceae 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
NPT71 Cell Line HEK293 Homo sapiens Inhibition = 9.8 % PMID[574045]

☑ 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 NPC35877 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 NPC95392
1.0 High Similarity NPC55715
0.9648 High Similarity NPC276753
0.9648 High Similarity NPC205796
0.9514 High Similarity NPC248132
0.9514 High Similarity NPC130449
0.9507 High Similarity NPC471063
0.9448 High Similarity NPC51328
0.9448 High Similarity NPC286235
0.9448 High Similarity NPC55158
0.9384 High Similarity NPC238140
0.9384 High Similarity NPC475224
0.9366 High Similarity NPC246947
0.9362 High Similarity NPC226547
0.931 High Similarity NPC39657
0.9247 High Similarity NPC270751
0.9236 High Similarity NPC187774
0.9236 High Similarity NPC473046
0.9236 High Similarity NPC472713
0.9236 High Similarity NPC472712
0.9236 High Similarity NPC118385
0.922 High Similarity NPC283949
0.9172 High Similarity NPC38041
0.9172 High Similarity NPC22150
0.9172 High Similarity NPC279298
0.9155 High Similarity NPC156376
0.9122 High Similarity NPC472709
0.9122 High Similarity NPC472710
0.911 High Similarity NPC112861
0.9097 High Similarity NPC472714
0.9097 High Similarity NPC5262
0.9091 High Similarity NPC56091
0.9091 High Similarity NPC46591
0.9085 High Similarity NPC185908
0.9078 High Similarity NPC236522
0.9078 High Similarity NPC150534
0.9041 High Similarity NPC277867
0.9041 High Similarity NPC18979
0.9041 High Similarity NPC161700
0.9034 High Similarity NPC278961
0.9034 High Similarity NPC185307
0.9034 High Similarity NPC477898
0.9034 High Similarity NPC470950
0.9034 High Similarity NPC113680
0.9028 High Similarity NPC108674
0.9028 High Similarity NPC471908
0.9 High Similarity NPC302610
0.898 High Similarity NPC125755
0.898 High Similarity NPC241846
0.898 High Similarity NPC93610
0.8973 High Similarity NPC84181
0.8973 High Similarity NPC79429
0.8973 High Similarity NPC217635
0.8973 High Similarity NPC283995
0.8973 High Similarity NPC473045
0.8973 High Similarity NPC25292
0.8973 High Similarity NPC129417
0.8973 High Similarity NPC471667
0.8973 High Similarity NPC470235
0.8966 High Similarity NPC189115
0.8966 High Similarity NPC469559
0.8966 High Similarity NPC287124
0.8966 High Similarity NPC302506
0.8966 High Similarity NPC476356
0.8958 High Similarity NPC177868
0.8944 High Similarity NPC470236
0.8936 High Similarity NPC215833
0.8936 High Similarity NPC69513
0.8933 High Similarity NPC473621
0.8926 High Similarity NPC470826
0.8926 High Similarity NPC473266
0.8926 High Similarity NPC470098
0.8917 High Similarity NPC59516
0.8912 High Similarity NPC476301
0.8912 High Similarity NPC475096
0.8912 High Similarity NPC43508
0.8904 High Similarity NPC37793
0.8904 High Similarity NPC12728
0.8904 High Similarity NPC46092
0.8904 High Similarity NPC473044
0.8904 High Similarity NPC185071
0.8897 High Similarity NPC472711
0.8897 High Similarity NPC469661
0.8881 High Similarity NPC164857
0.8881 High Similarity NPC25695
0.8881 High Similarity NPC172818
0.8873 High Similarity NPC48863
0.8873 High Similarity NPC187194
0.8873 High Similarity NPC251981
0.8873 High Similarity NPC476411
0.8873 High Similarity NPC13745
0.8867 High Similarity NPC98624
0.8865 High Similarity NPC261812
0.8865 High Similarity NPC72046
0.8865 High Similarity NPC65183
0.8859 High Similarity NPC280945
0.8859 High Similarity NPC71726
0.8859 High Similarity NPC226153
0.8859 High Similarity NPC304048
0.8859 High Similarity NPC301961
0.8859 High Similarity NPC166584
0.8851 High Similarity NPC190714
0.8851 High Similarity NPC212890
0.8851 High Similarity NPC99515
0.8851 High Similarity NPC226540
0.8851 High Similarity NPC162193
0.8844 High Similarity NPC141569
0.8844 High Similarity NPC76176
0.8844 High Similarity NPC168579
0.8844 High Similarity NPC470097
0.8844 High Similarity NPC166884
0.8844 High Similarity NPC114119
0.8844 High Similarity NPC477701
0.8844 High Similarity NPC471415
0.8844 High Similarity NPC469313
0.8844 High Similarity NPC179521
0.8844 High Similarity NPC138227
0.8836 High Similarity NPC80326
0.8828 High Similarity NPC106944
0.8819 High Similarity NPC474039
0.8811 High Similarity NPC148893
0.8811 High Similarity NPC49235
0.8811 High Similarity NPC25333
0.8808 High Similarity NPC329343
0.8808 High Similarity NPC321972
0.8808 High Similarity NPC324517
0.8803 High Similarity NPC196937
0.8803 High Similarity NPC136750
0.8803 High Similarity NPC266848
0.88 High Similarity NPC240521
0.8797 High Similarity NPC306475
0.8792 High Similarity NPC327412
0.8792 High Similarity NPC193473
0.8792 High Similarity NPC15538
0.8792 High Similarity NPC213074
0.8792 High Similarity NPC320970
0.8792 High Similarity NPC15956
0.8792 High Similarity NPC275284
0.8792 High Similarity NPC473480
0.8792 High Similarity NPC31325
0.8792 High Similarity NPC114505
0.8792 High Similarity NPC320671
0.8792 High Similarity NPC224674
0.8792 High Similarity NPC328567
0.8792 High Similarity NPC227902
0.8784 High Similarity NPC178014
0.8784 High Similarity NPC42716
0.8784 High Similarity NPC307466
0.8784 High Similarity NPC474749
0.8784 High Similarity NPC477702
0.8784 High Similarity NPC180953
0.8784 High Similarity NPC11422
0.8784 High Similarity NPC469586
0.8782 High Similarity NPC115624
0.8776 High Similarity NPC255566
0.8776 High Similarity NPC298317
0.8774 High Similarity NPC241600
0.8774 High Similarity NPC173726
0.8767 High Similarity NPC58137
0.8767 High Similarity NPC273932
0.8767 High Similarity NPC89686
0.8767 High Similarity NPC257095
0.8767 High Similarity NPC300798
0.8766 High Similarity NPC11411
0.8759 High Similarity NPC98777
0.8759 High Similarity NPC212770
0.8758 High Similarity NPC159922
0.875 High Similarity NPC40664
0.875 High Similarity NPC121651
0.875 High Similarity NPC138350
0.875 High Similarity NPC165482
0.875 High Similarity NPC3293
0.875 High Similarity NPC197723
0.8742 High Similarity NPC185955
0.8742 High Similarity NPC9933
0.8742 High Similarity NPC214326
0.8742 High Similarity NPC260781
0.8742 High Similarity NPC469706
0.8742 High Similarity NPC145979
0.8742 High Similarity NPC218041
0.8742 High Similarity NPC182368
0.8742 High Similarity NPC469707
0.8742 High Similarity NPC225815
0.8741 High Similarity NPC31530
0.8734 High Similarity NPC222531
0.8733 High Similarity NPC175976
0.8732 High Similarity NPC299144
0.8732 High Similarity NPC162093
0.8725 High Similarity NPC317053
0.8725 High Similarity NPC324492
0.8718 High Similarity NPC1253
0.8718 High Similarity NPC100936
0.8707 High Similarity NPC472353
0.8707 High Similarity NPC475084
0.8707 High Similarity NPC174522
0.869 High Similarity NPC470413
0.869 High Similarity NPC59324
0.869 High Similarity NPC65530
0.869 High Similarity NPC138738
0.8681 High Similarity NPC141765

  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 NPC35877 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
0.8509 High Similarity NPD7228 Approved
0.8415 Intermediate Similarity NPD7240 Approved
0.8291 Intermediate Similarity NPD4965 Approved
0.8291 Intermediate Similarity NPD4966 Approved
0.8291 Intermediate Similarity NPD4967 Phase 2
0.8267 Intermediate Similarity NPD6674 Discontinued
0.8187 Intermediate Similarity NPD6234 Discontinued
0.8138 Intermediate Similarity NPD3027 Phase 3
0.8101 Intermediate Similarity NPD37 Approved
0.8095 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.8095 Intermediate Similarity NPD1613 Approved
0.8086 Intermediate Similarity NPD7199 Phase 2
0.7964 Intermediate Similarity NPD7472 Approved
0.7964 Intermediate Similarity NPD7074 Phase 3
0.7929 Intermediate Similarity NPD7808 Phase 3
0.7904 Intermediate Similarity NPD7054 Approved
0.7895 Intermediate Similarity NPD7266 Discontinued
0.7879 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7877 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7848 Intermediate Similarity NPD1653 Approved
0.7832 Intermediate Similarity NPD3705 Approved
0.7823 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7765 Intermediate Similarity NPD7251 Discontinued
0.7738 Intermediate Similarity NPD3818 Discontinued
0.7716 Intermediate Similarity NPD8455 Phase 2
0.7706 Intermediate Similarity NPD6797 Phase 2
0.7703 Intermediate Similarity NPD4908 Phase 1
0.7611 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.76 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7586 Intermediate Similarity NPD1091 Approved
0.7541 Intermediate Similarity NPD7680 Approved
0.7532 Intermediate Similarity NPD5058 Phase 3
0.7485 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.747 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.747 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7466 Intermediate Similarity NPD1610 Phase 2
0.7455 Intermediate Similarity NPD6374 Clinical (unspecified phase)
0.7414 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7412 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7412 Intermediate Similarity NPD6166 Phase 2
0.7412 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.741 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.74 Intermediate Similarity NPD2861 Phase 2
0.7386 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7381 Intermediate Similarity NPD5494 Approved
0.7379 Intermediate Similarity NPD1357 Approved
0.7375 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7365 Intermediate Similarity NPD2982 Phase 2
0.7365 Intermediate Similarity NPD2983 Phase 2
0.7362 Intermediate Similarity NPD6055 Clinical (unspecified phase)
0.7356 Intermediate Similarity NPD7685 Pre-registration
0.7356 Intermediate Similarity NPD6559 Discontinued
0.7346 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD1934 Approved
0.733 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7324 Intermediate Similarity NPD5283 Phase 1
0.7299 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7297 Intermediate Similarity NPD2981 Phase 2
0.7285 Intermediate Similarity NPD3018 Phase 2
0.7254 Intermediate Similarity NPD7843 Approved
0.7248 Intermediate Similarity NPD4749 Approved
0.7233 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD5735 Approved
0.7222 Intermediate Similarity NPD7157 Approved
0.7207 Intermediate Similarity NPD6842 Approved
0.7207 Intermediate Similarity NPD6843 Phase 3
0.7207 Intermediate Similarity NPD6841 Approved
0.7197 Intermediate Similarity NPD5588 Approved
0.7186 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7184 Intermediate Similarity NPD5844 Phase 1
0.7161 Intermediate Similarity NPD3620 Phase 2
0.7161 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD3817 Phase 2
0.7135 Intermediate Similarity NPD8127 Discontinued
0.7134 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD4536 Approved
0.7134 Intermediate Similarity NPD4538 Approved
0.7134 Intermediate Similarity NPD7097 Phase 1
0.7126 Intermediate Similarity NPD3384 Approved
0.7126 Intermediate Similarity NPD3382 Approved
0.7126 Intermediate Similarity NPD3383 Approved
0.7107 Intermediate Similarity NPD1375 Discontinued
0.7095 Intermediate Similarity NPD5126 Approved
0.7095 Intermediate Similarity NPD5125 Phase 3
0.7093 Intermediate Similarity NPD3787 Discontinued
0.7086 Intermediate Similarity NPD8651 Approved
0.7083 Intermediate Similarity NPD1465 Phase 2
0.7079 Intermediate Similarity NPD8313 Approved
0.7079 Intermediate Similarity NPD8312 Approved
0.7078 Intermediate Similarity NPD4625 Phase 3
0.7075 Intermediate Similarity NPD1548 Phase 1
0.7048 Intermediate Similarity NPD4005 Discontinued
0.7037 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7032 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD1652 Phase 2
0.7006 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD5124 Phase 1
0.7006 Intermediate Similarity NPD6355 Discontinued
0.7 Intermediate Similarity NPD5762 Approved
0.7 Intermediate Similarity NPD3882 Suspended
0.7 Intermediate Similarity NPD5763 Approved
0.6993 Remote Similarity NPD6917 Clinical (unspecified phase)
0.6982 Remote Similarity NPD2977 Approved
0.6982 Remote Similarity NPD7819 Suspended
0.6982 Remote Similarity NPD2801 Approved
0.6982 Remote Similarity NPD2978 Approved
0.6981 Remote Similarity NPD6028 Clinical (unspecified phase)
0.6981 Remote Similarity NPD4108 Discontinued
0.6981 Remote Similarity NPD6029 Clinical (unspecified phase)
0.6981 Remote Similarity NPD5960 Phase 3
0.6975 Remote Similarity NPD6331 Phase 2
0.6975 Remote Similarity NPD7466 Approved
0.6975 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6975 Remote Similarity NPD4110 Phase 3
0.6972 Remote Similarity NPD2684 Approved
0.6968 Remote Similarity NPD7095 Approved
0.6943 Remote Similarity NPD4060 Phase 1
0.6941 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6927 Remote Similarity NPD7549 Discontinued
0.6914 Remote Similarity NPD4237 Approved
0.6914 Remote Similarity NPD4236 Phase 3
0.6909 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6905 Remote Similarity NPD4678 Approved
0.6905 Remote Similarity NPD7028 Phase 2
0.6905 Remote Similarity NPD4675 Approved
0.6905 Remote Similarity NPD4380 Phase 2
0.6897 Remote Similarity NPD3051 Approved
0.689 Remote Similarity NPD6783 Clinical (unspecified phase)
0.689 Remote Similarity NPD7124 Phase 2
0.6882 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6871 Remote Similarity NPD3892 Phase 2
0.686 Remote Similarity NPD7075 Discontinued
0.6857 Remote Similarity NPD2970 Approved
0.6857 Remote Similarity NPD2969 Approved
0.6855 Remote Similarity NPD6653 Approved
0.6851 Remote Similarity NPD8054 Approved
0.6851 Remote Similarity NPD8053 Approved
0.6836 Remote Similarity NPD3751 Discontinued
0.6835 Remote Similarity NPD4140 Approved
0.6832 Remote Similarity NPD6100 Approved
0.6832 Remote Similarity NPD2161 Phase 2
0.6832 Remote Similarity NPD6099 Approved
0.6831 Remote Similarity NPD7906 Approved
0.6829 Remote Similarity NPD5084 Clinical (unspecified phase)
0.6828 Remote Similarity NPD228 Approved
0.6824 Remote Similarity NPD7945 Clinical (unspecified phase)
0.6813 Remote Similarity NPD6111 Discontinued
0.681 Remote Similarity NPD5177 Phase 3
0.6807 Remote Similarity NPD7447 Phase 1
0.68 Remote Similarity NPD7229 Phase 3
0.6798 Remote Similarity NPD8156 Discontinued
0.6797 Remote Similarity NPD5327 Phase 3
0.679 Remote Similarity NPD3540 Phase 1
0.6784 Remote Similarity NPD5773 Approved
0.6784 Remote Similarity NPD5772 Approved
0.678 Remote Similarity NPD7473 Discontinued
0.6772 Remote Similarity NPD6233 Phase 2
0.6768 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6768 Remote Similarity NPD4628 Phase 3
0.6766 Remote Similarity NPD1940 Clinical (unspecified phase)
0.6766 Remote Similarity NPD7526 Approved
0.6766 Remote Similarity NPD7527 Clinical (unspecified phase)
0.6766 Remote Similarity NPD52 Approved
0.6765 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6755 Remote Similarity NPD5846 Approved
0.6755 Remote Similarity NPD6516 Phase 2
0.675 Remote Similarity NPD6353 Approved
0.6747 Remote Similarity NPD7213 Phase 3
0.6747 Remote Similarity NPD1511 Approved
0.6747 Remote Similarity NPD7212 Phase 2
0.6744 Remote Similarity NPD5402 Approved
0.6743 Remote Similarity NPD6959 Discontinued
0.6742 Remote Similarity NPD8251 Approved
0.6742 Remote Similarity NPD8099 Discontinued
0.6742 Remote Similarity NPD8252 Approved
0.6739 Remote Similarity NPD7243 Clinical (unspecified phase)
0.673 Remote Similarity NPD1558 Phase 1
0.6728 Remote Similarity NPD3454 Phase 3
0.6728 Remote Similarity NPD3539 Phase 1
0.6727 Remote Similarity NPD2677 Approved
0.6723 Remote Similarity NPD2489 Approved
0.6723 Remote Similarity NPD27 Approved
0.672 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6718 Remote Similarity NPD8151 Discontinued
0.6709 Remote Similarity NPD6798 Discontinued
0.6707 Remote Similarity NPD4162 Approved
0.6705 Remote Similarity NPD6232 Discontinued
0.6705 Remote Similarity NPD6071 Discontinued
0.6703 Remote Similarity NPD7313 Approved
0.6703 Remote Similarity NPD7311 Approved
0.6703 Remote Similarity NPD7310 Approved
0.6703 Remote Similarity NPD7312 Approved
0.669 Remote Similarity NPD3022 Approved
0.669 Remote Similarity NPD3021 Approved
0.6688 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6688 Remote Similarity NPD3685 Discontinued
0.6688 Remote Similarity NPD5752 Clinical (unspecified phase)
0.6687 Remote Similarity NPD3657 Discovery
0.6686 Remote Similarity NPD5563 Clinical (unspecified phase)

  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