Structure

Physi-Chem Properties

Molecular Weight:  436.21
Volume:  443.754
LogP:  2.233
LogD:  2.84
LogS:  -3.822
# Rotatable Bonds:  12
TPSA:  106.84
# H-Bond Aceptor:  8
# H-Bond Donor:  3
# Rings:  2
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.466
Synthetic Accessibility Score:  3.709
Fsp3:  0.478
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.691
MDCK Permeability:  1.7835745893535204e-05
Pgp-inhibitor:  0.16
Pgp-substrate:  0.225
Human Intestinal Absorption (HIA):  0.014
20% Bioavailability (F20%):  0.043
30% Bioavailability (F30%):  0.11

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.068
Plasma Protein Binding (PPB):  93.51065063476562%
Volume Distribution (VD):  0.528
Pgp-substrate:  6.580844402313232%

ADMET: Metabolism

CYP1A2-inhibitor:  0.022
CYP1A2-substrate:  0.764
CYP2C19-inhibitor:  0.031
CYP2C19-substrate:  0.881
CYP2C9-inhibitor:  0.064
CYP2C9-substrate:  0.574
CYP2D6-inhibitor:  0.075
CYP2D6-substrate:  0.878
CYP3A4-inhibitor:  0.527
CYP3A4-substrate:  0.907

ADMET: Excretion

Clearance (CL):  13.271
Half-life (T1/2):  0.826

ADMET: Toxicity

hERG Blockers:  0.051
Human Hepatotoxicity (H-HT):  0.232
Drug-inuced Liver Injury (DILI):  0.035
AMES Toxicity:  0.167
Rat Oral Acute Toxicity:  0.045
Maximum Recommended Daily Dose:  0.272
Skin Sensitization:  0.834
Carcinogencity:  0.046
Eye Corrosion:  0.003
Eye Irritation:  0.024
Respiratory Toxicity:  0.14

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

  Natural Product: NPC470096

Natural Product ID:  NPC470096
Common Name*:   (-)-Threo-4,9,4',9'-Tetrahydroxy-3,5,7,3'-Tetramethoxy-8-O-8'-Neolignan
IUPAC Name:   4-[2-[1-hydroxy-3-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy-1-methoxybutyl]-2,6-dimethoxyphenol
Synonyms:  
Standard InCHIKey:  IXDWWAKFBJRMEW-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C23H32O8/c1-6-18(23(30-5)15-11-20(28-3)22(26)21(12-15)29-4)31-16(13-24)9-14-7-8-17(25)19(10-14)27-2/h7-8,10-12,16,18,23-26H,6,9,13H2,1-5H3
SMILES:  OCC(OC(C(c1cc(OC)c(c(c1)OC)O)OC)CC)Cc1ccc(c(c1)OC)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1761709
PubChem CID:   54582333
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000134] Phenols
        • [CHEMONTID:0000190] Methoxyphenols

*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
NPO29118 Euonymus alatus Species Celastraceae Eukaryota leaves and twigs n.a. n.a. PMID[21435874]
NPO29118 Euonymus alatus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29118 Euonymus alatus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29118 Euonymus alatus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29118 Euonymus alatus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29118 Euonymus alatus Species Celastraceae 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
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 41900.0 nM PMID[554297]

☑ 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 NPC470096 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 NPC470095
0.9762 High Similarity NPC184447
0.9762 High Similarity NPC7903
0.9762 High Similarity NPC35932
0.9762 High Similarity NPC160991
0.9762 High Similarity NPC16208
0.9683 High Similarity NPC472597
0.9683 High Similarity NPC469613
0.9683 High Similarity NPC30043
0.9683 High Similarity NPC469625
0.968 High Similarity NPC170844
0.968 High Similarity NPC476968
0.9609 High Similarity NPC170694
0.9609 High Similarity NPC310854
0.9606 High Similarity NPC253105
0.9606 High Similarity NPC201587
0.9606 High Similarity NPC470752
0.9603 High Similarity NPC469614
0.9603 High Similarity NPC469612
0.9603 High Similarity NPC472338
0.96 High Similarity NPC206615
0.96 High Similarity NPC470213
0.96 High Similarity NPC98631
0.96 High Similarity NPC186843
0.9528 High Similarity NPC309787
0.9528 High Similarity NPC474017
0.9524 High Similarity NPC226788
0.9524 High Similarity NPC285339
0.9524 High Similarity NPC218856
0.9524 High Similarity NPC202582
0.9524 High Similarity NPC222004
0.9524 High Similarity NPC3439
0.9524 High Similarity NPC273295
0.9524 High Similarity NPC210623
0.9524 High Similarity NPC190629
0.9524 High Similarity NPC470258
0.9457 High Similarity NPC244983
0.9457 High Similarity NPC326095
0.9457 High Similarity NPC287745
0.9394 High Similarity NPC266197
0.9394 High Similarity NPC291101
0.9385 High Similarity NPC472337
0.938 High Similarity NPC475840
0.938 High Similarity NPC158331
0.937 High Similarity NPC212015
0.9365 High Similarity NPC147821
0.9365 High Similarity NPC118787
0.9365 High Similarity NPC183181
0.9365 High Similarity NPC210355
0.9365 High Similarity NPC163332
0.9365 High Similarity NPC111247
0.9365 High Similarity NPC474119
0.9365 High Similarity NPC41706
0.9365 High Similarity NPC319625
0.9365 High Similarity NPC292056
0.936 High Similarity NPC203133
0.936 High Similarity NPC233410
0.936 High Similarity NPC208950
0.936 High Similarity NPC298757
0.936 High Similarity NPC193544
0.936 High Similarity NPC472093
0.936 High Similarity NPC116907
0.936 High Similarity NPC251855
0.936 High Similarity NPC17943
0.936 High Similarity NPC221077
0.936 High Similarity NPC117214
0.936 High Similarity NPC475169
0.936 High Similarity NPC57490
0.9355 High Similarity NPC220598
0.9355 High Similarity NPC165375
0.9318 High Similarity NPC22517
0.9313 High Similarity NPC306441
0.9313 High Similarity NPC471719
0.9313 High Similarity NPC16435
0.9313 High Similarity NPC472336
0.9313 High Similarity NPC472334
0.9302 High Similarity NPC204215
0.9302 High Similarity NPC175067
0.9291 High Similarity NPC252307
0.9291 High Similarity NPC245826
0.9291 High Similarity NPC474178
0.9286 High Similarity NPC18924
0.9286 High Similarity NPC58607
0.9286 High Similarity NPC78974
0.9286 High Similarity NPC214406
0.9286 High Similarity NPC223136
0.9286 High Similarity NPC178284
0.9286 High Similarity NPC28730
0.9286 High Similarity NPC103823
0.9286 High Similarity NPC191037
0.9286 High Similarity NPC44748
0.9274 High Similarity NPC71579
0.9274 High Similarity NPC262253
0.9274 High Similarity NPC473411
0.9254 High Similarity NPC469559
0.9248 High Similarity NPC267291
0.9237 High Similarity NPC234333
0.9237 High Similarity NPC165155
0.9237 High Similarity NPC99572
0.9237 High Similarity NPC94750
0.9237 High Similarity NPC24490
0.9237 High Similarity NPC47398
0.9237 High Similarity NPC121812
0.9237 High Similarity NPC61946
0.9237 High Similarity NPC34103
0.9237 High Similarity NPC470356
0.9237 High Similarity NPC126409
0.9237 High Similarity NPC112246
0.9237 High Similarity NPC256262
0.9237 High Similarity NPC474206
0.9237 High Similarity NPC141765
0.9237 High Similarity NPC112939
0.9237 High Similarity NPC260898
0.9231 High Similarity NPC168059
0.9231 High Similarity NPC229442
0.9219 High Similarity NPC86030
0.9219 High Similarity NPC58164
0.9219 High Similarity NPC10225
0.9219 High Similarity NPC5851
0.9213 High Similarity NPC124452
0.9213 High Similarity NPC118533
0.9213 High Similarity NPC282000
0.9213 High Similarity NPC159968
0.9213 High Similarity NPC165045
0.9213 High Similarity NPC242032
0.9213 High Similarity NPC293054
0.9213 High Similarity NPC236791
0.9213 High Similarity NPC470699
0.9213 High Similarity NPC324112
0.9213 High Similarity NPC127587
0.9213 High Similarity NPC169474
0.9213 High Similarity NPC246620
0.9213 High Similarity NPC74817
0.9213 High Similarity NPC82679
0.9206 High Similarity NPC60885
0.9206 High Similarity NPC234400
0.9206 High Similarity NPC194519
0.9206 High Similarity NPC299584
0.9206 High Similarity NPC265483
0.9206 High Similarity NPC82483
0.92 High Similarity NPC471693
0.92 High Similarity NPC282496
0.92 High Similarity NPC197757
0.92 High Similarity NPC136319
0.92 High Similarity NPC228922
0.92 High Similarity NPC233526
0.9194 High Similarity NPC470804
0.9194 High Similarity NPC49341
0.9167 High Similarity NPC474639
0.9167 High Similarity NPC227503
0.9167 High Similarity NPC230734
0.9167 High Similarity NPC302701
0.9167 High Similarity NPC269091
0.916 High Similarity NPC309744
0.916 High Similarity NPC107478
0.9147 High Similarity NPC187998
0.9147 High Similarity NPC77040
0.9147 High Similarity NPC153739
0.9147 High Similarity NPC42300
0.9147 High Similarity NPC311680
0.9147 High Similarity NPC51840
0.9147 High Similarity NPC64201
0.9147 High Similarity NPC299221
0.9147 High Similarity NPC92164
0.9147 High Similarity NPC174495
0.9147 High Similarity NPC257582
0.9147 High Similarity NPC145305
0.9147 High Similarity NPC242807
0.9147 High Similarity NPC234488
0.9147 High Similarity NPC241522
0.9141 High Similarity NPC72529
0.9134 High Similarity NPC76451
0.9134 High Similarity NPC181361
0.9127 High Similarity NPC228972
0.9127 High Similarity NPC94276
0.9127 High Similarity NPC293701
0.9127 High Similarity NPC122792
0.9127 High Similarity NPC48990
0.9127 High Similarity NPC114901
0.9127 High Similarity NPC109822
0.912 High Similarity NPC41562
0.9118 High Similarity NPC470097
0.9118 High Similarity NPC114119
0.9118 High Similarity NPC471415
0.9113 High Similarity NPC166759
0.9111 High Similarity NPC472714
0.9111 High Similarity NPC193722
0.9111 High Similarity NPC5262
0.9111 High Similarity NPC189115
0.9111 High Similarity NPC278469
0.9098 High Similarity NPC107551
0.9098 High Similarity NPC326797
0.9098 High Similarity NPC474282
0.9098 High Similarity NPC211549
0.9098 High Similarity NPC102904
0.9098 High Similarity NPC176051
0.9098 High Similarity NPC474390
0.9098 High Similarity NPC103976
0.9091 High Similarity NPC164787
0.9091 High Similarity NPC151224

  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 NPC470096 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
0.968 High Similarity NPD3027 Phase 3
0.9008 High Similarity NPD1612 Clinical (unspecified phase)
0.9008 High Similarity NPD1613 Approved
0.8702 High Similarity NPD1529 Clinical (unspecified phase)
0.8626 High Similarity NPD1530 Clinical (unspecified phase)
0.8462 Intermediate Similarity NPD2983 Phase 2
0.8462 Intermediate Similarity NPD2982 Phase 2
0.8385 Intermediate Similarity NPD2981 Phase 2
0.8346 Intermediate Similarity NPD3018 Phase 2
0.8306 Intermediate Similarity NPD228 Approved
0.8085 Intermediate Similarity NPD7266 Discontinued
0.8054 Intermediate Similarity NPD1934 Approved
0.8045 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.8031 Intermediate Similarity NPD5283 Phase 1
0.8027 Intermediate Similarity NPD1653 Approved
0.8015 Intermediate Similarity NPD4908 Phase 1
0.8 Intermediate Similarity NPD1548 Phase 1
0.7908 Intermediate Similarity NPD6234 Discontinued
0.7899 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7895 Intermediate Similarity NPD1610 Phase 2
0.7885 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7885 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7885 Intermediate Similarity NPD6166 Phase 2
0.7881 Intermediate Similarity NPD2801 Approved
0.7881 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7848 Intermediate Similarity NPD7054 Approved
0.7815 Intermediate Similarity NPD37 Approved
0.7812 Intermediate Similarity NPD7843 Approved
0.7799 Intermediate Similarity NPD7074 Phase 3
0.7799 Intermediate Similarity NPD7472 Approved
0.7786 Intermediate Similarity NPD3620 Phase 2
0.7786 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7786 Intermediate Similarity NPD1558 Phase 1
0.7785 Intermediate Similarity NPD7228 Approved
0.7778 Intermediate Similarity NPD3882 Suspended
0.7778 Intermediate Similarity NPD4966 Approved
0.7778 Intermediate Similarity NPD4967 Phase 2
0.7778 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD4965 Approved
0.7769 Intermediate Similarity NPD7157 Approved
0.7761 Intermediate Similarity NPD3705 Approved
0.774 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7727 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7724 Intermediate Similarity NPD3060 Approved
0.7717 Intermediate Similarity NPD3021 Approved
0.7717 Intermediate Similarity NPD3022 Approved
0.7712 Intermediate Similarity NPD6374 Clinical (unspecified phase)
0.7708 Intermediate Similarity NPD3540 Phase 1
0.7682 Intermediate Similarity NPD4678 Approved
0.7682 Intermediate Similarity NPD4675 Approved
0.7681 Intermediate Similarity NPD2861 Phase 2
0.7673 Intermediate Similarity NPD3818 Discontinued
0.7669 Intermediate Similarity NPD1357 Approved
0.7643 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7643 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7639 Intermediate Similarity NPD3539 Phase 1
0.7638 Intermediate Similarity NPD2684 Approved
0.7635 Intermediate Similarity NPD1511 Approved
0.763 Intermediate Similarity NPD1091 Approved
0.7619 Intermediate Similarity NPD6190 Approved
0.7616 Intermediate Similarity NPD6055 Clinical (unspecified phase)
0.7609 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7603 Intermediate Similarity NPD4236 Phase 3
0.7603 Intermediate Similarity NPD4237 Approved
0.7597 Intermediate Similarity NPD3817 Phase 2
0.7593 Intermediate Similarity NPD7251 Discontinued
0.7571 Intermediate Similarity NPD4625 Phase 3
0.7566 Intermediate Similarity NPD4380 Phase 2
0.7546 Intermediate Similarity NPD7808 Phase 3
0.7533 Intermediate Similarity NPD1512 Approved
0.7531 Intermediate Similarity NPD6797 Phase 2
0.7519 Intermediate Similarity NPD5536 Phase 2
0.7518 Intermediate Similarity NPD4749 Approved
0.7517 Intermediate Similarity NPD4357 Discontinued
0.75 Intermediate Similarity NPD4536 Approved
0.75 Intermediate Similarity NPD4538 Approved
0.75 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD1242 Phase 1
0.75 Intermediate Similarity NPD4005 Discontinued
0.7483 Intermediate Similarity NPD230 Phase 1
0.7483 Intermediate Similarity NPD6674 Discontinued
0.7483 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7468 Intermediate Similarity NPD7199 Phase 2
0.745 Intermediate Similarity NPD7124 Phase 2
0.7439 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7422 Intermediate Similarity NPD290 Approved
0.7419 Intermediate Similarity NPD2978 Approved
0.7419 Intermediate Similarity NPD2977 Approved
0.7413 Intermediate Similarity NPD4060 Phase 1
0.7383 Intermediate Similarity NPD2219 Phase 1
0.7376 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7372 Intermediate Similarity NPD422 Phase 1
0.7368 Intermediate Similarity NPD6671 Approved
0.7365 Intermediate Similarity NPD1652 Phase 2
0.7365 Intermediate Similarity NPD5177 Phase 3
0.7365 Intermediate Similarity NPD4162 Approved
0.7351 Intermediate Similarity NPD4123 Phase 3
0.7347 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7344 Intermediate Similarity NPD968 Approved
0.7343 Intermediate Similarity NPD2674 Phase 3
0.7338 Intermediate Similarity NPD8651 Approved
0.7329 Intermediate Similarity NPD5960 Phase 3
0.7329 Intermediate Similarity NPD5588 Approved
0.7317 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7312 Intermediate Similarity NPD6232 Discontinued
0.7302 Intermediate Similarity NPD291 Approved
0.7301 Intermediate Similarity NPD5844 Phase 1
0.7292 Intermediate Similarity NPD2238 Phase 2
0.7285 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7284 Intermediate Similarity NPD7473 Discontinued
0.7278 Intermediate Similarity NPD7075 Discontinued
0.7278 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD7240 Approved
0.7267 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD2677 Approved
0.7266 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.726 Intermediate Similarity NPD6111 Discontinued
0.7255 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD5735 Approved
0.7237 Intermediate Similarity NPD7447 Phase 1
0.7234 Intermediate Similarity NPD6584 Phase 3
0.7226 Intermediate Similarity NPD5846 Approved
0.7226 Intermediate Similarity NPD6516 Phase 2
0.7222 Intermediate Similarity NPD6233 Phase 2
0.7219 Intermediate Similarity NPD5058 Phase 3
0.7208 Intermediate Similarity NPD3687 Approved
0.7208 Intermediate Similarity NPD3686 Approved
0.7203 Intermediate Similarity NPD7095 Approved
0.72 Intermediate Similarity NPD4628 Phase 3
0.7197 Intermediate Similarity NPD5772 Approved
0.7197 Intermediate Similarity NPD1465 Phase 2
0.7197 Intermediate Similarity NPD5773 Approved
0.7197 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7194 Intermediate Similarity NPD2235 Phase 2
0.7194 Intermediate Similarity NPD2231 Phase 2
0.7192 Intermediate Similarity NPD5314 Approved
0.7192 Intermediate Similarity NPD6653 Approved
0.719 Intermediate Similarity NPD1940 Clinical (unspecified phase)
0.7183 Intermediate Similarity NPD9494 Approved
0.7172 Intermediate Similarity NPD3059 Approved
0.7172 Intermediate Similarity NPD3061 Approved
0.7172 Intermediate Similarity NPD3062 Approved
0.7171 Intermediate Similarity NPD7212 Phase 2
0.7171 Intermediate Similarity NPD7213 Phase 3
0.7169 Intermediate Similarity NPD7685 Pre-registration
0.7165 Intermediate Similarity NPD940 Approved
0.7165 Intermediate Similarity NPD846 Approved
0.7153 Intermediate Similarity NPD3145 Approved
0.7153 Intermediate Similarity NPD3144 Approved
0.7152 Intermediate Similarity NPD5241 Discontinued
0.7152 Intermediate Similarity NPD5402 Approved
0.7124 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7123 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7123 Intermediate Similarity NPD5124 Phase 1
0.7123 Intermediate Similarity NPD6355 Discontinued
0.7114 Intermediate Similarity NPD5762 Approved
0.7114 Intermediate Similarity NPD5763 Approved
0.7114 Intermediate Similarity NPD1375 Discontinued
0.7114 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7114 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7103 Intermediate Similarity NPD1726 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD9384 Approved
0.7101 Intermediate Similarity NPD9381 Approved
0.7097 Intermediate Similarity NPD9296 Approved
0.7097 Intermediate Similarity NPD2934 Approved
0.7097 Intermediate Similarity NPD2933 Approved
0.7095 Intermediate Similarity NPD1510 Phase 2
0.7091 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7089 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD6331 Phase 2
0.7086 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD4110 Phase 3
0.7086 Intermediate Similarity NPD3892 Phase 2
0.7081 Intermediate Similarity NPD5494 Approved
0.7078 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7078 Intermediate Similarity NPD7527 Clinical (unspecified phase)
0.7078 Intermediate Similarity NPD7526 Approved
0.7078 Intermediate Similarity NPD52 Approved
0.7075 Intermediate Similarity NPD2568 Approved
0.7067 Intermediate Similarity NPD1549 Phase 2
0.7066 Intermediate Similarity NPD6559 Discontinued
0.7063 Intermediate Similarity NPD4055 Discovery
0.7059 Intermediate Similarity NPD6799 Approved
0.7059 Intermediate Similarity NPD1774 Approved
0.7055 Intermediate Similarity NPD1240 Approved
0.7047 Intermediate Similarity NPD6100 Approved
0.7047 Intermediate Similarity NPD6099 Approved
0.7045 Intermediate Similarity NPD4750 Phase 3
0.7044 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7042 Intermediate Similarity NPD3094 Phase 2
0.7041 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD8053 Approved
0.7041 Intermediate Similarity NPD8054 Approved
0.704 Intermediate Similarity NPD2859 Approved
0.704 Intermediate Similarity NPD2860 Approved
0.7034 Intermediate Similarity NPD6798 Discontinued
0.7034 Intermediate Similarity NPD5718 Phase 2
0.7034 Intermediate Similarity NPD5109 Approved
0.7034 Intermediate Similarity NPD5110 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