Structure

Physi-Chem Properties

Molecular Weight:  740.2
Volume:  695.033
LogP:  2.926
LogD:  2.125
LogS:  -4.685
# Rotatable Bonds:  12
TPSA:  264.5
# H-Bond Aceptor:  17
# H-Bond Donor:  8
# Rings:  6
# Heavy Atoms:  17

MedChem Properties

QED Drug-Likeness Score:  0.077
Synthetic Accessibility Score:  4.95
Fsp3:  0.333
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.513
MDCK Permeability:  1.9440214600763284e-05
Pgp-inhibitor:  0.026
Pgp-substrate:  0.997
Human Intestinal Absorption (HIA):  0.805
20% Bioavailability (F20%):  0.451
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.05
Plasma Protein Binding (PPB):  97.6274185180664%
Volume Distribution (VD):  0.59
Pgp-substrate:  8.017640113830566%

ADMET: Metabolism

CYP1A2-inhibitor:  0.073
CYP1A2-substrate:  0.102
CYP2C19-inhibitor:  0.054
CYP2C19-substrate:  0.053
CYP2C9-inhibitor:  0.395
CYP2C9-substrate:  0.336
CYP2D6-inhibitor:  0.301
CYP2D6-substrate:  0.165
CYP3A4-inhibitor:  0.646
CYP3A4-substrate:  0.104

ADMET: Excretion

Clearance (CL):  2.058
Half-life (T1/2):  0.752

ADMET: Toxicity

hERG Blockers:  0.302
Human Hepatotoxicity (H-HT):  0.168
Drug-inuced Liver Injury (DILI):  0.881
AMES Toxicity:  0.706
Rat Oral Acute Toxicity:  0.018
Maximum Recommended Daily Dose:  0.031
Skin Sensitization:  0.92
Carcinogencity:  0.233
Eye Corrosion:  0.003
Eye Irritation:  0.027
Respiratory Toxicity:  0.027

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

  Natural Product: NPC199172

Natural Product ID:  NPC199172
Common Name*:   Apigenin-7-O-[2''-O-(5'''-O-Feruloyl)-Beta-D-Apiofuranosyl]-Beta-D-Glucopyranoside
IUPAC Name:   [(3S,4R,5S)-5-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-2-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy-6-(hydroxymethyl)oxan-3-yl]oxy-3,4-dihydroxyoxolan-3-yl]methyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Synonyms:  
Standard InCHIKey:  CNNDXKQLSAQYHQ-DQPLZYKKSA-N
Standard InCHI:  InChI=1S/C36H36O17/c1-47-25-10-17(2-8-21(25)39)3-9-28(42)48-15-36(46)16-49-35(33(36)45)53-32-31(44)30(43)27(14-37)52-34(32)50-20-11-22(40)29-23(41)13-24(51-26(29)12-20)18-4-6-19(38)7-5-18/h2-13,27,30-35,37-40,43-46H,14-16H2,1H3/b9-3+/t27-,30-,31+,32-,33+,34-,35+,36-/m1/s1
SMILES:  COc1cc(ccc1O)/C=C/C(=O)OC[C@]1(CO[C@H]([C@@H]1O)O[C@@H]1[C@H]([C@@H]([C@@H](CO)O[C@H]1Oc1cc(c2c(=O)cc(c3ccc(cc3)O)oc2c1)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1077549
PubChem CID:   44478942
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0001111] Flavonoid glycosides
          • [CHEMONTID:0001583] Flavonoid O-glycosides
            • [CHEMONTID:0003533] Flavonoid-7-O-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
NPO26721 Apium graveolens Species Apiaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.jfca.2004.07.004]
NPO26721 Apium graveolens Species Apiaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.jfca.2005.08.001]
NPO26721 Apium graveolens Species Apiaceae Eukaryota n.a. n.a. 1996-Sep PMID[10352947]
NPO26721 Apium graveolens Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[18460139]
NPO26721 Apium graveolens Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[19778086]
NPO26721 Apium graveolens Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[21800857]
NPO26721 Apium graveolens Species Apiaceae Eukaryota Leaf Wax n.a. n.a. Database[FooDB]
NPO26721 Apium graveolens Species Apiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO26721 Apium graveolens Species Apiaceae Eukaryota Pt n.a. n.a. Database[FooDB]
NPO26721 Apium graveolens Species Apiaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO26721 Apium graveolens Species Apiaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO26721 Apium graveolens Species Apiaceae Eukaryota Seed Essent. Oil n.a. n.a. Database[FooDB]
NPO26721 Apium graveolens Species Apiaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO26721 Apium graveolens Species Apiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO26721 Apium graveolens Species Apiaceae Eukaryota Roots n.a. Database[FooDB]
NPO26721 Apium graveolens Species Apiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO26721 Apium graveolens Species Apiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO26721 Apium graveolens Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26721 Apium graveolens Species Apiaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO26721 Apium graveolens Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26721 Apium graveolens Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26721 Apium graveolens Species Apiaceae 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 > 20000.0 nM PMID[475255]

☑ 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 NPC199172 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 NPC35924
0.9704 High Similarity NPC469371
0.9645 High Similarity NPC471030
0.9641 High Similarity NPC472993
0.9591 High Similarity NPC470717
0.9591 High Similarity NPC21359
0.9591 High Similarity NPC470713
0.9591 High Similarity NPC460984
0.9591 High Similarity NPC470720
0.9591 High Similarity NPC25946
0.9535 High Similarity NPC104910
0.9535 High Similarity NPC295625
0.9535 High Similarity NPC474093
0.9535 High Similarity NPC473554
0.9535 High Similarity NPC470719
0.9532 High Similarity NPC470718
0.9532 High Similarity NPC241781
0.9532 High Similarity NPC156785
0.9532 High Similarity NPC162394
0.9524 High Similarity NPC175230
0.9524 High Similarity NPC172033
0.9524 High Similarity NPC88560
0.948 High Similarity NPC475179
0.9477 High Similarity NPC275977
0.9477 High Similarity NPC249560
0.9477 High Similarity NPC223860
0.9471 High Similarity NPC139571
0.9471 High Similarity NPC217520
0.9471 High Similarity NPC477895
0.9471 High Similarity NPC120952
0.9464 High Similarity NPC235575
0.9422 High Similarity NPC33083
0.9412 High Similarity NPC472991
0.9412 High Similarity NPC472992
0.9405 High Similarity NPC204937
0.9405 High Similarity NPC149011
0.9368 High Similarity NPC97817
0.9368 High Similarity NPC30011
0.9368 High Similarity NPC72554
0.9364 High Similarity NPC470416
0.9357 High Similarity NPC196127
0.9357 High Similarity NPC173837
0.9357 High Similarity NPC258044
0.9357 High Similarity NPC293626
0.9357 High Similarity NPC267680
0.9357 High Similarity NPC113836
0.9357 High Similarity NPC253521
0.9357 High Similarity NPC217387
0.9357 High Similarity NPC35167
0.9357 High Similarity NPC37668
0.9357 High Similarity NPC241196
0.9353 High Similarity NPC34267
0.9353 High Similarity NPC214621
0.9353 High Similarity NPC198199
0.9353 High Similarity NPC223426
0.9353 High Similarity NPC81042
0.9349 High Similarity NPC261254
0.9349 High Similarity NPC47140
0.9349 High Similarity NPC67134
0.9349 High Similarity NPC180918
0.9345 High Similarity NPC86008
0.9345 High Similarity NPC209296
0.9345 High Similarity NPC195257
0.9306 High Similarity NPC297503
0.9306 High Similarity NPC36138
0.9306 High Similarity NPC97119
0.9306 High Similarity NPC135831
0.9298 High Similarity NPC89127
0.9298 High Similarity NPC61904
0.9298 High Similarity NPC471669
0.9298 High Similarity NPC257714
0.9298 High Similarity NPC296018
0.9298 High Similarity NPC154741
0.9298 High Similarity NPC144097
0.9298 High Similarity NPC473862
0.929 High Similarity NPC212748
0.929 High Similarity NPC231194
0.929 High Similarity NPC51326
0.9286 High Similarity NPC116745
0.9286 High Similarity NPC229729
0.9281 High Similarity NPC22832
0.9281 High Similarity NPC311830
0.9253 High Similarity NPC470455
0.9253 High Similarity NPC470451
0.9244 High Similarity NPC476618
0.9244 High Similarity NPC476619
0.9244 High Similarity NPC476623
0.9244 High Similarity NPC89052
0.9244 High Similarity NPC476773
0.9244 High Similarity NPC476622
0.9244 High Similarity NPC476620
0.9244 High Similarity NPC472387
0.9244 High Similarity NPC251417
0.9244 High Similarity NPC476621
0.924 High Similarity NPC220173
0.924 High Similarity NPC476472
0.924 High Similarity NPC473327
0.924 High Similarity NPC19108
0.924 High Similarity NPC16194
0.924 High Similarity NPC169645
0.924 High Similarity NPC84482
0.924 High Similarity NPC294815
0.9235 High Similarity NPC153755
0.9235 High Similarity NPC245452
0.9235 High Similarity NPC254540
0.9235 High Similarity NPC172807
0.9235 High Similarity NPC211594
0.9231 High Similarity NPC197708
0.9231 High Similarity NPC658
0.9226 High Similarity NPC8856
0.9226 High Similarity NPC210073
0.9226 High Similarity NPC115674
0.9222 High Similarity NPC191306
0.9222 High Similarity NPC19709
0.9222 High Similarity NPC222936
0.9222 High Similarity NPC284960
0.9222 High Similarity NPC168822
0.9222 High Similarity NPC88023
0.9222 High Similarity NPC309025
0.9222 High Similarity NPC270335
0.9222 High Similarity NPC243930
0.9195 High Similarity NPC470447
0.9195 High Similarity NPC473072
0.9195 High Similarity NPC470445
0.9195 High Similarity NPC470449
0.9195 High Similarity NPC470446
0.9191 High Similarity NPC192539
0.9186 High Similarity NPC122467
0.9186 High Similarity NPC202908
0.9186 High Similarity NPC219043
0.9186 High Similarity NPC14187
0.9186 High Similarity NPC255799
0.9186 High Similarity NPC48984
0.9186 High Similarity NPC292019
0.9181 High Similarity NPC208668
0.9181 High Similarity NPC4390
0.9181 High Similarity NPC25724
0.9181 High Similarity NPC204693
0.9176 High Similarity NPC476365
0.9176 High Similarity NPC79056
0.9176 High Similarity NPC67105
0.9176 High Similarity NPC177731
0.9176 High Similarity NPC285197
0.9176 High Similarity NPC116864
0.9176 High Similarity NPC76047
0.9176 High Similarity NPC44328
0.9176 High Similarity NPC206123
0.9176 High Similarity NPC244776
0.9176 High Similarity NPC105095
0.9167 High Similarity NPC475366
0.9167 High Similarity NPC15358
0.9167 High Similarity NPC284277
0.9167 High Similarity NPC475497
0.9162 High Similarity NPC77660
0.9162 High Similarity NPC473043
0.9162 High Similarity NPC189142
0.9148 High Similarity NPC65489
0.9143 High Similarity NPC231254
0.9138 High Similarity NPC473071
0.9138 High Similarity NPC473073
0.9133 High Similarity NPC267549
0.9128 High Similarity NPC477848
0.9128 High Similarity NPC253685
0.9123 High Similarity NPC307518
0.9123 High Similarity NPC256760
0.9123 High Similarity NPC3583
0.9123 High Similarity NPC474522
0.9123 High Similarity NPC48773
0.9123 High Similarity NPC175107
0.9123 High Similarity NPC176740
0.9123 High Similarity NPC155877
0.9123 High Similarity NPC259152
0.9123 High Similarity NPC102851
0.9123 High Similarity NPC471725
0.9123 High Similarity NPC205076
0.9123 High Similarity NPC60735
0.9123 High Similarity NPC5786
0.9123 High Similarity NPC26230
0.9123 High Similarity NPC203259
0.9123 High Similarity NPC190003
0.9123 High Similarity NPC471748
0.9123 High Similarity NPC134532
0.9123 High Similarity NPC33054
0.9118 High Similarity NPC226294
0.9118 High Similarity NPC45638
0.9118 High Similarity NPC203050
0.9118 High Similarity NPC475942
0.9118 High Similarity NPC293629
0.9118 High Similarity NPC105283
0.9118 High Similarity NPC43587
0.9118 High Similarity NPC105025
0.9118 High Similarity NPC186807
0.9118 High Similarity NPC120099
0.9118 High Similarity NPC201292
0.9118 High Similarity NPC227508
0.9118 High Similarity NPC93337
0.9118 High Similarity NPC469931
0.9118 High Similarity NPC219904
0.9118 High Similarity NPC225434
0.9118 High Similarity NPC223747

  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 NPC199172 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
0.9405 High Similarity NPD7472 Approved
0.9345 High Similarity NPD7054 Approved
0.924 High Similarity NPD7808 Phase 3
0.9181 High Similarity NPD7251 Discontinued
0.9176 High Similarity NPD7074 Phase 3
0.9172 High Similarity NPD3818 Discontinued
0.9123 High Similarity NPD6797 Phase 2
0.9017 High Similarity NPD4338 Clinical (unspecified phase)
0.883 High Similarity NPD6168 Clinical (unspecified phase)
0.883 High Similarity NPD6167 Clinical (unspecified phase)
0.883 High Similarity NPD6166 Phase 2
0.881 High Similarity NPD4381 Clinical (unspecified phase)
0.8678 High Similarity NPD7804 Clinical (unspecified phase)
0.8639 High Similarity NPD4868 Clinical (unspecified phase)
0.858 High Similarity NPD7993 Clinical (unspecified phase)
0.8571 High Similarity NPD1934 Approved
0.8531 High Similarity NPD6559 Discontinued
0.8471 Intermediate Similarity NPD3817 Phase 2
0.8421 Intermediate Similarity NPD3882 Suspended
0.8412 Intermediate Similarity NPD2801 Approved
0.8412 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8324 Intermediate Similarity NPD7685 Pre-registration
0.8274 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.8266 Intermediate Similarity NPD7075 Discontinued
0.8235 Intermediate Similarity NPD4380 Phase 2
0.8232 Intermediate Similarity NPD8312 Approved
0.8232 Intermediate Similarity NPD8313 Approved
0.8216 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8204 Intermediate Similarity NPD1511 Approved
0.8202 Intermediate Similarity NPD7228 Approved
0.8156 Intermediate Similarity NPD5844 Phase 1
0.8142 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.8125 Intermediate Similarity NPD7199 Phase 2
0.8118 Intermediate Similarity NPD1653 Approved
0.8108 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.8107 Intermediate Similarity NPD1512 Approved
0.8092 Intermediate Similarity NPD7819 Suspended
0.8092 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8081 Intermediate Similarity NPD7411 Suspended
0.8068 Intermediate Similarity NPD5494 Approved
0.8046 Intermediate Similarity NPD5402 Approved
0.8046 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8045 Intermediate Similarity NPD7473 Discontinued
0.8035 Intermediate Similarity NPD6801 Discontinued
0.7989 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7978 Intermediate Similarity NPD6232 Discontinued
0.7959 Intermediate Similarity NPD8151 Discontinued
0.7953 Intermediate Similarity NPD5403 Approved
0.7941 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7933 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.791 Intermediate Similarity NPD6234 Discontinued
0.7886 Intermediate Similarity NPD8455 Phase 2
0.7886 Intermediate Similarity NPD1465 Phase 2
0.7882 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7882 Intermediate Similarity NPD6799 Approved
0.7853 Intermediate Similarity NPD3749 Approved
0.7836 Intermediate Similarity NPD5401 Approved
0.7829 Intermediate Similarity NPD37 Approved
0.7826 Intermediate Similarity NPD7240 Approved
0.7821 Intermediate Similarity NPD6959 Discontinued
0.7802 Intermediate Similarity NPD3751 Discontinued
0.7798 Intermediate Similarity NPD1549 Phase 2
0.7797 Intermediate Similarity NPD4966 Approved
0.7797 Intermediate Similarity NPD4965 Approved
0.7797 Intermediate Similarity NPD4967 Phase 2
0.7797 Intermediate Similarity NPD7768 Phase 2
0.7738 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7738 Intermediate Similarity NPD7266 Discontinued
0.7738 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7733 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7709 Intermediate Similarity NPD919 Approved
0.7704 Intermediate Similarity NPD7435 Discontinued
0.77 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.77 Intermediate Similarity NPD7783 Phase 2
0.768 Intermediate Similarity NPD3787 Discontinued
0.7679 Intermediate Similarity NPD2796 Approved
0.7619 Intermediate Similarity NPD1510 Phase 2
0.7614 Intermediate Similarity NPD6599 Discontinued
0.7602 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7588 Intermediate Similarity NPD7584 Approved
0.7577 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7576 Intermediate Similarity NPD7871 Phase 2
0.7576 Intermediate Similarity NPD7870 Phase 2
0.7562 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7562 Intermediate Similarity NPD7874 Approved
0.7558 Intermediate Similarity NPD6190 Approved
0.7551 Intermediate Similarity NPD6777 Approved
0.7551 Intermediate Similarity NPD6776 Approved
0.7551 Intermediate Similarity NPD6780 Approved
0.7551 Intermediate Similarity NPD6778 Approved
0.7551 Intermediate Similarity NPD6779 Approved
0.7551 Intermediate Similarity NPD6781 Approved
0.7551 Intermediate Similarity NPD6782 Approved
0.7545 Intermediate Similarity NPD1933 Approved
0.7541 Intermediate Similarity NPD3926 Phase 2
0.7526 Intermediate Similarity NPD8434 Phase 2
0.7525 Intermediate Similarity NPD7680 Approved
0.7525 Intermediate Similarity NPD7697 Approved
0.7525 Intermediate Similarity NPD7696 Phase 3
0.7525 Intermediate Similarity NPD7698 Approved
0.75 Intermediate Similarity NPD3750 Approved
0.7485 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7463 Intermediate Similarity NPD7701 Phase 2
0.7442 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.744 Intermediate Similarity NPD230 Phase 1
0.7435 Intermediate Similarity NPD8150 Discontinued
0.7432 Intermediate Similarity NPD1247 Approved
0.7411 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.74 Intermediate Similarity NPD8319 Approved
0.74 Intermediate Similarity NPD8320 Phase 1
0.7399 Intermediate Similarity NPD4628 Phase 3
0.7387 Intermediate Similarity NPD6823 Phase 2
0.7381 Intermediate Similarity NPD1240 Approved
0.7381 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7381 Intermediate Similarity NPD1613 Approved
0.7376 Intermediate Similarity NPD7585 Approved
0.7368 Intermediate Similarity NPD1551 Phase 2
0.7365 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.736 Intermediate Similarity NPD7699 Phase 2
0.736 Intermediate Similarity NPD7458 Discontinued
0.736 Intermediate Similarity NPD7700 Phase 2
0.7353 Intermediate Similarity NPD7801 Approved
0.7345 Intermediate Similarity NPD920 Approved
0.7337 Intermediate Similarity NPD447 Suspended
0.733 Intermediate Similarity NPD2533 Approved
0.733 Intermediate Similarity NPD2534 Approved
0.733 Intermediate Similarity NPD2532 Approved
0.733 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7327 Intermediate Similarity NPD7583 Approved
0.7296 Intermediate Similarity NPD6535 Approved
0.7296 Intermediate Similarity NPD6534 Approved
0.7294 Intermediate Similarity NPD1607 Approved
0.7286 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD943 Approved
0.7267 Intermediate Similarity NPD2935 Discontinued
0.7243 Intermediate Similarity NPD8127 Discontinued
0.7241 Intermediate Similarity NPD1243 Approved
0.7232 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7216 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7209 Intermediate Similarity NPD3748 Approved
0.7209 Intermediate Similarity NPD7033 Discontinued
0.7202 Intermediate Similarity NPD3027 Phase 3
0.7167 Intermediate Similarity NPD3226 Approved
0.7163 Intermediate Similarity NPD7930 Approved
0.7143 Intermediate Similarity NPD6832 Phase 2
0.7143 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD7549 Discontinued
0.7128 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.712 Intermediate Similarity NPD5953 Discontinued
0.7114 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD7286 Phase 2
0.7102 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7072 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7065 Intermediate Similarity NPD5353 Approved
0.7062 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7056 Intermediate Similarity NPD5619 Clinical (unspecified phase)
0.7047 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7045 Intermediate Similarity NPD6674 Discontinued
0.7045 Intermediate Similarity NPD2800 Approved
0.7029 Intermediate Similarity NPD2344 Approved
0.7021 Intermediate Similarity NPD7229 Phase 3
0.7005 Intermediate Similarity NPD4287 Approved
0.6995 Remote Similarity NPD7039 Approved
0.6995 Remote Similarity NPD7038 Approved
0.6985 Remote Similarity NPD6213 Phase 3
0.6985 Remote Similarity NPD6212 Phase 3
0.6985 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6983 Remote Similarity NPD7390 Discontinued
0.6971 Remote Similarity NPD6099 Approved
0.6971 Remote Similarity NPD6100 Approved
0.6964 Remote Similarity NPD1203 Approved
0.6961 Remote Similarity NPD5005 Approved
0.6961 Remote Similarity NPD5006 Approved
0.6959 Remote Similarity NPD6798 Discontinued
0.6959 Remote Similarity NPD2313 Discontinued
0.6959 Remote Similarity NPD8059 Phase 3
0.6959 Remote Similarity NPD8058 Clinical (unspecified phase)
0.6957 Remote Similarity NPD6844 Discontinued
0.6954 Remote Similarity NPD7097 Phase 1
0.6949 Remote Similarity NPD1652 Phase 2
0.6941 Remote Similarity NPD4908 Phase 1
0.6936 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6936 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6936 Remote Similarity NPD5124 Phase 1
0.6932 Remote Similarity NPD2346 Discontinued
0.6931 Remote Similarity NPD5710 Approved
0.6931 Remote Similarity NPD5711 Approved
0.6919 Remote Similarity NPD6233 Phase 2
0.6914 Remote Similarity NPD2799 Discontinued
0.6914 Remote Similarity NPD651 Clinical (unspecified phase)
0.691 Remote Similarity NPD8166 Discontinued
0.6902 Remote Similarity NPD6385 Approved
0.6902 Remote Similarity NPD6386 Approved
0.6897 Remote Similarity NPD8285 Discontinued
0.6895 Remote Similarity NPD5242 Approved
0.6882 Remote Similarity NPD9494 Approved
0.6875 Remote Similarity NPD7799 Discontinued
0.6872 Remote Similarity NPD2309 Approved
0.6866 Remote Similarity NPD4360 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