Structure

Physi-Chem Properties

Molecular Weight:  476.39
Volume:  525.735
LogP:  5.015
LogD:  4.807
LogS:  -4.717
# Rotatable Bonds:  4
TPSA:  80.92
# H-Bond Aceptor:  4
# H-Bond Donor:  4
# Rings:  4
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.406
Synthetic Accessibility Score:  5.052
Fsp3:  0.933
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:  -4.813
MDCK Permeability:  3.810740599874407e-05
Pgp-inhibitor:  0.865
Pgp-substrate:  0.088
Human Intestinal Absorption (HIA):  0.012
20% Bioavailability (F20%):  0.976
30% Bioavailability (F30%):  0.925

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.07
Plasma Protein Binding (PPB):  90.48589324951172%
Volume Distribution (VD):  1.056
Pgp-substrate:  4.367894649505615%

ADMET: Metabolism

CYP1A2-inhibitor:  0.014
CYP1A2-substrate:  0.175
CYP2C19-inhibitor:  0.041
CYP2C19-substrate:  0.873
CYP2C9-inhibitor:  0.167
CYP2C9-substrate:  0.634
CYP2D6-inhibitor:  0.006
CYP2D6-substrate:  0.128
CYP3A4-inhibitor:  0.418
CYP3A4-substrate:  0.232

ADMET: Excretion

Clearance (CL):  5.059
Half-life (T1/2):  0.18

ADMET: Toxicity

hERG Blockers:  0.09
Human Hepatotoxicity (H-HT):  0.297
Drug-inuced Liver Injury (DILI):  0.012
AMES Toxicity:  0.002
Rat Oral Acute Toxicity:  0.216
Maximum Recommended Daily Dose:  0.184
Skin Sensitization:  0.647
Carcinogencity:  0.006
Eye Corrosion:  0.068
Eye Irritation:  0.143
Respiratory Toxicity:  0.895

Download Data

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

  Natural Product: NPC102253

Natural Product ID:  NPC102253
Common Name*:   20(R)-Protopanaxatriol
IUPAC Name:   (3S,5R,6S,8R,9R,10R,12R,13R,14R,17S)-17-[(2R)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,6,12-triol
Synonyms:  
Standard InCHIKey:  SHCBCKBYTHZQGZ-DLHMIPLTSA-N
Standard InCHI:  InChI=1S/C30H52O4/c1-18(2)10-9-13-30(8,34)19-11-15-28(6)24(19)20(31)16-22-27(5)14-12-23(33)26(3,4)25(27)21(32)17-29(22,28)7/h10,19-25,31-34H,9,11-17H2,1-8H3/t19-,20+,21-,22+,23-,24-,25-,27+,28+,29+,30+/m0/s1
SMILES:  CC(=CCC[C@]([C@H]1CC[C@@]2([C@@H]1[C@H](O)C[C@H]1[C@@]2(C)C[C@@H]([C@@H]2[C@]1(C)CC[C@@H](C2(C)C)O)O)C)(O)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3634637
PubChem CID:   9847853
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001553] Triterpenoids

*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
NPO210 Uvaria calamistrata Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[10075755]
NPO210 Uvaria calamistrata Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[11000019]
NPO11248 Tachigalia paniculata n.a. n.a. n.a. leaves n.a. n.a. PMID[12444671]
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]
NPO10540 Passiflora incarnata Species Passifloraceae Eukaryota n.a. n.a. n.a. PMID[2026709]
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]
NPO20712 Panax quinquefolius Species Araliaceae Eukaryota leaves and stems n.a. n.a. PMID[25442304]
NPO41756 Saccharomyces cerevisiae D20RG1 [UGTPg29, UGTPg45] Strain Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[25769286]
NPO29141 Panax ginseng Species Araliaceae Eukaryota stems-leaves n.a. n.a. PMID[26420067]
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]
NPO10540 Passiflora incarnata Species Passifloraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
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]
NPO10540 Passiflora incarnata Species Passifloraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20712 Panax quinquefolius Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29141 Panax ginseng 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]
NPO20712 Panax quinquefolius 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]
NPO5189 Glycine tomentella Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11488 Alstonia muelleriana Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12001 Saccharomyces pastori Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14354 Artemisia cina Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21854 Pterocladiella tenuis Species Gelidiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10540 Passiflora incarnata Species Passifloraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18805 Tripolium pannonicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO210 Uvaria calamistrata Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11642 Dacrydium cupressinum Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14255 Streptomyces flocculus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO12684 Trigonella grandiflora Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19635 Coreopsis nodosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13568 Hypoxylon rubiginosum Species Xylariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7998 Senecio paludaffinis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20712 Panax quinquefolius Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22666 Haematococcus lacustris Species Haematococcaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13166 Nicotiana undulata Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11248 Tachigalia paniculata n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO731 Panax schinseng 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
NPT116 Cell Line HL-60 Homo sapiens IC50 = 28680.0 nM PMID[507869]
NPT65 Cell Line HepG2 Homo sapiens IC50 = 58290.0 nM PMID[507869]

☑ 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 NPC102253 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 NPC236237
1.0 High Similarity NPC322313
0.9865 High Similarity NPC273410
0.9865 High Similarity NPC80530
0.973 High Similarity NPC244385
0.973 High Similarity NPC285761
0.973 High Similarity NPC167037
0.973 High Similarity NPC6978
0.973 High Similarity NPC138621
0.961 High Similarity NPC207013
0.9474 High Similarity NPC13554
0.9459 High Similarity NPC237460
0.9359 High Similarity NPC110778
0.9324 High Similarity NPC3403
0.925 High Similarity NPC201273
0.9231 High Similarity NPC296701
0.9231 High Similarity NPC30166
0.9231 High Similarity NPC218616
0.9211 High Similarity NPC85346
0.9211 High Similarity NPC301707
0.9211 High Similarity NPC302041
0.9211 High Similarity NPC65897
0.92 High Similarity NPC189883
0.9114 High Similarity NPC141941
0.9114 High Similarity NPC193870
0.9114 High Similarity NPC477818
0.9091 High Similarity NPC1319
0.9079 High Similarity NPC214570
0.9079 High Similarity NPC198968
0.9079 High Similarity NPC318495
0.9079 High Similarity NPC155986
0.9067 High Similarity NPC471723
0.9067 High Similarity NPC141071
0.9067 High Similarity NPC257347
0.9012 High Similarity NPC24277
0.9012 High Similarity NPC6605
0.9 High Similarity NPC124172
0.9 High Similarity NPC478102
0.9 High Similarity NPC475798
0.9 High Similarity NPC127606
0.8974 High Similarity NPC236112
0.8961 High Similarity NPC312328
0.8961 High Similarity NPC275910
0.8947 High Similarity NPC240604
0.8947 High Similarity NPC300324
0.8947 High Similarity NPC14112
0.8947 High Similarity NPC321016
0.8947 High Similarity NPC202642
0.8947 High Similarity NPC134330
0.8947 High Similarity NPC129165
0.8947 High Similarity NPC46160
0.8947 High Similarity NPC321381
0.8947 High Similarity NPC86305
0.8947 High Similarity NPC107059
0.8947 High Similarity NPC73875
0.8947 High Similarity NPC91573
0.8919 High Similarity NPC167706
0.8919 High Similarity NPC111234
0.8889 High Similarity NPC318390
0.8875 High Similarity NPC113978
0.8875 High Similarity NPC134481
0.8875 High Similarity NPC470558
0.8875 High Similarity NPC82623
0.8861 High Similarity NPC474531
0.8846 High Similarity NPC472463
0.8846 High Similarity NPC328714
0.8846 High Similarity NPC30986
0.8846 High Similarity NPC209430
0.8831 High Similarity NPC470758
0.8831 High Similarity NPC470711
0.8816 High Similarity NPC230301
0.8816 High Similarity NPC22105
0.8816 High Similarity NPC136188
0.8816 High Similarity NPC322353
0.8816 High Similarity NPC212879
0.8816 High Similarity NPC285893
0.8816 High Similarity NPC240235
0.8816 High Similarity NPC230704
0.8816 High Similarity NPC288035
0.8816 High Similarity NPC118508
0.8816 High Similarity NPC134847
0.8816 High Similarity NPC185536
0.8816 High Similarity NPC178383
0.8816 High Similarity NPC162742
0.8816 High Similarity NPC121744
0.8816 High Similarity NPC304309
0.8816 High Similarity NPC28657
0.8816 High Similarity NPC104387
0.8816 High Similarity NPC70982
0.8816 High Similarity NPC231256
0.88 High Similarity NPC474140
0.8795 High Similarity NPC67872
0.8784 High Similarity NPC45296
0.878 High Similarity NPC6391
0.878 High Similarity NPC139724
0.878 High Similarity NPC261266
0.8765 High Similarity NPC470077
0.8765 High Similarity NPC205845
0.8765 High Similarity NPC474493
0.8765 High Similarity NPC209802
0.875 High Similarity NPC248886
0.875 High Similarity NPC101462
0.875 High Similarity NPC470614
0.875 High Similarity NPC87489
0.875 High Similarity NPC470049
0.875 High Similarity NPC1272
0.875 High Similarity NPC49964
0.8734 High Similarity NPC209944
0.8734 High Similarity NPC164840
0.8734 High Similarity NPC241290
0.8734 High Similarity NPC78545
0.8734 High Similarity NPC71535
0.8718 High Similarity NPC186191
0.8718 High Similarity NPC87604
0.8718 High Similarity NPC205455
0.8718 High Similarity NPC473943
0.8718 High Similarity NPC472342
0.8718 High Similarity NPC42853
0.8718 High Similarity NPC477817
0.8718 High Similarity NPC477819
0.8718 High Similarity NPC31828
0.8718 High Similarity NPC474216
0.8718 High Similarity NPC300499
0.8718 High Similarity NPC477522
0.8701 High Similarity NPC78067
0.8701 High Similarity NPC470362
0.8701 High Similarity NPC470749
0.8701 High Similarity NPC93662
0.8701 High Similarity NPC113733
0.8701 High Similarity NPC278091
0.869 High Similarity NPC105495
0.869 High Similarity NPC109744
0.8684 High Similarity NPC145552
0.8684 High Similarity NPC196358
0.8684 High Similarity NPC192638
0.8684 High Similarity NPC308440
0.8684 High Similarity NPC62657
0.8684 High Similarity NPC25511
0.8684 High Similarity NPC100334
0.8684 High Similarity NPC472503
0.8684 High Similarity NPC5046
0.8684 High Similarity NPC49168
0.8684 High Similarity NPC254509
0.8675 High Similarity NPC474657
0.8675 High Similarity NPC470620
0.8675 High Similarity NPC186145
0.8642 High Similarity NPC85095
0.8642 High Similarity NPC216420
0.8642 High Similarity NPC474634
0.8642 High Similarity NPC232023
0.8642 High Similarity NPC211135
0.8625 High Similarity NPC264245
0.8625 High Similarity NPC47761
0.8625 High Similarity NPC470383
0.8625 High Similarity NPC6707
0.8625 High Similarity NPC70927
0.8608 High Similarity NPC49599
0.8608 High Similarity NPC28862
0.8608 High Similarity NPC84694
0.8608 High Similarity NPC49627
0.8608 High Similarity NPC81306
0.8608 High Similarity NPC109546
0.8608 High Similarity NPC291379
0.8608 High Similarity NPC143182
0.8608 High Similarity NPC47982
0.859 High Similarity NPC248830
0.859 High Similarity NPC119355
0.859 High Similarity NPC202540
0.859 High Similarity NPC34177
0.859 High Similarity NPC40394
0.859 High Similarity NPC90979
0.859 High Similarity NPC472805
0.859 High Similarity NPC257191
0.859 High Similarity NPC331618
0.859 High Similarity NPC138502
0.859 High Similarity NPC101475
0.859 High Similarity NPC212241
0.859 High Similarity NPC157996
0.859 High Similarity NPC34019
0.8588 High Similarity NPC473956
0.8588 High Similarity NPC475751
0.8571 High Similarity NPC133588
0.8571 High Similarity NPC474668
0.8571 High Similarity NPC291503
0.8571 High Similarity NPC470542
0.8571 High Similarity NPC103822
0.8571 High Similarity NPC319090
0.8571 High Similarity NPC193360
0.8571 High Similarity NPC200243
0.8571 High Similarity NPC328104
0.8571 High Similarity NPC475664
0.8554 High Similarity NPC474970
0.8554 High Similarity NPC299068
0.8554 High Similarity NPC125399
0.8554 High Similarity NPC94462
0.8554 High Similarity NPC71520
0.8554 High Similarity NPC269058
0.8553 High Similarity NPC182717
0.8553 High Similarity NPC195489
0.8553 High Similarity NPC201373

  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 NPC102253 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
1.0 High Similarity NPD7525 Registered
0.8816 High Similarity NPD7339 Approved
0.8816 High Similarity NPD6942 Approved
0.8462 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.8442 Intermediate Similarity NPD6926 Approved
0.8442 Intermediate Similarity NPD6924 Approved
0.8375 Intermediate Similarity NPD7645 Phase 2
0.8228 Intermediate Similarity NPD6933 Approved
0.8182 Intermediate Similarity NPD4243 Approved
0.8095 Intermediate Similarity NPD4786 Approved
0.8049 Intermediate Similarity NPD7509 Discontinued
0.8046 Intermediate Similarity NPD5328 Approved
0.7978 Intermediate Similarity NPD4202 Approved
0.7975 Intermediate Similarity NPD4784 Approved
0.7975 Intermediate Similarity NPD4785 Approved
0.7949 Intermediate Similarity NPD7150 Approved
0.7949 Intermediate Similarity NPD7151 Approved
0.7949 Intermediate Similarity NPD7152 Approved
0.7922 Intermediate Similarity NPD6922 Approved
0.7922 Intermediate Similarity NPD4267 Clinical (unspecified phase)
0.7922 Intermediate Similarity NPD6923 Approved
0.7907 Intermediate Similarity NPD3618 Phase 1
0.7882 Intermediate Similarity NPD7338 Clinical (unspecified phase)
0.7865 Intermediate Similarity NPD6079 Approved
0.7857 Intermediate Similarity NPD3667 Approved
0.7831 Intermediate Similarity NPD6930 Phase 2
0.7831 Intermediate Similarity NPD6931 Approved
0.7831 Intermediate Similarity NPD4748 Discontinued
0.7826 Intermediate Similarity NPD4755 Approved
0.7821 Intermediate Similarity NPD7143 Approved
0.7821 Intermediate Similarity NPD7144 Approved
0.7816 Intermediate Similarity NPD4751 Clinical (unspecified phase)
0.7791 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7765 Intermediate Similarity NPD6695 Phase 3
0.7711 Intermediate Similarity NPD6929 Approved
0.7683 Intermediate Similarity NPD6932 Approved
0.766 Intermediate Similarity NPD4696 Approved
0.766 Intermediate Similarity NPD5285 Approved
0.766 Intermediate Similarity NPD4700 Approved
0.766 Intermediate Similarity NPD5286 Approved
0.7654 Intermediate Similarity NPD5275 Approved
0.7654 Intermediate Similarity NPD4190 Phase 3
0.7582 Intermediate Similarity NPD6399 Phase 3
0.7579 Intermediate Similarity NPD5223 Approved
0.7553 Intermediate Similarity NPD7638 Approved
0.7527 Intermediate Similarity NPD4697 Phase 3
0.7527 Intermediate Similarity NPD5221 Approved
0.7527 Intermediate Similarity NPD5222 Approved
0.7527 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD5225 Approved
0.75 Intermediate Similarity NPD5211 Phase 2
0.75 Intermediate Similarity NPD4633 Approved
0.75 Intermediate Similarity NPD6683 Phase 2
0.75 Intermediate Similarity NPD4195 Approved
0.75 Intermediate Similarity NPD5226 Approved
0.75 Intermediate Similarity NPD5224 Approved
0.7474 Intermediate Similarity NPD7640 Approved
0.7474 Intermediate Similarity NPD7639 Approved
0.7473 Intermediate Similarity NPD7515 Phase 2
0.7473 Intermediate Similarity NPD8035 Phase 2
0.7473 Intermediate Similarity NPD8034 Phase 2
0.7471 Intermediate Similarity NPD3666 Approved
0.7471 Intermediate Similarity NPD3133 Approved
0.7471 Intermediate Similarity NPD3665 Phase 1
0.747 Intermediate Similarity NPD6925 Approved
0.747 Intermediate Similarity NPD5776 Phase 2
0.7449 Intermediate Similarity NPD6402 Approved
0.7449 Intermediate Similarity NPD5739 Approved
0.7449 Intermediate Similarity NPD6675 Approved
0.7449 Intermediate Similarity NPD7128 Approved
0.7447 Intermediate Similarity NPD5173 Approved
0.7444 Intermediate Similarity NPD4753 Phase 2
0.7423 Intermediate Similarity NPD5174 Approved
0.7423 Intermediate Similarity NPD5175 Approved
0.7423 Intermediate Similarity NPD4754 Approved
0.7416 Intermediate Similarity NPD7750 Discontinued
0.7416 Intermediate Similarity NPD7524 Approved
0.7412 Intermediate Similarity NPD7514 Phase 3
0.7386 Intermediate Similarity NPD6893 Approved
0.7381 Intermediate Similarity NPD7322 Clinical (unspecified phase)
0.7381 Intermediate Similarity NPD7145 Approved
0.7375 Intermediate Similarity NPD4787 Phase 1
0.7356 Intermediate Similarity NPD4788 Approved
0.7347 Intermediate Similarity NPD5141 Approved
0.73 Intermediate Similarity NPD6881 Approved
0.73 Intermediate Similarity NPD7320 Approved
0.73 Intermediate Similarity NPD6899 Approved
0.7273 Intermediate Similarity NPD4767 Approved
0.7273 Intermediate Similarity NPD4768 Approved
0.7273 Intermediate Similarity NPD3668 Phase 3
0.7262 Intermediate Similarity NPD6116 Phase 1
0.7241 Intermediate Similarity NPD4221 Approved
0.7241 Intermediate Similarity NPD4223 Phase 3
0.7228 Intermediate Similarity NPD6372 Approved
0.7228 Intermediate Similarity NPD6373 Approved
0.7209 Intermediate Similarity NPD7332 Phase 2
0.72 Intermediate Similarity NPD5701 Approved
0.72 Intermediate Similarity NPD5697 Approved
0.7191 Intermediate Similarity NPD5329 Approved
0.7157 Intermediate Similarity NPD7290 Approved
0.7157 Intermediate Similarity NPD6883 Approved
0.7157 Intermediate Similarity NPD7102 Approved
0.7143 Intermediate Similarity NPD6117 Approved
0.7129 Intermediate Similarity NPD6011 Approved
0.7129 Intermediate Similarity NPD4729 Approved
0.7129 Intermediate Similarity NPD5128 Approved
0.7129 Intermediate Similarity NPD4730 Approved
0.7128 Intermediate Similarity NPD7748 Approved
0.7126 Intermediate Similarity NPD6902 Approved
0.7126 Intermediate Similarity NPD6898 Phase 1
0.7111 Intermediate Similarity NPD5279 Phase 3
0.7111 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD7087 Discontinued
0.7087 Intermediate Similarity NPD8130 Phase 1
0.7087 Intermediate Similarity NPD6617 Approved
0.7087 Intermediate Similarity NPD6650 Approved
0.7087 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7087 Intermediate Similarity NPD6649 Approved
0.7087 Intermediate Similarity NPD6847 Approved
0.7087 Intermediate Similarity NPD6869 Approved
0.7083 Intermediate Similarity NPD6084 Phase 2
0.7083 Intermediate Similarity NPD6083 Phase 2
0.7083 Intermediate Similarity NPD7902 Approved
0.7079 Intermediate Similarity NPD4197 Approved
0.7073 Intermediate Similarity NPD4809 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD4808 Clinical (unspecified phase)
0.7065 Intermediate Similarity NPD6051 Approved
0.7059 Intermediate Similarity NPD6014 Approved
0.7059 Intermediate Similarity NPD6012 Approved
0.7059 Intermediate Similarity NPD6013 Approved
0.7053 Intermediate Similarity NPD5210 Approved
0.7053 Intermediate Similarity NPD4629 Approved
0.7024 Intermediate Similarity NPD8264 Approved
0.7019 Intermediate Similarity NPD8297 Approved
0.7019 Intermediate Similarity NPD6882 Approved
0.701 Intermediate Similarity NPD5290 Discontinued
0.699 Remote Similarity NPD5169 Approved
0.699 Remote Similarity NPD5134 Clinical (unspecified phase)
0.699 Remote Similarity NPD5249 Phase 3
0.699 Remote Similarity NPD5247 Approved
0.699 Remote Similarity NPD4634 Approved
0.699 Remote Similarity NPD5250 Approved
0.699 Remote Similarity NPD5135 Approved
0.699 Remote Similarity NPD5251 Approved
0.699 Remote Similarity NPD5248 Approved
0.6977 Remote Similarity NPD6114 Approved
0.6977 Remote Similarity NPD6115 Approved
0.6977 Remote Similarity NPD6697 Approved
0.6977 Remote Similarity NPD6118 Approved
0.6923 Remote Similarity NPD4688 Approved
0.6923 Remote Similarity NPD5127 Approved
0.6923 Remote Similarity NPD5215 Approved
0.6923 Remote Similarity NPD5217 Approved
0.6923 Remote Similarity NPD4138 Approved
0.6923 Remote Similarity NPD4689 Approved
0.6923 Remote Similarity NPD4693 Phase 3
0.6923 Remote Similarity NPD5216 Approved
0.6923 Remote Similarity NPD4690 Approved
0.6923 Remote Similarity NPD5205 Approved
0.6905 Remote Similarity NPD6113 Clinical (unspecified phase)
0.6852 Remote Similarity NPD7328 Approved
0.6852 Remote Similarity NPD7327 Approved
0.6829 Remote Similarity NPD3699 Clinical (unspecified phase)
0.6829 Remote Similarity NPD3700 Clinical (unspecified phase)
0.68 Remote Similarity NPD7632 Discontinued
0.6796 Remote Similarity NPD5168 Approved
0.6795 Remote Similarity NPD368 Approved
0.6792 Remote Similarity NPD4632 Approved
0.6789 Remote Similarity NPD7516 Approved
0.6774 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6774 Remote Similarity NPD4722 Approved
0.6774 Remote Similarity NPD6672 Approved
0.6774 Remote Similarity NPD5737 Approved
0.6774 Remote Similarity NPD4723 Approved
0.6771 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6771 Remote Similarity NPD7900 Approved
0.6739 Remote Similarity NPD4694 Approved
0.6739 Remote Similarity NPD6409 Approved
0.6739 Remote Similarity NPD5330 Approved
0.6739 Remote Similarity NPD7521 Approved
0.6739 Remote Similarity NPD6684 Approved
0.6739 Remote Similarity NPD5690 Phase 2
0.6739 Remote Similarity NPD5280 Approved
0.6739 Remote Similarity NPD7334 Approved
0.6739 Remote Similarity NPD7146 Approved
0.6737 Remote Similarity NPD5281 Approved
0.6737 Remote Similarity NPD5284 Approved
0.6729 Remote Similarity NPD5167 Approved
0.6727 Remote Similarity NPD8377 Approved
0.6727 Remote Similarity NPD8294 Approved
0.6707 Remote Similarity NPD5360 Phase 3
0.6707 Remote Similarity NPD5361 Clinical (unspecified phase)
0.6701 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6701 Remote Similarity NPD5695 Phase 3
0.6697 Remote Similarity NPD6335 Approved
0.6667 Remote Similarity NPD8380 Approved
0.6667 Remote Similarity NPD8335 Approved
0.6667 Remote Similarity NPD8379 Approved
0.6667 Remote Similarity NPD8296 Approved
0.6667 Remote Similarity NPD8033 Approved

  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