Structure

Physi-Chem Properties

Molecular Weight:  222.09
Volume:  223.61
LogP:  3.156
LogD:  1.957
LogS:  -2.845
# Rotatable Bonds:  0
TPSA:  66.76
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.659
Synthetic Accessibility Score:  3.625
Fsp3:  0.417
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.708
MDCK Permeability:  1.3969955034554005e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.005
30% Bioavailability (F30%):  0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.368
Plasma Protein Binding (PPB):  96.45348358154297%
Volume Distribution (VD):  0.639
Pgp-substrate:  2.9746451377868652%

ADMET: Metabolism

CYP1A2-inhibitor:  0.968
CYP1A2-substrate:  0.928
CYP2C19-inhibitor:  0.21
CYP2C19-substrate:  0.098
CYP2C9-inhibitor:  0.651
CYP2C9-substrate:  0.817
CYP2D6-inhibitor:  0.734
CYP2D6-substrate:  0.231
CYP3A4-inhibitor:  0.451
CYP3A4-substrate:  0.168

ADMET: Excretion

Clearance (CL):  10.577
Half-life (T1/2):  0.704

ADMET: Toxicity

hERG Blockers:  0.008
Human Hepatotoxicity (H-HT):  0.107
Drug-inuced Liver Injury (DILI):  0.781
AMES Toxicity:  0.12
Rat Oral Acute Toxicity:  0.059
Maximum Recommended Daily Dose:  0.573
Skin Sensitization:  0.193
Carcinogencity:  0.086
Eye Corrosion:  0.086
Eye Irritation:  0.959
Respiratory Toxicity:  0.363

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

  Natural Product: NPC88269

Natural Product ID:  NPC88269
Common Name*:   PPEPKULENIXILK-IYSWYEEDSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  PPEPKULENIXILK-IYSWYEEDSA-N
Standard InCHI:  InChI=1S/C12H14O4/c1-5-7(3)16-12(15)11-9(14)4-8(13)6(2)10(5)11/h4-5,7,13-14H,1-3H3/t5-,7-/m1/s1
SMILES:  C[C@H]1OC(=O)c2c([C@@H]1C)c(C)c(cc2O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3609765
PubChem CID:   NA
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives
        • [CHEMONTID:0000176] Benzoic acids and derivatives
          • [CHEMONTID:0001248] Hydroxybenzoic acid derivatives

*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
NPO19366 Penicillium citrinum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[15730261]
NPO19366 Penicillium citrinum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[15973055]
NPO19366 Penicillium citrinum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[18656987]
NPO19812 Pimelea simplex Species Thymelaeaceae Eukaryota n.a. n.a. n.a. PMID[21049973]
NPO19366 Penicillium citrinum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21053938]
NPO20842 Beauveria felina Species Cordycipitaceae Eukaryota n.a. n.a. n.a. PMID[21438588]
NPO19366 Penicillium citrinum Species Aspergillaceae Eukaryota n.a. Moroccan n.a. PMID[23713692]
NPO20842 Beauveria felina Species Cordycipitaceae Eukaryota n.a. n.a. n.a. PMID[23822585]
NPO20842 Beauveria felina Species Cordycipitaceae Eukaryota n.a. n.a. n.a. PMID[26295595]
NPO19366 Penicillium citrinum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[26295595]
NPO12352 Magnolia baillonii Species Magnoliaceae Eukaryota n.a. n.a. n.a. PMID[3437284]
NPO19366 Penicillium citrinum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[7766039]
NPO19551 Cocculus pendulus Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19812 Pimelea simplex Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19812 Pimelea simplex Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19551 Cocculus pendulus Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16902 Dendroctonus brevicomis Species Curculionidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11741 Glycosmis parviflora Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18651 Piper lolot Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20842 Beauveria felina Species Cordycipitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18223 Dictyostelium brefeldianum Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19146 Cosmos bipinnatus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19551 Cocculus pendulus Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19681 Hypoxis filiformis Species Hypoxidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14131 Phyllanthus maderaspatensis Species Phyllanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18898 Madhuca utilis Species Sapotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17984 Aplysia angasi Species Aplysiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19366 Penicillium citrinum Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10921 Cercospora ligustri Species Mycosphaerellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12352 Magnolia baillonii Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19611 Ipomoea tuberosa Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19812 Pimelea simplex Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13189 Carex folliculata Species Cyperaceae 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
NPT1845 Organism Vibrio alginolyticus Vibrio alginolyticus MIC = 8.0 ug.mL-1 PMID[483018]

☑ 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 NPC88269 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.9776 High Similarity NPC472601
0.9776 High Similarity NPC472600
0.9704 High Similarity NPC472604
0.9704 High Similarity NPC472603
0.9704 High Similarity NPC472605
0.9624 High Similarity NPC235115
0.9562 High Similarity NPC472610
0.9562 High Similarity NPC159721
0.9493 High Similarity NPC151607
0.9493 High Similarity NPC42540
0.9481 High Similarity NPC472602
0.9481 High Similarity NPC221104
0.9478 High Similarity NPC291454
0.9478 High Similarity NPC50455
0.9424 High Similarity NPC473692
0.942 High Similarity NPC471731
0.9416 High Similarity NPC53649
0.9412 High Similarity NPC275356
0.9407 High Similarity NPC70380
0.9407 High Similarity NPC245058
0.9398 High Similarity NPC153783
0.9357 High Similarity NPC473023
0.9348 High Similarity NPC82913
0.9348 High Similarity NPC471733
0.9343 High Similarity NPC155205
0.9338 High Similarity NPC212693
0.9338 High Similarity NPC94248
0.9338 High Similarity NPC191835
0.9333 High Similarity NPC158481
0.9333 High Similarity NPC156967
0.9281 High Similarity NPC469542
0.9275 High Similarity NPC470842
0.9275 High Similarity NPC37530
0.927 High Similarity NPC139634
0.927 High Similarity NPC32360
0.927 High Similarity NPC105456
0.927 High Similarity NPC268052
0.9265 High Similarity NPC194579
0.9248 High Similarity NPC219892
0.9248 High Similarity NPC189823
0.9209 High Similarity NPC322112
0.9203 High Similarity NPC99441
0.9197 High Similarity NPC33144
0.9197 High Similarity NPC478200
0.9191 High Similarity NPC472599
0.9185 High Similarity NPC175943
0.9155 High Similarity NPC471734
0.9143 High Similarity NPC478202
0.9137 High Similarity NPC67650
0.9137 High Similarity NPC478217
0.9137 High Similarity NPC158634
0.9137 High Similarity NPC1704
0.9137 High Similarity NPC313123
0.9124 High Similarity NPC135837
0.9124 High Similarity NPC71256
0.9124 High Similarity NPC261292
0.9124 High Similarity NPC301915
0.9118 High Similarity NPC142027
0.9118 High Similarity NPC27407
0.9104 High Similarity NPC214702
0.9104 High Similarity NPC470831
0.9085 High Similarity NPC260946
0.9085 High Similarity NPC471735
0.9071 High Similarity NPC469579
0.9065 High Similarity NPC165172
0.9065 High Similarity NPC64664
0.9065 High Similarity NPC158472
0.9044 High Similarity NPC475645
0.9037 High Similarity NPC476389
0.903 High Similarity NPC296158
0.9021 High Similarity NPC53362
0.9021 High Similarity NPC166583
0.9007 High Similarity NPC472006
0.9007 High Similarity NPC51106
0.9 High Similarity NPC478201
0.9 High Similarity NPC472035
0.9 High Similarity NPC244923
0.8993 High Similarity NPC52358
0.8993 High Similarity NPC92655
0.8993 High Similarity NPC247409
0.8986 High Similarity NPC474771
0.8986 High Similarity NPC474849
0.8986 High Similarity NPC65837
0.8986 High Similarity NPC149372
0.8986 High Similarity NPC178467
0.8978 High Similarity NPC182496
0.8978 High Similarity NPC180905
0.8936 High Similarity NPC474385
0.8929 High Similarity NPC168471
0.8921 High Similarity NPC472403
0.8921 High Similarity NPC475974
0.8912 High Similarity NPC472799
0.8905 High Similarity NPC474394
0.8897 High Similarity NPC77325
0.8897 High Similarity NPC270160
0.8897 High Similarity NPC4423
0.8897 High Similarity NPC237440
0.8889 High Similarity NPC476463
0.8881 High Similarity NPC83272
0.8865 High Similarity NPC149533
0.8865 High Similarity NPC90411
0.8865 High Similarity NPC475730
0.8857 High Similarity NPC474655
0.8844 High Similarity NPC167903
0.8841 High Similarity NPC278375
0.8841 High Similarity NPC290803
0.8841 High Similarity NPC470844
0.8836 High Similarity NPC179178
0.8836 High Similarity NPC119929
0.8836 High Similarity NPC150928
0.8828 High Similarity NPC221352
0.8819 High Similarity NPC107625
0.8819 High Similarity NPC163846
0.8819 High Similarity NPC267509
0.8819 High Similarity NPC225173
0.8811 High Similarity NPC478203
0.8811 High Similarity NPC126882
0.8811 High Similarity NPC210966
0.8811 High Similarity NPC210425
0.8811 High Similarity NPC86373
0.8811 High Similarity NPC280404
0.8811 High Similarity NPC277426
0.8803 High Similarity NPC250755
0.8797 High Similarity NPC201728
0.8797 High Similarity NPC262671
0.8786 High Similarity NPC177307
0.8786 High Similarity NPC9121
0.8786 High Similarity NPC126739
0.8786 High Similarity NPC197666
0.8784 High Similarity NPC192189
0.8784 High Similarity NPC470102
0.8776 High Similarity NPC215921
0.8776 High Similarity NPC70016
0.8767 High Similarity NPC233267
0.8767 High Similarity NPC291049
0.8759 High Similarity NPC125801
0.875 High Similarity NPC257558
0.875 High Similarity NPC472034
0.875 High Similarity NPC32470
0.875 High Similarity NPC134621
0.8732 High Similarity NPC220106
0.8723 High Similarity NPC471819
0.8716 High Similarity NPC271681
0.8716 High Similarity NPC273483
0.8716 High Similarity NPC87708
0.8707 High Similarity NPC158866
0.8699 High Similarity NPC37139
0.8699 High Similarity NPC153417
0.8699 High Similarity NPC240253
0.8699 High Similarity NPC105415
0.8699 High Similarity NPC471642
0.8699 High Similarity NPC240622
0.8699 High Similarity NPC471641
0.8696 High Similarity NPC48036
0.8696 High Similarity NPC37299
0.8696 High Similarity NPC180261
0.8696 High Similarity NPC470988
0.869 High Similarity NPC470570
0.869 High Similarity NPC51513
0.869 High Similarity NPC237208
0.869 High Similarity NPC202112
0.869 High Similarity NPC472033
0.8681 High Similarity NPC66404
0.8681 High Similarity NPC48762
0.8681 High Similarity NPC95123
0.8671 High Similarity NPC94076
0.8671 High Similarity NPC182255
0.8671 High Similarity NPC105648
0.8662 High Similarity NPC187690
0.8662 High Similarity NPC156872
0.8658 High Similarity NPC281477
0.8649 High Similarity NPC72958
0.8649 High Similarity NPC232645
0.8649 High Similarity NPC133856
0.8643 High Similarity NPC118919
0.8639 High Similarity NPC198927
0.8639 High Similarity NPC476684
0.8633 High Similarity NPC470984
0.863 High Similarity NPC14098
0.863 High Similarity NPC472036
0.863 High Similarity NPC8817
0.863 High Similarity NPC81835
0.863 High Similarity NPC210320
0.8627 High Similarity NPC473022
0.8623 High Similarity NPC27490
0.8621 High Similarity NPC75694
0.8621 High Similarity NPC34482
0.8621 High Similarity NPC312789
0.8621 High Similarity NPC29577
0.8613 High Similarity NPC17840
0.8613 High Similarity NPC247477
0.8613 High Similarity NPC62219
0.8611 High Similarity NPC354984
0.8611 High Similarity NPC471643
0.8611 High Similarity NPC310340
0.8611 High Similarity NPC84266
0.8611 High Similarity NPC471639
0.8603 High Similarity NPC41263
0.8601 High Similarity NPC130485
0.8601 High Similarity NPC275734

  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 NPC88269 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
0.913 High Similarity NPD970 Clinical (unspecified phase)
0.8621 High Similarity NPD2532 Approved
0.8621 High Similarity NPD2534 Approved
0.8621 High Similarity NPD2533 Approved
0.8533 High Similarity NPD7819 Suspended
0.8264 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8264 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8252 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.8207 Intermediate Similarity NPD1549 Phase 2
0.8205 Intermediate Similarity NPD6959 Discontinued
0.817 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8169 Intermediate Similarity NPD230 Phase 1
0.8129 Intermediate Similarity NPD7075 Discontinued
0.8125 Intermediate Similarity NPD1510 Phase 2
0.8117 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8099 Intermediate Similarity NPD1240 Approved
0.8052 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8039 Intermediate Similarity NPD7411 Suspended
0.8038 Intermediate Similarity NPD5710 Approved
0.8038 Intermediate Similarity NPD5711 Approved
0.8038 Intermediate Similarity NPD6232 Discontinued
0.8 Intermediate Similarity NPD7473 Discontinued
0.8 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7987 Intermediate Similarity NPD1934 Approved
0.7986 Intermediate Similarity NPD1607 Approved
0.7974 Intermediate Similarity NPD4380 Phase 2
0.7945 Intermediate Similarity NPD2935 Discontinued
0.7926 Intermediate Similarity NPD9545 Approved
0.7905 Intermediate Similarity NPD2800 Approved
0.7871 Intermediate Similarity NPD6801 Discontinued
0.7862 Intermediate Similarity NPD6651 Approved
0.7852 Intermediate Similarity NPD3750 Approved
0.7834 Intermediate Similarity NPD7768 Phase 2
0.7826 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7823 Intermediate Similarity NPD1551 Phase 2
0.7815 Intermediate Similarity NPD7390 Discontinued
0.7791 Intermediate Similarity NPD5844 Phase 1
0.7785 Intermediate Similarity NPD3749 Approved
0.7785 Intermediate Similarity NPD1243 Approved
0.7778 Intermediate Similarity NPD920 Approved
0.7778 Intermediate Similarity NPD9493 Approved
0.7733 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7733 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7724 Intermediate Similarity NPD943 Approved
0.7722 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7707 Intermediate Similarity NPD1465 Phase 2
0.7703 Intermediate Similarity NPD2796 Approved
0.7703 Intermediate Similarity NPD5406 Approved
0.7703 Intermediate Similarity NPD5405 Approved
0.7703 Intermediate Similarity NPD5404 Approved
0.7703 Intermediate Similarity NPD5408 Approved
0.7697 Intermediate Similarity NPD1511 Approved
0.7697 Intermediate Similarity NPD6799 Approved
0.7647 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7635 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7632 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7628 Intermediate Similarity NPD6599 Discontinued
0.7606 Intermediate Similarity NPD1164 Approved
0.7597 Intermediate Similarity NPD1512 Approved
0.7586 Intermediate Similarity NPD3764 Approved
0.7586 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7578 Intermediate Similarity NPD5494 Approved
0.7571 Intermediate Similarity NPD1201 Approved
0.7564 Intermediate Similarity NPD3226 Approved
0.7562 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.755 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7547 Intermediate Similarity NPD3817 Phase 2
0.7533 Intermediate Similarity NPD2346 Discontinued
0.7532 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7517 Intermediate Similarity NPD3748 Approved
0.7517 Intermediate Similarity NPD2799 Discontinued
0.7516 Intermediate Similarity NPD919 Approved
0.75 Intermediate Similarity NPD3882 Suspended
0.75 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6166 Phase 2
0.7484 Intermediate Similarity NPD2801 Approved
0.7483 Intermediate Similarity NPD1470 Approved
0.747 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7467 Intermediate Similarity NPD6099 Approved
0.7467 Intermediate Similarity NPD6100 Approved
0.7452 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.744 Intermediate Similarity NPD6559 Discontinued
0.7427 Intermediate Similarity NPD8150 Discontinued
0.7425 Intermediate Similarity NPD7074 Phase 3
0.7413 Intermediate Similarity NPD1283 Approved
0.7394 Intermediate Similarity NPD9269 Phase 2
0.7394 Intermediate Similarity NPD9717 Approved
0.7394 Intermediate Similarity NPD1608 Approved
0.7386 Intermediate Similarity NPD4628 Phase 3
0.7381 Intermediate Similarity NPD5953 Discontinued
0.7365 Intermediate Similarity NPD7054 Approved
0.7365 Intermediate Similarity NPD7286 Phase 2
0.7361 Intermediate Similarity NPD1203 Approved
0.7357 Intermediate Similarity NPD9268 Approved
0.7356 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7347 Intermediate Similarity NPD1699 Clinical (unspecified phase)
0.7324 Intermediate Similarity NPD422 Phase 1
0.7321 Intermediate Similarity NPD7472 Approved
0.7315 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7315 Intermediate Similarity NPD5124 Phase 1
0.7312 Intermediate Similarity NPD37 Approved
0.7308 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7305 Intermediate Similarity NPD3818 Discontinued
0.7301 Intermediate Similarity NPD6234 Discontinued
0.7294 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7284 Intermediate Similarity NPD4966 Approved
0.7284 Intermediate Similarity NPD4965 Approved
0.7284 Intermediate Similarity NPD4967 Phase 2
0.7278 Intermediate Similarity NPD6797 Phase 2
0.7273 Intermediate Similarity NPD7229 Phase 3
0.7266 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7235 Intermediate Similarity NPD7251 Discontinued
0.723 Intermediate Similarity NPD411 Approved
0.723 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD5402 Approved
0.7215 Intermediate Similarity NPD5403 Approved
0.7203 Intermediate Similarity NPD1281 Approved
0.7203 Intermediate Similarity NPD1610 Phase 2
0.72 Intermediate Similarity NPD447 Suspended
0.7197 Intermediate Similarity NPD5401 Approved
0.7197 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7193 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7193 Intermediate Similarity NPD7808 Phase 3
0.7185 Intermediate Similarity NPD9266 Approved
0.7185 Intermediate Similarity NPD74 Approved
0.7183 Intermediate Similarity NPD4626 Approved
0.7183 Intermediate Similarity NPD17 Approved
0.7176 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7161 Intermediate Similarity NPD7003 Approved
0.7151 Intermediate Similarity NPD8313 Approved
0.7151 Intermediate Similarity NPD8312 Approved
0.7143 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7133 Intermediate Similarity NPD4060 Phase 1
0.7114 Intermediate Similarity NPD2313 Discontinued
0.7113 Intermediate Similarity NPD5691 Approved
0.7111 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7111 Intermediate Similarity NPD9267 Approved
0.7111 Intermediate Similarity NPD9264 Approved
0.7111 Intermediate Similarity NPD9263 Approved
0.7108 Intermediate Similarity NPD1247 Approved
0.7108 Intermediate Similarity NPD7199 Phase 2
0.7101 Intermediate Similarity NPD7228 Approved
0.7095 Intermediate Similarity NPD4908 Phase 1
0.7095 Intermediate Similarity NPD6832 Phase 2
0.7086 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7078 Intermediate Similarity NPD2344 Approved
0.7067 Intermediate Similarity NPD6663 Approved
0.7067 Intermediate Similarity NPD520 Approved
0.7059 Intermediate Similarity NPD7033 Discontinued
0.7047 Intermediate Similarity NPD4625 Phase 3
0.7045 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7044 Intermediate Similarity NPD6273 Approved
0.7043 Intermediate Similarity NPD8151 Discontinued
0.7027 Intermediate Similarity NPD5736 Approved
0.7024 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.702 Intermediate Similarity NPD2979 Phase 3
0.7019 Intermediate Similarity NPD7458 Discontinued
0.7013 Intermediate Similarity NPD2438 Suspended
0.7012 Intermediate Similarity NPD4288 Approved
0.7012 Intermediate Similarity NPD5353 Approved
0.7011 Intermediate Similarity NPD8320 Phase 1
0.7011 Intermediate Similarity NPD8319 Approved
0.7007 Intermediate Similarity NPD2797 Approved
0.7006 Intermediate Similarity NPD6190 Approved
0.7 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD1296 Phase 2
0.7 Intermediate Similarity NPD3268 Approved
0.7 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.6993 Remote Similarity NPD4196 Clinical (unspecified phase)
0.6987 Remote Similarity NPD2654 Approved
0.6986 Remote Similarity NPD4749 Approved
0.6983 Remote Similarity NPD4363 Phase 3
0.6983 Remote Similarity NPD6535 Approved
0.6983 Remote Similarity NPD4360 Phase 2
0.6983 Remote Similarity NPD6534 Approved
0.6968 Remote Similarity NPD6002 Phase 3
0.6968 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6968 Remote Similarity NPD6005 Phase 3
0.6968 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6968 Remote Similarity NPD6004 Phase 3
0.6966 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6959 Remote Similarity NPD1019 Discontinued
0.6959 Remote Similarity NPD2798 Approved
0.6959 Remote Similarity NPD6917 Clinical (unspecified phase)
0.6957 Remote Similarity NPD7435 Discontinued
0.6943 Remote Similarity NPD8166 Discontinued
0.6918 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6908 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6908 Remote Similarity NPD1613 Approved
0.6903 Remote Similarity NPD4476 Approved
0.6903 Remote Similarity NPD4477 Approved
0.6901 Remote Similarity NPD3751 Discontinued
0.6901 Remote Similarity NPD7177 Discontinued
0.6899 Remote Similarity NPD2309 Approved
0.6885 Remote Similarity NPD6780 Approved
0.6885 Remote Similarity NPD7501 Clinical (unspecified phase)
0.6885 Remote Similarity NPD6776 Approved
0.6885 Remote Similarity NPD6777 Approved
0.6885 Remote Similarity NPD6781 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