Structure

Physi-Chem Properties

Molecular Weight:  748.29
Volume:  728.561
LogP:  2.819
LogD:  1.409
LogS:  -4.216
# Rotatable Bonds:  16
TPSA:  228.47
# H-Bond Aceptor:  16
# H-Bond Donor:  2
# Rings:  4
# Heavy Atoms:  16

MedChem Properties

QED Drug-Likeness Score:  0.135
Synthetic Accessibility Score:  5.934
Fsp3:  0.649
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.426
MDCK Permeability:  0.00015164374781306833
Pgp-inhibitor:  0.859
Pgp-substrate:  0.903
Human Intestinal Absorption (HIA):  0.954
20% Bioavailability (F20%):  0.981
30% Bioavailability (F30%):  0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.051
Plasma Protein Binding (PPB):  54.243682861328125%
Volume Distribution (VD):  1.086
Pgp-substrate:  27.649572372436523%

ADMET: Metabolism

CYP1A2-inhibitor:  0.003
CYP1A2-substrate:  0.027
CYP2C19-inhibitor:  0.016
CYP2C19-substrate:  0.119
CYP2C9-inhibitor:  0.024
CYP2C9-substrate:  0.003
CYP2D6-inhibitor:  0.013
CYP2D6-substrate:  0.029
CYP3A4-inhibitor:  0.714
CYP3A4-substrate:  0.464

ADMET: Excretion

Clearance (CL):  3.191
Half-life (T1/2):  0.449

ADMET: Toxicity

hERG Blockers:  0.017
Human Hepatotoxicity (H-HT):  0.795
Drug-inuced Liver Injury (DILI):  0.925
AMES Toxicity:  0.058
Rat Oral Acute Toxicity:  0.648
Maximum Recommended Daily Dose:  0.932
Skin Sensitization:  0.138
Carcinogencity:  0.033
Eye Corrosion:  0.003
Eye Irritation:  0.021
Respiratory Toxicity:  0.93

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

  Natural Product: NPC471632

Natural Product ID:  NPC471632
Common Name*:   Prieurianin
IUPAC Name:   methyl (2S,3R,4R,5S)-4-[(1S,3aS,5R,6R,7R,7aR)-6-formyloxy-1-(furan-3-yl)-3a-hydroxy-7-[(2R,3R)-2-hydroxy-3-methylpentanoyl]oxy-7a-methyl-4-methylidene-3-oxo-2,5,6,7-tetrahydro-1H-inden-5-yl]-5-acetyloxy-2-(acetyloxymethyl)-2,4-dimethyl-7-oxooxepane-3-carboxylate
Synonyms:  
Standard InCHIKey:  KEIRAXFVAMECMP-VFOAQDGDSA-N
Standard InCHI:  InChI=1S/C37H48O16/c1-10-18(2)28(43)32(44)52-31-29(50-17-38)27(19(3)37(46)24(41)13-23(36(31,37)8)22-11-12-48-15-22)35(7)25(51-21(5)40)14-26(42)53-34(6,16-49-20(4)39)30(35)33(45)47-9/h11-12,15,17-18,23,25,27-31,43,46H,3,10,13-14,16H2,1-2,4-9H3/t18-,23+,25+,27-,28-,29-,30+,31+,34-,35-,36-,37-/m1/s1
SMILES:  CCC(C)C(C(=O)OC1C(C(C(=C)C2(C1(C(CC2=O)C3=COC=C3)C)O)C4(C(CC(=O)OC(C4C(=O)OC)(C)COC(=O)C)OC(=O)C)C)OC=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3085392
PubChem CID:   76313482
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0000265] Carboxylic acids and derivatives
        • [CHEMONTID:0002967] Hexacarboxylic acids and 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
NPO9173 Munronia henryi Species Meliaceae Eukaryota whole plants Wenshan, Yunnan Province, China 2012-Nov PMID[25798528]
NPO9173 Munronia henryi Species Meliaceae 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
NPT168 Cell Line P388 Mus musculus ED50 = 4.4 ug ml-1 PMID[494770]
NPT116 Cell Line HL-60 Homo sapiens IC50 = 4800.0 nM PMID[494774]
NPT659 Cell Line SMMC-7721 Homo sapiens IC50 = 730.0 nM PMID[494774]
NPT81 Cell Line A549 Homo sapiens IC50 = 1000.0 nM PMID[494774]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 2200.0 nM PMID[494774]
NPT660 Cell Line SW480 Homo sapiens IC50 = 1200.0 nM PMID[494774]
NPT1579 Organism Heliothis virescens Heliothis virescens Activity = 60.0 % PMID[494771]
NPT1579 Organism Heliothis virescens Heliothis virescens Activity = 30.0 % PMID[494771]
NPT1579 Organism Heliothis virescens Heliothis virescens Activity = 0.0 % PMID[494771]
NPT3062 Organism Spodoptera eridania Spodoptera eridania Activity = 30.0 % PMID[494771]
NPT3062 Organism Spodoptera eridania Spodoptera eridania Activity = 0.0 % PMID[494771]
NPT3773 Organism Epilachna varivestis Epilachna varivestis Activity = 60.0 % PMID[494771]
NPT3773 Organism Epilachna varivestis Epilachna varivestis Activity = 30.0 % PMID[494771]
NPT3773 Organism Epilachna varivestis Epilachna varivestis Activity = 0.0 % PMID[494771]
NPT3915 Organism Helicoverpa armigera Helicoverpa armigera GI = 60.0 % PMID[494772]
NPT3915 Organism Helicoverpa armigera Helicoverpa armigera Inhibition = 57.7 % PMID[494772]
NPT3915 Organism Helicoverpa armigera Helicoverpa armigera Activity = 21.6 % PMID[494772]
NPT3915 Organism Helicoverpa armigera Helicoverpa armigera Activity = 22.1 % PMID[494772]
NPT3915 Organism Helicoverpa armigera Helicoverpa armigera Ratio = 3.79 n.a. PMID[494772]
NPT3915 Organism Helicoverpa armigera Helicoverpa armigera Ratio = 3.74 n.a. PMID[494772]
NPT3915 Organism Helicoverpa armigera Helicoverpa armigera Ratio = 0.82 n.a. PMID[494772]
NPT3915 Organism Helicoverpa armigera Helicoverpa armigera Ratio = 0.83 n.a. PMID[494772]
NPT3915 Organism Helicoverpa armigera Helicoverpa armigera Activity = 19.8 % PMID[494772]
NPT3915 Organism Helicoverpa armigera Helicoverpa armigera Activity = 20.0 % PMID[494772]
NPT3915 Organism Helicoverpa armigera Helicoverpa armigera Ratio = 1.63 n.a. PMID[494772]
NPT3915 Organism Helicoverpa armigera Helicoverpa armigera Ratio = 2.04 n.a. PMID[494772]
NPT3915 Organism Helicoverpa armigera Helicoverpa armigera Ratio = 0.32 n.a. PMID[494772]
NPT3915 Organism Helicoverpa armigera Helicoverpa armigera Ratio = 0.41 n.a. PMID[494772]
NPT3915 Organism Helicoverpa armigera Helicoverpa armigera EC50 = 92.2 ppm PMID[494772]
NPT3915 Organism Helicoverpa armigera Helicoverpa armigera DI50 = 91.4 ppm PMID[494772]
NPT3915 Organism Helicoverpa armigera Helicoverpa armigera EC95 = 169.2 ppm PMID[494772]
NPT3915 Organism Helicoverpa armigera Helicoverpa armigera EC50 = 18.8 ppm PMID[494772]
NPT72 Individual Protein Solute carrier organic anion transporter family member 1B3 Homo sapiens IC50 = 3388.44 nM PMID[494773]
NPT72 Individual Protein Solute carrier organic anion transporter family member 1B3 Homo sapiens Ki = 2630.0 nM PMID[494773]
NPT73 Individual Protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Inhibition = 22.79 % PMID[494773]
NPT73 Individual Protein Solute carrier organic anion transporter family member 1B1 Homo sapiens IC50 = 2344.23 nM PMID[494773]
NPT73 Individual Protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Ki = 1280.0 nM PMID[494773]
NPT72 Individual Protein Solute carrier organic anion transporter family member 1B3 Homo sapiens Inhibition = 25.49 % PMID[494773]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 75.9 % PMID[494774]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 68.1 % PMID[494774]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 45.7 % PMID[494774]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 41.6 % PMID[494774]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 70.5 % PMID[494774]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 39.3 % PMID[494774]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 35.6 % PMID[494774]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 11.7 % PMID[494774]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 3.5 % PMID[494774]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus IC50 = 44.4 ug.mL-1 PMID[494774]

☑ 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 NPC471632 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
0.9329 High Similarity NPC472659
0.9268 High Similarity NPC472765
0.9268 High Similarity NPC472766
0.9207 High Similarity NPC472764
0.9193 High Similarity NPC472779
0.9146 High Similarity NPC149945
0.9091 High Similarity NPC476224
0.9091 High Similarity NPC472775
0.9091 High Similarity NPC472774
0.9085 High Similarity NPC259943
0.908 High Similarity NPC472767
0.9053 High Similarity NPC478177
0.9048 High Similarity NPC471437
0.9042 High Similarity NPC285227
0.9024 High Similarity NPC472669
0.9018 High Similarity NPC470789
0.9012 High Similarity NPC105395
0.9012 High Similarity NPC247563
0.9012 High Similarity NPC242068
0.8982 High Similarity NPC472650
0.8963 High Similarity NPC471166
0.8963 High Similarity NPC471167
0.8935 High Similarity NPC94763
0.8909 High Similarity NPC472773
0.8848 High Similarity NPC472771
0.8848 High Similarity NPC329938
0.8848 High Similarity NPC5741
0.8848 High Similarity NPC472668
0.8848 High Similarity NPC6326
0.8834 High Similarity NPC204663
0.8824 High Similarity NPC236004
0.881 High Similarity NPC472673
0.8802 High Similarity NPC470875
0.8795 High Similarity NPC471168
0.8788 High Similarity NPC477402
0.878 High Similarity NPC195131
0.8772 High Similarity NPC469633
0.8765 High Similarity NPC469848
0.875 High Similarity NPC476853
0.8743 High Similarity NPC470940
0.8743 High Similarity NPC469849
0.8743 High Similarity NPC276551
0.8728 High Similarity NPC470938
0.8727 High Similarity NPC475226
0.8713 High Similarity NPC469576
0.8698 High Similarity NPC471397
0.8698 High Similarity NPC160651
0.8698 High Similarity NPC472652
0.869 High Similarity NPC478178
0.8683 High Similarity NPC477405
0.8683 High Similarity NPC663
0.8683 High Similarity NPC469338
0.8683 High Similarity NPC292389
0.8683 High Similarity NPC224394
0.8667 High Similarity NPC197137
0.8667 High Similarity NPC167142
0.8667 High Similarity NPC475066
0.8667 High Similarity NPC45101
0.8667 High Similarity NPC472772
0.8667 High Similarity NPC173544
0.8647 High Similarity NPC470995
0.8639 High Similarity NPC476850
0.8639 High Similarity NPC478179
0.8639 High Similarity NPC173516
0.8639 High Similarity NPC472282
0.8639 High Similarity NPC476861
0.8639 High Similarity NPC472651
0.8631 High Similarity NPC476856
0.8631 High Similarity NPC476858
0.8631 High Similarity NPC476857
0.8623 High Similarity NPC200782
0.8623 High Similarity NPC82851
0.8623 High Similarity NPC470792
0.8623 High Similarity NPC69028
0.8614 High Similarity NPC472671
0.8614 High Similarity NPC477403
0.8614 High Similarity NPC475967
0.8606 High Similarity NPC469485
0.8606 High Similarity NPC471169
0.8606 High Similarity NPC175964
0.8596 High Similarity NPC159232
0.8588 High Similarity NPC327922
0.858 High Similarity NPC23387
0.858 High Similarity NPC125182
0.858 High Similarity NPC69647
0.858 High Similarity NPC472670
0.858 High Similarity NPC307781
0.858 High Similarity NPC214600
0.8571 High Similarity NPC165218
0.8554 High Similarity NPC36655
0.8554 High Similarity NPC261597
0.8554 High Similarity NPC470118
0.8545 High Similarity NPC471175
0.8545 High Similarity NPC92979
0.8545 High Similarity NPC264943
0.8537 High Similarity NPC84063
0.8528 High Similarity NPC156189
0.8521 High Similarity NPC123088
0.8521 High Similarity NPC271657
0.8521 High Similarity NPC476860
0.8512 High Similarity NPC263432
0.8512 High Similarity NPC197596
0.8512 High Similarity NPC193798
0.8503 High Similarity NPC474932
0.8485 Intermediate Similarity NPC253201
0.8485 Intermediate Similarity NPC302054
0.848 Intermediate Similarity NPC271235
0.8471 Intermediate Similarity NPC121995
0.8471 Intermediate Similarity NPC472141
0.8466 Intermediate Similarity NPC470790
0.8466 Intermediate Similarity NPC472654
0.8466 Intermediate Similarity NPC470791
0.8457 Intermediate Similarity NPC255414
0.8452 Intermediate Similarity NPC25255
0.8452 Intermediate Similarity NPC472653
0.8452 Intermediate Similarity NPC191828
0.8443 Intermediate Similarity NPC470119
0.8443 Intermediate Similarity NPC214495
0.8443 Intermediate Similarity NPC249021
0.8443 Intermediate Similarity NPC472776
0.8443 Intermediate Similarity NPC472778
0.8443 Intermediate Similarity NPC472777
0.8434 Intermediate Similarity NPC214541
0.8434 Intermediate Similarity NPC44675
0.843 Intermediate Similarity NPC82602
0.8424 Intermediate Similarity NPC33938
0.8424 Intermediate Similarity NPC268905
0.8424 Intermediate Similarity NPC182427
0.8424 Intermediate Similarity NPC472672
0.8424 Intermediate Similarity NPC29695
0.8412 Intermediate Similarity NPC261184
0.8402 Intermediate Similarity NPC18347
0.8402 Intermediate Similarity NPC149896
0.8402 Intermediate Similarity NPC18986
0.8393 Intermediate Similarity NPC237155
0.8382 Intermediate Similarity NPC160818
0.8382 Intermediate Similarity NPC169299
0.8371 Intermediate Similarity NPC186746
0.8364 Intermediate Similarity NPC116717
0.8363 Intermediate Similarity NPC97574
0.8363 Intermediate Similarity NPC93172
0.8353 Intermediate Similarity NPC302369
0.8353 Intermediate Similarity NPC234660
0.8353 Intermediate Similarity NPC472139
0.8353 Intermediate Similarity NPC88841
0.8353 Intermediate Similarity NPC288602
0.8353 Intermediate Similarity NPC39986
0.8353 Intermediate Similarity NPC51568
0.8353 Intermediate Similarity NPC134254
0.8333 Intermediate Similarity NPC469847
0.8333 Intermediate Similarity NPC187149
0.8333 Intermediate Similarity NPC5676
0.8333 Intermediate Similarity NPC472283
0.8333 Intermediate Similarity NPC299038
0.8323 Intermediate Similarity NPC296807
0.8323 Intermediate Similarity NPC155939
0.8323 Intermediate Similarity NPC469336
0.8323 Intermediate Similarity NPC141538
0.8323 Intermediate Similarity NPC476262
0.8314 Intermediate Similarity NPC270312
0.8314 Intermediate Similarity NPC100333
0.8313 Intermediate Similarity NPC470996
0.8313 Intermediate Similarity NPC75906
0.8304 Intermediate Similarity NPC470182
0.8303 Intermediate Similarity NPC470997
0.8294 Intermediate Similarity NPC68848
0.8294 Intermediate Similarity NPC5079
0.8294 Intermediate Similarity NPC188649
0.8294 Intermediate Similarity NPC470939
0.8276 Intermediate Similarity NPC475641
0.8276 Intermediate Similarity NPC475237
0.8266 Intermediate Similarity NPC242334
0.8263 Intermediate Similarity NPC282445
0.8263 Intermediate Similarity NPC178932
0.8263 Intermediate Similarity NPC98206
0.8263 Intermediate Similarity NPC34421
0.8263 Intermediate Similarity NPC237259
0.8256 Intermediate Similarity NPC475779
0.8253 Intermediate Similarity NPC272590
0.8253 Intermediate Similarity NPC18135
0.8246 Intermediate Similarity NPC283209
0.8246 Intermediate Similarity NPC476197
0.8246 Intermediate Similarity NPC285567
0.8246 Intermediate Similarity NPC469846
0.8246 Intermediate Similarity NPC198047
0.8242 Intermediate Similarity NPC470998
0.8242 Intermediate Similarity NPC234494
0.8239 Intermediate Similarity NPC262386
0.8235 Intermediate Similarity NPC287559
0.8235 Intermediate Similarity NPC335761
0.8225 Intermediate Similarity NPC88007
0.8225 Intermediate Similarity NPC194499
0.8225 Intermediate Similarity NPC195954
0.8218 Intermediate Similarity NPC118086
0.8214 Intermediate Similarity NPC281258
0.821 Intermediate Similarity NPC243577
0.8204 Intermediate Similarity NPC308205
0.8204 Intermediate Similarity NPC322546
0.8204 Intermediate Similarity NPC469503
0.8204 Intermediate Similarity NPC476201

  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 NPC471632 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
0.8523 High Similarity NPD8434 Phase 2
0.8434 Intermediate Similarity NPD5761 Phase 2
0.8434 Intermediate Similarity NPD5760 Phase 2
0.7833 Intermediate Similarity NPD6764 Approved
0.7833 Intermediate Similarity NPD6765 Approved
0.7714 Intermediate Similarity NPD5537 Clinical (unspecified phase)
0.7663 Intermediate Similarity NPD6784 Approved
0.7663 Intermediate Similarity NPD6785 Approved
0.7473 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.734 Intermediate Similarity NPD8404 Phase 2
0.7228 Intermediate Similarity NPD7799 Discontinued
0.7098 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7093 Intermediate Similarity NPD4628 Phase 3
0.7074 Intermediate Similarity NPD6559 Discontinued
0.7072 Intermediate Similarity NPD7075 Discontinued
0.7022 Intermediate Similarity NPD6599 Discontinued
0.7 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.6984 Remote Similarity NPD7685 Pre-registration
0.6957 Remote Similarity NPD8127 Discontinued
0.6957 Remote Similarity NPD1247 Approved
0.6944 Remote Similarity NPD6801 Discontinued
0.6914 Remote Similarity NPD7236 Approved
0.6911 Remote Similarity NPD8313 Approved
0.6911 Remote Similarity NPD8312 Approved
0.6906 Remote Similarity NPD7819 Suspended
0.6875 Remote Similarity NPD8407 Phase 2
0.6868 Remote Similarity NPD5402 Approved
0.6862 Remote Similarity NPD3818 Discontinued
0.6848 Remote Similarity NPD919 Approved
0.6842 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6831 Remote Similarity NPD3882 Suspended
0.6825 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6821 Remote Similarity NPD5763 Approved
0.6821 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6821 Remote Similarity NPD6005 Phase 3
0.6821 Remote Similarity NPD5762 Approved
0.6821 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6821 Remote Similarity NPD6004 Phase 3
0.6821 Remote Similarity NPD6002 Phase 3
0.6816 Remote Similarity NPD7239 Suspended
0.6806 Remote Similarity NPD8368 Discontinued
0.6804 Remote Similarity NPD8150 Discontinued
0.6798 Remote Similarity NPD6273 Approved
0.6791 Remote Similarity NPD7184 Clinical (unspecified phase)
0.678 Remote Similarity NPD6799 Approved
0.6778 Remote Similarity NPD3226 Approved
0.6776 Remote Similarity NPD3817 Phase 2
0.6776 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6774 Remote Similarity NPD7199 Phase 2
0.6771 Remote Similarity NPD7808 Phase 3
0.6771 Remote Similarity NPD4338 Clinical (unspecified phase)
0.676 Remote Similarity NPD920 Approved
0.6749 Remote Similarity NPD7497 Discontinued
0.6742 Remote Similarity NPD2532 Approved
0.6742 Remote Similarity NPD2534 Approved
0.6742 Remote Similarity NPD2533 Approved
0.6737 Remote Similarity NPD5844 Phase 1
0.6724 Remote Similarity NPD1471 Phase 3
0.672 Remote Similarity NPD7473 Discontinued
0.672 Remote Similarity NPD5494 Approved
0.6719 Remote Similarity NPD7251 Discontinued
0.6707 Remote Similarity NPD5647 Approved
0.6703 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6703 Remote Similarity NPD7411 Suspended
0.6667 Remote Similarity NPD6797 Phase 2
0.6667 Remote Similarity NPD7435 Discontinued
0.6667 Remote Similarity NPD6166 Phase 2
0.6667 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5403 Approved
0.6649 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6649 Remote Similarity NPD4965 Approved
0.6649 Remote Similarity NPD4966 Approved
0.6649 Remote Similarity NPD4967 Phase 2
0.6648 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6648 Remote Similarity NPD4380 Phase 2
0.6648 Remote Similarity NPD642 Clinical (unspecified phase)
0.663 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6629 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6615 Remote Similarity NPD7472 Approved
0.6615 Remote Similarity NPD7074 Phase 3
0.6613 Remote Similarity NPD3749 Approved
0.6609 Remote Similarity NPD2799 Discontinued
0.6597 Remote Similarity NPD3751 Discontinued
0.6597 Remote Similarity NPD7893 Clinical (unspecified phase)
0.659 Remote Similarity NPD6653 Approved
0.6579 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6578 Remote Similarity NPD6234 Discontinued
0.6576 Remote Similarity NPD1934 Approved
0.6576 Remote Similarity NPD37 Approved
0.6566 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6566 Remote Similarity NPD8360 Approved
0.6566 Remote Similarity NPD8361 Approved
0.6562 Remote Similarity NPD7054 Approved
0.6561 Remote Similarity NPD6232 Discontinued
0.6558 Remote Similarity NPD7907 Approved
0.6556 Remote Similarity NPD5401 Approved
0.6556 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6556 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6555 Remote Similarity NPD7874 Approved
0.6555 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6541 Remote Similarity NPD2801 Approved
0.6536 Remote Similarity NPD643 Clinical (unspecified phase)
0.6532 Remote Similarity NPD6355 Discontinued
0.6526 Remote Similarity NPD3926 Phase 2
0.652 Remote Similarity NPD6781 Approved
0.652 Remote Similarity NPD6778 Approved
0.652 Remote Similarity NPD6780 Approved
0.652 Remote Similarity NPD6776 Approved
0.652 Remote Similarity NPD6779 Approved
0.652 Remote Similarity NPD6777 Approved
0.652 Remote Similarity NPD6782 Approved
0.6517 Remote Similarity NPD6398 Clinical (unspecified phase)
0.651 Remote Similarity NPD7228 Approved
0.6505 Remote Similarity NPD7697 Approved
0.6505 Remote Similarity NPD7696 Phase 3
0.6505 Remote Similarity NPD7698 Approved
0.6503 Remote Similarity NPD7458 Discontinued
0.6498 Remote Similarity NPD5619 Clinical (unspecified phase)
0.6482 Remote Similarity NPD8435 Approved
0.648 Remote Similarity NPD6190 Approved
0.6474 Remote Similarity NPD3787 Discontinued
0.6474 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6473 Remote Similarity NPD7871 Phase 2
0.6473 Remote Similarity NPD7870 Phase 2
0.6471 Remote Similarity NPD7057 Phase 3
0.6471 Remote Similarity NPD7058 Phase 2
0.6467 Remote Similarity NPD7028 Phase 2
0.6465 Remote Similarity NPD4665 Approved
0.6465 Remote Similarity NPD4111 Phase 1
0.6461 Remote Similarity NPD2800 Approved
0.6459 Remote Similarity NPD7701 Phase 2
0.6445 Remote Similarity NPD7801 Approved
0.642 Remote Similarity NPD7033 Discontinued
0.6412 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6404 Remote Similarity NPD970 Clinical (unspecified phase)
0.6394 Remote Similarity NPD8320 Phase 1
0.6394 Remote Similarity NPD8319 Approved
0.6392 Remote Similarity NPD8470 Clinical (unspecified phase)
0.6384 Remote Similarity NPD1551 Phase 2
0.6383 Remote Similarity NPD7768 Phase 2
0.6378 Remote Similarity NPD7240 Approved
0.6373 Remote Similarity NPD8485 Approved
0.6369 Remote Similarity NPD1243 Approved
0.6364 Remote Similarity NPD8455 Phase 2
0.6351 Remote Similarity NPD8151 Discontinued
0.6348 Remote Similarity NPD2346 Discontinued
0.6348 Remote Similarity NPD2344 Approved
0.6343 Remote Similarity NPD447 Suspended
0.6341 Remote Similarity NPD7699 Phase 2
0.6341 Remote Similarity NPD7700 Phase 2
0.634 Remote Similarity NPD2163 Approved
0.6339 Remote Similarity NPD1512 Approved
0.6335 Remote Similarity NPD6959 Discontinued
0.6333 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6321 Remote Similarity NPD2403 Approved
0.6319 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6313 Remote Similarity NPD1549 Phase 2
0.6304 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6298 Remote Similarity NPD3057 Approved
0.6293 Remote Similarity NPD8090 Clinical (unspecified phase)
0.6292 Remote Similarity NPD2796 Approved
0.6292 Remote Similarity NPD6100 Approved
0.6292 Remote Similarity NPD2935 Discontinued
0.6292 Remote Similarity NPD6099 Approved
0.6291 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6291 Remote Similarity NPD7783 Phase 2
0.6286 Remote Similarity NPD4140 Approved
0.6284 Remote Similarity NPD7410 Clinical (unspecified phase)
0.628 Remote Similarity NPD8486 Clinical (unspecified phase)
0.6279 Remote Similarity NPD7930 Approved
0.6277 Remote Similarity NPD1465 Phase 2
0.6275 Remote Similarity NPD6535 Approved
0.6275 Remote Similarity NPD6534 Approved
0.6264 Remote Similarity NPD1699 Clinical (unspecified phase)
0.6262 Remote Similarity NPD8462 Phase 1
0.6257 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6257 Remote Similarity NPD7319 Approved
0.6257 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6256 Remote Similarity NPD8155 Clinical (unspecified phase)
0.625 Remote Similarity NPD5735 Approved
0.625 Remote Similarity NPD230 Phase 1
0.6243 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6243 Remote Similarity NPD3750 Approved
0.6243 Remote Similarity NPD4110 Phase 3
0.6237 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6237 Remote Similarity NPD4575 Clinical (unspecified phase)
0.623 Remote Similarity NPD1511 Approved
0.6229 Remote Similarity NPD8032 Phase 2
0.622 Remote Similarity NPD6823 Phase 2
0.622 Remote Similarity NPD3533 Approved
0.622 Remote Similarity NPD2972 Approved
0.6219 Remote Similarity NPD8424 Clinical (unspecified phase)
0.6218 Remote Similarity NPD7315 Approved
0.6218 Remote Similarity NPD5711 Approved
0.6218 Remote Similarity NPD6808 Phase 2
0.6218 Remote Similarity NPD5710 Approved
0.6209 Remote Similarity NPD2309 Approved
0.6205 Remote Similarity NPD9092 Discovery
0.6202 Remote Similarity NPD4107 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