Structure

Physi-Chem Properties

Molecular Weight:  436.26
Volume:  469.404
LogP:  4.373
LogD:  2.998
LogS:  -4.021
# Rotatable Bonds:  0
TPSA:  77.76
# H-Bond Aceptor:  4
# H-Bond Donor:  3
# Rings:  5
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.54
Synthetic Accessibility Score:  5.195
Fsp3:  0.607
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.19
MDCK Permeability:  1.7432654203730635e-05
Pgp-inhibitor:  0.106
Pgp-substrate:  0.917
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.04
30% Bioavailability (F30%):  0.578

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.773
Plasma Protein Binding (PPB):  95.74797058105469%
Volume Distribution (VD):  1.424
Pgp-substrate:  10.672402381896973%

ADMET: Metabolism

CYP1A2-inhibitor:  0.023
CYP1A2-substrate:  0.899
CYP2C19-inhibitor:  0.035
CYP2C19-substrate:  0.734
CYP2C9-inhibitor:  0.159
CYP2C9-substrate:  0.15
CYP2D6-inhibitor:  0.082
CYP2D6-substrate:  0.043
CYP3A4-inhibitor:  0.614
CYP3A4-substrate:  0.929

ADMET: Excretion

Clearance (CL):  13.873
Half-life (T1/2):  0.771

ADMET: Toxicity

hERG Blockers:  0.033
Human Hepatotoxicity (H-HT):  0.455
Drug-inuced Liver Injury (DILI):  0.037
AMES Toxicity:  0.08
Rat Oral Acute Toxicity:  0.181
Maximum Recommended Daily Dose:  0.901
Skin Sensitization:  0.207
Carcinogencity:  0.849
Eye Corrosion:  0.003
Eye Irritation:  0.105
Respiratory Toxicity:  0.972

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Structure MOL file  
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Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC68148

Natural Product ID:  NPC68148
Common Name*:   20Alpha-Hydroxytingenone
IUPAC Name:   (6aS,6bS,8aS,11S,12aR,14aR)-3,11-dihydroxy-4,6a,6b,8a,11,14a-hexamethyl-8,9,12,12a,13,14-hexahydro-7H-picene-2,10-dione
Synonyms:   20Alpha-Hydroxytingenone
Standard InCHIKey:  LLINHWDEBZOLGN-UNQYGWCUSA-N
Standard InCHI:  InChI=1S/C28H36O4/c1-16-17-7-8-20-25(3,18(17)13-19(29)23(16)31)10-12-27(5)21-14-28(6,32)22(30)15-24(21,2)9-11-26(20,27)4/h7-8,13,21,31-32H,9-12,14-15H2,1-6H3/t21-,24+,25+,26-,27+,28+/m1/s1
SMILES:  CC1=C(C(=O)C=C2C1=CC=C1[C@@]2(C)CC[C@@]2(C)[C@@H]3C[C@@](C)(C(=O)C[C@]3(C)CC[C@]12C)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1651342
PubChem CID:   10717799
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0001831] Carbonyl compounds
          • [CHEMONTID:0002088] Acyloins

*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
NPO9112 Maytenus sp. Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[10637057]
NPO21438 Cladiella kashmani Species Alcyoniidae Eukaryota n.a. African soft coral n.a. PMID[11087607]
NPO26894 Kokoona zeylanica Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[11678653]
NPO27680 Zanthoxylum syncarpum Species Rutaceae Eukaryota n.a. stem n.a. PMID[14738394]
NPO27680 Zanthoxylum syncarpum Species Rutaceae Eukaryota leaves n.a. n.a. PMID[16124784]
NPO13187 Sclerotinia homoeocarpa Species Sclerotiniaceae Eukaryota n.a. n.a. n.a. PMID[19928902]
NPO25224 Maytenus retusa Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[21090801]
NPO27616 Berberis lambertii Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9112 Maytenus sp. Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27616 Berberis lambertii Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3480 Lathyrus hirsutus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25224 Maytenus retusa Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11178 Argemone munita Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27616 Berberis lambertii Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13187 Sclerotinia homoeocarpa Species Sclerotiniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27660 Thunbergia grandiflora Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21438 Cladiella kashmani Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26894 Kokoona zeylanica Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10220 Lobelia davidii Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13945 Ariocarpus retusus Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27680 Zanthoxylum syncarpum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10617 Tenodera aridifolia Species Mantidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2523 Polycitorella mariae Species Polycitoridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26873 Echinochloa crus-galli Species Poaceae 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 = 400.0 nM PMID[459052]
NPT83 Cell Line MCF7 Homo sapiens Inhibition = 100.0 % PMID[459052]
NPT83 Cell Line MCF7 Homo sapiens Inhibition = 85.0 % PMID[459052]
NPT83 Cell Line MCF7 Homo sapiens Inhibition = 14.0 % PMID[459052]
NPT116 Cell Line HL-60 Homo sapiens Inhibition = 87.0 % PMID[459052]
NPT116 Cell Line HL-60 Homo sapiens Inhibition = 100.0 % PMID[459052]
NPT116 Cell Line HL-60 Homo sapiens Inhibition = 25.0 % PMID[459052]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 4700.0 nM PMID[459052]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae Activity = 185.0 ug ml-1 PMID[459051]
NPT1637 Organism Cydia pomonella Cydia pomonella Activity = 0.0 n.a. PMID[459053]
NPT1637 Organism Cydia pomonella Cydia pomonella Activity = 0.3 n.a. PMID[459053]
NPT1637 Organism Cydia pomonella Cydia pomonella Activity = 0.2 n.a. PMID[459053]
NPT1637 Organism Cydia pomonella Cydia pomonella Activity = 0.6 n.a. PMID[459053]
NPT1637 Organism Cydia pomonella Cydia pomonella Activity = 1.4 n.a. PMID[459053]
NPT1637 Organism Cydia pomonella Cydia pomonella Activity = 1.2 n.a. PMID[459053]
NPT1637 Organism Cydia pomonella Cydia pomonella Activity = 0.1 n.a. PMID[459053]
NPT1637 Organism Cydia pomonella Cydia pomonella Activity = 100.0 % PMID[459053]
NPT1637 Organism Cydia pomonella Cydia pomonella Activity = 3.3 % PMID[459053]
NPT1637 Organism Cydia pomonella Cydia pomonella Activity = 6.7 % PMID[459053]
NPT1637 Organism Cydia pomonella Cydia pomonella LC50 = 8500.0 ug.mL-1 PMID[459053]
NPT1637 Organism Cydia pomonella Cydia pomonella mortality = 100.0 % PMID[459053]
NPT1637 Organism Cydia pomonella Cydia pomonella mortality = 0.0 % PMID[459053]
NPT1637 Organism Cydia pomonella Cydia pomonella mortality = 3.3 % PMID[459053]
NPT1637 Organism Cydia pomonella Cydia pomonella LC50 = 13000.0 ug.mL-1 PMID[459053]
NPT1637 Organism Cydia pomonella Cydia pomonella mortality = 10.0 % PMID[459053]
NPT1637 Organism Cydia pomonella Cydia pomonella Activity = 46.7 % PMID[459053]
NPT1637 Organism Cydia pomonella Cydia pomonella mortality = 23.3 % PMID[459053]
NPT1637 Organism Cydia pomonella Cydia pomonella Activity = 83.3 % PMID[459053]
NPT1637 Organism Cydia pomonella Cydia pomonella mortality = 53.3 % PMID[459053]
NPT1637 Organism Cydia pomonella Cydia pomonella Activity = 53.3 % PMID[459053]
NPT1637 Organism Cydia pomonella Cydia pomonella Activity = 36.7 % PMID[459053]
NPT1637 Organism Cydia pomonella Cydia pomonella mortality = 43.3 % PMID[459053]
NPT1637 Organism Cydia pomonella Cydia pomonella Activity = 80.0 % PMID[459053]
NPT1637 Organism Cydia pomonella Cydia pomonella mortality = 60.0 % PMID[459053]
NPT1637 Organism Cydia pomonella Cydia pomonella Activity = 33.3 % PMID[459053]
NPT1637 Organism Cydia pomonella Cydia pomonella mortality = 93.3 % PMID[459053]
NPT1637 Organism Cydia pomonella Cydia pomonella mortality = 16.7 % PMID[459053]
NPT1637 Organism Cydia pomonella Cydia pomonella mortality = 86.7 % PMID[459053]
NPT1637 Organism Cydia pomonella Cydia pomonella Activity = 90.0 % PMID[459053]
NPT1637 Organism Cydia pomonella Cydia pomonella Activity = 96.7 % PMID[459053]
NPT1637 Organism Cydia pomonella Cydia pomonella mortality = 6.7 % PMID[459053]

☑ 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 NPC68148 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 NPC65615
0.9302 High Similarity NPC112454
0.9205 High Similarity NPC211230
0.9101 High Similarity NPC474328
0.9091 High Similarity NPC174167
0.9091 High Similarity NPC470036
0.9048 High Similarity NPC53733
0.9036 High Similarity NPC475863
0.8989 High Similarity NPC263780
0.8916 High Similarity NPC287063
0.8889 High Similarity NPC474882
0.8889 High Similarity NPC160413
0.8889 High Similarity NPC23170
0.881 High Similarity NPC470034
0.8791 High Similarity NPC777
0.8791 High Similarity NPC147232
0.869 High Similarity NPC18955
0.8675 High Similarity NPC476808
0.8621 High Similarity NPC469993
0.8605 High Similarity NPC309309
0.8605 High Similarity NPC291999
0.8588 High Similarity NPC225515
0.8588 High Similarity NPC55869
0.8539 High Similarity NPC230387
0.8506 High Similarity NPC53385
0.8471 Intermediate Similarity NPC108955
0.8454 Intermediate Similarity NPC213366
0.8452 Intermediate Similarity NPC30321
0.8434 Intermediate Similarity NPC92080
0.8409 Intermediate Similarity NPC33881
0.8391 Intermediate Similarity NPC105803
0.8372 Intermediate Similarity NPC473217
0.8353 Intermediate Similarity NPC27817
0.8352 Intermediate Similarity NPC475823
0.8352 Intermediate Similarity NPC474209
0.8295 Intermediate Similarity NPC96095
0.8256 Intermediate Similarity NPC476809
0.8242 Intermediate Similarity NPC474918
0.8235 Intermediate Similarity NPC189485
0.8214 Intermediate Similarity NPC112680
0.8202 Intermediate Similarity NPC6185
0.8202 Intermediate Similarity NPC263997
0.8202 Intermediate Similarity NPC241512
0.8202 Intermediate Similarity NPC474537
0.8202 Intermediate Similarity NPC132228
0.8202 Intermediate Similarity NPC474680
0.8202 Intermediate Similarity NPC8518
0.8182 Intermediate Similarity NPC70834
0.8163 Intermediate Similarity NPC179208
0.8161 Intermediate Similarity NPC121984
0.8161 Intermediate Similarity NPC471898
0.8161 Intermediate Similarity NPC142244
0.8152 Intermediate Similarity NPC46441
0.814 Intermediate Similarity NPC192329
0.8111 Intermediate Similarity NPC56588
0.8105 Intermediate Similarity NPC157113
0.8105 Intermediate Similarity NPC62516
0.809 Intermediate Similarity NPC180834
0.8085 Intermediate Similarity NPC80365
0.8068 Intermediate Similarity NPC251779
0.8068 Intermediate Similarity NPC310989
0.8068 Intermediate Similarity NPC103486
0.8068 Intermediate Similarity NPC69101
0.8065 Intermediate Similarity NPC301244
0.8065 Intermediate Similarity NPC474525
0.8065 Intermediate Similarity NPC233455
0.8065 Intermediate Similarity NPC145067
0.8065 Intermediate Similarity NPC158030
0.8065 Intermediate Similarity NPC4036
0.8065 Intermediate Similarity NPC65120
0.8046 Intermediate Similarity NPC37038
0.8046 Intermediate Similarity NPC469637
0.8046 Intermediate Similarity NPC2482
0.8022 Intermediate Similarity NPC73064
0.8 Intermediate Similarity NPC110725
0.8 Intermediate Similarity NPC133954
0.8 Intermediate Similarity NPC32037
0.8 Intermediate Similarity NPC292589
0.8 Intermediate Similarity NPC280725
0.7979 Intermediate Similarity NPC214756
0.7979 Intermediate Similarity NPC272075
0.7979 Intermediate Similarity NPC295643
0.7957 Intermediate Similarity NPC252737
0.7955 Intermediate Similarity NPC274050
0.7955 Intermediate Similarity NPC267691
0.7955 Intermediate Similarity NPC162632
0.7955 Intermediate Similarity NPC278459
0.7955 Intermediate Similarity NPC263272
0.7955 Intermediate Similarity NPC3915
0.7935 Intermediate Similarity NPC206060
0.7935 Intermediate Similarity NPC472802
0.7931 Intermediate Similarity NPC231431
0.7931 Intermediate Similarity NPC199595
0.7917 Intermediate Similarity NPC473158
0.7917 Intermediate Similarity NPC88847
0.7917 Intermediate Similarity NPC9487
0.7912 Intermediate Similarity NPC213412
0.7912 Intermediate Similarity NPC158393
0.7912 Intermediate Similarity NPC475862
0.7912 Intermediate Similarity NPC74363
0.7912 Intermediate Similarity NPC94666
0.7907 Intermediate Similarity NPC266193
0.7907 Intermediate Similarity NPC257666
0.7895 Intermediate Similarity NPC196485
0.7895 Intermediate Similarity NPC74751
0.7895 Intermediate Similarity NPC245972
0.7889 Intermediate Similarity NPC144258
0.7882 Intermediate Similarity NPC175079
0.7872 Intermediate Similarity NPC248913
0.7872 Intermediate Similarity NPC235704
0.7872 Intermediate Similarity NPC473167
0.7865 Intermediate Similarity NPC48362
0.7849 Intermediate Similarity NPC118011
0.7849 Intermediate Similarity NPC477973
0.7849 Intermediate Similarity NPC472676
0.7849 Intermediate Similarity NPC198664
0.7849 Intermediate Similarity NPC474686
0.7849 Intermediate Similarity NPC472688
0.7849 Intermediate Similarity NPC474245
0.7849 Intermediate Similarity NPC161751
0.7849 Intermediate Similarity NPC36668
0.7849 Intermediate Similarity NPC143232
0.7849 Intermediate Similarity NPC474972
0.7849 Intermediate Similarity NPC95246
0.7849 Intermediate Similarity NPC274330
0.7835 Intermediate Similarity NPC21728
0.7835 Intermediate Similarity NPC473456
0.7826 Intermediate Similarity NPC470523
0.7826 Intermediate Similarity NPC71507
0.7822 Intermediate Similarity NPC478052
0.7816 Intermediate Similarity NPC110094
0.7816 Intermediate Similarity NPC260385
0.7816 Intermediate Similarity NPC471409
0.7816 Intermediate Similarity NPC275494
0.7816 Intermediate Similarity NPC280654
0.7812 Intermediate Similarity NPC148523
0.7812 Intermediate Similarity NPC139570
0.7802 Intermediate Similarity NPC33663
0.7802 Intermediate Similarity NPC133652
0.7791 Intermediate Similarity NPC1254
0.7789 Intermediate Similarity NPC12722
0.7789 Intermediate Similarity NPC474806
0.7789 Intermediate Similarity NPC202728
0.7789 Intermediate Similarity NPC158059
0.7789 Intermediate Similarity NPC118519
0.7789 Intermediate Similarity NPC133579
0.7778 Intermediate Similarity NPC118964
0.7766 Intermediate Similarity NPC126369
0.7766 Intermediate Similarity NPC291028
0.7766 Intermediate Similarity NPC111110
0.7766 Intermediate Similarity NPC223093
0.7766 Intermediate Similarity NPC470589
0.7766 Intermediate Similarity NPC212369
0.7766 Intermediate Similarity NPC474728
0.7766 Intermediate Similarity NPC85173
0.7766 Intermediate Similarity NPC129913
0.7765 Intermediate Similarity NPC162164
0.7753 Intermediate Similarity NPC474085
0.7753 Intermediate Similarity NPC44963
0.7753 Intermediate Similarity NPC472684
0.7742 Intermediate Similarity NPC470524
0.7742 Intermediate Similarity NPC470629
0.7742 Intermediate Similarity NPC290690
0.7742 Intermediate Similarity NPC182797
0.7742 Intermediate Similarity NPC52169
0.7742 Intermediate Similarity NPC473242
0.7742 Intermediate Similarity NPC1753
0.7742 Intermediate Similarity NPC474474
0.7742 Intermediate Similarity NPC17733
0.7742 Intermediate Similarity NPC185059
0.7742 Intermediate Similarity NPC471722
0.7742 Intermediate Similarity NPC58271
0.7742 Intermediate Similarity NPC48107
0.7742 Intermediate Similarity NPC474512
0.7742 Intermediate Similarity NPC474511
0.7742 Intermediate Similarity NPC181225
0.7742 Intermediate Similarity NPC475001
0.7742 Intermediate Similarity NPC72397
0.7732 Intermediate Similarity NPC98874
0.7732 Intermediate Similarity NPC269492
0.7727 Intermediate Similarity NPC215843
0.7727 Intermediate Similarity NPC16394
0.7727 Intermediate Similarity NPC474113
0.7727 Intermediate Similarity NPC170394
0.7717 Intermediate Similarity NPC51014
0.7717 Intermediate Similarity NPC145879
0.7717 Intermediate Similarity NPC235341
0.7717 Intermediate Similarity NPC95594
0.7717 Intermediate Similarity NPC72638
0.7717 Intermediate Similarity NPC31564
0.7717 Intermediate Similarity NPC474778
0.7717 Intermediate Similarity NPC203795
0.7717 Intermediate Similarity NPC474733
0.7717 Intermediate Similarity NPC474732
0.7717 Intermediate Similarity NPC477579
0.7708 Intermediate Similarity NPC148964
0.7708 Intermediate Similarity NPC191412
0.7708 Intermediate Similarity NPC114159
0.7708 Intermediate Similarity NPC212812
0.7708 Intermediate Similarity NPC6818

  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 NPC68148 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
0.9302 High Similarity NPD7285 Clinical (unspecified phase)
0.8471 Intermediate Similarity NPD4695 Discontinued
0.8111 Intermediate Similarity NPD4694 Approved
0.8111 Intermediate Similarity NPD5280 Approved
0.8065 Intermediate Similarity NPD7515 Phase 2
0.8023 Intermediate Similarity NPD3617 Approved
0.8 Intermediate Similarity NPD5329 Approved
0.7895 Intermediate Similarity NPD7748 Approved
0.7889 Intermediate Similarity NPD4197 Approved
0.7717 Intermediate Similarity NPD5279 Phase 3
0.7717 Intermediate Similarity NPD5690 Phase 2
0.7717 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.7667 Intermediate Similarity NPD4221 Approved
0.7667 Intermediate Similarity NPD4223 Phase 3
0.766 Intermediate Similarity NPD4753 Phase 2
0.7653 Intermediate Similarity NPD7902 Approved
0.7604 Intermediate Similarity NPD5133 Approved
0.7551 Intermediate Similarity NPD7614 Phase 1
0.7527 Intermediate Similarity NPD3618 Phase 1
0.75 Intermediate Similarity NPD5281 Approved
0.75 Intermediate Similarity NPD4786 Approved
0.75 Intermediate Similarity NPD5284 Approved
0.75 Intermediate Similarity NPD6050 Approved
0.7475 Intermediate Similarity NPD4755 Approved
0.7474 Intermediate Similarity NPD5328 Approved
0.7473 Intermediate Similarity NPD3667 Approved
0.7444 Intermediate Similarity NPD8259 Clinical (unspecified phase)
0.7396 Intermediate Similarity NPD5692 Phase 3
0.7374 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7374 Intermediate Similarity NPD4697 Phase 3
0.7374 Intermediate Similarity NPD5221 Approved
0.7374 Intermediate Similarity NPD5222 Approved
0.7347 Intermediate Similarity NPD7900 Approved
0.7347 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.734 Intermediate Similarity NPD4688 Approved
0.734 Intermediate Similarity NPD4623 Approved
0.734 Intermediate Similarity NPD4689 Approved
0.734 Intermediate Similarity NPD4138 Approved
0.734 Intermediate Similarity NPD4519 Discontinued
0.734 Intermediate Similarity NPD4690 Approved
0.734 Intermediate Similarity NPD4693 Phase 3
0.734 Intermediate Similarity NPD5205 Approved
0.7327 Intermediate Similarity NPD4696 Approved
0.7327 Intermediate Similarity NPD5285 Approved
0.7327 Intermediate Similarity NPD5286 Approved
0.7327 Intermediate Similarity NPD4700 Approved
0.732 Intermediate Similarity NPD6079 Approved
0.732 Intermediate Similarity NPD5694 Approved
0.7312 Intermediate Similarity NPD3666 Approved
0.7312 Intermediate Similarity NPD3133 Approved
0.7312 Intermediate Similarity NPD3665 Phase 1
0.73 Intermediate Similarity NPD6083 Phase 2
0.73 Intermediate Similarity NPD5173 Approved
0.73 Intermediate Similarity NPD6084 Phase 2
0.7292 Intermediate Similarity NPD6904 Approved
0.7292 Intermediate Similarity NPD6080 Approved
0.7292 Intermediate Similarity NPD6673 Approved
0.7273 Intermediate Similarity NPD4629 Approved
0.7273 Intermediate Similarity NPD5695 Phase 3
0.7273 Intermediate Similarity NPD5210 Approved
0.7263 Intermediate Similarity NPD3573 Approved
0.7255 Intermediate Similarity NPD5223 Approved
0.7245 Intermediate Similarity NPD4202 Approved
0.7216 Intermediate Similarity NPD4096 Approved
0.7188 Intermediate Similarity NPD6672 Approved
0.7188 Intermediate Similarity NPD5737 Approved
0.7188 Intermediate Similarity NPD4518 Approved
0.7184 Intermediate Similarity NPD5211 Phase 2
0.7184 Intermediate Similarity NPD5225 Approved
0.7184 Intermediate Similarity NPD5226 Approved
0.7184 Intermediate Similarity NPD4633 Approved
0.7184 Intermediate Similarity NPD5224 Approved
0.7159 Intermediate Similarity NPD5733 Approved
0.7143 Intermediate Similarity NPD7128 Approved
0.7143 Intermediate Similarity NPD5739 Approved
0.7143 Intermediate Similarity NPD6402 Approved
0.7143 Intermediate Similarity NPD6675 Approved
0.7128 Intermediate Similarity NPD3668 Phase 3
0.7115 Intermediate Similarity NPD4754 Approved
0.7115 Intermediate Similarity NPD5175 Approved
0.7115 Intermediate Similarity NPD5174 Approved
0.71 Intermediate Similarity NPD5654 Approved
0.7071 Intermediate Similarity NPD6399 Phase 3
0.7059 Intermediate Similarity NPD5696 Approved
0.7053 Intermediate Similarity NPD1696 Phase 3
0.7048 Intermediate Similarity NPD5141 Approved
0.703 Intermediate Similarity NPD7732 Phase 3
0.7021 Intermediate Similarity NPD4788 Approved
0.701 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7009 Intermediate Similarity NPD6881 Approved
0.7009 Intermediate Similarity NPD6899 Approved
0.7009 Intermediate Similarity NPD7320 Approved
0.6989 Remote Similarity NPD4692 Approved
0.6989 Remote Similarity NPD4139 Approved
0.6989 Remote Similarity NPD8028 Phase 2
0.6981 Remote Similarity NPD4767 Approved
0.6981 Remote Similarity NPD4768 Approved
0.6979 Remote Similarity NPD6098 Approved
0.697 Remote Similarity NPD5693 Phase 1
0.6966 Remote Similarity NPD4058 Approved
0.6966 Remote Similarity NPD4687 Approved
0.6961 Remote Similarity NPD5959 Approved
0.6957 Remote Similarity NPD4195 Approved
0.6957 Remote Similarity NPD7645 Phase 2
0.6944 Remote Similarity NPD6372 Approved
0.6944 Remote Similarity NPD6373 Approved
0.6932 Remote Similarity NPD5276 Approved
0.6916 Remote Similarity NPD5697 Approved
0.6916 Remote Similarity NPD5701 Approved
0.6897 Remote Similarity NPD4137 Phase 3
0.6881 Remote Similarity NPD6883 Approved
0.6881 Remote Similarity NPD7290 Approved
0.6881 Remote Similarity NPD7102 Approved
0.6869 Remote Similarity NPD5207 Approved
0.6857 Remote Similarity NPD5091 Approved
0.6852 Remote Similarity NPD4730 Approved
0.6852 Remote Similarity NPD5128 Approved
0.6852 Remote Similarity NPD6011 Approved
0.6852 Remote Similarity NPD4729 Approved
0.6824 Remote Similarity NPD7341 Phase 2
0.6818 Remote Similarity NPD6869 Approved
0.6818 Remote Similarity NPD8130 Phase 1
0.6818 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6818 Remote Similarity NPD6649 Approved
0.6818 Remote Similarity NPD4691 Approved
0.6818 Remote Similarity NPD4747 Approved
0.6818 Remote Similarity NPD6847 Approved
0.6818 Remote Similarity NPD6650 Approved
0.6818 Remote Similarity NPD6617 Approved
0.6804 Remote Similarity NPD7146 Approved
0.6804 Remote Similarity NPD7521 Approved
0.6804 Remote Similarity NPD6409 Approved
0.6804 Remote Similarity NPD7334 Approved
0.6804 Remote Similarity NPD5330 Approved
0.6804 Remote Similarity NPD6684 Approved
0.68 Remote Similarity NPD6411 Approved
0.6789 Remote Similarity NPD6012 Approved
0.6789 Remote Similarity NPD6013 Approved
0.6789 Remote Similarity NPD6014 Approved
0.6786 Remote Similarity NPD2664 Clinical (unspecified phase)
0.6782 Remote Similarity NPD5360 Phase 3
0.6782 Remote Similarity NPD5361 Clinical (unspecified phase)
0.6765 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6757 Remote Similarity NPD8297 Approved
0.6757 Remote Similarity NPD6882 Approved
0.6744 Remote Similarity NPD7331 Phase 2
0.6727 Remote Similarity NPD5135 Approved
0.6727 Remote Similarity NPD5250 Approved
0.6727 Remote Similarity NPD5247 Approved
0.6727 Remote Similarity NPD5169 Approved
0.6727 Remote Similarity NPD5248 Approved
0.6727 Remote Similarity NPD4634 Approved
0.6727 Remote Similarity NPD5249 Phase 3
0.6727 Remote Similarity NPD5251 Approved
0.6727 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6702 Remote Similarity NPD7525 Registered
0.6701 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6697 Remote Similarity NPD5168 Approved
0.6667 Remote Similarity NPD6903 Approved
0.6667 Remote Similarity NPD5217 Approved
0.6667 Remote Similarity NPD5215 Approved
0.6667 Remote Similarity NPD5127 Approved
0.6667 Remote Similarity NPD5208 Approved
0.6667 Remote Similarity NPD5216 Approved
0.66 Remote Similarity NPD6101 Approved
0.66 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6593 Remote Similarity NPD4784 Approved
0.6593 Remote Similarity NPD4785 Approved
0.6571 Remote Similarity NPD7638 Approved
0.6556 Remote Similarity NPD4243 Approved
0.6549 Remote Similarity NPD4632 Approved
0.6522 Remote Similarity NPD7339 Approved
0.6522 Remote Similarity NPD6942 Approved
0.6522 Remote Similarity NPD7115 Discovery
0.6509 Remote Similarity NPD7639 Approved
0.6509 Remote Similarity NPD6404 Discontinued
0.6509 Remote Similarity NPD7640 Approved
0.6505 Remote Similarity NPD6001 Approved
0.6491 Remote Similarity NPD5167 Approved
0.6471 Remote Similarity NPD8034 Phase 2
0.6471 Remote Similarity NPD8035 Phase 2
0.6471 Remote Similarity NPD8328 Phase 3
0.6466 Remote Similarity NPD6335 Approved
0.6455 Remote Similarity NPD6412 Phase 2
0.6452 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6444 Remote Similarity NPD4789 Approved
0.6435 Remote Similarity NPD6868 Approved
0.6435 Remote Similarity NPD6274 Approved
0.6413 Remote Similarity NPD6926 Approved
0.6413 Remote Similarity NPD6924 Approved
0.641 Remote Similarity NPD7610 Discontinued
0.641 Remote Similarity NPD7100 Approved
0.641 Remote Similarity NPD7101 Approved
0.6404 Remote Similarity NPD3621 Clinical (unspecified phase)
0.6379 Remote Similarity NPD6009 Approved
0.6379 Remote Similarity NPD6317 Approved
0.6374 Remote Similarity NPD4809 Clinical (unspecified phase)
0.6374 Remote Similarity NPD4758 Discontinued
0.6374 Remote Similarity NPD4808 Clinical (unspecified phase)
0.6364 Remote Similarity NPD6008 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