Structure

Physi-Chem Properties

Molecular Weight:  570.15
Volume:  561.681
LogP:  5.925
LogD:  2.513
LogS:  -4.928
# Rotatable Bonds:  5
TPSA:  137.8
# H-Bond Aceptor:  10
# H-Bond Donor:  2
# Rings:  6
# Heavy Atoms:  10

MedChem Properties

QED Drug-Likeness Score:  0.24
Synthetic Accessibility Score:  3.331
Fsp3:  0.188
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:  -5.054
MDCK Permeability:  2.4668881451361813e-05
Pgp-inhibitor:  0.976
Pgp-substrate:  0.105
Human Intestinal Absorption (HIA):  0.367
20% Bioavailability (F20%):  0.001
30% Bioavailability (F30%):  0.242

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.001
Plasma Protein Binding (PPB):  64.1922607421875%
Volume Distribution (VD):  0.449
Pgp-substrate:  51.24867630004883%

ADMET: Metabolism

CYP1A2-inhibitor:  0.172
CYP1A2-substrate:  0.99
CYP2C19-inhibitor:  0.44
CYP2C19-substrate:  0.616
CYP2C9-inhibitor:  0.758
CYP2C9-substrate:  0.934
CYP2D6-inhibitor:  0.004
CYP2D6-substrate:  0.909
CYP3A4-inhibitor:  0.077
CYP3A4-substrate:  0.283

ADMET: Excretion

Clearance (CL):  2.759
Half-life (T1/2):  0.133

ADMET: Toxicity

hERG Blockers:  0.002
Human Hepatotoxicity (H-HT):  0.14
Drug-inuced Liver Injury (DILI):  0.98
AMES Toxicity:  0.126
Rat Oral Acute Toxicity:  0.193
Maximum Recommended Daily Dose:  0.873
Skin Sensitization:  0.127
Carcinogencity:  0.017
Eye Corrosion:  0.003
Eye Irritation:  0.358
Respiratory Toxicity:  0.096

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  Natural Product: NPC189552

Natural Product ID:  NPC189552
Common Name*:   Aurasperone A
IUPAC Name:   5-hydroxy-7-(5-hydroxy-6,8-dimethoxy-2-methyl-4-oxobenzo[g]chromen-10-yl)-6,8-dimethoxy-2-methylbenzo[g]chromen-4-one
Synonyms:  
Standard InCHIKey:  QAHRSPAZSGMZMT-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C32H26O10/c1-13-7-18(33)26-22(41-13)10-15-9-20(38-4)28(31(40-6)23(15)29(26)35)25-17-11-16(37-3)12-21(39-5)24(17)30(36)27-19(34)8-14(2)42-32(25)27/h7-12,35-36H,1-6H3
SMILES:  Cc1cc(=O)c2c(cc3cc(c(c4c5cc(cc(c5c(c5c(=O)cc(C)oc45)O)OC)OC)c(c3c2O)OC)OC)o1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL450763
PubChem CID:   3084216
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001640] Naphthopyrans
        • [CHEMONTID:0001641] Naphthopyranones

*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
NPO24266 Aspergillus fonsecaeus Species Aspergillaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0040-4020(01)88792-5]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0040-4039(01)88611-1]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. DOI[10.1021/np058103o]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. DOI[10.1039/JR9620000040]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. DOI[10.1080/00021369.1966.10858561]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. DOI[10.1080/00021369.1972.10860562]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. DOI[10.1080/00021369.1985.10867263]
NPO8911 Aspergillus aculeatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[10075772]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. mycelium n.a. PMID[10695672]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[12458767]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[12542363]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[15387655]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. sponge-derived n.a. PMID[15387655]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[15556711]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[15620260]
NPO8911 Aspergillus aculeatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[16155971]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[17653510]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[17827758]
NPO8911 Aspergillus aculeatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[19824618]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[20014861]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[20028011]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21176790]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21543515]
NPO8911 Aspergillus aculeatus Species Aspergillaceae Eukaryota n.a. mycelium n.a. PMID[21667999]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. mycelium n.a. PMID[21774474]
NPO8911 Aspergillus aculeatus Species Aspergillaceae Eukaryota n.a. latex n.a. PMID[21854017]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. latex n.a. PMID[21854017]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21854017]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[22921072]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[24684908]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[25044953]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[25062661]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[25293978]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[26040782]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[26132344]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[26414728]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[27245874]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[32159958]
NPO8911 Aspergillus aculeatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[324959]
NPO24266 Aspergillus fonsecaeus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[4837062]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[6073032]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. mycelium n.a. Database[Article]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO8911 Aspergillus aculeatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[Title]
NPO14234 Aspergillus niger Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17535 Scabrethia scabra Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24266 Aspergillus fonsecaeus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24042 Pseudococcus cryptus Species Pseudococcidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8911 Aspergillus aculeatus Species Aspergillaceae 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
NPT144 Individual Protein Telomerase reverse transcriptase Homo sapiens Inhibition = 52.0 % PMID[470601]
NPT4623 Individual Protein Taq polymerase 1 Thermus aquaticus Inhibition = 49.0 % PMID[470601]

☑ 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 NPC189552 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 NPC273467
0.9934 High Similarity NPC312993
0.9934 High Similarity NPC186325
0.9868 High Similarity NPC177650
0.9806 High Similarity NPC469664
0.9739 High Similarity NPC18699
0.9739 High Similarity NPC55443
0.9542 High Similarity NPC215203
0.9542 High Similarity NPC52611
0.9542 High Similarity NPC159707
0.9542 High Similarity NPC150908
0.9542 High Similarity NPC158027
0.9542 High Similarity NPC121649
0.9542 High Similarity NPC248739
0.9542 High Similarity NPC254351
0.9542 High Similarity NPC14606
0.9542 High Similarity NPC186227
0.9542 High Similarity NPC100049
0.9542 High Similarity NPC205026
0.9542 High Similarity NPC265624
0.9477 High Similarity NPC194593
0.9477 High Similarity NPC290830
0.9477 High Similarity NPC72425
0.9477 High Similarity NPC71061
0.9477 High Similarity NPC303485
0.9427 High Similarity NPC15374
0.9423 High Similarity NPC470342
0.9423 High Similarity NPC472052
0.9423 High Similarity NPC472060
0.9351 High Similarity NPC329844
0.9346 High Similarity NPC67322
0.9346 High Similarity NPC222713
0.9346 High Similarity NPC111112
0.9346 High Similarity NPC138299
0.9342 High Similarity NPC158338
0.9342 High Similarity NPC288036
0.9342 High Similarity NPC65589
0.9342 High Similarity NPC97029
0.9342 High Similarity NPC100985
0.9342 High Similarity NPC97028
0.9325 High Similarity NPC216307
0.9276 High Similarity NPC256672
0.9276 High Similarity NPC27221
0.9276 High Similarity NPC7025
0.925 High Similarity NPC30027
0.9241 High Similarity NPC18380
0.9236 High Similarity NPC51760
0.9221 High Similarity NPC474417
0.9221 High Similarity NPC149526
0.9211 High Similarity NPC123202
0.9211 High Similarity NPC22005
0.9211 High Similarity NPC7943
0.9177 High Similarity NPC292863
0.9177 High Similarity NPC184326
0.9167 High Similarity NPC182555
0.9167 High Similarity NPC226656
0.9167 High Similarity NPC66508
0.9167 High Similarity NPC66441
0.9119 High Similarity NPC472261
0.9119 High Similarity NPC312273
0.9119 High Similarity NPC137232
0.9119 High Similarity NPC301256
0.9114 High Similarity NPC324736
0.9114 High Similarity NPC195167
0.9108 High Similarity NPC56049
0.9108 High Similarity NPC146211
0.9108 High Similarity NPC54830
0.9103 High Similarity NPC169990
0.9103 High Similarity NPC210942
0.9097 High Similarity NPC232645
0.9097 High Similarity NPC72958
0.9097 High Similarity NPC478148
0.9091 High Similarity NPC288840
0.9091 High Similarity NPC291746
0.9085 High Similarity NPC34802
0.9074 High Similarity NPC253730
0.9074 High Similarity NPC286230
0.9074 High Similarity NPC76647
0.9068 High Similarity NPC169471
0.9062 High Similarity NPC473012
0.9057 High Similarity NPC121647
0.9045 High Similarity NPC300668
0.9045 High Similarity NPC134171
0.9038 High Similarity NPC154683
0.9038 High Similarity NPC40356
0.9038 High Similarity NPC87708
0.9024 High Similarity NPC477836
0.9013 High Similarity NPC189650
0.9012 High Similarity NPC251336
0.9012 High Similarity NPC477835
0.9006 High Similarity NPC290160
0.9006 High Similarity NPC473009
0.8994 High Similarity NPC105584
0.8994 High Similarity NPC228654
0.8987 High Similarity NPC32867
0.8987 High Similarity NPC180924
0.8981 High Similarity NPC324447
0.8981 High Similarity NPC214632
0.8974 High Similarity NPC258249
0.8968 High Similarity NPC329933
0.8957 High Similarity NPC324522
0.8957 High Similarity NPC105414
0.8957 High Similarity NPC470341
0.8957 High Similarity NPC234497
0.8957 High Similarity NPC472058
0.8951 High Similarity NPC473010
0.8951 High Similarity NPC259757
0.8947 High Similarity NPC84266
0.8938 High Similarity NPC195136
0.8938 High Similarity NPC476506
0.8931 High Similarity NPC246647
0.8931 High Similarity NPC212967
0.8931 High Similarity NPC164110
0.8931 High Similarity NPC96342
0.8931 High Similarity NPC1796
0.8931 High Similarity NPC475184
0.8931 High Similarity NPC257166
0.8931 High Similarity NPC183
0.8924 High Similarity NPC55662
0.8924 High Similarity NPC166054
0.8917 High Similarity NPC45934
0.8917 High Similarity NPC217447
0.8917 High Similarity NPC174086
0.891 High Similarity NPC325983
0.891 High Similarity NPC202595
0.8902 High Similarity NPC300307
0.8896 High Similarity NPC272502
0.8889 High Similarity NPC227841
0.8882 High Similarity NPC219686
0.8882 High Similarity NPC94076
0.8882 High Similarity NPC182255
0.8882 High Similarity NPC66288
0.8875 High Similarity NPC51247
0.8875 High Similarity NPC15815
0.8875 High Similarity NPC90497
0.8875 High Similarity NPC295090
0.8868 High Similarity NPC192587
0.8868 High Similarity NPC69531
0.8868 High Similarity NPC137100
0.8861 High Similarity NPC178964
0.8861 High Similarity NPC280530
0.8861 High Similarity NPC95842
0.8861 High Similarity NPC121568
0.8854 High Similarity NPC133856
0.8846 High Similarity NPC233267
0.8846 High Similarity NPC65775
0.8846 High Similarity NPC474052
0.8846 High Similarity NPC291049
0.8846 High Similarity NPC269420
0.8846 High Similarity NPC3642
0.8846 High Similarity NPC10027
0.8846 High Similarity NPC473978
0.8839 High Similarity NPC126767
0.8839 High Similarity NPC190648
0.8839 High Similarity NPC261271
0.8839 High Similarity NPC290194
0.8839 High Similarity NPC259632
0.8839 High Similarity NPC289042
0.8839 High Similarity NPC312929
0.8839 High Similarity NPC118027
0.8839 High Similarity NPC56433
0.8839 High Similarity NPC475348
0.8839 High Similarity NPC245584
0.8831 High Similarity NPC194949
0.8831 High Similarity NPC282957
0.8827 High Similarity NPC473011
0.8824 High Similarity NPC310340
0.882 High Similarity NPC470810
0.882 High Similarity NPC98023
0.882 High Similarity NPC226462
0.882 High Similarity NPC42965
0.8812 High Similarity NPC263483
0.8812 High Similarity NPC287789
0.8812 High Similarity NPC272196
0.8812 High Similarity NPC271741
0.8812 High Similarity NPC268360
0.8805 High Similarity NPC37253
0.8805 High Similarity NPC79375
0.8805 High Similarity NPC275575
0.8805 High Similarity NPC148938
0.8802 High Similarity NPC300657
0.8802 High Similarity NPC477991
0.8802 High Similarity NPC477992
0.8797 High Similarity NPC208011
0.8797 High Similarity NPC39154
0.8797 High Similarity NPC78324
0.8797 High Similarity NPC175978
0.8797 High Similarity NPC142527
0.8797 High Similarity NPC273483
0.8797 High Similarity NPC115601
0.8795 High Similarity NPC4200
0.879 High Similarity NPC227122
0.879 High Similarity NPC472633
0.879 High Similarity NPC307780
0.879 High Similarity NPC147735
0.879 High Similarity NPC294646
0.879 High Similarity NPC309979
0.879 High Similarity NPC470568
0.8788 High Similarity NPC475212
0.8788 High Similarity NPC188079

  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 NPC189552 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
0.9487 High Similarity NPD6959 Discontinued
0.8889 High Similarity NPD7390 Discontinued
0.872 High Similarity NPD7852 Clinical (unspecified phase)
0.871 High Similarity NPD7410 Clinical (unspecified phase)
0.871 High Similarity NPD4378 Clinical (unspecified phase)
0.8688 High Similarity NPD8443 Clinical (unspecified phase)
0.8625 High Similarity NPD7819 Suspended
0.8598 High Similarity NPD6232 Discontinued
0.8554 High Similarity NPD7473 Discontinued
0.8519 High Similarity NPD7768 Phase 2
0.8395 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8385 Intermediate Similarity NPD7411 Suspended
0.8323 Intermediate Similarity NPD4380 Phase 2
0.8274 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8274 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8274 Intermediate Similarity NPD6166 Phase 2
0.8242 Intermediate Similarity NPD3749 Approved
0.8239 Intermediate Similarity NPD2532 Approved
0.8239 Intermediate Similarity NPD2533 Approved
0.8239 Intermediate Similarity NPD2534 Approved
0.8235 Intermediate Similarity NPD5844 Phase 1
0.8205 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.8176 Intermediate Similarity NPD1511 Approved
0.8171 Intermediate Similarity NPD2801 Approved
0.8148 Intermediate Similarity NPD3226 Approved
0.8141 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8141 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8129 Intermediate Similarity NPD1510 Phase 2
0.8129 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.8129 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8117 Intermediate Similarity NPD1607 Approved
0.811 Intermediate Similarity NPD1934 Approved
0.8101 Intermediate Similarity NPD3750 Approved
0.8089 Intermediate Similarity NPD1549 Phase 2
0.8077 Intermediate Similarity NPD2796 Approved
0.8075 Intermediate Similarity NPD1512 Approved
0.8024 Intermediate Similarity NPD7075 Discontinued
0.8024 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD8312 Approved
0.8 Intermediate Similarity NPD8313 Approved
0.7989 Intermediate Similarity NPD6559 Discontinued
0.7987 Intermediate Similarity NPD1240 Approved
0.7978 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7964 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7962 Intermediate Similarity NPD5404 Approved
0.7962 Intermediate Similarity NPD5406 Approved
0.7962 Intermediate Similarity NPD5408 Approved
0.7962 Intermediate Similarity NPD5405 Approved
0.7931 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7925 Intermediate Similarity NPD2800 Approved
0.7919 Intermediate Similarity NPD7054 Approved
0.7904 Intermediate Similarity NPD3817 Phase 2
0.7892 Intermediate Similarity NPD6801 Discontinued
0.7889 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7874 Intermediate Similarity NPD7074 Phase 3
0.7874 Intermediate Similarity NPD7472 Approved
0.7848 Intermediate Similarity NPD6100 Approved
0.7848 Intermediate Similarity NPD6099 Approved
0.7844 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7841 Intermediate Similarity NPD7808 Phase 3
0.7829 Intermediate Similarity NPD6797 Phase 2
0.7824 Intermediate Similarity NPD5494 Approved
0.7812 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7799 Intermediate Similarity NPD2346 Discontinued
0.7791 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7785 Intermediate Similarity NPD3748 Approved
0.7784 Intermediate Similarity NPD7251 Discontinued
0.7771 Intermediate Similarity NPD6599 Discontinued
0.7764 Intermediate Similarity NPD7003 Approved
0.7759 Intermediate Similarity NPD3818 Discontinued
0.7751 Intermediate Similarity NPD3882 Suspended
0.7738 Intermediate Similarity NPD1465 Phase 2
0.7737 Intermediate Similarity NPD8151 Discontinued
0.7736 Intermediate Similarity NPD2935 Discontinued
0.7711 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7702 Intermediate Similarity NPD1243 Approved
0.7692 Intermediate Similarity NPD5402 Approved
0.7677 Intermediate Similarity NPD4625 Phase 3
0.7658 Intermediate Similarity NPD6651 Approved
0.7657 Intermediate Similarity NPD7177 Discontinued
0.763 Intermediate Similarity NPD5711 Approved
0.763 Intermediate Similarity NPD5710 Approved
0.7628 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7625 Intermediate Similarity NPD1551 Phase 2
0.7622 Intermediate Similarity NPD6799 Approved
0.759 Intermediate Similarity NPD920 Approved
0.759 Intermediate Similarity NPD5403 Approved
0.7578 Intermediate Similarity NPD2344 Approved
0.7576 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7546 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7542 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7542 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD7229 Phase 3
0.7526 Intermediate Similarity NPD7871 Phase 2
0.7526 Intermediate Similarity NPD7870 Phase 2
0.75 Intermediate Similarity NPD6781 Approved
0.75 Intermediate Similarity NPD6777 Approved
0.75 Intermediate Similarity NPD6776 Approved
0.75 Intermediate Similarity NPD6780 Approved
0.75 Intermediate Similarity NPD6778 Approved
0.75 Intermediate Similarity NPD6779 Approved
0.75 Intermediate Similarity NPD6782 Approved
0.75 Intermediate Similarity NPD4908 Phase 1
0.7486 Intermediate Similarity NPD3926 Phase 2
0.7474 Intermediate Similarity NPD7698 Approved
0.7474 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7474 Intermediate Similarity NPD7697 Approved
0.7474 Intermediate Similarity NPD7783 Phase 2
0.7474 Intermediate Similarity NPD7696 Phase 3
0.747 Intermediate Similarity NPD5401 Approved
0.747 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7455 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7453 Intermediate Similarity NPD2799 Discontinued
0.743 Intermediate Similarity NPD5953 Discontinued
0.7429 Intermediate Similarity NPD3787 Discontinued
0.7427 Intermediate Similarity NPD8455 Phase 2
0.7405 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7405 Intermediate Similarity NPD2313 Discontinued
0.7396 Intermediate Similarity NPD7458 Discontinued
0.7394 Intermediate Similarity NPD2309 Approved
0.7386 Intermediate Similarity NPD1201 Approved
0.7382 Intermediate Similarity NPD7435 Discontinued
0.7377 Intermediate Similarity NPD8150 Discontinued
0.7371 Intermediate Similarity NPD1247 Approved
0.736 Intermediate Similarity NPD3751 Discontinued
0.7356 Intermediate Similarity NPD919 Approved
0.734 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD4628 Phase 3
0.7326 Intermediate Similarity NPD4363 Phase 3
0.7326 Intermediate Similarity NPD4360 Phase 2
0.732 Intermediate Similarity NPD7701 Phase 2
0.7318 Intermediate Similarity NPD7286 Phase 2
0.7308 Intermediate Similarity NPD1470 Approved
0.7297 Intermediate Similarity NPD4287 Approved
0.7278 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD7199 Phase 2
0.7267 Intermediate Similarity NPD37 Approved
0.7257 Intermediate Similarity NPD6234 Discontinued
0.7245 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7245 Intermediate Similarity NPD7874 Approved
0.7241 Intermediate Similarity NPD4967 Phase 2
0.7241 Intermediate Similarity NPD4966 Approved
0.7241 Intermediate Similarity NPD4965 Approved
0.724 Intermediate Similarity NPD6823 Phase 2
0.7234 Intermediate Similarity NPD6534 Approved
0.7234 Intermediate Similarity NPD6535 Approved
0.7229 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7225 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD6273 Approved
0.7211 Intermediate Similarity NPD7700 Phase 2
0.7211 Intermediate Similarity NPD7699 Phase 2
0.7208 Intermediate Similarity NPD7801 Approved
0.7205 Intermediate Similarity NPD943 Approved
0.7191 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.719 Intermediate Similarity NPD1651 Approved
0.7188 Intermediate Similarity NPD3268 Approved
0.7184 Intermediate Similarity NPD7654 Discontinued
0.7184 Intermediate Similarity NPD4288 Approved
0.7179 Intermediate Similarity NPD4749 Approved
0.7167 Intermediate Similarity NPD7228 Approved
0.7152 Intermediate Similarity NPD2798 Approved
0.7134 Intermediate Similarity NPD4308 Phase 3
0.7134 Intermediate Similarity NPD1283 Approved
0.7105 Intermediate Similarity NPD4361 Phase 2
0.7105 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7089 Intermediate Similarity NPD1203 Approved
0.7089 Intermediate Similarity NPD2797 Approved
0.7083 Intermediate Similarity NPD8285 Discontinued
0.7081 Intermediate Similarity NPD3764 Approved
0.7081 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7077 Intermediate Similarity NPD8319 Approved
0.7077 Intermediate Similarity NPD8320 Phase 1
0.7072 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD6832 Phase 2
0.7055 Intermediate Similarity NPD5124 Phase 1
0.7055 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7051 Intermediate Similarity NPD1610 Phase 2
0.7048 Intermediate Similarity NPD1471 Phase 3
0.7043 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD7033 Discontinued
0.7025 Intermediate Similarity NPD3225 Approved
0.7013 Intermediate Similarity NPD1548 Phase 1
0.7006 Intermediate Similarity NPD1608 Approved
0.7006 Intermediate Similarity NPD3972 Approved
0.7005 Intermediate Similarity NPD8434 Phase 2
0.7 Intermediate Similarity NPD6213 Phase 3
0.7 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD6212 Phase 3
0.6994 Remote Similarity NPD2979 Phase 3
0.6976 Remote Similarity NPD8155 Clinical (unspecified phase)
0.6975 Remote Similarity NPD411 Approved
0.6975 Remote Similarity NPD1699 Clinical (unspecified phase)
0.6964 Remote Similarity NPD2654 Approved
0.6964 Remote Similarity NPD5698 Clinical (unspecified phase)
0.6957 Remote Similarity NPD1529 Clinical (unspecified phase)
0.6951 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6951 Remote Similarity NPD230 Phase 1

  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