Structure

Physi-Chem Properties

Molecular Weight:  288.1
Volume:  281.835
LogP:  1.676
LogD:  1.19
LogS:  -3.607
# Rotatable Bonds:  0
TPSA:  72.83
# H-Bond Aceptor:  5
# H-Bond Donor:  1
# Rings:  4
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.536
Synthetic Accessibility Score:  5.306
Fsp3:  0.5
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
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:  -5.23
MDCK Permeability:  2.465683064656332e-05
Pgp-inhibitor:  0.275
Pgp-substrate:  0.25
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.996
30% Bioavailability (F30%):  0.102

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.969
Plasma Protein Binding (PPB):  62.818939208984375%
Volume Distribution (VD):  0.502
Pgp-substrate:  58.38120651245117%

ADMET: Metabolism

CYP1A2-inhibitor:  0.024
CYP1A2-substrate:  0.14
CYP2C19-inhibitor:  0.017
CYP2C19-substrate:  0.38
CYP2C9-inhibitor:  0.012
CYP2C9-substrate:  0.039
CYP2D6-inhibitor:  0.001
CYP2D6-substrate:  0.026
CYP3A4-inhibitor:  0.347
CYP3A4-substrate:  0.587

ADMET: Excretion

Clearance (CL):  7.961
Half-life (T1/2):  0.865

ADMET: Toxicity

hERG Blockers:  0.006
Human Hepatotoxicity (H-HT):  0.05
Drug-inuced Liver Injury (DILI):  0.458
AMES Toxicity:  0.215
Rat Oral Acute Toxicity:  0.977
Maximum Recommended Daily Dose:  0.96
Skin Sensitization:  0.941
Carcinogencity:  0.474
Eye Corrosion:  0.902
Eye Irritation:  0.887
Respiratory Toxicity:  0.951

Download Data

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

  Natural Product: NPC244456

Natural Product ID:  NPC244456
Common Name*:   HBGYEPXELMLLBL-PDGPNTQRSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  HBGYEPXELMLLBL-PDGPNTQRSA-N
Standard InCHI:  InChI=1S/C16H16O5/c1-15-4-3-11(17)16(2)13(15)10(21-14(16)19)5-8-7-20-12(18)6-9(8)15/h3-6,10-11,13,17H,7H2,1-2H3/t10-,11+,13-,15-,16+/m1/s1
SMILES:  O=C1OCC2=C[C@@H]3[C@@H]4[C@](C2=C1)(C)C=C[C@@H]([C@]4(C)C(=O)O3)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2011693
PubChem CID:   60151312
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001640] Naphthopyrans

*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
NPO32742 aspergillus wentii en-48 Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[22283451]

☑ 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
NPT165 Cell Line HeLa Homo sapiens IC50 = 63000.0 nM PMID[456480]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 38000.0 nM PMID[456480]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 = 42000.0 nM PMID[456480]
NPT397 Cell Line NCI-H460 Homo sapiens IC50 = 42000.0 nM PMID[456480]
NPT1312 Cell Line SW1990 Homo sapiens IC50 = 63000.0 nM PMID[456480]
NPT20 Organism Candida albicans Candida albicans MIC = 16.0 ug.mL-1 PMID[456480]

☑ 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 NPC244456 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 NPC469657
0.9082 High Similarity NPC235369
0.9032 High Similarity NPC469372
0.8725 High Similarity NPC91034
0.87 High Similarity NPC273005
0.87 High Similarity NPC31058
0.87 High Similarity NPC469606
0.8641 High Similarity NPC220155
0.8632 High Similarity NPC212679
0.8632 High Similarity NPC469595
0.8632 High Similarity NPC220454
0.8571 High Similarity NPC474315
0.85 High Similarity NPC476299
0.85 High Similarity NPC474012
0.8454 Intermediate Similarity NPC115021
0.8447 Intermediate Similarity NPC469607
0.8381 Intermediate Similarity NPC137911
0.8381 Intermediate Similarity NPC228477
0.8367 Intermediate Similarity NPC53685
0.8367 Intermediate Similarity NPC477130
0.8367 Intermediate Similarity NPC477129
0.8316 Intermediate Similarity NPC312561
0.8302 Intermediate Similarity NPC29133
0.83 Intermediate Similarity NPC53844
0.83 Intermediate Similarity NPC208094
0.8283 Intermediate Similarity NPC209355
0.8273 Intermediate Similarity NPC284707
0.8269 Intermediate Similarity NPC477125
0.8257 Intermediate Similarity NPC64318
0.8247 Intermediate Similarity NPC232426
0.8247 Intermediate Similarity NPC281942
0.8224 Intermediate Similarity NPC470961
0.8218 Intermediate Similarity NPC141191
0.8218 Intermediate Similarity NPC316598
0.82 Intermediate Similarity NPC112654
0.8182 Intermediate Similarity NPC469684
0.8182 Intermediate Similarity NPC98249
0.8182 Intermediate Similarity NPC53396
0.8173 Intermediate Similarity NPC296950
0.8173 Intermediate Similarity NPC309190
0.8173 Intermediate Similarity NPC146731
0.8163 Intermediate Similarity NPC472814
0.8163 Intermediate Similarity NPC177037
0.8163 Intermediate Similarity NPC141831
0.8148 Intermediate Similarity NPC191620
0.8144 Intermediate Similarity NPC218927
0.8144 Intermediate Similarity NPC168131
0.8144 Intermediate Similarity NPC206001
0.8131 Intermediate Similarity NPC478209
0.8119 Intermediate Similarity NPC169205
0.8119 Intermediate Similarity NPC202705
0.8108 Intermediate Similarity NPC186525
0.81 Intermediate Similarity NPC183012
0.81 Intermediate Similarity NPC295347
0.8073 Intermediate Similarity NPC469496
0.8073 Intermediate Similarity NPC469454
0.8073 Intermediate Similarity NPC469463
0.8073 Intermediate Similarity NPC122056
0.8061 Intermediate Similarity NPC469368
0.8058 Intermediate Similarity NPC472637
0.8056 Intermediate Similarity NPC304180
0.8056 Intermediate Similarity NPC179798
0.8041 Intermediate Similarity NPC477128
0.8041 Intermediate Similarity NPC476805
0.8041 Intermediate Similarity NPC477302
0.8041 Intermediate Similarity NPC136879
0.8041 Intermediate Similarity NPC24816
0.8039 Intermediate Similarity NPC23364
0.8021 Intermediate Similarity NPC305475
0.8021 Intermediate Similarity NPC475461
0.802 Intermediate Similarity NPC185553
0.802 Intermediate Similarity NPC242848
0.8019 Intermediate Similarity NPC469853
0.8 Intermediate Similarity NPC147912
0.8 Intermediate Similarity NPC167219
0.8 Intermediate Similarity NPC67259
0.7982 Intermediate Similarity NPC236217
0.7981 Intermediate Similarity NPC475320
0.7981 Intermediate Similarity NPC114540
0.7981 Intermediate Similarity NPC155332
0.7981 Intermediate Similarity NPC32577
0.798 Intermediate Similarity NPC36491
0.798 Intermediate Similarity NPC186363
0.798 Intermediate Similarity NPC233345
0.7963 Intermediate Similarity NPC37116
0.7963 Intermediate Similarity NPC5103
0.7963 Intermediate Similarity NPC235014
0.7961 Intermediate Similarity NPC477720
0.7959 Intermediate Similarity NPC5509
0.7959 Intermediate Similarity NPC284561
0.7946 Intermediate Similarity NPC50774
0.7946 Intermediate Similarity NPC709
0.7941 Intermediate Similarity NPC70145
0.7941 Intermediate Similarity NPC91695
0.7941 Intermediate Similarity NPC475709
0.7941 Intermediate Similarity NPC474343
0.7925 Intermediate Similarity NPC478208
0.7925 Intermediate Similarity NPC266570
0.7921 Intermediate Similarity NPC193645
0.7921 Intermediate Similarity NPC20546
0.7921 Intermediate Similarity NPC48803
0.7921 Intermediate Similarity NPC275960
0.7921 Intermediate Similarity NPC90121
0.7917 Intermediate Similarity NPC147921
0.7917 Intermediate Similarity NPC470755
0.7917 Intermediate Similarity NPC255307
0.7909 Intermediate Similarity NPC478212
0.7909 Intermediate Similarity NPC56448
0.7909 Intermediate Similarity NPC25909
0.7905 Intermediate Similarity NPC159533
0.7905 Intermediate Similarity NPC475526
0.7905 Intermediate Similarity NPC183570
0.7905 Intermediate Similarity NPC329345
0.7905 Intermediate Similarity NPC473283
0.79 Intermediate Similarity NPC271652
0.79 Intermediate Similarity NPC166346
0.789 Intermediate Similarity NPC188738
0.789 Intermediate Similarity NPC324683
0.7885 Intermediate Similarity NPC99411
0.7885 Intermediate Similarity NPC115899
0.7885 Intermediate Similarity NPC63249
0.7885 Intermediate Similarity NPC146822
0.7879 Intermediate Similarity NPC51486
0.7879 Intermediate Similarity NPC472307
0.7879 Intermediate Similarity NPC15059
0.787 Intermediate Similarity NPC475065
0.7864 Intermediate Similarity NPC98868
0.7864 Intermediate Similarity NPC124512
0.7864 Intermediate Similarity NPC166745
0.7864 Intermediate Similarity NPC478056
0.7864 Intermediate Similarity NPC159763
0.7864 Intermediate Similarity NPC278386
0.7864 Intermediate Similarity NPC216478
0.7864 Intermediate Similarity NPC471717
0.7864 Intermediate Similarity NPC235464
0.7857 Intermediate Similarity NPC72397
0.7857 Intermediate Similarity NPC312824
0.7857 Intermediate Similarity NPC167606
0.7857 Intermediate Similarity NPC470493
0.7857 Intermediate Similarity NPC476803
0.7857 Intermediate Similarity NPC183580
0.7857 Intermediate Similarity NPC226863
0.7857 Intermediate Similarity NPC140055
0.7857 Intermediate Similarity NPC470492
0.7857 Intermediate Similarity NPC286528
0.7857 Intermediate Similarity NPC20302
0.785 Intermediate Similarity NPC473284
0.785 Intermediate Similarity NPC330011
0.785 Intermediate Similarity NPC329048
0.7843 Intermediate Similarity NPC240673
0.7843 Intermediate Similarity NPC17578
0.7838 Intermediate Similarity NPC474181
0.7835 Intermediate Similarity NPC316426
0.7835 Intermediate Similarity NPC315395
0.783 Intermediate Similarity NPC475676
0.783 Intermediate Similarity NPC220964
0.7826 Intermediate Similarity NPC287236
0.7822 Intermediate Similarity NPC470697
0.7822 Intermediate Similarity NPC474555
0.7822 Intermediate Similarity NPC7165
0.7822 Intermediate Similarity NPC298973
0.7822 Intermediate Similarity NPC104925
0.7818 Intermediate Similarity NPC69291
0.7818 Intermediate Similarity NPC269530
0.7812 Intermediate Similarity NPC114979
0.7812 Intermediate Similarity NPC158756
0.7812 Intermediate Similarity NPC476804
0.7812 Intermediate Similarity NPC191476
0.781 Intermediate Similarity NPC476081
0.781 Intermediate Similarity NPC134077
0.781 Intermediate Similarity NPC476890
0.781 Intermediate Similarity NPC164551
0.7807 Intermediate Similarity NPC474370
0.7807 Intermediate Similarity NPC31641
0.7807 Intermediate Similarity NPC473145
0.78 Intermediate Similarity NPC72845
0.78 Intermediate Similarity NPC300312
0.78 Intermediate Similarity NPC45269
0.78 Intermediate Similarity NPC252433
0.78 Intermediate Similarity NPC111114
0.78 Intermediate Similarity NPC303697
0.78 Intermediate Similarity NPC261607
0.7798 Intermediate Similarity NPC478211
0.7789 Intermediate Similarity NPC89555
0.7788 Intermediate Similarity NPC117685
0.7788 Intermediate Similarity NPC469864
0.7788 Intermediate Similarity NPC54705
0.7788 Intermediate Similarity NPC47024
0.7788 Intermediate Similarity NPC469872
0.7788 Intermediate Similarity NPC227865
0.7788 Intermediate Similarity NPC108581
0.7788 Intermediate Similarity NPC478206
0.7788 Intermediate Similarity NPC266955
0.7788 Intermediate Similarity NPC475913
0.7788 Intermediate Similarity NPC478205
0.7778 Intermediate Similarity NPC50488
0.7778 Intermediate Similarity NPC275539
0.7778 Intermediate Similarity NPC118011
0.7778 Intermediate Similarity NPC97577
0.7778 Intermediate Similarity NPC474396

  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 NPC244456 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
0.798 Intermediate Similarity NPD6411 Approved
0.7921 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.79 Intermediate Similarity NPD5779 Approved
0.79 Intermediate Similarity NPD5778 Approved
0.7864 Intermediate Similarity NPD4225 Approved
0.7857 Intermediate Similarity NPD7115 Discovery
0.7778 Intermediate Similarity NPD5764 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD6101 Approved
0.77 Intermediate Similarity NPD5785 Approved
0.7551 Intermediate Similarity NPD1694 Approved
0.7451 Intermediate Similarity NPD5281 Approved
0.7451 Intermediate Similarity NPD5284 Approved
0.7379 Intermediate Similarity NPD6399 Phase 3
0.729 Intermediate Similarity NPD7640 Approved
0.729 Intermediate Similarity NPD7639 Approved
0.7288 Intermediate Similarity NPD8513 Phase 3
0.7282 Intermediate Similarity NPD7637 Suspended
0.7245 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7238 Intermediate Similarity NPD5695 Phase 3
0.72 Intermediate Similarity NPD5363 Approved
0.7196 Intermediate Similarity NPD7638 Approved
0.7193 Intermediate Similarity NPD6053 Discontinued
0.7184 Intermediate Similarity NPD5207 Approved
0.7168 Intermediate Similarity NPD6371 Approved
0.7143 Intermediate Similarity NPD5282 Discontinued
0.7143 Intermediate Similarity NPD8515 Approved
0.7143 Intermediate Similarity NPD8517 Approved
0.7143 Intermediate Similarity NPD8516 Approved
0.7143 Intermediate Similarity NPD6686 Approved
0.7129 Intermediate Similarity NPD5279 Phase 3
0.7115 Intermediate Similarity NPD7983 Approved
0.7103 Intermediate Similarity NPD6083 Phase 2
0.7103 Intermediate Similarity NPD6084 Phase 2
0.7103 Intermediate Similarity NPD7902 Approved
0.71 Intermediate Similarity NPD6400 Clinical (unspecified phase)
0.7071 Intermediate Similarity NPD4270 Approved
0.7071 Intermediate Similarity NPD5209 Approved
0.7071 Intermediate Similarity NPD4269 Approved
0.7054 Intermediate Similarity NPD5697 Approved
0.7037 Intermediate Similarity NPD5696 Approved
0.7019 Intermediate Similarity NPD46 Approved
0.7019 Intermediate Similarity NPD6698 Approved
0.7 Intermediate Similarity NPD7154 Phase 3
0.6991 Remote Similarity NPD6899 Approved
0.6991 Remote Similarity NPD6881 Approved
0.6981 Remote Similarity NPD7748 Approved
0.6964 Remote Similarity NPD5739 Approved
0.6964 Remote Similarity NPD7128 Approved
0.6964 Remote Similarity NPD6675 Approved
0.6964 Remote Similarity NPD6402 Approved
0.6961 Remote Similarity NPD3618 Phase 1
0.6961 Remote Similarity NPD5330 Approved
0.6961 Remote Similarity NPD5786 Approved
0.6961 Remote Similarity NPD7146 Approved
0.6961 Remote Similarity NPD6684 Approved
0.6961 Remote Similarity NPD7334 Approved
0.6961 Remote Similarity NPD7521 Approved
0.6961 Remote Similarity NPD6409 Approved
0.6957 Remote Similarity NPD6650 Approved
0.6957 Remote Similarity NPD6649 Approved
0.6957 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6952 Remote Similarity NPD5694 Approved
0.6952 Remote Similarity NPD7515 Phase 2
0.6931 Remote Similarity NPD3133 Approved
0.6931 Remote Similarity NPD3666 Approved
0.6931 Remote Similarity NPD3665 Phase 1
0.693 Remote Similarity NPD6372 Approved
0.693 Remote Similarity NPD6012 Approved
0.693 Remote Similarity NPD6373 Approved
0.693 Remote Similarity NPD6014 Approved
0.693 Remote Similarity NPD6013 Approved
0.693 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6923 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6903 Remote Similarity NPD5701 Approved
0.6903 Remote Similarity NPD7899 Clinical (unspecified phase)
0.69 Remote Similarity NPD3667 Approved
0.6881 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6875 Remote Similarity NPD8039 Approved
0.687 Remote Similarity NPD6883 Approved
0.687 Remote Similarity NPD7290 Approved
0.687 Remote Similarity NPD5955 Clinical (unspecified phase)
0.687 Remote Similarity NPD7102 Approved
0.6869 Remote Similarity NPD4252 Approved
0.6869 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6857 Remote Similarity NPD5692 Phase 3
0.6857 Remote Similarity NPD7838 Discovery
0.6855 Remote Similarity NPD8074 Phase 3
0.6852 Remote Similarity NPD7839 Suspended
0.6847 Remote Similarity NPD5211 Phase 2
0.6842 Remote Similarity NPD7320 Approved
0.6842 Remote Similarity NPD6011 Approved
0.6837 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6832 Remote Similarity NPD5362 Discontinued
0.6827 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6827 Remote Similarity NPD5737 Approved
0.6827 Remote Similarity NPD6903 Approved
0.6827 Remote Similarity NPD6672 Approved
0.6822 Remote Similarity NPD7900 Approved
0.6822 Remote Similarity NPD7901 Clinical (unspecified phase)
0.681 Remote Similarity NPD6869 Approved
0.681 Remote Similarity NPD6847 Approved
0.681 Remote Similarity NPD8130 Phase 1
0.681 Remote Similarity NPD6617 Approved
0.68 Remote Similarity NPD5369 Approved
0.6796 Remote Similarity NPD4519 Discontinued
0.6796 Remote Similarity NPD4623 Approved
0.6792 Remote Similarity NPD6050 Approved
0.6792 Remote Similarity NPD5693 Phase 1
0.6772 Remote Similarity NPD7260 Phase 2
0.6765 Remote Similarity NPD4786 Approved
0.6762 Remote Similarity NPD4753 Phase 2
0.6759 Remote Similarity NPD5210 Approved
0.6759 Remote Similarity NPD4629 Approved
0.6752 Remote Similarity NPD6882 Approved
0.6752 Remote Similarity NPD8297 Approved
0.6726 Remote Similarity NPD5141 Approved
0.67 Remote Similarity NPD4819 Approved
0.67 Remote Similarity NPD4820 Approved
0.67 Remote Similarity NPD4821 Approved
0.67 Remote Similarity NPD4822 Approved
0.6696 Remote Similarity NPD7632 Discontinued
0.6667 Remote Similarity NPD6404 Discontinued
0.6667 Remote Similarity NPD6008 Approved
0.6667 Remote Similarity NPD5286 Approved
0.6667 Remote Similarity NPD4696 Approved
0.6667 Remote Similarity NPD5285 Approved
0.6667 Remote Similarity NPD4271 Approved
0.6667 Remote Similarity NPD4268 Approved
0.6639 Remote Similarity NPD6319 Approved
0.6636 Remote Similarity NPD4755 Approved
0.6636 Remote Similarity NPD6079 Approved
0.6635 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6635 Remote Similarity NPD5280 Approved
0.6635 Remote Similarity NPD4249 Approved
0.6635 Remote Similarity NPD4694 Approved
0.6609 Remote Similarity NPD6412 Phase 2
0.6609 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6606 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6604 Remote Similarity NPD5328 Approved
0.6585 Remote Similarity NPD7503 Approved
0.6574 Remote Similarity NPD4202 Approved
0.6571 Remote Similarity NPD4250 Approved
0.6571 Remote Similarity NPD4251 Approved
0.6569 Remote Similarity NPD6435 Approved
0.656 Remote Similarity NPD7492 Approved
0.6552 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6549 Remote Similarity NPD5226 Approved
0.6549 Remote Similarity NPD5225 Approved
0.6549 Remote Similarity NPD5224 Approved
0.6549 Remote Similarity NPD4633 Approved
0.6545 Remote Similarity NPD5222 Approved
0.6545 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6545 Remote Similarity NPD4697 Phase 3
0.6545 Remote Similarity NPD5221 Approved
0.6538 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6535 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6535 Remote Similarity NPD4695 Discontinued
0.6531 Remote Similarity NPD8264 Approved
0.6525 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6518 Remote Similarity NPD4700 Approved
0.6509 Remote Similarity NPD4518 Approved
0.6508 Remote Similarity NPD6616 Approved
0.6504 Remote Similarity NPD6054 Approved
0.6491 Remote Similarity NPD5175 Approved
0.6491 Remote Similarity NPD5174 Approved
0.6486 Remote Similarity NPD5173 Approved
0.6484 Remote Similarity NPD7319 Approved
0.6481 Remote Similarity NPD8034 Phase 2
0.6481 Remote Similarity NPD8035 Phase 2
0.6476 Remote Similarity NPD5690 Phase 2
0.6462 Remote Similarity NPD6845 Suspended
0.646 Remote Similarity NPD5223 Approved
0.6457 Remote Similarity NPD7078 Approved
0.6455 Remote Similarity NPD5654 Approved
0.6452 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6452 Remote Similarity NPD6015 Approved
0.6452 Remote Similarity NPD6016 Approved
0.6449 Remote Similarity NPD6673 Approved
0.6449 Remote Similarity NPD1695 Approved
0.6449 Remote Similarity NPD6080 Approved
0.6449 Remote Similarity NPD6051 Approved
0.6449 Remote Similarity NPD6904 Approved
0.6446 Remote Similarity NPD6274 Approved
0.6442 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6442 Remote Similarity NPD3668 Phase 3
0.6441 Remote Similarity NPD4634 Approved
0.6423 Remote Similarity NPD7101 Approved
0.6423 Remote Similarity NPD7100 Approved
0.6417 Remote Similarity NPD4632 Approved
0.6415 Remote Similarity NPD3573 Approved
0.6408 Remote Similarity NPD4223 Phase 3
0.6408 Remote Similarity NPD4221 Approved
0.6406 Remote Similarity NPD7736 Approved
0.64 Remote Similarity NPD4756 Discovery
0.64 Remote Similarity NPD5988 Approved
0.64 Remote Similarity NPD6370 Approved
0.6393 Remote Similarity NPD6317 Approved
0.6381 Remote Similarity NPD1696 Phase 3
0.6378 Remote Similarity NPD7507 Approved
0.6373 Remote Similarity NPD5368 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