Structure

Physi-Chem Properties

Molecular Weight:  304.09
Volume:  284.705
LogP:  1.399
LogD:  1.086
LogS:  -4.023
# Rotatable Bonds:  0
TPSA:  85.36
# H-Bond Aceptor:  6
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.517
Synthetic Accessibility Score:  5.489
Fsp3:  0.625
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:  -5.328
MDCK Permeability:  2.4606662918813527e-05
Pgp-inhibitor:  0.866
Pgp-substrate:  0.569
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.996
30% Bioavailability (F30%):  0.75

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.891
Plasma Protein Binding (PPB):  57.625553131103516%
Volume Distribution (VD):  0.454
Pgp-substrate:  61.870121002197266%

ADMET: Metabolism

CYP1A2-inhibitor:  0.035
CYP1A2-substrate:  0.14
CYP2C19-inhibitor:  0.021
CYP2C19-substrate:  0.538
CYP2C9-inhibitor:  0.009
CYP2C9-substrate:  0.034
CYP2D6-inhibitor:  0.003
CYP2D6-substrate:  0.075
CYP3A4-inhibitor:  0.037
CYP3A4-substrate:  0.421

ADMET: Excretion

Clearance (CL):  8.67
Half-life (T1/2):  0.868

ADMET: Toxicity

hERG Blockers:  0.004
Human Hepatotoxicity (H-HT):  0.177
Drug-inuced Liver Injury (DILI):  0.665
AMES Toxicity:  0.313
Rat Oral Acute Toxicity:  0.87
Maximum Recommended Daily Dose:  0.57
Skin Sensitization:  0.922
Carcinogencity:  0.396
Eye Corrosion:  0.906
Eye Irritation:  0.362
Respiratory Toxicity:  0.953

Download Data

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

  Natural Product: NPC53396

Natural Product ID:  NPC53396
Common Name*:   Asperolide B
IUPAC Name:   n.a.
Synonyms:   Asperolide B
Standard InCHIKey:  MJENRSWOSGZXHW-IPWFQQAISA-N
Standard InCHI:  InChI=1S/C16H16O6/c1-15-7-4-9(17)20-5-6(7)3-8-11(15)16(2,14(19)21-8)13-10(22-13)12(15)18/h3-4,8,10-13,18H,5H2,1-2H3/t8-,10+,11-,12-,13+,15-,16-/m1/s1
SMILES:  C[C@@]12C3=CC(=O)OCC3=C[C@@H]3[C@H]1[C@](C)([C@@H]1[C@H]([C@H]2O)O1)C(=O)O3
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2011692
PubChem CID:   70695738
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 = 56000.0 nM PMID[522528]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 63000.0 nM PMID[522528]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 = 35000.0 nM PMID[522528]
NPT397 Cell Line NCI-H460 Homo sapiens IC50 = 63000.0 nM PMID[522528]
NPT1312 Cell Line SW1990 Homo sapiens IC50 = 69000.0 nM PMID[522528]

☑ 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 NPC53396 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 NPC98249
0.9907 High Similarity NPC284707
0.9455 High Similarity NPC478204
0.9455 High Similarity NPC469684
0.9369 High Similarity NPC478205
0.9369 High Similarity NPC108581
0.9369 High Similarity NPC478206
0.9279 High Similarity NPC58662
0.9182 High Similarity NPC478212
0.9174 High Similarity NPC474846
0.9174 High Similarity NPC469655
0.9174 High Similarity NPC469656
0.9065 High Similarity NPC469607
0.9009 High Similarity NPC475966
0.8991 High Similarity NPC469370
0.8938 High Similarity NPC13713
0.8909 High Similarity NPC478209
0.8829 High Similarity NPC247031
0.8829 High Similarity NPC188738
0.8829 High Similarity NPC97939
0.8829 High Similarity NPC132790
0.8829 High Similarity NPC100329
0.8818 High Similarity NPC478210
0.8814 High Similarity NPC293112
0.8807 High Similarity NPC180744
0.8803 High Similarity NPC11895
0.8785 High Similarity NPC31058
0.8785 High Similarity NPC273005
0.8785 High Similarity NPC469606
0.875 High Similarity NPC269530
0.8739 High Similarity NPC253906
0.8739 High Similarity NPC478211
0.8729 High Similarity NPC172154
0.8729 High Similarity NPC81736
0.8718 High Similarity NPC170538
0.8673 High Similarity NPC471204
0.8655 High Similarity NPC473635
0.8644 High Similarity NPC67251
0.8644 High Similarity NPC469789
0.8621 High Similarity NPC470186
0.8596 High Similarity NPC117712
0.8584 High Similarity NPC476801
0.8584 High Similarity NPC472002
0.8583 High Similarity NPC476008
0.8571 High Similarity NPC24651
0.8571 High Similarity NPC210005
0.8571 High Similarity NPC8369
0.8559 High Similarity NPC312833
0.8547 High Similarity NPC475003
0.8547 High Similarity NPC268530
0.8547 High Similarity NPC154491
0.8547 High Similarity NPC251226
0.8545 High Similarity NPC102352
0.8545 High Similarity NPC478208
0.8532 High Similarity NPC159533
0.8522 High Similarity NPC477509
0.8522 High Similarity NPC478216
0.8522 High Similarity NPC207217
0.8509 High Similarity NPC469496
0.8509 High Similarity NPC469463
0.8509 High Similarity NPC469454
0.8509 High Similarity NPC477126
0.85 High Similarity NPC198209
0.85 High Similarity NPC477745
0.8496 Intermediate Similarity NPC304180
0.8496 Intermediate Similarity NPC179798
0.8487 Intermediate Similarity NPC265557
0.8487 Intermediate Similarity NPC91693
0.8487 Intermediate Similarity NPC105926
0.8487 Intermediate Similarity NPC18945
0.8475 Intermediate Similarity NPC67569
0.8475 Intermediate Similarity NPC102822
0.8475 Intermediate Similarity NPC477046
0.8475 Intermediate Similarity NPC159456
0.8475 Intermediate Similarity NPC4021
0.8468 Intermediate Similarity NPC3316
0.8468 Intermediate Similarity NPC230541
0.8468 Intermediate Similarity NPC144854
0.8462 Intermediate Similarity NPC42673
0.8455 Intermediate Similarity NPC146731
0.8455 Intermediate Similarity NPC296950
0.8448 Intermediate Similarity NPC97908
0.8448 Intermediate Similarity NPC470775
0.8448 Intermediate Similarity NPC470854
0.8448 Intermediate Similarity NPC176513
0.8448 Intermediate Similarity NPC473968
0.8448 Intermediate Similarity NPC474654
0.8448 Intermediate Similarity NPC122033
0.8448 Intermediate Similarity NPC473590
0.8448 Intermediate Similarity NPC287343
0.844 Intermediate Similarity NPC295791
0.8435 Intermediate Similarity NPC73314
0.8421 Intermediate Similarity NPC42658
0.8421 Intermediate Similarity NPC222834
0.8417 Intermediate Similarity NPC476729
0.8407 Intermediate Similarity NPC5103
0.8403 Intermediate Similarity NPC269642
0.8403 Intermediate Similarity NPC470265
0.8403 Intermediate Similarity NPC23786
0.8393 Intermediate Similarity NPC189075
0.8393 Intermediate Similarity NPC277017
0.8393 Intermediate Similarity NPC275539
0.8393 Intermediate Similarity NPC154608
0.8393 Intermediate Similarity NPC192813
0.8376 Intermediate Similarity NPC251310
0.8376 Intermediate Similarity NPC106644
0.8376 Intermediate Similarity NPC470776
0.8376 Intermediate Similarity NPC17772
0.8362 Intermediate Similarity NPC270478
0.8362 Intermediate Similarity NPC179626
0.8348 Intermediate Similarity NPC49451
0.8348 Intermediate Similarity NPC56448
0.8347 Intermediate Similarity NPC181999
0.8333 Intermediate Similarity NPC216478
0.8333 Intermediate Similarity NPC317107
0.8319 Intermediate Similarity NPC474243
0.8319 Intermediate Similarity NPC143706
0.8319 Intermediate Similarity NPC472534
0.8319 Intermediate Similarity NPC299590
0.8319 Intermediate Similarity NPC470779
0.8319 Intermediate Similarity NPC141350
0.8305 Intermediate Similarity NPC476529
0.8305 Intermediate Similarity NPC473636
0.8305 Intermediate Similarity NPC475041
0.8305 Intermediate Similarity NPC77689
0.8305 Intermediate Similarity NPC230513
0.8305 Intermediate Similarity NPC475775
0.8304 Intermediate Similarity NPC67321
0.8304 Intermediate Similarity NPC110496
0.8304 Intermediate Similarity NPC187435
0.8291 Intermediate Similarity NPC476712
0.8291 Intermediate Similarity NPC134430
0.8291 Intermediate Similarity NPC476713
0.8291 Intermediate Similarity NPC474518
0.8288 Intermediate Similarity NPC258532
0.8273 Intermediate Similarity NPC235369
0.8264 Intermediate Similarity NPC470922
0.8264 Intermediate Similarity NPC469790
0.8261 Intermediate Similarity NPC474516
0.8261 Intermediate Similarity NPC473877
0.8261 Intermediate Similarity NPC317687
0.8257 Intermediate Similarity NPC474012
0.8257 Intermediate Similarity NPC476299
0.8257 Intermediate Similarity NPC47024
0.8246 Intermediate Similarity NPC286880
0.8246 Intermediate Similarity NPC235014
0.8246 Intermediate Similarity NPC472215
0.8246 Intermediate Similarity NPC472214
0.8235 Intermediate Similarity NPC109607
0.8235 Intermediate Similarity NPC475885
0.8235 Intermediate Similarity NPC107338
0.8235 Intermediate Similarity NPC112038
0.823 Intermediate Similarity NPC37628
0.823 Intermediate Similarity NPC476802
0.823 Intermediate Similarity NPC94377
0.823 Intermediate Similarity NPC89171
0.823 Intermediate Similarity NPC469916
0.823 Intermediate Similarity NPC472439
0.822 Intermediate Similarity NPC709
0.822 Intermediate Similarity NPC204552
0.822 Intermediate Similarity NPC240509
0.822 Intermediate Similarity NPC188667
0.822 Intermediate Similarity NPC50774
0.822 Intermediate Similarity NPC186525
0.8214 Intermediate Similarity NPC477125
0.8205 Intermediate Similarity NPC96312
0.8205 Intermediate Similarity NPC328374
0.8205 Intermediate Similarity NPC476710
0.8205 Intermediate Similarity NPC474734
0.8205 Intermediate Similarity NPC476711
0.8205 Intermediate Similarity NPC251236
0.8205 Intermediate Similarity NPC40632
0.8198 Intermediate Similarity NPC23584
0.8197 Intermediate Similarity NPC203702
0.8197 Intermediate Similarity NPC225049
0.8197 Intermediate Similarity NPC120994
0.8197 Intermediate Similarity NPC471939
0.819 Intermediate Similarity NPC208998
0.819 Intermediate Similarity NPC51978
0.819 Intermediate Similarity NPC194273
0.819 Intermediate Similarity NPC94509
0.819 Intermediate Similarity NPC25909
0.819 Intermediate Similarity NPC7921
0.8182 Intermediate Similarity NPC308824
0.8182 Intermediate Similarity NPC469657
0.8182 Intermediate Similarity NPC244456
0.8174 Intermediate Similarity NPC474229
0.8174 Intermediate Similarity NPC201992
0.8174 Intermediate Similarity NPC146945
0.8174 Intermediate Similarity NPC171888
0.8167 Intermediate Similarity NPC46570
0.8165 Intermediate Similarity NPC222303
0.8158 Intermediate Similarity NPC42662
0.8158 Intermediate Similarity NPC153239
0.8151 Intermediate Similarity NPC305260
0.8151 Intermediate Similarity NPC473839
0.8151 Intermediate Similarity NPC211093
0.8151 Intermediate Similarity NPC470777
0.8151 Intermediate Similarity NPC270850
0.8151 Intermediate Similarity NPC156745

  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 NPC53396 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
0.8319 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.8136 Intermediate Similarity NPD7115 Discovery
0.8087 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD4225 Approved
0.7826 Intermediate Similarity NPD5954 Clinical (unspecified phase)
0.7759 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7724 Intermediate Similarity NPD8513 Phase 3
0.7586 Intermediate Similarity NPD6008 Approved
0.7581 Intermediate Similarity NPD8516 Approved
0.7581 Intermediate Similarity NPD8515 Approved
0.7581 Intermediate Similarity NPD8517 Approved
0.7578 Intermediate Similarity NPD7319 Approved
0.7522 Intermediate Similarity NPD7638 Approved
0.75 Intermediate Similarity NPD6319 Approved
0.7458 Intermediate Similarity NPD6686 Approved
0.7456 Intermediate Similarity NPD7639 Approved
0.7456 Intermediate Similarity NPD7640 Approved
0.7391 Intermediate Similarity NPD5344 Discontinued
0.7387 Intermediate Similarity NPD5778 Approved
0.7387 Intermediate Similarity NPD5779 Approved
0.7364 Intermediate Similarity NPD6698 Approved
0.7364 Intermediate Similarity NPD46 Approved
0.7344 Intermediate Similarity NPD7507 Approved
0.7323 Intermediate Similarity NPD8328 Phase 3
0.7304 Intermediate Similarity NPD6648 Approved
0.7297 Intermediate Similarity NPD6411 Approved
0.7295 Intermediate Similarity NPD4632 Approved
0.7287 Intermediate Similarity NPD8074 Phase 3
0.7266 Intermediate Similarity NPD7492 Approved
0.7222 Intermediate Similarity NPD6059 Approved
0.7222 Intermediate Similarity NPD6054 Approved
0.7213 Intermediate Similarity NPD6053 Discontinued
0.7209 Intermediate Similarity NPD6616 Approved
0.719 Intermediate Similarity NPD6371 Approved
0.7165 Intermediate Similarity NPD6016 Approved
0.7165 Intermediate Similarity NPD6015 Approved
0.7154 Intermediate Similarity NPD7078 Approved
0.7154 Intermediate Similarity NPD8293 Discontinued
0.7143 Intermediate Similarity NPD6402 Approved
0.7143 Intermediate Similarity NPD7128 Approved
0.7143 Intermediate Similarity NPD7983 Approved
0.7143 Intermediate Similarity NPD5739 Approved
0.7143 Intermediate Similarity NPD6675 Approved
0.712 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7117 Intermediate Similarity NPD5764 Clinical (unspecified phase)
0.7117 Intermediate Similarity NPD6101 Approved
0.7109 Intermediate Similarity NPD5988 Approved
0.7109 Intermediate Similarity NPD6370 Approved
0.7107 Intermediate Similarity NPD6372 Approved
0.7107 Intermediate Similarity NPD6373 Approved
0.7105 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7099 Intermediate Similarity NPD7736 Approved
0.7083 Intermediate Similarity NPD5701 Approved
0.7083 Intermediate Similarity NPD5697 Approved
0.7073 Intermediate Similarity NPD8297 Approved
0.7054 Intermediate Similarity NPD7838 Discovery
0.7049 Intermediate Similarity NPD4634 Approved
0.7031 Intermediate Similarity NPD7503 Approved
0.7031 Intermediate Similarity NPD6921 Approved
0.7025 Intermediate Similarity NPD6881 Approved
0.7025 Intermediate Similarity NPD7320 Approved
0.7025 Intermediate Similarity NPD6899 Approved
0.7008 Intermediate Similarity NPD7516 Approved
0.6992 Remote Similarity NPD6650 Approved
0.6992 Remote Similarity NPD6649 Approved
0.6984 Remote Similarity NPD6009 Approved
0.6983 Remote Similarity NPD7902 Approved
0.6967 Remote Similarity NPD6013 Approved
0.6967 Remote Similarity NPD6014 Approved
0.6967 Remote Similarity NPD6012 Approved
0.6967 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6942 Remote Similarity NPD6412 Phase 2
0.6942 Remote Similarity NPD7899 Clinical (unspecified phase)
0.694 Remote Similarity NPD7260 Phase 2
0.693 Remote Similarity NPD6399 Phase 3
0.6929 Remote Similarity NPD7327 Approved
0.6929 Remote Similarity NPD7328 Approved
0.6923 Remote Similarity NPD7604 Phase 2
0.6911 Remote Similarity NPD6883 Approved
0.6911 Remote Similarity NPD7290 Approved
0.6911 Remote Similarity NPD7102 Approved
0.6909 Remote Similarity NPD1694 Approved
0.6899 Remote Similarity NPD5983 Phase 2
0.6891 Remote Similarity NPD7632 Discontinued
0.6885 Remote Similarity NPD6011 Approved
0.687 Remote Similarity NPD7748 Approved
0.6855 Remote Similarity NPD6869 Approved
0.6855 Remote Similarity NPD8130 Phase 1
0.6855 Remote Similarity NPD6617 Approved
0.6855 Remote Similarity NPD6847 Approved
0.6847 Remote Similarity NPD3618 Phase 1
0.6842 Remote Similarity NPD7515 Phase 2
0.6842 Remote Similarity NPD7637 Suspended
0.6838 Remote Similarity NPD4755 Approved
0.6814 Remote Similarity NPD5328 Approved
0.68 Remote Similarity NPD6882 Approved
0.6769 Remote Similarity NPD8296 Approved
0.6769 Remote Similarity NPD8033 Approved
0.6769 Remote Similarity NPD8378 Approved
0.6769 Remote Similarity NPD8335 Approved
0.6769 Remote Similarity NPD8380 Approved
0.6769 Remote Similarity NPD8379 Approved
0.6765 Remote Similarity NPD6845 Suspended
0.6757 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6752 Remote Similarity NPD4697 Phase 3
0.675 Remote Similarity NPD5211 Phase 2
0.6724 Remote Similarity NPD7900 Approved
0.6724 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6723 Remote Similarity NPD4700 Approved
0.6723 Remote Similarity NPD5286 Approved
0.6723 Remote Similarity NPD4696 Approved
0.6723 Remote Similarity NPD5285 Approved
0.672 Remote Similarity NPD6401 Clinical (unspecified phase)
0.672 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6716 Remote Similarity NPD6033 Approved
0.6696 Remote Similarity NPD6079 Approved
0.6692 Remote Similarity NPD6336 Discontinued
0.6692 Remote Similarity NPD8377 Approved
0.6692 Remote Similarity NPD8294 Approved
0.6641 Remote Similarity NPD6274 Approved
0.6639 Remote Similarity NPD5141 Approved
0.6636 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6614 Remote Similarity NPD8133 Approved
0.6612 Remote Similarity NPD5224 Approved
0.6612 Remote Similarity NPD5226 Approved
0.6612 Remote Similarity NPD5225 Approved
0.6612 Remote Similarity NPD4633 Approved
0.661 Remote Similarity NPD5220 Clinical (unspecified phase)
0.661 Remote Similarity NPD5222 Approved
0.661 Remote Similarity NPD5221 Approved
0.6581 Remote Similarity NPD5282 Discontinued
0.6557 Remote Similarity NPD5174 Approved
0.6557 Remote Similarity NPD5175 Approved
0.6555 Remote Similarity NPD6084 Phase 2
0.6555 Remote Similarity NPD5173 Approved
0.6555 Remote Similarity NPD6083 Phase 2
0.6552 Remote Similarity NPD5281 Approved
0.6552 Remote Similarity NPD5284 Approved
0.6541 Remote Similarity NPD7830 Approved
0.6541 Remote Similarity NPD7829 Approved
0.6529 Remote Similarity NPD1700 Approved
0.6529 Remote Similarity NPD5223 Approved
0.6525 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6525 Remote Similarity NPD5695 Phase 3
0.6515 Remote Similarity NPD6291 Clinical (unspecified phase)
0.65 Remote Similarity NPD5696 Approved
0.65 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6496 Remote Similarity NPD4202 Approved
0.6491 Remote Similarity NPD3573 Approved
0.6491 Remote Similarity NPD7524 Approved
0.6489 Remote Similarity NPD7101 Approved
0.6489 Remote Similarity NPD7100 Approved
0.6486 Remote Similarity NPD3667 Approved
0.6466 Remote Similarity NPD5785 Approved
0.6462 Remote Similarity NPD6317 Approved
0.6454 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6452 Remote Similarity NPD4768 Approved
0.6452 Remote Similarity NPD4767 Approved
0.6423 Remote Similarity NPD4754 Approved
0.6418 Remote Similarity NPD6067 Discontinued
0.6412 Remote Similarity NPD6313 Approved
0.6412 Remote Similarity NPD6314 Approved
0.6412 Remote Similarity NPD6335 Approved
0.641 Remote Similarity NPD8035 Phase 2
0.641 Remote Similarity NPD8034 Phase 2
0.6404 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6404 Remote Similarity NPD7146 Approved
0.6404 Remote Similarity NPD7334 Approved
0.6404 Remote Similarity NPD6684 Approved
0.6404 Remote Similarity NPD5279 Phase 3
0.6404 Remote Similarity NPD6409 Approved
0.6404 Remote Similarity NPD7521 Approved
0.6404 Remote Similarity NPD5330 Approved
0.6393 Remote Similarity NPD4159 Approved
0.6391 Remote Similarity NPD6909 Approved
0.6391 Remote Similarity NPD6908 Approved
0.6385 Remote Similarity NPD6868 Approved
0.6379 Remote Similarity NPD1695 Approved
0.6372 Remote Similarity NPD3666 Approved
0.6372 Remote Similarity NPD4786 Approved
0.6372 Remote Similarity NPD3133 Approved
0.6372 Remote Similarity NPD3665 Phase 1
0.6349 Remote Similarity NPD5128 Approved
0.6349 Remote Similarity NPD4729 Approved
0.6349 Remote Similarity NPD4730 Approved
0.6333 Remote Similarity NPD7839 Suspended
0.6325 Remote Similarity NPD5207 Approved
0.6303 Remote Similarity NPD6001 Approved
0.6293 Remote Similarity NPD6672 Approved
0.6293 Remote Similarity NPD6903 Approved
0.6293 Remote Similarity NPD5737 Approved
0.6293 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6271 Remote Similarity NPD5693 Phase 1
0.625 Remote Similarity NPD5251 Approved
0.625 Remote Similarity NPD5250 Approved
0.625 Remote Similarity NPD5247 Approved
0.625 Remote Similarity NPD5248 Approved
0.625 Remote Similarity NPD5249 Phase 3
0.6239 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6239 Remote Similarity NPD4753 Phase 2

  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