Structure

Physi-Chem Properties

Molecular Weight:  306.11
Volume:  287.342
LogP:  1.348
LogD:  0.905
LogS:  -3.623
# 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:  0.513
Synthetic Accessibility Score:  5.741
Fsp3:  0.75
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:  -5.471
MDCK Permeability:  2.7561802198761143e-05
Pgp-inhibitor:  0.013
Pgp-substrate:  0.743
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.85
30% Bioavailability (F30%):  0.923

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.906
Plasma Protein Binding (PPB):  17.537254333496094%
Volume Distribution (VD):  0.697
Pgp-substrate:  69.0760498046875%

ADMET: Metabolism

CYP1A2-inhibitor:  0.008
CYP1A2-substrate:  0.978
CYP2C19-inhibitor:  0.029
CYP2C19-substrate:  0.751
CYP2C9-inhibitor:  0.036
CYP2C9-substrate:  0.022
CYP2D6-inhibitor:  0.003
CYP2D6-substrate:  0.033
CYP3A4-inhibitor:  0.788
CYP3A4-substrate:  0.786

ADMET: Excretion

Clearance (CL):  7.727
Half-life (T1/2):  0.573

ADMET: Toxicity

hERG Blockers:  0.068
Human Hepatotoxicity (H-HT):  0.157
Drug-inuced Liver Injury (DILI):  0.143
AMES Toxicity:  0.836
Rat Oral Acute Toxicity:  0.437
Maximum Recommended Daily Dose:  0.936
Skin Sensitization:  0.331
Carcinogencity:  0.925
Eye Corrosion:  0.116
Eye Irritation:  0.042
Respiratory Toxicity:  0.962

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

  Natural Product: NPC469655

Natural Product ID:  NPC469655
Common Name*:   JOSOPKAOCNWFFZ-OINCPMMYSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  JOSOPKAOCNWFFZ-OINCPMMYSA-N
Standard InCHI:  InChI=1S/C16H18O6/c1-14-4-7(17)5-15(2)11(14)10(21-13(15)19)12-16(22-12)6-20-9(18)3-8(14)16/h3,7,10-12,17H,4-6H2,1-2H3/t7-,10-,11?,12+,14+,15-,16-/m0/s1
SMILES:  O=C1OC[C@@]23C(=C1)[C@@]1(C)C[C@H](O)C[C@]4(C1[C@@H]([C@H]3O2)OC4=O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1096684
PubChem CID:   44613660
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
NPO13187 Sclerotinia homoeocarpa Species Sclerotiniaceae Eukaryota n.a. n.a. n.a. PMID[19928902]
NPO13187 Sclerotinia homoeocarpa Species Sclerotiniaceae 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
NPT189 Cell Line Vero Chlorocebus aethiops IC50 = 3.3 ug.mL-1 PMID[490049]
NPT146 Cell Line SK-OV-3 Homo sapiens IC50 = 10.0 ug.mL-1 PMID[490049]
NPT457 Cell Line BT-549 Homo sapiens IC50 = 10.0 ug.mL-1 PMID[490049]
NPT91 Cell Line KB Homo sapiens IC50 = 6.8 ug.mL-1 PMID[490049]
NPT916 Cell Line SK-MEL Homo sapiens IC50 = 1.1 ug.mL-1 PMID[490049]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 0.82 ug.mL-1 PMID[490049]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 0.74 ug.mL-1 PMID[490049]
NPT2 Others Unspecified Ratio IC50 = 4.5 n.a. PMID[490049]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 4.2 ug.mL-1 PMID[490049]
NPT2 Others Unspecified Ratio IC50 = 4.0 n.a. PMID[490049]
NPT854 Organism Lemna paucicostata Lemna paucicostata IC50 = 3320.0 nM PMID[490049]

☑ 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 NPC469655 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 NPC474846
1.0 High Similarity NPC469656
0.9608 High Similarity NPC180744
0.9533 High Similarity NPC58662
0.9533 High Similarity NPC13713
0.9352 High Similarity NPC469684
0.9238 High Similarity NPC469370
0.9174 High Similarity NPC98249
0.9174 High Similarity NPC478204
0.9174 High Similarity NPC53396
0.9159 High Similarity NPC222834
0.9151 High Similarity NPC253906
0.9091 High Similarity NPC478206
0.9091 High Similarity NPC478205
0.9091 High Similarity NPC108581
0.9091 High Similarity NPC284707
0.9074 High Similarity NPC475966
0.8981 High Similarity NPC472002
0.8899 High Similarity NPC478212
0.8889 High Similarity NPC247031
0.8889 High Similarity NPC100329
0.8889 High Similarity NPC97939
0.8889 High Similarity NPC132790
0.8879 High Similarity NPC478210
0.8807 High Similarity NPC269530
0.8796 High Similarity NPC478211
0.8796 High Similarity NPC478209
0.8774 High Similarity NPC469607
0.8774 High Similarity NPC478208
0.8761 High Similarity NPC251226
0.8761 High Similarity NPC154491
0.8761 High Similarity NPC268530
0.8727 High Similarity NPC25909
0.8707 High Similarity NPC293112
0.8704 High Similarity NPC299590
0.8696 High Similarity NPC11895
0.8692 High Similarity NPC67321
0.8692 High Similarity NPC187435
0.8684 High Similarity NPC159456
0.8684 High Similarity NPC4021
0.8673 High Similarity NPC42673
0.8667 High Similarity NPC476081
0.8661 High Similarity NPC473590
0.8654 High Similarity NPC47024
0.8624 High Similarity NPC472215
0.8624 High Similarity NPC472214
0.8621 High Similarity NPC81736
0.8621 High Similarity NPC172154
0.8611 High Similarity NPC189075
0.8611 High Similarity NPC275539
0.8609 High Similarity NPC170538
0.8598 High Similarity NPC102352
0.8571 High Similarity NPC478216
0.8571 High Similarity NPC179626
0.8571 High Similarity NPC475958
0.8559 High Similarity NPC477126
0.8559 High Similarity NPC49451
0.8547 High Similarity NPC473635
0.8547 High Similarity NPC198209
0.8534 High Similarity NPC67251
0.8534 High Similarity NPC469789
0.8519 High Similarity NPC144854
0.8519 High Similarity NPC3316
0.8519 High Similarity NPC230541
0.8519 High Similarity NPC110496
0.8509 High Similarity NPC230513
0.8509 High Similarity NPC475041
0.8505 High Similarity NPC477127
0.8496 Intermediate Similarity NPC473968
0.8491 Intermediate Similarity NPC295791
0.8491 Intermediate Similarity NPC31058
0.8491 Intermediate Similarity NPC273005
0.8491 Intermediate Similarity NPC469606
0.8482 Intermediate Similarity NPC473798
0.8482 Intermediate Similarity NPC117712
0.8468 Intermediate Similarity NPC42658
0.8468 Intermediate Similarity NPC474516
0.8462 Intermediate Similarity NPC469790
0.8462 Intermediate Similarity NPC8369
0.8462 Intermediate Similarity NPC24651
0.8455 Intermediate Similarity NPC5103
0.8448 Intermediate Similarity NPC312833
0.844 Intermediate Similarity NPC277017
0.844 Intermediate Similarity NPC192813
0.844 Intermediate Similarity NPC154608
0.844 Intermediate Similarity NPC306265
0.844 Intermediate Similarity NPC472439
0.844 Intermediate Similarity NPC469916
0.8435 Intermediate Similarity NPC143755
0.8421 Intermediate Similarity NPC240509
0.8411 Intermediate Similarity NPC120321
0.8411 Intermediate Similarity NPC61442
0.8407 Intermediate Similarity NPC40632
0.8407 Intermediate Similarity NPC328374
0.8407 Intermediate Similarity NPC471127
0.8407 Intermediate Similarity NPC207217
0.8407 Intermediate Similarity NPC474734
0.8407 Intermediate Similarity NPC96312
0.8407 Intermediate Similarity NPC251236
0.8407 Intermediate Similarity NPC234858
0.8407 Intermediate Similarity NPC154363
0.8407 Intermediate Similarity NPC471816
0.8396 Intermediate Similarity NPC471412
0.8393 Intermediate Similarity NPC471204
0.839 Intermediate Similarity NPC120994
0.839 Intermediate Similarity NPC203702
0.8381 Intermediate Similarity NPC216478
0.8378 Intermediate Similarity NPC188738
0.8376 Intermediate Similarity NPC265557
0.8376 Intermediate Similarity NPC105926
0.8376 Intermediate Similarity NPC91693
0.8376 Intermediate Similarity NPC18945
0.8364 Intermediate Similarity NPC141350
0.8364 Intermediate Similarity NPC474243
0.8364 Intermediate Similarity NPC143706
0.8364 Intermediate Similarity NPC472534
0.8362 Intermediate Similarity NPC102822
0.8362 Intermediate Similarity NPC470779
0.8362 Intermediate Similarity NPC477046
0.8362 Intermediate Similarity NPC67569
0.8348 Intermediate Similarity NPC472667
0.8348 Intermediate Similarity NPC475775
0.8348 Intermediate Similarity NPC469380
0.8348 Intermediate Similarity NPC476529
0.8333 Intermediate Similarity NPC470854
0.8333 Intermediate Similarity NPC55296
0.8333 Intermediate Similarity NPC474654
0.8333 Intermediate Similarity NPC470775
0.8333 Intermediate Similarity NPC287343
0.8333 Intermediate Similarity NPC283850
0.8333 Intermediate Similarity NPC146731
0.8333 Intermediate Similarity NPC10721
0.8333 Intermediate Similarity NPC258532
0.8333 Intermediate Similarity NPC296950
0.8333 Intermediate Similarity NPC176513
0.8333 Intermediate Similarity NPC97908
0.8333 Intermediate Similarity NPC122033
0.8333 Intermediate Similarity NPC65523
0.8319 Intermediate Similarity NPC284915
0.8318 Intermediate Similarity NPC162973
0.8318 Intermediate Similarity NPC165250
0.8305 Intermediate Similarity NPC476729
0.8304 Intermediate Similarity NPC12046
0.8304 Intermediate Similarity NPC194951
0.8302 Intermediate Similarity NPC471413
0.8291 Intermediate Similarity NPC269642
0.8291 Intermediate Similarity NPC23786
0.8291 Intermediate Similarity NPC470265
0.8286 Intermediate Similarity NPC473963
0.8286 Intermediate Similarity NPC474921
0.8286 Intermediate Similarity NPC136781
0.8276 Intermediate Similarity NPC107338
0.8276 Intermediate Similarity NPC109607
0.8269 Intermediate Similarity NPC157686
0.8269 Intermediate Similarity NPC259042
0.8261 Intermediate Similarity NPC17772
0.8261 Intermediate Similarity NPC146280
0.8261 Intermediate Similarity NPC251310
0.8261 Intermediate Similarity NPC470776
0.8261 Intermediate Similarity NPC124676
0.8257 Intermediate Similarity NPC181357
0.8257 Intermediate Similarity NPC127609
0.8257 Intermediate Similarity NPC34768
0.8246 Intermediate Similarity NPC476710
0.8246 Intermediate Similarity NPC476711
0.8246 Intermediate Similarity NPC270478
0.8241 Intermediate Similarity NPC474822
0.8241 Intermediate Similarity NPC72842
0.8241 Intermediate Similarity NPC254202
0.8241 Intermediate Similarity NPC159533
0.8241 Intermediate Similarity NPC99510
0.8235 Intermediate Similarity NPC477745
0.823 Intermediate Similarity NPC317210
0.823 Intermediate Similarity NPC94509
0.823 Intermediate Similarity NPC469454
0.823 Intermediate Similarity NPC33360
0.823 Intermediate Similarity NPC157441
0.823 Intermediate Similarity NPC51978
0.823 Intermediate Similarity NPC469463
0.823 Intermediate Similarity NPC469496
0.823 Intermediate Similarity NPC472757
0.8214 Intermediate Similarity NPC304180
0.8214 Intermediate Similarity NPC201992
0.8214 Intermediate Similarity NPC179798
0.8208 Intermediate Similarity NPC476806
0.8208 Intermediate Similarity NPC476807
0.8208 Intermediate Similarity NPC222303
0.8205 Intermediate Similarity NPC310511
0.8198 Intermediate Similarity NPC5475
0.8198 Intermediate Similarity NPC154906
0.8198 Intermediate Similarity NPC284828
0.8198 Intermediate Similarity NPC472216
0.8198 Intermediate Similarity NPC273433
0.8198 Intermediate Similarity NPC173905
0.819 Intermediate Similarity NPC470186
0.819 Intermediate Similarity NPC256227
0.819 Intermediate Similarity NPC473964
0.819 Intermediate Similarity NPC470777
0.819 Intermediate Similarity NPC473636
0.819 Intermediate Similarity NPC236918

  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 NPC469655 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
0.8704 High Similarity NPD4061 Clinical (unspecified phase)
0.8624 High Similarity NPD5955 Clinical (unspecified phase)
0.8349 Intermediate Similarity NPD5954 Clinical (unspecified phase)
0.8017 Intermediate Similarity NPD7115 Discovery
0.7946 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7928 Intermediate Similarity NPD6008 Approved
0.787 Intermediate Similarity NPD7638 Approved
0.787 Intermediate Similarity NPD4225 Approved
0.7798 Intermediate Similarity NPD7640 Approved
0.7798 Intermediate Similarity NPD7639 Approved
0.7642 Intermediate Similarity NPD7507 Approved
0.7632 Intermediate Similarity NPD6686 Approved
0.76 Intermediate Similarity NPD7319 Approved
0.7568 Intermediate Similarity NPD5344 Discontinued
0.7458 Intermediate Similarity NPD4632 Approved
0.7456 Intermediate Similarity NPD6675 Approved
0.7456 Intermediate Similarity NPD7128 Approved
0.7456 Intermediate Similarity NPD6402 Approved
0.7456 Intermediate Similarity NPD5739 Approved
0.7414 Intermediate Similarity NPD6373 Approved
0.7414 Intermediate Similarity NPD6372 Approved
0.7391 Intermediate Similarity NPD5701 Approved
0.7391 Intermediate Similarity NPD5697 Approved
0.7383 Intermediate Similarity NPD6698 Approved
0.7383 Intermediate Similarity NPD46 Approved
0.7377 Intermediate Similarity NPD6319 Approved
0.7373 Intermediate Similarity NPD6053 Discontinued
0.7373 Intermediate Similarity NPD8297 Approved
0.7345 Intermediate Similarity NPD7632 Discontinued
0.7328 Intermediate Similarity NPD7320 Approved
0.7328 Intermediate Similarity NPD6899 Approved
0.7328 Intermediate Similarity NPD6881 Approved
0.7321 Intermediate Similarity NPD6648 Approved
0.7295 Intermediate Similarity NPD7516 Approved
0.7288 Intermediate Similarity NPD6649 Approved
0.7288 Intermediate Similarity NPD6650 Approved
0.728 Intermediate Similarity NPD7492 Approved
0.7273 Intermediate Similarity NPD6009 Approved
0.7265 Intermediate Similarity NPD6012 Approved
0.7265 Intermediate Similarity NPD6014 Approved
0.7265 Intermediate Similarity NPD6013 Approved
0.7236 Intermediate Similarity NPD6054 Approved
0.7236 Intermediate Similarity NPD6059 Approved
0.7222 Intermediate Similarity NPD6616 Approved
0.7213 Intermediate Similarity NPD7327 Approved
0.7213 Intermediate Similarity NPD7328 Approved
0.7203 Intermediate Similarity NPD7290 Approved
0.7203 Intermediate Similarity NPD6883 Approved
0.7203 Intermediate Similarity NPD7102 Approved
0.72 Intermediate Similarity NPD7604 Phase 2
0.7179 Intermediate Similarity NPD6011 Approved
0.7177 Intermediate Similarity NPD8513 Phase 3
0.7177 Intermediate Similarity NPD6016 Approved
0.7177 Intermediate Similarity NPD5983 Phase 2
0.7177 Intermediate Similarity NPD6015 Approved
0.7177 Intermediate Similarity NPD6921 Approved
0.7165 Intermediate Similarity NPD8293 Discontinued
0.7165 Intermediate Similarity NPD7078 Approved
0.7143 Intermediate Similarity NPD8130 Phase 1
0.7143 Intermediate Similarity NPD4755 Approved
0.7143 Intermediate Similarity NPD6869 Approved
0.7143 Intermediate Similarity NPD6617 Approved
0.7143 Intermediate Similarity NPD7902 Approved
0.7143 Intermediate Similarity NPD6847 Approved
0.712 Intermediate Similarity NPD5988 Approved
0.712 Intermediate Similarity NPD6370 Approved
0.7119 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7109 Intermediate Similarity NPD7736 Approved
0.7091 Intermediate Similarity NPD6399 Phase 3
0.7083 Intermediate Similarity NPD6882 Approved
0.7075 Intermediate Similarity NPD1694 Approved
0.7075 Intermediate Similarity NPD1733 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD8328 Phase 3
0.7059 Intermediate Similarity NPD6371 Approved
0.7043 Intermediate Similarity NPD5211 Phase 2
0.704 Intermediate Similarity NPD8296 Approved
0.704 Intermediate Similarity NPD8516 Approved
0.704 Intermediate Similarity NPD8380 Approved
0.704 Intermediate Similarity NPD8378 Approved
0.704 Intermediate Similarity NPD8379 Approved
0.704 Intermediate Similarity NPD8033 Approved
0.704 Intermediate Similarity NPD8515 Approved
0.704 Intermediate Similarity NPD8517 Approved
0.704 Intermediate Similarity NPD8335 Approved
0.7027 Intermediate Similarity NPD7748 Approved
0.7018 Intermediate Similarity NPD5286 Approved
0.7018 Intermediate Similarity NPD5285 Approved
0.7018 Intermediate Similarity NPD4700 Approved
0.7018 Intermediate Similarity NPD4696 Approved
0.7009 Intermediate Similarity NPD3618 Phase 1
0.7 Intermediate Similarity NPD7515 Phase 2
0.7 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.6992 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6972 Remote Similarity NPD5328 Approved
0.6964 Remote Similarity NPD1698 Clinical (unspecified phase)
0.696 Remote Similarity NPD8377 Approved
0.696 Remote Similarity NPD8294 Approved
0.6953 Remote Similarity NPD6336 Discontinued
0.6952 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6949 Remote Similarity NPD6412 Phase 2
0.6923 Remote Similarity NPD5141 Approved
0.6917 Remote Similarity NPD4634 Approved
0.6911 Remote Similarity NPD6274 Approved
0.6905 Remote Similarity NPD7503 Approved
0.6903 Remote Similarity NPD4697 Phase 3
0.6897 Remote Similarity NPD4633 Approved
0.6897 Remote Similarity NPD5226 Approved
0.6897 Remote Similarity NPD5225 Approved
0.6897 Remote Similarity NPD5224 Approved
0.6885 Remote Similarity NPD8133 Approved
0.6875 Remote Similarity NPD7900 Approved
0.6875 Remote Similarity NPD7901 Clinical (unspecified phase)
0.686 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6847 Remote Similarity NPD6079 Approved
0.6842 Remote Similarity NPD6083 Phase 2
0.6842 Remote Similarity NPD6084 Phase 2
0.6838 Remote Similarity NPD5174 Approved
0.6838 Remote Similarity NPD5175 Approved
0.6814 Remote Similarity NPD6356 Clinical (unspecified phase)
0.681 Remote Similarity NPD5223 Approved
0.6807 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6789 Remote Similarity NPD3573 Approved
0.6786 Remote Similarity NPD5779 Approved
0.6786 Remote Similarity NPD5778 Approved
0.6786 Remote Similarity NPD4202 Approved
0.6783 Remote Similarity NPD5696 Approved
0.6772 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6769 Remote Similarity NPD8074 Phase 3
0.6757 Remote Similarity NPD7838 Discovery
0.6754 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6754 Remote Similarity NPD5222 Approved
0.6754 Remote Similarity NPD5221 Approved
0.6746 Remote Similarity NPD7101 Approved
0.6746 Remote Similarity NPD7100 Approved
0.6723 Remote Similarity NPD4767 Approved
0.6723 Remote Similarity NPD4768 Approved
0.672 Remote Similarity NPD6317 Approved
0.6718 Remote Similarity NPD6033 Approved
0.6696 Remote Similarity NPD6411 Approved
0.6696 Remote Similarity NPD8035 Phase 2
0.6696 Remote Similarity NPD8034 Phase 2
0.6696 Remote Similarity NPD5173 Approved
0.6695 Remote Similarity NPD4754 Approved
0.6692 Remote Similarity NPD7260 Phase 2
0.6667 Remote Similarity NPD6314 Approved
0.6667 Remote Similarity NPD6335 Approved
0.6667 Remote Similarity NPD5695 Phase 3
0.6667 Remote Similarity NPD4159 Approved
0.6667 Remote Similarity NPD6313 Approved
0.6667 Remote Similarity NPD1700 Approved
0.6667 Remote Similarity NPD1695 Approved
0.6642 Remote Similarity NPD6845 Suspended
0.6641 Remote Similarity NPD6908 Approved
0.6641 Remote Similarity NPD6909 Approved
0.6636 Remote Similarity NPD3667 Approved
0.6612 Remote Similarity NPD4730 Approved
0.6612 Remote Similarity NPD4729 Approved
0.6612 Remote Similarity NPD5128 Approved
0.6579 Remote Similarity NPD5282 Discontinued
0.6579 Remote Similarity NPD6001 Approved
0.6549 Remote Similarity NPD7983 Approved
0.6549 Remote Similarity NPD7637 Suspended
0.6549 Remote Similarity NPD5693 Phase 1
0.6545 Remote Similarity NPD7334 Approved
0.6545 Remote Similarity NPD6409 Approved
0.6545 Remote Similarity NPD7521 Approved
0.6545 Remote Similarity NPD6684 Approved
0.6545 Remote Similarity NPD5330 Approved
0.6545 Remote Similarity NPD7146 Approved
0.6545 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6538 Remote Similarity NPD6067 Discontinued
0.6518 Remote Similarity NPD4753 Phase 2
0.6518 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6518 Remote Similarity NPD6101 Approved
0.6514 Remote Similarity NPD3665 Phase 1
0.6514 Remote Similarity NPD3666 Approved
0.6514 Remote Similarity NPD4786 Approved
0.6514 Remote Similarity NPD3133 Approved
0.6508 Remote Similarity NPD6868 Approved
0.6504 Remote Similarity NPD5249 Phase 3
0.6504 Remote Similarity NPD5248 Approved
0.6504 Remote Similarity NPD5250 Approved
0.6504 Remote Similarity NPD5251 Approved
0.6504 Remote Similarity NPD5247 Approved
0.6496 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6486 Remote Similarity NPD7524 Approved
0.6455 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6452 Remote Similarity NPD5217 Approved
0.6452 Remote Similarity NPD5216 Approved
0.6452 Remote Similarity NPD5215 Approved
0.6429 Remote Similarity NPD5737 Approved
0.6429 Remote Similarity NPD6903 Approved
0.6429 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6429 Remote Similarity NPD6672 Approved
0.6404 Remote Similarity NPD5284 Approved
0.6404 Remote Similarity NPD5281 Approved
0.6379 Remote Similarity NPD5210 Approved
0.6379 Remote Similarity NPD4629 Approved
0.6371 Remote Similarity NPD5169 Approved
0.6371 Remote Similarity NPD5134 Clinical (unspecified phase)

  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