Structure

Physi-Chem Properties

Molecular Weight:  264.14
Volume:  269.578
LogP:  0.916
LogD:  1.201
LogS:  -2.569
# Rotatable Bonds:  0
TPSA:  66.76
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.392
Synthetic Accessibility Score:  4.793
Fsp3:  0.667
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  2
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.89
MDCK Permeability:  3.056227069464512e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.021
20% Bioavailability (F20%):  0.062
30% Bioavailability (F30%):  0.084

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.519
Plasma Protein Binding (PPB):  44.522804260253906%
Volume Distribution (VD):  1.12
Pgp-substrate:  66.21905517578125%

ADMET: Metabolism

CYP1A2-inhibitor:  0.065
CYP1A2-substrate:  0.187
CYP2C19-inhibitor:  0.021
CYP2C19-substrate:  0.603
CYP2C9-inhibitor:  0.019
CYP2C9-substrate:  0.162
CYP2D6-inhibitor:  0.008
CYP2D6-substrate:  0.197
CYP3A4-inhibitor:  0.022
CYP3A4-substrate:  0.252

ADMET: Excretion

Clearance (CL):  8.456
Half-life (T1/2):  0.289

ADMET: Toxicity

hERG Blockers:  0.028
Human Hepatotoxicity (H-HT):  0.242
Drug-inuced Liver Injury (DILI):  0.117
AMES Toxicity:  0.076
Rat Oral Acute Toxicity:  0.912
Maximum Recommended Daily Dose:  0.793
Skin Sensitization:  0.352
Carcinogencity:  0.816
Eye Corrosion:  0.194
Eye Irritation:  0.103
Respiratory Toxicity:  0.976

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

  Natural Product: NPC469596

Natural Product ID:  NPC469596
Common Name*:   Anthemin B
IUPAC Name:   (3aS,4R,4aS,8R,8aS,9aS)-4,8-dihydroxy-8a-methyl-3,5-dimethylidene-3a,4,4a,6,7,8,9,9a-octahydrobenzo[f][1]benzofuran-2-one
Synonyms:  
Standard InCHIKey:  XUTVRCGEUDNRBV-VUZIRADBSA-N
Standard InCHI:  InChI=1S/C15H20O4/c1-7-4-5-10(16)15(3)6-9-11(13(17)12(7)15)8(2)14(18)19-9/h9-13,16-17H,1-2,4-6H2,3H3/t9-,10+,11+,12+,13-,15+/m0/s1
SMILES:  CC12CC3C(C(C1C(=C)CCC2O)O)C(=C)C(=O)O3
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1092158
PubChem CID:   46183870
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001283] Terpene lactones
          • [CHEMONTID:0001543] Sesquiterpene lactones
            • [CHEMONTID:0001772] Eudesmanolides, secoeudesmanolides, and derivatives

*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
NPO8759 Anthemis melanolepis Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[20112996]

☑ 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
NPT395 Cell Line SF-268 Homo sapiens GI50 = 52300.0 nM PMID[469149]
NPT395 Cell Line SF-268 Homo sapiens TGI = 80300.0 nM PMID[469149]

☑ 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 NPC469596 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 NPC225474
1.0 High Similarity NPC148000
0.9886 High Similarity NPC259042
0.9886 High Similarity NPC157686
0.9775 High Similarity NPC93245
0.9773 High Similarity NPC24861
0.9667 High Similarity NPC473963
0.9556 High Similarity NPC473964
0.954 High Similarity NPC116620
0.9457 High Similarity NPC47024
0.9451 High Similarity NPC136781
0.9432 High Similarity NPC475776
0.9355 High Similarity NPC475958
0.9348 High Similarity NPC216478
0.9348 High Similarity NPC476807
0.9348 High Similarity NPC476806
0.9341 High Similarity NPC165528
0.9341 High Similarity NPC228766
0.9341 High Similarity NPC284518
0.9318 High Similarity NPC194642
0.931 High Similarity NPC305029
0.9195 High Similarity NPC85698
0.9158 High Similarity NPC61442
0.9091 High Similarity NPC175293
0.9091 High Similarity NPC181103
0.9053 High Similarity NPC164551
0.9022 High Similarity NPC90014
0.9 High Similarity NPC153853
0.8977 High Similarity NPC9231
0.8977 High Similarity NPC185638
0.8966 High Similarity NPC97505
0.8958 High Similarity NPC72842
0.8947 High Similarity NPC242666
0.8947 High Similarity NPC308824
0.8913 High Similarity NPC473434
0.8913 High Similarity NPC474841
0.8913 High Similarity NPC471446
0.8878 High Similarity NPC78966
0.8878 High Similarity NPC284732
0.883 High Similarity NPC474921
0.883 High Similarity NPC474395
0.8817 High Similarity NPC56369
0.8804 High Similarity NPC147272
0.8788 High Similarity NPC37628
0.8764 High Similarity NPC477920
0.8763 High Similarity NPC99510
0.8763 High Similarity NPC156681
0.875 High Similarity NPC111292
0.8736 High Similarity NPC226988
0.87 High Similarity NPC474243
0.8696 High Similarity NPC186363
0.8696 High Similarity NPC233345
0.8673 High Similarity NPC283850
0.8667 High Similarity NPC470012
0.866 High Similarity NPC476081
0.8621 High Similarity NPC223330
0.8621 High Similarity NPC209318
0.8587 High Similarity NPC158488
0.8571 High Similarity NPC277771
0.8542 High Similarity NPC98837
0.8542 High Similarity NPC89099
0.8542 High Similarity NPC38296
0.8542 High Similarity NPC20479
0.8542 High Similarity NPC162459
0.8542 High Similarity NPC38471
0.8542 High Similarity NPC28864
0.8469 Intermediate Similarity NPC170615
0.8454 Intermediate Similarity NPC293866
0.8438 Intermediate Similarity NPC70145
0.8438 Intermediate Similarity NPC10864
0.8438 Intermediate Similarity NPC91695
0.8421 Intermediate Similarity NPC183012
0.8416 Intermediate Similarity NPC275539
0.8416 Intermediate Similarity NPC189075
0.8404 Intermediate Similarity NPC199543
0.8384 Intermediate Similarity NPC120321
0.8367 Intermediate Similarity NPC46848
0.8351 Intermediate Similarity NPC78427
0.8351 Intermediate Similarity NPC473155
0.8351 Intermediate Similarity NPC16911
0.8333 Intermediate Similarity NPC29410
0.8333 Intermediate Similarity NPC134072
0.8333 Intermediate Similarity NPC470011
0.8333 Intermediate Similarity NPC256227
0.8333 Intermediate Similarity NPC234993
0.8333 Intermediate Similarity NPC200054
0.8317 Intermediate Similarity NPC110496
0.8317 Intermediate Similarity NPC67321
0.8317 Intermediate Similarity NPC187435
0.8316 Intermediate Similarity NPC250075
0.8316 Intermediate Similarity NPC57117
0.8316 Intermediate Similarity NPC66581
0.83 Intermediate Similarity NPC477127
0.8298 Intermediate Similarity NPC72845
0.8283 Intermediate Similarity NPC76866
0.8283 Intermediate Similarity NPC273005
0.8283 Intermediate Similarity NPC286519
0.8283 Intermediate Similarity NPC88203
0.8283 Intermediate Similarity NPC246736
0.8283 Intermediate Similarity NPC165250
0.8283 Intermediate Similarity NPC469606
0.8283 Intermediate Similarity NPC31058
0.8283 Intermediate Similarity NPC304832
0.8283 Intermediate Similarity NPC275990
0.8283 Intermediate Similarity NPC214946
0.8283 Intermediate Similarity NPC58329
0.8283 Intermediate Similarity NPC148628
0.8265 Intermediate Similarity NPC287676
0.8247 Intermediate Similarity NPC111348
0.8229 Intermediate Similarity NPC98639
0.8222 Intermediate Similarity NPC243347
0.8222 Intermediate Similarity NPC194637
0.8218 Intermediate Similarity NPC469607
0.8218 Intermediate Similarity NPC295366
0.8218 Intermediate Similarity NPC28791
0.8218 Intermediate Similarity NPC34768
0.8211 Intermediate Similarity NPC139692
0.8202 Intermediate Similarity NPC38642
0.8202 Intermediate Similarity NPC475743
0.82 Intermediate Similarity NPC87927
0.82 Intermediate Similarity NPC221421
0.819 Intermediate Similarity NPC477126
0.8182 Intermediate Similarity NPC289148
0.8182 Intermediate Similarity NPC52899
0.8182 Intermediate Similarity NPC471412
0.8182 Intermediate Similarity NPC163963
0.8182 Intermediate Similarity NPC121218
0.8182 Intermediate Similarity NPC253886
0.8173 Intermediate Similarity NPC469655
0.8173 Intermediate Similarity NPC469656
0.8173 Intermediate Similarity NPC474846
0.8172 Intermediate Similarity NPC136879
0.8172 Intermediate Similarity NPC477302
0.8163 Intermediate Similarity NPC471038
0.8163 Intermediate Similarity NPC23364
0.8163 Intermediate Similarity NPC474793
0.8152 Intermediate Similarity NPC250981
0.8152 Intermediate Similarity NPC6979
0.8144 Intermediate Similarity NPC202833
0.8137 Intermediate Similarity NPC302788
0.8137 Intermediate Similarity NPC251824
0.8137 Intermediate Similarity NPC86852
0.8137 Intermediate Similarity NPC143609
0.8132 Intermediate Similarity NPC219011
0.8125 Intermediate Similarity NPC3359
0.8125 Intermediate Similarity NPC47853
0.8119 Intermediate Similarity NPC296950
0.8119 Intermediate Similarity NPC84928
0.8119 Intermediate Similarity NPC301787
0.8105 Intermediate Similarity NPC130840
0.8105 Intermediate Similarity NPC198054
0.81 Intermediate Similarity NPC162973
0.8095 Intermediate Similarity NPC194951
0.8095 Intermediate Similarity NPC12046
0.8085 Intermediate Similarity NPC77001
0.8085 Intermediate Similarity NPC206001
0.8085 Intermediate Similarity NPC253618
0.8085 Intermediate Similarity NPC218927
0.8085 Intermediate Similarity NPC155935
0.8081 Intermediate Similarity NPC471413
0.8081 Intermediate Similarity NPC477656
0.8081 Intermediate Similarity NPC293890
0.8081 Intermediate Similarity NPC267921
0.8081 Intermediate Similarity NPC477655
0.8081 Intermediate Similarity NPC476303
0.8077 Intermediate Similarity NPC478209
0.8077 Intermediate Similarity NPC124053
0.8061 Intermediate Similarity NPC474343
0.8061 Intermediate Similarity NPC253586
0.8058 Intermediate Similarity NPC218123
0.8058 Intermediate Similarity NPC255082
0.8058 Intermediate Similarity NPC306265
0.8058 Intermediate Similarity NPC112895
0.8058 Intermediate Similarity NPC273155
0.8058 Intermediate Similarity NPC231278
0.8046 Intermediate Similarity NPC92489
0.8041 Intermediate Similarity NPC210214
0.8041 Intermediate Similarity NPC276110
0.8041 Intermediate Similarity NPC470232
0.8039 Intermediate Similarity NPC37600
0.8039 Intermediate Similarity NPC478208
0.8039 Intermediate Similarity NPC222833
0.8039 Intermediate Similarity NPC138908
0.8039 Intermediate Similarity NPC111952
0.8039 Intermediate Similarity NPC200957
0.8022 Intermediate Similarity NPC15091
0.8021 Intermediate Similarity NPC294263
0.802 Intermediate Similarity NPC216114
0.802 Intermediate Similarity NPC96217
0.802 Intermediate Similarity NPC36688
0.802 Intermediate Similarity NPC159533
0.802 Intermediate Similarity NPC139347
0.802 Intermediate Similarity NPC254202
0.802 Intermediate Similarity NPC476237
0.8019 Intermediate Similarity NPC157441
0.8019 Intermediate Similarity NPC25909
0.8 Intermediate Similarity NPC236585
0.8 Intermediate Similarity NPC475951
0.8 Intermediate Similarity NPC148279
0.8 Intermediate Similarity NPC94650

  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 NPC469596 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
0.78 Intermediate Similarity NPD7638 Approved
0.78 Intermediate Similarity NPD4225 Approved
0.7723 Intermediate Similarity NPD7639 Approved
0.7723 Intermediate Similarity NPD7640 Approved
0.7642 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.757 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7551 Intermediate Similarity NPD8035 Phase 2
0.7551 Intermediate Similarity NPD8034 Phase 2
0.7547 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7383 Intermediate Similarity NPD6686 Approved
0.73 Intermediate Similarity NPD6399 Phase 3
0.7292 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7292 Intermediate Similarity NPD1694 Approved
0.729 Intermediate Similarity NPD5954 Clinical (unspecified phase)
0.7238 Intermediate Similarity NPD7632 Discontinued
0.7207 Intermediate Similarity NPD8133 Approved
0.7196 Intermediate Similarity NPD6008 Approved
0.7184 Intermediate Similarity NPD7902 Approved
0.7168 Intermediate Similarity NPD7115 Discovery
0.7158 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7157 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.713 Intermediate Similarity NPD5697 Approved
0.7064 Intermediate Similarity NPD6899 Approved
0.7064 Intermediate Similarity NPD6881 Approved
0.7059 Intermediate Similarity NPD7748 Approved
0.7041 Intermediate Similarity NPD3618 Phase 1
0.7037 Intermediate Similarity NPD5739 Approved
0.7037 Intermediate Similarity NPD6402 Approved
0.7037 Intermediate Similarity NPD7128 Approved
0.7037 Intermediate Similarity NPD6675 Approved
0.703 Intermediate Similarity NPD7515 Phase 2
0.7027 Intermediate Similarity NPD6649 Approved
0.7027 Intermediate Similarity NPD6650 Approved
0.7 Intermediate Similarity NPD6014 Approved
0.7 Intermediate Similarity NPD6372 Approved
0.7 Intermediate Similarity NPD6013 Approved
0.7 Intermediate Similarity NPD6012 Approved
0.7 Intermediate Similarity NPD6373 Approved
0.6972 Remote Similarity NPD5701 Approved
0.6937 Remote Similarity NPD7290 Approved
0.6937 Remote Similarity NPD6883 Approved
0.6937 Remote Similarity NPD7102 Approved
0.6915 Remote Similarity NPD6115 Approved
0.6915 Remote Similarity NPD6114 Approved
0.6915 Remote Similarity NPD6697 Approved
0.6915 Remote Similarity NPD6118 Approved
0.6909 Remote Similarity NPD6011 Approved
0.6909 Remote Similarity NPD7320 Approved
0.6903 Remote Similarity NPD4632 Approved
0.6893 Remote Similarity NPD7900 Approved
0.6893 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6875 Remote Similarity NPD6869 Approved
0.6875 Remote Similarity NPD8130 Phase 1
0.6875 Remote Similarity NPD6847 Approved
0.6875 Remote Similarity NPD6617 Approved
0.6847 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6838 Remote Similarity NPD6319 Approved
0.6833 Remote Similarity NPD7507 Approved
0.6832 Remote Similarity NPD1695 Approved
0.6822 Remote Similarity NPD5344 Discontinued
0.6814 Remote Similarity NPD8297 Approved
0.6814 Remote Similarity NPD6882 Approved
0.6809 Remote Similarity NPD6116 Phase 1
0.6804 Remote Similarity NPD3667 Approved
0.6803 Remote Similarity NPD7319 Approved
0.678 Remote Similarity NPD6921 Approved
0.6765 Remote Similarity NPD46 Approved
0.6765 Remote Similarity NPD6698 Approved
0.6759 Remote Similarity NPD5211 Phase 2
0.675 Remote Similarity NPD7492 Approved
0.6729 Remote Similarity NPD4696 Approved
0.6729 Remote Similarity NPD5285 Approved
0.6729 Remote Similarity NPD5286 Approved
0.6724 Remote Similarity NPD6009 Approved
0.6702 Remote Similarity NPD6117 Approved
0.6699 Remote Similarity NPD6079 Approved
0.6699 Remote Similarity NPD7637 Suspended
0.6698 Remote Similarity NPD6084 Phase 2
0.6698 Remote Similarity NPD4755 Approved
0.6698 Remote Similarity NPD6083 Phase 2
0.6695 Remote Similarity NPD6054 Approved
0.6694 Remote Similarity NPD6616 Approved
0.6667 Remote Similarity NPD5328 Approved
0.6667 Remote Similarity NPD4786 Approved
0.6667 Remote Similarity NPD7328 Approved
0.6667 Remote Similarity NPD7327 Approved
0.6667 Remote Similarity NPD6053 Discontinued
0.6667 Remote Similarity NPD6412 Phase 2
0.6639 Remote Similarity NPD6015 Approved
0.6639 Remote Similarity NPD5983 Phase 2
0.6639 Remote Similarity NPD7078 Approved
0.6639 Remote Similarity NPD6016 Approved
0.6638 Remote Similarity NPD6274 Approved
0.6637 Remote Similarity NPD6371 Approved
0.6636 Remote Similarity NPD5141 Approved
0.6636 Remote Similarity NPD5696 Approved
0.6635 Remote Similarity NPD4202 Approved
0.6635 Remote Similarity NPD5778 Approved
0.6635 Remote Similarity NPD5779 Approved
0.661 Remote Similarity NPD7516 Approved
0.6606 Remote Similarity NPD5225 Approved
0.6606 Remote Similarity NPD5226 Approved
0.6606 Remote Similarity NPD4633 Approved
0.6606 Remote Similarity NPD5224 Approved
0.6604 Remote Similarity NPD5221 Approved
0.6604 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6604 Remote Similarity NPD5222 Approved
0.6604 Remote Similarity NPD4697 Phase 3
0.66 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6585 Remote Similarity NPD7736 Approved
0.6583 Remote Similarity NPD6370 Approved
0.6583 Remote Similarity NPD5988 Approved
0.6581 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6579 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6574 Remote Similarity NPD6648 Approved
0.6574 Remote Similarity NPD4700 Approved
0.6571 Remote Similarity NPD5282 Discontinued
0.6566 Remote Similarity NPD4788 Approved
0.6555 Remote Similarity NPD6059 Approved
0.6545 Remote Similarity NPD5174 Approved
0.6545 Remote Similarity NPD5175 Approved
0.6542 Remote Similarity NPD5173 Approved
0.6538 Remote Similarity NPD6411 Approved
0.6535 Remote Similarity NPD5330 Approved
0.6535 Remote Similarity NPD6684 Approved
0.6535 Remote Similarity NPD6409 Approved
0.6535 Remote Similarity NPD7334 Approved
0.6535 Remote Similarity NPD7521 Approved
0.6535 Remote Similarity NPD7146 Approved
0.6529 Remote Similarity NPD8328 Phase 3
0.6529 Remote Similarity NPD7604 Phase 2
0.6518 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6514 Remote Similarity NPD5223 Approved
0.6509 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6509 Remote Similarity NPD5695 Phase 3
0.6504 Remote Similarity NPD8293 Discontinued
0.65 Remote Similarity NPD8296 Approved
0.65 Remote Similarity NPD3133 Approved
0.65 Remote Similarity NPD8380 Approved
0.65 Remote Similarity NPD6291 Clinical (unspecified phase)
0.65 Remote Similarity NPD7338 Clinical (unspecified phase)
0.65 Remote Similarity NPD3666 Approved
0.65 Remote Similarity NPD8033 Approved
0.65 Remote Similarity NPD8379 Approved
0.65 Remote Similarity NPD8335 Approved
0.65 Remote Similarity NPD8378 Approved
0.65 Remote Similarity NPD3665 Phase 1
0.6491 Remote Similarity NPD4634 Approved
0.6489 Remote Similarity NPD6113 Clinical (unspecified phase)
0.6471 Remote Similarity NPD3573 Approved
0.6471 Remote Similarity NPD7101 Approved
0.6471 Remote Similarity NPD7100 Approved
0.6442 Remote Similarity NPD5785 Approved
0.6441 Remote Similarity NPD6317 Approved
0.6423 Remote Similarity NPD6336 Discontinued
0.6421 Remote Similarity NPD3703 Phase 2
0.6417 Remote Similarity NPD8294 Approved
0.6417 Remote Similarity NPD8377 Approved
0.6408 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6408 Remote Similarity NPD5737 Approved
0.6408 Remote Similarity NPD6672 Approved
0.6408 Remote Similarity NPD6903 Approved
0.64 Remote Similarity NPD6695 Phase 3
0.6387 Remote Similarity NPD6313 Approved
0.6387 Remote Similarity NPD6314 Approved
0.6387 Remote Similarity NPD6335 Approved
0.6381 Remote Similarity NPD5693 Phase 1
0.6373 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6364 Remote Similarity NPD8517 Approved
0.6364 Remote Similarity NPD1700 Approved
0.6364 Remote Similarity NPD8513 Phase 3
0.6364 Remote Similarity NPD8516 Approved
0.6364 Remote Similarity NPD7503 Approved
0.6364 Remote Similarity NPD8515 Approved
0.6356 Remote Similarity NPD6868 Approved
0.6355 Remote Similarity NPD5210 Approved
0.6355 Remote Similarity NPD4629 Approved
0.6346 Remote Similarity NPD6101 Approved
0.6346 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6346 Remote Similarity NPD4753 Phase 2
0.6337 Remote Similarity NPD3668 Phase 3
0.6316 Remote Similarity NPD4729 Approved
0.6316 Remote Similarity NPD5128 Approved
0.6316 Remote Similarity NPD4730 Approved
0.6293 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6286 Remote Similarity NPD7838 Discovery
0.6283 Remote Similarity NPD4768 Approved
0.6283 Remote Similarity NPD4767 Approved
0.6263 Remote Similarity NPD4695 Discontinued
0.6263 Remote Similarity NPD7525 Registered
0.6262 Remote Similarity NPD6001 Approved
0.626 Remote Similarity NPD6067 Discontinued
0.625 Remote Similarity NPD4754 Approved
0.6237 Remote Similarity NPD3700 Clinical (unspecified phase)
0.6237 Remote Similarity NPD3699 Clinical (unspecified phase)
0.623 Remote Similarity NPD6908 Approved
0.623 Remote Similarity NPD6909 Approved
0.6226 Remote Similarity NPD5284 Approved
0.6226 Remote Similarity NPD5281 Approved
0.6214 Remote Similarity NPD4249 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