Structure

Physi-Chem Properties

Molecular Weight:  332.2
Volume:  347.502
LogP:  3.21
LogD:  3.158
LogS:  -2.829
# Rotatable Bonds:  1
TPSA:  62.83
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  4
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.751
Synthetic Accessibility Score:  4.637
Fsp3:  0.7
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -5.088
MDCK Permeability:  1.0757104064396117e-05
Pgp-inhibitor:  0.004
Pgp-substrate:  0.083
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.017
30% Bioavailability (F30%):  0.038

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.135
Plasma Protein Binding (PPB):  95.21234893798828%
Volume Distribution (VD):  2.206
Pgp-substrate:  3.737248420715332%

ADMET: Metabolism

CYP1A2-inhibitor:  0.028
CYP1A2-substrate:  0.201
CYP2C19-inhibitor:  0.035
CYP2C19-substrate:  0.557
CYP2C9-inhibitor:  0.278
CYP2C9-substrate:  0.37
CYP2D6-inhibitor:  0.015
CYP2D6-substrate:  0.423
CYP3A4-inhibitor:  0.063
CYP3A4-substrate:  0.29

ADMET: Excretion

Clearance (CL):  14.425
Half-life (T1/2):  0.277

ADMET: Toxicity

hERG Blockers:  0.044
Human Hepatotoxicity (H-HT):  0.117
Drug-inuced Liver Injury (DILI):  0.081
AMES Toxicity:  0.014
Rat Oral Acute Toxicity:  0.964
Maximum Recommended Daily Dose:  0.972
Skin Sensitization:  0.231
Carcinogencity:  0.678
Eye Corrosion:  0.004
Eye Irritation:  0.054
Respiratory Toxicity:  0.97

Download Data

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

  Natural Product: NPC474012

Natural Product ID:  NPC474012
Common Name*:   Aulacocarpinolide
IUPAC Name:   4-[(2R,6aR,8S,10aS)-8-hydroxy-7,7,10a-trimethyl-2,4,5,6,6a,8,9,10-octahydro-1H-benzo[f]isochromen-2-yl]-2H-furan-5-one
Synonyms:   aulacocarpinolide
Standard InCHIKey:  ZZHKBSPZAYQQQT-NHAYFPRASA-N
Standard InCHI:  InChI=1S/C20H28O4/c1-19(2)16-5-4-12-11-24-15(13-7-9-23-18(13)22)10-14(12)20(16,3)8-6-17(19)21/h7,15-17,21H,4-6,8-11H2,1-3H3/t15-,16+,17+,20-/m1/s1
SMILES:  CC1(C)[C@@H]2CCC3=C(C[C@H](C4=CCOC4=O)OC3)[C@@]2(C)CC[C@@H]1O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL458314
PubChem CID:   44559677
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001283] Terpene lactones
          • [CHEMONTID:0001538] Diterpene lactones

*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
NPO594 Alpinia densespicata Species Staphylinidae Eukaryota n.a. n.a. n.a. PMID[19555124]
NPO17467 Aframomum aulacocarpos Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[7964787]
NPO594 Alpinia densespicata Species Staphylinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17467 Aframomum aulacocarpos Species Zingiberaceae 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
NPT137 Cell Line L1210 Mus musculus ED50 = 12.5 ug ml-1 PMID[559445]
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 44600.0 nM PMID[559446]
NPT113 Cell Line RAW264.7 Mus musculus Activity > 80.0 % PMID[559446]
NPT79 Organism Bacillus subtilis Bacillus subtilis MIC = 25.0 ug.mL-1 PMID[559445]
NPT2526 Organism Rhizomucor miehei Rhizomucor miehei MIC = 50.0 ug.mL-1 PMID[559445]

☑ 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 NPC474012 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 NPC476299
0.9255 High Similarity NPC242848
0.914 High Similarity NPC139692
0.914 High Similarity NPC115021
0.8969 High Similarity NPC117685
0.8947 High Similarity NPC183012
0.8854 High Similarity NPC234993
0.8854 High Similarity NPC134072
0.8842 High Similarity NPC470697
0.883 High Similarity NPC177037
0.883 High Similarity NPC472814
0.8817 High Similarity NPC5509
0.8723 High Similarity NPC51486
0.87 High Similarity NPC476889
0.87 High Similarity NPC112009
0.8673 High Similarity NPC316598
0.8667 High Similarity NPC122056
0.8654 High Similarity NPC474315
0.8632 High Similarity NPC233345
0.8632 High Similarity NPC72845
0.8632 High Similarity NPC186363
0.8627 High Similarity NPC91034
0.8617 High Similarity NPC174342
0.8602 High Similarity NPC312561
0.86 High Similarity NPC273005
0.86 High Similarity NPC31058
0.86 High Similarity NPC469606
0.86 High Similarity NPC476081
0.86 High Similarity NPC40918
0.86 High Similarity NPC476890
0.8586 High Similarity NPC201406
0.8585 High Similarity NPC67259
0.8585 High Similarity NPC147912
0.8571 High Similarity NPC224356
0.8571 High Similarity NPC53844
0.8571 High Similarity NPC253826
0.8571 High Similarity NPC132753
0.8571 High Similarity NPC151681
0.8571 High Similarity NPC73911
0.8571 High Similarity NPC175351
0.8571 High Similarity NPC121402
0.8571 High Similarity NPC475709
0.8557 High Similarity NPC209355
0.8544 High Similarity NPC220155
0.8542 High Similarity NPC162615
0.8542 High Similarity NPC205034
0.8542 High Similarity NPC152778
0.8529 High Similarity NPC266570
0.8529 High Similarity NPC469607
0.8526 High Similarity NPC280149
0.8526 High Similarity NPC232426
0.8526 High Similarity NPC221111
0.8526 High Similarity NPC281942
0.8526 High Similarity NPC78973
0.8526 High Similarity NPC8062
0.8515 High Similarity NPC159533
0.8515 High Similarity NPC180204
0.8515 High Similarity NPC120321
0.8515 High Similarity NPC95899
0.8505 High Similarity NPC64318
0.85 High Similarity NPC244456
0.85 High Similarity NPC476888
0.85 High Similarity NPC93744
0.85 High Similarity NPC471412
0.85 High Similarity NPC469657
0.8495 Intermediate Similarity NPC131813
0.8485 Intermediate Similarity NPC478056
0.8485 Intermediate Similarity NPC159763
0.8485 Intermediate Similarity NPC216478
0.8485 Intermediate Similarity NPC124512
0.8485 Intermediate Similarity NPC278386
0.8469 Intermediate Similarity NPC240673
0.8469 Intermediate Similarity NPC472363
0.8469 Intermediate Similarity NPC17578
0.8469 Intermediate Similarity NPC154526
0.8469 Intermediate Similarity NPC472362
0.8469 Intermediate Similarity NPC202833
0.8454 Intermediate Similarity NPC53685
0.8454 Intermediate Similarity NPC84893
0.8454 Intermediate Similarity NPC474555
0.8438 Intermediate Similarity NPC141831
0.8426 Intermediate Similarity NPC167606
0.8426 Intermediate Similarity NPC470493
0.8426 Intermediate Similarity NPC470492
0.8426 Intermediate Similarity NPC312824
0.8426 Intermediate Similarity NPC286528
0.8426 Intermediate Similarity NPC20302
0.8426 Intermediate Similarity NPC183580
0.8426 Intermediate Similarity NPC140055
0.8421 Intermediate Similarity NPC168131
0.8416 Intermediate Similarity NPC32577
0.8416 Intermediate Similarity NPC165250
0.8416 Intermediate Similarity NPC114540
0.8416 Intermediate Similarity NPC155332
0.84 Intermediate Similarity NPC47024
0.84 Intermediate Similarity NPC471413
0.8396 Intermediate Similarity NPC277769
0.8396 Intermediate Similarity NPC69291
0.8387 Intermediate Similarity NPC86316
0.8387 Intermediate Similarity NPC189311
0.8387 Intermediate Similarity NPC106416
0.8387 Intermediate Similarity NPC65661
0.8384 Intermediate Similarity NPC38530
0.8384 Intermediate Similarity NPC84335
0.8384 Intermediate Similarity NPC474343
0.8381 Intermediate Similarity NPC29133
0.8365 Intermediate Similarity NPC90946
0.8365 Intermediate Similarity NPC189075
0.8365 Intermediate Similarity NPC275539
0.8365 Intermediate Similarity NPC473483
0.8365 Intermediate Similarity NPC476802
0.8365 Intermediate Similarity NPC300614
0.8365 Intermediate Similarity NPC89171
0.8351 Intermediate Similarity NPC472303
0.8351 Intermediate Similarity NPC271652
0.835 Intermediate Similarity NPC1679
0.8349 Intermediate Similarity NPC709
0.8349 Intermediate Similarity NPC50774
0.8349 Intermediate Similarity NPC186525
0.8333 Intermediate Similarity NPC220454
0.8333 Intermediate Similarity NPC310479
0.8333 Intermediate Similarity NPC469595
0.8333 Intermediate Similarity NPC212679
0.8317 Intermediate Similarity NPC472637
0.8317 Intermediate Similarity NPC303559
0.8317 Intermediate Similarity NPC81530
0.8317 Intermediate Similarity NPC471075
0.8316 Intermediate Similarity NPC477302
0.8316 Intermediate Similarity NPC277771
0.8316 Intermediate Similarity NPC104560
0.8316 Intermediate Similarity NPC226863
0.8316 Intermediate Similarity NPC473229
0.8302 Intermediate Similarity NPC470961
0.83 Intermediate Similarity NPC98868
0.83 Intermediate Similarity NPC57079
0.83 Intermediate Similarity NPC108368
0.8298 Intermediate Similarity NPC473226
0.8288 Intermediate Similarity NPC476204
0.8288 Intermediate Similarity NPC170084
0.8286 Intermediate Similarity NPC228477
0.8286 Intermediate Similarity NPC31522
0.8286 Intermediate Similarity NPC137911
0.8286 Intermediate Similarity NPC475065
0.8283 Intermediate Similarity NPC120708
0.8283 Intermediate Similarity NPC16967
0.8283 Intermediate Similarity NPC98874
0.828 Intermediate Similarity NPC30486
0.8273 Intermediate Similarity NPC264954
0.8269 Intermediate Similarity NPC329048
0.8269 Intermediate Similarity NPC475570
0.8269 Intermediate Similarity NPC187435
0.8269 Intermediate Similarity NPC330011
0.8269 Intermediate Similarity NPC110496
0.8269 Intermediate Similarity NPC67321
0.8265 Intermediate Similarity NPC477130
0.8265 Intermediate Similarity NPC191521
0.8265 Intermediate Similarity NPC104925
0.8265 Intermediate Similarity NPC477129
0.8265 Intermediate Similarity NPC298973
0.8265 Intermediate Similarity NPC474554
0.8265 Intermediate Similarity NPC57117
0.8265 Intermediate Similarity NPC91010
0.8257 Intermediate Similarity NPC469684
0.8257 Intermediate Similarity NPC53396
0.8257 Intermediate Similarity NPC243065
0.8257 Intermediate Similarity NPC98249
0.8252 Intermediate Similarity NPC146731
0.8252 Intermediate Similarity NPC296950
0.8247 Intermediate Similarity NPC303697
0.8247 Intermediate Similarity NPC289479
0.8235 Intermediate Similarity NPC295791
0.8235 Intermediate Similarity NPC58329
0.8235 Intermediate Similarity NPC162973
0.8235 Intermediate Similarity NPC136289
0.8229 Intermediate Similarity NPC50488
0.8229 Intermediate Similarity NPC218927
0.8229 Intermediate Similarity NPC474396
0.8229 Intermediate Similarity NPC206001
0.8229 Intermediate Similarity NPC73995
0.8224 Intermediate Similarity NPC4573
0.8224 Intermediate Similarity NPC191620
0.8224 Intermediate Similarity NPC470063
0.8224 Intermediate Similarity NPC269530
0.8224 Intermediate Similarity NPC90952
0.8218 Intermediate Similarity NPC476767
0.8218 Intermediate Similarity NPC54705
0.8218 Intermediate Similarity NPC472644
0.8211 Intermediate Similarity NPC171722
0.8208 Intermediate Similarity NPC472666
0.8208 Intermediate Similarity NPC179642
0.8208 Intermediate Similarity NPC478209
0.82 Intermediate Similarity NPC287668
0.82 Intermediate Similarity NPC208094
0.82 Intermediate Similarity NPC89225
0.82 Intermediate Similarity NPC2049
0.82 Intermediate Similarity NPC26413
0.8198 Intermediate Similarity NPC474370
0.819 Intermediate Similarity NPC473482
0.819 Intermediate Similarity NPC318363
0.819 Intermediate Similarity NPC306265

  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 NPC474012 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
0.8485 Intermediate Similarity NPD4225 Approved
0.8426 Intermediate Similarity NPD7115 Discovery
0.8119 Intermediate Similarity NPD7638 Approved
0.8065 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.8039 Intermediate Similarity NPD7640 Approved
0.8039 Intermediate Similarity NPD7639 Approved
0.79 Intermediate Similarity NPD7748 Approved
0.7879 Intermediate Similarity NPD7515 Phase 2
0.7812 Intermediate Similarity NPD1694 Approved
0.7778 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7757 Intermediate Similarity NPD5697 Approved
0.7732 Intermediate Similarity NPD3618 Phase 1
0.77 Intermediate Similarity NPD6411 Approved
0.7685 Intermediate Similarity NPD6686 Approved
0.7685 Intermediate Similarity NPD6899 Approved
0.7685 Intermediate Similarity NPD6881 Approved
0.767 Intermediate Similarity NPD7902 Approved
0.7664 Intermediate Similarity NPD6402 Approved
0.7664 Intermediate Similarity NPD7128 Approved
0.7664 Intermediate Similarity NPD6675 Approved
0.7664 Intermediate Similarity NPD5739 Approved
0.7624 Intermediate Similarity NPD6399 Phase 3
0.7615 Intermediate Similarity NPD6012 Approved
0.7615 Intermediate Similarity NPD6013 Approved
0.7615 Intermediate Similarity NPD6014 Approved
0.7593 Intermediate Similarity NPD5701 Approved
0.7545 Intermediate Similarity NPD7290 Approved
0.7545 Intermediate Similarity NPD6883 Approved
0.7545 Intermediate Similarity NPD7102 Approved
0.7545 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7525 Intermediate Similarity NPD6079 Approved
0.7523 Intermediate Similarity NPD6011 Approved
0.7523 Intermediate Similarity NPD7320 Approved
0.75 Intermediate Similarity NPD6083 Phase 2
0.75 Intermediate Similarity NPD6101 Approved
0.75 Intermediate Similarity NPD3667 Approved
0.75 Intermediate Similarity NPD6084 Phase 2
0.75 Intermediate Similarity NPD5764 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD5328 Approved
0.7477 Intermediate Similarity NPD6650 Approved
0.7477 Intermediate Similarity NPD6617 Approved
0.7477 Intermediate Similarity NPD6649 Approved
0.7477 Intermediate Similarity NPD6847 Approved
0.7477 Intermediate Similarity NPD6869 Approved
0.7477 Intermediate Similarity NPD8130 Phase 1
0.7476 Intermediate Similarity NPD5695 Phase 3
0.7476 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7455 Intermediate Similarity NPD6373 Approved
0.7455 Intermediate Similarity NPD6372 Approved
0.7451 Intermediate Similarity NPD5778 Approved
0.7451 Intermediate Similarity NPD5779 Approved
0.7426 Intermediate Similarity NPD5785 Approved
0.7411 Intermediate Similarity NPD8297 Approved
0.7411 Intermediate Similarity NPD6882 Approved
0.7404 Intermediate Similarity NPD5221 Approved
0.7404 Intermediate Similarity NPD5222 Approved
0.7404 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7383 Intermediate Similarity NPD7632 Discontinued
0.7383 Intermediate Similarity NPD5211 Phase 2
0.7379 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7379 Intermediate Similarity NPD7900 Approved
0.7374 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.7374 Intermediate Similarity NPD6409 Approved
0.7374 Intermediate Similarity NPD7146 Approved
0.7374 Intermediate Similarity NPD6684 Approved
0.7374 Intermediate Similarity NPD7521 Approved
0.7374 Intermediate Similarity NPD7334 Approved
0.7374 Intermediate Similarity NPD5330 Approved
0.7358 Intermediate Similarity NPD5286 Approved
0.7358 Intermediate Similarity NPD5285 Approved
0.7358 Intermediate Similarity NPD4696 Approved
0.7347 Intermediate Similarity NPD3133 Approved
0.7347 Intermediate Similarity NPD3665 Phase 1
0.7347 Intermediate Similarity NPD4786 Approved
0.7347 Intermediate Similarity NPD3666 Approved
0.7347 Intermediate Similarity NPD6400 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD5173 Approved
0.7333 Intermediate Similarity NPD4755 Approved
0.73 Intermediate Similarity NPD3573 Approved
0.7282 Intermediate Similarity NPD4202 Approved
0.7273 Intermediate Similarity NPD5954 Clinical (unspecified phase)
0.7265 Intermediate Similarity NPD6319 Approved
0.7264 Intermediate Similarity NPD5696 Approved
0.7257 Intermediate Similarity NPD6053 Discontinued
0.7248 Intermediate Similarity NPD5141 Approved
0.7238 Intermediate Similarity NPD4697 Phase 3
0.7228 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7228 Intermediate Similarity NPD6903 Approved
0.7228 Intermediate Similarity NPD6672 Approved
0.7228 Intermediate Similarity NPD5737 Approved
0.7222 Intermediate Similarity NPD5224 Approved
0.7222 Intermediate Similarity NPD5226 Approved
0.7222 Intermediate Similarity NPD4633 Approved
0.7222 Intermediate Similarity NPD5225 Approved
0.7217 Intermediate Similarity NPD6274 Approved
0.7213 Intermediate Similarity NPD7319 Approved
0.7196 Intermediate Similarity NPD4700 Approved
0.7184 Intermediate Similarity NPD5693 Phase 1
0.7168 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7157 Intermediate Similarity NPD4753 Phase 2
0.7156 Intermediate Similarity NPD5174 Approved
0.7156 Intermediate Similarity NPD5175 Approved
0.713 Intermediate Similarity NPD5223 Approved
0.7113 Intermediate Similarity NPD4695 Discontinued
0.7107 Intermediate Similarity NPD7507 Approved
0.71 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.708 Intermediate Similarity NPD4634 Approved
0.7069 Intermediate Similarity NPD6868 Approved
0.7043 Intermediate Similarity NPD4632 Approved
0.7034 Intermediate Similarity NPD7100 Approved
0.7034 Intermediate Similarity NPD7101 Approved
0.703 Intermediate Similarity NPD5279 Phase 3
0.7027 Intermediate Similarity NPD6008 Approved
0.7025 Intermediate Similarity NPD7492 Approved
0.7019 Intermediate Similarity NPD8035 Phase 2
0.7019 Intermediate Similarity NPD7637 Suspended
0.7019 Intermediate Similarity NPD8034 Phase 2
0.7009 Intermediate Similarity NPD6317 Approved
0.7 Intermediate Similarity NPD3668 Phase 3
0.6981 Remote Similarity NPD4629 Approved
0.6981 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6981 Remote Similarity NPD5210 Approved
0.6975 Remote Similarity NPD6054 Approved
0.6967 Remote Similarity NPD6616 Approved
0.6949 Remote Similarity NPD6335 Approved
0.6949 Remote Similarity NPD6314 Approved
0.6949 Remote Similarity NPD6313 Approved
0.6931 Remote Similarity NPD5363 Approved
0.693 Remote Similarity NPD6371 Approved
0.6923 Remote Similarity NPD6698 Approved
0.6923 Remote Similarity NPD46 Approved
0.6917 Remote Similarity NPD6015 Approved
0.6917 Remote Similarity NPD6016 Approved
0.6911 Remote Similarity NPD7078 Approved
0.6903 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6903 Remote Similarity NPD4729 Approved
0.6903 Remote Similarity NPD4730 Approved
0.6903 Remote Similarity NPD5128 Approved
0.6875 Remote Similarity NPD4768 Approved
0.6875 Remote Similarity NPD4767 Approved
0.6864 Remote Similarity NPD6009 Approved
0.6863 Remote Similarity NPD4623 Approved
0.6863 Remote Similarity NPD4519 Discontinued
0.686 Remote Similarity NPD5988 Approved
0.686 Remote Similarity NPD6370 Approved
0.6857 Remote Similarity NPD5284 Approved
0.6857 Remote Similarity NPD5281 Approved
0.6855 Remote Similarity NPD7736 Approved
0.6847 Remote Similarity NPD4754 Approved
0.6837 Remote Similarity NPD7645 Phase 2
0.6833 Remote Similarity NPD6059 Approved
0.6827 Remote Similarity NPD6051 Approved
0.6827 Remote Similarity NPD6673 Approved
0.6827 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6827 Remote Similarity NPD6080 Approved
0.6827 Remote Similarity NPD6904 Approved
0.6818 Remote Similarity NPD5344 Discontinued
0.6814 Remote Similarity NPD6412 Phase 2
0.6807 Remote Similarity NPD7327 Approved
0.6807 Remote Similarity NPD7328 Approved
0.6803 Remote Similarity NPD8328 Phase 3
0.68 Remote Similarity NPD5209 Approved
0.68 Remote Similarity NPD4221 Approved
0.68 Remote Similarity NPD4223 Phase 3
0.6783 Remote Similarity NPD5248 Approved
0.6783 Remote Similarity NPD5251 Approved
0.6783 Remote Similarity NPD5247 Approved
0.6783 Remote Similarity NPD5250 Approved
0.6783 Remote Similarity NPD5249 Phase 3
0.6777 Remote Similarity NPD6908 Approved
0.6777 Remote Similarity NPD6909 Approved
0.6777 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6777 Remote Similarity NPD5983 Phase 2
0.6777 Remote Similarity NPD7503 Approved
0.6777 Remote Similarity NPD8033 Approved
0.6777 Remote Similarity NPD8513 Phase 3
0.6774 Remote Similarity NPD8293 Discontinued
0.6762 Remote Similarity NPD5692 Phase 3
0.6754 Remote Similarity NPD5168 Approved
0.675 Remote Similarity NPD7516 Approved
0.6733 Remote Similarity NPD7154 Phase 3
0.6731 Remote Similarity NPD5208 Approved
0.6729 Remote Similarity NPD6001 Approved
0.6724 Remote Similarity NPD5215 Approved
0.6724 Remote Similarity NPD5217 Approved
0.6724 Remote Similarity NPD5216 Approved
0.6701 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6699 Remote Similarity NPD5690 Phase 2
0.6698 Remote Similarity NPD6050 Approved
0.6698 Remote Similarity NPD5694 Approved
0.6694 Remote Similarity NPD8377 Approved
0.6694 Remote Similarity NPD8294 Approved
0.6667 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7604 Phase 2
0.6667 Remote Similarity NPD4197 Approved
0.6639 Remote Similarity NPD8335 Approved
0.6639 Remote Similarity NPD8380 Approved
0.6639 Remote Similarity NPD8516 Approved
0.6639 Remote Similarity NPD8517 Approved
0.6639 Remote Similarity NPD8379 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