Structure

Physi-Chem Properties

Molecular Weight:  252.14
Volume:  260.839
LogP:  1.806
LogD:  1.524
LogS:  -1.937
# Rotatable Bonds:  3
TPSA:  66.76
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.744
Synthetic Accessibility Score:  4.74
Fsp3:  0.643
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:  -4.635
MDCK Permeability:  0.00013897080498281866
Pgp-inhibitor:  0.001
Pgp-substrate:  0.003
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.006
30% Bioavailability (F30%):  0.075

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.736
Plasma Protein Binding (PPB):  71.93872833251953%
Volume Distribution (VD):  0.38
Pgp-substrate:  15.306041717529297%

ADMET: Metabolism

CYP1A2-inhibitor:  0.014
CYP1A2-substrate:  0.498
CYP2C19-inhibitor:  0.068
CYP2C19-substrate:  0.816
CYP2C9-inhibitor:  0.034
CYP2C9-substrate:  0.314
CYP2D6-inhibitor:  0.011
CYP2D6-substrate:  0.183
CYP3A4-inhibitor:  0.072
CYP3A4-substrate:  0.421

ADMET: Excretion

Clearance (CL):  6.803
Half-life (T1/2):  0.441

ADMET: Toxicity

hERG Blockers:  0.014
Human Hepatotoxicity (H-HT):  0.187
Drug-inuced Liver Injury (DILI):  0.037
AMES Toxicity:  0.05
Rat Oral Acute Toxicity:  0.169
Maximum Recommended Daily Dose:  0.942
Skin Sensitization:  0.382
Carcinogencity:  0.927
Eye Corrosion:  0.049
Eye Irritation:  0.633
Respiratory Toxicity:  0.795

Download Data

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

  Natural Product: NPC228415

Natural Product ID:  NPC228415
Common Name*:   Illifunone C
IUPAC Name:   (2R,3aS,5R)-3a-hydroxy-2-(2-hydroxypropan-2-yl)-5-prop-2-enyl-2,3,4,5-tetrahydro-1-benzofuran-6-one
Synonyms:   Illifunone C
Standard InCHIKey:  WTNZYSLGDGRFTH-IUPBHXKESA-N
Standard InCHI:  InChI=1S/C14H20O4/c1-4-5-9-7-14(17)8-12(13(2,3)16)18-11(14)6-10(9)15/h4,6,9,12,16-17H,1,5,7-8H2,2-3H3/t9-,12-,14+/m1/s1
SMILES:  C=CC[C@@H]1C[C@]2(O)C[C@@H](OC2=CC1=O)C(O)(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL559236
PubChem CID:   15700250
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000301] Benzofurans

*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
NPO31423 Illicium oligandrum Species Schisandraceae Eukaryota pericarps n.a. n.a. PMID[19159273]
NPO31423 Illicium oligandrum Species Schisandraceae Eukaryota stem bark n.a. n.a. PMID[19496609]
NPO31423 Illicium oligandrum Species Schisandraceae Eukaryota n.a. stem n.a. PMID[21524101]
NPO31423 Illicium oligandrum Species Schisandraceae Eukaryota n.a. root n.a. PMID[25966312]

☑ 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
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = -9.4 % PMID[527722]

☑ 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 NPC228415 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 NPC87189
0.8817 High Similarity NPC9878
0.8387 Intermediate Similarity NPC135576
0.8387 Intermediate Similarity NPC93271
0.8235 Intermediate Similarity NPC291260
0.8229 Intermediate Similarity NPC471401
0.8152 Intermediate Similarity NPC476705
0.8043 Intermediate Similarity NPC166554
0.7979 Intermediate Similarity NPC14322
0.7979 Intermediate Similarity NPC469819
0.7979 Intermediate Similarity NPC114162
0.7959 Intermediate Similarity NPC70369
0.7912 Intermediate Similarity NPC23622
0.7872 Intermediate Similarity NPC61275
0.7872 Intermediate Similarity NPC475912
0.7849 Intermediate Similarity NPC265856
0.7843 Intermediate Similarity NPC471400
0.7835 Intermediate Similarity NPC300584
0.7826 Intermediate Similarity NPC476706
0.7826 Intermediate Similarity NPC476707
0.7812 Intermediate Similarity NPC8803
0.7766 Intermediate Similarity NPC475441
0.7766 Intermediate Similarity NPC146852
0.7732 Intermediate Similarity NPC40812
0.7732 Intermediate Similarity NPC27105
0.7732 Intermediate Similarity NPC20066
0.7727 Intermediate Similarity NPC472948
0.7727 Intermediate Similarity NPC470945
0.7727 Intermediate Similarity NPC470946
0.7727 Intermediate Similarity NPC470947
0.7717 Intermediate Similarity NPC472007
0.7708 Intermediate Similarity NPC36954
0.7708 Intermediate Similarity NPC270013
0.7708 Intermediate Similarity NPC14961
0.7684 Intermediate Similarity NPC295204
0.7684 Intermediate Similarity NPC288240
0.7684 Intermediate Similarity NPC476300
0.7684 Intermediate Similarity NPC162205
0.7684 Intermediate Similarity NPC273579
0.7674 Intermediate Similarity NPC474197
0.766 Intermediate Similarity NPC51004
0.766 Intermediate Similarity NPC473448
0.766 Intermediate Similarity NPC478003
0.766 Intermediate Similarity NPC158388
0.766 Intermediate Similarity NPC179394
0.766 Intermediate Similarity NPC478004
0.766 Intermediate Similarity NPC144133
0.7653 Intermediate Similarity NPC471330
0.7653 Intermediate Similarity NPC472687
0.7653 Intermediate Similarity NPC99657
0.7653 Intermediate Similarity NPC83895
0.7653 Intermediate Similarity NPC471331
0.7653 Intermediate Similarity NPC203388
0.7653 Intermediate Similarity NPC187761
0.7634 Intermediate Similarity NPC476704
0.7634 Intermediate Similarity NPC472008
0.7609 Intermediate Similarity NPC472009
0.7604 Intermediate Similarity NPC474035
0.7604 Intermediate Similarity NPC81386
0.7604 Intermediate Similarity NPC477241
0.76 Intermediate Similarity NPC149371
0.7579 Intermediate Similarity NPC30515
0.7579 Intermediate Similarity NPC230623
0.7579 Intermediate Similarity NPC184463
0.7556 Intermediate Similarity NPC474252
0.7553 Intermediate Similarity NPC307411
0.7551 Intermediate Similarity NPC266842
0.7551 Intermediate Similarity NPC239895
0.7549 Intermediate Similarity NPC472749
0.7549 Intermediate Similarity NPC472751
0.7549 Intermediate Similarity NPC471333
0.7549 Intermediate Similarity NPC471332
0.7528 Intermediate Similarity NPC162741
0.7528 Intermediate Similarity NPC91332
0.7527 Intermediate Similarity NPC179659
0.7525 Intermediate Similarity NPC475871
0.7525 Intermediate Similarity NPC472747
0.7525 Intermediate Similarity NPC472750
0.7525 Intermediate Similarity NPC475945
0.75 Intermediate Similarity NPC28887
0.75 Intermediate Similarity NPC81419
0.75 Intermediate Similarity NPC212486
0.75 Intermediate Similarity NPC474742
0.75 Intermediate Similarity NPC179746
0.75 Intermediate Similarity NPC472753
0.75 Intermediate Similarity NPC47880
0.7475 Intermediate Similarity NPC255592
0.7475 Intermediate Similarity NPC261377
0.7475 Intermediate Similarity NPC473326
0.7475 Intermediate Similarity NPC306908
0.7475 Intermediate Similarity NPC187268
0.7475 Intermediate Similarity NPC308567
0.7474 Intermediate Similarity NPC471399
0.7474 Intermediate Similarity NPC475855
0.7474 Intermediate Similarity NPC469464
0.7474 Intermediate Similarity NPC474761
0.7474 Intermediate Similarity NPC476004
0.7473 Intermediate Similarity NPC477785
0.7473 Intermediate Similarity NPC477784
0.7473 Intermediate Similarity NPC477786
0.7453 Intermediate Similarity NPC207251
0.7451 Intermediate Similarity NPC472756
0.7451 Intermediate Similarity NPC474741
0.7451 Intermediate Similarity NPC100487
0.7451 Intermediate Similarity NPC472748
0.7449 Intermediate Similarity NPC476315
0.7449 Intermediate Similarity NPC279621
0.7447 Intermediate Similarity NPC202672
0.7447 Intermediate Similarity NPC476708
0.7444 Intermediate Similarity NPC470241
0.7429 Intermediate Similarity NPC5103
0.7429 Intermediate Similarity NPC99760
0.7426 Intermediate Similarity NPC472754
0.7426 Intermediate Similarity NPC474747
0.7423 Intermediate Similarity NPC303942
0.7423 Intermediate Similarity NPC196227
0.7423 Intermediate Similarity NPC57405
0.7416 Intermediate Similarity NPC475210
0.74 Intermediate Similarity NPC288876
0.7396 Intermediate Similarity NPC252433
0.7396 Intermediate Similarity NPC12172
0.7396 Intermediate Similarity NPC111114
0.7396 Intermediate Similarity NPC116726
0.7396 Intermediate Similarity NPC473321
0.7396 Intermediate Similarity NPC261607
0.7396 Intermediate Similarity NPC208886
0.7396 Intermediate Similarity NPC300312
0.7391 Intermediate Similarity NPC295799
0.7391 Intermediate Similarity NPC472958
0.7391 Intermediate Similarity NPC472957
0.7368 Intermediate Similarity NPC295448
0.7368 Intermediate Similarity NPC473564
0.7368 Intermediate Similarity NPC473100
0.7358 Intermediate Similarity NPC304180
0.7358 Intermediate Similarity NPC179798
0.7353 Intermediate Similarity NPC472755
0.7353 Intermediate Similarity NPC473624
0.7353 Intermediate Similarity NPC110989
0.7347 Intermediate Similarity NPC304886
0.7347 Intermediate Similarity NPC91408
0.734 Intermediate Similarity NPC300779
0.734 Intermediate Similarity NPC237540
0.734 Intermediate Similarity NPC160138
0.7333 Intermediate Similarity NPC101018
0.7333 Intermediate Similarity NPC38154
0.7327 Intermediate Similarity NPC474339
0.7327 Intermediate Similarity NPC476270
0.7327 Intermediate Similarity NPC185141
0.7327 Intermediate Similarity NPC128733
0.7327 Intermediate Similarity NPC181645
0.7327 Intermediate Similarity NPC133907
0.7327 Intermediate Similarity NPC46998
0.7327 Intermediate Similarity NPC164598
0.7327 Intermediate Similarity NPC110443
0.732 Intermediate Similarity NPC469692
0.732 Intermediate Similarity NPC475838
0.732 Intermediate Similarity NPC125674
0.732 Intermediate Similarity NPC469645
0.732 Intermediate Similarity NPC228451
0.7315 Intermediate Similarity NPC326542
0.7312 Intermediate Similarity NPC125290
0.7312 Intermediate Similarity NPC21469
0.7312 Intermediate Similarity NPC475206
0.7312 Intermediate Similarity NPC307126
0.7312 Intermediate Similarity NPC68303
0.7312 Intermediate Similarity NPC165162
0.7303 Intermediate Similarity NPC231739
0.73 Intermediate Similarity NPC475284
0.73 Intermediate Similarity NPC278008
0.73 Intermediate Similarity NPC281608
0.73 Intermediate Similarity NPC470541
0.73 Intermediate Similarity NPC35717
0.73 Intermediate Similarity NPC474213
0.7292 Intermediate Similarity NPC214844
0.7292 Intermediate Similarity NPC473619
0.7292 Intermediate Similarity NPC15059
0.7292 Intermediate Similarity NPC473099
0.7292 Intermediate Similarity NPC129419
0.729 Intermediate Similarity NPC66108
0.729 Intermediate Similarity NPC472002
0.7283 Intermediate Similarity NPC250315
0.7283 Intermediate Similarity NPC185256
0.7282 Intermediate Similarity NPC296950
0.7282 Intermediate Similarity NPC258532
0.7282 Intermediate Similarity NPC220964
0.7282 Intermediate Similarity NPC146731
0.7282 Intermediate Similarity NPC475676
0.7282 Intermediate Similarity NPC203659
0.7273 Intermediate Similarity NPC472733
0.7273 Intermediate Similarity NPC472734
0.7263 Intermediate Similarity NPC153805
0.7263 Intermediate Similarity NPC473715
0.7255 Intermediate Similarity NPC303653
0.7255 Intermediate Similarity NPC86077
0.7255 Intermediate Similarity NPC223834
0.7255 Intermediate Similarity NPC189609
0.7255 Intermediate Similarity NPC39996
0.7255 Intermediate Similarity NPC225353
0.7255 Intermediate Similarity NPC291500
0.7255 Intermediate Similarity NPC140591

  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 NPC228415 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
0.7604 Intermediate Similarity NPD5282 Discontinued
0.7473 Intermediate Similarity NPD6110 Phase 1
0.7113 Intermediate Similarity NPD6698 Approved
0.7113 Intermediate Similarity NPD46 Approved
0.7041 Intermediate Similarity NPD7983 Approved
0.6915 Remote Similarity NPD7154 Phase 3
0.6875 Remote Similarity NPD4249 Approved
0.6832 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6822 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6804 Remote Similarity NPD4251 Approved
0.6804 Remote Similarity NPD4250 Approved
0.68 Remote Similarity NPD5778 Approved
0.68 Remote Similarity NPD5779 Approved
0.6789 Remote Similarity NPD6371 Approved
0.6771 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6727 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6632 Remote Similarity NPD6435 Approved
0.6628 Remote Similarity NPD7331 Phase 2
0.66 Remote Similarity NPD7838 Discovery
0.6598 Remote Similarity NPD5363 Approved
0.6598 Remote Similarity NPD1694 Approved
0.6531 Remote Similarity NPD5786 Approved
0.6518 Remote Similarity NPD6053 Discontinued
0.6514 Remote Similarity NPD6412 Phase 2
0.6512 Remote Similarity NPD7341 Phase 2
0.6509 Remote Similarity NPD5344 Discontinued
0.6476 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6476 Remote Similarity NPD4225 Approved
0.6458 Remote Similarity NPD4800 Clinical (unspecified phase)
0.6458 Remote Similarity NPD4269 Approved
0.6458 Remote Similarity NPD4270 Approved
0.6455 Remote Similarity NPD6686 Approved
0.6449 Remote Similarity NPD5211 Phase 2
0.6436 Remote Similarity NPD5785 Approved
0.6435 Remote Similarity NPD7115 Discovery
0.6421 Remote Similarity NPD4822 Approved
0.6421 Remote Similarity NPD4819 Approved
0.6421 Remote Similarity NPD5368 Approved
0.6421 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6421 Remote Similarity NPD4820 Approved
0.6421 Remote Similarity NPD4821 Approved
0.6396 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6383 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6364 Remote Similarity NPD4519 Discontinued
0.6364 Remote Similarity NPD4623 Approved
0.6356 Remote Similarity NPD8513 Phase 3
0.6356 Remote Similarity NPD8517 Approved
0.6356 Remote Similarity NPD8516 Approved
0.6356 Remote Similarity NPD8515 Approved
0.6354 Remote Similarity NPD5369 Approved
0.6339 Remote Similarity NPD4634 Approved
0.6339 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6337 Remote Similarity NPD1695 Approved
0.633 Remote Similarity NPD5141 Approved
0.6316 Remote Similarity NPD4632 Approved
0.63 Remote Similarity NPD7524 Approved
0.6286 Remote Similarity NPD7839 Suspended
0.6277 Remote Similarity NPD4756 Discovery
0.6271 Remote Similarity NPD6319 Approved
0.6271 Remote Similarity NPD6054 Approved
0.6262 Remote Similarity NPD6648 Approved
0.6262 Remote Similarity NPD5285 Approved
0.6262 Remote Similarity NPD4696 Approved
0.6262 Remote Similarity NPD5286 Approved
0.625 Remote Similarity NPD4252 Approved
0.6228 Remote Similarity NPD8297 Approved
0.6226 Remote Similarity NPD4755 Approved
0.6224 Remote Similarity NPD5362 Discontinued
0.6218 Remote Similarity NPD6015 Approved
0.6218 Remote Similarity NPD6016 Approved
0.6216 Remote Similarity NPD5697 Approved
0.6211 Remote Similarity NPD4268 Approved
0.6211 Remote Similarity NPD4271 Approved
0.62 Remote Similarity NPD3618 Phase 1
0.619 Remote Similarity NPD4629 Approved
0.619 Remote Similarity NPD5210 Approved
0.619 Remote Similarity NPD5695 Phase 3
0.6176 Remote Similarity NPD4753 Phase 2
0.6176 Remote Similarity NPD6101 Approved
0.6176 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6168 Remote Similarity NPD5696 Approved
0.6167 Remote Similarity NPD5988 Approved
0.6167 Remote Similarity NPD6370 Approved
0.6162 Remote Similarity NPD3665 Phase 1
0.6162 Remote Similarity NPD3133 Approved
0.6162 Remote Similarity NPD3666 Approved
0.6161 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6161 Remote Similarity NPD6899 Approved
0.6161 Remote Similarity NPD6881 Approved
0.6154 Remote Similarity NPD6399 Phase 3
0.6147 Remote Similarity NPD5225 Approved
0.6147 Remote Similarity NPD5226 Approved
0.6147 Remote Similarity NPD4633 Approved
0.6147 Remote Similarity NPD5224 Approved
0.614 Remote Similarity NPD6650 Approved
0.614 Remote Similarity NPD6649 Approved
0.6134 Remote Similarity NPD6059 Approved
0.6126 Remote Similarity NPD6008 Approved
0.6126 Remote Similarity NPD5739 Approved
0.6126 Remote Similarity NPD7128 Approved
0.6126 Remote Similarity NPD6402 Approved
0.6126 Remote Similarity NPD6675 Approved
0.6111 Remote Similarity NPD4700 Approved
0.6106 Remote Similarity NPD6372 Approved
0.6106 Remote Similarity NPD6012 Approved
0.6106 Remote Similarity NPD6013 Approved
0.6106 Remote Similarity NPD6014 Approved
0.6106 Remote Similarity NPD6373 Approved
0.6098 Remote Similarity NPD8074 Phase 3
0.6091 Remote Similarity NPD5174 Approved
0.6091 Remote Similarity NPD5175 Approved
0.6082 Remote Similarity NPD4695 Discontinued
0.6075 Remote Similarity NPD6084 Phase 2
0.6075 Remote Similarity NPD6083 Phase 2
0.6075 Remote Similarity NPD7902 Approved
0.6071 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6071 Remote Similarity NPD5701 Approved
0.6067 Remote Similarity NPD3704 Approved
0.6066 Remote Similarity NPD7492 Approved
0.6058 Remote Similarity NPD6079 Approved
0.6058 Remote Similarity NPD6411 Approved
0.6058 Remote Similarity NPD5281 Approved
0.6058 Remote Similarity NPD5284 Approved
0.6055 Remote Similarity NPD5223 Approved
0.6053 Remote Similarity NPD7290 Approved
0.6053 Remote Similarity NPD7102 Approved
0.6053 Remote Similarity NPD6883 Approved
0.604 Remote Similarity NPD5279 Phase 3
0.6019 Remote Similarity NPD5328 Approved
0.6018 Remote Similarity NPD7320 Approved
0.6018 Remote Similarity NPD6011 Approved
0.6017 Remote Similarity NPD6009 Approved
0.6016 Remote Similarity NPD6616 Approved
0.6 Remote Similarity NPD8130 Phase 1
0.6 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6 Remote Similarity NPD6869 Approved
0.6 Remote Similarity NPD4202 Approved
0.6 Remote Similarity NPD6617 Approved
0.6 Remote Similarity NPD6847 Approved
0.5984 Remote Similarity NPD7642 Approved
0.5981 Remote Similarity NPD5221 Approved
0.5981 Remote Similarity NPD5220 Clinical (unspecified phase)
0.5981 Remote Similarity NPD4697 Phase 3
0.5981 Remote Similarity NPD5222 Approved
0.5977 Remote Similarity NPD368 Approved
0.5968 Remote Similarity NPD7078 Approved
0.5966 Remote Similarity NPD7641 Discontinued
0.5963 Remote Similarity NPD7640 Approved
0.5963 Remote Similarity NPD7639 Approved
0.596 Remote Similarity NPD3667 Approved
0.596 Remote Similarity NPD4221 Approved
0.596 Remote Similarity NPD4752 Clinical (unspecified phase)
0.596 Remote Similarity NPD4223 Phase 3
0.595 Remote Similarity NPD5983 Phase 2
0.5948 Remote Similarity NPD6882 Approved
0.5943 Remote Similarity NPD7748 Approved
0.5941 Remote Similarity NPD1696 Phase 3
0.5935 Remote Similarity NPD8342 Approved
0.5935 Remote Similarity NPD8340 Approved
0.5935 Remote Similarity NPD8341 Approved
0.5935 Remote Similarity NPD8299 Approved
0.5926 Remote Similarity NPD5173 Approved
0.592 Remote Similarity NPD7736 Approved
0.5909 Remote Similarity NPD2664 Clinical (unspecified phase)
0.5906 Remote Similarity NPD7260 Phase 2
0.5905 Remote Similarity NPD7637 Suspended
0.5905 Remote Similarity NPD4810 Clinical (unspecified phase)
0.59 Remote Similarity NPD6695 Phase 3
0.5889 Remote Similarity NPD6108 Clinical (unspecified phase)
0.5887 Remote Similarity NPD7507 Approved
0.5882 Remote Similarity NPD5690 Phase 2
0.5882 Remote Similarity NPD6409 Approved
0.5882 Remote Similarity NPD7521 Approved
0.5882 Remote Similarity NPD7500 Approved
0.5882 Remote Similarity NPD3574 Clinical (unspecified phase)
0.5882 Remote Similarity NPD6684 Approved
0.5882 Remote Similarity NPD7334 Approved
0.5882 Remote Similarity NPD5330 Approved
0.5882 Remote Similarity NPD7146 Approved
0.5877 Remote Similarity NPD4730 Approved
0.5877 Remote Similarity NPD4729 Approved
0.5872 Remote Similarity NPD7638 Approved
0.5865 Remote Similarity NPD5370 Suspended
0.5862 Remote Similarity NPD7116 Clinical (unspecified phase)
0.5854 Remote Similarity NPD7604 Phase 2
0.5854 Remote Similarity NPD8328 Phase 3
0.5842 Remote Similarity NPD4786 Approved
0.5842 Remote Similarity NPD4197 Approved
0.5841 Remote Similarity NPD4768 Approved
0.5841 Remote Similarity NPD4767 Approved
0.584 Remote Similarity NPD8293 Discontinued
0.5826 Remote Similarity NPD8132 Clinical (unspecified phase)
0.582 Remote Similarity NPD7503 Approved
0.581 Remote Similarity NPD5207 Approved
0.5804 Remote Similarity NPD4754 Approved
0.5802 Remote Similarity NPD7966 Clinical (unspecified phase)
0.5794 Remote Similarity NPD7901 Clinical (unspecified phase)
0.5794 Remote Similarity NPD7900 Approved
0.5785 Remote Similarity NPD4522 Approved
0.5784 Remote Similarity NPD5329 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