Structure

Physi-Chem Properties

Molecular Weight:  348.19
Volume:  368.132
LogP:  2.535
LogD:  2.354
LogS:  -3.977
# Rotatable Bonds:  7
TPSA:  80.67
# H-Bond Aceptor:  5
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.331
Synthetic Accessibility Score:  5.413
Fsp3:  0.65
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  2
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.611
MDCK Permeability:  3.097427179454826e-05
Pgp-inhibitor:  0.979
Pgp-substrate:  0.038
Human Intestinal Absorption (HIA):  0.008
20% Bioavailability (F20%):  0.014
30% Bioavailability (F30%):  0.032

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.955
Plasma Protein Binding (PPB):  85.85163116455078%
Volume Distribution (VD):  1.089
Pgp-substrate:  12.94567584991455%

ADMET: Metabolism

CYP1A2-inhibitor:  0.007
CYP1A2-substrate:  0.354
CYP2C19-inhibitor:  0.027
CYP2C19-substrate:  0.839
CYP2C9-inhibitor:  0.016
CYP2C9-substrate:  0.054
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.05
CYP3A4-inhibitor:  0.805
CYP3A4-substrate:  0.807

ADMET: Excretion

Clearance (CL):  8.985
Half-life (T1/2):  0.388

ADMET: Toxicity

hERG Blockers:  0.037
Human Hepatotoxicity (H-HT):  0.123
Drug-inuced Liver Injury (DILI):  0.216
AMES Toxicity:  0.168
Rat Oral Acute Toxicity:  0.77
Maximum Recommended Daily Dose:  0.929
Skin Sensitization:  0.855
Carcinogencity:  0.912
Eye Corrosion:  0.851
Eye Irritation:  0.257
Respiratory Toxicity:  0.979

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

  Natural Product: NPC85529

Natural Product ID:  NPC85529
Common Name*:   Rezishanone B
IUPAC Name:   (1S,2S,4R,6E,8S)-8-butoxy-2-hydroxy-6-[(2E,4E)-1-hydroxyhexa-2,4-dienylidene]-2,4-dimethylbicyclo[2.2.2]octane-3,5-dione
Synonyms:  
Standard InCHIKey:  SSIULBZZANASKU-JMHWJZGWSA-N
Standard InCHI:  InChI=1S/C20H28O5/c1-5-7-9-10-14(21)16-13-12-15(25-11-8-6-2)19(3,17(16)22)18(23)20(13,4)24/h5,7,9-10,13,15,21,24H,6,8,11-12H2,1-4H3/b7-5+,10-9+,16-14+/t13-,15-,19+,20-/m0/s1
SMILES:  C/C=C/C=C/C(=C1/[C@@H]2C[C@@H]([C@](C)(C1=O)C(=O)[C@@]2(C)O)OCCCC)/O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL518881
PubChem CID:   44584010
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0001831] Carbonyl compounds
          • [CHEMONTID:0002088] Acyloins

*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
NPO32492 penicillium notatum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[15974609]

☑ 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
NPT79 Organism Bacillus subtilis Bacillus subtilis IZ = 12.0 mm PMID[533893]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus IZ = 12.0 mm PMID[533893]
NPT20 Organism Candida albicans Candida albicans IZ = 13.0 mm PMID[533893]

☑ 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 NPC85529 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 NPC32006
0.9485 High Similarity NPC46761
0.8611 High Similarity NPC474271
0.8318 Intermediate Similarity NPC168883
0.8241 Intermediate Similarity NPC300026
0.8182 Intermediate Similarity NPC472676
0.8182 Intermediate Similarity NPC472688
0.8155 Intermediate Similarity NPC273269
0.81 Intermediate Similarity NPC134321
0.8095 Intermediate Similarity NPC115862
0.8095 Intermediate Similarity NPC470184
0.8077 Intermediate Similarity NPC316598
0.8073 Intermediate Similarity NPC220705
0.8058 Intermediate Similarity NPC269492
0.8037 Intermediate Similarity NPC325769
0.8019 Intermediate Similarity NPC163249
0.7981 Intermediate Similarity NPC471916
0.7963 Intermediate Similarity NPC478052
0.7963 Intermediate Similarity NPC1679
0.7961 Intermediate Similarity NPC280725
0.7944 Intermediate Similarity NPC72151
0.7944 Intermediate Similarity NPC131366
0.7944 Intermediate Similarity NPC320294
0.7925 Intermediate Similarity NPC472637
0.7921 Intermediate Similarity NPC128672
0.7913 Intermediate Similarity NPC268958
0.7909 Intermediate Similarity NPC20192
0.7909 Intermediate Similarity NPC87335
0.7905 Intermediate Similarity NPC153776
0.7905 Intermediate Similarity NPC472730
0.7905 Intermediate Similarity NPC177680
0.7905 Intermediate Similarity NPC472729
0.789 Intermediate Similarity NPC473284
0.789 Intermediate Similarity NPC185
0.787 Intermediate Similarity NPC213366
0.787 Intermediate Similarity NPC118911
0.7864 Intermediate Similarity NPC196227
0.7864 Intermediate Similarity NPC299100
0.7864 Intermediate Similarity NPC212812
0.7864 Intermediate Similarity NPC293086
0.7864 Intermediate Similarity NPC474690
0.7857 Intermediate Similarity NPC193948
0.785 Intermediate Similarity NPC320447
0.783 Intermediate Similarity NPC472728
0.783 Intermediate Similarity NPC474802
0.783 Intermediate Similarity NPC266955
0.783 Intermediate Similarity NPC472727
0.7826 Intermediate Similarity NPC21326
0.7826 Intermediate Similarity NPC251310
0.7822 Intermediate Similarity NPC118011
0.7822 Intermediate Similarity NPC36668
0.781 Intermediate Similarity NPC474785
0.781 Intermediate Similarity NPC474938
0.781 Intermediate Similarity NPC170131
0.7798 Intermediate Similarity NPC472645
0.7788 Intermediate Similarity NPC180950
0.7788 Intermediate Similarity NPC134067
0.7788 Intermediate Similarity NPC316215
0.7788 Intermediate Similarity NPC476245
0.7788 Intermediate Similarity NPC272617
0.7778 Intermediate Similarity NPC329345
0.7778 Intermediate Similarity NPC475526
0.7778 Intermediate Similarity NPC475050
0.7778 Intermediate Similarity NPC271059
0.7778 Intermediate Similarity NPC473283
0.7778 Intermediate Similarity NPC25666
0.7778 Intermediate Similarity NPC90177
0.7778 Intermediate Similarity NPC275583
0.7757 Intermediate Similarity NPC115899
0.7757 Intermediate Similarity NPC207885
0.7757 Intermediate Similarity NPC472685
0.7757 Intermediate Similarity NPC472702
0.7757 Intermediate Similarity NPC323441
0.7757 Intermediate Similarity NPC112613
0.7757 Intermediate Similarity NPC81530
0.7757 Intermediate Similarity NPC282524
0.7748 Intermediate Similarity NPC470615
0.7736 Intermediate Similarity NPC109059
0.7736 Intermediate Similarity NPC288
0.7723 Intermediate Similarity NPC471791
0.7723 Intermediate Similarity NPC471793
0.7723 Intermediate Similarity NPC58271
0.7719 Intermediate Similarity NPC247069
0.7714 Intermediate Similarity NPC165616
0.7714 Intermediate Similarity NPC472734
0.7714 Intermediate Similarity NPC472733
0.77 Intermediate Similarity NPC203795
0.7699 Intermediate Similarity NPC475970
0.7699 Intermediate Similarity NPC264634
0.7699 Intermediate Similarity NPC147180
0.7692 Intermediate Similarity NPC472976
0.7692 Intermediate Similarity NPC472977
0.7692 Intermediate Similarity NPC103527
0.7692 Intermediate Similarity NPC478051
0.7685 Intermediate Similarity NPC80781
0.7685 Intermediate Similarity NPC136289
0.7677 Intermediate Similarity NPC40687
0.7677 Intermediate Similarity NPC251170
0.767 Intermediate Similarity NPC248913
0.767 Intermediate Similarity NPC472978
0.767 Intermediate Similarity NPC116726
0.767 Intermediate Similarity NPC172101
0.7664 Intermediate Similarity NPC117685
0.7664 Intermediate Similarity NPC174314
0.7664 Intermediate Similarity NPC198880
0.7658 Intermediate Similarity NPC318363
0.7658 Intermediate Similarity NPC102843
0.7658 Intermediate Similarity NPC475418
0.7658 Intermediate Similarity NPC473482
0.7647 Intermediate Similarity NPC472973
0.7647 Intermediate Similarity NPC474918
0.7642 Intermediate Similarity NPC472732
0.7642 Intermediate Similarity NPC474343
0.7642 Intermediate Similarity NPC254496
0.7642 Intermediate Similarity NPC208094
0.7642 Intermediate Similarity NPC472731
0.7642 Intermediate Similarity NPC473161
0.7636 Intermediate Similarity NPC477125
0.7636 Intermediate Similarity NPC166607
0.7632 Intermediate Similarity NPC472929
0.7632 Intermediate Similarity NPC326264
0.7624 Intermediate Similarity NPC220930
0.7624 Intermediate Similarity NPC471792
0.7624 Intermediate Similarity NPC272039
0.7623 Intermediate Similarity NPC221414
0.7619 Intermediate Similarity NPC295347
0.7615 Intermediate Similarity NPC473624
0.7615 Intermediate Similarity NPC311612
0.7615 Intermediate Similarity NPC473144
0.7615 Intermediate Similarity NPC249187
0.7615 Intermediate Similarity NPC247957
0.7615 Intermediate Similarity NPC194323
0.7615 Intermediate Similarity NPC230918
0.7615 Intermediate Similarity NPC297281
0.7611 Intermediate Similarity NPC171888
0.7611 Intermediate Similarity NPC179798
0.7611 Intermediate Similarity NPC472928
0.7611 Intermediate Similarity NPC304180
0.7611 Intermediate Similarity NPC34315
0.7611 Intermediate Similarity NPC146945
0.7607 Intermediate Similarity NPC472933
0.76 Intermediate Similarity NPC79573
0.7596 Intermediate Similarity NPC477436
0.7596 Intermediate Similarity NPC477435
0.7596 Intermediate Similarity NPC131840
0.7593 Intermediate Similarity NPC472643
0.7593 Intermediate Similarity NPC476240
0.7593 Intermediate Similarity NPC476223
0.7593 Intermediate Similarity NPC224720
0.7589 Intermediate Similarity NPC214644
0.7589 Intermediate Similarity NPC475065
0.7586 Intermediate Similarity NPC472934
0.7586 Intermediate Similarity NPC474518
0.7586 Intermediate Similarity NPC472927
0.7586 Intermediate Similarity NPC477116
0.7586 Intermediate Similarity NPC27999
0.7573 Intermediate Similarity NPC113393
0.757 Intermediate Similarity NPC278008
0.757 Intermediate Similarity NPC478056
0.7568 Intermediate Similarity NPC329048
0.7568 Intermediate Similarity NPC330011
0.7565 Intermediate Similarity NPC261330
0.7549 Intermediate Similarity NPC307298
0.7547 Intermediate Similarity NPC223169
0.7547 Intermediate Similarity NPC250757
0.7547 Intermediate Similarity NPC272411
0.7547 Intermediate Similarity NPC301534
0.7547 Intermediate Similarity NPC94337
0.7547 Intermediate Similarity NPC21681
0.7547 Intermediate Similarity NPC249954
0.7547 Intermediate Similarity NPC471153
0.7547 Intermediate Similarity NPC472675
0.7545 Intermediate Similarity NPC40170
0.7545 Intermediate Similarity NPC160843
0.7525 Intermediate Similarity NPC94666
0.7525 Intermediate Similarity NPC470955
0.7524 Intermediate Similarity NPC474328
0.7524 Intermediate Similarity NPC474882
0.7524 Intermediate Similarity NPC477439
0.7524 Intermediate Similarity NPC38830
0.7523 Intermediate Similarity NPC308726
0.7523 Intermediate Similarity NPC114540
0.7523 Intermediate Similarity NPC162973
0.7523 Intermediate Similarity NPC272472
0.7523 Intermediate Similarity NPC87351
0.7523 Intermediate Similarity NPC155332
0.7523 Intermediate Similarity NPC119601
0.7523 Intermediate Similarity NPC32577
0.7522 Intermediate Similarity NPC286880
0.7522 Intermediate Similarity NPC478209
0.7522 Intermediate Similarity NPC272898
0.7522 Intermediate Similarity NPC473036
0.7521 Intermediate Similarity NPC225049
0.75 Intermediate Similarity NPC99380
0.75 Intermediate Similarity NPC168027
0.75 Intermediate Similarity NPC478216
0.75 Intermediate Similarity NPC185936
0.75 Intermediate Similarity NPC35751
0.75 Intermediate Similarity NPC295244
0.75 Intermediate Similarity NPC476274

  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 NPC85529 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
0.7685 Intermediate Similarity NPD5211 Phase 2
0.7545 Intermediate Similarity NPD5141 Approved
0.75 Intermediate Similarity NPD5286 Approved
0.75 Intermediate Similarity NPD5285 Approved
0.75 Intermediate Similarity NPD4696 Approved
0.7477 Intermediate Similarity NPD4755 Approved
0.7431 Intermediate Similarity NPD5223 Approved
0.7411 Intermediate Similarity NPD5697 Approved
0.7383 Intermediate Similarity NPD5222 Approved
0.7383 Intermediate Similarity NPD4697 Phase 3
0.7383 Intermediate Similarity NPD5221 Approved
0.7383 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7364 Intermediate Similarity NPD4633 Approved
0.7364 Intermediate Similarity NPD5225 Approved
0.7364 Intermediate Similarity NPD5224 Approved
0.7364 Intermediate Similarity NPD5226 Approved
0.7345 Intermediate Similarity NPD6899 Approved
0.7345 Intermediate Similarity NPD6881 Approved
0.7345 Intermediate Similarity NPD6011 Approved
0.7339 Intermediate Similarity NPD4700 Approved
0.7321 Intermediate Similarity NPD6402 Approved
0.7321 Intermediate Similarity NPD5739 Approved
0.7321 Intermediate Similarity NPD6675 Approved
0.7321 Intermediate Similarity NPD7128 Approved
0.7315 Intermediate Similarity NPD5173 Approved
0.7304 Intermediate Similarity NPD6649 Approved
0.7304 Intermediate Similarity NPD6650 Approved
0.7297 Intermediate Similarity NPD5174 Approved
0.7297 Intermediate Similarity NPD5175 Approved
0.7281 Intermediate Similarity NPD6013 Approved
0.7281 Intermediate Similarity NPD6373 Approved
0.7281 Intermediate Similarity NPD6372 Approved
0.7281 Intermediate Similarity NPD6014 Approved
0.7281 Intermediate Similarity NPD6012 Approved
0.7257 Intermediate Similarity NPD5701 Approved
0.7217 Intermediate Similarity NPD7290 Approved
0.7217 Intermediate Similarity NPD7102 Approved
0.7217 Intermediate Similarity NPD6883 Approved
0.7217 Intermediate Similarity NPD4634 Approved
0.7196 Intermediate Similarity NPD5282 Discontinued
0.7193 Intermediate Similarity NPD7320 Approved
0.7184 Intermediate Similarity NPD3618 Phase 1
0.717 Intermediate Similarity NPD6079 Approved
0.7156 Intermediate Similarity NPD7902 Approved
0.7155 Intermediate Similarity NPD8130 Phase 1
0.7155 Intermediate Similarity NPD6617 Approved
0.7155 Intermediate Similarity NPD6869 Approved
0.7155 Intermediate Similarity NPD6847 Approved
0.7143 Intermediate Similarity NPD7115 Discovery
0.7143 Intermediate Similarity NPD5328 Approved
0.7143 Intermediate Similarity NPD4754 Approved
0.713 Intermediate Similarity NPD4629 Approved
0.713 Intermediate Similarity NPD5210 Approved
0.7103 Intermediate Similarity NPD5778 Approved
0.7103 Intermediate Similarity NPD5779 Approved
0.71 Intermediate Similarity NPD4695 Discontinued
0.7094 Intermediate Similarity NPD8297 Approved
0.7094 Intermediate Similarity NPD6882 Approved
0.7091 Intermediate Similarity NPD5696 Approved
0.7091 Intermediate Similarity NPD4225 Approved
0.7043 Intermediate Similarity NPD4730 Approved
0.7043 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7043 Intermediate Similarity NPD4729 Approved
0.7037 Intermediate Similarity NPD7748 Approved
0.7019 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD4767 Approved
0.7018 Intermediate Similarity NPD4768 Approved
0.7009 Intermediate Similarity NPD6411 Approved
0.7009 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.6967 Remote Similarity NPD6054 Approved
0.6967 Remote Similarity NPD6319 Approved
0.6952 Remote Similarity NPD3573 Approved
0.6944 Remote Similarity NPD6399 Phase 3
0.6944 Remote Similarity NPD4202 Approved
0.6923 Remote Similarity NPD1696 Phase 3
0.6923 Remote Similarity NPD5250 Approved
0.6923 Remote Similarity NPD5247 Approved
0.6923 Remote Similarity NPD5135 Approved
0.6923 Remote Similarity NPD5169 Approved
0.6923 Remote Similarity NPD5249 Phase 3
0.6923 Remote Similarity NPD5248 Approved
0.6923 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6923 Remote Similarity NPD5251 Approved
0.6911 Remote Similarity NPD6016 Approved
0.6911 Remote Similarity NPD6015 Approved
0.6897 Remote Similarity NPD5128 Approved
0.6891 Remote Similarity NPD4632 Approved
0.6881 Remote Similarity NPD7900 Approved
0.6881 Remote Similarity NPD7901 Clinical (unspecified phase)
0.687 Remote Similarity NPD6008 Approved
0.6864 Remote Similarity NPD5217 Approved
0.6864 Remote Similarity NPD5127 Approved
0.6864 Remote Similarity NPD5215 Approved
0.6864 Remote Similarity NPD5216 Approved
0.686 Remote Similarity NPD6317 Approved
0.6857 Remote Similarity NPD5279 Phase 3
0.6857 Remote Similarity NPD4519 Discontinued
0.6857 Remote Similarity NPD4623 Approved
0.6855 Remote Similarity NPD6370 Approved
0.6855 Remote Similarity NPD5988 Approved
0.6852 Remote Similarity NPD7515 Phase 2
0.6829 Remote Similarity NPD6059 Approved
0.6822 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6822 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6822 Remote Similarity NPD4753 Phase 2
0.6822 Remote Similarity NPD6101 Approved
0.6803 Remote Similarity NPD6314 Approved
0.6803 Remote Similarity NPD6335 Approved
0.6803 Remote Similarity NPD6313 Approved
0.6796 Remote Similarity NPD3667 Approved
0.6777 Remote Similarity NPD6274 Approved
0.6774 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6765 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6752 Remote Similarity NPD5168 Approved
0.6748 Remote Similarity NPD7100 Approved
0.6748 Remote Similarity NPD7101 Approved
0.6746 Remote Similarity NPD7492 Approved
0.6726 Remote Similarity NPD7639 Approved
0.6726 Remote Similarity NPD7640 Approved
0.6721 Remote Similarity NPD6009 Approved
0.6698 Remote Similarity NPD4694 Approved
0.6698 Remote Similarity NPD5280 Approved
0.6697 Remote Similarity NPD5281 Approved
0.6697 Remote Similarity NPD5284 Approved
0.6696 Remote Similarity NPD6084 Phase 2
0.6696 Remote Similarity NPD6083 Phase 2
0.6694 Remote Similarity NPD5167 Approved
0.6693 Remote Similarity NPD6616 Approved
0.6692 Remote Similarity NPD7260 Phase 2
0.6667 Remote Similarity NPD3665 Phase 1
0.6667 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5695 Phase 3
0.6667 Remote Similarity NPD3133 Approved
0.6667 Remote Similarity NPD4786 Approved
0.6667 Remote Similarity NPD4197 Approved
0.6667 Remote Similarity NPD3666 Approved
0.6667 Remote Similarity NPD8328 Phase 3
0.6641 Remote Similarity NPD7078 Approved
0.664 Remote Similarity NPD5983 Phase 2
0.6639 Remote Similarity NPD6868 Approved
0.6637 Remote Similarity NPD7638 Approved
0.6604 Remote Similarity NPD5329 Approved
0.6604 Remote Similarity NPD1694 Approved
0.6589 Remote Similarity NPD7736 Approved
0.6574 Remote Similarity NPD6672 Approved
0.6574 Remote Similarity NPD5737 Approved
0.6569 Remote Similarity NPD3617 Approved
0.6545 Remote Similarity NPD7637 Suspended
0.6545 Remote Similarity NPD5694 Approved
0.6542 Remote Similarity NPD5690 Phase 2
0.6535 Remote Similarity NPD7604 Phase 2
0.6512 Remote Similarity NPD8293 Discontinued
0.6509 Remote Similarity NPD3668 Phase 3
0.6508 Remote Similarity NPD6908 Approved
0.6508 Remote Similarity NPD6909 Approved
0.65 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6476 Remote Similarity NPD4221 Approved
0.6476 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6476 Remote Similarity NPD4800 Clinical (unspecified phase)
0.6476 Remote Similarity NPD4223 Phase 3
0.6466 Remote Similarity NPD5091 Approved
0.6462 Remote Similarity NPD6033 Approved
0.6455 Remote Similarity NPD5692 Phase 3
0.6455 Remote Similarity NPD5785 Approved
0.6434 Remote Similarity NPD6336 Discontinued
0.6417 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6396 Remote Similarity NPD8034 Phase 2
0.6396 Remote Similarity NPD7983 Approved
0.6396 Remote Similarity NPD8035 Phase 2
0.6396 Remote Similarity NPD6050 Approved
0.6396 Remote Similarity NPD5693 Phase 1
0.6389 Remote Similarity NPD7146 Approved
0.6389 Remote Similarity NPD7521 Approved
0.6389 Remote Similarity NPD6409 Approved
0.6389 Remote Similarity NPD6684 Approved
0.6389 Remote Similarity NPD5330 Approved
0.6389 Remote Similarity NPD7334 Approved
0.6389 Remote Similarity NPD5786 Approved
0.6378 Remote Similarity NPD6921 Approved
0.6372 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6364 Remote Similarity NPD6080 Approved
0.6364 Remote Similarity NPD6673 Approved
0.6364 Remote Similarity NPD6904 Approved
0.6355 Remote Similarity NPD7338 Clinical (unspecified phase)
0.632 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6306 Remote Similarity NPD5207 Approved
0.6296 Remote Similarity NPD5363 Approved
0.6293 Remote Similarity NPD6648 Approved
0.6288 Remote Similarity NPD7319 Approved
0.6286 Remote Similarity NPD7525 Registered
0.6275 Remote Similarity NPD8264 Approved
0.6273 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6273 Remote Similarity NPD6903 Approved
0.6269 Remote Similarity NPD6845 Suspended
0.6262 Remote Similarity NPD6695 Phase 3
0.625 Remote Similarity NPD8513 Phase 3
0.625 Remote Similarity NPD8516 Approved
0.625 Remote Similarity NPD8517 Approved
0.625 Remote Similarity NPD8515 Approved
0.625 Remote Similarity NPD5954 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