Structure

Physi-Chem Properties

Molecular Weight:  344.24
Volume:  379.224
LogP:  4.666
LogD:  3.938
LogS:  -5.393
# Rotatable Bonds:  4
TPSA:  46.53
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.636
Synthetic Accessibility Score:  3.713
Fsp3:  0.682
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.894
MDCK Permeability:  1.9441175027168356e-05
Pgp-inhibitor:  0.95
Pgp-substrate:  0.015
Human Intestinal Absorption (HIA):  0.013
20% Bioavailability (F20%):  0.992
30% Bioavailability (F30%):  0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.248
Plasma Protein Binding (PPB):  96.08879089355469%
Volume Distribution (VD):  1.148
Pgp-substrate:  3.0747220516204834%

ADMET: Metabolism

CYP1A2-inhibitor:  0.487
CYP1A2-substrate:  0.482
CYP2C19-inhibitor:  0.202
CYP2C19-substrate:  0.913
CYP2C9-inhibitor:  0.225
CYP2C9-substrate:  0.448
CYP2D6-inhibitor:  0.112
CYP2D6-substrate:  0.608
CYP3A4-inhibitor:  0.633
CYP3A4-substrate:  0.555

ADMET: Excretion

Clearance (CL):  5.601
Half-life (T1/2):  0.219

ADMET: Toxicity

hERG Blockers:  0.014
Human Hepatotoxicity (H-HT):  0.014
Drug-inuced Liver Injury (DILI):  0.474
AMES Toxicity:  0.021
Rat Oral Acute Toxicity:  0.43
Maximum Recommended Daily Dose:  0.909
Skin Sensitization:  0.737
Carcinogencity:  0.053
Eye Corrosion:  0.004
Eye Irritation:  0.223
Respiratory Toxicity:  0.507

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

  Natural Product: NPC249425

Natural Product ID:  NPC249425
Common Name*:   O-Acetyl-18-Hydroxyferruginol
IUPAC Name:   [(4bS,8R,8aR)-8-(hydroxymethyl)-4b,8-dimethyl-2-propan-2-yl-5,6,7,8a,9,10-hexahydrophenanthren-3-yl] acetate
Synonyms:  
Standard InCHIKey:  BNZJGBGPSWQEAU-FDFHNCONSA-N
Standard InCHI:  InChI=1S/C22H32O3/c1-14(2)17-11-16-7-8-20-21(4,13-23)9-6-10-22(20,5)18(16)12-19(17)25-15(3)24/h11-12,14,20,23H,6-10,13H2,1-5H3/t20-,21-,22+/m0/s1
SMILES:  OC[C@]1(C)CCC[C@]2([C@H]1CCc1c2cc(c(c1)C(C)C)OC(=O)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1277754
PubChem CID:   52945977
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001551] Diterpenoids

*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
NPO28466 Torreya nucifera Species Taxaceae 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
NPT1595 Individual Protein Replicase polyprotein 1ab SARS coronavirus Inhibition = 78.6 % PMID[504294]
NPT1595 Individual Protein Replicase polyprotein 1ab SARS coronavirus IC50 = 128900.0 nM PMID[504294]

☑ 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 NPC249425 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
0.8915 High Similarity NPC176590
0.8889 High Similarity NPC152946
0.8837 High Similarity NPC186889
0.8779 High Similarity NPC196193
0.8777 High Similarity NPC471608
0.8682 High Similarity NPC4286
0.8682 High Similarity NPC76119
0.8657 High Similarity NPC213122
0.8626 High Similarity NPC223912
0.8615 High Similarity NPC128321
0.8594 High Similarity NPC473464
0.8594 High Similarity NPC476332
0.8507 High Similarity NPC289624
0.8507 High Similarity NPC27578
0.848 Intermediate Similarity NPC312105
0.845 Intermediate Similarity NPC478058
0.8433 Intermediate Similarity NPC153019
0.8433 Intermediate Similarity NPC258073
0.8417 Intermediate Similarity NPC138149
0.8406 Intermediate Similarity NPC265335
0.84 Intermediate Similarity NPC35797
0.84 Intermediate Similarity NPC192948
0.837 Intermediate Similarity NPC85595
0.8359 Intermediate Similarity NPC135467
0.8359 Intermediate Similarity NPC260832
0.8358 Intermediate Similarity NPC475102
0.8357 Intermediate Similarity NPC20631
0.8357 Intermediate Similarity NPC93640
0.8346 Intermediate Similarity NPC81261
0.8346 Intermediate Similarity NPC201069
0.8333 Intermediate Similarity NPC308311
0.8333 Intermediate Similarity NPC477137
0.8333 Intermediate Similarity NPC131198
0.8333 Intermediate Similarity NPC38893
0.8321 Intermediate Similarity NPC265413
0.8321 Intermediate Similarity NPC10154
0.8321 Intermediate Similarity NPC75432
0.8309 Intermediate Similarity NPC211352
0.8309 Intermediate Similarity NPC227719
0.8306 Intermediate Similarity NPC280760
0.8288 Intermediate Similarity NPC476452
0.8284 Intermediate Similarity NPC206028
0.8273 Intermediate Similarity NPC76032
0.8273 Intermediate Similarity NPC132723
0.8271 Intermediate Similarity NPC156298
0.8271 Intermediate Similarity NPC471077
0.8268 Intermediate Similarity NPC172219
0.8268 Intermediate Similarity NPC25648
0.8268 Intermediate Similarity NPC304510
0.8248 Intermediate Similarity NPC27394
0.8239 Intermediate Similarity NPC474599
0.8231 Intermediate Similarity NPC475839
0.8231 Intermediate Similarity NPC168707
0.8231 Intermediate Similarity NPC48623
0.8231 Intermediate Similarity NPC162935
0.8231 Intermediate Similarity NPC249340
0.8226 Intermediate Similarity NPC470723
0.8217 Intermediate Similarity NPC103916
0.8214 Intermediate Similarity NPC79372
0.8209 Intermediate Similarity NPC47288
0.8203 Intermediate Similarity NPC471671
0.8201 Intermediate Similarity NPC306365
0.8195 Intermediate Similarity NPC470724
0.8189 Intermediate Similarity NPC219112
0.8182 Intermediate Similarity NPC111088
0.8182 Intermediate Similarity NPC248557
0.8175 Intermediate Similarity NPC268160
0.8168 Intermediate Similarity NPC188997
0.8168 Intermediate Similarity NPC121168
0.8156 Intermediate Similarity NPC472523
0.8154 Intermediate Similarity NPC129176
0.8154 Intermediate Similarity NPC45663
0.8154 Intermediate Similarity NPC322569
0.814 Intermediate Similarity NPC469644
0.8138 Intermediate Similarity NPC95990
0.8138 Intermediate Similarity NPC303013
0.8138 Intermediate Similarity NPC474940
0.8138 Intermediate Similarity NPC474795
0.8138 Intermediate Similarity NPC159697
0.8138 Intermediate Similarity NPC130959
0.8129 Intermediate Similarity NPC68292
0.8125 Intermediate Similarity NPC238075
0.8125 Intermediate Similarity NPC477136
0.812 Intermediate Similarity NPC470726
0.812 Intermediate Similarity NPC124030
0.8112 Intermediate Similarity NPC36732
0.811 Intermediate Similarity NPC147179
0.8108 Intermediate Similarity NPC44606
0.8106 Intermediate Similarity NPC471187
0.8106 Intermediate Similarity NPC261992
0.8085 Intermediate Similarity NPC473049
0.8085 Intermediate Similarity NPC472794
0.8085 Intermediate Similarity NPC76312
0.8082 Intermediate Similarity NPC471852
0.8082 Intermediate Similarity NPC146388
0.808 Intermediate Similarity NPC260323
0.808 Intermediate Similarity NPC176279
0.8077 Intermediate Similarity NPC478121
0.8077 Intermediate Similarity NPC474131
0.806 Intermediate Similarity NPC325294
0.806 Intermediate Similarity NPC321822
0.8056 Intermediate Similarity NPC290038
0.8047 Intermediate Similarity NPC471668
0.8047 Intermediate Similarity NPC469663
0.8047 Intermediate Similarity NPC308828
0.8047 Intermediate Similarity NPC92
0.8047 Intermediate Similarity NPC33900
0.8045 Intermediate Similarity NPC61685
0.8045 Intermediate Similarity NPC474532
0.8045 Intermediate Similarity NPC181334
0.8045 Intermediate Similarity NPC474237
0.8043 Intermediate Similarity NPC472524
0.8043 Intermediate Similarity NPC469610
0.8043 Intermediate Similarity NPC49742
0.8041 Intermediate Similarity NPC48671
0.803 Intermediate Similarity NPC11250
0.8029 Intermediate Similarity NPC8899
0.8029 Intermediate Similarity NPC164295
0.8028 Intermediate Similarity NPC155552
0.8015 Intermediate Similarity NPC241001
0.8015 Intermediate Similarity NPC131684
0.8015 Intermediate Similarity NPC212559
0.8015 Intermediate Similarity NPC86257
0.8014 Intermediate Similarity NPC474834
0.8014 Intermediate Similarity NPC117788
0.8014 Intermediate Similarity NPC474856
0.8014 Intermediate Similarity NPC290902
0.8014 Intermediate Similarity NPC291326
0.8 Intermediate Similarity NPC475872
0.8 Intermediate Similarity NPC471670
0.8 Intermediate Similarity NPC474610
0.8 Intermediate Similarity NPC32152
0.8 Intermediate Similarity NPC108164
0.8 Intermediate Similarity NPC115861
0.8 Intermediate Similarity NPC98748
0.7985 Intermediate Similarity NPC279118
0.7973 Intermediate Similarity NPC140133
0.7972 Intermediate Similarity NPC186033
0.7971 Intermediate Similarity NPC321086
0.7971 Intermediate Similarity NPC469611
0.7971 Intermediate Similarity NPC165612
0.7959 Intermediate Similarity NPC475940
0.7959 Intermediate Similarity NPC181452
0.7959 Intermediate Similarity NPC474893
0.7959 Intermediate Similarity NPC220006
0.7958 Intermediate Similarity NPC221134
0.7956 Intermediate Similarity NPC470727
0.7956 Intermediate Similarity NPC473048
0.7956 Intermediate Similarity NPC470725
0.7939 Intermediate Similarity NPC232295
0.7931 Intermediate Similarity NPC260152
0.7931 Intermediate Similarity NPC307205
0.7931 Intermediate Similarity NPC86069
0.7926 Intermediate Similarity NPC100414
0.7926 Intermediate Similarity NPC43000
0.7926 Intermediate Similarity NPC101894
0.7923 Intermediate Similarity NPC154030
0.7923 Intermediate Similarity NPC139047
0.7923 Intermediate Similarity NPC469609
0.7914 Intermediate Similarity NPC185777
0.7905 Intermediate Similarity NPC474305
0.7905 Intermediate Similarity NPC146014
0.7905 Intermediate Similarity NPC183380
0.7902 Intermediate Similarity NPC472791
0.7902 Intermediate Similarity NPC472792
0.7899 Intermediate Similarity NPC312341
0.7899 Intermediate Similarity NPC160623
0.7899 Intermediate Similarity NPC191395
0.7899 Intermediate Similarity NPC239134
0.7895 Intermediate Similarity NPC150026
0.7895 Intermediate Similarity NPC302211
0.7891 Intermediate Similarity NPC195922
0.7891 Intermediate Similarity NPC212142
0.7891 Intermediate Similarity NPC470757
0.7887 Intermediate Similarity NPC202260
0.7887 Intermediate Similarity NPC307883
0.7883 Intermediate Similarity NPC472797
0.7874 Intermediate Similarity NPC228425
0.7874 Intermediate Similarity NPC250323
0.7872 Intermediate Similarity NPC92932
0.7872 Intermediate Similarity NPC472800
0.7868 Intermediate Similarity NPC473993
0.7867 Intermediate Similarity NPC469699
0.7863 Intermediate Similarity NPC126002
0.7863 Intermediate Similarity NPC42657
0.7863 Intermediate Similarity NPC234956
0.7863 Intermediate Similarity NPC471449
0.7863 Intermediate Similarity NPC93071
0.7862 Intermediate Similarity NPC164183
0.7862 Intermediate Similarity NPC473845
0.7857 Intermediate Similarity NPC473107
0.7857 Intermediate Similarity NPC132720
0.7857 Intermediate Similarity NPC141782
0.7857 Intermediate Similarity NPC11266
0.7852 Intermediate Similarity NPC293801
0.7852 Intermediate Similarity NPC170749
0.7852 Intermediate Similarity NPC105031
0.7852 Intermediate Similarity NPC137750
0.7852 Intermediate Similarity NPC81641
0.7852 Intermediate Similarity NPC137416

  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 NPC249425 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
0.9077 High Similarity NPD4140 Approved
0.8571 High Similarity NPD5691 Approved
0.8507 High Similarity NPD4060 Phase 1
0.8504 High Similarity NPD4626 Approved
0.8433 Intermediate Similarity NPD8032 Phase 2
0.8385 Intermediate Similarity NPD5327 Phase 3
0.8309 Intermediate Similarity NPD5735 Approved
0.8231 Intermediate Similarity NPD1611 Approved
0.8194 Intermediate Similarity NPD6273 Approved
0.8182 Intermediate Similarity NPD1283 Approved
0.8148 Intermediate Similarity NPD7095 Approved
0.8143 Intermediate Similarity NPD5763 Approved
0.8143 Intermediate Similarity NPD5762 Approved
0.8125 Intermediate Similarity NPD7644 Approved
0.8116 Intermediate Similarity NPD6353 Approved
0.8088 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.8077 Intermediate Similarity NPD1778 Approved
0.8016 Intermediate Similarity NPD5535 Approved
0.8 Intermediate Similarity NPD5736 Approved
0.7986 Intermediate Similarity NPD4097 Suspended
0.7972 Intermediate Similarity NPD7003 Approved
0.7956 Intermediate Similarity NPD7985 Registered
0.7955 Intermediate Similarity NPD1281 Approved
0.7926 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7926 Intermediate Similarity NPD4624 Approved
0.791 Intermediate Similarity NPD6696 Suspended
0.7902 Intermediate Similarity NPD6674 Discontinued
0.7863 Intermediate Similarity NPD5585 Approved
0.7842 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7842 Intermediate Similarity NPD3620 Phase 2
0.7842 Intermediate Similarity NPD2979 Phase 3
0.7836 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7829 Intermediate Similarity NPD7157 Approved
0.7817 Intermediate Similarity NPD4477 Approved
0.7817 Intermediate Similarity NPD4476 Approved
0.7786 Intermediate Similarity NPD6355 Discontinued
0.7785 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD8651 Approved
0.777 Intermediate Similarity NPD6663 Approved
0.7769 Intermediate Similarity NPD7340 Approved
0.7755 Intermediate Similarity NPD7446 Clinical (unspecified phase)
0.7755 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7754 Intermediate Similarity NPD4625 Phase 3
0.7744 Intermediate Similarity NPD3496 Discontinued
0.774 Intermediate Similarity NPD6667 Approved
0.774 Intermediate Similarity NPD6666 Approved
0.7737 Intermediate Similarity NPD2237 Approved
0.773 Intermediate Similarity NPD4579 Clinical (unspecified phase)
0.7727 Intermediate Similarity NPD1651 Approved
0.7724 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7721 Intermediate Similarity NPD2797 Approved
0.7698 Intermediate Similarity NPD6798 Discontinued
0.7698 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD6099 Approved
0.7692 Intermediate Similarity NPD6100 Approved
0.7676 Intermediate Similarity NPD7097 Phase 1
0.7652 Intermediate Similarity NPD3091 Approved
0.7639 Intermediate Similarity NPD2346 Discontinued
0.7628 Intermediate Similarity NPD8127 Discontinued
0.7609 Intermediate Similarity NPD2861 Phase 2
0.7603 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7603 Intermediate Similarity NPD4110 Phase 3
0.7574 Intermediate Similarity NPD4749 Approved
0.7574 Intermediate Similarity NPD4359 Approved
0.7571 Intermediate Similarity NPD7294 Phase 1
0.7571 Intermediate Similarity NPD6812 Clinical (unspecified phase)
0.7569 Intermediate Similarity NPD2531 Phase 2
0.7569 Intermediate Similarity NPD2438 Suspended
0.7559 Intermediate Similarity NPD2684 Approved
0.7557 Intermediate Similarity NPD6671 Approved
0.7554 Intermediate Similarity NPD4908 Phase 1
0.755 Intermediate Similarity NPD7458 Discontinued
0.7538 Intermediate Similarity NPD1398 Phase 1
0.7537 Intermediate Similarity NPD3095 Discontinued
0.7535 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7535 Intermediate Similarity NPD5124 Phase 1
0.7533 Intermediate Similarity NPD7427 Discontinued
0.7533 Intermediate Similarity NPD5699 Approved
0.75 Intermediate Similarity NPD1608 Approved
0.75 Intermediate Similarity NPD2799 Discontinued
0.7483 Intermediate Similarity NPD4628 Phase 3
0.7483 Intermediate Similarity NPD2157 Approved
0.7468 Intermediate Similarity NPD7819 Suspended
0.7467 Intermediate Similarity NPD2675 Approved
0.7467 Intermediate Similarity NPD2676 Approved
0.7462 Intermediate Similarity NPD7843 Approved
0.7447 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7447 Intermediate Similarity NPD3268 Approved
0.7447 Intermediate Similarity NPD1699 Clinical (unspecified phase)
0.7434 Intermediate Similarity NPD3226 Approved
0.7426 Intermediate Similarity NPD3092 Approved
0.7426 Intermediate Similarity NPD1610 Phase 2
0.7415 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.741 Intermediate Similarity NPD6584 Phase 3
0.7407 Intermediate Similarity NPD3019 Approved
0.7402 Intermediate Similarity NPD3134 Approved
0.7389 Intermediate Similarity NPD5709 Phase 3
0.7388 Intermediate Similarity NPD1894 Discontinued
0.7365 Intermediate Similarity NPD8166 Discontinued
0.7365 Intermediate Similarity NPD7982 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD7229 Phase 3
0.7347 Intermediate Similarity NPD7037 Approved
0.7346 Intermediate Similarity NPD5844 Phase 1
0.7342 Intermediate Similarity NPD4666 Phase 3
0.7328 Intermediate Similarity NPD7635 Approved
0.7305 Intermediate Similarity NPD2614 Approved
0.7299 Intermediate Similarity NPD422 Phase 1
0.7293 Intermediate Similarity NPD4198 Discontinued
0.7292 Intermediate Similarity NPD3657 Discovery
0.729 Intermediate Similarity NPD37 Approved
0.7286 Intermediate Similarity NPD3691 Phase 2
0.7286 Intermediate Similarity NPD3690 Phase 2
0.7279 Intermediate Similarity NPD17 Approved
0.7279 Intermediate Similarity NPD6516 Phase 2
0.7279 Intermediate Similarity NPD5846 Approved
0.7279 Intermediate Similarity NPD2932 Approved
0.7273 Intermediate Similarity NPD5283 Phase 1
0.7273 Intermediate Similarity NPD6233 Phase 2
0.7273 Intermediate Similarity NPD4870 Approved
0.7261 Intermediate Similarity NPD4965 Approved
0.7261 Intermediate Similarity NPD4967 Phase 2
0.7261 Intermediate Similarity NPD4966 Approved
0.726 Intermediate Similarity NPD4108 Discontinued
0.7248 Intermediate Similarity NPD7976 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD6653 Approved
0.7237 Intermediate Similarity NPD4319 Phase 2
0.7237 Intermediate Similarity NPD6090 Discontinued
0.7234 Intermediate Similarity NPD1712 Approved
0.723 Intermediate Similarity NPD4534 Discontinued
0.7226 Intermediate Similarity NPD3847 Discontinued
0.7219 Intermediate Similarity NPD7041 Phase 2
0.7219 Intermediate Similarity NPD7040 Clinical (unspecified phase)
0.7214 Intermediate Similarity NPD3266 Approved
0.7214 Intermediate Similarity NPD3094 Phase 2
0.7214 Intermediate Similarity NPD3267 Approved
0.7211 Intermediate Similarity NPD2935 Discontinued
0.7211 Intermediate Similarity NPD6032 Approved
0.7209 Intermediate Similarity NPD2342 Discontinued
0.7209 Intermediate Similarity NPD290 Approved
0.7206 Intermediate Similarity NPD3443 Approved
0.7206 Intermediate Similarity NPD3445 Approved
0.7206 Intermediate Similarity NPD3444 Approved
0.7194 Intermediate Similarity NPD6583 Phase 3
0.7194 Intermediate Similarity NPD6582 Phase 2
0.7194 Intermediate Similarity NPD1669 Approved
0.7188 Intermediate Similarity NPD7199 Phase 2
0.7188 Intermediate Similarity NPD9697 Approved
0.7164 Intermediate Similarity NPD709 Approved
0.7162 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7162 Intermediate Similarity NPD6004 Phase 3
0.7162 Intermediate Similarity NPD5865 Clinical (unspecified phase)
0.7162 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7162 Intermediate Similarity NPD6005 Phase 3
0.7162 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7162 Intermediate Similarity NPD6002 Phase 3
0.7153 Intermediate Similarity NPD7265 Discontinued
0.7153 Intermediate Similarity NPD4059 Approved
0.7143 Intermediate Similarity NPD4308 Phase 3
0.7143 Intermediate Similarity NPD7033 Discontinued
0.7134 Intermediate Similarity NPD5929 Approved
0.7134 Intermediate Similarity NPD8455 Phase 2
0.7133 Intermediate Similarity NPD5163 Phase 2
0.7132 Intermediate Similarity NPD1548 Phase 1
0.7122 Intermediate Similarity NPD2235 Phase 2
0.7122 Intermediate Similarity NPD2232 Approved
0.7122 Intermediate Similarity NPD2230 Approved
0.7122 Intermediate Similarity NPD2233 Approved
0.7122 Intermediate Similarity NPD2231 Phase 2
0.7115 Intermediate Similarity NPD6677 Suspended
0.7103 Intermediate Similarity NPD3109 Approved
0.7103 Intermediate Similarity NPD3110 Approved
0.7101 Intermediate Similarity NPD3023 Approved
0.7101 Intermediate Similarity NPD3026 Approved
0.7099 Intermediate Similarity NPD5451 Approved
0.7092 Intermediate Similarity NPD987 Approved
0.7092 Intermediate Similarity NPD6362 Approved
0.7083 Intermediate Similarity NPD2313 Discontinued
0.708 Intermediate Similarity NPD3025 Approved
0.708 Intermediate Similarity NPD6830 Clinical (unspecified phase)
0.708 Intermediate Similarity NPD3024 Approved
0.7077 Intermediate Similarity NPD1358 Approved
0.7071 Intermediate Similarity NPD3685 Discontinued
0.707 Intermediate Similarity NPD5714 Approved
0.7068 Intermediate Similarity NPD821 Approved
0.7063 Intermediate Similarity NPD6234 Discontinued
0.7063 Intermediate Similarity NPD6832 Phase 2
0.7059 Intermediate Similarity NPD7019 Approved
0.7059 Intermediate Similarity NPD2533 Approved
0.7059 Intermediate Similarity NPD7020 Approved
0.7059 Intermediate Similarity NPD2534 Approved
0.7059 Intermediate Similarity NPD1578 Phase 2
0.7059 Intermediate Similarity NPD2532 Approved
0.7055 Intermediate Similarity NPD4622 Approved
0.7055 Intermediate Similarity NPD4481 Phase 3
0.7055 Intermediate Similarity NPD4618 Approved
0.7047 Intermediate Similarity NPD6800 Clinical (unspecified phase)
0.7044 Intermediate Similarity NPD7768 Phase 2
0.7044 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD3051 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