Structure

Physi-Chem Properties

Molecular Weight:  402.35
Volume:  456.266
LogP:  6.422
LogD:  5.53
LogS:  -5.578
# Rotatable Bonds:  5
TPSA:  40.46
# H-Bond Aceptor:  2
# H-Bond Donor:  2
# Rings:  4
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.525
Synthetic Accessibility Score:  4.41
Fsp3:  0.926
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.663
MDCK Permeability:  1.8489039575797506e-05
Pgp-inhibitor:  0.873
Pgp-substrate:  0.72
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.982
30% Bioavailability (F30%):  0.118

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.292
Plasma Protein Binding (PPB):  95.28862762451172%
Volume Distribution (VD):  1.104
Pgp-substrate:  1.5441415309906006%

ADMET: Metabolism

CYP1A2-inhibitor:  0.165
CYP1A2-substrate:  0.294
CYP2C19-inhibitor:  0.196
CYP2C19-substrate:  0.881
CYP2C9-inhibitor:  0.336
CYP2C9-substrate:  0.235
CYP2D6-inhibitor:  0.036
CYP2D6-substrate:  0.278
CYP3A4-inhibitor:  0.476
CYP3A4-substrate:  0.254

ADMET: Excretion

Clearance (CL):  8.909
Half-life (T1/2):  0.09

ADMET: Toxicity

hERG Blockers:  0.316
Human Hepatotoxicity (H-HT):  0.19
Drug-inuced Liver Injury (DILI):  0.124
AMES Toxicity:  0.003
Rat Oral Acute Toxicity:  0.031
Maximum Recommended Daily Dose:  0.43
Skin Sensitization:  0.877
Carcinogencity:  0.119
Eye Corrosion:  0.138
Eye Irritation:  0.273
Respiratory Toxicity:  0.956

Download Data

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

  Natural Product: NPC109546

Natural Product ID:  NPC109546
Common Name*:   7Alpha-Hydroxycholesterol
IUPAC Name:   (3S,7S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol
Synonyms:  
Standard InCHIKey:  OYXZMSRRJOYLLO-RVOWOUOISA-N
Standard InCHI:  InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h16-18,20-25,28-29H,6-15H2,1-5H3/t18-,20+,21-,22+,23+,24-,25+,26+,27-/m1/s1
SMILES:  CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@]12C)[C@@]1(C)CC[C@@H](CC1=C[C@H]3O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL497207
PubChem CID:   107722
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0003566] Cholestane steroids
          • [CHEMONTID:0001469] Cholesterols and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. DOI[10.1172/JCI16309]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. DOI[10.1371/journal.pone.0115359]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[10557354]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[11034610]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[11419736]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[11530998]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[1175644]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[12391014]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[12812989]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[12840027]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[12878451]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[15084647]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[1521032]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[15230696]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[15314235]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[16112079]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[16770722]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[1687010]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[17116739]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[17190852]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[17875433]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[18311922]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[18544912]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[18799520]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[19425150]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[19961175]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[20506249]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[20601097]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. faeces n.a. PMID[20708442]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. bile n.a. PMID[20708442]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. urine n.a. PMID[20708442]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[20876113]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[21798258]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[2268561]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[22711758]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[23315938]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[23717534]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[23752203]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[23810710]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[23811455]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[23868375]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[23919613]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[24101735]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[24399466]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[24494566]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[24558969]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[24816727]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[25114169]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[25181601]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[25293588]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[25644343]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[26236990]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[27471436]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[3179836]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[347637]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[4696527]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[5432584]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[6121420]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[6780563]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[8600370]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[8987136]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[9192820]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[9800648]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. Database[MetaboLights]
NPO20338 Mus musculus Species Muridae 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
NPT139 Cell Line HT-29 Homo sapiens IC50 = 15500.0 nM PMID[522567]
NPT139 Cell Line HT-29 Homo sapiens IC50 = 15500.0 nM PMID[522568]
NPT139 Cell Line HT-29 Homo sapiens IC50 = 15500.0 nM PMID[522569]
NPT76 Cell Line C6 Rattus norvegicus IC50 = 40000.0 nM PMID[522570]
NPT76 Cell Line C6 Rattus norvegicus LD50 >= 160.0 uM PMID[522570]
NPT599 Individual Protein Nuclear receptor ROR-alpha Homo sapiens Ki = 12.0 nM PMID[522571]
NPT103 Individual Protein Nuclear receptor ROR-gamma Homo sapiens Ki = 10.0 nM PMID[522571]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 >= 160000.0 nM PMID[522570]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. LD50 > 160.0 uM PMID[522570]
NPT27 Others Unspecified IC50 = 15000.0 nM PMID[522570]
NPT27 Others Unspecified LD50 = 60.0 uM PMID[522570]

☑ 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 NPC109546 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 NPC47982
1.0 High Similarity NPC84694
1.0 High Similarity NPC28862
1.0 High Similarity NPC143182
1.0 High Similarity NPC81306
0.9865 High Similarity NPC234193
0.9863 High Similarity NPC474216
0.9733 High Similarity NPC23852
0.9733 High Similarity NPC264245
0.9733 High Similarity NPC209620
0.973 High Similarity NPC209430
0.973 High Similarity NPC30986
0.9605 High Similarity NPC189972
0.9605 High Similarity NPC50964
0.9605 High Similarity NPC101462
0.9605 High Similarity NPC49964
0.96 High Similarity NPC241290
0.96 High Similarity NPC209944
0.96 High Similarity NPC164840
0.9595 High Similarity NPC473943
0.9589 High Similarity NPC244488
0.9589 High Similarity NPC321016
0.9589 High Similarity NPC107059
0.9589 High Similarity NPC321381
0.9589 High Similarity NPC247325
0.9481 High Similarity NPC317458
0.9481 High Similarity NPC475789
0.9481 High Similarity NPC474634
0.9474 High Similarity NPC7505
0.9474 High Similarity NPC82986
0.9474 High Similarity NPC474752
0.9474 High Similarity NPC474683
0.9474 High Similarity NPC474731
0.9474 High Similarity NPC47761
0.9474 High Similarity NPC474759
0.9459 High Similarity NPC198968
0.9459 High Similarity NPC155986
0.9459 High Similarity NPC318495
0.9452 High Similarity NPC285893
0.9452 High Similarity NPC288035
0.9452 High Similarity NPC230301
0.9452 High Similarity NPC28657
0.9452 High Similarity NPC304309
0.9452 High Similarity NPC162742
0.9452 High Similarity NPC136188
0.9452 High Similarity NPC134847
0.9452 High Similarity NPC22105
0.9359 High Similarity NPC205845
0.9359 High Similarity NPC185568
0.9333 High Similarity NPC477522
0.9333 High Similarity NPC87604
0.9324 High Similarity NPC113733
0.9324 High Similarity NPC300324
0.9324 High Similarity NPC240604
0.9241 High Similarity NPC274448
0.9241 High Similarity NPC266511
0.9211 High Similarity NPC328714
0.92 High Similarity NPC34019
0.9189 High Similarity NPC471723
0.9189 High Similarity NPC141071
0.9189 High Similarity NPC257347
0.9125 High Similarity NPC152808
0.9125 High Similarity NPC6391
0.9125 High Similarity NPC293287
0.9125 High Similarity NPC261266
0.9114 High Similarity NPC238485
0.9114 High Similarity NPC474047
0.9103 High Similarity NPC202389
0.9103 High Similarity NPC296701
0.9103 High Similarity NPC218616
0.9103 High Similarity NPC470049
0.9103 High Similarity NPC87489
0.9091 High Similarity NPC26117
0.9079 High Similarity NPC18603
0.9079 High Similarity NPC167891
0.9079 High Similarity NPC275910
0.9079 High Similarity NPC477514
0.9079 High Similarity NPC307965
0.9079 High Similarity NPC83351
0.9079 High Similarity NPC76931
0.9067 High Similarity NPC189883
0.9067 High Similarity NPC96319
0.9067 High Similarity NPC134330
0.9067 High Similarity NPC129165
0.9054 High Similarity NPC469593
0.9054 High Similarity NPC469533
0.9054 High Similarity NPC469534
0.9012 High Similarity NPC149224
0.9 High Similarity NPC157257
0.8987 High Similarity NPC470384
0.8974 High Similarity NPC474531
0.8974 High Similarity NPC470383
0.8961 High Similarity NPC1319
0.8947 High Similarity NPC214570
0.8947 High Similarity NPC91594
0.8919 High Similarity NPC474140
0.8919 High Similarity NPC471799
0.8904 High Similarity NPC34834
0.8902 High Similarity NPC474668
0.8875 High Similarity NPC470077
0.8875 High Similarity NPC231310
0.8861 High Similarity NPC1272
0.8861 High Similarity NPC470614
0.8861 High Similarity NPC5985
0.8846 High Similarity NPC236112
0.8831 High Similarity NPC476314
0.8831 High Similarity NPC285761
0.8831 High Similarity NPC167037
0.8831 High Similarity NPC6978
0.8831 High Similarity NPC138621
0.8831 High Similarity NPC244385
0.8816 High Similarity NPC73875
0.8816 High Similarity NPC470362
0.8816 High Similarity NPC237460
0.8816 High Similarity NPC46160
0.8816 High Similarity NPC202642
0.88 High Similarity NPC471797
0.8795 High Similarity NPC470361
0.8795 High Similarity NPC477606
0.8795 High Similarity NPC146554
0.8765 High Similarity NPC471224
0.8765 High Similarity NPC470360
0.8765 High Similarity NPC318390
0.875 High Similarity NPC82623
0.8734 High Similarity NPC476646
0.8718 High Similarity NPC273410
0.8718 High Similarity NPC80530
0.8701 High Similarity NPC470711
0.8701 High Similarity NPC470758
0.869 High Similarity NPC11216
0.869 High Similarity NPC48010
0.869 High Similarity NPC204188
0.869 High Similarity NPC295668
0.869 High Similarity NPC329596
0.869 High Similarity NPC80561
0.869 High Similarity NPC3345
0.869 High Similarity NPC291484
0.8684 High Similarity NPC118508
0.8684 High Similarity NPC322353
0.8684 High Similarity NPC185536
0.8684 High Similarity NPC121744
0.8675 High Similarity NPC133588
0.8675 High Similarity NPC67872
0.8675 High Similarity NPC471952
0.8667 High Similarity NPC474743
0.8659 High Similarity NPC299068
0.8642 High Similarity NPC472265
0.8642 High Similarity NPC221758
0.8642 High Similarity NPC209802
0.8642 High Similarity NPC59453
0.8642 High Similarity NPC124172
0.8642 High Similarity NPC33913
0.863 High Similarity NPC160209
0.863 High Similarity NPC208999
0.8625 High Similarity NPC248886
0.8625 High Similarity NPC201852
0.8625 High Similarity NPC30166
0.8608 High Similarity NPC236237
0.8608 High Similarity NPC13554
0.8608 High Similarity NPC295131
0.8608 High Similarity NPC322313
0.8608 High Similarity NPC96362
0.8608 High Similarity NPC102253
0.859 High Similarity NPC205455
0.859 High Similarity NPC65897
0.859 High Similarity NPC11908
0.859 High Similarity NPC186191
0.859 High Similarity NPC302041
0.859 High Similarity NPC85346
0.8588 High Similarity NPC41554
0.8588 High Similarity NPC97404
0.8571 High Similarity NPC262858
0.8571 High Similarity NPC309603
0.8571 High Similarity NPC265588
0.8571 High Similarity NPC253190
0.8571 High Similarity NPC470749
0.8571 High Similarity NPC473999
0.8571 High Similarity NPC472240
0.8554 High Similarity NPC470620
0.8553 High Similarity NPC476366
0.8553 High Similarity NPC306727
0.8553 High Similarity NPC27395
0.8553 High Similarity NPC201048
0.8553 High Similarity NPC477138
0.8553 High Similarity NPC243342
0.8553 High Similarity NPC329090
0.8537 High Similarity NPC474189
0.8537 High Similarity NPC474083
0.8537 High Similarity NPC474349
0.8533 High Similarity NPC242001
0.8519 High Similarity NPC470558
0.8519 High Similarity NPC134481
0.8493 Intermediate Similarity NPC68703
0.8493 Intermediate Similarity NPC69649
0.8493 Intermediate Similarity NPC114651
0.8481 Intermediate Similarity NPC472463
0.8462 Intermediate Similarity NPC257191
0.8462 Intermediate Similarity NPC248830
0.8462 Intermediate Similarity NPC212241
0.8462 Intermediate Similarity NPC119355

  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 NPC109546 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
0.9452 High Similarity NPD7339 Approved
0.9452 High Similarity NPD6942 Approved
0.9067 High Similarity NPD3701 Clinical (unspecified phase)
0.878 High Similarity NPD4751 Clinical (unspecified phase)
0.8642 High Similarity NPD4786 Approved
0.8608 High Similarity NPD7525 Registered
0.8553 High Similarity NPD6926 Approved
0.8553 High Similarity NPD6924 Approved
0.8481 Intermediate Similarity NPD6929 Approved
0.8395 Intermediate Similarity NPD3667 Approved
0.8375 Intermediate Similarity NPD6930 Phase 2
0.8375 Intermediate Similarity NPD6931 Approved
0.8333 Intermediate Similarity NPD6933 Approved
0.8312 Intermediate Similarity NPD4784 Approved
0.8312 Intermediate Similarity NPD4785 Approved
0.8289 Intermediate Similarity NPD7152 Approved
0.8289 Intermediate Similarity NPD7151 Approved
0.8289 Intermediate Similarity NPD7150 Approved
0.8289 Intermediate Similarity NPD4243 Approved
0.8267 Intermediate Similarity NPD6923 Approved
0.8267 Intermediate Similarity NPD6922 Approved
0.8228 Intermediate Similarity NPD6925 Approved
0.8228 Intermediate Similarity NPD5776 Phase 2
0.8158 Intermediate Similarity NPD7143 Approved
0.8158 Intermediate Similarity NPD7144 Approved
0.8148 Intermediate Similarity NPD7514 Phase 3
0.8125 Intermediate Similarity NPD7145 Approved
0.8125 Intermediate Similarity NPD7322 Clinical (unspecified phase)
0.8072 Intermediate Similarity NPD6695 Phase 3
0.8049 Intermediate Similarity NPD6902 Approved
0.8025 Intermediate Similarity NPD7645 Phase 2
0.7976 Intermediate Similarity NPD7338 Clinical (unspecified phase)
0.7975 Intermediate Similarity NPD8264 Approved
0.7931 Intermediate Similarity NPD5328 Approved
0.7927 Intermediate Similarity NPD4748 Discontinued
0.7927 Intermediate Similarity NPD7332 Phase 2
0.7882 Intermediate Similarity NPD6893 Approved
0.7791 Intermediate Similarity NPD3618 Phase 1
0.7778 Intermediate Similarity NPD6932 Approved
0.7765 Intermediate Similarity NPD3133 Approved
0.7765 Intermediate Similarity NPD3666 Approved
0.7765 Intermediate Similarity NPD3665 Phase 1
0.7753 Intermediate Similarity NPD6079 Approved
0.775 Intermediate Similarity NPD5275 Approved
0.775 Intermediate Similarity NPD4190 Phase 3
0.7711 Intermediate Similarity NPD7509 Discontinued
0.7701 Intermediate Similarity NPD7524 Approved
0.7701 Intermediate Similarity NPD7750 Discontinued
0.7667 Intermediate Similarity NPD6399 Phase 3
0.7619 Intermediate Similarity NPD6898 Phase 1
0.759 Intermediate Similarity NPD4195 Approved
0.759 Intermediate Similarity NPD6683 Phase 2
0.7558 Intermediate Similarity NPD3668 Phase 3
0.7473 Intermediate Similarity NPD4202 Approved
0.7386 Intermediate Similarity NPD5279 Phase 3
0.7368 Intermediate Similarity NPD7640 Approved
0.7368 Intermediate Similarity NPD7639 Approved
0.7363 Intermediate Similarity NPD7087 Discontinued
0.7333 Intermediate Similarity NPD4753 Phase 2
0.7333 Intermediate Similarity NPD6051 Approved
0.7326 Intermediate Similarity NPD4223 Phase 3
0.7326 Intermediate Similarity NPD4221 Approved
0.7273 Intermediate Similarity NPD5329 Approved
0.7273 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7263 Intermediate Similarity NPD7638 Approved
0.7234 Intermediate Similarity NPD5221 Approved
0.7234 Intermediate Similarity NPD4697 Phase 3
0.7234 Intermediate Similarity NPD5222 Approved
0.7234 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7216 Intermediate Similarity NPD5211 Phase 2
0.7174 Intermediate Similarity NPD7637 Suspended
0.7159 Intermediate Similarity NPD4197 Approved
0.7158 Intermediate Similarity NPD5173 Approved
0.7158 Intermediate Similarity NPD4755 Approved
0.7105 Intermediate Similarity NPD368 Approved
0.7071 Intermediate Similarity NPD5141 Approved
0.7045 Intermediate Similarity NPD4788 Approved
0.701 Intermediate Similarity NPD5286 Approved
0.701 Intermediate Similarity NPD4696 Approved
0.701 Intermediate Similarity NPD4700 Approved
0.701 Intermediate Similarity NPD5285 Approved
0.7 Intermediate Similarity NPD4138 Approved
0.7 Intermediate Similarity NPD5205 Approved
0.7 Intermediate Similarity NPD4688 Approved
0.7 Intermediate Similarity NPD4519 Discontinued
0.7 Intermediate Similarity NPD7521 Approved
0.7 Intermediate Similarity NPD4689 Approved
0.7 Intermediate Similarity NPD4693 Phase 3
0.7 Intermediate Similarity NPD7146 Approved
0.7 Intermediate Similarity NPD6684 Approved
0.7 Intermediate Similarity NPD4690 Approved
0.7 Intermediate Similarity NPD4623 Approved
0.7 Intermediate Similarity NPD5330 Approved
0.7 Intermediate Similarity NPD6409 Approved
0.7 Intermediate Similarity NPD7334 Approved
0.6989 Remote Similarity NPD7515 Phase 2
0.6986 Remote Similarity NPD342 Phase 1
0.6979 Remote Similarity NPD6084 Phase 2
0.6979 Remote Similarity NPD6083 Phase 2
0.6947 Remote Similarity NPD5210 Approved
0.6947 Remote Similarity NPD4629 Approved
0.6939 Remote Similarity NPD5223 Approved
0.6914 Remote Similarity NPD4267 Clinical (unspecified phase)
0.6907 Remote Similarity NPD5290 Discontinued
0.6882 Remote Similarity NPD7136 Phase 2
0.6869 Remote Similarity NPD5224 Approved
0.6869 Remote Similarity NPD5225 Approved
0.6869 Remote Similarity NPD5226 Approved
0.6869 Remote Similarity NPD4633 Approved
0.686 Remote Similarity NPD3617 Approved
0.686 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6848 Remote Similarity NPD4723 Approved
0.6848 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6848 Remote Similarity NPD5737 Approved
0.6848 Remote Similarity NPD6903 Approved
0.6848 Remote Similarity NPD4722 Approved
0.6848 Remote Similarity NPD6672 Approved
0.6832 Remote Similarity NPD5739 Approved
0.6832 Remote Similarity NPD6675 Approved
0.6832 Remote Similarity NPD6402 Approved
0.6832 Remote Similarity NPD7128 Approved
0.6829 Remote Similarity NPD4787 Phase 1
0.6822 Remote Similarity NPD7115 Discovery
0.6813 Remote Similarity NPD5690 Phase 2
0.6813 Remote Similarity NPD4694 Approved
0.6813 Remote Similarity NPD5280 Approved
0.68 Remote Similarity NPD4754 Approved
0.68 Remote Similarity NPD5175 Approved
0.68 Remote Similarity NPD5174 Approved
0.6768 Remote Similarity NPD4159 Approved
0.6747 Remote Similarity NPD4809 Clinical (unspecified phase)
0.6747 Remote Similarity NPD4808 Clinical (unspecified phase)
0.6735 Remote Similarity NPD4225 Approved
0.6705 Remote Similarity NPD4695 Discontinued
0.67 Remote Similarity NPD7632 Discontinued
0.6699 Remote Similarity NPD7320 Approved
0.6699 Remote Similarity NPD6881 Approved
0.6699 Remote Similarity NPD6899 Approved
0.6667 Remote Similarity NPD5331 Approved
0.6667 Remote Similarity NPD5362 Discontinued
0.6667 Remote Similarity NPD4768 Approved
0.6667 Remote Similarity NPD4767 Approved
0.6667 Remote Similarity NPD7748 Approved
0.6667 Remote Similarity NPD5332 Approved
0.6635 Remote Similarity NPD6373 Approved
0.6635 Remote Similarity NPD6372 Approved
0.6632 Remote Similarity NPD8035 Phase 2
0.6632 Remote Similarity NPD8034 Phase 2
0.663 Remote Similarity NPD6098 Approved
0.663 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6629 Remote Similarity NPD4139 Approved
0.6629 Remote Similarity NPD4692 Approved
0.6629 Remote Similarity NPD4790 Discontinued
0.6627 Remote Similarity NPD4747 Approved
0.6602 Remote Similarity NPD5701 Approved
0.6602 Remote Similarity NPD5697 Approved
0.6598 Remote Similarity NPD5695 Phase 3
0.6588 Remote Similarity NPD6113 Clinical (unspecified phase)
0.6571 Remote Similarity NPD7290 Approved
0.6571 Remote Similarity NPD7102 Approved
0.6571 Remote Similarity NPD6883 Approved
0.6566 Remote Similarity NPD5696 Approved
0.6538 Remote Similarity NPD4729 Approved
0.6538 Remote Similarity NPD4730 Approved
0.6538 Remote Similarity NPD5128 Approved
0.6538 Remote Similarity NPD6011 Approved
0.6538 Remote Similarity NPD5168 Approved
0.6522 Remote Similarity NPD1696 Phase 3
0.6517 Remote Similarity NPD4819 Approved
0.6517 Remote Similarity NPD4821 Approved
0.6517 Remote Similarity NPD4822 Approved
0.6517 Remote Similarity NPD4820 Approved
0.6509 Remote Similarity NPD6869 Approved
0.6509 Remote Similarity NPD6617 Approved
0.6509 Remote Similarity NPD6649 Approved
0.6509 Remote Similarity NPD6847 Approved
0.6509 Remote Similarity NPD6650 Approved
0.6509 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6509 Remote Similarity NPD8130 Phase 1
0.6506 Remote Similarity NPD4137 Phase 3
0.6506 Remote Similarity NPD3700 Clinical (unspecified phase)
0.6506 Remote Similarity NPD3699 Clinical (unspecified phase)
0.65 Remote Similarity NPD6404 Discontinued
0.6495 Remote Similarity NPD5771 Approved
0.6477 Remote Similarity NPD4271 Approved
0.6477 Remote Similarity NPD4268 Approved
0.6476 Remote Similarity NPD6014 Approved
0.6476 Remote Similarity NPD6012 Approved
0.6476 Remote Similarity NPD6013 Approved
0.6465 Remote Similarity NPD7902 Approved
0.6458 Remote Similarity NPD5281 Approved
0.6458 Remote Similarity NPD5284 Approved
0.6449 Remote Similarity NPD6882 Approved
0.6449 Remote Similarity NPD8297 Approved
0.6447 Remote Similarity NPD4219 Approved
0.6442 Remote Similarity NPD6412 Phase 2
0.6437 Remote Similarity NPD6117 Approved
0.6429 Remote Similarity NPD4244 Approved
0.6429 Remote Similarity NPD4691 Approved
0.6429 Remote Similarity NPD4789 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