Structure

Physi-Chem Properties

Molecular Weight:  290.22
Volume:  317.898
LogP:  3.452
LogD:  3.791
LogS:  -0.939
# Rotatable Bonds:  0
TPSA:  37.3
# H-Bond Aceptor:  2
# H-Bond Donor:  1
# Rings:  4
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.733
Synthetic Accessibility Score:  3.994
Fsp3:  0.947
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.731
MDCK Permeability:  1.6121894077514298e-05
Pgp-inhibitor:  0.988
Pgp-substrate:  0.733
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.971
30% Bioavailability (F30%):  0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.51
Plasma Protein Binding (PPB):  79.47183990478516%
Volume Distribution (VD):  0.897
Pgp-substrate:  6.769050598144531%

ADMET: Metabolism

CYP1A2-inhibitor:  0.116
CYP1A2-substrate:  0.295
CYP2C19-inhibitor:  0.043
CYP2C19-substrate:  0.717
CYP2C9-inhibitor:  0.081
CYP2C9-substrate:  0.105
CYP2D6-inhibitor:  0.006
CYP2D6-substrate:  0.401
CYP3A4-inhibitor:  0.129
CYP3A4-substrate:  0.298

ADMET: Excretion

Clearance (CL):  21.078
Half-life (T1/2):  0.816

ADMET: Toxicity

hERG Blockers:  0.48
Human Hepatotoxicity (H-HT):  0.592
Drug-inuced Liver Injury (DILI):  0.486
AMES Toxicity:  0.011
Rat Oral Acute Toxicity:  0.461
Maximum Recommended Daily Dose:  0.843
Skin Sensitization:  0.943
Carcinogencity:  0.708
Eye Corrosion:  0.698
Eye Irritation:  0.323
Respiratory Toxicity:  0.979

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Similar NPs/Drugs  

  Natural Product: NPC321732

Natural Product ID:  NPC321732
Common Name*:   (5R,8R,9S,10S,13S,14S,17S)-17-Hydroxy-10,13-Dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-Tetradecahydrocyclopenta[A]Phenanthren-3-One
IUPAC Name:   (5R,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
Synonyms:  
Standard InCHIKey:  NVKAWKQGWWIWPM-MISPCMORSA-N
Standard InCHI:  InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12,14-17,21H,3-11H2,1-2H3/t12-,14+,15+,16+,17+,18+,19+/m1/s1
SMILES:  O=C1CC[C@]2([C@@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2O)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL373357
PubChem CID:   11302
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0003568] Androstane steroids
          • [CHEMONTID:0001467] Androgens 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. 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. faeces 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
NPT299 Individual Protein Androgen Receptor Rattus norvegicus IC50 = 380.19 nM PMID[534852]
NPT101 Individual Protein Glucagon-like peptide 1 receptor Homo sapiens Potency n.a. 7943.3 nM PMID[534854]
NPT153 Individual Protein Androgen Receptor Homo sapiens Activity = 190.0 % PMID[534856]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 2616.9 nM PMID[534853]
NPT7 Individual Protein Thioredoxin reductase 1, cytoplasmic Rattus norvegicus Potency n.a. 89125.1 nM PMID[534854]
NPT8 Individual Protein DNA polymerase iota Homo sapiens Potency n.a. 89125.1 nM PMID[534854]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 16511.3 nM PMID[534853]
NPT2 Others Unspecified Potency n.a. 25118.9 nM PMID[534854]
NPT697 Individual Protein UDP-glucuronosyltransferase 2B7 Homo sapiens Activity = 12.0 total picomoles PMID[534855]
NPT2 Others Unspecified Potency n.a. 31622.8 nM PMID[534854]

☑ 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 NPC321732 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 NPC324607
0.9552 High Similarity NPC310766
0.9394 High Similarity NPC327728
0.9394 High Similarity NPC213178
0.9394 High Similarity NPC6120
0.9394 High Similarity NPC131892
0.913 High Similarity NPC472854
0.9118 High Similarity NPC151018
0.9118 High Similarity NPC89310
0.9118 High Similarity NPC320549
0.9118 High Similarity NPC58057
0.9118 High Similarity NPC156277
0.8986 High Similarity NPC232112
0.8857 High Similarity NPC254340
0.8857 High Similarity NPC133922
0.8841 High Similarity NPC473267
0.8732 High Similarity NPC125767
0.8732 High Similarity NPC24014
0.8732 High Similarity NPC195155
0.8732 High Similarity NPC27349
0.8732 High Similarity NPC273366
0.8732 High Similarity NPC97534
0.8732 High Similarity NPC21220
0.8732 High Similarity NPC174964
0.8732 High Similarity NPC159789
0.8696 High Similarity NPC476731
0.8649 High Similarity NPC470609
0.8611 High Similarity NPC472486
0.8611 High Similarity NPC5767
0.8611 High Similarity NPC475742
0.8611 High Similarity NPC472487
0.8592 High Similarity NPC167702
0.8592 High Similarity NPC280026
0.8551 High Similarity NPC252032
0.8551 High Similarity NPC476734
0.8551 High Similarity NPC319671
0.8551 High Similarity NPC469941
0.8533 High Similarity NPC469745
0.8514 High Similarity NPC472310
0.8493 Intermediate Similarity NPC23884
0.8493 Intermediate Similarity NPC221420
0.8493 Intermediate Similarity NPC474404
0.8493 Intermediate Similarity NPC180199
0.8493 Intermediate Similarity NPC477919
0.8493 Intermediate Similarity NPC475031
0.8493 Intermediate Similarity NPC264602
0.8472 Intermediate Similarity NPC212733
0.8472 Intermediate Similarity NPC472311
0.8429 Intermediate Similarity NPC477850
0.8429 Intermediate Similarity NPC477929
0.8421 Intermediate Similarity NPC317066
0.8421 Intermediate Similarity NPC328007
0.8406 Intermediate Similarity NPC473225
0.8406 Intermediate Similarity NPC2568
0.8406 Intermediate Similarity NPC474954
0.8406 Intermediate Similarity NPC103647
0.8406 Intermediate Similarity NPC260319
0.8406 Intermediate Similarity NPC180777
0.8378 Intermediate Similarity NPC199965
0.8378 Intermediate Similarity NPC185465
0.8378 Intermediate Similarity NPC476732
0.8358 Intermediate Similarity NPC167995
0.8358 Intermediate Similarity NPC281540
0.8358 Intermediate Similarity NPC118937
0.8358 Intermediate Similarity NPC159654
0.8356 Intermediate Similarity NPC4209
0.8312 Intermediate Similarity NPC327451
0.831 Intermediate Similarity NPC126642
0.8289 Intermediate Similarity NPC77311
0.8286 Intermediate Similarity NPC64466
0.8267 Intermediate Similarity NPC320144
0.8243 Intermediate Similarity NPC317913
0.8243 Intermediate Similarity NPC143133
0.8243 Intermediate Similarity NPC298168
0.8243 Intermediate Similarity NPC207010
0.8194 Intermediate Similarity NPC68426
0.8194 Intermediate Similarity NPC282905
0.8194 Intermediate Similarity NPC477229
0.8182 Intermediate Similarity NPC46881
0.8169 Intermediate Similarity NPC108131
0.8158 Intermediate Similarity NPC472853
0.8133 Intermediate Similarity NPC80089
0.8133 Intermediate Similarity NPC171426
0.8133 Intermediate Similarity NPC324700
0.8133 Intermediate Similarity NPC224802
0.8133 Intermediate Similarity NPC34046
0.8116 Intermediate Similarity NPC268736
0.8116 Intermediate Similarity NPC42060
0.8116 Intermediate Similarity NPC477931
0.8116 Intermediate Similarity NPC44122
0.8082 Intermediate Similarity NPC159325
0.8082 Intermediate Similarity NPC168511
0.8082 Intermediate Similarity NPC477930
0.8082 Intermediate Similarity NPC130011
0.8077 Intermediate Similarity NPC472498
0.8077 Intermediate Similarity NPC245866
0.8077 Intermediate Similarity NPC259173
0.8056 Intermediate Similarity NPC469940
0.8056 Intermediate Similarity NPC290058
0.8028 Intermediate Similarity NPC474962
0.8028 Intermediate Similarity NPC196197
0.8026 Intermediate Similarity NPC31302
0.8026 Intermediate Similarity NPC245029
0.8026 Intermediate Similarity NPC52951
0.8026 Intermediate Similarity NPC201276
0.8026 Intermediate Similarity NPC80891
0.8026 Intermediate Similarity NPC201459
0.8 Intermediate Similarity NPC472984
0.8 Intermediate Similarity NPC476727
0.8 Intermediate Similarity NPC477918
0.8 Intermediate Similarity NPC474221
0.8 Intermediate Similarity NPC474448
0.8 Intermediate Similarity NPC476726
0.8 Intermediate Similarity NPC130459
0.8 Intermediate Similarity NPC478180
0.8 Intermediate Similarity NPC106078
0.7975 Intermediate Similarity NPC161423
0.7975 Intermediate Similarity NPC82902
0.7975 Intermediate Similarity NPC321187
0.7975 Intermediate Similarity NPC58841
0.7975 Intermediate Similarity NPC329043
0.7975 Intermediate Similarity NPC227064
0.7973 Intermediate Similarity NPC267753
0.7971 Intermediate Similarity NPC475943
0.7971 Intermediate Similarity NPC243469
0.7971 Intermediate Similarity NPC190827
0.7949 Intermediate Similarity NPC477935
0.7949 Intermediate Similarity NPC30583
0.7949 Intermediate Similarity NPC170985
0.7949 Intermediate Similarity NPC289486
0.7949 Intermediate Similarity NPC61107
0.7949 Intermediate Similarity NPC477858
0.7949 Intermediate Similarity NPC110780
0.7949 Intermediate Similarity NPC145143
0.7945 Intermediate Similarity NPC81759
0.7945 Intermediate Similarity NPC474123
0.7941 Intermediate Similarity NPC114891
0.7922 Intermediate Similarity NPC477851
0.7895 Intermediate Similarity NPC329117
0.7879 Intermediate Similarity NPC476735
0.7875 Intermediate Similarity NPC474218
0.7867 Intermediate Similarity NPC477932
0.7867 Intermediate Similarity NPC477933
0.7867 Intermediate Similarity NPC108840
0.7848 Intermediate Similarity NPC268578
0.7848 Intermediate Similarity NPC475726
0.7848 Intermediate Similarity NPC292458
0.7848 Intermediate Similarity NPC217559
0.7848 Intermediate Similarity NPC472743
0.7848 Intermediate Similarity NPC472744
0.7821 Intermediate Similarity NPC474484
0.7821 Intermediate Similarity NPC12933
0.7821 Intermediate Similarity NPC103754
0.7821 Intermediate Similarity NPC58631
0.7812 Intermediate Similarity NPC53245
0.7812 Intermediate Similarity NPC288296
0.7808 Intermediate Similarity NPC472309
0.7794 Intermediate Similarity NPC71460
0.7794 Intermediate Similarity NPC218585
0.7794 Intermediate Similarity NPC148174
0.7778 Intermediate Similarity NPC472272
0.7778 Intermediate Similarity NPC469994
0.7778 Intermediate Similarity NPC477820
0.7778 Intermediate Similarity NPC80590
0.7763 Intermediate Similarity NPC472746
0.7763 Intermediate Similarity NPC149249
0.775 Intermediate Similarity NPC50438
0.775 Intermediate Similarity NPC474996
0.775 Intermediate Similarity NPC471044
0.775 Intermediate Similarity NPC474482
0.775 Intermediate Similarity NPC263974
0.775 Intermediate Similarity NPC474233
0.775 Intermediate Similarity NPC473336
0.775 Intermediate Similarity NPC475745
0.7746 Intermediate Similarity NPC63190
0.7733 Intermediate Similarity NPC477934
0.7733 Intermediate Similarity NPC179858
0.7722 Intermediate Similarity NPC268040
0.7722 Intermediate Similarity NPC151519
0.7722 Intermediate Similarity NPC477936
0.7722 Intermediate Similarity NPC121121
0.7692 Intermediate Similarity NPC164999
0.7692 Intermediate Similarity NPC261616
0.7683 Intermediate Similarity NPC317590
0.7683 Intermediate Similarity NPC472495
0.7683 Intermediate Similarity NPC472497
0.7683 Intermediate Similarity NPC134197
0.7681 Intermediate Similarity NPC209686
0.7681 Intermediate Similarity NPC236099
0.7681 Intermediate Similarity NPC249078
0.7671 Intermediate Similarity NPC232925
0.7671 Intermediate Similarity NPC251201
0.7671 Intermediate Similarity NPC63588
0.7662 Intermediate Similarity NPC26029
0.7654 Intermediate Similarity NPC102292
0.7654 Intermediate Similarity NPC292553
0.7654 Intermediate Similarity NPC76518
0.7639 Intermediate Similarity NPC100917
0.7639 Intermediate Similarity NPC31187
0.7639 Intermediate Similarity NPC478228

  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 NPC321732 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
1.0 High Similarity NPD3698 Phase 2
0.9846 High Similarity NPD4244 Approved
0.9846 High Similarity NPD4245 Approved
0.9394 High Similarity NPD3699 Clinical (unspecified phase)
0.9394 High Similarity NPD3700 Clinical (unspecified phase)
0.9118 High Similarity NPD4809 Clinical (unspecified phase)
0.9118 High Similarity NPD4808 Clinical (unspecified phase)
0.9077 High Similarity NPD3171 Clinical (unspecified phase)
0.8971 High Similarity NPD4789 Approved
0.8732 High Similarity NPD3703 Phase 2
0.8592 High Similarity NPD6113 Clinical (unspecified phase)
0.8571 High Similarity NPD5777 Approved
0.8406 Intermediate Similarity NPD5361 Clinical (unspecified phase)
0.8406 Intermediate Similarity NPD5360 Phase 3
0.8382 Intermediate Similarity NPD4224 Phase 2
0.8378 Intermediate Similarity NPD3671 Phase 1
0.8356 Intermediate Similarity NPD6117 Approved
0.8243 Intermediate Similarity NPD6116 Phase 1
0.8219 Intermediate Similarity NPD3702 Approved
0.8133 Intermediate Similarity NPD6118 Approved
0.8133 Intermediate Similarity NPD6697 Approved
0.8133 Intermediate Similarity NPD6114 Approved
0.8133 Intermediate Similarity NPD6115 Approved
0.8077 Intermediate Similarity NPD4788 Approved
0.8056 Intermediate Similarity NPD6081 Approved
0.8056 Intermediate Similarity NPD4758 Discontinued
0.7975 Intermediate Similarity NPD3665 Phase 1
0.7975 Intermediate Similarity NPD3133 Approved
0.7975 Intermediate Similarity NPD3666 Approved
0.7722 Intermediate Similarity NPD3667 Approved
0.7671 Intermediate Similarity NPD4787 Phase 1
0.7531 Intermediate Similarity NPD4786 Approved
0.75 Intermediate Similarity NPD3198 Approved
0.7439 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD5364 Discontinued
0.7349 Intermediate Similarity NPD3618 Phase 1
0.7297 Intermediate Similarity NPD4267 Clinical (unspecified phase)
0.7294 Intermediate Similarity NPD4753 Phase 2
0.7284 Intermediate Similarity NPD4223 Phase 3
0.7284 Intermediate Similarity NPD4221 Approved
0.7241 Intermediate Similarity NPD4202 Approved
0.7215 Intermediate Similarity NPD3617 Approved
0.716 Intermediate Similarity NPD4692 Approved
0.716 Intermediate Similarity NPD4139 Approved
0.7108 Intermediate Similarity NPD4197 Approved
0.7093 Intermediate Similarity NPD5328 Approved
0.7024 Intermediate Similarity NPD5329 Approved
0.6977 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6962 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6941 Remote Similarity NPD4688 Approved
0.6941 Remote Similarity NPD4690 Approved
0.6941 Remote Similarity NPD4689 Approved
0.6941 Remote Similarity NPD4693 Phase 3
0.6941 Remote Similarity NPD7521 Approved
0.6941 Remote Similarity NPD5205 Approved
0.6941 Remote Similarity NPD4138 Approved
0.6941 Remote Similarity NPD5279 Phase 3
0.6941 Remote Similarity NPD6409 Approved
0.6941 Remote Similarity NPD7146 Approved
0.6941 Remote Similarity NPD7334 Approved
0.6941 Remote Similarity NPD5330 Approved
0.6941 Remote Similarity NPD6684 Approved
0.6932 Remote Similarity NPD6079 Approved
0.6923 Remote Similarity NPD4755 Approved
0.6905 Remote Similarity NPD3668 Phase 3
0.6889 Remote Similarity NPD5210 Approved
0.6889 Remote Similarity NPD4629 Approved
0.6829 Remote Similarity NPD6928 Phase 2
0.6782 Remote Similarity NPD6903 Approved
0.6774 Remote Similarity NPD5286 Approved
0.6774 Remote Similarity NPD4696 Approved
0.6774 Remote Similarity NPD5285 Approved
0.6774 Remote Similarity NPD4700 Approved
0.6744 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6744 Remote Similarity NPD4694 Approved
0.6744 Remote Similarity NPD5690 Phase 2
0.6744 Remote Similarity NPD5280 Approved
0.6742 Remote Similarity NPD8034 Phase 2
0.6742 Remote Similarity NPD8035 Phase 2
0.6739 Remote Similarity NPD6084 Phase 2
0.6739 Remote Similarity NPD6083 Phase 2
0.6702 Remote Similarity NPD5223 Approved
0.6667 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6399 Phase 3
0.6632 Remote Similarity NPD5226 Approved
0.6632 Remote Similarity NPD5211 Phase 2
0.6632 Remote Similarity NPD5225 Approved
0.6632 Remote Similarity NPD5224 Approved
0.6632 Remote Similarity NPD4633 Approved
0.663 Remote Similarity NPD4697 Phase 3
0.663 Remote Similarity NPD5222 Approved
0.663 Remote Similarity NPD5221 Approved
0.663 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6562 Remote Similarity NPD5175 Approved
0.6562 Remote Similarity NPD5174 Approved
0.6562 Remote Similarity NPD4754 Approved
0.6559 Remote Similarity NPD5173 Approved
0.6556 Remote Similarity NPD7515 Phase 2
0.6522 Remote Similarity NPD5695 Phase 3
0.6522 Remote Similarity NPD3729 Clinical (unspecified phase)
0.6522 Remote Similarity NPD615 Clinical (unspecified phase)
0.6506 Remote Similarity NPD4195 Approved
0.6495 Remote Similarity NPD5141 Approved
0.6494 Remote Similarity NPD6705 Phase 1
0.6489 Remote Similarity NPD5696 Approved
0.6429 Remote Similarity NPD6675 Approved
0.6429 Remote Similarity NPD4768 Approved
0.6429 Remote Similarity NPD6402 Approved
0.6429 Remote Similarity NPD4748 Discontinued
0.6429 Remote Similarity NPD5739 Approved
0.6429 Remote Similarity NPD4767 Approved
0.6429 Remote Similarity NPD7128 Approved
0.6429 Remote Similarity NPD7525 Registered
0.6421 Remote Similarity NPD8418 Phase 2
0.642 Remote Similarity NPD6942 Approved
0.642 Remote Similarity NPD7339 Approved
0.6386 Remote Similarity NPD4802 Phase 2
0.6386 Remote Similarity NPD4238 Approved
0.6374 Remote Similarity NPD5281 Approved
0.6374 Remote Similarity NPD5284 Approved
0.6364 Remote Similarity NPD6098 Approved
0.6364 Remote Similarity NPD5697 Approved
0.6364 Remote Similarity NPD6412 Phase 2
0.6364 Remote Similarity NPD5701 Approved
0.6316 Remote Similarity NPD7638 Approved
0.6304 Remote Similarity NPD5133 Approved
0.63 Remote Similarity NPD4729 Approved
0.63 Remote Similarity NPD5128 Approved
0.63 Remote Similarity NPD6011 Approved
0.63 Remote Similarity NPD4730 Approved
0.63 Remote Similarity NPD6881 Approved
0.63 Remote Similarity NPD6899 Approved
0.63 Remote Similarity NPD7320 Approved
0.6264 Remote Similarity NPD4096 Approved
0.6263 Remote Similarity NPD6920 Discontinued
0.625 Remote Similarity NPD4243 Approved
0.625 Remote Similarity NPD7640 Approved
0.625 Remote Similarity NPD7639 Approved
0.6238 Remote Similarity NPD6012 Approved
0.6238 Remote Similarity NPD6372 Approved
0.6238 Remote Similarity NPD6014 Approved
0.6238 Remote Similarity NPD6373 Approved
0.6238 Remote Similarity NPD6013 Approved
0.6237 Remote Similarity NPD7748 Approved
0.6235 Remote Similarity NPD4695 Discontinued
0.6222 Remote Similarity NPD5737 Approved
0.6222 Remote Similarity NPD5208 Approved
0.6222 Remote Similarity NPD6672 Approved
0.6212 Remote Similarity NPD384 Approved
0.6212 Remote Similarity NPD385 Approved
0.6203 Remote Similarity NPD4137 Phase 3
0.619 Remote Similarity NPD4776 Phase 2
0.619 Remote Similarity NPD4777 Suspended
0.618 Remote Similarity NPD4519 Discontinued
0.618 Remote Similarity NPD4623 Approved
0.6176 Remote Similarity NPD5251 Approved
0.6176 Remote Similarity NPD4634 Approved
0.6176 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6176 Remote Similarity NPD5249 Phase 3
0.6176 Remote Similarity NPD7290 Approved
0.6176 Remote Similarity NPD5250 Approved
0.6176 Remote Similarity NPD7102 Approved
0.6176 Remote Similarity NPD5135 Approved
0.6176 Remote Similarity NPD5169 Approved
0.6176 Remote Similarity NPD6883 Approved
0.6176 Remote Similarity NPD5247 Approved
0.6176 Remote Similarity NPD5248 Approved
0.6154 Remote Similarity NPD6904 Approved
0.6154 Remote Similarity NPD6673 Approved
0.6154 Remote Similarity NPD6080 Approved
0.6139 Remote Similarity NPD6415 Discontinued
0.6125 Remote Similarity NPD4691 Approved
0.6125 Remote Similarity NPD4747 Approved
0.6122 Remote Similarity NPD7632 Discontinued
0.6117 Remote Similarity NPD5216 Approved
0.6117 Remote Similarity NPD6847 Approved
0.6117 Remote Similarity NPD6649 Approved
0.6117 Remote Similarity NPD5217 Approved
0.6117 Remote Similarity NPD5215 Approved
0.6117 Remote Similarity NPD6617 Approved
0.6117 Remote Similarity NPD6869 Approved
0.6117 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6117 Remote Similarity NPD6650 Approved
0.6117 Remote Similarity NPD5127 Approved
0.6117 Remote Similarity NPD8130 Phase 1
0.6111 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6098 Remote Similarity NPD6924 Approved
0.6098 Remote Similarity NPD6926 Approved
0.6098 Remote Similarity NPD4785 Approved
0.6098 Remote Similarity NPD4784 Approved
0.6076 Remote Similarity NPD3621 Clinical (unspecified phase)
0.6058 Remote Similarity NPD6882 Approved
0.6058 Remote Similarity NPD8297 Approved
0.6047 Remote Similarity NPD5368 Approved
0.6044 Remote Similarity NPD4518 Approved
0.6042 Remote Similarity NPD7902 Approved
0.6024 Remote Similarity NPD5275 Approved
0.6024 Remote Similarity NPD4190 Phase 3
0.6022 Remote Similarity NPD5693 Phase 1
0.6 Remote Similarity NPD4632 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