Structure

Physi-Chem Properties

Molecular Weight:  258.16
Volume:  301.713
LogP:  2.712
LogD:  2.284
LogS:  -4.193
# Rotatable Bonds:  7
TPSA:  40.46
# H-Bond Aceptor:  2
# H-Bond Donor:  2
# Rings:  0
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.544
Synthetic Accessibility Score:  4.153
Fsp3:  0.412
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.016
MDCK Permeability:  0.00012391922064125538
Pgp-inhibitor:  0.001
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.058
20% Bioavailability (F20%):  0.131
30% Bioavailability (F30%):  0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.004
Plasma Protein Binding (PPB):  99.36621856689453%
Volume Distribution (VD):  0.516
Pgp-substrate:  2.1080245971679688%

ADMET: Metabolism

CYP1A2-inhibitor:  0.756
CYP1A2-substrate:  0.307
CYP2C19-inhibitor:  0.964
CYP2C19-substrate:  0.764
CYP2C9-inhibitor:  0.916
CYP2C9-substrate:  0.996
CYP2D6-inhibitor:  0.921
CYP2D6-substrate:  0.921
CYP3A4-inhibitor:  0.925
CYP3A4-substrate:  0.221

ADMET: Excretion

Clearance (CL):  4.75
Half-life (T1/2):  0.393

ADMET: Toxicity

hERG Blockers:  0.007
Human Hepatotoxicity (H-HT):  0.919
Drug-inuced Liver Injury (DILI):  0.983
AMES Toxicity:  0.775
Rat Oral Acute Toxicity:  0.037
Maximum Recommended Daily Dose:  0.913
Skin Sensitization:  0.962
Carcinogencity:  0.808
Eye Corrosion:  0.961
Eye Irritation:  0.993
Respiratory Toxicity:  0.852

Download Data

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

  Natural Product: NPC71046

Natural Product ID:  NPC71046
Common Name*:   Demethylracemosol
IUPAC Name:   n.a.
Synonyms:   Demethylracemosol
Standard InCHIKey:  VKSWXZSFBSSEFC-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C20H22O4/c1-10-16(22)8-11-4-5-13-12(6-7-15(21)18(13)23)14-9-20(2,3)24-19(10)17(11)14/h6-8,14,21-23H,4-5,9H2,1-3H3
SMILES:  Cc1c(cc2CCc3c(ccc(c3O)O)C3CC(C)(C)Oc1c23)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1173441
PubChem CID:   10404106
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000019] Dibenzocycloheptenes

*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
NPO33638 Bauhinia malabarica Species Fabaceae Eukaryota Roots n.a. n.a. PMID[19299148]
NPO7233 Piliostigma malabaricum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7233 Piliostigma malabaricum Species Fabaceae 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
NPT6 Organism Plasmodium falciparum Plasmodium falciparum EC50 = 2.0 ug.mL-1 PMID[519006]

☑ 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 NPC71046 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
0.9779 High Similarity NPC469795
0.9416 High Similarity NPC265075
0.9338 High Similarity NPC35550
0.927 High Similarity NPC32630
0.922 High Similarity NPC233980
0.9214 High Similarity NPC473845
0.9203 High Similarity NPC198038
0.9155 High Similarity NPC474397
0.913 High Similarity NPC260741
0.913 High Similarity NPC70682
0.9124 High Similarity NPC234952
0.9104 High Similarity NPC474481
0.9078 High Similarity NPC473108
0.9071 High Similarity NPC204347
0.9071 High Similarity NPC59841
0.9071 High Similarity NPC2613
0.9071 High Similarity NPC475891
0.9065 High Similarity NPC234568
0.9058 High Similarity NPC242715
0.9058 High Similarity NPC56329
0.9051 High Similarity NPC313081
0.9051 High Similarity NPC473413
0.9037 High Similarity NPC160623
0.9037 High Similarity NPC15543
0.903 High Similarity NPC16577
0.9 High Similarity NPC35216
0.8993 High Similarity NPC220344
0.8993 High Similarity NPC243996
0.8993 High Similarity NPC275061
0.8993 High Similarity NPC132804
0.8986 High Similarity NPC248727
0.8986 High Similarity NPC30632
0.8986 High Similarity NPC270456
0.8986 High Similarity NPC162659
0.8986 High Similarity NPC265433
0.8978 High Similarity NPC317380
0.8978 High Similarity NPC209199
0.8973 High Similarity NPC160196
0.8971 High Similarity NPC469611
0.8944 High Similarity NPC50250
0.8929 High Similarity NPC12668
0.8929 High Similarity NPC308768
0.8929 High Similarity NPC259519
0.8921 High Similarity NPC266453
0.8921 High Similarity NPC200935
0.8921 High Similarity NPC94994
0.8921 High Similarity NPC22902
0.8921 High Similarity NPC230919
0.8913 High Similarity NPC151224
0.8913 High Similarity NPC158142
0.8913 High Similarity NPC69029
0.8913 High Similarity NPC200557
0.8913 High Similarity NPC294884
0.8913 High Similarity NPC108198
0.8913 High Similarity NPC10314
0.8913 High Similarity NPC241241
0.8905 High Similarity NPC469610
0.8905 High Similarity NPC11060
0.8905 High Similarity NPC36661
0.8904 High Similarity NPC2745
0.8897 High Similarity NPC469907
0.8897 High Similarity NPC8899
0.8889 High Similarity NPC222108
0.8889 High Similarity NPC96719
0.8881 High Similarity NPC469557
0.8857 High Similarity NPC218131
0.8857 High Similarity NPC25966
0.8857 High Similarity NPC243759
0.8857 High Similarity NPC319647
0.8857 High Similarity NPC245207
0.8857 High Similarity NPC105847
0.8857 High Similarity NPC184613
0.8857 High Similarity NPC127218
0.8851 High Similarity NPC80918
0.8851 High Similarity NPC188578
0.8849 High Similarity NPC143139
0.8849 High Similarity NPC230734
0.8849 High Similarity NPC472800
0.8849 High Similarity NPC227503
0.8849 High Similarity NPC470802
0.8849 High Similarity NPC474639
0.8849 High Similarity NPC202846
0.8844 High Similarity NPC157783
0.8841 High Similarity NPC473107
0.8841 High Similarity NPC125649
0.8836 High Similarity NPC195561
0.8836 High Similarity NPC158784
0.8832 High Similarity NPC202762
0.8832 High Similarity NPC86655
0.8832 High Similarity NPC161958
0.8832 High Similarity NPC14224
0.8832 High Similarity NPC127624
0.8828 High Similarity NPC473876
0.8824 High Similarity NPC126836
0.8819 High Similarity NPC87794
0.8819 High Similarity NPC211758
0.8819 High Similarity NPC112251
0.8815 High Similarity NPC46274
0.8815 High Similarity NPC226331
0.8811 High Similarity NPC12641
0.8811 High Similarity NPC93323
0.8811 High Similarity NPC45257
0.8811 High Similarity NPC280092
0.8803 High Similarity NPC175838
0.8803 High Similarity NPC183709
0.8794 High Similarity NPC309124
0.8794 High Similarity NPC184797
0.8786 High Similarity NPC276490
0.8786 High Similarity NPC151656
0.8786 High Similarity NPC266006
0.8777 High Similarity NPC164787
0.8777 High Similarity NPC470356
0.8777 High Similarity NPC94750
0.8777 High Similarity NPC112246
0.8777 High Similarity NPC112939
0.8777 High Similarity NPC474206
0.8777 High Similarity NPC121812
0.8776 High Similarity NPC302915
0.8768 High Similarity NPC32778
0.8759 High Similarity NPC21776
0.8759 High Similarity NPC16269
0.875 High Similarity NPC472457
0.875 High Similarity NPC90645
0.8741 High Similarity NPC250432
0.8741 High Similarity NPC155392
0.8741 High Similarity NPC46978
0.8741 High Similarity NPC473134
0.8741 High Similarity NPC474104
0.8741 High Similarity NPC135767
0.8741 High Similarity NPC47633
0.8741 High Similarity NPC85264
0.8741 High Similarity NPC274721
0.8741 High Similarity NPC5447
0.8741 High Similarity NPC102044
0.8732 High Similarity NPC471389
0.8732 High Similarity NPC87725
0.8732 High Similarity NPC263261
0.8731 High Similarity NPC105031
0.8723 High Similarity NPC114171
0.8723 High Similarity NPC230124
0.8723 High Similarity NPC79622
0.8723 High Similarity NPC473739
0.8723 High Similarity NPC212942
0.8723 High Similarity NPC232164
0.8723 High Similarity NPC6300
0.8723 High Similarity NPC236306
0.8723 High Similarity NPC29868
0.8716 High Similarity NPC325860
0.8714 High Similarity NPC173660
0.8714 High Similarity NPC269091
0.8714 High Similarity NPC126101
0.8714 High Similarity NPC306441
0.8714 High Similarity NPC302701
0.8714 High Similarity NPC16435
0.8705 High Similarity NPC160697
0.8705 High Similarity NPC478085
0.8699 High Similarity NPC212142
0.8681 High Similarity NPC63879
0.8681 High Similarity NPC317237
0.8681 High Similarity NPC44530
0.8681 High Similarity NPC277951
0.8676 High Similarity NPC53986
0.8676 High Similarity NPC28765
0.8676 High Similarity NPC38664
0.8671 High Similarity NPC470917
0.8671 High Similarity NPC107161
0.8662 High Similarity NPC73505
0.8662 High Similarity NPC295719
0.8662 High Similarity NPC20520
0.8662 High Similarity NPC34431
0.8662 High Similarity NPC165026
0.8662 High Similarity NPC109240
0.8662 High Similarity NPC61783
0.8652 High Similarity NPC211549
0.8652 High Similarity NPC102904
0.8652 High Similarity NPC326797
0.8652 High Similarity NPC474282
0.8652 High Similarity NPC107551
0.8652 High Similarity NPC176051
0.8652 High Similarity NPC103976
0.8643 High Similarity NPC234333
0.8643 High Similarity NPC47398
0.8643 High Similarity NPC180602
0.8643 High Similarity NPC55239
0.8643 High Similarity NPC195022
0.8643 High Similarity NPC281521
0.8643 High Similarity NPC255147
0.8643 High Similarity NPC214853
0.8643 High Similarity NPC201357
0.8643 High Similarity NPC260898
0.8643 High Similarity NPC61946
0.8643 High Similarity NPC240279
0.8633 High Similarity NPC475840
0.8633 High Similarity NPC92805
0.8633 High Similarity NPC229442
0.8633 High Similarity NPC168059
0.863 High Similarity NPC101376
0.8623 High Similarity NPC244888
0.8623 High Similarity NPC118683
0.8623 High Similarity NPC293203

  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 NPC71046 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
0.903 High Similarity NPD4625 Phase 3
0.8815 High Similarity NPD1529 Clinical (unspecified phase)
0.8741 High Similarity NPD1530 Clinical (unspecified phase)
0.8582 High Similarity NPD4749 Approved
0.8561 High Similarity NPD1613 Approved
0.8561 High Similarity NPD1612 Clinical (unspecified phase)
0.8551 High Similarity NPD4907 Clinical (unspecified phase)
0.8406 Intermediate Similarity NPD4908 Phase 1
0.8296 Intermediate Similarity NPD1610 Phase 2
0.8286 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.8214 Intermediate Similarity NPD3027 Phase 3
0.8095 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.8014 Intermediate Similarity NPD6099 Approved
0.8014 Intermediate Similarity NPD6100 Approved
0.8 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7917 Intermediate Similarity NPD4060 Phase 1
0.7868 Intermediate Similarity NPD1548 Phase 1
0.7852 Intermediate Similarity NPD6674 Discontinued
0.7817 Intermediate Similarity NPD2861 Phase 2
0.78 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7786 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7746 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.773 Intermediate Similarity NPD6696 Suspended
0.7707 Intermediate Similarity NPD1934 Approved
0.7688 Intermediate Similarity NPD6234 Discontinued
0.7647 Intermediate Similarity NPD1511 Approved
0.7636 Intermediate Similarity NPD5844 Phase 1
0.7594 Intermediate Similarity NPD3021 Approved
0.7594 Intermediate Similarity NPD3022 Approved
0.7591 Intermediate Similarity NPD7340 Approved
0.7569 Intermediate Similarity NPD3018 Phase 2
0.7551 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7551 Intermediate Similarity NPD3620 Phase 2
0.7548 Intermediate Similarity NPD1512 Approved
0.7547 Intermediate Similarity NPD2801 Approved
0.7546 Intermediate Similarity NPD6232 Discontinued
0.7518 Intermediate Similarity NPD6671 Approved
0.7515 Intermediate Similarity NPD7473 Discontinued
0.75 Intermediate Similarity NPD5124 Phase 1
0.75 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD5283 Phase 1
0.75 Intermediate Similarity NPD1398 Phase 1
0.7485 Intermediate Similarity NPD7199 Phase 2
0.7484 Intermediate Similarity NPD37 Approved
0.747 Intermediate Similarity NPD7228 Approved
0.7463 Intermediate Similarity NPD4750 Phase 3
0.7453 Intermediate Similarity NPD4966 Approved
0.7453 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7453 Intermediate Similarity NPD4967 Phase 2
0.7453 Intermediate Similarity NPD4965 Approved
0.7451 Intermediate Similarity NPD3750 Approved
0.745 Intermediate Similarity NPD4097 Suspended
0.7438 Intermediate Similarity NPD1465 Phase 2
0.7438 Intermediate Similarity NPD7819 Suspended
0.7413 Intermediate Similarity NPD2983 Phase 2
0.7413 Intermediate Similarity NPD2982 Phase 2
0.7394 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD422 Phase 1
0.7383 Intermediate Similarity NPD5735 Approved
0.7378 Intermediate Similarity NPD6959 Discontinued
0.7376 Intermediate Similarity NPD4626 Approved
0.7372 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7361 Intermediate Similarity NPD8651 Approved
0.7353 Intermediate Similarity NPD228 Approved
0.7349 Intermediate Similarity NPD6166 Phase 2
0.7349 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7349 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7346 Intermediate Similarity NPD3882 Suspended
0.7343 Intermediate Similarity NPD2981 Phase 2
0.7342 Intermediate Similarity NPD1653 Approved
0.7338 Intermediate Similarity NPD3892 Phase 2
0.7325 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7315 Intermediate Similarity NPD1558 Phase 1
0.7297 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7284 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD1611 Approved
0.7267 Intermediate Similarity NPD8053 Approved
0.7267 Intermediate Similarity NPD8054 Approved
0.7261 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7261 Intermediate Similarity NPD7447 Phase 1
0.7255 Intermediate Similarity NPD5763 Approved
0.7255 Intermediate Similarity NPD5762 Approved
0.723 Intermediate Similarity NPD7095 Approved
0.7222 Intermediate Similarity NPD5929 Approved
0.7212 Intermediate Similarity NPD5494 Approved
0.7197 Intermediate Similarity NPD7213 Phase 3
0.7197 Intermediate Similarity NPD7212 Phase 2
0.7195 Intermediate Similarity NPD7075 Discontinued
0.7183 Intermediate Similarity NPD5691 Approved
0.7176 Intermediate Similarity NPD7074 Phase 3
0.7174 Intermediate Similarity NPD7635 Approved
0.7172 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7172 Intermediate Similarity NPD5327 Phase 3
0.7171 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7171 Intermediate Similarity NPD4538 Approved
0.7171 Intermediate Similarity NPD4536 Approved
0.7152 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD27 Approved
0.7143 Intermediate Similarity NPD4624 Approved
0.7143 Intermediate Similarity NPD2489 Approved
0.7143 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD4380 Phase 2
0.7126 Intermediate Similarity NPD7229 Phase 3
0.7124 Intermediate Similarity NPD3748 Approved
0.7123 Intermediate Similarity NPD1283 Approved
0.7118 Intermediate Similarity NPD7054 Approved
0.7117 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD7466 Approved
0.711 Intermediate Similarity NPD7313 Approved
0.711 Intermediate Similarity NPD7310 Approved
0.711 Intermediate Similarity NPD4578 Approved
0.711 Intermediate Similarity NPD7311 Approved
0.711 Intermediate Similarity NPD7312 Approved
0.711 Intermediate Similarity NPD4577 Approved
0.7107 Intermediate Similarity NPD1940 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD6353 Approved
0.7099 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD1549 Phase 2
0.7093 Intermediate Similarity NPD6559 Discontinued
0.7091 Intermediate Similarity NPD4055 Discovery
0.7089 Intermediate Similarity NPD7041 Phase 2
0.7089 Intermediate Similarity NPD7040 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD4663 Approved
0.7086 Intermediate Similarity NPD4140 Approved
0.7083 Intermediate Similarity NPD2969 Approved
0.7083 Intermediate Similarity NPD2970 Approved
0.7081 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD4005 Discontinued
0.7076 Intermediate Similarity NPD7472 Approved
0.7075 Intermediate Similarity NPD2797 Approved
0.7073 Intermediate Similarity NPD3817 Phase 2
0.7069 Intermediate Similarity NPD7309 Approved
0.7068 Intermediate Similarity NPD846 Approved
0.7068 Intermediate Similarity NPD940 Approved
0.7063 Intermediate Similarity NPD1651 Approved
0.7059 Intermediate Similarity NPD3818 Discontinued
0.7059 Intermediate Similarity NPD2342 Discontinued
0.7052 Intermediate Similarity NPD7549 Discontinued
0.7045 Intermediate Similarity NPD7906 Approved
0.7044 Intermediate Similarity NPD2532 Approved
0.7044 Intermediate Similarity NPD2534 Approved
0.7044 Intermediate Similarity NPD2533 Approved
0.7035 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7035 Intermediate Similarity NPD6797 Phase 2
0.7034 Intermediate Similarity NPD1091 Approved
0.7034 Intermediate Similarity NPD3705 Approved
0.7032 Intermediate Similarity NPD3540 Phase 1
0.7032 Intermediate Similarity NPD2346 Discontinued
0.703 Intermediate Similarity NPD7768 Phase 2
0.7029 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7027 Intermediate Similarity NPD6584 Phase 3
0.7025 Intermediate Similarity NPD5058 Phase 3
0.7024 Intermediate Similarity NPD3051 Approved
0.7021 Intermediate Similarity NPD7157 Approved
0.7013 Intermediate Similarity NPD5588 Approved
0.7013 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7013 Intermediate Similarity NPD4108 Discontinued
0.7013 Intermediate Similarity NPD5960 Phase 3
0.7013 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7007 Intermediate Similarity NPD2684 Approved
0.7006 Intermediate Similarity NPD4666 Phase 3
0.7006 Intermediate Similarity NPD6331 Phase 2
0.6994 Remote Similarity NPD7240 Approved
0.6994 Remote Similarity NPD7411 Suspended
0.6994 Remote Similarity NPD7251 Discontinued
0.6994 Remote Similarity NPD6072 Discontinued
0.6993 Remote Similarity NPD1607 Approved
0.6992 Remote Similarity NPD1242 Phase 1
0.6988 Remote Similarity NPD3749 Approved
0.6987 Remote Similarity NPD7037 Approved
0.6986 Remote Similarity NPD1608 Approved
0.6975 Remote Similarity NPD3226 Approved
0.6974 Remote Similarity NPD2238 Phase 2
0.6971 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6968 Remote Similarity NPD3539 Phase 1
0.6962 Remote Similarity NPD2677 Approved
0.6962 Remote Similarity NPD5307 Clinical (unspecified phase)
0.6959 Remote Similarity NPD3094 Phase 2
0.6954 Remote Similarity NPD5109 Approved
0.6954 Remote Similarity NPD6812 Clinical (unspecified phase)
0.6954 Remote Similarity NPD5110 Phase 2
0.6954 Remote Similarity NPD5111 Phase 2
0.6954 Remote Similarity NPD3268 Approved
0.6946 Remote Similarity NPD5709 Phase 3
0.6943 Remote Similarity NPD1652 Phase 2
0.6933 Remote Similarity NPD4675 Approved
0.6933 Remote Similarity NPD4678 Approved
0.6933 Remote Similarity NPD6599 Discontinued
0.6929 Remote Similarity NPD7843 Approved
0.6929 Remote Similarity NPD5535 Approved
0.6928 Remote Similarity NPD6355 Discontinued
0.6923 Remote Similarity NPD3787 Discontinued
0.6923 Remote Similarity NPD7266 Discontinued
0.6923 Remote Similarity NPD7644 Approved
0.6918 Remote Similarity NPD1281 Approved
0.6918 Remote Similarity NPD3092 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