Structure

Physi-Chem Properties

Molecular Weight:  342.15
Volume:  360.223
LogP:  3.292
LogD:  2.679
LogS:  -4.748
# Rotatable Bonds:  8
TPSA:  68.15
# H-Bond Aceptor:  5
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.705
Synthetic Accessibility Score:  3.043
Fsp3:  0.2
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.738
MDCK Permeability:  1.5848210750846192e-05
Pgp-inhibitor:  0.997
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.012
20% Bioavailability (F20%):  0.363
30% Bioavailability (F30%):  0.173

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.039
Plasma Protein Binding (PPB):  95.6078109741211%
Volume Distribution (VD):  0.898
Pgp-substrate:  3.226233720779419%

ADMET: Metabolism

CYP1A2-inhibitor:  0.818
CYP1A2-substrate:  0.951
CYP2C19-inhibitor:  0.682
CYP2C19-substrate:  0.689
CYP2C9-inhibitor:  0.77
CYP2C9-substrate:  0.899
CYP2D6-inhibitor:  0.669
CYP2D6-substrate:  0.909
CYP3A4-inhibitor:  0.762
CYP3A4-substrate:  0.796

ADMET: Excretion

Clearance (CL):  6.598
Half-life (T1/2):  0.757

ADMET: Toxicity

hERG Blockers:  0.037
Human Hepatotoxicity (H-HT):  0.008
Drug-inuced Liver Injury (DILI):  0.04
AMES Toxicity:  0.017
Rat Oral Acute Toxicity:  0.212
Maximum Recommended Daily Dose:  0.96
Skin Sensitization:  0.899
Carcinogencity:  0.215
Eye Corrosion:  0.003
Eye Irritation:  0.218
Respiratory Toxicity:  0.36

Download Data

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

  Natural Product: NPC472597

Natural Product ID:  NPC472597
Common Name*:   QVYOUKVMJPODTK-OAHLLOKOSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  QVYOUKVMJPODTK-OAHLLOKOSA-N
Standard InCHI:  InChI=1S/C20H22O5/c1-5-7-13-8-9-16(17(10-13)23-3)25-19-12-14(15(21)6-2)11-18(24-4)20(19)22/h5-6,8-12,15,21-22H,1-2,7H2,3-4H3/t15-/m1/s1
SMILES:  COC1=C(C=CC(=C1)CC=C)OC2=CC(=CC(=C2O)OC)C(C=C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3577780
PubChem CID:   n.a.
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives
        • [CHEMONTID:0004155] Diphenylethers

*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
NPO32850 nectandra leucantha Species Lauraceae Eukaryota n.a. n.a. n.a. PMID[25835647]

☑ 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
NPT27 Others Unspecified CC50 > 292100.0 nM PMID[464334]
NPT633 Organism Leishmania donovani Leishmania donovani IC50 = 101900.0 nM PMID[464334]
NPT2 Others Unspecified Ratio CC50/IC50 > 2.9 n.a. PMID[464334]

☑ 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 NPC472597 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
0.992 High Similarity NPC16208
0.992 High Similarity NPC7903
0.992 High Similarity NPC160991
0.992 High Similarity NPC184447
0.992 High Similarity NPC35932
0.9919 High Similarity NPC472338
0.9839 High Similarity NPC210623
0.9839 High Similarity NPC222004
0.9839 High Similarity NPC226788
0.9839 High Similarity NPC273295
0.9839 High Similarity NPC3439
0.9839 High Similarity NPC218856
0.9839 High Similarity NPC470258
0.9839 High Similarity NPC285339
0.9839 High Similarity NPC202582
0.9839 High Similarity NPC190629
0.9764 High Similarity NPC310854
0.9764 High Similarity NPC170694
0.9762 High Similarity NPC470752
0.9688 High Similarity NPC472337
0.9685 High Similarity NPC475840
0.9683 High Similarity NPC309787
0.9683 High Similarity NPC470096
0.9683 High Similarity NPC469613
0.9683 High Similarity NPC30043
0.9683 High Similarity NPC469625
0.9683 High Similarity NPC470095
0.968 High Similarity NPC170844
0.968 High Similarity NPC476968
0.9677 High Similarity NPC163332
0.9677 High Similarity NPC319625
0.9677 High Similarity NPC210355
0.9677 High Similarity NPC183181
0.9677 High Similarity NPC147821
0.9677 High Similarity NPC292056
0.9677 High Similarity NPC111247
0.9677 High Similarity NPC474119
0.9677 High Similarity NPC41706
0.9677 High Similarity NPC118787
0.9612 High Similarity NPC472336
0.9612 High Similarity NPC306441
0.9612 High Similarity NPC472334
0.9612 High Similarity NPC16435
0.9606 High Similarity NPC253105
0.9606 High Similarity NPC201587
0.9603 High Similarity NPC469614
0.9603 High Similarity NPC469612
0.96 High Similarity NPC470213
0.96 High Similarity NPC98631
0.96 High Similarity NPC206615
0.96 High Similarity NPC186843
0.9597 High Similarity NPC58607
0.9597 High Similarity NPC178284
0.9597 High Similarity NPC191037
0.9535 High Similarity NPC234333
0.9535 High Similarity NPC112939
0.9535 High Similarity NPC94750
0.9535 High Similarity NPC260898
0.9535 High Similarity NPC47398
0.9535 High Similarity NPC470356
0.9535 High Similarity NPC474206
0.9535 High Similarity NPC61946
0.9535 High Similarity NPC112246
0.9535 High Similarity NPC121812
0.9531 High Similarity NPC168059
0.9531 High Similarity NPC229442
0.9528 High Similarity NPC474017
0.9524 High Similarity NPC5851
0.9524 High Similarity NPC86030
0.9516 High Similarity NPC194519
0.9466 High Similarity NPC22517
0.9462 High Similarity NPC230734
0.9462 High Similarity NPC269091
0.9462 High Similarity NPC474639
0.9462 High Similarity NPC227503
0.9462 High Similarity NPC302701
0.9457 High Similarity NPC287745
0.9444 High Similarity NPC72529
0.9435 High Similarity NPC109822
0.9435 High Similarity NPC293701
0.9435 High Similarity NPC114901
0.9435 High Similarity NPC228972
0.9435 High Similarity NPC48990
0.9435 High Similarity NPC94276
0.9435 High Similarity NPC122792
0.9394 High Similarity NPC266197
0.9394 High Similarity NPC267291
0.9394 High Similarity NPC291101
0.9389 High Similarity NPC474390
0.9389 High Similarity NPC103976
0.9389 High Similarity NPC326797
0.9389 High Similarity NPC474282
0.9389 High Similarity NPC107551
0.9389 High Similarity NPC211549
0.9389 High Similarity NPC102904
0.9389 High Similarity NPC176051
0.9385 High Similarity NPC151224
0.9385 High Similarity NPC164787
0.938 High Similarity NPC158331
0.938 High Similarity NPC11060
0.938 High Similarity NPC263064
0.937 High Similarity NPC212015
0.9365 High Similarity NPC470699
0.936 High Similarity NPC203133
0.936 High Similarity NPC233410
0.936 High Similarity NPC208950
0.936 High Similarity NPC298757
0.936 High Similarity NPC193544
0.936 High Similarity NPC472093
0.936 High Similarity NPC116907
0.936 High Similarity NPC117214
0.936 High Similarity NPC475169
0.936 High Similarity NPC251855
0.936 High Similarity NPC17943
0.936 High Similarity NPC221077
0.936 High Similarity NPC57490
0.9355 High Similarity NPC165375
0.9355 High Similarity NPC220598
0.9323 High Similarity NPC87725
0.9323 High Similarity NPC224876
0.9323 High Similarity NPC471389
0.9323 High Similarity NPC263261
0.9323 High Similarity NPC83375
0.9313 High Similarity NPC25695
0.9313 High Similarity NPC248727
0.9313 High Similarity NPC265433
0.9313 High Similarity NPC471719
0.9313 High Similarity NPC172818
0.9313 High Similarity NPC270456
0.9313 High Similarity NPC470802
0.9313 High Similarity NPC162659
0.9308 High Similarity NPC326095
0.9308 High Similarity NPC317380
0.9308 High Similarity NPC244983
0.9302 High Similarity NPC127624
0.9302 High Similarity NPC219876
0.9302 High Similarity NPC86655
0.9302 High Similarity NPC202762
0.9302 High Similarity NPC204215
0.9302 High Similarity NPC126029
0.9302 High Similarity NPC261619
0.9302 High Similarity NPC175067
0.9302 High Similarity NPC61477
0.9302 High Similarity NPC185604
0.9302 High Similarity NPC15658
0.9302 High Similarity NPC78770
0.9297 High Similarity NPC214860
0.9297 High Similarity NPC91291
0.9291 High Similarity NPC252307
0.9291 High Similarity NPC245826
0.9291 High Similarity NPC474178
0.9286 High Similarity NPC28730
0.9286 High Similarity NPC18924
0.9286 High Similarity NPC78974
0.9286 High Similarity NPC214406
0.9286 High Similarity NPC223136
0.9286 High Similarity NPC181361
0.9286 High Similarity NPC103823
0.9286 High Similarity NPC44748
0.9274 High Similarity NPC71090
0.9274 High Similarity NPC71579
0.9274 High Similarity NPC261661
0.9274 High Similarity NPC262253
0.9274 High Similarity NPC473411
0.9254 High Similarity NPC189115
0.9254 High Similarity NPC193722
0.9254 High Similarity NPC278469
0.9254 High Similarity NPC469559
0.9248 High Similarity NPC160283
0.9248 High Similarity NPC184797
0.9248 High Similarity NPC254759
0.9248 High Similarity NPC22317
0.9248 High Similarity NPC309124
0.9242 High Similarity NPC276490
0.9237 High Similarity NPC473413
0.9237 High Similarity NPC99572
0.9237 High Similarity NPC134968
0.9237 High Similarity NPC126409
0.9237 High Similarity NPC256262
0.9225 High Similarity NPC42760
0.9225 High Similarity NPC268266
0.9225 High Similarity NPC268342
0.9225 High Similarity NPC220825
0.9219 High Similarity NPC45824
0.9219 High Similarity NPC58164
0.9219 High Similarity NPC10225
0.9213 High Similarity NPC124452
0.9213 High Similarity NPC118533
0.9213 High Similarity NPC236791
0.9213 High Similarity NPC282000
0.9213 High Similarity NPC159968
0.9213 High Similarity NPC242032
0.9213 High Similarity NPC293054
0.9213 High Similarity NPC165045
0.9213 High Similarity NPC74817
0.9213 High Similarity NPC324112
0.9213 High Similarity NPC127587
0.9213 High Similarity NPC169474
0.9213 High Similarity NPC246620
0.9213 High Similarity NPC82679

  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 NPC472597 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
0.968 High Similarity NPD3027 Phase 3
0.9302 High Similarity NPD1612 Clinical (unspecified phase)
0.9302 High Similarity NPD1613 Approved
0.8992 High Similarity NPD1529 Clinical (unspecified phase)
0.8915 High Similarity NPD1530 Clinical (unspecified phase)
0.8321 Intermediate Similarity NPD2983 Phase 2
0.8321 Intermediate Similarity NPD2982 Phase 2
0.8306 Intermediate Similarity NPD228 Approved
0.8299 Intermediate Similarity NPD1934 Approved
0.8284 Intermediate Similarity NPD4908 Phase 1
0.8281 Intermediate Similarity NPD1548 Phase 1
0.8244 Intermediate Similarity NPD2981 Phase 2
0.8209 Intermediate Similarity NPD3018 Phase 2
0.8168 Intermediate Similarity NPD1610 Phase 2
0.8162 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.8151 Intermediate Similarity NPD1653 Approved
0.8121 Intermediate Similarity NPD2801 Approved
0.8121 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8045 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.8043 Intermediate Similarity NPD1558 Phase 1
0.8031 Intermediate Similarity NPD5283 Phase 1
0.8013 Intermediate Similarity NPD3882 Suspended
0.8 Intermediate Similarity NPD6166 Phase 2
0.8 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7941 Intermediate Similarity NPD2861 Phase 2
0.792 Intermediate Similarity NPD2684 Approved
0.7919 Intermediate Similarity NPD4678 Approved
0.7919 Intermediate Similarity NPD4675 Approved
0.7895 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7895 Intermediate Similarity NPD1091 Approved
0.7877 Intermediate Similarity NPD1511 Approved
0.7848 Intermediate Similarity NPD7054 Approved
0.7832 Intermediate Similarity NPD7266 Discontinued
0.7826 Intermediate Similarity NPD4625 Phase 3
0.7812 Intermediate Similarity NPD7843 Approved
0.7799 Intermediate Similarity NPD7074 Phase 3
0.7799 Intermediate Similarity NPD7472 Approved
0.7792 Intermediate Similarity NPD6234 Discontinued
0.7786 Intermediate Similarity NPD3620 Phase 2
0.7786 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7785 Intermediate Similarity NPD3818 Discontinued
0.7778 Intermediate Similarity NPD4749 Approved
0.777 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.777 Intermediate Similarity NPD1512 Approved
0.777 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7769 Intermediate Similarity NPD7157 Approved
0.7761 Intermediate Similarity NPD3705 Approved
0.7746 Intermediate Similarity NPD4538 Approved
0.7746 Intermediate Similarity NPD4536 Approved
0.7746 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.774 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7724 Intermediate Similarity NPD3060 Approved
0.7724 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7717 Intermediate Similarity NPD3021 Approved
0.7717 Intermediate Similarity NPD3022 Approved
0.7712 Intermediate Similarity NPD6374 Clinical (unspecified phase)
0.7712 Intermediate Similarity NPD3817 Phase 2
0.7698 Intermediate Similarity NPD290 Approved
0.7697 Intermediate Similarity NPD37 Approved
0.7669 Intermediate Similarity NPD1357 Approved
0.7662 Intermediate Similarity NPD4966 Approved
0.7662 Intermediate Similarity NPD4967 Phase 2
0.7662 Intermediate Similarity NPD4965 Approved
0.766 Intermediate Similarity NPD4060 Phase 1
0.764 Intermediate Similarity NPD6797 Phase 2
0.763 Intermediate Similarity NPD422 Phase 1
0.7619 Intermediate Similarity NPD968 Approved
0.7616 Intermediate Similarity NPD6055 Clinical (unspecified phase)
0.7603 Intermediate Similarity NPD4162 Approved
0.7603 Intermediate Similarity NPD6674 Discontinued
0.7603 Intermediate Similarity NPD1652 Phase 2
0.7603 Intermediate Similarity NPD4236 Phase 3
0.7603 Intermediate Similarity NPD4237 Approved
0.7593 Intermediate Similarity NPD7251 Discontinued
0.7586 Intermediate Similarity NPD3540 Phase 1
0.7584 Intermediate Similarity NPD4123 Phase 3
0.7581 Intermediate Similarity NPD291 Approved
0.758 Intermediate Similarity NPD7199 Phase 2
0.7569 Intermediate Similarity NPD5960 Phase 3
0.7569 Intermediate Similarity NPD5588 Approved
0.7562 Intermediate Similarity NPD7228 Approved
0.7546 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7546 Intermediate Similarity NPD7808 Phase 3
0.7519 Intermediate Similarity NPD5536 Phase 2
0.7517 Intermediate Similarity NPD3539 Phase 1
0.7517 Intermediate Similarity NPD4357 Discontinued
0.7516 Intermediate Similarity NPD5844 Phase 1
0.75 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6190 Approved
0.75 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD2677 Approved
0.75 Intermediate Similarity NPD6671 Approved
0.75 Intermediate Similarity NPD1242 Phase 1
0.75 Intermediate Similarity NPD4005 Discontinued
0.7483 Intermediate Similarity NPD230 Phase 1
0.7482 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7482 Intermediate Similarity NPD6584 Phase 3
0.7481 Intermediate Similarity NPD5846 Approved
0.7481 Intermediate Similarity NPD6516 Phase 2
0.7465 Intermediate Similarity NPD6233 Phase 2
0.7464 Intermediate Similarity NPD8651 Approved
0.7451 Intermediate Similarity NPD4380 Phase 2
0.745 Intermediate Similarity NPD5058 Phase 3
0.7445 Intermediate Similarity NPD2235 Phase 2
0.7445 Intermediate Similarity NPD2231 Phase 2
0.7434 Intermediate Similarity NPD3686 Approved
0.7434 Intermediate Similarity NPD3687 Approved
0.7432 Intermediate Similarity NPD4628 Phase 3
0.7423 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7419 Intermediate Similarity NPD2978 Approved
0.7419 Intermediate Similarity NPD2977 Approved
0.7417 Intermediate Similarity NPD1940 Clinical (unspecified phase)
0.74 Intermediate Similarity NPD7213 Phase 3
0.74 Intermediate Similarity NPD7212 Phase 2
0.7389 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7383 Intermediate Similarity NPD2219 Phase 1
0.7375 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7365 Intermediate Similarity NPD5177 Phase 3
0.7361 Intermediate Similarity NPD5124 Phase 1
0.7361 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7361 Intermediate Similarity NPD5735 Approved
0.7351 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7351 Intermediate Similarity NPD7447 Phase 1
0.7347 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7347 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7347 Intermediate Similarity NPD1375 Discontinued
0.7347 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7343 Intermediate Similarity NPD1726 Clinical (unspecified phase)
0.7343 Intermediate Similarity NPD2674 Phase 3
0.7333 Intermediate Similarity NPD7124 Phase 2
0.7324 Intermediate Similarity NPD7095 Approved
0.7315 Intermediate Similarity NPD3892 Phase 2
0.7315 Intermediate Similarity NPD6331 Phase 2
0.7315 Intermediate Similarity NPD4110 Phase 3
0.7315 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.731 Intermediate Similarity NPD6653 Approved
0.7308 Intermediate Similarity NPD5773 Approved
0.7308 Intermediate Similarity NPD1465 Phase 2
0.7308 Intermediate Similarity NPD5772 Approved
0.7303 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7297 Intermediate Similarity NPD1549 Phase 2
0.7296 Intermediate Similarity NPD5494 Approved
0.7292 Intermediate Similarity NPD2238 Phase 2
0.7285 Intermediate Similarity NPD1774 Approved
0.7285 Intermediate Similarity NPD6799 Approved
0.7285 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD7075 Discontinued
0.7273 Intermediate Similarity NPD6798 Discontinued
0.7266 Intermediate Similarity NPD6583 Phase 3
0.7266 Intermediate Similarity NPD6582 Phase 2
0.7266 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7261 Intermediate Similarity NPD5402 Approved
0.7241 Intermediate Similarity NPD6355 Discontinued
0.7241 Intermediate Similarity NPD4340 Discontinued
0.723 Intermediate Similarity NPD5763 Approved
0.723 Intermediate Similarity NPD5762 Approved
0.7222 Intermediate Similarity NPD4062 Phase 3
0.7205 Intermediate Similarity NPD6232 Discontinued
0.7203 Intermediate Similarity NPD3180 Approved
0.7203 Intermediate Similarity NPD3179 Approved
0.72 Intermediate Similarity NPD4535 Phase 3
0.7197 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7192 Intermediate Similarity NPD3052 Approved
0.7192 Intermediate Similarity NPD3054 Approved
0.719 Intermediate Similarity NPD7526 Approved
0.719 Intermediate Similarity NPD52 Approved
0.719 Intermediate Similarity NPD7527 Clinical (unspecified phase)
0.7183 Intermediate Similarity NPD9494 Approved
0.7181 Intermediate Similarity NPD2424 Discontinued
0.7174 Intermediate Similarity NPD3496 Discontinued
0.7172 Intermediate Similarity NPD5837 Clinical (unspecified phase)
0.7172 Intermediate Similarity NPD3061 Approved
0.7172 Intermediate Similarity NPD3062 Approved
0.7172 Intermediate Similarity NPD3059 Approved
0.7169 Intermediate Similarity NPD6559 Discontinued
0.7165 Intermediate Similarity NPD940 Approved
0.7165 Intermediate Similarity NPD846 Approved
0.7162 Intermediate Similarity NPD2796 Approved
0.7162 Intermediate Similarity NPD6099 Approved
0.7162 Intermediate Similarity NPD2161 Phase 2
0.7162 Intermediate Similarity NPD6100 Approved
0.7153 Intermediate Similarity NPD3145 Approved
0.7153 Intermediate Similarity NPD3144 Approved
0.7152 Intermediate Similarity NPD5241 Discontinued
0.7152 Intermediate Similarity NPD2563 Approved
0.7152 Intermediate Similarity NPD2560 Approved
0.7143 Intermediate Similarity NPD821 Approved
0.7143 Intermediate Similarity NPD5403 Approved
0.7143 Intermediate Similarity NPD5535 Approved
0.7143 Intermediate Similarity NPD8053 Approved
0.7143 Intermediate Similarity NPD6111 Discontinued
0.7143 Intermediate Similarity NPD8054 Approved
0.7143 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD6801 Discontinued
0.7126 Intermediate Similarity NPD7549 Discontinued
0.7124 Intermediate Similarity NPD3536 Discontinued
0.7101 Intermediate Similarity NPD9384 Approved
0.7101 Intermediate Similarity NPD9381 Approved
0.7099 Intermediate Similarity NPD3787 Discontinued

  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