Structure

Physi-Chem Properties

Molecular Weight:  284.21
Volume:  338.891
LogP:  5.87
LogD:  4.631
LogS:  -5.876
# Rotatable Bonds:  8
TPSA:  9.23
# H-Bond Aceptor:  1
# H-Bond Donor:  0
# Rings:  1
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.529
Synthetic Accessibility Score:  3.192
Fsp3:  0.4
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.529
MDCK Permeability:  2.019281055254396e-05
Pgp-inhibitor:  0.836
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.018
30% Bioavailability (F30%):  0.316

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.03
Plasma Protein Binding (PPB):  96.65137481689453%
Volume Distribution (VD):  1.657
Pgp-substrate:  4.180630683898926%

ADMET: Metabolism

CYP1A2-inhibitor:  0.945
CYP1A2-substrate:  0.304
CYP2C19-inhibitor:  0.932
CYP2C19-substrate:  0.773
CYP2C9-inhibitor:  0.794
CYP2C9-substrate:  0.845
CYP2D6-inhibitor:  0.917
CYP2D6-substrate:  0.069
CYP3A4-inhibitor:  0.958
CYP3A4-substrate:  0.561

ADMET: Excretion

Clearance (CL):  7.108
Half-life (T1/2):  0.061

ADMET: Toxicity

hERG Blockers:  0.523
Human Hepatotoxicity (H-HT):  0.169
Drug-inuced Liver Injury (DILI):  0.046
AMES Toxicity:  0.062
Rat Oral Acute Toxicity:  0.015
Maximum Recommended Daily Dose:  0.118
Skin Sensitization:  0.93
Carcinogencity:  0.175
Eye Corrosion:  0.006
Eye Irritation:  0.892
Respiratory Toxicity:  0.038

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

  Natural Product: NPC471576

Natural Product ID:  NPC471576
Common Name*:   O-Ethylbakuchiol
IUPAC Name:   1-[(1E,3S)-3-ethenyl-3,7-dimethylocta-1,6-dienyl]-4-ethoxybenzene
Synonyms:   O-Ethylbakuchiol
Standard InCHIKey:  YMUXTTVGTPYRPO-KETLNSEPSA-N
Standard InCHI:  InChI=1S/C20H28O/c1-6-20(5,15-8-9-17(3)4)16-14-18-10-12-19(13-11-18)21-7-2/h6,9-14,16H,1,7-8,15H2,2-5H3/b16-14+/t20-/m1/s1
SMILES:  CCOC1=CC=C(C=C1)C=CC(C)(CCC=C(C)C)C=C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL260776
PubChem CID:   44229629
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001549] Monoterpenoids
          • [CHEMONTID:0000051] Aromatic monoterpenoids

*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
NPO30150 Psoralea corylifolia Species Fabaceae Eukaryota seeds n.a. n.a. PMID[18359631]
NPO30150 Psoralea corylifolia Species Fabaceae Eukaryota Fruits n.a. n.a. PMID[25710081]
NPO30150 Psoralea corylifolia Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[3069958]
NPO30150 Psoralea corylifolia Species Fabaceae Eukaryota n.a. seed n.a. PMID[8759164]
NPO30150 Psoralea corylifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30150 Psoralea corylifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]

☑ 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
NPT196 Cell Line AGS Homo sapiens IC50 > 50000.0 nM PMID[497492]
NPT165 Cell Line HeLa Homo sapiens IC50 > 50000.0 nM PMID[497492]
NPT21802 PROTEIN FAMILY Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha Homo sapiens IC50 = 26300.0 nM PMID[497492]
NPT2 Others Unspecified IC50 = 12200.0 nM PMID[497492]

☑ 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 NPC471576 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
0.9565 High Similarity NPC471581
0.9278 High Similarity NPC192596
0.9175 High Similarity NPC51633
0.913 High Similarity NPC99886
0.913 High Similarity NPC8002
0.913 High Similarity NPC177844
0.913 High Similarity NPC259134
0.9091 High Similarity NPC473393
0.9091 High Similarity NPC470393
0.9032 High Similarity NPC71853
0.899 High Similarity NPC108875
0.899 High Similarity NPC38079
0.8936 High Similarity NPC321956
0.8911 High Similarity NPC157473
0.8911 High Similarity NPC151530
0.89 High Similarity NPC473855
0.8812 High Similarity NPC176971
0.88 High Similarity NPC283546
0.8725 High Similarity NPC258171
0.8713 High Similarity NPC128730
0.8687 High Similarity NPC107101
0.8673 High Similarity NPC95755
0.8627 High Similarity NPC326447
0.86 High Similarity NPC307425
0.8586 High Similarity NPC100870
0.8529 High Similarity NPC8302
0.8515 High Similarity NPC179686
0.85 High Similarity NPC13755
0.8491 Intermediate Similarity NPC165646
0.8485 Intermediate Similarity NPC470161
0.8485 Intermediate Similarity NPC175298
0.8476 Intermediate Similarity NPC46844
0.8462 Intermediate Similarity NPC291837
0.8447 Intermediate Similarity NPC326801
0.8396 Intermediate Similarity NPC55300
0.835 Intermediate Similarity NPC238115
0.8333 Intermediate Similarity NPC305205
0.8302 Intermediate Similarity NPC25067
0.8302 Intermediate Similarity NPC88868
0.8302 Intermediate Similarity NPC231251
0.8288 Intermediate Similarity NPC163036
0.8269 Intermediate Similarity NPC113457
0.8252 Intermediate Similarity NPC109637
0.8241 Intermediate Similarity NPC26524
0.8235 Intermediate Similarity NPC300166
0.8235 Intermediate Similarity NPC310905
0.8235 Intermediate Similarity NPC12714
0.8224 Intermediate Similarity NPC266932
0.8208 Intermediate Similarity NPC474272
0.819 Intermediate Similarity NPC194034
0.8155 Intermediate Similarity NPC298224
0.8148 Intermediate Similarity NPC115379
0.8144 Intermediate Similarity NPC98772
0.8131 Intermediate Similarity NPC106141
0.8113 Intermediate Similarity NPC201959
0.8077 Intermediate Similarity NPC241224
0.8077 Intermediate Similarity NPC2518
0.8077 Intermediate Similarity NPC474603
0.8077 Intermediate Similarity NPC292792
0.8077 Intermediate Similarity NPC12987
0.8077 Intermediate Similarity NPC38209
0.8073 Intermediate Similarity NPC90903
0.8058 Intermediate Similarity NPC84325
0.8056 Intermediate Similarity NPC245552
0.8043 Intermediate Similarity NPC124576
0.8037 Intermediate Similarity NPC82016
0.8037 Intermediate Similarity NPC259554
0.8036 Intermediate Similarity NPC159916
0.8036 Intermediate Similarity NPC293424
0.8019 Intermediate Similarity NPC227894
0.8019 Intermediate Similarity NPC251306
0.8 Intermediate Similarity NPC125306
0.8 Intermediate Similarity NPC235250
0.8 Intermediate Similarity NPC252004
0.8 Intermediate Similarity NPC161696
0.8 Intermediate Similarity NPC42383
0.7981 Intermediate Similarity NPC24327
0.7981 Intermediate Similarity NPC62351
0.7981 Intermediate Similarity NPC12870
0.798 Intermediate Similarity NPC270547
0.7965 Intermediate Similarity NPC172253
0.7965 Intermediate Similarity NPC256369
0.7965 Intermediate Similarity NPC59561
0.7965 Intermediate Similarity NPC234956
0.7963 Intermediate Similarity NPC475852
0.7963 Intermediate Similarity NPC473809
0.7963 Intermediate Similarity NPC137685
0.7944 Intermediate Similarity NPC75440
0.7938 Intermediate Similarity NPC184169
0.7925 Intermediate Similarity NPC1065
0.7909 Intermediate Similarity NPC301735
0.7909 Intermediate Similarity NPC303522
0.7895 Intermediate Similarity NPC263835
0.789 Intermediate Similarity NPC166837
0.7879 Intermediate Similarity NPC318429
0.787 Intermediate Similarity NPC149545
0.7864 Intermediate Similarity NPC171843
0.7857 Intermediate Similarity NPC312105
0.7857 Intermediate Similarity NPC33900
0.785 Intermediate Similarity NPC35543
0.783 Intermediate Similarity NPC475269
0.7826 Intermediate Similarity NPC235190
0.7826 Intermediate Similarity NPC180006
0.7826 Intermediate Similarity NPC199023
0.7818 Intermediate Similarity NPC474920
0.7812 Intermediate Similarity NPC23837
0.7807 Intermediate Similarity NPC37858
0.7807 Intermediate Similarity NPC43435
0.7798 Intermediate Similarity NPC179309
0.7778 Intermediate Similarity NPC146530
0.7778 Intermediate Similarity NPC280347
0.7778 Intermediate Similarity NPC97811
0.7778 Intermediate Similarity NPC245115
0.7778 Intermediate Similarity NPC177420
0.7778 Intermediate Similarity NPC309982
0.7768 Intermediate Similarity NPC51345
0.7767 Intermediate Similarity NPC313918
0.7757 Intermediate Similarity NPC135464
0.7757 Intermediate Similarity NPC92623
0.7748 Intermediate Similarity NPC35344
0.7748 Intermediate Similarity NPC141003
0.7748 Intermediate Similarity NPC165106
0.7732 Intermediate Similarity NPC248817
0.7727 Intermediate Similarity NPC139617
0.7727 Intermediate Similarity NPC139946
0.7727 Intermediate Similarity NPC275627
0.7727 Intermediate Similarity NPC470723
0.7727 Intermediate Similarity NPC57879
0.7727 Intermediate Similarity NPC203924
0.7727 Intermediate Similarity NPC78918
0.7719 Intermediate Similarity NPC277460
0.7719 Intermediate Similarity NPC101503
0.7714 Intermediate Similarity NPC101025
0.7714 Intermediate Similarity NPC471578
0.7706 Intermediate Similarity NPC246358
0.7706 Intermediate Similarity NPC234639
0.7706 Intermediate Similarity NPC7097
0.7706 Intermediate Similarity NPC36108
0.7706 Intermediate Similarity NPC233731
0.7706 Intermediate Similarity NPC127326
0.77 Intermediate Similarity NPC55561
0.7699 Intermediate Similarity NPC81067
0.7699 Intermediate Similarity NPC9341
0.7692 Intermediate Similarity NPC261661
0.7692 Intermediate Similarity NPC100099
0.7692 Intermediate Similarity NPC36016
0.7692 Intermediate Similarity NPC150026
0.7692 Intermediate Similarity NPC71090
0.7685 Intermediate Similarity NPC233320
0.7679 Intermediate Similarity NPC228287
0.7679 Intermediate Similarity NPC180508
0.7677 Intermediate Similarity NPC25493
0.7677 Intermediate Similarity NPC113460
0.7677 Intermediate Similarity NPC104216
0.7672 Intermediate Similarity NPC469412
0.7672 Intermediate Similarity NPC472596
0.7672 Intermediate Similarity NPC198734
0.7672 Intermediate Similarity NPC267064
0.7672 Intermediate Similarity NPC163200
0.7664 Intermediate Similarity NPC288760
0.7664 Intermediate Similarity NPC233396
0.7664 Intermediate Similarity NPC154899
0.7664 Intermediate Similarity NPC139891
0.7664 Intermediate Similarity NPC227255
0.7658 Intermediate Similarity NPC199462
0.7658 Intermediate Similarity NPC280760
0.7653 Intermediate Similarity NPC197783
0.7652 Intermediate Similarity NPC295259
0.7652 Intermediate Similarity NPC281356
0.7652 Intermediate Similarity NPC98748
0.7652 Intermediate Similarity NPC471449
0.7647 Intermediate Similarity NPC27323
0.7647 Intermediate Similarity NPC316301
0.7642 Intermediate Similarity NPC304638
0.7636 Intermediate Similarity NPC183648
0.7636 Intermediate Similarity NPC2682
0.7632 Intermediate Similarity NPC164386
0.7632 Intermediate Similarity NPC86947
0.7632 Intermediate Similarity NPC183154
0.7632 Intermediate Similarity NPC142042
0.7632 Intermediate Similarity NPC263754
0.7629 Intermediate Similarity NPC124436
0.7629 Intermediate Similarity NPC265146
0.7627 Intermediate Similarity NPC21238
0.7627 Intermediate Similarity NPC38761
0.7627 Intermediate Similarity NPC76465
0.7627 Intermediate Similarity NPC320287
0.7627 Intermediate Similarity NPC279379
0.7627 Intermediate Similarity NPC328267
0.7627 Intermediate Similarity NPC108545
0.7627 Intermediate Similarity NPC255253
0.7624 Intermediate Similarity NPC155908
0.7615 Intermediate Similarity NPC241549
0.7611 Intermediate Similarity NPC473264
0.7611 Intermediate Similarity NPC185541
0.7611 Intermediate Similarity NPC47194
0.7611 Intermediate Similarity NPC464
0.7611 Intermediate Similarity NPC296526
0.7611 Intermediate Similarity NPC475815
0.7611 Intermediate Similarity NPC473718

  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 NPC471576 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
0.8824 High Similarity NPD2684 Approved
0.8627 High Similarity NPD3134 Approved
0.8598 High Similarity NPD7157 Approved
0.8491 Intermediate Similarity NPD7843 Approved
0.8365 Intermediate Similarity NPD1358 Approved
0.8318 Intermediate Similarity NPD821 Approved
0.819 Intermediate Similarity NPD290 Approved
0.8182 Intermediate Similarity NPD3596 Phase 2
0.8148 Intermediate Similarity NPD5535 Approved
0.8095 Intermediate Similarity NPD968 Approved
0.8073 Intermediate Similarity NPD1241 Discontinued
0.8037 Intermediate Similarity NPD5451 Approved
0.8036 Intermediate Similarity NPD6581 Approved
0.8036 Intermediate Similarity NPD6580 Approved
0.7965 Intermediate Similarity NPD6830 Clinical (unspecified phase)
0.7965 Intermediate Similarity NPD5585 Approved
0.7931 Intermediate Similarity NPD5327 Phase 3
0.7928 Intermediate Similarity NPD2557 Approved
0.7879 Intermediate Similarity NPD9365 Approved
0.7748 Intermediate Similarity NPD592 Approved
0.7748 Intermediate Similarity NPD594 Approved
0.7748 Intermediate Similarity NPD5283 Phase 1
0.7739 Intermediate Similarity NPD6516 Phase 2
0.7739 Intermediate Similarity NPD5846 Approved
0.7739 Intermediate Similarity NPD1778 Approved
0.7672 Intermediate Similarity NPD3496 Discontinued
0.7664 Intermediate Similarity NPD9697 Approved
0.7652 Intermediate Similarity NPD2595 Approved
0.7652 Intermediate Similarity NPD3445 Approved
0.7652 Intermediate Similarity NPD5691 Approved
0.7652 Intermediate Similarity NPD3444 Approved
0.7652 Intermediate Similarity NPD1357 Approved
0.7652 Intermediate Similarity NPD3443 Approved
0.7652 Intermediate Similarity NPD2594 Approved
0.7652 Intermediate Similarity NPD3049 Approved
0.7647 Intermediate Similarity NPD1432 Clinical (unspecified phase)
0.7629 Intermediate Similarity NPD111 Approved
0.7627 Intermediate Similarity NPD2429 Approved
0.7627 Intermediate Similarity NPD6543 Approved
0.7627 Intermediate Similarity NPD6542 Approved
0.7627 Intermediate Similarity NPD6540 Phase 3
0.7627 Intermediate Similarity NPD6582 Phase 2
0.7627 Intermediate Similarity NPD4359 Approved
0.7627 Intermediate Similarity NPD2428 Approved
0.7627 Intermediate Similarity NPD3685 Discontinued
0.7627 Intermediate Similarity NPD6539 Approved
0.7627 Intermediate Similarity NPD6583 Phase 3
0.7611 Intermediate Similarity NPD6671 Approved
0.7586 Intermediate Similarity NPD2554 Approved
0.7586 Intermediate Similarity NPD2556 Approved
0.7568 Intermediate Similarity NPD228 Approved
0.7565 Intermediate Similarity NPD1182 Approved
0.7565 Intermediate Similarity NPD1894 Discontinued
0.7565 Intermediate Similarity NPD1548 Phase 1
0.7563 Intermediate Similarity NPD6541 Approved
0.7563 Intermediate Similarity NPD8651 Approved
0.7563 Intermediate Similarity NPD6538 Approved
0.7523 Intermediate Similarity NPD5373 Approved
0.7523 Intermediate Similarity NPD5374 Approved
0.75 Intermediate Similarity NPD6382 Discontinued
0.748 Intermediate Similarity NPD7294 Phase 1
0.7479 Intermediate Similarity NPD4129 Approved
0.7478 Intermediate Similarity NPD5536 Phase 2
0.7476 Intermediate Similarity NPD2933 Approved
0.7476 Intermediate Similarity NPD2934 Approved
0.7438 Intermediate Similarity NPD3690 Phase 2
0.7438 Intermediate Similarity NPD7018 Phase 2
0.7438 Intermediate Similarity NPD6584 Phase 3
0.7438 Intermediate Similarity NPD3691 Phase 2
0.7419 Intermediate Similarity NPD3058 Clinical (unspecified phase)
0.7414 Intermediate Similarity NPD2486 Discontinued
0.7404 Intermediate Similarity NPD2859 Approved
0.7404 Intermediate Similarity NPD2860 Approved
0.7395 Intermediate Similarity NPD3972 Approved
0.7383 Intermediate Similarity NPD291 Approved
0.7377 Intermediate Similarity NPD4993 Discontinued
0.736 Intermediate Similarity NPD4140 Approved
0.7355 Intermediate Similarity NPD3567 Approved
0.7355 Intermediate Similarity NPD3568 Approved
0.7355 Intermediate Similarity NPD1818 Approved
0.7355 Intermediate Similarity NPD1819 Approved
0.7355 Intermediate Similarity NPD1817 Approved
0.7355 Intermediate Similarity NPD1820 Approved
0.7327 Intermediate Similarity NPD9295 Approved
0.7317 Intermediate Similarity NPD4908 Phase 1
0.7317 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7311 Intermediate Similarity NPD1610 Phase 2
0.7311 Intermediate Similarity NPD3705 Approved
0.7302 Intermediate Similarity NPD5735 Approved
0.7288 Intermediate Similarity NPD4626 Approved
0.7288 Intermediate Similarity NPD2667 Approved
0.7288 Intermediate Similarity NPD2668 Approved
0.7288 Intermediate Similarity NPD2423 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD7258 Clinical (unspecified phase)
0.7258 Intermediate Similarity NPD3164 Approved
0.7258 Intermediate Similarity NPD3179 Approved
0.7258 Intermediate Similarity NPD3166 Approved
0.7258 Intermediate Similarity NPD7095 Approved
0.7258 Intermediate Similarity NPD5163 Phase 2
0.7258 Intermediate Similarity NPD5746 Approved
0.7258 Intermediate Similarity NPD3180 Approved
0.7258 Intermediate Similarity NPD3165 Approved
0.7258 Intermediate Similarity NPD3167 Approved
0.7257 Intermediate Similarity NPD1139 Approved
0.7257 Intermediate Similarity NPD1137 Approved
0.725 Intermediate Similarity NPD2235 Phase 2
0.725 Intermediate Similarity NPD2231 Phase 2
0.725 Intermediate Similarity NPD1840 Phase 2
0.7244 Intermediate Similarity NPD6353 Approved
0.7238 Intermediate Similarity NPD1809 Phase 2
0.7236 Intermediate Similarity NPD2861 Phase 2
0.7227 Intermediate Similarity NPD3847 Discontinued
0.7227 Intermediate Similarity NPD3294 Phase 2
0.7217 Intermediate Similarity NPD593 Approved
0.7217 Intermediate Similarity NPD595 Approved
0.7213 Intermediate Similarity NPD4098 Discontinued
0.7203 Intermediate Similarity NPD1651 Approved
0.72 Intermediate Similarity NPD3374 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD6798 Discontinued
0.72 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD6812 Clinical (unspecified phase)
0.7196 Intermediate Similarity NPD3020 Approved
0.7193 Intermediate Similarity NPD1138 Approved
0.7168 Intermediate Similarity NPD2671 Approved
0.7168 Intermediate Similarity NPD2673 Approved
0.7167 Intermediate Similarity NPD1091 Approved
0.7167 Intermediate Similarity NPD422 Phase 1
0.7154 Intermediate Similarity NPD4624 Approved
0.7154 Intermediate Similarity NPD2990 Approved
0.7154 Intermediate Similarity NPD2987 Approved
0.7143 Intermediate Similarity NPD6233 Phase 2
0.7143 Intermediate Similarity NPD7265 Discontinued
0.7143 Intermediate Similarity NPD5745 Approved
0.7143 Intermediate Similarity NPD8032 Phase 2
0.7143 Intermediate Similarity NPD4870 Approved
0.7143 Intermediate Similarity NPD2107 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD4062 Phase 3
0.713 Intermediate Similarity NPD3028 Approved
0.712 Intermediate Similarity NPD6179 Discontinued
0.7107 Intermediate Similarity NPD2981 Phase 2
0.7091 Intermediate Similarity NPD9501 Approved
0.7087 Intermediate Similarity NPD4060 Phase 1
0.7087 Intermediate Similarity NPD3142 Approved
0.7087 Intermediate Similarity NPD3140 Approved
0.7087 Intermediate Similarity NPD5837 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD1794 Approved
0.7073 Intermediate Similarity NPD1770 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7054 Intermediate Similarity NPD9624 Approved
0.7049 Intermediate Similarity NPD2982 Phase 2
0.7049 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7049 Intermediate Similarity NPD2983 Phase 2
0.7049 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7049 Intermediate Similarity NPD3676 Clinical (unspecified phase)
0.704 Intermediate Similarity NPD6832 Phase 2
0.7031 Intermediate Similarity NPD6355 Discontinued
0.7025 Intermediate Similarity NPD776 Approved
0.7025 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD1535 Discovery
0.7009 Intermediate Similarity NPD6387 Discontinued
0.7008 Intermediate Similarity NPD1423 Approved
0.7008 Intermediate Similarity NPD1726 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD17 Approved
0.7 Intermediate Similarity NPD7425 Clinical (unspecified phase)
0.6992 Remote Similarity NPD6696 Suspended
0.6981 Remote Similarity NPD9296 Approved
0.6977 Remote Similarity NPD2157 Approved
0.6977 Remote Similarity NPD3052 Approved
0.6977 Remote Similarity NPD3054 Approved
0.697 Remote Similarity NPD4534 Discontinued
0.6967 Remote Similarity NPD1481 Phase 2
0.696 Remote Similarity NPD1712 Approved
0.696 Remote Similarity NPD454 Approved
0.696 Remote Similarity NPD2237 Approved
0.6935 Remote Similarity NPD987 Approved
0.6935 Remote Similarity NPD6362 Approved
0.6935 Remote Similarity NPD2797 Approved
0.693 Remote Similarity NPD556 Approved
0.6929 Remote Similarity NPD3056 Clinical (unspecified phase)
0.6923 Remote Similarity NPD4537 Clinical (unspecified phase)
0.6923 Remote Similarity NPD7097 Phase 1
0.6923 Remote Similarity NPD4536 Approved
0.6923 Remote Similarity NPD4538 Approved
0.6916 Remote Similarity NPD844 Approved
0.6911 Remote Similarity NPD1669 Approved
0.6911 Remote Similarity NPD4749 Approved
0.6909 Remote Similarity NPD940 Approved
0.6909 Remote Similarity NPD846 Approved
0.6905 Remote Similarity NPD682 Discontinued
0.6905 Remote Similarity NPD2614 Approved
0.6903 Remote Similarity NPD9552 Approved
0.6899 Remote Similarity NPD4340 Discontinued
0.6897 Remote Similarity NPD769 Approved
0.6887 Remote Similarity NPD845 Approved
0.6885 Remote Similarity NPD1611 Approved
0.6885 Remote Similarity NPD1281 Approved
0.688 Remote Similarity NPD558 Phase 2
0.688 Remote Similarity NPD6917 Clinical (unspecified phase)
0.688 Remote Similarity NPD1019 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