Structure

Physi-Chem Properties

Molecular Weight:  290.19
Volume:  324.516
LogP:  2.88
LogD:  2.7
LogS:  -2.411
# Rotatable Bonds:  7
TPSA:  60.69
# H-Bond Aceptor:  3
# H-Bond Donor:  3
# Rings:  1
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.673
Synthetic Accessibility Score:  3.755
Fsp3:  0.444
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:  -4.591
MDCK Permeability:  2.0774410586454906e-05
Pgp-inhibitor:  0.003
Pgp-substrate:  0.088
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.005
30% Bioavailability (F30%):  0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.203
Plasma Protein Binding (PPB):  92.03848266601562%
Volume Distribution (VD):  1.942
Pgp-substrate:  6.277937412261963%

ADMET: Metabolism

CYP1A2-inhibitor:  0.033
CYP1A2-substrate:  0.233
CYP2C19-inhibitor:  0.08
CYP2C19-substrate:  0.28
CYP2C9-inhibitor:  0.188
CYP2C9-substrate:  0.871
CYP2D6-inhibitor:  0.467
CYP2D6-substrate:  0.069
CYP3A4-inhibitor:  0.824
CYP3A4-substrate:  0.314

ADMET: Excretion

Clearance (CL):  9.738
Half-life (T1/2):  0.782

ADMET: Toxicity

hERG Blockers:  0.055
Human Hepatotoxicity (H-HT):  0.221
Drug-inuced Liver Injury (DILI):  0.011
AMES Toxicity:  0.006
Rat Oral Acute Toxicity:  0.902
Maximum Recommended Daily Dose:  0.897
Skin Sensitization:  0.912
Carcinogencity:  0.118
Eye Corrosion:  0.022
Eye Irritation:  0.455
Respiratory Toxicity:  0.941

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

  Natural Product: NPC101025

Natural Product ID:  NPC101025
Common Name*:   12,13-Dihydroxybakuchiol
IUPAC Name:   (E,3R,6S)-6-ethenyl-8-(4-hydroxyphenyl)-2,6-dimethyloct-7-ene-2,3-diol
Synonyms:  
Standard InCHIKey:  QIXGHNLALDUHDP-BDULIULHSA-N
Standard InCHI:  InChI=1S/C18H26O3/c1-5-18(4,13-11-16(20)17(2,3)21)12-10-14-6-8-15(19)9-7-14/h5-10,12,16,19-21H,1,11,13H2,2-4H3/b12-10+/t16-,18+/m1/s1
SMILES:  C=C[C@@](C)(/C=C/c1ccc(cc1)O)CC[C@H](C(C)(C)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3577255
PubChem CID:   36222828
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0003909] Fatty Acyls
        • [CHEMONTID:0001334] Fatty alcohols

*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
NPT81 Cell Line A549 Homo sapiens IC50 > 10000.0 nM PMID[515906]
NPT111 Cell Line K562 Homo sapiens IC50 > 10000.0 nM PMID[515906]

☑ 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 NPC101025 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 NPC471578
0.9286 High Similarity NPC62351
0.9149 High Similarity NPC270547
0.8936 High Similarity NPC98772
0.8854 High Similarity NPC325292
0.8854 High Similarity NPC138117
0.883 High Similarity NPC104216
0.8788 High Similarity NPC51333
0.8788 High Similarity NPC78119
0.8788 High Similarity NPC132078
0.8788 High Similarity NPC216468
0.8763 High Similarity NPC27323
0.8763 High Similarity NPC316301
0.875 High Similarity NPC155908
0.8723 High Similarity NPC184169
0.87 High Similarity NPC213730
0.8687 High Similarity NPC474073
0.8673 High Similarity NPC313650
0.8646 High Similarity NPC300017
0.8641 High Similarity NPC477814
0.8614 High Similarity NPC7686
0.8614 High Similarity NPC91461
0.8614 High Similarity NPC40258
0.86 High Similarity NPC128723
0.86 High Similarity NPC131587
0.86 High Similarity NPC92730
0.8571 High Similarity NPC62258
0.8571 High Similarity NPC55617
0.8544 High Similarity NPC154899
0.8544 High Similarity NPC233396
0.8542 High Similarity NPC242240
0.8542 High Similarity NPC318325
0.8542 High Similarity NPC177420
0.8542 High Similarity NPC123273
0.8542 High Similarity NPC280347
0.8515 High Similarity NPC294741
0.8515 High Similarity NPC225506
0.8511 High Similarity NPC248817
0.8505 High Similarity NPC228425
0.85 High Similarity NPC225464
0.8491 Intermediate Similarity NPC120982
0.8491 Intermediate Similarity NPC226401
0.8491 Intermediate Similarity NPC79793
0.8491 Intermediate Similarity NPC44732
0.8491 Intermediate Similarity NPC174096
0.8491 Intermediate Similarity NPC147634
0.8485 Intermediate Similarity NPC26244
0.8468 Intermediate Similarity NPC163036
0.8462 Intermediate Similarity NPC92623
0.8462 Intermediate Similarity NPC135464
0.8454 Intermediate Similarity NPC300478
0.8454 Intermediate Similarity NPC55561
0.8447 Intermediate Similarity NPC120719
0.844 Intermediate Similarity NPC474486
0.8438 Intermediate Similarity NPC113460
0.8438 Intermediate Similarity NPC25493
0.8431 Intermediate Similarity NPC110764
0.8431 Intermediate Similarity NPC472585
0.8421 Intermediate Similarity NPC197783
0.8416 Intermediate Similarity NPC122005
0.8416 Intermediate Similarity NPC252821
0.8411 Intermediate Similarity NPC187583
0.8411 Intermediate Similarity NPC308689
0.8411 Intermediate Similarity NPC257430
0.8411 Intermediate Similarity NPC179002
0.8404 Intermediate Similarity NPC265146
0.8404 Intermediate Similarity NPC124436
0.84 Intermediate Similarity NPC132271
0.84 Intermediate Similarity NPC292730
0.84 Intermediate Similarity NPC473388
0.84 Intermediate Similarity NPC216520
0.84 Intermediate Similarity NPC82664
0.8396 Intermediate Similarity NPC473524
0.8384 Intermediate Similarity NPC151715
0.8384 Intermediate Similarity NPC152415
0.8367 Intermediate Similarity NPC304541
0.8351 Intermediate Similarity NPC258219
0.835 Intermediate Similarity NPC196479
0.8349 Intermediate Similarity NPC12656
0.8333 Intermediate Similarity NPC23167
0.8316 Intermediate Similarity NPC175313
0.8302 Intermediate Similarity NPC262365
0.8302 Intermediate Similarity NPC317305
0.83 Intermediate Similarity NPC107522
0.8288 Intermediate Similarity NPC320864
0.8283 Intermediate Similarity NPC162314
0.8283 Intermediate Similarity NPC3358
0.8283 Intermediate Similarity NPC210497
0.8283 Intermediate Similarity NPC94139
0.8283 Intermediate Similarity NPC306884
0.8283 Intermediate Similarity NPC147284
0.8283 Intermediate Similarity NPC55903
0.8269 Intermediate Similarity NPC12278
0.8265 Intermediate Similarity NPC192
0.8265 Intermediate Similarity NPC312304
0.8241 Intermediate Similarity NPC470355
0.8241 Intermediate Similarity NPC139946
0.8208 Intermediate Similarity NPC61033
0.8208 Intermediate Similarity NPC474352
0.8208 Intermediate Similarity NPC305603
0.8198 Intermediate Similarity NPC474358
0.8198 Intermediate Similarity NPC257540
0.8198 Intermediate Similarity NPC154511
0.8198 Intermediate Similarity NPC137496
0.8198 Intermediate Similarity NPC474387
0.8198 Intermediate Similarity NPC247858
0.8182 Intermediate Similarity NPC306074
0.8182 Intermediate Similarity NPC120280
0.8182 Intermediate Similarity NPC45040
0.8182 Intermediate Similarity NPC204210
0.8182 Intermediate Similarity NPC473137
0.8173 Intermediate Similarity NPC235762
0.8173 Intermediate Similarity NPC471228
0.8155 Intermediate Similarity NPC211885
0.8155 Intermediate Similarity NPC174911
0.8148 Intermediate Similarity NPC63345
0.8148 Intermediate Similarity NPC46844
0.8137 Intermediate Similarity NPC109955
0.8137 Intermediate Similarity NPC475078
0.8137 Intermediate Similarity NPC77492
0.8125 Intermediate Similarity NPC150837
0.8125 Intermediate Similarity NPC164386
0.8125 Intermediate Similarity NPC477136
0.8119 Intermediate Similarity NPC274678
0.8119 Intermediate Similarity NPC286006
0.8119 Intermediate Similarity NPC222146
0.8119 Intermediate Similarity NPC144682
0.8113 Intermediate Similarity NPC53740
0.8108 Intermediate Similarity NPC147179
0.81 Intermediate Similarity NPC181709
0.8095 Intermediate Similarity NPC475225
0.8095 Intermediate Similarity NPC323810
0.8087 Intermediate Similarity NPC77569
0.8087 Intermediate Similarity NPC142198
0.8081 Intermediate Similarity NPC47950
0.8077 Intermediate Similarity NPC252105
0.807 Intermediate Similarity NPC223451
0.8061 Intermediate Similarity NPC19680
0.8061 Intermediate Similarity NPC27974
0.8058 Intermediate Similarity NPC299762
0.8058 Intermediate Similarity NPC33675
0.8058 Intermediate Similarity NPC171843
0.8056 Intermediate Similarity NPC254833
0.8056 Intermediate Similarity NPC228343
0.8053 Intermediate Similarity NPC164649
0.8053 Intermediate Similarity NPC48342
0.8037 Intermediate Similarity NPC66834
0.8037 Intermediate Similarity NPC251306
0.8036 Intermediate Similarity NPC477137
0.8036 Intermediate Similarity NPC38893
0.8036 Intermediate Similarity NPC219112
0.8036 Intermediate Similarity NPC308311
0.8036 Intermediate Similarity NPC308828
0.802 Intermediate Similarity NPC128062
0.802 Intermediate Similarity NPC76938
0.802 Intermediate Similarity NPC289769
0.8019 Intermediate Similarity NPC138942
0.8019 Intermediate Similarity NPC47284
0.8018 Intermediate Similarity NPC268160
0.8 Intermediate Similarity NPC108497
0.8 Intermediate Similarity NPC477802
0.8 Intermediate Similarity NPC477801
0.8 Intermediate Similarity NPC192596
0.8 Intermediate Similarity NPC168829
0.7982 Intermediate Similarity NPC321252
0.7982 Intermediate Similarity NPC475018
0.7982 Intermediate Similarity NPC311595
0.7982 Intermediate Similarity NPC252544
0.7982 Intermediate Similarity NPC24474
0.7982 Intermediate Similarity NPC470215
0.7982 Intermediate Similarity NPC109371
0.7982 Intermediate Similarity NPC470214
0.7981 Intermediate Similarity NPC129373
0.7981 Intermediate Similarity NPC248396
0.7981 Intermediate Similarity NPC48730
0.7981 Intermediate Similarity NPC223393
0.7981 Intermediate Similarity NPC72729
0.798 Intermediate Similarity NPC70436
0.7965 Intermediate Similarity NPC200988
0.7965 Intermediate Similarity NPC145023
0.7965 Intermediate Similarity NPC610
0.7965 Intermediate Similarity NPC175799
0.7963 Intermediate Similarity NPC201959
0.7961 Intermediate Similarity NPC201967
0.7961 Intermediate Similarity NPC152097
0.7959 Intermediate Similarity NPC307235
0.7959 Intermediate Similarity NPC407
0.7946 Intermediate Similarity NPC35797
0.7946 Intermediate Similarity NPC192948
0.7944 Intermediate Similarity NPC19149
0.7944 Intermediate Similarity NPC155072
0.7944 Intermediate Similarity NPC113457
0.7944 Intermediate Similarity NPC310456
0.7941 Intermediate Similarity NPC32714
0.7941 Intermediate Similarity NPC8392
0.7938 Intermediate Similarity NPC286904
0.7928 Intermediate Similarity NPC176730
0.7928 Intermediate Similarity NPC123175
0.7925 Intermediate Similarity NPC52087
0.7925 Intermediate Similarity NPC79672

  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 NPC101025 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
0.8763 High Similarity NPD1432 Clinical (unspecified phase)
0.8485 Intermediate Similarity NPD2860 Approved
0.8485 Intermediate Similarity NPD2859 Approved
0.8416 Intermediate Similarity NPD3020 Approved
0.8404 Intermediate Similarity NPD111 Approved
0.8384 Intermediate Similarity NPD2933 Approved
0.8384 Intermediate Similarity NPD2934 Approved
0.8119 Intermediate Similarity NPD1809 Phase 2
0.8087 Intermediate Similarity NPD3092 Approved
0.8056 Intermediate Similarity NPD3021 Approved
0.8056 Intermediate Similarity NPD3022 Approved
0.8053 Intermediate Similarity NPD3091 Approved
0.7981 Intermediate Similarity NPD289 Clinical (unspecified phase)
0.7963 Intermediate Similarity NPD2684 Approved
0.7946 Intermediate Similarity NPD7157 Approved
0.7941 Intermediate Similarity NPD844 Approved
0.7905 Intermediate Similarity NPD940 Approved
0.7905 Intermediate Similarity NPD846 Approved
0.7815 Intermediate Similarity NPD3094 Phase 2
0.7768 Intermediate Similarity NPD7159 Clinical (unspecified phase)
0.7748 Intermediate Similarity NPD6124 Clinical (unspecified phase)
0.7745 Intermediate Similarity NPD845 Approved
0.7692 Intermediate Similarity NPD288 Approved
0.7679 Intermediate Similarity NPD7843 Approved
0.7672 Intermediate Similarity NPD1357 Approved
0.7642 Intermediate Similarity NPD1242 Phase 1
0.7611 Intermediate Similarity NPD2229 Approved
0.7611 Intermediate Similarity NPD2234 Approved
0.7611 Intermediate Similarity NPD2228 Approved
0.7607 Intermediate Similarity NPD3095 Discontinued
0.7589 Intermediate Similarity NPD228 Approved
0.7568 Intermediate Similarity NPD9380 Clinical (unspecified phase)
0.7545 Intermediate Similarity NPD290 Approved
0.7479 Intermediate Similarity NPD5351 Clinical (unspecified phase)
0.7479 Intermediate Similarity NPD5350 Clinical (unspecified phase)
0.7458 Intermediate Similarity NPD5238 Clinical (unspecified phase)
0.7458 Intermediate Similarity NPD4059 Approved
0.7368 Intermediate Similarity NPD9294 Approved
0.735 Intermediate Similarity NPD16 Approved
0.735 Intermediate Similarity NPD856 Approved
0.7315 Intermediate Similarity NPD3028 Approved
0.7311 Intermediate Similarity NPD2932 Approved
0.7311 Intermediate Similarity NPD3019 Approved
0.7311 Intermediate Similarity NPD9381 Approved
0.7311 Intermediate Similarity NPD9384 Approved
0.7297 Intermediate Similarity NPD1445 Approved
0.7297 Intermediate Similarity NPD1444 Approved
0.728 Intermediate Similarity NPD3027 Phase 3
0.7273 Intermediate Similarity NPD9610 Approved
0.7273 Intermediate Similarity NPD9608 Approved
0.7258 Intermediate Similarity NPD5736 Approved
0.7257 Intermediate Similarity NPD4750 Phase 3
0.7244 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7244 Intermediate Similarity NPD3620 Phase 2
0.7241 Intermediate Similarity NPD9618 Approved
0.7241 Intermediate Similarity NPD9614 Approved
0.7236 Intermediate Similarity NPD4104 Clinical (unspecified phase)
0.7236 Intermediate Similarity NPD4103 Phase 2
0.7234 Intermediate Similarity NPD9087 Approved
0.7217 Intermediate Similarity NPD9377 Approved
0.7217 Intermediate Similarity NPD9379 Approved
0.7213 Intermediate Similarity NPD4659 Approved
0.7213 Intermediate Similarity NPD9622 Approved
0.7203 Intermediate Similarity NPD317 Approved
0.7203 Intermediate Similarity NPD318 Approved
0.7182 Intermediate Similarity NPD9500 Approved
0.7179 Intermediate Similarity NPD6671 Approved
0.7167 Intermediate Similarity NPD4589 Approved
0.7143 Intermediate Similarity NPD968 Approved
0.7143 Intermediate Similarity NPD3134 Approved
0.7131 Intermediate Similarity NPD2561 Approved
0.7131 Intermediate Similarity NPD2562 Approved
0.7113 Intermediate Similarity NPD9088 Approved
0.7105 Intermediate Similarity NPD1792 Phase 2
0.7094 Intermediate Similarity NPD1791 Approved
0.7094 Intermediate Similarity NPD1793 Approved
0.7094 Intermediate Similarity NPD2629 Approved
0.708 Intermediate Similarity NPD1358 Approved
0.7073 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7069 Intermediate Similarity NPD821 Approved
0.7069 Intermediate Similarity NPD7635 Approved
0.7059 Intermediate Similarity NPD9613 Approved
0.7059 Intermediate Similarity NPD9616 Approved
0.7059 Intermediate Similarity NPD9615 Approved
0.7054 Intermediate Similarity NPD5735 Approved
0.7043 Intermediate Similarity NPD9280 Clinical (unspecified phase)
0.704 Intermediate Similarity NPD9620 Approved
0.704 Intermediate Similarity NPD9619 Approved
0.704 Intermediate Similarity NPD9621 Approved
0.7031 Intermediate Similarity NPD6663 Approved
0.7027 Intermediate Similarity NPD5700 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD5846 Approved
0.7025 Intermediate Similarity NPD2667 Approved
0.7025 Intermediate Similarity NPD2668 Approved
0.7025 Intermediate Similarity NPD6516 Phase 2
0.7025 Intermediate Similarity NPD1751 Approved
0.7016 Intermediate Similarity NPD8651 Approved
0.7009 Intermediate Similarity NPD5283 Phase 1
0.7 Intermediate Similarity NPD316 Approved
0.6972 Remote Similarity NPD9273 Approved
0.6972 Remote Similarity NPD9495 Approved
0.6967 Remote Similarity NPD3421 Phase 3
0.696 Remote Similarity NPD1135 Approved
0.696 Remote Similarity NPD1131 Approved
0.696 Remote Similarity NPD1129 Approved
0.696 Remote Similarity NPD1133 Approved
0.696 Remote Similarity NPD1134 Approved
0.6957 Remote Similarity NPD5451 Approved
0.6953 Remote Similarity NPD597 Approved
0.6953 Remote Similarity NPD598 Approved
0.6953 Remote Similarity NPD601 Approved
0.6942 Remote Similarity NPD4196 Clinical (unspecified phase)
0.6942 Remote Similarity NPD4093 Discontinued
0.6942 Remote Similarity NPD4235 Clinical (unspecified phase)
0.6935 Remote Similarity NPD6582 Phase 2
0.6935 Remote Similarity NPD3600 Clinical (unspecified phase)
0.6935 Remote Similarity NPD6583 Phase 3
0.6935 Remote Similarity NPD3685 Discontinued
0.693 Remote Similarity NPD2342 Discontinued
0.6905 Remote Similarity NPD4624 Approved
0.6905 Remote Similarity NPD6584 Phase 3
0.6899 Remote Similarity NPD1130 Approved
0.6899 Remote Similarity NPD1132 Approved
0.6899 Remote Similarity NPD1136 Approved
0.6894 Remote Similarity NPD7743 Approved
0.6894 Remote Similarity NPD7742 Approved
0.6891 Remote Similarity NPD255 Approved
0.6891 Remote Similarity NPD256 Approved
0.6891 Remote Similarity NPD4198 Discontinued
0.6887 Remote Similarity NPD9365 Approved
0.6885 Remote Similarity NPD4626 Approved
0.6875 Remote Similarity NPD7095 Approved
0.6864 Remote Similarity NPD4869 Clinical (unspecified phase)
0.686 Remote Similarity NPD5304 Approved
0.686 Remote Similarity NPD9545 Approved
0.686 Remote Similarity NPD5303 Approved
0.6857 Remote Similarity NPD9295 Approved
0.6852 Remote Similarity NPD9296 Approved
0.685 Remote Similarity NPD2861 Phase 2
0.6846 Remote Similarity NPD4060 Phase 1
0.6846 Remote Similarity NPD4140 Approved
0.6846 Remote Similarity NPD3062 Approved
0.6846 Remote Similarity NPD3061 Approved
0.6846 Remote Similarity NPD3059 Approved
0.6832 Remote Similarity NPD9089 Approved
0.6829 Remote Similarity NPD3143 Discontinued
0.6825 Remote Similarity NPD4339 Clinical (unspecified phase)
0.6825 Remote Similarity NPD3055 Approved
0.6825 Remote Similarity NPD3053 Approved
0.6822 Remote Similarity NPD6410 Clinical (unspecified phase)
0.6807 Remote Similarity NPD475 Phase 2
0.68 Remote Similarity NPD5327 Phase 3
0.6797 Remote Similarity NPD4908 Phase 1
0.6786 Remote Similarity NPD291 Approved
0.6783 Remote Similarity NPD9265 Clinical (unspecified phase)
0.6774 Remote Similarity NPD1610 Phase 2
0.6774 Remote Similarity NPD1091 Approved
0.6772 Remote Similarity NPD2194 Approved
0.6772 Remote Similarity NPD3691 Phase 2
0.6772 Remote Similarity NPD2195 Approved
0.6772 Remote Similarity NPD3690 Phase 2
0.6772 Remote Similarity NPD6917 Clinical (unspecified phase)
0.6769 Remote Similarity NPD6407 Approved
0.6769 Remote Similarity NPD6405 Approved
0.6765 Remote Similarity NPD4628 Phase 3
0.6762 Remote Similarity NPD9094 Approved
0.6748 Remote Similarity NPD2286 Discontinued
0.6748 Remote Similarity NPD1778 Approved
0.6746 Remote Similarity NPD5310 Approved
0.6746 Remote Similarity NPD5311 Approved
0.6742 Remote Similarity NPD5314 Approved
0.6742 Remote Similarity NPD823 Approved
0.6742 Remote Similarity NPD817 Approved
0.6742 Remote Similarity NPD6353 Approved
0.6733 Remote Similarity NPD9093 Approved
0.6721 Remote Similarity NPD7741 Discontinued
0.6721 Remote Similarity NPD7330 Discontinued
0.6721 Remote Similarity NPD1548 Phase 1
0.672 Remote Similarity NPD2233 Approved
0.672 Remote Similarity NPD2232 Approved
0.672 Remote Similarity NPD2235 Phase 2
0.672 Remote Similarity NPD2230 Approved
0.672 Remote Similarity NPD3070 Discontinued
0.672 Remote Similarity NPD2337 Clinical (unspecified phase)
0.672 Remote Similarity NPD2231 Phase 2
0.6719 Remote Similarity NPD3635 Approved
0.6719 Remote Similarity NPD3636 Approved
0.6719 Remote Similarity NPD3637 Approved
0.6719 Remote Similarity NPD9494 Approved
0.6719 Remote Similarity NPD4208 Discontinued
0.6718 Remote Similarity NPD5837 Clinical (unspecified phase)
0.6718 Remote Similarity NPD826 Approved
0.6718 Remote Similarity NPD2238 Phase 2
0.6718 Remote Similarity NPD825 Approved
0.6718 Remote Similarity NPD1613 Approved
0.6718 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6694 Remote Similarity NPD3847 Discontinued
0.6694 Remote Similarity NPD3026 Approved
0.6694 Remote Similarity NPD3023 Approved
0.6694 Remote Similarity NPD2688 Clinical (unspecified phase)

  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