Structure

Physi-Chem Properties

Molecular Weight:  222.2
Volume:  262.957
LogP:  5.587
LogD:  3.976
LogS:  -3.988
# Rotatable Bonds:  4
TPSA:  20.23
# H-Bond Aceptor:  1
# H-Bond Donor:  1
# Rings:  1
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.706
Synthetic Accessibility Score:  3.673
Fsp3:  0.733
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:  -4.45
MDCK Permeability:  1.7293450582656078e-05
Pgp-inhibitor:  0.896
Pgp-substrate:  0.003
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.906
30% Bioavailability (F30%):  0.104

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.091
Plasma Protein Binding (PPB):  93.58374786376953%
Volume Distribution (VD):  2.439
Pgp-substrate:  4.715256214141846%

ADMET: Metabolism

CYP1A2-inhibitor:  0.536
CYP1A2-substrate:  0.147
CYP2C19-inhibitor:  0.321
CYP2C19-substrate:  0.858
CYP2C9-inhibitor:  0.19
CYP2C9-substrate:  0.586
CYP2D6-inhibitor:  0.075
CYP2D6-substrate:  0.093
CYP3A4-inhibitor:  0.163
CYP3A4-substrate:  0.218

ADMET: Excretion

Clearance (CL):  16.481
Half-life (T1/2):  0.198

ADMET: Toxicity

hERG Blockers:  0.032
Human Hepatotoxicity (H-HT):  0.825
Drug-inuced Liver Injury (DILI):  0.026
AMES Toxicity:  0.002
Rat Oral Acute Toxicity:  0.008
Maximum Recommended Daily Dose:  0.056
Skin Sensitization:  0.938
Carcinogencity:  0.4
Eye Corrosion:  0.784
Eye Irritation:  0.974
Respiratory Toxicity:  0.029

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  Natural Product: NPC179169

Natural Product ID:  NPC179169
Common Name*:   R-Bisabolol
IUPAC Name:   (2S)-6-methyl-2-[(1R)-4-methylcyclohex-3-en-1-yl]hept-5-en-2-ol
Synonyms:   R-Bisabolol
Standard InCHIKey:  RGZSQWQPBWRIAQ-GJZGRUSLSA-N
Standard InCHI:  InChI=1S/C15H26O/c1-12(2)6-5-11-15(4,16)14-9-7-13(3)8-10-14/h6-7,14,16H,5,8-11H2,1-4H3/t14-,15-/m0/s1
SMILES:  CC(=CCC[C@@]([C@@H]1CCC(=CC1)C)(O)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL519167
PubChem CID:   1201551
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO2768 Berchemia floribunda Species Rhamnaceae Eukaryota n.a. n.a. n.a. DOI[10.1002/cbdv.200690067]
NPO11979 Bugula neritina Species Bugulidae Eukaryota n.a. n.a. n.a. DOI[10.1021/ja00388a092]
NPO11702 Plexaurella grisea Species Plexauridae Eukaryota n.a. n.a. n.a. PMID[11325216]
NPO17377 Pittosporum viridiflorum Species Pittosporaceae Eukaryota n.a. n.a. n.a. PMID[11809069]
NPO15579 Mycale laxissima Species Mycalidae Eukaryota n.a. n.a. n.a. PMID[12932129]
NPO16634 Sinularia manaarensis Species Alcyoniidae Eukaryota n.a. n.a. n.a. PMID[16933863]
NPO7664 Pseudocedrela kotschyi Species Meliaceae Eukaryota roots n.a. n.a. PMID[17253841]
NPO13975 Calanthe arisanensis Species Orchidaceae Eukaryota n.a. n.a. n.a. PMID[18640035]
NPO13975 Calanthe arisanensis Species Orchidaceae Eukaryota n.a. n.a. n.a. PMID[19193043]
NPO5018 Nervilia fordii Species Orchidaceae Eukaryota whole plant n.a. n.a. PMID[19422205]
NPO11979 Bugula neritina Species Bugulidae Eukaryota n.a. South China Sea n.a. PMID[25932671]
NPO11979 Bugula neritina Species Bugulidae Eukaryota n.a. Gulf of Aomori, Japan n.a. PMID[8691208]
NPO10969 Epimedium sagittatum Species Berberidaceae Eukaryota n.a. leaf n.a. PMID[8699184]
NPO11979 Bugula neritina Species Bugulidae Eukaryota n.a. n.a. n.a. PMID[8882431]
NPO16120 Swertia decora Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO10969 Epimedium sagittatum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22541 Channa argus Species Channidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15904 Chrysosplenium oppositifolium Species Saxifragaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14127 Veratrum eschscholtzii Species Melanthiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10969 Epimedium sagittatum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9964 Aglaia lawii Species Meliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10969 Epimedium sagittatum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO10969 Epimedium sagittatum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO27420 Venidium hirsutum n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO16878 Roldana barba-johannis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27425 Pseudotaxus chienii Species Taxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16223 Serratula xeranthemoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13130 0tholaena peninsularis Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13410 Mcneillia graminifolia Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2768 Berchemia floribunda Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16789 Erythrina sandwicensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15341 Mucuna sloanei Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16713 Choisya arizonica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9964 Aglaia lawii Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14625 Santolina rosmarinifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22394 Hyacinthoides hispanica Species Hyacinthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8782 Arnica sachalinensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14127 Veratrum eschscholtzii Species Melanthiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16553 Theonella cupola Species Theonellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16466 Baccharis santelicis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1780 Sphaeria doliolum n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO16313 Ochrocarpos odoratus Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15579 Mycale laxissima Species Mycalidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11413 Incarvillea emodi Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6899 Hepialus hecta Species Hepialidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13773 Eriogonum nudum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11702 Plexaurella grisea Species Plexauridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13975 Calanthe arisanensis Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15194 Euphorbia balsamifera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16634 Sinularia manaarensis Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5018 Nervilia fordii Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1354 Myelochroa rhytidodes Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15452 Senecio othonniformis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO752 Oligonychus bessardi Species Tetranychidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13296 Pinus sitchensis Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9425 Punctelia microsticta Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11979 Bugula neritina Species Bugulidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7664 Pseudocedrela kotschyi Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17447 Agathosma betulina Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21773 Rothmannia urcelliformis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3742 Betula maximowicziana Species Betulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10969 Epimedium sagittatum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12087 Amaioua guianensis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15904 Chrysosplenium oppositifolium Species Saxifragaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17377 Pittosporum viridiflorum Species Pittosporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16120 Swertia decora Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26942 Vicoa vestita n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO8298 Sphaeria biglobosa n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO5824 Hygrophila polysperma Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1988 Conocliniopsis prasiifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29072 Tritomaria quinquedentata Species Scapaniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15691 Senecio coahuilensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1428 Linzia glabra Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22541 Channa argus Species Channidae 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
NPT886 Cell Line NIH3T3 Mus musculus GI50 = 8.0 ug.mL-1 PMID[463471]
NPT31 Individual Protein Cyclooxygenase-2 Homo sapiens Inhibition < 30.0 % PMID[463472]
NPT886 Cell Line NIH3T3 Mus musculus GI50 = 54700.0 nM PMID[463473]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 = 32800.0 nM PMID[463473]
NPT1773 Cell Line ME-180 Homo sapiens GI50 = 18200.0 nM PMID[463473]
NPT90 Cell Line DU-145 Homo sapiens GI50 = 25800.0 nM PMID[463473]
NPT83 Cell Line MCF7 Homo sapiens GI50 = 30000.0 nM PMID[463473]
NPT387 Cell Line M14 Homo sapiens GI50 = 15100.0 nM PMID[463473]
NPT139 Cell Line HT-29 Homo sapiens GI50 = 28900.0 nM PMID[463473]
NPT306 Cell Line PC-3 Homo sapiens GI50 = 28500.0 nM PMID[463473]
NPT111 Cell Line K562 Homo sapiens GI50 = 40500.0 nM PMID[463473]
NPT32 Organism Mus musculus Mus musculus ED50 = 155.0 mg.kg-1 PMID[463471]
NPT32 Organism Mus musculus Mus musculus ED50 = 155.0 mg.kg-1 PMID[463473]

☑ 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 NPC179169 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 NPC181255
1.0 High Similarity NPC35519
1.0 High Similarity NPC306195
1.0 High Similarity NPC157781
0.9792 High Similarity NPC26906
0.9792 High Similarity NPC214584
0.92 High Similarity NPC71506
0.92 High Similarity NPC177112
0.88 High Similarity NPC329773
0.8421 Intermediate Similarity NPC79576
0.8421 Intermediate Similarity NPC194208
0.8421 Intermediate Similarity NPC282694
0.84 Intermediate Similarity NPC100445
0.8276 Intermediate Similarity NPC174956
0.8246 Intermediate Similarity NPC135648
0.8246 Intermediate Similarity NPC66020
0.8182 Intermediate Similarity NPC179024
0.8113 Intermediate Similarity NPC294358
0.8113 Intermediate Similarity NPC40417
0.8103 Intermediate Similarity NPC207007
0.8103 Intermediate Similarity NPC321867
0.8103 Intermediate Similarity NPC68679
0.8036 Intermediate Similarity NPC278550
0.8 Intermediate Similarity NPC471200
0.7931 Intermediate Similarity NPC240506
0.7917 Intermediate Similarity NPC188596
0.7869 Intermediate Similarity NPC279434
0.7857 Intermediate Similarity NPC39068
0.7857 Intermediate Similarity NPC274396
0.7857 Intermediate Similarity NPC141699
0.7778 Intermediate Similarity NPC68014
0.7759 Intermediate Similarity NPC5698
0.7759 Intermediate Similarity NPC469321
0.7719 Intermediate Similarity NPC165808
0.7679 Intermediate Similarity NPC130209
0.7679 Intermediate Similarity NPC218525
0.7679 Intermediate Similarity NPC148216
0.7679 Intermediate Similarity NPC232247
0.7679 Intermediate Similarity NPC148163
0.7679 Intermediate Similarity NPC251666
0.7667 Intermediate Similarity NPC81615
0.7647 Intermediate Similarity NPC210560
0.7647 Intermediate Similarity NPC165651
0.7647 Intermediate Similarity NPC24824
0.7636 Intermediate Similarity NPC192962
0.7627 Intermediate Similarity NPC252809
0.7627 Intermediate Similarity NPC323153
0.76 Intermediate Similarity NPC15162
0.7593 Intermediate Similarity NPC244038
0.7581 Intermediate Similarity NPC267027
0.7581 Intermediate Similarity NPC202017
0.7581 Intermediate Similarity NPC326310
0.7544 Intermediate Similarity NPC264779
0.7541 Intermediate Similarity NPC290367
0.75 Intermediate Similarity NPC475251
0.75 Intermediate Similarity NPC63111
0.75 Intermediate Similarity NPC210346
0.746 Intermediate Similarity NPC114651
0.7458 Intermediate Similarity NPC475931
0.7385 Intermediate Similarity NPC475728
0.7377 Intermediate Similarity NPC474480
0.7344 Intermediate Similarity NPC208999
0.7344 Intermediate Similarity NPC96484
0.7344 Intermediate Similarity NPC94192
0.7308 Intermediate Similarity NPC87439
0.7302 Intermediate Similarity NPC222366
0.7302 Intermediate Similarity NPC286669
0.7302 Intermediate Similarity NPC476039
0.7292 Intermediate Similarity NPC297643
0.7292 Intermediate Similarity NPC229262
0.7292 Intermediate Similarity NPC139717
0.7288 Intermediate Similarity NPC189290
0.7288 Intermediate Similarity NPC474769
0.7288 Intermediate Similarity NPC155025
0.7273 Intermediate Similarity NPC23954
0.7273 Intermediate Similarity NPC164022
0.7273 Intermediate Similarity NPC242992
0.7258 Intermediate Similarity NPC107540
0.7258 Intermediate Similarity NPC300593
0.7258 Intermediate Similarity NPC225415
0.7258 Intermediate Similarity NPC96793
0.7258 Intermediate Similarity NPC323424
0.7241 Intermediate Similarity NPC48891
0.7231 Intermediate Similarity NPC471560
0.7231 Intermediate Similarity NPC473893
0.7231 Intermediate Similarity NPC474248
0.7231 Intermediate Similarity NPC476431
0.7213 Intermediate Similarity NPC225342
0.7213 Intermediate Similarity NPC469728
0.7213 Intermediate Similarity NPC274704
0.7188 Intermediate Similarity NPC82337
0.7188 Intermediate Similarity NPC171225
0.7188 Intermediate Similarity NPC197805
0.7167 Intermediate Similarity NPC122239
0.7164 Intermediate Similarity NPC265485
0.7164 Intermediate Similarity NPC220939
0.7143 Intermediate Similarity NPC163678
0.7143 Intermediate Similarity NPC205618
0.7143 Intermediate Similarity NPC469326
0.7143 Intermediate Similarity NPC261782
0.7121 Intermediate Similarity NPC92801
0.7121 Intermediate Similarity NPC34834
0.7115 Intermediate Similarity NPC202189
0.7115 Intermediate Similarity NPC248411
0.7097 Intermediate Similarity NPC279200
0.7097 Intermediate Similarity NPC474155
0.7097 Intermediate Similarity NPC473759
0.7097 Intermediate Similarity NPC473508
0.7091 Intermediate Similarity NPC131623
0.7083 Intermediate Similarity NPC76145
0.7083 Intermediate Similarity NPC34764
0.7083 Intermediate Similarity NPC190810
0.7077 Intermediate Similarity NPC216460
0.7069 Intermediate Similarity NPC223604
0.7069 Intermediate Similarity NPC67508
0.7069 Intermediate Similarity NPC84824
0.7069 Intermediate Similarity NPC281590
0.7069 Intermediate Similarity NPC227135
0.7059 Intermediate Similarity NPC209279
0.7059 Intermediate Similarity NPC194586
0.7059 Intermediate Similarity NPC68889
0.7059 Intermediate Similarity NPC180871
0.7059 Intermediate Similarity NPC177470
0.7059 Intermediate Similarity NPC108494
0.7059 Intermediate Similarity NPC88079
0.7059 Intermediate Similarity NPC67761
0.7059 Intermediate Similarity NPC51758
0.7049 Intermediate Similarity NPC99487
0.7049 Intermediate Similarity NPC176621
0.7031 Intermediate Similarity NPC250977
0.7031 Intermediate Similarity NPC197089
0.7018 Intermediate Similarity NPC268564
0.7015 Intermediate Similarity NPC167706
0.7 Intermediate Similarity NPC475830
0.7 Intermediate Similarity NPC10017
0.7 Intermediate Similarity NPC181872
0.6984 Remote Similarity NPC234767
0.6984 Remote Similarity NPC309300
0.6981 Remote Similarity NPC296337
0.697 Remote Similarity NPC469914
0.6935 Remote Similarity NPC41160
0.6923 Remote Similarity NPC472255
0.6923 Remote Similarity NPC136813
0.6923 Remote Similarity NPC269862
0.6923 Remote Similarity NPC472253
0.6912 Remote Similarity NPC130665
0.6912 Remote Similarity NPC474140
0.6912 Remote Similarity NPC471799
0.6912 Remote Similarity NPC182717
0.6909 Remote Similarity NPC62755
0.6897 Remote Similarity NPC168518
0.6897 Remote Similarity NPC105780
0.6875 Remote Similarity NPC64123
0.6875 Remote Similarity NPC238352
0.6875 Remote Similarity NPC477009
0.6875 Remote Similarity NPC19569
0.6875 Remote Similarity NPC308844
0.6875 Remote Similarity NPC61503
0.6866 Remote Similarity NPC145498
0.6863 Remote Similarity NPC144023
0.6857 Remote Similarity NPC151622
0.6857 Remote Similarity NPC186554
0.6857 Remote Similarity NPC76966
0.6857 Remote Similarity NPC472305
0.6857 Remote Similarity NPC265588
0.6857 Remote Similarity NPC7629
0.6833 Remote Similarity NPC52012
0.6825 Remote Similarity NPC211291
0.6825 Remote Similarity NPC133368
0.6818 Remote Similarity NPC224532
0.6818 Remote Similarity NPC160209
0.6818 Remote Similarity NPC32055
0.6812 Remote Similarity NPC201048
0.6812 Remote Similarity NPC471797
0.6812 Remote Similarity NPC476366
0.6812 Remote Similarity NPC100334
0.6786 Remote Similarity NPC182102
0.6786 Remote Similarity NPC26960
0.678 Remote Similarity NPC298299
0.6769 Remote Similarity NPC272125
0.6769 Remote Similarity NPC311736
0.6769 Remote Similarity NPC149680
0.6765 Remote Similarity NPC242001
0.6765 Remote Similarity NPC110799
0.6765 Remote Similarity NPC160817
0.6761 Remote Similarity NPC318495
0.6761 Remote Similarity NPC477426
0.6761 Remote Similarity NPC325946
0.6761 Remote Similarity NPC40049
0.6761 Remote Similarity NPC474826
0.6761 Remote Similarity NPC257666
0.6761 Remote Similarity NPC477425
0.6761 Remote Similarity NPC198968
0.6761 Remote Similarity NPC155986
0.6761 Remote Similarity NPC266193
0.6761 Remote Similarity NPC34110
0.6761 Remote Similarity NPC477427
0.6727 Remote Similarity NPC91962
0.6724 Remote Similarity NPC165755
0.6721 Remote Similarity NPC226848

  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 NPC179169 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
0.8103 Intermediate Similarity NPD368 Approved
0.7679 Intermediate Similarity NPD342 Phase 1
0.7273 Intermediate Similarity NPD4243 Approved
0.7083 Intermediate Similarity NPD319 Phase 1
0.7059 Intermediate Similarity NPD4784 Approved
0.7059 Intermediate Similarity NPD4785 Approved
0.7031 Intermediate Similarity NPD7331 Phase 2
0.6957 Remote Similarity NPD5275 Approved
0.6957 Remote Similarity NPD4190 Phase 3
0.6716 Remote Similarity NPD6923 Approved
0.6716 Remote Similarity NPD6922 Approved
0.6714 Remote Similarity NPD7339 Approved
0.6714 Remote Similarity NPD6942 Approved
0.662 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6618 Remote Similarity NPD7143 Approved
0.6618 Remote Similarity NPD7144 Approved
0.6615 Remote Similarity NPD7341 Phase 2
0.6575 Remote Similarity NPD4195 Approved
0.6571 Remote Similarity NPD6924 Approved
0.6571 Remote Similarity NPD6926 Approved
0.6522 Remote Similarity NPD7152 Approved
0.6522 Remote Similarity NPD7150 Approved
0.6522 Remote Similarity NPD7151 Approved
0.6479 Remote Similarity NPD8264 Approved
0.6393 Remote Similarity NPD4219 Approved
0.6389 Remote Similarity NPD6933 Approved
0.6364 Remote Similarity NPD388 Approved
0.6364 Remote Similarity NPD386 Approved
0.6351 Remote Similarity NPD7645 Phase 2
0.6316 Remote Similarity NPD4223 Phase 3
0.6316 Remote Similarity NPD4221 Approved
0.6301 Remote Similarity NPD6932 Approved
0.6267 Remote Similarity NPD7525 Registered
0.6232 Remote Similarity NPD791 Approved
0.6232 Remote Similarity NPD15 Approved
0.6216 Remote Similarity NPD7322 Clinical (unspecified phase)
0.619 Remote Similarity NPD287 Approved
0.6154 Remote Similarity NPD4197 Approved
0.6133 Remote Similarity NPD6683 Phase 2
0.6111 Remote Similarity NPD1799 Clinical (unspecified phase)
0.6104 Remote Similarity NPD3667 Approved
0.6081 Remote Similarity NPD6925 Approved
0.6081 Remote Similarity NPD5776 Phase 2
0.6076 Remote Similarity NPD5329 Approved
0.6053 Remote Similarity NPD6931 Approved
0.6053 Remote Similarity NPD6930 Phase 2
0.6053 Remote Similarity NPD7509 Discontinued
0.6053 Remote Similarity NPD7514 Phase 3
0.6053 Remote Similarity NPD7332 Phase 2
0.6053 Remote Similarity NPD4695 Discontinued
0.6 Remote Similarity NPD7145 Approved
0.6 Remote Similarity NPD1082 Approved
0.6 Remote Similarity NPD4519 Discontinued
0.6 Remote Similarity NPD4138 Approved
0.6 Remote Similarity NPD1145 Discontinued
0.6 Remote Similarity NPD4694 Approved
0.6 Remote Similarity NPD5205 Approved
0.6 Remote Similarity NPD4688 Approved
0.6 Remote Similarity NPD5280 Approved
0.6 Remote Similarity NPD4693 Phase 3
0.6 Remote Similarity NPD4690 Approved
0.6 Remote Similarity NPD4623 Approved
0.6 Remote Similarity NPD4689 Approved
0.6 Remote Similarity NPD5690 Phase 2
0.5974 Remote Similarity NPD6898 Phase 1
0.5965 Remote Similarity NPD384 Approved
0.5965 Remote Similarity NPD385 Approved
0.5949 Remote Similarity NPD3133 Approved
0.5949 Remote Similarity NPD4786 Approved
0.5949 Remote Similarity NPD3666 Approved
0.5949 Remote Similarity NPD3665 Phase 1
0.5946 Remote Similarity NPD1346 Approved
0.5926 Remote Similarity NPD4751 Clinical (unspecified phase)
0.5921 Remote Similarity NPD6929 Approved
0.5909 Remote Similarity NPD4194 Approved
0.5909 Remote Similarity NPD4191 Approved
0.5909 Remote Similarity NPD4193 Approved
0.5909 Remote Similarity NPD4192 Approved
0.5882 Remote Similarity NPD2685 Clinical (unspecified phase)
0.5857 Remote Similarity NPD3621 Clinical (unspecified phase)
0.5854 Remote Similarity NPD4722 Approved
0.5854 Remote Similarity NPD4723 Approved
0.5844 Remote Similarity NPD4748 Discontinued
0.5823 Remote Similarity NPD6695 Phase 3
0.5821 Remote Similarity NPD2664 Clinical (unspecified phase)
0.5802 Remote Similarity NPD3574 Clinical (unspecified phase)
0.5802 Remote Similarity NPD3618 Phase 1
0.5789 Remote Similarity NPD4265 Approved
0.5789 Remote Similarity NPD3617 Approved
0.5783 Remote Similarity NPD4753 Phase 2
0.5775 Remote Similarity NPD4137 Phase 3
0.5769 Remote Similarity NPD6902 Approved
0.5769 Remote Similarity NPD4139 Approved
0.5769 Remote Similarity NPD4692 Approved
0.5763 Remote Similarity NPD8262 Approved
0.5753 Remote Similarity NPD4732 Discontinued
0.575 Remote Similarity NPD7338 Clinical (unspecified phase)
0.5714 Remote Similarity NPD367 Approved
0.5694 Remote Similarity NPD4691 Approved
0.5694 Remote Similarity NPD4747 Approved
0.5679 Remote Similarity NPD1696 Phase 3
0.5679 Remote Similarity NPD6893 Approved
0.5672 Remote Similarity NPD834 Approved
0.5672 Remote Similarity NPD835 Approved
0.5663 Remote Similarity NPD4518 Approved
0.5647 Remote Similarity NPD5281 Approved
0.5647 Remote Similarity NPD5284 Approved
0.5645 Remote Similarity NPD3172 Approved
0.5641 Remote Similarity NPD4822 Approved
0.5641 Remote Similarity NPD4820 Approved
0.5641 Remote Similarity NPD4821 Approved
0.5641 Remote Similarity NPD4819 Approved
0.561 Remote Similarity NPD5279 Phase 3

  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