Structure

Physi-Chem Properties

Molecular Weight:  220.18
Volume:  248.481
LogP:  4.821
LogD:  4.262
LogS:  -5.237
# Rotatable Bonds:  0
TPSA:  12.53
# H-Bond Aceptor:  1
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.445
Synthetic Accessibility Score:  4.59
Fsp3:  0.867
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:  -4.649
MDCK Permeability:  2.1190320694586262e-05
Pgp-inhibitor:  0.005
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.131
30% Bioavailability (F30%):  0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.113
Plasma Protein Binding (PPB):  80.97466278076172%
Volume Distribution (VD):  1.023
Pgp-substrate:  22.76235580444336%

ADMET: Metabolism

CYP1A2-inhibitor:  0.175
CYP1A2-substrate:  0.491
CYP2C19-inhibitor:  0.135
CYP2C19-substrate:  0.924
CYP2C9-inhibitor:  0.243
CYP2C9-substrate:  0.242
CYP2D6-inhibitor:  0.02
CYP2D6-substrate:  0.698
CYP3A4-inhibitor:  0.155
CYP3A4-substrate:  0.381

ADMET: Excretion

Clearance (CL):  11.004
Half-life (T1/2):  0.095

ADMET: Toxicity

hERG Blockers:  0.05
Human Hepatotoxicity (H-HT):  0.235
Drug-inuced Liver Injury (DILI):  0.335
AMES Toxicity:  0.011
Rat Oral Acute Toxicity:  0.15
Maximum Recommended Daily Dose:  0.673
Skin Sensitization:  0.52
Carcinogencity:  0.315
Eye Corrosion:  0.595
Eye Irritation:  0.644
Respiratory Toxicity:  0.873

Download Data

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

  Natural Product: NPC65786

Natural Product ID:  NPC65786
Common Name*:   NVEQFIOZRFFVFW-BHPKHCPMSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  NVEQFIOZRFFVFW-BHPKHCPMSA-N
Standard InCHI:  InChI=1S/C15H24O/c1-10-5-6-13-15(4,16-13)8-7-12-11(10)9-14(12,2)3/h11-13H,1,5-9H2,2-4H3/t11-,12-,13-,15+/m1/s1
SMILES:  C=C1CC[C@@H]2[C@](C)(CC[C@@H]3[C@@H]1CC3(C)C)O2
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL479134
PubChem CID:   9991037
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]
NPO6363 Conyza filaginoides Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[11374974]
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]
NPO2804 Calophyllum inophyllum Species Calophyllaceae Eukaryota n.a. n.a. n.a. PMID[15678383]
NPO2804 Calophyllum inophyllum Species Calophyllaceae Eukaryota n.a. n.a. n.a. PMID[16045947]
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]
NPO8764 Laurencia decumbens Species Rhodomelaceae Eukaryota n.a. n.a. n.a. PMID[17711344]
NPO13916 Nephthea erecta Species Nephtheidae Eukaryota n.a. formosan soft coral n.a. PMID[17845002]
NPO13975 Calanthe arisanensis Species Orchidaceae Eukaryota n.a. n.a. n.a. PMID[18640035]
NPO8653 Leuconostoc mesenteroides Species Leuconostocaceae Bacteria n.a. n.a. n.a. PMID[19025748]
NPO13975 Calanthe arisanensis Species Orchidaceae Eukaryota n.a. n.a. n.a. PMID[19193043]
NPO24671 Lycopodium japonicum Species Lycopodiaceae Eukaryota n.a. n.a. n.a. PMID[19245240]
NPO5018 Nervilia fordii Species Orchidaceae Eukaryota whole plant n.a. n.a. PMID[19422205]
NPO2804 Calophyllum inophyllum Species Calophyllaceae Eukaryota n.a. stem n.a. PMID[20188156]
NPO3123 Anthemis cretica Species Asteraceae Eukaryota n.a. aerial part n.a. PMID[22351977]
NPO22864 Purpureocillium lilacinum Species Ophiocordycipitaceae Eukaryota n.a. n.a. n.a. PMID[23876004]
NPO13916 Nephthea erecta Species Nephtheidae Eukaryota n.a. Formosan soft coral n.a. PMID[24370010]
NPO11979 Bugula neritina Species Bugulidae Eukaryota n.a. South China Sea n.a. PMID[25932671]
NPO2804 Calophyllum inophyllum Species Calophyllaceae Eukaryota n.a. Malaysian n.a. PMID[7506311]
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]
NPO13916 Nephthea erecta Species Nephtheidae Eukaryota n.a. n.a. n.a. PMID[9722490]
NPO16120 Swertia decora Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO12854 Iris potaninii Species Iridaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24671 Lycopodium japonicum Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2804 Calophyllum inophyllum Species Calophyllaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
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]
NPO28741 Afrocarpus gracilior Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24671 Lycopodium japonicum Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15904 Chrysosplenium oppositifolium Species Saxifragaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9964 Aglaia lawii Species Meliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3123 Anthemis cretica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12854 Iris potaninii Species Iridaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2804 Calophyllum inophyllum Species Calophyllaceae 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]
NPO10969 Epimedium sagittatum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24671 Lycopodium japonicum Species Lycopodiaceae 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]
NPO9425 Punctelia microsticta Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5018 Nervilia fordii Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27420 Venidium hirsutum n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO12854 Iris potaninii Species Iridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19826 Helicoverpa armigera Species 0ctuidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4962 Lophozia ventricosa Species Scapaniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13296 Pinus sitchensis Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11866 Colubrina greggii Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16223 Serratula xeranthemoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16713 Choisya arizonica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11702 Plexaurella grisea Species Plexauridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17447 Agathosma betulina Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7664 Pseudocedrela kotschyi Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6766 Antiphiona pinnatisecta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8782 Arnica sachalinensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16313 Ochrocarpos odoratus Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16634 Sinularia manaarensis Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3742 Betula maximowicziana Species Betulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28741 Afrocarpus gracilior Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2768 Berchemia floribunda Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13916 Nephthea erecta Species Nephtheidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1649 Marsypianthes chamaedrys Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO752 Oligonychus bessardi Species Tetranychidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2804 Calophyllum inophyllum Species Calophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9567 Enicosanthum cupulare Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13992 Bonnemaisonia hamifera Species Bonnemaisoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11979 Bugula neritina Species Bugulidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15904 Chrysosplenium oppositifolium Species Saxifragaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12087 Amaioua guianensis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10977 Guatteria leiophylla Species Annonaceae 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]
NPO24671 Lycopodium japonicum Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12099 Lepia marginata n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO15341 Mucuna sloanei Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22394 Hyacinthoides hispanica Species Hyacinthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13773 Eriogonum nudum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12725 Streptomyces avellaneus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO21773 Rothmannia urcelliformis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16120 Swertia decora Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11091 Baccharis eggersii 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]
NPO13897 Lamium maculatum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10969 Epimedium sagittatum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27425 Pseudotaxus chienii Species Taxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5824 Hygrophila polysperma Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8653 Leuconostoc mesenteroides Species Leuconostocaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO8764 Laurencia decumbens Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17377 Pittosporum viridiflorum Species Pittosporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13410 Mcneillia graminifolia Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15691 Senecio coahuilensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6899 Hepialus hecta Species Hepialidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14625 Santolina rosmarinifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9136 Pseudocyclosorus subochthodes Species Thelypteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16878 Roldana barba-johannis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11095 Parmelia leucotyliza Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15194 Euphorbia balsamifera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16466 Baccharis santelicis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12312 Nepeta cadmea Species Lamiaceae Eukaryota 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]
NPO10648 Bazzania tridens Species Lepidoziaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13130 0tholaena peninsularis Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8201 Tium alpinum n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO2012 Turnera diffusa Species Passifloraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6363 Conyza filaginoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15238 Baccharis alaternoides 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]
NPO14383 Senecio pauciligulatus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16789 Erythrina sandwicensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2495 Agave xylonacantha Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15579 Mycale laxissima Species Mycalidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22541 Channa argus Species Channidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10991 Maackia tashiroi Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3123 Anthemis cretica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9964 Aglaia lawii Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11413 Incarvillea emodi Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15452 Senecio othonniformis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26103 Streptomyces bobili Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO14127 Veratrum eschscholtzii Species Melanthiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22864 Purpureocillium lilacinum Species Ophiocordycipitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1354 Myelochroa rhytidodes Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13975 Calanthe arisanensis Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20234 Stephania micrantha Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16553 Theonella cupola Species Theonellidae 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
NPT992 Organism Entamoeba histolytica Entamoeba histolytica IC50 = 71.3 ug.mL-1 PMID[489392]
NPT2645 Organism Giardia intestinalis Giardia intestinalis IC50 = 53.8 ug.mL-1 PMID[489392]

☑ 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 NPC65786 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 NPC27853
1.0 High Similarity NPC7491
1.0 High Similarity NPC13789
1.0 High Similarity NPC101285
0.8548 High Similarity NPC33583
0.8548 High Similarity NPC161612
0.85 High Similarity NPC50435
0.807 Intermediate Similarity NPC286752
0.791 Intermediate Similarity NPC329763
0.7797 Intermediate Similarity NPC210316
0.7778 Intermediate Similarity NPC287744
0.7778 Intermediate Similarity NPC140233
0.7681 Intermediate Similarity NPC474419
0.7627 Intermediate Similarity NPC223604
0.7586 Intermediate Similarity NPC165755
0.7246 Intermediate Similarity NPC40327
0.7077 Intermediate Similarity NPC474155
0.7077 Intermediate Similarity NPC473759
0.7049 Intermediate Similarity NPC300189
0.7015 Intermediate Similarity NPC469328
0.6974 Remote Similarity NPC145963
0.6923 Remote Similarity NPC253204
0.6901 Remote Similarity NPC92909
0.6901 Remote Similarity NPC107783
0.6818 Remote Similarity NPC283247
0.6806 Remote Similarity NPC167049
0.6806 Remote Similarity NPC469691
0.678 Remote Similarity NPC142103
0.6769 Remote Similarity NPC40206
0.6769 Remote Similarity NPC162109
0.6765 Remote Similarity NPC473929
0.6765 Remote Similarity NPC475897
0.6765 Remote Similarity NPC327815
0.6719 Remote Similarity NPC240206
0.6716 Remote Similarity NPC219940
0.6716 Remote Similarity NPC101128
0.6712 Remote Similarity NPC475771
0.6712 Remote Similarity NPC469669
0.6712 Remote Similarity NPC469678
0.6712 Remote Similarity NPC475861
0.6667 Remote Similarity NPC474477
0.6667 Remote Similarity NPC251335
0.6667 Remote Similarity NPC15152
0.6667 Remote Similarity NPC228574
0.6667 Remote Similarity NPC87439
0.6667 Remote Similarity NPC39068
0.6667 Remote Similarity NPC294304
0.6667 Remote Similarity NPC264779
0.6622 Remote Similarity NPC226242
0.6622 Remote Similarity NPC476607
0.6618 Remote Similarity NPC61503
0.6615 Remote Similarity NPC83838
0.6615 Remote Similarity NPC184049
0.6615 Remote Similarity NPC143810
0.6615 Remote Similarity NPC99480
0.6533 Remote Similarity NPC186109
0.6533 Remote Similarity NPC471454
0.6515 Remote Similarity NPC127824
0.6508 Remote Similarity NPC67508
0.6508 Remote Similarity NPC84824
0.6479 Remote Similarity NPC329656
0.6479 Remote Similarity NPC239373
0.6479 Remote Similarity NPC74722
0.6479 Remote Similarity NPC329989
0.6479 Remote Similarity NPC304690
0.6479 Remote Similarity NPC22301
0.6479 Remote Similarity NPC474248
0.6471 Remote Similarity NPC68656
0.6471 Remote Similarity NPC144650
0.6471 Remote Similarity NPC309300
0.6471 Remote Similarity NPC225415
0.6462 Remote Similarity NPC474769
0.6462 Remote Similarity NPC189290
0.6452 Remote Similarity NPC161473
0.6447 Remote Similarity NPC474005
0.6447 Remote Similarity NPC207186
0.6438 Remote Similarity NPC470237
0.6438 Remote Similarity NPC476709
0.6429 Remote Similarity NPC269077
0.6429 Remote Similarity NPC185874
0.6429 Remote Similarity NPC139207
0.6429 Remote Similarity NPC253303
0.6429 Remote Similarity NPC259299
0.6406 Remote Similarity NPC24443
0.64 Remote Similarity NPC472472
0.64 Remote Similarity NPC268111
0.6393 Remote Similarity NPC474331
0.6377 Remote Similarity NPC172613
0.6377 Remote Similarity NPC60837
0.6377 Remote Similarity NPC238352
0.6377 Remote Similarity NPC477009
0.6377 Remote Similarity NPC2728
0.6377 Remote Similarity NPC474768
0.6377 Remote Similarity NPC208198
0.6377 Remote Similarity NPC282619
0.6377 Remote Similarity NPC11555
0.6377 Remote Similarity NPC300442
0.6377 Remote Similarity NPC258595
0.6364 Remote Similarity NPC5698
0.6351 Remote Similarity NPC190859
0.6351 Remote Similarity NPC71152
0.6338 Remote Similarity NPC245795
0.6338 Remote Similarity NPC276616
0.6338 Remote Similarity NPC305698
0.6338 Remote Similarity NPC244790
0.6286 Remote Similarity NPC476406
0.6282 Remote Similarity NPC304795
0.6282 Remote Similarity NPC475946
0.6269 Remote Similarity NPC135648
0.6269 Remote Similarity NPC323153
0.6267 Remote Similarity NPC93213
0.6267 Remote Similarity NPC113639
0.625 Remote Similarity NPC477448
0.625 Remote Similarity NPC477449
0.625 Remote Similarity NPC9942
0.625 Remote Similarity NPC269841
0.6234 Remote Similarity NPC475980
0.6234 Remote Similarity NPC474056
0.6232 Remote Similarity NPC107540
0.6232 Remote Similarity NPC469723
0.6232 Remote Similarity NPC290367
0.6232 Remote Similarity NPC300593
0.6212 Remote Similarity NPC475830
0.6212 Remote Similarity NPC10017
0.6203 Remote Similarity NPC478262
0.6203 Remote Similarity NPC472471
0.6197 Remote Similarity NPC469868
0.6197 Remote Similarity NPC477791
0.6197 Remote Similarity NPC74885
0.6197 Remote Similarity NPC308522
0.6197 Remote Similarity NPC136813
0.6197 Remote Similarity NPC171225
0.6184 Remote Similarity NPC310643
0.6184 Remote Similarity NPC471726
0.6184 Remote Similarity NPC474527
0.6184 Remote Similarity NPC470766
0.6184 Remote Similarity NPC170148
0.6176 Remote Similarity NPC41160
0.6176 Remote Similarity NPC147524
0.6176 Remote Similarity NPC225342
0.6176 Remote Similarity NPC475251
0.6167 Remote Similarity NPC100445
0.6164 Remote Similarity NPC283316
0.6164 Remote Similarity NPC133873
0.6164 Remote Similarity NPC475310
0.6154 Remote Similarity NPC325869
0.6154 Remote Similarity NPC179024
0.6143 Remote Similarity NPC19569
0.6143 Remote Similarity NPC471200
0.6133 Remote Similarity NPC475517
0.6133 Remote Similarity NPC471525
0.6133 Remote Similarity NPC227814
0.6133 Remote Similarity NPC474524
0.6133 Remote Similarity NPC144995
0.6125 Remote Similarity NPC471159
0.6125 Remote Similarity NPC475936
0.6125 Remote Similarity NPC123880
0.6111 Remote Similarity NPC476945
0.6111 Remote Similarity NPC96484
0.6111 Remote Similarity NPC208999
0.6111 Remote Similarity NPC139785
0.6111 Remote Similarity NPC167527
0.6104 Remote Similarity NPC476703
0.6104 Remote Similarity NPC283619
0.6104 Remote Similarity NPC470750
0.6104 Remote Similarity NPC470751
0.6104 Remote Similarity NPC211279
0.6087 Remote Similarity NPC133368
0.6087 Remote Similarity NPC211291
0.6081 Remote Similarity NPC471662
0.6081 Remote Similarity NPC167706
0.6081 Remote Similarity NPC477084
0.6081 Remote Similarity NPC164022
0.6076 Remote Similarity NPC472470
0.6071 Remote Similarity NPC78551
0.6071 Remote Similarity NPC227632
0.6071 Remote Similarity NPC62086
0.6061 Remote Similarity NPC278550
0.6056 Remote Similarity NPC267027
0.6053 Remote Similarity NPC12696
0.6053 Remote Similarity NPC36479
0.6049 Remote Similarity NPC475842
0.6049 Remote Similarity NPC53867
0.6049 Remote Similarity NPC260852
0.6049 Remote Similarity NPC475622
0.6049 Remote Similarity NPC108045
0.6034 Remote Similarity NPC109813
0.6034 Remote Similarity NPC60556
0.6034 Remote Similarity NPC15162
0.6032 Remote Similarity NPC306195
0.6032 Remote Similarity NPC157781
0.6032 Remote Similarity NPC35519
0.6032 Remote Similarity NPC179169
0.6032 Remote Similarity NPC181255
0.6029 Remote Similarity NPC475412
0.6029 Remote Similarity NPC66020
0.6029 Remote Similarity NPC252809
0.6027 Remote Similarity NPC261398
0.6027 Remote Similarity NPC471560
0.6027 Remote Similarity NPC5714

  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 NPC65786 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
0.661 Remote Similarity NPD9410 Clinical (unspecified phase)
0.6515 Remote Similarity NPD1145 Discontinued
0.6143 Remote Similarity NPD2685 Clinical (unspecified phase)
0.5921 Remote Similarity NPD6924 Approved
0.5921 Remote Similarity NPD6926 Approved
0.5769 Remote Similarity NPD6933 Approved
0.5763 Remote Similarity NPD367 Approved
0.5714 Remote Similarity NPD368 Approved
0.5663 Remote Similarity NPD6695 Phase 3
0.5641 Remote Similarity NPD7339 Approved
0.5641 Remote Similarity NPD6942 Approved
0.56 Remote Similarity NPD6922 Approved
0.56 Remote Similarity NPD6923 Approved

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data