NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	196.15
Volume:	213.939
LogP:	3.245
LogD:	3.143
LogS:	-3.433
# Rotatable Bonds:	2
TPSA:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.603
Synthetic Accessibility Score:	4.086
Fsp3:	0.917
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.589
MDCK Permeability:	2.662108454387635e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.022

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.418
Plasma Protein Binding (PPB):	84.66986846923828%
Volume Distribution (VD):	1.24
Pgp-substrate:	23.682477951049805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.497
CYP1A2-substrate:	0.187
CYP2C19-inhibitor:	0.182
CYP2C19-substrate:	0.876
CYP2C9-inhibitor:	0.234
CYP2C9-substrate:	0.678
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.399
CYP3A4-inhibitor:	0.152
CYP3A4-substrate:	0.234

ADMET: Excretion

Clearance (CL):	4.093
Half-life (T1/2):	0.399

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.096
Drug-inuced Liver Injury (DILI):	0.449
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.016
Maximum Recommended Daily Dose:	0.106
Skin Sensitization:	0.918
Carcinogencity:	0.1
Eye Corrosion:	0.989
Eye Irritation:	0.987
Respiratory Toxicity:	0.173

Download Data

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

Natural Product: NPC230070

Natural Product ID:	NPC230070
*Common Name:**	[(1R,3R,4R)-4,7,7-Trimethyl-3-Bicyclo[2.2.1]Heptanyl] Acetate
IUPAC Name:	[(1R,3R,4R)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] acetate
Synonyms:
Standard InCHIKey:	KGEKLUUHTZCSIP-FOGDFJRCSA-N
Standard InCHI:	InChI=1S/C12H20O2/c1-8(13)14-10-7-9-5-6-12(10,4)11(9,2)3/h9-10H,5-7H2,1-4H3/t9-,10-,12+/m1/s1
SMILES:	CC(=O)O[C@@H]1C[C@@H]2C([C@@]1(C)CC2)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3183823
PubChem CID:	637531
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0001564] Bicyclic 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
NPO163	Daucus carota	Species	Apiaceae	Eukaryota		n.a.	n.a.	DOI[10.1016/0045-6535(91)90110-Y]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodchem.2009.03.042]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2004.07.004]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2005.08.001]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	retail stores, supermarkets and market stalls in Forssa and in the Helsinki area	2003–2005	DOI[10.1016/j.jfca.2006.05.007]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	DOI[10.1021/np100392m]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.3136/fstr.15.499]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.5897/AJB10.140]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.5897/AJB2010.000-3252]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.5897/JMPR.9000078]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	1996-Sep	PMID[10352947]
NPO17755	Inula helenium	Species	Asteraceae	Eukaryota	n.a.	root	n.a.	PMID[10364842]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	flower	n.a.	PMID[12130858]
NPO17755	Inula helenium	Species	Asteraceae	Eukaryota	n.a.	root	n.a.	PMID[12392098]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15877880]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	Northeastern Regional Plant Introduction Station at Geneva	1966, 1967, and 1968 crop seasons	PMID[18460139]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[20879743]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800857]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[21800857]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	exocarp	n.a.	PMID[21800857]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21807513]
NPO17755	Inula helenium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23738470]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	n.a.	root	n.a.	PMID[23738470]
NPO18068	Curcuma phaeocaulis	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[23755850]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	Tongxiang, China	n.a.	PMID[24621197]
NPO17755	Inula helenium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24996657]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[25275213]
NPO17755	Inula helenium	Species	Asteraceae	Eukaryota	n.a.	root	n.a.	PMID[25767328]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26099993]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	PMID[28156114]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	PMID[28248102]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2831703]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29400471]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[30726671]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6821187]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9868158]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Tissue Culture	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Roots	n.a.		Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17755	Inula helenium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17755	Inula helenium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17755	Inula helenium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18068	Curcuma phaeocaulis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18068	Curcuma phaeocaulis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17755	Inula helenium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO163	Daucus carota	Species	Apiaceae	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

Activity Type	# Activity
Potency	3

Activity Type	# Activity
Individual Protein	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	54482.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	21875.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	10870.7	nM	PubChem BioAssay data set

☑ 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 NPC230070 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	450
0.1-0.2	7401
0.2-0.3	17345
0.3-0.4	7989
0.4-0.5	7263
0.5-0.6	2058
0.6-0.7	166
0.7-0.8	12
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC87828
1.0	High Similarity	NPC9880
0.9821	High Similarity	NPC66145
0.9649	High Similarity	NPC83088
0.8462	Intermediate Similarity	NPC168596
0.8462	Intermediate Similarity	NPC94632
0.8197	Intermediate Similarity	NPC84218
0.7966	Intermediate Similarity	NPC89069
0.7966	Intermediate Similarity	NPC166894
0.7966	Intermediate Similarity	NPC283655
0.7966	Intermediate Similarity	NPC277917
0.7966	Intermediate Similarity	NPC178223
0.7895	Intermediate Similarity	NPC274261
0.7895	Intermediate Similarity	NPC291724
0.7705	Intermediate Similarity	NPC150713
0.7705	Intermediate Similarity	NPC29976
0.7324	Intermediate Similarity	NPC474524
0.7324	Intermediate Similarity	NPC475517
0.7246	Intermediate Similarity	NPC22301
0.7164	Intermediate Similarity	NPC157518
0.7162	Intermediate Similarity	NPC471045
0.7143	Intermediate Similarity	NPC29342
0.7143	Intermediate Similarity	NPC2572
0.7143	Intermediate Similarity	NPC69953
0.7123	Intermediate Similarity	NPC472472
0.7083	Intermediate Similarity	NPC272359
0.7077	Intermediate Similarity	NPC204173
0.7067	Intermediate Similarity	NPC476176
0.7027	Intermediate Similarity	NPC171658
0.6986	Remote Similarity	NPC478105
0.6986	Remote Similarity	NPC186851
0.6974	Remote Similarity	NPC474714
0.6944	Remote Similarity	NPC248567
0.6875	Remote Similarity	NPC64862
0.6875	Remote Similarity	NPC131365
0.6842	Remote Similarity	NPC477287
0.68	Remote Similarity	NPC474404
0.68	Remote Similarity	NPC212453
0.68	Remote Similarity	NPC471151
0.679	Remote Similarity	NPC5943
0.6769	Remote Similarity	NPC240206
0.6757	Remote Similarity	NPC155441
0.6753	Remote Similarity	NPC80622
0.6753	Remote Similarity	NPC472470
0.6667	Remote Similarity	NPC190940
0.6667	Remote Similarity	NPC471046
0.6667	Remote Similarity	NPC58631
0.6667	Remote Similarity	NPC472471
0.6625	Remote Similarity	NPC291310
0.6623	Remote Similarity	NPC47808
0.6623	Remote Similarity	NPC305835
0.6623	Remote Similarity	NPC220379
0.6622	Remote Similarity	NPC477867
0.6622	Remote Similarity	NPC472945
0.6622	Remote Similarity	NPC472944
0.6618	Remote Similarity	NPC209686
0.6618	Remote Similarity	NPC236099
0.6618	Remote Similarity	NPC249078
0.6615	Remote Similarity	NPC291147
0.6582	Remote Similarity	NPC286719
0.6582	Remote Similarity	NPC13494
0.6582	Remote Similarity	NPC477286
0.6582	Remote Similarity	NPC477284
0.6579	Remote Similarity	NPC186109
0.6575	Remote Similarity	NPC470243
0.6567	Remote Similarity	NPC478126
0.6543	Remote Similarity	NPC266651
0.6538	Remote Similarity	NPC206735
0.6538	Remote Similarity	NPC261616
0.6538	Remote Similarity	NPC304194
0.6533	Remote Similarity	NPC212733
0.6528	Remote Similarity	NPC98711
0.6528	Remote Similarity	NPC475062
0.65	Remote Similarity	NPC111582
0.65	Remote Similarity	NPC477285
0.65	Remote Similarity	NPC472473
0.6486	Remote Similarity	NPC474755
0.6486	Remote Similarity	NPC14352
0.6486	Remote Similarity	NPC109510
0.6486	Remote Similarity	NPC234527
0.6479	Remote Similarity	NPC476928
0.6471	Remote Similarity	NPC185547
0.6471	Remote Similarity	NPC306750
0.6471	Remote Similarity	NPC95804
0.6462	Remote Similarity	NPC3025
0.6456	Remote Similarity	NPC73515
0.6452	Remote Similarity	NPC314084
0.6447	Remote Similarity	NPC4209
0.6429	Remote Similarity	NPC472234
0.6429	Remote Similarity	NPC165069
0.6429	Remote Similarity	NPC472233
0.6418	Remote Similarity	NPC475968
0.641	Remote Similarity	NPC80891
0.641	Remote Similarity	NPC201276
0.6406	Remote Similarity	NPC202146
0.6406	Remote Similarity	NPC32222
0.6406	Remote Similarity	NPC319589
0.64	Remote Similarity	NPC167702
0.64	Remote Similarity	NPC55508
0.64	Remote Similarity	NPC280026
0.64	Remote Similarity	NPC477508
0.6389	Remote Similarity	NPC474756
0.6389	Remote Similarity	NPC119838
0.6375	Remote Similarity	NPC61107
0.6375	Remote Similarity	NPC154043
0.6375	Remote Similarity	NPC60018
0.6375	Remote Similarity	NPC289486
0.6375	Remote Similarity	NPC202688
0.6364	Remote Similarity	NPC316546
0.6364	Remote Similarity	NPC207010
0.6364	Remote Similarity	NPC298168
0.6364	Remote Similarity	NPC143133
0.6364	Remote Similarity	NPC169389
0.6364	Remote Similarity	NPC317913
0.6351	Remote Similarity	NPC197701
0.6351	Remote Similarity	NPC469940
0.6338	Remote Similarity	NPC44122
0.6338	Remote Similarity	NPC84562
0.6329	Remote Similarity	NPC472853
0.6329	Remote Similarity	NPC66766
0.6329	Remote Similarity	NPC117137
0.6322	Remote Similarity	NPC39453
0.6316	Remote Similarity	NPC132064
0.6316	Remote Similarity	NPC131584
0.6316	Remote Similarity	NPC113639
0.6316	Remote Similarity	NPC139765
0.6316	Remote Similarity	NPC179922
0.6316	Remote Similarity	NPC313185
0.6308	Remote Similarity	NPC300189
0.6301	Remote Similarity	NPC477820
0.6301	Remote Similarity	NPC196197
0.6301	Remote Similarity	NPC5714
0.6296	Remote Similarity	NPC157328
0.6296	Remote Similarity	NPC5280
0.6296	Remote Similarity	NPC477667
0.6296	Remote Similarity	NPC259173
0.6296	Remote Similarity	NPC473742
0.6296	Remote Similarity	NPC139206
0.629	Remote Similarity	NPC305182
0.6286	Remote Similarity	NPC159654
0.6286	Remote Similarity	NPC118937
0.6286	Remote Similarity	NPC281540
0.6286	Remote Similarity	NPC167995
0.6282	Remote Similarity	NPC34046
0.6282	Remote Similarity	NPC324700
0.6282	Remote Similarity	NPC171426
0.6282	Remote Similarity	NPC224802
0.6282	Remote Similarity	NPC199965
0.6282	Remote Similarity	NPC80089
0.6282	Remote Similarity	NPC476732
0.6279	Remote Similarity	NPC474065
0.6279	Remote Similarity	NPC473066
0.6265	Remote Similarity	NPC103782
0.6265	Remote Similarity	NPC286153
0.6265	Remote Similarity	NPC155531
0.6265	Remote Similarity	NPC114378
0.6265	Remote Similarity	NPC477283
0.6265	Remote Similarity	NPC215968
0.6265	Remote Similarity	NPC477668
0.625	Remote Similarity	NPC63190
0.6234	Remote Similarity	NPC92489
0.6234	Remote Similarity	NPC470145
0.622	Remote Similarity	NPC239362
0.622	Remote Similarity	NPC475509
0.622	Remote Similarity	NPC471044
0.622	Remote Similarity	NPC473336
0.622	Remote Similarity	NPC319909
0.6216	Remote Similarity	NPC477929
0.6216	Remote Similarity	NPC251201
0.6216	Remote Similarity	NPC63588
0.6216	Remote Similarity	NPC282454
0.6216	Remote Similarity	NPC232925
0.6207	Remote Similarity	NPC182740
0.6207	Remote Similarity	NPC122083
0.6207	Remote Similarity	NPC472231
0.6207	Remote Similarity	NPC472232
0.6207	Remote Similarity	NPC35164
0.6207	Remote Similarity	NPC211845
0.6207	Remote Similarity	NPC256104
0.6203	Remote Similarity	NPC44083
0.6203	Remote Similarity	NPC474754
0.6203	Remote Similarity	NPC320144
0.6203	Remote Similarity	NPC153987
0.6197	Remote Similarity	NPC474768
0.6184	Remote Similarity	NPC71152
0.6184	Remote Similarity	NPC215030
0.6184	Remote Similarity	NPC475458
0.6184	Remote Similarity	NPC74639
0.6173	Remote Similarity	NPC164289
0.6173	Remote Similarity	NPC296734
0.6173	Remote Similarity	NPC477936
0.6173	Remote Similarity	NPC100366
0.6173	Remote Similarity	NPC24556
0.6173	Remote Similarity	NPC477935
0.6173	Remote Similarity	NPC311642
0.6173	Remote Similarity	NPC148740
0.6173	Remote Similarity	NPC470611
0.6173	Remote Similarity	NPC472504
0.6173	Remote Similarity	NPC102156
0.6173	Remote Similarity	NPC212340

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 NPC230070 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	670
0.1-0.2	5012
0.2-0.3	2506
0.3-0.4	529
0.4-0.5	335
0.5-0.6	89
0.6-0.7	9
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7042	Intermediate Similarity	NPD5777	Approved
0.6757	Remote Similarity	NPD3702	Approved
0.6719	Remote Similarity	NPD586	Phase 1
0.6667	Remote Similarity	NPD3198	Approved
0.6447	Remote Similarity	NPD6117	Approved
0.64	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD229	Approved
0.6364	Remote Similarity	NPD6116	Phase 1
0.6282	Remote Similarity	NPD6114	Approved
0.6282	Remote Similarity	NPD6697	Approved
0.6282	Remote Similarity	NPD6115	Approved
0.6282	Remote Similarity	NPD6118	Approved
0.6125	Remote Similarity	NPD6928	Phase 2
0.6118	Remote Similarity	NPD6903	Approved
0.6081	Remote Similarity	NPD3698	Phase 2
0.6066	Remote Similarity	NPD385	Approved
0.6066	Remote Similarity	NPD344	Approved
0.6066	Remote Similarity	NPD384	Approved
0.6066	Remote Similarity	NPD343	Approved
0.6066	Remote Similarity	NPD345	Approved
0.6	Remote Similarity	NPD4245	Approved
0.6	Remote Similarity	NPD4244	Approved
0.6	Remote Similarity	NPD4787	Phase 1
0.5972	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.5972	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5921	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.5921	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.589	Remote Similarity	NPD4224	Phase 2
0.5882	Remote Similarity	NPD6684	Approved
0.5882	Remote Similarity	NPD5330	Approved
0.5882	Remote Similarity	NPD7146	Approved
0.5882	Remote Similarity	NPD7334	Approved
0.5882	Remote Similarity	NPD7521	Approved
0.5882	Remote Similarity	NPD6409	Approved
0.5875	Remote Similarity	NPD4238	Approved
0.5875	Remote Similarity	NPD4802	Phase 2
0.5867	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.5867	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.5867	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD6051	Approved
0.5765	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5765	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5747	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5745	Remote Similarity	NPD1700	Approved
0.573	Remote Similarity	NPD8035	Phase 2
0.573	Remote Similarity	NPD8034	Phase 2
0.5714	Remote Similarity	NPD6081	Approved
0.5714	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5696	Remote Similarity	NPD3703	Phase 2
0.5672	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD387	Clinical (unspecified phase)
0.5604	Remote Similarity	NPD6001	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