NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	158.07
Volume:	177.307
LogP:	2.356
LogD:	2.517
LogS:	-2.423
# Rotatable Bonds:	1
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.675
Synthetic Accessibility Score:	1.462
Fsp3:	0.091
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.319
MDCK Permeability:	2.1597999875666574e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.971
30% Bioavailability (F30%):	0.142

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.914
Plasma Protein Binding (PPB):	91.12635040283203%
Volume Distribution (VD):	1.526
Pgp-substrate:	9.759949684143066%

ADMET: Metabolism

CYP1A2-inhibitor:	0.97
CYP1A2-substrate:	0.595
CYP2C19-inhibitor:	0.594
CYP2C19-substrate:	0.187
CYP2C9-inhibitor:	0.066
CYP2C9-substrate:	0.169
CYP2D6-inhibitor:	0.162
CYP2D6-substrate:	0.896
CYP3A4-inhibitor:	0.032
CYP3A4-substrate:	0.278

ADMET: Excretion

Clearance (CL):	9.855
Half-life (T1/2):	0.805

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.021
Drug-inuced Liver Injury (DILI):	0.423
AMES Toxicity:	0.528
Rat Oral Acute Toxicity:	0.063
Maximum Recommended Daily Dose:	0.019
Skin Sensitization:	0.88
Carcinogencity:	0.757
Eye Corrosion:	0.044
Eye Irritation:	0.993
Respiratory Toxicity:	0.254

Download Data

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

Natural Product: NPC199567

Natural Product ID:	NPC199567
*Common Name:**	Naphthalen-1-Yl-Methanol
IUPAC Name:	naphthalen-1-ylmethanol
Synonyms:	Naphthalen-1-Yl-Methanol
Standard InCHIKey:	PBLNHHSDYFYZNC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H10O/c12-8-10-6-3-5-9-4-1-2-7-11(9)10/h1-7,12H,8H2
SMILES:	c1ccc2c(c1)cccc2CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1288
PubChem CID:	20908
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes

*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
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1172/JCI16309]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1371/journal.pone.0115359]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[10557354]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11034610]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11419736]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11530998]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1175644]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12391014]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12812989]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12840027]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12878451]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15084647]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1521032]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15230696]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15314235]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[16112079]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[16770722]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1687010]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17116739]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17190852]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17875433]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18311922]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18544912]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18799520]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[19425150]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[19961175]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20506249]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20601097]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	bile	n.a.	PMID[20708442]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	faeces	n.a.	PMID[20708442]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	urine	n.a.	PMID[20708442]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20876113]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[21798258]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[2268561]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[22711758]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23315938]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23717534]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23752203]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23810710]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23811455]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23868375]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23919613]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24101735]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24399466]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24494566]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24558969]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24816727]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25114169]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25181601]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25293588]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25644343]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[26236990]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[27471436]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[3179836]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[347637]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[4696527]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[5432584]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[6121420]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[6780563]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[8600370]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[8987136]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9192820]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9800648]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO20338	Mus musculus	Species	Muridae	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
Others	4

Activity Type	# Activity
Individual Protein	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1817	Individual Protein	Aryl sulfotransferase	Rattus norvegicus	Km	=	30000.0	nM	PMID[473062]
NPT1817	Individual Protein	Aryl sulfotransferase	Rattus norvegicus	Vmax	=	26.0	nM min-1	PMID[473062]
NPT1817	Individual Protein	Aryl sulfotransferase	Rattus norvegicus	Ratio	=	29.4	n.a.	PMID[473062]
NPT703	Individual Protein	UDP-glucuronosyltransferase 1-9	Homo sapiens	Activity	=	130.0	pm/min/mg	PMID[473063]

☑ 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 NPC199567 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	409
0.1-0.2	1882
0.2-0.3	5219
0.3-0.4	14009
0.4-0.5	11894
0.5-0.6	7490
0.6-0.7	1505
0.7-0.8	267
0.8-0.85	17
0.85-0.9	3
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9651	High Similarity	NPC128645
0.9048	High Similarity	NPC172984
0.8901	High Similarity	NPC21959
0.8588	High Similarity	NPC117180
0.8554	High Similarity	NPC66655
0.8523	High Similarity	NPC93843
0.8506	High Similarity	NPC304538
0.8488	Intermediate Similarity	NPC103326
0.8488	Intermediate Similarity	NPC87299
0.8488	Intermediate Similarity	NPC329319
0.8488	Intermediate Similarity	NPC99394
0.8372	Intermediate Similarity	NPC133050
0.837	Intermediate Similarity	NPC314690
0.8351	Intermediate Similarity	NPC19856
0.8276	Intermediate Similarity	NPC475199
0.8276	Intermediate Similarity	NPC283012
0.8242	Intermediate Similarity	NPC1793
0.8235	Intermediate Similarity	NPC224544
0.8202	Intermediate Similarity	NPC99482
0.8193	Intermediate Similarity	NPC108218
0.8182	Intermediate Similarity	NPC243601
0.8144	Intermediate Similarity	NPC289117
0.8144	Intermediate Similarity	NPC469481
0.809	Intermediate Similarity	NPC168855
0.8085	Intermediate Similarity	NPC271440
0.8081	Intermediate Similarity	NPC238696
0.8065	Intermediate Similarity	NPC79917
0.8046	Intermediate Similarity	NPC164449
0.8046	Intermediate Similarity	NPC184030
0.802	Intermediate Similarity	NPC27252
0.802	Intermediate Similarity	NPC472980
0.802	Intermediate Similarity	NPC472979
0.8	Intermediate Similarity	NPC474354
0.7955	Intermediate Similarity	NPC165212
0.7952	Intermediate Similarity	NPC208302
0.7941	Intermediate Similarity	NPC262365
0.7941	Intermediate Similarity	NPC64642
0.7941	Intermediate Similarity	NPC472982
0.7941	Intermediate Similarity	NPC149455
0.7938	Intermediate Similarity	NPC156313
0.7938	Intermediate Similarity	NPC32674
0.7912	Intermediate Similarity	NPC474211
0.79	Intermediate Similarity	NPC315794
0.7889	Intermediate Similarity	NPC95429
0.7872	Intermediate Similarity	NPC220596
0.7865	Intermediate Similarity	NPC73637
0.7865	Intermediate Similarity	NPC121478
0.7857	Intermediate Similarity	NPC216468
0.7857	Intermediate Similarity	NPC51333
0.7857	Intermediate Similarity	NPC78119
0.7857	Intermediate Similarity	NPC132078
0.7841	Intermediate Similarity	NPC328178
0.7826	Intermediate Similarity	NPC211237
0.7822	Intermediate Similarity	NPC471133
0.7812	Intermediate Similarity	NPC172925
0.78	Intermediate Similarity	NPC168829
0.7789	Intermediate Similarity	NPC45040
0.7788	Intermediate Similarity	NPC44732
0.7788	Intermediate Similarity	NPC133308
0.7778	Intermediate Similarity	NPC213730
0.7778	Intermediate Similarity	NPC294741
0.7767	Intermediate Similarity	NPC318327
0.7736	Intermediate Similarity	NPC196673
0.7723	Intermediate Similarity	NPC327811
0.7723	Intermediate Similarity	NPC288411
0.7723	Intermediate Similarity	NPC254965
0.7723	Intermediate Similarity	NPC323810
0.7714	Intermediate Similarity	NPC111108
0.7714	Intermediate Similarity	NPC308689
0.7714	Intermediate Similarity	NPC471188
0.77	Intermediate Similarity	NPC91461
0.77	Intermediate Similarity	NPC40258
0.77	Intermediate Similarity	NPC51015
0.77	Intermediate Similarity	NPC7686
0.7692	Intermediate Similarity	NPC58865
0.7692	Intermediate Similarity	NPC314187
0.7684	Intermediate Similarity	NPC300017
0.7677	Intermediate Similarity	NPC128723
0.7674	Intermediate Similarity	NPC189371
0.7647	Intermediate Similarity	NPC138942
0.7629	Intermediate Similarity	NPC76938
0.7629	Intermediate Similarity	NPC128062
0.7629	Intermediate Similarity	NPC151715
0.7629	Intermediate Similarity	NPC289769
0.7624	Intermediate Similarity	NPC255676
0.7624	Intermediate Similarity	NPC168393
0.7624	Intermediate Similarity	NPC233827
0.7619	Intermediate Similarity	NPC132720
0.759	Intermediate Similarity	NPC239931
0.759	Intermediate Similarity	NPC82770
0.759	Intermediate Similarity	NPC78954
0.7576	Intermediate Similarity	NPC225464
0.7573	Intermediate Similarity	NPC54765
0.7551	Intermediate Similarity	NPC26244
0.7551	Intermediate Similarity	NPC32714
0.7551	Intermediate Similarity	NPC274678
0.7551	Intermediate Similarity	NPC8392
0.7549	Intermediate Similarity	NPC249067
0.7547	Intermediate Similarity	NPC66208
0.7547	Intermediate Similarity	NPC95716
0.7526	Intermediate Similarity	NPC325292
0.7526	Intermediate Similarity	NPC138117
0.75	Intermediate Similarity	NPC213570
0.75	Intermediate Similarity	NPC12656
0.75	Intermediate Similarity	NPC139416
0.75	Intermediate Similarity	NPC211439
0.75	Intermediate Similarity	NPC246822
0.75	Intermediate Similarity	NPC473137
0.75	Intermediate Similarity	NPC92730
0.7477	Intermediate Similarity	NPC228425
0.7477	Intermediate Similarity	NPC228988
0.7477	Intermediate Similarity	NPC46940
0.7476	Intermediate Similarity	NPC117115
0.7476	Intermediate Similarity	NPC154899
0.7476	Intermediate Similarity	NPC233396
0.7475	Intermediate Similarity	NPC473388
0.7475	Intermediate Similarity	NPC132271
0.7475	Intermediate Similarity	NPC292730
0.7475	Intermediate Similarity	NPC216520
0.7475	Intermediate Similarity	NPC324602
0.7475	Intermediate Similarity	NPC82664
0.7475	Intermediate Similarity	NPC289201
0.7474	Intermediate Similarity	NPC104216
0.7449	Intermediate Similarity	NPC215351
0.7449	Intermediate Similarity	NPC206764
0.7449	Intermediate Similarity	NPC245187
0.7449	Intermediate Similarity	NPC20142
0.7447	Intermediate Similarity	NPC155393
0.7429	Intermediate Similarity	NPC95344
0.7429	Intermediate Similarity	NPC11554
0.7426	Intermediate Similarity	NPC211885
0.7423	Intermediate Similarity	NPC306074
0.7423	Intermediate Similarity	NPC265521
0.7423	Intermediate Similarity	NPC204210
0.7423	Intermediate Similarity	NPC304541
0.7412	Intermediate Similarity	NPC251490
0.7407	Intermediate Similarity	NPC322239
0.7407	Intermediate Similarity	NPC715
0.7407	Intermediate Similarity	NPC471485
0.7407	Intermediate Similarity	NPC321589
0.7404	Intermediate Similarity	NPC135464
0.7404	Intermediate Similarity	NPC92623
0.7404	Intermediate Similarity	NPC271274
0.7404	Intermediate Similarity	NPC67250
0.74	Intermediate Similarity	NPC77492
0.74	Intermediate Similarity	NPC474073
0.7396	Intermediate Similarity	NPC123273
0.7396	Intermediate Similarity	NPC258219
0.7396	Intermediate Similarity	NPC70436
0.7396	Intermediate Similarity	NPC242240
0.7396	Intermediate Similarity	NPC318325
0.7383	Intermediate Similarity	NPC151537
0.7379	Intermediate Similarity	NPC472222
0.7379	Intermediate Similarity	NPC472221
0.7379	Intermediate Similarity	NPC56168
0.7374	Intermediate Similarity	NPC222146
0.7374	Intermediate Similarity	NPC144682
0.7374	Intermediate Similarity	NPC313650
0.7368	Intermediate Similarity	NPC307235
0.7368	Intermediate Similarity	NPC407
0.7368	Intermediate Similarity	NPC23167
0.7364	Intermediate Similarity	NPC469663
0.7364	Intermediate Similarity	NPC472862
0.7364	Intermediate Similarity	NPC92
0.7364	Intermediate Similarity	NPC212891
0.7363	Intermediate Similarity	NPC242628
0.7353	Intermediate Similarity	NPC12221
0.7347	Intermediate Similarity	NPC55903
0.734	Intermediate Similarity	NPC175313
0.7339	Intermediate Similarity	NPC306740
0.7339	Intermediate Similarity	NPC268160
0.7339	Intermediate Similarity	NPC195922
0.7339	Intermediate Similarity	NPC249270
0.7333	Intermediate Similarity	NPC151477
0.7327	Intermediate Similarity	NPC122005
0.7327	Intermediate Similarity	NPC252821
0.7326	Intermediate Similarity	NPC135433
0.7326	Intermediate Similarity	NPC158028
0.7326	Intermediate Similarity	NPC87099
0.7326	Intermediate Similarity	NPC193578
0.7326	Intermediate Similarity	NPC280135
0.7326	Intermediate Similarity	NPC39799
0.7326	Intermediate Similarity	NPC226999
0.7326	Intermediate Similarity	NPC1008
0.7321	Intermediate Similarity	NPC151197
0.732	Intermediate Similarity	NPC47950
0.732	Intermediate Similarity	NPC312304
0.732	Intermediate Similarity	NPC192
0.732	Intermediate Similarity	NPC300478
0.7315	Intermediate Similarity	NPC302371
0.7308	Intermediate Similarity	NPC99557
0.7308	Intermediate Similarity	NPC471186
0.7308	Intermediate Similarity	NPC211551
0.7308	Intermediate Similarity	NPC105899
0.7308	Intermediate Similarity	NPC471350
0.7308	Intermediate Similarity	NPC219286
0.73	Intermediate Similarity	NPC202986
0.7297	Intermediate Similarity	NPC477136
0.7292	Intermediate Similarity	NPC25493
0.7292	Intermediate Similarity	NPC19680

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 NPC199567 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	395
0.1-0.2	1028
0.2-0.3	1285
0.3-0.4	3156
0.4-0.5	2036
0.5-0.6	976
0.6-0.7	245
0.7-0.8	27
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8737	High Similarity	NPD5700	Clinical (unspecified phase)
0.8554	High Similarity	NPD9294	Approved
0.7905	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD2342	Discontinued
0.7812	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD845	Approved
0.76	Intermediate Similarity	NPD1616	Discontinued
0.7551	Intermediate Similarity	NPD2860	Approved
0.7551	Intermediate Similarity	NPD2859	Approved
0.7549	Intermediate Similarity	NPD179	Clinical (unspecified phase)
0.7549	Intermediate Similarity	NPD1237	Approved
0.75	Intermediate Similarity	NPD3020	Approved
0.7477	Intermediate Similarity	NPD7635	Approved
0.7477	Intermediate Similarity	NPD1710	Approved
0.7449	Intermediate Similarity	NPD2934	Approved
0.7449	Intermediate Similarity	NPD2933	Approved
0.7423	Intermediate Similarity	NPD159	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD1809	Phase 2
0.7333	Intermediate Similarity	NPD4095	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD1239	Approved
0.7282	Intermediate Similarity	NPD4656	Approved
0.7282	Intermediate Similarity	NPD4658	Approved
0.7273	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD2227	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD9609	Approved
0.7228	Intermediate Similarity	NPD9611	Approved
0.7228	Intermediate Similarity	NPD9612	Approved
0.7228	Intermediate Similarity	NPD9495	Approved
0.7212	Intermediate Similarity	NPD3047	Approved
0.7212	Intermediate Similarity	NPD3048	Approved
0.7212	Intermediate Similarity	NPD3046	Approved
0.7207	Intermediate Similarity	NPD6775	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD4818	Approved
0.7184	Intermediate Similarity	NPD4817	Approved
0.7182	Intermediate Similarity	NPD5951	Approved
0.7174	Intermediate Similarity	NPD9250	Approved
0.713	Intermediate Similarity	NPD4025	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD288	Approved
0.7115	Intermediate Similarity	NPD4231	Approved
0.7115	Intermediate Similarity	NPD3680	Approved
0.7115	Intermediate Similarity	NPD3682	Approved
0.7115	Intermediate Similarity	NPD4229	Approved
0.7108	Intermediate Similarity	NPD675	Discontinued
0.7105	Intermediate Similarity	NPD5126	Approved
0.7105	Intermediate Similarity	NPD5125	Phase 3
0.708	Intermediate Similarity	NPD7741	Discontinued
0.708	Intermediate Similarity	NPD3091	Approved
0.7071	Intermediate Similarity	NPD9251	Approved
0.7053	Intermediate Similarity	NPD111	Approved
0.703	Intermediate Similarity	NPD844	Approved
0.7021	Intermediate Similarity	NPD3971	Phase 1
0.7019	Intermediate Similarity	NPD854	Approved
0.7019	Intermediate Similarity	NPD855	Approved
0.7019	Intermediate Similarity	NPD4719	Phase 2
0.701	Intermediate Similarity	NPD531	Approved
0.6961	Remote Similarity	NPD1564	Approved
0.6961	Remote Similarity	NPD1565	Approved
0.6961	Remote Similarity	NPD2487	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD1566	Phase 3
0.6957	Remote Similarity	NPD2286	Discontinued
0.6952	Remote Similarity	NPD3683	Approved
0.6952	Remote Similarity	NPD3681	Approved
0.6944	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD3772	Phase 3
0.6923	Remote Similarity	NPD2549	Approved
0.6923	Remote Similarity	NPD2555	Approved
0.6923	Remote Similarity	NPD2550	Approved
0.6923	Remote Similarity	NPD2552	Approved
0.6923	Remote Similarity	NPD2553	Approved
0.6923	Remote Similarity	NPD2558	Approved
0.6923	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD968	Approved
0.6903	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD314	Approved
0.6887	Remote Similarity	NPD310	Approved
0.6887	Remote Similarity	NPD10	Approved
0.6887	Remote Similarity	NPD309	Approved
0.6887	Remote Similarity	NPD311	Approved
0.6887	Remote Similarity	NPD315	Approved
0.6881	Remote Similarity	NPD1792	Phase 2
0.6881	Remote Similarity	NPD3022	Approved
0.6881	Remote Similarity	NPD3021	Approved
0.6875	Remote Similarity	NPD2629	Approved
0.6875	Remote Similarity	NPD497	Approved
0.6863	Remote Similarity	NPD1989	Approved
0.6857	Remote Similarity	NPD4188	Approved
0.6857	Remote Similarity	NPD4189	Approved
0.6842	Remote Similarity	NPD9491	Approved
0.6838	Remote Similarity	NPD3092	Approved
0.6837	Remote Similarity	NPD1101	Approved
0.681	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.681	Remote Similarity	NPD3095	Discontinued
0.6796	Remote Similarity	NPD1875	Phase 1
0.6792	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD1930	Approved
0.6792	Remote Similarity	NPD1929	Approved
0.6786	Remote Similarity	NPD495	Approved
0.6786	Remote Similarity	NPD496	Approved
0.6786	Remote Similarity	NPD498	Approved
0.6783	Remote Similarity	NPD2106	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6049	Phase 2
0.6765	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD1242	Phase 1
0.6757	Remote Similarity	NPD2500	Approved
0.6757	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD2499	Approved
0.6733	Remote Similarity	NPD752	Approved
0.6724	Remote Similarity	NPD4093	Discontinued
0.6723	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.67	Remote Similarity	NPD1086	Approved
0.67	Remote Similarity	NPD1089	Approved
0.67	Remote Similarity	NPD1090	Approved
0.67	Remote Similarity	NPD9258	Approved
0.67	Remote Similarity	NPD9256	Approved
0.6698	Remote Similarity	NPD846	Approved
0.6698	Remote Similarity	NPD940	Approved
0.6697	Remote Similarity	NPD9532	Phase 3
0.6667	Remote Similarity	NPD1238	Approved
0.6667	Remote Similarity	NPD4254	Approved
0.6667	Remote Similarity	NPD7008	Discontinued
0.6667	Remote Similarity	NPD5048	Discontinued
0.6667	Remote Similarity	NPD1563	Approved
0.6667	Remote Similarity	NPD1202	Approved
0.6667	Remote Similarity	NPD720	Approved
0.6667	Remote Similarity	NPD4253	Approved
0.6667	Remote Similarity	NPD7725	Approved
0.6667	Remote Similarity	NPD1283	Approved
0.6667	Remote Similarity	NPD719	Approved
0.6638	Remote Similarity	NPD5304	Approved
0.6638	Remote Similarity	NPD5303	Approved
0.6637	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD4717	Approved
0.6636	Remote Similarity	NPD4720	Approved
0.6636	Remote Similarity	NPD4718	Approved
0.6634	Remote Similarity	NPD530	Approved
0.6632	Remote Similarity	NPD226	Approved
0.6612	Remote Similarity	NPD3094	Phase 2
0.6606	Remote Similarity	NPD3526	Approved
0.6606	Remote Similarity	NPD1444	Approved
0.6606	Remote Similarity	NPD1445	Approved
0.6606	Remote Similarity	NPD2551	Approved
0.6606	Remote Similarity	NPD2559	Approved
0.6606	Remote Similarity	NPD3524	Approved
0.6604	Remote Similarity	NPD3028	Approved
0.6602	Remote Similarity	NPD4814	Discontinued
0.66	Remote Similarity	NPD800	Approved
0.66	Remote Similarity	NPD9249	Phase 1
0.6587	Remote Similarity	NPD7431	Approved
0.6587	Remote Similarity	NPD7430	Approved
0.6583	Remote Similarity	NPD1669	Approved
0.6581	Remote Similarity	NPD1651	Approved
0.6579	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD1088	Approved
0.6566	Remote Similarity	NPD9538	Approved
0.6555	Remote Similarity	NPD1201	Approved
0.6555	Remote Similarity	NPD2173	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD4119	Approved
0.6532	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD3019	Approved
0.6525	Remote Similarity	NPD1751	Approved
0.6525	Remote Similarity	NPD4589	Approved
0.6525	Remote Similarity	NPD4059	Approved
0.6525	Remote Similarity	NPD2932	Approved
0.6522	Remote Similarity	NPD9716	Approved
0.6522	Remote Similarity	NPD4198	Discontinued
0.6522	Remote Similarity	NPD709	Approved
0.6518	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD9497	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD9712	Approved
0.6509	Remote Similarity	NPD2066	Phase 3
0.6505	Remote Similarity	NPD3719	Approved
0.6505	Remote Similarity	NPD1409	Phase 3
0.6505	Remote Similarity	NPD3718	Approved
0.6496	Remote Similarity	NPD7330	Discontinued
0.6491	Remote Similarity	NPD2229	Approved
0.6491	Remote Similarity	NPD2234	Approved
0.6491	Remote Similarity	NPD2228	Approved
0.6486	Remote Similarity	NPD2684	Approved
0.6481	Remote Similarity	NPD1542	Approved
0.6481	Remote Similarity	NPD6647	Phase 2
0.6481	Remote Similarity	NPD9500	Approved
0.6471	Remote Similarity	NPD3897	Approved
0.6471	Remote Similarity	NPD3898	Approved
0.6471	Remote Similarity	NPD3895	Approved
0.6471	Remote Similarity	NPD3896	Approved
0.6471	Remote Similarity	NPD4135	Approved
0.6471	Remote Similarity	NPD4106	Approved
0.6471	Remote Similarity	NPD4136	Approved
0.6466	Remote Similarity	NPD3123	Discovery
0.6442	Remote Similarity	NPD1693	Approved
0.6436	Remote Similarity	NPD689	Discontinued
0.6434	Remote Similarity	NPD6587	Approved
0.6434	Remote Similarity	NPD6586	Approved
0.6429	Remote Similarity	NPD4750	Phase 3
0.6423	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD5909	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data