NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	183.09
Volume:	185.122
LogP:	-0.537
LogD:	-0.412
LogS:	-2.492
# Rotatable Bonds:	3
TPSA:	75.71
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.633
Synthetic Accessibility Score:	2.485
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.146
MDCK Permeability:	7.683601143071428e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.481
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.025

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.131
Plasma Protein Binding (PPB):	14.635885238647461%
Volume Distribution (VD):	1.328
Pgp-substrate:	78.67802429199219%

ADMET: Metabolism

CYP1A2-inhibitor:	0.083
CYP1A2-substrate:	0.743
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.501
CYP2C9-inhibitor:	0.021
CYP2C9-substrate:	0.826
CYP2D6-inhibitor:	0.032
CYP2D6-substrate:	0.859
CYP3A4-inhibitor:	0.024
CYP3A4-substrate:	0.189

ADMET: Excretion

Clearance (CL):	9.194
Half-life (T1/2):	0.843

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.15
Drug-inuced Liver Injury (DILI):	0.036
AMES Toxicity:	0.319
Rat Oral Acute Toxicity:	0.777
Maximum Recommended Daily Dose:	0.941
Skin Sensitization:	0.692
Carcinogencity:	0.047
Eye Corrosion:	0.657
Eye Irritation:	0.169
Respiratory Toxicity:	0.914

Download Data

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

Natural Product: NPC326599

Natural Product ID:	NPC326599
*Common Name:**	4-[(1R)-2-Amino-1-Hydroxyethyl]-2-Methoxyphenol
IUPAC Name:	4-[(1R)-2-amino-1-hydroxyethyl]-2-methoxyphenol
Synonyms:
Standard InCHIKey:	YNYAYWLBAHXHLL-QMMMGPOBSA-N
Standard InCHI:	InChI=1S/C9H13NO3/c1-13-9-4-6(8(12)5-10)2-3-7(9)11/h2-4,8,11-12H,5,10H2,1H3/t8-/m0/s1
SMILES:	NC[C@@H](c1ccc(c(c1)OC)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1559460
PubChem CID:	688100
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0000190] Methoxyphenols

*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.	faeces	n.a.	PMID[20708442]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	bile	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
Potency	4

Activity Type	# Activity
Individual Protein	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT163	Individual Protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	Potency	=	5011.9	nM	PMID[482728]
NPT95	Individual Protein	Muscarinic acetylcholine receptor M1	Rattus norvegicus	Potency	=	89.1	nM	PMID[482728]
NPT2	Others	Unspecified		Potency	n.a.	29081.0	nM	PMID[482728]

☑ 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 NPC326599 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	227
0.1-0.2	1469
0.2-0.3	7193
0.3-0.4	11992
0.4-0.5	5099
0.5-0.6	9655
0.6-0.7	5426
0.7-0.8	1516
0.8-0.85	96
0.85-0.9	17
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC329595
0.9431	High Similarity	NPC140359
0.9431	High Similarity	NPC13020
0.9106	High Similarity	NPC118522
0.9106	High Similarity	NPC169207
0.9106	High Similarity	NPC115627
0.8862	High Similarity	NPC120075
0.876	High Similarity	NPC236347
0.876	High Similarity	NPC323775
0.872	High Similarity	NPC181969
0.872	High Similarity	NPC320987
0.8667	High Similarity	NPC14600
0.8667	High Similarity	NPC312770
0.8667	High Similarity	NPC41473
0.8667	High Similarity	NPC160607
0.8667	High Similarity	NPC204848
0.8651	High Similarity	NPC35071
0.8651	High Similarity	NPC177475
0.8651	High Similarity	NPC148615
0.864	High Similarity	NPC255675
0.8629	High Similarity	NPC221049
0.855	High Similarity	NPC153990
0.8516	High Similarity	NPC470804
0.8516	High Similarity	NPC476343
0.8478	Intermediate Similarity	NPC66518
0.8467	Intermediate Similarity	NPC299583
0.8462	Intermediate Similarity	NPC105513
0.8455	Intermediate Similarity	NPC146422
0.845	Intermediate Similarity	NPC209567
0.845	Intermediate Similarity	NPC298486
0.8425	Intermediate Similarity	NPC135961
0.8425	Intermediate Similarity	NPC37205
0.8425	Intermediate Similarity	NPC160931
0.8413	Intermediate Similarity	NPC164386
0.8374	Intermediate Similarity	NPC8547
0.8374	Intermediate Similarity	NPC139617
0.8374	Intermediate Similarity	NPC257124
0.8374	Intermediate Similarity	NPC156840
0.8374	Intermediate Similarity	NPC78918
0.8374	Intermediate Similarity	NPC173746
0.8296	Intermediate Similarity	NPC130595
0.8296	Intermediate Similarity	NPC214869
0.8296	Intermediate Similarity	NPC93882
0.8295	Intermediate Similarity	NPC183262
0.8281	Intermediate Similarity	NPC24474
0.8281	Intermediate Similarity	NPC311595
0.8271	Intermediate Similarity	NPC291847
0.8252	Intermediate Similarity	NPC115144
0.8252	Intermediate Similarity	NPC277857
0.8244	Intermediate Similarity	NPC471693
0.8244	Intermediate Similarity	NPC165375
0.8244	Intermediate Similarity	NPC220598
0.8235	Intermediate Similarity	NPC285078
0.8235	Intermediate Similarity	NPC6854
0.8235	Intermediate Similarity	NPC313737
0.8231	Intermediate Similarity	NPC211992
0.8222	Intermediate Similarity	NPC114102
0.8211	Intermediate Similarity	NPC246358
0.8211	Intermediate Similarity	NPC233731
0.8211	Intermediate Similarity	NPC145638
0.8211	Intermediate Similarity	NPC290566
0.8211	Intermediate Similarity	NPC36108
0.8211	Intermediate Similarity	NPC7097
0.8209	Intermediate Similarity	NPC155838
0.8203	Intermediate Similarity	NPC85276
0.8195	Intermediate Similarity	NPC191037
0.8195	Intermediate Similarity	NPC58607
0.8195	Intermediate Similarity	NPC178284
0.8175	Intermediate Similarity	NPC218530
0.8154	Intermediate Similarity	NPC207613
0.8148	Intermediate Similarity	NPC262641
0.8148	Intermediate Similarity	NPC35961
0.8148	Intermediate Similarity	NPC195749
0.8148	Intermediate Similarity	NPC52029
0.8145	Intermediate Similarity	NPC137685
0.814	Intermediate Similarity	NPC20674
0.8134	Intermediate Similarity	NPC292056
0.8134	Intermediate Similarity	NPC165045
0.8134	Intermediate Similarity	NPC183181
0.8134	Intermediate Similarity	NPC319625
0.8134	Intermediate Similarity	NPC118533
0.8134	Intermediate Similarity	NPC111247
0.8134	Intermediate Similarity	NPC118787
0.8134	Intermediate Similarity	NPC41706
0.8134	Intermediate Similarity	NPC163332
0.8134	Intermediate Similarity	NPC147821
0.812	Intermediate Similarity	NPC194519
0.812	Intermediate Similarity	NPC148627
0.8092	Intermediate Similarity	NPC312675
0.8092	Intermediate Similarity	NPC470212
0.8092	Intermediate Similarity	NPC473853
0.8092	Intermediate Similarity	NPC184651
0.8092	Intermediate Similarity	NPC49341
0.8092	Intermediate Similarity	NPC113865
0.8092	Intermediate Similarity	NPC54872
0.8092	Intermediate Similarity	NPC324571
0.8092	Intermediate Similarity	NPC262156
0.8092	Intermediate Similarity	NPC343720
0.8088	Intermediate Similarity	NPC255550
0.8088	Intermediate Similarity	NPC308885
0.808	Intermediate Similarity	NPC195873
0.8077	Intermediate Similarity	NPC229401
0.8074	Intermediate Similarity	NPC252307
0.8074	Intermediate Similarity	NPC474178
0.8074	Intermediate Similarity	NPC245826
0.8069	Intermediate Similarity	NPC470935
0.8069	Intermediate Similarity	NPC471032
0.806	Intermediate Similarity	NPC301713
0.8049	Intermediate Similarity	NPC227894
0.8045	Intermediate Similarity	NPC114901
0.8045	Intermediate Similarity	NPC293701
0.8045	Intermediate Similarity	NPC48990
0.8045	Intermediate Similarity	NPC109822
0.8045	Intermediate Similarity	NPC94276
0.8042	Intermediate Similarity	NPC294249
0.803	Intermediate Similarity	NPC85488
0.8015	Intermediate Similarity	NPC170844
0.8015	Intermediate Similarity	NPC476968
0.8015	Intermediate Similarity	NPC86030
0.8015	Intermediate Similarity	NPC5851
0.8015	Intermediate Similarity	NPC475875
0.8	Intermediate Similarity	NPC251571
0.8	Intermediate Similarity	NPC5428
0.7984	Intermediate Similarity	NPC259638
0.7984	Intermediate Similarity	NPC137096
0.7984	Intermediate Similarity	NPC293619
0.797	Intermediate Similarity	NPC318777
0.797	Intermediate Similarity	NPC280704
0.7969	Intermediate Similarity	NPC10286
0.7969	Intermediate Similarity	NPC213
0.7956	Intermediate Similarity	NPC143483
0.7956	Intermediate Similarity	NPC187998
0.7956	Intermediate Similarity	NPC195292
0.7956	Intermediate Similarity	NPC145305
0.7956	Intermediate Similarity	NPC153739
0.7956	Intermediate Similarity	NPC257582
0.7956	Intermediate Similarity	NPC242807
0.7956	Intermediate Similarity	NPC64201
0.7956	Intermediate Similarity	NPC92164
0.7956	Intermediate Similarity	NPC241522
0.7956	Intermediate Similarity	NPC42300
0.7956	Intermediate Similarity	NPC174495
0.7956	Intermediate Similarity	NPC77040
0.7955	Intermediate Similarity	NPC127389
0.7955	Intermediate Similarity	NPC290451
0.7943	Intermediate Similarity	NPC296898
0.7941	Intermediate Similarity	NPC98631
0.7941	Intermediate Similarity	NPC45774
0.7941	Intermediate Similarity	NPC470213
0.7941	Intermediate Similarity	NPC11258
0.7941	Intermediate Similarity	NPC282703
0.7941	Intermediate Similarity	NPC21867
0.7941	Intermediate Similarity	NPC206615
0.7941	Intermediate Similarity	NPC72529
0.7941	Intermediate Similarity	NPC186843
0.7941	Intermediate Similarity	NPC184733
0.7941	Intermediate Similarity	NPC129570
0.7941	Intermediate Similarity	NPC128208
0.7937	Intermediate Similarity	NPC21890
0.7929	Intermediate Similarity	NPC131204
0.7929	Intermediate Similarity	NPC301050
0.7923	Intermediate Similarity	NPC470626
0.7907	Intermediate Similarity	NPC193067
0.7903	Intermediate Similarity	NPC251306
0.7899	Intermediate Similarity	NPC474017
0.7899	Intermediate Similarity	NPC277804
0.7899	Intermediate Similarity	NPC472597
0.7899	Intermediate Similarity	NPC65942
0.7899	Intermediate Similarity	NPC470096
0.7899	Intermediate Similarity	NPC470095
0.7899	Intermediate Similarity	NPC248307
0.7895	Intermediate Similarity	NPC41562
0.7895	Intermediate Similarity	NPC71090
0.7891	Intermediate Similarity	NPC142599
0.7886	Intermediate Similarity	NPC42383
0.7883	Intermediate Similarity	NPC212015
0.7868	Intermediate Similarity	NPC186898
0.7863	Intermediate Similarity	NPC281298
0.7863	Intermediate Similarity	NPC310338
0.7863	Intermediate Similarity	NPC477803
0.7863	Intermediate Similarity	NPC299406
0.7846	Intermediate Similarity	NPC39793
0.7842	Intermediate Similarity	NPC253105
0.7842	Intermediate Similarity	NPC7903
0.7842	Intermediate Similarity	NPC35932
0.7842	Intermediate Similarity	NPC160991
0.7842	Intermediate Similarity	NPC106739
0.7842	Intermediate Similarity	NPC16208
0.7842	Intermediate Similarity	NPC184447
0.7842	Intermediate Similarity	NPC201587
0.784	Intermediate Similarity	NPC97811
0.7836	Intermediate Similarity	NPC228922
0.7836	Intermediate Similarity	NPC197757
0.7826	Intermediate Similarity	NPC142985
0.7826	Intermediate Similarity	NPC472338
0.782	Intermediate Similarity	NPC285289
0.781	Intermediate Similarity	NPC472968
0.781	Intermediate Similarity	NPC470084
0.7805	Intermediate Similarity	NPC292792
0.7805	Intermediate Similarity	NPC12278

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 NPC326599 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	783
0.2-0.3	1609
0.3-0.4	2454
0.4-0.5	2156
0.5-0.6	1186
0.6-0.7	598
0.7-0.8	170
0.8-0.85	27
0.85-0.9	5
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9106	High Similarity	NPD9384	Approved
0.9106	High Similarity	NPD9381	Approved
0.8968	High Similarity	NPD9622	Approved
0.8824	High Similarity	NPD3060	Approved
0.876	High Similarity	NPD9620	Approved
0.876	High Similarity	NPD9619	Approved
0.876	High Similarity	NPD9621	Approved
0.8496	Intermediate Similarity	NPD601	Approved
0.8496	Intermediate Similarity	NPD598	Approved
0.8496	Intermediate Similarity	NPD597	Approved
0.8455	Intermediate Similarity	NPD9377	Approved
0.8455	Intermediate Similarity	NPD9379	Approved
0.8433	Intermediate Similarity	NPD1130	Approved
0.8433	Intermediate Similarity	NPD1136	Approved
0.8433	Intermediate Similarity	NPD1132	Approved
0.8425	Intermediate Similarity	NPD2977	Approved
0.8425	Intermediate Similarity	NPD2978	Approved
0.8374	Intermediate Similarity	NPD228	Approved
0.8333	Intermediate Similarity	NPD3686	Approved
0.8333	Intermediate Similarity	NPD3687	Approved
0.8296	Intermediate Similarity	NPD2674	Phase 3
0.8286	Intermediate Similarity	NPD4162	Approved
0.8273	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD3061	Approved
0.8235	Intermediate Similarity	NPD3062	Approved
0.8235	Intermediate Similarity	NPD3059	Approved
0.8211	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.8209	Intermediate Similarity	NPD600	Approved
0.8209	Intermediate Similarity	NPD596	Approved
0.8175	Intermediate Similarity	NPD9618	Approved
0.8175	Intermediate Similarity	NPD9614	Approved
0.8116	Intermediate Similarity	NPD823	Approved
0.8116	Intermediate Similarity	NPD5314	Approved
0.8116	Intermediate Similarity	NPD817	Approved
0.8088	Intermediate Similarity	NPD3144	Approved
0.8088	Intermediate Similarity	NPD3145	Approved
0.8085	Intermediate Similarity	NPD7153	Discontinued
0.806	Intermediate Similarity	NPD558	Phase 2
0.803	Intermediate Similarity	NPD2231	Phase 2
0.803	Intermediate Similarity	NPD2235	Phase 2
0.8015	Intermediate Similarity	NPD3027	Phase 3
0.7984	Intermediate Similarity	NPD9615	Approved
0.7984	Intermediate Similarity	NPD9613	Approved
0.7984	Intermediate Similarity	NPD9616	Approved
0.7945	Intermediate Similarity	NPD7526	Approved
0.7945	Intermediate Similarity	NPD52	Approved
0.7945	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD9570	Approved
0.7923	Intermediate Similarity	NPD316	Approved
0.7899	Intermediate Similarity	NPD839	Approved
0.7899	Intermediate Similarity	NPD840	Approved
0.7899	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7887	Intermediate Similarity	NPD1375	Discontinued
0.7877	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD3052	Approved
0.7857	Intermediate Similarity	NPD3054	Approved
0.7846	Intermediate Similarity	NPD317	Approved
0.7846	Intermediate Similarity	NPD318	Approved
0.7846	Intermediate Similarity	NPD16	Approved
0.7846	Intermediate Similarity	NPD856	Approved
0.7842	Intermediate Similarity	NPD1558	Phase 1
0.7793	Intermediate Similarity	NPD5241	Discontinued
0.7786	Intermediate Similarity	NPD555	Phase 2
0.7778	Intermediate Similarity	NPD4236	Phase 3
0.7778	Intermediate Similarity	NPD4237	Approved
0.7778	Intermediate Similarity	NPD9634	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD259	Phase 1
0.7721	Intermediate Similarity	NPD3053	Approved
0.7721	Intermediate Similarity	NPD1820	Approved
0.7721	Intermediate Similarity	NPD1818	Approved
0.7721	Intermediate Similarity	NPD1817	Approved
0.7721	Intermediate Similarity	NPD3055	Approved
0.7721	Intermediate Similarity	NPD1819	Approved
0.7703	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD2161	Phase 2
0.7687	Intermediate Similarity	NPD1774	Approved
0.7681	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD2677	Approved
0.7647	Intermediate Similarity	NPD5310	Approved
0.7647	Intermediate Similarity	NPD5311	Approved
0.7635	Intermediate Similarity	NPD4123	Phase 3
0.7635	Intermediate Similarity	NPD3536	Discontinued
0.7626	Intermediate Similarity	NPD3179	Approved
0.7626	Intermediate Similarity	NPD3180	Approved
0.7609	Intermediate Similarity	NPD9569	Approved
0.7606	Intermediate Similarity	NPD2653	Approved
0.7594	Intermediate Similarity	NPD1357	Approved
0.7589	Intermediate Similarity	NPD1613	Approved
0.7589	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD2238	Phase 2
0.7582	Intermediate Similarity	NPD5772	Approved
0.7582	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD5773	Approved
0.755	Intermediate Similarity	NPD3455	Phase 2
0.7536	Intermediate Similarity	NPD602	Approved
0.7536	Intermediate Similarity	NPD599	Approved
0.7536	Intermediate Similarity	NPD858	Approved
0.7536	Intermediate Similarity	NPD859	Approved
0.7534	Intermediate Similarity	NPD5177	Phase 3
0.752	Intermediate Similarity	NPD9610	Approved
0.752	Intermediate Similarity	NPD9608	Approved
0.7518	Intermediate Similarity	NPD1423	Approved
0.7517	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1771	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3165	Approved
0.75	Intermediate Similarity	NPD3166	Approved
0.75	Intermediate Similarity	NPD3164	Approved
0.75	Intermediate Similarity	NPD2562	Approved
0.75	Intermediate Similarity	NPD2561	Approved
0.75	Intermediate Similarity	NPD3167	Approved
0.7483	Intermediate Similarity	NPD6331	Phase 2
0.7483	Intermediate Similarity	NPD2568	Approved
0.7466	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD825	Approved
0.7465	Intermediate Similarity	NPD826	Approved
0.7464	Intermediate Similarity	NPD1794	Approved
0.7447	Intermediate Similarity	NPD5718	Phase 2
0.7447	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD257	Approved
0.741	Intermediate Similarity	NPD258	Approved
0.74	Intermediate Similarity	NPD3158	Phase 1
0.74	Intermediate Similarity	NPD3157	Approved
0.7394	Intermediate Similarity	NPD3532	Approved
0.7394	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD3530	Approved
0.7394	Intermediate Similarity	NPD3531	Approved
0.7391	Intermediate Similarity	NPD196	Phase 1
0.7386	Intermediate Similarity	NPD4678	Approved
0.7386	Intermediate Similarity	NPD4675	Approved
0.7376	Intermediate Similarity	NPD9537	Phase 1
0.7376	Intermediate Similarity	NPD9536	Phase 1
0.7376	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD3620	Phase 2
0.7342	Intermediate Similarity	NPD4666	Phase 3
0.7338	Intermediate Similarity	NPD1134	Approved
0.7338	Intermediate Similarity	NPD1129	Approved
0.7338	Intermediate Similarity	NPD1133	Approved
0.7338	Intermediate Similarity	NPD1131	Approved
0.7338	Intermediate Similarity	NPD1135	Approved
0.7329	Intermediate Similarity	NPD3175	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD4005	Discontinued
0.7319	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7038	Approved
0.7317	Intermediate Similarity	NPD7039	Approved
0.7315	Intermediate Similarity	NPD302	Approved
0.7308	Intermediate Similarity	NPD2560	Approved
0.7308	Intermediate Similarity	NPD2563	Approved
0.7305	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD2684	Approved
0.7286	Intermediate Similarity	NPD6584	Phase 3
0.7286	Intermediate Similarity	NPD3691	Phase 2
0.7286	Intermediate Similarity	NPD3690	Phase 2
0.7285	Intermediate Similarity	NPD4739	Approved
0.7285	Intermediate Similarity	NPD1424	Approved
0.7279	Intermediate Similarity	NPD2667	Approved
0.7279	Intermediate Similarity	NPD2668	Approved
0.7278	Intermediate Similarity	NPD5709	Phase 3
0.7273	Intermediate Similarity	NPD5283	Phase 1
0.7267	Intermediate Similarity	NPD3122	Phase 3
0.7267	Intermediate Similarity	NPD27	Approved
0.7267	Intermediate Similarity	NPD2489	Approved
0.726	Intermediate Similarity	NPD2156	Approved
0.726	Intermediate Similarity	NPD2154	Approved
0.726	Intermediate Similarity	NPD2155	Approved
0.7246	Intermediate Similarity	NPD2232	Approved
0.7246	Intermediate Similarity	NPD2233	Approved
0.7246	Intermediate Similarity	NPD2230	Approved
0.7234	Intermediate Similarity	NPD9494	Approved
0.7234	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD593	Approved
0.7218	Intermediate Similarity	NPD595	Approved
0.7209	Intermediate Similarity	NPD290	Approved
0.7208	Intermediate Similarity	NPD3866	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD1798	Approved
0.7206	Intermediate Similarity	NPD1797	Approved
0.72	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD1669	Approved
0.7192	Intermediate Similarity	NPD6895	Approved
0.7192	Intermediate Similarity	NPD6896	Approved
0.719	Intermediate Similarity	NPD6031	Approved
0.719	Intermediate Similarity	NPD6030	Approved
0.719	Intermediate Similarity	NPD5976	Discontinued
0.7176	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD3705	Approved
0.7154	Intermediate Similarity	NPD9296	Approved
0.7153	Intermediate Similarity	NPD6405	Approved
0.7153	Intermediate Similarity	NPD3162	Approved
0.7153	Intermediate Similarity	NPD6407	Approved
0.7153	Intermediate Similarity	NPD3163	Approved
0.7143	Intermediate Similarity	NPD4210	Discontinued
0.7143	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD9611	Approved
0.712	Intermediate Similarity	NPD9612	Approved
0.712	Intermediate Similarity	NPD9609	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