NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	168.08
Volume:	174.125
LogP:	0.612
LogD:	1.027
LogS:	-0.524
# Rotatable Bonds:	3
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.706
Synthetic Accessibility Score:	1.752
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:	-4.288
MDCK Permeability:	1.5747573343105614e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.039
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.168
30% Bioavailability (F30%):	0.331

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.121
Plasma Protein Binding (PPB):	31.659423828125%
Volume Distribution (VD):	1.235
Pgp-substrate:	43.72002029418945%

ADMET: Metabolism

CYP1A2-inhibitor:	0.611
CYP1A2-substrate:	0.882
CYP2C19-inhibitor:	0.155
CYP2C19-substrate:	0.7
CYP2C9-inhibitor:	0.043
CYP2C9-substrate:	0.852
CYP2D6-inhibitor:	0.081
CYP2D6-substrate:	0.878
CYP3A4-inhibitor:	0.067
CYP3A4-substrate:	0.296

ADMET: Excretion

Clearance (CL):	12.615
Half-life (T1/2):	0.901

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.094
Drug-inuced Liver Injury (DILI):	0.046
AMES Toxicity:	0.177
Rat Oral Acute Toxicity:	0.026
Maximum Recommended Daily Dose:	0.051
Skin Sensitization:	0.773
Carcinogencity:	0.355
Eye Corrosion:	0.776
Eye Irritation:	0.988
Respiratory Toxicity:	0.049

Download Data

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

Natural Product: NPC221049

Natural Product ID:	NPC221049
*Common Name:**	4-Hydroxy-3-Methoxyphenylethanol
IUPAC Name:	4-(2-hydroxyethyl)-2-methoxyphenol
Synonyms:
Standard InCHIKey:	XHUBSJRBOQIZNI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H12O3/c1-12-9-6-7(4-5-10)2-3-8(9)11/h2-3,6,10-11H,4-5H2,1H3
SMILES:	COc1cc(ccc1O)CCO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3747068
PubChem CID:	16928
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
NPO1756	Cremastra appendiculata	Species	Orchidaceae	Eukaryota	n.a.	bulb	n.a.	PMID[14994197]
NPO1756	Cremastra appendiculata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844951]
NPO1756	Cremastra appendiculata	Species	Orchidaceae	Eukaryota	tubers	n.a.	n.a.	PMID[16792409]
NPO17553	Pleione bulbocodioides	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23627123]
NPO16066	Urtica cannabina	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4203	Phlomoides rotata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16066	Urtica cannabina	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1756	Cremastra appendiculata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16066	Urtica cannabina	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1756	Cremastra appendiculata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12875	Pleione yunnanensis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17553	Pleione bulbocodioides	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4203	Phlomoides rotata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1756	Cremastra appendiculata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12875	Pleione yunnanensis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17553	Pleione bulbocodioides	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17553	Pleione bulbocodioides	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4203	Phlomoides rotata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16066	Urtica cannabina	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12875	Pleione yunnanensis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1756	Cremastra appendiculata	Species	Orchidaceae	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
NPO42044	NPC221049	n.a.	Roots	2	n.a.	n.a.	mg/g of DW	PMID[35056798]

☑ 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	20

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	15
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT466	Cell Line	U-937	Homo sapiens	MNCC	>	1000.0	uM	PMID[526693]
NPT466	Cell Line	U-937	Homo sapiens	Inhibition	=	0.9	%	PMID[526693]
NPT466	Cell Line	U-937	Homo sapiens	Inhibition	=	1.1	%	PMID[526693]
NPT466	Cell Line	U-937	Homo sapiens	Inhibition	=	1.2	%	PMID[526693]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	0.0	%	PMID[526692]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	2.6	%	PMID[526692]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	8.3	%	PMID[526692]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	6.0	%	PMID[526692]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	5.2	%	PMID[526692]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	24.4	%	PMID[526692]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	17.4	%	PMID[526692]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	11.3	%	PMID[526692]
NPT27	Others	Unspecified		Activity	>	1000.0	uM	PMID[526692]

☑ 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 NPC221049 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	383
0.1-0.2	1792
0.2-0.3	5881
0.3-0.4	13233
0.4-0.5	4100
0.5-0.6	5916
0.6-0.7	7833
0.7-0.8	2673
0.8-0.85	592
0.85-0.9	245
0.9-0.95	40
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9818	High Similarity	NPC255675
0.973	High Similarity	NPC320987
0.973	High Similarity	NPC181969
0.9643	High Similarity	NPC148615
0.9643	High Similarity	NPC177475
0.9643	High Similarity	NPC35071
0.9537	High Similarity	NPC156840
0.9537	High Similarity	NPC257124
0.9537	High Similarity	NPC139617
0.9537	High Similarity	NPC8547
0.9537	High Similarity	NPC78918
0.9537	High Similarity	NPC173746
0.9474	High Similarity	NPC470804
0.9391	High Similarity	NPC209567
0.9381	High Similarity	NPC135961
0.9381	High Similarity	NPC20674
0.9375	High Similarity	NPC164386
0.9352	High Similarity	NPC36108
0.9352	High Similarity	NPC233731
0.9352	High Similarity	NPC7097
0.9352	High Similarity	NPC246358
0.931	High Similarity	NPC471693
0.9304	High Similarity	NPC476343
0.9304	High Similarity	NPC49341
0.9298	High Similarity	NPC229401
0.9266	High Similarity	NPC137685
0.9211	High Similarity	NPC24474
0.9211	High Similarity	NPC311595
0.9204	High Similarity	NPC259638
0.9182	High Similarity	NPC195873
0.9167	High Similarity	NPC227894
0.9153	High Similarity	NPC148627
0.9153	High Similarity	NPC194519
0.9145	High Similarity	NPC165375
0.9145	High Similarity	NPC220598
0.9115	High Similarity	NPC193067
0.9076	High Similarity	NPC191037
0.9076	High Similarity	NPC178284
0.9076	High Similarity	NPC58607
0.9052	High Similarity	NPC207613
0.9035	High Similarity	NPC293619
0.9	High Similarity	NPC163332
0.9	High Similarity	NPC111247
0.9	High Similarity	NPC165045
0.9	High Similarity	NPC183181
0.9	High Similarity	NPC147821
0.9	High Similarity	NPC319625
0.9	High Similarity	NPC118787
0.9	High Similarity	NPC292056
0.9	High Similarity	NPC5428
0.9	High Similarity	NPC118533
0.9	High Similarity	NPC41706
0.8991	High Similarity	NPC251306
0.8974	High Similarity	NPC184651
0.8974	High Similarity	NPC473853
0.8974	High Similarity	NPC113865
0.8974	High Similarity	NPC54872
0.8974	High Similarity	NPC470212
0.8974	High Similarity	NPC324571
0.8974	High Similarity	NPC262156
0.8974	High Similarity	NPC343720
0.8974	High Similarity	NPC312675
0.8957	High Similarity	NPC470626
0.8957	High Similarity	NPC63083
0.8926	High Similarity	NPC252307
0.8926	High Similarity	NPC245826
0.8926	High Similarity	NPC470213
0.8926	High Similarity	NPC474178
0.8926	High Similarity	NPC98631
0.8926	High Similarity	NPC206615
0.8926	High Similarity	NPC186843
0.8908	High Similarity	NPC114901
0.8908	High Similarity	NPC206487
0.8908	High Similarity	NPC94276
0.8908	High Similarity	NPC109822
0.8908	High Similarity	NPC48990
0.8908	High Similarity	NPC293701
0.8908	High Similarity	NPC5796
0.8898	High Similarity	NPC41562
0.8898	High Similarity	NPC71090
0.8898	High Similarity	NPC85488
0.8889	High Similarity	NPC12278
0.8889	High Similarity	NPC292792
0.8879	High Similarity	NPC310338
0.8879	High Similarity	NPC299406
0.8879	High Similarity	NPC281298
0.887	High Similarity	NPC39793
0.8852	High Similarity	NPC5851
0.8852	High Similarity	NPC170844
0.8852	High Similarity	NPC476968
0.8852	High Similarity	NPC86030
0.8843	High Similarity	NPC106511
0.8839	High Similarity	NPC55300
0.8833	High Similarity	NPC234400
0.8833	High Similarity	NPC251855
0.8833	High Similarity	NPC208950
0.8833	High Similarity	NPC17943
0.8833	High Similarity	NPC60885
0.8833	High Similarity	NPC203133
0.8833	High Similarity	NPC193544
0.8833	High Similarity	NPC233410
0.8833	High Similarity	NPC57490
0.8833	High Similarity	NPC475169
0.8833	High Similarity	NPC116907
0.8833	High Similarity	NPC472093
0.8833	High Similarity	NPC298757
0.8833	High Similarity	NPC221077
0.8833	High Similarity	NPC117214
0.8824	High Similarity	NPC280704
0.8824	High Similarity	NPC197757
0.8824	High Similarity	NPC228922
0.8814	High Similarity	NPC127389
0.8814	High Similarity	NPC290451
0.8814	High Similarity	NPC285289
0.8803	High Similarity	NPC227217
0.8803	High Similarity	NPC56214
0.8803	High Similarity	NPC232316
0.8803	High Similarity	NPC61516
0.8803	High Similarity	NPC10932
0.8803	High Similarity	NPC165133
0.8803	High Similarity	NPC247364
0.8803	High Similarity	NPC232084
0.8803	High Similarity	NPC242885
0.8803	High Similarity	NPC95614
0.8803	High Similarity	NPC117780
0.8796	High Similarity	NPC305205
0.878	High Similarity	NPC92164
0.878	High Similarity	NPC472338
0.878	High Similarity	NPC241522
0.878	High Similarity	NPC42300
0.878	High Similarity	NPC257582
0.878	High Similarity	NPC153739
0.878	High Similarity	NPC187998
0.878	High Similarity	NPC143483
0.878	High Similarity	NPC64201
0.878	High Similarity	NPC77040
0.878	High Similarity	NPC242807
0.878	High Similarity	NPC145305
0.878	High Similarity	NPC174495
0.877	High Similarity	NPC128208
0.877	High Similarity	NPC472968
0.877	High Similarity	NPC11258
0.877	High Similarity	NPC282703
0.877	High Similarity	NPC21867
0.877	High Similarity	NPC72529
0.877	High Similarity	NPC184733
0.877	High Similarity	NPC45774
0.877	High Similarity	NPC129570
0.8761	High Similarity	NPC165646
0.876	High Similarity	NPC78974
0.876	High Similarity	NPC214406
0.876	High Similarity	NPC18924
0.876	High Similarity	NPC28730
0.876	High Similarity	NPC44748
0.876	High Similarity	NPC103823
0.876	High Similarity	NPC223136
0.875	High Similarity	NPC183446
0.8739	High Similarity	NPC71579
0.8739	High Similarity	NPC473411
0.8739	High Similarity	NPC262253
0.8718	High Similarity	NPC226629
0.8718	High Similarity	NPC477803
0.871	High Similarity	NPC472597
0.871	High Similarity	NPC248307
0.871	High Similarity	NPC470096
0.871	High Similarity	NPC474017
0.871	High Similarity	NPC470095
0.871	High Similarity	NPC65942
0.871	High Similarity	NPC277804
0.8707	High Similarity	NPC86947
0.8704	High Similarity	NPC12714
0.8704	High Similarity	NPC110764
0.8704	High Similarity	NPC310905
0.8699	High Similarity	NPC475875
0.8699	High Similarity	NPC212015
0.8689	High Similarity	NPC21563
0.8689	High Similarity	NPC169474
0.8689	High Similarity	NPC210355
0.8689	High Similarity	NPC124452
0.8689	High Similarity	NPC127587
0.8689	High Similarity	NPC246620
0.8689	High Similarity	NPC266555
0.8689	High Similarity	NPC82679
0.8689	High Similarity	NPC282000
0.8689	High Similarity	NPC324112
0.8689	High Similarity	NPC159968
0.8689	High Similarity	NPC281020
0.8689	High Similarity	NPC74817
0.8689	High Similarity	NPC236791
0.8689	High Similarity	NPC293054
0.8684	High Similarity	NPC204120
0.8678	High Similarity	NPC82483
0.8678	High Similarity	NPC299584
0.8678	High Similarity	NPC271985
0.8678	High Similarity	NPC265483
0.8667	High Similarity	NPC31344
0.8667	High Similarity	NPC238810
0.8667	High Similarity	NPC233526
0.8667	High Similarity	NPC84086
0.8667	High Similarity	NPC136319

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 NPC221049 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	356
0.1-0.2	979
0.2-0.3	1988
0.3-0.4	2688
0.4-0.5	1521
0.5-0.6	916
0.6-0.7	578
0.7-0.8	113
0.8-0.85	9
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9537	High Similarity	NPD228	Approved
0.8852	High Similarity	NPD3027	Phase 3
0.8403	Intermediate Similarity	NPD1357	Approved
0.8346	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8346	Intermediate Similarity	NPD1613	Approved
0.8246	Intermediate Similarity	NPD2684	Approved
0.8211	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD5283	Phase 1
0.8203	Intermediate Similarity	NPD1558	Phase 1
0.8175	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD9296	Approved
0.8095	Intermediate Similarity	NPD9494	Approved
0.8095	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8062	Intermediate Similarity	NPD3620	Phase 2
0.8062	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD3705	Approved
0.8	Intermediate Similarity	NPD290	Approved
0.7984	Intermediate Similarity	NPD2674	Phase 3
0.7966	Intermediate Similarity	NPD7843	Approved
0.7917	Intermediate Similarity	NPD7157	Approved
0.7863	Intermediate Similarity	NPD3022	Approved
0.7863	Intermediate Similarity	NPD3021	Approved
0.7778	Intermediate Similarity	NPD2982	Phase 2
0.7778	Intermediate Similarity	NPD2983	Phase 2
0.7769	Intermediate Similarity	NPD3145	Approved
0.7769	Intermediate Similarity	NPD3144	Approved
0.7742	Intermediate Similarity	NPD9384	Approved
0.7742	Intermediate Similarity	NPD9381	Approved
0.7724	Intermediate Similarity	NPD1548	Phase 1
0.7721	Intermediate Similarity	NPD3060	Approved
0.7719	Intermediate Similarity	NPD291	Approved
0.7698	Intermediate Similarity	NPD2981	Phase 2
0.7674	Intermediate Similarity	NPD3018	Phase 2
0.7642	Intermediate Similarity	NPD5536	Phase 2
0.7638	Intermediate Similarity	NPD9622	Approved
0.7619	Intermediate Similarity	NPD1610	Phase 2
0.7607	Intermediate Similarity	NPD968	Approved
0.7591	Intermediate Similarity	NPD4237	Approved
0.7591	Intermediate Similarity	NPD4236	Phase 3
0.7538	Intermediate Similarity	NPD2861	Phase 2
0.7521	Intermediate Similarity	NPD9379	Approved
0.7521	Intermediate Similarity	NPD821	Approved
0.7521	Intermediate Similarity	NPD9377	Approved
0.75	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD1091	Approved
0.748	Intermediate Similarity	NPD6671	Approved
0.7462	Intermediate Similarity	NPD9620	Approved
0.7462	Intermediate Similarity	NPD9621	Approved
0.7462	Intermediate Similarity	NPD9619	Approved
0.7445	Intermediate Similarity	NPD1375	Discontinued
0.7445	Intermediate Similarity	NPD7266	Discontinued
0.7444	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD8651	Approved
0.7413	Intermediate Similarity	NPD1653	Approved
0.7395	Intermediate Similarity	NPD1358	Approved
0.7388	Intermediate Similarity	NPD4060	Phase 1
0.7387	Intermediate Similarity	NPD9365	Approved
0.7364	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD4908	Phase 1
0.7348	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD2934	Approved
0.7345	Intermediate Similarity	NPD2933	Approved
0.7344	Intermediate Similarity	NPD422	Phase 1
0.7333	Intermediate Similarity	NPD230	Phase 1
0.7329	Intermediate Similarity	NPD1934	Approved
0.7328	Intermediate Similarity	NPD6584	Phase 3
0.7328	Intermediate Similarity	NPD1242	Phase 1
0.7328	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD6516	Phase 2
0.7323	Intermediate Similarity	NPD4626	Approved
0.7323	Intermediate Similarity	NPD5846	Approved
0.7323	Intermediate Similarity	NPD1778	Approved
0.7315	Intermediate Similarity	NPD111	Approved
0.7292	Intermediate Similarity	NPD3687	Approved
0.7292	Intermediate Similarity	NPD3686	Approved
0.7281	Intermediate Similarity	NPD844	Approved
0.7281	Intermediate Similarity	NPD2860	Approved
0.7281	Intermediate Similarity	NPD2859	Approved
0.7279	Intermediate Similarity	NPD2977	Approved
0.7279	Intermediate Similarity	NPD2978	Approved
0.7265	Intermediate Similarity	NPD846	Approved
0.7265	Intermediate Similarity	NPD940	Approved
0.7254	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD2161	Phase 2
0.7241	Intermediate Similarity	NPD3020	Approved
0.7239	Intermediate Similarity	NPD601	Approved
0.7239	Intermediate Similarity	NPD598	Approved
0.7239	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD597	Approved
0.7234	Intermediate Similarity	NPD5241	Discontinued
0.7231	Intermediate Similarity	NPD4749	Approved
0.7217	Intermediate Similarity	NPD288	Approved
0.7214	Intermediate Similarity	NPD4162	Approved
0.7207	Intermediate Similarity	NPD9295	Approved
0.7206	Intermediate Similarity	NPD5735	Approved
0.7203	Intermediate Similarity	NPD4123	Phase 3
0.7194	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD1136	Approved
0.7185	Intermediate Similarity	NPD1132	Approved
0.7185	Intermediate Similarity	NPD1130	Approved
0.7181	Intermediate Similarity	NPD3882	Suspended
0.7179	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD3134	Approved
0.7165	Intermediate Similarity	NPD9545	Approved
0.7164	Intermediate Similarity	NPD3179	Approved
0.7164	Intermediate Similarity	NPD3180	Approved
0.7162	Intermediate Similarity	NPD2801	Approved
0.7154	Intermediate Similarity	NPD1608	Approved
0.7154	Intermediate Similarity	NPD2231	Phase 2
0.7154	Intermediate Similarity	NPD2235	Phase 2
0.7153	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7153	Discontinued
0.7133	Intermediate Similarity	NPD1511	Approved
0.7133	Intermediate Similarity	NPD1774	Approved
0.7132	Intermediate Similarity	NPD3496	Discontinued
0.7132	Intermediate Similarity	NPD2238	Phase 2
0.7131	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD5451	Approved
0.7131	Intermediate Similarity	NPD556	Approved
0.7121	Intermediate Similarity	NPD1817	Approved
0.7121	Intermediate Similarity	NPD1820	Approved
0.7121	Intermediate Similarity	NPD1819	Approved
0.7121	Intermediate Similarity	NPD1818	Approved
0.7113	Intermediate Similarity	NPD2677	Approved
0.7113	Intermediate Similarity	NPD2219	Phase 1
0.7111	Intermediate Similarity	NPD5111	Phase 2
0.7111	Intermediate Similarity	NPD5110	Phase 2
0.7111	Intermediate Similarity	NPD5718	Phase 2
0.7111	Intermediate Similarity	NPD5109	Approved
0.7109	Intermediate Similarity	NPD5691	Approved
0.7101	Intermediate Similarity	NPD4536	Approved
0.7101	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD4538	Approved
0.7101	Intermediate Similarity	NPD6111	Discontinued
0.7099	Intermediate Similarity	NPD6582	Phase 2
0.7099	Intermediate Similarity	NPD6583	Phase 3
0.7092	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD6674	Discontinued
0.7092	Intermediate Similarity	NPD5177	Phase 3
0.7083	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD3092	Approved
0.7071	Intermediate Similarity	NPD3540	Phase 1
0.7063	Intermediate Similarity	NPD709	Approved
0.7059	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD2667	Approved
0.7054	Intermediate Similarity	NPD2668	Approved
0.7047	Intermediate Similarity	NPD5773	Approved
0.7047	Intermediate Similarity	NPD5772	Approved
0.7047	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD2922	Phase 1
0.7045	Intermediate Similarity	NPD1283	Approved
0.7045	Intermediate Similarity	NPD6696	Suspended
0.7042	Intermediate Similarity	NPD4628	Phase 3
0.7042	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD6331	Phase 2
0.7042	Intermediate Similarity	NPD4110	Phase 3
0.704	Intermediate Similarity	NPD1241	Discontinued
0.7037	Intermediate Similarity	NPD7095	Approved
0.7037	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4625	Phase 3
0.7034	Intermediate Similarity	NPD1512	Approved
0.7031	Intermediate Similarity	NPD1182	Approved
0.7029	Intermediate Similarity	NPD6653	Approved
0.7023	Intermediate Similarity	NPD2232	Approved
0.7023	Intermediate Similarity	NPD2233	Approved
0.7023	Intermediate Similarity	NPD2230	Approved
0.7014	Intermediate Similarity	NPD4357	Discontinued
0.7007	Intermediate Similarity	NPD3061	Approved
0.7007	Intermediate Similarity	NPD3062	Approved
0.7007	Intermediate Similarity	NPD3059	Approved
0.7007	Intermediate Similarity	NPD4005	Discontinued
0.7	Intermediate Similarity	NPD2563	Approved
0.7	Intermediate Similarity	NPD3539	Phase 1
0.7	Intermediate Similarity	NPD2560	Approved
0.6993	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6190	Approved
0.6992	Remote Similarity	NPD987	Approved
0.6986	Remote Similarity	NPD2122	Discontinued
0.6984	Remote Similarity	NPD9299	Approved
0.698	Remote Similarity	NPD37	Approved
0.6977	Remote Similarity	NPD1651	Approved
0.6974	Remote Similarity	NPD6234	Discontinued
0.697	Remote Similarity	NPD3685	Discontinued
0.697	Remote Similarity	NPD1669	Approved
0.6968	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6166	Phase 2
0.6968	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD600	Approved
0.6963	Remote Similarity	NPD596	Approved
0.6959	Remote Similarity	NPD4675	Approved
0.6959	Remote Similarity	NPD4678	Approved
0.6957	Remote Similarity	NPD4340	Discontinued
0.6957	Remote Similarity	NPD3657	Discovery
0.6957	Remote Similarity	NPD447	Suspended
0.695	Remote Similarity	NPD5763	Approved
0.695	Remote Similarity	NPD5762	Approved
0.694	Remote Similarity	NPD3690	Phase 2

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