NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	124.05
Volume:	130.743
LogP:	1.505
LogD:	1.448
LogS:	-0.524
# Rotatable Bonds:	1
TPSA:	29.46
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.613
Synthetic Accessibility Score:	1.432
Fsp3:	0.143
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:	-4.38
MDCK Permeability:	1.876496935437899e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.116
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.469

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.131
Plasma Protein Binding (PPB):	64.96714782714844%
Volume Distribution (VD):	2.166
Pgp-substrate:	20.010427474975586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.933
CYP1A2-substrate:	0.885
CYP2C19-inhibitor:	0.524
CYP2C19-substrate:	0.684
CYP2C9-inhibitor:	0.087
CYP2C9-substrate:	0.941
CYP2D6-inhibitor:	0.615
CYP2D6-substrate:	0.9
CYP3A4-inhibitor:	0.152
CYP3A4-substrate:	0.233

ADMET: Excretion

Clearance (CL):	13.132
Half-life (T1/2):	0.893

ADMET: Toxicity

hERG Blockers:	0.044
Human Hepatotoxicity (H-HT):	0.057
Drug-inuced Liver Injury (DILI):	0.044
AMES Toxicity:	0.031
Rat Oral Acute Toxicity:	0.165
Maximum Recommended Daily Dose:	0.077
Skin Sensitization:	0.903
Carcinogencity:	0.409
Eye Corrosion:	0.972
Eye Irritation:	0.993
Respiratory Toxicity:	0.309

Download Data

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

Natural Product: NPC16649

Natural Product ID:	NPC16649
*Common Name:**	1-Hydroxy-3-Methoxybenzene
IUPAC Name:	3-methoxyphenol
Synonyms:	3-Methoxy-Phenol; 3-Methoxyphenol
Standard InCHIKey:	ASHGTJPOSUFTGB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C7H8O2/c1-9-7-4-2-3-6(8)5-7/h2-5,8H,1H3
SMILES:	COc1cccc(c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL57891
PubChem CID:	9007
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
NPO31390	Cynanchum paniculatum	Species	Apocynaceae	Eukaryota	roots	n.a.	n.a.	PMID[14738392]
NPO18093	Rosa chinensis	Species	Rosaceae	Eukaryota	Flowers	Muyang, China	n.a.	PMID[24621197]
NPO18093	Rosa chinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31390	Cynanchum paniculatum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18093	Rosa chinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24694	Vincetoxicum pycnostelma	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18093	Rosa chinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31390	Cynanchum paniculatum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18093	Rosa chinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24694	Vincetoxicum pycnostelma	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

☑ 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	11

Activity Type	# Activity
Cell Line	3
Individual Protein	1
Organism	1
Others	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT589	Individual Protein	Serum albumin	Bos taurus	Log 1/C	=	3.54	n.a.	PMID[470680]
NPT137	Cell Line	L1210	Mus musculus	log(1/ID50)	=	1.31	n.a.	PMID[470682]
NPT137	Cell Line	L1210	Mus musculus	log(1/ID50)	=	3.71	n.a.	PMID[470682]
NPT137	Cell Line	L1210	Mus musculus	Activity	<	15.0	%	PMID[470682]
NPT27	Others	Unspecified		Log k' w	=	1.254	n.a.	PMID[470680]
NPT35	Others	n.a.		LogP	=	1.58	n.a.	PMID[470680]
NPT35	Others	n.a.		Log PNalk	=	-0.88	n.a.	PMID[470681]
NPT27	Others	Unspecified		log Ks	=	2.11	n.a.	PMID[470683]
NPT1365	Organism	Trichoplusia ni	Trichoplusia ni	Activity	=	44.7	%	PMID[470685]
NPT35	Others	n.a.		LogP	=	1.58	n.a.	PMID[470686]
NPT35	Others	n.a.		LogP	=	1.28	n.a.	PMID[470686]

☑ 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 NPC16649 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	416
0.1-0.2	4227
0.2-0.3	12878
0.3-0.4	6493
0.4-0.5	5698
0.5-0.6	8918
0.6-0.7	3453
0.7-0.8	560
0.8-0.85	42
0.85-0.9	8
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9326	High Similarity	NPC302546
0.9213	High Similarity	NPC47422
0.9072	High Similarity	NPC307875
0.898	High Similarity	NPC473653
0.8889	High Similarity	NPC124712
0.8791	High Similarity	NPC157213
0.8788	High Similarity	NPC164576
0.8788	High Similarity	NPC232654
0.8636	High Similarity	NPC270094
0.8627	High Similarity	NPC94045
0.8523	High Similarity	NPC4154
0.8462	Intermediate Similarity	NPC280606
0.8447	Intermediate Similarity	NPC168657
0.8409	Intermediate Similarity	NPC124576
0.8365	Intermediate Similarity	NPC296920
0.8365	Intermediate Similarity	NPC90520
0.8333	Intermediate Similarity	NPC114325
0.8302	Intermediate Similarity	NPC180508
0.8302	Intermediate Similarity	NPC22610
0.8302	Intermediate Similarity	NPC276737
0.8302	Intermediate Similarity	NPC228287
0.8269	Intermediate Similarity	NPC247871
0.8224	Intermediate Similarity	NPC167934
0.8224	Intermediate Similarity	NPC185541
0.8224	Intermediate Similarity	NPC53906
0.8224	Intermediate Similarity	NPC464
0.819	Intermediate Similarity	NPC255068
0.8152	Intermediate Similarity	NPC23837
0.8148	Intermediate Similarity	NPC54507
0.8148	Intermediate Similarity	NPC203113
0.8148	Intermediate Similarity	NPC229147
0.8148	Intermediate Similarity	NPC150624
0.8148	Intermediate Similarity	NPC141090
0.8148	Intermediate Similarity	NPC85292
0.8119	Intermediate Similarity	NPC305205
0.8085	Intermediate Similarity	NPC280254
0.8073	Intermediate Similarity	NPC50521
0.8073	Intermediate Similarity	NPC221549
0.8073	Intermediate Similarity	NPC470759
0.8073	Intermediate Similarity	NPC69261
0.8073	Intermediate Similarity	NPC195466
0.8073	Intermediate Similarity	NPC33270
0.8073	Intermediate Similarity	NPC474933
0.8073	Intermediate Similarity	NPC244816
0.8073	Intermediate Similarity	NPC15860
0.8073	Intermediate Similarity	NPC259638
0.8073	Intermediate Similarity	NPC127894
0.8073	Intermediate Similarity	NPC219070
0.8056	Intermediate Similarity	NPC808
0.8	Intermediate Similarity	NPC131118
0.7982	Intermediate Similarity	NPC193067
0.7982	Intermediate Similarity	NPC114064
0.7981	Intermediate Similarity	NPC35543
0.7928	Intermediate Similarity	NPC184302
0.7928	Intermediate Similarity	NPC226629
0.7928	Intermediate Similarity	NPC20674
0.7905	Intermediate Similarity	NPC245115
0.7895	Intermediate Similarity	NPC206876
0.7857	Intermediate Similarity	NPC295295
0.7857	Intermediate Similarity	NPC229401
0.7838	Intermediate Similarity	NPC74821
0.7838	Intermediate Similarity	NPC190514
0.7835	Intermediate Similarity	NPC288923
0.7835	Intermediate Similarity	NPC318429
0.783	Intermediate Similarity	NPC82016
0.7822	Intermediate Similarity	NPC314803
0.7822	Intermediate Similarity	NPC307039
0.781	Intermediate Similarity	NPC251306
0.7788	Intermediate Similarity	NPC166759
0.7788	Intermediate Similarity	NPC102639
0.7788	Intermediate Similarity	NPC8302
0.7768	Intermediate Similarity	NPC137294
0.7768	Intermediate Similarity	NPC85895
0.7768	Intermediate Similarity	NPC295259
0.7757	Intermediate Similarity	NPC2682
0.7757	Intermediate Similarity	NPC106141
0.7757	Intermediate Similarity	NPC303521
0.7727	Intermediate Similarity	NPC100980
0.7719	Intermediate Similarity	NPC476633
0.7719	Intermediate Similarity	NPC75713
0.7719	Intermediate Similarity	NPC212965
0.7719	Intermediate Similarity	NPC285289
0.7699	Intermediate Similarity	NPC93398
0.7699	Intermediate Similarity	NPC10932
0.7699	Intermediate Similarity	NPC474565
0.7699	Intermediate Similarity	NPC232084
0.7699	Intermediate Similarity	NPC61516
0.7699	Intermediate Similarity	NPC247364
0.7699	Intermediate Similarity	NPC258979
0.7699	Intermediate Similarity	NPC8283
0.7692	Intermediate Similarity	NPC12987
0.7692	Intermediate Similarity	NPC474603
0.7685	Intermediate Similarity	NPC203924
0.7664	Intermediate Similarity	NPC165386
0.7652	Intermediate Similarity	NPC473411
0.7652	Intermediate Similarity	NPC120638
0.7652	Intermediate Similarity	NPC36016
0.7652	Intermediate Similarity	NPC262253
0.7652	Intermediate Similarity	NPC474864
0.7652	Intermediate Similarity	NPC18128
0.7652	Intermediate Similarity	NPC71579
0.7652	Intermediate Similarity	NPC77789
0.7652	Intermediate Similarity	NPC100099
0.7647	Intermediate Similarity	NPC100870
0.7647	Intermediate Similarity	NPC80027
0.7632	Intermediate Similarity	NPC218753
0.7589	Intermediate Similarity	NPC76915
0.7589	Intermediate Similarity	NPC151617
0.7586	Intermediate Similarity	NPC238810
0.7586	Intermediate Similarity	NPC233526
0.7586	Intermediate Similarity	NPC84086
0.7586	Intermediate Similarity	NPC282496
0.7586	Intermediate Similarity	NPC38761
0.7586	Intermediate Similarity	NPC136319
0.7586	Intermediate Similarity	NPC95168
0.7586	Intermediate Similarity	NPC474160
0.7586	Intermediate Similarity	NPC76465
0.7582	Intermediate Similarity	NPC65517
0.7579	Intermediate Similarity	NPC125306
0.7573	Intermediate Similarity	NPC166761
0.757	Intermediate Similarity	NPC241549
0.7565	Intermediate Similarity	NPC54972
0.7565	Intermediate Similarity	NPC52247
0.7565	Intermediate Similarity	NPC193364
0.7565	Intermediate Similarity	NPC49341
0.7551	Intermediate Similarity	NPC99886
0.7551	Intermediate Similarity	NPC259134
0.7551	Intermediate Similarity	NPC8002
0.7551	Intermediate Similarity	NPC177844
0.7549	Intermediate Similarity	NPC291789
0.7547	Intermediate Similarity	NPC113457
0.7545	Intermediate Similarity	NPC204120
0.7522	Intermediate Similarity	NPC63083
0.7521	Intermediate Similarity	NPC5796
0.7521	Intermediate Similarity	NPC134195
0.7521	Intermediate Similarity	NPC246648
0.7521	Intermediate Similarity	NPC228503
0.7521	Intermediate Similarity	NPC206487
0.7521	Intermediate Similarity	NPC221090
0.7521	Intermediate Similarity	NPC106914
0.7521	Intermediate Similarity	NPC98509
0.7521	Intermediate Similarity	NPC138248
0.7521	Intermediate Similarity	NPC86502
0.7521	Intermediate Similarity	NPC197351
0.7521	Intermediate Similarity	NPC270030
0.7521	Intermediate Similarity	NPC183446
0.75	Intermediate Similarity	NPC152722
0.75	Intermediate Similarity	NPC51633
0.75	Intermediate Similarity	NPC74137
0.75	Intermediate Similarity	NPC41562
0.7478	Intermediate Similarity	NPC199023
0.7477	Intermediate Similarity	NPC233320
0.7477	Intermediate Similarity	NPC142319
0.7475	Intermediate Similarity	NPC71853
0.7458	Intermediate Similarity	NPC105031
0.7458	Intermediate Similarity	NPC251855
0.7458	Intermediate Similarity	NPC278955
0.7458	Intermediate Similarity	NPC188022
0.7458	Intermediate Similarity	NPC271985
0.7458	Intermediate Similarity	NPC234400
0.7458	Intermediate Similarity	NPC57490
0.7458	Intermediate Similarity	NPC113495
0.7458	Intermediate Similarity	NPC17943
0.7458	Intermediate Similarity	NPC103420
0.7458	Intermediate Similarity	NPC299584
0.7458	Intermediate Similarity	NPC472093
0.7458	Intermediate Similarity	NPC17809
0.7458	Intermediate Similarity	NPC117214
0.7458	Intermediate Similarity	NPC475169
0.7458	Intermediate Similarity	NPC102540
0.7458	Intermediate Similarity	NPC203133
0.7458	Intermediate Similarity	NPC298757
0.7458	Intermediate Similarity	NPC476254
0.7458	Intermediate Similarity	NPC131397
0.7458	Intermediate Similarity	NPC221077
0.7458	Intermediate Similarity	NPC300326
0.7458	Intermediate Similarity	NPC105718
0.7458	Intermediate Similarity	NPC105925
0.7458	Intermediate Similarity	NPC265483
0.7458	Intermediate Similarity	NPC285040
0.7458	Intermediate Similarity	NPC116907
0.7458	Intermediate Similarity	NPC193544
0.7458	Intermediate Similarity	NPC58279
0.7458	Intermediate Similarity	NPC60885
0.7458	Intermediate Similarity	NPC82483
0.7458	Intermediate Similarity	NPC233410
0.7458	Intermediate Similarity	NPC208950
0.7456	Intermediate Similarity	NPC214289
0.7436	Intermediate Similarity	NPC220598
0.7436	Intermediate Similarity	NPC197757
0.7436	Intermediate Similarity	NPC165375
0.7436	Intermediate Similarity	NPC121115
0.7436	Intermediate Similarity	NPC192810
0.7436	Intermediate Similarity	NPC228922
0.7429	Intermediate Similarity	NPC146798
0.7429	Intermediate Similarity	NPC222522
0.7429	Intermediate Similarity	NPC242342
0.7429	Intermediate Similarity	NPC106396
0.7429	Intermediate Similarity	NPC302219
0.7429	Intermediate Similarity	NPC71002

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 NPC16649 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	385
0.1-0.2	1257
0.2-0.3	2714
0.3-0.4	2533
0.4-0.5	1310
0.5-0.6	781
0.6-0.7	146
0.7-0.8	19
0.8-0.85	2
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8791	High Similarity	NPD9295	Approved
0.8636	High Similarity	NPD9089	Approved
0.8523	High Similarity	NPD9093	Approved
0.8333	Intermediate Similarity	NPD9296	Approved
0.8085	Intermediate Similarity	NPD9094	Approved
0.7838	Intermediate Similarity	NPD1548	Phase 1
0.7835	Intermediate Similarity	NPD9365	Approved
0.7727	Intermediate Similarity	NPD9087	Approved
0.767	Intermediate Similarity	NPD291	Approved
0.7582	Intermediate Similarity	NPD9088	Approved
0.7565	Intermediate Similarity	NPD422	Phase 1
0.7565	Intermediate Similarity	NPD1610	Phase 2
0.75	Intermediate Similarity	NPD940	Approved
0.75	Intermediate Similarity	NPD846	Approved
0.7404	Intermediate Similarity	NPD1242	Phase 1
0.7383	Intermediate Similarity	NPD968	Approved
0.7315	Intermediate Similarity	NPD290	Approved
0.7288	Intermediate Similarity	NPD4749	Approved
0.7281	Intermediate Similarity	NPD1408	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4908	Phase 1
0.7217	Intermediate Similarity	NPD7533	Approved
0.7217	Intermediate Similarity	NPD7534	Approved
0.7216	Intermediate Similarity	NPD111	Approved
0.7213	Intermediate Similarity	NPD3027	Phase 3
0.7207	Intermediate Similarity	NPD228	Approved
0.7156	Intermediate Similarity	NPD9552	Approved
0.7154	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD4625	Phase 3
0.704	Intermediate Similarity	NPD1240	Approved
0.7037	Intermediate Similarity	NPD9501	Approved
0.7027	Intermediate Similarity	NPD556	Approved
0.7018	Intermediate Similarity	NPD9299	Approved
0.7016	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2982	Phase 2
0.7	Intermediate Similarity	NPD2983	Phase 2
0.6992	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD1091	Approved
0.6937	Remote Similarity	NPD2684	Approved
0.6929	Remote Similarity	NPD1607	Approved
0.6917	Remote Similarity	NPD2981	Phase 2
0.6911	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD1613	Approved
0.688	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4750	Phase 3
0.6869	Remote Similarity	NPD9073	Approved
0.6842	Remote Similarity	NPD821	Approved
0.681	Remote Similarity	NPD6671	Approved
0.6774	Remote Similarity	NPD3018	Phase 2
0.6762	Remote Similarity	NPD2934	Approved
0.6762	Remote Similarity	NPD2933	Approved
0.6757	Remote Similarity	NPD3134	Approved
0.6698	Remote Similarity	NPD2860	Approved
0.6698	Remote Similarity	NPD2859	Approved
0.6696	Remote Similarity	NPD1358	Approved
0.6696	Remote Similarity	NPD7843	Approved
0.6692	Remote Similarity	NPD1510	Phase 2
0.6667	Remote Similarity	NPD1778	Approved
0.6641	Remote Similarity	NPD1551	Phase 2
0.6639	Remote Similarity	NPD9545	Approved
0.661	Remote Similarity	NPD9493	Approved
0.6604	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD3537	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD1357	Approved
0.6579	Remote Similarity	NPD5451	Approved
0.6574	Remote Similarity	NPD9273	Approved
0.6567	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.656	Remote Similarity	NPD1469	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD5374	Approved
0.6549	Remote Similarity	NPD9624	Approved
0.6549	Remote Similarity	NPD5373	Approved
0.6542	Remote Similarity	NPD844	Approved
0.6541	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD1549	Phase 2
0.6538	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD3225	Approved
0.6525	Remote Similarity	NPD191	Approved
0.6525	Remote Similarity	NPD7157	Approved
0.6522	Remote Similarity	NPD2671	Approved
0.6522	Remote Similarity	NPD2673	Approved
0.6515	Remote Similarity	NPD6100	Approved
0.6515	Remote Similarity	NPD6099	Approved
0.6514	Remote Similarity	NPD3020	Approved
0.6509	Remote Similarity	NPD845	Approved
0.6508	Remote Similarity	NPD2861	Phase 2
0.6504	Remote Similarity	NPD1608	Approved
0.6504	Remote Similarity	NPD9717	Approved
0.6481	Remote Similarity	NPD288	Approved
0.6462	Remote Similarity	NPD5124	Phase 1
0.6462	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6583	Phase 3
0.6452	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6582	Phase 2
0.6452	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD5788	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD7213	Phase 3
0.6423	Remote Similarity	NPD7212	Phase 2
0.6417	Remote Similarity	NPD254	Approved
0.641	Remote Similarity	NPD1138	Approved
0.641	Remote Similarity	NPD769	Approved
0.64	Remote Similarity	NPD6696	Suspended
0.6393	Remote Similarity	NPD4626	Approved
0.6393	Remote Similarity	NPD2667	Approved
0.6393	Remote Similarity	NPD2668	Approved
0.6387	Remote Similarity	NPD709	Approved
0.6385	Remote Similarity	NPD2238	Phase 2
0.6377	Remote Similarity	NPD7447	Phase 1
0.6377	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD9697	Approved
0.6371	Remote Similarity	NPD2233	Approved
0.6371	Remote Similarity	NPD2232	Approved
0.6371	Remote Similarity	NPD2230	Approved
0.637	Remote Similarity	NPD1652	Phase 2
0.6356	Remote Similarity	NPD1241	Discontinued
0.6356	Remote Similarity	NPD5283	Phase 1
0.6349	Remote Similarity	NPD1203	Approved
0.6349	Remote Similarity	NPD2797	Approved
0.6341	Remote Similarity	NPD3847	Discontinued
0.6341	Remote Similarity	NPD3496	Discontinued
0.6336	Remote Similarity	NPD230	Phase 1
0.6328	Remote Similarity	NPD600	Approved
0.6328	Remote Similarity	NPD596	Approved
0.6325	Remote Similarity	NPD1139	Approved
0.6325	Remote Similarity	NPD1137	Approved
0.6324	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD3750	Approved
0.6311	Remote Similarity	NPD1797	Approved
0.6311	Remote Similarity	NPD1798	Approved
0.6304	Remote Similarity	NPD4357	Discontinued
0.6299	Remote Similarity	NPD6584	Phase 3
0.6293	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.629	Remote Similarity	NPD1535	Discovery
0.6277	Remote Similarity	NPD2219	Phase 1
0.6273	Remote Similarity	NPD68	Approved
0.6273	Remote Similarity	NPD9096	Approved
0.6273	Remote Similarity	NPD9095	Approved
0.6273	Remote Similarity	NPD9097	Approved
0.6271	Remote Similarity	NPD5535	Approved
0.626	Remote Similarity	NPD17	Approved
0.626	Remote Similarity	NPD1558	Phase 1
0.625	Remote Similarity	NPD9494	Approved
0.6241	Remote Similarity	NPD2200	Suspended
0.624	Remote Similarity	NPD2231	Phase 2
0.624	Remote Similarity	NPD1481	Phase 2
0.624	Remote Similarity	NPD2235	Phase 2
0.6239	Remote Similarity	NPD1809	Phase 2
0.6231	Remote Similarity	NPD1296	Phase 2
0.6231	Remote Similarity	NPD1048	Approved
0.623	Remote Similarity	NPD1894	Discontinued
0.6224	Remote Similarity	NPD9294	Approved
0.6222	Remote Similarity	NPD3540	Phase 1
0.622	Remote Similarity	NPD3827	Clinical (unspecified phase)
0.622	Remote Similarity	NPD6362	Approved
0.622	Remote Similarity	NPD2082	Clinical (unspecified phase)
0.621	Remote Similarity	NPD915	Approved
0.6204	Remote Similarity	NPD3892	Phase 2
0.6194	Remote Similarity	NPD7033	Discontinued
0.619	Remote Similarity	NPD3685	Discontinued
0.619	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6187	Remote Similarity	NPD1511	Approved
0.6183	Remote Similarity	NPD840	Approved
0.6183	Remote Similarity	NPD839	Approved
0.6172	Remote Similarity	NPD5647	Approved
0.6172	Remote Similarity	NPD3690	Phase 2
0.6172	Remote Similarity	NPD3691	Phase 2
0.6167	Remote Similarity	NPD595	Approved
0.6167	Remote Similarity	NPD593	Approved
0.6165	Remote Similarity	NPD3052	Approved
0.6165	Remote Similarity	NPD3054	Approved
0.616	Remote Similarity	NPD3705	Approved
0.6154	Remote Similarity	NPD3180	Approved
0.6154	Remote Similarity	NPD3179	Approved
0.6148	Remote Similarity	NPD1103	Approved
0.6148	Remote Similarity	NPD2796	Approved
0.6148	Remote Similarity	NPD3539	Phase 1
0.6148	Remote Similarity	NPD9092	Discovery
0.6148	Remote Similarity	NPD5536	Phase 2
0.6148	Remote Similarity	NPD1102	Approved
0.6143	Remote Similarity	NPD3157	Approved
0.6143	Remote Similarity	NPD3158	Phase 1
0.6143	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD1283	Approved
0.6142	Remote Similarity	NPD8651	Approved
0.614	Remote Similarity	NPD9610	Approved
0.614	Remote Similarity	NPD9608	Approved
0.6129	Remote Similarity	NPD5846	Approved
0.6129	Remote Similarity	NPD6516	Phase 2
0.6127	Remote Similarity	NPD1653	Approved
0.6121	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD9507	Approved
0.6119	Remote Similarity	NPD6111	Discontinued
0.6116	Remote Similarity	NPD2557	Approved
0.6107	Remote Similarity	NPD3145	Approved
0.6107	Remote Similarity	NPD3144	Approved
0.6107	Remote Similarity	NPD3056	Clinical (unspecified phase)

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