NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	152.05
Volume:	154.193
LogP:	1.846
LogD:	1.879
LogS:	-1.579
# Rotatable Bonds:	2
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.614
Synthetic Accessibility Score:	1.519
Fsp3:	0.125
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:	-4.417
MDCK Permeability:	2.2051766791264527e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.888

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.601
Plasma Protein Binding (PPB):	78.03795623779297%
Volume Distribution (VD):	0.818
Pgp-substrate:	16.39533042907715%

ADMET: Metabolism

CYP1A2-inhibitor:	0.95
CYP1A2-substrate:	0.735
CYP2C19-inhibitor:	0.474
CYP2C19-substrate:	0.135
CYP2C9-inhibitor:	0.132
CYP2C9-substrate:	0.888
CYP2D6-inhibitor:	0.278
CYP2D6-substrate:	0.606
CYP3A4-inhibitor:	0.116
CYP3A4-substrate:	0.197

ADMET: Excretion

Clearance (CL):	13.577
Half-life (T1/2):	0.91

ADMET: Toxicity

hERG Blockers:	0.05
Human Hepatotoxicity (H-HT):	0.035
Drug-inuced Liver Injury (DILI):	0.44
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.027
Maximum Recommended Daily Dose:	0.016
Skin Sensitization:	0.368
Carcinogencity:	0.039
Eye Corrosion:	0.213
Eye Irritation:	0.989
Respiratory Toxicity:	0.112

Download Data

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

Natural Product: NPC81808

Natural Product ID:	NPC81808
*Common Name:**	Methyl 3-Hydroxybenzoate
IUPAC Name:	methyl 3-hydroxybenzoate
Synonyms:
Standard InCHIKey:	YKUCHDXIBAQWSF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C8H8O3/c1-11-8(10)6-3-2-4-7(9)5-6/h2-5,9H,1H3
SMILES:	COC(=O)c1cccc(c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2272613
PubChem CID:	88068
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001350] Benzoic acid esters [CHEMONTID:0004699] m-Hydroxybenzoic acid esters

*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
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29099182]
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1436	Houttuynia cordata	Species	Saururaceae	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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT331	Organism	Ralstonia solanacearum	Ralstonia solanacearum	IZ	=	23.0	mm	PMID[458347]

☑ 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 NPC81808 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	274
0.1-0.2	1679
0.2-0.3	4298
0.3-0.4	9890
0.4-0.5	8440
0.5-0.6	5902
0.6-0.7	9968
0.7-0.8	2052
0.8-0.85	168
0.85-0.9	23
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9545	High Similarity	NPC240664
0.9245	High Similarity	NPC187913
0.9052	High Similarity	NPC46634
0.8981	High Similarity	NPC34715
0.8938	High Similarity	NPC131192
0.8938	High Similarity	NPC128825
0.8868	High Similarity	NPC94343
0.886	High Similarity	NPC160199
0.8833	High Similarity	NPC158654
0.8833	High Similarity	NPC71525
0.8783	High Similarity	NPC94298
0.8783	High Similarity	NPC27633
0.8783	High Similarity	NPC94637
0.8739	High Similarity	NPC145134
0.8707	High Similarity	NPC90522
0.8707	High Similarity	NPC328459
0.8689	High Similarity	NPC226855
0.8632	High Similarity	NPC72977
0.8624	High Similarity	NPC163734
0.8583	High Similarity	NPC4012
0.8571	High Similarity	NPC217756
0.8559	High Similarity	NPC165197
0.8547	High Similarity	NPC61779
0.8522	High Similarity	NPC240163
0.8509	High Similarity	NPC98543
0.8496	Intermediate Similarity	NPC54626
0.8487	Intermediate Similarity	NPC25168
0.848	Intermediate Similarity	NPC111888
0.8475	Intermediate Similarity	NPC233282
0.8468	Intermediate Similarity	NPC285776
0.8455	Intermediate Similarity	NPC288760
0.8448	Intermediate Similarity	NPC312800
0.844	Intermediate Similarity	NPC13426
0.8435	Intermediate Similarity	NPC41851
0.843	Intermediate Similarity	NPC91475
0.843	Intermediate Similarity	NPC265910
0.843	Intermediate Similarity	NPC117794
0.8426	Intermediate Similarity	NPC253746
0.8421	Intermediate Similarity	NPC17693
0.8417	Intermediate Similarity	NPC297193
0.8417	Intermediate Similarity	NPC67300
0.8413	Intermediate Similarity	NPC295406
0.8413	Intermediate Similarity	NPC200422
0.8413	Intermediate Similarity	NPC283823
0.8413	Intermediate Similarity	NPC159418
0.8413	Intermediate Similarity	NPC289572
0.8413	Intermediate Similarity	NPC157478
0.8413	Intermediate Similarity	NPC472591
0.84	Intermediate Similarity	NPC264145
0.84	Intermediate Similarity	NPC7012
0.8396	Intermediate Similarity	NPC257182
0.8393	Intermediate Similarity	NPC85493
0.8387	Intermediate Similarity	NPC94810
0.8378	Intermediate Similarity	NPC317592
0.8376	Intermediate Similarity	NPC269414
0.8376	Intermediate Similarity	NPC125252
0.8362	Intermediate Similarity	NPC322358
0.8362	Intermediate Similarity	NPC161304
0.8361	Intermediate Similarity	NPC287473
0.8361	Intermediate Similarity	NPC472592
0.8347	Intermediate Similarity	NPC477153
0.8333	Intermediate Similarity	NPC228609
0.8319	Intermediate Similarity	NPC234639
0.8306	Intermediate Similarity	NPC473744
0.8305	Intermediate Similarity	NPC41567
0.8304	Intermediate Similarity	NPC226699
0.8304	Intermediate Similarity	NPC29883
0.8302	Intermediate Similarity	NPC130398
0.8293	Intermediate Similarity	NPC475236
0.8281	Intermediate Similarity	NPC204257
0.8281	Intermediate Similarity	NPC254832
0.8281	Intermediate Similarity	NPC29317
0.8281	Intermediate Similarity	NPC176102
0.8281	Intermediate Similarity	NPC267539
0.8281	Intermediate Similarity	NPC229638
0.8281	Intermediate Similarity	NPC71108
0.8279	Intermediate Similarity	NPC184219
0.8276	Intermediate Similarity	NPC163154
0.8276	Intermediate Similarity	NPC197513
0.8273	Intermediate Similarity	NPC304638
0.8268	Intermediate Similarity	NPC1321
0.8268	Intermediate Similarity	NPC304929
0.8268	Intermediate Similarity	NPC239855
0.8268	Intermediate Similarity	NPC156124
0.8264	Intermediate Similarity	NPC477151
0.8264	Intermediate Similarity	NPC132518
0.8264	Intermediate Similarity	NPC69403
0.8264	Intermediate Similarity	NPC291189
0.8261	Intermediate Similarity	NPC231717
0.8257	Intermediate Similarity	NPC52472
0.8246	Intermediate Similarity	NPC260818
0.8235	Intermediate Similarity	NPC156654
0.8235	Intermediate Similarity	NPC472593
0.823	Intermediate Similarity	NPC100551
0.823	Intermediate Similarity	NPC224584
0.8226	Intermediate Similarity	NPC181715
0.8226	Intermediate Similarity	NPC16651
0.8226	Intermediate Similarity	NPC32163
0.822	Intermediate Similarity	NPC150919
0.8214	Intermediate Similarity	NPC184658
0.8214	Intermediate Similarity	NPC6984
0.8211	Intermediate Similarity	NPC49938
0.8211	Intermediate Similarity	NPC4164
0.8205	Intermediate Similarity	NPC220540
0.8205	Intermediate Similarity	NPC188907
0.8198	Intermediate Similarity	NPC93831
0.8197	Intermediate Similarity	NPC275145
0.8197	Intermediate Similarity	NPC477152
0.819	Intermediate Similarity	NPC211421
0.819	Intermediate Similarity	NPC148969
0.819	Intermediate Similarity	NPC11824
0.819	Intermediate Similarity	NPC190212
0.819	Intermediate Similarity	NPC109241
0.8174	Intermediate Similarity	NPC226250
0.8174	Intermediate Similarity	NPC321852
0.8167	Intermediate Similarity	NPC260837
0.8165	Intermediate Similarity	NPC203925
0.8165	Intermediate Similarity	NPC245561
0.8158	Intermediate Similarity	NPC95172
0.8148	Intermediate Similarity	NPC276775
0.8148	Intermediate Similarity	NPC92754
0.8148	Intermediate Similarity	NPC249912
0.8148	Intermediate Similarity	NPC253423
0.8145	Intermediate Similarity	NPC110211
0.8145	Intermediate Similarity	NPC95309
0.8145	Intermediate Similarity	NPC204579
0.8145	Intermediate Similarity	NPC154275
0.8142	Intermediate Similarity	NPC141523
0.814	Intermediate Similarity	NPC18646
0.8136	Intermediate Similarity	NPC128249
0.813	Intermediate Similarity	NPC221798
0.8125	Intermediate Similarity	NPC43627
0.8125	Intermediate Similarity	NPC227255
0.8115	Intermediate Similarity	NPC311219
0.811	Intermediate Similarity	NPC214702
0.811	Intermediate Similarity	NPC473777
0.811	Intermediate Similarity	NPC470831
0.8103	Intermediate Similarity	NPC26615
0.8099	Intermediate Similarity	NPC159760
0.8099	Intermediate Similarity	NPC115188
0.8099	Intermediate Similarity	NPC292665
0.8099	Intermediate Similarity	NPC178395
0.8099	Intermediate Similarity	NPC244994
0.8099	Intermediate Similarity	NPC179092
0.8099	Intermediate Similarity	NPC222876
0.8099	Intermediate Similarity	NPC26433
0.8099	Intermediate Similarity	NPC35856
0.8099	Intermediate Similarity	NPC301987
0.8099	Intermediate Similarity	NPC272454
0.8095	Intermediate Similarity	NPC261759
0.8091	Intermediate Similarity	NPC70624
0.8087	Intermediate Similarity	NPC476003
0.8083	Intermediate Similarity	NPC233165
0.8083	Intermediate Similarity	NPC184579
0.808	Intermediate Similarity	NPC203719
0.808	Intermediate Similarity	NPC470841
0.808	Intermediate Similarity	NPC117237
0.8077	Intermediate Similarity	NPC475111
0.8077	Intermediate Similarity	NPC156892
0.8073	Intermediate Similarity	NPC35448
0.8073	Intermediate Similarity	NPC78701
0.8073	Intermediate Similarity	NPC225060
0.807	Intermediate Similarity	NPC31274
0.807	Intermediate Similarity	NPC206341
0.8067	Intermediate Similarity	NPC217423
0.8067	Intermediate Similarity	NPC45104
0.8062	Intermediate Similarity	NPC474097
0.8062	Intermediate Similarity	NPC155098
0.8056	Intermediate Similarity	NPC246679
0.8053	Intermediate Similarity	NPC1065
0.8036	Intermediate Similarity	NPC2518
0.8036	Intermediate Similarity	NPC31786
0.8034	Intermediate Similarity	NPC95381
0.8034	Intermediate Similarity	NPC153053
0.8033	Intermediate Similarity	NPC194416
0.8033	Intermediate Similarity	NPC177291
0.8018	Intermediate Similarity	NPC25458
0.8018	Intermediate Similarity	NPC188895
0.8017	Intermediate Similarity	NPC23332
0.8017	Intermediate Similarity	NPC212718
0.8017	Intermediate Similarity	NPC7151
0.8017	Intermediate Similarity	NPC216297
0.8017	Intermediate Similarity	NPC114682
0.8017	Intermediate Similarity	NPC206778
0.8017	Intermediate Similarity	NPC473662
0.8017	Intermediate Similarity	NPC285829
0.8016	Intermediate Similarity	NPC2596
0.8015	Intermediate Similarity	NPC95679
0.8015	Intermediate Similarity	NPC112068
0.8015	Intermediate Similarity	NPC25305
0.8015	Intermediate Similarity	NPC125417
0.8015	Intermediate Similarity	NPC110899
0.8	Intermediate Similarity	NPC273282
0.8	Intermediate Similarity	NPC51037
0.8	Intermediate Similarity	NPC171843
0.8	Intermediate Similarity	NPC474890
0.8	Intermediate Similarity	NPC166591
0.8	Intermediate Similarity	NPC75272
0.8	Intermediate Similarity	NPC280869
0.8	Intermediate Similarity	NPC471954

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 NPC81808 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	265
0.1-0.2	938
0.2-0.3	1460
0.3-0.4	2627
0.4-0.5	2003
0.5-0.6	1268
0.6-0.7	488
0.7-0.8	88
0.8-0.85	11
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8938	High Similarity	NPD9493	Approved
0.8783	High Similarity	NPD9545	Approved
0.8304	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.8268	Intermediate Similarity	NPD230	Phase 1
0.823	Intermediate Similarity	NPD9266	Approved
0.823	Intermediate Similarity	NPD74	Approved
0.8142	Intermediate Similarity	NPD9267	Approved
0.8142	Intermediate Similarity	NPD9264	Approved
0.8142	Intermediate Similarity	NPD9263	Approved
0.8125	Intermediate Similarity	NPD447	Suspended
0.8115	Intermediate Similarity	NPD9717	Approved
0.808	Intermediate Similarity	NPD9494	Approved
0.8036	Intermediate Similarity	NPD164	Approved
0.8015	Intermediate Similarity	NPD2935	Discontinued
0.7983	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD9258	Approved
0.7925	Intermediate Similarity	NPD9256	Approved
0.792	Intermediate Similarity	NPD1203	Approved
0.7891	Intermediate Similarity	NPD411	Approved
0.7891	Intermediate Similarity	NPD3764	Approved
0.7838	Intermediate Similarity	NPD1238	Approved
0.7823	Intermediate Similarity	NPD9269	Phase 2
0.7788	Intermediate Similarity	NPD9261	Approved
0.7787	Intermediate Similarity	NPD9268	Approved
0.7759	Intermediate Similarity	NPD2182	Approved
0.7698	Intermediate Similarity	NPD1283	Approved
0.768	Intermediate Similarity	NPD1608	Approved
0.7667	Intermediate Similarity	NPD9281	Approved
0.7627	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD2313	Discontinued
0.7583	Intermediate Similarity	NPD1241	Discontinued
0.7581	Intermediate Similarity	NPD1778	Approved
0.7578	Intermediate Similarity	NPD1019	Discontinued
0.7576	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD2346	Discontinued
0.7547	Intermediate Similarity	NPD9259	Approved
0.7547	Intermediate Similarity	NPD9257	Approved
0.754	Intermediate Similarity	NPD1481	Phase 2
0.752	Intermediate Similarity	NPD3496	Discontinued
0.7518	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1470	Approved
0.75	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1164	Approved
0.7481	Intermediate Similarity	NPD1551	Phase 2
0.746	Intermediate Similarity	NPD1281	Approved
0.746	Intermediate Similarity	NPD1535	Discovery
0.746	Intermediate Similarity	NPD1201	Approved
0.7442	Intermediate Similarity	NPD2798	Approved
0.744	Intermediate Similarity	NPD17	Approved
0.744	Intermediate Similarity	NPD4626	Approved
0.7436	Intermediate Similarity	NPD3134	Approved
0.7426	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD3684	Discontinued
0.7407	Intermediate Similarity	NPD4308	Phase 3
0.7407	Intermediate Similarity	NPD2799	Discontinued
0.7387	Intermediate Similarity	NPD1202	Approved
0.7377	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD1358	Approved
0.7368	Intermediate Similarity	NPD1240	Approved
0.7364	Intermediate Similarity	NPD2797	Approved
0.7361	Intermediate Similarity	NPD2672	Discontinued
0.736	Intermediate Similarity	NPD5585	Approved
0.7344	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD6832	Phase 2
0.7317	Intermediate Similarity	NPD256	Approved
0.7317	Intermediate Similarity	NPD255	Approved
0.7311	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD520	Approved
0.7287	Intermediate Similarity	NPD1876	Approved
0.7281	Intermediate Similarity	NPD9495	Approved
0.728	Intermediate Similarity	NPD1894	Discontinued
0.7273	Intermediate Similarity	NPD228	Approved
0.7266	Intermediate Similarity	NPD4628	Phase 3
0.7266	Intermediate Similarity	NPD7003	Approved
0.7266	Intermediate Similarity	NPD3972	Approved
0.7265	Intermediate Similarity	NPD1237	Approved
0.7259	Intermediate Similarity	NPD1607	Approved
0.7257	Intermediate Similarity	NPD844	Approved
0.7222	Intermediate Similarity	NPD3226	Approved
0.7222	Intermediate Similarity	NPD3455	Phase 2
0.7222	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD6190	Approved
0.7203	Intermediate Similarity	NPD9697	Approved
0.7194	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD288	Approved
0.7188	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1929	Approved
0.7179	Intermediate Similarity	NPD1930	Approved
0.7179	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD2344	Approved
0.7153	Intermediate Similarity	NPD1510	Phase 2
0.7143	Intermediate Similarity	NPD968	Approved
0.7143	Intermediate Similarity	NPD8166	Discontinued
0.7143	Intermediate Similarity	NPD3750	Approved
0.7133	Intermediate Similarity	NPD6273	Approved
0.7131	Intermediate Similarity	NPD9508	Approved
0.7131	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD111	Approved
0.712	Intermediate Similarity	NPD9568	Approved
0.7111	Intermediate Similarity	NPD943	Approved
0.7111	Intermediate Similarity	NPD4307	Phase 2
0.7109	Intermediate Similarity	NPD3847	Discontinued
0.7103	Intermediate Similarity	NPD9491	Approved
0.7097	Intermediate Similarity	NPD5951	Approved
0.709	Intermediate Similarity	NPD3268	Approved
0.7087	Intermediate Similarity	NPD1651	Approved
0.7087	Intermediate Similarity	NPD5691	Approved
0.7077	Intermediate Similarity	NPD4359	Approved
0.7073	Intermediate Similarity	NPD5277	Phase 2
0.7063	Intermediate Similarity	NPD5536	Phase 2
0.7063	Intermediate Similarity	NPD2533	Approved
0.7063	Intermediate Similarity	NPD2532	Approved
0.7063	Intermediate Similarity	NPD2534	Approved
0.7059	Intermediate Similarity	NPD1933	Approved
0.7054	Intermediate Similarity	NPD422	Phase 1
0.7045	Intermediate Similarity	NPD258	Approved
0.7045	Intermediate Similarity	NPD257	Approved
0.7042	Intermediate Similarity	NPD7440	Discontinued
0.704	Intermediate Similarity	NPD6671	Approved
0.7037	Intermediate Similarity	NPD6663	Approved
0.7037	Intermediate Similarity	NPD259	Phase 1
0.7031	Intermediate Similarity	NPD3019	Approved
0.7031	Intermediate Similarity	NPD2932	Approved
0.7029	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD196	Phase 1
0.7023	Intermediate Similarity	NPD3225	Approved
0.7021	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD2933	Approved
0.7018	Intermediate Similarity	NPD9260	Approved
0.7018	Intermediate Similarity	NPD2934	Approved
0.7015	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD7008	Discontinued
0.7014	Intermediate Similarity	NPD9509	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD1759	Phase 1
0.7007	Intermediate Similarity	NPD6653	Approved
0.6993	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD454	Approved
0.6992	Remote Similarity	NPD5736	Approved
0.6986	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD826	Approved
0.6985	Remote Similarity	NPD825	Approved
0.6985	Remote Similarity	NPD2979	Phase 3
0.6978	Remote Similarity	NPD5408	Approved
0.6978	Remote Similarity	NPD5406	Approved
0.6978	Remote Similarity	NPD5404	Approved
0.6978	Remote Similarity	NPD5405	Approved
0.6975	Remote Similarity	NPD5909	Discontinued
0.6972	Remote Similarity	NPD2309	Approved
0.6967	Remote Similarity	NPD2067	Discontinued
0.696	Remote Similarity	NPD2629	Approved
0.6957	Remote Similarity	NPD2859	Approved
0.6957	Remote Similarity	NPD2860	Approved
0.6949	Remote Similarity	NPD1932	Approved
0.6947	Remote Similarity	NPD1755	Approved
0.6934	Remote Similarity	NPD555	Phase 2
0.6933	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD1758	Phase 1
0.6923	Remote Similarity	NPD6287	Discontinued
0.6923	Remote Similarity	NPD2066	Phase 3
0.6923	Remote Similarity	NPD3020	Approved
0.6917	Remote Similarity	NPD5647	Approved
0.6916	Remote Similarity	NPD226	Approved
0.6912	Remote Similarity	NPD6233	Phase 2
0.6906	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1549	Phase 2
0.6875	Remote Similarity	NPD800	Approved
0.6875	Remote Similarity	NPD1511	Approved
0.6875	Remote Similarity	NPD9295	Approved
0.6871	Remote Similarity	NPD824	Approved
0.6871	Remote Similarity	NPD7458	Discontinued
0.6867	Remote Similarity	NPD5402	Approved
0.6866	Remote Similarity	NPD9569	Approved
0.6864	Remote Similarity	NPD1242	Phase 1
0.6857	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD2354	Approved
0.6842	Remote Similarity	NPD3266	Approved
0.6842	Remote Similarity	NPD3267	Approved
0.6838	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD6798	Discontinued
0.6828	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6232	Discontinued
0.6815	Remote Similarity	NPD2614	Approved
0.6814	Remote Similarity	NPD1086	Approved
0.6814	Remote Similarity	NPD1090	Approved
0.6814	Remote Similarity	NPD1089	Approved
0.6812	Remote Similarity	NPD6355	Discontinued
0.6812	Remote Similarity	NPD1184	Approved
0.6809	Remote Similarity	NPD7266	Discontinued
0.6809	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD290	Approved
0.68	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.68	Remote Similarity	NPD2801	Approved
0.68	Remote Similarity	NPD7819	Suspended
0.6794	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD4062	Phase 3
0.6786	Remote Similarity	NPD3748	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