NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	168.04
Volume:	162.983
LogP:	1.594
LogD:	0.919
LogS:	-1.817
# Rotatable Bonds:	1
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.586
Synthetic Accessibility Score:	2.146
Fsp3:	0.125
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:	-5.469
MDCK Permeability:	4.697382337326417e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.092
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.432
30% Bioavailability (F30%):	0.921

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.094
Plasma Protein Binding (PPB):	71.66934204101562%
Volume Distribution (VD):	0.434
Pgp-substrate:	25.474267959594727%

ADMET: Metabolism

CYP1A2-inhibitor:	0.122
CYP1A2-substrate:	0.118
CYP2C19-inhibitor:	0.039
CYP2C19-substrate:	0.049
CYP2C9-inhibitor:	0.124
CYP2C9-substrate:	0.156
CYP2D6-inhibitor:	0.039
CYP2D6-substrate:	0.142
CYP3A4-inhibitor:	0.055
CYP3A4-substrate:	0.053

ADMET: Excretion

Clearance (CL):	8.896
Half-life (T1/2):	0.925

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.478
Drug-inuced Liver Injury (DILI):	0.92
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.064
Maximum Recommended Daily Dose:	0.026
Skin Sensitization:	0.382
Carcinogencity:	0.032
Eye Corrosion:	0.024
Eye Irritation:	0.969
Respiratory Toxicity:	0.757

Download Data

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

Natural Product: NPC262671

Natural Product ID:	NPC262671
*Common Name:**	Orsellinic Acid
IUPAC Name:	2,4-dihydroxy-6-methylbenzoic acid
Synonyms:	Orsellinic Acid
Standard InCHIKey:	AMKYESDOVDKZKV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C8H8O4/c1-4-2-5(9)3-6(10)7(4)8(11)12/h2-3,9-10H,1H3,(H,11,12)
SMILES:	Oc1cc(C)c(c(c1)O)C(=O)O
Synthetic Gene Cluster:	BGC0000057;
ChEMBL Identifier:	CHEMBL457583
PubChem CID:	68072
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001248] Hydroxybenzoic acid derivatives

*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
NPO41362	Aspergillus nidulans + Escherichia coli	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[19666480]
NPO28689	Armillaria mellea	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19795841]
NPO29948	Penicillium purpurogenum	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2010354]
NPO29948	Penicillium purpurogenum	Species	Trichocomaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21879714]
NPO33336	Penicillium sp. HN29-3B1	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26230970]
NPO41562	Trametes versicolor + Ganoderma applanatum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[27616058]
NPO41562	Trametes versicolor + Ganoderma applanatum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[29375514]
NPO29948	Penicillium purpurogenum	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32293887]
NPO28689	Armillaria mellea	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[4040154]
NPO2602	Usnea longissima	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12127	Parmelia saxatilis	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22230	Rhodiola crenulata	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14975	Adenanthera pavonina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22553	Thalictrum fendleri	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2602	Usnea longissima	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22230	Rhodiola crenulata	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12127	Parmelia saxatilis	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22553	Thalictrum fendleri	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20890	Anemone begoniifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14975	Adenanthera pavonina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28689	Armillaria mellea	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12127	Parmelia saxatilis	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22230	Rhodiola crenulata	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22230	Rhodiola crenulata	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20689	Roystonea regia	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22553	Thalictrum fendleri	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19958	Helichrysum tomentosulum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22230	Rhodiola crenulata	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2258	Johnius belangerii	Species	Sciaenidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20304	Astragalus pectinatus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20890	Anemone begoniifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17423	Solanum coccineum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22172	Cosmos hybridus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14975	Adenanthera pavonina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19943	Fleischmannia hymenophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20699	Melampodium rosei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21406	Pteris polypodioides	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22694	Croton plumieri	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5926	Panisea uniflora	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28689	Armillaria mellea	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2602	Usnea longissima	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18807	Coffea pseudozanguebariae	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17140	Clonostachys rosea f. catenulata	Species	Bionectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17684	Teucrium sandrasicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13015	Pilosella officinarum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12127	Parmelia saxatilis	Species	Parmeliaceae	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
IC50	2
Others	5
Potency	3

Activity Type	# Activity
Individual Protein	7
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	45.0	%	PMID[522423]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	25118.9	nM	PMID[522424]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	8.9	nM	PMID[522424]
NPT60	Individual Protein	Lysosomal alpha-glucosidase	Homo sapiens	IC50	>	100000.0	nM	PMID[522426]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	66.07	%	PMID[522425]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	86.96	%	PMID[522425]
NPT35	Others	n.a.		Activity	<	50.0	%	PMID[522427]
NPT2	Others	Unspecified		Inhibition	=	10.0	%	PMID[522427]
NPT2	Others	Unspecified		IC50	=	143000.0	nM	PMID[522428]

☑ 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 NPC262671 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	343
0.1-0.2	1690
0.2-0.3	4374
0.3-0.4	11287
0.4-0.5	7516
0.5-0.6	5312
0.6-0.7	7276
0.7-0.8	4244
0.8-0.85	426
0.85-0.9	185
0.9-0.95	36
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC201728
0.9752	High Similarity	NPC41263
0.9593	High Similarity	NPC247477
0.9593	High Similarity	NPC17840
0.9516	High Similarity	NPC219892
0.9516	High Similarity	NPC189823
0.9365	High Similarity	NPC153783
0.9365	High Similarity	NPC48036
0.9365	High Similarity	NPC180261
0.9365	High Similarity	NPC37299
0.9344	High Similarity	NPC477454
0.9291	High Similarity	NPC175943
0.9268	High Similarity	NPC473691
0.9219	High Similarity	NPC290803
0.9219	High Similarity	NPC180905
0.9219	High Similarity	NPC278375
0.9219	High Similarity	NPC182496
0.916	High Similarity	NPC40649
0.916	High Similarity	NPC209486
0.9147	High Similarity	NPC158481
0.9147	High Similarity	NPC235115
0.9147	High Similarity	NPC223836
0.9147	High Similarity	NPC118919
0.9091	High Similarity	NPC146642
0.9077	High Similarity	NPC149372
0.9077	High Similarity	NPC474849
0.9077	High Similarity	NPC135837
0.9077	High Similarity	NPC71256
0.9077	High Similarity	NPC194579
0.9077	High Similarity	NPC178467
0.9077	High Similarity	NPC65837
0.9077	High Similarity	NPC70380
0.9077	High Similarity	NPC474771
0.9076	High Similarity	NPC125252
0.9048	High Similarity	NPC92624
0.904	High Similarity	NPC209959
0.9016	High Similarity	NPC198336
0.9008	High Similarity	NPC9121
0.9008	High Similarity	NPC177307
0.9008	High Similarity	NPC472403
0.9008	High Similarity	NPC294037
0.9008	High Similarity	NPC212693
0.9008	High Similarity	NPC94248
0.9008	High Similarity	NPC478200
0.9008	High Similarity	NPC475974
0.9008	High Similarity	NPC33144
0.9008	High Similarity	NPC191835
0.9	High Similarity	NPC50455
0.9	High Similarity	NPC241089
0.8992	High Similarity	NPC474394
0.8976	High Similarity	NPC147757
0.8976	High Similarity	NPC62219
0.8976	High Similarity	NPC259942
0.8968	High Similarity	NPC179898
0.8952	High Similarity	NPC13238
0.8943	High Similarity	NPC283514
0.8939	High Similarity	NPC32360
0.8939	High Similarity	NPC52358
0.8939	High Similarity	NPC139634
0.8939	High Similarity	NPC474655
0.8939	High Similarity	NPC471819
0.8939	High Similarity	NPC92655
0.8939	High Similarity	NPC268052
0.8939	High Similarity	NPC105456
0.8934	High Similarity	NPC149246
0.8926	High Similarity	NPC161617
0.8915	High Similarity	NPC267205
0.888	High Similarity	NPC10926
0.8872	High Similarity	NPC158472
0.8872	High Similarity	NPC165172
0.8872	High Similarity	NPC99441
0.8864	High Similarity	NPC472602
0.8862	High Similarity	NPC215392
0.8846	High Similarity	NPC474519
0.8846	High Similarity	NPC282780
0.8846	High Similarity	NPC166480
0.8837	High Similarity	NPC478190
0.8819	High Similarity	NPC95537
0.881	High Similarity	NPC8745
0.881	High Similarity	NPC95309
0.8806	High Similarity	NPC220106
0.8806	High Similarity	NPC158634
0.8806	High Similarity	NPC67650
0.8806	High Similarity	NPC90411
0.8806	High Similarity	NPC478201
0.8806	High Similarity	NPC1704
0.8806	High Similarity	NPC53649
0.8806	High Similarity	NPC244923
0.8806	High Similarity	NPC472035
0.8806	High Similarity	NPC478217
0.8806	High Similarity	NPC313123
0.8806	High Similarity	NPC37530
0.8806	High Similarity	NPC475730
0.8797	High Similarity	NPC88269
0.8797	High Similarity	NPC275356
0.8797	High Similarity	NPC247409
0.879	High Similarity	NPC91105
0.878	High Similarity	NPC159760
0.878	High Similarity	NPC272454
0.878	High Similarity	NPC35856
0.878	High Similarity	NPC179092
0.878	High Similarity	NPC178395
0.878	High Similarity	NPC301987
0.878	High Similarity	NPC222876
0.878	High Similarity	NPC244994
0.878	High Similarity	NPC115188
0.878	High Similarity	NPC26433
0.878	High Similarity	NPC292665
0.877	High Similarity	NPC233165
0.877	High Similarity	NPC184579
0.8741	High Similarity	NPC105648
0.8741	High Similarity	NPC250755
0.8741	High Similarity	NPC474385
0.8739	High Similarity	NPC223004
0.8731	High Similarity	NPC472601
0.8731	High Similarity	NPC155205
0.8731	High Similarity	NPC472600
0.873	High Similarity	NPC475733
0.872	High Similarity	NPC65761
0.872	High Similarity	NPC472029
0.8712	High Similarity	NPC191976
0.8712	High Similarity	NPC254847
0.871	High Similarity	NPC267552
0.871	High Similarity	NPC45438
0.871	High Similarity	NPC115159
0.871	High Similarity	NPC224273
0.871	High Similarity	NPC242895
0.871	High Similarity	NPC73532
0.871	High Similarity	NPC143427
0.871	High Similarity	NPC19174
0.871	High Similarity	NPC226275
0.8702	High Similarity	NPC44437
0.8682	High Similarity	NPC296158
0.8676	High Similarity	NPC159721
0.8676	High Similarity	NPC354984
0.8676	High Similarity	NPC478202
0.8676	High Similarity	NPC469542
0.8676	High Similarity	NPC51106
0.8676	High Similarity	NPC472006
0.8672	High Similarity	NPC293453
0.8667	High Similarity	NPC472605
0.8667	High Similarity	NPC472603
0.8667	High Similarity	NPC472604
0.8667	High Similarity	NPC276111
0.8667	High Similarity	NPC118288
0.8667	High Similarity	NPC290550
0.8647	High Similarity	NPC290030
0.8647	High Similarity	NPC53414
0.8647	High Similarity	NPC471905
0.8647	High Similarity	NPC471452
0.8647	High Similarity	NPC53206
0.864	High Similarity	NPC133909
0.864	High Similarity	NPC32032
0.864	High Similarity	NPC309765
0.8636	High Similarity	NPC161632
0.8629	High Similarity	NPC297186
0.8615	High Similarity	NPC198249
0.8615	High Similarity	NPC470831
0.8615	High Similarity	NPC214702
0.8613	High Similarity	NPC86373
0.8613	High Similarity	NPC210966
0.8613	High Similarity	NPC95123
0.8613	High Similarity	NPC66404
0.8613	High Similarity	NPC280404
0.8613	High Similarity	NPC478203
0.8613	High Similarity	NPC42540
0.8613	High Similarity	NPC126882
0.8613	High Similarity	NPC210425
0.8613	High Similarity	NPC151607
0.8613	High Similarity	NPC277426
0.8607	High Similarity	NPC230349
0.8603	High Similarity	NPC82913
0.8603	High Similarity	NPC322112
0.8594	High Similarity	NPC214620
0.8583	High Similarity	NPC240744
0.8583	High Similarity	NPC167055
0.8571	High Similarity	NPC291454
0.8571	High Similarity	NPC475955
0.8571	High Similarity	NPC242712
0.8571	High Similarity	NPC474726
0.856	High Similarity	NPC303737
0.856	High Similarity	NPC156139
0.8551	High Similarity	NPC32470
0.8551	High Similarity	NPC257558
0.8551	High Similarity	NPC312789
0.8551	High Similarity	NPC134621
0.8551	High Similarity	NPC472034
0.8551	High Similarity	NPC83272
0.8551	High Similarity	NPC29577
0.855	High Similarity	NPC175738
0.8548	High Similarity	NPC294964
0.854	High Similarity	NPC472610
0.854	High Similarity	NPC471731
0.8538	High Similarity	NPC307732
0.8538	High Similarity	NPC42292
0.8538	High Similarity	NPC26697
0.8538	High Similarity	NPC233056
0.8519	High Similarity	NPC143438
0.8519	High Similarity	NPC162939
0.8519	High Similarity	NPC57380

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 NPC262671 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	317
0.1-0.2	993
0.2-0.3	1813
0.3-0.4	2855
0.4-0.5	1781
0.5-0.6	972
0.6-0.7	319
0.7-0.8	79
0.8-0.85	20
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8939	High Similarity	NPD970	Clinical (unspecified phase)
0.8712	High Similarity	NPD1509	Clinical (unspecified phase)
0.8571	High Similarity	NPD651	Clinical (unspecified phase)
0.8409	Intermediate Similarity	NPD943	Approved
0.8346	Intermediate Similarity	NPD9269	Phase 2
0.832	Intermediate Similarity	NPD9268	Approved
0.8214	Intermediate Similarity	NPD7390	Discontinued
0.8167	Intermediate Similarity	NPD9266	Approved
0.8167	Intermediate Similarity	NPD74	Approved
0.8156	Intermediate Similarity	NPD2533	Approved
0.8156	Intermediate Similarity	NPD2532	Approved
0.8156	Intermediate Similarity	NPD2534	Approved
0.8125	Intermediate Similarity	NPD1201	Approved
0.8102	Intermediate Similarity	NPD5404	Approved
0.8102	Intermediate Similarity	NPD5408	Approved
0.8102	Intermediate Similarity	NPD5406	Approved
0.8102	Intermediate Similarity	NPD5405	Approved
0.8083	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.8083	Intermediate Similarity	NPD9263	Approved
0.8083	Intermediate Similarity	NPD9267	Approved
0.8083	Intermediate Similarity	NPD9264	Approved
0.808	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.808	Intermediate Similarity	NPD9493	Approved
0.8074	Intermediate Similarity	NPD230	Phase 1
0.8015	Intermediate Similarity	NPD1470	Approved
0.8015	Intermediate Similarity	NPD1164	Approved
0.8	Intermediate Similarity	NPD1240	Approved
0.7899	Intermediate Similarity	NPD1510	Phase 2
0.7883	Intermediate Similarity	NPD1607	Approved
0.7838	Intermediate Similarity	NPD7819	Suspended
0.7812	Intermediate Similarity	NPD9545	Approved
0.7778	Intermediate Similarity	NPD9281	Approved
0.775	Intermediate Similarity	NPD9261	Approved
0.7746	Intermediate Similarity	NPD3750	Approved
0.7714	Intermediate Similarity	NPD2935	Discontinued
0.7712	Intermediate Similarity	NPD6232	Discontinued
0.7708	Intermediate Similarity	NPD1511	Approved
0.766	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD9717	Approved
0.7622	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD1549	Phase 2
0.7603	Intermediate Similarity	NPD1512	Approved
0.7589	Intermediate Similarity	NPD1551	Phase 2
0.7566	Intermediate Similarity	NPD3749	Approved
0.7564	Intermediate Similarity	NPD7473	Discontinued
0.7534	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD846	Approved
0.7521	Intermediate Similarity	NPD940	Approved
0.7481	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD1203	Approved
0.7466	Intermediate Similarity	NPD6799	Approved
0.7464	Intermediate Similarity	NPD411	Approved
0.7464	Intermediate Similarity	NPD3764	Approved
0.7431	Intermediate Similarity	NPD1243	Approved
0.7431	Intermediate Similarity	NPD2800	Approved
0.7429	Intermediate Similarity	NPD447	Suspended
0.7417	Intermediate Similarity	NPD1934	Approved
0.7394	Intermediate Similarity	NPD3748	Approved
0.7381	Intermediate Similarity	NPD4750	Phase 3
0.7372	Intermediate Similarity	NPD5710	Approved
0.7372	Intermediate Similarity	NPD5711	Approved
0.7368	Intermediate Similarity	NPD2801	Approved
0.7368	Intermediate Similarity	NPD1465	Phase 2
0.7368	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD7411	Suspended
0.7338	Intermediate Similarity	NPD7075	Discontinued
0.7338	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD3817	Phase 2
0.7313	Intermediate Similarity	NPD422	Phase 1
0.7308	Intermediate Similarity	NPD6959	Discontinued
0.7297	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD1242	Phase 1
0.7285	Intermediate Similarity	NPD6599	Discontinued
0.7273	Intermediate Similarity	NPD3882	Suspended
0.7273	Intermediate Similarity	NPD7768	Phase 2
0.726	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD6651	Approved
0.7222	Intermediate Similarity	NPD2796	Approved
0.7219	Intermediate Similarity	NPD3226	Approved
0.7208	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD2346	Discontinued
0.7171	Intermediate Similarity	NPD4380	Phase 2
0.717	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD520	Approved
0.7161	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD2799	Discontinued
0.7132	Intermediate Similarity	NPD1608	Approved
0.7103	Intermediate Similarity	NPD6100	Approved
0.7103	Intermediate Similarity	NPD6099	Approved
0.7086	Intermediate Similarity	NPD920	Approved
0.7078	Intermediate Similarity	NPD6801	Discontinued
0.7075	Intermediate Similarity	NPD2654	Approved
0.7055	Intermediate Similarity	NPD2344	Approved
0.7047	Intermediate Similarity	NPD3300	Phase 2
0.7047	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD5844	Phase 1
0.7037	Intermediate Similarity	NPD2932	Approved
0.7037	Intermediate Similarity	NPD3019	Approved
0.7037	Intermediate Similarity	NPD4626	Approved
0.7029	Intermediate Similarity	NPD1283	Approved
0.7015	Intermediate Similarity	NPD1759	Phase 1
0.7006	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD919	Approved
0.6959	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6166	Phase 2
0.6954	Remote Similarity	NPD642	Clinical (unspecified phase)
0.695	Remote Similarity	NPD6832	Phase 2
0.6944	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.694	Remote Similarity	NPD1758	Phase 1
0.6933	Remote Similarity	NPD7054	Approved
0.6929	Remote Similarity	NPD2798	Approved
0.6929	Remote Similarity	NPD1019	Discontinued
0.6917	Remote Similarity	NPD255	Approved
0.6917	Remote Similarity	NPD256	Approved
0.6913	Remote Similarity	NPD4628	Phase 3
0.6912	Remote Similarity	NPD17	Approved
0.6911	Remote Similarity	NPD288	Approved
0.689	Remote Similarity	NPD7074	Phase 3
0.689	Remote Similarity	NPD7472	Approved
0.688	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD9494	Approved
0.6879	Remote Similarity	NPD5402	Approved
0.6879	Remote Similarity	NPD4288	Approved
0.6871	Remote Similarity	NPD3818	Discontinued
0.6867	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD2309	Approved
0.6863	Remote Similarity	NPD5403	Approved
0.6863	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD2797	Approved
0.6853	Remote Similarity	NPD2313	Discontinued
0.6853	Remote Similarity	NPD3268	Approved
0.6853	Remote Similarity	NPD1296	Phase 2
0.6848	Remote Similarity	NPD6797	Phase 2
0.6848	Remote Similarity	NPD5953	Discontinued
0.6842	Remote Similarity	NPD5401	Approved
0.6833	Remote Similarity	NPD9258	Approved
0.6833	Remote Similarity	NPD9256	Approved
0.6829	Remote Similarity	NPD6020	Phase 2
0.6829	Remote Similarity	NPD844	Approved
0.6812	Remote Similarity	NPD1281	Approved
0.6809	Remote Similarity	NPD257	Approved
0.6809	Remote Similarity	NPD258	Approved
0.6807	Remote Similarity	NPD7251	Discontinued
0.6806	Remote Similarity	NPD6663	Approved
0.6803	Remote Similarity	NPD4308	Phase 3
0.6803	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7003	Approved
0.6769	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD7808	Phase 3
0.6761	Remote Similarity	NPD5736	Approved
0.6757	Remote Similarity	NPD9570	Approved
0.6755	Remote Similarity	NPD6190	Approved
0.6752	Remote Similarity	NPD37	Approved
0.6748	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD9568	Approved
0.6727	Remote Similarity	NPD7286	Phase 2
0.6727	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD164	Approved
0.6716	Remote Similarity	NPD5951	Approved
0.6715	Remote Similarity	NPD5691	Approved
0.6714	Remote Similarity	NPD1755	Approved
0.6708	Remote Similarity	NPD5494	Approved
0.6707	Remote Similarity	NPD6559	Discontinued
0.6694	Remote Similarity	NPD1809	Phase 2
0.6689	Remote Similarity	NPD1196	Approved
0.6689	Remote Similarity	NPD3400	Discontinued
0.6667	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3225	Approved
0.6667	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1778	Approved
0.6667	Remote Similarity	NPD3020	Approved
0.6667	Remote Similarity	NPD1543	Discontinued
0.6667	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7199	Phase 2
0.6647	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6234	Discontinued
0.6644	Remote Similarity	NPD468	Phase 1
0.6643	Remote Similarity	NPD9569	Approved
0.6643	Remote Similarity	NPD1481	Phase 2
0.6628	Remote Similarity	NPD4287	Approved
0.6626	Remote Similarity	NPD7229	Phase 3
0.6625	Remote Similarity	NPD4967	Phase 2
0.6625	Remote Similarity	NPD4965	Approved
0.6625	Remote Similarity	NPD4966	Approved
0.6623	Remote Similarity	NPD1195	Approved
0.6623	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD9279	Approved
0.6621	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.662	Remote Similarity	NPD3267	Approved
0.662	Remote Similarity	NPD3266	Approved
0.6619	Remote Similarity	NPD3026	Approved
0.6619	Remote Similarity	NPD3023	Approved
0.6613	Remote Similarity	NPD2933	Approved
0.6613	Remote Similarity	NPD2934	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