NPASS Compound

Structure

NPC114918 OpenBabel07101719402D 31 31 0 0 0 0 0 0 0 0999 V2000 -1.7321 -10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -11.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -7.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 21 1 0 0 0 0 5 22 1 0 0 0 0 6 9 1 0 0 0 0 6 13 1 0 0 0 0 7 10 1 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 8 14 1 0 0 0 0 9 19 2 0 0 0 0 10 20 2 0 0 0 0 11 21 1 0 0 0 0 12 20 1 0 0 0 0 13 23 1 0 0 0 0 14 23 2 0 0 0 0 15 16 1 0 0 0 0 15 21 2 0 0 0 0 16 24 1 0 0 0 0 17 22 1 0 0 0 0 17 25 2 0 0 0 0 18 24 2 0 0 0 0 18 25 1 0 0 0 0 22 26 2 0 0 0 0 23 27 1 0 0 0 0 24 26 1 0 0 0 0 25 28 1 0 0 0 0 26 29 1 0 0 0 0 27 30 2 0 0 0 0 27 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	426.28
Volume:	481.061
LogP:	6.512
LogD:	4.769
LogS:	-3.496
# Rotatable Bonds:	12
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.188
Synthetic Accessibility Score:	3.203
Fsp3:	0.444
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.063
MDCK Permeability:	2.6733236154541373e-05
Pgp-inhibitor:	0.097
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.274
20% Bioavailability (F20%):	0.874
30% Bioavailability (F30%):	0.392

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02
Plasma Protein Binding (PPB):	97.2999496459961%
Volume Distribution (VD):	0.18
Pgp-substrate:	0.719439685344696%

ADMET: Metabolism

CYP1A2-inhibitor:	0.491
CYP1A2-substrate:	0.239
CYP2C19-inhibitor:	0.258
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.713
CYP2C9-substrate:	0.943
CYP2D6-inhibitor:	0.912
CYP2D6-substrate:	0.743
CYP3A4-inhibitor:	0.106
CYP3A4-substrate:	0.082

ADMET: Excretion

Clearance (CL):	2.976
Half-life (T1/2):	0.817

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.913
Drug-inuced Liver Injury (DILI):	0.003
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.933
Skin Sensitization:	0.967
Carcinogencity:	0.029
Eye Corrosion:	0.01
Eye Irritation:	0.693
Respiratory Toxicity:	0.087

Download Data

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

Natural Product: NPC114918

Natural Product ID:	NPC114918
*Common Name:**	Sargahydroquinoic Acid
IUPAC Name:	(2Z,6E,10E)-12-(2,5-dihydroxy-3-methylphenyl)-6,10-dimethyl-2-(4-methylpent-3-enyl)dodeca-2,6,10-trienoic acid
Synonyms:	Sargahydroquinoic Acid
Standard InCHIKey:	ASCPFLQSHKBTRD-FWXQPYBBSA-N
Standard InCHI:	InChI=1S/C27H38O4/c1-19(2)9-6-13-23(27(30)31)14-8-12-20(3)10-7-11-21(4)15-16-24-18-25(28)17-22(5)26(24)29/h9-10,14-15,17-18,28-29H,6-8,11-13,16H2,1-5H3,(H,30,31)/b20-10+,21-15+,23-14-
SMILES:	CC(=CCC/C(=C/CC/C(=C/CC/C(=C/Cc1cc(cc(C)c1O)O)/C)/C)/C(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL261063
PubChem CID:	10202734
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO19171	Sargassum micracanthum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15684504]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921416]
NPO19171	Sargassum micracanthum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18372174]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	subtidal zone (0-2 m) off the southwestern shore of Jeju Island, Korea	2003-Apr	PMID[18817444]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19006667]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21377877]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28720331]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19171	Sargassum micracanthum	Species	Sargassaceae	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
EC50	2
IC50	5
Ki	1
Others	2

Activity Type	# Activity
Individual Protein	5
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1087	Individual Protein	Isocitrate lyase	Candida albicans	IC50	=	50.0	ug.mL-1	PMID[452398]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	IC50	=	124300.0	nM	PMID[452399]
NPT610	Others	Molecular identity unknown		EC50	=	11800.0	nM	PMID[452397]
NPT610	Others	Molecular identity unknown		EC50	=	140000.0	nM	PMID[452397]
NPT2	Others	Unspecified		Ratio EC50	=	11.9	n.a.	PMID[452397]
NPT2	Others	Unspecified		IC50	>	200.0	ug.mL-1	PMID[452398]
NPT1	Others	Radical scavenging activity		RC50	=	0.17	ug ml-1	PMID[452398]
NPT67	Individual Protein	Cholinesterase	Equus caballus	IC50	=	15200.0	nM	PMID[452399]
NPT740	Individual Protein	Beta-secretase 1	Homo sapiens	IC50	=	4400.0	nM	PMID[452399]
NPT740	Individual Protein	Beta-secretase 1	Homo sapiens	Ki	=	1600.0	nM	PMID[452399]

☑ 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 NPC114918 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	239
0.1-0.2	1243
0.2-0.3	3484
0.3-0.4	9741
0.4-0.5	9959
0.5-0.6	8411
0.6-0.7	8073
0.7-0.8	1390
0.8-0.85	121
0.85-0.9	22
0.9-0.95	12
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9533	High Similarity	NPC228609
0.9439	High Similarity	NPC208229
0.9346	High Similarity	NPC26013
0.9346	High Similarity	NPC282855
0.9273	High Similarity	NPC197513
0.9252	High Similarity	NPC68260
0.9252	High Similarity	NPC279887
0.9182	High Similarity	NPC28784
0.9182	High Similarity	NPC296144
0.9099	High Similarity	NPC473931
0.9099	High Similarity	NPC474114
0.9099	High Similarity	NPC474050
0.8879	High Similarity	NPC93831
0.8707	High Similarity	NPC476020
0.8678	High Similarity	NPC142087
0.8678	High Similarity	NPC95034
0.8655	High Similarity	NPC477153
0.8649	High Similarity	NPC98392
0.8624	High Similarity	NPC303141
0.8624	High Similarity	NPC243677
0.8618	High Similarity	NPC163169
0.8618	High Similarity	NPC123
0.8611	High Similarity	NPC108497
0.8598	High Similarity	NPC129373
0.8598	High Similarity	NPC48730
0.8598	High Similarity	NPC248396
0.8571	High Similarity	NPC132518
0.8571	High Similarity	NPC471535
0.8571	High Similarity	NPC477151
0.8545	High Similarity	NPC469913
0.8534	High Similarity	NPC160199
0.8519	High Similarity	NPC477685
0.8505	High Similarity	NPC260775
0.85	High Similarity	NPC275145
0.85	High Similarity	NPC477152
0.8443	Intermediate Similarity	NPC474944
0.8443	Intermediate Similarity	NPC474945
0.8443	Intermediate Similarity	NPC476022
0.844	Intermediate Similarity	NPC269212
0.844	Intermediate Similarity	NPC470202
0.8435	Intermediate Similarity	NPC41851
0.843	Intermediate Similarity	NPC474237
0.8426	Intermediate Similarity	NPC12931
0.8426	Intermediate Similarity	NPC70677
0.8426	Intermediate Similarity	NPC130756
0.8417	Intermediate Similarity	NPC49441
0.8411	Intermediate Similarity	NPC152097
0.8403	Intermediate Similarity	NPC474175
0.8403	Intermediate Similarity	NPC165197
0.8393	Intermediate Similarity	NPC470039
0.8376	Intermediate Similarity	NPC269414
0.8333	Intermediate Similarity	NPC329427
0.8333	Intermediate Similarity	NPC25168
0.8333	Intermediate Similarity	NPC317601
0.8319	Intermediate Similarity	NPC75272
0.8319	Intermediate Similarity	NPC471954
0.8306	Intermediate Similarity	NPC476024
0.8305	Intermediate Similarity	NPC206205
0.8305	Intermediate Similarity	NPC273282
0.8305	Intermediate Similarity	NPC474890
0.8305	Intermediate Similarity	NPC161943
0.8291	Intermediate Similarity	NPC83718
0.8264	Intermediate Similarity	NPC475192
0.8264	Intermediate Similarity	NPC297193
0.825	Intermediate Similarity	NPC222876
0.825	Intermediate Similarity	NPC244994
0.825	Intermediate Similarity	NPC164852
0.825	Intermediate Similarity	NPC272454
0.825	Intermediate Similarity	NPC115188
0.825	Intermediate Similarity	NPC26433
0.825	Intermediate Similarity	NPC292665
0.825	Intermediate Similarity	NPC159760
0.825	Intermediate Similarity	NPC179092
0.825	Intermediate Similarity	NPC178395
0.825	Intermediate Similarity	NPC35856
0.825	Intermediate Similarity	NPC301987
0.8241	Intermediate Similarity	NPC475078
0.8226	Intermediate Similarity	NPC319422
0.8226	Intermediate Similarity	NPC477214
0.8226	Intermediate Similarity	NPC477212
0.8226	Intermediate Similarity	NPC477211
0.8226	Intermediate Similarity	NPC209959
0.8224	Intermediate Similarity	NPC257182
0.8224	Intermediate Similarity	NPC246679
0.8214	Intermediate Similarity	NPC155072
0.8205	Intermediate Similarity	NPC240163
0.8198	Intermediate Similarity	NPC272029
0.819	Intermediate Similarity	NPC190212
0.8182	Intermediate Similarity	NPC80800
0.8174	Intermediate Similarity	NPC469912
0.8167	Intermediate Similarity	NPC478121
0.8145	Intermediate Similarity	NPC306765
0.8136	Intermediate Similarity	NPC312800
0.813	Intermediate Similarity	NPC117794
0.8125	Intermediate Similarity	NPC47284
0.8115	Intermediate Similarity	NPC302211
0.8115	Intermediate Similarity	NPC327070
0.8115	Intermediate Similarity	NPC325301
0.811	Intermediate Similarity	NPC258073
0.8108	Intermediate Similarity	NPC13426
0.8103	Intermediate Similarity	NPC26615
0.8099	Intermediate Similarity	NPC241001
0.8083	Intermediate Similarity	NPC184579
0.8083	Intermediate Similarity	NPC233165
0.8065	Intermediate Similarity	NPC167055
0.8065	Intermediate Similarity	NPC131799
0.8065	Intermediate Similarity	NPC240744
0.8065	Intermediate Similarity	NPC477213
0.8065	Intermediate Similarity	NPC472592
0.8062	Intermediate Similarity	NPC204582
0.8062	Intermediate Similarity	NPC27394
0.8053	Intermediate Similarity	NPC53740
0.8053	Intermediate Similarity	NPC187913
0.8049	Intermediate Similarity	NPC174991
0.8037	Intermediate Similarity	NPC3358
0.8037	Intermediate Similarity	NPC210497
0.8037	Intermediate Similarity	NPC162314
0.8037	Intermediate Similarity	NPC29373
0.8037	Intermediate Similarity	NPC94139
0.8037	Intermediate Similarity	NPC147284
0.8037	Intermediate Similarity	NPC306884
0.8034	Intermediate Similarity	NPC211421
0.8034	Intermediate Similarity	NPC242136
0.8033	Intermediate Similarity	NPC249340
0.8033	Intermediate Similarity	NPC162935
0.8031	Intermediate Similarity	NPC196621
0.8031	Intermediate Similarity	NPC31539
0.8018	Intermediate Similarity	NPC94343
0.8016	Intermediate Similarity	NPC81261
0.8	Intermediate Similarity	NPC49647
0.8	Intermediate Similarity	NPC473751
0.8	Intermediate Similarity	NPC136342
0.8	Intermediate Similarity	NPC295202
0.8	Intermediate Similarity	NPC227741
0.7984	Intermediate Similarity	NPC276962
0.7984	Intermediate Similarity	NPC190086
0.7984	Intermediate Similarity	NPC147896
0.7983	Intermediate Similarity	NPC477453
0.7982	Intermediate Similarity	NPC320439
0.7982	Intermediate Similarity	NPC474352
0.7982	Intermediate Similarity	NPC34715
0.7982	Intermediate Similarity	NPC228737
0.7967	Intermediate Similarity	NPC244351
0.7967	Intermediate Similarity	NPC121168
0.7966	Intermediate Similarity	NPC81808
0.7953	Intermediate Similarity	NPC271832
0.7953	Intermediate Similarity	NPC59654
0.7949	Intermediate Similarity	NPC62867
0.7949	Intermediate Similarity	NPC302371
0.7949	Intermediate Similarity	NPC286222
0.7949	Intermediate Similarity	NPC177962
0.7939	Intermediate Similarity	NPC472308
0.7934	Intermediate Similarity	NPC160235
0.7934	Intermediate Similarity	NPC473767
0.7931	Intermediate Similarity	NPC222905
0.792	Intermediate Similarity	NPC287473
0.7917	Intermediate Similarity	NPC125252
0.7913	Intermediate Similarity	NPC31274
0.7907	Intermediate Similarity	NPC251549
0.7899	Intermediate Similarity	NPC161304
0.7895	Intermediate Similarity	NPC54765
0.7895	Intermediate Similarity	NPC317592
0.789	Intermediate Similarity	NPC222146
0.7886	Intermediate Similarity	NPC154696
0.7876	Intermediate Similarity	NPC475580
0.7874	Intermediate Similarity	NPC473744
0.7874	Intermediate Similarity	NPC229894
0.7863	Intermediate Similarity	NPC470770
0.7863	Intermediate Similarity	NPC77772
0.7863	Intermediate Similarity	NPC266937
0.7857	Intermediate Similarity	NPC252105
0.7857	Intermediate Similarity	NPC472585
0.7857	Intermediate Similarity	NPC12221
0.7851	Intermediate Similarity	NPC203124
0.7851	Intermediate Similarity	NPC41567
0.785	Intermediate Similarity	NPC192
0.7846	Intermediate Similarity	NPC239855
0.7846	Intermediate Similarity	NPC180261
0.7846	Intermediate Similarity	NPC472591
0.7846	Intermediate Similarity	NPC37299
0.7845	Intermediate Similarity	NPC88141
0.7845	Intermediate Similarity	NPC473524
0.784	Intermediate Similarity	NPC469568
0.7838	Intermediate Similarity	NPC245561
0.7833	Intermediate Similarity	NPC69539
0.783	Intermediate Similarity	NPC19680
0.7829	Intermediate Similarity	NPC85342
0.7823	Intermediate Similarity	NPC67300
0.7823	Intermediate Similarity	NPC46634
0.7823	Intermediate Similarity	NPC282577
0.7812	Intermediate Similarity	NPC117899
0.7807	Intermediate Similarity	NPC138942
0.7807	Intermediate Similarity	NPC117115
0.7803	Intermediate Similarity	NPC64157
0.7803	Intermediate Similarity	NPC278832
0.7798	Intermediate Similarity	NPC81010
0.7798	Intermediate Similarity	NPC32977
0.7797	Intermediate Similarity	NPC98372
0.7797	Intermediate Similarity	NPC199462
0.7797	Intermediate Similarity	NPC228988

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 NPC114918 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	230
0.1-0.2	862
0.2-0.3	1536
0.3-0.4	2698
0.4-0.5	2130
0.5-0.6	1214
0.6-0.7	414
0.7-0.8	65
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8091	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD2935	Discontinued
0.7949	Intermediate Similarity	NPD7635	Approved
0.789	Intermediate Similarity	NPD844	Approved
0.7805	Intermediate Similarity	NPD3496	Discontinued
0.7724	Intermediate Similarity	NPD4626	Approved
0.7706	Intermediate Similarity	NPD845	Approved
0.7658	Intermediate Similarity	NPD288	Approved
0.7642	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD74	Approved
0.7607	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD9266	Approved
0.7603	Intermediate Similarity	NPD6671	Approved
0.7568	Intermediate Similarity	NPD1809	Phase 2
0.7541	Intermediate Similarity	NPD9493	Approved
0.7521	Intermediate Similarity	NPD9263	Approved
0.7521	Intermediate Similarity	NPD9267	Approved
0.7521	Intermediate Similarity	NPD9264	Approved
0.75	Intermediate Similarity	NPD1164	Approved
0.7411	Intermediate Similarity	NPD2860	Approved
0.7411	Intermediate Similarity	NPD2859	Approved
0.7398	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD4750	Phase 3
0.7391	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD5736	Approved
0.7373	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3020	Approved
0.7364	Intermediate Similarity	NPD1470	Approved
0.736	Intermediate Similarity	NPD5691	Approved
0.7353	Intermediate Similarity	NPD5408	Approved
0.7353	Intermediate Similarity	NPD5404	Approved
0.7353	Intermediate Similarity	NPD5406	Approved
0.7353	Intermediate Similarity	NPD5405	Approved
0.7323	Intermediate Similarity	NPD1201	Approved
0.7321	Intermediate Similarity	NPD2934	Approved
0.7321	Intermediate Similarity	NPD2933	Approved
0.7321	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD3019	Approved
0.7302	Intermediate Similarity	NPD2932	Approved
0.728	Intermediate Similarity	NPD1759	Phase 1
0.7273	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD3021	Approved
0.725	Intermediate Similarity	NPD3022	Approved
0.7241	Intermediate Similarity	NPD940	Approved
0.7241	Intermediate Similarity	NPD846	Approved
0.7236	Intermediate Similarity	NPD9281	Approved
0.7231	Intermediate Similarity	NPD2797	Approved
0.7227	Intermediate Similarity	NPD2342	Discontinued
0.7218	Intermediate Similarity	NPD2313	Discontinued
0.72	Intermediate Similarity	NPD1758	Phase 1
0.7188	Intermediate Similarity	NPD1611	Approved
0.7179	Intermediate Similarity	NPD9261	Approved
0.7177	Intermediate Similarity	NPD256	Approved
0.7177	Intermediate Similarity	NPD255	Approved
0.7174	Intermediate Similarity	NPD2346	Discontinued
0.7165	Intermediate Similarity	NPD1778	Approved
0.7164	Intermediate Similarity	NPD6663	Approved
0.7154	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD6696	Suspended
0.7153	Intermediate Similarity	NPD2799	Discontinued
0.7143	Intermediate Similarity	NPD9545	Approved
0.7143	Intermediate Similarity	NPD8166	Discontinued
0.7132	Intermediate Similarity	NPD9269	Phase 2
0.7132	Intermediate Similarity	NPD9717	Approved
0.7111	Intermediate Similarity	NPD4060	Phase 1
0.7097	Intermediate Similarity	NPD497	Approved
0.7097	Intermediate Similarity	NPD5951	Approved
0.709	Intermediate Similarity	NPD3268	Approved
0.7087	Intermediate Similarity	NPD9268	Approved
0.7059	Intermediate Similarity	NPD447	Suspended
0.7054	Intermediate Similarity	NPD1535	Discovery
0.7045	Intermediate Similarity	NPD258	Approved
0.7045	Intermediate Similarity	NPD257	Approved
0.7034	Intermediate Similarity	NPD9500	Approved
0.7034	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD1930	Approved
0.7034	Intermediate Similarity	NPD1929	Approved
0.7034	Intermediate Similarity	NPD6647	Phase 2
0.7029	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD1283	Approved
0.7016	Intermediate Similarity	NPD496	Approved
0.7016	Intermediate Similarity	NPD498	Approved
0.7016	Intermediate Similarity	NPD495	Approved
0.7	Intermediate Similarity	NPD1445	Approved
0.7	Intermediate Similarity	NPD1481	Phase 2
0.7	Intermediate Similarity	NPD1444	Approved
0.6992	Remote Similarity	NPD4208	Discontinued
0.6984	Remote Similarity	NPD7340	Approved
0.6977	Remote Similarity	NPD3847	Discontinued
0.6972	Remote Similarity	NPD111	Approved
0.697	Remote Similarity	NPD1203	Approved
0.6964	Remote Similarity	NPD9258	Approved
0.6964	Remote Similarity	NPD9256	Approved
0.6963	Remote Similarity	NPD3764	Approved
0.6963	Remote Similarity	NPD411	Approved
0.695	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.694	Remote Similarity	NPD4207	Discontinued
0.6934	Remote Similarity	NPD230	Phase 1
0.693	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD7644	Approved
0.6923	Remote Similarity	NPD2066	Phase 3
0.6917	Remote Similarity	NPD2798	Approved
0.6906	Remote Similarity	NPD4308	Phase 3
0.6906	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7003	Approved
0.6894	Remote Similarity	NPD3225	Approved
0.6889	Remote Similarity	NPD7095	Approved
0.6884	Remote Similarity	NPD6653	Approved
0.688	Remote Similarity	NPD1398	Phase 1
0.6875	Remote Similarity	NPD7390	Discontinued
0.6871	Remote Similarity	NPD3226	Approved
0.687	Remote Similarity	NPD1608	Approved
0.6861	Remote Similarity	NPD943	Approved
0.6861	Remote Similarity	NPD825	Approved
0.6861	Remote Similarity	NPD826	Approved
0.686	Remote Similarity	NPD3134	Approved
0.685	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.685	Remote Similarity	NPD9568	Approved
0.6846	Remote Similarity	NPD3026	Approved
0.6846	Remote Similarity	NPD3023	Approved
0.6838	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD7985	Registered
0.6829	Remote Similarity	NPD1792	Phase 2
0.6828	Remote Similarity	NPD2533	Approved
0.6828	Remote Similarity	NPD2534	Approved
0.6828	Remote Similarity	NPD2532	Approved
0.6825	Remote Similarity	NPD2629	Approved
0.6822	Remote Similarity	NPD5585	Approved
0.6822	Remote Similarity	NPD3025	Approved
0.6822	Remote Similarity	NPD3024	Approved
0.6818	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1755	Approved
0.6815	Remote Similarity	NPD6832	Phase 2
0.6812	Remote Similarity	NPD6355	Discontinued
0.6809	Remote Similarity	NPD6004	Phase 3
0.6809	Remote Similarity	NPD7266	Discontinued
0.6809	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6002	Phase 3
0.6809	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6005	Phase 3
0.6809	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD3300	Phase 2
0.6803	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD1358	Approved
0.6794	Remote Similarity	NPD1281	Approved
0.6794	Remote Similarity	NPD422	Phase 1
0.6788	Remote Similarity	NPD4248	Discontinued
0.6783	Remote Similarity	NPD3400	Discontinued
0.6777	Remote Similarity	NPD9697	Approved
0.6769	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7458	Discontinued
0.675	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD3091	Approved
0.6744	Remote Similarity	NPD7330	Discontinued
0.6741	Remote Similarity	NPD4212	Discontinued
0.6741	Remote Similarity	NPD2237	Approved
0.6741	Remote Similarity	NPD9569	Approved
0.6739	Remote Similarity	NPD2979	Phase 3
0.6739	Remote Similarity	NPD6346	Approved
0.6738	Remote Similarity	NPD6032	Approved
0.6736	Remote Similarity	NPD6190	Approved
0.6726	Remote Similarity	NPD5347	Phase 2
0.6726	Remote Similarity	NPD800	Approved
0.6726	Remote Similarity	NPD5346	Phase 2
0.6723	Remote Similarity	NPD1242	Phase 1
0.6716	Remote Similarity	NPD3266	Approved
0.6716	Remote Similarity	NPD3267	Approved
0.6715	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD6798	Discontinued
0.6712	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD4793	Discontinued
0.6695	Remote Similarity	NPD9495	Approved
0.6694	Remote Similarity	NPD5909	Discontinued
0.6693	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD1651	Approved
0.6691	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD274	Approved
0.6691	Remote Similarity	NPD275	Approved
0.6689	Remote Similarity	NPD7819	Suspended
0.6667	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD520	Approved
0.6667	Remote Similarity	NPD5535	Approved
0.6667	Remote Similarity	NPD1086	Approved
0.6667	Remote Similarity	NPD7976	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6233	Phase 2
0.6667	Remote Similarity	NPD1090	Approved
0.6667	Remote Similarity	NPD3750	Approved
0.6667	Remote Similarity	NPD259	Phase 1
0.6667	Remote Similarity	NPD5536	Phase 2
0.6667	Remote Similarity	NPD1089	Approved
0.6642	Remote Similarity	NPD9537	Phase 1
0.6642	Remote Similarity	NPD3136	Phase 2
0.6642	Remote Similarity	NPD9536	Phase 1
0.6641	Remote Similarity	NPD17	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