NPASS Compound

Structure

NPC473931 OpenBabel07101719512D 31 31 0 0 1 0 0 0 0 0999 V2000 -2.5981 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 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 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 5 21 1 0 0 0 0 6 22 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 19 2 0 0 0 0 9 20 1 0 0 0 0 10 11 1 0 0 0 0 10 21 2 0 0 0 0 11 23 1 0 0 0 0 12 18 2 0 0 0 0 12 24 1 0 0 0 0 13 19 1 0 0 0 0 13 24 1 0 0 0 0 14 20 2 0 0 0 0 14 25 1 0 0 0 0 15 21 1 0 0 0 0 15 25 1 0 0 0 0 16 22 1 0 0 0 0 16 26 2 0 0 0 0 17 23 2 0 0 0 0 17 26 1 0 0 0 0 22 27 2 0 0 0 0 23 27 1 0 0 0 0 24 28 1 0 0 0 0 25 29 2 0 0 0 0 26 30 1 0 0 0 0 27 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	426.28
Volume:	481.061
LogP:	5.356
LogD:	3.832
LogS:	-3.986
# Rotatable Bonds:	11
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.222
Synthetic Accessibility Score:	3.948
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:	-4.777
MDCK Permeability:	1.5995281501091085e-05
Pgp-inhibitor:	0.615
Pgp-substrate:	0.894
Human Intestinal Absorption (HIA):	0.666
20% Bioavailability (F20%):	0.993
30% Bioavailability (F30%):	0.745

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021
Plasma Protein Binding (PPB):	95.9005355834961%
Volume Distribution (VD):	0.559
Pgp-substrate:	1.046620488166809%

ADMET: Metabolism

CYP1A2-inhibitor:	0.35
CYP1A2-substrate:	0.378
CYP2C19-inhibitor:	0.815
CYP2C19-substrate:	0.361
CYP2C9-inhibitor:	0.886
CYP2C9-substrate:	0.979
CYP2D6-inhibitor:	0.837
CYP2D6-substrate:	0.7
CYP3A4-inhibitor:	0.639
CYP3A4-substrate:	0.243

ADMET: Excretion

Clearance (CL):	10.264
Half-life (T1/2):	0.927

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.663
Drug-inuced Liver Injury (DILI):	0.042
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.031
Maximum Recommended Daily Dose:	0.93
Skin Sensitization:	0.948
Carcinogencity:	0.229
Eye Corrosion:	0.004
Eye Irritation:	0.639
Respiratory Toxicity:	0.783

Download Data

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

Natural Product: NPC473931

Natural Product ID:	NPC473931
*Common Name:**	(2E,6Z,10E)-1-(2,5-Dihydroxy-3-Methylphenyl)-13-Hydroxy-3,7,11,15-Tetramethylhexadeca-2,6,10,14-Tetraen-5-One
IUPAC Name:	(2E,6Z,10E)-1-(2,5-dihydroxy-3-methylphenyl)-13-hydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-5-one
Synonyms:
Standard InCHIKey:	OZNBGGKJHMIWEF-SFBWPCFQSA-N
Standard InCHI:	InChI=1S/C27H38O4/c1-18(2)12-24(28)13-19(3)8-7-9-20(4)14-25(29)15-21(5)10-11-23-17-26(30)16-22(6)27(23)31/h8,10,12,14,16-17,24,28,30-31H,7,9,11,13,15H2,1-6H3/b19-8+,20-14-,21-10+
SMILES:	CC1=CC(=CC(=C1O)CC=C(C)CC(=O)C=C(C)CCC=C(C)CC(C=C(C)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL455585
PubChem CID:	11069948
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
NPO8863	Cystoseira crinita	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12880316]
NPO8863	Cystoseira crinita	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
Others	11

Activity Type	# Activity
NON-MOLECULAR	5
Others	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		Activity	=	9.7	%	PMID[486662]
NPT1	Others	Radical scavenging activity		Activity	=	5.8	%	PMID[486662]
NPT1	Others	Radical scavenging activity		Activity	=	17.1	%	PMID[486662]
NPT1	Others	Radical scavenging activity		Activity	=	55.2	%	PMID[486662]
NPT1	Others	Radical scavenging activity		Activity	=	95.5	%	PMID[486662]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	4.9	%	PMID[486662]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	10.4	%	PMID[486662]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	19.2	%	PMID[486662]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	60.4	%	PMID[486662]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	70.3	%	PMID[486662]

☑ 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 NPC473931 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	211
0.1-0.2	1087
0.2-0.3	3235
0.3-0.4	9563
0.4-0.5	10535
0.5-0.6	7983
0.6-0.7	8539
0.7-0.8	1397
0.8-0.85	111
0.85-0.9	24
0.9-0.95	2
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474114
1.0	High Similarity	NPC474050
0.9906	High Similarity	NPC28784
0.9906	High Similarity	NPC296144
0.9623	High Similarity	NPC208229
0.9528	High Similarity	NPC26013
0.9528	High Similarity	NPC282855
0.9434	High Similarity	NPC68260
0.9434	High Similarity	NPC279887
0.9375	High Similarity	NPC476020
0.9099	High Similarity	NPC114918
0.8929	High Similarity	NPC197513
0.8833	High Similarity	NPC319422
0.8833	High Similarity	NPC477211
0.8833	High Similarity	NPC477214
0.8833	High Similarity	NPC477212
0.8818	High Similarity	NPC98392
0.8739	High Similarity	NPC471535
0.8689	High Similarity	NPC59654
0.8667	High Similarity	NPC477213
0.8661	High Similarity	NPC228609
0.8636	High Similarity	NPC474352
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
0.8595	High Similarity	NPC474944
0.8571	High Similarity	NPC49441
0.8545	High Similarity	NPC469913
0.8537	High Similarity	NPC271832
0.8519	High Similarity	NPC477685
0.8505	High Similarity	NPC260775
0.8482	Intermediate Similarity	NPC473524
0.8455	Intermediate Similarity	NPC476024
0.8443	Intermediate Similarity	NPC474945
0.8443	Intermediate Similarity	NPC476022
0.844	Intermediate Similarity	NPC269212
0.8426	Intermediate Similarity	NPC12931
0.8426	Intermediate Similarity	NPC130756
0.8426	Intermediate Similarity	NPC70677
0.8421	Intermediate Similarity	NPC302371
0.8411	Intermediate Similarity	NPC152097
0.8411	Intermediate Similarity	NPC474073
0.8403	Intermediate Similarity	NPC474175
0.839	Intermediate Similarity	NPC473767
0.832	Intermediate Similarity	NPC475880
0.8305	Intermediate Similarity	NPC206205
0.8279	Intermediate Similarity	NPC276962
0.8279	Intermediate Similarity	NPC190086
0.8273	Intermediate Similarity	NPC235762
0.8273	Intermediate Similarity	NPC471228
0.8264	Intermediate Similarity	NPC477151
0.8264	Intermediate Similarity	NPC132518
0.8257	Intermediate Similarity	NPC130103
0.8257	Intermediate Similarity	NPC174911
0.8254	Intermediate Similarity	NPC474143
0.8254	Intermediate Similarity	NPC474246
0.8246	Intermediate Similarity	NPC132720
0.8241	Intermediate Similarity	NPC475078
0.8235	Intermediate Similarity	NPC182240
0.822	Intermediate Similarity	NPC269414
0.8214	Intermediate Similarity	NPC155072
0.8211	Intermediate Similarity	NPC131799
0.8205	Intermediate Similarity	NPC474486
0.8198	Intermediate Similarity	NPC272029
0.8198	Intermediate Similarity	NPC93831
0.8198	Intermediate Similarity	NPC475225
0.8189	Intermediate Similarity	NPC242358
0.8189	Intermediate Similarity	NPC110609
0.8189	Intermediate Similarity	NPC246693
0.8182	Intermediate Similarity	NPC80800
0.8174	Intermediate Similarity	NPC469912
0.8167	Intermediate Similarity	NPC473136
0.8167	Intermediate Similarity	NPC232295
0.8165	Intermediate Similarity	NPC128723
0.8151	Intermediate Similarity	NPC41567
0.8145	Intermediate Similarity	NPC136342
0.8145	Intermediate Similarity	NPC295202
0.8145	Intermediate Similarity	NPC49647
0.8145	Intermediate Similarity	NPC227741
0.813	Intermediate Similarity	NPC152525
0.813	Intermediate Similarity	NPC147896
0.813	Intermediate Similarity	NPC68756
0.8125	Intermediate Similarity	NPC47284
0.812	Intermediate Similarity	NPC41851
0.8115	Intermediate Similarity	NPC204535
0.8115	Intermediate Similarity	NPC46586
0.8115	Intermediate Similarity	NPC475192
0.8103	Intermediate Similarity	NPC228425
0.8095	Intermediate Similarity	NPC474546
0.8091	Intermediate Similarity	NPC294741
0.8083	Intermediate Similarity	NPC323074
0.8083	Intermediate Similarity	NPC32152
0.8073	Intermediate Similarity	NPC88420
0.807	Intermediate Similarity	NPC262365
0.807	Intermediate Similarity	NPC317305
0.8067	Intermediate Similarity	NPC320864
0.8065	Intermediate Similarity	NPC167055
0.8065	Intermediate Similarity	NPC240744
0.8062	Intermediate Similarity	NPC477210
0.8053	Intermediate Similarity	NPC53740
0.8051	Intermediate Similarity	NPC240163
0.8049	Intermediate Similarity	NPC477153
0.8049	Intermediate Similarity	NPC474130
0.8049	Intermediate Similarity	NPC471187
0.8047	Intermediate Similarity	NPC251549
0.8047	Intermediate Similarity	NPC329427
0.8047	Intermediate Similarity	NPC317601
0.8037	Intermediate Similarity	NPC162314
0.8037	Intermediate Similarity	NPC3358
0.8037	Intermediate Similarity	NPC210497
0.8037	Intermediate Similarity	NPC29373
0.8037	Intermediate Similarity	NPC94139
0.8037	Intermediate Similarity	NPC147284
0.8037	Intermediate Similarity	NPC306884
0.8036	Intermediate Similarity	NPC323810
0.8034	Intermediate Similarity	NPC190212
0.8033	Intermediate Similarity	NPC31936
0.8017	Intermediate Similarity	NPC477037
0.8017	Intermediate Similarity	NPC325544
0.8017	Intermediate Similarity	NPC474131
0.8017	Intermediate Similarity	NPC318581
0.8017	Intermediate Similarity	NPC308689
0.8	Intermediate Similarity	NPC306765
0.7984	Intermediate Similarity	NPC474237
0.7984	Intermediate Similarity	NPC234890
0.7984	Intermediate Similarity	NPC181334
0.7984	Intermediate Similarity	NPC74507
0.7984	Intermediate Similarity	NPC474803
0.7983	Intermediate Similarity	NPC477453
0.7982	Intermediate Similarity	NPC320439
0.7982	Intermediate Similarity	NPC66834
0.7982	Intermediate Similarity	NPC305603
0.7982	Intermediate Similarity	NPC61033
0.7982	Intermediate Similarity	NPC228737
0.7969	Intermediate Similarity	NPC85342
0.7966	Intermediate Similarity	NPC285350
0.7966	Intermediate Similarity	NPC12656
0.7965	Intermediate Similarity	NPC243677
0.7965	Intermediate Similarity	NPC303141
0.7949	Intermediate Similarity	NPC62867
0.7949	Intermediate Similarity	NPC228988
0.7949	Intermediate Similarity	NPC26615
0.7949	Intermediate Similarity	NPC98372
0.7949	Intermediate Similarity	NPC177962
0.7949	Intermediate Similarity	NPC286222
0.7939	Intermediate Similarity	NPC278832
0.7939	Intermediate Similarity	NPC64157
0.7937	Intermediate Similarity	NPC95034
0.7937	Intermediate Similarity	NPC142087
0.7934	Intermediate Similarity	NPC151197
0.7931	Intermediate Similarity	NPC44732
0.7923	Intermediate Similarity	NPC204582
0.792	Intermediate Similarity	NPC472592
0.7903	Intermediate Similarity	NPC477152
0.7899	Intermediate Similarity	NPC23402
0.7895	Intermediate Similarity	NPC54765
0.7891	Intermediate Similarity	NPC196621
0.789	Intermediate Similarity	NPC222146
0.7886	Intermediate Similarity	NPC154696
0.7881	Intermediate Similarity	NPC242136
0.7879	Intermediate Similarity	NPC305060
0.7876	Intermediate Similarity	NPC475580
0.7876	Intermediate Similarity	NPC130817
0.7869	Intermediate Similarity	NPC223451
0.7869	Intermediate Similarity	NPC473662
0.7869	Intermediate Similarity	NPC216297
0.7869	Intermediate Similarity	NPC7151
0.7863	Intermediate Similarity	NPC177576
0.7863	Intermediate Similarity	NPC77772
0.7863	Intermediate Similarity	NPC266937
0.7863	Intermediate Similarity	NPC470770
0.7863	Intermediate Similarity	NPC54373
0.7857	Intermediate Similarity	NPC252105
0.7857	Intermediate Similarity	NPC71610
0.7857	Intermediate Similarity	NPC12221
0.7852	Intermediate Similarity	NPC474154
0.7851	Intermediate Similarity	NPC48781
0.7851	Intermediate Similarity	NPC9592
0.785	Intermediate Similarity	NPC192
0.785	Intermediate Similarity	NPC312304
0.7845	Intermediate Similarity	NPC471954
0.7845	Intermediate Similarity	NPC75272
0.784	Intermediate Similarity	NPC231767
0.784	Intermediate Similarity	NPC117794
0.7833	Intermediate Similarity	NPC308828
0.7833	Intermediate Similarity	NPC477137
0.7833	Intermediate Similarity	NPC38893
0.7833	Intermediate Similarity	NPC69539
0.7833	Intermediate Similarity	NPC469663
0.7833	Intermediate Similarity	NPC92
0.7833	Intermediate Similarity	NPC308311
0.783	Intermediate Similarity	NPC19680
0.7829	Intermediate Similarity	NPC476847
0.7829	Intermediate Similarity	NPC471851
0.7826	Intermediate Similarity	NPC233320
0.7826	Intermediate Similarity	NPC34715
0.7823	Intermediate Similarity	NPC325301

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 NPC473931 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	196
0.1-0.2	849
0.2-0.3	1561
0.3-0.4	2763
0.4-0.5	2052
0.5-0.6	1244
0.6-0.7	450
0.7-0.8	34
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)
0.7949	Intermediate Similarity	NPD7635	Approved
0.789	Intermediate Similarity	NPD844	Approved
0.7706	Intermediate Similarity	NPD845	Approved
0.7661	Intermediate Similarity	NPD3496	Discontinued
0.7658	Intermediate Similarity	NPD288	Approved
0.7603	Intermediate Similarity	NPD6671	Approved
0.7583	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD1809	Phase 2
0.7563	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD2935	Discontinued
0.744	Intermediate Similarity	NPD4626	Approved
0.7411	Intermediate Similarity	NPD2860	Approved
0.7411	Intermediate Similarity	NPD2859	Approved
0.7395	Intermediate Similarity	NPD4750	Phase 3
0.7368	Intermediate Similarity	NPD3020	Approved
0.7323	Intermediate Similarity	NPD1201	Approved
0.7321	Intermediate Similarity	NPD2934	Approved
0.7321	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD2933	Approved
0.7302	Intermediate Similarity	NPD2932	Approved
0.7302	Intermediate Similarity	NPD3019	Approved
0.728	Intermediate Similarity	NPD3091	Approved
0.7258	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD5736	Approved
0.725	Intermediate Similarity	NPD3021	Approved
0.725	Intermediate Similarity	NPD3022	Approved
0.7241	Intermediate Similarity	NPD846	Approved
0.7241	Intermediate Similarity	NPD940	Approved
0.7231	Intermediate Similarity	NPD1470	Approved
0.7227	Intermediate Similarity	NPD2342	Discontinued
0.7222	Intermediate Similarity	NPD5691	Approved
0.7154	Intermediate Similarity	NPD6696	Suspended
0.7122	Intermediate Similarity	NPD2424	Discontinued
0.7121	Intermediate Similarity	NPD4208	Discontinued
0.7099	Intermediate Similarity	NPD3094	Phase 2
0.7097	Intermediate Similarity	NPD9618	Approved
0.7097	Intermediate Similarity	NPD497	Approved
0.7097	Intermediate Similarity	NPD9614	Approved
0.7077	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD3092	Approved
0.7037	Intermediate Similarity	NPD6663	Approved
0.7034	Intermediate Similarity	NPD9500	Approved
0.7034	Intermediate Similarity	NPD6647	Phase 2
0.7031	Intermediate Similarity	NPD3095	Discontinued
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	NPD1444	Approved
0.6992	Remote Similarity	NPD2861	Phase 2
0.6985	Remote Similarity	NPD4060	Phase 1
0.6984	Remote Similarity	NPD7340	Approved
0.6984	Remote Similarity	NPD9493	Approved
0.6975	Remote Similarity	NPD1237	Approved
0.6972	Remote Similarity	NPD111	Approved
0.694	Remote Similarity	NPD4207	Discontinued
0.6929	Remote Similarity	NPD9613	Approved
0.6929	Remote Similarity	NPD9615	Approved
0.6929	Remote Similarity	NPD9616	Approved
0.6917	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD8166	Discontinued
0.6899	Remote Similarity	NPD1778	Approved
0.6885	Remote Similarity	NPD74	Approved
0.6885	Remote Similarity	NPD9266	Approved
0.6885	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD6653	Approved
0.688	Remote Similarity	NPD1398	Phase 1
0.6875	Remote Similarity	NPD316	Approved
0.6875	Remote Similarity	NPD7390	Discontinued
0.686	Remote Similarity	NPD968	Approved
0.685	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD3026	Approved
0.6846	Remote Similarity	NPD3023	Approved
0.6842	Remote Similarity	NPD1164	Approved
0.6838	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD7985	Registered
0.6829	Remote Similarity	NPD1792	Phase 2
0.6828	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD2629	Approved
0.6822	Remote Similarity	NPD3025	Approved
0.6822	Remote Similarity	NPD1651	Approved
0.6822	Remote Similarity	NPD3024	Approved
0.6818	Remote Similarity	NPD1755	Approved
0.6815	Remote Similarity	NPD600	Approved
0.6815	Remote Similarity	NPD596	Approved
0.6809	Remote Similarity	NPD6004	Phase 3
0.6809	Remote Similarity	NPD7266	Discontinued
0.6809	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6005	Phase 3
0.6809	Remote Similarity	NPD6002	Phase 3
0.6806	Remote Similarity	NPD3300	Phase 2
0.6803	Remote Similarity	NPD9263	Approved
0.6803	Remote Similarity	NPD9267	Approved
0.6803	Remote Similarity	NPD9264	Approved
0.6803	Remote Similarity	NPD290	Approved
0.68	Remote Similarity	NPD7843	Approved
0.68	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD5536	Phase 2
0.6794	Remote Similarity	NPD1611	Approved
0.6788	Remote Similarity	NPD4248	Discontinued
0.6788	Remote Similarity	NPD839	Approved
0.6788	Remote Similarity	NPD6407	Approved
0.6788	Remote Similarity	NPD6405	Approved
0.6788	Remote Similarity	NPD840	Approved
0.6783	Remote Similarity	NPD3400	Discontinued
0.6783	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD7157	Approved
0.6765	Remote Similarity	NPD3027	Phase 3
0.675	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.675	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD2684	Approved
0.6744	Remote Similarity	NPD1759	Phase 1
0.6744	Remote Similarity	NPD9545	Approved
0.6744	Remote Similarity	NPD7330	Discontinued
0.6739	Remote Similarity	NPD943	Approved
0.6738	Remote Similarity	NPD5405	Approved
0.6738	Remote Similarity	NPD5406	Approved
0.6738	Remote Similarity	NPD5408	Approved
0.6738	Remote Similarity	NPD5404	Approved
0.6738	Remote Similarity	NPD6032	Approved
0.6733	Remote Similarity	NPD6844	Discontinued
0.6723	Remote Similarity	NPD1242	Phase 1
0.672	Remote Similarity	NPD228	Approved
0.6716	Remote Similarity	NPD1129	Approved
0.6716	Remote Similarity	NPD2797	Approved
0.6716	Remote Similarity	NPD1133	Approved
0.6716	Remote Similarity	NPD1135	Approved
0.6716	Remote Similarity	NPD1134	Approved
0.6716	Remote Similarity	NPD1131	Approved
0.6715	Remote Similarity	NPD3268	Approved
0.6715	Remote Similarity	NPD2313	Discontinued
0.6715	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD4380	Phase 2
0.6695	Remote Similarity	NPD9495	Approved
0.6694	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD6355	Discontinued
0.669	Remote Similarity	NPD5762	Approved
0.669	Remote Similarity	NPD5763	Approved
0.669	Remote Similarity	NPD2346	Discontinued
0.6667	Remote Similarity	NPD2799	Discontinued
0.6667	Remote Similarity	NPD1758	Phase 1
0.6667	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2798	Approved
0.6644	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD1283	Approved
0.6641	Remote Similarity	NPD4059	Approved
0.6641	Remote Similarity	NPD255	Approved
0.6641	Remote Similarity	NPD9384	Approved
0.6641	Remote Similarity	NPD256	Approved
0.6641	Remote Similarity	NPD9381	Approved
0.6641	Remote Similarity	NPD4589	Approved
0.6641	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.664	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD9088	Approved
0.6621	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD6190	Approved
0.662	Remote Similarity	NPD6100	Approved
0.662	Remote Similarity	NPD6099	Approved
0.6619	Remote Similarity	NPD826	Approved
0.6619	Remote Similarity	NPD825	Approved
0.6618	Remote Similarity	NPD4212	Discontinued
0.6618	Remote Similarity	NPD2237	Approved
0.6617	Remote Similarity	NPD2232	Approved
0.6617	Remote Similarity	NPD2230	Approved
0.6617	Remote Similarity	NPD2235	Phase 2
0.6617	Remote Similarity	NPD2233	Approved
0.6617	Remote Similarity	NPD2231	Phase 2
0.6615	Remote Similarity	NPD5303	Approved
0.6615	Remote Similarity	NPD5304	Approved
0.6615	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD2228	Approved
0.6614	Remote Similarity	NPD2229	Approved
0.6614	Remote Similarity	NPD1241	Discontinued
0.6614	Remote Similarity	NPD2234	Approved
0.6614	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD2532	Approved
0.6599	Remote Similarity	NPD2534	Approved
0.6599	Remote Similarity	NPD2533	Approved
0.6596	Remote Similarity	NPD7097	Phase 1
0.6594	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD6798	Discontinued
0.6593	Remote Similarity	NPD6362	Approved
0.6591	Remote Similarity	NPD3847	Discontinued
0.6589	Remote Similarity	NPD7636	Approved
0.6585	Remote Similarity	NPD3134	Approved
0.6583	Remote Similarity	NPD3028	Approved
0.6573	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD230	Phase 1
0.6571	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD5124	Phase 1

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