NPASS Compound

Structure

NPC208229 OpenBabel07101719132D 31 31 0 0 0 0 0 0 0 0999 V2000 -8.6603 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 0.5000 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 -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 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 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 -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 -9.5263 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 2.0000 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 -9.5263 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 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 -8.6603 3.0000 0.0000 C 0 0 0 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 -7.7942 3.5000 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 2 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:	292.09
Volume:	270.046
LogP:	1.743
LogD:	1.593
LogS:	-3.528
# Rotatable Bonds:	0
TPSA:	84.73
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.578
Synthetic Accessibility Score:	6.263
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.334
MDCK Permeability:	3.819402991211973e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.973

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.527
Plasma Protein Binding (PPB):	66.72042846679688%
Volume Distribution (VD):	1.326
Pgp-substrate:	37.0731086730957%

ADMET: Metabolism

CYP1A2-inhibitor:	0.045
CYP1A2-substrate:	0.591
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.784
CYP2C9-inhibitor:	0.018
CYP2C9-substrate:	0.045
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.154
CYP3A4-inhibitor:	0.079
CYP3A4-substrate:	0.376

ADMET: Excretion

Clearance (CL):	11.832
Half-life (T1/2):	0.371

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.54
Drug-inuced Liver Injury (DILI):	0.885
AMES Toxicity:	0.08
Rat Oral Acute Toxicity:	0.656
Maximum Recommended Daily Dose:	0.565
Skin Sensitization:	0.285
Carcinogencity:	0.428
Eye Corrosion:	0.004
Eye Irritation:	0.019
Respiratory Toxicity:	0.915

Download Data

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

Natural Product: NPC208229

Natural Product ID:	NPC208229
*Common Name:**	(6E,10E,14E)-16-(2,5-Dihydroxy-3-Methylphenyl)-2,6,10,14-Tetramethylhexadeca-2,6,10,14-Tetraene-4,12-Dione
IUPAC Name:	(6E,10E,14E)-16-(2,5-dihydroxy-3-methylphenyl)-2,6,10,14-tetramethylhexadeca-2,6,10,14-tetraene-4,12-dione
Synonyms:
Standard InCHIKey:	SKFIILPFPHFEQW-WJNRHBMWSA-N
Standard InCHI:	InChI=1S/C27H36O4/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/h8,10,12,14,16-17,30-31H,7,9,11,13,15H2,1-6H3/b19-8+,20-14+,21-10+
SMILES:	C/C(=CC(=O)C/C(=C/Cc1cc(O)cc(c1O)C)/C)/CC/C=C(/CC(=O)C=C(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462111
PubChem CID:	10387653
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	13

Activity Type	# Activity
NON-MOLECULAR	5
Others	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		Activity	=	7.6	%	PMID[530009]
NPT1	Others	Radical scavenging activity		Activity	=	14.3	%	PMID[530009]
NPT1	Others	Radical scavenging activity		Activity	=	29.1	%	PMID[530009]
NPT1	Others	Radical scavenging activity		Activity	=	80.8	%	PMID[530009]
NPT1	Others	Radical scavenging activity		Activity	=	95.7	%	PMID[530009]
NPT1	Others	Radical scavenging activity		Activity	=	95.5	%	PMID[530009]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	13.6	%	PMID[530009]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	20.3	%	PMID[530009]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	39.9	%	PMID[530009]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	70.1	%	PMID[530009]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	72.2	%	PMID[530009]
NPT35	Others	n.a.		Activity	=	0.37	mmol/L	PMID[530009]
NPT2	Others	Unspecified		Activity	=	1.39	mmol/L	PMID[530009]

☑ 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 NPC208229 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	230
0.1-0.2	1348
0.2-0.3	3698
0.3-0.4	11597
0.4-0.5	8319
0.5-0.6	8595
0.6-0.7	7429
0.7-0.8	1321
0.8-0.85	117
0.85-0.9	32
0.9-0.95	1
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9902	High Similarity	NPC282855
0.9902	High Similarity	NPC26013
0.9804	High Similarity	NPC279887
0.9804	High Similarity	NPC68260
0.9714	High Similarity	NPC296144
0.9714	High Similarity	NPC28784
0.9623	High Similarity	NPC473931
0.9623	High Similarity	NPC474050
0.9623	High Similarity	NPC474114
0.9439	High Similarity	NPC114918
0.9018	High Similarity	NPC476020
0.8981	High Similarity	NPC228609
0.8942	High Similarity	NPC108497
0.8932	High Similarity	NPC129373
0.8932	High Similarity	NPC248396
0.8932	High Similarity	NPC48730
0.8868	High Similarity	NPC469913
0.8846	High Similarity	NPC477685
0.8835	High Similarity	NPC260775
0.8796	High Similarity	NPC98392
0.8762	High Similarity	NPC269212
0.875	High Similarity	NPC12931
0.875	High Similarity	NPC130756
0.875	High Similarity	NPC70677
0.8739	High Similarity	NPC197513
0.8738	High Similarity	NPC152097
0.8716	High Similarity	NPC471535
0.8707	High Similarity	NPC49441
0.8696	High Similarity	NPC474175
0.8558	High Similarity	NPC475078
0.8519	High Similarity	NPC155072
0.8509	High Similarity	NPC269414
0.8505	High Similarity	NPC272029
0.8505	High Similarity	NPC93831
0.85	High Similarity	NPC319422
0.85	High Similarity	NPC477211
0.85	High Similarity	NPC477212
0.85	High Similarity	NPC477214
0.8491	Intermediate Similarity	NPC80800
0.8468	Intermediate Similarity	NPC469912
0.8426	Intermediate Similarity	NPC47284
0.8361	Intermediate Similarity	NPC59654
0.835	Intermediate Similarity	NPC162314
0.835	Intermediate Similarity	NPC306884
0.835	Intermediate Similarity	NPC147284
0.835	Intermediate Similarity	NPC210497
0.835	Intermediate Similarity	NPC94139
0.835	Intermediate Similarity	NPC29373
0.835	Intermediate Similarity	NPC3358
0.8349	Intermediate Similarity	NPC53740
0.8333	Intermediate Similarity	NPC240163
0.8333	Intermediate Similarity	NPC477213
0.8319	Intermediate Similarity	NPC477153
0.8293	Intermediate Similarity	NPC123
0.8293	Intermediate Similarity	NPC163169
0.8273	Intermediate Similarity	NPC474352
0.8273	Intermediate Similarity	NPC228737
0.8273	Intermediate Similarity	NPC320439
0.8264	Intermediate Similarity	NPC474944
0.8264	Intermediate Similarity	NPC306765
0.8261	Intermediate Similarity	NPC477453
0.8257	Intermediate Similarity	NPC303141
0.8257	Intermediate Similarity	NPC243677
0.825	Intermediate Similarity	NPC474237
0.825	Intermediate Similarity	NPC276962
0.825	Intermediate Similarity	NPC190086
0.823	Intermediate Similarity	NPC62867
0.823	Intermediate Similarity	NPC302371
0.823	Intermediate Similarity	NPC177962
0.823	Intermediate Similarity	NPC286222
0.8211	Intermediate Similarity	NPC271832
0.8197	Intermediate Similarity	NPC142087
0.8197	Intermediate Similarity	NPC95034
0.819	Intermediate Similarity	NPC222146
0.8182	Intermediate Similarity	NPC54765
0.8182	Intermediate Similarity	NPC131799
0.8165	Intermediate Similarity	NPC475580
0.816	Intermediate Similarity	NPC251549
0.8158	Intermediate Similarity	NPC242136
0.8155	Intermediate Similarity	NPC192
0.8151	Intermediate Similarity	NPC154696
0.8148	Intermediate Similarity	NPC252105
0.8148	Intermediate Similarity	NPC12221
0.8145	Intermediate Similarity	NPC196621
0.8142	Intermediate Similarity	NPC77772
0.8142	Intermediate Similarity	NPC266937
0.8142	Intermediate Similarity	NPC470770
0.8137	Intermediate Similarity	NPC19680
0.813	Intermediate Similarity	NPC476024
0.8125	Intermediate Similarity	NPC473524
0.812	Intermediate Similarity	NPC206205
0.8115	Intermediate Similarity	NPC49647
0.8115	Intermediate Similarity	NPC476022
0.8115	Intermediate Similarity	NPC227741
0.8115	Intermediate Similarity	NPC474945
0.8115	Intermediate Similarity	NPC136342
0.8115	Intermediate Similarity	NPC295202
0.8108	Intermediate Similarity	NPC34715
0.8103	Intermediate Similarity	NPC69539
0.8099	Intermediate Similarity	NPC147896
0.8091	Intermediate Similarity	NPC117115
0.8091	Intermediate Similarity	NPC138942
0.8087	Intermediate Similarity	NPC41851
0.8083	Intermediate Similarity	NPC477151
0.8083	Intermediate Similarity	NPC132518
0.8073	Intermediate Similarity	NPC235762
0.8073	Intermediate Similarity	NPC470202
0.8073	Intermediate Similarity	NPC471228
0.807	Intermediate Similarity	NPC98372
0.8056	Intermediate Similarity	NPC225506
0.8056	Intermediate Similarity	NPC72729
0.8056	Intermediate Similarity	NPC174911
0.8056	Intermediate Similarity	NPC130103
0.8053	Intermediate Similarity	NPC132720
0.8053	Intermediate Similarity	NPC222905
0.8051	Intermediate Similarity	NPC473767
0.8049	Intermediate Similarity	NPC471530
0.8037	Intermediate Similarity	NPC474073
0.8037	Intermediate Similarity	NPC79241
0.8037	Intermediate Similarity	NPC77492
0.8037	Intermediate Similarity	NPC6597
0.8036	Intermediate Similarity	NPC470039
0.8036	Intermediate Similarity	NPC95344
0.8034	Intermediate Similarity	NPC187993
0.8034	Intermediate Similarity	NPC238176
0.8034	Intermediate Similarity	NPC160199
0.8019	Intermediate Similarity	NPC32714
0.8018	Intermediate Similarity	NPC201662
0.8018	Intermediate Similarity	NPC99836
0.8018	Intermediate Similarity	NPC70843
0.8018	Intermediate Similarity	NPC12640
0.8017	Intermediate Similarity	NPC161304
0.8017	Intermediate Similarity	NPC273683
0.8017	Intermediate Similarity	NPC477152
0.8017	Intermediate Similarity	NPC275145
0.8	Intermediate Similarity	NPC475880
0.8	Intermediate Similarity	NPC62546
0.8	Intermediate Similarity	NPC190212
0.8	Intermediate Similarity	NPC162113
0.8	Intermediate Similarity	NPC475225
0.8	Intermediate Similarity	NPC288411
0.7984	Intermediate Similarity	NPC24869
0.7982	Intermediate Similarity	NPC147310
0.7982	Intermediate Similarity	NPC472585
0.7982	Intermediate Similarity	NPC137415
0.7982	Intermediate Similarity	NPC54373
0.7982	Intermediate Similarity	NPC11280
0.7982	Intermediate Similarity	NPC24407
0.7982	Intermediate Similarity	NPC166313
0.7982	Intermediate Similarity	NPC294186
0.7982	Intermediate Similarity	NPC192032
0.7966	Intermediate Similarity	NPC41567
0.7965	Intermediate Similarity	NPC75272
0.7965	Intermediate Similarity	NPC471954
0.7965	Intermediate Similarity	NPC88141
0.7963	Intermediate Similarity	NPC299762
0.7963	Intermediate Similarity	NPC122005
0.7963	Intermediate Similarity	NPC252821
0.7963	Intermediate Similarity	NPC33675
0.7963	Intermediate Similarity	NPC128723
0.7961	Intermediate Similarity	NPC27974
0.7951	Intermediate Similarity	NPC199273
0.7949	Intermediate Similarity	NPC141001
0.7946	Intermediate Similarity	NPC204901
0.7946	Intermediate Similarity	NPC151477
0.7946	Intermediate Similarity	NPC233320
0.7946	Intermediate Similarity	NPC232523
0.7946	Intermediate Similarity	NPC158253
0.7944	Intermediate Similarity	NPC312132
0.7944	Intermediate Similarity	NPC259512
0.7937	Intermediate Similarity	NPC85342
0.7937	Intermediate Similarity	NPC474143
0.7937	Intermediate Similarity	NPC474246
0.7934	Intermediate Similarity	NPC302211
0.7934	Intermediate Similarity	NPC282577
0.7928	Intermediate Similarity	NPC37802
0.7925	Intermediate Similarity	NPC152415
0.7925	Intermediate Similarity	NPC76938
0.7925	Intermediate Similarity	NPC289769
0.7925	Intermediate Similarity	NPC245187
0.792	Intermediate Similarity	NPC278928
0.7917	Intermediate Similarity	NPC178395
0.7917	Intermediate Similarity	NPC159760
0.7917	Intermediate Similarity	NPC32322
0.7917	Intermediate Similarity	NPC244994
0.7917	Intermediate Similarity	NPC164852
0.7917	Intermediate Similarity	NPC272454
0.7917	Intermediate Similarity	NPC115188
0.7917	Intermediate Similarity	NPC179092
0.7917	Intermediate Similarity	NPC292665
0.7917	Intermediate Similarity	NPC35856
0.7917	Intermediate Similarity	NPC26433
0.7917	Intermediate Similarity	NPC222876
0.7917	Intermediate Similarity	NPC165197
0.7917	Intermediate Similarity	NPC301987
0.7917	Intermediate Similarity	NPC190971
0.7917	Intermediate Similarity	NPC259703
0.7913	Intermediate Similarity	NPC26615
0.7913	Intermediate Similarity	NPC43525
0.7913	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 NPC208229 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	226
0.1-0.2	953
0.2-0.3	1458
0.3-0.4	2859
0.4-0.5	2053
0.5-0.6	1173
0.6-0.7	382
0.7-0.8	43
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8396	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.823	Intermediate Similarity	NPD7635	Approved
0.819	Intermediate Similarity	NPD844	Approved
0.8	Intermediate Similarity	NPD845	Approved
0.7944	Intermediate Similarity	NPD288	Approved
0.7863	Intermediate Similarity	NPD6671	Approved
0.785	Intermediate Similarity	NPD1809	Phase 2
0.775	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7685	Intermediate Similarity	NPD2860	Approved
0.7685	Intermediate Similarity	NPD2859	Approved
0.7652	Intermediate Similarity	NPD4750	Phase 3
0.7636	Intermediate Similarity	NPD3020	Approved
0.7623	Intermediate Similarity	NPD3496	Discontinued
0.7593	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD2933	Approved
0.7593	Intermediate Similarity	NPD2934	Approved
0.7576	Intermediate Similarity	NPD2935	Discontinued
0.7561	Intermediate Similarity	NPD1201	Approved
0.7541	Intermediate Similarity	NPD4626	Approved
0.7541	Intermediate Similarity	NPD2932	Approved
0.7541	Intermediate Similarity	NPD3019	Approved
0.7521	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3021	Approved
0.75	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD940	Approved
0.75	Intermediate Similarity	NPD3022	Approved
0.75	Intermediate Similarity	NPD846	Approved
0.7478	Intermediate Similarity	NPD2342	Discontinued
0.746	Intermediate Similarity	NPD1470	Approved
0.7395	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD6696	Suspended
0.7333	Intermediate Similarity	NPD497	Approved
0.7281	Intermediate Similarity	NPD9500	Approved
0.725	Intermediate Similarity	NPD496	Approved
0.725	Intermediate Similarity	NPD495	Approved
0.725	Intermediate Similarity	NPD498	Approved
0.7241	Intermediate Similarity	NPD1444	Approved
0.7241	Intermediate Similarity	NPD1445	Approved
0.7238	Intermediate Similarity	NPD111	Approved
0.7213	Intermediate Similarity	NPD7340	Approved
0.7177	Intermediate Similarity	NPD5691	Approved
0.7165	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD9266	Approved
0.7119	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD74	Approved
0.7111	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1398	Phase 1
0.7077	Intermediate Similarity	NPD4208	Discontinued
0.7077	Intermediate Similarity	NPD5736	Approved
0.7073	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD9493	Approved
0.7071	Intermediate Similarity	NPD7390	Discontinued
0.7063	Intermediate Similarity	NPD3023	Approved
0.7063	Intermediate Similarity	NPD3026	Approved
0.7059	Intermediate Similarity	NPD1792	Phase 2
0.7054	Intermediate Similarity	NPD1164	Approved
0.704	Intermediate Similarity	NPD3024	Approved
0.704	Intermediate Similarity	NPD3025	Approved
0.7034	Intermediate Similarity	NPD9263	Approved
0.7034	Intermediate Similarity	NPD9264	Approved
0.7034	Intermediate Similarity	NPD9267	Approved
0.7031	Intermediate Similarity	NPD1755	Approved
0.7023	Intermediate Similarity	NPD4207	Discontinued
0.7008	Intermediate Similarity	NPD1611	Approved
0.7	Intermediate Similarity	NPD3300	Phase 2
0.6978	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.696	Remote Similarity	NPD7330	Discontinued
0.696	Remote Similarity	NPD1759	Phase 1
0.696	Remote Similarity	NPD3091	Approved
0.6957	Remote Similarity	NPD1242	Phase 1
0.694	Remote Similarity	NPD943	Approved
0.694	Remote Similarity	NPD4060	Phase 1
0.6934	Remote Similarity	NPD5408	Approved
0.6934	Remote Similarity	NPD5405	Approved
0.6934	Remote Similarity	NPD5404	Approved
0.6934	Remote Similarity	NPD5406	Approved
0.6923	Remote Similarity	NPD2797	Approved
0.6917	Remote Similarity	NPD2313	Discontinued
0.6917	Remote Similarity	NPD3268	Approved
0.6905	Remote Similarity	NPD1651	Approved
0.6893	Remote Similarity	NPD9088	Approved
0.6891	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD2346	Discontinued
0.688	Remote Similarity	NPD1758	Phase 1
0.688	Remote Similarity	NPD5536	Phase 2
0.687	Remote Similarity	NPD2798	Approved
0.6866	Remote Similarity	NPD6663	Approved
0.6861	Remote Similarity	NPD2799	Discontinued
0.6857	Remote Similarity	NPD8166	Discontinued
0.6855	Remote Similarity	NPD256	Approved
0.6855	Remote Similarity	NPD255	Approved
0.685	Remote Similarity	NPD1778	Approved
0.685	Remote Similarity	NPD4059	Approved
0.685	Remote Similarity	NPD4589	Approved
0.6835	Remote Similarity	NPD2424	Discontinued
0.6829	Remote Similarity	NPD2234	Approved
0.6829	Remote Similarity	NPD2229	Approved
0.6829	Remote Similarity	NPD2228	Approved
0.6825	Remote Similarity	NPD5303	Approved
0.6825	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD5304	Approved
0.6818	Remote Similarity	NPD2861	Phase 2
0.6818	Remote Similarity	NPD4212	Discontinued
0.6812	Remote Similarity	NPD6099	Approved
0.6812	Remote Similarity	NPD6100	Approved
0.681	Remote Similarity	NPD3028	Approved
0.6807	Remote Similarity	NPD968	Approved
0.6803	Remote Similarity	NPD228	Approved
0.68	Remote Similarity	NPD7636	Approved
0.6794	Remote Similarity	NPD3094	Phase 2
0.6783	Remote Similarity	NPD9273	Approved
0.6783	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD1793	Approved
0.6774	Remote Similarity	NPD9618	Approved
0.6774	Remote Similarity	NPD1791	Approved
0.6774	Remote Similarity	NPD9281	Approved
0.6774	Remote Similarity	NPD9614	Approved
0.6772	Remote Similarity	NPD4093	Discontinued
0.6772	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD4749	Approved
0.6746	Remote Similarity	NPD7644	Approved
0.6744	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD1535	Discovery
0.6744	Remote Similarity	NPD3092	Approved
0.6742	Remote Similarity	NPD258	Approved
0.6742	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD257	Approved
0.6739	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD3095	Discontinued
0.6719	Remote Similarity	NPD2286	Discontinued
0.6718	Remote Similarity	NPD1283	Approved
0.6716	Remote Similarity	NPD7095	Approved
0.6716	Remote Similarity	NPD4625	Phase 3
0.6695	Remote Similarity	NPD6647	Phase 2
0.6695	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD1930	Approved
0.6695	Remote Similarity	NPD1929	Approved
0.6695	Remote Similarity	NPD9261	Approved
0.6693	Remote Similarity	NPD9545	Approved
0.6692	Remote Similarity	NPD9269	Phase 2
0.6692	Remote Similarity	NPD2230	Approved
0.6692	Remote Similarity	NPD2233	Approved
0.6692	Remote Similarity	NPD2232	Approved
0.6692	Remote Similarity	NPD1481	Phase 2
0.6692	Remote Similarity	NPD9717	Approved
0.6667	Remote Similarity	NPD3847	Discontinued
0.6667	Remote Similarity	NPD7985	Registered
0.6667	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3143	Discontinued
0.6667	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD447	Suspended
0.6641	Remote Similarity	NPD9268	Approved
0.664	Remote Similarity	NPD5951	Approved
0.6639	Remote Similarity	NPD9610	Approved
0.6639	Remote Similarity	NPD1237	Approved
0.6639	Remote Similarity	NPD9608	Approved
0.6618	Remote Similarity	NPD4248	Discontinued
0.6615	Remote Similarity	NPD422	Phase 1
0.6614	Remote Similarity	NPD9615	Approved
0.6614	Remote Similarity	NPD9616	Approved
0.6614	Remote Similarity	NPD9613	Approved
0.6613	Remote Similarity	NPD1138	Approved
0.6613	Remote Similarity	NPD9377	Approved
0.6613	Remote Similarity	NPD9379	Approved
0.6613	Remote Similarity	NPD7843	Approved
0.6606	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD3226	Approved
0.6594	Remote Similarity	NPD6653	Approved
0.6591	Remote Similarity	NPD3225	Approved
0.6589	Remote Similarity	NPD1751	Approved
0.6587	Remote Similarity	NPD7157	Approved
0.6587	Remote Similarity	NPD6387	Discontinued
0.6585	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD2066	Phase 3
0.6571	Remote Similarity	NPD6032	Approved
0.6569	Remote Similarity	NPD6346	Approved
0.6569	Remote Similarity	NPD1240	Approved
0.6569	Remote Similarity	NPD825	Approved
0.6569	Remote Similarity	NPD826	Approved
0.6567	Remote Similarity	NPD2237	Approved
0.6565	Remote Similarity	NPD1608	Approved
0.6565	Remote Similarity	NPD3070	Discontinued
0.6562	Remote Similarity	NPD316	Approved
0.656	Remote Similarity	NPD1241	Discontinued
0.656	Remote Similarity	NPD5283	Phase 1
0.6557	Remote Similarity	NPD2684	Approved
0.6552	Remote Similarity	NPD2532	Approved
0.6552	Remote Similarity	NPD2533	Approved
0.6552	Remote Similarity	NPD2534	Approved
0.6544	Remote Similarity	NPD411	Approved
0.6544	Remote Similarity	NPD3764	Approved
0.6544	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD4339	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data