NPASS Compound

Structure

NPC282855 OpenBabel07101719252D 30 30 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 -8.6603 3.0000 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 -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 -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 -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 -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 -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 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 23 1 0 0 0 0 7 9 1 0 0 0 0 7 10 1 0 0 0 0 8 11 1 0 0 0 0 8 12 1 0 0 0 0 9 19 2 0 0 0 0 10 20 1 0 0 0 0 11 20 2 0 0 0 0 12 21 1 0 0 0 0 13 14 1 0 0 0 0 13 22 2 0 0 0 0 14 24 1 0 0 0 0 15 21 2 0 0 0 0 15 25 1 0 0 0 0 16 22 1 0 0 0 0 16 25 1 0 0 0 0 17 23 1 0 0 0 0 17 26 2 0 0 0 0 18 24 2 0 0 0 0 18 26 1 0 0 0 0 23 27 2 0 0 0 0 24 27 1 0 0 0 0 25 28 2 0 0 0 0 26 29 1 0 0 0 0 27 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	410.28
Volume:	472.271
LogP:	6.74
LogD:	4.527
LogS:	-4.524
# Rotatable Bonds:	11
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.229
Synthetic Accessibility Score:	3.329
Fsp3:	0.444
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.848
MDCK Permeability:	2.2212512703845277e-05
Pgp-inhibitor:	0.534
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.044
20% Bioavailability (F20%):	0.994
30% Bioavailability (F30%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021
Plasma Protein Binding (PPB):	96.3975601196289%
Volume Distribution (VD):	3.508
Pgp-substrate:	0.7645395398139954%

ADMET: Metabolism

CYP1A2-inhibitor:	0.742
CYP1A2-substrate:	0.244
CYP2C19-inhibitor:	0.872
CYP2C19-substrate:	0.221
CYP2C9-inhibitor:	0.901
CYP2C9-substrate:	0.983
CYP2D6-inhibitor:	0.894
CYP2D6-substrate:	0.8
CYP3A4-inhibitor:	0.783
CYP3A4-substrate:	0.196

ADMET: Excretion

Clearance (CL):	10.185
Half-life (T1/2):	0.825

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.825
Drug-inuced Liver Injury (DILI):	0.031
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.015
Maximum Recommended Daily Dose:	0.929
Skin Sensitization:	0.965
Carcinogencity:	0.224
Eye Corrosion:	0.61
Eye Irritation:	0.938
Respiratory Toxicity:	0.875

Download Data

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

Natural Product: NPC282855

Natural Product ID:	NPC282855
*Common Name:**	(2E,6E,10E)-1-(2,5-Dihydroxy-3-Methylphenyl)-3,7,11,15-Tetramethylhexadeca-2,6,10,14-Tetraen-5-One
IUPAC Name:	(2E,6E,10E)-1-(2,5-dihydroxy-3-methylphenyl)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-5-one
Synonyms:
Standard InCHIKey:	NESKDGGRNAMQOK-WGOVEGMISA-N
Standard InCHI:	InChI=1S/C27H38O3/c1-19(2)9-7-10-20(3)11-8-12-21(4)15-25(28)16-22(5)13-14-24-18-26(29)17-23(6)27(24)30/h9,11,13,15,17-18,29-30H,7-8,10,12,14,16H2,1-6H3/b20-11+,21-15+,22-13+
SMILES:	C/C(=CC(=O)C/C(=C/Cc1cc(O)cc(c1O)C)/C)/CC/C=C(/CCC=C(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL459195
PubChem CID:	10251029
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	=	8.6	%	PMID[484908]
NPT1	Others	Radical scavenging activity		Activity	=	6.0	%	PMID[484908]
NPT1	Others	Radical scavenging activity		Activity	=	24.4	%	PMID[484908]
NPT1	Others	Radical scavenging activity		Activity	=	67.4	%	PMID[484908]
NPT1	Others	Radical scavenging activity		Activity	=	95.0	%	PMID[484908]
NPT1	Others	Radical scavenging activity		Activity	=	94.4	%	PMID[484908]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	13.3	%	PMID[484908]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	17.0	%	PMID[484908]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	24.3	%	PMID[484908]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	61.7	%	PMID[484908]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	70.8	%	PMID[484908]

☑ 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 NPC282855 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	231
0.1-0.2	1412
0.2-0.3	3817
0.3-0.4	12025
0.4-0.5	7896
0.5-0.6	9055
0.6-0.7	6850
0.7-0.8	1233
0.8-0.85	134
0.85-0.9	33
0.9-0.95	1
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC26013
0.9902	High Similarity	NPC208229
0.9901	High Similarity	NPC68260
0.9901	High Similarity	NPC279887
0.9619	High Similarity	NPC296144
0.9619	High Similarity	NPC28784
0.9528	High Similarity	NPC473931
0.9528	High Similarity	NPC474114
0.9528	High Similarity	NPC474050
0.9346	High Similarity	NPC114918
0.9029	High Similarity	NPC108497
0.902	High Similarity	NPC129373
0.902	High Similarity	NPC248396
0.902	High Similarity	NPC48730
0.8952	High Similarity	NPC469913
0.8932	High Similarity	NPC477685
0.8929	High Similarity	NPC476020
0.8922	High Similarity	NPC260775
0.8889	High Similarity	NPC228609
0.8879	High Similarity	NPC98392
0.8846	High Similarity	NPC269212
0.8835	High Similarity	NPC70677
0.8835	High Similarity	NPC12931
0.8835	High Similarity	NPC130756
0.8824	High Similarity	NPC152097
0.8649	High Similarity	NPC197513
0.8641	High Similarity	NPC475078
0.8624	High Similarity	NPC471535
0.8621	High Similarity	NPC49441
0.8609	High Similarity	NPC474175
0.8598	High Similarity	NPC155072
0.8585	High Similarity	NPC272029
0.8584	High Similarity	NPC269414
0.8571	High Similarity	NPC80800
0.8545	High Similarity	NPC469912
0.8505	High Similarity	NPC47284
0.8431	Intermediate Similarity	NPC162314
0.8431	Intermediate Similarity	NPC94139
0.8431	Intermediate Similarity	NPC3358
0.8431	Intermediate Similarity	NPC210497
0.8431	Intermediate Similarity	NPC29373
0.8431	Intermediate Similarity	NPC306884
0.8431	Intermediate Similarity	NPC147284
0.8426	Intermediate Similarity	NPC53740
0.8417	Intermediate Similarity	NPC319422
0.8417	Intermediate Similarity	NPC477214
0.8417	Intermediate Similarity	NPC477211
0.8417	Intermediate Similarity	NPC477212
0.8411	Intermediate Similarity	NPC93831
0.8407	Intermediate Similarity	NPC240163
0.8349	Intermediate Similarity	NPC320439
0.8349	Intermediate Similarity	NPC228737
0.8333	Intermediate Similarity	NPC303141
0.8333	Intermediate Similarity	NPC477453
0.8333	Intermediate Similarity	NPC243677
0.8319	Intermediate Similarity	NPC276962
0.8319	Intermediate Similarity	NPC190086
0.8304	Intermediate Similarity	NPC286222
0.8304	Intermediate Similarity	NPC177962
0.8304	Intermediate Similarity	NPC302371
0.8304	Intermediate Similarity	NPC62867
0.8279	Intermediate Similarity	NPC59654
0.8269	Intermediate Similarity	NPC222146
0.8257	Intermediate Similarity	NPC54765
0.825	Intermediate Similarity	NPC477213
0.825	Intermediate Similarity	NPC131799
0.8241	Intermediate Similarity	NPC475580
0.8235	Intermediate Similarity	NPC477153
0.8235	Intermediate Similarity	NPC192
0.823	Intermediate Similarity	NPC242136
0.8224	Intermediate Similarity	NPC252105
0.8224	Intermediate Similarity	NPC12221
0.822	Intermediate Similarity	NPC154696
0.8218	Intermediate Similarity	NPC19680
0.8214	Intermediate Similarity	NPC266937
0.8214	Intermediate Similarity	NPC470770
0.8214	Intermediate Similarity	NPC77772
0.8211	Intermediate Similarity	NPC123
0.8211	Intermediate Similarity	NPC163169
0.8211	Intermediate Similarity	NPC196621
0.8182	Intermediate Similarity	NPC474352
0.8182	Intermediate Similarity	NPC227741
0.8182	Intermediate Similarity	NPC49647
0.8182	Intermediate Similarity	NPC474944
0.8182	Intermediate Similarity	NPC306765
0.8182	Intermediate Similarity	NPC295202
0.8182	Intermediate Similarity	NPC136342
0.8182	Intermediate Similarity	NPC34715
0.8174	Intermediate Similarity	NPC69539
0.8167	Intermediate Similarity	NPC147896
0.8167	Intermediate Similarity	NPC474237
0.8165	Intermediate Similarity	NPC138942
0.8165	Intermediate Similarity	NPC117115
0.8158	Intermediate Similarity	NPC41851
0.8148	Intermediate Similarity	NPC235762
0.8148	Intermediate Similarity	NPC470202
0.8148	Intermediate Similarity	NPC471228
0.8142	Intermediate Similarity	NPC98372
0.8131	Intermediate Similarity	NPC225506
0.8131	Intermediate Similarity	NPC72729
0.8131	Intermediate Similarity	NPC130103
0.8131	Intermediate Similarity	NPC174911
0.813	Intermediate Similarity	NPC271832
0.8125	Intermediate Similarity	NPC132720
0.812	Intermediate Similarity	NPC473767
0.8115	Intermediate Similarity	NPC142087
0.8115	Intermediate Similarity	NPC95034
0.8113	Intermediate Similarity	NPC77492
0.8113	Intermediate Similarity	NPC474073
0.8113	Intermediate Similarity	NPC79241
0.8113	Intermediate Similarity	NPC6597
0.8108	Intermediate Similarity	NPC470039
0.8108	Intermediate Similarity	NPC95344
0.8103	Intermediate Similarity	NPC187993
0.8103	Intermediate Similarity	NPC160199
0.8103	Intermediate Similarity	NPC238176
0.8095	Intermediate Similarity	NPC32714
0.8091	Intermediate Similarity	NPC99836
0.8091	Intermediate Similarity	NPC201662
0.8091	Intermediate Similarity	NPC12640
0.8087	Intermediate Similarity	NPC161304
0.8083	Intermediate Similarity	NPC275145
0.8083	Intermediate Similarity	NPC273683
0.808	Intermediate Similarity	NPC251549
0.8073	Intermediate Similarity	NPC475225
0.8073	Intermediate Similarity	NPC288411
0.807	Intermediate Similarity	NPC162113
0.807	Intermediate Similarity	NPC190212
0.807	Intermediate Similarity	NPC62546
0.8056	Intermediate Similarity	NPC166313
0.8056	Intermediate Similarity	NPC11280
0.8056	Intermediate Similarity	NPC24407
0.8056	Intermediate Similarity	NPC147310
0.8056	Intermediate Similarity	NPC137415
0.8056	Intermediate Similarity	NPC294186
0.8056	Intermediate Similarity	NPC192032
0.8056	Intermediate Similarity	NPC472585
0.8053	Intermediate Similarity	NPC54373
0.8049	Intermediate Similarity	NPC476024
0.8039	Intermediate Similarity	NPC27974
0.8037	Intermediate Similarity	NPC33675
0.8037	Intermediate Similarity	NPC299762
0.8037	Intermediate Similarity	NPC252821
0.8037	Intermediate Similarity	NPC122005
0.8037	Intermediate Similarity	NPC128723
0.8036	Intermediate Similarity	NPC471954
0.8036	Intermediate Similarity	NPC75272
0.8036	Intermediate Similarity	NPC473524
0.8034	Intermediate Similarity	NPC206205
0.8034	Intermediate Similarity	NPC41567
0.8033	Intermediate Similarity	NPC474945
0.8033	Intermediate Similarity	NPC476022
0.8019	Intermediate Similarity	NPC259512
0.8019	Intermediate Similarity	NPC312132
0.8018	Intermediate Similarity	NPC204901
0.8018	Intermediate Similarity	NPC232523
0.8018	Intermediate Similarity	NPC158253
0.8018	Intermediate Similarity	NPC151477
0.8018	Intermediate Similarity	NPC233320
0.8017	Intermediate Similarity	NPC199273
0.8017	Intermediate Similarity	NPC141001
0.8	Intermediate Similarity	NPC477151
0.8	Intermediate Similarity	NPC245187
0.8	Intermediate Similarity	NPC132518
0.8	Intermediate Similarity	NPC76938
0.8	Intermediate Similarity	NPC289769
0.8	Intermediate Similarity	NPC282577
0.8	Intermediate Similarity	NPC152415
0.8	Intermediate Similarity	NPC37802
0.7983	Intermediate Similarity	NPC115188
0.7983	Intermediate Similarity	NPC26433
0.7983	Intermediate Similarity	NPC159760
0.7983	Intermediate Similarity	NPC35856
0.7983	Intermediate Similarity	NPC272454
0.7983	Intermediate Similarity	NPC292665
0.7983	Intermediate Similarity	NPC179092
0.7983	Intermediate Similarity	NPC222876
0.7983	Intermediate Similarity	NPC190971
0.7983	Intermediate Similarity	NPC301987
0.7983	Intermediate Similarity	NPC259703
0.7983	Intermediate Similarity	NPC32322
0.7983	Intermediate Similarity	NPC244994
0.7983	Intermediate Similarity	NPC178395
0.7982	Intermediate Similarity	NPC168303
0.7982	Intermediate Similarity	NPC222522
0.7982	Intermediate Similarity	NPC249828
0.7982	Intermediate Similarity	NPC53051
0.7982	Intermediate Similarity	NPC94351
0.7982	Intermediate Similarity	NPC302219
0.7982	Intermediate Similarity	NPC228988
0.7982	Intermediate Similarity	NPC24404
0.7982	Intermediate Similarity	NPC146798
0.7982	Intermediate Similarity	NPC168829
0.7982	Intermediate Similarity	NPC106396
0.7982	Intermediate Similarity	NPC233827
0.7982	Intermediate Similarity	NPC71002
0.7982	Intermediate Similarity	NPC313030
0.7982	Intermediate Similarity	NPC242342
0.7982	Intermediate Similarity	NPC26615
0.7982	Intermediate Similarity	NPC85479

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 NPC282855 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	242
0.1-0.2	974
0.2-0.3	1424
0.3-0.4	2897
0.4-0.5	2028
0.5-0.6	1178
0.6-0.7	363
0.7-0.8	39
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8476	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8304	Intermediate Similarity	NPD7635	Approved
0.8269	Intermediate Similarity	NPD844	Approved
0.8077	Intermediate Similarity	NPD845	Approved
0.8019	Intermediate Similarity	NPD288	Approved
0.7931	Intermediate Similarity	NPD6671	Approved
0.7925	Intermediate Similarity	NPD1809	Phase 2
0.7815	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7757	Intermediate Similarity	NPD2859	Approved
0.7757	Intermediate Similarity	NPD2860	Approved
0.7719	Intermediate Similarity	NPD4750	Phase 3
0.7706	Intermediate Similarity	NPD3020	Approved
0.7664	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD2934	Approved
0.7664	Intermediate Similarity	NPD2933	Approved
0.7623	Intermediate Similarity	NPD1201	Approved
0.7603	Intermediate Similarity	NPD4626	Approved
0.7603	Intermediate Similarity	NPD2932	Approved
0.7603	Intermediate Similarity	NPD3019	Approved
0.7568	Intermediate Similarity	NPD940	Approved
0.7568	Intermediate Similarity	NPD846	Approved
0.7563	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD2342	Discontinued
0.7541	Intermediate Similarity	NPD3496	Discontinued
0.75	Intermediate Similarity	NPD2935	Discontinued
0.744	Intermediate Similarity	NPD6696	Suspended
0.7436	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD3022	Approved
0.7414	Intermediate Similarity	NPD3021	Approved
0.7381	Intermediate Similarity	NPD1470	Approved
0.7345	Intermediate Similarity	NPD9500	Approved
0.7311	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD111	Approved
0.7304	Intermediate Similarity	NPD1445	Approved
0.7304	Intermediate Similarity	NPD1444	Approved
0.7273	Intermediate Similarity	NPD7340	Approved
0.725	Intermediate Similarity	NPD497	Approved
0.7236	Intermediate Similarity	NPD5691	Approved
0.7179	Intermediate Similarity	NPD74	Approved
0.7179	Intermediate Similarity	NPD9266	Approved
0.7167	Intermediate Similarity	NPD496	Approved
0.7167	Intermediate Similarity	NPD1398	Phase 1
0.7167	Intermediate Similarity	NPD495	Approved
0.7167	Intermediate Similarity	NPD498	Approved
0.7132	Intermediate Similarity	NPD5736	Approved
0.7132	Intermediate Similarity	NPD4208	Discontinued
0.7131	Intermediate Similarity	NPD9493	Approved
0.7119	Intermediate Similarity	NPD1792	Phase 2
0.7109	Intermediate Similarity	NPD1164	Approved
0.7094	Intermediate Similarity	NPD9263	Approved
0.7094	Intermediate Similarity	NPD9267	Approved
0.7094	Intermediate Similarity	NPD9264	Approved
0.7087	Intermediate Similarity	NPD1755	Approved
0.7087	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD4207	Discontinued
0.7037	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD1242	Phase 1
0.7016	Intermediate Similarity	NPD7330	Discontinued
0.7016	Intermediate Similarity	NPD3091	Approved
0.7	Intermediate Similarity	NPD7390	Discontinued
0.6992	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD3026	Approved
0.6984	Remote Similarity	NPD3023	Approved
0.6977	Remote Similarity	NPD2797	Approved
0.6961	Remote Similarity	NPD9088	Approved
0.696	Remote Similarity	NPD3025	Approved
0.696	Remote Similarity	NPD1651	Approved
0.696	Remote Similarity	NPD3024	Approved
0.6949	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD3300	Phase 2
0.6929	Remote Similarity	NPD1611	Approved
0.6923	Remote Similarity	NPD2798	Approved
0.6917	Remote Similarity	NPD6663	Approved
0.6911	Remote Similarity	NPD256	Approved
0.6911	Remote Similarity	NPD255	Approved
0.6906	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD1778	Approved
0.6905	Remote Similarity	NPD4589	Approved
0.6905	Remote Similarity	NPD4059	Approved
0.6885	Remote Similarity	NPD2229	Approved
0.6885	Remote Similarity	NPD2228	Approved
0.6885	Remote Similarity	NPD2234	Approved
0.688	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.688	Remote Similarity	NPD5304	Approved
0.688	Remote Similarity	NPD1759	Phase 1
0.688	Remote Similarity	NPD5303	Approved
0.687	Remote Similarity	NPD4212	Discontinued
0.687	Remote Similarity	NPD2861	Phase 2
0.6866	Remote Similarity	NPD943	Approved
0.6866	Remote Similarity	NPD4060	Phase 1
0.6864	Remote Similarity	NPD968	Approved
0.6861	Remote Similarity	NPD5404	Approved
0.6861	Remote Similarity	NPD5406	Approved
0.6861	Remote Similarity	NPD5408	Approved
0.6861	Remote Similarity	NPD5405	Approved
0.6861	Remote Similarity	NPD6099	Approved
0.6861	Remote Similarity	NPD6100	Approved
0.686	Remote Similarity	NPD228	Approved
0.6855	Remote Similarity	NPD7636	Approved
0.6842	Remote Similarity	NPD2313	Discontinued
0.6842	Remote Similarity	NPD3268	Approved
0.6842	Remote Similarity	NPD9273	Approved
0.6829	Remote Similarity	NPD9618	Approved
0.6829	Remote Similarity	NPD9614	Approved
0.6829	Remote Similarity	NPD1791	Approved
0.6829	Remote Similarity	NPD1793	Approved
0.6825	Remote Similarity	NPD4093	Discontinued
0.6825	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD4749	Approved
0.6812	Remote Similarity	NPD2346	Discontinued
0.68	Remote Similarity	NPD1758	Phase 1
0.68	Remote Similarity	NPD5536	Phase 2
0.68	Remote Similarity	NPD7644	Approved
0.6797	Remote Similarity	NPD3092	Approved
0.6797	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD2799	Discontinued
0.6786	Remote Similarity	NPD8166	Discontinued
0.6772	Remote Similarity	NPD2286	Discontinued
0.6769	Remote Similarity	NPD1283	Approved
0.6767	Remote Similarity	NPD4625	Phase 3
0.6763	Remote Similarity	NPD2424	Discontinued
0.6752	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD1929	Approved
0.6752	Remote Similarity	NPD1930	Approved
0.6752	Remote Similarity	NPD9261	Approved
0.6746	Remote Similarity	NPD9545	Approved
0.6744	Remote Similarity	NPD2233	Approved
0.6744	Remote Similarity	NPD2232	Approved
0.6744	Remote Similarity	NPD2230	Approved
0.6724	Remote Similarity	NPD3028	Approved
0.6719	Remote Similarity	NPD3143	Discontinued
0.6718	Remote Similarity	NPD3094	Phase 2
0.6716	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD1237	Approved
0.6695	Remote Similarity	NPD9608	Approved
0.6695	Remote Similarity	NPD9610	Approved
0.6694	Remote Similarity	NPD5951	Approved
0.6694	Remote Similarity	NPD9281	Approved
0.6667	Remote Similarity	NPD9616	Approved
0.6667	Remote Similarity	NPD9377	Approved
0.6667	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9613	Approved
0.6667	Remote Similarity	NPD9615	Approved
0.6667	Remote Similarity	NPD9379	Approved
0.6667	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD258	Approved
0.6667	Remote Similarity	NPD422	Phase 1
0.6667	Remote Similarity	NPD257	Approved
0.6667	Remote Similarity	NPD1535	Discovery
0.6642	Remote Similarity	NPD7095	Approved
0.6641	Remote Similarity	NPD3095	Discontinued
0.6641	Remote Similarity	NPD1751	Approved
0.6638	Remote Similarity	NPD2066	Phase 3
0.6637	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD1240	Approved
0.6617	Remote Similarity	NPD2237	Approved
0.6615	Remote Similarity	NPD1608	Approved
0.6615	Remote Similarity	NPD9269	Phase 2
0.6615	Remote Similarity	NPD9717	Approved
0.6615	Remote Similarity	NPD3070	Discontinued
0.6615	Remote Similarity	NPD1481	Phase 2
0.6614	Remote Similarity	NPD316	Approved
0.6613	Remote Similarity	NPD1241	Discontinued
0.6612	Remote Similarity	NPD2684	Approved
0.661	Remote Similarity	NPD6647	Phase 2
0.6596	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD7985	Registered
0.6589	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD3847	Discontinued
0.6587	Remote Similarity	NPD9568	Approved
0.6583	Remote Similarity	NPD3134	Approved
0.6577	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD9295	Approved
0.6571	Remote Similarity	NPD2344	Approved
0.6571	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD9087	Approved
0.6569	Remote Similarity	NPD447	Suspended
0.6567	Remote Similarity	NPD600	Approved
0.6567	Remote Similarity	NPD596	Approved
0.6562	Remote Similarity	NPD5585	Approved
0.6562	Remote Similarity	NPD9268	Approved
0.656	Remote Similarity	NPD2629	Approved
0.656	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD7003	Approved
0.6544	Remote Similarity	NPD4248	Discontinued
0.6538	Remote Similarity	NPD1281	Approved
0.6532	Remote Similarity	NPD1138	Approved
0.6532	Remote Similarity	NPD7843	Approved
0.6531	Remote Similarity	NPD3226	Approved
0.6529	Remote Similarity	NPD290	Approved
0.6522	Remote Similarity	NPD1607	Approved
0.6522	Remote Similarity	NPD6653	Approved
0.6518	Remote Similarity	NPD9258	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