NPASS Compound

Structure

NPC475880 OpenBabel07101718182D 31 32 0 0 1 0 0 0 0 0999 V2000 -6.7309 -5.6578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4040 -5.2095 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0567 -1.9836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6275 -2.3117 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 -0.7355 0.4914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4368 -0.8282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5391 -0.0517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7297 -1.5353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5050 -0.3105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4028 -1.0870 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 -1.8320 -0.7588 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 -7.1792 -3.9848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4380 -4.9507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7638 -1.2765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6616 -2.0529 0.0000 C 0 0 3 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2133 -3.7259 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9545 -2.7600 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 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5062 -4.4331 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9885 -2.5012 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 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 7 9 1 0 0 0 0 7 11 2 0 0 0 0 8 10 1 0 0 0 0 8 13 1 0 0 0 0 9 19 1 0 0 0 0 10 19 2 0 0 0 0 11 20 1 0 0 0 0 12 14 1 0 0 0 0 12 22 1 0 0 0 0 13 27 1 0 0 0 0 14 27 1 0 0 0 0 15 18 1 0 0 0 0 15 24 1 0 0 0 0 16 21 1 0 0 0 0 16 23 2 0 0 0 0 17 22 2 0 0 0 0 17 23 1 0 0 0 0 20 25 1 0 0 0 0 21 26 2 0 0 0 0 22 26 1 0 0 0 0 23 28 1 0 0 0 0 24 25 1 0 0 0 0 24 29 1 6 0 0 0 25 30 2 0 0 0 0 26 31 1 0 0 0 0 27 6 1 6 0 0 0 27 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	428.29
Volume:	477.777
LogP:	6.411
LogD:	5.19
LogS:	-4.684
# Rotatable Bonds:	11
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.323
Synthetic Accessibility Score:	3.921
Fsp3:	0.63
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.871
MDCK Permeability:	1.656227686908096e-05
Pgp-inhibitor:	0.548
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.927
30% Bioavailability (F30%):	0.851

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.676
Plasma Protein Binding (PPB):	98.7415542602539%
Volume Distribution (VD):	0.405
Pgp-substrate:	0.7119580507278442%

ADMET: Metabolism

CYP1A2-inhibitor:	0.173
CYP1A2-substrate:	0.665
CYP2C19-inhibitor:	0.657
CYP2C19-substrate:	0.658
CYP2C9-inhibitor:	0.627
CYP2C9-substrate:	0.957
CYP2D6-inhibitor:	0.757
CYP2D6-substrate:	0.508
CYP3A4-inhibitor:	0.874
CYP3A4-substrate:	0.24

ADMET: Excretion

Clearance (CL):	6.508
Half-life (T1/2):	0.301

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.221
Drug-inuced Liver Injury (DILI):	0.086
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.038
Maximum Recommended Daily Dose:	0.55
Skin Sensitization:	0.788
Carcinogencity:	0.046
Eye Corrosion:	0.003
Eye Irritation:	0.103
Respiratory Toxicity:	0.457

Download Data

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

Natural Product: NPC475880

Natural Product ID:	NPC475880
*Common Name:**	Sargachromanol H
IUPAC Name:	(4R,7Z,10E)-4-hydroxy-13-[(2R)-6-hydroxy-2,8-dimethyl-3,4-dihydrochromen-2-yl]-2,6,10-trimethyltrideca-7,10-dien-5-one
Synonyms:	Sargachromanol H
Standard InCHIKey:	CHKKJDHXYINKDR-NTNCAPJNSA-N
Standard InCHI:	InChI=1S/C27H40O4/c1-18(2)15-24(29)25(30)20(4)11-7-9-19(3)10-8-13-27(6)14-12-22-17-23(28)16-21(5)26(22)31-27/h7,10-11,16-18,20,24,28-29H,8-9,12-15H2,1-6H3/b11-7-,19-10+/t20?,24-,27-/m1/s1
SMILES:	CC1=CC(=CC2=C1OC(CC2)(C)CCC=C(C)CC=CC(C)C(=O)C(CC(C)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517913
PubChem CID:	11384853
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001534] Quinone and hydroquinone lipids [CHEMONTID:0001546] Vitamin E compounds

*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
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921416]
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]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2
MIC	6
Others	1

Activity Type	# Activity
Individual Protein	1
Organism	6
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1087	Individual Protein	Isocitrate lyase	Candida albicans	IC50	>	200.0	ug.mL-1	PMID[493512]
NPT1	Others	Radical scavenging activity		Activity	=	87.8	%	PMID[493511]
NPT2	Others	Unspecified		IC50	=	4600.0	nM	PMID[493512]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[493512]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	100.0	ug.mL-1	PMID[493512]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	100.0	ug.mL-1	PMID[493512]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	>	100.0	ug.mL-1	PMID[493512]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	>	100.0	ug.mL-1	PMID[493512]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[493512]

☑ 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 NPC475880 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	264
0.1-0.2	1250
0.2-0.3	3292
0.3-0.4	9189
0.4-0.5	10162
0.5-0.6	4346
0.6-0.7	10813
0.7-0.8	3271
0.8-0.85	53
0.85-0.9	35
0.9-0.95	18
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.976	High Similarity	NPC474143
0.976	High Similarity	NPC474246
0.96	High Similarity	NPC59654
0.9444	High Similarity	NPC271832
0.928	High Similarity	NPC477213
0.9231	High Similarity	NPC477210
0.9134	High Similarity	NPC319422
0.9134	High Similarity	NPC477212
0.9134	High Similarity	NPC477214
0.9134	High Similarity	NPC477211
0.9106	High Similarity	NPC232295
0.9106	High Similarity	NPC474131
0.9048	High Similarity	NPC474237
0.904	High Similarity	NPC46586
0.904	High Similarity	NPC204535
0.9024	High Similarity	NPC32152
0.8968	High Similarity	NPC474130
0.8898	High Similarity	NPC276962
0.8898	High Similarity	NPC190086
0.8862	High Similarity	NPC187993
0.8862	High Similarity	NPC238176
0.8815	High Similarity	NPC475028
0.8815	High Similarity	NPC476025
0.8788	High Similarity	NPC329427
0.8788	High Similarity	NPC317601
0.878	High Similarity	NPC69539
0.8779	High Similarity	NPC196621
0.875	High Similarity	NPC147896
0.8692	High Similarity	NPC95034
0.8692	High Similarity	NPC142087
0.8686	High Similarity	NPC475063
0.8686	High Similarity	NPC475044
0.864	High Similarity	NPC283616
0.8626	High Similarity	NPC201419
0.8593	High Similarity	NPC475011
0.8561	High Similarity	NPC474154
0.8548	High Similarity	NPC473718
0.854	High Similarity	NPC474943
0.854	High Similarity	NPC475005
0.8516	High Similarity	NPC48623
0.8516	High Similarity	NPC168707
0.8478	Intermediate Similarity	NPC475045
0.845	Intermediate Similarity	NPC49441
0.845	Intermediate Similarity	NPC302211
0.8444	Intermediate Similarity	NPC470871
0.8438	Intermediate Similarity	NPC45663
0.8438	Intermediate Similarity	NPC473875
0.8425	Intermediate Similarity	NPC51341
0.8394	Intermediate Similarity	NPC474610
0.8385	Intermediate Similarity	NPC261992
0.8372	Intermediate Similarity	NPC476165
0.837	Intermediate Similarity	NPC27578
0.837	Intermediate Similarity	NPC118253
0.837	Intermediate Similarity	NPC289624
0.8345	Intermediate Similarity	NPC76312
0.8321	Intermediate Similarity	NPC475029
0.8321	Intermediate Similarity	NPC476018
0.832	Intermediate Similarity	NPC473931
0.832	Intermediate Similarity	NPC474050
0.832	Intermediate Similarity	NPC474114
0.8309	Intermediate Similarity	NPC211352
0.8308	Intermediate Similarity	NPC188997
0.8306	Intermediate Similarity	NPC474920
0.8298	Intermediate Similarity	NPC329493
0.8296	Intermediate Similarity	NPC153019
0.8281	Intermediate Similarity	NPC476020
0.8261	Intermediate Similarity	NPC64157
0.8261	Intermediate Similarity	NPC194847
0.8261	Intermediate Similarity	NPC278832
0.8261	Intermediate Similarity	NPC21797
0.824	Intermediate Similarity	NPC296144
0.824	Intermediate Similarity	NPC28784
0.8239	Intermediate Similarity	NPC316691
0.8239	Intermediate Similarity	NPC474599
0.8235	Intermediate Similarity	NPC251549
0.8214	Intermediate Similarity	NPC79372
0.8203	Intermediate Similarity	NPC139047
0.8189	Intermediate Similarity	NPC154256
0.8189	Intermediate Similarity	NPC290470
0.8182	Intermediate Similarity	NPC61685
0.8182	Intermediate Similarity	NPC471600
0.8182	Intermediate Similarity	NPC248557
0.8162	Intermediate Similarity	NPC258073
0.8148	Intermediate Similarity	NPC206028
0.8143	Intermediate Similarity	NPC265335
0.814	Intermediate Similarity	NPC471449
0.8134	Intermediate Similarity	NPC473993
0.811	Intermediate Similarity	NPC301321
0.8088	Intermediate Similarity	NPC470725
0.8074	Intermediate Similarity	NPC176590
0.8074	Intermediate Similarity	NPC47288
0.8074	Intermediate Similarity	NPC476024
0.8071	Intermediate Similarity	NPC98804
0.8049	Intermediate Similarity	NPC233320
0.8047	Intermediate Similarity	NPC242580
0.8047	Intermediate Similarity	NPC236070
0.8047	Intermediate Similarity	NPC126759
0.8028	Intermediate Similarity	NPC477535
0.8016	Intermediate Similarity	NPC98372
0.8015	Intermediate Similarity	NPC472795
0.8015	Intermediate Similarity	NPC97326
0.8015	Intermediate Similarity	NPC475529
0.8015	Intermediate Similarity	NPC472796
0.8	Intermediate Similarity	NPC208229
0.7985	Intermediate Similarity	NPC320847
0.7985	Intermediate Similarity	NPC81641
0.7985	Intermediate Similarity	NPC476254
0.7985	Intermediate Similarity	NPC131397
0.7971	Intermediate Similarity	NPC312560
0.7958	Intermediate Similarity	NPC475012
0.7958	Intermediate Similarity	NPC472794
0.7958	Intermediate Similarity	NPC473049
0.7955	Intermediate Similarity	NPC475839
0.7945	Intermediate Similarity	NPC474422
0.7943	Intermediate Similarity	NPC309452
0.7943	Intermediate Similarity	NPC470722
0.7943	Intermediate Similarity	NPC470721
0.7943	Intermediate Similarity	NPC156888
0.7943	Intermediate Similarity	NPC130976
0.7943	Intermediate Similarity	NPC6100
0.7941	Intermediate Similarity	NPC274717
0.7941	Intermediate Similarity	NPC38604
0.7941	Intermediate Similarity	NPC211179
0.7941	Intermediate Similarity	NPC81261
0.7937	Intermediate Similarity	NPC275627
0.7931	Intermediate Similarity	NPC477409
0.7929	Intermediate Similarity	NPC161856
0.7929	Intermediate Similarity	NPC51087
0.7929	Intermediate Similarity	NPC281169
0.7929	Intermediate Similarity	NPC291119
0.7926	Intermediate Similarity	NPC474944
0.792	Intermediate Similarity	NPC26013
0.792	Intermediate Similarity	NPC282855
0.7902	Intermediate Similarity	NPC477537
0.7899	Intermediate Similarity	NPC141549
0.7895	Intermediate Similarity	NPC477151
0.7895	Intermediate Similarity	NPC132518
0.7895	Intermediate Similarity	NPC150026
0.7895	Intermediate Similarity	NPC281137
0.7895	Intermediate Similarity	NPC282390
0.7883	Intermediate Similarity	NPC472797
0.7883	Intermediate Similarity	NPC93962
0.7879	Intermediate Similarity	NPC96423
0.7879	Intermediate Similarity	NPC129176
0.7872	Intermediate Similarity	NPC475628
0.7872	Intermediate Similarity	NPC472800
0.7857	Intermediate Similarity	NPC27394
0.7857	Intermediate Similarity	NPC265793
0.7852	Intermediate Similarity	NPC279118
0.7852	Intermediate Similarity	NPC28476
0.7852	Intermediate Similarity	NPC224657
0.7852	Intermediate Similarity	NPC37348
0.7852	Intermediate Similarity	NPC133407
0.7847	Intermediate Similarity	NPC184053
0.7842	Intermediate Similarity	NPC13005
0.784	Intermediate Similarity	NPC68260
0.784	Intermediate Similarity	NPC241549
0.784	Intermediate Similarity	NPC279887
0.7832	Intermediate Similarity	NPC477408
0.7829	Intermediate Similarity	NPC215917
0.7829	Intermediate Similarity	NPC10754
0.7829	Intermediate Similarity	NPC20530
0.7826	Intermediate Similarity	NPC278787
0.7826	Intermediate Similarity	NPC123
0.7826	Intermediate Similarity	NPC11089
0.7826	Intermediate Similarity	NPC475102
0.7826	Intermediate Similarity	NPC163169
0.7826	Intermediate Similarity	NPC325003
0.7823	Intermediate Similarity	NPC472333
0.7823	Intermediate Similarity	NPC208507
0.7815	Intermediate Similarity	NPC193200
0.7812	Intermediate Similarity	NPC190212
0.781	Intermediate Similarity	NPC278308
0.781	Intermediate Similarity	NPC38664
0.781	Intermediate Similarity	NPC226661
0.781	Intermediate Similarity	NPC53986
0.7803	Intermediate Similarity	NPC193193
0.7803	Intermediate Similarity	NPC31314
0.7803	Intermediate Similarity	NPC473136
0.7801	Intermediate Similarity	NPC22222
0.7801	Intermediate Similarity	NPC281513
0.7794	Intermediate Similarity	NPC128321
0.7794	Intermediate Similarity	NPC276212
0.7793	Intermediate Similarity	NPC229916
0.7786	Intermediate Similarity	NPC206205
0.7786	Intermediate Similarity	NPC26394
0.7785	Intermediate Similarity	NPC241636
0.7778	Intermediate Similarity	NPC472791
0.7778	Intermediate Similarity	NPC472792
0.777	Intermediate Similarity	NPC472590
0.777	Intermediate Similarity	NPC228369
0.777	Intermediate Similarity	NPC12875
0.777	Intermediate Similarity	NPC280653
0.777	Intermediate Similarity	NPC68205
0.777	Intermediate Similarity	NPC473982
0.777	Intermediate Similarity	NPC473133
0.777	Intermediate Similarity	NPC164804
0.777	Intermediate Similarity	NPC17343
0.777	Intermediate Similarity	NPC293203
0.777	Intermediate Similarity	NPC164574

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 NPC475880 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	249
0.1-0.2	873
0.2-0.3	1584
0.3-0.4	2485
0.4-0.5	2006
0.5-0.6	1168
0.6-0.7	676
0.7-0.8	106
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8699	High Similarity	NPD6671	Approved
0.8102	Intermediate Similarity	NPD4060	Phase 1
0.8047	Intermediate Similarity	NPD7340	Approved
0.8015	Intermediate Similarity	NPD3496	Discontinued
0.8	Intermediate Similarity	NPD2861	Phase 2
0.7914	Intermediate Similarity	NPD6355	Discontinued
0.7832	Intermediate Similarity	NPD2424	Discontinued
0.7826	Intermediate Similarity	NPD7985	Registered
0.7826	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD1398	Phase 1
0.7778	Intermediate Similarity	NPD6696	Suspended
0.7762	Intermediate Similarity	NPD5762	Approved
0.7762	Intermediate Similarity	NPD5763	Approved
0.773	Intermediate Similarity	NPD6653	Approved
0.7698	Intermediate Similarity	NPD6798	Discontinued
0.7692	Intermediate Similarity	NPD2935	Discontinued
0.7692	Intermediate Similarity	NPD6099	Approved
0.7692	Intermediate Similarity	NPD6100	Approved
0.768	Intermediate Similarity	NPD968	Approved
0.7676	Intermediate Similarity	NPD7097	Phase 1
0.7669	Intermediate Similarity	NPD1778	Approved
0.7643	Intermediate Similarity	NPD6233	Phase 2
0.7639	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD6002	Phase 3
0.7639	Intermediate Similarity	NPD6005	Phase 3
0.7639	Intermediate Similarity	NPD6004	Phase 3
0.7639	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD7095	Approved
0.7603	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD5585	Approved
0.7576	Intermediate Similarity	NPD7644	Approved
0.7574	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD4749	Approved
0.7571	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD1611	Approved
0.7517	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7033	Discontinued
0.75	Intermediate Similarity	NPD2235	Phase 2
0.75	Intermediate Similarity	NPD2231	Phase 2
0.75	Intermediate Similarity	NPD4625	Phase 3
0.7483	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD290	Approved
0.7468	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD6362	Approved
0.7464	Intermediate Similarity	NPD2797	Approved
0.7462	Intermediate Similarity	NPD7843	Approved
0.7448	Intermediate Similarity	NPD6032	Approved
0.7447	Intermediate Similarity	NPD3268	Approved
0.7434	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD4908	Phase 1
0.7426	Intermediate Similarity	NPD1535	Discovery
0.7424	Intermediate Similarity	NPD7157	Approved
0.7422	Intermediate Similarity	NPD2684	Approved
0.7413	Intermediate Similarity	NPD5124	Phase 1
0.7413	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD4626	Approved
0.7403	Intermediate Similarity	NPD6844	Discontinued
0.74	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD2346	Discontinued
0.7379	Intermediate Similarity	NPD2799	Discontinued
0.7372	Intermediate Similarity	NPD1481	Phase 2
0.7372	Intermediate Similarity	NPD1608	Approved
0.7343	Intermediate Similarity	NPD1613	Approved
0.7343	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD4140	Approved
0.7333	Intermediate Similarity	NPD5691	Approved
0.7333	Intermediate Similarity	NPD1651	Approved
0.7328	Intermediate Similarity	NPD7635	Approved
0.7325	Intermediate Similarity	NPD7075	Discontinued
0.7324	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD2313	Discontinued
0.7319	Intermediate Similarity	NPD4359	Approved
0.7308	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD1610	Phase 2
0.7299	Intermediate Similarity	NPD1091	Approved
0.7299	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD5647	Approved
0.7286	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1241	Discontinued
0.7273	Intermediate Similarity	NPD4062	Phase 3
0.7266	Intermediate Similarity	NPD8651	Approved
0.7266	Intermediate Similarity	NPD1283	Approved
0.7255	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD2232	Approved
0.7246	Intermediate Similarity	NPD2233	Approved
0.7246	Intermediate Similarity	NPD2230	Approved
0.7244	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD6090	Discontinued
0.7234	Intermediate Similarity	NPD2237	Approved
0.7226	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2979	Phase 3
0.7211	Intermediate Similarity	NPD4477	Approved
0.7211	Intermediate Similarity	NPD4476	Approved
0.7197	Intermediate Similarity	NPD5402	Approved
0.7194	Intermediate Similarity	NPD5327	Phase 3
0.7194	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1934	Approved
0.7172	Intermediate Similarity	NPD5735	Approved
0.7171	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD3691	Phase 2
0.7163	Intermediate Similarity	NPD3690	Phase 2
0.7163	Intermediate Similarity	NPD6584	Phase 3
0.7162	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD4380	Phase 2
0.716	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6166	Phase 2
0.716	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD4870	Approved
0.7153	Intermediate Similarity	NPD8032	Phase 2
0.7153	Intermediate Similarity	NPD17	Approved
0.7152	Intermediate Similarity	NPD6666	Approved
0.7152	Intermediate Similarity	NPD6667	Approved
0.7143	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD5929	Approved
0.7134	Intermediate Similarity	NPD7819	Suspended
0.7134	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD7976	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD3027	Phase 3
0.7133	Intermediate Similarity	NPD4110	Phase 3
0.7133	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD1894	Discontinued
0.7123	Intermediate Similarity	NPD6353	Approved
0.7114	Intermediate Similarity	NPD1549	Phase 2
0.7113	Intermediate Similarity	NPD5736	Approved
0.7103	Intermediate Similarity	NPD2238	Phase 2
0.7101	Intermediate Similarity	NPD3847	Discontinued
0.7092	Intermediate Similarity	NPD3267	Approved
0.7092	Intermediate Similarity	NPD3266	Approved
0.7075	Intermediate Similarity	NPD4536	Approved
0.7075	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD4538	Approved
0.7071	Intermediate Similarity	NPD3685	Discontinued
0.7068	Intermediate Similarity	NPD5535	Approved
0.7067	Intermediate Similarity	NPD6674	Discontinued
0.7063	Intermediate Similarity	NPD596	Approved
0.7063	Intermediate Similarity	NPD600	Approved
0.7063	Intermediate Similarity	NPD6832	Phase 2
0.7063	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4622	Approved
0.7055	Intermediate Similarity	NPD4618	Approved
0.705	Intermediate Similarity	NPD1281	Approved
0.7047	Intermediate Similarity	NPD6800	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD2798	Approved
0.7037	Intermediate Similarity	NPD3787	Discontinued
0.7034	Intermediate Similarity	NPD839	Approved
0.7034	Intermediate Similarity	NPD840	Approved
0.703	Intermediate Similarity	NPD5844	Phase 1
0.7027	Intermediate Similarity	NPD4308	Phase 3
0.7025	Intermediate Similarity	NPD2801	Approved
0.7025	Intermediate Similarity	NPD8455	Phase 2
0.7021	Intermediate Similarity	NPD3225	Approved
0.702	Intermediate Similarity	NPD4628	Phase 3
0.7019	Intermediate Similarity	NPD5494	Approved
0.7015	Intermediate Similarity	NPD5283	Phase 1
0.7013	Intermediate Similarity	NPD2676	Approved
0.7013	Intermediate Similarity	NPD2675	Approved
0.7013	Intermediate Similarity	NPD6273	Approved
0.7007	Intermediate Similarity	NPD2157	Approved
0.7007	Intermediate Similarity	NPD1548	Phase 1
0.7	Intermediate Similarity	NPD9717	Approved
0.7	Intermediate Similarity	NPD4534	Discontinued
0.7	Intermediate Similarity	NPD5958	Discontinued
0.7	Intermediate Similarity	NPD2897	Discontinued
0.7	Intermediate Similarity	NPD3453	Discontinued
0.6993	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1712	Approved
0.6993	Remote Similarity	NPD7041	Phase 2
0.6993	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD228	Approved
0.6987	Remote Similarity	NPD3226	Approved
0.698	Remote Similarity	NPD2438	Suspended
0.6975	Remote Similarity	NPD6959	Discontinued
0.6972	Remote Similarity	NPD1203	Approved
0.6972	Remote Similarity	NPD987	Approved
0.6966	Remote Similarity	NPD1048	Approved
0.6963	Remote Similarity	NPD2629	Approved
0.6962	Remote Similarity	NPD6801	Discontinued
0.696	Remote Similarity	NPD844	Approved
0.6959	Remote Similarity	NPD5688	Approved
0.6959	Remote Similarity	NPD5689	Approved
0.6957	Remote Similarity	NPD5709	Phase 3
0.695	Remote Similarity	NPD6583	Phase 3
0.695	Remote Similarity	NPD6582	Phase 2
0.6948	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD2614	Approved
0.694	Remote Similarity	NPD821	Approved
0.694	Remote Similarity	NPD1138	Approved
0.6939	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD447	Suspended
0.6937	Remote Similarity	NPD3882	Suspended
0.6936	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD845	Approved
0.6934	Remote Similarity	NPD5536	Phase 2
0.6933	Remote Similarity	NPD2344	Approved
0.6929	Remote Similarity	NPD422	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