NPASS Compound

Structure

NPC271832 OpenBabel07101718282D 31 32 0 0 1 0 0 0 0 0999 V2000 -10.1971 1.4826 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9724 2.7074 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 -6.8510 0.5860 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 -8.5241 1.0343 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 -9.2312 1.7414 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 -7.1099 -0.3799 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7829 0.0684 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.0758 -0.6387 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 -9.7488 -0.1904 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3346 -1.6046 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 1 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 2 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 2 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:	426.28
Volume:	475.141
LogP:	6.117
LogD:	4.969
LogS:	-4.656
# Rotatable Bonds:	10
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.353
Synthetic Accessibility Score:	4.172
Fsp3:	0.556
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.764
MDCK Permeability:	1.7937001757672988e-05
Pgp-inhibitor:	0.148
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.018
30% Bioavailability (F30%):	0.07

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.181
Plasma Protein Binding (PPB):	99.74868774414062%
Volume Distribution (VD):	0.306
Pgp-substrate:	0.7444658279418945%

ADMET: Metabolism

CYP1A2-inhibitor:	0.276
CYP1A2-substrate:	0.542
CYP2C19-inhibitor:	0.785
CYP2C19-substrate:	0.518
CYP2C9-inhibitor:	0.804
CYP2C9-substrate:	0.957
CYP2D6-inhibitor:	0.849
CYP2D6-substrate:	0.278
CYP3A4-inhibitor:	0.906
CYP3A4-substrate:	0.238

ADMET: Excretion

Clearance (CL):	7.229
Half-life (T1/2):	0.351

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.093
Drug-inuced Liver Injury (DILI):	0.14
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.036
Maximum Recommended Daily Dose:	0.464
Skin Sensitization:	0.383
Carcinogencity:	0.047
Eye Corrosion:	0.004
Eye Irritation:	0.094
Respiratory Toxicity:	0.35

Download Data

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

Natural Product: NPC271832

Natural Product ID:	NPC271832
*Common Name:**	Sargachromanol G
IUPAC Name:	(4R,6E,10E)-4-hydroxy-13-[(2R)-6-hydroxy-2,8-dimethyl-3,4-dihydrochromen-2-yl]-2,6,10-trimethyltrideca-2,6,10-trien-5-one
Synonyms:	Sargachromanol G
Standard InCHIKey:	CBIUHPWNXBUXBG-AZIDNILZSA-N
Standard InCHI:	InChI=1S/C27H38O4/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/h10-11,15-17,24,28-29H,7-9,12-14H2,1-6H3/b19-10+,20-11+/t24-,27-/m1/s1
SMILES:	C/C(=CCC[C@]1(C)CCc2c(O1)c(C)cc(c2)O)/CC/C=C(/C(=O)[C@@H](C=C(C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462917
PubChem CID:	11407674
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 [CHEMONTID:0002092] Tocotrienols

*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	2

Activity Type	# Activity
Individual Protein	2
Organism	6
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT439	Individual Protein	Butyrylcholinesterase	Homo sapiens	Inhibition	=	82.7	%	PMID[495177]
NPT1087	Individual Protein	Isocitrate lyase	Candida albicans	IC50	>	200.0	ug.mL-1	PMID[495178]
NPT1	Others	Radical scavenging activity		Activity	=	90.4	%	PMID[495177]
NPT2	Others	Unspecified		IC50	=	24400.0	nM	PMID[495178]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[495178]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	100.0	ug.mL-1	PMID[495178]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	100.0	ug.mL-1	PMID[495178]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	>	100.0	ug.mL-1	PMID[495178]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	>	100.0	ug.mL-1	PMID[495178]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[495178]

☑ 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 NPC271832 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	269
0.1-0.2	1328
0.2-0.3	3871
0.3-0.4	9699
0.4-0.5	9254
0.5-0.6	4310
0.6-0.7	10903
0.7-0.8	2953
0.8-0.85	53
0.85-0.9	32
0.9-0.95	23
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9837	High Similarity	NPC59654
0.9444	High Similarity	NPC475880
0.937	High Similarity	NPC474246
0.937	High Similarity	NPC474143
0.9274	High Similarity	NPC147896
0.9274	High Similarity	NPC276962
0.9274	High Similarity	NPC190086
0.918	High Similarity	NPC232295
0.9113	High Similarity	NPC204535
0.9113	High Similarity	NPC46586
0.9098	High Similarity	NPC32152
0.9055	High Similarity	NPC319422
0.9055	High Similarity	NPC477211
0.9055	High Similarity	NPC477214
0.9055	High Similarity	NPC477212
0.904	High Similarity	NPC474130
0.9024	High Similarity	NPC474131
0.9008	High Similarity	NPC477210
0.8898	High Similarity	NPC477213
0.8855	High Similarity	NPC329427
0.8855	High Similarity	NPC317601
0.8852	High Similarity	NPC69539
0.8846	High Similarity	NPC196621
0.8819	High Similarity	NPC474237
0.879	High Similarity	NPC476020
0.878	High Similarity	NPC238176
0.878	High Similarity	NPC187993
0.876	High Similarity	NPC95034
0.876	High Similarity	NPC142087
0.873	High Similarity	NPC476165
0.8623	High Similarity	NPC474154
0.8571	High Similarity	NPC118253
0.856	High Similarity	NPC283616
0.855	High Similarity	NPC201419
0.854	High Similarity	NPC475045
0.8537	High Similarity	NPC473931
0.8537	High Similarity	NPC474114
0.8537	High Similarity	NPC474050
0.8516	High Similarity	NPC49441
0.8516	High Similarity	NPC302211
0.8504	High Similarity	NPC45663
0.8478	Intermediate Similarity	NPC475044
0.8478	Intermediate Similarity	NPC475063
0.8473	Intermediate Similarity	NPC473993
0.8468	Intermediate Similarity	NPC473718
0.8467	Intermediate Similarity	NPC474943
0.8467	Intermediate Similarity	NPC475005
0.8456	Intermediate Similarity	NPC64157
0.8456	Intermediate Similarity	NPC278832
0.8455	Intermediate Similarity	NPC296144
0.8455	Intermediate Similarity	NPC28784
0.8438	Intermediate Similarity	NPC168707
0.8438	Intermediate Similarity	NPC48623
0.837	Intermediate Similarity	NPC470871
0.8359	Intermediate Similarity	NPC473875
0.8333	Intermediate Similarity	NPC475028
0.8333	Intermediate Similarity	NPC476025
0.8296	Intermediate Similarity	NPC251549
0.8296	Intermediate Similarity	NPC289624
0.8296	Intermediate Similarity	NPC27578
0.8271	Intermediate Similarity	NPC81261
0.8268	Intermediate Similarity	NPC139047
0.8227	Intermediate Similarity	NPC329493
0.8226	Intermediate Similarity	NPC474920
0.8211	Intermediate Similarity	NPC208229
0.8203	Intermediate Similarity	NPC51341
0.8188	Intermediate Similarity	NPC194847
0.8188	Intermediate Similarity	NPC21797
0.8169	Intermediate Similarity	NPC316691
0.8168	Intermediate Similarity	NPC261992
0.813	Intermediate Similarity	NPC282855
0.813	Intermediate Similarity	NPC26013
0.8116	Intermediate Similarity	NPC475011
0.8112	Intermediate Similarity	NPC471600
0.811	Intermediate Similarity	NPC154256
0.811	Intermediate Similarity	NPC290470
0.8106	Intermediate Similarity	NPC61685
0.8102	Intermediate Similarity	NPC211352
0.8092	Intermediate Similarity	NPC188997
0.8088	Intermediate Similarity	NPC153019
0.808	Intermediate Similarity	NPC98372
0.8062	Intermediate Similarity	NPC98748
0.8062	Intermediate Similarity	NPC471449
0.8049	Intermediate Similarity	NPC68260
0.8049	Intermediate Similarity	NPC279887
0.8043	Intermediate Similarity	NPC265793
0.8031	Intermediate Similarity	NPC301321
0.8015	Intermediate Similarity	NPC163169
0.8015	Intermediate Similarity	NPC251259
0.8015	Intermediate Similarity	NPC123
0.8	Intermediate Similarity	NPC14177
0.8	Intermediate Similarity	NPC130976
0.8	Intermediate Similarity	NPC309452
0.7986	Intermediate Similarity	NPC476018
0.7986	Intermediate Similarity	NPC475029
0.7971	Intermediate Similarity	NPC31849
0.797	Intermediate Similarity	NPC248557
0.7969	Intermediate Similarity	NPC236070
0.7969	Intermediate Similarity	NPC126759
0.7969	Intermediate Similarity	NPC163398
0.7969	Intermediate Similarity	NPC242580
0.7967	Intermediate Similarity	NPC233320
0.7959	Intermediate Similarity	NPC241636
0.7958	Intermediate Similarity	NPC477535
0.7958	Intermediate Similarity	NPC152771
0.7958	Intermediate Similarity	NPC195357
0.7958	Intermediate Similarity	NPC477537
0.7956	Intermediate Similarity	NPC141549
0.7955	Intermediate Similarity	NPC132518
0.7955	Intermediate Similarity	NPC477151
0.7953	Intermediate Similarity	NPC114918
0.7943	Intermediate Similarity	NPC98395
0.7943	Intermediate Similarity	NPC151946
0.7943	Intermediate Similarity	NPC279573
0.7943	Intermediate Similarity	NPC211110
0.7941	Intermediate Similarity	NPC472796
0.7941	Intermediate Similarity	NPC97326
0.7941	Intermediate Similarity	NPC472795
0.7939	Intermediate Similarity	NPC475529
0.7939	Intermediate Similarity	NPC322569
0.7939	Intermediate Similarity	NPC131868
0.7929	Intermediate Similarity	NPC474610
0.7929	Intermediate Similarity	NPC115861
0.792	Intermediate Similarity	NPC471535
0.791	Intermediate Similarity	NPC131397
0.791	Intermediate Similarity	NPC224657
0.791	Intermediate Similarity	NPC476254
0.7907	Intermediate Similarity	NPC183154
0.7907	Intermediate Similarity	NPC263754
0.7902	Intermediate Similarity	NPC184053
0.7899	Intermediate Similarity	NPC312560
0.7899	Intermediate Similarity	NPC194277
0.7895	Intermediate Similarity	NPC248786
0.7887	Intermediate Similarity	NPC76312
0.7887	Intermediate Similarity	NPC475012
0.7887	Intermediate Similarity	NPC312881
0.7887	Intermediate Similarity	NPC477408
0.7883	Intermediate Similarity	NPC278787
0.7872	Intermediate Similarity	NPC155963
0.7868	Intermediate Similarity	NPC47288
0.7868	Intermediate Similarity	NPC274717
0.7868	Intermediate Similarity	NPC38604
0.7868	Intermediate Similarity	NPC176590
0.7868	Intermediate Similarity	NPC211179
0.7863	Intermediate Similarity	NPC31314
0.7863	Intermediate Similarity	NPC193193
0.7862	Intermediate Similarity	NPC477409
0.7862	Intermediate Similarity	NPC469642
0.7857	Intermediate Similarity	NPC281513
0.7857	Intermediate Similarity	NPC51087
0.7857	Intermediate Similarity	NPC161856
0.7857	Intermediate Similarity	NPC275627
0.7857	Intermediate Similarity	NPC291119
0.7857	Intermediate Similarity	NPC22222
0.7857	Intermediate Similarity	NPC281169
0.784	Intermediate Similarity	NPC98392
0.7832	Intermediate Similarity	NPC287286
0.7829	Intermediate Similarity	NPC281137
0.7829	Intermediate Similarity	NPC282390
0.7826	Intermediate Similarity	NPC258073
0.7823	Intermediate Similarity	NPC91902
0.782	Intermediate Similarity	NPC325301
0.7812	Intermediate Similarity	NPC87563
0.7812	Intermediate Similarity	NPC114144
0.7812	Intermediate Similarity	NPC41851
0.7812	Intermediate Similarity	NPC197513
0.781	Intermediate Similarity	NPC939
0.781	Intermediate Similarity	NPC472797
0.781	Intermediate Similarity	NPC206028
0.7803	Intermediate Similarity	NPC96423
0.7803	Intermediate Similarity	NPC129176
0.7801	Intermediate Similarity	NPC26954
0.7801	Intermediate Similarity	NPC38099
0.7801	Intermediate Similarity	NPC472800
0.7793	Intermediate Similarity	NPC264706
0.7793	Intermediate Similarity	NPC474599
0.7793	Intermediate Similarity	NPC93433
0.7793	Intermediate Similarity	NPC284881
0.7793	Intermediate Similarity	NPC474444
0.7792	Intermediate Similarity	NPC3629
0.7786	Intermediate Similarity	NPC213173
0.7786	Intermediate Similarity	NPC326600
0.7786	Intermediate Similarity	NPC27394
0.7786	Intermediate Similarity	NPC62366
0.7786	Intermediate Similarity	NPC50896
0.7786	Intermediate Similarity	NPC204353
0.7786	Intermediate Similarity	NPC224475
0.7786	Intermediate Similarity	NPC180716
0.7785	Intermediate Similarity	NPC37348
0.7785	Intermediate Similarity	NPC61258
0.7778	Intermediate Similarity	NPC469564
0.7778	Intermediate Similarity	NPC320847
0.7778	Intermediate Similarity	NPC81641
0.7778	Intermediate Similarity	NPC133407
0.7778	Intermediate Similarity	NPC28476
0.777	Intermediate Similarity	NPC2190
0.777	Intermediate Similarity	NPC51262
0.7762	Intermediate Similarity	NPC472794
0.7762	Intermediate Similarity	NPC79372
0.7762	Intermediate Similarity	NPC268691

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 NPC271832 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	245
0.1-0.2	913
0.2-0.3	1664
0.3-0.4	2579
0.4-0.5	1919
0.5-0.6	1141
0.6-0.7	615
0.7-0.8	72
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8618	High Similarity	NPD6671	Approved
0.8217	Intermediate Similarity	NPD3496	Discontinued
0.7969	Intermediate Similarity	NPD7340	Approved
0.7899	Intermediate Similarity	NPD4060	Phase 1
0.7887	Intermediate Similarity	NPD2424	Discontinued
0.7874	Intermediate Similarity	NPD1398	Phase 1
0.7836	Intermediate Similarity	NPD6696	Suspended
0.7794	Intermediate Similarity	NPD2861	Phase 2
0.7754	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD2935	Discontinued
0.7655	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD7985	Registered
0.76	Intermediate Similarity	NPD968	Approved
0.7594	Intermediate Similarity	NPD4626	Approved
0.7569	Intermediate Similarity	NPD5762	Approved
0.7569	Intermediate Similarity	NPD5763	Approved
0.7519	Intermediate Similarity	NPD5691	Approved
0.75	Intermediate Similarity	NPD4749	Approved
0.75	Intermediate Similarity	NPD7644	Approved
0.7481	Intermediate Similarity	NPD1611	Approved
0.7465	Intermediate Similarity	NPD6355	Discontinued
0.7465	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD5124	Phase 1
0.7451	Intermediate Similarity	NPD6844	Discontinued
0.745	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD2346	Discontinued
0.7429	Intermediate Similarity	NPD7095	Approved
0.7429	Intermediate Similarity	NPD4625	Phase 3
0.7403	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD290	Approved
0.7385	Intermediate Similarity	NPD7843	Approved
0.7379	Intermediate Similarity	NPD6099	Approved
0.7379	Intermediate Similarity	NPD6100	Approved
0.7376	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD2313	Discontinued
0.7376	Intermediate Similarity	NPD6798	Discontinued
0.7372	Intermediate Similarity	NPD7075	Discontinued
0.7372	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD7097	Phase 1
0.7353	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD7157	Approved
0.7347	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD2684	Approved
0.7333	Intermediate Similarity	NPD1778	Approved
0.7328	Intermediate Similarity	NPD1241	Discontinued
0.7324	Intermediate Similarity	NPD6233	Phase 2
0.731	Intermediate Similarity	NPD2799	Discontinued
0.7299	Intermediate Similarity	NPD2235	Phase 2
0.7299	Intermediate Similarity	NPD2231	Phase 2
0.7292	Intermediate Similarity	NPD6653	Approved
0.729	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1613	Approved
0.7266	Intermediate Similarity	NPD2797	Approved
0.726	Intermediate Similarity	NPD6032	Approved
0.7254	Intermediate Similarity	NPD3268	Approved
0.7244	Intermediate Similarity	NPD5402	Approved
0.7234	Intermediate Similarity	NPD4908	Phase 1
0.723	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1091	Approved
0.7214	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD6004	Phase 3
0.7211	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD6002	Phase 3
0.7211	Intermediate Similarity	NPD6005	Phase 3
0.7208	Intermediate Similarity	NPD4380	Phase 2
0.7194	Intermediate Similarity	NPD8651	Approved
0.7192	Intermediate Similarity	NPD7033	Discontinued
0.719	Intermediate Similarity	NPD1653	Approved
0.7179	Intermediate Similarity	NPD7819	Suspended
0.7171	Intermediate Similarity	NPD6090	Discontinued
0.7163	Intermediate Similarity	NPD2237	Approved
0.7162	Intermediate Similarity	NPD1549	Phase 2
0.7153	Intermediate Similarity	NPD4140	Approved
0.7134	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD5585	Approved
0.7121	Intermediate Similarity	NPD7635	Approved
0.7115	Intermediate Similarity	NPD1934	Approved
0.7113	Intermediate Similarity	NPD6832	Phase 2
0.7111	Intermediate Similarity	NPD5536	Phase 2
0.7109	Intermediate Similarity	NPD9697	Approved
0.7101	Intermediate Similarity	NPD422	Phase 1
0.7101	Intermediate Similarity	NPD1535	Discovery
0.7101	Intermediate Similarity	NPD1610	Phase 2
0.7099	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6166	Phase 2
0.7099	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD6584	Phase 3
0.7092	Intermediate Similarity	NPD3690	Phase 2
0.7092	Intermediate Similarity	NPD3691	Phase 2
0.7075	Intermediate Similarity	NPD4308	Phase 3
0.7073	Intermediate Similarity	NPD5844	Phase 1
0.7073	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD5929	Approved
0.7067	Intermediate Similarity	NPD4628	Phase 3
0.7067	Intermediate Similarity	NPD7976	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD3027	Phase 3
0.7059	Intermediate Similarity	NPD2675	Approved
0.7059	Intermediate Similarity	NPD2676	Approved
0.7054	Intermediate Similarity	NPD3134	Approved
0.705	Intermediate Similarity	NPD2232	Approved
0.705	Intermediate Similarity	NPD2233	Approved
0.705	Intermediate Similarity	NPD2230	Approved
0.705	Intermediate Similarity	NPD9717	Approved
0.705	Intermediate Similarity	NPD1481	Phase 2
0.7042	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD3226	Approved
0.7025	Intermediate Similarity	NPD2415	Discontinued
0.7021	Intermediate Similarity	NPD1203	Approved
0.7021	Intermediate Similarity	NPD6362	Approved
0.7019	Intermediate Similarity	NPD6959	Discontinued
0.7014	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1651	Approved
0.7007	Intermediate Similarity	NPD4536	Approved
0.7007	Intermediate Similarity	NPD4538	Approved
0.7006	Intermediate Similarity	NPD6801	Discontinued
0.7	Intermediate Similarity	NPD6674	Discontinued
0.7	Intermediate Similarity	NPD1358	Approved
0.7	Intermediate Similarity	NPD5327	Phase 3
0.6993	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD600	Approved
0.6993	Remote Similarity	NPD596	Approved
0.6993	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD5535	Approved
0.6986	Remote Similarity	NPD447	Suspended
0.6986	Remote Similarity	NPD5735	Approved
0.6986	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD3882	Suspended
0.6981	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.698	Remote Similarity	NPD2344	Approved
0.6977	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD6667	Approved
0.6974	Remote Similarity	NPD6666	Approved
0.6972	Remote Similarity	NPD2798	Approved
0.6966	Remote Similarity	NPD839	Approved
0.6966	Remote Similarity	NPD4062	Phase 3
0.6966	Remote Similarity	NPD840	Approved
0.6962	Remote Similarity	NPD2801	Approved
0.6957	Remote Similarity	NPD5494	Approved
0.695	Remote Similarity	NPD3225	Approved
0.6948	Remote Similarity	NPD6273	Approved
0.6948	Remote Similarity	NPD5049	Phase 3
0.6946	Remote Similarity	NPD6559	Discontinued
0.6943	Remote Similarity	NPD7411	Suspended
0.6939	Remote Similarity	NPD6353	Approved
0.6937	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD1548	Phase 1
0.6929	Remote Similarity	NPD1608	Approved
0.6918	Remote Similarity	NPD2238	Phase 2
0.6917	Remote Similarity	NPD228	Approved
0.6913	Remote Similarity	NPD4477	Approved
0.6913	Remote Similarity	NPD4476	Approved
0.6913	Remote Similarity	NPD2796	Approved
0.6909	Remote Similarity	NPD3751	Discontinued
0.6903	Remote Similarity	NPD5403	Approved
0.6901	Remote Similarity	NPD3267	Approved
0.6901	Remote Similarity	NPD3266	Approved
0.6897	Remote Similarity	NPD411	Approved
0.6897	Remote Similarity	NPD1048	Approved
0.6894	Remote Similarity	NPD5709	Phase 3
0.6887	Remote Similarity	NPD1652	Phase 2
0.6886	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD1578	Phase 2
0.688	Remote Similarity	NPD844	Approved
0.6879	Remote Similarity	NPD6582	Phase 2
0.6879	Remote Similarity	NPD4359	Approved
0.6879	Remote Similarity	NPD3685	Discontinued
0.6879	Remote Similarity	NPD6583	Phase 3
0.6875	Remote Similarity	NPD7768	Phase 2
0.6867	Remote Similarity	NPD7266	Discontinued
0.6866	Remote Similarity	NPD821	Approved
0.6864	Remote Similarity	NPD8312	Approved
0.6864	Remote Similarity	NPD8313	Approved
0.6859	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD558	Phase 2
0.6853	Remote Similarity	NPD5647	Approved
0.6852	Remote Similarity	NPD4666	Phase 3
0.6846	Remote Similarity	NPD5588	Approved
0.6846	Remote Similarity	NPD1510	Phase 2
0.6846	Remote Similarity	NPD5960	Phase 3
0.6845	Remote Similarity	NPD7251	Discontinued
0.6842	Remote Similarity	NPD7835	Discontinued
0.6842	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3750	Approved
0.6839	Remote Similarity	NPD1512	Approved
0.6839	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD2557	Approved
0.6835	Remote Similarity	NPD7615	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