NPASS Compound

Structure

NPC471380 OpenBabel07101719252D 40 45 0 0 1 0 0 0 0 0999 V2000 -3.0777 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8260 3.7128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1619 2.8973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4688 0.9045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4899 0.0770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0777 2.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0777 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4899 3.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3318 4.0111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 3.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3558 2.5091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 4.7361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 2.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4899 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7815 3.4180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3709 3.5090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6027 1.4045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9899 0.9430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 3.7361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5943 3.2822 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6027 2.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1386 3.9506 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9021 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4899 1.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3951 4.3177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9021 2.6180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6728 5.2361 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9899 0.9430 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 2.9271 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2213 4.8810 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7601 -0.2788 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4899 1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6335 4.5906 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 15 1 0 0 0 0 2 16 1 0 0 0 0 3 17 2 0 0 0 0 4 18 1 0 0 0 0 5 19 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 15 1 0 0 0 0 8 20 2 0 0 0 0 9 15 2 0 0 0 0 10 16 1 0 0 0 0 11 20 1 0 0 0 0 11 23 1 0 0 0 0 12 22 1 0 0 0 0 13 20 1 0 0 0 0 13 33 1 0 0 0 0 16 31 1 1 0 0 0 17 21 1 0 0 0 0 17 29 1 0 0 0 0 18 22 2 0 0 0 0 18 26 1 0 0 0 0 19 34 2 0 0 0 0 19 38 1 0 0 0 0 21 12 1 1 0 0 0 21 24 1 0 0 0 0 22 31 1 0 0 0 0 23 27 1 0 0 0 0 23 35 1 6 0 0 0 24 10 1 6 0 0 0 24 39 1 0 0 0 0 25 9 1 1 0 0 0 25 27 1 0 0 0 0 25 40 1 0 0 0 0 26 28 1 0 0 0 0 26 32 1 6 0 0 0 27 32 1 6 0 0 0 28 31 1 1 0 0 0 28 38 1 0 0 0 0 29 36 2 0 0 0 0 29 39 1 0 0 0 0 30 32 1 0 0 0 0 30 37 2 0 0 0 0 30 40 1 0 0 0 0 31 14 1 6 0 0 0 32 14 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	552.27
Volume:	562.556
LogP:	2.227
LogD:	2.543
LogS:	-3.914
# Rotatable Bonds:	3
TPSA:	119.36
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.23
Synthetic Accessibility Score:	7.549
Fsp3:	0.656
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.157
MDCK Permeability:	6.882521120132878e-05
Pgp-inhibitor:	0.304
Pgp-substrate:	0.387
Human Intestinal Absorption (HIA):	0.966
20% Bioavailability (F20%):	0.045
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.642
Plasma Protein Binding (PPB):	80.99009704589844%
Volume Distribution (VD):	0.91
Pgp-substrate:	13.529101371765137%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.071
CYP2C19-inhibitor:	0.041
CYP2C19-substrate:	0.18
CYP2C9-inhibitor:	0.185
CYP2C9-substrate:	0.032
CYP2D6-inhibitor:	0.033
CYP2D6-substrate:	0.074
CYP3A4-inhibitor:	0.84
CYP3A4-substrate:	0.315

ADMET: Excretion

Clearance (CL):	6.932
Half-life (T1/2):	0.254

ADMET: Toxicity

hERG Blockers:	0.234
Human Hepatotoxicity (H-HT):	0.32
Drug-inuced Liver Injury (DILI):	0.595
AMES Toxicity:	0.05
Rat Oral Acute Toxicity:	0.878
Maximum Recommended Daily Dose:	0.772
Skin Sensitization:	0.811
Carcinogencity:	0.356
Eye Corrosion:	0.01
Eye Irritation:	0.018
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC471380

Natural Product ID:	NPC471380
*Common Name:**	GNGQKLZFBUPHJG-ZVHISUOZSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GNGQKLZFBUPHJG-ZVHISUOZSA-N
Standard InCHI:	InChI=1S/C32H40O8/c1-15-7-6-8-20(13-33)11-23(35)27-25(9-15)40-30(37)32(27)14-31-16(2)10-24-21(17(3)29(36)39-24)12-22(31)18(4)26(32)28(31)38-19(5)34/h8-9,16,21,23-28,33,35H,3,6-7,10-14H2,1-2,4-5H3/b15-9+,20-8-/t16-,21+,23-,24-,25-,26-,27-,28-,31-,32+/m0/s1
SMILES:	OC/C/1=CCC/C(=C/[C@H]2[C@H]([C@H](C1)O)[C@]1(C[C@]34[C@H]([C@@H]1C(=C4C[C@H]1[C@H](C[C@@H]3C)OC(=O)C1=C)C)OC(=O)C)C(=O)O2)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2426506
PubChem CID:	73353798
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000513] Eicosanoids [CHEMONTID:0000514] Prostaglandins and related 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
NPO32526	lineariifolia turcz	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[24044895]

☑ 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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2257	Cell Line	MCF-10A	Homo sapiens	IC50	=	26400.0	nM	PMID[564478]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	5700.0	nM	PMID[564478]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	3700.0	nM	PMID[564478]

☑ 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 NPC471380 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	270
0.1-0.2	1648
0.2-0.3	5883
0.3-0.4	14213
0.4-0.5	10224
0.5-0.6	7070
0.6-0.7	2874
0.7-0.8	465
0.8-0.85	36
0.85-0.9	12
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9189	High Similarity	NPC161060
0.9099	High Similarity	NPC36754
0.9091	High Similarity	NPC471382
0.8919	High Similarity	NPC123117
0.8559	High Similarity	NPC471884
0.8496	Intermediate Similarity	NPC209058
0.8407	Intermediate Similarity	NPC23967
0.8364	Intermediate Similarity	NPC475217
0.8304	Intermediate Similarity	NPC475588
0.8198	Intermediate Similarity	NPC252234
0.8182	Intermediate Similarity	NPC474775
0.8167	Intermediate Similarity	NPC129992
0.8165	Intermediate Similarity	NPC171759
0.8131	Intermediate Similarity	NPC24956
0.8131	Intermediate Similarity	NPC18019
0.812	Intermediate Similarity	NPC475323
0.8113	Intermediate Similarity	NPC470010
0.8113	Intermediate Similarity	NPC323008
0.8113	Intermediate Similarity	NPC470013
0.8113	Intermediate Similarity	NPC262133
0.8113	Intermediate Similarity	NPC198853
0.8091	Intermediate Similarity	NPC86077
0.807	Intermediate Similarity	NPC474923
0.807	Intermediate Similarity	NPC48305
0.8056	Intermediate Similarity	NPC161493
0.8051	Intermediate Similarity	NPC475372
0.8037	Intermediate Similarity	NPC52044
0.8037	Intermediate Similarity	NPC67584
0.8036	Intermediate Similarity	NPC223450
0.8036	Intermediate Similarity	NPC243998
0.8	Intermediate Similarity	NPC297474
0.8	Intermediate Similarity	NPC54065
0.7983	Intermediate Similarity	NPC469380
0.7983	Intermediate Similarity	NPC312536
0.7966	Intermediate Similarity	NPC473656
0.7963	Intermediate Similarity	NPC142529
0.7963	Intermediate Similarity	NPC91771
0.7963	Intermediate Similarity	NPC213078
0.7944	Intermediate Similarity	NPC90453
0.7944	Intermediate Similarity	NPC477131
0.7925	Intermediate Similarity	NPC35959
0.7925	Intermediate Similarity	NPC171360
0.7925	Intermediate Similarity	NPC57304
0.7925	Intermediate Similarity	NPC293001
0.7925	Intermediate Similarity	NPC475925
0.7925	Intermediate Similarity	NPC29821
0.7925	Intermediate Similarity	NPC131209
0.7925	Intermediate Similarity	NPC133698
0.7925	Intermediate Similarity	NPC63193
0.7925	Intermediate Similarity	NPC133888
0.7905	Intermediate Similarity	NPC155935
0.7881	Intermediate Similarity	NPC148458
0.787	Intermediate Similarity	NPC213698
0.787	Intermediate Similarity	NPC304886
0.787	Intermediate Similarity	NPC170120
0.7863	Intermediate Similarity	NPC312017
0.7863	Intermediate Similarity	NPC9848
0.7845	Intermediate Similarity	NPC287311
0.7838	Intermediate Similarity	NPC150923
0.783	Intermediate Similarity	NPC35809
0.7818	Intermediate Similarity	NPC141191
0.7818	Intermediate Similarity	NPC221615
0.7815	Intermediate Similarity	NPC475238
0.781	Intermediate Similarity	NPC217983
0.781	Intermediate Similarity	NPC207114
0.7807	Intermediate Similarity	NPC26617
0.7805	Intermediate Similarity	NPC144625
0.7798	Intermediate Similarity	NPC126156
0.7788	Intermediate Similarity	NPC203659
0.7778	Intermediate Similarity	NPC127019
0.7778	Intermediate Similarity	NPC126691
0.7769	Intermediate Similarity	NPC143755
0.7757	Intermediate Similarity	NPC221282
0.7757	Intermediate Similarity	NPC290651
0.775	Intermediate Similarity	NPC288679
0.7748	Intermediate Similarity	NPC241221
0.7736	Intermediate Similarity	NPC283409
0.7736	Intermediate Similarity	NPC215556
0.7731	Intermediate Similarity	NPC277583
0.7727	Intermediate Similarity	NPC108475
0.7727	Intermediate Similarity	NPC169205
0.7727	Intermediate Similarity	NPC170143
0.7727	Intermediate Similarity	NPC213947
0.7724	Intermediate Similarity	NPC469382
0.7724	Intermediate Similarity	NPC469352
0.7719	Intermediate Similarity	NPC54737
0.7706	Intermediate Similarity	NPC36954
0.7706	Intermediate Similarity	NPC476053
0.7706	Intermediate Similarity	NPC163228
0.7699	Intermediate Similarity	NPC110989
0.7698	Intermediate Similarity	NPC470851
0.7698	Intermediate Similarity	NPC13071
0.7692	Intermediate Similarity	NPC474750
0.7686	Intermediate Similarity	NPC472667
0.7685	Intermediate Similarity	NPC200237
0.7685	Intermediate Similarity	NPC135776
0.7679	Intermediate Similarity	NPC477950
0.7672	Intermediate Similarity	NPC59489
0.7672	Intermediate Similarity	NPC273433
0.7672	Intermediate Similarity	NPC139838
0.7667	Intermediate Similarity	NPC239273
0.7664	Intermediate Similarity	NPC301969
0.7664	Intermediate Similarity	NPC216284
0.7664	Intermediate Similarity	NPC19087
0.7664	Intermediate Similarity	NPC469368
0.7664	Intermediate Similarity	NPC37607
0.7661	Intermediate Similarity	NPC86346
0.7661	Intermediate Similarity	NPC75856
0.7661	Intermediate Similarity	NPC469379
0.7658	Intermediate Similarity	NPC23364
0.7647	Intermediate Similarity	NPC474872
0.7647	Intermediate Similarity	NPC90472
0.7647	Intermediate Similarity	NPC474181
0.7642	Intermediate Similarity	NPC471149
0.7642	Intermediate Similarity	NPC91248
0.7642	Intermediate Similarity	NPC79549
0.7636	Intermediate Similarity	NPC185553
0.7636	Intermediate Similarity	NPC476315
0.7632	Intermediate Similarity	NPC100487
0.7632	Intermediate Similarity	NPC473577
0.7632	Intermediate Similarity	NPC474550
0.7632	Intermediate Similarity	NPC475585
0.7627	Intermediate Similarity	NPC475524
0.7627	Intermediate Similarity	NPC258711
0.7627	Intermediate Similarity	NPC95290
0.7627	Intermediate Similarity	NPC221144
0.7627	Intermediate Similarity	NPC100267
0.7627	Intermediate Similarity	NPC189338
0.7627	Intermediate Similarity	NPC35069
0.7623	Intermediate Similarity	NPC19336
0.7623	Intermediate Similarity	NPC185876
0.7623	Intermediate Similarity	NPC4548
0.7619	Intermediate Similarity	NPC56593
0.7619	Intermediate Similarity	NPC172823
0.7619	Intermediate Similarity	NPC187661
0.7619	Intermediate Similarity	NPC470850
0.7615	Intermediate Similarity	NPC474247
0.7611	Intermediate Similarity	NPC475320
0.7611	Intermediate Similarity	NPC225353
0.7607	Intermediate Similarity	NPC206595
0.7607	Intermediate Similarity	NPC257240
0.7607	Intermediate Similarity	NPC477103
0.7593	Intermediate Similarity	NPC184063
0.7593	Intermediate Similarity	NPC286341
0.7593	Intermediate Similarity	NPC191339
0.7589	Intermediate Similarity	NPC280963
0.7589	Intermediate Similarity	NPC218383
0.7586	Intermediate Similarity	NPC308191
0.7586	Intermediate Similarity	NPC476479
0.7583	Intermediate Similarity	NPC138372
0.7583	Intermediate Similarity	NPC49492
0.7583	Intermediate Similarity	NPC266728
0.7583	Intermediate Similarity	NPC106228
0.7581	Intermediate Similarity	NPC1538
0.757	Intermediate Similarity	NPC38392
0.757	Intermediate Similarity	NPC232747
0.757	Intermediate Similarity	NPC474032
0.757	Intermediate Similarity	NPC295312
0.7568	Intermediate Similarity	NPC471150
0.7568	Intermediate Similarity	NPC477949
0.7565	Intermediate Similarity	NPC60315
0.7565	Intermediate Similarity	NPC475290
0.7565	Intermediate Similarity	NPC179891
0.7565	Intermediate Similarity	NPC166115
0.7563	Intermediate Similarity	NPC474937
0.7563	Intermediate Similarity	NPC52634
0.7563	Intermediate Similarity	NPC473535
0.7563	Intermediate Similarity	NPC71889
0.7561	Intermediate Similarity	NPC52839
0.7559	Intermediate Similarity	NPC475371
0.7547	Intermediate Similarity	NPC24728
0.7545	Intermediate Similarity	NPC90121
0.7545	Intermediate Similarity	NPC193645
0.7545	Intermediate Similarity	NPC37408
0.7545	Intermediate Similarity	NPC472873
0.7545	Intermediate Similarity	NPC48803
0.7545	Intermediate Similarity	NPC275960
0.7545	Intermediate Similarity	NPC471142
0.7544	Intermediate Similarity	NPC69171
0.7544	Intermediate Similarity	NPC475334
0.7544	Intermediate Similarity	NPC475623
0.7544	Intermediate Similarity	NPC474165
0.7544	Intermediate Similarity	NPC473694
0.7544	Intermediate Similarity	NPC124881
0.7544	Intermediate Similarity	NPC221421
0.7544	Intermediate Similarity	NPC476237
0.7544	Intermediate Similarity	NPC140723
0.7542	Intermediate Similarity	NPC475668
0.7542	Intermediate Similarity	NPC473921
0.7542	Intermediate Similarity	NPC475480
0.7541	Intermediate Similarity	NPC9674
0.7541	Intermediate Similarity	NPC180640
0.7541	Intermediate Similarity	NPC477092
0.7541	Intermediate Similarity	NPC19028
0.7524	Intermediate Similarity	NPC255307
0.7523	Intermediate Similarity	NPC258216
0.7523	Intermediate Similarity	NPC81419
0.7523	Intermediate Similarity	NPC308656
0.7523	Intermediate Similarity	NPC473234
0.7523	Intermediate Similarity	NPC475838

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 NPC471380 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	278
0.1-0.2	2305
0.2-0.3	3969
0.3-0.4	1860
0.4-0.5	410
0.5-0.6	264
0.6-0.7	56
0.7-0.8	8
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7807	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD6053	Discontinued
0.7607	Intermediate Similarity	NPD6371	Approved
0.7545	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD1695	Approved
0.7182	Intermediate Similarity	NPD5785	Approved
0.717	Intermediate Similarity	NPD5362	Discontinued
0.713	Intermediate Similarity	NPD7640	Approved
0.713	Intermediate Similarity	NPD7639	Approved
0.7064	Intermediate Similarity	NPD4251	Approved
0.7064	Intermediate Similarity	NPD4250	Approved
0.7054	Intermediate Similarity	NPD7507	Approved
0.7043	Intermediate Similarity	NPD7638	Approved
0.6975	Remote Similarity	NPD6008	Approved
0.6972	Remote Similarity	NPD4249	Approved
0.6967	Remote Similarity	NPD6650	Approved
0.6967	Remote Similarity	NPD6649	Approved
0.6942	Remote Similarity	NPD6373	Approved
0.6942	Remote Similarity	NPD6372	Approved
0.6911	Remote Similarity	NPD8297	Approved
0.6894	Remote Similarity	NPD7319	Approved
0.6881	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6899	Approved
0.686	Remote Similarity	NPD6881	Approved
0.686	Remote Similarity	NPD7320	Approved
0.686	Remote Similarity	NPD6686	Approved
0.6833	Remote Similarity	NPD6675	Approved
0.6833	Remote Similarity	NPD7128	Approved
0.6833	Remote Similarity	NPD5739	Approved
0.6833	Remote Similarity	NPD6402	Approved
0.6829	Remote Similarity	NPD8130	Phase 1
0.6818	Remote Similarity	NPD5786	Approved
0.6814	Remote Similarity	NPD7983	Approved
0.6777	Remote Similarity	NPD5697	Approved
0.6774	Remote Similarity	NPD6882	Approved
0.6759	Remote Similarity	NPD6435	Approved
0.6754	Remote Similarity	NPD6399	Phase 3
0.6748	Remote Similarity	NPD7102	Approved
0.6748	Remote Similarity	NPD6883	Approved
0.6748	Remote Similarity	NPD7290	Approved
0.6742	Remote Similarity	NPD7078	Approved
0.6729	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD5363	Approved
0.6726	Remote Similarity	NPD46	Approved
0.6726	Remote Similarity	NPD6698	Approved
0.6718	Remote Similarity	NPD7492	Approved
0.6697	Remote Similarity	NPD7154	Phase 3
0.6694	Remote Similarity	NPD6847	Approved
0.6694	Remote Similarity	NPD6617	Approved
0.6694	Remote Similarity	NPD6869	Approved
0.6693	Remote Similarity	NPD7115	Discovery
0.6692	Remote Similarity	NPD7736	Approved
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD6014	Approved
0.6667	Remote Similarity	NPD6013	Approved
0.6667	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD6012	Approved
0.6667	Remote Similarity	NPD4790	Discontinued
0.6667	Remote Similarity	NPD6054	Approved
0.6667	Remote Similarity	NPD6319	Approved
0.6639	Remote Similarity	NPD5701	Approved
0.6617	Remote Similarity	NPD8293	Discontinued
0.6615	Remote Similarity	NPD8033	Approved
0.661	Remote Similarity	NPD4225	Approved
0.6609	Remote Similarity	NPD5778	Approved
0.6609	Remote Similarity	NPD5779	Approved
0.6606	Remote Similarity	NPD4269	Approved
0.6606	Remote Similarity	NPD4270	Approved
0.6587	Remote Similarity	NPD4632	Approved
0.6585	Remote Similarity	NPD6011	Approved
0.6583	Remote Similarity	NPD5211	Phase 2
0.6583	Remote Similarity	NPD7632	Discontinued
0.6579	Remote Similarity	NPD7838	Discovery
0.6574	Remote Similarity	NPD4821	Approved
0.6574	Remote Similarity	NPD4819	Approved
0.6574	Remote Similarity	NPD4820	Approved
0.6574	Remote Similarity	NPD4822	Approved
0.6574	Remote Similarity	NPD5368	Approved
0.6565	Remote Similarity	NPD6370	Approved
0.6545	Remote Similarity	NPD5331	Approved
0.6545	Remote Similarity	NPD5332	Approved
0.6542	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD4268	Approved
0.6542	Remote Similarity	NPD4271	Approved
0.6538	Remote Similarity	NPD6059	Approved
0.6538	Remote Similarity	NPD8377	Approved
0.6538	Remote Similarity	NPD8294	Approved
0.6522	Remote Similarity	NPD7637	Suspended
0.6512	Remote Similarity	NPD7328	Approved
0.6512	Remote Similarity	NPD7327	Approved
0.6504	Remote Similarity	NPD6412	Phase 2
0.6496	Remote Similarity	NPD5695	Phase 3
0.6489	Remote Similarity	NPD6015	Approved
0.6489	Remote Similarity	NPD8378	Approved
0.6489	Remote Similarity	NPD8380	Approved
0.6489	Remote Similarity	NPD8296	Approved
0.6489	Remote Similarity	NPD6016	Approved
0.6489	Remote Similarity	NPD8379	Approved
0.6489	Remote Similarity	NPD8335	Approved
0.6475	Remote Similarity	NPD5141	Approved
0.6471	Remote Similarity	NPD5696	Approved
0.6462	Remote Similarity	NPD7516	Approved
0.6439	Remote Similarity	NPD5988	Approved
0.6434	Remote Similarity	NPD6009	Approved
0.6429	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD7260	Phase 2
0.6422	Remote Similarity	NPD4252	Approved
0.6417	Remote Similarity	NPD5286	Approved
0.6417	Remote Similarity	NPD5285	Approved
0.6417	Remote Similarity	NPD4696	Approved
0.641	Remote Similarity	NPD5282	Discontinued
0.6404	Remote Similarity	NPD6903	Approved
0.6391	Remote Similarity	NPD7604	Phase 2
0.6387	Remote Similarity	NPD4755	Approved
0.6377	Remote Similarity	NPD6845	Suspended
0.6372	Remote Similarity	NPD7146	Approved
0.6372	Remote Similarity	NPD5330	Approved
0.6372	Remote Similarity	NPD7521	Approved
0.6372	Remote Similarity	NPD6684	Approved
0.6372	Remote Similarity	NPD7334	Approved
0.6372	Remote Similarity	NPD6409	Approved
0.6364	Remote Similarity	NPD8513	Phase 3
0.6364	Remote Similarity	NPD8516	Approved
0.6364	Remote Similarity	NPD5369	Approved
0.6364	Remote Similarity	NPD8517	Approved
0.6364	Remote Similarity	NPD7503	Approved
0.6364	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD8515	Approved
0.6364	Remote Similarity	NPD5983	Phase 2
0.6357	Remote Similarity	NPD6274	Approved
0.6356	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD7101	Approved
0.6336	Remote Similarity	NPD7100	Approved
0.6333	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD8133	Approved
0.6311	Remote Similarity	NPD5226	Approved
0.6311	Remote Similarity	NPD5225	Approved
0.6311	Remote Similarity	NPD5224	Approved
0.6311	Remote Similarity	NPD4633	Approved
0.6306	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD7839	Suspended
0.6296	Remote Similarity	NPD6336	Discontinued
0.6281	Remote Similarity	NPD4700	Approved
0.6261	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.626	Remote Similarity	NPD6335	Approved
0.626	Remote Similarity	NPD5174	Approved
0.626	Remote Similarity	NPD5175	Approved
0.6239	Remote Similarity	NPD8035	Phase 2
0.6239	Remote Similarity	NPD5693	Phase 1
0.6239	Remote Similarity	NPD5281	Approved
0.6239	Remote Similarity	NPD6411	Approved
0.6239	Remote Similarity	NPD8034	Phase 2
0.6239	Remote Similarity	NPD5284	Approved
0.6239	Remote Similarity	NPD6079	Approved
0.623	Remote Similarity	NPD5223	Approved
0.622	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.622	Remote Similarity	NPD4634	Approved
0.6218	Remote Similarity	NPD5210	Approved
0.6218	Remote Similarity	NPD4629	Approved
0.6207	Remote Similarity	NPD5328	Approved
0.6207	Remote Similarity	NPD4753	Phase 2
0.6207	Remote Similarity	NPD6051	Approved
0.6195	Remote Similarity	NPD4786	Approved
0.6195	Remote Similarity	NPD3665	Phase 1
0.6195	Remote Similarity	NPD3133	Approved
0.6195	Remote Similarity	NPD3666	Approved
0.6195	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.619	Remote Similarity	NPD4729	Approved
0.619	Remote Similarity	NPD4730	Approved
0.6183	Remote Similarity	NPD6317	Approved
0.616	Remote Similarity	NPD4767	Approved
0.616	Remote Similarity	NPD4768	Approved
0.6154	Remote Similarity	NPD5207	Approved
0.6142	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.614	Remote Similarity	NPD1694	Approved
0.6136	Remote Similarity	NPD6314	Approved
0.6136	Remote Similarity	NPD6313	Approved
0.6131	Remote Similarity	NPD8074	Phase 3
0.6121	Remote Similarity	NPD6672	Approved
0.6121	Remote Similarity	NPD5737	Approved
0.6119	Remote Similarity	NPD6908	Approved
0.6119	Remote Similarity	NPD6909	Approved
0.6116	Remote Similarity	NPD7902	Approved
0.6106	Remote Similarity	NPD6695	Phase 3
0.6098	Remote Similarity	NPD5344	Discontinued
0.6094	Remote Similarity	NPD5249	Phase 3
0.6094	Remote Similarity	NPD5248	Approved
0.6094	Remote Similarity	NPD5247	Approved
0.6094	Remote Similarity	NPD5250	Approved
0.6094	Remote Similarity	NPD5251	Approved
0.6087	Remote Similarity	NPD6033	Approved
0.6068	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD6904	Approved
0.6068	Remote Similarity	NPD6673	Approved
0.6068	Remote Similarity	NPD6101	Approved
0.6068	Remote Similarity	NPD6080	Approved
0.6063	Remote Similarity	NPD5128	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