NPASS Compound

Structure

CID216917 OpenBabel06191716002D 24 26 0 0 1 0 0 0 0 0999 V2000 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 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 -3.4641 -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 -4.3301 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 2 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 -0.0000 2.0000 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 -2.5981 1.5000 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 -0.8660 0.5000 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 -1.7321 2.0000 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 -1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 21 1 0 0 0 0 4 22 1 0 0 0 0 5 23 1 0 0 0 0 6 8 1 0 0 0 0 6 10 1 0 0 0 0 7 11 2 0 0 0 0 7 12 1 0 0 0 0 8 1 1 6 0 0 0 8 24 1 0 0 0 0 9 2 1 6 0 0 0 9 13 1 0 0 0 0 9 24 1 0 0 0 0 10 13 2 0 0 0 0 10 16 1 0 0 0 0 11 14 1 0 0 0 0 11 21 1 0 0 0 0 12 18 2 0 0 0 0 12 22 1 0 0 0 0 13 17 1 0 0 0 0 14 15 2 0 0 0 0 14 17 1 0 0 0 0 15 16 1 0 0 0 0 15 18 1 0 0 0 0 16 19 2 0 0 0 0 17 20 2 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.13
Volume:	331.137
LogP:	3.73
LogD:	2.807
LogS:	-4.125
# Rotatable Bonds:	3
TPSA:	77.38
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.834
Synthetic Accessibility Score:	3.594
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.834
MDCK Permeability:	1.55304678628454e-05
Pgp-inhibitor:	0.483
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.038
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.025
Plasma Protein Binding (PPB):	91.53753662109375%
Volume Distribution (VD):	0.812
Pgp-substrate:	10.511528968811035%

ADMET: Metabolism

CYP1A2-inhibitor:	0.308
CYP1A2-substrate:	0.976
CYP2C19-inhibitor:	0.099
CYP2C19-substrate:	0.898
CYP2C9-inhibitor:	0.477
CYP2C9-substrate:	0.861
CYP2D6-inhibitor:	0.081
CYP2D6-substrate:	0.566
CYP3A4-inhibitor:	0.176
CYP3A4-substrate:	0.62

ADMET: Excretion

Clearance (CL):	6.152
Half-life (T1/2):	0.593

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.385
Drug-inuced Liver Injury (DILI):	0.913
AMES Toxicity:	0.483
Rat Oral Acute Toxicity:	0.757
Maximum Recommended Daily Dose:	0.672
Skin Sensitization:	0.735
Carcinogencity:	0.374
Eye Corrosion:	0.004
Eye Irritation:	0.579
Respiratory Toxicity:	0.757

Download Data

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

Natural Product: NPC216917

Natural Product ID:	NPC216917
*Common Name:**	Ventiloquinone E
IUPAC Name:	(1R,3S)-6,7,9-trimethoxy-1,3-dimethyl-3,4-dihydro-1H-benzo[g]isochromene-5,10-dione
Synonyms:
Standard InCHIKey:	AIEBVACSHFUVDU-DTWKUNHWSA-N
Standard InCHI:	InChI=1S/C18H20O6/c1-8-6-10-13(9(2)24-8)17(20)14-11(21-3)7-12(22-4)18(23-5)15(14)16(10)19/h7-9H,6H2,1-5H3/t8-,9+/m0/s1
SMILES:	COc1cc(OC)c2c(c1OC)C(=O)C1=C(C2=O)[C@@H](C)O[C@H](C1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2269916
PubChem CID:	11013000
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001649] Isochromanequinones [CHEMONTID:0002355] Benzoisochromanequinones

*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
NPO8179	Laccaria amethystea	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11213295]
NPO8179	Laccaria amethystea	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2091	Abies pectinata	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO835	Diatraea saccharalis	Species	Crambidae	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	8

Activity Type	# Activity
Organism	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1369	Organism	Henosepilachna vigintioctopunctata	Henosepilachna vigintioctopunctata	Activity	=	0.21	cm2	PMID[520164]
NPT1369	Organism	Henosepilachna vigintioctopunctata	Henosepilachna vigintioctopunctata	Activity	=	0.39	cm2	PMID[520164]
NPT1369	Organism	Henosepilachna vigintioctopunctata	Henosepilachna vigintioctopunctata	Activity	=	0.58	cm2	PMID[520164]
NPT1369	Organism	Henosepilachna vigintioctopunctata	Henosepilachna vigintioctopunctata	Activity	=	29.0	%	PMID[520164]
NPT1175	Organism	Spodoptera litura	Spodoptera litura	Activity	=	13.3	cm2	PMID[520164]
NPT1175	Organism	Spodoptera litura	Spodoptera litura	Activity	=	23.3	cm2	PMID[520164]
NPT1175	Organism	Spodoptera litura	Spodoptera litura	Activity	=	35.1	cm2	PMID[520164]
NPT1175	Organism	Spodoptera litura	Spodoptera litura	Activity	=	25.0	%	PMID[520164]

☑ 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 NPC216917 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	470
0.1-0.2	1802
0.2-0.3	4724
0.3-0.4	11110
0.4-0.5	6921
0.5-0.6	3849
0.6-0.7	5853
0.7-0.8	6563
0.8-0.85	1207
0.85-0.9	187
0.9-0.95	10
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9241	High Similarity	NPC277369
0.9241	High Similarity	NPC215451
0.92	High Similarity	NPC38469
0.9189	High Similarity	NPC476058
0.9178	High Similarity	NPC182842
0.9054	High Similarity	NPC120924
0.9054	High Similarity	NPC195919
0.9054	High Similarity	NPC216314
0.9034	High Similarity	NPC109007
0.8986	High Similarity	NPC165512
0.8968	High Similarity	NPC155302
0.8968	High Similarity	NPC161947
0.8926	High Similarity	NPC40818
0.8926	High Similarity	NPC302408
0.8926	High Similarity	NPC283002
0.8926	High Similarity	NPC106461
0.8926	High Similarity	NPC110639
0.8926	High Similarity	NPC215932
0.8926	High Similarity	NPC14958
0.8917	High Similarity	NPC197168
0.891	High Similarity	NPC474186
0.891	High Similarity	NPC66288
0.891	High Similarity	NPC87431
0.8889	High Similarity	NPC128961
0.8874	High Similarity	NPC238366
0.8867	High Similarity	NPC85233
0.8867	High Similarity	NPC205522
0.8867	High Similarity	NPC474999
0.8861	High Similarity	NPC25361
0.8854	High Similarity	NPC108767
0.8854	High Similarity	NPC215612
0.8851	High Similarity	NPC476054
0.8846	High Similarity	NPC475886
0.8846	High Similarity	NPC474287
0.8839	High Similarity	NPC217677
0.8839	High Similarity	NPC179732
0.8839	High Similarity	NPC165977
0.8839	High Similarity	NPC19097
0.8831	High Similarity	NPC472048
0.8824	High Similarity	NPC166201
0.8819	High Similarity	NPC143649
0.8816	High Similarity	NPC239363
0.8808	High Similarity	NPC10304
0.8808	High Similarity	NPC63256
0.8808	High Similarity	NPC476342
0.8797	High Similarity	NPC476822
0.8797	High Similarity	NPC249181
0.8797	High Similarity	NPC270837
0.8792	High Similarity	NPC23955
0.8792	High Similarity	NPC27106
0.879	High Similarity	NPC165549
0.879	High Similarity	NPC65746
0.879	High Similarity	NPC474187
0.879	High Similarity	NPC475883
0.879	High Similarity	NPC474351
0.8784	High Similarity	NPC29536
0.8784	High Similarity	NPC185607
0.8782	High Similarity	NPC477410
0.8774	High Similarity	NPC180340
0.8766	High Similarity	NPC473664
0.8766	High Similarity	NPC186507
0.8766	High Similarity	NPC472408
0.8766	High Similarity	NPC280937
0.8758	High Similarity	NPC473732
0.8758	High Similarity	NPC262623
0.8758	High Similarity	NPC279061
0.875	High Similarity	NPC134293
0.875	High Similarity	NPC69752
0.875	High Similarity	NPC181250
0.8742	High Similarity	NPC326520
0.8742	High Similarity	NPC191930
0.8734	High Similarity	NPC229632
0.8734	High Similarity	NPC294965
0.8733	High Similarity	NPC471590
0.8733	High Similarity	NPC136278
0.8726	High Similarity	NPC228785
0.8726	High Similarity	NPC84571
0.8726	High Similarity	NPC14353
0.8726	High Similarity	NPC298093
0.8726	High Similarity	NPC56085
0.8725	High Similarity	NPC70853
0.8725	High Similarity	NPC9966
0.8718	High Similarity	NPC300727
0.8718	High Similarity	NPC241904
0.8716	High Similarity	NPC58229
0.871	High Similarity	NPC234485
0.871	High Similarity	NPC478238
0.871	High Similarity	NPC134287
0.871	High Similarity	NPC37392
0.871	High Similarity	NPC130589
0.8701	High Similarity	NPC40033
0.8701	High Similarity	NPC475116
0.8701	High Similarity	NPC52623
0.8693	High Similarity	NPC103509
0.8693	High Similarity	NPC259058
0.8693	High Similarity	NPC156953
0.8693	High Similarity	NPC201547
0.8688	High Similarity	NPC20237
0.8688	High Similarity	NPC170245
0.8679	High Similarity	NPC236132
0.8679	High Similarity	NPC475055
0.8679	High Similarity	NPC7483
0.8679	High Similarity	NPC475985
0.8675	High Similarity	NPC231013
0.8671	High Similarity	NPC311740
0.8671	High Similarity	NPC40491
0.8671	High Similarity	NPC61010
0.8671	High Similarity	NPC278052
0.8667	High Similarity	NPC113089
0.8662	High Similarity	NPC476242
0.8662	High Similarity	NPC100123
0.8662	High Similarity	NPC329091
0.8658	High Similarity	NPC214919
0.8658	High Similarity	NPC124467
0.8654	High Similarity	NPC470762
0.8654	High Similarity	NPC317383
0.8654	High Similarity	NPC472050
0.8654	High Similarity	NPC274730
0.8654	High Similarity	NPC474167
0.8645	High Similarity	NPC155686
0.8645	High Similarity	NPC127172
0.8645	High Similarity	NPC250557
0.8645	High Similarity	NPC57211
0.8645	High Similarity	NPC124714
0.8645	High Similarity	NPC478213
0.8639	High Similarity	NPC46947
0.8636	High Similarity	NPC45291
0.8636	High Similarity	NPC474414
0.8636	High Similarity	NPC19980
0.8636	High Similarity	NPC208043
0.8636	High Similarity	NPC46882
0.8636	High Similarity	NPC132990
0.8636	High Similarity	NPC226973
0.8634	High Similarity	NPC283041
0.8634	High Similarity	NPC477154
0.8634	High Similarity	NPC6588
0.8634	High Similarity	NPC117854
0.8627	High Similarity	NPC328119
0.8625	High Similarity	NPC472450
0.8625	High Similarity	NPC275780
0.8625	High Similarity	NPC239752
0.8618	High Similarity	NPC470511
0.8616	High Similarity	NPC81679
0.8616	High Similarity	NPC52204
0.8609	High Similarity	NPC49282
0.8609	High Similarity	NPC472917
0.8608	High Similarity	NPC320359
0.8608	High Similarity	NPC299436
0.8608	High Similarity	NPC36217
0.86	High Similarity	NPC167663
0.8599	High Similarity	NPC470402
0.8599	High Similarity	NPC156057
0.8599	High Similarity	NPC48208
0.8599	High Similarity	NPC78103
0.8599	High Similarity	NPC37543
0.8599	High Similarity	NPC475267
0.8599	High Similarity	NPC181960
0.8599	High Similarity	NPC469584
0.8599	High Similarity	NPC474836
0.8599	High Similarity	NPC199463
0.8599	High Similarity	NPC476981
0.8599	High Similarity	NPC223787
0.8599	High Similarity	NPC162869
0.8599	High Similarity	NPC474208
0.859	High Similarity	NPC213622
0.859	High Similarity	NPC79998
0.859	High Similarity	NPC39184
0.859	High Similarity	NPC68727
0.859	High Similarity	NPC16082
0.859	High Similarity	NPC82592
0.859	High Similarity	NPC472909
0.8581	High Similarity	NPC148497
0.8581	High Similarity	NPC131266
0.8581	High Similarity	NPC51824
0.8581	High Similarity	NPC470340
0.8581	High Similarity	NPC209487
0.8581	High Similarity	NPC269451
0.8581	High Similarity	NPC113608
0.8581	High Similarity	NPC181209
0.8581	High Similarity	NPC245382
0.8581	High Similarity	NPC216769
0.8581	High Similarity	NPC268992
0.8581	High Similarity	NPC474993
0.8581	High Similarity	NPC35763
0.8581	High Similarity	NPC134677
0.8581	High Similarity	NPC100263
0.8581	High Similarity	NPC100971
0.8581	High Similarity	NPC291802
0.8581	High Similarity	NPC470337
0.8581	High Similarity	NPC153008
0.8581	High Similarity	NPC121522
0.8581	High Similarity	NPC470338
0.858	High Similarity	NPC99613
0.858	High Similarity	NPC49487
0.8571	High Similarity	NPC29160
0.8571	High Similarity	NPC157944
0.8571	High Similarity	NPC189270
0.8571	High Similarity	NPC37870
0.8571	High Similarity	NPC120593
0.8571	High Similarity	NPC43319

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 NPC216917 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	396
0.1-0.2	1029
0.2-0.3	2014
0.3-0.4	2715
0.4-0.5	1656
0.5-0.6	863
0.6-0.7	352
0.7-0.8	113
0.8-0.85	11
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8726	High Similarity	NPD5494	Approved
0.8526	High Similarity	NPD2801	Approved
0.8385	Intermediate Similarity	NPD6232	Discontinued
0.8344	Intermediate Similarity	NPD1934	Approved
0.8344	Intermediate Similarity	NPD7473	Discontinued
0.8291	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD3817	Phase 2
0.821	Intermediate Similarity	NPD1247	Approved
0.82	Intermediate Similarity	NPD2796	Approved
0.8133	Intermediate Similarity	NPD5844	Phase 1
0.8013	Intermediate Similarity	NPD2532	Approved
0.8013	Intermediate Similarity	NPD2533	Approved
0.8013	Intermediate Similarity	NPD2534	Approved
0.7988	Intermediate Similarity	NPD6959	Discontinued
0.7987	Intermediate Similarity	NPD4380	Phase 2
0.7974	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD3818	Discontinued
0.7963	Intermediate Similarity	NPD3882	Suspended
0.7952	Intermediate Similarity	NPD6166	Phase 2
0.7952	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD7819	Suspended
0.7949	Intermediate Similarity	NPD1511	Approved
0.7898	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD3926	Phase 2
0.7866	Intermediate Similarity	NPD919	Approved
0.7848	Intermediate Similarity	NPD1512	Approved
0.7836	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD7054	Approved
0.7778	Intermediate Similarity	NPD1510	Phase 2
0.7778	Intermediate Similarity	NPD6801	Discontinued
0.7765	Intermediate Similarity	NPD7074	Phase 3
0.7765	Intermediate Similarity	NPD7472	Approved
0.7744	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD2800	Approved
0.7688	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD920	Approved
0.7683	Intermediate Similarity	NPD5402	Approved
0.7677	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD37	Approved
0.7662	Intermediate Similarity	NPD3748	Approved
0.7654	Intermediate Similarity	NPD6599	Discontinued
0.7636	Intermediate Similarity	NPD4966	Approved
0.7636	Intermediate Similarity	NPD4965	Approved
0.7636	Intermediate Similarity	NPD4967	Phase 2
0.763	Intermediate Similarity	NPD7808	Phase 3
0.7628	Intermediate Similarity	NPD1549	Phase 2
0.7622	Intermediate Similarity	NPD1465	Phase 2
0.7616	Intermediate Similarity	NPD6797	Phase 2
0.761	Intermediate Similarity	NPD6799	Approved
0.759	Intermediate Similarity	NPD7075	Discontinued
0.759	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD7251	Discontinued
0.7548	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD6234	Discontinued
0.7532	Intermediate Similarity	NPD1607	Approved
0.7516	Intermediate Similarity	NPD1240	Approved
0.7486	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD5353	Approved
0.7468	Intermediate Similarity	NPD1243	Approved
0.7453	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD2403	Approved
0.7421	Intermediate Similarity	NPD3750	Approved
0.7419	Intermediate Similarity	NPD6651	Approved
0.7412	Intermediate Similarity	NPD5711	Approved
0.7412	Intermediate Similarity	NPD5710	Approved
0.7399	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7411	Suspended
0.7389	Intermediate Similarity	NPD2935	Discontinued
0.7378	Intermediate Similarity	NPD3226	Approved
0.7368	Intermediate Similarity	NPD5242	Approved
0.7355	Intermediate Similarity	NPD230	Phase 1
0.7341	Intermediate Similarity	NPD3751	Discontinued
0.7329	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD943	Approved
0.7284	Intermediate Similarity	NPD7390	Discontinued
0.7273	Intermediate Similarity	NPD6559	Discontinued
0.7256	Intermediate Similarity	NPD5403	Approved
0.7251	Intermediate Similarity	NPD7199	Phase 2
0.725	Intermediate Similarity	NPD2654	Approved
0.7244	Intermediate Similarity	NPD447	Suspended
0.7241	Intermediate Similarity	NPD7228	Approved
0.7239	Intermediate Similarity	NPD5401	Approved
0.7235	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD2346	Discontinued
0.7209	Intermediate Similarity	NPD3787	Discontinued
0.7207	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD6776	Approved
0.7204	Intermediate Similarity	NPD6781	Approved
0.7204	Intermediate Similarity	NPD6782	Approved
0.7204	Intermediate Similarity	NPD6778	Approved
0.7204	Intermediate Similarity	NPD6777	Approved
0.7204	Intermediate Similarity	NPD6780	Approved
0.7204	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD6779	Approved
0.7176	Intermediate Similarity	NPD3749	Approved
0.717	Intermediate Similarity	NPD6100	Approved
0.717	Intermediate Similarity	NPD6099	Approved
0.7168	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD8434	Phase 2
0.7134	Intermediate Similarity	NPD1933	Approved
0.7126	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD1471	Phase 3
0.7118	Intermediate Similarity	NPD7768	Phase 2
0.7099	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD4628	Phase 3
0.7097	Intermediate Similarity	NPD3027	Phase 3
0.709	Intermediate Similarity	NPD7435	Discontinued
0.709	Intermediate Similarity	NPD7698	Approved
0.709	Intermediate Similarity	NPD7696	Phase 3
0.709	Intermediate Similarity	NPD7697	Approved
0.7083	Intermediate Similarity	NPD6386	Approved
0.7083	Intermediate Similarity	NPD8151	Discontinued
0.7083	Intermediate Similarity	NPD6385	Approved
0.7079	Intermediate Similarity	NPD7240	Approved
0.7073	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD8150	Discontinued
0.7053	Intermediate Similarity	NPD7871	Phase 2
0.7053	Intermediate Similarity	NPD7870	Phase 2
0.7051	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD5005	Approved
0.7037	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD5006	Approved
0.703	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD3705	Approved
0.702	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD2798	Approved
0.7006	Intermediate Similarity	NPD1653	Approved
0.7	Intermediate Similarity	NPD2799	Discontinued
0.6974	Remote Similarity	NPD3972	Approved
0.6968	Remote Similarity	NPD9494	Approved
0.6962	Remote Similarity	NPD1613	Approved
0.6962	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2438	Suspended
0.6957	Remote Similarity	NPD1551	Phase 2
0.6948	Remote Similarity	NPD1470	Approved
0.6944	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD7701	Phase 2
0.6943	Remote Similarity	NPD2313	Discontinued
0.6935	Remote Similarity	NPD6535	Approved
0.6935	Remote Similarity	NPD6534	Approved
0.6933	Remote Similarity	NPD5691	Approved
0.6933	Remote Similarity	NPD1651	Approved
0.6927	Remote Similarity	NPD5953	Discontinued
0.6923	Remote Similarity	NPD6832	Phase 2
0.6918	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD4420	Approved
0.6914	Remote Similarity	NPD7229	Phase 3
0.6914	Remote Similarity	NPD2344	Approved
0.6913	Remote Similarity	NPD5536	Phase 2
0.691	Remote Similarity	NPD7286	Phase 2
0.6906	Remote Similarity	NPD8313	Approved
0.6906	Remote Similarity	NPD8312	Approved
0.6886	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD1876	Approved
0.6878	Remote Similarity	NPD8285	Discontinued
0.6872	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7874	Approved
0.686	Remote Similarity	NPD5977	Approved
0.686	Remote Similarity	NPD5978	Approved
0.6859	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD3018	Phase 2
0.6859	Remote Similarity	NPD6823	Phase 2
0.6857	Remote Similarity	NPD8127	Discontinued
0.6855	Remote Similarity	NPD2979	Phase 3
0.6854	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6190	Approved
0.6842	Remote Similarity	NPD6844	Discontinued
0.6837	Remote Similarity	NPD7801	Approved
0.6825	Remote Similarity	NPD7699	Phase 2
0.6825	Remote Similarity	NPD7700	Phase 2
0.6815	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD1201	Approved
0.6796	Remote Similarity	NPD7685	Pre-registration
0.6795	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD5089	Approved
0.6784	Remote Similarity	NPD5090	Approved
0.6776	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7458	Discontinued
0.6763	Remote Similarity	NPD4288	Approved
0.6757	Remote Similarity	NPD5283	Phase 1
0.6757	Remote Similarity	NPD1241	Discontinued
0.6755	Remote Similarity	NPD4363	Phase 3
0.6755	Remote Similarity	NPD4360	Phase 2
0.6753	Remote Similarity	NPD2981	Phase 2
0.6751	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD7783	Phase 2
0.6747	Remote Similarity	NPD2309	Approved
0.6742	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD1609	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