NPASS Compound

Structure

CID171916 OpenBabel06191715542D 31 33 0 0 0 0 0 0 0 0999 V2000 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 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 -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 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 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 4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 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 2.5981 1.5000 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 -0.8660 1.5000 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 -2.5981 3.5000 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 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 -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 -4.3301 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 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 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 14 1 0 0 0 0 5 8 1 0 0 0 0 5 13 2 0 0 0 0 6 9 1 0 0 0 0 6 14 2 0 0 0 0 7 10 2 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 10 19 1 0 0 0 0 11 15 2 0 0 0 0 11 20 1 0 0 0 0 12 18 2 0 0 0 0 12 31 1 0 0 0 0 15 18 1 0 0 0 0 16 22 2 0 0 0 0 16 23 1 0 0 0 0 17 22 1 0 0 0 0 17 25 2 0 0 0 0 18 24 1 0 0 0 0 19 20 2 0 0 0 0 19 26 1 0 0 0 0 20 27 1 0 0 0 0 21 23 2 0 0 0 0 21 24 1 0 0 0 0 21 25 1 0 0 0 0 22 28 1 0 0 0 0 23 29 1 0 0 0 0 24 30 2 0 0 0 0 25 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	422.17
Volume:	441.663
LogP:	6.019
LogD:	2.853
LogS:	-2.968
# Rotatable Bonds:	5
TPSA:	111.13
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.328
Synthetic Accessibility Score:	3.12
Fsp3:	0.24
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.933
MDCK Permeability:	1.06873285403708e-05
Pgp-inhibitor:	0.521
Pgp-substrate:	0.855
Human Intestinal Absorption (HIA):	0.044
20% Bioavailability (F20%):	0.968
30% Bioavailability (F30%):	0.806

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	91.24172973632812%
Volume Distribution (VD):	0.792
Pgp-substrate:	10.277190208435059%

ADMET: Metabolism

CYP1A2-inhibitor:	0.463
CYP1A2-substrate:	0.155
CYP2C19-inhibitor:	0.671
CYP2C19-substrate:	0.05
CYP2C9-inhibitor:	0.814
CYP2C9-substrate:	0.602
CYP2D6-inhibitor:	0.273
CYP2D6-substrate:	0.176
CYP3A4-inhibitor:	0.093
CYP3A4-substrate:	0.054

ADMET: Excretion

Clearance (CL):	9.377
Half-life (T1/2):	0.75

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.782
Drug-inuced Liver Injury (DILI):	0.753
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.72
Maximum Recommended Daily Dose:	0.031
Skin Sensitization:	0.938
Carcinogencity:	0.102
Eye Corrosion:	0.003
Eye Irritation:	0.588
Respiratory Toxicity:	0.143

Download Data

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

Natural Product: NPC171916

Natural Product ID:	NPC171916
*Common Name:**	6,8-Diprenylorobo
IUPAC Name:	3-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6,8-bis(3-methylbut-2-enyl)chromen-4-one
Synonyms:
Standard InCHIKey:	OAUIRSVJXOFAOO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H26O6/c1-13(2)5-8-16-22(28)17(9-6-14(3)4)25-21(23(16)29)24(30)18(12-31-25)15-7-10-19(26)20(27)11-15/h5-7,10-12,26-29H,8-9H2,1-4H3
SMILES:	CC(=CCc1c(c(CC=C(C)C)c2c(c1O)c(=O)c(co2)c1ccc(c(c1)O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2442947
PubChem CID:	21148065
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0001612] Isoflavans [CHEMONTID:0001827] Isoflavanones [CHEMONTID:0003526] 6-prenylated isoflavanones

*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
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16441081]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16675659]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[22074222]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22074222]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[23867078]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23867078]
NPO4010	Flemingia philippinensis	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24054487]
NPO4010	Flemingia philippinensis	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[24412339]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24479468]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[24957203]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25445757]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25744461]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26841168]
NPO40204	Millettia extensa	Species	Fabaceae	Eukaryota	Stems	n.a.	n.a.	PMID[30106294]
NPO40204	Millettia extensa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31403786]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32196343]
NPO4010	Flemingia philippinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4010	Flemingia philippinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4010	Flemingia philippinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4010	Flemingia philippinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10026	Mitracarpus scaber	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7786	Lentinus tigrinus	Species	Lentinaceae	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	3
Ki	2
MIC	9
Others	1

Activity Type	# Activity
Cell Line	2
Individual Protein	4
Organism	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT344	Individual Protein	Sialidase	Clostridium perfringens	Ki	=	1020.0	nM	PMID[548408]
NPT344	Individual Protein	Sialidase	Clostridium perfringens	IC50	=	1070.0	nM	PMID[548408]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	2400.0	nM	PMID[548409]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Ki	=	2500.0	nM	PMID[548409]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	14300.0	nM	PMID[548410]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	90.2	%	PMID[548410]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	16.0	ug.mL-1	PMID[548410]
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	MIC	=	16.0	ug.mL-1	PMID[548410]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	128.0	ug.mL-1	PMID[548410]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	16.0	ug.mL-1	PMID[548410]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	32.0	ug.mL-1	PMID[548410]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	=	128.0	ug.mL-1	PMID[548410]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	128.0	ug.mL-1	PMID[548410]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	128.0	ug.mL-1	PMID[548410]
NPT2909	Organism	Shigella flexneri	Shigella flexneri	MIC	=	128.0	ug.mL-1	PMID[548410]

☑ 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 NPC171916 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	415
0.1-0.2	1688
0.2-0.3	4138
0.3-0.4	10750
0.4-0.5	7476
0.5-0.6	3472
0.6-0.7	5038
0.7-0.8	5078
0.8-0.85	2378
0.85-0.9	1666
0.9-0.95	556
0.95-1	42

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC38545
0.993	High Similarity	NPC238279
0.993	High Similarity	NPC166036
0.993	High Similarity	NPC203077
0.9861	High Similarity	NPC256406
0.9793	High Similarity	NPC323626
0.9793	High Similarity	NPC324233
0.9655	High Similarity	NPC85131
0.9653	High Similarity	NPC194653
0.9653	High Similarity	NPC80710
0.9653	High Similarity	NPC254702
0.9653	High Similarity	NPC139364
0.9653	High Similarity	NPC203747
0.9648	High Similarity	NPC242893
0.9648	High Similarity	NPC38065
0.9595	High Similarity	NPC282307
0.9595	High Similarity	NPC170026
0.9592	High Similarity	NPC93552
0.9589	High Similarity	NPC154345
0.9586	High Similarity	NPC40290
0.9586	High Similarity	NPC264550
0.9586	High Similarity	NPC195763
0.9586	High Similarity	NPC264289
0.9586	High Similarity	NPC142876
0.9586	High Similarity	NPC333691
0.9586	High Similarity	NPC69430
0.9586	High Similarity	NPC200060
0.9586	High Similarity	NPC139293
0.9577	High Similarity	NPC471417
0.9527	High Similarity	NPC130589
0.9527	High Similarity	NPC234255
0.9527	High Similarity	NPC39184
0.9527	High Similarity	NPC134287
0.9521	High Similarity	NPC88804
0.9521	High Similarity	NPC10467
0.9521	High Similarity	NPC3825
0.9521	High Similarity	NPC472279
0.9514	High Similarity	NPC12377
0.951	High Similarity	NPC105213
0.9507	High Similarity	NPC301178
0.9507	High Similarity	NPC284556
0.9467	High Similarity	NPC184755
0.9467	High Similarity	NPC74178
0.9463	High Similarity	NPC472455
0.9459	High Similarity	NPC213896
0.9459	High Similarity	NPC192083
0.9459	High Similarity	NPC124714
0.9448	High Similarity	NPC188074
0.9448	High Similarity	NPC125449
0.9444	High Similarity	NPC157133
0.9441	High Similarity	NPC287722
0.9437	High Similarity	NPC326109
0.9437	High Similarity	NPC215311
0.9437	High Similarity	NPC48624
0.9437	High Similarity	NPC213659
0.9437	High Similarity	NPC259166
0.9437	High Similarity	NPC219917
0.9437	High Similarity	NPC144118
0.9437	High Similarity	NPC172250
0.9437	High Similarity	NPC204985
0.9437	High Similarity	NPC80962
0.9404	High Similarity	NPC28241
0.9404	High Similarity	NPC328102
0.94	High Similarity	NPC52889
0.94	High Similarity	NPC291508
0.94	High Similarity	NPC78103
0.9396	High Similarity	NPC133392
0.9396	High Similarity	NPC472280
0.9396	High Similarity	NPC321779
0.9396	High Similarity	NPC152951
0.9396	High Similarity	NPC117992
0.9396	High Similarity	NPC168247
0.9396	High Similarity	NPC57674
0.9396	High Similarity	NPC230149
0.9392	High Similarity	NPC121522
0.9392	High Similarity	NPC471982
0.9392	High Similarity	NPC100263
0.9392	High Similarity	NPC216769
0.9392	High Similarity	NPC245382
0.9392	High Similarity	NPC37684
0.9392	High Similarity	NPC131266
0.9392	High Similarity	NPC100971
0.9392	High Similarity	NPC291802
0.9392	High Similarity	NPC63187
0.9392	High Similarity	NPC237994
0.9392	High Similarity	NPC106976
0.9392	High Similarity	NPC209487
0.9392	High Similarity	NPC269451
0.9392	High Similarity	NPC35763
0.9392	High Similarity	NPC181209
0.9392	High Similarity	NPC157784
0.9384	High Similarity	NPC218490
0.9371	High Similarity	NPC26051
0.9371	High Similarity	NPC469404
0.9371	High Similarity	NPC55832
0.9371	High Similarity	NPC268204
0.9371	High Similarity	NPC52789
0.9366	High Similarity	NPC283429
0.9366	High Similarity	NPC295384
0.9338	High Similarity	NPC204879
0.9333	High Similarity	NPC278778
0.9333	High Similarity	NPC291878
0.9333	High Similarity	NPC195796
0.9333	High Similarity	NPC35038
0.9329	High Similarity	NPC250557
0.9329	High Similarity	NPC273462
0.9329	High Similarity	NPC74924
0.9329	High Similarity	NPC33051
0.9329	High Similarity	NPC170492
0.9329	High Similarity	NPC227337
0.9329	High Similarity	NPC49402
0.9329	High Similarity	NPC70433
0.9329	High Similarity	NPC298692
0.9324	High Similarity	NPC59162
0.9324	High Similarity	NPC45291
0.9324	High Similarity	NPC19980
0.9324	High Similarity	NPC304295
0.9324	High Similarity	NPC262623
0.9324	High Similarity	NPC205046
0.932	High Similarity	NPC105512
0.9315	High Similarity	NPC222298
0.9315	High Similarity	NPC95864
0.9315	High Similarity	NPC108406
0.9315	High Similarity	NPC51070
0.9306	High Similarity	NPC119663
0.9306	High Similarity	NPC254659
0.9306	High Similarity	NPC476054
0.9301	High Similarity	NPC101366
0.9301	High Similarity	NPC253822
0.9276	High Similarity	NPC476283
0.9276	High Similarity	NPC192686
0.9276	High Similarity	NPC119209
0.9276	High Similarity	NPC118256
0.9276	High Similarity	NPC476980
0.9272	High Similarity	NPC218313
0.9272	High Similarity	NPC27337
0.9272	High Similarity	NPC222689
0.9272	High Similarity	NPC35598
0.9272	High Similarity	NPC471209
0.9272	High Similarity	NPC474055
0.9272	High Similarity	NPC472598
0.9272	High Similarity	NPC474681
0.9267	High Similarity	NPC470327
0.9267	High Similarity	NPC45849
0.9267	High Similarity	NPC200761
0.9267	High Similarity	NPC256925
0.9267	High Similarity	NPC113906
0.9267	High Similarity	NPC477503
0.9262	High Similarity	NPC249570
0.9262	High Similarity	NPC472912
0.9262	High Similarity	NPC60972
0.9262	High Similarity	NPC474993
0.9262	High Similarity	NPC257648
0.9262	High Similarity	NPC477231
0.9262	High Similarity	NPC39732
0.9257	High Similarity	NPC156953
0.9257	High Similarity	NPC239363
0.9252	High Similarity	NPC119059
0.9252	High Similarity	NPC3036
0.9241	High Similarity	NPC117836
0.9241	High Similarity	NPC51887
0.9241	High Similarity	NPC207732
0.9241	High Similarity	NPC142165
0.9241	High Similarity	NPC476178
0.9241	High Similarity	NPC475705
0.9236	High Similarity	NPC185607
0.9225	High Similarity	NPC181124
0.9225	High Similarity	NPC209560
0.9225	High Similarity	NPC116632
0.9225	High Similarity	NPC294409
0.9225	High Similarity	NPC212767
0.9225	High Similarity	NPC7013
0.9225	High Similarity	NPC303644
0.9225	High Similarity	NPC162680
0.9216	High Similarity	NPC26326
0.9216	High Similarity	NPC258331
0.9216	High Similarity	NPC198829
0.9216	High Similarity	NPC474038
0.9211	High Similarity	NPC53545
0.9211	High Similarity	NPC117418
0.9211	High Similarity	NPC469658
0.9211	High Similarity	NPC22192
0.9211	High Similarity	NPC210459
0.9205	High Similarity	NPC3980
0.9205	High Similarity	NPC472626
0.9205	High Similarity	NPC133970
0.9205	High Similarity	NPC209614
0.9205	High Similarity	NPC6633
0.9205	High Similarity	NPC5322
0.9205	High Similarity	NPC471985
0.9205	High Similarity	NPC470328
0.9205	High Similarity	NPC276444
0.92	High Similarity	NPC107109
0.92	High Similarity	NPC469550
0.92	High Similarity	NPC18727
0.92	High Similarity	NPC476631
0.92	High Similarity	NPC189130
0.9195	High Similarity	NPC260895
0.9195	High Similarity	NPC31363
0.9189	High Similarity	NPC87125

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 NPC171916 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	370
0.1-0.2	970
0.2-0.3	1653
0.3-0.4	2643
0.4-0.5	1869
0.5-0.6	1044
0.6-0.7	418
0.7-0.8	118
0.8-0.85	43
0.85-0.9	17
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9459	High Similarity	NPD2393	Clinical (unspecified phase)
0.9133	High Similarity	NPD1934	Approved
0.911	High Similarity	NPD1511	Approved
0.9085	High Similarity	NPD1510	Phase 2
0.9073	High Similarity	NPD2801	Approved
0.9	High Similarity	NPD4380	Phase 2
0.8986	High Similarity	NPD1512	Approved
0.8954	High Similarity	NPD3882	Suspended
0.8919	High Similarity	NPD4378	Clinical (unspecified phase)
0.8803	High Similarity	NPD1240	Approved
0.8688	High Similarity	NPD3818	Discontinued
0.8681	High Similarity	NPD1607	Approved
0.8679	High Similarity	NPD6167	Clinical (unspecified phase)
0.8679	High Similarity	NPD6168	Clinical (unspecified phase)
0.8679	High Similarity	NPD6166	Phase 2
0.8671	High Similarity	NPD943	Approved
0.8667	High Similarity	NPD7410	Clinical (unspecified phase)
0.8654	High Similarity	NPD7075	Discontinued
0.8645	High Similarity	NPD3817	Phase 2
0.8639	High Similarity	NPD1549	Phase 2
0.863	High Similarity	NPD2796	Approved
0.8581	High Similarity	NPD7096	Clinical (unspecified phase)
0.8581	High Similarity	NPD7819	Suspended
0.8571	High Similarity	NPD1552	Clinical (unspecified phase)
0.8571	High Similarity	NPD1550	Clinical (unspecified phase)
0.8553	High Similarity	NPD6232	Discontinued
0.8519	High Similarity	NPD7054	Approved
0.8516	High Similarity	NPD6801	Discontinued
0.8509	High Similarity	NPD7473	Discontinued
0.8471	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD7472	Approved
0.8466	Intermediate Similarity	NPD7074	Phase 3
0.8452	Intermediate Similarity	NPD7411	Suspended
0.8428	Intermediate Similarity	NPD5494	Approved
0.8418	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8415	Intermediate Similarity	NPD6797	Phase 2
0.8408	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8378	Intermediate Similarity	NPD2935	Discontinued
0.8364	Intermediate Similarity	NPD7251	Discontinued
0.8355	Intermediate Similarity	NPD6799	Approved
0.8267	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD7808	Phase 3
0.8204	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD6599	Discontinued
0.8148	Intermediate Similarity	NPD6959	Discontinued
0.8137	Intermediate Similarity	NPD919	Approved
0.8125	Intermediate Similarity	NPD7768	Phase 2
0.811	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD230	Phase 1
0.8092	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD5844	Phase 1
0.8067	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD2532	Approved
0.8065	Intermediate Similarity	NPD2534	Approved
0.8065	Intermediate Similarity	NPD2533	Approved
0.8054	Intermediate Similarity	NPD6651	Approved
0.8039	Intermediate Similarity	NPD3750	Approved
0.8039	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD1247	Approved
0.8036	Intermediate Similarity	NPD6559	Discontinued
0.7976	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD5403	Approved
0.7959	Intermediate Similarity	NPD3027	Phase 3
0.795	Intermediate Similarity	NPD5402	Approved
0.7947	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD1551	Phase 2
0.7888	Intermediate Similarity	NPD1465	Phase 2
0.7857	Intermediate Similarity	NPD2800	Approved
0.7857	Intermediate Similarity	NPD1243	Approved
0.7848	Intermediate Similarity	NPD920	Approved
0.7834	Intermediate Similarity	NPD5401	Approved
0.7831	Intermediate Similarity	NPD3926	Phase 2
0.7823	Intermediate Similarity	NPD9494	Approved
0.7821	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD1613	Approved
0.7793	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD7390	Discontinued
0.777	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD5953	Discontinued
0.7755	Intermediate Similarity	NPD2798	Approved
0.7744	Intermediate Similarity	NPD3749	Approved
0.7722	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD2799	Discontinued
0.7712	Intermediate Similarity	NPD3748	Approved
0.7703	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD4628	Phase 3
0.7667	Intermediate Similarity	NPD2313	Discontinued
0.7658	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7286	Phase 2
0.764	Intermediate Similarity	NPD3226	Approved
0.7624	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD2344	Approved
0.761	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD6234	Discontinued
0.755	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD6099	Approved
0.7548	Intermediate Similarity	NPD6100	Approved
0.7532	Intermediate Similarity	NPD6190	Approved
0.7531	Intermediate Similarity	NPD7458	Discontinued
0.7528	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD447	Suspended
0.75	Intermediate Similarity	NPD2346	Discontinued
0.75	Intermediate Similarity	NPD7199	Phase 2
0.75	Intermediate Similarity	NPD37	Approved
0.7483	Intermediate Similarity	NPD9269	Phase 2
0.7468	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD5710	Approved
0.7456	Intermediate Similarity	NPD5711	Approved
0.745	Intermediate Similarity	NPD1470	Approved
0.745	Intermediate Similarity	NPD1203	Approved
0.7443	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD5406	Approved
0.7436	Intermediate Similarity	NPD5405	Approved
0.7436	Intermediate Similarity	NPD5408	Approved
0.7436	Intermediate Similarity	NPD5404	Approved
0.7421	Intermediate Similarity	NPD2309	Approved
0.7417	Intermediate Similarity	NPD6832	Phase 2
0.7417	Intermediate Similarity	NPD4908	Phase 1
0.7415	Intermediate Similarity	NPD1201	Approved
0.7415	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD2654	Approved
0.7403	Intermediate Similarity	NPD1933	Approved
0.7379	Intermediate Similarity	NPD1548	Phase 1
0.7372	Intermediate Similarity	NPD7033	Discontinued
0.7365	Intermediate Similarity	NPD4967	Phase 2
0.7365	Intermediate Similarity	NPD4966	Approved
0.7365	Intermediate Similarity	NPD4965	Approved
0.7365	Intermediate Similarity	NPD3972	Approved
0.7362	Intermediate Similarity	NPD1653	Approved
0.7348	Intermediate Similarity	NPD4363	Phase 3
0.7348	Intermediate Similarity	NPD4360	Phase 2
0.732	Intermediate Similarity	NPD3268	Approved
0.7314	Intermediate Similarity	NPD7685	Pre-registration
0.731	Intermediate Similarity	NPD5536	Phase 2
0.731	Intermediate Similarity	NPD5242	Approved
0.7308	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4361	Phase 2
0.7297	Intermediate Similarity	NPD1610	Phase 2
0.729	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7228	Approved
0.7283	Intermediate Similarity	NPD3751	Discontinued
0.7261	Intermediate Similarity	NPD4308	Phase 3
0.726	Intermediate Similarity	NPD9545	Approved
0.7255	Intermediate Similarity	NPD4625	Phase 3
0.725	Intermediate Similarity	NPD7003	Approved
0.725	Intermediate Similarity	NPD8166	Discontinued
0.7248	Intermediate Similarity	NPD9717	Approved
0.7243	Intermediate Similarity	NPD6780	Approved
0.7243	Intermediate Similarity	NPD6778	Approved
0.7243	Intermediate Similarity	NPD6782	Approved
0.7243	Intermediate Similarity	NPD6776	Approved
0.7243	Intermediate Similarity	NPD6779	Approved
0.7243	Intermediate Similarity	NPD6777	Approved
0.7243	Intermediate Similarity	NPD6781	Approved
0.7241	Intermediate Similarity	NPD9493	Approved
0.7237	Intermediate Similarity	NPD3018	Phase 2
0.7232	Intermediate Similarity	NPD8313	Approved
0.7232	Intermediate Similarity	NPD8312	Approved
0.7222	Intermediate Similarity	NPD4357	Discontinued
0.7219	Intermediate Similarity	NPD1164	Approved
0.7219	Intermediate Similarity	NPD2797	Approved
0.7212	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD8151	Discontinued
0.7211	Intermediate Similarity	NPD9268	Approved
0.7207	Intermediate Similarity	NPD8150	Discontinued
0.72	Intermediate Similarity	NPD1729	Discontinued
0.7196	Intermediate Similarity	NPD7584	Approved
0.7181	Intermediate Similarity	NPD422	Phase 1
0.7179	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD5124	Phase 1
0.7178	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7229	Phase 3
0.7151	Intermediate Similarity	NPD3787	Discontinued
0.7133	Intermediate Similarity	NPD1608	Approved
0.7128	Intermediate Similarity	NPD7435	Discontinued
0.7126	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6386	Approved
0.7126	Intermediate Similarity	NPD6385	Approved
0.7115	Intermediate Similarity	NPD4060	Phase 1
0.7111	Intermediate Similarity	NPD8434	Phase 2
0.7101	Intermediate Similarity	NPD4288	Approved
0.7101	Intermediate Similarity	NPD5353	Approved
0.7097	Intermediate Similarity	NPD6798	Discontinued
0.7097	Intermediate Similarity	NPD411	Approved
0.7097	Intermediate Similarity	NPD3764	Approved
0.7095	Intermediate Similarity	NPD1651	Approved
0.7086	Intermediate Similarity	NPD2983	Phase 2
0.7086	Intermediate Similarity	NPD2982	Phase 2
0.7083	Intermediate Similarity	NPD6844	Discontinued
0.7063	Intermediate Similarity	NPD7266	Discontinued
0.7039	Intermediate Similarity	NPD1876	Approved
0.7039	Intermediate Similarity	NPD3225	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