NPASS Compound

Structure

CID18189 OpenBabel06191715342D 25 29 0 0 1 0 0 0 0 0999 V2000 1.0179 0.9697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5093 1.8512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7223 -2.9091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8824 -3.3943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6798 0.9704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8397 1.4552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5202 -0.4843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8820 -1.4536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8404 -1.4548 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5209 -3.3950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6801 0.0004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7221 -1.9385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5205 -1.4543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0418 -2.9094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8402 -0.4848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6806 -1.9395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0416 -1.9389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3611 -1.9392 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0003 0.9700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3613 -2.9098 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.5880 -1.4384 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3615 -3.9098 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6808 -2.9101 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2015 -1.4540 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 19 1 0 0 0 0 2 19 1 0 0 0 0 3 4 2 0 0 0 0 3 12 1 0 0 0 0 4 14 1 0 0 0 0 5 6 2 0 0 0 0 5 11 1 0 0 0 0 6 19 1 0 0 0 0 7 11 2 0 0 0 0 7 13 1 0 0 0 0 8 12 2 0 0 0 0 8 17 1 0 0 0 0 9 15 2 0 0 0 0 9 16 1 0 0 0 0 10 20 1 0 0 0 0 10 23 1 0 0 0 0 11 15 1 0 0 0 0 12 21 1 0 0 0 0 13 16 2 0 0 0 0 13 18 1 0 0 0 0 14 17 2 0 0 0 0 14 20 1 0 0 0 0 15 25 1 0 0 0 0 16 23 1 0 0 0 0 17 24 1 0 0 0 0 18 20 1 1 0 0 0 18 24 1 0 0 0 0 19 25 1 0 0 0 0 20 22 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	338.12
Volume:	337.19
LogP:	4.01
LogD:	3.61
LogS:	-4.294
# Rotatable Bonds:	0
TPSA:	68.15
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.771
Synthetic Accessibility Score:	4.001
Fsp3:	0.3
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.817
MDCK Permeability:	1.7490036043454893e-05
Pgp-inhibitor:	0.029
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.071
Plasma Protein Binding (PPB):	98.3336181640625%
Volume Distribution (VD):	0.866
Pgp-substrate:	1.8384344577789307%

ADMET: Metabolism

CYP1A2-inhibitor:	0.922
CYP1A2-substrate:	0.615
CYP2C19-inhibitor:	0.75
CYP2C19-substrate:	0.709
CYP2C9-inhibitor:	0.681
CYP2C9-substrate:	0.905
CYP2D6-inhibitor:	0.902
CYP2D6-substrate:	0.858
CYP3A4-inhibitor:	0.684
CYP3A4-substrate:	0.683

ADMET: Excretion

Clearance (CL):	13.14
Half-life (T1/2):	0.184

ADMET: Toxicity

hERG Blockers:	0.087
Human Hepatotoxicity (H-HT):	0.899
Drug-inuced Liver Injury (DILI):	0.286
AMES Toxicity:	0.916
Rat Oral Acute Toxicity:	0.26
Maximum Recommended Daily Dose:	0.905
Skin Sensitization:	0.091
Carcinogencity:	0.946
Eye Corrosion:	0.003
Eye Irritation:	0.324
Respiratory Toxicity:	0.926

Download Data

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

Natural Product: NPC18189

Natural Product ID:	NPC18189
*Common Name:**	Glyceollin Ii
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DDJVLBCETGUEBO-AZUAARDMSA-N
Standard InCHI:	InChI=1S/C20H18O5/c1-19(2)6-5-11-7-13-16(9-15(11)25-19)23-10-20(22)14-4-3-12(21)8-17(14)24-18(13)20/h3-9,18,21-22H,10H2,1-2H3/t18-,20+/m0/s1
SMILES:	CC1(C)C=Cc2cc3c(cc2O1)OC[C@]1(c2ccc(cc2O[C@@H]31)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2229451
PubChem CID:	181883
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002617] Furanoisoflavonoids [CHEMONTID:0001608] Pterocarpans

*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
NPO25867	Malpighia emarginata	Species	Malpighiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[15725651]
NPO24543	Platymiscium floribundum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15787450]
NPO26402	Caesalpinia crista	Species	Fabaceae	Eukaryota	n.a.	seed kernel	n.a.	PMID[15921414]
NPO26402	Caesalpinia crista	Species	Fabaceae	Eukaryota	n.a.	Indonesia	n.a.	PMID[15921414]
NPO26158	Aspergillus carbonarius	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18205129]
NPO25841	Caulophyllum thalictroides	Species	Berberidaceae	Eukaryota	underground parts	n.a.	n.a.	PMID[19449879]
NPO26756	Karlodinium veneficum	Species	Kareniaceae	Eukaryota	n.a.	Delaware Inland Bays, USA	n.a.	PMID[20795740]
NPO26158	Aspergillus carbonarius	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21854017]
NPO26158	Aspergillus carbonarius	Species	Aspergillaceae	Eukaryota	n.a.	latex	n.a.	PMID[21854017]
NPO24543	Platymiscium floribundum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21866899]
NPO26158	Aspergillus carbonarius	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[4837062]
NPO25867	Malpighia emarginata	Species	Malpighiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO25867	Malpighia emarginata	Species	Malpighiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO26402	Caesalpinia crista	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26158	Aspergillus carbonarius	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28160	Alchemilla vulgaris	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25841	Caulophyllum thalictroides	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7552	Alligator mississippiensis	Species	Alligatoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26831	Buxus harlandi	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26756	Karlodinium veneficum	Species	Kareniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25652	Clavulinopsis pulchra	Species	Clavariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25867	Malpighia emarginata	Species	Malpighiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24543	Platymiscium floribundum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26530	Passiflora bryonioides	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26402	Caesalpinia crista	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26748	Leptoclinides dubius	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25267	Ardisia brevicaulis	Species	Primulaceae	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
MIC	4
Others	16

Activity Type	# Activity
Organism	20

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT636	Organism	Phytophthora capsici	Phytophthora capsici	MIC	=	25.0	ug.mL-1	PMID[473758]
NPT637	Organism	Fusarium oxysporum	Fusarium oxysporum	MIC	=	250.0	ug.mL-1	PMID[473758]
NPT635	Organism	Botryotinia fuckeliana	Botryotinia fuckeliana	Inhibition	=	22.1	%	PMID[473758]
NPT635	Organism	Botryotinia fuckeliana	Botryotinia fuckeliana	Inhibition	=	10.9	%	PMID[473758]
NPT638	Organism	Sclerotinia sclerotiorum	Sclerotinia sclerotiorum	Inhibition	=	61.0	%	PMID[473758]
NPT638	Organism	Sclerotinia sclerotiorum	Sclerotinia sclerotiorum	Inhibition	=	48.2	%	PMID[473758]
NPT636	Organism	Phytophthora capsici	Phytophthora capsici	Inhibition	=	40.5	%	PMID[473758]
NPT636	Organism	Phytophthora capsici	Phytophthora capsici	Inhibition	=	37.5	%	PMID[473758]
NPT637	Organism	Fusarium oxysporum	Fusarium oxysporum	Inhibition	=	40.1	%	PMID[473758]
NPT637	Organism	Fusarium oxysporum	Fusarium oxysporum	Inhibition	=	27.4	%	PMID[473758]
NPT636	Organism	Phytophthora capsici	Phytophthora capsici	Inhibition	=	100.0	%	PMID[473758]
NPT636	Organism	Phytophthora capsici	Phytophthora capsici	Inhibition	=	95.0	%	PMID[473758]
NPT636	Organism	Phytophthora capsici	Phytophthora capsici	Inhibition	=	50.0	%	PMID[473758]
NPT635	Organism	Botryotinia fuckeliana	Botryotinia fuckeliana	Inhibition	=	40.0	%	PMID[473758]
NPT637	Organism	Fusarium oxysporum	Fusarium oxysporum	Inhibition	=	40.0	%	PMID[473758]
NPT638	Organism	Sclerotinia sclerotiorum	Sclerotinia sclerotiorum	Inhibition	=	100.0	%	PMID[473758]
NPT635	Organism	Botryotinia fuckeliana	Botryotinia fuckeliana	MIC	=	750.0	ug.mL-1	PMID[473758]
NPT638	Organism	Sclerotinia sclerotiorum	Sclerotinia sclerotiorum	MIC	=	50.0	ug.mL-1	PMID[473758]

☑ 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 NPC18189 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	400
0.1-0.2	1427
0.2-0.3	3707
0.3-0.4	10450
0.4-0.5	8361
0.5-0.6	3729
0.6-0.7	7203
0.7-0.8	5767
0.8-0.85	1158
0.85-0.9	363
0.9-0.95	110
0.95-1	22

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC262585
1.0	High Similarity	NPC20829
0.9845	High Similarity	NPC124085
0.9845	High Similarity	NPC117048
0.9767	High Similarity	NPC92805
0.9767	High Similarity	NPC85435
0.9697	High Similarity	NPC475836
0.9695	High Similarity	NPC3049
0.9692	High Similarity	NPC223008
0.9692	High Similarity	NPC97834
0.9692	High Similarity	NPC115335
0.9692	High Similarity	NPC198154
0.9692	High Similarity	NPC296915
0.9692	High Similarity	NPC225696
0.9621	High Similarity	NPC474687
0.9612	High Similarity	NPC162801
0.9538	High Similarity	NPC13005
0.9462	High Similarity	NPC17343
0.9462	High Similarity	NPC207892
0.9462	High Similarity	NPC103799
0.9462	High Similarity	NPC164574
0.9462	High Similarity	NPC129106
0.9462	High Similarity	NPC129784
0.9462	High Similarity	NPC206224
0.9462	High Similarity	NPC244888
0.9462	High Similarity	NPC228369
0.9462	High Similarity	NPC196765
0.9462	High Similarity	NPC236014
0.9462	High Similarity	NPC268917
0.9462	High Similarity	NPC118683
0.9462	High Similarity	NPC12875
0.9462	High Similarity	NPC68205
0.9462	High Similarity	NPC280653
0.9462	High Similarity	NPC476166
0.9462	High Similarity	NPC164804
0.9462	High Similarity	NPC300875
0.9462	High Similarity	NPC150011
0.9462	High Similarity	NPC211413
0.9462	High Similarity	NPC118114
0.9462	High Similarity	NPC293203
0.9385	High Similarity	NPC27187
0.9385	High Similarity	NPC470225
0.938	High Similarity	NPC87224
0.938	High Similarity	NPC222572
0.9318	High Similarity	NPC77196
0.9313	High Similarity	NPC271945
0.9313	High Similarity	NPC181497
0.9308	High Similarity	NPC134360
0.9302	High Similarity	NPC149796
0.9281	High Similarity	NPC21776
0.9281	High Similarity	NPC16269
0.9275	High Similarity	NPC469557
0.9265	High Similarity	NPC5155
0.9231	High Similarity	NPC274717
0.9231	High Similarity	NPC47283
0.9231	High Similarity	NPC53986
0.9231	High Similarity	NPC38664
0.9231	High Similarity	NPC39064
0.9197	High Similarity	NPC204347
0.9197	High Similarity	NPC59841
0.9197	High Similarity	NPC475891
0.9197	High Similarity	NPC2613
0.9173	High Similarity	NPC215037
0.916	High Similarity	NPC93962
0.9147	High Similarity	NPC102540
0.9147	High Similarity	NPC103420
0.9147	High Similarity	NPC17809
0.9147	High Similarity	NPC285040
0.9147	High Similarity	NPC188022
0.9077	High Similarity	NPC276212
0.9077	High Similarity	NPC50315
0.9077	High Similarity	NPC262573
0.9077	High Similarity	NPC230479
0.9077	High Similarity	NPC471215
0.9077	High Similarity	NPC283049
0.9077	High Similarity	NPC26879
0.9071	High Similarity	NPC233980
0.907	High Similarity	NPC106914
0.907	High Similarity	NPC197351
0.907	High Similarity	NPC134195
0.907	High Similarity	NPC246648
0.907	High Similarity	NPC86502
0.9065	High Similarity	NPC475492
0.9065	High Similarity	NPC280092
0.9065	High Similarity	NPC45257
0.9065	High Similarity	NPC12641
0.9065	High Similarity	NPC93323
0.9058	High Similarity	NPC472353
0.9051	High Similarity	NPC309124
0.9051	High Similarity	NPC184797
0.9037	High Similarity	NPC151224
0.9037	High Similarity	NPC473413
0.9007	High Similarity	NPC101376
0.9	High Similarity	NPC167571
0.9	High Similarity	NPC207179
0.9	High Similarity	NPC278552
0.8993	High Similarity	NPC85264
0.8993	High Similarity	NPC47633
0.8993	High Similarity	NPC102044
0.8992	High Similarity	NPC76465
0.8992	High Similarity	NPC38761
0.8986	High Similarity	NPC263261
0.8986	High Similarity	NPC100482
0.8986	High Similarity	NPC87725
0.8986	High Similarity	NPC277331
0.8978	High Similarity	NPC70682
0.8978	High Similarity	NPC236306
0.8978	High Similarity	NPC260741
0.8978	High Similarity	NPC232164
0.8978	High Similarity	NPC32630
0.8978	High Similarity	NPC473739
0.8971	High Similarity	NPC227503
0.8971	High Similarity	NPC470802
0.8971	High Similarity	NPC474639
0.8971	High Similarity	NPC126101
0.8971	High Similarity	NPC230734
0.8963	High Similarity	NPC473107
0.8958	High Similarity	NPC160196
0.8929	High Similarity	NPC473108
0.8929	High Similarity	NPC63879
0.8923	High Similarity	NPC256015
0.8923	High Similarity	NPC294156
0.8921	High Similarity	NPC107161
0.8915	High Similarity	NPC100099
0.8915	High Similarity	NPC36016
0.8913	High Similarity	NPC27495
0.8905	High Similarity	NPC211549
0.8905	High Similarity	NPC477938
0.8897	High Similarity	NPC470356
0.8897	High Similarity	NPC94750
0.8897	High Similarity	NPC474206
0.8897	High Similarity	NPC61946
0.8897	High Similarity	NPC125579
0.8897	High Similarity	NPC164787
0.8897	High Similarity	NPC112246
0.8897	High Similarity	NPC121812
0.8897	High Similarity	NPC112939
0.8889	High Similarity	NPC11060
0.8873	High Similarity	NPC474397
0.8857	High Similarity	NPC81638
0.8855	High Similarity	NPC81641
0.8849	High Similarity	NPC247291
0.8849	High Similarity	NPC265075
0.8849	High Similarity	NPC108674
0.8849	High Similarity	NPC35216
0.8846	High Similarity	NPC474160
0.8837	High Similarity	NPC97432
0.8837	High Similarity	NPC190454
0.8836	High Similarity	NPC188578
0.8836	High Similarity	NPC80918
0.8836	High Similarity	NPC159922
0.8832	High Similarity	NPC162659
0.8832	High Similarity	NPC327735
0.8832	High Similarity	NPC302701
0.8832	High Similarity	NPC234952
0.8832	High Similarity	NPC471522
0.8832	High Similarity	NPC265433
0.8832	High Similarity	NPC248727
0.8832	High Similarity	NPC16435
0.8832	High Similarity	NPC306441
0.8832	High Similarity	NPC269091
0.8832	High Similarity	NPC270456
0.8811	High Similarity	NPC473876
0.8811	High Similarity	NPC227516
0.8811	High Similarity	NPC20757
0.8803	High Similarity	NPC260397
0.8794	High Similarity	NPC50250
0.8794	High Similarity	NPC471824
0.8786	High Similarity	NPC49542
0.8786	High Similarity	NPC230718
0.8786	High Similarity	NPC128337
0.8786	High Similarity	NPC84207
0.8786	High Similarity	NPC5253
0.8786	High Similarity	NPC139976
0.8779	High Similarity	NPC159132
0.8777	High Similarity	NPC254759
0.8777	High Similarity	NPC160283
0.8777	High Similarity	NPC259519
0.8769	High Similarity	NPC150026
0.8768	High Similarity	NPC262328
0.8768	High Similarity	NPC474282
0.8768	High Similarity	NPC470308
0.8768	High Similarity	NPC107551
0.8768	High Similarity	NPC102904
0.8768	High Similarity	NPC326797
0.8768	High Similarity	NPC176051
0.8768	High Similarity	NPC470307
0.8768	High Similarity	NPC103976
0.8768	High Similarity	NPC87777
0.8759	High Similarity	NPC260898
0.8759	High Similarity	NPC234333
0.8759	High Similarity	NPC47398
0.875	High Similarity	NPC168059
0.875	High Similarity	NPC229442
0.875	High Similarity	NPC263064
0.8732	High Similarity	NPC469701
0.8732	High Similarity	NPC181615
0.8723	High Similarity	NPC184607
0.8723	High Similarity	NPC474104
0.8714	High Similarity	NPC195357

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 NPC18189 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	332
0.1-0.2	850
0.2-0.3	1699
0.3-0.4	2639
0.4-0.5	1770
0.5-0.6	1007
0.6-0.7	685
0.7-0.8	155
0.8-0.85	6
0.85-0.9	6
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9091	High Similarity	NPD4907	Clinical (unspecified phase)
0.8939	High Similarity	NPD4908	Phase 1
0.8692	High Similarity	NPD1610	Phase 2
0.8676	High Similarity	NPD1613	Approved
0.8676	High Similarity	NPD1612	Clinical (unspecified phase)
0.8527	High Similarity	NPD1548	Phase 1
0.8519	High Similarity	NPD1529	Clinical (unspecified phase)
0.8456	Intermediate Similarity	NPD4625	Phase 3
0.8444	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8321	Intermediate Similarity	NPD3027	Phase 3
0.8309	Intermediate Similarity	NPD2861	Phase 2
0.8214	Intermediate Similarity	NPD5124	Phase 1
0.8214	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD4749	Approved
0.8133	Intermediate Similarity	NPD4380	Phase 2
0.8129	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8069	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.8042	Intermediate Similarity	NPD5588	Approved
0.8027	Intermediate Similarity	NPD5058	Phase 3
0.7974	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD7212	Phase 2
0.7973	Intermediate Similarity	NPD7213	Phase 3
0.7972	Intermediate Similarity	NPD4538	Approved
0.7972	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD4536	Approved
0.7956	Intermediate Similarity	NPD8651	Approved
0.7919	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD7447	Phase 1
0.7887	Intermediate Similarity	NPD4060	Phase 1
0.7868	Intermediate Similarity	NPD1091	Approved
0.7823	Intermediate Similarity	NPD1652	Phase 2
0.7821	Intermediate Similarity	NPD7075	Discontinued
0.7821	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD5960	Phase 3
0.7792	Intermediate Similarity	NPD1934	Approved
0.777	Intermediate Similarity	NPD7466	Approved
0.7755	Intermediate Similarity	NPD2424	Discontinued
0.7746	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD422	Phase 1
0.7716	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD3750	Approved
0.7643	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD1549	Phase 2
0.7615	Intermediate Similarity	NPD2684	Approved
0.7613	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7612	Intermediate Similarity	NPD6671	Approved
0.7612	Intermediate Similarity	NPD7157	Approved
0.761	Intermediate Similarity	NPD5494	Approved
0.7586	Intermediate Similarity	NPD6355	Discontinued
0.7584	Intermediate Similarity	NPD6674	Discontinued
0.7576	Intermediate Similarity	NPD6559	Discontinued
0.7571	Intermediate Similarity	NPD6696	Suspended
0.7564	Intermediate Similarity	NPD6801	Discontinued
0.7551	Intermediate Similarity	NPD7033	Discontinued
0.7547	Intermediate Similarity	NPD6234	Discontinued
0.7538	Intermediate Similarity	NPD290	Approved
0.7532	Intermediate Similarity	NPD7768	Phase 2
0.7532	Intermediate Similarity	NPD1653	Approved
0.7531	Intermediate Similarity	NPD6166	Phase 2
0.7531	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD7843	Approved
0.7516	Intermediate Similarity	NPD8455	Phase 2
0.7516	Intermediate Similarity	NPD2801	Approved
0.75	Intermediate Similarity	NPD6099	Approved
0.75	Intermediate Similarity	NPD2796	Approved
0.75	Intermediate Similarity	NPD6100	Approved
0.75	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6798	Discontinued
0.75	Intermediate Similarity	NPD7411	Suspended
0.75	Intermediate Similarity	NPD5844	Phase 1
0.75	Intermediate Similarity	NPD6072	Discontinued
0.7483	Intermediate Similarity	NPD7097	Phase 1
0.7465	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD5125	Phase 3
0.7464	Intermediate Similarity	NPD5126	Approved
0.7453	Intermediate Similarity	NPD6959	Discontinued
0.7452	Intermediate Similarity	NPD37	Approved
0.7439	Intermediate Similarity	NPD3818	Discontinued
0.7439	Intermediate Similarity	NPD7228	Approved
0.7432	Intermediate Similarity	NPD1510	Phase 2
0.7421	Intermediate Similarity	NPD4965	Approved
0.7421	Intermediate Similarity	NPD4967	Phase 2
0.7421	Intermediate Similarity	NPD4966	Approved
0.7421	Intermediate Similarity	NPD3882	Suspended
0.7417	Intermediate Similarity	NPD4535	Phase 3
0.7417	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD3018	Phase 2
0.7405	Intermediate Similarity	NPD7819	Suspended
0.7394	Intermediate Similarity	NPD7054	Approved
0.7386	Intermediate Similarity	NPD1511	Approved
0.7355	Intermediate Similarity	NPD5403	Approved
0.7349	Intermediate Similarity	NPD7472	Approved
0.7349	Intermediate Similarity	NPD7074	Phase 3
0.7347	Intermediate Similarity	NPD5735	Approved
0.7346	Intermediate Similarity	NPD7199	Phase 2
0.7338	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD6516	Phase 2
0.7338	Intermediate Similarity	NPD5846	Approved
0.7333	Intermediate Similarity	NPD5762	Approved
0.7333	Intermediate Similarity	NPD6005	Phase 3
0.7333	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6004	Phase 3
0.7333	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6002	Phase 3
0.7333	Intermediate Similarity	NPD5763	Approved
0.7329	Intermediate Similarity	NPD6233	Phase 2
0.7328	Intermediate Similarity	NPD968	Approved
0.7317	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD3748	Approved
0.731	Intermediate Similarity	NPD7095	Approved
0.7305	Intermediate Similarity	NPD6797	Phase 2
0.7303	Intermediate Similarity	NPD4628	Phase 3
0.7303	Intermediate Similarity	NPD3892	Phase 2
0.7301	Intermediate Similarity	NPD7229	Phase 3
0.7296	Intermediate Similarity	NPD5929	Approved
0.729	Intermediate Similarity	NPD1512	Approved
0.7287	Intermediate Similarity	NPD940	Approved
0.7287	Intermediate Similarity	NPD846	Approved
0.7279	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6799	Approved
0.7273	Intermediate Similarity	NPD2797	Approved
0.7267	Intermediate Similarity	NPD3749	Approved
0.7262	Intermediate Similarity	NPD7251	Discontinued
0.7256	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD2982	Phase 2
0.7254	Intermediate Similarity	NPD2983	Phase 2
0.7254	Intermediate Similarity	NPD6582	Phase 2
0.7254	Intermediate Similarity	NPD6583	Phase 3
0.725	Intermediate Similarity	NPD5402	Approved
0.725	Intermediate Similarity	NPD3817	Phase 2
0.7237	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD2800	Approved
0.723	Intermediate Similarity	NPD4340	Discontinued
0.7226	Intermediate Similarity	NPD5401	Approved
0.7222	Intermediate Similarity	NPD6584	Phase 3
0.7219	Intermediate Similarity	NPD7549	Discontinued
0.7219	Intermediate Similarity	NPD7808	Phase 3
0.7215	Intermediate Similarity	NPD6599	Discontinued
0.7206	Intermediate Similarity	NPD5283	Phase 1
0.7203	Intermediate Similarity	NPD3225	Approved
0.7195	Intermediate Similarity	NPD3787	Discontinued
0.719	Intermediate Similarity	NPD6331	Phase 2
0.7183	Intermediate Similarity	NPD2981	Phase 2
0.7162	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1240	Approved
0.7162	Intermediate Similarity	NPD3620	Phase 2
0.7162	Intermediate Similarity	NPD2238	Phase 2
0.7161	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD7041	Phase 2
0.7152	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2415	Discontinued
0.7143	Intermediate Similarity	NPD2677	Approved
0.7143	Intermediate Similarity	NPD3268	Approved
0.7133	Intermediate Similarity	NPD5327	Phase 3
0.7132	Intermediate Similarity	NPD5535	Approved
0.7125	Intermediate Similarity	NPD4433	Discontinued
0.7118	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD2532	Approved
0.7115	Intermediate Similarity	NPD2534	Approved
0.7115	Intermediate Similarity	NPD2533	Approved
0.7113	Intermediate Similarity	NPD3705	Approved
0.711	Intermediate Similarity	NPD7906	Approved
0.7105	Intermediate Similarity	NPD7266	Discontinued
0.7105	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD3690	Phase 2
0.7103	Intermediate Similarity	NPD3691	Phase 2
0.7101	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6667	Approved
0.7097	Intermediate Similarity	NPD3122	Phase 3
0.7097	Intermediate Similarity	NPD6666	Approved
0.7091	Intermediate Similarity	NPD6232	Discontinued
0.7086	Intermediate Similarity	NPD3846	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD1465	Phase 2
0.708	Intermediate Similarity	NPD1398	Phase 1
0.7076	Intermediate Similarity	NPD7310	Approved
0.7076	Intermediate Similarity	NPD4578	Approved
0.7076	Intermediate Similarity	NPD7311	Approved
0.7076	Intermediate Similarity	NPD7312	Approved
0.7076	Intermediate Similarity	NPD4577	Approved
0.7076	Intermediate Similarity	NPD7313	Approved
0.7071	Intermediate Similarity	NPD7741	Discontinued
0.7067	Intermediate Similarity	NPD1607	Approved
0.7067	Intermediate Similarity	NPD6353	Approved
0.7067	Intermediate Similarity	NPD4097	Suspended
0.7059	Intermediate Similarity	NPD7240	Approved
0.7059	Intermediate Similarity	NPD228	Approved
0.7059	Intermediate Similarity	NPD7037	Approved
0.7052	Intermediate Similarity	NPD4663	Approved
0.705	Intermediate Similarity	NPD7340	Approved
0.7048	Intermediate Similarity	NPD2970	Approved
0.7048	Intermediate Similarity	NPD2969	Approved
0.7047	Intermediate Similarity	NPD4140	Approved
0.7044	Intermediate Similarity	NPD6055	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