NPASS Compound

Structure

CID178574 OpenBabel06191715552D 29 32 0 0 1 0 0 0 0 0999 V2000 3.1277 1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2617 6.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9937 4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3956 2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5296 4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5296 3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 1.0827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0685 4.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2617 3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3956 4.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 2.5827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3364 1.5827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0685 1.5827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2617 4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 5.5827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8005 4.5827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 1.0827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3849 1.1215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1277 2.5827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3956 5.5827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1277 4.5827 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 26 1 0 0 0 0 2 27 1 0 0 0 0 3 28 1 0 0 0 0 4 9 2 0 0 0 0 4 15 1 0 0 0 0 5 9 1 0 0 0 0 5 16 2 0 0 0 0 6 10 2 0 0 0 0 6 13 1 0 0 0 0 7 11 2 0 0 0 0 7 14 1 0 0 0 0 8 29 1 0 0 0 0 10 11 1 0 0 0 0 10 17 1 0 0 0 0 11 19 1 0 0 0 0 12 8 1 6 0 0 0 12 18 1 0 0 0 0 12 19 1 0 0 0 0 13 14 2 0 0 0 0 13 22 1 0 0 0 0 14 23 1 0 0 0 0 15 20 2 0 0 0 0 15 26 1 0 0 0 0 16 20 1 0 0 0 0 16 27 1 0 0 0 0 17 9 1 1 0 0 0 17 18 1 0 0 0 0 18 21 1 1 0 0 0 19 24 1 1 0 0 0 20 28 1 0 0 0 0 21 25 2 0 0 0 0 21 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	402.13
Volume:	389.413
LogP:	1.235
LogD:	1.54
LogS:	-3.251
# Rotatable Bonds:	4
TPSA:	114.68
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.526
Synthetic Accessibility Score:	3.769
Fsp3:	0.381
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:	-4.962
MDCK Permeability:	9.245663932233583e-06
Pgp-inhibitor:	0.011
Pgp-substrate:	0.131
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.023

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.035
Plasma Protein Binding (PPB):	92.57587432861328%
Volume Distribution (VD):	0.965
Pgp-substrate:	8.354425430297852%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.915
CYP2C19-inhibitor:	0.048
CYP2C19-substrate:	0.821
CYP2C9-inhibitor:	0.197
CYP2C9-substrate:	0.787
CYP2D6-inhibitor:	0.025
CYP2D6-substrate:	0.268
CYP3A4-inhibitor:	0.494
CYP3A4-substrate:	0.892

ADMET: Excretion

Clearance (CL):	9.157
Half-life (T1/2):	0.795

ADMET: Toxicity

hERG Blockers:	0.088
Human Hepatotoxicity (H-HT):	0.18
Drug-inuced Liver Injury (DILI):	0.407
AMES Toxicity:	0.085
Rat Oral Acute Toxicity:	0.239
Maximum Recommended Daily Dose:	0.947
Skin Sensitization:	0.28
Carcinogencity:	0.02
Eye Corrosion:	0.003
Eye Irritation:	0.175
Respiratory Toxicity:	0.706

Download Data

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

Natural Product: NPC178574

Natural Product ID:	NPC178574
*Common Name:**	6,7-O,O-Demethylenepodophyllotoxin
IUPAC Name:	(3aR,4R,9R,9aR)-4,6,7-trihydroxy-9-(3,4,5-trimethoxyphenyl)-3a,4,9,9a-tetrahydro-3H-benzo[f][2]benzofuran-1-one
Synonyms:	3',4'-Demethylene-Podophyllotoxin
Standard InCHIKey:	AIEQNTGIFXFNRB-BTINSWFASA-N
Standard InCHI:	InChI=1S/C21H22O8/c1-26-15-4-9(5-16(27-2)20(15)28-3)17-10-6-13(22)14(23)7-11(10)19(24)12-8-29-21(25)18(12)17/h4-7,12,17-19,22-24H,8H2,1-3H3/t12-,17+,18-,19-/m0/s1
SMILES:	COc1cc(cc(c1OC)OC)[C@H]1[C@H]2C(=O)OC[C@@H]2[C@H](c2c1cc(O)c(c2)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL329250
PubChem CID:	3010625
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001510] Lignan lactones

*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
NPO14752	Sinopodophyllum emodi	Species	Berberidaceae	Eukaryota	roots and rhizomes	n.a.	n.a.	PMID[21570846]
NPO11163	Methylobacterium organophilum	Species	Methylobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26032177]
NPO10903	Sinopodophyllum hexandrum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26359402]
NPO11163	Methylobacterium organophilum	Species	Methylobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[3928379]
NPO10903	Sinopodophyllum hexandrum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4464	Senecio mexicanus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6893	Dimorphotheca sinuata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14752	Sinopodophyllum emodi	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3025	Schefflera capitata	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11163	Methylobacterium organophilum	Species	Methylobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO11417	Gesneria cardinalis	Species	Crambidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10903	Sinopodophyllum hexandrum	Species	Berberidaceae	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
Others	32

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	2
Organism	31

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	100000.0	nM	PMID[447990]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	100000.0	nM	PMID[447990]
NPT32	Organism	Mus musculus	Mus musculus	IC50	=	0.00563	ug.mL-1	PMID[447989]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Cytotoxicity	>	27.5	ug ml-1	PMID[447989]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Ratio	>	4885.0	n.a.	PMID[447989]
NPT32	Organism	Mus musculus	Mus musculus	Body weight	=	16.3	g	PMID[447989]
NPT32	Organism	Mus musculus	Mus musculus	Body weight	=	16.8	g	PMID[447989]
NPT32	Organism	Mus musculus	Mus musculus	Body weight	=	16.5	g	PMID[447989]
NPT32	Organism	Mus musculus	Mus musculus	Weight change	=	1.8	%	PMID[447989]
NPT32	Organism	Mus musculus	Mus musculus	Weight change	=	2.9	%	PMID[447989]
NPT32	Organism	Mus musculus	Mus musculus	Weight change	=	-1.8	%	PMID[447989]
NPT32	Organism	Mus musculus	Mus musculus	Spleen weight	=	5.75	g	PMID[447989]
NPT32	Organism	Mus musculus	Mus musculus	Spleen weight	=	5.2	g	PMID[447989]
NPT32	Organism	Mus musculus	Mus musculus	Spleen weight	=	4.1	g	PMID[447989]
NPT32	Organism	Mus musculus	Mus musculus	SI	=	1.15	n.a.	PMID[447989]
NPT32	Organism	Mus musculus	Mus musculus	SI	=	1.04	n.a.	PMID[447989]
NPT32	Organism	Mus musculus	Mus musculus	SI	=	0.82	n.a.	PMID[447989]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	44.0	%	PMID[447989]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	85.0	%	PMID[447989]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	167.0	%	PMID[447989]
NPT32	Organism	Mus musculus	Mus musculus	Body weight	=	17.8	g	PMID[447989]
NPT32	Organism	Mus musculus	Mus musculus	Body weight	=	18.5	g	PMID[447989]
NPT32	Organism	Mus musculus	Mus musculus	Body weight	=	18.7	g	PMID[447989]
NPT32	Organism	Mus musculus	Mus musculus	Body weight	=	1.6	g	PMID[447989]
NPT32	Organism	Mus musculus	Mus musculus	Body weight	=	1.0	g	PMID[447989]
NPT32	Organism	Mus musculus	Mus musculus	Body weight	=	0.7	g	PMID[447989]
NPT32	Organism	Mus musculus	Mus musculus	Mean graft survival	=	10.7	day	PMID[447989]
NPT32	Organism	Mus musculus	Mus musculus	Mean graft survival	=	12.5	day	PMID[447989]
NPT32	Organism	Mus musculus	Mus musculus	Mean graft survival	=	10.0	day	PMID[447989]
NPT32	Organism	Mus musculus	Mus musculus	graft survival	=	1.09	day	PMID[447989]
NPT32	Organism	Mus musculus	Mus musculus	graft survival	=	1.28	day	PMID[447989]
NPT32	Organism	Mus musculus	Mus musculus	graft survival	=	1.02	day	PMID[447989]
NPT1769	Organism	Mythimna separata	Mythimna separata	mortality	=	0.0	%	PMID[447991]
NPT1769	Organism	Mythimna separata	Mythimna separata	mortality	=	6.7	%	PMID[447991]
NPT1769	Organism	Mythimna separata	Mythimna separata	mortality	=	23.3	%	PMID[447991]

☑ 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 NPC178574 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	326
0.1-0.2	1250
0.2-0.3	2935
0.3-0.4	6206
0.4-0.5	11262
0.5-0.6	5127
0.6-0.7	6492
0.7-0.8	7896
0.8-0.85	996
0.85-0.9	171
0.9-0.95	31
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC65591
0.9603	High Similarity	NPC150943
0.9603	High Similarity	NPC268718
0.9603	High Similarity	NPC91634
0.9463	High Similarity	NPC245948
0.9416	High Similarity	NPC116759
0.9416	High Similarity	NPC14294
0.9404	High Similarity	NPC237946
0.9404	High Similarity	NPC32373
0.9342	High Similarity	NPC181168
0.9342	High Similarity	NPC19947
0.9342	High Similarity	NPC115281
0.9342	High Similarity	NPC207584
0.9342	High Similarity	NPC163527
0.931	High Similarity	NPC470811
0.931	High Similarity	NPC477697
0.931	High Similarity	NPC477696
0.9272	High Similarity	NPC103197
0.9272	High Similarity	NPC30009
0.9267	High Similarity	NPC476434
0.9236	High Similarity	NPC185498
0.9221	High Similarity	NPC119910
0.9195	High Similarity	NPC125570
0.9178	High Similarity	NPC273657
0.9178	High Similarity	NPC106920
0.9161	High Similarity	NPC152424
0.9161	High Similarity	NPC100465
0.9161	High Similarity	NPC288149
0.9133	High Similarity	NPC24425
0.9119	High Similarity	NPC179240
0.9097	High Similarity	NPC96593
0.9079	High Similarity	NPC473236
0.9073	High Similarity	NPC210642
0.9073	High Similarity	NPC13985
0.9041	High Similarity	NPC29599
0.9041	High Similarity	NPC100675
0.9038	High Similarity	NPC115624
0.902	High Similarity	NPC136757
0.8987	High Similarity	NPC222531
0.8961	High Similarity	NPC238834
0.894	High Similarity	NPC174512
0.894	High Similarity	NPC474965
0.894	High Similarity	NPC477695
0.894	High Similarity	NPC293757
0.894	High Similarity	NPC668
0.8931	High Similarity	NPC306475
0.8912	High Similarity	NPC470991
0.8904	High Similarity	NPC230124
0.8904	High Similarity	NPC6300
0.8904	High Similarity	NPC114171
0.8903	High Similarity	NPC165483
0.8896	High Similarity	NPC273578
0.8889	High Similarity	NPC477699
0.8882	High Similarity	NPC149505
0.8867	High Similarity	NPC474054
0.8859	High Similarity	NPC27159
0.8859	High Similarity	NPC87883
0.8854	High Similarity	NPC24627
0.8846	High Similarity	NPC143328
0.8831	High Similarity	NPC474606
0.8828	High Similarity	NPC72796
0.8828	High Similarity	NPC44245
0.8824	High Similarity	NPC475756
0.8824	High Similarity	NPC477700
0.882	High Similarity	NPC117911
0.8816	High Similarity	NPC216223
0.8816	High Similarity	NPC145569
0.8808	High Similarity	NPC65574
0.8808	High Similarity	NPC80230
0.8808	High Similarity	NPC304687
0.8808	High Similarity	NPC101755
0.8808	High Similarity	NPC104024
0.88	High Similarity	NPC223185
0.8797	High Similarity	NPC139540
0.8797	High Similarity	NPC177100
0.8797	High Similarity	NPC109061
0.8776	High Similarity	NPC184613
0.8766	High Similarity	NPC471154
0.8766	High Similarity	NPC56184
0.8759	High Similarity	NPC244983
0.8759	High Similarity	NPC326095
0.8758	High Similarity	NPC215802
0.8758	High Similarity	NPC167231
0.8758	High Similarity	NPC311912
0.875	High Similarity	NPC252402
0.875	High Similarity	NPC102934
0.875	High Similarity	NPC304821
0.8742	High Similarity	NPC212890
0.8742	High Similarity	NPC42797
0.8742	High Similarity	NPC473445
0.8734	High Similarity	NPC472055
0.8726	High Similarity	NPC77679
0.8726	High Similarity	NPC84935
0.8726	High Similarity	NPC190020
0.8725	High Similarity	NPC253722
0.8725	High Similarity	NPC31751
0.8725	High Similarity	NPC253481
0.8718	High Similarity	NPC476642
0.871	High Similarity	NPC115466
0.871	High Similarity	NPC61604
0.871	High Similarity	NPC299706
0.871	High Similarity	NPC245615
0.8707	High Similarity	NPC281780
0.8704	High Similarity	NPC88557
0.8701	High Similarity	NPC32079
0.8699	High Similarity	NPC211386
0.8699	High Similarity	NPC113295
0.8696	High Similarity	NPC174734
0.8696	High Similarity	NPC474042
0.8693	High Similarity	NPC474347
0.8693	High Similarity	NPC474393
0.8693	High Similarity	NPC477698
0.8693	High Similarity	NPC262455
0.8693	High Similarity	NPC177476
0.8688	High Similarity	NPC291977
0.8679	High Similarity	NPC124747
0.8679	High Similarity	NPC155754
0.8675	High Similarity	NPC477702
0.8671	High Similarity	NPC98083
0.8671	High Similarity	NPC166456
0.8671	High Similarity	NPC94220
0.8671	High Similarity	NPC7543
0.8671	High Similarity	NPC24339
0.8671	High Similarity	NPC470339
0.8662	High Similarity	NPC150227
0.8654	High Similarity	NPC43872
0.8654	High Similarity	NPC116850
0.8654	High Similarity	NPC144801
0.8654	High Similarity	NPC238672
0.8654	High Similarity	NPC197188
0.8654	High Similarity	NPC287504
0.8654	High Similarity	NPC291510
0.865	High Similarity	NPC91043
0.8645	High Similarity	NPC93498
0.8645	High Similarity	NPC163883
0.8645	High Similarity	NPC267091
0.8639	High Similarity	NPC471988
0.8636	High Similarity	NPC260781
0.8636	High Similarity	NPC218041
0.8636	High Similarity	NPC469706
0.8636	High Similarity	NPC182368
0.8636	High Similarity	NPC470916
0.8636	High Similarity	NPC145979
0.8636	High Similarity	NPC9933
0.8636	High Similarity	NPC185955
0.8636	High Similarity	NPC225815
0.8636	High Similarity	NPC469707
0.8636	High Similarity	NPC214326
0.863	High Similarity	NPC4982
0.863	High Similarity	NPC176814
0.863	High Similarity	NPC68779
0.863	High Similarity	NPC67247
0.863	High Similarity	NPC287745
0.863	High Similarity	NPC471942
0.863	High Similarity	NPC300776
0.863	High Similarity	NPC5310
0.8627	High Similarity	NPC325720
0.8627	High Similarity	NPC477879
0.8627	High Similarity	NPC316676
0.8625	High Similarity	NPC55121
0.8621	High Similarity	NPC204215
0.8621	High Similarity	NPC175067
0.8621	High Similarity	NPC14224
0.8621	High Similarity	NPC161958
0.8618	High Similarity	NPC474799
0.8618	High Similarity	NPC260397
0.8618	High Similarity	NPC112251
0.8609	High Similarity	NPC18211
0.8609	High Similarity	NPC143092
0.86	High Similarity	NPC131971
0.86	High Similarity	NPC67467
0.86	High Similarity	NPC191231
0.86	High Similarity	NPC52664
0.8599	High Similarity	NPC142479
0.8599	High Similarity	NPC16082
0.8599	High Similarity	NPC79998
0.8599	High Similarity	NPC155015
0.8599	High Similarity	NPC199926
0.8599	High Similarity	NPC38699
0.8599	High Similarity	NPC82592
0.8599	High Similarity	NPC476065
0.8598	High Similarity	NPC471181
0.8591	High Similarity	NPC147379
0.859	High Similarity	NPC475141
0.859	High Similarity	NPC146277
0.859	High Similarity	NPC149735
0.859	High Similarity	NPC19380
0.8581	High Similarity	NPC303519
0.8581	High Similarity	NPC243891
0.8581	High Similarity	NPC164082
0.858	High Similarity	NPC43065
0.858	High Similarity	NPC472452
0.8571	High Similarity	NPC165155
0.8571	High Similarity	NPC34103
0.8571	High Similarity	NPC223006
0.8571	High Similarity	NPC272750
0.8571	High Similarity	NPC134047
0.8571	High Similarity	NPC141765
0.8571	High Similarity	NPC173729
0.8571	High Similarity	NPC313081

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 NPC178574 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	273
0.1-0.2	821
0.2-0.3	1688
0.3-0.4	2517
0.4-0.5	2106
0.5-0.6	1008
0.6-0.7	588
0.7-0.8	132
0.8-0.85	12
0.85-0.9	0
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9536	High Similarity	NPD6234	Discontinued
0.9463	High Similarity	NPD37	Approved
0.9404	High Similarity	NPD4967	Phase 2
0.9404	High Similarity	NPD4966	Approved
0.9404	High Similarity	NPD4965	Approved
0.9236	High Similarity	NPD7228	Approved
0.8659	High Similarity	NPD7240	Approved
0.8562	High Similarity	NPD7199	Phase 2
0.8428	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8395	Intermediate Similarity	NPD6232	Discontinued
0.8354	Intermediate Similarity	NPD7473	Discontinued
0.8344	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8288	Intermediate Similarity	NPD3027	Phase 3
0.8284	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD5844	Phase 1
0.8239	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD3818	Discontinued
0.8075	Intermediate Similarity	NPD1465	Phase 2
0.8056	Intermediate Similarity	NPD7680	Approved
0.8012	Intermediate Similarity	NPD1934	Approved
0.8	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1613	Approved
0.7964	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD6166	Phase 2
0.7964	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD6190	Approved
0.7941	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD2533	Approved
0.7911	Intermediate Similarity	NPD2534	Approved
0.7911	Intermediate Similarity	NPD2532	Approved
0.7892	Intermediate Similarity	NPD8127	Discontinued
0.7881	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD3620	Phase 2
0.7866	Intermediate Similarity	NPD3882	Suspended
0.7853	Intermediate Similarity	NPD2801	Approved
0.7848	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD7229	Phase 3
0.7812	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD3817	Phase 2
0.7785	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7074	Phase 3
0.7746	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD5494	Approved
0.7719	Intermediate Similarity	NPD7054	Approved
0.7712	Intermediate Similarity	NPD230	Phase 1
0.7688	Intermediate Similarity	NPD6559	Discontinued
0.7688	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD7472	Approved
0.7669	Intermediate Similarity	NPD4380	Phase 2
0.7658	Intermediate Similarity	NPD4110	Phase 3
0.7658	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD1653	Approved
0.7647	Intermediate Similarity	NPD4060	Phase 1
0.7643	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD7819	Suspended
0.7632	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD2438	Suspended
0.7605	Intermediate Similarity	NPD7075	Discontinued
0.7597	Intermediate Similarity	NPD6355	Discontinued
0.7595	Intermediate Similarity	NPD6674	Discontinued
0.7586	Intermediate Similarity	NPD7685	Pre-registration
0.7574	Intermediate Similarity	NPD6959	Discontinued
0.7547	Intermediate Similarity	NPD4628	Phase 3
0.7547	Intermediate Similarity	NPD8166	Discontinued
0.7547	Intermediate Similarity	NPD3750	Approved
0.7529	Intermediate Similarity	NPD6797	Phase 2
0.7516	Intermediate Similarity	NPD6798	Discontinued
0.7516	Intermediate Similarity	NPD6099	Approved
0.7516	Intermediate Similarity	NPD6100	Approved
0.7516	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1511	Approved
0.7515	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4908	Phase 1
0.7486	Intermediate Similarity	NPD7251	Discontinued
0.7485	Intermediate Similarity	NPD5402	Approved
0.747	Intermediate Similarity	NPD6801	Discontinued
0.7468	Intermediate Similarity	NPD5762	Approved
0.7468	Intermediate Similarity	NPD7266	Discontinued
0.7468	Intermediate Similarity	NPD5763	Approved
0.7468	Intermediate Similarity	NPD6233	Phase 2
0.7467	Intermediate Similarity	NPD1283	Approved
0.7443	Intermediate Similarity	NPD7808	Phase 3
0.7427	Intermediate Similarity	NPD3787	Discontinued
0.7425	Intermediate Similarity	NPD8455	Phase 2
0.7425	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD1512	Approved
0.7423	Intermediate Similarity	NPD6273	Approved
0.7419	Intermediate Similarity	NPD2979	Phase 3
0.7419	Intermediate Similarity	NPD4140	Approved
0.7403	Intermediate Similarity	NPD3764	Approved
0.7403	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD8312	Approved
0.7401	Intermediate Similarity	NPD8313	Approved
0.7396	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD3705	Approved
0.7381	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD8434	Phase 2
0.7362	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6004	Phase 3
0.7358	Intermediate Similarity	NPD6005	Phase 3
0.7358	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6002	Phase 3
0.7355	Intermediate Similarity	NPD6663	Approved
0.7344	Intermediate Similarity	NPD7827	Phase 1
0.7338	Intermediate Similarity	NPD4625	Phase 3
0.7337	Intermediate Similarity	NPD7768	Phase 2
0.7326	Intermediate Similarity	NPD5711	Approved
0.7326	Intermediate Similarity	NPD5710	Approved
0.732	Intermediate Similarity	NPD5736	Approved
0.7305	Intermediate Similarity	NPD7411	Suspended
0.7296	Intermediate Similarity	NPD2935	Discontinued
0.7294	Intermediate Similarity	NPD3749	Approved
0.729	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD3226	Approved
0.7285	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7097	Phase 1
0.7273	Intermediate Similarity	NPD5403	Approved
0.7267	Intermediate Similarity	NPD1610	Phase 2
0.7267	Intermediate Similarity	NPD1281	Approved
0.7267	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD3751	Discontinued
0.7256	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6599	Discontinued
0.7244	Intermediate Similarity	NPD8032	Phase 2
0.7233	Intermediate Similarity	NPD7033	Discontinued
0.7233	Intermediate Similarity	NPD3748	Approved
0.7226	Intermediate Similarity	NPD7095	Approved
0.7219	Intermediate Similarity	NPD1608	Approved
0.7216	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6653	Approved
0.7209	Intermediate Similarity	NPD6746	Phase 2
0.7208	Intermediate Similarity	NPD3018	Phase 2
0.7208	Intermediate Similarity	NPD2861	Phase 2
0.7195	Intermediate Similarity	NPD6799	Approved
0.719	Intermediate Similarity	NPD2797	Approved
0.7188	Intermediate Similarity	NPD8151	Discontinued
0.7184	Intermediate Similarity	NPD5242	Approved
0.7182	Intermediate Similarity	NPD8150	Discontinued
0.7181	Intermediate Similarity	NPD2494	Approved
0.7181	Intermediate Similarity	NPD2493	Approved
0.7176	Intermediate Similarity	NPD5353	Approved
0.7171	Intermediate Similarity	NPD2982	Phase 2
0.7171	Intermediate Similarity	NPD4749	Approved
0.7171	Intermediate Similarity	NPD2983	Phase 2
0.716	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD4582	Approved
0.7158	Intermediate Similarity	NPD4583	Approved
0.7152	Intermediate Similarity	NPD5124	Phase 1
0.7152	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD5735	Approved
0.7152	Intermediate Similarity	NPD5401	Approved
0.7151	Intermediate Similarity	NPD919	Approved
0.7143	Intermediate Similarity	NPD7028	Phase 2
0.7143	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD1510	Phase 2
0.7123	Intermediate Similarity	NPD5283	Phase 1
0.7117	Intermediate Similarity	NPD7003	Approved
0.7108	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4004	Approved
0.7105	Intermediate Similarity	NPD2981	Phase 2
0.7105	Intermediate Similarity	NPD4002	Approved
0.7099	Intermediate Similarity	NPD1549	Phase 2
0.7091	Intermediate Similarity	NPD4357	Discontinued
0.709	Intermediate Similarity	NPD3450	Approved
0.709	Intermediate Similarity	NPD3452	Approved
0.7086	Intermediate Similarity	NPD3926	Phase 2
0.7083	Intermediate Similarity	NPD4005	Discontinued
0.7081	Intermediate Similarity	NPD1551	Phase 2
0.7081	Intermediate Similarity	NPD2531	Phase 2
0.7078	Intermediate Similarity	NPD3094	Phase 2
0.707	Intermediate Similarity	NPD3268	Approved
0.7067	Intermediate Similarity	NPD1651	Approved
0.7065	Intermediate Similarity	NPD2488	Approved
0.7065	Intermediate Similarity	NPD2490	Approved
0.7056	Intermediate Similarity	NPD7549	Discontinued
0.7055	Intermediate Similarity	NPD1652	Phase 2
0.7048	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD3657	Discovery
0.7044	Intermediate Similarity	NPD447	Suspended
0.7037	Intermediate Similarity	NPD2346	Discontinued
0.7032	Intermediate Similarity	NPD5647	Approved
0.7025	Intermediate Similarity	NPD4062	Phase 3
0.702	Intermediate Similarity	NPD17	Approved
0.702	Intermediate Similarity	NPD3019	Approved
0.702	Intermediate Similarity	NPD4626	Approved
0.7019	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD7435	Discontinued
0.7012	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1607	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