NPASS Compound

Structure

CID60973 OpenBabel06191715392D 32 37 0 0 1 0 0 0 0 0999 V2000 -3.0165 -1.5910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5034 -2.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.9211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5297 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 -2.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 -3.8947 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2624 -0.5777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 -3.4079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 -1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9140 -1.3012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 -0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4747 -1.9420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3729 -0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9474 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6865 -1.9474 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5297 -3.4079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 -0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5297 -0.4868 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8432 0.4868 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6865 0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5297 -2.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 -2.4342 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6865 -0.9737 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.9737 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8432 -0.4868 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3729 -3.8947 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 0.4868 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 1.9474 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4271 -2.1445 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5297 0.4868 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 22 1 0 0 0 0 2 22 1 0 0 0 0 4 24 1 0 0 0 0 5 25 1 0 0 0 0 6 10 1 0 0 0 0 6 15 1 0 0 0 0 7 9 2 0 0 0 0 7 17 1 0 0 0 0 8 11 2 0 0 0 0 8 14 1 0 0 0 0 9 23 1 0 0 0 0 10 24 1 0 0 0 0 11 30 1 0 0 0 0 12 16 1 0 0 0 0 12 18 1 0 0 0 0 13 14 2 0 0 0 0 13 30 1 0 0 0 0 14 19 1 0 0 0 0 15 23 1 6 0 0 0 15 25 1 0 0 0 0 16 22 1 0 0 0 0 16 23 1 6 0 0 0 17 22 1 0 0 0 0 17 27 2 0 0 0 0 18 25 1 0 0 0 0 18 28 2 0 0 0 0 19 24 1 1 0 0 0 19 31 1 0 0 0 0 20 21 1 0 0 0 0 20 26 1 1 0 0 0 20 32 1 0 0 0 0 21 29 2 0 0 0 0 21 31 1 0 0 0 0 23 3 1 6 0 0 0 24 26 1 1 0 0 0 25 26 1 1 0 0 0 26 32 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	438.2
Volume:	443.836
LogP:	3.406
LogD:	2.871
LogS:	-4.927
# Rotatable Bonds:	1
TPSA:	86.11
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.483
Synthetic Accessibility Score:	5.523
Fsp3:	0.654
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.348
MDCK Permeability:	2.046844019787386e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.671
30% Bioavailability (F30%):	0.97

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.473
Plasma Protein Binding (PPB):	84.52136993408203%
Volume Distribution (VD):	1.838
Pgp-substrate:	15.170578956604004%

ADMET: Metabolism

CYP1A2-inhibitor:	0.029
CYP1A2-substrate:	0.474
CYP2C19-inhibitor:	0.225
CYP2C19-substrate:	0.725
CYP2C9-inhibitor:	0.431
CYP2C9-substrate:	0.026
CYP2D6-inhibitor:	0.142
CYP2D6-substrate:	0.062
CYP3A4-inhibitor:	0.839
CYP3A4-substrate:	0.772

ADMET: Excretion

Clearance (CL):	10.223
Half-life (T1/2):	0.579

ADMET: Toxicity

hERG Blockers:	0.079
Human Hepatotoxicity (H-HT):	0.246
Drug-inuced Liver Injury (DILI):	0.108
AMES Toxicity:	0.038
Rat Oral Acute Toxicity:	0.974
Maximum Recommended Daily Dose:	0.913
Skin Sensitization:	0.145
Carcinogencity:	0.696
Eye Corrosion:	0.007
Eye Irritation:	0.101
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC60973

Natural Product ID:	NPC60973
*Common Name:**	Deacetoxy-7-Oxogedunin
IUPAC Name:	n.a.
Synonyms:	7-Ketogedunin; 7-Oxo-Gedunin; 7-Oxogedunin
Standard InCHIKey:	PMISPNORJONCHB-OASIGRBWSA-N
Standard InCHI:	InChI=1S/C26H30O6/c1-22(2)16-12-18(28)25(5)15(23(16,3)9-7-17(22)27)6-10-24(4)19(14-8-11-30-13-14)31-21(29)20-26(24,25)32-20/h7-9,11,13,15-16,19-20H,6,10,12H2,1-5H3/t15-,16+,19+,20-,23-,24+,25+,26-/m1/s1
SMILES:	CC1(C)[C@@H]2CC(=O)[C@]3(C)[C@H](CC[C@@]4(C)[C@H](c5ccoc5)OC(=O)[C@@H]5[C@]34O5)[C@@]2(C)C=CC1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL452232
PubChem CID:	21594780
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans

*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
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	n.a.	rind	n.a.	DOI[10.1002/hlca.200800177]
NPO7664	Pseudocedrela kotschyi	Species	Meliaceae	Eukaryota	roots	n.a.	n.a.	PMID[17253841]
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	seeds	n.a.	n.a.	PMID[17323995]
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	n.a.	bark	n.a.	PMID[17450509]
NPO3494	Swietenia mahagoni	Species	Meliaceae	Eukaryota	fruits	n.a.	n.a.	PMID[19902967]
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	seed kernels	n.a.	n.a.	PMID[19908853]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20112995]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	seeds	n.a.	n.a.	PMID[20146503]
NPO4899	Streptomyces fungicidicus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20353165]
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20411928]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	seeds	Thai	n.a.	PMID[21733687]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	seeds	n.a.	n.a.	PMID[22724531]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	seeds	n.a.	n.a.	PMID[26114936]
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31895570]
NPO20413	Meliaceae spp.	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9134742]
NPO20413	Meliaceae spp.	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10266	Alaria nana	Species	Alariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3494	Swietenia mahagoni	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7417	Pieris melete	Species	Pieridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9736	Artemisia arctica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1469	Cyperus compressus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8937	Ferreirea spectabilis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO7664	Pseudocedrela kotschyi	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4899	Streptomyces fungicidicus	Species	Streptomycetaceae	Bacteria	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	10
Others	5

Activity Type	# Activity
Cell Line	5
Individual Protein	2
Organism	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT839	Cell Line	L6	Rattus norvegicus	IC50	>	90.0	ug.mL-1	PMID[496710]
NPT91	Cell Line	KB	Homo sapiens	Activity	=	99.0	%	PMID[496711]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	16170.0	nM	PMID[496715]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	22800.0	nM	PMID[496716]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	16680.0	nM	PMID[496716]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1.775	ug.mL-1	PMID[496710]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	0.994	ug.mL-1	PMID[496710]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	3.4	ug.mL-1	PMID[496710]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	>	30.0	ug.mL-1	PMID[496710]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	>	10.0	ug.mL-1	PMID[496711]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Activity	<	0.39	%	PMID[496711]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Activity	<	0.0005	%	PMID[496711]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	85.14	%	PMID[496717]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	40.28	%	PMID[496717]

☑ 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 NPC60973 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	431
0.1-0.2	1565
0.2-0.3	3387
0.3-0.4	6418
0.4-0.5	10779
0.5-0.6	9963
0.6-0.7	8641
0.7-0.8	1165
0.8-0.85	210
0.85-0.9	71
0.9-0.95	50
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
0.9732	High Similarity	NPC263265
0.9732	High Similarity	NPC209364
0.9669	High Similarity	NPC305016
0.9667	High Similarity	NPC286722
0.9605	High Similarity	NPC470939
0.9603	High Similarity	NPC475295
0.9603	High Similarity	NPC473473
0.9603	High Similarity	NPC237155
0.96	High Similarity	NPC107646
0.9539	High Similarity	NPC25255
0.9536	High Similarity	NPC472283
0.9484	High Similarity	NPC473753
0.9484	High Similarity	NPC473766
0.9477	High Similarity	NPC193798
0.9477	High Similarity	NPC5079
0.9474	High Similarity	NPC473368
0.9416	High Similarity	NPC234660
0.9416	High Similarity	NPC51568
0.9412	High Similarity	NPC475381
0.9404	High Similarity	NPC469850
0.9359	High Similarity	NPC173516
0.9355	High Similarity	NPC476860
0.9355	High Similarity	NPC476856
0.9355	High Similarity	NPC476857
0.9355	High Similarity	NPC123088
0.9355	High Similarity	NPC476858
0.9346	High Similarity	NPC477403
0.9342	High Similarity	NPC126723
0.9299	High Similarity	NPC471397
0.9295	High Similarity	NPC23387
0.929	High Similarity	NPC469338
0.929	High Similarity	NPC292389
0.9286	High Similarity	NPC335761
0.9267	High Similarity	NPC196864
0.9267	High Similarity	NPC159927
0.9267	High Similarity	NPC46551
0.9267	High Similarity	NPC469335
0.9267	High Similarity	NPC477404
0.9252	High Similarity	NPC86935
0.9236	High Similarity	NPC472282
0.9236	High Similarity	NPC476853
0.9236	High Similarity	NPC476850
0.9236	High Similarity	NPC476861
0.9231	High Similarity	NPC469849
0.9231	High Similarity	NPC276551
0.9231	High Similarity	NPC470940
0.9226	High Similarity	NPC69028
0.9177	High Similarity	NPC160651
0.9172	High Similarity	NPC470875
0.9167	High Similarity	NPC469846
0.9167	High Similarity	NPC134254
0.9167	High Similarity	NPC39986
0.9167	High Similarity	NPC476197
0.9167	High Similarity	NPC302369
0.9167	High Similarity	NPC477405
0.9161	High Similarity	NPC477402
0.9161	High Similarity	NPC472653
0.9128	High Similarity	NPC262198
0.9119	High Similarity	NPC302392
0.9103	High Similarity	NPC117986
0.9103	High Similarity	NPC149896
0.9103	High Similarity	NPC96443
0.9103	High Similarity	NPC197596
0.9103	High Similarity	NPC263432
0.9103	High Similarity	NPC290400
0.9085	High Similarity	NPC178932
0.9038	High Similarity	NPC191828
0.9032	High Similarity	NPC167142
0.9032	High Similarity	NPC187149
0.9026	High Similarity	NPC469336
0.9026	High Similarity	NPC214541
0.9026	High Similarity	NPC44675
0.9026	High Similarity	NPC264943
0.902	High Similarity	NPC75906
0.902	High Similarity	NPC476201
0.8993	High Similarity	NPC142113
0.8981	High Similarity	NPC82851
0.8981	High Similarity	NPC18347
0.8981	High Similarity	NPC329938
0.8968	High Similarity	NPC469485
0.8954	High Similarity	NPC18135
0.894	High Similarity	NPC221809
0.8938	High Similarity	NPC271235
0.891	High Similarity	NPC173544
0.891	High Similarity	NPC299038
0.891	High Similarity	NPC249021
0.891	High Similarity	NPC261597
0.8903	High Similarity	NPC476262
0.8903	High Similarity	NPC281258
0.8896	High Similarity	NPC44577
0.8889	High Similarity	NPC476122
0.8875	High Similarity	NPC472774
0.8875	High Similarity	NPC472775
0.8875	High Similarity	NPC472651
0.8868	High Similarity	NPC271657
0.8861	High Similarity	NPC472771
0.8854	High Similarity	NPC475967
0.8844	High Similarity	NPC476943
0.8839	High Similarity	NPC57998
0.882	High Similarity	NPC472652
0.8816	High Similarity	NPC470941
0.8812	High Similarity	NPC475779
0.8805	High Similarity	NPC472773
0.8805	High Similarity	NPC224394
0.8805	High Similarity	NPC663
0.879	High Similarity	NPC45101
0.879	High Similarity	NPC472772
0.879	High Similarity	NPC36655
0.8776	High Similarity	NPC310830
0.8774	High Similarity	NPC469503
0.8773	High Similarity	NPC469848
0.8734	High Similarity	NPC307383
0.8718	High Similarity	NPC30222
0.8718	High Similarity	NPC282445
0.8716	High Similarity	NPC220094
0.8688	High Similarity	NPC419
0.8667	High Similarity	NPC167340
0.8667	High Similarity	NPC262386
0.8662	High Similarity	NPC35000
0.865	High Similarity	NPC470995
0.8642	High Similarity	NPC476224
0.8636	High Similarity	NPC19747
0.8634	High Similarity	NPC470182
0.8627	High Similarity	NPC346
0.8625	High Similarity	NPC200782
0.8625	High Similarity	NPC207978
0.8625	High Similarity	NPC471167
0.8625	High Similarity	NPC6326
0.8625	High Similarity	NPC471166
0.8614	High Similarity	NPC478177
0.8598	High Similarity	NPC159232
0.8598	High Similarity	NPC160818
0.8598	High Similarity	NPC169299
0.8589	High Similarity	NPC327922
0.858	High Similarity	NPC478178
0.8571	High Similarity	NPC471168
0.8571	High Similarity	NPC250228
0.8562	High Similarity	NPC287559
0.8553	High Similarity	NPC470741
0.8553	High Similarity	NPC223415
0.8544	High Similarity	NPC75310
0.8537	High Similarity	NPC82602
0.8535	High Similarity	NPC268905
0.8526	High Similarity	NPC156189
0.8519	High Similarity	NPC146991
0.8509	High Similarity	NPC472668
0.8509	High Similarity	NPC18986
0.8509	High Similarity	NPC211777
0.85	High Similarity	NPC474932
0.85	High Similarity	NPC262872
0.8497	Intermediate Similarity	NPC476944
0.8497	Intermediate Similarity	NPC137295
0.8494	Intermediate Similarity	NPC471437
0.8494	Intermediate Similarity	NPC236004
0.8491	Intermediate Similarity	NPC204663
0.8487	Intermediate Similarity	NPC473152
0.8471	Intermediate Similarity	NPC242068
0.8471	Intermediate Similarity	NPC247563
0.8471	Intermediate Similarity	NPC272590
0.8471	Intermediate Similarity	NPC116717
0.8466	Intermediate Similarity	NPC121995
0.8462	Intermediate Similarity	NPC195325
0.8462	Intermediate Similarity	NPC471001
0.8457	Intermediate Similarity	NPC198047
0.8457	Intermediate Similarity	NPC472669
0.8452	Intermediate Similarity	NPC255414
0.8447	Intermediate Similarity	NPC333139
0.8438	Intermediate Similarity	NPC195131
0.8431	Intermediate Similarity	NPC243577
0.8431	Intermediate Similarity	NPC267632
0.8428	Intermediate Similarity	NPC92979
0.8421	Intermediate Similarity	NPC20500
0.8418	Intermediate Similarity	NPC475777
0.8415	Intermediate Similarity	NPC478179
0.8408	Intermediate Similarity	NPC5180
0.8405	Intermediate Similarity	NPC56358
0.84	Intermediate Similarity	NPC42400
0.8395	Intermediate Similarity	NPC188649
0.8393	Intermediate Similarity	NPC472665
0.8387	Intermediate Similarity	NPC62799
0.8387	Intermediate Similarity	NPC471292
0.8385	Intermediate Similarity	NPC474611
0.8383	Intermediate Similarity	NPC94763
0.8377	Intermediate Similarity	NPC199044
0.8377	Intermediate Similarity	NPC251865
0.8377	Intermediate Similarity	NPC238843
0.8373	Intermediate Similarity	NPC285227
0.8366	Intermediate Similarity	NPC121158
0.8365	Intermediate Similarity	NPC114880
0.8364	Intermediate Similarity	NPC296558
0.8363	Intermediate Similarity	NPC105395
0.8355	Intermediate Similarity	NPC90296
0.8354	Intermediate Similarity	NPC291150
0.8354	Intermediate Similarity	NPC149945
0.8354	Intermediate Similarity	NPC97574
0.8354	Intermediate Similarity	NPC93172
0.8344	Intermediate Similarity	NPC472654
0.8344	Intermediate Similarity	NPC88841
0.8344	Intermediate Similarity	NPC329180
0.8344	Intermediate Similarity	NPC288602

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 NPC60973 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	362
0.1-0.2	1054
0.2-0.3	2231
0.3-0.4	2710
0.4-0.5	1796
0.5-0.6	742
0.6-0.7	242
0.7-0.8	13
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8447	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD8434	Phase 2
0.8086	Intermediate Similarity	NPD5760	Phase 2
0.8086	Intermediate Similarity	NPD5761	Phase 2
0.7803	Intermediate Similarity	NPD6764	Approved
0.7803	Intermediate Similarity	NPD6765	Approved
0.7627	Intermediate Similarity	NPD6785	Approved
0.7627	Intermediate Similarity	NPD6784	Approved
0.7484	Intermediate Similarity	NPD1471	Phase 3
0.747	Intermediate Similarity	NPD6599	Discontinued
0.744	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD5494	Approved
0.7384	Intermediate Similarity	NPD1247	Approved
0.7368	Intermediate Similarity	NPD919	Approved
0.731	Intermediate Similarity	NPD7075	Discontinued
0.7289	Intermediate Similarity	NPD920	Approved
0.7212	Intermediate Similarity	NPD6799	Approved
0.7193	Intermediate Similarity	NPD5402	Approved
0.7176	Intermediate Similarity	NPD6801	Discontinued
0.7169	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7819	Suspended
0.7134	Intermediate Similarity	NPD4628	Phase 3
0.7118	Intermediate Similarity	NPD7411	Suspended
0.7111	Intermediate Similarity	NPD6559	Discontinued
0.711	Intermediate Similarity	NPD3749	Approved
0.7101	Intermediate Similarity	NPD3226	Approved
0.7093	Intermediate Similarity	NPD3817	Phase 2
0.7083	Intermediate Similarity	NPD5403	Approved
0.7079	Intermediate Similarity	NPD3751	Discontinued
0.7066	Intermediate Similarity	NPD5401	Approved
0.7066	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8285	Discontinued
0.6994	Remote Similarity	NPD2796	Approved
0.6994	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD4107	Approved
0.6957	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD3882	Suspended
0.6951	Remote Similarity	NPD2346	Discontinued
0.695	Remote Similarity	NPD8404	Phase 2
0.6949	Remote Similarity	NPD3787	Discontinued
0.6946	Remote Similarity	NPD7236	Approved
0.6944	Remote Similarity	NPD5844	Phase 1
0.6933	Remote Similarity	NPD3748	Approved
0.6928	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD8150	Discontinued
0.691	Remote Similarity	NPD3926	Phase 2
0.6889	Remote Similarity	NPD7799	Discontinued
0.6879	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD2403	Approved
0.6872	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD1243	Approved
0.6864	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.686	Remote Similarity	NPD4380	Phase 2
0.6857	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD8313	Approved
0.6848	Remote Similarity	NPD8312	Approved
0.6839	Remote Similarity	NPD4482	Phase 3
0.6839	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD6273	Approved
0.6818	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD3887	Approved
0.6782	Remote Similarity	NPD1934	Approved
0.6778	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD6166	Phase 2
0.6772	Remote Similarity	NPD3266	Approved
0.6772	Remote Similarity	NPD3267	Approved
0.6765	Remote Similarity	NPD2533	Approved
0.6765	Remote Similarity	NPD2532	Approved
0.6765	Remote Similarity	NPD2534	Approved
0.676	Remote Similarity	NPD6808	Phase 2
0.675	Remote Similarity	NPD6832	Phase 2
0.6744	Remote Similarity	NPD7239	Suspended
0.674	Remote Similarity	NPD7473	Discontinued
0.6727	Remote Similarity	NPD2799	Discontinued
0.6726	Remote Similarity	NPD3750	Approved
0.6707	Remote Similarity	NPD1549	Phase 2
0.6705	Remote Similarity	NPD7458	Discontinued
0.6704	Remote Similarity	NPD6959	Discontinued
0.6704	Remote Similarity	NPD8127	Discontinued
0.6703	Remote Similarity	NPD3818	Discontinued
0.6687	Remote Similarity	NPD6099	Approved
0.6687	Remote Similarity	NPD6100	Approved
0.6687	Remote Similarity	NPD1551	Phase 2
0.6686	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD6797	Phase 2
0.6685	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD7435	Discontinued
0.6667	Remote Similarity	NPD2313	Discontinued
0.6667	Remote Similarity	NPD6232	Discontinued
0.6667	Remote Similarity	NPD3268	Approved
0.6667	Remote Similarity	NPD2800	Approved
0.6649	Remote Similarity	NPD7251	Discontinued
0.6647	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6355	Discontinued
0.6646	Remote Similarity	NPD1933	Approved
0.6634	Remote Similarity	NPD4111	Phase 1
0.6631	Remote Similarity	NPD8407	Phase 2
0.6629	Remote Similarity	NPD5890	Approved
0.6629	Remote Similarity	NPD5889	Approved
0.6627	Remote Similarity	NPD7033	Discontinued
0.6624	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD7808	Phase 3
0.6603	Remote Similarity	NPD17	Approved
0.6593	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD4307	Phase 2
0.6573	Remote Similarity	NPD7768	Phase 2
0.6571	Remote Similarity	NPD6585	Discontinued
0.657	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.657	Remote Similarity	NPD7907	Approved
0.6559	Remote Similarity	NPD8368	Discontinued
0.6559	Remote Similarity	NPD7685	Pre-registration
0.6554	Remote Similarity	NPD2801	Approved
0.6553	Remote Similarity	NPD4665	Approved
0.6548	Remote Similarity	NPD2353	Approved
0.6548	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD5763	Approved
0.6548	Remote Similarity	NPD3057	Approved
0.6548	Remote Similarity	NPD5762	Approved
0.6548	Remote Similarity	NPD2344	Approved
0.6541	Remote Similarity	NPD7074	Phase 3
0.6538	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD5980	Discovery
0.6532	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD6779	Approved
0.6531	Remote Similarity	NPD6781	Approved
0.6531	Remote Similarity	NPD6780	Approved
0.6531	Remote Similarity	NPD6782	Approved
0.6531	Remote Similarity	NPD6776	Approved
0.6531	Remote Similarity	NPD6777	Approved
0.6531	Remote Similarity	NPD6778	Approved
0.6524	Remote Similarity	NPD8032	Phase 2
0.6517	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD2897	Discontinued
0.6497	Remote Similarity	NPD37	Approved
0.6497	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD2935	Discontinued
0.6486	Remote Similarity	NPD7054	Approved
0.6485	Remote Similarity	NPD7874	Approved
0.6485	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.648	Remote Similarity	NPD4967	Phase 2
0.648	Remote Similarity	NPD7058	Phase 2
0.648	Remote Similarity	NPD4965	Approved
0.648	Remote Similarity	NPD4966	Approved
0.648	Remote Similarity	NPD7057	Phase 3
0.6478	Remote Similarity	NPD1608	Approved
0.6478	Remote Similarity	NPD3972	Approved
0.6465	Remote Similarity	NPD2972	Approved
0.6465	Remote Similarity	NPD3533	Approved
0.6463	Remote Similarity	NPD6798	Discontinued
0.6461	Remote Similarity	NPD1465	Phase 2
0.6452	Remote Similarity	NPD7472	Approved
0.6447	Remote Similarity	NPD4580	Approved
0.6446	Remote Similarity	NPD447	Suspended
0.6437	Remote Similarity	NPD1512	Approved
0.6433	Remote Similarity	NPD7003	Approved
0.6433	Remote Similarity	NPD5585	Approved
0.6432	Remote Similarity	NPD7696	Phase 3
0.6432	Remote Similarity	NPD2163	Approved
0.6432	Remote Similarity	NPD7698	Approved
0.6432	Remote Similarity	NPD7697	Approved
0.6429	Remote Similarity	NPD1510	Phase 2
0.6429	Remote Similarity	NPD4308	Phase 3
0.6424	Remote Similarity	NPD6233	Phase 2
0.642	Remote Similarity	NPD1019	Discontinued
0.642	Remote Similarity	NPD2798	Approved
0.6409	Remote Similarity	NPD6234	Discontinued
0.6406	Remote Similarity	NPD8435	Approved
0.6402	Remote Similarity	NPD2968	Approved
0.6402	Remote Similarity	NPD2971	Approved
0.6402	Remote Similarity	NPD7095	Approved
0.64	Remote Similarity	NPD8319	Approved
0.64	Remote Similarity	NPD8320	Phase 1
0.64	Remote Similarity	NPD7871	Phase 2
0.64	Remote Similarity	NPD7870	Phase 2
0.6395	Remote Similarity	NPD2354	Approved
0.6395	Remote Similarity	NPD2309	Approved
0.6393	Remote Similarity	NPD5710	Approved
0.6393	Remote Similarity	NPD7229	Phase 3
0.6393	Remote Similarity	NPD5711	Approved
0.6391	Remote Similarity	NPD2438	Suspended
0.6387	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD2975	Approved
0.6378	Remote Similarity	NPD2974	Approved
0.6378	Remote Similarity	NPD2973	Approved
0.6369	Remote Similarity	NPD7097	Phase 1

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