NPASS Compound

Structure

CID83744 OpenBabel06191715422D 34 37 0 0 1 0 0 0 0 0999 V2000 -2.4109 -1.1170 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4024 -2.4834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5349 -0.5240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0006 -1.9862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2430 -3.3276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6897 -0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6891 -0.9746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8446 -1.4632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6888 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 1.4633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3800 1.9504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8331 -2.2619 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3795 -0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5122 -2.0865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6900 -0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8452 0.4876 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5355 1.4628 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7233 -2.6589 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6906 1.9509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2243 1.4623 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2240 0.4866 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8454 -1.4627 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0442 -2.8344 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5352 0.4871 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0003 -0.9751 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8460 -2.4374 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8246 -3.6283 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6909 2.9620 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1002 1.9675 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0996 -0.0190 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1455 -3.8038 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8154 -2.5387 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 4 25 1 0 0 0 0 6 8 1 0 0 0 0 6 15 1 0 0 0 0 7 9 1 0 0 0 0 7 22 1 0 0 0 0 8 25 1 0 0 0 0 9 27 1 0 0 0 0 10 16 2 0 0 0 0 10 19 1 0 0 0 0 11 17 1 0 0 0 0 11 20 1 0 0 0 0 12 18 1 0 0 0 0 12 23 1 0 0 0 0 13 21 1 0 0 0 0 13 24 1 0 0 0 0 14 18 1 0 0 0 0 15 16 1 0 0 0 0 15 24 1 6 0 0 0 16 27 1 0 0 0 0 17 19 1 0 0 0 0 17 24 1 1 0 0 0 18 28 1 6 0 0 0 19 29 2 0 0 0 0 20 21 1 0 0 0 0 20 30 1 6 0 0 0 21 31 1 6 0 0 0 22 25 1 6 0 0 0 22 26 1 0 0 0 0 23 26 1 0 0 0 0 23 32 1 6 0 0 0 24 3 1 6 0 0 0 25 27 1 6 0 0 0 26 5 1 6 0 0 0 26 33 1 0 0 0 0 27 34 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	480.31
Volume:	497.581
LogP:	1.704
LogD:	0.526
LogS:	-3.313
# Rotatable Bonds:	5
TPSA:	138.45
# H-Bond Aceptor:	7
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.33
Synthetic Accessibility Score:	5.441
Fsp3:	0.889
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:	-5.131
MDCK Permeability:	4.857718522544019e-06
Pgp-inhibitor:	0.026
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.069
20% Bioavailability (F20%):	0.879
30% Bioavailability (F30%):	0.241

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.26
Plasma Protein Binding (PPB):	47.007102966308594%
Volume Distribution (VD):	1.415
Pgp-substrate:	29.407400131225586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.237
CYP2C19-inhibitor:	0.004
CYP2C19-substrate:	0.734
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.078
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.032
CYP3A4-inhibitor:	0.141
CYP3A4-substrate:	0.658

ADMET: Excretion

Clearance (CL):	2.746
Half-life (T1/2):	0.568

ADMET: Toxicity

hERG Blockers:	0.069
Human Hepatotoxicity (H-HT):	0.304
Drug-inuced Liver Injury (DILI):	0.066
AMES Toxicity:	0.26
Rat Oral Acute Toxicity:	0.641
Maximum Recommended Daily Dose:	0.968
Skin Sensitization:	0.431
Carcinogencity:	0.306
Eye Corrosion:	0.007
Eye Irritation:	0.038
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC83744

Natural Product ID:	NPC83744
*Common Name:**	Pterosterone
IUPAC Name:	(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(2R,3R,5S)-2,3,5-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
Synonyms:	Pterosterone
Standard InCHIKey:	UMMBJCYNGLCGEF-OAUIFJKNSA-N
Standard InCHI:	InChI=1S/C27H44O7/c1-14(2)18(28)12-23(32)26(5,33)22-7-9-27(34)16-10-19(29)17-11-20(30)21(31)13-24(17,3)15(16)6-8-25(22,27)4/h10,14-15,17-18,20-23,28,30-34H,6-9,11-13H2,1-5H3/t15-,17-,18-,20+,21-,22-,23+,24+,25+,26+,27+/m0/s1
SMILES:	CC(C)[C@H](C[C@H]([C@@](C)([C@H]1CC[C@]2(C3=CC(=O)[C@@H]4C[C@H]([C@H](C[C@]4(C)[C@H]3CC[C@]12C)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2087151
PubChem CID:	441836
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, alcohols and derivatives [CHEMONTID:0002194] Hydroxy bile acids, alcohols and derivatives

*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
NPO29535	Samadera indica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1039/C39770000295]
NPO7574	Garcinia pyrifera	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10978200]
NPO29535	Samadera indica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11429258]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	stem bark	Medicinal Plant Garden, College of Pharmacy, Ewha Womans University	2013-DEC	PMID[28787158]
NPO29535	Samadera indica	Species	Simaroubaceae	Eukaryota	n.a.	stem	n.a.	PMID[8945767]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9599262]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11785	Citrus hassaku	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8681	Artemisia lactiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13087	Pteridium aquilinum	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2551	Plumbagella micrantha	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8681	Artemisia lactiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11785	Citrus hassaku	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2551	Plumbagella micrantha	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13087	Pteridium aquilinum	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10861	Dipsacus asper	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12030	Streptomyces yokosukanensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO29535	Samadera indica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27659	Tanacetum parthenifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11214	Rivina humilis	Species	Petiveriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10861	Dipsacus asper	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11785	Citrus hassaku	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11032	Coutarea latifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12516	Phalaris canariensis	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2551	Plumbagella micrantha	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12858	Jacaranda chelonia	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8389	Ophryosporus floribundus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7574	Garcinia pyrifera	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO716	Greenwayodendron oliveri	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13121	Crepidiastrum sonchifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12971	Payena lucida	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5727	Hymenothrix wislizenii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11531	Duguetia calycina	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12411	Eriostemon spicatus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7313	Epirrhoe sperryi	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1776	Attalea excelsa	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8681	Artemisia lactiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13087	Pteridium aquilinum	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	4

Activity Type	# Activity
Individual Protein	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio	=	0.56	n.a.	PMID[454600]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	FICI	=	1.32	n.a.	PMID[454600]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	FICI	=	0.84	n.a.	PMID[454600]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	FICI	=	0.54	n.a.	PMID[454600]

☑ 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 NPC83744 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	205
0.1-0.2	1302
0.2-0.3	4353
0.3-0.4	8307
0.4-0.5	12800
0.5-0.6	6577
0.6-0.7	5992
0.7-0.8	2793
0.8-0.85	276
0.85-0.9	49
0.9-0.95	15
0.95-1	28

Similarity Score	Similarity Level	Natural Product ID
0.9899	High Similarity	NPC329417
0.9898	High Similarity	NPC319077
0.9898	High Similarity	NPC302607
0.9898	High Similarity	NPC296945
0.9898	High Similarity	NPC85829
0.9898	High Similarity	NPC171137
0.9898	High Similarity	NPC49958
0.9898	High Similarity	NPC97202
0.9898	High Similarity	NPC214264
0.9898	High Similarity	NPC202167
0.9898	High Similarity	NPC260268
0.9898	High Similarity	NPC150531
0.9898	High Similarity	NPC476027
0.9898	High Similarity	NPC152695
0.9898	High Similarity	NPC50692
0.9898	High Similarity	NPC48733
0.9798	High Similarity	NPC220229
0.9798	High Similarity	NPC475060
0.9798	High Similarity	NPC477916
0.9796	High Similarity	NPC204833
0.9796	High Similarity	NPC209502
0.97	High Similarity	NPC217201
0.9697	High Similarity	NPC149047
0.9604	High Similarity	NPC11710
0.9592	High Similarity	NPC477915
0.9515	High Similarity	NPC207251
0.9423	High Similarity	NPC108721
0.9423	High Similarity	NPC317210
0.9423	High Similarity	NPC73300
0.9388	High Similarity	NPC154072
0.9333	High Similarity	NPC326542
0.932	High Similarity	NPC76084
0.9314	High Similarity	NPC65941
0.9238	High Similarity	NPC250109
0.9238	High Similarity	NPC962
0.9223	High Similarity	NPC214644
0.9109	High Similarity	NPC191892
0.9065	High Similarity	NPC266728
0.9065	High Similarity	NPC49492
0.901	High Similarity	NPC473424
0.898	High Similarity	NPC271195
0.8932	High Similarity	NPC323834
0.8932	High Similarity	NPC257353
0.8878	High Similarity	NPC111015
0.8846	High Similarity	NPC165873
0.8818	High Similarity	NPC475041
0.88	High Similarity	NPC18509
0.875	High Similarity	NPC28532
0.875	High Similarity	NPC222688
0.875	High Similarity	NPC166607
0.8739	High Similarity	NPC109973
0.8738	High Similarity	NPC249187
0.8738	High Similarity	NPC311612
0.8738	High Similarity	NPC247957
0.8738	High Similarity	NPC117185
0.87	High Similarity	NPC249954
0.87	High Similarity	NPC49371
0.8687	High Similarity	NPC196227
0.8667	High Similarity	NPC185
0.8654	High Similarity	NPC72255
0.8654	High Similarity	NPC160843
0.8654	High Similarity	NPC75531
0.8654	High Similarity	NPC149124
0.8641	High Similarity	NPC87351
0.8636	High Similarity	NPC471854
0.8627	High Similarity	NPC144956
0.8614	High Similarity	NPC190554
0.86	High Similarity	NPC259286
0.86	High Similarity	NPC473170
0.86	High Similarity	NPC200702
0.86	High Similarity	NPC472932
0.8598	High Similarity	NPC235077
0.8586	High Similarity	NPC472930
0.8586	High Similarity	NPC472496
0.8586	High Similarity	NPC69454
0.8584	High Similarity	NPC269642
0.8558	High Similarity	NPC55872
0.8529	High Similarity	NPC103051
0.8515	High Similarity	NPC471463
0.85	High Similarity	NPC472977
0.85	High Similarity	NPC8993
0.85	High Similarity	NPC472976
0.8491	Intermediate Similarity	NPC58370
0.8491	Intermediate Similarity	NPC144459
0.8491	Intermediate Similarity	NPC43285
0.8485	Intermediate Similarity	NPC473998
0.8485	Intermediate Similarity	NPC63748
0.8485	Intermediate Similarity	NPC155304
0.8485	Intermediate Similarity	NPC116726
0.8485	Intermediate Similarity	NPC233116
0.8485	Intermediate Similarity	NPC472978
0.8485	Intermediate Similarity	NPC475806
0.8476	Intermediate Similarity	NPC28656
0.8469	Intermediate Similarity	NPC477943
0.8469	Intermediate Similarity	NPC309603
0.8469	Intermediate Similarity	NPC473999
0.8462	Intermediate Similarity	NPC22388
0.8462	Intermediate Similarity	NPC204450
0.8462	Intermediate Similarity	NPC195290
0.8447	Intermediate Similarity	NPC316964
0.8447	Intermediate Similarity	NPC15390
0.8447	Intermediate Similarity	NPC474720
0.8447	Intermediate Similarity	NPC218383
0.8447	Intermediate Similarity	NPC83709
0.8447	Intermediate Similarity	NPC110149
0.844	Intermediate Similarity	NPC280782
0.8431	Intermediate Similarity	NPC474938
0.8431	Intermediate Similarity	NPC474785
0.8416	Intermediate Similarity	NPC472824
0.8416	Intermediate Similarity	NPC472485
0.84	Intermediate Similarity	NPC109305
0.8396	Intermediate Similarity	NPC60681
0.8393	Intermediate Similarity	NPC257457
0.8393	Intermediate Similarity	NPC311554
0.8384	Intermediate Similarity	NPC48010
0.8384	Intermediate Similarity	NPC100313
0.8384	Intermediate Similarity	NPC134321
0.8384	Intermediate Similarity	NPC136801
0.8381	Intermediate Similarity	NPC236390
0.8381	Intermediate Similarity	NPC111323
0.8381	Intermediate Similarity	NPC26478
0.8378	Intermediate Similarity	NPC196931
0.8367	Intermediate Similarity	NPC470417
0.8367	Intermediate Similarity	NPC328539
0.8348	Intermediate Similarity	NPC473979
0.8333	Intermediate Similarity	NPC117133
0.8333	Intermediate Similarity	NPC470257
0.8319	Intermediate Similarity	NPC61520
0.8317	Intermediate Similarity	NPC280804
0.8317	Intermediate Similarity	NPC196485
0.8317	Intermediate Similarity	NPC245972
0.8317	Intermediate Similarity	NPC103527
0.8304	Intermediate Similarity	NPC218970
0.8302	Intermediate Similarity	NPC471293
0.8302	Intermediate Similarity	NPC477812
0.83	Intermediate Similarity	NPC185936
0.83	Intermediate Similarity	NPC168027
0.8291	Intermediate Similarity	NPC470882
0.8286	Intermediate Similarity	NPC136289
0.8286	Intermediate Similarity	NPC293753
0.8286	Intermediate Similarity	NPC185530
0.8286	Intermediate Similarity	NPC234892
0.8283	Intermediate Similarity	NPC32830
0.8283	Intermediate Similarity	NPC472973
0.8283	Intermediate Similarity	NPC31985
0.8283	Intermediate Similarity	NPC1015
0.8283	Intermediate Similarity	NPC186688
0.8283	Intermediate Similarity	NPC86319
0.8283	Intermediate Similarity	NPC275740
0.8283	Intermediate Similarity	NPC2983
0.8283	Intermediate Similarity	NPC77263
0.8283	Intermediate Similarity	NPC250592
0.8273	Intermediate Similarity	NPC472002
0.8269	Intermediate Similarity	NPC476274
0.8265	Intermediate Similarity	NPC90652
0.8252	Intermediate Similarity	NPC107243
0.8252	Intermediate Similarity	NPC320306
0.8252	Intermediate Similarity	NPC170978
0.8241	Intermediate Similarity	NPC472825
0.8241	Intermediate Similarity	NPC177064
0.8241	Intermediate Similarity	NPC472218
0.8241	Intermediate Similarity	NPC472219
0.8241	Intermediate Similarity	NPC472217
0.8235	Intermediate Similarity	NPC272617
0.8235	Intermediate Similarity	NPC53565
0.8235	Intermediate Similarity	NPC266899
0.8235	Intermediate Similarity	NPC180950
0.8235	Intermediate Similarity	NPC297199
0.823	Intermediate Similarity	NPC329736
0.822	Intermediate Similarity	NPC473888
0.8218	Intermediate Similarity	NPC470376
0.8218	Intermediate Similarity	NPC475255
0.8218	Intermediate Similarity	NPC470375
0.8218	Intermediate Similarity	NPC474736
0.8214	Intermediate Similarity	NPC148458
0.8208	Intermediate Similarity	NPC140723
0.8205	Intermediate Similarity	NPC293112
0.82	Intermediate Similarity	NPC320026
0.82	Intermediate Similarity	NPC128672
0.82	Intermediate Similarity	NPC171441
0.82	Intermediate Similarity	NPC473099
0.8198	Intermediate Similarity	NPC178981
0.8198	Intermediate Similarity	NPC52634
0.8198	Intermediate Similarity	NPC194100
0.819	Intermediate Similarity	NPC81530
0.819	Intermediate Similarity	NPC471401
0.819	Intermediate Similarity	NPC472924
0.819	Intermediate Similarity	NPC476897
0.819	Intermediate Similarity	NPC469789
0.819	Intermediate Similarity	NPC476240
0.819	Intermediate Similarity	NPC163372
0.819	Intermediate Similarity	NPC476223
0.819	Intermediate Similarity	NPC302537
0.819	Intermediate Similarity	NPC224720
0.8182	Intermediate Similarity	NPC133588
0.8182	Intermediate Similarity	NPC474668
0.8182	Intermediate Similarity	NPC143767
0.8182	Intermediate Similarity	NPC193360
0.8182	Intermediate Similarity	NPC131470
0.8174	Intermediate Similarity	NPC46570

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 NPC83744 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	174
0.1-0.2	1583
0.2-0.3	3975
0.3-0.4	2264
0.4-0.5	664
0.5-0.6	168
0.6-0.7	154
0.7-0.8	102
0.8-0.85	50
0.85-0.9	16
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8824	High Similarity	NPD5211	Phase 2
0.88	High Similarity	NPD4755	Approved
0.8654	High Similarity	NPD5141	Approved
0.8627	High Similarity	NPD4700	Approved
0.8627	High Similarity	NPD4696	Approved
0.8627	High Similarity	NPD5285	Approved
0.8627	High Similarity	NPD5286	Approved
0.8598	High Similarity	NPD4634	Approved
0.8469	Intermediate Similarity	NPD5328	Approved
0.8462	Intermediate Similarity	NPD5225	Approved
0.8462	Intermediate Similarity	NPD4633	Approved
0.8462	Intermediate Similarity	NPD5226	Approved
0.8462	Intermediate Similarity	NPD5224	Approved
0.84	Intermediate Similarity	NPD4202	Approved
0.8396	Intermediate Similarity	NPD6675	Approved
0.8396	Intermediate Similarity	NPD7128	Approved
0.8396	Intermediate Similarity	NPD5739	Approved
0.8396	Intermediate Similarity	NPD6402	Approved
0.8381	Intermediate Similarity	NPD5174	Approved
0.8381	Intermediate Similarity	NPD5175	Approved
0.8365	Intermediate Similarity	NPD5223	Approved
0.8333	Intermediate Similarity	NPD6373	Approved
0.8333	Intermediate Similarity	NPD6372	Approved
0.83	Intermediate Similarity	NPD6079	Approved
0.8241	Intermediate Similarity	NPD6881	Approved
0.8241	Intermediate Similarity	NPD7320	Approved
0.8241	Intermediate Similarity	NPD6899	Approved
0.8224	Intermediate Similarity	NPD4768	Approved
0.8224	Intermediate Similarity	NPD4767	Approved
0.8208	Intermediate Similarity	NPD4754	Approved
0.8198	Intermediate Similarity	NPD4632	Approved
0.8182	Intermediate Similarity	NPD6650	Approved
0.8182	Intermediate Similarity	NPD6649	Approved
0.8163	Intermediate Similarity	NPD3618	Phase 1
0.8155	Intermediate Similarity	NPD4697	Phase 3
0.8148	Intermediate Similarity	NPD5697	Approved
0.8148	Intermediate Similarity	NPD5701	Approved
0.8108	Intermediate Similarity	NPD8297	Approved
0.81	Intermediate Similarity	NPD4753	Phase 2
0.8091	Intermediate Similarity	NPD6883	Approved
0.8091	Intermediate Similarity	NPD7290	Approved
0.8091	Intermediate Similarity	NPD7102	Approved
0.8073	Intermediate Similarity	NPD5128	Approved
0.8073	Intermediate Similarity	NPD4730	Approved
0.8073	Intermediate Similarity	NPD4729	Approved
0.8018	Intermediate Similarity	NPD6847	Approved
0.8018	Intermediate Similarity	NPD6617	Approved
0.8018	Intermediate Similarity	NPD6869	Approved
0.8018	Intermediate Similarity	NPD8130	Phase 1
0.8	Intermediate Similarity	NPD6014	Approved
0.8	Intermediate Similarity	NPD6013	Approved
0.8	Intermediate Similarity	NPD6012	Approved
0.7981	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7981	Intermediate Similarity	NPD5221	Approved
0.7981	Intermediate Similarity	NPD5222	Approved
0.7959	Intermediate Similarity	NPD3666	Approved
0.7959	Intermediate Similarity	NPD3133	Approved
0.7959	Intermediate Similarity	NPD3665	Phase 1
0.7946	Intermediate Similarity	NPD6882	Approved
0.7931	Intermediate Similarity	NPD6319	Approved
0.7931	Intermediate Similarity	NPD6054	Approved
0.7931	Intermediate Similarity	NPD6059	Approved
0.7928	Intermediate Similarity	NPD5251	Approved
0.7928	Intermediate Similarity	NPD5248	Approved
0.7928	Intermediate Similarity	NPD5249	Phase 3
0.7928	Intermediate Similarity	NPD5250	Approved
0.7928	Intermediate Similarity	NPD5247	Approved
0.7909	Intermediate Similarity	NPD6011	Approved
0.7905	Intermediate Similarity	NPD5173	Approved
0.789	Intermediate Similarity	NPD6008	Approved
0.7885	Intermediate Similarity	NPD4629	Approved
0.7885	Intermediate Similarity	NPD5210	Approved
0.7857	Intermediate Similarity	NPD5216	Approved
0.7857	Intermediate Similarity	NPD5217	Approved
0.7857	Intermediate Similarity	NPD5215	Approved
0.7857	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD7115	Discovery
0.7826	Intermediate Similarity	NPD6009	Approved
0.7818	Intermediate Similarity	NPD6412	Phase 2
0.7797	Intermediate Similarity	NPD6370	Approved
0.7778	Intermediate Similarity	NPD4786	Approved
0.7768	Intermediate Similarity	NPD5169	Approved
0.7768	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7768	Intermediate Similarity	NPD5135	Approved
0.7757	Intermediate Similarity	NPD7640	Approved
0.7757	Intermediate Similarity	NPD7639	Approved
0.7755	Intermediate Similarity	NPD4221	Approved
0.7755	Intermediate Similarity	NPD4223	Phase 3
0.775	Intermediate Similarity	NPD7507	Approved
0.7736	Intermediate Similarity	NPD6083	Phase 2
0.7736	Intermediate Similarity	NPD6084	Phase 2
0.7712	Intermediate Similarity	NPD6016	Approved
0.7712	Intermediate Similarity	NPD6015	Approved
0.77	Intermediate Similarity	NPD5329	Approved
0.7699	Intermediate Similarity	NPD5127	Approved
0.7667	Intermediate Similarity	NPD7492	Approved
0.7664	Intermediate Similarity	NPD7638	Approved
0.7647	Intermediate Similarity	NPD5988	Approved
0.7624	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD6616	Approved
0.76	Intermediate Similarity	NPD4197	Approved
0.7586	Intermediate Similarity	NPD6274	Approved
0.7583	Intermediate Similarity	NPD7604	Phase 2
0.7576	Intermediate Similarity	NPD3667	Approved
0.7563	Intermediate Similarity	NPD5983	Phase 2
0.7561	Intermediate Similarity	NPD7319	Approved
0.7542	Intermediate Similarity	NPD7100	Approved
0.7542	Intermediate Similarity	NPD7101	Approved
0.7541	Intermediate Similarity	NPD7078	Approved
0.7541	Intermediate Similarity	NPD8293	Discontinued
0.7524	Intermediate Similarity	NPD6399	Phase 3
0.75	Intermediate Similarity	NPD5696	Approved
0.75	Intermediate Similarity	NPD5167	Approved
0.748	Intermediate Similarity	NPD7736	Approved
0.7459	Intermediate Similarity	NPD6336	Discontinued
0.7458	Intermediate Similarity	NPD6335	Approved
0.7451	Intermediate Similarity	NPD4689	Approved
0.7451	Intermediate Similarity	NPD4688	Approved
0.7451	Intermediate Similarity	NPD5205	Approved
0.7451	Intermediate Similarity	NPD4690	Approved
0.7451	Intermediate Similarity	NPD4138	Approved
0.7451	Intermediate Similarity	NPD4693	Phase 3
0.7429	Intermediate Similarity	NPD5284	Approved
0.7429	Intermediate Similarity	NPD7515	Phase 2
0.7429	Intermediate Similarity	NPD5281	Approved
0.7417	Intermediate Similarity	NPD6909	Approved
0.7417	Intermediate Similarity	NPD6908	Approved
0.7383	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD5695	Phase 3
0.7379	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7525	Registered
0.7373	Intermediate Similarity	NPD6317	Approved
0.7368	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD6033	Approved
0.7328	Intermediate Similarity	NPD6053	Discontinued
0.7327	Intermediate Similarity	NPD4788	Approved
0.7311	Intermediate Similarity	NPD6314	Approved
0.7311	Intermediate Similarity	NPD6313	Approved
0.7282	Intermediate Similarity	NPD7146	Approved
0.7282	Intermediate Similarity	NPD4694	Approved
0.7282	Intermediate Similarity	NPD6409	Approved
0.7282	Intermediate Similarity	NPD5280	Approved
0.7282	Intermediate Similarity	NPD5330	Approved
0.7282	Intermediate Similarity	NPD7521	Approved
0.7282	Intermediate Similarity	NPD7334	Approved
0.7282	Intermediate Similarity	NPD6684	Approved
0.7282	Intermediate Similarity	NPD5279	Phase 3
0.7282	Intermediate Similarity	NPD5690	Phase 2
0.7281	Intermediate Similarity	NPD5168	Approved
0.7273	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD4522	Approved
0.725	Intermediate Similarity	NPD7516	Approved
0.7248	Intermediate Similarity	NPD7902	Approved
0.7167	Intermediate Similarity	NPD7327	Approved
0.7167	Intermediate Similarity	NPD7328	Approved
0.7155	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7632	Discontinued
0.7143	Intermediate Similarity	NPD6903	Approved
0.7143	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD7748	Approved
0.713	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD4623	Approved
0.7115	Intermediate Similarity	NPD4519	Discontinued
0.71	Intermediate Similarity	NPD4195	Approved
0.7087	Intermediate Similarity	NPD3668	Phase 3
0.7075	Intermediate Similarity	NPD6904	Approved
0.7075	Intermediate Similarity	NPD6673	Approved
0.7075	Intermediate Similarity	NPD6080	Approved
0.7049	Intermediate Similarity	NPD8377	Approved
0.7049	Intermediate Similarity	NPD8294	Approved
0.7048	Intermediate Similarity	NPD7524	Approved
0.7027	Intermediate Similarity	NPD4225	Approved
0.7019	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD8328	Phase 3
0.7016	Intermediate Similarity	NPD6067	Discontinued
0.7	Intermediate Similarity	NPD6868	Approved
0.6992	Remote Similarity	NPD8033	Approved
0.6992	Remote Similarity	NPD7503	Approved
0.6992	Remote Similarity	NPD8296	Approved
0.6992	Remote Similarity	NPD8380	Approved
0.6992	Remote Similarity	NPD8379	Approved
0.6992	Remote Similarity	NPD8335	Approved
0.6992	Remote Similarity	NPD8378	Approved
0.6983	Remote Similarity	NPD6686	Approved
0.6981	Remote Similarity	NPD5737	Approved
0.6981	Remote Similarity	NPD6672	Approved
0.6972	Remote Similarity	NPD7900	Approved
0.6972	Remote Similarity	NPD6001	Approved
0.6972	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.697	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD8035	Phase 2
0.6944	Remote Similarity	NPD8034	Phase 2
0.6944	Remote Similarity	NPD5693	Phase 1
0.6923	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD6942	Approved
0.6869	Remote Similarity	NPD7339	Approved
0.6869	Remote Similarity	NPD3703	Phase 2
0.6864	Remote Similarity	NPD6371	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