NPASS Compound

Structure

NPC471586 OpenBabel07101718272D 51 55 0 0 1 0 0 0 0 0999 V2000 -7.1803 -3.3215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0741 -5.4205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0446 -3.6925 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6129 -0.2542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3143 1.4519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0694 -5.2834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8296 -1.7589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6933 0.8223 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1341 -1.9517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5385 -2.5547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5534 -2.7271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9116 -1.9603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9266 -2.1327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2847 -1.3659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6874 2.0463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9507 -3.5554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3925 -2.7257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7024 1.8739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5661 -0.0040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3911 -1.4370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9114 -0.3820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4211 -1.6801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9861 0.3402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6170 -0.0585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9114 1.1301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5148 1.3078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9095 2.2959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5135 -4.5222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6279 -0.4266 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3292 1.2795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5112 -4.4537 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8320 -1.8275 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8297 0.5582 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5661 0.7520 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6655 -0.4754 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2738 -0.9977 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2566 0.7520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0605 2.6407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9700 0.2431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9285 1.0552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6655 1.2234 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2566 -0.0040 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2745 -0.9616 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2677 1.5290 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0755 2.4683 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.5663 3.2351 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4321 1.2520 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4037 3.5800 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8881 2.1983 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6418 0.7668 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 28 1 0 0 0 0 3 28 1 0 0 0 0 5 30 1 0 0 0 0 9 43 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 29 1 0 0 0 0 15 18 2 0 0 0 0 15 30 1 0 0 0 0 16 17 2 0 0 0 0 16 31 1 0 0 0 0 17 32 1 0 0 0 0 18 38 1 0 0 0 0 19 21 1 0 0 0 0 19 34 1 0 0 0 0 20 22 1 0 0 0 0 20 35 1 0 0 0 0 21 42 1 0 0 0 0 22 43 1 0 0 0 0 23 29 1 0 0 0 0 23 30 2 0 0 0 0 24 33 1 0 0 0 0 24 36 1 0 0 0 0 25 34 1 0 0 0 0 25 37 2 0 0 0 0 26 33 1 0 0 0 0 26 44 1 0 0 0 0 27 47 2 0 0 0 0 28 31 1 0 0 0 0 29 4 1 6 0 0 0 31 6 1 1 0 0 0 32 7 1 1 0 0 0 32 36 1 0 0 0 0 33 45 1 6 0 0 0 34 48 1 1 0 0 0 35 39 1 0 0 0 0 35 42 1 1 0 0 0 36 43 1 1 0 0 0 37 41 1 0 0 0 0 37 42 1 0 0 0 0 38 46 2 3 0 0 0 38 49 1 0 0 0 0 39 40 2 0 0 0 0 39 45 1 0 0 0 0 40 41 1 0 0 0 0 40 44 1 0 0 0 0 41 50 2 0 0 0 0 42 8 1 1 0 0 0 43 45 1 1 0 0 0 44 27 1 6 0 0 0 44 46 1 0 0 0 0 45 51 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	701.5
Volume:	777.95
LogP:	6.936
LogD:	5.41
LogS:	-3.239
# Rotatable Bonds:	15
TPSA:	100.54
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.081
Synthetic Accessibility Score:	5.998
Fsp3:	0.733
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.19
MDCK Permeability:	2.1521540475077927e-05
Pgp-inhibitor:	0.952
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.111
20% Bioavailability (F20%):	0.97
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.357
Plasma Protein Binding (PPB):	81.28079986572266%
Volume Distribution (VD):	1.551
Pgp-substrate:	1.6678071022033691%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.589
CYP2C19-inhibitor:	0.314
CYP2C19-substrate:	0.865
CYP2C9-inhibitor:	0.507
CYP2C9-substrate:	0.05
CYP2D6-inhibitor:	0.136
CYP2D6-substrate:	0.042
CYP3A4-inhibitor:	0.973
CYP3A4-substrate:	0.931

ADMET: Excretion

Clearance (CL):	2.05
Half-life (T1/2):	0.144

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.706
Drug-inuced Liver Injury (DILI):	0.18
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.985
Maximum Recommended Daily Dose:	0.91
Skin Sensitization:	0.923
Carcinogencity:	0.012
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.833

Download Data

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

Natural Product: NPC471586

Natural Product ID:	NPC471586
*Common Name:**	Gymnasterone A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	TVFMBZOZGJABCW-DNZREWLKSA-N
Standard InCHI:	InChI=1S/C45H67NO5/c1-10-11-12-13-14-29(4)23-30(5)15-18-38(49)46-44(27-47)26-33-24-36(32(7)17-16-31(6)28(2)3)43(9)22-20-35-39(45(33,43)51)40(44)41(50)37-25-34(48)19-21-42(35,37)8/h15-18,23,25,27-29,31-36,48,51H,10-14,19-22,24,26H2,1-9H3,(H,46,49)/b17-16+,18-15+,30-23+/t29-,31-,32+,33+,34-,35-,36+,42+,43+,44-,45-/m0/s1
SMILES:	CCCCCCC(C)C=C(C)C=CC(=O)NC1(CC2CC(C3(C2(C4=C1C(=O)C5=CC(CCC5(C4CC3)C)O)O)C)C(C)C=CC(C)C(C)C)C=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL266060
PubChem CID:	44445555
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids

*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
NPO33119	gymnascella dankaliensis	Species	Gymnoascaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17067147]
NPO33119	gymnascella dankaliensis	Species	Gymnoascaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17988094]
NPO33119	gymnascella dankaliensis	Species	Gymnoascaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18284207]
NPO33119	gymnascella dankaliensis	Species	Gymnoascaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25600409]

☑ 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
GI50	39

Activity Type	# Activity
Cell Line	34
NON-MOLECULAR	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	=	67608.3	nM	PMID[522331]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	<	100000.0	nM	PMID[522331]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	58884.37	nM	PMID[522331]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	<	100000.0	nM	PMID[522331]
NPT380	Cell Line	U-251	Homo sapiens	GI50	<	100000.0	nM	PMID[522331]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	=	21877.62	nM	PMID[522331]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	=	87096.36	nM	PMID[522331]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	=	50118.72	nM	PMID[522331]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	<	100000.0	nM	PMID[522331]
NPT578	Cell Line	SNB-78	Homo sapiens	GI50	=	12882.5	nM	PMID[522331]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	<	100000.0	nM	PMID[522331]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	<	100000.0	nM	PMID[522331]
NPT386	Cell Line	KM12	Homo sapiens	GI50	<	100000.0	nM	PMID[522331]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	<	100000.0	nM	PMID[522331]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	<	100000.0	nM	PMID[522331]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	<	100000.0	nM	PMID[522331]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	=	28183.83	nM	PMID[522331]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	=	28183.83	nM	PMID[522331]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	<	100000.0	nM	PMID[522331]
NPT81	Cell Line	A549	Homo sapiens	GI50	<	100000.0	nM	PMID[522331]
NPT572	Cell Line	DMS-273	Homo sapiens	GI50	<	100000.0	nM	PMID[522331]
NPT576	Cell Line	DMS-114	Homo sapiens	GI50	=	72443.6	nM	PMID[522331]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	<	100000.0	nM	PMID[522331]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	=	39810.72	nM	PMID[522331]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	<	100000.0	nM	PMID[522331]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	<	100000.0	nM	PMID[522331]
NPT2722	Cell Line	St-4	Homo sapiens	GI50	<	100000.0	nM	PMID[522331]
NPT2398	Cell Line	MKN-7	Homo sapiens	GI50	=	53703.18	nM	PMID[522331]
NPT1179	Cell Line	MKN-28	Homo sapiens	GI50	<	38018.94	nM	PMID[522331]
NPT1097	Cell Line	MKN-45	Homo sapiens	GI50	<	100000.0	nM	PMID[522331]
NPT2723	Cell Line	MKN-74	Homo sapiens	GI50	=	28183.83	nM	PMID[522331]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	<	100000.0	nM	PMID[522331]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	<	100000.0	nM	PMID[522331]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	<	100000.0	nM	PMID[522331]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	<	100000.0	nM	PMID[522331]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	<	91201.08	nM	PMID[522331]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	12882.5	nM	PMID[522331]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	<	75857.76	nM	PMID[522331]

☑ 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 NPC471586 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	129
0.1-0.2	784
0.2-0.3	3062
0.3-0.4	17537
0.4-0.5	12650
0.5-0.6	7083
0.6-0.7	1404
0.7-0.8	47
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7581	Intermediate Similarity	NPC328052
0.7458	Intermediate Similarity	NPC249954
0.7438	Intermediate Similarity	NPC473424
0.7373	Intermediate Similarity	NPC259286
0.7236	Intermediate Similarity	NPC311612
0.7236	Intermediate Similarity	NPC111323
0.7227	Intermediate Similarity	NPC472932
0.7203	Intermediate Similarity	NPC472930
0.7203	Intermediate Similarity	NPC250575
0.7203	Intermediate Similarity	NPC69454
0.719	Intermediate Similarity	NPC235464
0.719	Intermediate Similarity	NPC166745
0.719	Intermediate Similarity	NPC197386
0.7165	Intermediate Similarity	NPC476290
0.7154	Intermediate Similarity	NPC87351
0.7154	Intermediate Similarity	NPC204450
0.7154	Intermediate Similarity	NPC477915
0.7154	Intermediate Similarity	NPC195290
0.7143	Intermediate Similarity	NPC299100
0.7143	Intermediate Similarity	NPC177064
0.7132	Intermediate Similarity	NPC73050
0.7119	Intermediate Similarity	NPC63748
0.7107	Intermediate Similarity	NPC161147
0.7097	Intermediate Similarity	NPC236390
0.7094	Intermediate Similarity	NPC123912
0.7087	Intermediate Similarity	NPC214644
0.7083	Intermediate Similarity	NPC180950
0.7073	Intermediate Similarity	NPC99411
0.7063	Intermediate Similarity	NPC185
0.7059	Intermediate Similarity	NPC472942
0.7054	Intermediate Similarity	NPC476269
0.7049	Intermediate Similarity	NPC471717
0.7049	Intermediate Similarity	NPC103051
0.704	Intermediate Similarity	NPC204833
0.704	Intermediate Similarity	NPC209502
0.7034	Intermediate Similarity	NPC69622
0.7034	Intermediate Similarity	NPC183283
0.7034	Intermediate Similarity	NPC191684
0.7008	Intermediate Similarity	NPC65941
0.7	Intermediate Similarity	NPC8993
0.6992	Remote Similarity	NPC51370
0.6992	Remote Similarity	NPC154072
0.6992	Remote Similarity	NPC144956
0.6992	Remote Similarity	NPC287833
0.6984	Remote Similarity	NPC85829
0.6984	Remote Similarity	NPC49958
0.6984	Remote Similarity	NPC48733
0.6984	Remote Similarity	NPC296945
0.6984	Remote Similarity	NPC319077
0.6984	Remote Similarity	NPC171137
0.6984	Remote Similarity	NPC149047
0.6984	Remote Similarity	NPC476027
0.6984	Remote Similarity	NPC152695
0.6984	Remote Similarity	NPC150531
0.6984	Remote Similarity	NPC50692
0.6984	Remote Similarity	NPC97202
0.6984	Remote Similarity	NPC60681
0.6984	Remote Similarity	NPC214264
0.6984	Remote Similarity	NPC202167
0.6984	Remote Similarity	NPC260268
0.6984	Remote Similarity	NPC302607
0.6975	Remote Similarity	NPC475806
0.6949	Remote Similarity	NPC275740
0.6949	Remote Similarity	NPC2983
0.6949	Remote Similarity	NPC86319
0.6942	Remote Similarity	NPC173875
0.6942	Remote Similarity	NPC174948
0.6942	Remote Similarity	NPC469995
0.6942	Remote Similarity	NPC318282
0.6935	Remote Similarity	NPC472924
0.6935	Remote Similarity	NPC163372
0.6935	Remote Similarity	NPC302537
0.6929	Remote Similarity	NPC477916
0.6929	Remote Similarity	NPC475060
0.6929	Remote Similarity	NPC83744
0.6929	Remote Similarity	NPC220229
0.6923	Remote Similarity	NPC287079
0.6911	Remote Similarity	NPC10364
0.6911	Remote Similarity	NPC48647
0.6911	Remote Similarity	NPC186810
0.6899	Remote Similarity	NPC197428
0.6891	Remote Similarity	NPC320026
0.6891	Remote Similarity	NPC129913
0.6885	Remote Similarity	NPC328371
0.6885	Remote Similarity	NPC301534
0.6885	Remote Similarity	NPC471463
0.6885	Remote Similarity	NPC472941
0.6885	Remote Similarity	NPC250757
0.6885	Remote Similarity	NPC192428
0.6885	Remote Similarity	NPC456
0.6885	Remote Similarity	NPC155676
0.688	Remote Similarity	NPC119601
0.688	Remote Similarity	NPC56498
0.688	Remote Similarity	NPC308726
0.6875	Remote Similarity	NPC329417
0.6875	Remote Similarity	NPC295244
0.6875	Remote Similarity	NPC217201
0.6864	Remote Similarity	NPC143767
0.6864	Remote Similarity	NPC131470
0.686	Remote Similarity	NPC474690
0.686	Remote Similarity	NPC469406
0.686	Remote Similarity	NPC292793
0.6855	Remote Similarity	NPC474720
0.6855	Remote Similarity	NPC205899
0.685	Remote Similarity	NPC257353
0.6842	Remote Similarity	NPC470275
0.6842	Remote Similarity	NPC476190
0.6842	Remote Similarity	NPC471854
0.6833	Remote Similarity	NPC19114
0.6833	Remote Similarity	NPC272746
0.6833	Remote Similarity	NPC472978
0.6833	Remote Similarity	NPC233116
0.6833	Remote Similarity	NPC473998
0.6833	Remote Similarity	NPC204341
0.6829	Remote Similarity	NPC18319
0.6829	Remote Similarity	NPC474938
0.6829	Remote Similarity	NPC18509
0.6829	Remote Similarity	NPC474785
0.6825	Remote Similarity	NPC55872
0.6825	Remote Similarity	NPC26478
0.6825	Remote Similarity	NPC474563
0.6822	Remote Similarity	NPC11710
0.6815	Remote Similarity	NPC184555
0.6807	Remote Similarity	NPC309603
0.6807	Remote Similarity	NPC472983
0.6807	Remote Similarity	NPC473999
0.6807	Remote Similarity	NPC472973
0.6807	Remote Similarity	NPC477943
0.6803	Remote Similarity	NPC127063
0.6803	Remote Similarity	NPC271195
0.68	Remote Similarity	NPC224720
0.68	Remote Similarity	NPC282524
0.68	Remote Similarity	NPC476223
0.68	Remote Similarity	NPC476240
0.6797	Remote Similarity	NPC475294
0.6797	Remote Similarity	NPC472925
0.6794	Remote Similarity	NPC475524
0.6794	Remote Similarity	NPC100267
0.6794	Remote Similarity	NPC221144
0.6794	Remote Similarity	NPC475970
0.678	Remote Similarity	NPC475772
0.678	Remote Similarity	NPC136548
0.6777	Remote Similarity	NPC134826
0.6777	Remote Similarity	NPC214697
0.6777	Remote Similarity	NPC474736
0.6774	Remote Similarity	NPC147954
0.6772	Remote Similarity	NPC472868
0.6772	Remote Similarity	NPC28656
0.6769	Remote Similarity	NPC37116
0.6769	Remote Similarity	NPC16270
0.6769	Remote Similarity	NPC76084
0.6767	Remote Similarity	NPC190286
0.6767	Remote Similarity	NPC148458
0.6765	Remote Similarity	NPC46570
0.6752	Remote Similarity	NPC474083
0.675	Remote Similarity	NPC48010
0.6748	Remote Similarity	NPC469545
0.6748	Remote Similarity	NPC117133
0.6748	Remote Similarity	NPC243525
0.6748	Remote Similarity	NPC5532
0.6748	Remote Similarity	NPC61369
0.6748	Remote Similarity	NPC247220
0.6748	Remote Similarity	NPC95565
0.6748	Remote Similarity	NPC40765
0.6746	Remote Similarity	NPC185530
0.6746	Remote Similarity	NPC293753
0.6746	Remote Similarity	NPC234892
0.6744	Remote Similarity	NPC307903
0.6744	Remote Similarity	NPC140251
0.6741	Remote Similarity	NPC305260
0.6741	Remote Similarity	NPC270850
0.6723	Remote Similarity	NPC328539
0.6723	Remote Similarity	NPC471722
0.6721	Remote Similarity	NPC473162
0.6721	Remote Similarity	NPC472977
0.6721	Remote Similarity	NPC472976
0.6721	Remote Similarity	NPC473172
0.6721	Remote Similarity	NPC111015
0.6721	Remote Similarity	NPC184870
0.6721	Remote Similarity	NPC166906
0.672	Remote Similarity	NPC266955
0.672	Remote Similarity	NPC476274
0.6719	Remote Similarity	NPC323834
0.6716	Remote Similarity	NPC474518
0.6715	Remote Similarity	NPC107493
0.6695	Remote Similarity	NPC94755
0.6695	Remote Similarity	NPC72133
0.6695	Remote Similarity	NPC469994
0.6694	Remote Similarity	NPC291634
0.6694	Remote Similarity	NPC212948
0.6694	Remote Similarity	NPC185936
0.6694	Remote Similarity	NPC168027
0.6694	Remote Similarity	NPC126815
0.6694	Remote Similarity	NPC190554
0.6694	Remote Similarity	NPC107243
0.6694	Remote Similarity	NPC320306
0.6694	Remote Similarity	NPC107690
0.6694	Remote Similarity	NPC106557
0.6694	Remote Similarity	NPC141401
0.6693	Remote Similarity	NPC98765

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 NPC471586 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	121
0.1-0.2	567
0.2-0.3	2838
0.3-0.4	4220
0.4-0.5	984
0.5-0.6	280
0.6-0.7	135
0.7-0.8	5
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
0.7273	Intermediate Similarity	NPD6404	Discontinued
0.7154	Intermediate Similarity	NPD5211	Phase 2
0.704	Intermediate Similarity	NPD5141	Approved
0.6992	Remote Similarity	NPD5285	Approved
0.6992	Remote Similarity	NPD5286	Approved
0.6992	Remote Similarity	NPD4696	Approved
0.6975	Remote Similarity	NPD6079	Approved
0.6935	Remote Similarity	NPD5223	Approved
0.6885	Remote Similarity	NPD4697	Phase 3
0.688	Remote Similarity	NPD5224	Approved
0.688	Remote Similarity	NPD5225	Approved
0.688	Remote Similarity	NPD5226	Approved
0.688	Remote Similarity	NPD4633	Approved
0.6875	Remote Similarity	NPD6334	Approved
0.6875	Remote Similarity	NPD6333	Approved
0.6829	Remote Similarity	NPD4755	Approved
0.6825	Remote Similarity	NPD5175	Approved
0.6825	Remote Similarity	NPD5174	Approved
0.6807	Remote Similarity	NPD5328	Approved
0.6748	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD5221	Approved
0.6748	Remote Similarity	NPD5222	Approved
0.6744	Remote Similarity	NPD6899	Approved
0.6744	Remote Similarity	NPD6881	Approved
0.672	Remote Similarity	NPD4700	Approved
0.6718	Remote Similarity	NPD6650	Approved
0.6718	Remote Similarity	NPD8130	Phase 1
0.6718	Remote Similarity	NPD6649	Approved
0.6694	Remote Similarity	NPD5173	Approved
0.6667	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD8297	Approved
0.6641	Remote Similarity	NPD7102	Approved
0.6641	Remote Similarity	NPD6883	Approved
0.6641	Remote Similarity	NPD7290	Approved
0.6639	Remote Similarity	NPD4202	Approved
0.6615	Remote Similarity	NPD4729	Approved
0.6615	Remote Similarity	NPD4730	Approved
0.6615	Remote Similarity	NPD6011	Approved
0.6612	Remote Similarity	NPD4096	Approved
0.6591	Remote Similarity	NPD6847	Approved
0.6591	Remote Similarity	NPD6869	Approved
0.6591	Remote Similarity	NPD6617	Approved
0.6589	Remote Similarity	NPD6675	Approved
0.6589	Remote Similarity	NPD7128	Approved
0.6589	Remote Similarity	NPD6402	Approved
0.6589	Remote Similarity	NPD5739	Approved
0.6565	Remote Similarity	NPD6012	Approved
0.6565	Remote Similarity	NPD6373	Approved
0.6565	Remote Similarity	NPD6013	Approved
0.6565	Remote Similarity	NPD6372	Approved
0.6565	Remote Similarity	NPD6014	Approved
0.6562	Remote Similarity	NPD4754	Approved
0.6557	Remote Similarity	NPD5284	Approved
0.6557	Remote Similarity	NPD5281	Approved
0.6555	Remote Similarity	NPD5280	Approved
0.6555	Remote Similarity	NPD5279	Phase 3
0.6555	Remote Similarity	NPD5690	Phase 2
0.6555	Remote Similarity	NPD4694	Approved
0.6541	Remote Similarity	NPD6882	Approved
0.6532	Remote Similarity	NPD4629	Approved
0.6532	Remote Similarity	NPD5210	Approved
0.6529	Remote Similarity	NPD4753	Phase 2
0.6525	Remote Similarity	NPD3665	Phase 1
0.6525	Remote Similarity	NPD3666	Approved
0.6525	Remote Similarity	NPD3133	Approved
0.6522	Remote Similarity	NPD6909	Approved
0.6522	Remote Similarity	NPD6908	Approved
0.6515	Remote Similarity	NPD5248	Approved
0.6515	Remote Similarity	NPD5135	Approved
0.6515	Remote Similarity	NPD5249	Phase 3
0.6515	Remote Similarity	NPD5247	Approved
0.6515	Remote Similarity	NPD5250	Approved
0.6515	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD4634	Approved
0.6515	Remote Similarity	NPD5251	Approved
0.6515	Remote Similarity	NPD5169	Approved
0.6489	Remote Similarity	NPD5128	Approved
0.6489	Remote Similarity	NPD7320	Approved
0.6466	Remote Similarity	NPD5217	Approved
0.6466	Remote Similarity	NPD5215	Approved
0.6466	Remote Similarity	NPD5127	Approved
0.6466	Remote Similarity	NPD5216	Approved
0.6462	Remote Similarity	NPD4768	Approved
0.6462	Remote Similarity	NPD4767	Approved
0.6429	Remote Similarity	NPD7604	Phase 2
0.6417	Remote Similarity	NPD3618	Phase 1
0.6412	Remote Similarity	NPD5701	Approved
0.637	Remote Similarity	NPD4632	Approved
0.6356	Remote Similarity	NPD4223	Phase 3
0.6356	Remote Similarity	NPD4221	Approved
0.635	Remote Similarity	NPD7115	Discovery
0.6343	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD5329	Approved
0.6324	Remote Similarity	NPD5167	Approved
0.632	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD4518	Approved
0.6304	Remote Similarity	NPD6335	Approved
0.6299	Remote Similarity	NPD6083	Phase 2
0.6299	Remote Similarity	NPD6084	Phase 2
0.6281	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD6914	Discontinued
0.627	Remote Similarity	NPD5695	Phase 3
0.6269	Remote Similarity	NPD6420	Discontinued
0.6259	Remote Similarity	NPD7101	Approved
0.6259	Remote Similarity	NPD7100	Approved
0.625	Remote Similarity	NPD4786	Approved
0.625	Remote Similarity	NPD4197	Approved
0.6241	Remote Similarity	NPD5168	Approved
0.6232	Remote Similarity	NPD6009	Approved
0.6232	Remote Similarity	NPD6317	Approved
0.6214	Remote Similarity	NPD6054	Approved
0.6187	Remote Similarity	NPD6314	Approved
0.6187	Remote Similarity	NPD6313	Approved
0.6167	Remote Similarity	NPD4788	Approved
0.616	Remote Similarity	NPD5694	Approved
0.616	Remote Similarity	NPD6050	Approved
0.616	Remote Similarity	NPD7515	Phase 2
0.6159	Remote Similarity	NPD6274	Approved
0.6148	Remote Similarity	NPD5205	Approved
0.6148	Remote Similarity	NPD4690	Approved
0.6148	Remote Similarity	NPD4689	Approved
0.6148	Remote Similarity	NPD4693	Phase 3
0.6148	Remote Similarity	NPD4138	Approved
0.6148	Remote Similarity	NPD4688	Approved
0.6138	Remote Similarity	NPD7736	Approved
0.6127	Remote Similarity	NPD6370	Approved
0.6122	Remote Similarity	NPD7260	Phase 2
0.6111	Remote Similarity	NPD7507	Approved
0.6111	Remote Similarity	NPD5133	Approved
0.6103	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD4195	Approved
0.6099	Remote Similarity	NPD6319	Approved
0.6083	Remote Similarity	NPD3667	Approved
0.608	Remote Similarity	NPD5207	Approved
0.608	Remote Similarity	NPD5692	Phase 3
0.6077	Remote Similarity	NPD7639	Approved
0.6077	Remote Similarity	NPD7640	Approved
0.6063	Remote Similarity	NPD7748	Approved
0.6063	Remote Similarity	NPD5771	Approved
0.6056	Remote Similarity	NPD6015	Approved
0.6056	Remote Similarity	NPD5983	Phase 2
0.6056	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD6016	Approved
0.6048	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD7902	Approved
0.6043	Remote Similarity	NPD6868	Approved
0.6042	Remote Similarity	NPD7492	Approved
0.6033	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD7146	Approved
0.6016	Remote Similarity	NPD7334	Approved
0.6016	Remote Similarity	NPD7521	Approved
0.6016	Remote Similarity	NPD6409	Approved
0.6016	Remote Similarity	NPD4623	Approved
0.6016	Remote Similarity	NPD4519	Discontinued
0.6016	Remote Similarity	NPD6684	Approved
0.6016	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD5330	Approved
0.6014	Remote Similarity	NPD5988	Approved
0.6	Remote Similarity	NPD7638	Approved
0.6	Remote Similarity	NPD5696	Approved
0.6	Remote Similarity	NPD6336	Discontinued
0.6	Remote Similarity	NPD6616	Approved
0.5986	Remote Similarity	NPD6059	Approved
0.5986	Remote Similarity	NPD7319	Approved
0.5984	Remote Similarity	NPD6399	Phase 3
0.597	Remote Similarity	NPD6008	Approved
0.5959	Remote Similarity	NPD7078	Approved
0.5952	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.5944	Remote Similarity	NPD7739	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD6412	Phase 2
0.592	Remote Similarity	NPD6903	Approved
0.5906	Remote Similarity	NPD7084	Phase 3
0.5906	Remote Similarity	NPD6411	Approved
0.5896	Remote Similarity	NPD7812	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD7500	Approved
0.5873	Remote Similarity	NPD6904	Approved
0.5873	Remote Similarity	NPD6080	Approved
0.5873	Remote Similarity	NPD6673	Approved
0.5868	Remote Similarity	NPD4692	Approved
0.5868	Remote Similarity	NPD4139	Approved
0.5865	Remote Similarity	NPD5091	Approved
0.5859	Remote Similarity	NPD5778	Approved
0.5859	Remote Similarity	NPD5779	Approved
0.5852	Remote Similarity	NPD7333	Discontinued
0.585	Remote Similarity	NPD8293	Discontinued
0.5846	Remote Similarity	NPD7614	Phase 1
0.584	Remote Similarity	NPD3573	Approved
0.5833	Remote Similarity	NPD7503	Approved
0.5827	Remote Similarity	NPD6053	Discontinued
0.5827	Remote Similarity	NPD5785	Approved
0.5814	Remote Similarity	NPD7900	Approved
0.5814	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD5733	Approved
0.5812	Remote Similarity	NPD4687	Approved
0.5811	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD1696	Phase 3
0.5806	Remote Similarity	NPD5363	Approved
0.5794	Remote Similarity	NPD5737	Approved
0.5794	Remote Similarity	NPD6672	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