NPASS Compound

Structure

CID69273 OpenBabel06191715402D 56 62 0 0 1 0 0 0 0 0999 V2000 9.2735 -4.6348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6748 -3.6168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2016 -2.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6500 -0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1143 -1.2181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4015 -1.9612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4041 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6803 -3.7213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 6.3986 -3.0827 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 9.0925 -2.9123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 8.5925 -1.3734 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.4641 4.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 6.8053 -2.1691 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 7.7835 -1.9612 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8986 -3.9487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5925 -0.3734 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 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 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0925 -2.9123 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 38 1 0 0 0 0 5 38 1 0 0 0 0 6 39 1 0 0 0 0 7 40 1 0 0 0 0 8 41 1 0 0 0 0 9 42 1 0 0 0 0 10 12 1 0 0 0 0 10 20 2 0 0 0 0 11 13 1 0 0 0 0 11 21 1 0 0 0 0 12 25 1 0 0 0 0 13 28 1 0 0 0 0 14 23 2 0 0 0 0 14 26 1 0 0 0 0 15 22 1 0 0 0 0 15 39 1 0 0 0 0 16 27 1 0 0 0 0 16 40 1 0 0 0 0 17 24 1 0 0 0 0 17 43 1 0 0 0 0 18 23 1 0 0 0 0 19 29 1 0 0 0 0 19 52 1 0 0 0 0 20 21 1 0 0 0 0 20 38 1 0 0 0 0 21 41 1 0 0 0 0 22 35 1 0 0 0 0 22 44 1 0 0 0 0 23 56 1 0 0 0 0 24 30 1 0 0 0 0 24 53 1 0 0 0 0 25 39 1 0 0 0 0 25 41 1 0 0 0 0 26 42 1 0 0 0 0 26 45 2 0 0 0 0 27 41 1 0 0 0 0 27 46 2 0 0 0 0 28 38 1 0 0 0 0 28 54 1 0 0 0 0 29 31 1 0 0 0 0 29 47 1 0 0 0 0 30 32 1 0 0 0 0 30 48 1 0 0 0 0 31 33 1 0 0 0 0 31 49 1 0 0 0 0 32 34 1 0 0 0 0 32 50 1 0 0 0 0 33 36 1 0 0 0 0 33 51 1 0 0 0 0 34 37 1 0 0 0 0 34 55 1 0 0 0 0 35 40 1 0 0 0 0 35 42 1 0 0 0 0 36 52 1 0 0 0 0 36 55 1 0 0 0 0 37 53 1 0 0 0 0 37 54 1 0 0 0 0 39 40 1 0 0 0 0 42 56 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	792.43
Volume:	787.61
LogP:	2.125
LogD:	2.863
LogS:	-3.467
# Rotatable Bonds:	6
TPSA:	221.9
# H-Bond Aceptor:	14
# H-Bond Donor:	7
# Rings:	7
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.191
Synthetic Accessibility Score:	6.256
Fsp3:	0.857
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:	-5.493
MDCK Permeability:	6.804095028201118e-05
Pgp-inhibitor:	0.985
Pgp-substrate:	0.927
Human Intestinal Absorption (HIA):	0.968
20% Bioavailability (F20%):	0.017
30% Bioavailability (F30%):	0.966

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.089
Plasma Protein Binding (PPB):	62.494911193847656%
Volume Distribution (VD):	0.461
Pgp-substrate:	19.584564208984375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.156
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.837
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.063
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.099
CYP3A4-inhibitor:	0.231
CYP3A4-substrate:	0.291

ADMET: Excretion

Clearance (CL):	1.749
Half-life (T1/2):	0.084

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.193
Drug-inuced Liver Injury (DILI):	0.117
AMES Toxicity:	0.125
Rat Oral Acute Toxicity:	0.977
Maximum Recommended Daily Dose:	0.081
Skin Sensitization:	0.004
Carcinogencity:	0.128
Eye Corrosion:	0.003
Eye Irritation:	0.002
Respiratory Toxicity:	0.946

Download Data

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

Natural Product: NPC69273

Natural Product ID:	NPC69273
*Common Name:**	2-[3-[4,5-Dihydroxy-6-(Hydroxymethyl)-3-(3,4,5-Trihydroxy-6-Methyloxan-2-Yl)Oxyoxan-2-Yl]Oxy-16-Hydroxy-4,4,9,13,14-Pentamethyl-11-Oxo-1,2,3,7,8,10,12,15,16,17-Decahydrocyclopenta[A]Phenanthren-17-Yl]-2-Methyl-5-Propan-2-Ylfuran-3-One
IUPAC Name:	2-[3-[4,5-dihydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxy-16-hydroxy-4,4,9,13,14-pentamethyl-11-oxo-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-2-methyl-5-propan-2-ylfuran-3-one
Synonyms:
Standard InCHIKey:	YRQJYHITIWJZQN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C42H64O14/c1-18(2)23-14-26(45)42(9,56-23)35-22(44)15-39(6)25-12-10-20-21(41(25,8)27(46)16-40(35,39)7)11-13-28(38(20,4)5)54-37-34(32(50)30(48)24(17-43)53-37)55-36-33(51)31(49)29(47)19(3)52-36/h10,14,18-19,21-22,24-25,28-37,43-44,47-51H,11-13,15-17H2,1-9H3
SMILES:	CC(C)C1=CC(=O)C(C)(C2C(CC3(C)C4CC=C5C(CCC(C5(C)C)OC5C(C(C(C(CO)O5)O)O)OC5C(C(C(C(C)O5)O)O)O)C4(C)C(=O)CC23C)O)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1967022
PubChem CID:	343256
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides [CHEMONTID:0002364] Steroidal saponins [CHEMONTID:0001687] Cucurbitacin glycosides

*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
NPO5523	Picria felterrae	Species	Linderniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5523	Picria felterrae	Species	Linderniaceae	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
GI50	55

Activity Type	# Activity
Cell Line	55

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[526121]

☑ 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 NPC69273 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	302
0.1-0.2	1799
0.2-0.3	5328
0.3-0.4	9567
0.4-0.5	11038
0.5-0.6	7413
0.6-0.7	4433
0.7-0.8	2205
0.8-0.85	517
0.85-0.9	85
0.9-0.95	5
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC168899
1.0	High Similarity	NPC293623
0.9832	High Similarity	NPC241008
0.9744	High Similarity	NPC475194
0.9333	High Similarity	NPC93368
0.925	High Similarity	NPC190846
0.925	High Similarity	NPC277191
0.9244	High Similarity	NPC475431
0.9167	High Similarity	NPC476542
0.916	High Similarity	NPC42675
0.9008	High Similarity	NPC141196
0.9008	High Similarity	NPC238005
0.9008	High Similarity	NPC1980
0.8992	High Similarity	NPC161738
0.8974	High Similarity	NPC474557
0.8943	High Similarity	NPC152091
0.8862	High Similarity	NPC198714
0.8843	High Similarity	NPC476543
0.8843	High Similarity	NPC249553
0.8843	High Similarity	NPC476544
0.8843	High Similarity	NPC476545
0.8843	High Similarity	NPC182900
0.8803	High Similarity	NPC474265
0.8803	High Similarity	NPC130427
0.8803	High Similarity	NPC210420
0.878	High Similarity	NPC473505
0.878	High Similarity	NPC30188
0.878	High Similarity	NPC177820
0.877	High Similarity	NPC305771
0.877	High Similarity	NPC169816
0.877	High Similarity	NPC28532
0.877	High Similarity	NPC94072
0.877	High Similarity	NPC15918
0.876	High Similarity	NPC471406
0.875	High Similarity	NPC475632
0.875	High Similarity	NPC86020
0.874	High Similarity	NPC475487
0.873	High Similarity	NPC213634
0.8729	High Similarity	NPC477944
0.8729	High Similarity	NPC260665
0.871	High Similarity	NPC47113
0.871	High Similarity	NPC174367
0.8678	High Similarity	NPC319570
0.8678	High Similarity	NPC473920
0.8678	High Similarity	NPC279143
0.8661	High Similarity	NPC473519
0.8661	High Similarity	NPC471855
0.8661	High Similarity	NPC473805
0.8655	High Similarity	NPC473882
0.864	High Similarity	NPC240070
0.864	High Similarity	NPC329784
0.8632	High Similarity	NPC154856
0.8632	High Similarity	NPC475317
0.8632	High Similarity	NPC52241
0.8618	High Similarity	NPC216866
0.8618	High Similarity	NPC131824
0.8607	High Similarity	NPC475187
0.8595	High Similarity	NPC176005
0.8594	High Similarity	NPC102015
0.8583	High Similarity	NPC279638
0.8571	High Similarity	NPC311534
0.856	High Similarity	NPC104427
0.855	High Similarity	NPC79250
0.855	High Similarity	NPC290746
0.8548	High Similarity	NPC227397
0.8548	High Similarity	NPC228701
0.8547	High Similarity	NPC246205
0.8537	High Similarity	NPC275675
0.8525	High Similarity	NPC127530
0.8512	High Similarity	NPC309433
0.8504	High Similarity	NPC188234
0.8504	High Similarity	NPC125077
0.8504	High Similarity	NPC276838
0.8504	High Similarity	NPC471407
0.8504	High Similarity	NPC329986
0.8504	High Similarity	NPC232785
0.8504	High Similarity	NPC140092
0.85	High Similarity	NPC165439
0.85	High Similarity	NPC74727
0.85	High Similarity	NPC477580
0.8492	Intermediate Similarity	NPC2757
0.8492	Intermediate Similarity	NPC292290
0.848	Intermediate Similarity	NPC7850
0.848	Intermediate Similarity	NPC130229
0.848	Intermediate Similarity	NPC469842
0.848	Intermediate Similarity	NPC469841
0.848	Intermediate Similarity	NPC6615
0.8468	Intermediate Similarity	NPC471965
0.8468	Intermediate Similarity	NPC156789
0.8462	Intermediate Similarity	NPC171619
0.845	Intermediate Similarity	NPC476221
0.845	Intermediate Similarity	NPC142756
0.845	Intermediate Similarity	NPC225385
0.845	Intermediate Similarity	NPC298783
0.845	Intermediate Similarity	NPC157817
0.845	Intermediate Similarity	NPC477709
0.845	Intermediate Similarity	NPC104585
0.8438	Intermediate Similarity	NPC173347
0.8438	Intermediate Similarity	NPC16569
0.8438	Intermediate Similarity	NPC159338
0.8438	Intermediate Similarity	NPC253456
0.8417	Intermediate Similarity	NPC194100
0.8417	Intermediate Similarity	NPC62696
0.8417	Intermediate Similarity	NPC293038
0.8417	Intermediate Similarity	NPC178981
0.8413	Intermediate Similarity	NPC285091
0.8403	Intermediate Similarity	NPC43775
0.84	Intermediate Similarity	NPC27363
0.84	Intermediate Similarity	NPC471961
0.84	Intermediate Similarity	NPC202666
0.84	Intermediate Similarity	NPC262199
0.84	Intermediate Similarity	NPC160084
0.84	Intermediate Similarity	NPC14617
0.84	Intermediate Similarity	NPC471964
0.8387	Intermediate Similarity	NPC169727
0.8387	Intermediate Similarity	NPC187950
0.8387	Intermediate Similarity	NPC131841
0.8387	Intermediate Similarity	NPC241310
0.8387	Intermediate Similarity	NPC475182
0.8387	Intermediate Similarity	NPC47567
0.8387	Intermediate Similarity	NPC412
0.8387	Intermediate Similarity	NPC258789
0.8387	Intermediate Similarity	NPC258815
0.8387	Intermediate Similarity	NPC194310
0.8387	Intermediate Similarity	NPC75417
0.8387	Intermediate Similarity	NPC278163
0.8387	Intermediate Similarity	NPC133506
0.8385	Intermediate Similarity	NPC478069
0.8374	Intermediate Similarity	NPC197003
0.8374	Intermediate Similarity	NPC190939
0.8372	Intermediate Similarity	NPC42670
0.8372	Intermediate Similarity	NPC19124
0.8372	Intermediate Similarity	NPC93416
0.8361	Intermediate Similarity	NPC477252
0.8359	Intermediate Similarity	NPC91
0.8359	Intermediate Similarity	NPC309096
0.8359	Intermediate Similarity	NPC54614
0.8347	Intermediate Similarity	NPC102088
0.8346	Intermediate Similarity	NPC305496
0.8333	Intermediate Similarity	NPC471962
0.8333	Intermediate Similarity	NPC596
0.8333	Intermediate Similarity	NPC473474
0.8333	Intermediate Similarity	NPC471963
0.8333	Intermediate Similarity	NPC247315
0.8321	Intermediate Similarity	NPC262813
0.8308	Intermediate Similarity	NPC116075
0.8308	Intermediate Similarity	NPC247190
0.8308	Intermediate Similarity	NPC146857
0.8308	Intermediate Similarity	NPC32793
0.8308	Intermediate Similarity	NPC469749
0.8306	Intermediate Similarity	NPC472257
0.8293	Intermediate Similarity	NPC475357
0.8291	Intermediate Similarity	NPC210178
0.8281	Intermediate Similarity	NPC475636
0.8281	Intermediate Similarity	NPC295220
0.8279	Intermediate Similarity	NPC235539
0.8279	Intermediate Similarity	NPC31797
0.8279	Intermediate Similarity	NPC134869
0.8279	Intermediate Similarity	NPC152199
0.8268	Intermediate Similarity	NPC181066
0.8268	Intermediate Similarity	NPC273962
0.8268	Intermediate Similarity	NPC469750
0.8268	Intermediate Similarity	NPC250556
0.8268	Intermediate Similarity	NPC469947
0.8268	Intermediate Similarity	NPC87662
0.8264	Intermediate Similarity	NPC251309
0.8258	Intermediate Similarity	NPC190065
0.8258	Intermediate Similarity	NPC59288
0.8258	Intermediate Similarity	NPC141215
0.8258	Intermediate Similarity	NPC251998
0.8258	Intermediate Similarity	NPC471089
0.8254	Intermediate Similarity	NPC256983
0.825	Intermediate Similarity	NPC274833
0.8244	Intermediate Similarity	NPC329636
0.824	Intermediate Similarity	NPC202051
0.824	Intermediate Similarity	NPC476675
0.8235	Intermediate Similarity	NPC118225
0.8226	Intermediate Similarity	NPC6377
0.8226	Intermediate Similarity	NPC214484
0.8226	Intermediate Similarity	NPC114441
0.8226	Intermediate Similarity	NPC309780
0.8226	Intermediate Similarity	NPC475171
0.8226	Intermediate Similarity	NPC472949
0.8226	Intermediate Similarity	NPC180550
0.8226	Intermediate Similarity	NPC157868
0.8226	Intermediate Similarity	NPC178548
0.8226	Intermediate Similarity	NPC208381
0.8226	Intermediate Similarity	NPC35405
0.8226	Intermediate Similarity	NPC469945
0.8226	Intermediate Similarity	NPC11551
0.8226	Intermediate Similarity	NPC473884
0.8226	Intermediate Similarity	NPC192791
0.8226	Intermediate Similarity	NPC39211
0.8226	Intermediate Similarity	NPC258592
0.8203	Intermediate Similarity	NPC471356
0.8203	Intermediate Similarity	NPC117702
0.8203	Intermediate Similarity	NPC179412
0.8203	Intermediate Similarity	NPC469757
0.8203	Intermediate Similarity	NPC471357
0.8203	Intermediate Similarity	NPC146456

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 NPC69273 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	257
0.1-0.2	1997
0.2-0.3	4094
0.3-0.4	1792
0.4-0.5	516
0.5-0.6	266
0.6-0.7	132
0.7-0.8	86
0.8-0.85	10
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8468	Intermediate Similarity	NPD6370	Approved
0.8425	Intermediate Similarity	NPD7736	Approved
0.84	Intermediate Similarity	NPD8328	Phase 3
0.8376	Intermediate Similarity	NPD6412	Phase 2
0.8346	Intermediate Similarity	NPD8293	Discontinued
0.8306	Intermediate Similarity	NPD6059	Approved
0.8306	Intermediate Similarity	NPD6054	Approved
0.8268	Intermediate Similarity	NPD7507	Approved
0.8095	Intermediate Similarity	NPD6016	Approved
0.8095	Intermediate Similarity	NPD6015	Approved
0.8095	Intermediate Similarity	NPD8033	Approved
0.8077	Intermediate Similarity	NPD7319	Approved
0.8065	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD7492	Approved
0.8033	Intermediate Similarity	NPD6882	Approved
0.8033	Intermediate Similarity	NPD8297	Approved
0.8031	Intermediate Similarity	NPD5988	Approved
0.8016	Intermediate Similarity	NPD8377	Approved
0.8016	Intermediate Similarity	NPD8294	Approved
0.7984	Intermediate Similarity	NPD6616	Approved
0.7953	Intermediate Similarity	NPD8379	Approved
0.7953	Intermediate Similarity	NPD8335	Approved
0.7953	Intermediate Similarity	NPD8380	Approved
0.7953	Intermediate Similarity	NPD8378	Approved
0.7953	Intermediate Similarity	NPD8296	Approved
0.7934	Intermediate Similarity	NPD6372	Approved
0.7934	Intermediate Similarity	NPD6373	Approved
0.7923	Intermediate Similarity	NPD7078	Approved
0.792	Intermediate Similarity	NPD6009	Approved
0.7874	Intermediate Similarity	NPD6319	Approved
0.7851	Intermediate Similarity	NPD7320	Approved
0.7833	Intermediate Similarity	NPD6402	Approved
0.7833	Intermediate Similarity	NPD7128	Approved
0.7833	Intermediate Similarity	NPD6675	Approved
0.7833	Intermediate Similarity	NPD5739	Approved
0.7805	Intermediate Similarity	NPD6650	Approved
0.7805	Intermediate Similarity	NPD6649	Approved
0.7727	Intermediate Similarity	NPD6033	Approved
0.7717	Intermediate Similarity	NPD7327	Approved
0.7717	Intermediate Similarity	NPD7328	Approved
0.7705	Intermediate Similarity	NPD6899	Approved
0.7705	Intermediate Similarity	NPD6881	Approved
0.768	Intermediate Similarity	NPD4632	Approved
0.7674	Intermediate Similarity	NPD7503	Approved
0.7661	Intermediate Similarity	NPD8130	Phase 1
0.7656	Intermediate Similarity	NPD7516	Approved
0.7642	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7623	Intermediate Similarity	NPD5697	Approved
0.7623	Intermediate Similarity	NPD5701	Approved
0.7603	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD6883	Approved
0.7581	Intermediate Similarity	NPD7290	Approved
0.7581	Intermediate Similarity	NPD7102	Approved
0.7542	Intermediate Similarity	NPD4755	Approved
0.754	Intermediate Similarity	NPD8133	Approved
0.752	Intermediate Similarity	NPD6869	Approved
0.752	Intermediate Similarity	NPD6847	Approved
0.752	Intermediate Similarity	NPD6617	Approved
0.75	Intermediate Similarity	NPD6012	Approved
0.75	Intermediate Similarity	NPD6014	Approved
0.75	Intermediate Similarity	NPD6013	Approved
0.744	Intermediate Similarity	NPD4634	Approved
0.7424	Intermediate Similarity	NPD7604	Phase 2
0.7419	Intermediate Similarity	NPD6011	Approved
0.7419	Intermediate Similarity	NPD6686	Approved
0.7417	Intermediate Similarity	NPD5286	Approved
0.7417	Intermediate Similarity	NPD4700	Approved
0.7417	Intermediate Similarity	NPD4696	Approved
0.7417	Intermediate Similarity	NPD5285	Approved
0.7405	Intermediate Similarity	NPD5983	Phase 2
0.7398	Intermediate Similarity	NPD6008	Approved
0.7395	Intermediate Similarity	NPD6083	Phase 2
0.7395	Intermediate Similarity	NPD6084	Phase 2
0.7381	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD6336	Discontinued
0.7295	Intermediate Similarity	NPD5224	Approved
0.7295	Intermediate Similarity	NPD5225	Approved
0.7295	Intermediate Similarity	NPD5226	Approved
0.7295	Intermediate Similarity	NPD4633	Approved
0.7295	Intermediate Similarity	NPD5211	Phase 2
0.7293	Intermediate Similarity	NPD6067	Discontinued
0.7258	Intermediate Similarity	NPD4768	Approved
0.7258	Intermediate Similarity	NPD4767	Approved
0.7236	Intermediate Similarity	NPD5175	Approved
0.7236	Intermediate Similarity	NPD5174	Approved
0.7213	Intermediate Similarity	NPD5223	Approved
0.719	Intermediate Similarity	NPD5696	Approved
0.7177	Intermediate Similarity	NPD5141	Approved
0.7154	Intermediate Similarity	NPD6274	Approved
0.7143	Intermediate Similarity	NPD8516	Approved
0.7143	Intermediate Similarity	NPD8513	Phase 3
0.7143	Intermediate Similarity	NPD4729	Approved
0.7143	Intermediate Similarity	NPD8515	Approved
0.7143	Intermediate Similarity	NPD8517	Approved
0.7143	Intermediate Similarity	NPD4730	Approved
0.7121	Intermediate Similarity	NPD7101	Approved
0.7121	Intermediate Similarity	NPD7100	Approved
0.7101	Intermediate Similarity	NPD5956	Approved
0.7097	Intermediate Similarity	NPD4754	Approved
0.7094	Intermediate Similarity	NPD4753	Phase 2
0.7083	Intermediate Similarity	NPD5695	Phase 3
0.7054	Intermediate Similarity	NPD6053	Discontinued
0.7045	Intermediate Similarity	NPD6335	Approved
0.7031	Intermediate Similarity	NPD5250	Approved
0.7031	Intermediate Similarity	NPD5251	Approved
0.7031	Intermediate Similarity	NPD5247	Approved
0.7031	Intermediate Similarity	NPD5248	Approved
0.7031	Intermediate Similarity	NPD5249	Phase 3
0.7025	Intermediate Similarity	NPD4697	Phase 3
0.7015	Intermediate Similarity	NPD6908	Approved
0.7015	Intermediate Similarity	NPD6909	Approved
0.7008	Intermediate Similarity	NPD5128	Approved
0.697	Remote Similarity	NPD7115	Discovery
0.697	Remote Similarity	NPD6317	Approved
0.6949	Remote Similarity	NPD5328	Approved
0.6942	Remote Similarity	NPD4629	Approved
0.6942	Remote Similarity	NPD5210	Approved
0.6917	Remote Similarity	NPD4202	Approved
0.6917	Remote Similarity	NPD6314	Approved
0.6917	Remote Similarity	NPD6313	Approved
0.6917	Remote Similarity	NPD6399	Phase 3
0.6889	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD5222	Approved
0.6885	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD5221	Approved
0.6846	Remote Similarity	NPD5215	Approved
0.6846	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD5217	Approved
0.6846	Remote Similarity	NPD5216	Approved
0.6838	Remote Similarity	NPD8080	Discontinued
0.6833	Remote Similarity	NPD6079	Approved
0.6829	Remote Similarity	NPD7902	Approved
0.6829	Remote Similarity	NPD5173	Approved
0.6807	Remote Similarity	NPD6080	Approved
0.6807	Remote Similarity	NPD6673	Approved
0.6807	Remote Similarity	NPD6904	Approved
0.6777	Remote Similarity	NPD8171	Discontinued
0.6769	Remote Similarity	NPD5169	Approved
0.6769	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD5135	Approved
0.6761	Remote Similarity	NPD8449	Approved
0.6752	Remote Similarity	NPD5329	Approved
0.6744	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD6672	Approved
0.6723	Remote Similarity	NPD5737	Approved
0.6721	Remote Similarity	NPD5282	Discontinued
0.6721	Remote Similarity	NPD7748	Approved
0.6718	Remote Similarity	NPD5127	Approved
0.6713	Remote Similarity	NPD8450	Suspended
0.6695	Remote Similarity	NPD3618	Phase 1
0.6667	Remote Similarity	NPD3133	Approved
0.6667	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3665	Phase 1
0.6667	Remote Similarity	NPD4786	Approved
0.6667	Remote Similarity	NPD4197	Approved
0.6667	Remote Similarity	NPD3666	Approved
0.6642	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD6868	Approved
0.664	Remote Similarity	NPD7638	Approved
0.6606	Remote Similarity	NPD7799	Discontinued
0.6596	Remote Similarity	NPD8336	Approved
0.6596	Remote Similarity	NPD8337	Approved
0.6587	Remote Similarity	NPD7639	Approved
0.6587	Remote Similarity	NPD7640	Approved
0.6585	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD7900	Approved
0.6583	Remote Similarity	NPD6903	Approved
0.6583	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD7260	Phase 2
0.6567	Remote Similarity	NPD5167	Approved
0.6565	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD5693	Phase 1
0.6557	Remote Similarity	NPD7515	Phase 2
0.6557	Remote Similarity	NPD6050	Approved
0.6555	Remote Similarity	NPD7521	Approved
0.6555	Remote Similarity	NPD7334	Approved
0.6555	Remote Similarity	NPD6684	Approved
0.6555	Remote Similarity	NPD5330	Approved
0.6555	Remote Similarity	NPD6409	Approved
0.6555	Remote Similarity	NPD6098	Approved
0.6555	Remote Similarity	NPD7146	Approved
0.6538	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD6333	Approved
0.6531	Remote Similarity	NPD6334	Approved
0.6515	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD7625	Phase 1
0.6496	Remote Similarity	NPD4522	Approved
0.6496	Remote Similarity	NPD4223	Phase 3
0.6496	Remote Similarity	NPD3667	Approved
0.6496	Remote Similarity	NPD4221	Approved
0.6475	Remote Similarity	NPD5692	Phase 3
0.6423	Remote Similarity	NPD8034	Phase 2
0.6423	Remote Similarity	NPD5694	Approved
0.6423	Remote Similarity	NPD8035	Phase 2
0.6423	Remote Similarity	NPD5284	Approved
0.6423	Remote Similarity	NPD5281	Approved
0.6417	Remote Similarity	NPD5279	Phase 3
0.6417	Remote Similarity	NPD5280	Approved
0.6417	Remote Similarity	NPD5690	Phase 2
0.6417	Remote Similarity	NPD4694	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