NPASS Compound

Structure

CID212660 OpenBabel06191716002D 48 56 0 0 1 0 0 0 0 0999 V2000 -2.6792 -0.5001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9659 -1.8548 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0406 -6.4200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9132 -5.9163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6493 -4.4619 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6493 -1.4678 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2307 0.0347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3453 -5.4122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4973 -4.9227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8879 -3.9436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0405 -3.4540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9534 -0.5195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9546 -3.4541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3452 -2.4756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1818 -4.5639 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1931 -2.9645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8008 -1.0080 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4763 -1.0069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.6713 -5.4113 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.9546 -2.4756 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1932 -4.9227 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4973 -3.9436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8879 -4.9226 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4972 -1.9860 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8014 -1.9861 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.1821 -6.2589 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -9.2035 -6.2591 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -8.7141 -5.4116 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8200 -1.4223 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9926 0.2104 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -6.0405 -5.4122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6493 -3.4541 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6493 -2.4756 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4994 -0.6687 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1932 -3.9436 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3452 -3.4541 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1067 -1.0090 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -4.9659 -0.1590 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.6499 -5.4112 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.6715 -7.1063 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7143 -7.1066 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4058 1.1370 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.2032 -4.5641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4972 -1.0069 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7355 -5.4118 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1073 -1.9871 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8123 -1.6338 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 2 18 1 0 0 0 0 3 31 1 0 0 0 0 4 31 1 0 0 0 0 5 32 1 0 0 0 0 8 9 1 0 0 0 0 8 21 1 0 0 0 0 9 22 2 0 0 0 0 10 11 1 0 0 0 0 10 23 1 0 0 0 0 11 35 1 0 0 0 0 12 17 1 0 0 0 0 12 37 1 0 0 0 0 13 32 1 0 0 0 0 14 24 1 0 0 0 0 15 19 1 0 0 0 0 15 43 1 0 0 0 0 16 35 1 0 0 0 0 16 36 1 0 0 0 0 17 1 1 6 0 0 0 17 25 1 0 0 0 0 18 38 2 0 0 0 0 18 44 1 0 0 0 0 19 26 1 0 0 0 0 19 39 1 0 0 0 0 20 13 1 1 0 0 0 20 25 1 0 0 0 0 20 46 1 0 0 0 0 21 31 1 0 0 0 0 21 35 1 1 0 0 0 22 32 1 0 0 0 0 22 36 1 0 0 0 0 23 31 1 0 0 0 0 23 45 1 1 0 0 0 24 33 1 1 0 0 0 24 44 1 0 0 0 0 25 33 1 1 0 0 0 26 27 1 0 0 0 0 26 40 1 0 0 0 0 27 28 1 0 0 0 0 27 41 1 0 0 0 0 28 43 1 0 0 0 0 28 45 1 0 0 0 0 29 34 1 6 0 0 0 29 37 1 0 0 0 0 29 47 1 0 0 0 0 30 34 1 0 0 0 0 30 42 1 0 0 0 0 30 48 1 0 0 0 0 32 33 1 6 0 0 0 33 6 1 1 0 0 0 34 7 1 6 0 0 0 34 47 1 0 0 0 0 35 36 1 6 0 0 0 36 14 1 6 0 0 0 37 46 1 0 0 0 0 37 48 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	674.37
Volume:	662.919
LogP:	3.923
LogD:	3.613
LogS:	-4.227
# Rotatable Bonds:	4
TPSA:	156.67
# H-Bond Aceptor:	11
# H-Bond Donor:	4
# Rings:	9
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.198
Synthetic Accessibility Score:	7.191
Fsp3:	0.919
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.435
MDCK Permeability:	2.860936183424201e-05
Pgp-inhibitor:	0.069
Pgp-substrate:	0.146
Human Intestinal Absorption (HIA):	0.118
20% Bioavailability (F20%):	0.084
30% Bioavailability (F30%):	0.553

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.046
Plasma Protein Binding (PPB):	51.30194091796875%
Volume Distribution (VD):	0.531
Pgp-substrate:	30.792007446289062%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.847
CYP2C19-inhibitor:	0.005
CYP2C19-substrate:	0.774
CYP2C9-inhibitor:	0.014
CYP2C9-substrate:	0.019
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.085
CYP3A4-inhibitor:	0.762
CYP3A4-substrate:	0.373

ADMET: Excretion

Clearance (CL):	1.094
Half-life (T1/2):	0.304

ADMET: Toxicity

hERG Blockers:	0.13
Human Hepatotoxicity (H-HT):	0.216
Drug-inuced Liver Injury (DILI):	0.106
AMES Toxicity:	0.932
Rat Oral Acute Toxicity:	0.767
Maximum Recommended Daily Dose:	0.948
Skin Sensitization:	0.149
Carcinogencity:	0.129
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC212660

Natural Product ID:	NPC212660
*Common Name:**	XUJMHSCMPCZWOV-XVGSJRLISA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XUJMHSCMPCZWOV-XVGSJRLISA-N
Standard InCHI:	InChI=1S/C37H54O11/c1-17-12-37(29-34(7,47-29)30(42)48-37)46-20-13-32(5)22-9-8-21-31(3,4)23(45-28-27(41)26(40)19(39)15-43-28)10-11-35(21)16-36(22,35)14-24(44-18(2)38)33(32,6)25(17)20/h9,17,19-21,23-30,39-42H,8,10-16H2,1-7H3/t17-,19?,20+,21+,23+,24-,25+,26?,27?,28?,29-,30?,32+,33-,34+,35-,36+,37?/m1/s1
SMILES:	C[C@@H]1CC2([C@H]3[C@@](C)(C(O)O2)O3)O[C@H]2C[C@@]3(C)C4=CC[C@H]5C(C)(C)[C@H](CC[C@]65C[C@@]46C[C@H]([C@]3(C)[C@@H]12)OC(=O)C)OC1C(C(C(CO1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1966457
PubChem CID:	399179
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols 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
NPO15890	Cimicifuga foetida	Species	Ranunculaceae	Eukaryota	Roots	n.a.	n.a.	PMID[20121210]
NPO15373	Actaea dahurica	Species	Ranunculaceae	Eukaryota	Roots	n.a.	n.a.	PMID[28558206]
NPO15373	Actaea dahurica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32031796]
NPO2727	Actaea simplex	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15890	Cimicifuga foetida	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15373	Actaea dahurica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO389	Actaea heracleifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO389	Actaea heracleifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15373	Actaea dahurica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2727	Actaea simplex	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15890	Cimicifuga foetida	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO389	Actaea heracleifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15373	Actaea dahurica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2727	Actaea simplex	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15890	Cimicifuga foetida	Species	Ranunculaceae	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	58

Activity Type	# Activity
Cell Line	58

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.	30902.95	nM	PMID[456558]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	31477.48	nM	PMID[456558]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	43451.02	nM	PMID[456558]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	34040.82	nM	PMID[456558]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	41783.04	nM	PMID[456558]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	54325.03	nM	PMID[456558]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	43151.91	nM	PMID[456558]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	7726.81	nM	PMID[456558]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	20796.97	nM	PMID[456558]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	19724.23	nM	PMID[456558]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	33189.45	nM	PMID[456558]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	32062.69	nM	PMID[456558]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	23768.4	nM	PMID[456558]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	12050.36	nM	PMID[456558]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	27352.69	nM	PMID[456558]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	43853.07	nM	PMID[456558]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	30690.22	nM	PMID[456558]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	41686.94	nM	PMID[456558]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	47533.52	nM	PMID[456558]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	21086.28	nM	PMID[456558]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	75162.29	nM	PMID[456558]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	35974.93	nM	PMID[456558]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	36475.39	nM	PMID[456558]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	22961.49	nM	PMID[456558]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	33651.16	nM	PMID[456558]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	47206.3	nM	PMID[456558]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	61094.2	nM	PMID[456558]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	19588.45	nM	PMID[456558]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	48417.24	nM	PMID[456558]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	23442.29	nM	PMID[456558]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	27925.44	nM	PMID[456558]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	19678.86	nM	PMID[456558]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	20606.3	nM	PMID[456558]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	48865.24	nM	PMID[456558]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[456558]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	31550.05	nM	PMID[456558]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	19408.86	nM	PMID[456558]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	58748.94	nM	PMID[456558]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	33419.5	nM	PMID[456558]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	22908.68	nM	PMID[456558]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	30760.97	nM	PMID[456558]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	30408.85	nM	PMID[456558]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	20796.97	nM	PMID[456558]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	25292.98	nM	PMID[456558]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	46131.76	nM	PMID[456558]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	21677.04	nM	PMID[456558]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	32359.37	nM	PMID[456558]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	25703.96	nM	PMID[456558]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	36475.39	nM	PMID[456558]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	40364.54	nM	PMID[456558]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	25176.77	nM	PMID[456558]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	26915.35	nM	PMID[456558]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	11694.99	nM	PMID[456558]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	35399.73	nM	PMID[456558]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	33189.45	nM	PMID[456558]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	41209.75	nM	PMID[456558]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	15885.47	nM	PMID[456558]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	21330.45	nM	PMID[456558]

☑ 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 NPC212660 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	287
0.1-0.2	2339
0.2-0.3	7800
0.3-0.4	13884
0.4-0.5	7388
0.5-0.6	5529
0.6-0.7	3355
0.7-0.8	1657
0.8-0.85	421
0.85-0.9	28
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9434	High Similarity	NPC476835
0.9091	High Similarity	NPC144068
0.9083	High Similarity	NPC114188
0.8981	High Similarity	NPC38217
0.8981	High Similarity	NPC472988
0.8981	High Similarity	NPC295980
0.8929	High Similarity	NPC477031
0.8929	High Similarity	NPC63609
0.8909	High Similarity	NPC197231
0.8899	High Similarity	NPC296761
0.8899	High Similarity	NPC51925
0.8899	High Similarity	NPC154085
0.8899	High Similarity	NPC43976
0.8899	High Similarity	NPC125361
0.8889	High Similarity	NPC234160
0.8879	High Similarity	NPC85593
0.8879	High Similarity	NPC31430
0.885	High Similarity	NPC477807
0.8839	High Similarity	NPC477808
0.8829	High Similarity	NPC19888
0.8807	High Similarity	NPC476538
0.8807	High Similarity	NPC476540
0.8807	High Similarity	NPC476541
0.8807	High Similarity	NPC7213
0.8807	High Similarity	NPC476539
0.8796	High Similarity	NPC242748
0.8796	High Similarity	NPC473199
0.8796	High Similarity	NPC26798
0.8796	High Similarity	NPC181845
0.8785	High Similarity	NPC139181
0.8785	High Similarity	NPC97260
0.8785	High Similarity	NPC476837
0.8772	High Similarity	NPC475403
0.8772	High Similarity	NPC160888
0.8739	High Similarity	NPC65167
0.8739	High Similarity	NPC470748
0.8727	High Similarity	NPC477026
0.8727	High Similarity	NPC477027
0.8727	High Similarity	NPC70204
0.8727	High Similarity	NPC475670
0.8727	High Similarity	NPC42482
0.8727	High Similarity	NPC306131
0.8727	High Similarity	NPC40440
0.8716	High Similarity	NPC226642
0.8716	High Similarity	NPC470432
0.8716	High Similarity	NPC305423
0.8716	High Similarity	NPC230507
0.8716	High Similarity	NPC161676
0.8716	High Similarity	NPC113044
0.8716	High Similarity	NPC14704
0.8716	High Similarity	NPC283829
0.8704	High Similarity	NPC221562
0.8704	High Similarity	NPC187400
0.8704	High Similarity	NPC471111
0.8704	High Similarity	NPC470885
0.8696	High Similarity	NPC470897
0.8696	High Similarity	NPC476085
0.8696	High Similarity	NPC30483
0.8696	High Similarity	NPC195560
0.8696	High Similarity	NPC229962
0.8696	High Similarity	NPC469756
0.8696	High Similarity	NPC236973
0.8696	High Similarity	NPC32177
0.8696	High Similarity	NPC292467
0.8696	High Similarity	NPC55532
0.8696	High Similarity	NPC473633
0.8673	High Similarity	NPC477810
0.8636	High Similarity	NPC220427
0.8636	High Similarity	NPC98696
0.8632	High Similarity	NPC43842
0.8624	High Similarity	NPC473923
0.8624	High Similarity	NPC474569
0.8624	High Similarity	NPC473476
0.8621	High Similarity	NPC475358
0.8621	High Similarity	NPC475629
0.8621	High Similarity	NPC233391
0.8621	High Similarity	NPC475556
0.8621	High Similarity	NPC107607
0.8621	High Similarity	NPC473566
0.8621	High Similarity	NPC72260
0.8621	High Similarity	NPC50689
0.8621	High Similarity	NPC207243
0.8621	High Similarity	NPC198325
0.8611	High Similarity	NPC286969
0.8611	High Similarity	NPC120123
0.8611	High Similarity	NPC131479
0.8611	High Similarity	NPC155010
0.8611	High Similarity	NPC31907
0.8611	High Similarity	NPC8039
0.8611	High Similarity	NPC211879
0.8611	High Similarity	NPC472252
0.8611	High Similarity	NPC157659
0.8611	High Similarity	NPC245280
0.8611	High Similarity	NPC16520
0.8611	High Similarity	NPC189852
0.8611	High Similarity	NPC473020
0.8611	High Similarity	NPC213190
0.8611	High Similarity	NPC114874
0.8609	High Similarity	NPC472080
0.8609	High Similarity	NPC218093
0.8609	High Similarity	NPC475357
0.8598	High Similarity	NPC108227
0.8598	High Similarity	NPC476512
0.8598	High Similarity	NPC472081
0.8596	High Similarity	NPC146652
0.8584	High Similarity	NPC476693
0.8571	High Similarity	NPC13190
0.8571	High Similarity	NPC477032
0.8571	High Similarity	NPC475247
0.8571	High Similarity	NPC477028
0.8571	High Similarity	NPC294129
0.8571	High Similarity	NPC476547
0.8571	High Similarity	NPC124677
0.8559	High Similarity	NPC73243
0.8559	High Similarity	NPC309278
0.8559	High Similarity	NPC250089
0.8559	High Similarity	NPC106589
0.8559	High Similarity	NPC157530
0.8559	High Similarity	NPC194207
0.8559	High Similarity	NPC218571
0.8559	High Similarity	NPC84956
0.8559	High Similarity	NPC475333
0.8559	High Similarity	NPC102016
0.8559	High Similarity	NPC171073
0.8559	High Similarity	NPC202261
0.8559	High Similarity	NPC300557
0.8559	High Similarity	NPC257207
0.8559	High Similarity	NPC244086
0.8559	High Similarity	NPC150372
0.8559	High Similarity	NPC224098
0.8559	High Similarity	NPC14630
0.8559	High Similarity	NPC249265
0.8559	High Similarity	NPC477809
0.8559	High Similarity	NPC475550
0.8559	High Similarity	NPC208383
0.8559	High Similarity	NPC95051
0.8559	High Similarity	NPC46190
0.8559	High Similarity	NPC232054
0.8559	High Similarity	NPC470433
0.8559	High Similarity	NPC22779
0.8559	High Similarity	NPC295133
0.8559	High Similarity	NPC6806
0.8559	High Similarity	NPC248746
0.8547	High Similarity	NPC474908
0.8547	High Similarity	NPC475419
0.8547	High Similarity	NPC314535
0.8547	High Similarity	NPC40749
0.8547	High Similarity	NPC173555
0.8547	High Similarity	NPC133506
0.8547	High Similarity	NPC120390
0.8547	High Similarity	NPC231518
0.8547	High Similarity	NPC475219
0.8547	High Similarity	NPC475590
0.8545	High Similarity	NPC473469
0.8545	High Similarity	NPC190395
0.8534	High Similarity	NPC291820
0.8534	High Similarity	NPC329905
0.8534	High Similarity	NPC81222
0.8532	High Similarity	NPC470057
0.8532	High Similarity	NPC470064
0.8532	High Similarity	NPC470061
0.8532	High Similarity	NPC165033
0.8532	High Similarity	NPC273879
0.8532	High Similarity	NPC470058
0.8532	High Similarity	NPC470059
0.8532	High Similarity	NPC470060
0.8532	High Similarity	NPC470043
0.8532	High Similarity	NPC475365
0.8532	High Similarity	NPC173583
0.8532	High Similarity	NPC470062
0.8522	High Similarity	NPC93883
0.8522	High Similarity	NPC290693
0.8522	High Similarity	NPC203862
0.8519	High Similarity	NPC310138
0.8519	High Similarity	NPC134967
0.8519	High Similarity	NPC470029
0.8519	High Similarity	NPC312553
0.8519	High Similarity	NPC114700
0.8519	High Similarity	NPC159036
0.8519	High Similarity	NPC288694
0.8509	High Similarity	NPC473882
0.8509	High Similarity	NPC167183
0.8509	High Similarity	NPC32707
0.8505	High Similarity	NPC470030
0.8505	High Similarity	NPC324598
0.8496	Intermediate Similarity	NPC112274
0.8496	Intermediate Similarity	NPC32361
0.8496	Intermediate Similarity	NPC31896
0.8496	Intermediate Similarity	NPC210569
0.8496	Intermediate Similarity	NPC263359
0.8496	Intermediate Similarity	NPC254255
0.8496	Intermediate Similarity	NPC244431
0.8482	Intermediate Similarity	NPC222202
0.8482	Intermediate Similarity	NPC23808
0.8482	Intermediate Similarity	NPC224314
0.8482	Intermediate Similarity	NPC141433
0.8482	Intermediate Similarity	NPC247037
0.8482	Intermediate Similarity	NPC101450
0.8482	Intermediate Similarity	NPC269297
0.8482	Intermediate Similarity	NPC477811

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 NPC212660 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	249
0.1-0.2	2523
0.2-0.3	4359
0.3-0.4	1283
0.4-0.5	378
0.5-0.6	242
0.6-0.7	92
0.7-0.8	13
0.8-0.85	11
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8621	High Similarity	NPD8294	Approved
0.8621	High Similarity	NPD8377	Approved
0.8547	High Similarity	NPD8296	Approved
0.8547	High Similarity	NPD8033	Approved
0.8547	High Similarity	NPD8335	Approved
0.8547	High Similarity	NPD8380	Approved
0.8547	High Similarity	NPD8378	Approved
0.8547	High Similarity	NPD8379	Approved
0.8291	Intermediate Similarity	NPD7327	Approved
0.8291	Intermediate Similarity	NPD7328	Approved
0.822	Intermediate Similarity	NPD7516	Approved
0.8083	Intermediate Similarity	NPD7503	Approved
0.7823	Intermediate Similarity	NPD7507	Approved
0.7797	Intermediate Similarity	NPD8133	Approved
0.7778	Intermediate Similarity	NPD8171	Discontinued
0.7759	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7739	Intermediate Similarity	NPD6412	Phase 2
0.7698	Intermediate Similarity	NPD7736	Approved
0.7638	Intermediate Similarity	NPD7319	Approved
0.7619	Intermediate Similarity	NPD8293	Discontinued
0.7459	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD6370	Approved
0.7414	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD8328	Phase 3
0.7323	Intermediate Similarity	NPD7492	Approved
0.728	Intermediate Similarity	NPD6059	Approved
0.728	Intermediate Similarity	NPD6054	Approved
0.7266	Intermediate Similarity	NPD6616	Approved
0.7209	Intermediate Similarity	NPD7078	Approved
0.7197	Intermediate Similarity	NPD8449	Approved
0.7143	Intermediate Similarity	NPD8450	Suspended
0.7131	Intermediate Similarity	NPD6882	Approved
0.7131	Intermediate Similarity	NPD8297	Approved
0.7087	Intermediate Similarity	NPD6016	Approved
0.7087	Intermediate Similarity	NPD6015	Approved
0.7083	Intermediate Similarity	NPD6686	Approved
0.7059	Intermediate Similarity	NPD6008	Approved
0.704	Intermediate Similarity	NPD6009	Approved
0.7031	Intermediate Similarity	NPD5988	Approved
0.7008	Intermediate Similarity	NPD6319	Approved
0.6977	Remote Similarity	NPD6067	Discontinued
0.6953	Remote Similarity	NPD8516	Approved
0.6953	Remote Similarity	NPD8513	Phase 3
0.6953	Remote Similarity	NPD8515	Approved
0.6953	Remote Similarity	NPD8517	Approved
0.6942	Remote Similarity	NPD7320	Approved
0.6935	Remote Similarity	NPD4632	Approved
0.6917	Remote Similarity	NPD6675	Approved
0.6917	Remote Similarity	NPD5739	Approved
0.6917	Remote Similarity	NPD7128	Approved
0.6917	Remote Similarity	NPD6402	Approved
0.6901	Remote Similarity	NPD7625	Phase 1
0.6885	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD6373	Approved
0.6885	Remote Similarity	NPD6372	Approved
0.6846	Remote Similarity	NPD7604	Phase 2
0.6838	Remote Similarity	NPD7638	Approved
0.6822	Remote Similarity	NPD6928	Phase 2
0.6803	Remote Similarity	NPD6899	Approved
0.6803	Remote Similarity	NPD6881	Approved
0.678	Remote Similarity	NPD7640	Approved
0.678	Remote Similarity	NPD7639	Approved
0.6774	Remote Similarity	NPD8130	Phase 1
0.6774	Remote Similarity	NPD6650	Approved
0.6774	Remote Similarity	NPD6649	Approved
0.6772	Remote Similarity	NPD7115	Discovery
0.6767	Remote Similarity	NPD6033	Approved
0.6724	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD5697	Approved
0.6721	Remote Similarity	NPD5701	Approved
0.6694	Remote Similarity	NPD6883	Approved
0.6694	Remote Similarity	NPD7290	Approved
0.6694	Remote Similarity	NPD7102	Approved
0.6694	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7525	Registered
0.664	Remote Similarity	NPD6869	Approved
0.664	Remote Similarity	NPD6617	Approved
0.664	Remote Similarity	NPD6847	Approved
0.6613	Remote Similarity	NPD6013	Approved
0.6613	Remote Similarity	NPD6012	Approved
0.6613	Remote Similarity	NPD6014	Approved
0.661	Remote Similarity	NPD6083	Phase 2
0.661	Remote Similarity	NPD6084	Phase 2
0.6565	Remote Similarity	NPD5983	Phase 2
0.6552	Remote Similarity	NPD6399	Phase 3
0.6532	Remote Similarity	NPD6011	Approved
0.6508	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD7748	Approved
0.6496	Remote Similarity	NPD6001	Approved
0.6493	Remote Similarity	NPD6336	Discontinued
0.6471	Remote Similarity	NPD4755	Approved
0.6471	Remote Similarity	NPD7902	Approved
0.6466	Remote Similarity	NPD8035	Phase 2
0.6466	Remote Similarity	NPD8034	Phase 2
0.6452	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD5344	Discontinued
0.6435	Remote Similarity	NPD6051	Approved
0.6429	Remote Similarity	NPD4634	Approved
0.6422	Remote Similarity	NPD7645	Phase 2
0.641	Remote Similarity	NPD4202	Approved
0.6404	Remote Similarity	NPD7524	Approved
0.6393	Remote Similarity	NPD7632	Discontinued
0.6364	Remote Similarity	NPD5286	Approved
0.6364	Remote Similarity	NPD4700	Approved
0.6364	Remote Similarity	NPD4696	Approved
0.6364	Remote Similarity	NPD5285	Approved
0.6325	Remote Similarity	NPD7515	Phase 2
0.6311	Remote Similarity	NPD4159	Approved
0.6308	Remote Similarity	NPD6274	Approved
0.6304	Remote Similarity	NPD5956	Approved
0.6303	Remote Similarity	NPD5695	Phase 3
0.6296	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD7101	Approved
0.6288	Remote Similarity	NPD7100	Approved
0.6283	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD4225	Approved
0.6281	Remote Similarity	NPD5696	Approved
0.627	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.626	Remote Similarity	NPD5225	Approved
0.626	Remote Similarity	NPD5224	Approved
0.626	Remote Similarity	NPD4633	Approved
0.626	Remote Similarity	NPD5211	Phase 2
0.626	Remote Similarity	NPD5226	Approved
0.624	Remote Similarity	NPD4767	Approved
0.624	Remote Similarity	NPD4768	Approved
0.6228	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD7900	Approved
0.6212	Remote Similarity	NPD6335	Approved
0.621	Remote Similarity	NPD5174	Approved
0.621	Remote Similarity	NPD5175	Approved
0.6207	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD6903	Approved
0.6204	Remote Similarity	NPD8074	Phase 3
0.6204	Remote Similarity	NPD6942	Approved
0.6204	Remote Similarity	NPD7339	Approved
0.6202	Remote Similarity	NPD6053	Discontinued
0.6195	Remote Similarity	NPD3669	Approved
0.6195	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD6695	Phase 3
0.6194	Remote Similarity	NPD6909	Approved
0.6194	Remote Similarity	NPD6908	Approved
0.6194	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD5223	Approved
0.6174	Remote Similarity	NPD5330	Approved
0.6174	Remote Similarity	NPD6684	Approved
0.6174	Remote Similarity	NPD7521	Approved
0.6174	Remote Similarity	NPD7334	Approved
0.6174	Remote Similarity	NPD6409	Approved
0.6174	Remote Similarity	NPD7146	Approved
0.6167	Remote Similarity	NPD7991	Discontinued
0.616	Remote Similarity	NPD5141	Approved
0.6159	Remote Similarity	NPD8336	Approved
0.6159	Remote Similarity	NPD8337	Approved
0.6154	Remote Similarity	NPD5328	Approved
0.6154	Remote Similarity	NPD4753	Phase 2
0.6142	Remote Similarity	NPD4730	Approved
0.6142	Remote Similarity	NPD4729	Approved
0.614	Remote Similarity	NPD4786	Approved
0.6136	Remote Similarity	NPD6317	Approved
0.6121	Remote Similarity	NPD7750	Discontinued
0.6102	Remote Similarity	NPD3168	Discontinued
0.6098	Remote Similarity	NPD6648	Approved
0.609	Remote Similarity	NPD6314	Approved
0.609	Remote Similarity	NPD6313	Approved
0.608	Remote Similarity	NPD4754	Approved
0.6075	Remote Similarity	NPD4243	Approved
0.6071	Remote Similarity	NPD4748	Discontinued
0.6061	Remote Similarity	NPD6940	Discontinued
0.605	Remote Similarity	NPD7637	Suspended
0.605	Remote Similarity	NPD6079	Approved
0.6047	Remote Similarity	NPD5249	Phase 3
0.6047	Remote Similarity	NPD5247	Approved
0.6047	Remote Similarity	NPD5251	Approved
0.6047	Remote Similarity	NPD5250	Approved
0.6047	Remote Similarity	NPD5248	Approved
0.6034	Remote Similarity	NPD6098	Approved
0.6034	Remote Similarity	NPD3618	Phase 1
0.6017	Remote Similarity	NPD6673	Approved
0.6017	Remote Similarity	NPD6904	Approved
0.6017	Remote Similarity	NPD6080	Approved
0.6016	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD5128	Approved
0.6	Remote Similarity	NPD3666	Approved
0.6	Remote Similarity	NPD3665	Phase 1
0.6	Remote Similarity	NPD3133	Approved
0.6	Remote Similarity	NPD6933	Approved
0.5986	Remote Similarity	NPD8338	Approved
0.5982	Remote Similarity	NPD4195	Approved
0.5966	Remote Similarity	NPD7838	Discovery
0.5966	Remote Similarity	NPD46	Approved
0.5966	Remote Similarity	NPD6698	Approved
0.5965	Remote Similarity	NPD3667	Approved
0.5963	Remote Similarity	NPD1810	Approved
0.5963	Remote Similarity	NPD4784	Approved
0.5963	Remote Similarity	NPD1811	Approved
0.5963	Remote Similarity	NPD4785	Approved
0.5939	Remote Similarity	NPD7799	Discontinued

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