NPASS Compound

Structure

CID254886 OpenBabel06191716062D 42 42 0 0 0 0 0 0 0 0999 V2000 -1.7321 9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 12.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 15.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 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 18.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 11.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 14.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 17.0000 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 -3.4641 9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 12.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 13.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 15.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 16.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 18.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 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 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 12.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 15.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 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 2.5981 18.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 19.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 20.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 20.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 31 1 0 0 0 0 2 32 1 0 0 0 0 3 33 1 0 0 0 0 4 34 1 0 0 0 0 5 35 1 0 0 0 0 6 36 1 0 0 0 0 7 37 1 0 0 0 0 8 40 1 0 0 0 0 9 40 1 0 0 0 0 10 11 2 0 0 0 0 10 17 1 0 0 0 0 11 18 1 0 0 0 0 12 19 2 0 0 0 0 12 21 1 0 0 0 0 13 22 2 0 0 0 0 13 23 1 0 0 0 0 14 20 2 0 0 0 0 14 24 1 0 0 0 0 15 25 2 0 0 0 0 15 26 1 0 0 0 0 16 27 1 0 0 0 0 16 30 1 0 0 0 0 17 31 2 0 0 0 0 18 32 2 0 0 0 0 19 31 1 0 0 0 0 20 32 1 0 0 0 0 21 33 2 0 0 0 0 22 33 1 0 0 0 0 23 34 2 0 0 0 0 24 35 2 0 0 0 0 25 34 1 0 0 0 0 26 37 2 0 0 0 0 27 36 1 0 0 0 0 28 29 2 0 0 0 0 28 35 1 0 0 0 0 29 38 1 0 0 0 0 30 40 1 0 0 0 0 36 38 2 0 0 0 0 37 39 1 0 0 0 0 38 40 1 0 0 0 0 39 41 2 0 0 0 0 39 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	564.4
Volume:	672.509
LogP:	5.521
LogD:	4.063
LogS:	-3.988
# Rotatable Bonds:	13
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.178
Synthetic Accessibility Score:	3.98
Fsp3:	0.325
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
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:	-5.453
MDCK Permeability:	1.2017152585030999e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	108.62925720214844%
Volume Distribution (VD):	0.465
Pgp-substrate:	3.600834369659424%

ADMET: Metabolism

CYP1A2-inhibitor:	0.671
CYP1A2-substrate:	0.394
CYP2C19-inhibitor:	0.583
CYP2C19-substrate:	0.234
CYP2C9-inhibitor:	0.692
CYP2C9-substrate:	1.0
CYP2D6-inhibitor:	0.857
CYP2D6-substrate:	0.99
CYP3A4-inhibitor:	0.742
CYP3A4-substrate:	0.063

ADMET: Excretion

Clearance (CL):	-0.216
Half-life (T1/2):	0.041

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.484
Drug-inuced Liver Injury (DILI):	0.628
AMES Toxicity:	0.064
Rat Oral Acute Toxicity:	0.14
Maximum Recommended Daily Dose:	0.852
Skin Sensitization:	0.636
Carcinogencity:	0.309
Eye Corrosion:	0.003
Eye Irritation:	0.422
Respiratory Toxicity:	0.198

Download Data

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

Natural Product: NPC254886

Natural Product ID:	NPC254886
*Common Name:**	(2E,4E,6E,8E,10E,12E,14E,16E,18E,20E,22E,24E)-2,6,10,14,19,23-Hexamethyl-25-(2,6,6-Trimethylcyclohexen-1-Yl)Pentacosa-2,4,6,8,10,12,14,16,18,20,22,24-Dodecaenoic Acid
IUPAC Name:	(2E,4E,6E,8E,10E,12E,14E,16E,18E,20E,22E,24E)-2,6,10,14,19,23-hexamethyl-25-(2,6,6-trimethylcyclohexen-1-yl)pentacosa-2,4,6,8,10,12,14,16,18,20,22,24-dodecaenoic acid
Synonyms:
Standard InCHIKey:	NESPPCWGYRQEJQ-VATUXEBJSA-N
Standard InCHI:	InChI=1S/C40H52O2/c1-31(19-12-21-33(3)22-13-23-34(4)25-15-26-37(7)39(41)42)17-10-11-18-32(2)20-14-24-35(5)28-29-38-36(6)27-16-30-40(38,8)9/h10-15,17-26,28-29H,16,27,30H2,1-9H3,(H,41,42)/b11-10+,19-12+,20-14+,22-13+,25-15+,29-28+,31-17+,32-18+,33-21+,34-23+,35-24+,37-26+
SMILES:	C/C(=CC=CC=C(/C)C=CC=C(/C)C=CC1=C(C)CCCC1(C)C)/C=C/C=C(C)/C=C/C=C(C)/C=C/C=C(C)/C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1980160
PubChem CID:	5281248
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001554] Tetraterpenoids [CHEMONTID:0001277] Carotenoids [CHEMONTID:0001410] Xanthophylls

*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
NPO12471	Rhodotorula mucilaginosa	Species	Sporidiobolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23490182]
NPO10874	Selaginella sanguinolenta	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10227	Erythrina lithosperma	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5275	Liriope muscari	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10874	Selaginella sanguinolenta	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10227	Erythrina lithosperma	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5275	Liriope muscari	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1640	Polyporus fibrillosus	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9767	Ferula badhysi	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10874	Selaginella sanguinolenta	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11109	Pityrogramma pallida	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2503	Eucomis bicolor	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10074	Asterospicularia randalli	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10227	Erythrina lithosperma	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5275	Liriope muscari	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12471	Rhodotorula mucilaginosa	Species	Sporidiobolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6682	Stenocereus stellatus	Species	Cactaceae	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
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT572	Cell Line	DMS-273	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT573	Cell Line	M19-MEL	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT574	Cell Line	XF498	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT575	Cell Line	KM-20L2	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	69023.98	nM	PMID[534586]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT576	Cell Line	DMS-114	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT731	Cell Line	LXFL 529	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT577	Cell Line	RXF 631	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT578	Cell Line	SNB-78	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT579	Cell Line	DLD-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[534586]
NPT732	Cell Line	HOP-18	Homo sapiens	GI50	n.a.	10.0	nM	PMID[534586]

☑ 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 NPC254886 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	167
0.1-0.2	1472
0.2-0.3	10932
0.3-0.4	16813
0.4-0.5	8422
0.5-0.6	4092
0.6-0.7	709
0.7-0.8	83
0.8-0.85	2
0.85-0.9	0
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9194	High Similarity	NPC329416
0.9194	High Similarity	NPC317025
0.9194	High Similarity	NPC317177
0.9194	High Similarity	NPC326645
0.8088	Intermediate Similarity	NPC242945
0.8088	Intermediate Similarity	NPC255781
0.8088	Intermediate Similarity	NPC259156
0.7941	Intermediate Similarity	NPC107258
0.7794	Intermediate Similarity	NPC226066
0.7703	Intermediate Similarity	NPC476346
0.7632	Intermediate Similarity	NPC169095
0.7595	Intermediate Similarity	NPC279639
0.7595	Intermediate Similarity	NPC3856
0.7571	Intermediate Similarity	NPC81907
0.7568	Intermediate Similarity	NPC213223
0.7538	Intermediate Similarity	NPC55412
0.7538	Intermediate Similarity	NPC249645
0.7536	Intermediate Similarity	NPC4638
0.7531	Intermediate Similarity	NPC211892
0.75	Intermediate Similarity	NPC87552
0.7468	Intermediate Similarity	NPC469799
0.7468	Intermediate Similarity	NPC469805
0.7468	Intermediate Similarity	NPC469804
0.7468	Intermediate Similarity	NPC324170
0.7468	Intermediate Similarity	NPC469806
0.7467	Intermediate Similarity	NPC166018
0.7467	Intermediate Similarity	NPC169056
0.7467	Intermediate Similarity	NPC225665
0.7432	Intermediate Similarity	NPC56747
0.7432	Intermediate Similarity	NPC180015
0.7432	Intermediate Similarity	NPC109576
0.7432	Intermediate Similarity	NPC276336
0.7432	Intermediate Similarity	NPC130016
0.7432	Intermediate Similarity	NPC153660
0.7424	Intermediate Similarity	NPC281986
0.7424	Intermediate Similarity	NPC22019
0.7424	Intermediate Similarity	NPC283502
0.7424	Intermediate Similarity	NPC208749
0.7424	Intermediate Similarity	NPC321568
0.7407	Intermediate Similarity	NPC109528
0.7368	Intermediate Similarity	NPC19907
0.7344	Intermediate Similarity	NPC69898
0.7344	Intermediate Similarity	NPC295777
0.7324	Intermediate Similarity	NPC142423
0.7324	Intermediate Similarity	NPC308294
0.7302	Intermediate Similarity	NPC43053
0.7297	Intermediate Similarity	NPC133253
0.7297	Intermediate Similarity	NPC21944
0.7297	Intermediate Similarity	NPC257618
0.7297	Intermediate Similarity	NPC95863
0.7286	Intermediate Similarity	NPC150162
0.7273	Intermediate Similarity	NPC262747
0.7273	Intermediate Similarity	NPC473756
0.725	Intermediate Similarity	NPC3511
0.725	Intermediate Similarity	NPC472867
0.725	Intermediate Similarity	NPC142253
0.725	Intermediate Similarity	NPC472239
0.7237	Intermediate Similarity	NPC68624
0.7237	Intermediate Similarity	NPC228978
0.7231	Intermediate Similarity	NPC474127
0.7229	Intermediate Similarity	NPC476293
0.7215	Intermediate Similarity	NPC469798
0.7215	Intermediate Similarity	NPC160582
0.7215	Intermediate Similarity	NPC469797
0.7179	Intermediate Similarity	NPC198240
0.7179	Intermediate Similarity	NPC209135
0.7179	Intermediate Similarity	NPC474816
0.7162	Intermediate Similarity	NPC203819
0.716	Intermediate Similarity	NPC97913
0.7143	Intermediate Similarity	NPC4509
0.7101	Intermediate Similarity	NPC176621
0.7093	Intermediate Similarity	NPC474018
0.7093	Intermediate Similarity	NPC473986
0.7083	Intermediate Similarity	NPC185587
0.7073	Intermediate Similarity	NPC472865
0.7073	Intermediate Similarity	NPC474865
0.7073	Intermediate Similarity	NPC470800
0.7073	Intermediate Similarity	NPC164577
0.7067	Intermediate Similarity	NPC181587
0.7067	Intermediate Similarity	NPC288667
0.7051	Intermediate Similarity	NPC132542
0.7051	Intermediate Similarity	NPC61952
0.7051	Intermediate Similarity	NPC97377
0.7037	Intermediate Similarity	NPC224455
0.7027	Intermediate Similarity	NPC136473
0.7013	Intermediate Similarity	NPC472327
0.7013	Intermediate Similarity	NPC476844
0.7013	Intermediate Similarity	NPC476795
0.7	Intermediate Similarity	NPC469728
0.6988	Remote Similarity	NPC329630
0.6988	Remote Similarity	NPC8571
0.6986	Remote Similarity	NPC106613
0.6962	Remote Similarity	NPC179028
0.6951	Remote Similarity	NPC57370
0.6951	Remote Similarity	NPC49019
0.6951	Remote Similarity	NPC474809
0.6941	Remote Similarity	NPC72397
0.6935	Remote Similarity	NPC308331
0.6933	Remote Similarity	NPC316029
0.6923	Remote Similarity	NPC27205
0.6914	Remote Similarity	NPC6663
0.6914	Remote Similarity	NPC475944
0.6905	Remote Similarity	NPC316426
0.6905	Remote Similarity	NPC315395
0.6901	Remote Similarity	NPC155849
0.6901	Remote Similarity	NPC322457
0.6897	Remote Similarity	NPC212948
0.6897	Remote Similarity	NPC204341
0.6892	Remote Similarity	NPC117804
0.6883	Remote Similarity	NPC168975
0.6883	Remote Similarity	NPC301065
0.6883	Remote Similarity	NPC75485
0.6883	Remote Similarity	NPC3753
0.6883	Remote Similarity	NPC237591
0.6875	Remote Similarity	NPC221467
0.6875	Remote Similarity	NPC190211
0.6867	Remote Similarity	NPC31086
0.6867	Remote Similarity	NPC16287
0.6867	Remote Similarity	NPC178025
0.6867	Remote Similarity	NPC472864
0.6867	Remote Similarity	NPC471301
0.6867	Remote Similarity	NPC181743
0.6867	Remote Similarity	NPC19849
0.6867	Remote Similarity	NPC302360
0.686	Remote Similarity	NPC118011
0.686	Remote Similarity	NPC36668
0.6849	Remote Similarity	NPC322035
0.6849	Remote Similarity	NPC100719
0.6849	Remote Similarity	NPC166791
0.6842	Remote Similarity	NPC160817
0.6829	Remote Similarity	NPC323251
0.6829	Remote Similarity	NPC16321
0.6829	Remote Similarity	NPC471298
0.6824	Remote Similarity	NPC236618
0.6824	Remote Similarity	NPC476409
0.6824	Remote Similarity	NPC199382
0.6818	Remote Similarity	NPC214697
0.6818	Remote Similarity	NPC37644
0.6812	Remote Similarity	NPC254095
0.6806	Remote Similarity	NPC329698
0.6795	Remote Similarity	NPC313179
0.6795	Remote Similarity	NPC65650
0.6795	Remote Similarity	NPC171148
0.6795	Remote Similarity	NPC69383
0.679	Remote Similarity	NPC74086
0.679	Remote Similarity	NPC281880
0.6786	Remote Similarity	NPC60350
0.6786	Remote Similarity	NPC471300
0.6786	Remote Similarity	NPC474860
0.6782	Remote Similarity	NPC182136
0.6782	Remote Similarity	NPC19771
0.6757	Remote Similarity	NPC45782
0.6753	Remote Similarity	NPC12815
0.6753	Remote Similarity	NPC222244
0.6753	Remote Similarity	NPC476490
0.6753	Remote Similarity	NPC16349
0.6753	Remote Similarity	NPC476489
0.6753	Remote Similarity	NPC215745
0.6753	Remote Similarity	NPC238948
0.6753	Remote Similarity	NPC35656
0.675	Remote Similarity	NPC475994
0.675	Remote Similarity	NPC105197
0.675	Remote Similarity	NPC74410
0.675	Remote Similarity	NPC471409
0.675	Remote Similarity	NPC239098
0.675	Remote Similarity	NPC275494
0.6747	Remote Similarity	NPC118423
0.6747	Remote Similarity	NPC102197
0.6747	Remote Similarity	NPC161045
0.6747	Remote Similarity	NPC79945
0.6747	Remote Similarity	NPC16488
0.6747	Remote Similarity	NPC474790
0.6747	Remote Similarity	NPC471297
0.6747	Remote Similarity	NPC474976
0.6744	Remote Similarity	NPC229612
0.6744	Remote Similarity	NPC7280
0.6719	Remote Similarity	NPC17810
0.6712	Remote Similarity	NPC471556
0.6712	Remote Similarity	NPC471565
0.6711	Remote Similarity	NPC469660
0.6711	Remote Similarity	NPC286154
0.6711	Remote Similarity	NPC315597
0.6709	Remote Similarity	NPC474463
0.6709	Remote Similarity	NPC180886
0.6709	Remote Similarity	NPC309399
0.6707	Remote Similarity	NPC40228
0.6707	Remote Similarity	NPC474980
0.6707	Remote Similarity	NPC159148
0.6707	Remote Similarity	NPC315731
0.6707	Remote Similarity	NPC278459
0.6706	Remote Similarity	NPC472869
0.6706	Remote Similarity	NPC186975
0.6703	Remote Similarity	NPC251579
0.6703	Remote Similarity	NPC99726
0.6703	Remote Similarity	NPC141401
0.6703	Remote Similarity	NPC133135
0.6667	Remote Similarity	NPC126518
0.6667	Remote Similarity	NPC251970
0.6667	Remote Similarity	NPC262043
0.6667	Remote Similarity	NPC146554

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 NPC254886 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	139
0.1-0.2	1924
0.2-0.3	4436
0.3-0.4	1979
0.4-0.5	512
0.5-0.6	142
0.6-0.7	10
0.7-0.8	4
0.8-0.85	0
0.85-0.9	0
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9194	High Similarity	NPD4193	Approved
0.9194	High Similarity	NPD4194	Approved
0.9194	High Similarity	NPD4192	Approved
0.9194	High Similarity	NPD4191	Approved
0.7794	Intermediate Similarity	NPD5325	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD4219	Approved
0.7258	Intermediate Similarity	NPD4220	Pre-registration
0.7237	Intermediate Similarity	NPD8039	Approved
0.6795	Remote Similarity	NPD8264	Approved
0.679	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD8262	Approved
0.6667	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD4058	Approved
0.642	Remote Similarity	NPD4756	Discovery
0.64	Remote Similarity	NPD7331	Phase 2
0.6389	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD6404	Discontinued
0.6341	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD7637	Suspended
0.625	Remote Similarity	NPD5733	Approved
0.625	Remote Similarity	NPD39	Approved
0.625	Remote Similarity	NPD4687	Approved
0.6222	Remote Similarity	NPD7838	Discovery
0.6207	Remote Similarity	NPD1696	Phase 3
0.6203	Remote Similarity	NPD5276	Approved
0.6163	Remote Similarity	NPD3971	Phase 1
0.6154	Remote Similarity	NPD5281	Approved
0.6154	Remote Similarity	NPD5284	Approved
0.6145	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD4623	Approved
0.6136	Remote Similarity	NPD4519	Discontinued
0.6129	Remote Similarity	NPD6049	Phase 2
0.6129	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD5778	Approved
0.6087	Remote Similarity	NPD5779	Approved
0.6076	Remote Similarity	NPD4691	Approved
0.6071	Remote Similarity	NPD4195	Approved
0.6053	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD5209	Approved
0.6044	Remote Similarity	NPD5785	Approved
0.604	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD5363	Approved
0.6	Remote Similarity	NPD3194	Approved
0.6	Remote Similarity	NPD3196	Approved
0.6	Remote Similarity	NPD3195	Phase 2
0.6	Remote Similarity	NPD4266	Approved
0.6	Remote Similarity	NPD7332	Phase 2
0.6	Remote Similarity	NPD7514	Phase 3
0.6	Remote Similarity	NPD4695	Discontinued
0.5978	Remote Similarity	NPD6411	Approved
0.5976	Remote Similarity	NPD9716	Approved
0.5952	Remote Similarity	NPD7145	Approved
0.5949	Remote Similarity	NPD4137	Phase 3
0.5938	Remote Similarity	NPD5326	Phase 3
0.593	Remote Similarity	NPD6902	Approved
0.589	Remote Similarity	NPD287	Approved
0.5875	Remote Similarity	NPD7143	Approved
0.5875	Remote Similarity	NPD4747	Approved
0.5875	Remote Similarity	NPD7144	Approved
0.5857	Remote Similarity	NPD3172	Approved
0.5851	Remote Similarity	NPD7748	Approved
0.5844	Remote Similarity	NPD7341	Phase 2
0.5833	Remote Similarity	NPD5776	Phase 2
0.5833	Remote Similarity	NPD6925	Approved
0.5824	Remote Similarity	NPD4518	Approved
0.5814	Remote Similarity	NPD4822	Approved
0.5814	Remote Similarity	NPD4819	Approved
0.5814	Remote Similarity	NPD4821	Approved
0.5814	Remote Similarity	NPD4820	Approved
0.5806	Remote Similarity	NPD7515	Phase 2
0.5806	Remote Similarity	NPD7983	Approved
0.5802	Remote Similarity	NPD7152	Approved
0.5802	Remote Similarity	NPD7151	Approved
0.5802	Remote Similarity	NPD7150	Approved
0.5795	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.5795	Remote Similarity	NPD7154	Phase 3
0.5795	Remote Similarity	NPD5332	Approved
0.5795	Remote Similarity	NPD5362	Discontinued
0.5795	Remote Similarity	NPD5331	Approved
0.5778	Remote Similarity	NPD5280	Approved
0.5778	Remote Similarity	NPD5279	Phase 3
0.5778	Remote Similarity	NPD5690	Phase 2
0.5778	Remote Similarity	NPD4694	Approved
0.5773	Remote Similarity	NPD4225	Approved
0.5765	Remote Similarity	NPD4271	Approved
0.5765	Remote Similarity	NPD4268	Approved
0.5761	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD6101	Approved
0.5758	Remote Similarity	NPD4222	Approved
0.575	Remote Similarity	NPD6922	Approved
0.575	Remote Similarity	NPD6923	Approved
0.5747	Remote Similarity	NPD4790	Discontinued
0.5735	Remote Similarity	NPD3173	Approved
0.5732	Remote Similarity	NPD4732	Discontinued
0.5729	Remote Similarity	NPD7839	Suspended
0.5714	Remote Similarity	NPD7640	Approved
0.5714	Remote Similarity	NPD7639	Approved
0.5714	Remote Similarity	NPD6648	Approved
0.5714	Remote Similarity	NPD3573	Approved
0.5699	Remote Similarity	NPD5207	Approved
0.5698	Remote Similarity	NPD6929	Approved
0.5696	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5696	Remote Similarity	NPD3709	Clinical (unspecified phase)
0.5694	Remote Similarity	NPD342	Phase 1
0.5692	Remote Similarity	NPD9411	Phase 1
0.5682	Remote Similarity	NPD4269	Approved
0.5682	Remote Similarity	NPD4223	Phase 3
0.5682	Remote Similarity	NPD4270	Approved
0.5682	Remote Similarity	NPD4221	Approved
0.567	Remote Similarity	NPD7902	Approved
0.5667	Remote Similarity	NPD5329	Approved
0.5667	Remote Similarity	NPD1694	Approved
0.5663	Remote Similarity	NPD6926	Approved
0.5663	Remote Similarity	NPD6924	Approved
0.5658	Remote Similarity	NPD368	Approved
0.5647	Remote Similarity	NPD6932	Approved
0.5638	Remote Similarity	NPD5694	Approved
0.5638	Remote Similarity	NPD6079	Approved
0.5638	Remote Similarity	NPD6050	Approved
0.5632	Remote Similarity	NPD6931	Approved
0.5632	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5632	Remote Similarity	NPD6930	Phase 2
0.5632	Remote Similarity	NPD4252	Approved
0.5612	Remote Similarity	NPD7638	Approved
0.5604	Remote Similarity	NPD7146	Approved
0.5604	Remote Similarity	NPD5330	Approved
0.5604	Remote Similarity	NPD7334	Approved
0.5604	Remote Similarity	NPD6684	Approved
0.5604	Remote Similarity	NPD6409	Approved
0.5604	Remote Similarity	NPD7521	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