NPASS Compound

Structure

CID225415 OpenBabel06191716022D 31 31 0 0 1 0 0 0 0 0999 V2000 12.9904 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.8564 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 3.0000 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 1.7321 -2.0000 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 -0.5000 0.8660 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 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1244 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 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 10.3923 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 1.5000 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 0.0000 -2.0000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9904 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 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 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 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 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 6 27 2 0 0 0 0 7 30 1 0 0 0 0 8 30 1 0 0 0 0 9 10 1 0 0 0 0 9 14 1 0 0 0 0 10 15 1 0 0 0 0 11 13 1 0 0 0 0 11 16 1 0 0 0 0 12 17 1 0 0 0 0 12 18 1 0 0 0 0 13 23 2 0 0 0 0 14 24 2 0 0 0 0 15 26 2 0 0 0 0 16 25 1 0 0 0 0 17 24 1 0 0 0 0 18 25 2 0 0 0 0 19 21 1 0 0 0 0 19 26 1 0 0 0 0 20 22 1 0 0 0 0 20 27 1 0 0 0 0 22 29 1 0 0 0 0 27 28 1 0 0 0 0 28 21 1 6 0 0 0 28 30 1 0 0 0 0 29 30 1 0 0 0 0 29 31 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	426.39
Volume:	514.487
LogP:	8.513
LogD:	6.216
LogS:	-6.11
# Rotatable Bonds:	12
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.243
Synthetic Accessibility Score:	4.107
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.856
MDCK Permeability:	1.4453519725066144e-05
Pgp-inhibitor:	0.378
Pgp-substrate:	0.041
Human Intestinal Absorption (HIA):	0.034
20% Bioavailability (F20%):	0.961
30% Bioavailability (F30%):	0.877

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.571
Plasma Protein Binding (PPB):	96.52234649658203%
Volume Distribution (VD):	1.943
Pgp-substrate:	1.2042425870895386%

ADMET: Metabolism

CYP1A2-inhibitor:	0.099
CYP1A2-substrate:	0.173
CYP2C19-inhibitor:	0.2
CYP2C19-substrate:	0.071
CYP2C9-inhibitor:	0.216
CYP2C9-substrate:	0.968
CYP2D6-inhibitor:	0.159
CYP2D6-substrate:	0.49
CYP3A4-inhibitor:	0.467
CYP3A4-substrate:	0.176

ADMET: Excretion

Clearance (CL):	4.524
Half-life (T1/2):	0.053

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.303
Drug-inuced Liver Injury (DILI):	0.004
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.986
Skin Sensitization:	0.947
Carcinogencity:	0.008
Eye Corrosion:	0.024
Eye Irritation:	0.612
Respiratory Toxicity:	0.041

Download Data

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

Natural Product: NPC225415

Natural Product ID:	NPC225415
*Common Name:**	(1S,3R)-2,2-Dimethyl-4-Methylidene-3-[(3E,7E,11E)-3,8,12,16-Tetramethylheptadeca-3,7,11,15-Tetraenyl]Cyclohexan-1-Ol
IUPAC Name:	(1S,3R)-2,2-dimethyl-4-methylidene-3-[(3E,7E,11E)-3,8,12,16-tetramethylheptadeca-3,7,11,15-tetraenyl]cyclohexan-1-ol
Synonyms:
Standard InCHIKey:	ANKPMKKGZZQDIC-HJSIMFEZSA-N
Standard InCHI:	InChI=1S/C30H50O/c1-23(2)13-11-16-25(4)18-12-17-24(3)14-9-10-15-26(5)19-21-28-27(6)20-22-29(31)30(28,7)8/h13-15,18,28-29,31H,6,9-12,16-17,19-22H2,1-5,7-8H3/b24-14+,25-18+,26-15+/t28-,29+/m1/s1
SMILES:	C/C(=CCC/C=C(/CC[C@@H]1C(=C)CC[C@@H](C1(C)C)O)C)/CC/C=C(/CCC=C(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1977780
PubChem CID:	5471312
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO10318	Myrospermum frutescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12880308]
NPO10318	Myrospermum frutescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497945]
NPO25515	Garcinia speciosa	Species	Clusiaceae	Eukaryota	barks	n.a.	n.a.	PMID[15620248]
NPO4157	Viguiera robusta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO8797	Cudrania tricuspidata	Species	Moraceae	Eukaryota	Root barks	n.a.	n.a.	PMID[25051453]
NPO8797	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27420919]
NPO25515	Garcinia speciosa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9602	Rosa multiflora	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9602	Rosa multiflora	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25515	Garcinia speciosa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8797	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9602	Rosa multiflora	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9602	Rosa multiflora	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9953	Euphorbia condylocarpa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4403	Dendrobium aphyllum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10578	Chloranthus glaber	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10318	Myrospermum frutescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4157	Viguiera robusta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25515	Garcinia speciosa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24841	Justicia prostrata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2160	Silene vulgaris	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8797	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9602	Rosa multiflora	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27330	Mucidula mucida	Species	Physalacriaceae	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
EC50	3
GI50	59

Activity Type	# Activity
Cell Line	59
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	66221.65	nM	PMID[481715]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[481715]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	45708.82	nM	PMID[481715]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[481715]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[481715]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[481715]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	13489.63	nM	PMID[481715]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[481715]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[481715]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	53951.06	nM	PMID[481715]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[481715]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[481715]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[481715]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[481715]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[481715]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[481715]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[481715]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[481715]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	57809.6	nM	PMID[481715]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[481715]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[481715]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[481715]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	59566.21	nM	PMID[481715]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[481715]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[481715]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	28973.44	nM	PMID[481715]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[481715]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[481715]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[481715]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[481715]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[481715]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[481715]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	46665.94	nM	PMID[481715]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[481715]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[481715]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	76559.66	nM	PMID[481715]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	43651.58	nM	PMID[481715]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	87297.14	nM	PMID[481715]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[481715]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	97949.0	nM	PMID[481715]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	27605.78	nM	PMID[481715]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[481715]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[481715]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	18749.95	nM	PMID[481715]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[481715]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[481715]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[481715]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[481715]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[481715]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[481715]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[481715]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[481715]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[481715]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	1815.52	nM	PMID[481715]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	69183.1	nM	PMID[481715]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[481715]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[481715]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[481715]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	13677.29	nM	PMID[481715]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	6500.0	nM	PMID[481716]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	>	50000.0	nM	PMID[481716]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	7200.0	nM	PMID[481716]

☑ 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 NPC225415 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	156
0.1-0.2	1570
0.2-0.3	9093
0.3-0.4	15276
0.4-0.5	7780
0.5-0.6	5887
0.6-0.7	2293
0.7-0.8	545
0.8-0.85	82
0.85-0.9	14
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8939	High Similarity	NPC167706
0.8806	High Similarity	NPC182717
0.8788	High Similarity	NPC145498
0.8769	High Similarity	NPC208999
0.873	High Similarity	NPC290367
0.8676	High Similarity	NPC477138
0.8676	High Similarity	NPC100334
0.8676	High Similarity	NPC243342
0.8676	High Similarity	NPC91858
0.8657	High Similarity	NPC242001
0.8657	High Similarity	NPC110799
0.8551	High Similarity	NPC66566
0.8551	High Similarity	NPC291503
0.8551	High Similarity	NPC477923
0.8529	High Similarity	NPC68443
0.8507	High Similarity	NPC34834
0.8507	High Similarity	NPC92801
0.8485	Intermediate Similarity	NPC96484
0.8462	Intermediate Similarity	NPC149680
0.8438	Intermediate Similarity	NPC309300
0.8429	Intermediate Similarity	NPC290598
0.8429	Intermediate Similarity	NPC167873
0.8429	Intermediate Similarity	NPC237460
0.8429	Intermediate Similarity	NPC202642
0.8429	Intermediate Similarity	NPC189883
0.8429	Intermediate Similarity	NPC27765
0.8429	Intermediate Similarity	NPC46160
0.8429	Intermediate Similarity	NPC122418
0.8429	Intermediate Similarity	NPC120098
0.8429	Intermediate Similarity	NPC265588
0.8429	Intermediate Similarity	NPC1973
0.8429	Intermediate Similarity	NPC30590
0.8429	Intermediate Similarity	NPC265328
0.8413	Intermediate Similarity	NPC475251
0.8406	Intermediate Similarity	NPC476366
0.8406	Intermediate Similarity	NPC306727
0.8406	Intermediate Similarity	NPC78527
0.8406	Intermediate Similarity	NPC201048
0.8382	Intermediate Similarity	NPC477792
0.8382	Intermediate Similarity	NPC164022
0.8333	Intermediate Similarity	NPC114651
0.8333	Intermediate Similarity	NPC197805
0.8333	Intermediate Similarity	NPC69649
0.8333	Intermediate Similarity	NPC68703
0.831	Intermediate Similarity	NPC472805
0.831	Intermediate Similarity	NPC34177
0.831	Intermediate Similarity	NPC40394
0.831	Intermediate Similarity	NPC470711
0.831	Intermediate Similarity	NPC214570
0.831	Intermediate Similarity	NPC101475
0.831	Intermediate Similarity	NPC477924
0.831	Intermediate Similarity	NPC470758
0.831	Intermediate Similarity	NPC130136
0.831	Intermediate Similarity	NPC90979
0.831	Intermediate Similarity	NPC157996
0.831	Intermediate Similarity	NPC91594
0.831	Intermediate Similarity	NPC471798
0.8308	Intermediate Similarity	NPC477009
0.8308	Intermediate Similarity	NPC238352
0.8286	Intermediate Similarity	NPC138374
0.8286	Intermediate Similarity	NPC141071
0.8286	Intermediate Similarity	NPC32832
0.8286	Intermediate Similarity	NPC34700
0.8286	Intermediate Similarity	NPC118508
0.8286	Intermediate Similarity	NPC257347
0.8286	Intermediate Similarity	NPC471723
0.8286	Intermediate Similarity	NPC121744
0.8286	Intermediate Similarity	NPC322353
0.8261	Intermediate Similarity	NPC471799
0.8261	Intermediate Similarity	NPC474140
0.8209	Intermediate Similarity	NPC160209
0.8209	Intermediate Similarity	NPC94192
0.8209	Intermediate Similarity	NPC471238
0.8209	Intermediate Similarity	NPC216460
0.8194	Intermediate Similarity	NPC302041
0.8194	Intermediate Similarity	NPC318136
0.8194	Intermediate Similarity	NPC167037
0.8194	Intermediate Similarity	NPC98386
0.8194	Intermediate Similarity	NPC244385
0.8194	Intermediate Similarity	NPC158662
0.8194	Intermediate Similarity	NPC6978
0.8194	Intermediate Similarity	NPC85346
0.8194	Intermediate Similarity	NPC474989
0.8194	Intermediate Similarity	NPC65897
0.8194	Intermediate Similarity	NPC138621
0.8194	Intermediate Similarity	NPC253807
0.8194	Intermediate Similarity	NPC312328
0.8194	Intermediate Similarity	NPC470396
0.8194	Intermediate Similarity	NPC285761
0.8194	Intermediate Similarity	NPC186191
0.8194	Intermediate Similarity	NPC275910
0.8194	Intermediate Similarity	NPC22955
0.8194	Intermediate Similarity	NPC300499
0.8194	Intermediate Similarity	NPC205455
0.8194	Intermediate Similarity	NPC99168
0.8194	Intermediate Similarity	NPC196753
0.8194	Intermediate Similarity	NPC230295
0.8182	Intermediate Similarity	NPC286669
0.8182	Intermediate Similarity	NPC222366
0.8182	Intermediate Similarity	NPC476039
0.8169	Intermediate Similarity	NPC477925
0.8169	Intermediate Similarity	NPC470362
0.8169	Intermediate Similarity	NPC274079
0.8169	Intermediate Similarity	NPC470749
0.8169	Intermediate Similarity	NPC134330
0.8169	Intermediate Similarity	NPC73875
0.8169	Intermediate Similarity	NPC106432
0.8169	Intermediate Similarity	NPC106364
0.8169	Intermediate Similarity	NPC300324
0.8169	Intermediate Similarity	NPC240604
0.8169	Intermediate Similarity	NPC129165
0.8154	Intermediate Similarity	NPC144650
0.8154	Intermediate Similarity	NPC101128
0.8154	Intermediate Similarity	NPC219940
0.8154	Intermediate Similarity	NPC96793
0.8154	Intermediate Similarity	NPC323424
0.8143	Intermediate Similarity	NPC27395
0.8143	Intermediate Similarity	NPC329090
0.8143	Intermediate Similarity	NPC471797
0.8143	Intermediate Similarity	NPC469533
0.8143	Intermediate Similarity	NPC469593
0.8143	Intermediate Similarity	NPC469534
0.8116	Intermediate Similarity	NPC471268
0.8116	Intermediate Similarity	NPC471272
0.8116	Intermediate Similarity	NPC471271
0.8088	Intermediate Similarity	NPC167272
0.8088	Intermediate Similarity	NPC474248
0.8088	Intermediate Similarity	NPC476431
0.8088	Intermediate Similarity	NPC269877
0.8088	Intermediate Similarity	NPC9942
0.8082	Intermediate Similarity	NPC80530
0.8082	Intermediate Similarity	NPC1319
0.8082	Intermediate Similarity	NPC53744
0.8082	Intermediate Similarity	NPC472463
0.8082	Intermediate Similarity	NPC291379
0.8082	Intermediate Similarity	NPC273410
0.8056	Intermediate Similarity	NPC470428
0.8056	Intermediate Similarity	NPC31037
0.8033	Intermediate Similarity	NPC84824
0.8033	Intermediate Similarity	NPC67508
0.803	Intermediate Similarity	NPC2728
0.803	Intermediate Similarity	NPC282619
0.803	Intermediate Similarity	NPC300442
0.803	Intermediate Similarity	NPC208198
0.803	Intermediate Similarity	NPC172613
0.803	Intermediate Similarity	NPC19569
0.803	Intermediate Similarity	NPC163678
0.803	Intermediate Similarity	NPC11555
0.803	Intermediate Similarity	NPC60837
0.8028	Intermediate Similarity	NPC285893
0.8028	Intermediate Similarity	NPC304309
0.8028	Intermediate Similarity	NPC230301
0.8028	Intermediate Similarity	NPC28657
0.8028	Intermediate Similarity	NPC22105
0.8028	Intermediate Similarity	NPC134847
0.8028	Intermediate Similarity	NPC328104
0.8028	Intermediate Similarity	NPC288035
0.8028	Intermediate Similarity	NPC162742
0.8028	Intermediate Similarity	NPC319090
0.8028	Intermediate Similarity	NPC136188
0.8	Intermediate Similarity	NPC201373
0.7973	Intermediate Similarity	NPC322313
0.7973	Intermediate Similarity	NPC236237
0.7973	Intermediate Similarity	NPC281880
0.7973	Intermediate Similarity	NPC13554
0.7973	Intermediate Similarity	NPC102253
0.7973	Intermediate Similarity	NPC287749
0.7973	Intermediate Similarity	NPC295131
0.7973	Intermediate Similarity	NPC236112
0.7973	Intermediate Similarity	NPC96362
0.7971	Intermediate Similarity	NPC49422
0.7971	Intermediate Similarity	NPC9161
0.7971	Intermediate Similarity	NPC45296
0.7945	Intermediate Similarity	NPC72507
0.7945	Intermediate Similarity	NPC11908
0.7945	Intermediate Similarity	NPC476314
0.7945	Intermediate Similarity	NPC476949
0.7941	Intermediate Similarity	NPC32055
0.7917	Intermediate Similarity	NPC247325
0.7917	Intermediate Similarity	NPC107059
0.7917	Intermediate Similarity	NPC113733
0.7917	Intermediate Similarity	NPC321016
0.7917	Intermediate Similarity	NPC321381
0.7917	Intermediate Similarity	NPC253190
0.7917	Intermediate Similarity	NPC250621
0.7917	Intermediate Similarity	NPC315261
0.7917	Intermediate Similarity	NPC244488
0.791	Intermediate Similarity	NPC279434
0.791	Intermediate Similarity	NPC250977
0.791	Intermediate Similarity	NPC476406
0.791	Intermediate Similarity	NPC473929
0.791	Intermediate Similarity	NPC202017
0.7879	Intermediate Similarity	NPC68656
0.7867	Intermediate Similarity	NPC476646
0.7867	Intermediate Similarity	NPC159148
0.7867	Intermediate Similarity	NPC242350
0.7867	Intermediate Similarity	NPC249423
0.7867	Intermediate Similarity	NPC142163
0.7867	Intermediate Similarity	NPC474531
0.7857	Intermediate Similarity	NPC301226

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 NPC225415 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	153
0.1-0.2	2165
0.2-0.3	4126
0.3-0.4	1899
0.4-0.5	469
0.5-0.6	255
0.6-0.7	58
0.7-0.8	25
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8143	Intermediate Similarity	NPD6926	Approved
0.8143	Intermediate Similarity	NPD6924	Approved
0.8088	Intermediate Similarity	NPD6922	Approved
0.8088	Intermediate Similarity	NPD6923	Approved
0.8082	Intermediate Similarity	NPD7645	Phase 2
0.8028	Intermediate Similarity	NPD6942	Approved
0.8028	Intermediate Similarity	NPD7339	Approved
0.7973	Intermediate Similarity	NPD7525	Registered
0.7971	Intermediate Similarity	NPD7144	Approved
0.7971	Intermediate Similarity	NPD7143	Approved
0.7917	Intermediate Similarity	NPD6933	Approved
0.7857	Intermediate Similarity	NPD7150	Approved
0.7857	Intermediate Similarity	NPD7151	Approved
0.7857	Intermediate Similarity	NPD7152	Approved
0.7733	Intermediate Similarity	NPD7509	Discontinued
0.7671	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD6929	Approved
0.7534	Intermediate Similarity	NPD8264	Approved
0.75	Intermediate Similarity	NPD6931	Approved
0.75	Intermediate Similarity	NPD6930	Phase 2
0.7361	Intermediate Similarity	NPD4243	Approved
0.7333	Intermediate Similarity	NPD6925	Approved
0.7333	Intermediate Similarity	NPD5776	Phase 2
0.7333	Intermediate Similarity	NPD6932	Approved
0.7313	Intermediate Similarity	NPD368	Approved
0.7237	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD7145	Approved
0.7215	Intermediate Similarity	NPD6695	Phase 3
0.7188	Intermediate Similarity	NPD342	Phase 1
0.7162	Intermediate Similarity	NPD4785	Approved
0.7162	Intermediate Similarity	NPD4784	Approved
0.716	Intermediate Similarity	NPD3618	Phase 1
0.7143	Intermediate Similarity	NPD6683	Phase 2
0.7125	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD4786	Approved
0.7108	Intermediate Similarity	NPD5328	Approved
0.7089	Intermediate Similarity	NPD3667	Approved
0.7051	Intermediate Similarity	NPD7514	Phase 3
0.7051	Intermediate Similarity	NPD7332	Phase 2
0.7037	Intermediate Similarity	NPD6893	Approved
0.7	Intermediate Similarity	NPD385	Approved
0.7	Intermediate Similarity	NPD384	Approved
0.6962	Remote Similarity	NPD6902	Approved
0.6962	Remote Similarity	NPD6898	Phase 1
0.6941	Remote Similarity	NPD6079	Approved
0.6941	Remote Similarity	NPD7515	Phase 2
0.6914	Remote Similarity	NPD3133	Approved
0.6914	Remote Similarity	NPD3666	Approved
0.6914	Remote Similarity	NPD3665	Phase 1
0.6867	Remote Similarity	NPD7524	Approved
0.6867	Remote Similarity	NPD7750	Discontinued
0.6842	Remote Similarity	NPD5275	Approved
0.6842	Remote Similarity	NPD4190	Phase 3
0.6835	Remote Similarity	NPD4748	Discontinued
0.6818	Remote Similarity	NPD4219	Approved
0.6747	Remote Similarity	NPD5279	Phase 3
0.6667	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4202	Approved
0.6627	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD7748	Approved
0.6552	Remote Similarity	NPD7087	Discontinued
0.6552	Remote Similarity	NPD6411	Approved
0.65	Remote Similarity	NPD4195	Approved
0.6484	Remote Similarity	NPD7638	Approved
0.6444	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD4697	Phase 3
0.6444	Remote Similarity	NPD5221	Approved
0.6444	Remote Similarity	NPD5222	Approved
0.642	Remote Similarity	NPD4695	Discontinued
0.642	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD7639	Approved
0.6413	Remote Similarity	NPD7640	Approved
0.6375	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD4755	Approved
0.6374	Remote Similarity	NPD7902	Approved
0.6374	Remote Similarity	NPD5173	Approved
0.6364	Remote Similarity	NPD4732	Discontinued
0.6322	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD6101	Approved
0.6322	Remote Similarity	NPD4753	Phase 2
0.631	Remote Similarity	NPD3668	Phase 3
0.6304	Remote Similarity	NPD5290	Discontinued
0.6304	Remote Similarity	NPD4225	Approved
0.6292	Remote Similarity	NPD6399	Phase 3
0.6265	Remote Similarity	NPD4221	Approved
0.6265	Remote Similarity	NPD4223	Phase 3
0.625	Remote Similarity	NPD7136	Phase 2
0.6237	Remote Similarity	NPD4696	Approved
0.6237	Remote Similarity	NPD5285	Approved
0.6237	Remote Similarity	NPD5286	Approved
0.6237	Remote Similarity	NPD4700	Approved
0.6235	Remote Similarity	NPD5329	Approved
0.6216	Remote Similarity	NPD7331	Phase 2
0.619	Remote Similarity	NPD4788	Approved
0.6184	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.618	Remote Similarity	NPD7637	Suspended
0.617	Remote Similarity	NPD5223	Approved
0.6163	Remote Similarity	NPD7334	Approved
0.6163	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD6684	Approved
0.6163	Remote Similarity	NPD5330	Approved
0.6163	Remote Similarity	NPD7146	Approved
0.6163	Remote Similarity	NPD7521	Approved
0.6163	Remote Similarity	NPD6409	Approved
0.6118	Remote Similarity	NPD4197	Approved
0.6111	Remote Similarity	NPD5779	Approved
0.6111	Remote Similarity	NPD5778	Approved
0.6105	Remote Similarity	NPD5226	Approved
0.6105	Remote Similarity	NPD5211	Phase 2
0.6105	Remote Similarity	NPD5224	Approved
0.6105	Remote Similarity	NPD5225	Approved
0.6105	Remote Similarity	NPD4633	Approved
0.6082	Remote Similarity	NPD6402	Approved
0.6082	Remote Similarity	NPD7128	Approved
0.6082	Remote Similarity	NPD5739	Approved
0.6082	Remote Similarity	NPD6675	Approved
0.6081	Remote Similarity	NPD7341	Phase 2
0.6067	Remote Similarity	NPD3168	Discontinued
0.6044	Remote Similarity	NPD7900	Approved
0.6044	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD5174	Approved
0.6042	Remote Similarity	NPD4754	Approved
0.6042	Remote Similarity	NPD5175	Approved
0.6032	Remote Similarity	NPD4265	Approved
0.6024	Remote Similarity	NPD5368	Approved
0.6024	Remote Similarity	NPD4822	Approved
0.6024	Remote Similarity	NPD4821	Approved
0.6024	Remote Similarity	NPD4820	Approved
0.6024	Remote Similarity	NPD4819	Approved
0.6023	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD6903	Approved
0.6022	Remote Similarity	NPD6083	Phase 2
0.6022	Remote Similarity	NPD6084	Phase 2
0.6	Remote Similarity	NPD5362	Discontinued
0.6	Remote Similarity	NPD5344	Discontinued
0.6	Remote Similarity	NPD5331	Approved
0.6	Remote Similarity	NPD9410	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5332	Approved
0.6	Remote Similarity	NPD8035	Phase 2
0.6	Remote Similarity	NPD8034	Phase 2
0.5979	Remote Similarity	NPD5141	Approved
0.5978	Remote Similarity	NPD4629	Approved
0.5978	Remote Similarity	NPD5210	Approved
0.5977	Remote Similarity	NPD4623	Approved
0.5977	Remote Similarity	NPD4519	Discontinued
0.5977	Remote Similarity	NPD5280	Approved
0.5977	Remote Similarity	NPD4689	Approved
0.5977	Remote Similarity	NPD4694	Approved
0.5977	Remote Similarity	NPD4693	Phase 3
0.5977	Remote Similarity	NPD5205	Approved
0.5977	Remote Similarity	NPD4690	Approved
0.5977	Remote Similarity	NPD4138	Approved
0.5977	Remote Similarity	NPD4688	Approved
0.5977	Remote Similarity	NPD5690	Phase 2
0.5976	Remote Similarity	NPD4268	Approved
0.5976	Remote Similarity	NPD3617	Approved
0.5976	Remote Similarity	NPD4271	Approved
0.596	Remote Similarity	NPD7320	Approved
0.596	Remote Similarity	NPD6881	Approved
0.596	Remote Similarity	NPD6899	Approved
0.5955	Remote Similarity	NPD6051	Approved
0.5952	Remote Similarity	NPD4790	Discontinued
0.5952	Remote Similarity	NPD5369	Approved
0.593	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD4767	Approved
0.5918	Remote Similarity	NPD4768	Approved
0.59	Remote Similarity	NPD6373	Approved
0.59	Remote Similarity	NPD6372	Approved
0.5897	Remote Similarity	NPD4787	Phase 1
0.5882	Remote Similarity	NPD4269	Approved
0.5882	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD4270	Approved
0.5882	Remote Similarity	NPD6435	Approved
0.5862	Remote Similarity	NPD1694	Approved
0.5862	Remote Similarity	NPD1696	Phase 3
0.5862	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD5697	Approved
0.5859	Remote Similarity	NPD5701	Approved
0.5843	Remote Similarity	NPD4723	Approved
0.5843	Remote Similarity	NPD5737	Approved
0.5843	Remote Similarity	NPD6672	Approved
0.5843	Remote Similarity	NPD4722	Approved
0.5842	Remote Similarity	NPD6883	Approved
0.5842	Remote Similarity	NPD7102	Approved
0.5842	Remote Similarity	NPD7290	Approved
0.5833	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5823	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.5823	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD7154	Phase 3
0.5806	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD5695	Phase 3
0.5802	Remote Similarity	NPD8039	Approved
0.58	Remote Similarity	NPD5128	Approved
0.58	Remote Similarity	NPD5168	Approved
0.58	Remote Similarity	NPD4729	Approved
0.58	Remote Similarity	NPD6011	Approved
0.58	Remote Similarity	NPD4730	Approved
0.5784	Remote Similarity	NPD6649	Approved
0.5784	Remote Similarity	NPD6650	Approved
0.5784	Remote Similarity	NPD6847	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