NPASS Compound

Structure

CID152186 OpenBabel06191715522D 24 25 0 0 0 0 0 0 0 0999 V2000 13.0754 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.2094 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8793 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7453 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6113 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3434 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.2094 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4773 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4773 -1.1910 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 11.3434 0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 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 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 8 10 2 0 0 0 0 9 17 1 0 0 0 0 10 20 1 0 0 0 0 11 12 2 0 0 0 0 11 17 1 0 0 0 0 12 18 1 0 0 0 0 13 17 2 0 0 0 0 13 19 1 0 0 0 0 14 16 1 0 0 0 0 14 21 1 0 0 0 0 15 23 1 0 0 0 0 15 24 1 0 0 0 0 18 19 2 0 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 20 21 2 3 0 0 0 20 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	329.2
Volume:	358.912
LogP:	4.343
LogD:	4.141
LogS:	-4.442
# Rotatable Bonds:	10
TPSA:	47.56
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.542
Synthetic Accessibility Score:	2.482
Fsp3:	0.45
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.788
MDCK Permeability:	2.604530891403556e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.223
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.308
Plasma Protein Binding (PPB):	98.01465606689453%
Volume Distribution (VD):	1.15
Pgp-substrate:	1.9090185165405273%

ADMET: Metabolism

CYP1A2-inhibitor:	0.9
CYP1A2-substrate:	0.252
CYP2C19-inhibitor:	0.952
CYP2C19-substrate:	0.45
CYP2C9-inhibitor:	0.807
CYP2C9-substrate:	0.965
CYP2D6-inhibitor:	0.911
CYP2D6-substrate:	0.881
CYP3A4-inhibitor:	0.941
CYP3A4-substrate:	0.177

ADMET: Excretion

Clearance (CL):	11.477
Half-life (T1/2):	0.409

ADMET: Toxicity

hERG Blockers:	0.803
Human Hepatotoxicity (H-HT):	0.249
Drug-inuced Liver Injury (DILI):	0.092
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.253
Skin Sensitization:	0.957
Carcinogencity:	0.658
Eye Corrosion:	0.032
Eye Irritation:	0.459
Respiratory Toxicity:	0.929

Download Data

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

Natural Product: NPC152186

Natural Product ID:	NPC152186
*Common Name:**	Retrofractamide C
IUPAC Name:	(2E,8E)-9-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)nona-2,8-dienamide
Synonyms:
Standard InCHIKey:	PAXQNYHJDFKFEU-FIFLTTCUSA-N
Standard InCHI:	InChI=1S/C20H27NO3/c1-16(2)14-21-20(22)10-8-6-4-3-5-7-9-17-11-12-18-19(13-17)24-15-23-18/h7-13,16H,3-6,14-15H2,1-2H3,(H,21,22)/b9-7+,10-8+
SMILES:	CC(C)CN=C(/C=C/CCCC/C=C/c1ccc2c(c1)OCO2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL271630
PubChem CID:	25255091
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000296] Benzodioxoles

*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
NPO10274	Pothomorphe peltata	n.a.	n.a.	n.a.	n.a.	Dominican Republic	n.a.	PMID[11430019]
NPO6544	Carpesium longifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14695795]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16872768]
NPO3968	Dracontium loretense	Species	Araceae	Eukaryota	corms	Iquitos, Peru	2005-MAY	PMID[19341262]
NPO3968	Dracontium loretense	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19341262]
NPO10666	Verbesina virginica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19485332]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	fruits	n.a.	n.a.	PMID[20839888]
NPO4251	Photorhabdus luminescens	Species	Morganellaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22909174]
NPO12125	Pseudomonas stutzeri	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23149469]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23434420]
NPO6648	Piper retrofractum	Species	Piperaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[23506561]
NPO6648	Piper retrofractum	Species	Piperaceae	Eukaryota	leaves	n.a.	n.a.	PMID[25127165]
NPO4251	Photorhabdus luminescens	Species	Morganellaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25988621]
NPO7158	Schefflera venulosa	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6544	Carpesium longifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6648	Piper retrofractum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6544	Carpesium longifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12383	Frullania brasiliensis	Species	Frullaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27487	Silene banksia	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7158	Schefflera venulosa	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2840	Podocarpus minor	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7536	Mycoplasma mycoides	Species	Mycoplasmataceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO11137	Dichotomanthes tristaniicarpa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO964	Homalium laurifolium	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4251	Photorhabdus luminescens	Species	Morganellaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO9950	Coelogyne nitida	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10459	Brickellia longifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3968	Dracontium loretense	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO230	Palisota barteri	Species	Commelinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10274	Pothomorphe peltata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO11511	Cochlearia officinalis	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9166	Monascus rubropunctatus	Species	Fellodistomidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO43	Leifsonia aquatica	Species	Microbacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO876	Didymosphaeria enalia	Species	Didymosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7158	Schefflera venulosa	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6880	Crocus corsicus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12488	Bupleurum rigidum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23642	Penicillium tardum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6544	Carpesium longifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2393	Matsumurella chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6648	Piper retrofractum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12125	Pseudomonas stutzeri	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO13059	Abies webbiana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12383	Frullania brasiliensis	Species	Frullaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10666	Verbesina virginica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6428	Euphorbia wangii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27487	Silene banksia	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8639	Agaricus xanthodermus	Species	Agaricaceae	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
IC50	9
Others	19

Activity Type	# Activity
Cell Line	23
Individual Protein	4
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	30.0	%	PMID[534758]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	51.0	%	PMID[534758]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	31.0	%	PMID[534758]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	37.0	%	PMID[534758]
NPT3836	Individual Protein	Intercellular adhesion molecule-1	Homo sapiens	Inhibition	=	36.0	%	PMID[534759]
NPT3836	Individual Protein	Intercellular adhesion molecule-1	Homo sapiens	Inhibition	=	35.9	%	PMID[534759]
NPT3836	Individual Protein	Intercellular adhesion molecule-1	Homo sapiens	Inhibition	=	29.9	%	PMID[534759]
NPT3836	Individual Protein	Intercellular adhesion molecule-1	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[534759]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	9.7	%	PMID[534760]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	15.0	%	PMID[534760]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	22.2	%	PMID[534760]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	15.4	%	PMID[534760]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	-18.0	%	PMID[534761]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	1.0	%	PMID[534761]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	37.0	%	PMID[534761]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	51.0	%	PMID[534761]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	0.0	%	PMID[534761]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	31.0	%	PMID[534761]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	30.0	%	PMID[534761]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[534762]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	40000.0	nM	PMID[534762]
NPT133	Cell Line	ZR-75-1	Homo sapiens	IC50	>	40000.0	nM	PMID[534762]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	>	40000.0	nM	PMID[534762]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	40000.0	nM	PMID[534762]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	>	40000.0	nM	PMID[534762]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	40000.0	nM	PMID[534762]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	40000.0	nM	PMID[534762]

☑ 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 NPC152186 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	165
0.1-0.2	1524
0.2-0.3	7701
0.3-0.4	11503
0.4-0.5	5934
0.5-0.6	10749
0.6-0.7	4273
0.7-0.8	778
0.8-0.85	43
0.85-0.9	6
0.9-0.95	6
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC207541
1.0	High Similarity	NPC170583
1.0	High Similarity	NPC182147
1.0	High Similarity	NPC246133
1.0	High Similarity	NPC71105
0.9916	High Similarity	NPC251466
0.9916	High Similarity	NPC156944
0.9915	High Similarity	NPC300955
0.9833	High Similarity	NPC157740
0.9833	High Similarity	NPC99798
0.9833	High Similarity	NPC291449
0.9833	High Similarity	NPC41331
0.9752	High Similarity	NPC147247
0.9752	High Similarity	NPC246974
0.9508	High Similarity	NPC191302
0.9355	High Similarity	NPC470706
0.9274	High Similarity	NPC469977
0.9213	High Similarity	NPC473463
0.9213	High Similarity	NPC284855
0.9213	High Similarity	NPC282477
0.8661	High Similarity	NPC301713
0.8657	High Similarity	NPC275150
0.8594	High Similarity	NPC186898
0.8594	High Similarity	NPC153990
0.8571	High Similarity	NPC254610
0.8571	High Similarity	NPC166837
0.8559	High Similarity	NPC127326
0.8527	High Similarity	NPC155838
0.8462	Intermediate Similarity	NPC35961
0.8462	Intermediate Similarity	NPC195749
0.8462	Intermediate Similarity	NPC52029
0.8425	Intermediate Similarity	NPC249788
0.8406	Intermediate Similarity	NPC327623
0.8397	Intermediate Similarity	NPC255550
0.8397	Intermediate Similarity	NPC308885
0.8333	Intermediate Similarity	NPC31279
0.8333	Intermediate Similarity	NPC214869
0.831	Intermediate Similarity	NPC474560
0.8308	Intermediate Similarity	NPC251571
0.8258	Intermediate Similarity	NPC114102
0.8254	Intermediate Similarity	NPC344161
0.8231	Intermediate Similarity	NPC274356
0.8209	Intermediate Similarity	NPC218530
0.8195	Intermediate Similarity	NPC130595
0.8195	Intermediate Similarity	NPC93882
0.8175	Intermediate Similarity	NPC69670
0.8175	Intermediate Similarity	NPC57501
0.8175	Intermediate Similarity	NPC77572
0.8145	Intermediate Similarity	NPC303370
0.8134	Intermediate Similarity	NPC285078
0.8134	Intermediate Similarity	NPC313737
0.8134	Intermediate Similarity	NPC6854
0.8125	Intermediate Similarity	NPC114845
0.8125	Intermediate Similarity	NPC301641
0.8125	Intermediate Similarity	NPC80241
0.8083	Intermediate Similarity	NPC227894
0.806	Intermediate Similarity	NPC318862
0.8049	Intermediate Similarity	NPC165646
0.8047	Intermediate Similarity	NPC183262
0.8029	Intermediate Similarity	NPC41473
0.8029	Intermediate Similarity	NPC312770
0.8029	Intermediate Similarity	NPC14600
0.8029	Intermediate Similarity	NPC204848
0.8029	Intermediate Similarity	NPC470707
0.8029	Intermediate Similarity	NPC160607
0.8016	Intermediate Similarity	NPC199209
0.8016	Intermediate Similarity	NPC212643
0.8016	Intermediate Similarity	NPC33271
0.7985	Intermediate Similarity	NPC275950
0.7971	Intermediate Similarity	NPC299583
0.7971	Intermediate Similarity	NPC296898
0.7967	Intermediate Similarity	NPC55300
0.7966	Intermediate Similarity	NPC12714
0.7966	Intermediate Similarity	NPC310905
0.7955	Intermediate Similarity	NPC213711
0.7955	Intermediate Similarity	NPC40352
0.7951	Intermediate Similarity	NPC233731
0.7951	Intermediate Similarity	NPC246358
0.7951	Intermediate Similarity	NPC7097
0.7951	Intermediate Similarity	NPC36108
0.7941	Intermediate Similarity	NPC94280
0.7941	Intermediate Similarity	NPC159150
0.7941	Intermediate Similarity	NPC328419
0.7941	Intermediate Similarity	NPC193673
0.7941	Intermediate Similarity	NPC45783
0.7941	Intermediate Similarity	NPC103947
0.7937	Intermediate Similarity	NPC111225
0.7926	Intermediate Similarity	NPC476345
0.7923	Intermediate Similarity	NPC256167
0.791	Intermediate Similarity	NPC470633
0.791	Intermediate Similarity	NPC228769
0.7907	Intermediate Similarity	NPC83279
0.7891	Intermediate Similarity	NPC256369
0.7891	Intermediate Similarity	NPC119949
0.7886	Intermediate Similarity	NPC137685
0.7883	Intermediate Similarity	NPC136330
0.7883	Intermediate Similarity	NPC196609
0.7883	Intermediate Similarity	NPC255817
0.7883	Intermediate Similarity	NPC230698
0.7883	Intermediate Similarity	NPC251454
0.7883	Intermediate Similarity	NPC96406
0.7883	Intermediate Similarity	NPC205178
0.7883	Intermediate Similarity	NPC73883
0.7883	Intermediate Similarity	NPC180647
0.7883	Intermediate Similarity	NPC277042
0.7879	Intermediate Similarity	NPC17348
0.7868	Intermediate Similarity	NPC219671
0.7868	Intermediate Similarity	NPC471505
0.7868	Intermediate Similarity	NPC227002
0.7868	Intermediate Similarity	NPC147616
0.7868	Intermediate Similarity	NPC104077
0.7868	Intermediate Similarity	NPC106739
0.7868	Intermediate Similarity	NPC259742
0.7852	Intermediate Similarity	NPC173308
0.7852	Intermediate Similarity	NPC63574
0.7852	Intermediate Similarity	NPC181079
0.7833	Intermediate Similarity	NPC292792
0.7829	Intermediate Similarity	NPC263835
0.7826	Intermediate Similarity	NPC145446
0.7826	Intermediate Similarity	NPC99078
0.7826	Intermediate Similarity	NPC137172
0.7823	Intermediate Similarity	NPC173746
0.7823	Intermediate Similarity	NPC257124
0.7823	Intermediate Similarity	NPC78918
0.7823	Intermediate Similarity	NPC139617
0.7823	Intermediate Similarity	NPC156840
0.7823	Intermediate Similarity	NPC8547
0.781	Intermediate Similarity	NPC167096
0.781	Intermediate Similarity	NPC169973
0.7795	Intermediate Similarity	NPC258992
0.7794	Intermediate Similarity	NPC217574
0.7787	Intermediate Similarity	NPC258171
0.7778	Intermediate Similarity	NPC294941
0.777	Intermediate Similarity	NPC220923
0.777	Intermediate Similarity	NPC28641
0.777	Intermediate Similarity	NPC95366
0.777	Intermediate Similarity	NPC248505
0.777	Intermediate Similarity	NPC194359
0.777	Intermediate Similarity	NPC252107
0.777	Intermediate Similarity	NPC225745
0.7761	Intermediate Similarity	NPC158737
0.7761	Intermediate Similarity	NPC64948
0.7761	Intermediate Similarity	NPC177167
0.7752	Intermediate Similarity	NPC310338
0.7752	Intermediate Similarity	NPC43275
0.7752	Intermediate Similarity	NPC281298
0.7737	Intermediate Similarity	NPC252833
0.7737	Intermediate Similarity	NPC97316
0.7734	Intermediate Similarity	NPC120075
0.7734	Intermediate Similarity	NPC164386
0.7734	Intermediate Similarity	NPC280001
0.773	Intermediate Similarity	NPC195814
0.7727	Intermediate Similarity	NPC31344
0.7727	Intermediate Similarity	NPC13020
0.7727	Intermediate Similarity	NPC317769
0.7727	Intermediate Similarity	NPC140359
0.7724	Intermediate Similarity	NPC146530
0.7721	Intermediate Similarity	NPC184814
0.7721	Intermediate Similarity	NPC134764
0.7721	Intermediate Similarity	NPC171550
0.771	Intermediate Similarity	NPC193484
0.7704	Intermediate Similarity	NPC226862
0.7704	Intermediate Similarity	NPC158471
0.7704	Intermediate Similarity	NPC57119
0.7704	Intermediate Similarity	NPC165128
0.7698	Intermediate Similarity	NPC184938
0.7698	Intermediate Similarity	NPC165106
0.7698	Intermediate Similarity	NPC135777
0.7698	Intermediate Similarity	NPC101624
0.7698	Intermediate Similarity	NPC174191
0.7698	Intermediate Similarity	NPC142547
0.7692	Intermediate Similarity	NPC53596
0.7692	Intermediate Similarity	NPC227217
0.7692	Intermediate Similarity	NPC289330
0.7692	Intermediate Similarity	NPC17388
0.7692	Intermediate Similarity	NPC471308
0.7692	Intermediate Similarity	NPC117780
0.7692	Intermediate Similarity	NPC95614
0.7692	Intermediate Similarity	NPC165133
0.7692	Intermediate Similarity	NPC160120
0.7692	Intermediate Similarity	NPC232316
0.7692	Intermediate Similarity	NPC56214
0.7692	Intermediate Similarity	NPC242885
0.7687	Intermediate Similarity	NPC473960
0.7681	Intermediate Similarity	NPC471390
0.7681	Intermediate Similarity	NPC25821
0.7681	Intermediate Similarity	NPC471391
0.7681	Intermediate Similarity	NPC196937
0.7681	Intermediate Similarity	NPC6836
0.7676	Intermediate Similarity	NPC100478
0.7676	Intermediate Similarity	NPC222039
0.7674	Intermediate Similarity	NPC470626
0.7674	Intermediate Similarity	NPC474040
0.7652	Intermediate Similarity	NPC298486
0.7647	Intermediate Similarity	NPC307110
0.7647	Intermediate Similarity	NPC476748
0.7647	Intermediate Similarity	NPC248355
0.7643	Intermediate Similarity	NPC193528
0.7639	Intermediate Similarity	NPC5462
0.763	Intermediate Similarity	NPC100129

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 NPC152186 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	128
0.1-0.2	784
0.2-0.3	1364
0.3-0.4	2604
0.4-0.5	2365
0.5-0.6	1292
0.6-0.7	540
0.7-0.8	69
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8468	Intermediate Similarity	NPD1357	Approved
0.8397	Intermediate Similarity	NPD3144	Approved
0.8397	Intermediate Similarity	NPD3145	Approved
0.8195	Intermediate Similarity	NPD2674	Phase 3
0.7971	Intermediate Similarity	NPD2161	Phase 2
0.7939	Intermediate Similarity	NPD2922	Phase 1
0.7926	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7883	Intermediate Similarity	NPD2492	Phase 1
0.7846	Intermediate Similarity	NPD3705	Approved
0.7838	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD228	Approved
0.7794	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD1375	Discontinued
0.7778	Intermediate Similarity	NPD4739	Approved
0.777	Intermediate Similarity	NPD4108	Discontinued
0.7746	Intermediate Similarity	NPD6331	Phase 2
0.771	Intermediate Similarity	NPD776	Approved
0.7698	Intermediate Similarity	NPD5283	Phase 1
0.7682	Intermediate Similarity	NPD5604	Discontinued
0.7651	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD7153	Discontinued
0.7594	Intermediate Similarity	NPD3685	Discontinued
0.7594	Intermediate Similarity	NPD1669	Approved
0.7594	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD5109	Approved
0.7591	Intermediate Similarity	NPD5110	Phase 2
0.7591	Intermediate Similarity	NPD5111	Phase 2
0.7569	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1712	Approved
0.75	Intermediate Similarity	NPD2157	Approved
0.7448	Intermediate Similarity	NPD2219	Phase 1
0.7445	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD709	Approved
0.7415	Intermediate Similarity	NPD4123	Phase 3
0.7397	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD2978	Approved
0.7368	Intermediate Similarity	NPD2977	Approved
0.7365	Intermediate Similarity	NPD7526	Approved
0.7365	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD52	Approved
0.7347	Intermediate Similarity	NPD4357	Discontinued
0.7344	Intermediate Similarity	NPD821	Approved
0.7338	Intermediate Similarity	NPD5718	Phase 2
0.7333	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD5536	Phase 2
0.7315	Intermediate Similarity	NPD2122	Discontinued
0.731	Intermediate Similarity	NPD4236	Phase 3
0.731	Intermediate Similarity	NPD4237	Approved
0.7293	Intermediate Similarity	NPD2668	Approved
0.7293	Intermediate Similarity	NPD2667	Approved
0.7259	Intermediate Similarity	NPD2233	Approved
0.7259	Intermediate Similarity	NPD2230	Approved
0.7259	Intermediate Similarity	NPD2232	Approved
0.7255	Intermediate Similarity	NPD5772	Approved
0.7255	Intermediate Similarity	NPD5773	Approved
0.7254	Intermediate Similarity	NPD2653	Approved
0.7248	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD4993	Discontinued
0.7246	Intermediate Similarity	NPD2040	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD1558	Phase 1
0.7226	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD6895	Approved
0.7203	Intermediate Similarity	NPD6896	Approved
0.7192	Intermediate Similarity	NPD3060	Approved
0.7174	Intermediate Similarity	NPD6584	Phase 3
0.7171	Intermediate Similarity	NPD4675	Approved
0.7171	Intermediate Similarity	NPD4678	Approved
0.7165	Intermediate Similarity	NPD2684	Approved
0.7153	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD1044	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD5241	Discontinued
0.7092	Intermediate Similarity	NPD1048	Approved
0.7083	Intermediate Similarity	NPD6111	Discontinued
0.708	Intermediate Similarity	NPD2982	Phase 2
0.708	Intermediate Similarity	NPD2983	Phase 2
0.7075	Intermediate Similarity	NPD4162	Approved
0.7075	Intermediate Similarity	NPD5177	Phase 3
0.7067	Intermediate Similarity	NPD1771	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD3656	Approved
0.7042	Intermediate Similarity	NPD839	Approved
0.7042	Intermediate Similarity	NPD840	Approved
0.7027	Intermediate Similarity	NPD4110	Phase 3
0.7027	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD1024	Discontinued
0.7021	Intermediate Similarity	NPD3027	Phase 3
0.7014	Intermediate Similarity	NPD4097	Suspended
0.7008	Intermediate Similarity	NPD3134	Approved
0.7007	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD2981	Phase 2
0.7007	Intermediate Similarity	NPD2231	Phase 2
0.7007	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD2808	Discontinued
0.7007	Intermediate Similarity	NPD2235	Phase 2
0.6993	Remote Similarity	NPD3620	Phase 2
0.6993	Remote Similarity	NPD3111	Phase 1
0.6993	Remote Similarity	NPD4005	Discontinued
0.6993	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD2358	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD556	Approved
0.6964	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6583	Phase 3
0.6957	Remote Similarity	NPD6582	Phase 2
0.6953	Remote Similarity	NPD1358	Approved
0.6947	Remote Similarity	NPD7843	Approved
0.6928	Remote Similarity	NPD4210	Discontinued
0.6928	Remote Similarity	NPD3687	Approved
0.6928	Remote Similarity	NPD3686	Approved
0.6923	Remote Similarity	NPD1423	Approved
0.6917	Remote Similarity	NPD7157	Approved
0.6912	Remote Similarity	NPD2423	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD4626	Approved
0.6903	Remote Similarity	NPD5089	Approved
0.6903	Remote Similarity	NPD5090	Approved
0.6901	Remote Similarity	NPD3166	Approved
0.6901	Remote Similarity	NPD3164	Approved
0.6901	Remote Similarity	NPD3165	Approved
0.6901	Remote Similarity	NPD3167	Approved
0.6897	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD1182	Approved
0.6887	Remote Similarity	NPD5297	Approved
0.6885	Remote Similarity	NPD9296	Approved
0.6879	Remote Similarity	NPD9494	Approved
0.6879	Remote Similarity	NPD2250	Discontinued
0.6879	Remote Similarity	NPD3018	Phase 2
0.6875	Remote Similarity	NPD2238	Phase 2
0.6866	Remote Similarity	NPD3596	Phase 2
0.6857	Remote Similarity	NPD1817	Approved
0.6857	Remote Similarity	NPD1819	Approved
0.6857	Remote Similarity	NPD1820	Approved
0.6857	Remote Similarity	NPD1818	Approved
0.6853	Remote Similarity	NPD1039	Discontinued
0.6846	Remote Similarity	NPD3021	Approved
0.6846	Remote Similarity	NPD3022	Approved
0.6839	Remote Similarity	NPD7028	Phase 2
0.6839	Remote Similarity	NPD1642	Discontinued
0.6821	Remote Similarity	NPD7124	Phase 2
0.6818	Remote Similarity	NPD9379	Approved
0.6818	Remote Similarity	NPD9377	Approved
0.6813	Remote Similarity	NPD2644	Approved
0.6806	Remote Similarity	NPD3058	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD4055	Discovery
0.679	Remote Similarity	NPD4083	Discontinued
0.6783	Remote Similarity	NPD3179	Approved
0.6783	Remote Similarity	NPD3180	Approved
0.6779	Remote Similarity	NPD4149	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD7037	Approved
0.6772	Remote Similarity	NPD2560	Approved
0.6772	Remote Similarity	NPD2563	Approved
0.677	Remote Similarity	NPD2821	Approved
0.6765	Remote Similarity	NPD6580	Approved
0.6765	Remote Similarity	NPD6581	Approved
0.6761	Remote Similarity	NPD2407	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD37	Approved
0.6752	Remote Similarity	NPD5722	Discontinued
0.6744	Remote Similarity	NPD1445	Approved
0.6744	Remote Similarity	NPD1444	Approved
0.6739	Remote Similarity	NPD3847	Discontinued
0.6735	Remote Similarity	NPD7119	Phase 2
0.6732	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD3146	Approved
0.6725	Remote Similarity	NPD3408	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD3657	Discovery
0.6711	Remote Similarity	NPD5756	Phase 2
0.6708	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD290	Approved
0.6692	Remote Similarity	NPD1138	Approved
0.6691	Remote Similarity	NPD1091	Approved
0.669	Remote Similarity	NPD3163	Approved
0.669	Remote Similarity	NPD3530	Approved
0.669	Remote Similarity	NPD3532	Approved
0.669	Remote Similarity	NPD558	Phase 2
0.669	Remote Similarity	NPD3531	Approved
0.669	Remote Similarity	NPD3162	Approved
0.669	Remote Similarity	NPD7477	Discontinued
0.6689	Remote Similarity	NPD5481	Discontinued
0.6689	Remote Similarity	NPD3693	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD1351	Approved
0.6688	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD1349	Approved
0.6688	Remote Similarity	NPD1350	Approved
0.6687	Remote Similarity	NPD7833	Phase 2
0.6687	Remote Similarity	NPD7831	Phase 2
0.6687	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD824	Approved
0.6667	Remote Similarity	NPD6387	Discontinued
0.6667	Remote Similarity	NPD2557	Approved
0.6667	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7258	Clinical (unspecified phase)

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