NPASS Compound

Structure

CID203819 OpenBabel06191715592D 30 30 0 0 0 0 0 0 0 0999 V2000 0.8660 -4.5000 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 -3.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 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 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.7321 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -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 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 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 0.8660 0.5000 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 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 6 18 1 0 0 0 0 7 19 1 0 0 0 0 8 19 1 0 0 0 0 9 10 1 0 0 0 0 9 16 2 0 0 0 0 10 20 1 0 0 0 0 11 13 1 0 0 0 0 11 17 2 0 0 0 0 12 14 1 0 0 0 0 12 18 2 0 0 0 0 13 26 1 0 0 0 0 14 26 1 0 0 0 0 15 19 1 0 0 0 0 15 21 1 0 0 0 0 20 23 2 0 0 0 0 20 24 1 0 0 0 0 21 22 1 0 0 0 0 21 27 2 0 0 0 0 22 23 1 0 0 0 0 22 25 2 0 0 0 0 23 28 1 0 0 0 0 24 26 1 0 0 0 0 24 29 2 0 0 0 0 25 26 1 0 0 0 0 25 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	414.28
Volume:	466.401
LogP:	6.33
LogD:	1.694
LogS:	-3.225
# Rotatable Bonds:	9
TPSA:	68.28
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.363
Synthetic Accessibility Score:	4.227
Fsp3:	0.615
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.723
MDCK Permeability:	1.70279381563887e-05
Pgp-inhibitor:	0.069
Pgp-substrate:	0.241
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.972
30% Bioavailability (F30%):	0.145

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.015
Plasma Protein Binding (PPB):	93.97078704833984%
Volume Distribution (VD):	1.761
Pgp-substrate:	6.859617710113525%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.183
CYP2C19-inhibitor:	0.301
CYP2C19-substrate:	0.916
CYP2C9-inhibitor:	0.336
CYP2C9-substrate:	0.946
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.04
CYP3A4-inhibitor:	0.557
CYP3A4-substrate:	0.49

ADMET: Excretion

Clearance (CL):	15.615
Half-life (T1/2):	0.188

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.525
Drug-inuced Liver Injury (DILI):	0.916
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.997
Maximum Recommended Daily Dose:	0.017
Skin Sensitization:	0.034
Carcinogencity:	0.313
Eye Corrosion:	0.899
Eye Irritation:	0.253
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC203819

Natural Product ID:	NPC203819
*Common Name:**	Lupulone
IUPAC Name:	n.a.
Synonyms:	Lupulone
Standard InCHIKey:	WPVSVIXDXMNGGN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C26H38O4/c1-16(2)9-10-20-23(28)22(21(27)15-19(7)8)25(30)26(24(20)29,13-11-17(3)4)14-12-18(5)6/h9,11-12,19,28,30H,10,13-15H2,1-8H3
SMILES:	CC(=CCC1=C(C(=C(C(CC=C(C)C)(CC=C(C)C)C1=O)O)C(=O)CC(C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL480267
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0003889] Vinylogous acids

*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
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.1002/ejlt.201100207]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.1007/s11746-010-1670-2]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.1016/j.foodcont.2016.09.002]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.1016/j.jfca.2010.08.006]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.1016/j.supflu.2010.06.003]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.1016/j.supflu.2010.12.007]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.1016/j.supflu.2016.02.010]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.1016/j.supflu.2018.06.017]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.12691/jfnr-2-5-9]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.5219/332]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	cone	n.a.	PMID[10336650]
NPO3492	Negombata magnifica	Species	Latrunculiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15217296]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679315]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16252923]
NPO3492	Negombata magnifica	Species	Latrunculiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499319]
NPO13478	Scorzonera pseudodivaricata	Species	Asteraceae	Eukaryota	n.a.	Mongolian	n.a.	PMID[17542634]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	cone	n.a.	PMID[17624889]
NPO3492	Negombata magnifica	Species	Latrunculiidae	Eukaryota	n.a.	sand-covered bottom at -10 to -15 m at Hurghada, on the Egyptian Red Sea coast	2003-JUN	PMID[18298079]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18611049]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18768384]
NPO3492	Negombata magnifica	Species	Latrunculiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18942825]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19476340]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		PMID[19628108]
NPO12855	Alkanna cappadocica	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20405844]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21912858]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	cone	n.a.	PMID[22111577]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	flower	n.a.	PMID[22166201]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		PMID[22538527]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23790907]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		PMID[24811150]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24948953]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25564559]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		PMID[28274428]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29154541]
NPO2722	Humulus japonicus	Species	Cannabaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[29254897]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		PMID[30236698]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	Guangzhou, China		PMID[30563201]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		PMID[30583361]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		PMID[30599958]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		PMID[31159190]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		PMID[31861466]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO2722	Humulus japonicus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2398	Millettia erythrocalyx	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24390.1	Juniperus rigida var. conferta	Varieties	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2722	Humulus japonicus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1834	Atalantia racemosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9313	Fritillaria ningguoensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2398	Millettia erythrocalyx	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2722	Humulus japonicus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9313	Fritillaria ningguoensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14578	Prorocentrum micans	Species	Prorocentraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13030	Artemisia dentata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21830	Buddleja cordata	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5930	Crambe tatarica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12855	Alkanna cappadocica	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12196	Buphane fischeri	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO1834	Atalantia racemosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12700	Diospyros eriantha	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2398	Millettia erythrocalyx	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6360	Xenoacremonium recifei	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11848	Lemaireocereus griseus	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3492	Negombata magnifica	Species	Latrunculiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24390.1	Juniperus rigida var. conferta	Varieties	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9313	Fritillaria ningguoensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13478	Scorzonera pseudodivaricata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13671	Ononis vaginalis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8928	Pteris semipinnata	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO252	Hoffmannia strigillosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9934	Mycobacterium leprae	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO2722	Humulus japonicus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10783	Syncarpia hillii	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13585	Rapanea lancifolia	Species	Primulaceae	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	3
Others	2

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	17000.0	nM	PMID[488346]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	<	40.0	%	PMID[488346]
NPT1	Others	Radical scavenging activity		IC50	=	25000.0	nM	PMID[488347]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	39000.0	nM	PMID[488347]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	50.0	%	PMID[488347]

☑ 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 NPC203819 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	158
0.1-0.2	1240
0.2-0.3	6909
0.3-0.4	17392
0.4-0.5	10470
0.5-0.6	5222
0.6-0.7	1196
0.7-0.8	107
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7927	Intermediate Similarity	NPC58532
0.7927	Intermediate Similarity	NPC472677
0.7831	Intermediate Similarity	NPC472688
0.7831	Intermediate Similarity	NPC472676
0.7805	Intermediate Similarity	NPC103743
0.7805	Intermediate Similarity	NPC113370
0.7805	Intermediate Similarity	NPC476079
0.775	Intermediate Similarity	NPC475083
0.7722	Intermediate Similarity	NPC275766
0.7703	Intermediate Similarity	NPC95863
0.7639	Intermediate Similarity	NPC278895
0.76	Intermediate Similarity	NPC153660
0.7564	Intermediate Similarity	NPC248624
0.7561	Intermediate Similarity	NPC307112
0.75	Intermediate Similarity	NPC122244
0.75	Intermediate Similarity	NPC72397
0.75	Intermediate Similarity	NPC44963
0.75	Intermediate Similarity	NPC472684
0.7465	Intermediate Similarity	NPC150162
0.7432	Intermediate Similarity	NPC473277
0.7429	Intermediate Similarity	NPC64985
0.7403	Intermediate Similarity	NPC225665
0.7403	Intermediate Similarity	NPC169056
0.7403	Intermediate Similarity	NPC166018
0.7397	Intermediate Similarity	NPC106613
0.7368	Intermediate Similarity	NPC186042
0.7342	Intermediate Similarity	NPC478122
0.7342	Intermediate Similarity	NPC471409
0.7342	Intermediate Similarity	NPC315765
0.7342	Intermediate Similarity	NPC275494
0.7324	Intermediate Similarity	NPC190049
0.7303	Intermediate Similarity	NPC93271
0.7303	Intermediate Similarity	NPC135576
0.7297	Intermediate Similarity	NPC117804
0.7284	Intermediate Similarity	NPC6663
0.7284	Intermediate Similarity	NPC189237
0.7273	Intermediate Similarity	NPC477241
0.7273	Intermediate Similarity	NPC215050
0.725	Intermediate Similarity	NPC170394
0.7237	Intermediate Similarity	NPC106309
0.7215	Intermediate Similarity	NPC203403
0.72	Intermediate Similarity	NPC136473
0.72	Intermediate Similarity	NPC469914
0.7195	Intermediate Similarity	NPC20262
0.7195	Intermediate Similarity	NPC256750
0.7176	Intermediate Similarity	NPC287079
0.7162	Intermediate Similarity	NPC254886
0.7162	Intermediate Similarity	NPC269985
0.716	Intermediate Similarity	NPC160582
0.716	Intermediate Similarity	NPC45495
0.7143	Intermediate Similarity	NPC247586
0.7143	Intermediate Similarity	NPC15807
0.7143	Intermediate Similarity	NPC12815
0.7143	Intermediate Similarity	NPC179006
0.7143	Intermediate Similarity	NPC215745
0.7143	Intermediate Similarity	NPC474853
0.7143	Intermediate Similarity	NPC238948
0.7125	Intermediate Similarity	NPC475994
0.7125	Intermediate Similarity	NPC189485
0.7125	Intermediate Similarity	NPC169095
0.7108	Intermediate Similarity	NPC258985
0.7108	Intermediate Similarity	NPC49019
0.7101	Intermediate Similarity	NPC268185
0.7101	Intermediate Similarity	NPC283502
0.7093	Intermediate Similarity	NPC53454
0.7089	Intermediate Similarity	NPC263582
0.7089	Intermediate Similarity	NPC110725
0.7089	Intermediate Similarity	NPC250621
0.7073	Intermediate Similarity	NPC225515
0.7073	Intermediate Similarity	NPC474980
0.7073	Intermediate Similarity	NPC470298
0.7059	Intermediate Similarity	NPC194417
0.7051	Intermediate Similarity	NPC147438
0.7037	Intermediate Similarity	NPC7232
0.7037	Intermediate Similarity	NPC308038
0.7033	Intermediate Similarity	NPC239895
0.7027	Intermediate Similarity	NPC166791
0.7027	Intermediate Similarity	NPC137163
0.7027	Intermediate Similarity	NPC315115
0.7027	Intermediate Similarity	NPC100719
0.7027	Intermediate Similarity	NPC142423
0.7027	Intermediate Similarity	NPC308294
0.7027	Intermediate Similarity	NPC322035
0.7024	Intermediate Similarity	NPC476412
0.7011	Intermediate Similarity	NPC474918
0.7011	Intermediate Similarity	NPC36668
0.7011	Intermediate Similarity	NPC118011
0.7	Intermediate Similarity	NPC61952
0.7	Intermediate Similarity	NPC316324
0.7	Intermediate Similarity	NPC266193
0.7	Intermediate Similarity	NPC86917
0.7	Intermediate Similarity	NPC471061
0.7	Intermediate Similarity	NPC97377
0.7	Intermediate Similarity	NPC257666
0.6988	Remote Similarity	NPC477271
0.6988	Remote Similarity	NPC92226
0.6988	Remote Similarity	NPC477269
0.6988	Remote Similarity	NPC129080
0.6988	Remote Similarity	NPC477270
0.6977	Remote Similarity	NPC476409
0.6962	Remote Similarity	NPC474885
0.6962	Remote Similarity	NPC472327
0.6951	Remote Similarity	NPC471514
0.6951	Remote Similarity	NPC148685
0.6951	Remote Similarity	NPC306095
0.6951	Remote Similarity	NPC157895
0.6951	Remote Similarity	NPC104120
0.6944	Remote Similarity	NPC317025
0.6944	Remote Similarity	NPC317177
0.6944	Remote Similarity	NPC326645
0.6944	Remote Similarity	NPC329416
0.6941	Remote Similarity	NPC255174
0.6932	Remote Similarity	NPC213636
0.6932	Remote Similarity	NPC253177
0.6932	Remote Similarity	NPC280592
0.6932	Remote Similarity	NPC145666
0.6923	Remote Similarity	NPC201562
0.6923	Remote Similarity	NPC323437
0.6923	Remote Similarity	NPC29542
0.6914	Remote Similarity	NPC297996
0.6914	Remote Similarity	NPC478247
0.6914	Remote Similarity	NPC264391
0.6914	Remote Similarity	NPC198240
0.6914	Remote Similarity	NPC478246
0.6914	Remote Similarity	NPC62336
0.6914	Remote Similarity	NPC74410
0.6905	Remote Similarity	NPC16488
0.6905	Remote Similarity	NPC97913
0.6905	Remote Similarity	NPC310470
0.6897	Remote Similarity	NPC474854
0.6892	Remote Similarity	NPC61473
0.6889	Remote Similarity	NPC474882
0.6883	Remote Similarity	NPC316029
0.6883	Remote Similarity	NPC315597
0.6875	Remote Similarity	NPC180886
0.6875	Remote Similarity	NPC51391
0.6875	Remote Similarity	NPC4492
0.6875	Remote Similarity	NPC26504
0.6875	Remote Similarity	NPC472305
0.6867	Remote Similarity	NPC116797
0.6867	Remote Similarity	NPC121984
0.6867	Remote Similarity	NPC278459
0.6867	Remote Similarity	NPC226068
0.6867	Remote Similarity	NPC55869
0.686	Remote Similarity	NPC477479
0.686	Remote Similarity	NPC315395
0.686	Remote Similarity	NPC477478
0.686	Remote Similarity	NPC470955
0.686	Remote Similarity	NPC316426
0.686	Remote Similarity	NPC476982
0.6854	Remote Similarity	NPC474018
0.6854	Remote Similarity	NPC45579
0.6854	Remote Similarity	NPC473986
0.6854	Remote Similarity	NPC471329
0.6854	Remote Similarity	NPC204341
0.6854	Remote Similarity	NPC296114
0.6849	Remote Similarity	NPC477707
0.6849	Remote Similarity	NPC322457
0.6848	Remote Similarity	NPC53844
0.6842	Remote Similarity	NPC313444
0.6835	Remote Similarity	NPC213223
0.6835	Remote Similarity	NPC7382
0.6829	Remote Similarity	NPC308545
0.6829	Remote Similarity	NPC301769
0.6829	Remote Similarity	NPC32758
0.6829	Remote Similarity	NPC82488
0.6829	Remote Similarity	NPC27817
0.6829	Remote Similarity	NPC281138
0.6829	Remote Similarity	NPC19900
0.6824	Remote Similarity	NPC472865
0.6824	Remote Similarity	NPC219966
0.6824	Remote Similarity	NPC164577
0.6818	Remote Similarity	NPC472983
0.6818	Remote Similarity	NPC123912
0.6795	Remote Similarity	NPC126061
0.6795	Remote Similarity	NPC288667
0.6795	Remote Similarity	NPC474884
0.6795	Remote Similarity	NPC67076
0.6795	Remote Similarity	NPC474539
0.6795	Remote Similarity	NPC84790
0.6795	Remote Similarity	NPC319163
0.679	Remote Similarity	NPC315394
0.679	Remote Similarity	NPC473825
0.679	Remote Similarity	NPC34110
0.679	Remote Similarity	NPC82666
0.679	Remote Similarity	NPC165711
0.679	Remote Similarity	NPC97173
0.679	Remote Similarity	NPC74995
0.679	Remote Similarity	NPC132542
0.679	Remote Similarity	NPC476007
0.6786	Remote Similarity	NPC93590
0.6786	Remote Similarity	NPC103486
0.6782	Remote Similarity	NPC220930
0.6782	Remote Similarity	NPC23622
0.6782	Remote Similarity	NPC136948
0.6782	Remote Similarity	NPC272039
0.6765	Remote Similarity	NPC37644
0.6757	Remote Similarity	NPC4638
0.6757	Remote Similarity	NPC7029
0.6753	Remote Similarity	NPC236208

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 NPC203819 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	140
0.1-0.2	1811
0.2-0.3	4151
0.3-0.4	2302
0.4-0.5	506
0.5-0.6	205
0.6-0.7	31
0.7-0.8	4
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
0.7027	Intermediate Similarity	NPD7331	Phase 2
0.6951	Remote Similarity	NPD4695	Discontinued
0.6944	Remote Similarity	NPD4194	Approved
0.6944	Remote Similarity	NPD4191	Approved
0.6944	Remote Similarity	NPD4193	Approved
0.6944	Remote Similarity	NPD4192	Approved
0.6892	Remote Similarity	NPD7341	Phase 2
0.679	Remote Similarity	NPD4756	Discovery
0.6747	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD6110	Phase 1
0.6667	Remote Similarity	NPD4623	Approved
0.6667	Remote Similarity	NPD4519	Discontinued
0.6629	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD5209	Approved
0.6571	Remote Similarity	NPD342	Phase 1
0.6543	Remote Similarity	NPD8264	Approved
0.6506	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD7637	Suspended
0.6477	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD5280	Approved
0.6477	Remote Similarity	NPD5279	Phase 3
0.6477	Remote Similarity	NPD4694	Approved
0.6413	Remote Similarity	NPD5778	Approved
0.6413	Remote Similarity	NPD5779	Approved
0.6395	Remote Similarity	NPD4223	Phase 3
0.6395	Remote Similarity	NPD4221	Approved
0.6395	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD5785	Approved
0.6364	Remote Similarity	NPD5363	Approved
0.6364	Remote Similarity	NPD5329	Approved
0.6364	Remote Similarity	NPD1696	Phase 3
0.6353	Remote Similarity	NPD4252	Approved
0.6351	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD4518	Approved
0.631	Remote Similarity	NPD3617	Approved
0.6304	Remote Similarity	NPD6411	Approved
0.6304	Remote Similarity	NPD5284	Approved
0.6304	Remote Similarity	NPD5281	Approved
0.6267	Remote Similarity	NPD368	Approved
0.625	Remote Similarity	NPD3665	Phase 1
0.625	Remote Similarity	NPD3666	Approved
0.625	Remote Similarity	NPD3133	Approved
0.625	Remote Similarity	NPD4197	Approved
0.625	Remote Similarity	NPD4219	Approved
0.6235	Remote Similarity	NPD4195	Approved
0.622	Remote Similarity	NPD5733	Approved
0.6207	Remote Similarity	NPD4269	Approved
0.6207	Remote Similarity	NPD4270	Approved
0.6196	Remote Similarity	NPD4096	Approved
0.6173	Remote Similarity	NPD5276	Approved
0.617	Remote Similarity	NPD5282	Discontinued
0.6164	Remote Similarity	NPD8779	Phase 3
0.6145	Remote Similarity	NPD8039	Approved
0.6129	Remote Similarity	NPD7515	Phase 2
0.6118	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD4690	Approved
0.6111	Remote Similarity	NPD4689	Approved
0.6111	Remote Similarity	NPD4693	Phase 3
0.6111	Remote Similarity	NPD4688	Approved
0.6111	Remote Similarity	NPD5690	Phase 2
0.6111	Remote Similarity	NPD3618	Phase 1
0.6111	Remote Similarity	NPD4138	Approved
0.6111	Remote Similarity	NPD5205	Approved
0.6098	Remote Similarity	NPD4732	Discontinued
0.6087	Remote Similarity	NPD5328	Approved
0.6087	Remote Similarity	NPD4753	Phase 2
0.6087	Remote Similarity	NPD6101	Approved
0.6087	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD4225	Approved
0.6081	Remote Similarity	NPD287	Approved
0.6067	Remote Similarity	NPD4786	Approved
0.6067	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD6929	Approved
0.6024	Remote Similarity	NPD4058	Approved
0.6024	Remote Similarity	NPD4687	Approved
0.6024	Remote Similarity	NPD6926	Approved
0.6024	Remote Similarity	NPD6924	Approved
0.6023	Remote Similarity	NPD3667	Approved
0.602	Remote Similarity	NPD6404	Discontinued
0.6	Remote Similarity	NPD5776	Phase 2
0.6	Remote Similarity	NPD6925	Approved
0.6	Remote Similarity	NPD7748	Approved
0.5977	Remote Similarity	NPD6931	Approved
0.5977	Remote Similarity	NPD7514	Phase 3
0.5977	Remote Similarity	NPD7332	Phase 2
0.5977	Remote Similarity	NPD6930	Phase 2
0.5957	Remote Similarity	NPD6079	Approved
0.5957	Remote Similarity	NPD7983	Approved
0.5957	Remote Similarity	NPD6050	Approved
0.5955	Remote Similarity	NPD6695	Phase 3
0.5955	Remote Similarity	NPD7154	Phase 3
0.5949	Remote Similarity	NPD3704	Approved
0.5949	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5942	Remote Similarity	NPD4220	Pre-registration
0.5934	Remote Similarity	NPD5786	Approved
0.593	Remote Similarity	NPD7145	Approved
0.593	Remote Similarity	NPD4271	Approved
0.593	Remote Similarity	NPD4268	Approved
0.5926	Remote Similarity	NPD6922	Approved
0.5926	Remote Similarity	NPD4137	Phase 3
0.5926	Remote Similarity	NPD6923	Approved
0.5909	Remote Similarity	NPD6902	Approved
0.5897	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD5133	Approved
0.5889	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD6933	Approved
0.5876	Remote Similarity	NPD7839	Suspended
0.5875	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD7639	Approved
0.5859	Remote Similarity	NPD7640	Approved
0.5854	Remote Similarity	NPD4691	Approved
0.5854	Remote Similarity	NPD4747	Approved
0.5854	Remote Similarity	NPD7143	Approved
0.5854	Remote Similarity	NPD7144	Approved
0.5851	Remote Similarity	NPD7838	Discovery
0.5851	Remote Similarity	NPD5692	Phase 3
0.5843	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD6084	Phase 2
0.5816	Remote Similarity	NPD6083	Phase 2
0.5816	Remote Similarity	NPD7902	Approved
0.5806	Remote Similarity	NPD5737	Approved
0.5806	Remote Similarity	NPD6672	Approved
0.5795	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5795	Remote Similarity	NPD4822	Approved
0.5795	Remote Similarity	NPD4821	Approved
0.5795	Remote Similarity	NPD4819	Approved
0.5795	Remote Similarity	NPD4820	Approved
0.5789	Remote Similarity	NPD5694	Approved
0.5789	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5783	Remote Similarity	NPD7151	Approved
0.5783	Remote Similarity	NPD7152	Approved
0.5783	Remote Similarity	NPD7150	Approved
0.5783	Remote Similarity	NPD4243	Approved
0.5778	Remote Similarity	NPD5331	Approved
0.5778	Remote Similarity	NPD5332	Approved
0.5778	Remote Similarity	NPD5362	Discontinued
0.5773	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD5210	Approved
0.5773	Remote Similarity	NPD5695	Phase 3
0.5773	Remote Similarity	NPD4629	Approved
0.5761	Remote Similarity	NPD5330	Approved
0.5761	Remote Similarity	NPD7334	Approved
0.5761	Remote Similarity	NPD6684	Approved
0.5761	Remote Similarity	NPD7521	Approved
0.5761	Remote Similarity	NPD6409	Approved
0.5761	Remote Similarity	NPD7146	Approved
0.5758	Remote Similarity	NPD7638	Approved
0.5758	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5745	Remote Similarity	NPD6080	Approved
0.5745	Remote Similarity	NPD6904	Approved
0.5745	Remote Similarity	NPD5370	Suspended
0.5745	Remote Similarity	NPD6673	Approved
0.5743	Remote Similarity	NPD5211	Phase 2
0.5735	Remote Similarity	NPD4265	Approved
0.573	Remote Similarity	NPD5369	Approved
0.573	Remote Similarity	NPD6898	Phase 1
0.573	Remote Similarity	NPD4790	Discontinued
0.5729	Remote Similarity	NPD4202	Approved
0.5729	Remote Similarity	NPD6399	Phase 3
0.5714	Remote Similarity	NPD3668	Phase 3
0.5714	Remote Similarity	NPD5222	Approved
0.5714	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4697	Phase 3
0.5714	Remote Similarity	NPD7614	Phase 1
0.5714	Remote Similarity	NPD5221	Approved
0.5699	Remote Similarity	NPD7750	Discontinued
0.5699	Remote Similarity	NPD7524	Approved
0.5686	Remote Similarity	NPD6647	Phase 2
0.5684	Remote Similarity	NPD6698	Approved
0.5684	Remote Similarity	NPD46	Approved
0.5684	Remote Similarity	NPD5207	Approved
0.567	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.566	Remote Similarity	NPD6371	Approved
0.5657	Remote Similarity	NPD5173	Approved
0.5657	Remote Similarity	NPD4755	Approved
0.5652	Remote Similarity	NPD6893	Approved
0.5652	Remote Similarity	NPD1694	Approved
0.5647	Remote Similarity	NPD4784	Approved
0.5647	Remote Similarity	NPD4785	Approved
0.5638	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD6903	Approved
0.5636	Remote Similarity	NPD7115	Discovery
0.5632	Remote Similarity	NPD6932	Approved
0.5631	Remote Similarity	NPD5141	Approved
0.5625	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD5693	Phase 1
0.5618	Remote Similarity	NPD7509	Discontinued
0.5604	Remote Similarity	NPD4788	Approved
0.56	Remote Similarity	NPD5696	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