NPASS Compound

Structure

CID275766 OpenBabel06191716082D 26 26 0 0 1 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 1.5000 2.5981 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 -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 1.0000 0.0000 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 1.0000 1.7321 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 1 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 0.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 4 13 1 0 0 0 0 5 14 1 0 0 0 0 6 14 1 0 0 0 0 7 8 1 0 0 0 0 7 12 2 0 0 0 0 8 15 1 0 0 0 0 9 10 1 0 0 0 0 9 13 2 0 0 0 0 10 21 1 0 0 0 0 11 14 1 0 0 0 0 11 16 1 0 0 0 0 15 18 1 0 0 0 0 15 19 2 0 0 0 0 16 17 1 0 0 0 0 16 22 2 0 0 0 0 17 18 2 0 0 0 0 17 20 1 0 0 0 0 18 23 1 0 0 0 0 19 21 1 0 0 0 0 19 24 1 0 0 0 0 20 21 1 0 0 0 0 20 25 2 0 0 0 0 21 26 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.21
Volume:	391.348
LogP:	4.332
LogD:	1.045
LogS:	-2.601
# Rotatable Bonds:	7
TPSA:	88.51
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.555
Synthetic Accessibility Score:	4.333
Fsp3:	0.619
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.644
MDCK Permeability:	1.8893808373832144e-05
Pgp-inhibitor:	0.755
Pgp-substrate:	0.59
Human Intestinal Absorption (HIA):	0.025
20% Bioavailability (F20%):	0.949
30% Bioavailability (F30%):	0.022

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	92.35216522216797%
Volume Distribution (VD):	1.538
Pgp-substrate:	5.316934108734131%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.118
CYP2C19-inhibitor:	0.042
CYP2C19-substrate:	0.879
CYP2C9-inhibitor:	0.034
CYP2C9-substrate:	0.444
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.042
CYP3A4-inhibitor:	0.221
CYP3A4-substrate:	0.652

ADMET: Excretion

Clearance (CL):	8.887
Half-life (T1/2):	0.344

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.299
Drug-inuced Liver Injury (DILI):	0.945
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.995
Maximum Recommended Daily Dose:	0.055
Skin Sensitization:	0.137
Carcinogencity:	0.182
Eye Corrosion:	0.92
Eye Irritation:	0.485
Respiratory Toxicity:	0.959

Download Data

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

Natural Product: NPC275766

Natural Product ID:	NPC275766
*Common Name:**	Humulone
IUPAC Name:	(6R)-3,5,6-trihydroxy-2-(3-methylbutanoyl)-4,6-bis(3-methylbut-2-enyl)cyclohexa-2,4-dien-1-one
Synonyms:
Standard InCHIKey:	VMSLCPKYRPDHLN-OAQYLSRUSA-N
Standard InCHI:	InChI=1S/C21H30O5/c1-12(2)7-8-15-18(23)17(16(22)11-14(5)6)20(25)21(26,19(15)24)10-9-13(3)4/h7,9,14,23-24,26H,8,10-11H2,1-6H3/t21-/m1/s1
SMILES:	CC(=CCC1=C([C@](CC=C(C)C)(C(=O)C(=C1O)C(=O)CC(C)C)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3814665
PubChem CID:	442911
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0002088] Acyloins

*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]
NPO40531	Humulus lupulus cv. 'Cascade'	Strain	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26918635]
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]
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]
NPO2398	Millettia erythrocalyx	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
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]
NPO24390.1	Juniperus rigida var. conferta	Varieties	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1834	Atalantia racemosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
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[TCM_Taiwan]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1834	Atalantia racemosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12855	Alkanna cappadocica	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2398	Millettia erythrocalyx	Species	Fabaceae	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]
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]
NPO13671	Ononis vaginalis	Species	Fabaceae	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]
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]
NPO10783	Syncarpia hillii	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14578	Prorocentrum micans	Species	Prorocentraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13585	Rapanea lancifolia	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5930	Crambe tatarica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13030	Artemisia dentata	Species	Asteraceae	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]
NPO21830	Buddleja cordata	Species	Scrophulariaceae	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	2
Others	2

Activity Type	# Activity
Individual Protein	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	IC50	=	9300.0	nM	PMID[525208]
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	IC50	>	10000.0	nM	PMID[525208]
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	Activity	=	63.1	%	PMID[525208]
NPT956	Individual Protein	Prostaglandin E synthase	Homo sapiens	Activity	=	49.7	%	PMID[525208]

☑ 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 NPC275766 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	186
0.1-0.2	1233
0.2-0.3	5801
0.3-0.4	12563
0.4-0.5	15244
0.5-0.6	5984
0.6-0.7	1516
0.7-0.8	152
0.8-0.85	13
0.85-0.9	2
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8375	Intermediate Similarity	NPC248624
0.8333	Intermediate Similarity	NPC187529
0.8148	Intermediate Similarity	NPC478122
0.814	Intermediate Similarity	NPC476079
0.814	Intermediate Similarity	NPC113370
0.814	Intermediate Similarity	NPC103743
0.8118	Intermediate Similarity	NPC307112
0.8095	Intermediate Similarity	NPC477784
0.8095	Intermediate Similarity	NPC477786
0.8095	Intermediate Similarity	NPC477785
0.7955	Intermediate Similarity	NPC472688
0.7955	Intermediate Similarity	NPC472676
0.7931	Intermediate Similarity	NPC472007
0.7882	Intermediate Similarity	NPC475083
0.7875	Intermediate Similarity	NPC122244
0.7841	Intermediate Similarity	NPC472008
0.7841	Intermediate Similarity	NPC472677
0.7841	Intermediate Similarity	NPC58532
0.7826	Intermediate Similarity	NPC93271
0.7826	Intermediate Similarity	NPC135576
0.7816	Intermediate Similarity	NPC472009
0.7802	Intermediate Similarity	NPC477241
0.7742	Intermediate Similarity	NPC239895
0.7727	Intermediate Similarity	NPC23622
0.7722	Intermediate Similarity	NPC203819
0.7674	Intermediate Similarity	NPC258985
0.7564	Intermediate Similarity	NPC278895
0.7556	Intermediate Similarity	NPC474918
0.75	Intermediate Similarity	NPC231739
0.7473	Intermediate Similarity	NPC131864
0.7473	Intermediate Similarity	NPC471399
0.7473	Intermediate Similarity	NPC316228
0.7442	Intermediate Similarity	NPC470298
0.7416	Intermediate Similarity	NPC203795
0.7403	Intermediate Similarity	NPC150162
0.7391	Intermediate Similarity	NPC45579
0.7391	Intermediate Similarity	NPC142838
0.7381	Intermediate Similarity	NPC82666
0.7381	Intermediate Similarity	NPC97173
0.7375	Intermediate Similarity	NPC474060
0.7375	Intermediate Similarity	NPC469914
0.7374	Intermediate Similarity	NPC469852
0.7368	Intermediate Similarity	NPC471694
0.7349	Intermediate Similarity	NPC175079
0.7326	Intermediate Similarity	NPC470946
0.7326	Intermediate Similarity	NPC470947
0.7326	Intermediate Similarity	NPC470945
0.732	Intermediate Similarity	NPC469851
0.7303	Intermediate Similarity	NPC79573
0.7303	Intermediate Similarity	NPC470177
0.7294	Intermediate Similarity	NPC315765
0.7283	Intermediate Similarity	NPC265856
0.7283	Intermediate Similarity	NPC469464
0.7283	Intermediate Similarity	NPC166554
0.7283	Intermediate Similarity	NPC477684
0.7273	Intermediate Similarity	NPC143168
0.7273	Intermediate Similarity	NPC53109
0.7273	Intermediate Similarity	NPC477830
0.7262	Intermediate Similarity	NPC151622
0.7262	Intermediate Similarity	NPC7629
0.7262	Intermediate Similarity	NPC110725
0.7253	Intermediate Similarity	NPC473658
0.7253	Intermediate Similarity	NPC53454
0.7253	Intermediate Similarity	NPC72397
0.7241	Intermediate Similarity	NPC67254
0.7241	Intermediate Similarity	NPC225515
0.7241	Intermediate Similarity	NPC44963
0.7241	Intermediate Similarity	NPC472684
0.7241	Intermediate Similarity	NPC189237
0.7228	Intermediate Similarity	NPC168883
0.7204	Intermediate Similarity	NPC166110
0.72	Intermediate Similarity	NPC85529
0.72	Intermediate Similarity	NPC32006
0.7195	Intermediate Similarity	NPC106309
0.7188	Intermediate Similarity	NPC20066
0.7179	Intermediate Similarity	NPC7029
0.7176	Intermediate Similarity	NPC316324
0.7176	Intermediate Similarity	NPC471061
0.7176	Intermediate Similarity	NPC34110
0.7176	Intermediate Similarity	NPC473536
0.7174	Intermediate Similarity	NPC307092
0.7157	Intermediate Similarity	NPC300026
0.7143	Intermediate Similarity	NPC471738
0.7129	Intermediate Similarity	NPC469853
0.7128	Intermediate Similarity	NPC248193
0.7128	Intermediate Similarity	NPC469692
0.7128	Intermediate Similarity	NPC469645
0.7115	Intermediate Similarity	NPC66108
0.7113	Intermediate Similarity	NPC300584
0.7113	Intermediate Similarity	NPC35717
0.7111	Intermediate Similarity	NPC15807
0.7111	Intermediate Similarity	NPC32037
0.7111	Intermediate Similarity	NPC255174
0.7108	Intermediate Similarity	NPC153660
0.7093	Intermediate Similarity	NPC475994
0.7089	Intermediate Similarity	NPC61473
0.7083	Intermediate Similarity	NPC472734
0.7083	Intermediate Similarity	NPC472733
0.7065	Intermediate Similarity	NPC87189
0.7065	Intermediate Similarity	NPC228415
0.7065	Intermediate Similarity	NPC26078
0.7065	Intermediate Similarity	NPC58271
0.7059	Intermediate Similarity	NPC477708
0.7059	Intermediate Similarity	NPC472305
0.7053	Intermediate Similarity	NPC469819
0.7053	Intermediate Similarity	NPC114162
0.7053	Intermediate Similarity	NPC121825
0.7051	Intermediate Similarity	NPC190049
0.7051	Intermediate Similarity	NPC477707
0.7045	Intermediate Similarity	NPC55869
0.7045	Intermediate Similarity	NPC171665
0.7033	Intermediate Similarity	NPC196381
0.7033	Intermediate Similarity	NPC234038
0.7024	Intermediate Similarity	NPC7382
0.7024	Intermediate Similarity	NPC215050
0.7021	Intermediate Similarity	NPC146852
0.7021	Intermediate Similarity	NPC116726
0.7011	Intermediate Similarity	NPC27817
0.701	Intermediate Similarity	NPC472731
0.701	Intermediate Similarity	NPC472732
0.7	Intermediate Similarity	NPC118902
0.7	Intermediate Similarity	NPC142423
0.7	Intermediate Similarity	NPC469980
0.7	Intermediate Similarity	NPC104161
0.7	Intermediate Similarity	NPC308294
0.7	Intermediate Similarity	NPC473144
0.7	Intermediate Similarity	NPC297281
0.6989	Remote Similarity	NPC95364
0.6989	Remote Similarity	NPC51358
0.6989	Remote Similarity	NPC142159
0.6989	Remote Similarity	NPC36668
0.6989	Remote Similarity	NPC118011
0.6988	Remote Similarity	NPC288667
0.6988	Remote Similarity	NPC84790
0.6979	Remote Similarity	NPC91408
0.6979	Remote Similarity	NPC31021
0.6977	Remote Similarity	NPC266124
0.6974	Remote Similarity	NPC320421
0.697	Remote Similarity	NPC185141
0.697	Remote Similarity	NPC224172
0.697	Remote Similarity	NPC46998
0.697	Remote Similarity	NPC110443
0.697	Remote Similarity	NPC128733
0.697	Remote Similarity	NPC133907
0.6966	Remote Similarity	NPC477271
0.6966	Remote Similarity	NPC129080
0.6966	Remote Similarity	NPC477269
0.6966	Remote Similarity	NPC477270
0.6957	Remote Similarity	NPC272039
0.6957	Remote Similarity	NPC179659
0.6957	Remote Similarity	NPC220930
0.6951	Remote Similarity	NPC67608
0.6951	Remote Similarity	NPC262673
0.6947	Remote Similarity	NPC61275
0.6941	Remote Similarity	NPC166018
0.6941	Remote Similarity	NPC89374
0.6941	Remote Similarity	NPC474885
0.6941	Remote Similarity	NPC199445
0.6941	Remote Similarity	NPC225665
0.6941	Remote Similarity	NPC169056
0.6939	Remote Similarity	NPC472729
0.6939	Remote Similarity	NPC472730
0.6939	Remote Similarity	NPC306908
0.6939	Remote Similarity	NPC278008
0.6939	Remote Similarity	NPC470541
0.6939	Remote Similarity	NPC177680
0.6939	Remote Similarity	NPC153776
0.6932	Remote Similarity	NPC108955
0.6932	Remote Similarity	NPC138492
0.6932	Remote Similarity	NPC233352
0.6932	Remote Similarity	NPC824
0.6923	Remote Similarity	NPC179006
0.6923	Remote Similarity	NPC70685
0.6923	Remote Similarity	NPC77971
0.6923	Remote Similarity	NPC64985
0.6923	Remote Similarity	NPC474853
0.6915	Remote Similarity	NPC280592
0.6915	Remote Similarity	NPC475879
0.6915	Remote Similarity	NPC253177
0.6915	Remote Similarity	NPC213636
0.6914	Remote Similarity	NPC243272
0.6907	Remote Similarity	NPC269492
0.6907	Remote Similarity	NPC473291
0.6905	Remote Similarity	NPC275098
0.6905	Remote Similarity	NPC238948
0.6905	Remote Similarity	NPC215745
0.6905	Remote Similarity	NPC12815
0.6905	Remote Similarity	NPC247586
0.69	Remote Similarity	NPC39996
0.6897	Remote Similarity	NPC189485
0.6897	Remote Similarity	NPC275494
0.6897	Remote Similarity	NPC471409
0.6897	Remote Similarity	NPC207772
0.6897	Remote Similarity	NPC476627
0.6897	Remote Similarity	NPC30321
0.6889	Remote Similarity	NPC16488
0.6882	Remote Similarity	NPC269677
0.6875	Remote Similarity	NPC101670
0.6875	Remote Similarity	NPC196227
0.6875	Remote Similarity	NPC473162

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 NPC275766 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	1749
0.2-0.3	3848
0.3-0.4	2362
0.4-0.5	722
0.5-0.6	247
0.6-0.7	34
0.7-0.8	7
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
0.7765	Intermediate Similarity	NPD4800	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7331	Phase 2
0.7381	Intermediate Similarity	NPD4756	Discovery
0.7273	Intermediate Similarity	NPD2664	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD4695	Discontinued
0.7089	Intermediate Similarity	NPD7341	Phase 2
0.7079	Intermediate Similarity	NPD6110	Phase 1
0.6923	Remote Similarity	NPD1696	Phase 3
0.6742	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD5363	Approved
0.6701	Remote Similarity	NPD5282	Discontinued
0.6667	Remote Similarity	NPD5280	Approved
0.6667	Remote Similarity	NPD4694	Approved
0.6667	Remote Similarity	NPD7983	Approved
0.6632	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD5778	Approved
0.6598	Remote Similarity	NPD5779	Approved
0.6593	Remote Similarity	NPD4269	Approved
0.6593	Remote Similarity	NPD4270	Approved
0.6585	Remote Similarity	NPD3704	Approved
0.6489	Remote Similarity	NPD5786	Approved
0.6489	Remote Similarity	NPD4519	Discontinued
0.6489	Remote Similarity	NPD5279	Phase 3
0.6489	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD4623	Approved
0.6452	Remote Similarity	NPD4197	Approved
0.6392	Remote Similarity	NPD5785	Approved
0.6386	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD5329	Approved
0.6374	Remote Similarity	NPD4252	Approved
0.6354	Remote Similarity	NPD4518	Approved
0.6333	Remote Similarity	NPD3617	Approved
0.6327	Remote Similarity	NPD5284	Approved
0.6327	Remote Similarity	NPD5281	Approved
0.6316	Remote Similarity	NPD5690	Phase 2
0.6304	Remote Similarity	NPD5369	Approved
0.6289	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD4753	Phase 2
0.6289	Remote Similarity	NPD6101	Approved
0.6238	Remote Similarity	NPD7839	Suspended
0.6237	Remote Similarity	NPD4221	Approved
0.6237	Remote Similarity	NPD4223	Phase 3
0.6224	Remote Similarity	NPD6698	Approved
0.6224	Remote Similarity	NPD46	Approved
0.617	Remote Similarity	NPD7154	Phase 3
0.6168	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD6411	Approved
0.6139	Remote Similarity	NPD4629	Approved
0.6139	Remote Similarity	NPD5210	Approved
0.6117	Remote Similarity	NPD4225	Approved
0.6117	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.61	Remote Similarity	NPD5133	Approved
0.6098	Remote Similarity	NPD4193	Approved
0.6098	Remote Similarity	NPD4191	Approved
0.6098	Remote Similarity	NPD4194	Approved
0.6098	Remote Similarity	NPD4192	Approved
0.6095	Remote Similarity	NPD5211	Phase 2
0.6078	Remote Similarity	NPD4697	Phase 3
0.6061	Remote Similarity	NPD4096	Approved
0.6061	Remote Similarity	NPD5692	Phase 3
0.6022	Remote Similarity	NPD4822	Approved
0.6022	Remote Similarity	NPD4821	Approved
0.6022	Remote Similarity	NPD4820	Approved
0.6022	Remote Similarity	NPD4819	Approved
0.6019	Remote Similarity	NPD4755	Approved
0.6	Remote Similarity	NPD4634	Approved
0.6	Remote Similarity	NPD5362	Discontinued
0.6	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5694	Approved
0.6	Remote Similarity	NPD6050	Approved
0.6	Remote Similarity	NPD6371	Approved
0.5981	Remote Similarity	NPD5141	Approved
0.598	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.598	Remote Similarity	NPD5695	Phase 3
0.5979	Remote Similarity	NPD4688	Approved
0.5979	Remote Similarity	NPD3618	Phase 1
0.5979	Remote Similarity	NPD4693	Phase 3
0.5979	Remote Similarity	NPD5205	Approved
0.5979	Remote Similarity	NPD4690	Approved
0.5979	Remote Similarity	NPD4138	Approved
0.5979	Remote Similarity	NPD4689	Approved
0.5978	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD7115	Discovery
0.5962	Remote Similarity	NPD5696	Approved
0.596	Remote Similarity	NPD5370	Suspended
0.5946	Remote Similarity	NPD7601	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD3665	Phase 1
0.5938	Remote Similarity	NPD3666	Approved
0.5938	Remote Similarity	NPD3133	Approved
0.5922	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD5222	Approved
0.5922	Remote Similarity	NPD5221	Approved
0.5905	Remote Similarity	NPD5285	Approved
0.5905	Remote Similarity	NPD5286	Approved
0.5905	Remote Similarity	NPD4696	Approved
0.5905	Remote Similarity	NPD4700	Approved
0.5904	Remote Similarity	NPD368	Approved
0.59	Remote Similarity	NPD7838	Discovery
0.5895	Remote Similarity	NPD5209	Approved
0.5895	Remote Similarity	NPD3667	Approved
0.5882	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD6084	Phase 2
0.5865	Remote Similarity	NPD6083	Phase 2
0.5865	Remote Similarity	NPD5173	Approved
0.5849	Remote Similarity	NPD5223	Approved
0.5843	Remote Similarity	NPD5276	Approved
0.5842	Remote Similarity	NPD7637	Suspended
0.5842	Remote Similarity	NPD5693	Phase 1
0.5833	Remote Similarity	NPD5332	Approved
0.5833	Remote Similarity	NPD5331	Approved
0.5826	Remote Similarity	NPD7500	Approved
0.5824	Remote Similarity	NPD8264	Approved
0.5824	Remote Similarity	NPD8039	Approved
0.5812	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD4271	Approved
0.5806	Remote Similarity	NPD4268	Approved
0.5802	Remote Similarity	NPD8779	Phase 3
0.58	Remote Similarity	NPD6080	Approved
0.58	Remote Similarity	NPD6673	Approved
0.58	Remote Similarity	NPD5328	Approved
0.58	Remote Similarity	NPD6904	Approved
0.5794	Remote Similarity	NPD5224	Approved
0.5794	Remote Similarity	NPD5091	Approved
0.5794	Remote Similarity	NPD5225	Approved
0.5794	Remote Similarity	NPD5226	Approved
0.5794	Remote Similarity	NPD4633	Approved
0.5789	Remote Similarity	NPD4790	Discontinued
0.5773	Remote Similarity	NPD4786	Approved
0.5765	Remote Similarity	NPD3197	Phase 1
0.5763	Remote Similarity	NPD8513	Phase 3
0.5763	Remote Similarity	NPD8516	Approved
0.5763	Remote Similarity	NPD8515	Approved
0.5763	Remote Similarity	NPD8517	Approved
0.5761	Remote Similarity	NPD6933	Approved
0.575	Remote Similarity	NPD342	Phase 1
0.5747	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5745	Remote Similarity	NPD4195	Approved
0.5743	Remote Similarity	NPD5207	Approved
0.5741	Remote Similarity	NPD5174	Approved
0.5741	Remote Similarity	NPD5175	Approved
0.5741	Remote Similarity	NPD4754	Approved
0.5714	Remote Similarity	NPD5733	Approved
0.5714	Remote Similarity	NPD4058	Approved
0.5714	Remote Similarity	NPD4687	Approved
0.57	Remote Similarity	NPD6672	Approved
0.57	Remote Similarity	NPD5737	Approved
0.5686	Remote Similarity	NPD6079	Approved
0.5686	Remote Similarity	NPD7515	Phase 2
0.5684	Remote Similarity	NPD5368	Approved
0.5684	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD5654	Approved
0.5664	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD6675	Approved
0.5636	Remote Similarity	NPD5739	Approved
0.5636	Remote Similarity	NPD4768	Approved
0.5636	Remote Similarity	NPD7128	Approved
0.5636	Remote Similarity	NPD6402	Approved
0.5636	Remote Similarity	NPD4767	Approved
0.5631	Remote Similarity	NPD4202	Approved
0.5631	Remote Similarity	NPD6399	Phase 3
0.5625	Remote Similarity	NPD6372	Approved
0.5625	Remote Similarity	NPD6373	Approved
0.5618	Remote Similarity	NPD4137	Phase 3
0.5612	Remote Similarity	NPD3668	Phase 3
0.5607	Remote Similarity	NPD6404	Discontinued
0.5603	Remote Similarity	NPD690	Clinical (unspecified phase)
0.56	Remote Similarity	NPD7524	Approved
0.56	Remote Similarity	NPD3573	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