NPASS Compound

Structure

NPC166770 OpenBabel07101719252D 28 29 0 0 1 0 0 0 0 0999 V2000 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 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 5.1962 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 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 1.7321 -2.0000 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 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 0.0000 C 0 0 2 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 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 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 3 13 1 0 0 0 0 6 19 2 0 0 0 0 7 8 2 0 0 0 0 7 12 1 0 0 0 0 8 15 1 0 0 0 0 9 15 2 0 0 0 0 9 16 1 0 0 0 0 10 18 1 0 0 0 0 10 20 1 0 0 0 0 11 17 2 0 0 0 0 11 28 1 0 0 0 0 12 2 1 1 0 0 0 12 14 1 0 0 0 0 13 16 2 0 0 0 0 13 20 1 0 0 0 0 14 4 1 1 0 0 0 14 24 1 0 0 0 0 15 28 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 18 22 1 6 0 0 0 19 21 1 0 0 0 0 19 23 1 0 0 0 0 20 25 2 0 0 0 0 21 22 1 0 0 0 0 21 26 2 0 0 0 0 22 5 1 6 0 0 0 22 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	406.15
Volume:	412.662
LogP:	3.39
LogD:	2.907
LogS:	-4.329
# Rotatable Bonds:	6
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.656
Synthetic Accessibility Score:	5.191
Fsp3:	0.455
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.601
MDCK Permeability:	1.9562388843041845e-05
Pgp-inhibitor:	0.049
Pgp-substrate:	0.044
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.02

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.853
Plasma Protein Binding (PPB):	78.8189697265625%
Volume Distribution (VD):	1.62
Pgp-substrate:	12.248531341552734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.894
CYP1A2-substrate:	0.512
CYP2C19-inhibitor:	0.636
CYP2C19-substrate:	0.782
CYP2C9-inhibitor:	0.474
CYP2C9-substrate:	0.075
CYP2D6-inhibitor:	0.675
CYP2D6-substrate:	0.039
CYP3A4-inhibitor:	0.892
CYP3A4-substrate:	0.519

ADMET: Excretion

Clearance (CL):	2.339
Half-life (T1/2):	0.418

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.919
Drug-inuced Liver Injury (DILI):	0.248
AMES Toxicity:	0.133
Rat Oral Acute Toxicity:	0.925
Maximum Recommended Daily Dose:	0.855
Skin Sensitization:	0.935
Carcinogencity:	0.937
Eye Corrosion:	0.004
Eye Irritation:	0.043
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC166770

Natural Product ID:	NPC166770
*Common Name:**	Chaetomugilin P
IUPAC Name:	(8S)-8-[(Z,2S)-4-chloro-2-hydroxy-3-oxohex-4-en-2-yl]-3-[(E,3R,4R)-4-hydroxy-3-methylpent-1-enyl]-5-methyl-7,8-dihydroisochromen-6-one
Synonyms:	Chaetomugilin P
Standard InCHIKey:	KLMQRLLJGPIKJE-NCZDROTISA-N
Standard InCHI:	InChI=1S/C22H27ClO5/c1-6-19(23)21(26)22(5,27)18-10-20(25)13(3)16-9-15(28-11-17(16)18)8-7-12(2)14(4)24/h6-9,11-12,14,18,24,27H,10H2,1-5H3/b8-7+,19-6-/t12-,14-,18+,22+/m1/s1
SMILES:	C/C=C(/C(=O)[C@]([C@H]1CC(=O)C(=C2C1=COC(=C2)/C=C/[C@H]([C@H](O)C)C)C)(O)C)Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1797229
PubChem CID:	53358091
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones [CHEMONTID:0004325] Cyclohexenones

*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
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12357398]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12483566]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497948]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921417]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16209910]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499339]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16872138]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16904330]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17125234]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17827664]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	Ginkgo biloba	n.a.	n.a.	PMID[19246197]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19246197]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19427327]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20225834]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20814854]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21548578]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	isolated from the leaves of Viguiera robusta	n.a.	n.a.	PMID[21548578]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21548578]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21640594]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21854043]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22112725]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22593034]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23072467]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	Xichang of Sichuan Province, China	n.a.	PMID[26125976]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26343828]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[5066072]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7116505]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[CiteXplore Id]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	0.0007	nM	PMID[493732]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	0.0012	nM	PMID[493732]
NPT137	Cell Line	L1210	Mus musculus	IC50	=	0.0015	nM	PMID[493732]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	0.0018	nM	PMID[493732]

☑ 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 NPC166770 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	203
0.1-0.2	1165
0.2-0.3	5084
0.3-0.4	12094
0.4-0.5	15976
0.5-0.6	6666
0.6-0.7	1419
0.7-0.8	77
0.8-0.85	6
0.85-0.9	0
0.9-0.95	3
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9891	High Similarity	NPC185253
0.9891	High Similarity	NPC215253
0.9674	High Similarity	NPC134083
0.9375	High Similarity	NPC297281
0.9375	High Similarity	NPC473144
0.8191	Intermediate Similarity	NPC203795
0.8108	Intermediate Similarity	NPC31641
0.8108	Intermediate Similarity	NPC476815
0.8039	Intermediate Similarity	NPC224172
0.8018	Intermediate Similarity	NPC245320
0.7981	Intermediate Similarity	NPC272528
0.7946	Intermediate Similarity	NPC473145
0.7857	Intermediate Similarity	NPC224270
0.7679	Intermediate Similarity	NPC243298
0.7664	Intermediate Similarity	NPC199107
0.7664	Intermediate Similarity	NPC232969
0.7549	Intermediate Similarity	NPC12727
0.7547	Intermediate Similarity	NPC320294
0.7451	Intermediate Similarity	NPC143210
0.7426	Intermediate Similarity	NPC32552
0.7404	Intermediate Similarity	NPC471694
0.7404	Intermediate Similarity	NPC208094
0.7383	Intermediate Similarity	NPC271059
0.7383	Intermediate Similarity	NPC25666
0.7379	Intermediate Similarity	NPC295347
0.7364	Intermediate Similarity	NPC228477
0.7364	Intermediate Similarity	NPC137911
0.7358	Intermediate Similarity	NPC469851
0.734	Intermediate Similarity	NPC478122
0.7339	Intermediate Similarity	NPC469853
0.73	Intermediate Similarity	NPC60765
0.7248	Intermediate Similarity	NPC469852
0.7228	Intermediate Similarity	NPC51358
0.7228	Intermediate Similarity	NPC307092
0.7228	Intermediate Similarity	NPC210216
0.7196	Intermediate Similarity	NPC472637
0.7172	Intermediate Similarity	NPC32037
0.7168	Intermediate Similarity	NPC66108
0.7158	Intermediate Similarity	NPC231739
0.7143	Intermediate Similarity	NPC16488
0.7143	Intermediate Similarity	NPC288281
0.7129	Intermediate Similarity	NPC26078
0.7129	Intermediate Similarity	NPC473658
0.71	Intermediate Similarity	NPC315395
0.71	Intermediate Similarity	NPC316426
0.7091	Intermediate Similarity	NPC32006
0.7091	Intermediate Similarity	NPC85529
0.7091	Intermediate Similarity	NPC478052
0.7091	Intermediate Similarity	NPC477125
0.7087	Intermediate Similarity	NPC166110
0.7087	Intermediate Similarity	NPC193396
0.7087	Intermediate Similarity	NPC32944
0.7083	Intermediate Similarity	NPC19900
0.7059	Intermediate Similarity	NPC212598
0.7053	Intermediate Similarity	NPC97173
0.7048	Intermediate Similarity	NPC91408
0.7048	Intermediate Similarity	NPC31021
0.7037	Intermediate Similarity	NPC469657
0.7037	Intermediate Similarity	NPC244456
0.703	Intermediate Similarity	NPC103743
0.703	Intermediate Similarity	NPC113370
0.703	Intermediate Similarity	NPC476079
0.7019	Intermediate Similarity	NPC248193
0.7019	Intermediate Similarity	NPC242637
0.7	Intermediate Similarity	NPC307112
0.7	Intermediate Similarity	NPC8518
0.7	Intermediate Similarity	NPC132228
0.7	Intermediate Similarity	NPC263997
0.7	Intermediate Similarity	NPC6185
0.7	Intermediate Similarity	NPC241512
0.7	Intermediate Similarity	NPC187529
0.699	Remote Similarity	NPC469372
0.699	Remote Similarity	NPC131864
0.699	Remote Similarity	NPC265856
0.6979	Remote Similarity	NPC475994
0.697	Remote Similarity	NPC477786
0.697	Remote Similarity	NPC477784
0.697	Remote Similarity	NPC477785
0.6961	Remote Similarity	NPC53454
0.6961	Remote Similarity	NPC307298
0.6957	Remote Similarity	NPC321496
0.6957	Remote Similarity	NPC326264
0.6952	Remote Similarity	NPC474882
0.6937	Remote Similarity	NPC266570
0.6937	Remote Similarity	NPC189863
0.6931	Remote Similarity	NPC234038
0.6931	Remote Similarity	NPC94666
0.6923	Remote Similarity	NPC303697
0.6923	Remote Similarity	NPC45579
0.6916	Remote Similarity	NPC239895
0.6916	Remote Similarity	NPC473161
0.6916	Remote Similarity	NPC202705
0.6916	Remote Similarity	NPC20066
0.6909	Remote Similarity	NPC473624
0.6909	Remote Similarity	NPC111323
0.6907	Remote Similarity	NPC27817
0.6907	Remote Similarity	NPC475681
0.6903	Remote Similarity	NPC23497
0.6893	Remote Similarity	NPC36668
0.6893	Remote Similarity	NPC471054
0.6893	Remote Similarity	NPC142159
0.6893	Remote Similarity	NPC474918
0.6893	Remote Similarity	NPC118011
0.6893	Remote Similarity	NPC95364
0.6893	Remote Similarity	NPC5509
0.6887	Remote Similarity	NPC476245
0.6887	Remote Similarity	NPC209355
0.6887	Remote Similarity	NPC279313
0.6881	Remote Similarity	NPC115862
0.6881	Remote Similarity	NPC471699
0.6875	Remote Similarity	NPC185
0.6875	Remote Similarity	NPC82666
0.6875	Remote Similarity	NPC475294
0.6875	Remote Similarity	NPC471061
0.687	Remote Similarity	NPC221144
0.6869	Remote Similarity	NPC279186
0.6869	Remote Similarity	NPC103486
0.6869	Remote Similarity	NPC158411
0.6869	Remote Similarity	NPC38796
0.6864	Remote Similarity	NPC146786
0.6857	Remote Similarity	NPC476049
0.6852	Remote Similarity	NPC35717
0.6852	Remote Similarity	NPC316598
0.6852	Remote Similarity	NPC57079
0.6852	Remote Similarity	NPC108368
0.6848	Remote Similarity	NPC474060
0.6832	Remote Similarity	NPC476426
0.6832	Remote Similarity	NPC471060
0.6832	Remote Similarity	NPC255174
0.6832	Remote Similarity	NPC28887
0.6827	Remote Similarity	NPC253177
0.6827	Remote Similarity	NPC469595
0.6827	Remote Similarity	NPC475823
0.6827	Remote Similarity	NPC212369
0.6827	Remote Similarity	NPC212679
0.6827	Remote Similarity	NPC474209
0.6827	Remote Similarity	NPC38952
0.6827	Remote Similarity	NPC476369
0.6827	Remote Similarity	NPC220454
0.6827	Remote Similarity	NPC476437
0.6827	Remote Similarity	NPC280592
0.6827	Remote Similarity	NPC113393
0.6827	Remote Similarity	NPC213636
0.6822	Remote Similarity	NPC318082
0.6818	Remote Similarity	NPC235369
0.6818	Remote Similarity	NPC87351
0.6818	Remote Similarity	NPC140591
0.6818	Remote Similarity	NPC189609
0.6818	Remote Similarity	NPC197835
0.6818	Remote Similarity	NPC291500
0.6818	Remote Similarity	NPC273005
0.6818	Remote Similarity	NPC31058
0.6818	Remote Similarity	NPC303653
0.6818	Remote Similarity	NPC469606
0.6814	Remote Similarity	NPC220155
0.681	Remote Similarity	NPC469463
0.681	Remote Similarity	NPC469454
0.681	Remote Similarity	NPC469496
0.681	Remote Similarity	NPC474271
0.68	Remote Similarity	NPC475083
0.6796	Remote Similarity	NPC7280
0.6796	Remote Similarity	NPC106051
0.6796	Remote Similarity	NPC229612
0.6792	Remote Similarity	NPC477129
0.6792	Remote Similarity	NPC299100
0.6792	Remote Similarity	NPC477130
0.6792	Remote Similarity	NPC78159
0.6792	Remote Similarity	NPC477241
0.6792	Remote Similarity	NPC38830
0.6789	Remote Similarity	NPC46761
0.6789	Remote Similarity	NPC54705
0.6783	Remote Similarity	NPC179798
0.6783	Remote Similarity	NPC474315
0.6783	Remote Similarity	NPC304180
0.6771	Remote Similarity	NPC26504
0.6771	Remote Similarity	NPC110725
0.6768	Remote Similarity	NPC6663
0.6768	Remote Similarity	NPC225515
0.6768	Remote Similarity	NPC55869
0.6768	Remote Similarity	NPC99308
0.6768	Remote Similarity	NPC275766
0.6768	Remote Similarity	NPC121984
0.6765	Remote Similarity	NPC116575
0.6765	Remote Similarity	NPC472974
0.6765	Remote Similarity	NPC194417
0.6765	Remote Similarity	NPC261721
0.6765	Remote Similarity	NPC291712
0.6762	Remote Similarity	NPC471329
0.6762	Remote Similarity	NPC296114
0.6762	Remote Similarity	NPC472975
0.6759	Remote Similarity	NPC53844
0.6759	Remote Similarity	NPC478233
0.6759	Remote Similarity	NPC273269
0.6757	Remote Similarity	NPC311612
0.6757	Remote Similarity	NPC476848
0.6737	Remote Similarity	NPC147438
0.6733	Remote Similarity	NPC7927
0.6733	Remote Similarity	NPC230527
0.6733	Remote Similarity	NPC14575
0.6733	Remote Similarity	NPC196487

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 NPC166770 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	186
0.1-0.2	1424
0.2-0.3	3718
0.3-0.4	2690
0.4-0.5	826
0.5-0.6	274
0.6-0.7	31
0.7-0.8	1
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
0.6972	Remote Similarity	NPD5091	Approved
0.6887	Remote Similarity	NPD5210	Approved
0.6887	Remote Similarity	NPD4629	Approved
0.6701	Remote Similarity	NPD4756	Discovery
0.6696	Remote Similarity	NPD5169	Approved
0.6667	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4695	Discontinued
0.6638	Remote Similarity	NPD5127	Approved
0.6602	Remote Similarity	NPD5279	Phase 3
0.6542	Remote Similarity	NPD5133	Approved
0.6522	Remote Similarity	NPD5128	Approved
0.6522	Remote Similarity	NPD5168	Approved
0.6509	Remote Similarity	NPD5785	Approved
0.6505	Remote Similarity	NPD1696	Phase 3
0.6496	Remote Similarity	NPD5216	Approved
0.6496	Remote Similarity	NPD5215	Approved
0.6496	Remote Similarity	NPD5217	Approved
0.6481	Remote Similarity	NPD5282	Discontinued
0.6471	Remote Similarity	NPD6110	Phase 1
0.6471	Remote Similarity	NPD5167	Approved
0.6446	Remote Similarity	NPD6314	Approved
0.6446	Remote Similarity	NPD6313	Approved
0.6446	Remote Similarity	NPD6335	Approved
0.6435	Remote Similarity	NPD6614	Approved
0.6415	Remote Similarity	NPD4753	Phase 2
0.6396	Remote Similarity	NPD5696	Approved
0.6372	Remote Similarity	NPD5211	Phase 2
0.6364	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5222	Approved
0.6364	Remote Similarity	NPD5221	Approved
0.6364	Remote Similarity	NPD7115	Discovery
0.6346	Remote Similarity	NPD1694	Approved
0.6346	Remote Similarity	NPD5363	Approved
0.6344	Remote Similarity	NPD3704	Approved
0.6339	Remote Similarity	NPD4696	Approved
0.6339	Remote Similarity	NPD5286	Approved
0.6339	Remote Similarity	NPD5285	Approved
0.6306	Remote Similarity	NPD5173	Approved
0.6303	Remote Similarity	NPD6053	Discontinued
0.6286	Remote Similarity	NPD5690	Phase 2
0.6286	Remote Similarity	NPD4694	Approved
0.6286	Remote Similarity	NPD5280	Approved
0.6286	Remote Similarity	NPD3618	Phase 1
0.6283	Remote Similarity	NPD5223	Approved
0.6281	Remote Similarity	NPD6868	Approved
0.6273	Remote Similarity	NPD5654	Approved
0.6262	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD5141	Approved
0.626	Remote Similarity	NPD7100	Approved
0.626	Remote Similarity	NPD7101	Approved
0.625	Remote Similarity	NPD3666	Approved
0.625	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3665	Phase 1
0.625	Remote Similarity	NPD3133	Approved
0.6239	Remote Similarity	NPD5779	Approved
0.6239	Remote Similarity	NPD5778	Approved
0.6231	Remote Similarity	NPD7260	Phase 2
0.6228	Remote Similarity	NPD5224	Approved
0.6228	Remote Similarity	NPD5226	Approved
0.6228	Remote Similarity	NPD5225	Approved
0.6228	Remote Similarity	NPD4633	Approved
0.6216	Remote Similarity	NPD4697	Phase 3
0.6214	Remote Similarity	NPD3667	Approved
0.6196	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD5175	Approved
0.6174	Remote Similarity	NPD5174	Approved
0.617	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD6084	Phase 2
0.6161	Remote Similarity	NPD5959	Approved
0.6161	Remote Similarity	NPD4755	Approved
0.6161	Remote Similarity	NPD6083	Phase 2
0.6154	Remote Similarity	NPD5697	Approved
0.6154	Remote Similarity	NPD7154	Phase 3
0.6147	Remote Similarity	NPD5284	Approved
0.6147	Remote Similarity	NPD6079	Approved
0.6147	Remote Similarity	NPD5281	Approved
0.6132	Remote Similarity	NPD4519	Discontinued
0.6132	Remote Similarity	NPD4623	Approved
0.6129	Remote Similarity	NPD4522	Approved
0.6126	Remote Similarity	NPD5695	Phase 3
0.6126	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD5369	Approved
0.6116	Remote Similarity	NPD4632	Approved
0.6111	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD6101	Approved
0.6102	Remote Similarity	NPD6881	Approved
0.6102	Remote Similarity	NPD6899	Approved
0.6102	Remote Similarity	NPD6011	Approved
0.6095	Remote Similarity	NPD4786	Approved
0.6095	Remote Similarity	NPD4197	Approved
0.6083	Remote Similarity	NPD6649	Approved
0.6083	Remote Similarity	NPD6650	Approved
0.608	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD4269	Approved
0.6058	Remote Similarity	NPD5209	Approved
0.6058	Remote Similarity	NPD4270	Approved
0.6055	Remote Similarity	NPD6698	Approved
0.6055	Remote Similarity	NPD46	Approved
0.6053	Remote Similarity	NPD4700	Approved
0.605	Remote Similarity	NPD6014	Approved
0.605	Remote Similarity	NPD6012	Approved
0.605	Remote Similarity	NPD6013	Approved
0.6038	Remote Similarity	NPD5329	Approved
0.6032	Remote Similarity	NPD5983	Phase 2
0.6019	Remote Similarity	NPD4252	Approved
0.6	Remote Similarity	NPD5362	Discontinued
0.6	Remote Similarity	NPD7102	Approved
0.6	Remote Similarity	NPD7331	Phase 2
0.6	Remote Similarity	NPD7290	Approved
0.6	Remote Similarity	NPD8264	Approved
0.6	Remote Similarity	NPD5694	Approved
0.6	Remote Similarity	NPD7515	Phase 2
0.6	Remote Similarity	NPD6411	Approved
0.6	Remote Similarity	NPD5693	Phase 1
0.6	Remote Similarity	NPD6883	Approved
0.5981	Remote Similarity	NPD5786	Approved
0.5981	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.598	Remote Similarity	NPD3617	Approved
0.598	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5969	Remote Similarity	NPD6336	Discontinued
0.5968	Remote Similarity	NPD6009	Approved
0.5966	Remote Similarity	NPD4730	Approved
0.5966	Remote Similarity	NPD4729	Approved
0.5965	Remote Similarity	NPD4225	Approved
0.5963	Remote Similarity	NPD5328	Approved
0.595	Remote Similarity	NPD8130	Phase 1
0.595	Remote Similarity	NPD6869	Approved
0.595	Remote Similarity	NPD6617	Approved
0.595	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.595	Remote Similarity	NPD6847	Approved
0.5946	Remote Similarity	NPD6399	Phase 3
0.5946	Remote Similarity	NPD4202	Approved
0.5932	Remote Similarity	NPD5739	Approved
0.5932	Remote Similarity	NPD6402	Approved
0.5932	Remote Similarity	NPD6675	Approved
0.5932	Remote Similarity	NPD7128	Approved
0.5917	Remote Similarity	NPD6373	Approved
0.5917	Remote Similarity	NPD6372	Approved
0.5909	Remote Similarity	NPD7838	Discovery
0.5909	Remote Similarity	NPD5692	Phase 3
0.5905	Remote Similarity	NPD4221	Approved
0.5905	Remote Similarity	NPD4223	Phase 3
0.5902	Remote Similarity	NPD6882	Approved
0.5902	Remote Similarity	NPD8297	Approved
0.59	Remote Similarity	NPD4058	Approved
0.5897	Remote Similarity	NPD4754	Approved
0.5893	Remote Similarity	NPD7748	Approved
0.5882	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD5701	Approved
0.5877	Remote Similarity	NPD7902	Approved
0.5872	Remote Similarity	NPD4518	Approved
0.5872	Remote Similarity	NPD5737	Approved
0.5872	Remote Similarity	NPD6672	Approved
0.5868	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5868	Remote Similarity	NPD4634	Approved
0.5868	Remote Similarity	NPD5247	Approved
0.5868	Remote Similarity	NPD5251	Approved
0.5868	Remote Similarity	NPD5248	Approved
0.5868	Remote Similarity	NPD5249	Phase 3
0.5868	Remote Similarity	NPD5250	Approved
0.5868	Remote Similarity	NPD5135	Approved
0.5856	Remote Similarity	NPD6050	Approved
0.5842	Remote Similarity	NPD8039	Approved
0.5833	Remote Similarity	NPD7320	Approved
0.5826	Remote Similarity	NPD7638	Approved
0.5821	Remote Similarity	NPD6845	Suspended
0.582	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.582	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5798	Remote Similarity	NPD4768	Approved
0.5798	Remote Similarity	NPD4767	Approved
0.5794	Remote Similarity	NPD3668	Phase 3
0.5794	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD5956	Approved
0.5789	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5781	Remote Similarity	NPD8513	Phase 3
0.5776	Remote Similarity	NPD7639	Approved
0.5776	Remote Similarity	NPD7640	Approved
0.5766	Remote Similarity	NPD5207	Approved
0.5758	Remote Similarity	NPD6033	Approved
0.5755	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5745	Remote Similarity	NPD368	Approved
0.5743	Remote Similarity	NPD4687	Approved
0.5738	Remote Similarity	NPD6371	Approved
0.5729	Remote Similarity	NPD7341	Phase 2
0.5714	Remote Similarity	NPD4819	Approved
0.5714	Remote Similarity	NPD4822	Approved
0.5714	Remote Similarity	NPD7983	Approved
0.5714	Remote Similarity	NPD6317	Approved
0.5714	Remote Similarity	NPD7637	Suspended
0.5714	Remote Similarity	NPD4820	Approved
0.5714	Remote Similarity	NPD4821	Approved
0.5702	Remote Similarity	NPD6686	Approved
0.5701	Remote Similarity	NPD4788	Approved
0.5691	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD4693	Phase 3
0.5688	Remote Similarity	NPD5330	Approved
0.5688	Remote Similarity	NPD7146	Approved
0.5688	Remote Similarity	NPD6684	Approved
0.5688	Remote Similarity	NPD7521	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data