NPASS Compound

Structure

NPC215253 OpenBabel07101718302D 28 29 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 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -4.5000 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 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 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 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 2.5981 0.5000 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 5.1962 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 -4.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -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 0.8660 0.5000 0.0000 C 0 0 1 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 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 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 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 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 12 1 0 0 0 0 6 12 2 0 0 0 0 7 8 2 0 0 0 0 7 13 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 19 1 0 0 0 0 11 17 2 0 0 0 0 11 28 1 0 0 0 0 12 19 1 0 0 0 0 13 3 1 6 0 0 0 13 14 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 16 20 2 0 0 0 0 17 18 1 0 0 0 0 18 22 1 1 0 0 0 19 25 2 0 0 0 0 20 21 1 0 0 0 0 20 23 1 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:	3.154
LogD:	2.738
LogS:	-4.161
# 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:	5.092
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:	-4.554
MDCK Permeability:	2.10297221201472e-05
Pgp-inhibitor:	0.03
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.024

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.938
Plasma Protein Binding (PPB):	77.55298614501953%
Volume Distribution (VD):	1.626
Pgp-substrate:	13.67484188079834%

ADMET: Metabolism

CYP1A2-inhibitor:	0.897
CYP1A2-substrate:	0.517
CYP2C19-inhibitor:	0.801
CYP2C19-substrate:	0.781
CYP2C9-inhibitor:	0.687
CYP2C9-substrate:	0.069
CYP2D6-inhibitor:	0.861
CYP2D6-substrate:	0.027
CYP3A4-inhibitor:	0.92
CYP3A4-substrate:	0.485

ADMET: Excretion

Clearance (CL):	3.604
Half-life (T1/2):	0.36

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.908
Drug-inuced Liver Injury (DILI):	0.402
AMES Toxicity:	0.036
Rat Oral Acute Toxicity:	0.934
Maximum Recommended Daily Dose:	0.919
Skin Sensitization:	0.915
Carcinogencity:	0.955
Eye Corrosion:	0.009
Eye Irritation:	0.107
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC215253

Natural Product ID:	NPC215253
*Common Name:**	11-Epi-Chaetomugilin I
IUPAC Name:	(7S,8S)-5-chloro-7-hydroxy-3-[(E,3S,4R)-4-hydroxy-3-methylpent-1-enyl]-7-methyl-8-[(E)-3-methyl-2-oxopent-3-enyl]-8H-isochromen-6-one
Synonyms:	11-Epi-Chaetomugilin I
Standard InCHIKey:	BYFBAJVBSPNIFS-FLPRNSHASA-N
Standard InCHI:	InChI=1S/C22H27ClO5/c1-6-12(2)19(25)10-18-17-11-28-15(8-7-13(3)14(4)24)9-16(17)20(23)21(26)22(18,5)27/h6-9,11,13-14,18,24,27H,10H2,1-5H3/b8-7+,12-6+/t13-,14+,18-,22-/m0/s1
SMILES:	C/C=C(C)/C(=O)C[C@H]1C2=COC(=CC2=C(C(=O)[C@@]1(C)O)Cl)/C=C/[C@H](C)[C@@H](C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1797232
PubChem CID:	53358201
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	n.a.	n.a.	n.a.	PMID[19246197]
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[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.	mycelium	n.a.	PMID[21548578]
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.	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	7
Others	4

Activity Type	# Activity
Cell Line	9
Others	2

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[486910]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	0.001	nM	PMID[486910]
NPT137	Cell Line	L1210	Mus musculus	IC50	=	0.0016	nM	PMID[486910]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	0.0012	nM	PMID[486910]
NPT71	Cell Line	HEK293	Homo sapiens	Survival	=	100.0	%	PMID[486911]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	99.6	%	PMID[486911]
NPT113	Cell Line	RAW264.7	Mus musculus	Survival	=	32.9	%	PMID[486911]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	800.0	nM	PMID[486911]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	6800.0	nM	PMID[486911]
NPT2	Others	Unspecified		Inhibition	=	99.9	%	PMID[486911]
NPT2	Others	Unspecified		IC50	=	900.0	nM	PMID[486911]

☑ 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 NPC215253 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
1.0	High Similarity	NPC185253
0.9891	High Similarity	NPC166770
0.9783	High Similarity	NPC134083
0.9479	High Similarity	NPC473144
0.9479	High Similarity	NPC297281
0.8298	Intermediate Similarity	NPC203795
0.8198	Intermediate Similarity	NPC476815
0.8198	Intermediate Similarity	NPC31641
0.8137	Intermediate Similarity	NPC224172
0.8108	Intermediate Similarity	NPC245320
0.8077	Intermediate Similarity	NPC272528
0.8036	Intermediate Similarity	NPC473145
0.7959	Intermediate Similarity	NPC224270
0.7768	Intermediate Similarity	NPC243298
0.7757	Intermediate Similarity	NPC232969
0.7757	Intermediate Similarity	NPC199107
0.7647	Intermediate Similarity	NPC12727
0.7642	Intermediate Similarity	NPC320294
0.7549	Intermediate Similarity	NPC143210
0.7525	Intermediate Similarity	NPC32552
0.75	Intermediate Similarity	NPC471694
0.7477	Intermediate Similarity	NPC25666
0.7477	Intermediate Similarity	NPC271059
0.7453	Intermediate Similarity	NPC469851
0.7431	Intermediate Similarity	NPC469853
0.7339	Intermediate Similarity	NPC469852
0.7333	Intermediate Similarity	NPC208094
0.7308	Intermediate Similarity	NPC295347
0.7297	Intermediate Similarity	NPC137911
0.7297	Intermediate Similarity	NPC228477
0.729	Intermediate Similarity	NPC472637
0.7273	Intermediate Similarity	NPC32037
0.7263	Intermediate Similarity	NPC478122
0.7228	Intermediate Similarity	NPC60765
0.7184	Intermediate Similarity	NPC166110
0.7184	Intermediate Similarity	NPC32944
0.7184	Intermediate Similarity	NPC193396
0.7182	Intermediate Similarity	NPC478052
0.7182	Intermediate Similarity	NPC32006
0.7182	Intermediate Similarity	NPC85529
0.7158	Intermediate Similarity	NPC97173
0.7157	Intermediate Similarity	NPC210216
0.7157	Intermediate Similarity	NPC51358
0.7157	Intermediate Similarity	NPC307092
0.7143	Intermediate Similarity	NPC31021
0.7115	Intermediate Similarity	NPC242637
0.7115	Intermediate Similarity	NPC248193
0.7105	Intermediate Similarity	NPC66108
0.71	Intermediate Similarity	NPC187529
0.7087	Intermediate Similarity	NPC131864
0.7083	Intermediate Similarity	NPC231739
0.7071	Intermediate Similarity	NPC16488
0.7071	Intermediate Similarity	NPC288281
0.7059	Intermediate Similarity	NPC26078
0.7059	Intermediate Similarity	NPC473658
0.7043	Intermediate Similarity	NPC321496
0.7043	Intermediate Similarity	NPC326264
0.703	Intermediate Similarity	NPC315395
0.703	Intermediate Similarity	NPC94666
0.703	Intermediate Similarity	NPC316426
0.7027	Intermediate Similarity	NPC477125
0.7027	Intermediate Similarity	NPC266570
0.7027	Intermediate Similarity	NPC189863
0.701	Intermediate Similarity	NPC19900
0.7	Intermediate Similarity	NPC473624
0.6991	Remote Similarity	NPC23497
0.699	Remote Similarity	NPC118011
0.699	Remote Similarity	NPC142159
0.699	Remote Similarity	NPC95364
0.699	Remote Similarity	NPC36668
0.699	Remote Similarity	NPC212598
0.6981	Remote Similarity	NPC476245
0.6981	Remote Similarity	NPC91408
0.6979	Remote Similarity	NPC82666
0.6972	Remote Similarity	NPC244456
0.6972	Remote Similarity	NPC469657
0.6972	Remote Similarity	NPC471699
0.6972	Remote Similarity	NPC115862
0.6964	Remote Similarity	NPC185
0.6961	Remote Similarity	NPC476079
0.6961	Remote Similarity	NPC103743
0.6961	Remote Similarity	NPC113370
0.6949	Remote Similarity	NPC146786
0.6944	Remote Similarity	NPC57079
0.6944	Remote Similarity	NPC108368
0.6944	Remote Similarity	NPC35717
0.6931	Remote Similarity	NPC6185
0.6931	Remote Similarity	NPC307112
0.6931	Remote Similarity	NPC8518
0.6931	Remote Similarity	NPC263997
0.6931	Remote Similarity	NPC132228
0.6931	Remote Similarity	NPC241512
0.6923	Remote Similarity	NPC475823
0.6923	Remote Similarity	NPC474209
0.6923	Remote Similarity	NPC469372
0.6923	Remote Similarity	NPC265856
0.6923	Remote Similarity	NPC212369
0.6923	Remote Similarity	NPC38952
0.6916	Remote Similarity	NPC318082
0.6909	Remote Similarity	NPC469606
0.6909	Remote Similarity	NPC273005
0.6909	Remote Similarity	NPC31058
0.6907	Remote Similarity	NPC475994
0.69	Remote Similarity	NPC477785
0.69	Remote Similarity	NPC477784
0.69	Remote Similarity	NPC477786
0.6897	Remote Similarity	NPC474271
0.6893	Remote Similarity	NPC7280
0.6893	Remote Similarity	NPC307298
0.6893	Remote Similarity	NPC53454
0.6893	Remote Similarity	NPC229612
0.6887	Remote Similarity	NPC474882
0.6887	Remote Similarity	NPC299100
0.6887	Remote Similarity	NPC78159
0.6887	Remote Similarity	NPC38830
0.6881	Remote Similarity	NPC46761
0.687	Remote Similarity	NPC474315
0.6863	Remote Similarity	NPC291712
0.6863	Remote Similarity	NPC234038
0.6863	Remote Similarity	NPC472974
0.6857	Remote Similarity	NPC45579
0.6857	Remote Similarity	NPC303697
0.6857	Remote Similarity	NPC472975
0.6852	Remote Similarity	NPC202705
0.6852	Remote Similarity	NPC239895
0.6852	Remote Similarity	NPC473161
0.6852	Remote Similarity	NPC20066
0.6847	Remote Similarity	NPC111323
0.6847	Remote Similarity	NPC476848
0.6837	Remote Similarity	NPC27817
0.6837	Remote Similarity	NPC475681
0.6827	Remote Similarity	NPC474918
0.6827	Remote Similarity	NPC471054
0.6827	Remote Similarity	NPC5509
0.6822	Remote Similarity	NPC471698
0.6822	Remote Similarity	NPC279313
0.6822	Remote Similarity	NPC180950
0.6822	Remote Similarity	NPC209355
0.6822	Remote Similarity	NPC280725
0.6822	Remote Similarity	NPC183012
0.6818	Remote Similarity	NPC207885
0.6814	Remote Similarity	NPC475294
0.681	Remote Similarity	NPC221144
0.6804	Remote Similarity	NPC471061
0.68	Remote Similarity	NPC158411
0.68	Remote Similarity	NPC279186
0.68	Remote Similarity	NPC38796
0.68	Remote Similarity	NPC103486
0.6796	Remote Similarity	NPC181327
0.6792	Remote Similarity	NPC282644
0.6792	Remote Similarity	NPC29798
0.6792	Remote Similarity	NPC476049
0.6792	Remote Similarity	NPC134826
0.6789	Remote Similarity	NPC222011
0.6789	Remote Similarity	NPC316598
0.6789	Remote Similarity	NPC306908
0.6786	Remote Similarity	NPC118911
0.6774	Remote Similarity	NPC474060
0.6768	Remote Similarity	NPC74086
0.6765	Remote Similarity	NPC255174
0.6765	Remote Similarity	NPC476426
0.6765	Remote Similarity	NPC281172
0.6765	Remote Similarity	NPC471060
0.6765	Remote Similarity	NPC28887
0.6762	Remote Similarity	NPC253177
0.6762	Remote Similarity	NPC469464
0.6762	Remote Similarity	NPC220454
0.6762	Remote Similarity	NPC469595
0.6762	Remote Similarity	NPC213636
0.6762	Remote Similarity	NPC113393
0.6762	Remote Similarity	NPC280592
0.6762	Remote Similarity	NPC476369
0.6762	Remote Similarity	NPC212679
0.6762	Remote Similarity	NPC476437
0.6759	Remote Similarity	NPC78473
0.6757	Remote Similarity	NPC87351
0.6757	Remote Similarity	NPC235369
0.6757	Remote Similarity	NPC303653
0.6757	Remote Similarity	NPC189609
0.6757	Remote Similarity	NPC140591
0.6757	Remote Similarity	NPC291500
0.6757	Remote Similarity	NPC114540
0.6757	Remote Similarity	NPC32577
0.6757	Remote Similarity	NPC155332
0.6757	Remote Similarity	NPC197835
0.6754	Remote Similarity	NPC327106
0.6754	Remote Similarity	NPC220155
0.6752	Remote Similarity	NPC469463
0.6752	Remote Similarity	NPC469454
0.6752	Remote Similarity	NPC469496
0.6733	Remote Similarity	NPC475083
0.6733	Remote Similarity	NPC297398
0.6731	Remote Similarity	NPC477302
0.6731	Remote Similarity	NPC106051
0.6729	Remote Similarity	NPC477130
0.6729	Remote Similarity	NPC477241
0.6729	Remote Similarity	NPC217624
0.6729	Remote Similarity	NPC191521
0.6729	Remote Similarity	NPC474328
0.6729	Remote Similarity	NPC474690

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 NPC215253 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
0.6909	Remote Similarity	NPD5091	Approved
0.6822	Remote Similarity	NPD4629	Approved
0.6822	Remote Similarity	NPD5210	Approved
0.6783	Remote Similarity	NPD5169	Approved
0.6768	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD5127	Approved
0.6633	Remote Similarity	NPD4756	Discovery
0.6609	Remote Similarity	NPD5168	Approved
0.6609	Remote Similarity	NPD5128	Approved
0.6602	Remote Similarity	NPD1696	Phase 3
0.66	Remote Similarity	NPD4695	Discontinued
0.6581	Remote Similarity	NPD5217	Approved
0.6581	Remote Similarity	NPD5215	Approved
0.6581	Remote Similarity	NPD5216	Approved
0.6555	Remote Similarity	NPD5167	Approved
0.6538	Remote Similarity	NPD5279	Phase 3
0.6529	Remote Similarity	NPD6314	Approved
0.6529	Remote Similarity	NPD6313	Approved
0.6529	Remote Similarity	NPD6335	Approved
0.6481	Remote Similarity	NPD5133	Approved
0.646	Remote Similarity	NPD5211	Phase 2
0.6455	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD5221	Approved
0.6455	Remote Similarity	NPD5222	Approved
0.6449	Remote Similarity	NPD5785	Approved
0.6446	Remote Similarity	NPD7115	Discovery
0.6429	Remote Similarity	NPD5285	Approved
0.6429	Remote Similarity	NPD5286	Approved
0.6429	Remote Similarity	NPD4696	Approved
0.6422	Remote Similarity	NPD5282	Discontinued
0.6408	Remote Similarity	NPD6110	Phase 1
0.6396	Remote Similarity	NPD5173	Approved
0.6381	Remote Similarity	NPD3618	Phase 1
0.6379	Remote Similarity	NPD6614	Approved
0.6372	Remote Similarity	NPD5223	Approved
0.6364	Remote Similarity	NPD6868	Approved
0.6355	Remote Similarity	NPD4753	Phase 2
0.6348	Remote Similarity	NPD5141	Approved
0.6341	Remote Similarity	NPD7100	Approved
0.6341	Remote Similarity	NPD7101	Approved
0.6339	Remote Similarity	NPD5696	Approved
0.6316	Remote Similarity	NPD5226	Approved
0.6316	Remote Similarity	NPD5225	Approved
0.6316	Remote Similarity	NPD5224	Approved
0.6316	Remote Similarity	NPD4633	Approved
0.6311	Remote Similarity	NPD3667	Approved
0.6306	Remote Similarity	NPD4697	Phase 3
0.6286	Remote Similarity	NPD1694	Approved
0.6286	Remote Similarity	NPD5363	Approved
0.6277	Remote Similarity	NPD3704	Approved
0.6261	Remote Similarity	NPD5175	Approved
0.6261	Remote Similarity	NPD5174	Approved
0.625	Remote Similarity	NPD6053	Discontinued
0.625	Remote Similarity	NPD4755	Approved
0.6239	Remote Similarity	NPD6079	Approved
0.6239	Remote Similarity	NPD5697	Approved
0.6226	Remote Similarity	NPD4694	Approved
0.6226	Remote Similarity	NPD5280	Approved
0.6226	Remote Similarity	NPD5690	Phase 2
0.6216	Remote Similarity	NPD5654	Approved
0.6204	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD4632	Approved
0.6195	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.619	Remote Similarity	NPD4786	Approved
0.619	Remote Similarity	NPD3665	Phase 1
0.619	Remote Similarity	NPD3133	Approved
0.619	Remote Similarity	NPD3666	Approved
0.6186	Remote Similarity	NPD6899	Approved
0.6186	Remote Similarity	NPD6881	Approved
0.6186	Remote Similarity	NPD6011	Approved
0.6183	Remote Similarity	NPD7260	Phase 2
0.6182	Remote Similarity	NPD5779	Approved
0.6182	Remote Similarity	NPD5778	Approved
0.6167	Remote Similarity	NPD6649	Approved
0.6167	Remote Similarity	NPD6650	Approved
0.614	Remote Similarity	NPD4700	Approved
0.6134	Remote Similarity	NPD6014	Approved
0.6134	Remote Similarity	NPD6012	Approved
0.6134	Remote Similarity	NPD6013	Approved
0.6129	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD5983	Phase 2
0.6106	Remote Similarity	NPD5959	Approved
0.6106	Remote Similarity	NPD6084	Phase 2
0.6106	Remote Similarity	NPD6083	Phase 2
0.6105	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.61	Remote Similarity	NPD8264	Approved
0.6095	Remote Similarity	NPD7154	Phase 3
0.6091	Remote Similarity	NPD5284	Approved
0.6091	Remote Similarity	NPD5281	Approved
0.6091	Remote Similarity	NPD7515	Phase 2
0.6083	Remote Similarity	NPD7102	Approved
0.6083	Remote Similarity	NPD6883	Approved
0.6083	Remote Similarity	NPD7290	Approved
0.608	Remote Similarity	NPD4522	Approved
0.6075	Remote Similarity	NPD4623	Approved
0.6075	Remote Similarity	NPD4519	Discontinued
0.6071	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD5695	Phase 3
0.6058	Remote Similarity	NPD5369	Approved
0.6055	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD6101	Approved
0.6055	Remote Similarity	NPD5328	Approved
0.6053	Remote Similarity	NPD4225	Approved
0.605	Remote Similarity	NPD4729	Approved
0.605	Remote Similarity	NPD4730	Approved
0.6048	Remote Similarity	NPD6009	Approved
0.6047	Remote Similarity	NPD6336	Discontinued
0.6038	Remote Similarity	NPD4197	Approved
0.6036	Remote Similarity	NPD6399	Phase 3
0.6036	Remote Similarity	NPD4202	Approved
0.6033	Remote Similarity	NPD6847	Approved
0.6033	Remote Similarity	NPD6617	Approved
0.6033	Remote Similarity	NPD8130	Phase 1
0.6033	Remote Similarity	NPD6869	Approved
0.6032	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD5739	Approved
0.6017	Remote Similarity	NPD6675	Approved
0.6017	Remote Similarity	NPD7128	Approved
0.6017	Remote Similarity	NPD6402	Approved
0.6	Remote Similarity	NPD6698	Approved
0.6	Remote Similarity	NPD6372	Approved
0.6	Remote Similarity	NPD4269	Approved
0.6	Remote Similarity	NPD4270	Approved
0.6	Remote Similarity	NPD5209	Approved
0.6	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6	Remote Similarity	NPD46	Approved
0.6	Remote Similarity	NPD6373	Approved
0.5984	Remote Similarity	NPD6882	Approved
0.5984	Remote Similarity	NPD8297	Approved
0.5983	Remote Similarity	NPD4754	Approved
0.5982	Remote Similarity	NPD7748	Approved
0.5981	Remote Similarity	NPD5329	Approved
0.5966	Remote Similarity	NPD5701	Approved
0.5965	Remote Similarity	NPD7902	Approved
0.5962	Remote Similarity	NPD4252	Approved
0.595	Remote Similarity	NPD5251	Approved
0.595	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.595	Remote Similarity	NPD5250	Approved
0.595	Remote Similarity	NPD5247	Approved
0.595	Remote Similarity	NPD5248	Approved
0.595	Remote Similarity	NPD5135	Approved
0.595	Remote Similarity	NPD4634	Approved
0.595	Remote Similarity	NPD5249	Phase 3
0.5946	Remote Similarity	NPD5693	Phase 1
0.5946	Remote Similarity	NPD6411	Approved
0.5946	Remote Similarity	NPD5694	Approved
0.5943	Remote Similarity	NPD5362	Discontinued
0.5938	Remote Similarity	NPD7331	Phase 2
0.5926	Remote Similarity	NPD5786	Approved
0.5926	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD3617	Approved
0.5917	Remote Similarity	NPD7320	Approved
0.5913	Remote Similarity	NPD7638	Approved
0.5902	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD3668	Phase 3
0.5882	Remote Similarity	NPD4767	Approved
0.5882	Remote Similarity	NPD4768	Approved
0.5862	Remote Similarity	NPD7640	Approved
0.5862	Remote Similarity	NPD7639	Approved
0.5859	Remote Similarity	NPD8513	Phase 3
0.5856	Remote Similarity	NPD7838	Discovery
0.5856	Remote Similarity	NPD5692	Phase 3
0.5849	Remote Similarity	NPD4223	Phase 3
0.5849	Remote Similarity	NPD4221	Approved
0.5842	Remote Similarity	NPD4058	Approved
0.5833	Remote Similarity	NPD6033	Approved
0.5833	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD6672	Approved
0.5818	Remote Similarity	NPD4518	Approved
0.5818	Remote Similarity	NPD5737	Approved
0.5804	Remote Similarity	NPD6050	Approved
0.5794	Remote Similarity	NPD6317	Approved
0.5784	Remote Similarity	NPD8039	Approved
0.5778	Remote Similarity	NPD6845	Suspended
0.5772	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.5772	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5772	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5746	Remote Similarity	NPD5956	Approved
0.5741	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5739	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5736	Remote Similarity	NPD8515	Approved
0.5736	Remote Similarity	NPD8516	Approved
0.5736	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5736	Remote Similarity	NPD8517	Approved
0.5727	Remote Similarity	NPD3573	Approved
0.5714	Remote Similarity	NPD5207	Approved
0.5714	Remote Similarity	NPD6274	Approved
0.5702	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD7900	Approved
0.5701	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5691	Remote Similarity	NPD6371	Approved
0.5686	Remote Similarity	NPD4687	Approved
0.5684	Remote Similarity	NPD368	Approved
0.567	Remote Similarity	NPD7341	Phase 2
0.5664	Remote Similarity	NPD7637	Suspended
0.5664	Remote Similarity	NPD7983	Approved
0.566	Remote Similarity	NPD4822	Approved
0.566	Remote Similarity	NPD4819	Approved
0.566	Remote Similarity	NPD4820	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