NPASS Compound

Structure

NPC224172 OpenBabel07101719522D 22 23 0 0 1 0 0 0 0 0999 V2000 6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 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 5.1962 -1.0000 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 2.5981 -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 6.0622 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 0.0000 C 0 0 1 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 2 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 1 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 1 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 6.9282 -3.0000 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 4 5 2 0 0 0 0 4 8 1 0 0 0 0 5 10 1 0 0 0 0 6 10 2 0 0 0 0 6 11 1 0 0 0 0 7 22 1 0 0 0 0 8 1 1 6 0 0 0 8 9 1 0 0 0 0 9 2 1 1 0 0 0 9 18 1 0 0 0 0 10 22 1 0 0 0 0 11 12 1 0 0 0 0 11 13 2 0 0 0 0 12 7 1 6 0 0 0 12 14 1 0 0 0 0 13 15 1 0 0 0 0 13 17 1 0 0 0 0 14 16 1 1 0 0 0 14 19 1 0 0 0 0 15 16 1 0 0 0 0 15 20 2 0 0 0 0 16 3 1 1 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.11
Volume:	316.796
LogP:	1.265
LogD:	1.829
LogS:	-2.436
# Rotatable Bonds:	3
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.675
Synthetic Accessibility Score:	5.203
Fsp3:	0.562
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.607
MDCK Permeability:	1.64515931828646e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.874
Human Intestinal Absorption (HIA):	0.026
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.03

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.969
Plasma Protein Binding (PPB):	81.74398040771484%
Volume Distribution (VD):	1.512
Pgp-substrate:	14.273476600646973%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.149
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.831
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.049
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.057
CYP3A4-inhibitor:	0.061
CYP3A4-substrate:	0.254

ADMET: Excretion

Clearance (CL):	5.519
Half-life (T1/2):	0.747

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.326
Drug-inuced Liver Injury (DILI):	0.954
AMES Toxicity:	0.283
Rat Oral Acute Toxicity:	0.922
Maximum Recommended Daily Dose:	0.981
Skin Sensitization:	0.942
Carcinogencity:	0.46
Eye Corrosion:	0.892
Eye Irritation:	0.49
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC224172

Natural Product ID:	NPC224172
*Common Name:**	Chaetomugilin R
IUPAC Name:	(7R,8S,8aS)-5-chloro-7,8-dihydroxy-3-[(E,3S,4S)-4-hydroxy-3-methylpent-1-enyl]-7-methyl-8,8a-dihydro-1H-isochromen-6-one
Synonyms:	Chaetomugilin R
Standard InCHIKey:	HYQLBUHERBRGKE-HKOMCDGQSA-N
Standard InCHI:	InChI=1S/C16H21ClO5/c1-8(9(2)18)4-5-10-6-11-12(7-22-10)14(19)16(3,21)15(20)13(11)17/h4-6,8-9,12,14,18-19,21H,7H2,1-3H3/b5-4+/t8-,9-,12+,14-,16+/m0/s1
SMILES:	C[C@@H](/C=C/C1=CC2=C(C(=O)[C@@](C)([C@H]([C@@H]2CO1)O)O)Cl)[C@H](C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1797231
PubChem CID:	53358200
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0003477] Azaphilones

*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	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[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	=	0.032	nM	PMID[491171]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	0.0518	nM	PMID[491171]
NPT137	Cell Line	L1210	Mus musculus	IC50	=	0.0671	nM	PMID[491171]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	0.0671	nM	PMID[491171]

☑ 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 NPC224172 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	204
0.1-0.2	1256
0.2-0.3	5318
0.3-0.4	10510
0.4-0.5	17973
0.5-0.6	6185
0.6-0.7	1136
0.7-0.8	100
0.8-0.85	13
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.8365	Intermediate Similarity	NPC199107
0.8365	Intermediate Similarity	NPC232969
0.8252	Intermediate Similarity	NPC297281
0.8252	Intermediate Similarity	NPC473144
0.8137	Intermediate Similarity	NPC185253
0.8137	Intermediate Similarity	NPC215253
0.8039	Intermediate Similarity	NPC166770
0.8	Intermediate Similarity	NPC143210
0.798	Intermediate Similarity	NPC32552
0.7941	Intermediate Similarity	NPC134083
0.7925	Intermediate Similarity	NPC469852
0.7921	Intermediate Similarity	NPC12727
0.7879	Intermediate Similarity	NPC224270
0.785	Intermediate Similarity	NPC469853
0.783	Intermediate Similarity	NPC272528
0.7807	Intermediate Similarity	NPC476815
0.7807	Intermediate Similarity	NPC31641
0.7778	Intermediate Similarity	NPC327106
0.7723	Intermediate Similarity	NPC282644
0.7723	Intermediate Similarity	NPC29798
0.7719	Intermediate Similarity	NPC245320
0.7714	Intermediate Similarity	NPC469851
0.7692	Intermediate Similarity	NPC35717
0.7652	Intermediate Similarity	NPC473145
0.7525	Intermediate Similarity	NPC469464
0.7524	Intermediate Similarity	NPC306908
0.7391	Intermediate Similarity	NPC243298
0.7374	Intermediate Similarity	NPC187529
0.7353	Intermediate Similarity	NPC131864
0.7297	Intermediate Similarity	NPC264819
0.7281	Intermediate Similarity	NPC321496
0.7264	Intermediate Similarity	NPC471694
0.7248	Intermediate Similarity	NPC473624
0.7228	Intermediate Similarity	NPC23622
0.7228	Intermediate Similarity	NPC113370
0.7228	Intermediate Similarity	NPC103743
0.7228	Intermediate Similarity	NPC476079
0.7207	Intermediate Similarity	NPC266514
0.72	Intermediate Similarity	NPC307112
0.72	Intermediate Similarity	NPC281172
0.7172	Intermediate Similarity	NPC475083
0.7143	Intermediate Similarity	NPC477241
0.7129	Intermediate Similarity	NPC291712
0.7129	Intermediate Similarity	NPC196381
0.7115	Intermediate Similarity	NPC193396
0.7115	Intermediate Similarity	NPC32944
0.7115	Intermediate Similarity	NPC166110
0.7091	Intermediate Similarity	NPC104161
0.7091	Intermediate Similarity	NPC271059
0.7091	Intermediate Similarity	NPC25666
0.7091	Intermediate Similarity	NPC320294
0.7091	Intermediate Similarity	NPC118902
0.7091	Intermediate Similarity	NPC469980
0.7087	Intermediate Similarity	NPC142159
0.7087	Intermediate Similarity	NPC95364
0.7083	Intermediate Similarity	NPC97173
0.7083	Intermediate Similarity	NPC82666
0.7075	Intermediate Similarity	NPC471698
0.7064	Intermediate Similarity	NPC207885
0.7048	Intermediate Similarity	NPC248193
0.7043	Intermediate Similarity	NPC66108
0.7019	Intermediate Similarity	NPC477684
0.7019	Intermediate Similarity	NPC316228
0.7019	Intermediate Similarity	NPC274075
0.701	Intermediate Similarity	NPC478122
0.7	Intermediate Similarity	NPC16488
0.699	Remote Similarity	NPC472008
0.697	Remote Similarity	NPC275766
0.6964	Remote Similarity	NPC32006
0.6964	Remote Similarity	NPC477125
0.6964	Remote Similarity	NPC85529
0.6961	Remote Similarity	NPC472009
0.6957	Remote Similarity	NPC317107
0.6944	Remote Similarity	NPC20066
0.6944	Remote Similarity	NPC239895
0.693	Remote Similarity	NPC475065
0.6923	Remote Similarity	NPC471054
0.6916	Remote Similarity	NPC227494
0.6916	Remote Similarity	NPC91408
0.6909	Remote Similarity	NPC112613
0.6909	Remote Similarity	NPC472637
0.6903	Remote Similarity	NPC330011
0.6903	Remote Similarity	NPC329048
0.6897	Remote Similarity	NPC317687
0.6893	Remote Similarity	NPC472007
0.6887	Remote Similarity	NPC242637
0.687	Remote Similarity	NPC99760
0.687	Remote Similarity	NPC89408
0.6857	Remote Similarity	NPC475879
0.6852	Remote Similarity	NPC94337
0.6852	Remote Similarity	NPC473291
0.6842	Remote Similarity	NPC473482
0.6842	Remote Similarity	NPC475418
0.6842	Remote Similarity	NPC322903
0.6842	Remote Similarity	NPC318363
0.6837	Remote Similarity	NPC248624
0.6832	Remote Similarity	NPC477784
0.6832	Remote Similarity	NPC477785
0.6832	Remote Similarity	NPC185256
0.6832	Remote Similarity	NPC477786
0.6827	Remote Similarity	NPC60765
0.6814	Remote Similarity	NPC478052
0.6796	Remote Similarity	NPC316426
0.6796	Remote Similarity	NPC203795
0.6796	Remote Similarity	NPC315395
0.6792	Remote Similarity	NPC142838
0.6792	Remote Similarity	NPC472010
0.6789	Remote Similarity	NPC471916
0.6789	Remote Similarity	NPC208094
0.6789	Remote Similarity	NPC245521
0.6783	Remote Similarity	NPC38154
0.6783	Remote Similarity	NPC87335
0.678	Remote Similarity	NPC247069
0.6777	Remote Similarity	NPC478051
0.6771	Remote Similarity	NPC122244
0.6759	Remote Similarity	NPC295347
0.6757	Remote Similarity	NPC244456
0.6757	Remote Similarity	NPC469657
0.6757	Remote Similarity	NPC472753
0.6757	Remote Similarity	NPC471699
0.6754	Remote Similarity	NPC473284
0.675	Remote Similarity	NPC284707
0.6731	Remote Similarity	NPC241054
0.6729	Remote Similarity	NPC189651
0.6729	Remote Similarity	NPC320552
0.6729	Remote Similarity	NPC475098
0.6727	Remote Similarity	NPC316598
0.6727	Remote Similarity	NPC161855
0.6723	Remote Similarity	NPC64318
0.672	Remote Similarity	NPC287903
0.672	Remote Similarity	NPC156797
0.67	Remote Similarity	NPC74086
0.6699	Remote Similarity	NPC15807
0.6698	Remote Similarity	NPC213636
0.6698	Remote Similarity	NPC327253
0.6698	Remote Similarity	NPC265856
0.6698	Remote Similarity	NPC471399
0.6698	Remote Similarity	NPC280592
0.6698	Remote Similarity	NPC253177
0.6696	Remote Similarity	NPC472507
0.6696	Remote Similarity	NPC39996
0.6696	Remote Similarity	NPC478176
0.6696	Remote Similarity	NPC472754
0.6696	Remote Similarity	NPC473807
0.6695	Remote Similarity	NPC469454
0.6695	Remote Similarity	NPC478212
0.6695	Remote Similarity	NPC469463
0.6695	Remote Similarity	NPC469496
0.6695	Remote Similarity	NPC326264
0.6667	Remote Similarity	NPC179798
0.6667	Remote Similarity	NPC474315
0.6667	Remote Similarity	NPC98249
0.6667	Remote Similarity	NPC266570
0.6667	Remote Similarity	NPC46761
0.6667	Remote Similarity	NPC44261
0.6667	Remote Similarity	NPC2003
0.6667	Remote Similarity	NPC476299
0.6667	Remote Similarity	NPC472011
0.6667	Remote Similarity	NPC1679
0.6667	Remote Similarity	NPC106051
0.6667	Remote Similarity	NPC304180
0.6667	Remote Similarity	NPC53396
0.6667	Remote Similarity	NPC474012
0.6667	Remote Similarity	NPC474518
0.6667	Remote Similarity	NPC25701
0.6641	Remote Similarity	NPC470185
0.6639	Remote Similarity	NPC147912
0.6639	Remote Similarity	NPC67259
0.6638	Remote Similarity	NPC228477
0.6638	Remote Similarity	NPC23497
0.6638	Remote Similarity	NPC101018
0.6638	Remote Similarity	NPC137911
0.6638	Remote Similarity	NPC20192
0.6638	Remote Similarity	NPC471400
0.6637	Remote Similarity	NPC475871
0.6637	Remote Similarity	NPC131366
0.6637	Remote Similarity	NPC475945
0.6637	Remote Similarity	NPC475050
0.6636	Remote Similarity	NPC303230
0.6636	Remote Similarity	NPC20078
0.6636	Remote Similarity	NPC474938
0.6636	Remote Similarity	NPC53844
0.6636	Remote Similarity	NPC146852
0.6636	Remote Similarity	NPC473574
0.6636	Remote Similarity	NPC6099
0.6636	Remote Similarity	NPC471329
0.6636	Remote Similarity	NPC114345
0.6636	Remote Similarity	NPC327760
0.6636	Remote Similarity	NPC296114
0.6636	Remote Similarity	NPC474785
0.6614	Remote Similarity	NPC221414
0.6612	Remote Similarity	NPC50774
0.6612	Remote Similarity	NPC709
0.6612	Remote Similarity	NPC315974
0.6612	Remote Similarity	NPC186525
0.6609	Remote Similarity	NPC473169
0.6607	Remote Similarity	NPC110443
0.6607	Remote Similarity	NPC169365
0.6607	Remote Similarity	NPC133907
0.6607	Remote Similarity	NPC128733

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 NPC224172 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	184
0.1-0.2	1472
0.2-0.3	3914
0.3-0.4	2514
0.4-0.5	809
0.5-0.6	242
0.6-0.7	15
0.7-0.8	0
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
0.67	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD5778	Approved
0.6574	Remote Similarity	NPD5779	Approved
0.6529	Remote Similarity	NPD7115	Discovery
0.6505	Remote Similarity	NPD6110	Phase 1
0.6449	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD6101	Approved
0.6441	Remote Similarity	NPD5169	Approved
0.641	Remote Similarity	NPD5128	Approved
0.6387	Remote Similarity	NPD5215	Approved
0.6387	Remote Similarity	NPD5216	Approved
0.6387	Remote Similarity	NPD5127	Approved
0.6387	Remote Similarity	NPD5217	Approved
0.6364	Remote Similarity	NPD5282	Discontinued
0.6341	Remote Similarity	NPD6314	Approved
0.6341	Remote Similarity	NPD6313	Approved
0.6341	Remote Similarity	NPD6335	Approved
0.633	Remote Similarity	NPD7983	Approved
0.633	Remote Similarity	NPD6411	Approved
0.632	Remote Similarity	NPD8513	Phase 3
0.6303	Remote Similarity	NPD4634	Approved
0.629	Remote Similarity	NPD7100	Approved
0.629	Remote Similarity	NPD7101	Approved
0.6283	Remote Similarity	NPD4225	Approved
0.6261	Remote Similarity	NPD5211	Phase 2
0.6239	Remote Similarity	NPD46	Approved
0.6239	Remote Similarity	NPD6698	Approved
0.623	Remote Similarity	NPD5167	Approved
0.6228	Remote Similarity	NPD4696	Approved
0.6228	Remote Similarity	NPD5286	Approved
0.6228	Remote Similarity	NPD5285	Approved
0.6226	Remote Similarity	NPD1696	Phase 3
0.6198	Remote Similarity	NPD6053	Discontinued
0.6195	Remote Similarity	NPD4755	Approved
0.619	Remote Similarity	NPD8516	Approved
0.619	Remote Similarity	NPD8515	Approved
0.619	Remote Similarity	NPD8517	Approved
0.6186	Remote Similarity	NPD5697	Approved
0.616	Remote Similarity	NPD4522	Approved
0.6154	Remote Similarity	NPD6033	Approved
0.6154	Remote Similarity	NPD5141	Approved
0.6148	Remote Similarity	NPD4632	Approved
0.6134	Remote Similarity	NPD6899	Approved
0.6134	Remote Similarity	NPD6881	Approved
0.6134	Remote Similarity	NPD5168	Approved
0.6121	Remote Similarity	NPD5224	Approved
0.6121	Remote Similarity	NPD4633	Approved
0.6121	Remote Similarity	NPD5226	Approved
0.6121	Remote Similarity	NPD5225	Approved
0.6111	Remote Similarity	NPD6319	Approved
0.6102	Remote Similarity	NPD7128	Approved
0.6102	Remote Similarity	NPD6675	Approved
0.6102	Remote Similarity	NPD5739	Approved
0.6102	Remote Similarity	NPD6402	Approved
0.6091	Remote Similarity	NPD7838	Discovery
0.6087	Remote Similarity	NPD4700	Approved
0.6083	Remote Similarity	NPD6012	Approved
0.6083	Remote Similarity	NPD6014	Approved
0.6083	Remote Similarity	NPD6013	Approved
0.6078	Remote Similarity	NPD4756	Discovery
0.6068	Remote Similarity	NPD5174	Approved
0.6068	Remote Similarity	NPD5175	Approved
0.6066	Remote Similarity	NPD8297	Approved
0.6063	Remote Similarity	NPD5983	Phase 2
0.605	Remote Similarity	NPD5701	Approved
0.6048	Remote Similarity	NPD6868	Approved
0.6034	Remote Similarity	NPD5223	Approved
0.6033	Remote Similarity	NPD7102	Approved
0.6033	Remote Similarity	NPD6883	Approved
0.6033	Remote Similarity	NPD7290	Approved
0.6018	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6336	Discontinued
0.6	Remote Similarity	NPD6011	Approved
0.6	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7320	Approved
0.5984	Remote Similarity	NPD6054	Approved
0.5984	Remote Similarity	NPD8130	Phase 1
0.5984	Remote Similarity	NPD6650	Approved
0.5984	Remote Similarity	NPD6617	Approved
0.5984	Remote Similarity	NPD6847	Approved
0.5984	Remote Similarity	NPD6649	Approved
0.5984	Remote Similarity	NPD6869	Approved
0.5965	Remote Similarity	NPD5222	Approved
0.5965	Remote Similarity	NPD5221	Approved
0.5965	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5954	Remote Similarity	NPD8074	Phase 3
0.595	Remote Similarity	NPD6373	Approved
0.595	Remote Similarity	NPD6372	Approved
0.5943	Remote Similarity	NPD5209	Approved
0.5938	Remote Similarity	NPD6015	Approved
0.5938	Remote Similarity	NPD6016	Approved
0.5935	Remote Similarity	NPD6882	Approved
0.5917	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD5173	Approved
0.5897	Remote Similarity	NPD5344	Discontinued
0.5893	Remote Similarity	NPD7637	Suspended
0.5891	Remote Similarity	NPD6370	Approved
0.5891	Remote Similarity	NPD5988	Approved
0.5888	Remote Similarity	NPD7154	Phase 3
0.5876	Remote Similarity	NPD3704	Approved
0.5873	Remote Similarity	NPD6009	Approved
0.5872	Remote Similarity	NPD5279	Phase 3
0.5868	Remote Similarity	NPD4729	Approved
0.5868	Remote Similarity	NPD4730	Approved
0.5859	Remote Similarity	NPD6059	Approved
0.5856	Remote Similarity	NPD4753	Phase 2
0.5854	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD5133	Approved
0.5833	Remote Similarity	NPD4767	Approved
0.5833	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD4768	Approved
0.5826	Remote Similarity	NPD4697	Phase 3
0.5826	Remote Similarity	NPD7839	Suspended
0.5821	Remote Similarity	NPD5956	Approved
0.582	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD7503	Approved
0.5812	Remote Similarity	NPD6648	Approved
0.5804	Remote Similarity	NPD5785	Approved
0.5802	Remote Similarity	NPD7492	Approved
0.5798	Remote Similarity	NPD4754	Approved
0.5776	Remote Similarity	NPD6084	Phase 2
0.5776	Remote Similarity	NPD6083	Phase 2
0.5772	Remote Similarity	NPD5251	Approved
0.5772	Remote Similarity	NPD6371	Approved
0.5772	Remote Similarity	NPD5249	Phase 3
0.5772	Remote Similarity	NPD5248	Approved
0.5772	Remote Similarity	NPD5247	Approved
0.5772	Remote Similarity	NPD5250	Approved
0.5758	Remote Similarity	NPD6616	Approved
0.5755	Remote Similarity	NPD4695	Discontinued
0.5752	Remote Similarity	NPD6079	Approved
0.5739	Remote Similarity	NPD4629	Approved
0.5739	Remote Similarity	NPD5210	Approved
0.5739	Remote Similarity	NPD5654	Approved
0.5739	Remote Similarity	NPD5695	Phase 3
0.5736	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD8264	Approved
0.5727	Remote Similarity	NPD3618	Phase 1
0.5726	Remote Similarity	NPD7601	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD7638	Approved
0.5725	Remote Similarity	NPD8328	Phase 3
0.5714	Remote Similarity	NPD7078	Approved
0.5714	Remote Similarity	NPD5328	Approved
0.5714	Remote Similarity	NPD5091	Approved
0.5702	Remote Similarity	NPD4202	Approved
0.5678	Remote Similarity	NPD7639	Approved
0.5678	Remote Similarity	NPD7640	Approved
0.5672	Remote Similarity	NPD7736	Approved
0.5669	Remote Similarity	NPD6274	Approved
0.5662	Remote Similarity	NPD7260	Phase 2
0.5652	Remote Similarity	NPD7748	Approved
0.5648	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5648	Remote Similarity	NPD3667	Approved
0.5645	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5645	Remote Similarity	NPD5135	Approved
0.5641	Remote Similarity	NPD5959	Approved
0.5641	Remote Similarity	NPD7902	Approved
0.5636	Remote Similarity	NPD1694	Approved
0.5636	Remote Similarity	NPD5363	Approved
0.563	Remote Similarity	NPD7319	Approved
0.5625	Remote Similarity	NPD6317	Approved
0.5614	Remote Similarity	NPD7515	Phase 2
0.561	Remote Similarity	NPD6686	Approved
0.5607	Remote Similarity	NPD4252	Approved
0.5607	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5606	Remote Similarity	NPD7829	Approved
0.5606	Remote Similarity	NPD7830	Approved
0.56	Remote Similarity	NPD7116	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data