NPASS Compound

Structure

NPC297281 OpenBabel07101718322D 29 30 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 -0.8660 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 -2.5981 1.5000 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 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 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 6.0622 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 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 2 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 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 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 6.9282 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 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 -0.5000 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 6 7 2 0 0 0 0 6 11 1 0 0 0 0 7 15 1 0 0 0 0 8 15 2 0 0 0 0 8 16 1 0 0 0 0 9 18 1 0 0 0 0 9 19 1 0 0 0 0 10 17 2 0 0 0 0 10 29 1 0 0 0 0 11 1 1 1 0 0 0 11 13 1 0 0 0 0 12 2 1 1 0 0 0 12 14 1 0 0 0 0 12 19 1 0 0 0 0 13 3 1 6 0 0 0 13 24 1 0 0 0 0 14 4 1 6 0 0 0 14 25 1 0 0 0 0 15 29 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 26 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 27 2 0 0 0 0 22 5 1 6 0 0 0 22 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	424.17
Volume:	424.089
LogP:	2.546
LogD:	1.995
LogS:	-3.192
# Rotatable Bonds:	7
TPSA:	104.06
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.58
Synthetic Accessibility Score:	5.249
Fsp3:	0.545
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:	-4.599
MDCK Permeability:	1.8538597942097113e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.64
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.034

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.781
Plasma Protein Binding (PPB):	74.56087493896484%
Volume Distribution (VD):	1.073
Pgp-substrate:	15.463956832885742%

ADMET: Metabolism

CYP1A2-inhibitor:	0.707
CYP1A2-substrate:	0.282
CYP2C19-inhibitor:	0.156
CYP2C19-substrate:	0.76
CYP2C9-inhibitor:	0.083
CYP2C9-substrate:	0.076
CYP2D6-inhibitor:	0.195
CYP2D6-substrate:	0.033
CYP3A4-inhibitor:	0.814
CYP3A4-substrate:	0.654

ADMET: Excretion

Clearance (CL):	3.696
Half-life (T1/2):	0.422

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.861
Drug-inuced Liver Injury (DILI):	0.737
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.947
Maximum Recommended Daily Dose:	0.361
Skin Sensitization:	0.678
Carcinogencity:	0.948
Eye Corrosion:	0.004
Eye Irritation:	0.027
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC297281

Natural Product ID:	NPC297281
*Common Name:**	Chaetomugilin Q
IUPAC Name:	(7S,8S)-5-chloro-7-hydroxy-8-[(3S,4S)-4-hydroxy-3-methyl-2-oxopentyl]-3-[(E,3R,4R)-4-hydroxy-3-methylpent-1-enyl]-7-methyl-8H-isochromen-6-one
Synonyms:	Chaetomugilin Q
Standard InCHIKey:	VWKWLVNURGSWPO-WGGDPNRLSA-N
Standard InCHI:	InChI=1S/C22H29ClO6/c1-11(13(3)24)6-7-15-8-16-17(10-29-15)18(9-19(26)12(2)14(4)25)22(5,28)21(27)20(16)23/h6-8,10-14,18,24-25,28H,9H2,1-5H3/b7-6+/t11-,12+,13-,14+,18+,22+/m1/s1
SMILES:	C[C@H]([C@@H](/C=C/C1=CC2=C(Cl)C(=O)[C@@]([C@H](C2=CO1)CC(=O)[C@H]([C@@H](O)C)C)(C)O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1797230
PubChem CID:	53358199
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	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	=	0.0495	nM	PMID[572897]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	0.0472	nM	PMID[572897]
NPT137	Cell Line	L1210	Mus musculus	IC50	=	0.0802	nM	PMID[572897]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	0.1	nM	PMID[572897]

☑ 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 NPC297281 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	215
0.1-0.2	1234
0.2-0.3	4559
0.3-0.4	10186
0.4-0.5	17150
0.5-0.6	7451
0.6-0.7	1767
0.7-0.8	116
0.8-0.85	12
0.85-0.9	1
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473144
0.9479	High Similarity	NPC185253
0.9479	High Similarity	NPC215253
0.9375	High Similarity	NPC166770
0.9271	High Similarity	NPC134083
0.8636	High Similarity	NPC476815
0.8636	High Similarity	NPC31641
0.8545	High Similarity	NPC245320
0.8468	Intermediate Similarity	NPC473145
0.8421	Intermediate Similarity	NPC203795
0.8252	Intermediate Similarity	NPC224172
0.8198	Intermediate Similarity	NPC243298
0.7925	Intermediate Similarity	NPC320294
0.7925	Intermediate Similarity	NPC271059
0.7925	Intermediate Similarity	NPC25666
0.787	Intermediate Similarity	NPC199107
0.787	Intermediate Similarity	NPC232969
0.785	Intermediate Similarity	NPC272528
0.7788	Intermediate Similarity	NPC471694
0.767	Intermediate Similarity	NPC143210
0.7615	Intermediate Similarity	NPC85529
0.7615	Intermediate Similarity	NPC32006
0.7596	Intermediate Similarity	NPC31021
0.7596	Intermediate Similarity	NPC12727
0.757	Intermediate Similarity	NPC469851
0.7549	Intermediate Similarity	NPC224270
0.7545	Intermediate Similarity	NPC469853
0.7476	Intermediate Similarity	NPC32552
0.7476	Intermediate Similarity	NPC166110
0.7455	Intermediate Similarity	NPC469852
0.7453	Intermediate Similarity	NPC208094
0.7429	Intermediate Similarity	NPC295347
0.7411	Intermediate Similarity	NPC23497
0.7407	Intermediate Similarity	NPC469657
0.7407	Intermediate Similarity	NPC244456
0.7404	Intermediate Similarity	NPC248193
0.7396	Intermediate Similarity	NPC478122
0.7353	Intermediate Similarity	NPC53454
0.7353	Intermediate Similarity	NPC307298
0.7315	Intermediate Similarity	NPC46761
0.7308	Intermediate Similarity	NPC32944
0.7308	Intermediate Similarity	NPC193396
0.7304	Intermediate Similarity	NPC321496
0.7304	Intermediate Similarity	NPC326264
0.7297	Intermediate Similarity	NPC478052
0.729	Intermediate Similarity	NPC473161
0.729	Intermediate Similarity	NPC239895
0.7282	Intermediate Similarity	NPC95364
0.7282	Intermediate Similarity	NPC142159
0.7264	Intermediate Similarity	NPC280725
0.7257	Intermediate Similarity	NPC137911
0.7257	Intermediate Similarity	NPC228477
0.7255	Intermediate Similarity	NPC113370
0.7255	Intermediate Similarity	NPC476079
0.7255	Intermediate Similarity	NPC103743
0.7248	Intermediate Similarity	NPC472637
0.7248	Intermediate Similarity	NPC471699
0.7248	Intermediate Similarity	NPC207885
0.7238	Intermediate Similarity	NPC242637
0.7228	Intermediate Similarity	NPC187529
0.7228	Intermediate Similarity	NPC307112
0.7222	Intermediate Similarity	NPC35717
0.7217	Intermediate Similarity	NPC66108
0.7212	Intermediate Similarity	NPC280592
0.7212	Intermediate Similarity	NPC131864
0.7212	Intermediate Similarity	NPC113393
0.7212	Intermediate Similarity	NPC253177
0.7212	Intermediate Similarity	NPC213636
0.717	Intermediate Similarity	NPC477241
0.7157	Intermediate Similarity	NPC94666
0.7156	Intermediate Similarity	NPC54705
0.7143	Intermediate Similarity	NPC296114
0.7143	Intermediate Similarity	NPC471329
0.713	Intermediate Similarity	NPC474315
0.713	Intermediate Similarity	NPC478233
0.713	Intermediate Similarity	NPC472073
0.713	Intermediate Similarity	NPC472074
0.713	Intermediate Similarity	NPC53844
0.7115	Intermediate Similarity	NPC307092
0.7115	Intermediate Similarity	NPC51358
0.7115	Intermediate Similarity	NPC118011
0.7115	Intermediate Similarity	NPC36668
0.7103	Intermediate Similarity	NPC91408
0.7103	Intermediate Similarity	NPC209355
0.7091	Intermediate Similarity	NPC112613
0.7087	Intermediate Similarity	NPC272039
0.7087	Intermediate Similarity	NPC220930
0.708	Intermediate Similarity	NPC330011
0.708	Intermediate Similarity	NPC329048
0.7075	Intermediate Similarity	NPC271652
0.7064	Intermediate Similarity	NPC306908
0.7064	Intermediate Similarity	NPC472729
0.7064	Intermediate Similarity	NPC177680
0.7064	Intermediate Similarity	NPC153776
0.7064	Intermediate Similarity	NPC472730
0.7064	Intermediate Similarity	NPC316598
0.7059	Intermediate Similarity	NPC32037
0.7059	Intermediate Similarity	NPC315974
0.7048	Intermediate Similarity	NPC469372
0.7048	Intermediate Similarity	NPC469464
0.7037	Intermediate Similarity	NPC94337
0.703	Intermediate Similarity	NPC477785
0.703	Intermediate Similarity	NPC477784
0.703	Intermediate Similarity	NPC16488
0.703	Intermediate Similarity	NPC477786
0.703	Intermediate Similarity	NPC475083
0.7027	Intermediate Similarity	NPC31058
0.7027	Intermediate Similarity	NPC273005
0.7027	Intermediate Similarity	NPC469606
0.7019	Intermediate Similarity	NPC143025
0.7019	Intermediate Similarity	NPC473658
0.7019	Intermediate Similarity	NPC26078
0.7019	Intermediate Similarity	NPC60765
0.7018	Intermediate Similarity	NPC220155
0.7018	Intermediate Similarity	NPC322903
0.7009	Intermediate Similarity	NPC474882
0.7009	Intermediate Similarity	NPC53685
0.7009	Intermediate Similarity	NPC38830
0.7009	Intermediate Similarity	NPC474271
0.7	Intermediate Similarity	NPC472728
0.7	Intermediate Similarity	NPC476299
0.7	Intermediate Similarity	NPC472727
0.7	Intermediate Similarity	NPC474012
0.7	Intermediate Similarity	NPC275766
0.6991	Remote Similarity	NPC266570
0.6991	Remote Similarity	NPC189863
0.6991	Remote Similarity	NPC477125
0.699	Remote Similarity	NPC261721
0.699	Remote Similarity	NPC315395
0.699	Remote Similarity	NPC194417
0.699	Remote Similarity	NPC316426
0.6981	Remote Similarity	NPC142838
0.6972	Remote Similarity	NPC273269
0.6972	Remote Similarity	NPC471916
0.6964	Remote Similarity	NPC131366
0.6964	Remote Similarity	NPC473624
0.6957	Remote Similarity	NPC475065
0.6952	Remote Similarity	NPC280833
0.6952	Remote Similarity	NPC474918
0.6952	Remote Similarity	NPC210216
0.6952	Remote Similarity	NPC472676
0.6952	Remote Similarity	NPC212598
0.6952	Remote Similarity	NPC472688
0.6944	Remote Similarity	NPC476245
0.6944	Remote Similarity	NPC471698
0.6939	Remote Similarity	NPC97173
0.6937	Remote Similarity	NPC115862
0.693	Remote Similarity	NPC91034
0.693	Remote Similarity	NPC266514
0.693	Remote Similarity	NPC185
0.6923	Remote Similarity	NPC181327
0.6923	Remote Similarity	NPC23622
0.6923	Remote Similarity	NPC472007
0.6917	Remote Similarity	NPC146786
0.6916	Remote Similarity	NPC282644
0.6916	Remote Similarity	NPC475302
0.6916	Remote Similarity	NPC29798
0.6909	Remote Similarity	NPC108368
0.6909	Remote Similarity	NPC57079
0.6897	Remote Similarity	NPC99760
0.6893	Remote Similarity	NPC132228
0.6893	Remote Similarity	NPC15807
0.6893	Remote Similarity	NPC281172
0.6893	Remote Similarity	NPC179006
0.6893	Remote Similarity	NPC474853
0.6893	Remote Similarity	NPC241512
0.6893	Remote Similarity	NPC6185
0.6893	Remote Similarity	NPC261380
0.6893	Remote Similarity	NPC8518
0.6893	Remote Similarity	NPC79573
0.6893	Remote Similarity	NPC263997
0.6887	Remote Similarity	NPC474209
0.6887	Remote Similarity	NPC145666
0.6887	Remote Similarity	NPC469595
0.6887	Remote Similarity	NPC220454
0.6887	Remote Similarity	NPC38952
0.6887	Remote Similarity	NPC212679
0.6887	Remote Similarity	NPC475823
0.6887	Remote Similarity	NPC212369
0.6881	Remote Similarity	NPC472734
0.6881	Remote Similarity	NPC21681
0.6881	Remote Similarity	NPC472675
0.6881	Remote Similarity	NPC78473
0.6881	Remote Similarity	NPC318082
0.6881	Remote Similarity	NPC269492
0.6881	Remote Similarity	NPC472733
0.688	Remote Similarity	NPC156797
0.688	Remote Similarity	NPC287903
0.6875	Remote Similarity	NPC163249
0.6875	Remote Similarity	NPC155332
0.6875	Remote Similarity	NPC235369
0.6875	Remote Similarity	NPC80781
0.6875	Remote Similarity	NPC114540
0.6875	Remote Similarity	NPC32577
0.687	Remote Similarity	NPC476802
0.687	Remote Similarity	NPC89171
0.687	Remote Similarity	NPC327106
0.687	Remote Similarity	NPC318363
0.687	Remote Similarity	NPC475418
0.687	Remote Similarity	NPC473482

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 NPC297281 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	191
0.1-0.2	1485
0.2-0.3	3567
0.3-0.4	2645
0.4-0.5	931
0.5-0.6	294
0.6-0.7	37
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
0.6875	Remote Similarity	NPD5091	Approved
0.6852	Remote Similarity	NPD5282	Discontinued
0.6789	Remote Similarity	NPD4629	Approved
0.6789	Remote Similarity	NPD5210	Approved
0.6752	Remote Similarity	NPD5169	Approved
0.6695	Remote Similarity	NPD5127	Approved
0.6694	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD5279	Phase 3
0.6606	Remote Similarity	NPD5778	Approved
0.6606	Remote Similarity	NPD5779	Approved
0.6606	Remote Similarity	NPD5133	Approved
0.6581	Remote Similarity	NPD5128	Approved
0.6581	Remote Similarity	NPD5168	Approved
0.6574	Remote Similarity	NPD5785	Approved
0.6569	Remote Similarity	NPD4695	Discontinued
0.6569	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD5216	Approved
0.6555	Remote Similarity	NPD5217	Approved
0.6555	Remote Similarity	NPD5215	Approved
0.6529	Remote Similarity	NPD5167	Approved
0.6509	Remote Similarity	NPD3618	Phase 1
0.6504	Remote Similarity	NPD6314	Approved
0.6504	Remote Similarity	NPD6335	Approved
0.6504	Remote Similarity	NPD6313	Approved
0.6481	Remote Similarity	NPD6101	Approved
0.6481	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD4753	Phase 2
0.646	Remote Similarity	NPD5696	Approved
0.6442	Remote Similarity	NPD3667	Approved
0.6436	Remote Similarity	NPD4756	Discovery
0.6435	Remote Similarity	NPD5211	Phase 2
0.6429	Remote Similarity	NPD5222	Approved
0.6429	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5221	Approved
0.6429	Remote Similarity	NPD4697	Phase 3
0.6415	Remote Similarity	NPD5363	Approved
0.6415	Remote Similarity	NPD1696	Phase 3
0.6404	Remote Similarity	NPD4696	Approved
0.6404	Remote Similarity	NPD5285	Approved
0.6404	Remote Similarity	NPD5286	Approved
0.6372	Remote Similarity	NPD4755	Approved
0.6372	Remote Similarity	NPD5173	Approved
0.6364	Remote Similarity	NPD6053	Discontinued
0.6364	Remote Similarity	NPD6411	Approved
0.6356	Remote Similarity	NPD6614	Approved
0.6355	Remote Similarity	NPD4694	Approved
0.6355	Remote Similarity	NPD5280	Approved
0.6348	Remote Similarity	NPD5223	Approved
0.6346	Remote Similarity	NPD5369	Approved
0.6341	Remote Similarity	NPD6868	Approved
0.6339	Remote Similarity	NPD5654	Approved
0.6339	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.633	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD5141	Approved
0.6321	Remote Similarity	NPD3665	Phase 1
0.6321	Remote Similarity	NPD3133	Approved
0.6321	Remote Similarity	NPD3666	Approved
0.6321	Remote Similarity	NPD4786	Approved
0.632	Remote Similarity	NPD4522	Approved
0.632	Remote Similarity	NPD7100	Approved
0.632	Remote Similarity	NPD7101	Approved
0.6316	Remote Similarity	NPD4225	Approved
0.6293	Remote Similarity	NPD5224	Approved
0.6293	Remote Similarity	NPD5225	Approved
0.6293	Remote Similarity	NPD4633	Approved
0.6293	Remote Similarity	NPD5226	Approved
0.6286	Remote Similarity	NPD4269	Approved
0.6286	Remote Similarity	NPD4270	Approved
0.6262	Remote Similarity	NPD1694	Approved
0.6261	Remote Similarity	NPD4700	Approved
0.625	Remote Similarity	NPD3704	Approved
0.6239	Remote Similarity	NPD5174	Approved
0.6239	Remote Similarity	NPD5175	Approved
0.6228	Remote Similarity	NPD5959	Approved
0.6228	Remote Similarity	NPD6083	Phase 2
0.6228	Remote Similarity	NPD6084	Phase 2
0.6226	Remote Similarity	NPD6110	Phase 1
0.6218	Remote Similarity	NPD5697	Approved
0.6216	Remote Similarity	NPD5281	Approved
0.6216	Remote Similarity	NPD5284	Approved
0.6216	Remote Similarity	NPD6079	Approved
0.6216	Remote Similarity	NPD7515	Phase 2
0.6204	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD5690	Phase 2
0.6204	Remote Similarity	NPD5786	Approved
0.6204	Remote Similarity	NPD4519	Discontinued
0.6204	Remote Similarity	NPD4623	Approved
0.6198	Remote Similarity	NPD4634	Approved
0.6195	Remote Similarity	NPD5695	Phase 3
0.6183	Remote Similarity	NPD6033	Approved
0.6182	Remote Similarity	NPD5328	Approved
0.6179	Remote Similarity	NPD4632	Approved
0.6168	Remote Similarity	NPD4197	Approved
0.6167	Remote Similarity	NPD6011	Approved
0.6167	Remote Similarity	NPD6881	Approved
0.6167	Remote Similarity	NPD6899	Approved
0.6165	Remote Similarity	NPD7260	Phase 2
0.6161	Remote Similarity	NPD4202	Approved
0.6161	Remote Similarity	NPD6399	Phase 3
0.6148	Remote Similarity	NPD6650	Approved
0.6148	Remote Similarity	NPD6649	Approved
0.6134	Remote Similarity	NPD6675	Approved
0.6134	Remote Similarity	NPD5739	Approved
0.6134	Remote Similarity	NPD7128	Approved
0.6134	Remote Similarity	NPD6402	Approved
0.6132	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD6372	Approved
0.6116	Remote Similarity	NPD6014	Approved
0.6116	Remote Similarity	NPD6013	Approved
0.6116	Remote Similarity	NPD6373	Approved
0.6116	Remote Similarity	NPD6012	Approved
0.6111	Remote Similarity	NPD5329	Approved
0.6106	Remote Similarity	NPD7748	Approved
0.6102	Remote Similarity	NPD4754	Approved
0.6095	Remote Similarity	NPD4252	Approved
0.6094	Remote Similarity	NPD5983	Phase 2
0.6094	Remote Similarity	NPD8513	Phase 3
0.6087	Remote Similarity	NPD7902	Approved
0.6083	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD5701	Approved
0.6075	Remote Similarity	NPD7154	Phase 3
0.6071	Remote Similarity	NPD5693	Phase 1
0.6071	Remote Similarity	NPD5694	Approved
0.6066	Remote Similarity	NPD6883	Approved
0.6066	Remote Similarity	NPD7290	Approved
0.6066	Remote Similarity	NPD7102	Approved
0.6058	Remote Similarity	NPD3617	Approved
0.6034	Remote Similarity	NPD7638	Approved
0.6034	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD4729	Approved
0.6033	Remote Similarity	NPD4730	Approved
0.6033	Remote Similarity	NPD7320	Approved
0.6032	Remote Similarity	NPD6009	Approved
0.6031	Remote Similarity	NPD6336	Discontinued
0.6019	Remote Similarity	NPD3668	Phase 3
0.6016	Remote Similarity	NPD8130	Phase 1
0.6016	Remote Similarity	NPD6847	Approved
0.6016	Remote Similarity	NPD6869	Approved
0.6016	Remote Similarity	NPD6617	Approved
0.6	Remote Similarity	NPD4767	Approved
0.6	Remote Similarity	NPD4768	Approved
0.5983	Remote Similarity	NPD7639	Approved
0.5983	Remote Similarity	NPD7640	Approved
0.5982	Remote Similarity	NPD46	Approved
0.5982	Remote Similarity	NPD6698	Approved
0.5982	Remote Similarity	NPD5692	Phase 3
0.5981	Remote Similarity	NPD5209	Approved
0.5981	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD4221	Approved
0.5981	Remote Similarity	NPD4223	Phase 3
0.597	Remote Similarity	NPD5956	Approved
0.5969	Remote Similarity	NPD8517	Approved
0.5969	Remote Similarity	NPD8515	Approved
0.5969	Remote Similarity	NPD8516	Approved
0.5968	Remote Similarity	NPD6882	Approved
0.5968	Remote Similarity	NPD8297	Approved
0.5946	Remote Similarity	NPD6672	Approved
0.5946	Remote Similarity	NPD5737	Approved
0.5946	Remote Similarity	NPD4518	Approved
0.5938	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD5249	Phase 3
0.5935	Remote Similarity	NPD5247	Approved
0.5935	Remote Similarity	NPD5251	Approved
0.5935	Remote Similarity	NPD5248	Approved
0.5935	Remote Similarity	NPD6371	Approved
0.5935	Remote Similarity	NPD5250	Approved
0.5935	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD5135	Approved
0.5929	Remote Similarity	NPD6050	Approved
0.5929	Remote Similarity	NPD7983	Approved
0.5926	Remote Similarity	NPD5362	Discontinued
0.5922	Remote Similarity	NPD8264	Approved
0.5918	Remote Similarity	NPD7331	Phase 2
0.5918	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5891	Remote Similarity	NPD6319	Approved
0.5891	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5891	Remote Similarity	NPD6054	Approved
0.5887	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD7839	Suspended
0.5846	Remote Similarity	NPD6016	Approved
0.5846	Remote Similarity	NPD6015	Approved
0.5841	Remote Similarity	NPD5207	Approved
0.5841	Remote Similarity	NPD7838	Discovery
0.5826	Remote Similarity	NPD7900	Approved
0.5826	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD7341	Phase 2
0.5802	Remote Similarity	NPD6370	Approved
0.5802	Remote Similarity	NPD5988	Approved
0.5789	Remote Similarity	NPD7637	Suspended
0.5781	Remote Similarity	NPD6317	Approved
0.5769	Remote Similarity	NPD6059	Approved
0.5769	Remote Similarity	NPD8039	Approved
0.5766	Remote Similarity	NPD4688	Approved
0.5766	Remote Similarity	NPD7521	Approved
0.5766	Remote Similarity	NPD4690	Approved
0.5766	Remote Similarity	NPD6845	Suspended
0.5766	Remote Similarity	NPD5205	Approved
0.5766	Remote Similarity	NPD7334	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