NPASS Compound

Structure

NPC243298 OpenBabel07101718322D 31 34 0 0 1 0 0 0 0 0999 V2000 6.1472 6.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 4.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1701 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9836 1.9316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3578 -0.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4538 -0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 5.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 4.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 4.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5823 0.9135 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9890 1.8271 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5491 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 2.5316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1810 3.3406 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4538 0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 3.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 2.6361 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 3 13 1 0 0 0 0 6 28 1 0 0 0 0 7 12 1 0 0 0 0 8 9 2 0 0 0 0 8 12 1 0 0 0 0 9 15 1 0 0 0 0 10 15 2 0 0 0 0 10 16 1 0 0 0 0 11 17 2 0 0 0 0 11 29 1 0 0 0 0 12 2 1 6 0 0 0 13 14 1 0 0 0 0 13 24 1 6 0 0 0 14 4 1 1 0 0 0 14 30 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 19 1 0 0 0 0 18 23 1 1 0 0 0 19 22 1 0 0 0 0 19 24 1 6 0 0 0 20 21 1 0 0 0 0 20 25 1 0 0 0 0 21 23 1 0 0 0 0 21 26 2 0 0 0 0 22 27 2 0 0 0 0 22 30 1 0 0 0 0 23 5 1 6 0 0 0 23 31 1 0 0 0 0 24 28 1 1 0 0 0 24 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	448.17
Volume:	441.568
LogP:	5.072
LogD:	4.201
LogS:	-5.347
# Rotatable Bonds:	4
TPSA:	71.06
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.593
Synthetic Accessibility Score:	5.499
Fsp3:	0.583
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.607
MDCK Permeability:	1.3178453627915587e-05
Pgp-inhibitor:	0.051
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.299
30% Bioavailability (F30%):	0.958

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.983
Plasma Protein Binding (PPB):	77.93340301513672%
Volume Distribution (VD):	2.505
Pgp-substrate:	18.896270751953125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.907
CYP1A2-substrate:	0.838
CYP2C19-inhibitor:	0.862
CYP2C19-substrate:	0.77
CYP2C9-inhibitor:	0.761
CYP2C9-substrate:	0.014
CYP2D6-inhibitor:	0.816
CYP2D6-substrate:	0.05
CYP3A4-inhibitor:	0.953
CYP3A4-substrate:	0.685

ADMET: Excretion

Clearance (CL):	8.304
Half-life (T1/2):	0.064

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.99
Drug-inuced Liver Injury (DILI):	0.944
AMES Toxicity:	0.143
Rat Oral Acute Toxicity:	0.857
Maximum Recommended Daily Dose:	0.813
Skin Sensitization:	0.919
Carcinogencity:	0.75
Eye Corrosion:	0.195
Eye Irritation:	0.072
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC243298

Natural Product ID:	NPC243298
*Common Name:**	XGXRGYADYVZCTF-OPLDBLFRSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XGXRGYADYVZCTF-OPLDBLFRSA-N
Standard InCHI:	InChI=1S/C24H29ClO6/c1-7-12(2)8-9-15-10-16-17(11-29-15)18-19-22(27)30-14(4)13(3)24(19,28-6)31-23(18,5)21(26)20(16)25/h8-14,18-19H,7H2,1-6H3/b9-8+/t12-,13+,14+,18+,19-,23-,24+/m0/s1
SMILES:	CC[C@@H](/C=C/C1=CC2=C(Cl)C(=O)[C@@]3([C@H](C2=CO1)[C@H]1C(=O)O[C@@H]([C@H]([C@]1(O3)OC)C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3621757
PubChem CID:	25148535
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001244] Delta valerolactones

*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	3
Others	4

Activity Type	# Activity
Cell Line	5
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT71	Cell Line	HEK293	Homo sapiens	Survival	=	100.0	%	PMID[470488]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	97.9	%	PMID[470488]
NPT113	Cell Line	RAW264.7	Mus musculus	Survival	=	28.0	%	PMID[470488]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	5800.0	nM	PMID[470488]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	39800.0	nM	PMID[470488]
NPT2	Others	Unspecified		Inhibition	=	88.5	%	PMID[470488]
NPT2	Others	Unspecified		IC50	=	11600.0	nM	PMID[470488]

☑ 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 NPC243298 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	250
0.1-0.2	1288
0.2-0.3	4647
0.3-0.4	9349
0.4-0.5	15535
0.5-0.6	8675
0.6-0.7	2785
0.7-0.8	160
0.8-0.85	3
0.85-0.9	0
0.9-0.95	1
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9636	High Similarity	NPC245320
0.955	High Similarity	NPC473145
0.955	High Similarity	NPC31641
0.9204	High Similarity	NPC476815
0.8624	High Similarity	NPC272528
0.8532	High Similarity	NPC271059
0.8532	High Similarity	NPC25666
0.8198	Intermediate Similarity	NPC297281
0.8198	Intermediate Similarity	NPC473144
0.8056	Intermediate Similarity	NPC31021
0.7798	Intermediate Similarity	NPC143210
0.7768	Intermediate Similarity	NPC215253
0.7768	Intermediate Similarity	NPC185253
0.7748	Intermediate Similarity	NPC134083
0.7727	Intermediate Similarity	NPC12727
0.7705	Intermediate Similarity	NPC158963
0.7699	Intermediate Similarity	NPC469851
0.7692	Intermediate Similarity	NPC23497
0.7679	Intermediate Similarity	NPC166770
0.7672	Intermediate Similarity	NPC199107
0.7672	Intermediate Similarity	NPC232969
0.7652	Intermediate Similarity	NPC474898
0.7615	Intermediate Similarity	NPC166110
0.7545	Intermediate Similarity	NPC248193
0.7544	Intermediate Similarity	NPC473384
0.7523	Intermediate Similarity	NPC224270
0.75	Intermediate Similarity	NPC476001
0.75	Intermediate Similarity	NPC318082
0.7455	Intermediate Similarity	NPC32944
0.7455	Intermediate Similarity	NPC193396
0.7438	Intermediate Similarity	NPC326264
0.7436	Intermediate Similarity	NPC469852
0.7431	Intermediate Similarity	NPC142159
0.7431	Intermediate Similarity	NPC95364
0.7414	Intermediate Similarity	NPC471364
0.7414	Intermediate Similarity	NPC471365
0.7414	Intermediate Similarity	NPC132395
0.7391	Intermediate Similarity	NPC244456
0.7391	Intermediate Similarity	NPC471699
0.7391	Intermediate Similarity	NPC224172
0.7391	Intermediate Similarity	NPC474912
0.7391	Intermediate Similarity	NPC474899
0.7391	Intermediate Similarity	NPC469657
0.7373	Intermediate Similarity	NPC469853
0.7368	Intermediate Similarity	NPC54843
0.7364	Intermediate Similarity	NPC469372
0.7345	Intermediate Similarity	NPC112654
0.7295	Intermediate Similarity	NPC321496
0.7257	Intermediate Similarity	NPC471698
0.725	Intermediate Similarity	NPC220705
0.7213	Intermediate Similarity	NPC66108
0.7207	Intermediate Similarity	NPC469595
0.7207	Intermediate Similarity	NPC212679
0.7207	Intermediate Similarity	NPC220454
0.719	Intermediate Similarity	NPC89408
0.7167	Intermediate Similarity	NPC327106
0.7156	Intermediate Similarity	NPC279859
0.7156	Intermediate Similarity	NPC38576
0.7154	Intermediate Similarity	NPC476008
0.7143	Intermediate Similarity	NPC268958
0.7143	Intermediate Similarity	NPC472645
0.7132	Intermediate Similarity	NPC24651
0.7117	Intermediate Similarity	NPC280833
0.7109	Intermediate Similarity	NPC312833
0.7105	Intermediate Similarity	NPC473369
0.7094	Intermediate Similarity	NPC472643
0.7091	Intermediate Similarity	NPC471739
0.7077	Intermediate Similarity	NPC477745
0.7073	Intermediate Similarity	NPC265391
0.7064	Intermediate Similarity	NPC281172
0.7059	Intermediate Similarity	NPC307846
0.7059	Intermediate Similarity	NPC596
0.7059	Intermediate Similarity	NPC305157
0.7054	Intermediate Similarity	NPC18945
0.7054	Intermediate Similarity	NPC91693
0.7054	Intermediate Similarity	NPC265557
0.7054	Intermediate Similarity	NPC105926
0.7049	Intermediate Similarity	NPC478209
0.7043	Intermediate Similarity	NPC299396
0.7043	Intermediate Similarity	NPC476275
0.7043	Intermediate Similarity	NPC172998
0.7043	Intermediate Similarity	NPC301596
0.704	Intermediate Similarity	NPC477509
0.704	Intermediate Similarity	NPC270478
0.7037	Intermediate Similarity	NPC262813
0.7034	Intermediate Similarity	NPC235369
0.7027	Intermediate Similarity	NPC475906
0.7027	Intermediate Similarity	NPC469631
0.7027	Intermediate Similarity	NPC469628
0.7027	Intermediate Similarity	NPC469653
0.7027	Intermediate Similarity	NPC471047
0.7027	Intermediate Similarity	NPC475902
0.7018	Intermediate Similarity	NPC477129
0.7018	Intermediate Similarity	NPC477130
0.7016	Intermediate Similarity	NPC474271
0.7015	Intermediate Similarity	NPC168879
0.7008	Intermediate Similarity	NPC476107
0.7	Intermediate Similarity	NPC476729
0.7	Intermediate Similarity	NPC291712
0.7	Intermediate Similarity	NPC203795
0.7	Intermediate Similarity	NPC470922
0.7	Intermediate Similarity	NPC85529
0.7	Intermediate Similarity	NPC469607
0.7	Intermediate Similarity	NPC32006
0.7	Intermediate Similarity	NPC477125
0.6992	Remote Similarity	NPC304180
0.6992	Remote Similarity	NPC179798
0.6991	Remote Similarity	NPC32552
0.6991	Remote Similarity	NPC20713
0.6985	Remote Similarity	NPC190065
0.6985	Remote Similarity	NPC141215
0.6985	Remote Similarity	NPC471089
0.6985	Remote Similarity	NPC243014
0.6985	Remote Similarity	NPC251998
0.6984	Remote Similarity	NPC23046
0.6983	Remote Similarity	NPC38530
0.6983	Remote Similarity	NPC84335
0.6977	Remote Similarity	NPC287236
0.6975	Remote Similarity	NPC320294
0.6975	Remote Similarity	NPC472750
0.6975	Remote Similarity	NPC472747
0.6967	Remote Similarity	NPC469370
0.6967	Remote Similarity	NPC228477
0.6967	Remote Similarity	NPC38154
0.6967	Remote Similarity	NPC137911
0.6964	Remote Similarity	NPC284561
0.6963	Remote Similarity	NPC242486
0.6963	Remote Similarity	NPC15215
0.6957	Remote Similarity	NPC474947
0.6957	Remote Similarity	NPC295347
0.6957	Remote Similarity	NPC234339
0.6957	Remote Similarity	NPC273197
0.6942	Remote Similarity	NPC133422
0.6942	Remote Similarity	NPC476958
0.6934	Remote Similarity	NPC140045
0.6934	Remote Similarity	NPC295885
0.693	Remote Similarity	NPC476597
0.693	Remote Similarity	NPC471571
0.693	Remote Similarity	NPC1108
0.693	Remote Similarity	NPC475302
0.693	Remote Similarity	NPC476598
0.693	Remote Similarity	NPC165383
0.6929	Remote Similarity	NPC21326
0.6929	Remote Similarity	NPC284707
0.6923	Remote Similarity	NPC67251
0.6917	Remote Similarity	NPC477510
0.6917	Remote Similarity	NPC325769
0.6917	Remote Similarity	NPC471143
0.6917	Remote Similarity	NPC221414
0.6917	Remote Similarity	NPC472756
0.6917	Remote Similarity	NPC472748
0.6917	Remote Similarity	NPC476851
0.6911	Remote Similarity	NPC206595
0.6905	Remote Similarity	NPC329869
0.6903	Remote Similarity	NPC280592
0.6903	Remote Similarity	NPC329857
0.6903	Remote Similarity	NPC469718
0.6903	Remote Similarity	NPC213636
0.6903	Remote Similarity	NPC253177
0.6899	Remote Similarity	NPC170880
0.6899	Remote Similarity	NPC472000
0.6899	Remote Similarity	NPC471999
0.6891	Remote Similarity	NPC273005
0.6891	Remote Similarity	NPC469606
0.6891	Remote Similarity	NPC31058
0.688	Remote Similarity	NPC159333
0.688	Remote Similarity	NPC469463
0.688	Remote Similarity	NPC56448
0.688	Remote Similarity	NPC469454
0.688	Remote Similarity	NPC478212
0.688	Remote Similarity	NPC469496
0.6875	Remote Similarity	NPC473151
0.687	Remote Similarity	NPC241456
0.687	Remote Similarity	NPC32868
0.687	Remote Similarity	NPC38830
0.687	Remote Similarity	NPC476596
0.687	Remote Similarity	NPC470697
0.6866	Remote Similarity	NPC476862
0.6866	Remote Similarity	NPC213634
0.6866	Remote Similarity	NPC476852
0.6866	Remote Similarity	NPC476863
0.6864	Remote Similarity	NPC472644
0.6864	Remote Similarity	NPC469551
0.686	Remote Similarity	NPC472749
0.686	Remote Similarity	NPC1679
0.686	Remote Similarity	NPC478208
0.686	Remote Similarity	NPC472751
0.6855	Remote Similarity	NPC470960
0.6855	Remote Similarity	NPC474315
0.685	Remote Similarity	NPC471145
0.685	Remote Similarity	NPC98249
0.685	Remote Similarity	NPC53396
0.685	Remote Similarity	NPC469684
0.6842	Remote Similarity	NPC111114
0.6842	Remote Similarity	NPC476859
0.6842	Remote Similarity	NPC150978
0.6842	Remote Similarity	NPC471329
0.6842	Remote Similarity	NPC300312
0.6842	Remote Similarity	NPC65513
0.6842	Remote Similarity	NPC261607

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 NPC243298 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	212
0.1-0.2	1384
0.2-0.3	3680
0.3-0.4	2622
0.4-0.5	877
0.5-0.6	258
0.6-0.7	117
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
0.6899	Remote Similarity	NPD8513	Phase 3
0.6769	Remote Similarity	NPD8515	Approved
0.6769	Remote Similarity	NPD8516	Approved
0.6769	Remote Similarity	NPD8517	Approved
0.6667	Remote Similarity	NPD6335	Approved
0.6667	Remote Similarity	NPD5654	Approved
0.6667	Remote Similarity	NPD6614	Approved
0.6667	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD6882	Approved
0.6667	Remote Similarity	NPD6313	Approved
0.6615	Remote Similarity	NPD7101	Approved
0.6615	Remote Similarity	NPD7100	Approved
0.6593	Remote Similarity	NPD6033	Approved
0.6581	Remote Similarity	NPD5282	Discontinued
0.6555	Remote Similarity	NPD5959	Approved
0.6535	Remote Similarity	NPD6053	Discontinued
0.6532	Remote Similarity	NPD5697	Approved
0.6525	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6101	Approved
0.6522	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD8074	Phase 3
0.65	Remote Similarity	NPD5696	Approved
0.6493	Remote Similarity	NPD7492	Approved
0.648	Remote Similarity	NPD6881	Approved
0.648	Remote Similarity	NPD6899	Approved
0.6462	Remote Similarity	NPD7115	Discovery
0.6462	Remote Similarity	NPD6009	Approved
0.646	Remote Similarity	NPD1694	Approved
0.6457	Remote Similarity	NPD6649	Approved
0.6457	Remote Similarity	NPD6650	Approved
0.6457	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6675	Approved
0.6452	Remote Similarity	NPD6402	Approved
0.6452	Remote Similarity	NPD7128	Approved
0.6452	Remote Similarity	NPD5739	Approved
0.6449	Remote Similarity	NPD7260	Phase 2
0.6444	Remote Similarity	NPD6616	Approved
0.6439	Remote Similarity	NPD6054	Approved
0.6429	Remote Similarity	NPD6012	Approved
0.6429	Remote Similarity	NPD6013	Approved
0.6429	Remote Similarity	NPD6372	Approved
0.6429	Remote Similarity	NPD6373	Approved
0.6429	Remote Similarity	NPD6014	Approved
0.641	Remote Similarity	NPD6411	Approved
0.641	Remote Similarity	NPD5693	Phase 1
0.641	Remote Similarity	NPD5694	Approved
0.64	Remote Similarity	NPD5701	Approved
0.6397	Remote Similarity	NPD7078	Approved
0.6391	Remote Similarity	NPD6015	Approved
0.6391	Remote Similarity	NPD6016	Approved
0.6385	Remote Similarity	NPD6868	Approved
0.6378	Remote Similarity	NPD7102	Approved
0.6378	Remote Similarity	NPD7290	Approved
0.6378	Remote Similarity	NPD6883	Approved
0.6356	Remote Similarity	NPD5778	Approved
0.6356	Remote Similarity	NPD5779	Approved
0.635	Remote Similarity	NPD7736	Approved
0.6349	Remote Similarity	NPD7320	Approved
0.6349	Remote Similarity	NPD6011	Approved
0.6343	Remote Similarity	NPD6370	Approved
0.6343	Remote Similarity	NPD5988	Approved
0.6338	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD6869	Approved
0.6328	Remote Similarity	NPD8130	Phase 1
0.6328	Remote Similarity	NPD6617	Approved
0.6328	Remote Similarity	NPD6847	Approved
0.6325	Remote Similarity	NPD5692	Phase 3
0.632	Remote Similarity	NPD6008	Approved
0.6316	Remote Similarity	NPD6059	Approved
0.6296	Remote Similarity	NPD8328	Phase 3
0.6293	Remote Similarity	NPD6672	Approved
0.6293	Remote Similarity	NPD5737	Approved
0.6279	Remote Similarity	NPD8297	Approved
0.6277	Remote Similarity	NPD8293	Discontinued
0.6271	Remote Similarity	NPD6050	Approved
0.6269	Remote Similarity	NPD5983	Phase 2
0.6259	Remote Similarity	NPD5956	Approved
0.625	Remote Similarity	NPD5169	Approved
0.625	Remote Similarity	NPD5695	Phase 3
0.622	Remote Similarity	NPD5128	Approved
0.6207	Remote Similarity	NPD3573	Approved
0.6204	Remote Similarity	NPD6336	Discontinued
0.6202	Remote Similarity	NPD5215	Approved
0.6202	Remote Similarity	NPD5127	Approved
0.6202	Remote Similarity	NPD5217	Approved
0.6202	Remote Similarity	NPD5216	Approved
0.6194	Remote Similarity	NPD6319	Approved
0.6186	Remote Similarity	NPD5207	Approved
0.617	Remote Similarity	NPD6845	Suspended
0.6148	Remote Similarity	NPD6084	Phase 2
0.6148	Remote Similarity	NPD6083	Phase 2
0.6142	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6107	Remote Similarity	NPD4632	Approved
0.6102	Remote Similarity	NPD6904	Approved
0.6102	Remote Similarity	NPD6080	Approved
0.6102	Remote Similarity	NPD6673	Approved
0.6098	Remote Similarity	NPD4225	Approved
0.6098	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD6686	Approved
0.6094	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD6399	Phase 3
0.608	Remote Similarity	NPD5091	Approved
0.608	Remote Similarity	NPD5211	Phase 2
0.6077	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD7319	Approved
0.6066	Remote Similarity	NPD7839	Suspended
0.6061	Remote Similarity	NPD5167	Approved
0.6053	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD5209	Approved
0.6048	Remote Similarity	NPD5285	Approved
0.6048	Remote Similarity	NPD4696	Approved
0.6048	Remote Similarity	NPD5286	Approved
0.6033	Remote Similarity	NPD7900	Approved
0.6033	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD7503	Approved
0.6016	Remote Similarity	NPD4755	Approved
0.6015	Remote Similarity	NPD6274	Approved
0.6	Remote Similarity	NPD5284	Approved
0.6	Remote Similarity	NPD5281	Approved
0.5984	Remote Similarity	NPD4629	Approved
0.5984	Remote Similarity	NPD5210	Approved
0.5984	Remote Similarity	NPD5141	Approved
0.5983	Remote Similarity	NPD5330	Approved
0.5983	Remote Similarity	NPD7521	Approved
0.5983	Remote Similarity	NPD6409	Approved
0.5983	Remote Similarity	NPD7146	Approved
0.5983	Remote Similarity	NPD6684	Approved
0.5983	Remote Similarity	NPD7334	Approved
0.5971	Remote Similarity	NPD7507	Approved
0.597	Remote Similarity	NPD6317	Approved
0.597	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5969	Remote Similarity	NPD5168	Approved
0.5952	Remote Similarity	NPD5225	Approved
0.5952	Remote Similarity	NPD5224	Approved
0.5952	Remote Similarity	NPD5226	Approved
0.5952	Remote Similarity	NPD4633	Approved
0.592	Remote Similarity	NPD4700	Approved
0.5917	Remote Similarity	NPD5785	Approved
0.5912	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5906	Remote Similarity	NPD5174	Approved
0.5906	Remote Similarity	NPD5175	Approved
0.5897	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD4756	Discovery
0.5891	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD7902	Approved
0.5882	Remote Similarity	NPD6903	Approved
0.5882	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5878	Remote Similarity	NPD2067	Discontinued
0.5878	Remote Similarity	NPD4634	Approved
0.5873	Remote Similarity	NPD5223	Approved
0.5868	Remote Similarity	NPD7983	Approved
0.5854	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD6098	Approved
0.5847	Remote Similarity	NPD5786	Approved
0.5833	Remote Similarity	NPD1695	Approved
0.5833	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.582	Remote Similarity	NPD5133	Approved
0.5806	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD5221	Approved
0.5806	Remote Similarity	NPD5222	Approved
0.5806	Remote Similarity	NPD4697	Phase 3
0.5797	Remote Similarity	NPD8444	Approved
0.5797	Remote Similarity	NPD6908	Approved
0.5797	Remote Similarity	NPD6909	Approved
0.5785	Remote Similarity	NPD6698	Approved
0.5785	Remote Similarity	NPD46	Approved
0.5775	Remote Similarity	NPD8337	Approved
0.5775	Remote Similarity	NPD8336	Approved
0.5772	Remote Similarity	NPD7748	Approved
0.5769	Remote Similarity	NPD6412	Phase 2
0.5766	Remote Similarity	NPD4522	Approved
0.5763	Remote Similarity	NPD5363	Approved
0.576	Remote Similarity	NPD5173	Approved
0.5758	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD6371	Approved
0.5755	Remote Similarity	NPD8080	Discontinued
0.5745	Remote Similarity	NPD8451	Approved
0.5726	Remote Similarity	NPD7154	Phase 3
0.5725	Remote Similarity	NPD4730	Approved
0.5725	Remote Similarity	NPD4729	Approved
0.5714	Remote Similarity	NPD7638	Approved
0.5714	Remote Similarity	NPD8039	Approved
0.5714	Remote Similarity	NPD7830	Approved
0.5714	Remote Similarity	NPD7604	Phase 2
0.5714	Remote Similarity	NPD7829	Approved
0.5714	Remote Similarity	NPD5279	Phase 3
0.5704	Remote Similarity	NPD8448	Approved
0.5702	Remote Similarity	NPD4753	Phase 2
0.5694	Remote Similarity	NPD8391	Approved
0.5694	Remote Similarity	NPD8390	Approved
0.5694	Remote Similarity	NPD8392	Approved
0.5692	Remote Similarity	NPD4768	Approved
0.5692	Remote Similarity	NPD4767	Approved
0.569	Remote Similarity	NPD5369	Approved
0.5682	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5677	Remote Similarity	NPD7236	Approved
0.5671	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.5669	Remote Similarity	NPD7639	Approved
0.5669	Remote Similarity	NPD7640	Approved
0.5659	Remote Similarity	NPD4754	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