NPASS Compound

Structure

NPC248758 OpenBabel07101719152D 24 27 0 0 1 0 0 0 0 0999 V2000 -1.2321 1.0185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3997 -1.9105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4942 0.0373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2172 1.6034 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7148 1.0829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6397 -1.0707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8653 0.3880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5050 -0.6827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0108 -0.7200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 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 0.5000 1.5388 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2579 -0.7014 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6182 0.3693 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2601 1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3998 -1.9254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2471 0.0187 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8868 -1.0520 0.0000 C 0 0 1 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 3.0032 0.5909 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4680 2.2382 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9127 -2.7839 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3999 -1.9404 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 7 1 0 0 0 0 3 8 1 0 0 0 0 4 5 1 0 0 0 0 5 15 1 0 0 0 0 6 9 1 0 0 0 0 6 14 1 0 0 0 0 7 18 1 0 0 0 0 8 19 1 0 0 0 0 10 12 1 0 0 0 0 10 20 1 0 0 0 0 11 13 2 0 0 0 0 11 20 1 0 0 0 0 12 4 1 1 0 0 0 12 13 1 0 0 0 0 13 16 1 0 0 0 0 14 18 1 6 0 0 0 14 19 1 0 0 0 0 15 18 1 6 0 0 0 15 20 1 0 0 0 0 16 21 2 0 0 0 0 16 22 1 0 0 0 0 17 19 1 0 0 0 0 17 23 2 0 0 0 0 17 24 1 0 0 0 0 18 1 1 6 0 0 0 19 2 1 1 0 0 0 20 9 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.2
Volume:	347.502
LogP:	2.504
LogD:	3.594
LogS:	-2.867
# Rotatable Bonds:	2
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.798
Synthetic Accessibility Score:	5.647
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.558
MDCK Permeability:	1.9140250515192747e-05
Pgp-inhibitor:	0.099
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.037
20% Bioavailability (F20%):	0.323
30% Bioavailability (F30%):	0.407

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.189
Plasma Protein Binding (PPB):	94.39767456054688%
Volume Distribution (VD):	0.348
Pgp-substrate:	5.304982662200928%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.472
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.107
CYP2C9-inhibitor:	0.064
CYP2C9-substrate:	0.068
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.109
CYP3A4-inhibitor:	0.124
CYP3A4-substrate:	0.084

ADMET: Excretion

Clearance (CL):	0.736
Half-life (T1/2):	0.65

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.678
Drug-inuced Liver Injury (DILI):	0.508
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.29
Maximum Recommended Daily Dose:	0.522
Skin Sensitization:	0.933
Carcinogencity:	0.55
Eye Corrosion:	0.331
Eye Irritation:	0.805
Respiratory Toxicity:	0.95

Download Data

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

Natural Product: NPC248758

Natural Product ID:	NPC248758
*Common Name:**	YQNLDLVKFNZFTI-POLCOUMTSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YQNLDLVKFNZFTI-POLCOUMTSA-N
Standard InCHI:	InChI=1S/C20H28O4/c1-18-7-3-8-19(2,17(23)24)14(18)6-9-20-10-12(4-5-15(18)20)13(11-20)16(21)22/h11-12,14-15H,3-10H2,1-2H3,(H,21,22)(H,23,24)/t12-,14+,15+,18-,19-,20+/m1/s1
SMILES:	C[C@@]12CCC[C@](C)([C@H]1CC[C@]13C[C@@H](CC[C@@H]23)C(=C1)C(=O)O)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3358082
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane diterpenoids

*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
NPO15810	Zea mays	Species	Poaceae	Eukaryota		n.a.	n.a.	DOI[10.1021/jf00055a023]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[11539687]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12713418]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21080643]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	husk	n.a.	PMID[21574561]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21574561]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[23292602]
NPO29744	Acanthopanax gracilistylus	n.a.	n.a.	n.a.	Root Bark	n.a.	n.a.	PMID[25338180]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29762032]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	pollen	n.a.	PMID[8987503]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Pollen Or Spore	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Seed Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Silk Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Silk Stigma Style	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Cob	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Husk Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Oil	n.a.	n.a.	Database[FooDB]
NPO29744	Acanthopanax gracilistylus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29744	Acanthopanax gracilistylus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15810	Zea mays	Species	Poaceae	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

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT927	Cell Line	PBMC	Homo sapiens	IC50	=	7500.0	nM	PMID[542353]
NPT927	Cell Line	PBMC	Homo sapiens	IC50	=	3.0	nM	PMID[542353]
NPT927	Cell Line	PBMC	Homo sapiens	IC50	=	2100.0	nM	PMID[542353]

☑ 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 NPC248758 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	176
0.1-0.2	1146
0.2-0.3	4953
0.3-0.4	14272
0.4-0.5	9149
0.5-0.6	6911
0.6-0.7	4571
0.7-0.8	1356
0.8-0.85	118
0.85-0.9	34
0.9-0.95	8
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.95	High Similarity	NPC472864
0.95	High Similarity	NPC19849
0.9268	High Similarity	NPC472869
0.9259	High Similarity	NPC472865
0.9231	High Similarity	NPC198240
0.9136	High Similarity	NPC97913
0.9136	High Similarity	NPC215893
0.9103	High Similarity	NPC61952
0.9048	High Similarity	NPC472870
0.9036	High Similarity	NPC186975
0.9024	High Similarity	NPC164577
0.8929	High Similarity	NPC236618
0.8837	High Similarity	NPC472866
0.8824	High Similarity	NPC117122
0.8721	High Similarity	NPC66344
0.8721	High Similarity	NPC262043
0.8706	High Similarity	NPC136948
0.8675	High Similarity	NPC167103
0.8675	High Similarity	NPC49019
0.8659	High Similarity	NPC278459
0.8652	High Similarity	NPC476174
0.8636	High Similarity	NPC472871
0.8608	High Similarity	NPC201027
0.8608	High Similarity	NPC476795
0.8605	High Similarity	NPC48107
0.8556	High Similarity	NPC29152
0.8554	High Similarity	NPC472867
0.8554	High Similarity	NPC142683
0.8523	High Similarity	NPC474018
0.8523	High Similarity	NPC470113
0.8523	High Similarity	NPC473986
0.8523	High Similarity	NPC289479
0.8519	High Similarity	NPC110094
0.8519	High Similarity	NPC280654
0.8519	High Similarity	NPC260385
0.8488	Intermediate Similarity	NPC476409
0.8478	Intermediate Similarity	NPC471041
0.8471	Intermediate Similarity	NPC65661
0.8471	Intermediate Similarity	NPC60350
0.8471	Intermediate Similarity	NPC29447
0.8471	Intermediate Similarity	NPC269638
0.8462	Intermediate Similarity	NPC156546
0.8434	Intermediate Similarity	NPC471898
0.8434	Intermediate Similarity	NPC40228
0.8427	Intermediate Similarity	NPC472303
0.8427	Intermediate Similarity	NPC151722
0.8415	Intermediate Similarity	NPC199595
0.8395	Intermediate Similarity	NPC107039
0.8395	Intermediate Similarity	NPC471899
0.8395	Intermediate Similarity	NPC97377
0.8395	Intermediate Similarity	NPC471897
0.8395	Intermediate Similarity	NPC165711
0.8391	Intermediate Similarity	NPC72397
0.8375	Intermediate Similarity	NPC192540
0.8375	Intermediate Similarity	NPC279666
0.8354	Intermediate Similarity	NPC35656
0.8353	Intermediate Similarity	NPC16287
0.8353	Intermediate Similarity	NPC96095
0.8353	Intermediate Similarity	NPC178025
0.8353	Intermediate Similarity	NPC181743
0.8333	Intermediate Similarity	NPC471040
0.8333	Intermediate Similarity	NPC469799
0.8333	Intermediate Similarity	NPC469806
0.8333	Intermediate Similarity	NPC235586
0.8333	Intermediate Similarity	NPC472239
0.8333	Intermediate Similarity	NPC320514
0.8315	Intermediate Similarity	NPC476187
0.8315	Intermediate Similarity	NPC204341
0.8313	Intermediate Similarity	NPC37038
0.8313	Intermediate Similarity	NPC104545
0.8295	Intermediate Similarity	NPC174342
0.8293	Intermediate Similarity	NPC59436
0.8293	Intermediate Similarity	NPC239098
0.8293	Intermediate Similarity	NPC74410
0.8293	Intermediate Similarity	NPC169095
0.8276	Intermediate Similarity	NPC128644
0.8272	Intermediate Similarity	NPC69143
0.8272	Intermediate Similarity	NPC246445
0.8272	Intermediate Similarity	NPC89294
0.8272	Intermediate Similarity	NPC180886
0.8261	Intermediate Similarity	NPC476253
0.8256	Intermediate Similarity	NPC86316
0.8256	Intermediate Similarity	NPC106416
0.8256	Intermediate Similarity	NPC474537
0.825	Intermediate Similarity	NPC241854
0.825	Intermediate Similarity	NPC183503
0.825	Intermediate Similarity	NPC283908
0.825	Intermediate Similarity	NPC103958
0.825	Intermediate Similarity	NPC476046
0.825	Intermediate Similarity	NPC251970
0.825	Intermediate Similarity	NPC161923
0.8242	Intermediate Similarity	NPC293052
0.8235	Intermediate Similarity	NPC472740
0.8235	Intermediate Similarity	NPC105803
0.8235	Intermediate Similarity	NPC3856
0.8235	Intermediate Similarity	NPC279639
0.8214	Intermediate Similarity	NPC147066
0.8214	Intermediate Similarity	NPC90055
0.8214	Intermediate Similarity	NPC221647
0.8214	Intermediate Similarity	NPC477372
0.8193	Intermediate Similarity	NPC16394
0.8193	Intermediate Similarity	NPC231431
0.8193	Intermediate Similarity	NPC158846
0.8182	Intermediate Similarity	NPC104560
0.8171	Intermediate Similarity	NPC212661
0.8171	Intermediate Similarity	NPC471035
0.8152	Intermediate Similarity	NPC471039
0.8152	Intermediate Similarity	NPC235053
0.8152	Intermediate Similarity	NPC472941
0.8152	Intermediate Similarity	NPC250757
0.8152	Intermediate Similarity	NPC301534
0.8152	Intermediate Similarity	NPC456
0.8148	Intermediate Similarity	NPC469803
0.8148	Intermediate Similarity	NPC472327
0.814	Intermediate Similarity	NPC476038
0.814	Intermediate Similarity	NPC194937
0.8125	Intermediate Similarity	NPC330659
0.8125	Intermediate Similarity	NPC161187
0.8125	Intermediate Similarity	NPC244708
0.8118	Intermediate Similarity	NPC142253
0.8118	Intermediate Similarity	NPC469804
0.8118	Intermediate Similarity	NPC469805
0.8118	Intermediate Similarity	NPC302661
0.8118	Intermediate Similarity	NPC200513
0.8118	Intermediate Similarity	NPC238991
0.8118	Intermediate Similarity	NPC3511
0.8111	Intermediate Similarity	NPC477783
0.8095	Intermediate Similarity	NPC477057
0.8095	Intermediate Similarity	NPC469797
0.8095	Intermediate Similarity	NPC469798
0.809	Intermediate Similarity	NPC477973
0.809	Intermediate Similarity	NPC5509
0.809	Intermediate Similarity	NPC281524
0.8085	Intermediate Similarity	NPC470074
0.8072	Intermediate Similarity	NPC179028
0.8068	Intermediate Similarity	NPC476293
0.8065	Intermediate Similarity	NPC253826
0.8049	Intermediate Similarity	NPC309399
0.8046	Intermediate Similarity	NPC474680
0.8046	Intermediate Similarity	NPC283733
0.8046	Intermediate Similarity	NPC8571
0.8046	Intermediate Similarity	NPC142649
0.8043	Intermediate Similarity	NPC139459
0.8025	Intermediate Similarity	NPC3753
0.8025	Intermediate Similarity	NPC237591
0.8023	Intermediate Similarity	NPC102197
0.8023	Intermediate Similarity	NPC470015
0.8023	Intermediate Similarity	NPC168188
0.8023	Intermediate Similarity	NPC200752
0.8022	Intermediate Similarity	NPC476416
0.8022	Intermediate Similarity	NPC476304
0.8	Intermediate Similarity	NPC118174
0.8	Intermediate Similarity	NPC263272
0.8	Intermediate Similarity	NPC267691
0.8	Intermediate Similarity	NPC162632
0.8	Intermediate Similarity	NPC133253
0.8	Intermediate Similarity	NPC14203
0.8	Intermediate Similarity	NPC229584
0.8	Intermediate Similarity	NPC476369
0.8	Intermediate Similarity	NPC274050
0.8	Intermediate Similarity	NPC201912
0.8	Intermediate Similarity	NPC21944
0.8	Intermediate Similarity	NPC473217
0.8	Intermediate Similarity	NPC51486
0.8	Intermediate Similarity	NPC142244
0.8	Intermediate Similarity	NPC38350
0.8	Intermediate Similarity	NPC477782
0.8	Intermediate Similarity	NPC476437
0.8	Intermediate Similarity	NPC160817
0.7979	Intermediate Similarity	NPC471717
0.7979	Intermediate Similarity	NPC98868
0.7979	Intermediate Similarity	NPC235464
0.7979	Intermediate Similarity	NPC166745
0.7979	Intermediate Similarity	NPC194196
0.7979	Intermediate Similarity	NPC197386
0.7976	Intermediate Similarity	NPC192329
0.7976	Intermediate Similarity	NPC170394
0.7976	Intermediate Similarity	NPC215843
0.7976	Intermediate Similarity	NPC477371
0.7955	Intermediate Similarity	NPC194417
0.7955	Intermediate Similarity	NPC322159
0.7955	Intermediate Similarity	NPC82979
0.7952	Intermediate Similarity	NPC132542
0.7952	Intermediate Similarity	NPC66105
0.7952	Intermediate Similarity	NPC68828
0.7952	Intermediate Similarity	NPC472300
0.7938	Intermediate Similarity	NPC472868
0.7935	Intermediate Similarity	NPC476186
0.7931	Intermediate Similarity	NPC87552
0.7931	Intermediate Similarity	NPC476412
0.7931	Intermediate Similarity	NPC156981
0.7931	Intermediate Similarity	NPC165064
0.7927	Intermediate Similarity	NPC476346
0.7927	Intermediate Similarity	NPC39362
0.7927	Intermediate Similarity	NPC476844
0.7912	Intermediate Similarity	NPC165904
0.7912	Intermediate Similarity	NPC177037
0.7912	Intermediate Similarity	NPC110923
0.7912	Intermediate Similarity	NPC472814
0.7912	Intermediate Similarity	NPC23217

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 NPC248758 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	169
0.1-0.2	1452
0.2-0.3	3816
0.3-0.4	2474
0.4-0.5	768
0.5-0.6	234
0.6-0.7	176
0.7-0.8	58
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8161	Intermediate Similarity	NPD4623	Approved
0.8161	Intermediate Similarity	NPD4519	Discontinued
0.8118	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD4223	Phase 3
0.7907	Intermediate Similarity	NPD4221	Approved
0.7882	Intermediate Similarity	NPD4695	Discontinued
0.7753	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD3133	Approved
0.7727	Intermediate Similarity	NPD3666	Approved
0.7727	Intermediate Similarity	NPD3665	Phase 1
0.7727	Intermediate Similarity	NPD4197	Approved
0.7717	Intermediate Similarity	NPD5284	Approved
0.7717	Intermediate Similarity	NPD7515	Phase 2
0.7717	Intermediate Similarity	NPD5281	Approved
0.7708	Intermediate Similarity	NPD7640	Approved
0.7708	Intermediate Similarity	NPD7639	Approved
0.7708	Intermediate Similarity	NPD6404	Discontinued
0.7692	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD3617	Approved
0.764	Intermediate Similarity	NPD5329	Approved
0.7604	Intermediate Similarity	NPD7638	Approved
0.7582	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD5737	Approved
0.7582	Intermediate Similarity	NPD6672	Approved
0.7556	Intermediate Similarity	NPD4688	Approved
0.7556	Intermediate Similarity	NPD4138	Approved
0.7556	Intermediate Similarity	NPD5690	Phase 2
0.7556	Intermediate Similarity	NPD6409	Approved
0.7556	Intermediate Similarity	NPD4689	Approved
0.7556	Intermediate Similarity	NPD4690	Approved
0.7556	Intermediate Similarity	NPD3618	Phase 1
0.7556	Intermediate Similarity	NPD7146	Approved
0.7556	Intermediate Similarity	NPD6684	Approved
0.7556	Intermediate Similarity	NPD4693	Phase 3
0.7556	Intermediate Similarity	NPD7521	Approved
0.7556	Intermediate Similarity	NPD7334	Approved
0.7556	Intermediate Similarity	NPD5205	Approved
0.7556	Intermediate Similarity	NPD5330	Approved
0.7553	Intermediate Similarity	NPD7748	Approved
0.7527	Intermediate Similarity	NPD5693	Phase 1
0.75	Intermediate Similarity	NPD6083	Phase 2
0.75	Intermediate Similarity	NPD4753	Phase 2
0.75	Intermediate Similarity	NPD6904	Approved
0.75	Intermediate Similarity	NPD3667	Approved
0.75	Intermediate Similarity	NPD6084	Phase 2
0.75	Intermediate Similarity	NPD6080	Approved
0.75	Intermediate Similarity	NPD6673	Approved
0.7474	Intermediate Similarity	NPD5695	Phase 3
0.7447	Intermediate Similarity	NPD6399	Phase 3
0.7439	Intermediate Similarity	NPD4691	Approved
0.7423	Intermediate Similarity	NPD5696	Approved
0.7396	Intermediate Similarity	NPD7614	Phase 1
0.7391	Intermediate Similarity	NPD6903	Approved
0.7391	Intermediate Similarity	NPD5208	Approved
0.7363	Intermediate Similarity	NPD5280	Approved
0.7363	Intermediate Similarity	NPD4694	Approved
0.7356	Intermediate Similarity	NPD4195	Approved
0.734	Intermediate Similarity	NPD6079	Approved
0.7333	Intermediate Similarity	NPD4786	Approved
0.732	Intermediate Similarity	NPD7902	Approved
0.7317	Intermediate Similarity	NPD4137	Phase 3
0.7312	Intermediate Similarity	NPD5328	Approved
0.7292	Intermediate Similarity	NPD4629	Approved
0.7292	Intermediate Similarity	NPD5210	Approved
0.7283	Intermediate Similarity	NPD3573	Approved
0.7253	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD5692	Phase 3
0.7229	Intermediate Similarity	NPD4747	Approved
0.7222	Intermediate Similarity	NPD4788	Approved
0.7216	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD5222	Approved
0.7216	Intermediate Similarity	NPD5221	Approved
0.72	Intermediate Similarity	NPD5211	Phase 2
0.7176	Intermediate Similarity	NPD4058	Approved
0.7174	Intermediate Similarity	NPD5279	Phase 3
0.7174	Intermediate Similarity	NPD6098	Approved
0.7158	Intermediate Similarity	NPD6050	Approved
0.7158	Intermediate Similarity	NPD5694	Approved
0.7143	Intermediate Similarity	NPD3668	Phase 3
0.7143	Intermediate Similarity	NPD5173	Approved
0.7113	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD5697	Approved
0.7083	Intermediate Similarity	NPD4202	Approved
0.7071	Intermediate Similarity	NPD4225	Approved
0.7059	Intermediate Similarity	NPD5141	Approved
0.7053	Intermediate Similarity	NPD5207	Approved
0.7045	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD4697	Phase 3
0.703	Intermediate Similarity	NPD7632	Discontinued
0.7019	Intermediate Similarity	NPD6899	Approved
0.7019	Intermediate Similarity	NPD6881	Approved
0.7019	Intermediate Similarity	NPD6686	Approved
0.7019	Intermediate Similarity	NPD6011	Approved
0.701	Intermediate Similarity	NPD7900	Approved
0.701	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD6001	Approved
0.7	Intermediate Similarity	NPD5286	Approved
0.7	Intermediate Similarity	NPD4696	Approved
0.7	Intermediate Similarity	NPD5285	Approved
0.699	Remote Similarity	NPD6402	Approved
0.699	Remote Similarity	NPD5739	Approved
0.699	Remote Similarity	NPD7128	Approved
0.699	Remote Similarity	NPD6675	Approved
0.6979	Remote Similarity	NPD8035	Phase 2
0.6979	Remote Similarity	NPD8034	Phase 2
0.6972	Remote Similarity	NPD7115	Discovery
0.697	Remote Similarity	NPD4755	Approved
0.6952	Remote Similarity	NPD6013	Approved
0.6952	Remote Similarity	NPD6012	Approved
0.6952	Remote Similarity	NPD6014	Approved
0.6951	Remote Similarity	NPD4224	Phase 2
0.6941	Remote Similarity	NPD6081	Approved
0.6931	Remote Similarity	NPD5223	Approved
0.6923	Remote Similarity	NPD5701	Approved
0.6887	Remote Similarity	NPD7102	Approved
0.6887	Remote Similarity	NPD7290	Approved
0.6887	Remote Similarity	NPD6883	Approved
0.6882	Remote Similarity	NPD1694	Approved
0.6882	Remote Similarity	NPD5363	Approved
0.6875	Remote Similarity	NPD5785	Approved
0.6875	Remote Similarity	NPD4096	Approved
0.6869	Remote Similarity	NPD7732	Phase 3
0.6863	Remote Similarity	NPD5224	Approved
0.6863	Remote Similarity	NPD5225	Approved
0.6863	Remote Similarity	NPD5091	Approved
0.6863	Remote Similarity	NPD4633	Approved
0.6863	Remote Similarity	NPD5226	Approved
0.6857	Remote Similarity	NPD7320	Approved
0.6848	Remote Similarity	NPD5362	Discontinued
0.6832	Remote Similarity	NPD4700	Approved
0.6822	Remote Similarity	NPD8130	Phase 1
0.6822	Remote Similarity	NPD6617	Approved
0.6822	Remote Similarity	NPD6869	Approved
0.6822	Remote Similarity	NPD6650	Approved
0.6822	Remote Similarity	NPD6649	Approved
0.6822	Remote Similarity	NPD6847	Approved
0.6813	Remote Similarity	NPD4139	Approved
0.6813	Remote Similarity	NPD4692	Approved
0.6796	Remote Similarity	NPD5174	Approved
0.6796	Remote Similarity	NPD5175	Approved
0.6792	Remote Similarity	NPD6373	Approved
0.6792	Remote Similarity	NPD6372	Approved
0.6786	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD5733	Approved
0.6782	Remote Similarity	NPD4687	Approved
0.6768	Remote Similarity	NPD5654	Approved
0.6759	Remote Similarity	NPD6882	Approved
0.6759	Remote Similarity	NPD8297	Approved
0.6744	Remote Similarity	NPD5276	Approved
0.6744	Remote Similarity	NPD4243	Approved
0.6735	Remote Similarity	NPD5133	Approved
0.6703	Remote Similarity	NPD7525	Registered
0.6697	Remote Similarity	NPD4632	Approved
0.6667	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4518	Approved
0.6667	Remote Similarity	NPD7154	Phase 3
0.6635	Remote Similarity	NPD6052	Approved
0.6635	Remote Similarity	NPD4754	Approved
0.6634	Remote Similarity	NPD5959	Approved
0.6633	Remote Similarity	NPD7637	Suspended
0.6629	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD6117	Approved
0.6604	Remote Similarity	NPD6412	Phase 2
0.6604	Remote Similarity	NPD6614	Approved
0.6598	Remote Similarity	NPD6051	Approved
0.6591	Remote Similarity	NPD4784	Approved
0.6591	Remote Similarity	NPD4785	Approved
0.6591	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD6868	Approved
0.6577	Remote Similarity	NPD5951	Approved
0.6577	Remote Similarity	NPD6274	Approved
0.6559	Remote Similarity	NPD4270	Approved
0.6559	Remote Similarity	NPD4269	Approved
0.6556	Remote Similarity	NPD6116	Phase 1
0.6542	Remote Similarity	NPD4729	Approved
0.6542	Remote Similarity	NPD5168	Approved
0.6542	Remote Similarity	NPD5128	Approved
0.6542	Remote Similarity	NPD4730	Approved
0.6526	Remote Similarity	NPD1696	Phase 3
0.6518	Remote Similarity	NPD6317	Approved
0.6518	Remote Similarity	NPD6009	Approved
0.6517	Remote Similarity	NPD7339	Approved
0.6517	Remote Similarity	NPD4190	Phase 3
0.6517	Remote Similarity	NPD5275	Approved
0.6517	Remote Similarity	NPD6942	Approved
0.6509	Remote Similarity	NPD4767	Approved
0.6509	Remote Similarity	NPD4768	Approved
0.6509	Remote Similarity	NPD6008	Approved
0.6484	Remote Similarity	NPD6697	Approved
0.6484	Remote Similarity	NPD6115	Approved
0.6484	Remote Similarity	NPD6114	Approved
0.6484	Remote Similarity	NPD6118	Approved
0.6481	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD6411	Approved
0.6463	Remote Similarity	NPD4193	Approved
0.6463	Remote Similarity	NPD4191	Approved
0.6463	Remote Similarity	NPD4194	Approved
0.6463	Remote Similarity	NPD4192	Approved
0.646	Remote Similarity	NPD6314	Approved
0.646	Remote Similarity	NPD6335	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