NPASS Compound

Structure

CID172998 OpenBabel06191715542D 26 28 0 0 1 0 0 0 0 0999 V2000 -2.5568 -4.6328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9726 -2.6765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4158 1.9563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1092 -1.0352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4349 -1.9131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8136 -3.9637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0215 -2.9855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6092 -0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7431 -0.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 -0.1045 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2784 -2.3164 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8605 0.3955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0704 -1.5522 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3273 -2.6254 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8387 0.6034 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4863 -1.3383 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 6 1 0 0 0 0 2 10 1 0 0 0 0 3 11 2 0 0 0 0 4 12 2 0 0 0 0 6 10 2 0 0 0 0 7 11 1 0 0 0 0 8 13 2 0 0 0 0 8 16 1 0 0 0 0 9 15 1 0 0 0 0 9 20 1 0 0 0 0 10 18 1 0 0 0 0 11 13 1 0 0 0 0 12 19 1 0 0 0 0 13 26 1 0 0 0 0 14 7 1 6 0 0 0 14 17 1 0 0 0 0 14 24 1 0 0 0 0 15 17 1 0 0 0 0 15 25 1 1 0 0 0 16 20 1 0 0 0 0 16 21 2 0 0 0 0 17 12 1 1 0 0 0 18 22 2 0 0 0 0 18 25 1 0 0 0 0 19 23 2 0 0 0 0 19 24 1 0 0 0 0 20 5 1 6 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	358.14
Volume:	363.093
LogP:	1.134
LogD:	1.113
LogS:	-2.835
# Rotatable Bonds:	3
TPSA:	78.9
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.558
Synthetic Accessibility Score:	5.9
Fsp3:	0.45
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:	-4.867
MDCK Permeability:	1.8737937352852896e-05
Pgp-inhibitor:	0.84
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.019
Plasma Protein Binding (PPB):	80.27288055419922%
Volume Distribution (VD):	1.71
Pgp-substrate:	15.947704315185547%

ADMET: Metabolism

CYP1A2-inhibitor:	0.236
CYP1A2-substrate:	0.211
CYP2C19-inhibitor:	0.926
CYP2C19-substrate:	0.385
CYP2C9-inhibitor:	0.916
CYP2C9-substrate:	0.059
CYP2D6-inhibitor:	0.365
CYP2D6-substrate:	0.041
CYP3A4-inhibitor:	0.859
CYP3A4-substrate:	0.221

ADMET: Excretion

Clearance (CL):	6.46
Half-life (T1/2):	0.582

ADMET: Toxicity

hERG Blockers:	0.16
Human Hepatotoxicity (H-HT):	0.856
Drug-inuced Liver Injury (DILI):	0.55
AMES Toxicity:	0.21
Rat Oral Acute Toxicity:	0.865
Maximum Recommended Daily Dose:	0.873
Skin Sensitization:	0.956
Carcinogencity:	0.763
Eye Corrosion:	0.005
Eye Irritation:	0.038
Respiratory Toxicity:	0.204

Download Data

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

Natural Product: NPC172998

Natural Product ID:	NPC172998
*Common Name:**	BITFKDUCQOBZDL-KZSDYASMSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BITFKDUCQOBZDL-KZSDYASMSA-N
Standard InCHI:	InChI=1S/C20H22O6/c1-6-10(2)18(22)25-15-9-20(5)16(21)8-13(26-20)11(3)7-14-17(15)12(4)19(23)24-14/h6,8,14-15,17H,3-4,7,9H2,1-2,5H3/b10-6+/t14-,15-,17+,20-/m1/s1
SMILES:	C/C=C(C)/C(=O)O[C@@H]1C[C@]2(C)C(=O)C=C(C(=C)C[C@@H]3[C@@H]1C(=C)C(=O)O3)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2380787
PubChem CID:	73350425
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000324] Fatty acid esters

*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
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12880314]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[1294695]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104516]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	leaves and twigs	Taiwan	n.a.	PMID[1659612]
NPO19278	Taxodium distichum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17869103]
NPO17167	Magnolia fargesii	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19110419]
NPO17777	Helianthus tuberosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	aerial parts	Nanning, Guangxi Zhuang Autonomous Region, Peoples Republic of China	2012-OCT	PMID[24955889]
NPO19278	Taxodium distichum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26905523]
NPO17167	Magnolia fargesii	Species	Magnoliaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[9644071]
NPO17777	Helianthus tuberosus	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO17777	Helianthus tuberosus	Species	Asteraceae	Eukaryota	Tuber	n.a.	n.a.	Database[FooDB]
NPO17777	Helianthus tuberosus	Species	Asteraceae	Eukaryota	Tubers	n.a.		Database[FooDB]
NPO19278	Taxodium distichum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19217	Senecio platyphyllus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17777	Helianthus tuberosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19217	Senecio platyphyllus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17777	Helianthus tuberosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19278	Taxodium distichum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17777	Helianthus tuberosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18643	Siphula ramalinoides	Species	Icmadophilaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19483	Cetrelia sanguinea	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19807	Rubus parkeri	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17167	Magnolia fargesii	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19407	Crotalaria emarginella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18396	Eria carinata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16229	Amelanchier ovalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4131	Delphinium nordhagenii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19142	Rhytidiadelphus squarrosus	Species	Hylocomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19278	Taxodium distichum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12184	Oxylobus glanduliferus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO7159	Strobilurus ohshimae	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19217	Senecio platyphyllus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	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
Individual Protein	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	1570.0	nM	PMID[561907]
NPT27	Others	Unspecified		IC50	=	12070.0	nM	PMID[561907]

☑ 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 NPC172998 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	252
0.1-0.2	1370
0.2-0.3	5035
0.3-0.4	10320
0.4-0.5	15607
0.5-0.6	7003
0.6-0.7	2540
0.7-0.8	546
0.8-0.85	9
0.85-0.9	3
0.9-0.95	5
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9888	High Similarity	NPC273197
0.9888	High Similarity	NPC234339
0.9778	High Similarity	NPC299396
0.9778	High Similarity	NPC301596
0.9263	High Similarity	NPC140591
0.9263	High Similarity	NPC303653
0.9263	High Similarity	NPC197835
0.9263	High Similarity	NPC291500
0.9263	High Similarity	NPC189609
0.8713	High Similarity	NPC38154
0.8316	Intermediate Similarity	NPC20713
0.828	Intermediate Similarity	NPC475703
0.8261	Intermediate Similarity	NPC215364
0.8242	Intermediate Similarity	NPC128429
0.8211	Intermediate Similarity	NPC469718
0.8211	Intermediate Similarity	NPC329857
0.8191	Intermediate Similarity	NPC469653
0.8191	Intermediate Similarity	NPC471047
0.8191	Intermediate Similarity	NPC475906
0.8191	Intermediate Similarity	NPC469628
0.8191	Intermediate Similarity	NPC469631
0.8172	Intermediate Similarity	NPC50637
0.8172	Intermediate Similarity	NPC284902
0.8144	Intermediate Similarity	NPC473330
0.8144	Intermediate Similarity	NPC140543
0.8144	Intermediate Similarity	NPC474338
0.8144	Intermediate Similarity	NPC473316
0.8105	Intermediate Similarity	NPC166919
0.8085	Intermediate Similarity	NPC160138
0.8061	Intermediate Similarity	NPC474947
0.8043	Intermediate Similarity	NPC474703
0.8022	Intermediate Similarity	NPC141810
0.8022	Intermediate Similarity	NPC25684
0.8022	Intermediate Similarity	NPC281949
0.8022	Intermediate Similarity	NPC301477
0.8021	Intermediate Similarity	NPC312042
0.8021	Intermediate Similarity	NPC179394
0.8021	Intermediate Similarity	NPC144133
0.802	Intermediate Similarity	NPC164598
0.802	Intermediate Similarity	NPC474339
0.8	Intermediate Similarity	NPC475902
0.798	Intermediate Similarity	NPC476275
0.7979	Intermediate Similarity	NPC279859
0.7979	Intermediate Similarity	NPC107787
0.7979	Intermediate Similarity	NPC38576
0.7961	Intermediate Similarity	NPC471143
0.7961	Intermediate Similarity	NPC477510
0.7959	Intermediate Similarity	NPC477131
0.7959	Intermediate Similarity	NPC476267
0.7957	Intermediate Similarity	NPC115786
0.7935	Intermediate Similarity	NPC173609
0.7917	Intermediate Similarity	NPC295312
0.7917	Intermediate Similarity	NPC242877
0.7917	Intermediate Similarity	NPC64913
0.79	Intermediate Similarity	NPC471462
0.79	Intermediate Similarity	NPC471140
0.7895	Intermediate Similarity	NPC231889
0.7879	Intermediate Similarity	NPC304886
0.7872	Intermediate Similarity	NPC78089
0.7872	Intermediate Similarity	NPC130030
0.7865	Intermediate Similarity	NPC123360
0.7857	Intermediate Similarity	NPC228451
0.7857	Intermediate Similarity	NPC475838
0.7857	Intermediate Similarity	NPC125674
0.7849	Intermediate Similarity	NPC272814
0.7849	Intermediate Similarity	NPC318468
0.7843	Intermediate Similarity	NPC476270
0.7843	Intermediate Similarity	NPC264477
0.7843	Intermediate Similarity	NPC477511
0.7835	Intermediate Similarity	NPC475748
0.7835	Intermediate Similarity	NPC62815
0.7835	Intermediate Similarity	NPC475855
0.7835	Intermediate Similarity	NPC80875
0.7826	Intermediate Similarity	NPC42470
0.7826	Intermediate Similarity	NPC471325
0.7822	Intermediate Similarity	NPC187268
0.7802	Intermediate Similarity	NPC617
0.7802	Intermediate Similarity	NPC178277
0.7802	Intermediate Similarity	NPC270126
0.78	Intermediate Similarity	NPC17585
0.7789	Intermediate Similarity	NPC64153
0.7789	Intermediate Similarity	NPC162071
0.7778	Intermediate Similarity	NPC474247
0.7778	Intermediate Similarity	NPC469632
0.7767	Intermediate Similarity	NPC149371
0.7755	Intermediate Similarity	NPC175842
0.7755	Intermediate Similarity	NPC32494
0.7755	Intermediate Similarity	NPC133698
0.7755	Intermediate Similarity	NPC166110
0.7732	Intermediate Similarity	NPC151770
0.7723	Intermediate Similarity	NPC471490
0.7708	Intermediate Similarity	NPC471739
0.77	Intermediate Similarity	NPC67584
0.7692	Intermediate Similarity	NPC128276
0.7692	Intermediate Similarity	NPC475871
0.7692	Intermediate Similarity	NPC475945
0.7684	Intermediate Similarity	NPC235792
0.7677	Intermediate Similarity	NPC81419
0.7677	Intermediate Similarity	NPC135776
0.7677	Intermediate Similarity	NPC179746
0.7677	Intermediate Similarity	NPC476300
0.7677	Intermediate Similarity	NPC59646
0.7677	Intermediate Similarity	NPC475912
0.7677	Intermediate Similarity	NPC475657
0.7677	Intermediate Similarity	NPC248193
0.767	Intermediate Similarity	NPC201718
0.767	Intermediate Similarity	NPC185141
0.767	Intermediate Similarity	NPC110443
0.767	Intermediate Similarity	NPC128733
0.767	Intermediate Similarity	NPC47880
0.767	Intermediate Similarity	NPC474742
0.767	Intermediate Similarity	NPC133907
0.767	Intermediate Similarity	NPC15993
0.767	Intermediate Similarity	NPC46998
0.766	Intermediate Similarity	NPC170286
0.766	Intermediate Similarity	NPC170377
0.766	Intermediate Similarity	NPC475947
0.766	Intermediate Similarity	NPC250315
0.7653	Intermediate Similarity	NPC51004
0.7647	Intermediate Similarity	NPC279561
0.7647	Intermediate Similarity	NPC208233
0.7647	Intermediate Similarity	NPC54843
0.7647	Intermediate Similarity	NPC473326
0.7642	Intermediate Similarity	NPC470192
0.764	Intermediate Similarity	NPC476355
0.7629	Intermediate Similarity	NPC202672
0.7624	Intermediate Similarity	NPC230800
0.7624	Intermediate Similarity	NPC213078
0.7624	Intermediate Similarity	NPC279621
0.7624	Intermediate Similarity	NPC35498
0.7619	Intermediate Similarity	NPC474741
0.7615	Intermediate Similarity	NPC66108
0.7609	Intermediate Similarity	NPC63649
0.7609	Intermediate Similarity	NPC472965
0.7609	Intermediate Similarity	NPC264227
0.7604	Intermediate Similarity	NPC305475
0.7604	Intermediate Similarity	NPC475461
0.7604	Intermediate Similarity	NPC261721
0.76	Intermediate Similarity	NPC470010
0.76	Intermediate Similarity	NPC262133
0.76	Intermediate Similarity	NPC127019
0.76	Intermediate Similarity	NPC476596
0.76	Intermediate Similarity	NPC198853
0.76	Intermediate Similarity	NPC323008
0.76	Intermediate Similarity	NPC470521
0.76	Intermediate Similarity	NPC121825
0.76	Intermediate Similarity	NPC470013
0.7596	Intermediate Similarity	NPC471148
0.7596	Intermediate Similarity	NPC324017
0.7596	Intermediate Similarity	NPC320019
0.7596	Intermediate Similarity	NPC474747
0.7582	Intermediate Similarity	NPC97516
0.7582	Intermediate Similarity	NPC476794
0.7582	Intermediate Similarity	NPC65603
0.7582	Intermediate Similarity	NPC171204
0.7582	Intermediate Similarity	NPC57744
0.7582	Intermediate Similarity	NPC141789
0.7582	Intermediate Similarity	NPC476028
0.7582	Intermediate Similarity	NPC180290
0.7582	Intermediate Similarity	NPC470240
0.7582	Intermediate Similarity	NPC471225
0.7576	Intermediate Similarity	NPC32944
0.7576	Intermediate Similarity	NPC193396
0.7576	Intermediate Similarity	NPC12172
0.7576	Intermediate Similarity	NPC30515
0.7576	Intermediate Similarity	NPC208886
0.7576	Intermediate Similarity	NPC131209
0.7576	Intermediate Similarity	NPC184463
0.7573	Intermediate Similarity	NPC469551
0.7573	Intermediate Similarity	NPC477512
0.7553	Intermediate Similarity	NPC221231
0.7553	Intermediate Similarity	NPC471326
0.7551	Intermediate Similarity	NPC4986
0.7551	Intermediate Similarity	NPC142159
0.7551	Intermediate Similarity	NPC475971
0.7551	Intermediate Similarity	NPC95364
0.7551	Intermediate Similarity	NPC307411
0.7549	Intermediate Similarity	NPC161493
0.7527	Intermediate Similarity	NPC281132
0.7527	Intermediate Similarity	NPC474510
0.7527	Intermediate Similarity	NPC302426
0.7526	Intermediate Similarity	NPC266957
0.7525	Intermediate Similarity	NPC36954
0.7525	Intermediate Similarity	NPC52044
0.7525	Intermediate Similarity	NPC14961
0.7525	Intermediate Similarity	NPC270013
0.7525	Intermediate Similarity	NPC224689
0.7525	Intermediate Similarity	NPC471141
0.7525	Intermediate Similarity	NPC213698
0.7525	Intermediate Similarity	NPC471492
0.7524	Intermediate Similarity	NPC271059
0.7524	Intermediate Similarity	NPC25666
0.7524	Intermediate Similarity	NPC472755
0.75	Intermediate Similarity	NPC476598
0.75	Intermediate Similarity	NPC150923
0.75	Intermediate Similarity	NPC471145
0.75	Intermediate Similarity	NPC474547
0.75	Intermediate Similarity	NPC212486
0.75	Intermediate Similarity	NPC476597
0.75	Intermediate Similarity	NPC165383

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 NPC172998 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	220
0.1-0.2	1833
0.2-0.3	3788
0.3-0.4	2261
0.4-0.5	738
0.5-0.6	265
0.6-0.7	41
0.7-0.8	4
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
0.7551	Intermediate Similarity	NPD1695	Approved
0.7477	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD5282	Discontinued
0.732	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD46	Approved
0.6961	Remote Similarity	NPD6698	Approved
0.6961	Remote Similarity	NPD7838	Discovery
0.6842	Remote Similarity	NPD4756	Discovery
0.6837	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD6371	Approved
0.68	Remote Similarity	NPD1694	Approved
0.6733	Remote Similarity	NPD4249	Approved
0.6696	Remote Similarity	NPD6053	Discontinued
0.6667	Remote Similarity	NPD4250	Approved
0.6667	Remote Similarity	NPD5209	Approved
0.6667	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2067	Discontinued
0.6667	Remote Similarity	NPD4251	Approved
0.6609	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.66	Remote Similarity	NPD7154	Phase 3
0.6571	Remote Similarity	NPD7983	Approved
0.6491	Remote Similarity	NPD6686	Approved
0.6476	Remote Similarity	NPD5785	Approved
0.646	Remote Similarity	NPD6008	Approved
0.6455	Remote Similarity	NPD6648	Approved
0.6415	Remote Similarity	NPD5693	Phase 1
0.6374	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD5778	Approved
0.6355	Remote Similarity	NPD5779	Approved
0.6321	Remote Similarity	NPD5692	Phase 3
0.6311	Remote Similarity	NPD5363	Approved
0.6289	Remote Similarity	NPD8039	Approved
0.6286	Remote Similarity	NPD6672	Approved
0.6286	Remote Similarity	NPD5737	Approved
0.6262	Remote Similarity	NPD5694	Approved
0.6262	Remote Similarity	NPD6050	Approved
0.6261	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD5695	Phase 3
0.6216	Remote Similarity	NPD4225	Approved
0.6216	Remote Similarity	NPD5696	Approved
0.6202	Remote Similarity	NPD7260	Phase 2
0.6168	Remote Similarity	NPD5207	Approved
0.6154	Remote Similarity	NPD6845	Suspended
0.6154	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD6084	Phase 2
0.6126	Remote Similarity	NPD6083	Phase 2
0.6121	Remote Similarity	NPD5697	Approved
0.6117	Remote Similarity	NPD5362	Discontinued
0.6117	Remote Similarity	NPD6110	Phase 1
0.6106	Remote Similarity	NPD5344	Discontinued
0.6102	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.609	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD5369	Approved
0.6075	Remote Similarity	NPD6080	Approved
0.6075	Remote Similarity	NPD6904	Approved
0.6075	Remote Similarity	NPD6673	Approved
0.6071	Remote Similarity	NPD7638	Approved
0.6068	Remote Similarity	NPD7320	Approved
0.6068	Remote Similarity	NPD6899	Approved
0.6068	Remote Similarity	NPD6881	Approved
0.605	Remote Similarity	NPD6650	Approved
0.605	Remote Similarity	NPD6649	Approved
0.6036	Remote Similarity	NPD7839	Suspended
0.6034	Remote Similarity	NPD6402	Approved
0.6034	Remote Similarity	NPD5739	Approved
0.6034	Remote Similarity	NPD7128	Approved
0.6034	Remote Similarity	NPD6675	Approved
0.6019	Remote Similarity	NPD4270	Approved
0.6019	Remote Similarity	NPD6435	Approved
0.6019	Remote Similarity	NPD4269	Approved
0.6018	Remote Similarity	NPD7639	Approved
0.6018	Remote Similarity	NPD7640	Approved
0.6017	Remote Similarity	NPD6373	Approved
0.6017	Remote Similarity	NPD6012	Approved
0.6017	Remote Similarity	NPD6372	Approved
0.6017	Remote Similarity	NPD6014	Approved
0.6017	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD6013	Approved
0.6	Remote Similarity	NPD8516	Approved
0.6	Remote Similarity	NPD8515	Approved
0.6	Remote Similarity	NPD8517	Approved
0.6	Remote Similarity	NPD8513	Phase 3
0.5984	Remote Similarity	NPD7492	Approved
0.5983	Remote Similarity	NPD5701	Approved
0.5981	Remote Similarity	NPD6903	Approved
0.598	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.598	Remote Similarity	NPD4819	Approved
0.598	Remote Similarity	NPD4820	Approved
0.598	Remote Similarity	NPD4822	Approved
0.598	Remote Similarity	NPD4821	Approved
0.5966	Remote Similarity	NPD7290	Approved
0.5966	Remote Similarity	NPD7102	Approved
0.5966	Remote Similarity	NPD6883	Approved
0.5946	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD5654	Approved
0.5943	Remote Similarity	NPD7334	Approved
0.5943	Remote Similarity	NPD5330	Approved
0.5943	Remote Similarity	NPD6684	Approved
0.5943	Remote Similarity	NPD7521	Approved
0.5943	Remote Similarity	NPD5786	Approved
0.5943	Remote Similarity	NPD7146	Approved
0.5943	Remote Similarity	NPD6409	Approved
0.5938	Remote Similarity	NPD6616	Approved
0.5935	Remote Similarity	NPD7115	Discovery
0.5932	Remote Similarity	NPD6011	Approved
0.5926	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD6101	Approved
0.592	Remote Similarity	NPD6319	Approved
0.592	Remote Similarity	NPD6054	Approved
0.5917	Remote Similarity	NPD6869	Approved
0.5917	Remote Similarity	NPD6617	Approved
0.5917	Remote Similarity	NPD8130	Phase 1
0.5917	Remote Similarity	NPD6847	Approved
0.5909	Remote Similarity	NPD6399	Phase 3
0.5891	Remote Similarity	NPD7078	Approved
0.5873	Remote Similarity	NPD6016	Approved
0.5873	Remote Similarity	NPD6015	Approved
0.5868	Remote Similarity	NPD8297	Approved
0.5868	Remote Similarity	NPD6882	Approved
0.5856	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD7900	Approved
0.5854	Remote Similarity	NPD690	Clinical (unspecified phase)
0.5846	Remote Similarity	NPD7736	Approved
0.5841	Remote Similarity	NPD5959	Approved
0.5833	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5827	Remote Similarity	NPD8080	Discontinued
0.5827	Remote Similarity	NPD5988	Approved
0.5827	Remote Similarity	NPD6370	Approved
0.5825	Remote Similarity	NPD4252	Approved
0.5825	Remote Similarity	NPD5368	Approved
0.5825	Remote Similarity	NPD4695	Discontinued
0.582	Remote Similarity	NPD4632	Approved
0.5818	Remote Similarity	NPD6411	Approved
0.5818	Remote Similarity	NPD7637	Suspended
0.5818	Remote Similarity	NPD5281	Approved
0.5818	Remote Similarity	NPD5284	Approved
0.5814	Remote Similarity	NPD7507	Approved
0.5806	Remote Similarity	NPD6009	Approved
0.5794	Remote Similarity	NPD6059	Approved
0.5794	Remote Similarity	NPD6098	Approved
0.5794	Remote Similarity	NPD5279	Phase 3
0.5789	Remote Similarity	NPD3704	Approved
0.5785	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD2204	Approved
0.5784	Remote Similarity	NPD4271	Approved
0.5784	Remote Similarity	NPD4268	Approved
0.5784	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.578	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD8293	Discontinued
0.5769	Remote Similarity	NPD8074	Phase 3
0.576	Remote Similarity	NPD7641	Discontinued
0.5758	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5748	Remote Similarity	NPD7503	Approved
0.5748	Remote Similarity	NPD5983	Phase 2
0.5726	Remote Similarity	NPD6274	Approved
0.5714	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6001	Approved
0.5702	Remote Similarity	NPD7902	Approved
0.5682	Remote Similarity	NPD7319	Approved
0.568	Remote Similarity	NPD7500	Approved
0.5669	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD5210	Approved
0.5664	Remote Similarity	NPD4629	Approved
0.566	Remote Similarity	NPD5332	Approved
0.566	Remote Similarity	NPD5331	Approved
0.5659	Remote Similarity	NPD7830	Approved
0.5659	Remote Similarity	NPD7642	Approved
0.5659	Remote Similarity	NPD7604	Phase 2
0.5659	Remote Similarity	NPD7829	Approved
0.5656	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD5211	Phase 2
0.5638	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD4753	Phase 2
0.5625	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD4790	Discontinued
0.5607	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5603	Remote Similarity	NPD5286	Approved
0.5603	Remote Similarity	NPD5285	Approved
0.5603	Remote Similarity	NPD4696	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