NPASS Compound

Structure

CID308331 OpenBabel06191716112D 22 21 0 0 0 0 0 0 0 0999 V2000 8.6603 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 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 8.6603 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 0.0000 C 0 0 0 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 9.5263 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 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 3.4641 0.0000 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 9.5263 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -2.5000 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 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 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 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 5 19 1 0 0 0 0 6 9 1 0 0 0 0 6 10 1 0 0 0 0 7 11 1 0 0 0 0 7 12 1 0 0 0 0 8 13 1 0 0 0 0 8 14 1 0 0 0 0 9 16 2 0 0 0 0 10 17 1 0 0 0 0 11 17 2 0 0 0 0 12 18 1 0 0 0 0 13 18 2 0 0 0 0 14 19 1 0 0 0 0 15 19 2 0 0 0 0 15 20 1 0 0 0 0 20 21 2 0 0 0 0 20 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	304.24
Volume:	358.874
LogP:	6.288
LogD:	4.805
LogS:	-4.684
# Rotatable Bonds:	10
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	0
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.487
Synthetic Accessibility Score:	3.097
Fsp3:	0.55
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.948
MDCK Permeability:	1.9174050976289436e-05
Pgp-inhibitor:	0.023
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.091
20% Bioavailability (F20%):	0.718
30% Bioavailability (F30%):	0.12

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.047
Plasma Protein Binding (PPB):	96.1907730102539%
Volume Distribution (VD):	0.487
Pgp-substrate:	2.4973273277282715%

ADMET: Metabolism

CYP1A2-inhibitor:	0.097
CYP1A2-substrate:	0.117
CYP2C19-inhibitor:	0.07
CYP2C19-substrate:	0.183
CYP2C9-inhibitor:	0.396
CYP2C9-substrate:	0.986
CYP2D6-inhibitor:	0.039
CYP2D6-substrate:	0.098
CYP3A4-inhibitor:	0.066
CYP3A4-substrate:	0.08

ADMET: Excretion

Clearance (CL):	3.994
Half-life (T1/2):	0.693

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.868
Drug-inuced Liver Injury (DILI):	0.027
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.002
Maximum Recommended Daily Dose:	0.189
Skin Sensitization:	0.974
Carcinogencity:	0.083
Eye Corrosion:	0.954
Eye Irritation:	0.98
Respiratory Toxicity:	0.321

Download Data

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

Natural Product: NPC308331

Natural Product ID:	NPC308331
*Common Name:**	Geranylgeranoic Acid
IUPAC Name:	(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenoic acid
Synonyms:	Geranylgeranoic Acid
Standard InCHIKey:	SZNLKILVMCHHSD-OZFNKYQOSA-N
Standard InCHI:	InChI=1S/C20H32O2/c1-16(2)9-6-10-17(3)11-7-12-18(4)13-8-14-19(5)15-20(21)22/h9,11,13,15H,6-8,10,12,14H2,1-5H3,(H,21,22)/b17-11+,18-13+,19-15+
SMILES:	C/C(=CCC/C(=C/C(=O)O)/C)/CC/C=C(/CCC=C(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL171326
PubChem CID:	5275521
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001357] Acyclic 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
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[12713396]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16441081]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562834]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16675659]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[20022509]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21123068]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21866899]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22074222]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[22074222]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23325115]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[23541646]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23867078]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[23867078]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	fruit	n.a.	PMID[24155209]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24479468]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[24957203]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24959987]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25302569]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25445757]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25744461]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26841168]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28140583]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28522265]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29641206]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32196343]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7381508]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	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	2
Others	2
Potency	4

Activity Type	# Activity
Individual Protein	6
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT442	Individual Protein	Ferritin light chain	Equus caballus	Potency	=	50118.7	nM	PMID[464584]
NPT55	Individual Protein	Putative fructose-1,6-bisphosphate aldolase	Giardia intestinalis	Potency	=	22334.2	nM	PMID[464584]
NPT443	Individual Protein	Histone acetyltransferase GCN5	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[464584]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[464584]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	-5.57	%	PMID[464585]
NPT20	Organism	Candida albicans	Candida albicans	IC50	>	100.0	ug.mL-1	PMID[464583]
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	-2.05	%	PMID[464585]

☑ 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 NPC308331 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	149
0.1-0.2	6979
0.2-0.3	21305
0.3-0.4	9249
0.4-0.5	3522
0.5-0.6	1184
0.6-0.7	242
0.7-0.8	53
0.8-0.85	10
0.85-0.9	1
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9535	High Similarity	NPC304079
0.9535	High Similarity	NPC6963
0.8298	Intermediate Similarity	NPC128280
0.8113	Intermediate Similarity	NPC129150
0.8113	Intermediate Similarity	NPC283502
0.8113	Intermediate Similarity	NPC293437
0.8113	Intermediate Similarity	NPC294938
0.8113	Intermediate Similarity	NPC249850
0.8085	Intermediate Similarity	NPC270706
0.8	Intermediate Similarity	NPC43053
0.8	Intermediate Similarity	NPC221250
0.7963	Intermediate Similarity	NPC254095
0.7963	Intermediate Similarity	NPC223679
0.7963	Intermediate Similarity	NPC21946
0.7885	Intermediate Similarity	NPC474127
0.7818	Intermediate Similarity	NPC82465
0.7778	Intermediate Similarity	NPC135863
0.7778	Intermediate Similarity	NPC8270
0.7674	Intermediate Similarity	NPC308418
0.766	Intermediate Similarity	NPC116934
0.7609	Intermediate Similarity	NPC269823
0.7551	Intermediate Similarity	NPC197467
0.7551	Intermediate Similarity	NPC87137
0.7451	Intermediate Similarity	NPC236338
0.7451	Intermediate Similarity	NPC221467
0.7447	Intermediate Similarity	NPC256766
0.7447	Intermediate Similarity	NPC213538
0.7347	Intermediate Similarity	NPC26600
0.7347	Intermediate Similarity	NPC160628
0.7347	Intermediate Similarity	NPC47946
0.7347	Intermediate Similarity	NPC140501
0.7321	Intermediate Similarity	NPC471619
0.7292	Intermediate Similarity	NPC270796
0.7255	Intermediate Similarity	NPC267110
0.7241	Intermediate Similarity	NPC329416
0.7241	Intermediate Similarity	NPC317025
0.7241	Intermediate Similarity	NPC317177
0.7241	Intermediate Similarity	NPC326645
0.7174	Intermediate Similarity	NPC182840
0.7174	Intermediate Similarity	NPC29091
0.7174	Intermediate Similarity	NPC255042
0.7174	Intermediate Similarity	NPC103213
0.7167	Intermediate Similarity	NPC107258
0.7167	Intermediate Similarity	NPC282760
0.7143	Intermediate Similarity	NPC138935
0.7143	Intermediate Similarity	NPC268185
0.7119	Intermediate Similarity	NPC68110
0.7059	Intermediate Similarity	NPC91495
0.7049	Intermediate Similarity	NPC259156
0.7049	Intermediate Similarity	NPC242945
0.7018	Intermediate Similarity	NPC474084
0.7	Intermediate Similarity	NPC117572
0.6981	Remote Similarity	NPC15129
0.6964	Remote Similarity	NPC472808
0.6964	Remote Similarity	NPC324224
0.6935	Remote Similarity	NPC254886
0.6923	Remote Similarity	NPC135698
0.6909	Remote Similarity	NPC218486
0.6909	Remote Similarity	NPC478120
0.6909	Remote Similarity	NPC189677
0.6885	Remote Similarity	NPC471565
0.6885	Remote Similarity	NPC471556
0.6885	Remote Similarity	NPC471566
0.68	Remote Similarity	NPC477686
0.68	Remote Similarity	NPC12907
0.6792	Remote Similarity	NPC15789
0.6792	Remote Similarity	NPC225974
0.6792	Remote Similarity	NPC59051
0.6792	Remote Similarity	NPC474460
0.6792	Remote Similarity	NPC20934
0.6792	Remote Similarity	NPC288381
0.6786	Remote Similarity	NPC146551
0.6786	Remote Similarity	NPC152668
0.6786	Remote Similarity	NPC470963
0.6786	Remote Similarity	NPC474513
0.6786	Remote Similarity	NPC478117
0.678	Remote Similarity	NPC79756
0.6774	Remote Similarity	NPC142423
0.6774	Remote Similarity	NPC308294
0.6667	Remote Similarity	NPC474495
0.6667	Remote Similarity	NPC96663
0.6667	Remote Similarity	NPC473672
0.6667	Remote Similarity	NPC48162
0.6667	Remote Similarity	NPC470964
0.6667	Remote Similarity	NPC178586
0.6667	Remote Similarity	NPC297363
0.6667	Remote Similarity	NPC55376
0.6667	Remote Similarity	NPC26810
0.6667	Remote Similarity	NPC311648
0.6667	Remote Similarity	NPC191337
0.6667	Remote Similarity	NPC12319
0.6667	Remote Similarity	NPC60675
0.6667	Remote Similarity	NPC18205
0.661	Remote Similarity	NPC322002
0.661	Remote Similarity	NPC322186
0.6607	Remote Similarity	NPC154626
0.6607	Remote Similarity	NPC322461
0.6604	Remote Similarity	NPC15912
0.6604	Remote Similarity	NPC149821
0.6604	Remote Similarity	NPC5413
0.6604	Remote Similarity	NPC122212
0.6604	Remote Similarity	NPC137419
0.6596	Remote Similarity	NPC180840
0.6596	Remote Similarity	NPC63598
0.6557	Remote Similarity	NPC155849
0.6557	Remote Similarity	NPC473737
0.6552	Remote Similarity	NPC265551
0.6552	Remote Similarity	NPC594
0.6552	Remote Similarity	NPC71755
0.6552	Remote Similarity	NPC48968
0.6552	Remote Similarity	NPC44542
0.6552	Remote Similarity	NPC212730
0.6552	Remote Similarity	NPC472445
0.6545	Remote Similarity	NPC92114
0.6538	Remote Similarity	NPC262558
0.6538	Remote Similarity	NPC8610
0.6515	Remote Similarity	NPC316185
0.6508	Remote Similarity	NPC255781
0.6508	Remote Similarity	NPC81907
0.6508	Remote Similarity	NPC146811
0.6508	Remote Similarity	NPC315115
0.65	Remote Similarity	NPC471278
0.65	Remote Similarity	NPC327112
0.6481	Remote Similarity	NPC26960
0.6481	Remote Similarity	NPC27264
0.6481	Remote Similarity	NPC182102
0.6462	Remote Similarity	NPC236208
0.6462	Remote Similarity	NPC151481
0.6458	Remote Similarity	NPC15934
0.6444	Remote Similarity	NPC12889
0.6441	Remote Similarity	NPC189700
0.6441	Remote Similarity	NPC34416
0.6429	Remote Similarity	NPC477780
0.6429	Remote Similarity	NPC217188
0.6429	Remote Similarity	NPC70387
0.6429	Remote Similarity	NPC321062
0.6429	Remote Similarity	NPC474496
0.6429	Remote Similarity	NPC477781
0.6415	Remote Similarity	NPC318549
0.6415	Remote Similarity	NPC207292
0.64	Remote Similarity	NPC51758
0.64	Remote Similarity	NPC67761
0.64	Remote Similarity	NPC88079
0.64	Remote Similarity	NPC108494
0.64	Remote Similarity	NPC194586
0.64	Remote Similarity	NPC102879
0.64	Remote Similarity	NPC209279
0.64	Remote Similarity	NPC57923
0.64	Remote Similarity	NPC180871
0.64	Remote Similarity	NPC68889
0.6393	Remote Similarity	NPC151648
0.6383	Remote Similarity	NPC185839
0.6379	Remote Similarity	NPC325977
0.6379	Remote Similarity	NPC245002
0.6364	Remote Similarity	NPC59558
0.6364	Remote Similarity	NPC477458
0.6364	Remote Similarity	NPC148056
0.6349	Remote Similarity	NPC470123
0.6349	Remote Similarity	NPC7940
0.6349	Remote Similarity	NPC273600
0.6346	Remote Similarity	NPC474202
0.6346	Remote Similarity	NPC474362
0.6333	Remote Similarity	NPC97570
0.6333	Remote Similarity	NPC106851
0.6333	Remote Similarity	NPC329249
0.6333	Remote Similarity	NPC274927
0.6333	Remote Similarity	NPC286189
0.6327	Remote Similarity	NPC111474
0.6327	Remote Similarity	NPC56917
0.6324	Remote Similarity	NPC315843
0.6324	Remote Similarity	NPC227396
0.6316	Remote Similarity	NPC88966
0.6316	Remote Similarity	NPC6095
0.6316	Remote Similarity	NPC85813
0.6316	Remote Similarity	NPC32467
0.6316	Remote Similarity	NPC424
0.6316	Remote Similarity	NPC290563
0.6316	Remote Similarity	NPC261831
0.6316	Remote Similarity	NPC154245
0.6316	Remote Similarity	NPC159535
0.6316	Remote Similarity	NPC281972
0.6316	Remote Similarity	NPC25417
0.6316	Remote Similarity	NPC151761
0.6316	Remote Similarity	NPC87564
0.6308	Remote Similarity	NPC249713
0.6308	Remote Similarity	NPC313444
0.6296	Remote Similarity	NPC234084
0.629	Remote Similarity	NPC210303
0.629	Remote Similarity	NPC322457
0.629	Remote Similarity	NPC77891
0.629	Remote Similarity	NPC44343
0.629	Remote Similarity	NPC217940
0.629	Remote Similarity	NPC475073
0.629	Remote Similarity	NPC179087
0.629	Remote Similarity	NPC2328
0.6279	Remote Similarity	NPC123965
0.6279	Remote Similarity	NPC115959
0.6275	Remote Similarity	NPC301972
0.6275	Remote Similarity	NPC216921
0.6269	Remote Similarity	NPC133253

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 NPC308331 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	118
0.1-0.2	4589
0.2-0.3	3603
0.3-0.4	668
0.4-0.5	119
0.5-0.6	31
0.6-0.7	13
0.7-0.8	8
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.913	High Similarity	NPD4220	Pre-registration
0.7347	Intermediate Similarity	NPD4265	Approved
0.7347	Intermediate Similarity	NPD39	Approved
0.7308	Intermediate Similarity	NPD6927	Phase 3
0.7292	Intermediate Similarity	NPD9411	Phase 1
0.7292	Intermediate Similarity	NPD5326	Phase 3
0.7241	Intermediate Similarity	NPD4193	Approved
0.7241	Intermediate Similarity	NPD4191	Approved
0.7241	Intermediate Similarity	NPD4194	Approved
0.7241	Intermediate Similarity	NPD4192	Approved
0.7	Intermediate Similarity	NPD4222	Approved
0.6809	Remote Similarity	NPD5783	Phase 3
0.6604	Remote Similarity	NPD3173	Approved
0.65	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6096	Approved
0.6471	Remote Similarity	NPD6097	Approved
0.6415	Remote Similarity	NPD5343	Approved
0.6346	Remote Similarity	NPD3174	Discontinued
0.6316	Remote Similarity	NPD3195	Phase 2
0.6316	Remote Similarity	NPD4266	Approved
0.6316	Remote Similarity	NPD3196	Approved
0.6316	Remote Similarity	NPD3194	Approved
0.614	Remote Similarity	NPD3172	Approved
0.6094	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD8573	Approved
0.6071	Remote Similarity	NPD28	Approved
0.6071	Remote Similarity	NPD29	Approved
0.5938	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD6109	Phase 1
0.5893	Remote Similarity	NPD2268	Discontinued
0.5833	Remote Similarity	NPD4756	Discovery
0.5778	Remote Similarity	NPD9114	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD8779	Phase 3

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