NPASS Compound

Structure

CID159750 OpenBabel06191715532D 44 46 0 0 1 0 0 0 0 0999 V2000 18.4410 -5.1422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1215 -1.3849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 18.1320 -4.1912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 17.1538 -3.9833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.4847 -4.7264 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.5065 -4.5185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.8374 -5.2616 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9904 1.3319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3212 0.5888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.8593 -5.0537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9685 1.1240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3431 0.7967 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.1901 -5.7969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6376 1.8671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6740 0.0535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.2120 -5.5890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6158 1.6592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6958 0.2614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5428 -6.3321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9248 0.7082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3794 -1.0169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0485 -0.2738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3046 -4.8641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5158 -1.2950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3046 -3.8641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5158 -2.2950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -0.9781 0.0000 C 0 0 1 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 4.0267 -0.4817 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.5647 -6.1242 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.2557 -0.0350 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.2557 -5.1731 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.5647 -0.9860 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.2557 -3.5551 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.5647 -2.6041 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3357 -1.4328 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.8956 -6.8673 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2775 0.1729 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4945 0.9706 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 10.8435 -4.3641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.9769 -1.7950 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 10 1 0 0 0 0 8 9 1 0 0 0 0 8 11 1 0 0 0 0 9 12 1 0 0 0 0 10 13 1 0 0 0 0 11 14 1 0 0 0 0 12 15 1 0 0 0 0 13 16 1 0 0 0 0 14 17 1 0 0 0 0 15 18 1 0 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 18 30 1 0 0 0 0 19 31 1 0 0 0 0 20 32 1 0 0 0 0 21 22 1 0 0 0 0 21 29 1 0 0 0 0 22 30 1 0 0 0 0 23 25 1 0 0 0 0 23 33 1 0 0 0 0 24 26 1 0 0 0 0 24 34 1 0 0 0 0 27 28 1 0 0 0 0 27 29 2 0 0 0 0 28 2 1 6 0 0 0 28 42 1 0 0 0 0 29 37 1 0 0 0 0 30 38 1 6 0 0 0 31 39 1 1 0 0 0 32 40 1 6 0 0 0 33 31 1 1 0 0 0 33 43 1 0 0 0 0 34 32 1 1 0 0 0 34 44 1 0 0 0 0 35 25 1 6 0 0 0 35 36 1 0 0 0 0 35 43 1 0 0 0 0 36 26 1 6 0 0 0 36 44 1 0 0 0 0 37 41 2 0 0 0 0 37 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	622.48
Volume:	679.097
LogP:	9.089
LogD:	4.931
LogS:	-6.337
# Rotatable Bonds:	25
TPSA:	112.52
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.081
Synthetic Accessibility Score:	4.681
Fsp3:	0.892
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.243
MDCK Permeability:	1.5754092601127923e-05
Pgp-inhibitor:	0.012
Pgp-substrate:	0.976
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.648

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	97.70967864990234%
Volume Distribution (VD):	0.859
Pgp-substrate:	2.9027559757232666%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.279
CYP2C19-inhibitor:	0.059
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.049
CYP2C9-substrate:	0.952
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.184
CYP3A4-inhibitor:	0.115
CYP3A4-substrate:	0.021

ADMET: Excretion

Clearance (CL):	3.914
Half-life (T1/2):	0.083

ADMET: Toxicity

hERG Blockers:	0.494
Human Hepatotoxicity (H-HT):	0.245
Drug-inuced Liver Injury (DILI):	0.095
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.27
Maximum Recommended Daily Dose:	0.581
Skin Sensitization:	0.969
Carcinogencity:	0.037
Eye Corrosion:	0.003
Eye Irritation:	0.02
Respiratory Toxicity:	0.23

Download Data

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

Natural Product: NPC159750

Natural Product ID:	NPC159750
*Common Name:**	Uvarigrandin A
IUPAC Name:	(2S)-4-[(3S,13R)-3,13-dihydroxy-13-[(2R,5R)-5-[(2R,5R)-5-[(1R)-1-hydroxyundecyl]oxolan-2-yl]oxolan-2-yl]tridecyl]-2-methyl-2H-furan-5-one
Synonyms:	Uvarigrandin A
Standard InCHIKey:	SXPGOPRMCQROGB-WGCJABNLSA-N
Standard InCHI:	InChI=1S/C37H66O7/c1-3-4-5-6-7-10-13-16-19-31(39)33-23-25-35(43-33)36-26-24-34(44-36)32(40)20-17-14-11-8-9-12-15-18-30(38)22-21-29-27-28(2)42-37(29)41/h27-28,30-36,38-40H,3-26H2,1-2H3/t28-,30-,31+,32+,33+,34+,35+,36+/m0/s1
SMILES:	CCCCCCCCCC[C@H]([C@H]1CC[C@@H](O1)[C@H]1CC[C@@H](O1)[C@@H](CCCCCCCCC[C@@H](CCC1=C[C@@H](OC1=O)C)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1933125
PubChem CID:	9986397
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols [CHEMONTID:0002518] Annonaceous acetogenins

*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
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11141125]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398544]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18419154]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19296389]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21910504]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	seed	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Barks	n.a.	n.a.	PMID[2348205]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	fruit	n.a.	PMID[8786370]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	bark	n.a.	n.a.	PMID[9214729]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2884	Annona squamosa	Species	Annonaceae	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	7

Activity Type	# Activity
Cell Line	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	0.08	ug.mL-1	PMID[490084]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	0.07	ug.mL-1	PMID[490084]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	0.096	ug.mL-1	PMID[490084]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	0.78	ug.mL-1	PMID[490084]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	0.0029	ug.mL-1	PMID[490084]
NPT1097	Cell Line	MKN-45	Homo sapiens	IC50	=	0.069	ug.mL-1	PMID[490084]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[490085]

☑ 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 NPC159750 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	193
0.1-0.2	1510
0.2-0.3	6176
0.3-0.4	14659
0.4-0.5	11058
0.5-0.6	6480
0.6-0.7	2139
0.7-0.8	301
0.8-0.85	23
0.85-0.9	71
0.9-0.95	57
0.95-1	30

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC154097
1.0	High Similarity	NPC470401
1.0	High Similarity	NPC473649
0.9753	High Similarity	NPC39167
0.9753	High Similarity	NPC77871
0.9753	High Similarity	NPC25764
0.9753	High Similarity	NPC319036
0.9753	High Similarity	NPC292809
0.9753	High Similarity	NPC473156
0.9753	High Similarity	NPC39279
0.9753	High Similarity	NPC477018
0.9753	High Similarity	NPC9678
0.9753	High Similarity	NPC100921
0.9753	High Similarity	NPC475268
0.9753	High Similarity	NPC473671
0.9753	High Similarity	NPC235809
0.9753	High Similarity	NPC470400
0.9753	High Similarity	NPC202055
0.9634	High Similarity	NPC241360
0.9634	High Similarity	NPC473840
0.9634	High Similarity	NPC132940
0.9634	High Similarity	NPC293136
0.9634	High Similarity	NPC219652
0.9634	High Similarity	NPC309211
0.9634	High Similarity	NPC477010
0.9634	High Similarity	NPC25703
0.9634	High Similarity	NPC282815
0.9518	High Similarity	NPC258068
0.9518	High Similarity	NPC20533
0.9518	High Similarity	NPC473995
0.9518	High Similarity	NPC476583
0.9405	High Similarity	NPC191929
0.9405	High Similarity	NPC169511
0.9405	High Similarity	NPC172821
0.9405	High Similarity	NPC81045
0.9405	High Similarity	NPC473905
0.9405	High Similarity	NPC320458
0.9405	High Similarity	NPC61257
0.9405	High Similarity	NPC151403
0.9405	High Similarity	NPC261952
0.9405	High Similarity	NPC287164
0.9405	High Similarity	NPC171135
0.9405	High Similarity	NPC39754
0.9405	High Similarity	NPC234077
0.9405	High Similarity	NPC242364
0.9405	High Similarity	NPC320569
0.9405	High Similarity	NPC274446
0.9405	High Similarity	NPC89001
0.9405	High Similarity	NPC100454
0.9405	High Similarity	NPC133730
0.939	High Similarity	NPC156804
0.9383	High Similarity	NPC145914
0.9383	High Similarity	NPC73310
0.9383	High Similarity	NPC11332
0.9383	High Similarity	NPC94875
0.9383	High Similarity	NPC180363
0.9383	High Similarity	NPC473780
0.9383	High Similarity	NPC131002
0.9383	High Similarity	NPC475159
0.9383	High Similarity	NPC329829
0.9383	High Similarity	NPC473712
0.9383	High Similarity	NPC65930
0.9383	High Similarity	NPC473529
0.9294	High Similarity	NPC477011
0.9294	High Similarity	NPC91067
0.9294	High Similarity	NPC20621
0.9294	High Similarity	NPC318963
0.9294	High Similarity	NPC477016
0.9294	High Similarity	NPC477017
0.9294	High Similarity	NPC40066
0.9294	High Similarity	NPC81778
0.9294	High Similarity	NPC473504
0.9294	High Similarity	NPC93794
0.9294	High Similarity	NPC42598
0.9277	High Similarity	NPC120398
0.9277	High Similarity	NPC329838
0.9277	High Similarity	NPC322529
0.9277	High Similarity	NPC329615
0.9277	High Similarity	NPC471567
0.9268	High Similarity	NPC144415
0.9268	High Similarity	NPC253801
0.9186	High Similarity	NPC239517
0.9167	High Similarity	NPC142117
0.9167	High Similarity	NPC231096
0.9167	High Similarity	NPC114694
0.9167	High Similarity	NPC107717
0.9167	High Similarity	NPC232555
0.9167	High Similarity	NPC171174
0.9167	High Similarity	NPC475581
0.9167	High Similarity	NPC240695
0.9167	High Similarity	NPC112685
0.9167	High Similarity	NPC62118
0.9157	High Similarity	NPC163093
0.907	High Similarity	NPC280612
0.9059	High Similarity	NPC477012
0.9048	High Similarity	NPC477014
0.9048	High Similarity	NPC66346
0.9048	High Similarity	NPC283085
0.9048	High Similarity	NPC110710
0.9048	High Similarity	NPC82795
0.9048	High Similarity	NPC223871
0.9048	High Similarity	NPC107986
0.9048	High Similarity	NPC286338
0.9048	High Similarity	NPC132496
0.9048	High Similarity	NPC473478
0.9048	High Similarity	NPC1083
0.9048	High Similarity	NPC473669
0.9048	High Similarity	NPC103284
0.9048	High Similarity	NPC473651
0.9048	High Similarity	NPC477013
0.9048	High Similarity	NPC231009
0.8977	High Similarity	NPC473520
0.8953	High Similarity	NPC48338
0.8953	High Similarity	NPC21208
0.8953	High Similarity	NPC40376
0.8953	High Similarity	NPC233551
0.8953	High Similarity	NPC280621
0.8953	High Similarity	NPC20339
0.8941	High Similarity	NPC69082
0.8941	High Similarity	NPC308412
0.8941	High Similarity	NPC473687
0.8941	High Similarity	NPC477015
0.8941	High Similarity	NPC134865
0.8941	High Similarity	NPC279267
0.8941	High Similarity	NPC134807
0.8941	High Similarity	NPC210218
0.8941	High Similarity	NPC204686
0.8941	High Similarity	NPC219498
0.8941	High Similarity	NPC134885
0.8941	High Similarity	NPC103523
0.8837	High Similarity	NPC178215
0.8764	High Similarity	NPC11456
0.875	High Similarity	NPC473904
0.8721	High Similarity	NPC47937
0.8636	High Similarity	NPC130359
0.8636	High Similarity	NPC14901
0.8636	High Similarity	NPC139418
0.8605	High Similarity	NPC182383
0.8556	High Similarity	NPC475173
0.8556	High Similarity	NPC473723
0.8556	High Similarity	NPC473561
0.8556	High Similarity	NPC473663
0.8444	Intermediate Similarity	NPC473707
0.8352	Intermediate Similarity	NPC81419
0.8352	Intermediate Similarity	NPC179746
0.8333	Intermediate Similarity	NPC476004
0.8333	Intermediate Similarity	NPC474761
0.8242	Intermediate Similarity	NPC12172
0.8242	Intermediate Similarity	NPC208886
0.8242	Intermediate Similarity	NPC30515
0.8222	Intermediate Similarity	NPC295312
0.8182	Intermediate Similarity	NPC21469
0.8132	Intermediate Similarity	NPC51004
0.8132	Intermediate Similarity	NPC473619
0.809	Intermediate Similarity	NPC164393
0.8043	Intermediate Similarity	NPC473321
0.8043	Intermediate Similarity	NPC184463
0.8022	Intermediate Similarity	NPC307411
0.8022	Intermediate Similarity	NPC474032
0.8	Intermediate Similarity	NPC248602
0.7979	Intermediate Similarity	NPC36954
0.7978	Intermediate Similarity	NPC137033
0.7957	Intermediate Similarity	NPC288240
0.7957	Intermediate Similarity	NPC476300
0.7957	Intermediate Similarity	NPC295204
0.7957	Intermediate Similarity	NPC273579
0.7957	Intermediate Similarity	NPC475912
0.7957	Intermediate Similarity	NPC162205
0.7955	Intermediate Similarity	NPC11620
0.7927	Intermediate Similarity	NPC84038
0.7917	Intermediate Similarity	NPC473326
0.7912	Intermediate Similarity	NPC58219
0.7912	Intermediate Similarity	NPC227379
0.7912	Intermediate Similarity	NPC153805
0.7912	Intermediate Similarity	NPC177629
0.7912	Intermediate Similarity	NPC474471
0.7912	Intermediate Similarity	NPC202672
0.7889	Intermediate Similarity	NPC284902
0.7872	Intermediate Similarity	NPC474035
0.7872	Intermediate Similarity	NPC81386
0.7865	Intermediate Similarity	NPC474780
0.7865	Intermediate Similarity	NPC474251
0.7831	Intermediate Similarity	NPC474705
0.7826	Intermediate Similarity	NPC92974
0.7802	Intermediate Similarity	NPC186148
0.7789	Intermediate Similarity	NPC14961
0.7789	Intermediate Similarity	NPC270013
0.7778	Intermediate Similarity	NPC329749
0.7778	Intermediate Similarity	NPC475206
0.7766	Intermediate Similarity	NPC212486
0.7742	Intermediate Similarity	NPC473448
0.7732	Intermediate Similarity	NPC187268
0.7717	Intermediate Similarity	NPC281516
0.7717	Intermediate Similarity	NPC473715
0.7708	Intermediate Similarity	NPC476315
0.7708	Intermediate Similarity	NPC477921
0.7692	Intermediate Similarity	NPC474949
0.7692	Intermediate Similarity	NPC475019
0.7677	Intermediate Similarity	NPC86077
0.7674	Intermediate Similarity	NPC475711

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 NPC159750 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	177
0.1-0.2	2299
0.2-0.3	4018
0.3-0.4	1858
0.4-0.5	550
0.5-0.6	214
0.6-0.7	33
0.7-0.8	1
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
0.7553	Intermediate Similarity	NPD46	Approved
0.7553	Intermediate Similarity	NPD6698	Approved
0.7292	Intermediate Similarity	NPD7983	Approved
0.7212	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7838	Discovery
0.7021	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6686	Approved
0.6733	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD6371	Approved
0.6667	Remote Similarity	NPD3197	Phase 1
0.6628	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD4250	Approved
0.6531	Remote Similarity	NPD4251	Approved
0.65	Remote Similarity	NPD5785	Approved
0.6486	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD5362	Discontinued
0.6458	Remote Similarity	NPD7154	Phase 3
0.6429	Remote Similarity	NPD6053	Discontinued
0.6429	Remote Similarity	NPD4249	Approved
0.6381	Remote Similarity	NPD7638	Approved
0.6381	Remote Similarity	NPD4225	Approved
0.6373	Remote Similarity	NPD5778	Approved
0.6373	Remote Similarity	NPD5779	Approved
0.6354	Remote Similarity	NPD6435	Approved
0.6354	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD7839	Suspended
0.6344	Remote Similarity	NPD4756	Discovery
0.6333	Remote Similarity	NPD7507	Approved
0.6327	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD5363	Approved
0.6321	Remote Similarity	NPD7640	Approved
0.6321	Remote Similarity	NPD7639	Approved
0.6289	Remote Similarity	NPD6110	Phase 1
0.6271	Remote Similarity	NPD8513	Phase 3
0.6271	Remote Similarity	NPD8517	Approved
0.6271	Remote Similarity	NPD8515	Approved
0.6271	Remote Similarity	NPD8516	Approved
0.6263	Remote Similarity	NPD5786	Approved
0.6262	Remote Similarity	NPD5344	Discontinued
0.6238	Remote Similarity	NPD1695	Approved
0.6179	Remote Similarity	NPD7319	Approved
0.6167	Remote Similarity	NPD7830	Approved
0.6167	Remote Similarity	NPD7829	Approved
0.6161	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD5368	Approved
0.6146	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD8039	Approved
0.6118	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD4790	Discontinued
0.6061	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.602	Remote Similarity	NPD4270	Approved
0.602	Remote Similarity	NPD5209	Approved
0.602	Remote Similarity	NPD4269	Approved
0.6016	Remote Similarity	NPD8074	Phase 3
0.6	Remote Similarity	NPD1694	Approved
0.5979	Remote Similarity	NPD4252	Approved
0.5976	Remote Similarity	NPD3195	Phase 2
0.5976	Remote Similarity	NPD3730	Approved
0.5976	Remote Similarity	NPD4266	Approved
0.5976	Remote Similarity	NPD3196	Approved
0.5976	Remote Similarity	NPD3728	Approved
0.5976	Remote Similarity	NPD3194	Approved
0.5969	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.596	Remote Similarity	NPD5331	Approved
0.596	Remote Similarity	NPD5332	Approved
0.5955	Remote Similarity	NPD7331	Phase 2
0.5948	Remote Similarity	NPD4632	Approved
0.5938	Remote Similarity	NPD4268	Approved
0.5938	Remote Similarity	NPD4271	Approved
0.5932	Remote Similarity	NPD7115	Discovery
0.5922	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD6101	Approved
0.5918	Remote Similarity	NPD5369	Approved
0.5902	Remote Similarity	NPD7642	Approved
0.5887	Remote Similarity	NPD7078	Approved
0.5882	Remote Similarity	NPD6109	Phase 1
0.5882	Remote Similarity	NPD7641	Discontinued
0.5872	Remote Similarity	NPD6648	Approved
0.5868	Remote Similarity	NPD8444	Approved
0.5862	Remote Similarity	NPD8297	Approved
0.5854	Remote Similarity	NPD7492	Approved
0.5854	Remote Similarity	NPD3172	Approved
0.5849	Remote Similarity	NPD5282	Discontinued
0.5841	Remote Similarity	NPD6412	Phase 2
0.584	Remote Similarity	NPD7736	Approved
0.5826	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD4820	Approved
0.5816	Remote Similarity	NPD4822	Approved
0.5816	Remote Similarity	NPD4821	Approved
0.5816	Remote Similarity	NPD4819	Approved
0.581	Remote Similarity	NPD6411	Approved
0.5806	Remote Similarity	NPD6616	Approved
0.5802	Remote Similarity	NPD6927	Phase 3
0.5795	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD8377	Approved
0.5785	Remote Similarity	NPD8294	Approved
0.5785	Remote Similarity	NPD6319	Approved
0.5785	Remote Similarity	NPD6054	Approved
0.5784	Remote Similarity	NPD6422	Discontinued
0.5778	Remote Similarity	NPD3704	Approved
0.5766	Remote Similarity	NPD7632	Discontinued
0.576	Remote Similarity	NPD8293	Discontinued
0.575	Remote Similarity	NPD7327	Approved
0.575	Remote Similarity	NPD7328	Approved
0.5738	Remote Similarity	NPD8380	Approved
0.5738	Remote Similarity	NPD8379	Approved
0.5738	Remote Similarity	NPD8033	Approved
0.5738	Remote Similarity	NPD8335	Approved
0.5738	Remote Similarity	NPD8296	Approved
0.5738	Remote Similarity	NPD8378	Approved
0.5703	Remote Similarity	NPD7260	Phase 2
0.5702	Remote Similarity	NPD7516	Approved
0.5701	Remote Similarity	NPD7748	Approved
0.5691	Remote Similarity	NPD6370	Approved
0.568	Remote Similarity	NPD8451	Approved
0.5667	Remote Similarity	NPD6009	Approved
0.566	Remote Similarity	NPD7637	Suspended
0.5659	Remote Similarity	NPD6845	Suspended
0.5656	Remote Similarity	NPD6059	Approved
0.5652	Remote Similarity	NPD7320	Approved
0.5652	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD6899	Approved
0.5652	Remote Similarity	NPD6881	Approved
0.5645	Remote Similarity	NPD8328	Phase 3
0.5645	Remote Similarity	NPD7604	Phase 2
0.5641	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD2204	Approved
0.5641	Remote Similarity	NPD8130	Phase 1
0.5635	Remote Similarity	NPD8448	Approved
0.5619	Remote Similarity	NPD5370	Suspended
0.5614	Remote Similarity	NPD5739	Approved
0.5614	Remote Similarity	NPD6402	Approved
0.5614	Remote Similarity	NPD6008	Approved
0.5614	Remote Similarity	NPD7128	Approved
0.5614	Remote Similarity	NPD6675	Approved
0.561	Remote Similarity	NPD8267	Approved
0.561	Remote Similarity	NPD5983	Phase 2
0.561	Remote Similarity	NPD8269	Approved
0.561	Remote Similarity	NPD29	Approved
0.561	Remote Similarity	NPD28	Approved
0.561	Remote Similarity	NPD8266	Approved
0.561	Remote Similarity	NPD6015	Approved
0.561	Remote Similarity	NPD8268	Approved
0.561	Remote Similarity	NPD6016	Approved
0.5604	Remote Similarity	NPD6108	Clinical (unspecified phase)

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