NPASS Compound

Structure

NPC469757 OpenBabel07101719142D 41 46 0 0 1 0 0 0 0 0999 V2000 5.9332 1.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1447 -2.3622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6952 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6952 0.9787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0489 -0.9787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 1.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8476 -0.4894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4736 -0.1869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7069 -3.0038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 -1.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8476 1.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2008 -3.4932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0856 0.9787 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7761 -2.7013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6952 0.9787 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4736 -1.7705 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6952 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8476 -0.4894 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6952 -1.9574 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7069 -3.9825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0856 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2380 -0.4894 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3904 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3904 0.9787 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.9574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5428 -1.4681 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.9787 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5428 -0.4894 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6952 -2.9362 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4987 -4.5578 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9332 -0.4894 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2380 -1.4681 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5428 -0.4894 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 -2.4468 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8476 -2.4468 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9574 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1447 0.4047 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7761 -4.2850 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2380 1.4681 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5428 1.4681 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 26 1 0 0 0 0 3 7 1 0 0 0 0 3 15 1 0 0 0 0 4 6 1 0 0 0 0 4 17 1 0 0 0 0 5 8 1 0 0 0 0 5 16 1 0 0 0 0 6 27 1 0 0 0 0 7 28 1 0 0 0 0 8 29 1 0 0 0 0 9 14 2 0 0 0 0 9 20 1 0 0 0 0 10 18 1 0 0 0 0 10 19 1 0 0 0 0 11 15 1 0 0 0 0 11 27 1 0 0 0 0 12 14 1 0 0 0 0 12 39 1 0 0 0 0 13 1 1 6 0 0 0 13 21 1 0 0 0 0 13 40 1 0 0 0 0 14 16 1 0 0 0 0 15 41 1 1 0 0 0 16 26 1 1 0 0 0 17 18 1 0 0 0 0 17 29 1 6 0 0 0 18 28 1 1 0 0 0 19 26 1 1 0 0 0 19 30 1 0 0 0 0 20 31 2 0 0 0 0 20 39 1 0 0 0 0 21 22 1 0 0 0 0 21 32 1 6 0 0 0 22 23 1 0 0 0 0 22 33 1 1 0 0 0 23 24 1 0 0 0 0 23 34 1 1 0 0 0 24 40 1 0 0 0 0 24 41 1 1 0 0 0 25 35 2 0 0 0 0 25 36 1 0 0 0 0 26 29 1 1 0 0 0 27 28 1 1 0 0 0 27 37 1 0 0 0 0 28 25 1 1 0 0 0 29 38 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	582.27
Volume:	556.375
LogP:	0.59
LogD:	-0.05
LogS:	-2.935
# Rotatable Bonds:	4
TPSA:	210.51
# H-Bond Aceptor:	12
# H-Bond Donor:	8
# Rings:	6
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.229
Synthetic Accessibility Score:	5.65
Fsp3:	0.828
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:	-6.654
MDCK Permeability:	5.942284406046383e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.911
20% Bioavailability (F20%):	0.984
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.161
Plasma Protein Binding (PPB):	54.47315979003906%
Volume Distribution (VD):	0.349
Pgp-substrate:	25.06243324279785%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.861
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.075
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.077
CYP3A4-inhibitor:	0.084
CYP3A4-substrate:	0.034

ADMET: Excretion

Clearance (CL):	1.231
Half-life (T1/2):	0.718

ADMET: Toxicity

hERG Blockers:	0.071
Human Hepatotoxicity (H-HT):	0.537
Drug-inuced Liver Injury (DILI):	0.016
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.887
Maximum Recommended Daily Dose:	0.958
Skin Sensitization:	0.102
Carcinogencity:	0.881
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC469757

Natural Product ID:	NPC469757
*Common Name:**	Antiaroside H
IUPAC Name:	(3S,5S,8R,9S,10S,12R,13S,14S,17R)-5,12,14-trihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2S,3R,4R,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carboxylic acid
Synonyms:	Antiaroside H
Standard InCHIKey:	PQWNIWYZNGKIOH-RTUNVJFFSA-N
Standard InCHI:	InChI=1S/C29H42O12/c1-13-21(32)22(33)23(34)24(40-13)41-15-3-7-28(25(35)36)18-10-19(30)26(2)16(14-9-20(31)39-12-14)5-8-29(26,38)17(18)4-6-27(28,37)11-15/h9,13,15-19,21-24,30,32-34,37-38H,3-8,10-12H2,1-2H3,(H,35,36)/t13-,15+,16-,17-,18+,19-,21+,22-,23-,24-,26+,27+,28-,29+/m1/s1
SMILES:	O=C1OCC(=C1)[C@H]1CC[C@]2([C@]1(C)[C@H](O)C[C@H]1[C@H]2CC[C@]2([C@@]1(CC[C@@H](C2)O[C@H]1O[C@H](C)[C@@H]([C@H]([C@H]1O)O)O)C(=O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1169853
PubChem CID:	49799053
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001555] Cardenolides and derivatives [CHEMONTID:0001559] Cardenolide glycosides and derivatives

*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
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20553004]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	latex	Xishuangbanna Tropical Botanical Garden, Chinese Academy of Sciences, Yunnan Province, China	2011-Mar	PMID[24033101]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	trunk bark	Yunnan, China	n.a.	PMID[24582402]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8369	Antiaris toxicaria	Species	Moraceae	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
ED50	10
Others	6

Activity Type	# Activity
Cell Line	7
NON-MOLECULAR	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	1.3	ug ml-1	PMID[547878]
NPT308	Cell Line	CAKI-1	Homo sapiens	ED50	=	1.5	ug ml-1	PMID[547878]
NPT309	Cell Line	1A9	Homo sapiens	ED50	=	1.4	ug ml-1	PMID[547878]
NPT306	Cell Line	PC-3	Homo sapiens	ED50	=	1.8	ug ml-1	PMID[547878]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	3.1	ug ml-1	PMID[547878]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	0.76	ug ml-1	PMID[547878]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	5.9	ug ml-1	PMID[547878]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	7.5	uM	PMID[547877]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	8.33	uM	PMID[547877]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	144.0	%	PMID[547877]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	260.0	%	PMID[547877]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Ratio	=	7.5	n.a.	PMID[547877]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Ratio	=	9.7	n.a.	PMID[547877]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	2.5	ug ml-1	PMID[547878]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	7.3	ug ml-1	PMID[547878]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	7.1	ug ml-1	PMID[547878]

☑ 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 NPC469757 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	287
0.1-0.2	1648
0.2-0.3	4731
0.3-0.4	7891
0.4-0.5	11540
0.5-0.6	7510
0.6-0.7	5291
0.7-0.8	2964
0.8-0.85	565
0.85-0.9	140
0.9-0.95	97
0.95-1	33

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471357
1.0	High Similarity	NPC146456
1.0	High Similarity	NPC117702
0.9831	High Similarity	NPC471359
0.9831	High Similarity	NPC219085
0.9831	High Similarity	NPC469751
0.9831	High Similarity	NPC471358
0.9831	High Similarity	NPC284406
0.9831	High Similarity	NPC17896
0.9831	High Similarity	NPC197707
0.9831	High Similarity	NPC70542
0.9831	High Similarity	NPC471352
0.9831	High Similarity	NPC9499
0.9831	High Similarity	NPC469753
0.9831	High Similarity	NPC86159
0.9831	High Similarity	NPC10823
0.9831	High Similarity	NPC469752
0.9831	High Similarity	NPC180079
0.9831	High Similarity	NPC6108
0.9831	High Similarity	NPC89514
0.9831	High Similarity	NPC251866
0.9831	High Similarity	NPC471361
0.9831	High Similarity	NPC469755
0.9831	High Similarity	NPC471360
0.9831	High Similarity	NPC469754
0.9741	High Similarity	NPC27363
0.9661	High Similarity	NPC471356
0.9661	High Similarity	NPC179412
0.9587	High Similarity	NPC32793
0.9587	High Similarity	NPC247190
0.9587	High Similarity	NPC469749
0.9587	High Similarity	NPC116075
0.9587	High Similarity	NPC146857
0.958	High Similarity	NPC311534
0.9576	High Similarity	NPC469750
0.9576	High Similarity	NPC250556
0.9508	High Similarity	NPC329636
0.9496	High Similarity	NPC329784
0.9496	High Similarity	NPC240070
0.9431	High Similarity	NPC194716
0.9355	High Similarity	NPC329675
0.9355	High Similarity	NPC59288
0.9344	High Similarity	NPC93416
0.9339	High Similarity	NPC125077
0.9339	High Similarity	NPC276838
0.9339	High Similarity	NPC188234
0.9339	High Similarity	NPC232785
0.9339	High Similarity	NPC140092
0.9339	High Similarity	NPC329986
0.9262	High Similarity	NPC159338
0.9262	High Similarity	NPC253456
0.9262	High Similarity	NPC16569
0.9224	High Similarity	NPC196429
0.9224	High Similarity	NPC244402
0.9224	High Similarity	NPC27507
0.9224	High Similarity	NPC99728
0.9224	High Similarity	NPC50305
0.9224	High Similarity	NPC34390
0.9224	High Similarity	NPC84987
0.9224	High Similarity	NPC471351
0.9224	High Similarity	NPC471353
0.9224	High Similarity	NPC158344
0.9224	High Similarity	NPC77319
0.9224	High Similarity	NPC309034
0.9224	High Similarity	NPC474418
0.9224	High Similarity	NPC157376
0.9224	High Similarity	NPC142066
0.9224	High Similarity	NPC471354
0.9224	High Similarity	NPC471355
0.9224	High Similarity	NPC473852
0.9224	High Similarity	NPC87250
0.9224	High Similarity	NPC243196
0.9187	High Similarity	NPC42670
0.9187	High Similarity	NPC19124
0.918	High Similarity	NPC91
0.9153	High Similarity	NPC470312
0.9145	High Similarity	NPC83287
0.9138	High Similarity	NPC310341
0.9138	High Similarity	NPC199428
0.9138	High Similarity	NPC193382
0.9138	High Similarity	NPC99620
0.9138	High Similarity	NPC5311
0.9113	High Similarity	NPC225385
0.9113	High Similarity	NPC476221
0.9113	High Similarity	NPC104585
0.9113	High Similarity	NPC477709
0.9113	High Similarity	NPC298783
0.9113	High Similarity	NPC157817
0.9113	High Similarity	NPC88668
0.9106	High Similarity	NPC173347
0.906	High Similarity	NPC93883
0.906	High Similarity	NPC152615
0.9052	High Similarity	NPC471633
0.9052	High Similarity	NPC69576
0.9052	High Similarity	NPC31354
0.9052	High Similarity	NPC84949
0.9048	High Similarity	NPC62172
0.9048	High Similarity	NPC289700
0.8992	High Similarity	NPC474466
0.8992	High Similarity	NPC475556
0.8992	High Similarity	NPC475629
0.8992	High Similarity	NPC475136
0.8968	High Similarity	NPC171619
0.896	High Similarity	NPC142756
0.8917	High Similarity	NPC314535
0.8917	High Similarity	NPC173555
0.8908	High Similarity	NPC470897
0.8908	High Similarity	NPC44899
0.8908	High Similarity	NPC292467
0.8908	High Similarity	NPC29639
0.8908	High Similarity	NPC304260
0.8908	High Similarity	NPC55532
0.8908	High Similarity	NPC329905
0.8908	High Similarity	NPC30483
0.8908	High Similarity	NPC236973
0.8908	High Similarity	NPC469756
0.8908	High Similarity	NPC32177
0.8908	High Similarity	NPC5883
0.8906	High Similarity	NPC75616
0.8898	High Similarity	NPC474483
0.8898	High Similarity	NPC203862
0.8898	High Similarity	NPC290693
0.8871	High Similarity	NPC231529
0.8843	High Similarity	NPC264336
0.8833	High Similarity	NPC72260
0.8833	High Similarity	NPC281840
0.8833	High Similarity	NPC472004
0.8814	High Similarity	NPC469794
0.8814	High Similarity	NPC72772
0.878	High Similarity	NPC47113
0.878	High Similarity	NPC174367
0.877	High Similarity	NPC117445
0.877	High Similarity	NPC208193
0.877	High Similarity	NPC308262
0.876	High Similarity	NPC475590
0.876	High Similarity	NPC475419
0.876	High Similarity	NPC474908
0.876	High Similarity	NPC40749
0.876	High Similarity	NPC120390
0.876	High Similarity	NPC231518
0.876	High Similarity	NPC475219
0.873	High Similarity	NPC471855
0.8729	High Similarity	NPC477580
0.871	High Similarity	NPC287423
0.871	High Similarity	NPC298841
0.871	High Similarity	NPC42399
0.8699	High Similarity	NPC318135
0.8689	High Similarity	NPC474423
0.8689	High Similarity	NPC193893
0.8689	High Similarity	NPC28532
0.8689	High Similarity	NPC115349
0.8689	High Similarity	NPC74259
0.8678	High Similarity	NPC476127
0.8678	High Similarity	NPC476150
0.8667	High Similarity	NPC239293
0.8667	High Similarity	NPC218093
0.8655	High Similarity	NPC471816
0.8655	High Similarity	NPC106228
0.8655	High Similarity	NPC138372
0.8644	High Similarity	NPC102619
0.864	High Similarity	NPC473620
0.864	High Similarity	NPC245094
0.8621	High Similarity	NPC475030
0.8621	High Similarity	NPC476759
0.8618	High Similarity	NPC41129
0.8595	High Similarity	NPC81222
0.8595	High Similarity	NPC19028
0.8595	High Similarity	NPC477071
0.8595	High Similarity	NPC291820
0.8595	High Similarity	NPC9674
0.8583	High Similarity	NPC155529
0.8571	High Similarity	NPC178289
0.8571	High Similarity	NPC471407
0.8571	High Similarity	NPC476966
0.8571	High Similarity	NPC472274
0.8547	High Similarity	NPC476766
0.8537	High Similarity	NPC269642
0.8525	High Similarity	NPC107607
0.85	High Similarity	NPC196931
0.8492	Intermediate Similarity	NPC114306
0.8492	Intermediate Similarity	NPC477490
0.8487	Intermediate Similarity	NPC260665
0.8475	Intermediate Similarity	NPC272242
0.8475	Intermediate Similarity	NPC471251
0.8473	Intermediate Similarity	NPC79250
0.8473	Intermediate Similarity	NPC290746
0.8468	Intermediate Similarity	NPC473979
0.8468	Intermediate Similarity	NPC472768
0.8462	Intermediate Similarity	NPC471250
0.8455	Intermediate Similarity	NPC476204
0.8455	Intermediate Similarity	NPC202051
0.8455	Intermediate Similarity	NPC170084
0.845	Intermediate Similarity	NPC248703
0.845	Intermediate Similarity	NPC471234
0.8443	Intermediate Similarity	NPC319570
0.8443	Intermediate Similarity	NPC268326
0.8443	Intermediate Similarity	NPC153085
0.8438	Intermediate Similarity	NPC231240
0.8438	Intermediate Similarity	NPC472769
0.8425	Intermediate Similarity	NPC472770

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 NPC469757 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	243
0.1-0.2	1831
0.2-0.3	3907
0.3-0.4	2022
0.4-0.5	599
0.5-0.6	299
0.6-0.7	169
0.7-0.8	63
0.8-0.85	4
0.85-0.9	8
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9831	High Similarity	NPD7319	Approved
0.9576	High Similarity	NPD7507	Approved
0.9145	High Similarity	NPD7327	Approved
0.9145	High Similarity	NPD7328	Approved
0.9068	High Similarity	NPD7516	Approved
0.8917	High Similarity	NPD8380	Approved
0.8917	High Similarity	NPD8379	Approved
0.8917	High Similarity	NPD8335	Approved
0.8917	High Similarity	NPD8378	Approved
0.8917	High Similarity	NPD8296	Approved
0.8833	High Similarity	NPD8377	Approved
0.8833	High Similarity	NPD8294	Approved
0.876	High Similarity	NPD8033	Approved
0.8492	Intermediate Similarity	NPD7736	Approved
0.8376	Intermediate Similarity	NPD6686	Approved
0.8268	Intermediate Similarity	NPD8293	Discontinued
0.824	Intermediate Similarity	NPD6370	Approved
0.8182	Intermediate Similarity	NPD8133	Approved
0.816	Intermediate Similarity	NPD7503	Approved
0.8136	Intermediate Similarity	NPD6412	Phase 2
0.811	Intermediate Similarity	NPD7492	Approved
0.808	Intermediate Similarity	NPD6059	Approved
0.808	Intermediate Similarity	NPD6054	Approved
0.8047	Intermediate Similarity	NPD6616	Approved
0.8031	Intermediate Similarity	NPD8328	Phase 3
0.7984	Intermediate Similarity	NPD7078	Approved
0.7937	Intermediate Similarity	NPD6319	Approved
0.7874	Intermediate Similarity	NPD6016	Approved
0.7874	Intermediate Similarity	NPD6015	Approved
0.7845	Intermediate Similarity	NPD7638	Approved
0.7812	Intermediate Similarity	NPD5988	Approved
0.7805	Intermediate Similarity	NPD6882	Approved
0.7778	Intermediate Similarity	NPD7639	Approved
0.7778	Intermediate Similarity	NPD7640	Approved
0.7698	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD7115	Discovery
0.7698	Intermediate Similarity	NPD6009	Approved
0.7661	Intermediate Similarity	NPD8297	Approved
0.7623	Intermediate Similarity	NPD7320	Approved
0.7603	Intermediate Similarity	NPD6675	Approved
0.7603	Intermediate Similarity	NPD6402	Approved
0.7603	Intermediate Similarity	NPD7128	Approved
0.7603	Intermediate Similarity	NPD5739	Approved
0.76	Intermediate Similarity	NPD4632	Approved
0.7597	Intermediate Similarity	NPD8516	Approved
0.7597	Intermediate Similarity	NPD8515	Approved
0.7597	Intermediate Similarity	NPD8513	Phase 3
0.7597	Intermediate Similarity	NPD8517	Approved
0.7561	Intermediate Similarity	NPD6372	Approved
0.7561	Intermediate Similarity	NPD6373	Approved
0.7561	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD6033	Approved
0.748	Intermediate Similarity	NPD6899	Approved
0.748	Intermediate Similarity	NPD6881	Approved
0.748	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD6649	Approved
0.744	Intermediate Similarity	NPD6650	Approved
0.7419	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD5701	Approved
0.7398	Intermediate Similarity	NPD5697	Approved
0.7381	Intermediate Similarity	NPD6053	Discontinued
0.7377	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD7290	Approved
0.736	Intermediate Similarity	NPD4634	Approved
0.736	Intermediate Similarity	NPD6883	Approved
0.736	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD7102	Approved
0.7317	Intermediate Similarity	NPD6008	Approved
0.7302	Intermediate Similarity	NPD6869	Approved
0.7302	Intermediate Similarity	NPD6847	Approved
0.7302	Intermediate Similarity	NPD8130	Phase 1
0.7302	Intermediate Similarity	NPD6617	Approved
0.728	Intermediate Similarity	NPD6014	Approved
0.728	Intermediate Similarity	NPD6013	Approved
0.728	Intermediate Similarity	NPD6012	Approved
0.7241	Intermediate Similarity	NPD7625	Phase 1
0.7218	Intermediate Similarity	NPD6067	Discontinued
0.7218	Intermediate Similarity	NPD7604	Phase 2
0.7213	Intermediate Similarity	NPD7632	Discontinued
0.72	Intermediate Similarity	NPD6011	Approved
0.7197	Intermediate Similarity	NPD5983	Phase 2
0.7167	Intermediate Similarity	NPD4755	Approved
0.7165	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD6336	Discontinued
0.7107	Intermediate Similarity	NPD4225	Approved
0.7073	Intermediate Similarity	NPD5211	Phase 2
0.7049	Intermediate Similarity	NPD5286	Approved
0.7049	Intermediate Similarity	NPD4700	Approved
0.7049	Intermediate Similarity	NPD4696	Approved
0.7049	Intermediate Similarity	NPD5285	Approved
0.7025	Intermediate Similarity	NPD6083	Phase 2
0.7025	Intermediate Similarity	NPD6084	Phase 2
0.6984	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.696	Remote Similarity	NPD5141	Approved
0.6957	Remote Similarity	NPD7799	Discontinued
0.6953	Remote Similarity	NPD6371	Approved
0.6947	Remote Similarity	NPD6274	Approved
0.694	Remote Similarity	NPD6921	Approved
0.6935	Remote Similarity	NPD5226	Approved
0.6935	Remote Similarity	NPD4633	Approved
0.6935	Remote Similarity	NPD5224	Approved
0.6935	Remote Similarity	NPD5225	Approved
0.6934	Remote Similarity	NPD8074	Phase 3
0.6917	Remote Similarity	NPD7100	Approved
0.6917	Remote Similarity	NPD7101	Approved
0.6905	Remote Similarity	NPD4767	Approved
0.6905	Remote Similarity	NPD4768	Approved
0.688	Remote Similarity	NPD5174	Approved
0.688	Remote Similarity	NPD5175	Approved
0.6864	Remote Similarity	NPD5328	Approved
0.6855	Remote Similarity	NPD5223	Approved
0.6842	Remote Similarity	NPD6335	Approved
0.6833	Remote Similarity	NPD4202	Approved
0.6815	Remote Similarity	NPD6909	Approved
0.6815	Remote Similarity	NPD6908	Approved
0.6807	Remote Similarity	NPD46	Approved
0.6807	Remote Similarity	NPD6698	Approved
0.6797	Remote Similarity	NPD4730	Approved
0.6797	Remote Similarity	NPD4729	Approved
0.6786	Remote Similarity	NPD5956	Approved
0.678	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD7748	Approved
0.6769	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD6317	Approved
0.675	Remote Similarity	NPD8035	Phase 2
0.675	Remote Similarity	NPD8034	Phase 2
0.675	Remote Similarity	NPD6079	Approved
0.675	Remote Similarity	NPD7515	Phase 2
0.6748	Remote Similarity	NPD7902	Approved
0.6746	Remote Similarity	NPD4754	Approved
0.6721	Remote Similarity	NPD5695	Phase 3
0.6721	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD6314	Approved
0.6716	Remote Similarity	NPD6313	Approved
0.6694	Remote Similarity	NPD8171	Discontinued
0.6694	Remote Similarity	NPD5696	Approved
0.6694	Remote Similarity	NPD6399	Phase 3
0.6692	Remote Similarity	NPD5251	Approved
0.6692	Remote Similarity	NPD5248	Approved
0.6692	Remote Similarity	NPD5249	Phase 3
0.6692	Remote Similarity	NPD5247	Approved
0.6692	Remote Similarity	NPD5250	Approved
0.6691	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.669	Remote Similarity	NPD8338	Approved
0.6667	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5128	Approved
0.6643	Remote Similarity	NPD8336	Approved
0.6643	Remote Similarity	NPD8337	Approved
0.6639	Remote Similarity	NPD6903	Approved
0.6612	Remote Similarity	NPD7637	Suspended
0.6612	Remote Similarity	NPD5693	Phase 1
0.661	Remote Similarity	NPD7334	Approved
0.661	Remote Similarity	NPD5330	Approved
0.661	Remote Similarity	NPD7146	Approved
0.661	Remote Similarity	NPD6409	Approved
0.661	Remote Similarity	NPD6684	Approved
0.661	Remote Similarity	NPD7521	Approved
0.6587	Remote Similarity	NPD5344	Discontinued
0.6583	Remote Similarity	NPD4753	Phase 2
0.6575	Remote Similarity	NPD6333	Approved
0.6575	Remote Similarity	NPD6334	Approved
0.6532	Remote Similarity	NPD5222	Approved
0.6532	Remote Similarity	NPD5221	Approved
0.6532	Remote Similarity	NPD4697	Phase 3
0.6532	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD5217	Approved
0.6515	Remote Similarity	NPD5215	Approved
0.6515	Remote Similarity	NPD5216	Approved
0.6504	Remote Similarity	NPD7900	Approved
0.6504	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD7260	Phase 2
0.648	Remote Similarity	NPD5173	Approved
0.6475	Remote Similarity	NPD7830	Approved
0.6475	Remote Similarity	NPD6411	Approved
0.6475	Remote Similarity	NPD7829	Approved
0.6475	Remote Similarity	NPD7983	Approved
0.6471	Remote Similarity	NPD3618	Phase 1
0.6446	Remote Similarity	NPD6673	Approved
0.6446	Remote Similarity	NPD6080	Approved
0.6446	Remote Similarity	NPD6051	Approved
0.6446	Remote Similarity	NPD6904	Approved
0.6444	Remote Similarity	NPD6868	Approved
0.6441	Remote Similarity	NPD3666	Approved
0.6441	Remote Similarity	NPD3133	Approved
0.6441	Remote Similarity	NPD3665	Phase 1
0.6439	Remote Similarity	NPD5169	Approved
0.6439	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD5135	Approved
0.6429	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD5778	Approved
0.6423	Remote Similarity	NPD5779	Approved
0.6417	Remote Similarity	NPD3573	Approved
0.641	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD5785	Approved
0.6391	Remote Similarity	NPD5127	Approved
0.6383	Remote Similarity	NPD8451	Approved
0.6379	Remote Similarity	NPD7525	Registered
0.6371	Remote Similarity	NPD6001	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