NPASS Compound

Structure

NPC472845 OpenBabel07101718332D 48 55 0 0 1 0 0 0 0 0999 V2000 6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6759 4.2239 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 0.3506 4.6778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1596 4.0900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6019 -0.8226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5629 4.2710 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2929 0.1285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9328 -1.5657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0551 3.0955 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 5.1962 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 -0.6674 3.2765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3147 0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9546 -1.3578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1416 2.6887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 1 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 3.4641 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4765 2.6887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8147 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4546 2.8966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1237 2.1535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1674 1.7377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9546 3.7627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0373 2.5602 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 -2.2855 -2.1009 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.1674 1.7377 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.9328 3.5547 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5479 4.6762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9033 2.0602 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 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 36 1 0 0 0 0 2 38 1 0 0 0 0 3 45 1 0 0 0 0 4 5 2 0 0 0 0 4 7 1 0 0 0 0 5 10 1 0 0 0 0 6 8 2 0 0 0 0 6 9 1 0 0 0 0 7 14 2 0 0 0 0 8 15 1 0 0 0 0 9 16 2 0 0 0 0 10 17 2 0 0 0 0 11 19 1 0 0 0 0 11 21 1 0 0 0 0 12 18 1 0 0 0 0 12 46 1 0 0 0 0 13 47 1 0 0 0 0 14 17 1 0 0 0 0 14 22 1 0 0 0 0 15 23 1 0 0 0 0 15 27 2 0 0 0 0 16 27 1 0 0 0 0 16 35 1 0 0 0 0 17 37 1 0 0 0 0 18 19 1 0 0 0 0 18 36 1 1 0 0 0 19 40 1 6 0 0 0 20 13 1 6 0 0 0 20 31 1 0 0 0 0 20 48 1 0 0 0 0 21 46 1 0 0 0 0 21 47 1 1 0 0 0 22 24 2 0 0 0 0 22 26 1 0 0 0 0 23 25 2 0 0 0 0 23 28 1 0 0 0 0 24 25 1 0 0 0 0 24 32 1 0 0 0 0 25 33 1 0 0 0 0 26 28 2 0 0 0 0 26 37 1 0 0 0 0 27 39 1 0 0 0 0 28 39 1 0 0 0 0 29 30 1 0 0 0 0 29 31 1 0 0 0 0 29 41 1 6 0 0 0 30 34 1 0 0 0 0 30 42 1 1 0 0 0 31 45 1 1 0 0 0 32 38 1 0 0 0 0 32 43 2 0 0 0 0 33 38 1 0 0 0 0 33 44 2 0 0 0 0 34 39 1 6 0 0 0 34 48 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	678.21
Volume:	637.477
LogP:	3.151
LogD:	2.823
LogS:	-7.178
# Rotatable Bonds:	6
TPSA:	167.74
# H-Bond Aceptor:	13
# H-Bond Donor:	5
# Rings:	8
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.169
Synthetic Accessibility Score:	5.004
Fsp3:	0.412
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.859
MDCK Permeability:	5.674133717548102e-06
Pgp-inhibitor:	0.118
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.876
20% Bioavailability (F20%):	0.453
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.173
Plasma Protein Binding (PPB):	90.86949920654297%
Volume Distribution (VD):	1.207
Pgp-substrate:	3.450939893722534%

ADMET: Metabolism

CYP1A2-inhibitor:	0.084
CYP1A2-substrate:	0.983
CYP2C19-inhibitor:	0.149
CYP2C19-substrate:	0.738
CYP2C9-inhibitor:	0.466
CYP2C9-substrate:	0.076
CYP2D6-inhibitor:	0.033
CYP2D6-substrate:	0.177
CYP3A4-inhibitor:	0.383
CYP3A4-substrate:	0.876

ADMET: Excretion

Clearance (CL):	4.341
Half-life (T1/2):	0.032

ADMET: Toxicity

hERG Blockers:	0.597
Human Hepatotoxicity (H-HT):	0.778
Drug-inuced Liver Injury (DILI):	0.978
AMES Toxicity:	0.885
Rat Oral Acute Toxicity:	0.104
Maximum Recommended Daily Dose:	0.971
Skin Sensitization:	0.635
Carcinogencity:	0.826
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.91

Download Data

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

Natural Product: NPC472845

Natural Product ID:	NPC472845
*Common Name:**	CGQSZYLXZOKJEJ-VYCQBBBDSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CGQSZYLXZOKJEJ-VYCQBBBDSA-N
Standard InCHI:	InChI=1S/C34H35ClN4O9/c1-36-18-12-46-21(11-19(18)40)47-13-20-31(45-3)29(41)30(42)34(48-20)39-27-15(8-6-9-16(27)35)23-25-24(32(43)38(2)33(25)44)22-14-7-4-5-10-17(14)37-26(22)28(23)39/h4-10,18-21,29-31,34,36-37,40-42H,11-13H2,1-3H3/t18-,19-,20+,21-,29+,30+,31+,34+/m0/s1
SMILES:	CO[C@@H]1[C@@H](CO[C@@H]2OC[C@@H]([C@H](C2)O)NC)O[C@H]([C@@H]([C@H]1O)O)n1c2c(Cl)cccc2c2c1c1[nH]c3c(c1c1c2c(=O)n(c1=O)C)cccc3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3589063
PubChem CID:	128141
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0000210] Carbazoles [CHEMONTID:0001865] Pyrrolocarbazoles [CHEMONTID:0001866] Indolocarbazoles

*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
NPO33195	actinomadura melliaura atcc 39691	Species	Thermomonosporaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26091285]

☑ 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
MIC	4
Others	3

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	2
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	76.4	nM	PMID[547729]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	106.2	nM	PMID[547729]
NPT81	Cell Line	A549	Homo sapiens	Activity	=	10.5	%	PMID[547729]
NPT306	Cell Line	PC-3	Homo sapiens	Activity	=	27.0	%	PMID[547729]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	56.8	nM	PMID[547729]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	20.8	%	PMID[547729]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	>	60000.0	nM	PMID[547729]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	=	7500.0	nM	PMID[547729]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	60000.0	nM	PMID[547729]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	60000.0	nM	PMID[547729]

☑ 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 NPC472845 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	519
0.1-0.2	2621
0.2-0.3	14202
0.3-0.4	17991
0.4-0.5	4181
0.5-0.6	2577
0.6-0.7	578
0.7-0.8	21
0.8-0.85	1
0.85-0.9	2
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9419	High Similarity	NPC472846
0.9336	High Similarity	NPC472843
0.9252	High Similarity	NPC472842
0.8755	High Similarity	NPC472207
0.8431	Intermediate Similarity	NPC1203
0.8031	Intermediate Similarity	NPC107836
0.748	Intermediate Similarity	NPC472844
0.7237	Intermediate Similarity	NPC56109
0.7237	Intermediate Similarity	NPC191382
0.7189	Intermediate Similarity	NPC45048
0.7154	Intermediate Similarity	NPC174788
0.7153	Intermediate Similarity	NPC279589
0.7121	Intermediate Similarity	NPC313884
0.7121	Intermediate Similarity	NPC98371
0.7043	Intermediate Similarity	NPC155444
0.7007	Intermediate Similarity	NPC476514
0.6992	Remote Similarity	NPC52254
0.6972	Remote Similarity	NPC162860
0.6969	Remote Similarity	NPC478157
0.6953	Remote Similarity	NPC82070
0.695	Remote Similarity	NPC475271
0.6941	Remote Similarity	NPC476114
0.6929	Remote Similarity	NPC31700
0.6905	Remote Similarity	NPC477548
0.6905	Remote Similarity	NPC478158
0.6892	Remote Similarity	NPC54420
0.6887	Remote Similarity	NPC281049
0.688	Remote Similarity	NPC57453
0.6842	Remote Similarity	NPC263937
0.6842	Remote Similarity	NPC94428
0.6824	Remote Similarity	NPC75634
0.678	Remote Similarity	NPC33949
0.6757	Remote Similarity	NPC477714
0.6742	Remote Similarity	NPC476492
0.6742	Remote Similarity	NPC476491
0.6719	Remote Similarity	NPC204303
0.6718	Remote Similarity	NPC477715
0.6704	Remote Similarity	NPC132329
0.6704	Remote Similarity	NPC478029
0.6703	Remote Similarity	NPC476515
0.6691	Remote Similarity	NPC471564
0.6654	Remote Similarity	NPC316411
0.6643	Remote Similarity	NPC473800
0.6642	Remote Similarity	NPC89987
0.6641	Remote Similarity	NPC274842
0.663	Remote Similarity	NPC478028
0.6627	Remote Similarity	NPC477065
0.6619	Remote Similarity	NPC476493
0.6617	Remote Similarity	NPC70155
0.6617	Remote Similarity	NPC323198
0.6617	Remote Similarity	NPC475258
0.6604	Remote Similarity	NPC315062
0.6604	Remote Similarity	NPC267853
0.6602	Remote Similarity	NPC236424
0.6602	Remote Similarity	NPC306644
0.6601	Remote Similarity	NPC9482
0.6601	Remote Similarity	NPC476874
0.6593	Remote Similarity	NPC325976
0.6584	Remote Similarity	NPC470205
0.6582	Remote Similarity	NPC160898
0.658	Remote Similarity	NPC244897
0.6577	Remote Similarity	NPC313640
0.6576	Remote Similarity	NPC107077
0.6576	Remote Similarity	NPC223791
0.6573	Remote Similarity	NPC478009
0.6573	Remote Similarity	NPC478010
0.6564	Remote Similarity	NPC244856
0.6562	Remote Similarity	NPC474905
0.6553	Remote Similarity	NPC471506
0.6543	Remote Similarity	NPC475969
0.6543	Remote Similarity	NPC475859
0.6538	Remote Similarity	NPC54744
0.6535	Remote Similarity	NPC193761
0.6535	Remote Similarity	NPC155143
0.6527	Remote Similarity	NPC249428
0.6527	Remote Similarity	NPC312645
0.6523	Remote Similarity	NPC14812
0.6517	Remote Similarity	NPC909
0.6517	Remote Similarity	NPC475338
0.651	Remote Similarity	NPC476115
0.6506	Remote Similarity	NPC477175
0.6506	Remote Similarity	NPC470730
0.6504	Remote Similarity	NPC64216
0.6502	Remote Similarity	NPC478006
0.6496	Remote Similarity	NPC475506
0.6493	Remote Similarity	NPC192712
0.6486	Remote Similarity	NPC475422
0.6477	Remote Similarity	NPC314882
0.6473	Remote Similarity	NPC87755
0.6464	Remote Similarity	NPC472285
0.6462	Remote Similarity	NPC320968
0.6458	Remote Similarity	NPC165743
0.6457	Remote Similarity	NPC195461
0.6457	Remote Similarity	NPC79129
0.6457	Remote Similarity	NPC49196
0.6457	Remote Similarity	NPC81654
0.6457	Remote Similarity	NPC249150
0.6457	Remote Similarity	NPC313985
0.6455	Remote Similarity	NPC79107
0.6455	Remote Similarity	NPC472762
0.6455	Remote Similarity	NPC475424
0.6451	Remote Similarity	NPC172355
0.645	Remote Similarity	NPC477979
0.6444	Remote Similarity	NPC326363
0.6443	Remote Similarity	NPC149708
0.6443	Remote Similarity	NPC171317
0.6439	Remote Similarity	NPC473310
0.6434	Remote Similarity	NPC91179
0.6424	Remote Similarity	NPC315467
0.6423	Remote Similarity	NPC234999
0.6421	Remote Similarity	NPC474877
0.6418	Remote Similarity	NPC131273
0.6418	Remote Similarity	NPC473441
0.6417	Remote Similarity	NPC100321
0.6412	Remote Similarity	NPC89508
0.6403	Remote Similarity	NPC116701
0.6386	Remote Similarity	NPC472436
0.6385	Remote Similarity	NPC260909
0.6384	Remote Similarity	NPC470729
0.6384	Remote Similarity	NPC477176
0.6381	Remote Similarity	NPC317701
0.6378	Remote Similarity	NPC473640
0.6378	Remote Similarity	NPC50503
0.6375	Remote Similarity	NPC115282
0.6374	Remote Similarity	NPC475778
0.6374	Remote Similarity	NPC63279
0.6371	Remote Similarity	NPC244741
0.6367	Remote Similarity	NPC474896
0.6364	Remote Similarity	NPC472027
0.636	Remote Similarity	NPC469470
0.636	Remote Similarity	NPC324091
0.636	Remote Similarity	NPC477177
0.636	Remote Similarity	NPC282033
0.636	Remote Similarity	NPC469501
0.6357	Remote Similarity	NPC476818
0.6353	Remote Similarity	NPC293917
0.635	Remote Similarity	NPC297642
0.635	Remote Similarity	NPC234078
0.635	Remote Similarity	NPC221100
0.635	Remote Similarity	NPC472291
0.6344	Remote Similarity	NPC472434
0.6344	Remote Similarity	NPC470901
0.6343	Remote Similarity	NPC31097
0.6341	Remote Similarity	NPC473565
0.634	Remote Similarity	NPC79386
0.6337	Remote Similarity	NPC63031
0.6335	Remote Similarity	NPC472097
0.6332	Remote Similarity	NPC277350
0.6331	Remote Similarity	NPC470843
0.6331	Remote Similarity	NPC94541
0.633	Remote Similarity	NPC272174
0.6324	Remote Similarity	NPC195314
0.6324	Remote Similarity	NPC69843
0.6322	Remote Similarity	NPC469743
0.632	Remote Similarity	NPC175474
0.631	Remote Similarity	NPC314058
0.631	Remote Similarity	NPC316359
0.631	Remote Similarity	NPC315617
0.631	Remote Similarity	NPC316018
0.6305	Remote Similarity	NPC237901
0.6305	Remote Similarity	NPC195788
0.6304	Remote Similarity	NPC104712
0.6302	Remote Similarity	NPC471192
0.6302	Remote Similarity	NPC470731
0.6298	Remote Similarity	NPC126066
0.6293	Remote Similarity	NPC478011
0.6293	Remote Similarity	NPC478012
0.6288	Remote Similarity	NPC229348
0.6284	Remote Similarity	NPC314957
0.6281	Remote Similarity	NPC472435
0.628	Remote Similarity	NPC17059
0.6279	Remote Similarity	NPC476073
0.6276	Remote Similarity	NPC242872
0.6276	Remote Similarity	NPC263117
0.6276	Remote Similarity	NPC125181
0.6275	Remote Similarity	NPC227582
0.6271	Remote Similarity	NPC314176
0.6268	Remote Similarity	NPC153400
0.6265	Remote Similarity	NPC199851
0.6265	Remote Similarity	NPC294909
0.6265	Remote Similarity	NPC254240
0.6265	Remote Similarity	NPC252338
0.6265	Remote Similarity	NPC128265
0.6265	Remote Similarity	NPC312870
0.6263	Remote Similarity	NPC310618
0.626	Remote Similarity	NPC85066
0.626	Remote Similarity	NPC181502
0.6259	Remote Similarity	NPC229893
0.6255	Remote Similarity	NPC323752
0.6255	Remote Similarity	NPC213629
0.6255	Remote Similarity	NPC165599
0.625	Remote Similarity	NPC110602
0.625	Remote Similarity	NPC31385
0.625	Remote Similarity	NPC75726
0.625	Remote Similarity	NPC153980
0.625	Remote Similarity	NPC472110
0.625	Remote Similarity	NPC6865
0.625	Remote Similarity	NPC139291
0.625	Remote Similarity	NPC131887
0.625	Remote Similarity	NPC191489

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 NPC472845 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	242
0.1-0.2	594
0.2-0.3	1202
0.3-0.4	2648
0.4-0.5	2783
0.5-0.6	1472
0.6-0.7	197
0.7-0.8	11
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
0.9256	High Similarity	NPD7772	Phase 3
0.7889	Intermediate Similarity	NPD7181	Phase 3
0.7606	Intermediate Similarity	NPD7921	Approved
0.7444	Intermediate Similarity	NPD6456	Discontinued
0.7326	Intermediate Similarity	NPD7950	Approved
0.7326	Intermediate Similarity	NPD7953	Approved
0.7326	Intermediate Similarity	NPD7951	Approved
0.7326	Intermediate Similarity	NPD7790	Approved
0.7326	Intermediate Similarity	NPD7789	Approved
0.7326	Intermediate Similarity	NPD7791	Approved
0.7326	Intermediate Similarity	NPD7952	Approved
0.7237	Intermediate Similarity	NPD7781	Approved
0.7237	Intermediate Similarity	NPD7780	Approved
0.7198	Intermediate Similarity	NPD6977	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD6978	Phase 2
0.7132	Intermediate Similarity	NPD7731	Approved
0.7132	Intermediate Similarity	NPD7730	Approved
0.7121	Intermediate Similarity	NPD6976	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7688	Phase 1
0.7109	Intermediate Similarity	NPD6995	Phase 1
0.7077	Intermediate Similarity	NPD7824	Approved
0.7054	Intermediate Similarity	NPD7271	Approved
0.7047	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.6938	Remote Similarity	NPD6615	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD7576	Discontinued
0.6899	Remote Similarity	NPD6717	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD7717	Approved
0.6885	Remote Similarity	NPD7716	Approved
0.6863	Remote Similarity	NPD5807	Phase 2
0.686	Remote Similarity	NPD6455	Phase 3
0.6825	Remote Similarity	NPD8322	Phase 2
0.6811	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.677	Remote Similarity	NPD7073	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD7454	Approved
0.6758	Remote Similarity	NPD7455	Approved
0.6746	Remote Similarity	NPD8114	Approved
0.6746	Remote Similarity	NPD8115	Approved
0.6693	Remote Similarity	NPD8093	Discontinued
0.6667	Remote Similarity	NPD7769	Phase 3
0.6655	Remote Similarity	NPD8463	Approved
0.6627	Remote Similarity	NPD7727	Phase 2
0.6604	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD8374	Phase 3
0.6564	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD8329	Phase 3
0.6527	Remote Similarity	NPD7185	Discontinued
0.6527	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6523	Remote Similarity	NPD7001	Phase 3
0.6523	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD3746	Discontinued
0.6509	Remote Similarity	NPD7770	Phase 3
0.6502	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD8317	Phase 2
0.6481	Remote Similarity	NPD8316	Phase 2
0.6471	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD4600	Approved
0.6457	Remote Similarity	NPD8524	Approved
0.6457	Remote Similarity	NPD4601	Approved
0.6455	Remote Similarity	NPD8289	Discontinued
0.6454	Remote Similarity	NPD7944	Discontinued
0.6453	Remote Similarity	NPD8046	Discontinued
0.6446	Remote Similarity	NPD5450	Discontinued
0.6439	Remote Similarity	NPD7878	Phase 2
0.6431	Remote Similarity	NPD7817	Phase 1
0.6426	Remote Similarity	NPD8421	Discontinued
0.6423	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.642	Remote Similarity	NPD5426	Phase 3
0.6412	Remote Similarity	NPD8094	Discontinued
0.6408	Remote Similarity	NPD7776	Approved
0.6407	Remote Similarity	NPD7888	Approved
0.6407	Remote Similarity	NPD7887	Approved
0.6395	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD7957	Phase 1
0.6393	Remote Similarity	NPD7397	Approved
0.6393	Remote Similarity	NPD7398	Approved
0.6385	Remote Similarity	NPD8460	Approved
0.6385	Remote Similarity	NPD8459	Approved
0.638	Remote Similarity	NPD8375	Approved
0.6374	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.637	Remote Similarity	NPD7787	Discontinued
0.636	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD8250	Phase 2
0.6357	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.635	Remote Similarity	NPD7502	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD7767	Approved
0.6346	Remote Similarity	NPD7666	Phase 3
0.6346	Remote Similarity	NPD7665	Phase 2
0.6337	Remote Similarity	NPD8119	Discontinued
0.6336	Remote Similarity	NPD7470	Discontinued
0.6336	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD8371	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6326	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.632	Remote Similarity	NPD1534	Approved
0.6308	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6305	Remote Similarity	NPD8465	Approved
0.6305	Remote Similarity	NPD8467	Approved
0.6305	Remote Similarity	NPD8466	Approved
0.6301	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6291	Remote Similarity	NPD6142	Phase 3
0.6289	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD5001	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD7860	Clinical (unspecified phase)
0.627	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD8364	Approved
0.6267	Remote Similarity	NPD8363	Approved
0.6265	Remote Similarity	NPD4501	Approved
0.6265	Remote Similarity	NPD4500	Approved
0.6264	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD8468	Phase 2
0.626	Remote Similarity	NPD5835	Phase 3
0.626	Remote Similarity	NPD5834	Phase 3
0.625	Remote Similarity	NPD3320	Approved
0.625	Remote Similarity	NPD8429	Approved
0.625	Remote Similarity	NPD7708	Approved
0.625	Remote Similarity	NPD3318	Approved
0.625	Remote Similarity	NPD8427	Approved
0.625	Remote Similarity	NPD3319	Phase 1
0.625	Remote Similarity	NPD8428	Approved
0.6241	Remote Similarity	NPD7218	Clinical (unspecified phase)
0.624	Remote Similarity	NPD5021	Discontinued
0.6238	Remote Similarity	NPD8349	Phase 1
0.623	Remote Similarity	NPD4112	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD6787	Phase 2
0.6225	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6221	Remote Similarity	NPD8425	Approved
0.6221	Remote Similarity	NPD8426	Approved
0.622	Remote Similarity	NPD7803	Approved
0.6215	Remote Similarity	NPD8431	Approved
0.6214	Remote Similarity	NPD6716	Phase 1
0.6211	Remote Similarity	NPD6724	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD6664	Approved
0.6209	Remote Similarity	NPD6986	Phase 1
0.6206	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6206	Remote Similarity	NPD8291	Clinical (unspecified phase)
0.6206	Remote Similarity	NPD5488	Discontinued
0.6203	Remote Similarity	NPD7970	Approved
0.6203	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6202	Remote Similarity	NPD8244	Phase 2
0.6201	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD4602	Approved
0.6194	Remote Similarity	NPD6531	Approved
0.6194	Remote Similarity	NPD6530	Approved
0.6182	Remote Similarity	NPD8238	Clinical (unspecified phase)
0.6178	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6178	Remote Similarity	NPD5017	Discontinued
0.6175	Remote Similarity	NPD5809	Phase 3
0.6169	Remote Similarity	NPD8272	Phase 2
0.6165	Remote Similarity	NPD7557	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD6999	Discontinued
0.6162	Remote Similarity	NPD8102	Discontinued
0.6162	Remote Similarity	NPD8523	Approved
0.6159	Remote Similarity	NPD7956	Approved
0.6159	Remote Similarity	NPD7955	Approved
0.6159	Remote Similarity	NPD4885	Approved
0.6157	Remote Similarity	NPD8325	Phase 3
0.6157	Remote Similarity	NPD8326	Phase 3
0.6157	Remote Similarity	NPD5821	Approved
0.6157	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.6157	Remote Similarity	NPD6710	Phase 3
0.6151	Remote Similarity	NPD7070	Clinical (unspecified phase)
0.614	Remote Similarity	NPD5482	Discontinued
0.6135	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.6128	Remote Similarity	NPD7656	Approved
0.6128	Remote Similarity	NPD8097	Phase 3
0.6128	Remote Similarity	NPD7657	Approved
0.6128	Remote Similarity	NPD8096	Phase 3
0.6122	Remote Similarity	NPD6328	Clinical (unspecified phase)
0.6113	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD6770	Approved
0.6109	Remote Similarity	NPD4848	Phase 1
0.6107	Remote Similarity	NPD6987	Phase 1
0.6107	Remote Similarity	NPD8098	Approved
0.6107	Remote Similarity	NPD5901	Discontinued
0.6105	Remote Similarity	NPD3243	Approved
0.6105	Remote Similarity	NPD2823	Clinical (unspecified phase)
0.61	Remote Similarity	NPD6249	Phase 2
0.61	Remote Similarity	NPD6248	Phase 2
0.6098	Remote Similarity	NPD2443	Approved
0.6098	Remote Similarity	NPD2442	Approved
0.6098	Remote Similarity	NPD2510	Approved
0.6098	Remote Similarity	NPD2509	Approved
0.6097	Remote Similarity	NPD6218	Discontinued
0.6096	Remote Similarity	NPD7564	Discontinued
0.6095	Remote Similarity	NPD7711	Discontinued
0.6094	Remote Similarity	NPD4348	Clinical (unspecified phase)
0.609	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD3280	Approved
0.6089	Remote Similarity	NPD6210	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