NPASS Compound

Structure

CID274507 OpenBabel06191716082D 46 51 0 0 1 0 0 0 0 0999 V2000 1.6987 -3.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.9423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8879 2.8109 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9071 2.8109 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5481 -0.4904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8494 -1.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6987 -0.9808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5481 -2.4519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6987 1.9615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2469 0.4904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3975 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8494 1.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5481 -1.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6987 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8494 0.4904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4937 1.9615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6987 -2.9423 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8494 -2.4519 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.9808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6443 1.4712 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5481 1.4712 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6987 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2469 1.4712 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8494 -1.4712 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.6443 0.4904 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7950 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9456 0.4904 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9456 1.4712 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5481 -0.4904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3975 1.9615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5481 0.4904 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8494 0.4904 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6987 -0.9808 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 -9.3431 1.4712 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4937 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7950 -0.9808 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5481 0.4904 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3975 -0.9808 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8494 2.4519 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8494 2.4519 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7950 1.9615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0962 1.9615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 32 1 0 0 0 0 4 32 1 0 0 0 0 6 34 1 0 0 0 0 7 8 1 0 0 0 0 7 20 2 0 0 0 0 8 23 1 0 0 0 0 9 14 1 0 0 0 0 9 18 1 0 0 0 0 10 13 1 0 0 0 0 10 22 1 0 0 0 0 11 12 1 0 0 0 0 11 24 1 0 0 0 0 12 33 1 0 0 0 0 13 34 1 0 0 0 0 14 35 1 0 0 0 0 15 16 1 0 0 0 0 15 35 1 0 0 0 0 16 36 1 0 0 0 0 17 37 1 0 0 0 0 18 1 1 1 0 0 0 18 19 1 0 0 0 0 19 2 1 6 0 0 0 19 25 1 0 0 0 0 20 25 1 0 0 0 0 20 36 1 0 0 0 0 21 17 1 1 0 0 0 21 26 1 0 0 0 0 21 45 1 0 0 0 0 22 32 1 0 0 0 0 22 33 1 6 0 0 0 23 33 1 6 0 0 0 23 34 1 0 0 0 0 24 32 1 0 0 0 0 24 46 1 6 0 0 0 25 35 1 1 0 0 0 26 27 1 0 0 0 0 26 38 1 6 0 0 0 27 28 1 0 0 0 0 27 39 1 1 0 0 0 28 29 1 0 0 0 0 28 40 1 6 0 0 0 29 45 1 0 0 0 0 29 46 1 1 0 0 0 30 41 2 0 0 0 0 30 42 1 0 0 0 0 31 43 2 0 0 0 0 31 44 1 0 0 0 0 33 5 1 6 0 0 0 34 36 1 1 0 0 0 35 30 1 6 0 0 0 36 31 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	406.31
Volume:	445.175
LogP:	4.936
LogD:	4.083
LogS:	-5.286
# Rotatable Bonds:	6
TPSA:	44.76
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.308
Synthetic Accessibility Score:	4.914
Fsp3:	0.88
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.892
MDCK Permeability:	2.596447848191019e-05
Pgp-inhibitor:	0.968
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.093

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.062
Plasma Protein Binding (PPB):	83.8459243774414%
Volume Distribution (VD):	1.493
Pgp-substrate:	8.550233840942383%

ADMET: Metabolism

CYP1A2-inhibitor:	0.049
CYP1A2-substrate:	0.801
CYP2C19-inhibitor:	0.141
CYP2C19-substrate:	0.954
CYP2C9-inhibitor:	0.18
CYP2C9-substrate:	0.296
CYP2D6-inhibitor:	0.079
CYP2D6-substrate:	0.738
CYP3A4-inhibitor:	0.932
CYP3A4-substrate:	0.621

ADMET: Excretion

Clearance (CL):	6.809
Half-life (T1/2):	0.12

ADMET: Toxicity

hERG Blockers:	0.651
Human Hepatotoxicity (H-HT):	0.409
Drug-inuced Liver Injury (DILI):	0.402
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.079
Maximum Recommended Daily Dose:	0.063
Skin Sensitization:	0.93
Carcinogencity:	0.049
Eye Corrosion:	0.123
Eye Irritation:	0.091
Respiratory Toxicity:	0.866

Download Data

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

Natural Product: NPC274507

Natural Product ID:	NPC274507
*Common Name:**	3-O-Beta-D-Glucopyranosyl Quinovic Acid
IUPAC Name:	(1S,2R,4aS,6aR,6aR,6bR,8aR,10S,12aR,14bS)-1,2,6b,9,9,12a-hexamethyl-10-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a,6a-dicarboxylic acid
Synonyms:
Standard InCHIKey:	AXNXSFBKZQIMPF-ZZZTYRQWSA-N
Standard InCHI:	InChI=1S/C36H56O10/c1-18-9-14-35(30(41)42)15-16-36(31(43)44)20(25(35)19(18)2)7-8-23-33(5)12-11-24(32(3,4)22(33)10-13-34(23,36)6)46-29-28(40)27(39)26(38)21(17-37)45-29/h7,18-19,21-29,37-40H,8-17H2,1-6H3,(H,41,42)(H,43,44)/t18-,19+,21-,22+,23-,24+,25+,26-,27+,28-,29+,33+,34-,35+,36-/m1/s1
SMILES:	OC[C@H]1O[C@@H](O[C@H]2CC[C@]3([C@H](C2(C)C)CC[C@@]2([C@@H]3CC=C3[C@]2(CC[C@@]2([C@H]3[C@@H](C)[C@H](C)CC2)C(=O)O)C(=O)O)C)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL508407
PubChem CID:	14194006
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

*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
NPO26547	Uncaria tomentosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1919590]
NPO25311	Guettarda platypoda	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2553871]
NPO26547	Uncaria tomentosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2553871]
NPO26547	Uncaria tomentosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22560	Strychnos parvifolia	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26547	Uncaria tomentosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22560	Strychnos parvifolia	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26547	Uncaria tomentosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22560	Strychnos parvifolia	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22475.1	Brachylaena discolor var. rotundata	Varieties	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22818	Acritopappus confertus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25311	Guettarda platypoda	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21220	Pulicaria uliginosa	Species	Asteraceae	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

Activity Type	# Activity
Individual Protein	2
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1044	Individual Protein	DNA topoisomerase II alpha	Homo sapiens	IC50	>	250000.0	nM	PMID[523505]
NPT143	Individual Protein	DNA topoisomerase I	Homo sapiens	IC50	>	250000.0	nM	PMID[523505]
NPT2516	Organism	Vesicular stomatitis Indiana virus	Vesicular stomatitis Indiana virus	MIC50	=	51000.0	nM	PMID[523504]
NPT27	Others	Unspecified		TC50	=	150.0	ug ml-1	PMID[523504]

☑ 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 NPC274507 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	261
0.1-0.2	1673
0.2-0.3	4867
0.3-0.4	11140
0.4-0.5	10865
0.5-0.6	6300
0.6-0.7	4278
0.7-0.8	1917
0.8-0.85	751
0.85-0.9	276
0.9-0.95	138
0.95-1	231

Similarity Score	Similarity Level	Natural Product ID
0.9902	High Similarity	NPC235841
0.9902	High Similarity	NPC108748
0.9902	High Similarity	NPC191763
0.9902	High Similarity	NPC473481
0.9902	High Similarity	NPC211798
0.9902	High Similarity	NPC297208
0.9902	High Similarity	NPC30397
0.9901	High Similarity	NPC306746
0.9901	High Similarity	NPC57362
0.9901	High Similarity	NPC167383
0.9901	High Similarity	NPC204407
0.9901	High Similarity	NPC237503
0.9806	High Similarity	NPC116794
0.9806	High Similarity	NPC256798
0.9806	High Similarity	NPC46388
0.9806	High Similarity	NPC128925
0.9806	High Similarity	NPC37739
0.9804	High Similarity	NPC59804
0.9804	High Similarity	NPC279554
0.9804	High Similarity	NPC102914
0.9804	High Similarity	NPC174679
0.9804	High Similarity	NPC476887
0.9804	High Similarity	NPC75747
0.9804	High Similarity	NPC90856
0.9804	High Similarity	NPC270667
0.9804	High Similarity	NPC68419
0.9804	High Similarity	NPC476885
0.9804	High Similarity	NPC199457
0.9804	High Similarity	NPC127056
0.9804	High Similarity	NPC475296
0.9804	High Similarity	NPC108709
0.9804	High Similarity	NPC136877
0.9804	High Similarity	NPC7870
0.9804	High Similarity	NPC476880
0.9804	High Similarity	NPC476882
0.9804	High Similarity	NPC476886
0.9804	High Similarity	NPC474589
0.9804	High Similarity	NPC476881
0.9804	High Similarity	NPC29069
0.9804	High Similarity	NPC56713
0.9804	High Similarity	NPC476883
0.9804	High Similarity	NPC476884
0.9804	High Similarity	NPC110139
0.9804	High Similarity	NPC164194
0.9802	High Similarity	NPC284807
0.9802	High Similarity	NPC177246
0.9802	High Similarity	NPC476123
0.9802	High Similarity	NPC28198
0.9712	High Similarity	NPC204458
0.9712	High Similarity	NPC138334
0.9712	High Similarity	NPC124296
0.9712	High Similarity	NPC271138
0.9712	High Similarity	NPC189884
0.9712	High Similarity	NPC258885
0.9712	High Similarity	NPC47063
0.9712	High Similarity	NPC269315
0.9709	High Similarity	NPC179434
0.9709	High Similarity	NPC164419
0.9709	High Similarity	NPC31839
0.9706	High Similarity	NPC137917
0.9706	High Similarity	NPC127853
0.9703	High Similarity	NPC283849
0.9703	High Similarity	NPC473538
0.9619	High Similarity	NPC475633
0.9615	High Similarity	NPC102439
0.9615	High Similarity	NPC292677
0.9615	High Similarity	NPC80843
0.9615	High Similarity	NPC1046
0.9615	High Similarity	NPC104400
0.9615	High Similarity	NPC139044
0.9615	High Similarity	NPC48249
0.9615	High Similarity	NPC475516
0.9615	High Similarity	NPC10320
0.9615	High Similarity	NPC257468
0.9615	High Similarity	NPC469946
0.9615	High Similarity	NPC471383
0.9615	High Similarity	NPC104071
0.9615	High Similarity	NPC324875
0.9615	High Similarity	NPC109079
0.9615	High Similarity	NPC276093
0.9615	High Similarity	NPC79718
0.9615	High Similarity	NPC139894
0.9615	High Similarity	NPC471967
0.9615	High Similarity	NPC475504
0.9615	High Similarity	NPC473383
0.9615	High Similarity	NPC101744
0.9615	High Similarity	NPC473373
0.9612	High Similarity	NPC242611
0.9612	High Similarity	NPC78046
0.9612	High Similarity	NPC220984
0.9612	High Similarity	NPC269095
0.9608	High Similarity	NPC285576
0.9604	High Similarity	NPC475611
0.9528	High Similarity	NPC58448
0.9528	High Similarity	NPC160415
0.9528	High Similarity	NPC471384
0.9528	High Similarity	NPC161674
0.9524	High Similarity	NPC475208
0.9524	High Similarity	NPC323341
0.9524	High Similarity	NPC150400
0.9524	High Similarity	NPC174720
0.9524	High Similarity	NPC166422
0.9524	High Similarity	NPC309714
0.9524	High Similarity	NPC96641
0.9524	High Similarity	NPC241909
0.9524	High Similarity	NPC295823
0.9524	High Similarity	NPC155410
0.9524	High Similarity	NPC163183
0.9524	High Similarity	NPC219180
0.9524	High Similarity	NPC238935
0.9524	High Similarity	NPC473826
0.9524	High Similarity	NPC73318
0.9524	High Similarity	NPC134835
0.9524	High Similarity	NPC473343
0.9524	High Similarity	NPC46665
0.9524	High Similarity	NPC114304
0.9524	High Similarity	NPC251263
0.9524	High Similarity	NPC475287
0.9524	High Similarity	NPC475467
0.9524	High Similarity	NPC114287
0.9524	High Similarity	NPC151543
0.9524	High Similarity	NPC133818
0.9524	High Similarity	NPC192600
0.9519	High Similarity	NPC190837
0.9439	High Similarity	NPC148417
0.9439	High Similarity	NPC68175
0.9439	High Similarity	NPC110633
0.9439	High Similarity	NPC136768
0.9434	High Similarity	NPC227551
0.9434	High Similarity	NPC119592
0.9434	High Similarity	NPC4328
0.9434	High Similarity	NPC41061
0.9434	High Similarity	NPC309907
0.9434	High Similarity	NPC469782
0.9434	High Similarity	NPC164389
0.9434	High Similarity	NPC43550
0.9434	High Similarity	NPC250247
0.9434	High Similarity	NPC471550
0.9434	High Similarity	NPC67857
0.9434	High Similarity	NPC476068
0.9434	High Similarity	NPC60557
0.9434	High Similarity	NPC76972
0.9434	High Similarity	NPC123199
0.9434	High Similarity	NPC100639
0.9434	High Similarity	NPC79643
0.9434	High Similarity	NPC473714
0.9434	High Similarity	NPC475486
0.9434	High Similarity	NPC54636
0.9434	High Similarity	NPC71065
0.9434	High Similarity	NPC65105
0.9434	High Similarity	NPC475140
0.9434	High Similarity	NPC475160
0.9434	High Similarity	NPC294453
0.9434	High Similarity	NPC236638
0.9434	High Similarity	NPC57484
0.9434	High Similarity	NPC70809
0.9434	High Similarity	NPC204414
0.9434	High Similarity	NPC293330
0.9434	High Similarity	NPC471385
0.9434	High Similarity	NPC261506
0.9434	High Similarity	NPC298034
0.9434	High Similarity	NPC202828
0.9434	High Similarity	NPC161717
0.9434	High Similarity	NPC224381
0.9434	High Similarity	NPC305981
0.9429	High Similarity	NPC161434
0.9429	High Similarity	NPC65590
0.9429	High Similarity	NPC195132
0.9429	High Similarity	NPC125923
0.9429	High Similarity	NPC212968
0.9429	High Similarity	NPC64106
0.9429	High Similarity	NPC100383
0.9352	High Similarity	NPC36831
0.9346	High Similarity	NPC37134
0.9346	High Similarity	NPC476992
0.9346	High Similarity	NPC288205
0.9346	High Similarity	NPC75287
0.9346	High Similarity	NPC305267
0.9346	High Similarity	NPC26626
0.9346	High Similarity	NPC291903
0.9346	High Similarity	NPC51465
0.934	High Similarity	NPC293038
0.934	High Similarity	NPC62696
0.9314	High Similarity	NPC173583
0.9259	High Similarity	NPC185466
0.9259	High Similarity	NPC471547
0.9259	High Similarity	NPC220160
0.9259	High Similarity	NPC323359
0.9259	High Similarity	NPC473405
0.9259	High Similarity	NPC475209
0.9259	High Similarity	NPC470876
0.9259	High Similarity	NPC85154
0.9259	High Similarity	NPC309223
0.9259	High Similarity	NPC33012
0.9259	High Similarity	NPC286457
0.9259	High Similarity	NPC475514
0.9259	High Similarity	NPC191827
0.9259	High Similarity	NPC69811
0.9259	High Similarity	NPC475119
0.9259	High Similarity	NPC473452

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 NPC274507 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	241
0.1-0.2	1965
0.2-0.3	3815
0.3-0.4	2025
0.4-0.5	636
0.5-0.6	290
0.6-0.7	145
0.7-0.8	20
0.8-0.85	10
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8962	High Similarity	NPD8132	Clinical (unspecified phase)
0.8909	High Similarity	NPD8295	Clinical (unspecified phase)
0.8772	High Similarity	NPD8328	Phase 3
0.8304	Intermediate Similarity	NPD8133	Approved
0.8257	Intermediate Similarity	NPD6412	Phase 2
0.8182	Intermediate Similarity	NPD6686	Approved
0.8077	Intermediate Similarity	NPD7748	Approved
0.8019	Intermediate Similarity	NPD7902	Approved
0.8	Intermediate Similarity	NPD7507	Approved
0.7966	Intermediate Similarity	NPD8033	Approved
0.7885	Intermediate Similarity	NPD7515	Phase 2
0.7881	Intermediate Similarity	NPD8294	Approved
0.7881	Intermediate Similarity	NPD8377	Approved
0.7815	Intermediate Similarity	NPD8380	Approved
0.7815	Intermediate Similarity	NPD8379	Approved
0.7815	Intermediate Similarity	NPD8296	Approved
0.7815	Intermediate Similarity	NPD8378	Approved
0.7815	Intermediate Similarity	NPD8335	Approved
0.7805	Intermediate Similarity	NPD7319	Approved
0.7736	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD7900	Approved
0.7724	Intermediate Similarity	NPD7736	Approved
0.7712	Intermediate Similarity	NPD7328	Approved
0.7712	Intermediate Similarity	NPD7327	Approved
0.7667	Intermediate Similarity	NPD8515	Approved
0.7667	Intermediate Similarity	NPD8517	Approved
0.7667	Intermediate Similarity	NPD8516	Approved
0.7667	Intermediate Similarity	NPD8513	Phase 3
0.7647	Intermediate Similarity	NPD7516	Approved
0.7521	Intermediate Similarity	NPD7503	Approved
0.75	Intermediate Similarity	NPD8293	Discontinued
0.7383	Intermediate Similarity	NPD8035	Phase 2
0.7383	Intermediate Similarity	NPD8034	Phase 2
0.7317	Intermediate Similarity	NPD6370	Approved
0.7315	Intermediate Similarity	NPD6399	Phase 3
0.7297	Intermediate Similarity	NPD7638	Approved
0.7288	Intermediate Similarity	NPD6882	Approved
0.7288	Intermediate Similarity	NPD8297	Approved
0.7281	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD7640	Approved
0.7232	Intermediate Similarity	NPD7639	Approved
0.7228	Intermediate Similarity	NPD7645	Phase 2
0.7203	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7492	Approved
0.719	Intermediate Similarity	NPD6009	Approved
0.7179	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD6319	Approved
0.7154	Intermediate Similarity	NPD6059	Approved
0.7154	Intermediate Similarity	NPD6054	Approved
0.7143	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6616	Approved
0.712	Intermediate Similarity	NPD6067	Discontinued
0.7094	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD7078	Approved
0.7083	Intermediate Similarity	NPD4632	Approved
0.7069	Intermediate Similarity	NPD7128	Approved
0.7069	Intermediate Similarity	NPD5739	Approved
0.7069	Intermediate Similarity	NPD6675	Approved
0.7069	Intermediate Similarity	NPD6402	Approved
0.7064	Intermediate Similarity	NPD6411	Approved
0.7049	Intermediate Similarity	NPD7115	Discovery
0.7034	Intermediate Similarity	NPD6372	Approved
0.7034	Intermediate Similarity	NPD6373	Approved
0.6975	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD46	Approved
0.6972	Remote Similarity	NPD6698	Approved
0.696	Remote Similarity	NPD6015	Approved
0.696	Remote Similarity	NPD6016	Approved
0.6949	Remote Similarity	NPD7320	Approved
0.6949	Remote Similarity	NPD6881	Approved
0.6949	Remote Similarity	NPD6899	Approved
0.6917	Remote Similarity	NPD6650	Approved
0.6917	Remote Similarity	NPD8130	Phase 1
0.6917	Remote Similarity	NPD6649	Approved
0.6905	Remote Similarity	NPD5988	Approved
0.6887	Remote Similarity	NPD4786	Approved
0.6881	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD6101	Approved
0.6864	Remote Similarity	NPD5701	Approved
0.6864	Remote Similarity	NPD5697	Approved
0.6857	Remote Similarity	NPD3667	Approved
0.6847	Remote Similarity	NPD8171	Discontinued
0.6842	Remote Similarity	NPD4225	Approved
0.6833	Remote Similarity	NPD7290	Approved
0.6833	Remote Similarity	NPD7102	Approved
0.6833	Remote Similarity	NPD6883	Approved
0.6822	Remote Similarity	NPD8074	Phase 3
0.6789	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6008	Approved
0.6777	Remote Similarity	NPD6847	Approved
0.6777	Remote Similarity	NPD6617	Approved
0.6777	Remote Similarity	NPD6869	Approved
0.6759	Remote Similarity	NPD3618	Phase 1
0.6757	Remote Similarity	NPD7983	Approved
0.6754	Remote Similarity	NPD6084	Phase 2
0.6754	Remote Similarity	NPD6083	Phase 2
0.675	Remote Similarity	NPD6014	Approved
0.675	Remote Similarity	NPD6013	Approved
0.675	Remote Similarity	NPD6012	Approved
0.6727	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD5328	Approved
0.6723	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD7604	Phase 2
0.6697	Remote Similarity	NPD3573	Approved
0.6696	Remote Similarity	NPD5779	Approved
0.6696	Remote Similarity	NPD5778	Approved
0.6693	Remote Similarity	NPD5983	Phase 2
0.6667	Remote Similarity	NPD7632	Discontinued
0.6667	Remote Similarity	NPD6011	Approved
0.6641	Remote Similarity	NPD6033	Approved
0.6639	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD6336	Discontinued
0.6609	Remote Similarity	NPD4755	Approved
0.6607	Remote Similarity	NPD6079	Approved
0.6606	Remote Similarity	NPD7334	Approved
0.6606	Remote Similarity	NPD6684	Approved
0.6606	Remote Similarity	NPD6409	Approved
0.6606	Remote Similarity	NPD5330	Approved
0.6606	Remote Similarity	NPD7521	Approved
0.6606	Remote Similarity	NPD7146	Approved
0.6567	Remote Similarity	NPD8449	Approved
0.6562	Remote Similarity	NPD6921	Approved
0.656	Remote Similarity	NPD6940	Discontinued
0.6557	Remote Similarity	NPD4634	Approved
0.6552	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD4202	Approved
0.6519	Remote Similarity	NPD8450	Suspended
0.6509	Remote Similarity	NPD7525	Registered
0.6496	Remote Similarity	NPD4696	Approved
0.6496	Remote Similarity	NPD5285	Approved
0.6496	Remote Similarity	NPD4700	Approved
0.6496	Remote Similarity	NPD5286	Approved
0.6486	Remote Similarity	NPD6672	Approved
0.6486	Remote Similarity	NPD6903	Approved
0.6486	Remote Similarity	NPD5737	Approved
0.6481	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD3669	Approved
0.6476	Remote Similarity	NPD6697	Approved
0.6476	Remote Similarity	NPD6115	Approved
0.6476	Remote Similarity	NPD6114	Approved
0.6476	Remote Similarity	NPD6118	Approved
0.6441	Remote Similarity	NPD5344	Discontinued
0.6435	Remote Similarity	NPD5695	Phase 3
0.6429	Remote Similarity	NPD6274	Approved
0.6422	Remote Similarity	NPD3668	Phase 3
0.6422	Remote Similarity	NPD3665	Phase 1
0.6422	Remote Similarity	NPD3666	Approved
0.6422	Remote Similarity	NPD3133	Approved
0.641	Remote Similarity	NPD5696	Approved
0.6406	Remote Similarity	NPD7101	Approved
0.6406	Remote Similarity	NPD7100	Approved
0.6387	Remote Similarity	NPD5226	Approved
0.6387	Remote Similarity	NPD5211	Phase 2
0.6387	Remote Similarity	NPD4633	Approved
0.6387	Remote Similarity	NPD5225	Approved
0.6387	Remote Similarity	NPD5224	Approved
0.6381	Remote Similarity	NPD6116	Phase 1
0.6379	Remote Similarity	NPD5222	Approved
0.6379	Remote Similarity	NPD7839	Suspended
0.6379	Remote Similarity	NPD4697	Phase 3
0.6379	Remote Similarity	NPD5221	Approved
0.6379	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD7838	Discovery
0.6364	Remote Similarity	NPD4767	Approved
0.6364	Remote Similarity	NPD4768	Approved
0.6333	Remote Similarity	NPD5175	Approved
0.6333	Remote Similarity	NPD5174	Approved
0.6328	Remote Similarity	NPD6335	Approved
0.6328	Remote Similarity	NPD7641	Discontinued
0.6325	Remote Similarity	NPD5173	Approved
0.632	Remote Similarity	NPD6053	Discontinued
0.6319	Remote Similarity	NPD7625	Phase 1
0.6316	Remote Similarity	NPD7637	Suspended
0.6308	Remote Similarity	NPD6909	Approved
0.6308	Remote Similarity	NPD6908	Approved
0.6303	Remote Similarity	NPD5223	Approved
0.6299	Remote Similarity	NPD6868	Approved
0.6296	Remote Similarity	NPD1779	Approved
0.6296	Remote Similarity	NPD1780	Approved
0.6293	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD8341	Approved
0.6288	Remote Similarity	NPD8299	Approved
0.6288	Remote Similarity	NPD8342	Approved
0.6288	Remote Similarity	NPD8340	Approved
0.6286	Remote Similarity	NPD6117	Approved
0.6283	Remote Similarity	NPD4753	Phase 2
0.6281	Remote Similarity	NPD5141	Approved
0.6269	Remote Similarity	NPD8337	Approved
0.6269	Remote Similarity	NPD8336	Approved
0.626	Remote Similarity	NPD4730	Approved
0.626	Remote Similarity	NPD4729	Approved
0.625	Remote Similarity	NPD7524	Approved
0.625	Remote Similarity	NPD6317	Approved
0.6241	Remote Similarity	NPD8451	Approved
0.6239	Remote Similarity	NPD7732	Phase 3
0.6239	Remote Similarity	NPD7614	Phase 1
0.6212	Remote Similarity	NPD7830	Approved
0.6212	Remote Similarity	NPD7829	Approved
0.6204	Remote Similarity	NPD4695	Discontinued

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