NPASS Compound

Structure

CID90693 OpenBabel06191715432D 36 39 0 0 1 0 0 0 0 0999 V2000 -4.5110 -2.2073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3949 -1.8881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7923 -3.7426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0735 1.8593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1470 0.7823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2682 -1.3716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4238 -1.8591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2682 -0.3966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1896 -3.2245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0646 -2.7944 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5795 -1.3716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4238 0.0909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2210 -3.1134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1311 0.0333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0918 0.1996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7351 0.0909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5402 -0.9848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5681 -1.9594 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.4412 -2.0908 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.1399 -3.0181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2386 1.3558 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5795 -0.3966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4662 -2.4962 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8907 -0.3966 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.4128 -0.6260 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.7888 -1.3662 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.1862 -3.2208 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.6524 -0.7246 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9899 -0.1800 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.1649 -1.5689 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.3850 1.8272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1151 -4.1481 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6221 -0.6227 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9018 0.1651 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2571 0.3810 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 19 1 0 0 0 0 3 20 2 0 0 0 0 4 21 1 0 0 0 0 5 29 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 11 1 0 0 0 0 8 12 2 0 0 0 0 9 10 1 0 0 0 0 9 13 2 3 0 0 0 10 18 1 0 0 0 0 11 22 2 0 0 0 0 12 22 1 0 0 0 0 13 23 1 0 0 0 0 14 15 2 3 0 0 0 14 25 1 0 0 0 0 15 29 1 0 0 0 0 16 22 1 0 0 0 0 16 24 1 0 0 0 0 17 18 1 0 0 0 0 17 29 1 0 0 0 0 19 20 1 0 0 0 0 19 26 1 0 0 0 0 20 27 1 0 0 0 0 21 32 2 0 0 0 0 21 36 1 0 0 0 0 23 27 1 0 0 0 0 23 30 1 0 0 0 0 24 26 1 0 0 0 0 24 31 1 0 0 0 0 25 30 1 0 0 0 0 25 36 1 0 0 0 0 26 30 1 0 0 0 0 27 33 1 0 0 0 0 28 30 1 0 0 0 0 28 31 2 0 0 0 0 28 34 1 0 0 0 0 29 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	493.28
Volume:	527.066
LogP:	3.246
LogD:	2.808
LogS:	-3.683
# Rotatable Bonds:	4
TPSA:	95.86
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.44
Synthetic Accessibility Score:	5.882
Fsp3:	0.533
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.905
MDCK Permeability:	7.231361087178811e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.095
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.951
Plasma Protein Binding (PPB):	83.8805923461914%
Volume Distribution (VD):	1.632
Pgp-substrate:	18.234161376953125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.122
CYP2C19-inhibitor:	0.245
CYP2C19-substrate:	0.622
CYP2C9-inhibitor:	0.184
CYP2C9-substrate:	0.284
CYP2D6-inhibitor:	0.037
CYP2D6-substrate:	0.113
CYP3A4-inhibitor:	0.912
CYP3A4-substrate:	0.479

ADMET: Excretion

Clearance (CL):	6.008
Half-life (T1/2):	0.023

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.04
Drug-inuced Liver Injury (DILI):	0.22
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.898
Maximum Recommended Daily Dose:	0.579
Skin Sensitization:	0.018
Carcinogencity:	0.104
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.934

Download Data

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

Natural Product: NPC90693

Natural Product ID:	NPC90693
*Common Name:**	NAEWXXDGBKTIMN-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NAEWXXDGBKTIMN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C30H39NO5/c1-18-10-9-13-23-27(33)20(3)19(2)26-24(16-22-11-7-6-8-12-22)31-28(34)30(23,26)25(36-21(4)32)14-15-29(5,35)17-18/h6-9,11-15,18-19,23-27,33,35H,3,10,16-17H2,1-2,4-5H3,(H,31,34)
SMILES:	CC(=O)OC1C=CC(C)(O)CC(CC=CC2C31C(=NC(C3C(C)C(=C)C2O)Cc1ccccc1)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1702179
PubChem CID:	2921
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001821] Cytochalasans

*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
NPO20608	Gleditsia sinensis	Species	Fabaceae	Eukaryota	anomalous fruits	n.a.	n.a.	PMID[25442304]
NPO7631	Gleditsia japonica	Species	Fabaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[7494144]
NPO20608	Gleditsia sinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20608	Gleditsia sinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20608	Gleditsia sinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20608	Gleditsia sinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7631	Gleditsia japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20608	Gleditsia sinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7631	Gleditsia japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
EC50	1
Potency	15

Activity Type	# Activity
Cell Line	1
Individual Protein	8
Others	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	2310.9	nM	PMID[476583]
NPT71	Cell Line	HEK293	Homo sapiens	Potency	n.a.	2238.7	nM	PMID[476583]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	651.3	nM	PMID[476583]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	3662.6	nM	PMID[476583]
NPT478	Individual Protein	Ataxin-2	Homo sapiens	Potency	n.a.	299.3	nM	PMID[476583]
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	354.8	nM	PMID[476583]
NPT1043	Individual Protein	Glycoprotein hormones alpha chain	Homo sapiens	Potency	n.a.	794.3	nM	PMID[476583]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	730.8	nM	PMID[476583]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	461.1	nM	PMID[476583]
NPT2	Others	Unspecified		Potency	n.a.	11582.1	nM	PMID[476583]
NPT2	Others	Unspecified		Potency	n.a.	3981.1	nM	PMID[476583]
NPT2	Others	Unspecified		EC50	=	448.0	nM	PMID[476583]
NPT2	Others	Unspecified		Potency	n.a.	2818.4	nM	PMID[476583]
NPT2	Others	Unspecified		Potency	n.a.	231.1	nM	PMID[476583]
NPT2	Others	Unspecified		Potency	n.a.	316.2	nM	PMID[476583]
NPT2	Others	Unspecified		Potency	n.a.	11220.2	nM	PMID[476583]

☑ 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 NPC90693 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	130
0.1-0.2	689
0.2-0.3	1750
0.3-0.4	5367
0.4-0.5	18586
0.5-0.6	14347
0.6-0.7	1713
0.7-0.8	85
0.8-0.85	11
0.85-0.9	10
0.9-0.95	3
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC64897
0.9615	High Similarity	NPC239770
0.9185	High Similarity	NPC262216
0.9104	High Similarity	NPC111586
0.9104	High Similarity	NPC261709
0.9104	High Similarity	NPC108852
0.9077	High Similarity	NPC42423
0.8978	High Similarity	NPC237240
0.8978	High Similarity	NPC31171
0.8786	High Similarity	NPC201692
0.876	High Similarity	NPC472414
0.8702	High Similarity	NPC71271
0.8692	High Similarity	NPC278097
0.8643	High Similarity	NPC173934
0.8561	High Similarity	NPC295478
0.8519	High Similarity	NPC228511
0.8456	Intermediate Similarity	NPC113325
0.8456	Intermediate Similarity	NPC279045
0.8394	Intermediate Similarity	NPC175870
0.8369	Intermediate Similarity	NPC49565
0.8321	Intermediate Similarity	NPC472415
0.8255	Intermediate Similarity	NPC156348
0.8162	Intermediate Similarity	NPC183722
0.8129	Intermediate Similarity	NPC208725
0.8027	Intermediate Similarity	NPC4108
0.7947	Intermediate Similarity	NPC235460
0.7933	Intermediate Similarity	NPC217801
0.7883	Intermediate Similarity	NPC472413
0.7754	Intermediate Similarity	NPC116057
0.7742	Intermediate Similarity	NPC15506
0.7704	Intermediate Similarity	NPC160493
0.7687	Intermediate Similarity	NPC328824
0.7616	Intermediate Similarity	NPC275839
0.76	Intermediate Similarity	NPC470274
0.7584	Intermediate Similarity	NPC476757
0.7556	Intermediate Similarity	NPC190663
0.7551	Intermediate Similarity	NPC473922
0.7519	Intermediate Similarity	NPC470820
0.7518	Intermediate Similarity	NPC473871
0.7518	Intermediate Similarity	NPC473870
0.7516	Intermediate Similarity	NPC477115
0.75	Intermediate Similarity	NPC473869
0.7467	Intermediate Similarity	NPC94602
0.745	Intermediate Similarity	NPC475578
0.745	Intermediate Similarity	NPC44649
0.7445	Intermediate Similarity	NPC473889
0.7376	Intermediate Similarity	NPC230331
0.7357	Intermediate Similarity	NPC45821
0.7357	Intermediate Similarity	NPC475933
0.7357	Intermediate Similarity	NPC470158
0.7338	Intermediate Similarity	NPC470815
0.7338	Intermediate Similarity	NPC472373
0.7333	Intermediate Similarity	NPC84129
0.7317	Intermediate Similarity	NPC203005
0.7305	Intermediate Similarity	NPC476971
0.7305	Intermediate Similarity	NPC5486
0.7305	Intermediate Similarity	NPC476972
0.7299	Intermediate Similarity	NPC477061
0.7299	Intermediate Similarity	NPC80150
0.7299	Intermediate Similarity	NPC45777
0.7286	Intermediate Similarity	NPC471758
0.7279	Intermediate Similarity	NPC473860
0.7266	Intermediate Similarity	NPC12016
0.726	Intermediate Similarity	NPC478140
0.7254	Intermediate Similarity	NPC58061
0.7241	Intermediate Similarity	NPC132847
0.7234	Intermediate Similarity	NPC476970
0.7234	Intermediate Similarity	NPC470816
0.7229	Intermediate Similarity	NPC475345
0.7219	Intermediate Similarity	NPC260194
0.7218	Intermediate Similarity	NPC273814
0.7214	Intermediate Similarity	NPC77691
0.7208	Intermediate Similarity	NPC472761
0.7203	Intermediate Similarity	NPC93632
0.7197	Intermediate Similarity	NPC323007
0.7194	Intermediate Similarity	NPC475328
0.7186	Intermediate Similarity	NPC475649
0.7163	Intermediate Similarity	NPC284022
0.7153	Intermediate Similarity	NPC310467
0.7143	Intermediate Similarity	NPC182333
0.7143	Intermediate Similarity	NPC273336
0.7134	Intermediate Similarity	NPC120667
0.7134	Intermediate Similarity	NPC278272
0.7133	Intermediate Similarity	NPC475128
0.7122	Intermediate Similarity	NPC311175
0.7122	Intermediate Similarity	NPC37641
0.7113	Intermediate Similarity	NPC275576
0.7108	Intermediate Similarity	NPC476113
0.7092	Intermediate Similarity	NPC140118
0.7092	Intermediate Similarity	NPC12881
0.7092	Intermediate Similarity	NPC307139
0.708	Intermediate Similarity	NPC169328
0.7071	Intermediate Similarity	NPC70973
0.7063	Intermediate Similarity	NPC169913
0.7059	Intermediate Similarity	NPC313414
0.7059	Intermediate Similarity	NPC188010
0.7055	Intermediate Similarity	NPC476976
0.7055	Intermediate Similarity	NPC3202
0.705	Intermediate Similarity	NPC478015
0.705	Intermediate Similarity	NPC478014
0.705	Intermediate Similarity	NPC478016
0.7045	Intermediate Similarity	NPC114741
0.7045	Intermediate Similarity	NPC182549
0.7042	Intermediate Similarity	NPC265413
0.7042	Intermediate Similarity	NPC474532
0.7042	Intermediate Similarity	NPC10154
0.7042	Intermediate Similarity	NPC47667
0.7029	Intermediate Similarity	NPC254233
0.7007	Intermediate Similarity	NPC242764
0.7007	Intermediate Similarity	NPC105141
0.7	Intermediate Similarity	NPC476184
0.7	Intermediate Similarity	NPC224610
0.7	Intermediate Similarity	NPC113326
0.7	Intermediate Similarity	NPC476281
0.7	Intermediate Similarity	NPC473439
0.7	Intermediate Similarity	NPC197921
0.7	Intermediate Similarity	NPC300827
0.7	Intermediate Similarity	NPC194390
0.7	Intermediate Similarity	NPC88267
0.6988	Remote Similarity	NPC211713
0.6988	Remote Similarity	NPC88378
0.6986	Remote Similarity	NPC476977
0.6986	Remote Similarity	NPC246079
0.698	Remote Similarity	NPC477557
0.6978	Remote Similarity	NPC470814
0.6957	Remote Similarity	NPC476750
0.6954	Remote Similarity	NPC91953
0.6954	Remote Similarity	NPC472547
0.6948	Remote Similarity	NPC473541
0.6944	Remote Similarity	NPC253681
0.694	Remote Similarity	NPC133308
0.6939	Remote Similarity	NPC313663
0.6939	Remote Similarity	NPC80599
0.6933	Remote Similarity	NPC39549
0.6929	Remote Similarity	NPC476183
0.6923	Remote Similarity	NPC114927
0.6923	Remote Similarity	NPC473083
0.6918	Remote Similarity	NPC472388
0.6918	Remote Similarity	NPC93343
0.6906	Remote Similarity	NPC89324
0.6906	Remote Similarity	NPC237420
0.6905	Remote Similarity	NPC58674
0.6901	Remote Similarity	NPC476278
0.6901	Remote Similarity	NPC108286
0.6894	Remote Similarity	NPC477251
0.6879	Remote Similarity	NPC327699
0.6875	Remote Similarity	NPC473110
0.6875	Remote Similarity	NPC473082
0.6875	Remote Similarity	NPC473111
0.6871	Remote Similarity	NPC246913
0.6867	Remote Similarity	NPC472551
0.6867	Remote Similarity	NPC472545
0.6866	Remote Similarity	NPC122926
0.6866	Remote Similarity	NPC113012
0.6863	Remote Similarity	NPC140021
0.6853	Remote Similarity	NPC476260
0.6853	Remote Similarity	NPC476241
0.6852	Remote Similarity	NPC67080
0.6849	Remote Similarity	NPC225103
0.6848	Remote Similarity	NPC476749
0.6846	Remote Similarity	NPC48929
0.6846	Remote Similarity	NPC126516
0.6842	Remote Similarity	NPC139243
0.6842	Remote Similarity	NPC27252
0.6842	Remote Similarity	NPC90614
0.6842	Remote Similarity	NPC469360
0.6842	Remote Similarity	NPC100913
0.6842	Remote Similarity	NPC472980
0.6842	Remote Similarity	NPC116742
0.6842	Remote Similarity	NPC472979
0.6842	Remote Similarity	NPC275592
0.6839	Remote Similarity	NPC472556
0.6835	Remote Similarity	NPC45794
0.6831	Remote Similarity	NPC369
0.6831	Remote Similarity	NPC293831
0.6831	Remote Similarity	NPC474862
0.6831	Remote Similarity	NPC473749
0.6828	Remote Similarity	NPC190849
0.6828	Remote Similarity	NPC171007
0.6828	Remote Similarity	NPC473220
0.6828	Remote Similarity	NPC470753
0.6818	Remote Similarity	NPC91703
0.6818	Remote Similarity	NPC211551
0.6813	Remote Similarity	NPC212699
0.6813	Remote Similarity	NPC207675
0.6812	Remote Similarity	NPC476476
0.6806	Remote Similarity	NPC476125
0.6806	Remote Similarity	NPC4974
0.6806	Remote Similarity	NPC476179
0.6803	Remote Similarity	NPC473443
0.6803	Remote Similarity	NPC288290
0.6803	Remote Similarity	NPC147561
0.6803	Remote Similarity	NPC475138
0.68	Remote Similarity	NPC473300
0.68	Remote Similarity	NPC453583
0.68	Remote Similarity	NPC11266
0.68	Remote Similarity	NPC471754
0.68	Remote Similarity	NPC471864
0.68	Remote Similarity	NPC317882
0.68	Remote Similarity	NPC475336

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 NPC90693 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	106
0.1-0.2	419
0.2-0.3	837
0.3-0.4	2057
0.4-0.5	3315
0.5-0.6	2012
0.6-0.7	401
0.7-0.8	2
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8978	High Similarity	NPD7274	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD5981	Approved
0.7154	Intermediate Similarity	NPD5706	Approved
0.7154	Intermediate Similarity	NPD5705	Approved
0.7154	Intermediate Similarity	NPD5704	Approved
0.7099	Intermediate Similarity	NPD6406	Approved
0.708	Intermediate Similarity	NPD7522	Discontinued
0.7068	Intermediate Similarity	NPD3644	Approved
0.7068	Intermediate Similarity	NPD3643	Approved
0.7068	Intermediate Similarity	NPD3642	Approved
0.7039	Intermediate Similarity	NPD7488	Clinical (unspecified phase)
0.695	Remote Similarity	NPD5618	Discontinued
0.6939	Remote Similarity	NPD7714	Approved
0.6939	Remote Similarity	NPD7715	Approved
0.6918	Remote Similarity	NPD4738	Phase 2
0.6906	Remote Similarity	NPD4479	Discontinued
0.6848	Remote Similarity	NPD7315	Approved
0.6846	Remote Similarity	NPD4719	Phase 2
0.6809	Remote Similarity	NPD7725	Approved
0.6806	Remote Similarity	NPD6325	Discontinued
0.6786	Remote Similarity	NPD2218	Phase 2
0.6786	Remote Similarity	NPD7741	Discontinued
0.6786	Remote Similarity	NPD2217	Approved
0.6783	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD2238	Phase 2
0.6769	Remote Similarity	NPD4760	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD5240	Approved
0.6741	Remote Similarity	NPD5236	Approved
0.6741	Remote Similarity	NPD5237	Approved
0.6741	Remote Similarity	NPD5239	Approved
0.6741	Remote Similarity	NPD5235	Approved
0.6732	Remote Similarity	NPD2174	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6667	Approved
0.6731	Remote Similarity	NPD6666	Approved
0.6713	Remote Similarity	NPD4215	Approved
0.6713	Remote Similarity	NPD2608	Approved
0.6713	Remote Similarity	NPD2612	Approved
0.6713	Remote Similarity	NPD3132	Approved
0.6713	Remote Similarity	NPD2610	Approved
0.6713	Remote Similarity	NPD4217	Approved
0.6713	Remote Similarity	NPD4216	Approved
0.6713	Remote Similarity	NPD3529	Phase 2
0.6713	Remote Similarity	NPD4218	Approved
0.6713	Remote Similarity	NPD4480	Approved
0.6713	Remote Similarity	NPD2611	Approved
0.6713	Remote Similarity	NPD3131	Approved
0.6713	Remote Similarity	NPD2609	Approved
0.671	Remote Similarity	NPD3400	Discontinued
0.6709	Remote Similarity	NPD52	Approved
0.6709	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD7526	Approved
0.6691	Remote Similarity	NPD4198	Discontinued
0.6689	Remote Similarity	NPD3136	Phase 2
0.6688	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2227	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6346	Approved
0.6667	Remote Similarity	NPD2161	Phase 2
0.6648	Remote Similarity	NPD8360	Approved
0.6648	Remote Similarity	NPD8361	Approved
0.6643	Remote Similarity	NPD2956	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD4814	Discontinued
0.6629	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD7236	Approved
0.6622	Remote Similarity	NPD2613	Approved
0.662	Remote Similarity	NPD4209	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD2629	Approved
0.6611	Remote Similarity	NPD8485	Approved
0.6609	Remote Similarity	NPD8407	Phase 2
0.6608	Remote Similarity	NPD5557	Phase 1
0.6606	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.66	Remote Similarity	NPD8118	Discontinued
0.6588	Remote Similarity	NPD3909	Discontinued
0.6579	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD7508	Discontinued
0.6569	Remote Similarity	NPD2201	Approved
0.6567	Remote Similarity	NPD5717	Approved
0.6561	Remote Similarity	NPD8323	Discontinued
0.6561	Remote Similarity	NPD3692	Discontinued
0.6554	Remote Similarity	NPD8435	Approved
0.6554	Remote Similarity	NPD5736	Approved
0.6552	Remote Similarity	NPD2230	Approved
0.6552	Remote Similarity	NPD2233	Approved
0.6552	Remote Similarity	NPD2232	Approved
0.6541	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD6647	Phase 2
0.6533	Remote Similarity	NPD4621	Approved
0.6533	Remote Similarity	NPD4619	Approved
0.6532	Remote Similarity	NPD8368	Discontinued
0.6527	Remote Similarity	NPD6746	Phase 2
0.6525	Remote Similarity	NPD4230	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7239	Suspended
0.6519	Remote Similarity	NPD6685	Approved
0.6516	Remote Similarity	NPD7978	Discontinued
0.6507	Remote Similarity	NPD6025	Phase 1
0.6507	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD1710	Approved
0.6503	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD6072	Discontinued
0.65	Remote Similarity	NPD6222	Approved
0.65	Remote Similarity	NPD6221	Approved
0.6497	Remote Similarity	NPD6331	Phase 2
0.6494	Remote Similarity	NPD4108	Discontinued
0.6494	Remote Similarity	NPD1753	Discontinued
0.6493	Remote Similarity	NPD179	Clinical (unspecified phase)
0.649	Remote Similarity	NPD2566	Approved
0.649	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.649	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.649	Remote Similarity	NPD7477	Discontinued
0.649	Remote Similarity	NPD2571	Approved
0.649	Remote Similarity	NPD839	Approved
0.649	Remote Similarity	NPD3088	Approved
0.649	Remote Similarity	NPD4745	Approved
0.649	Remote Similarity	NPD3089	Approved
0.649	Remote Similarity	NPD2573	Approved
0.649	Remote Similarity	NPD3090	Approved
0.649	Remote Similarity	NPD2570	Approved
0.649	Remote Similarity	NPD3614	Approved
0.649	Remote Similarity	NPD3087	Approved
0.649	Remote Similarity	NPD2574	Discontinued
0.649	Remote Similarity	NPD840	Approved
0.649	Remote Similarity	NPD3616	Approved
0.649	Remote Similarity	NPD3615	Approved
0.649	Remote Similarity	NPD4746	Phase 3
0.6486	Remote Similarity	NPD2194	Approved
0.6486	Remote Similarity	NPD2195	Approved
0.6483	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD4806	Approved
0.6483	Remote Similarity	NPD2173	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD4807	Approved
0.6481	Remote Similarity	NPD5811	Approved
0.6479	Remote Similarity	NPD6065	Approved
0.6475	Remote Similarity	NPD2607	Approved
0.6471	Remote Similarity	NPD4095	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD2157	Approved
0.6471	Remote Similarity	NPD4481	Phase 3
0.6467	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD5709	Phase 3
0.6466	Remote Similarity	NPD4818	Approved
0.6466	Remote Similarity	NPD4817	Approved
0.6458	Remote Similarity	NPD5305	Approved
0.6458	Remote Similarity	NPD5306	Approved
0.6447	Remote Similarity	NPD4140	Approved
0.6447	Remote Similarity	NPD8265	Approved
0.6443	Remote Similarity	NPD1712	Approved
0.6442	Remote Similarity	NPD5617	Suspended
0.6442	Remote Similarity	NPD6502	Phase 2
0.6438	Remote Similarity	NPD7250	Approved
0.6438	Remote Similarity	NPD7249	Approved
0.6433	Remote Similarity	NPD3638	Discontinued
0.6429	Remote Similarity	NPD6852	Discontinued
0.6429	Remote Similarity	NPD2650	Approved
0.6429	Remote Similarity	NPD6010	Discontinued
0.6429	Remote Similarity	NPD4666	Phase 3
0.6429	Remote Similarity	NPD2652	Approved
0.6419	Remote Similarity	NPD2627	Approved
0.6419	Remote Similarity	NPD2159	Approved
0.6419	Remote Similarity	NPD2628	Approved
0.6419	Remote Similarity	NPD2625	Approved
0.6419	Remote Similarity	NPD2626	Approved
0.6419	Remote Similarity	NPD2160	Approved
0.6412	Remote Similarity	NPD2970	Approved
0.6412	Remote Similarity	NPD2969	Approved
0.641	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD6775	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD3123	Discovery
0.6405	Remote Similarity	NPD4686	Approved
0.6405	Remote Similarity	NPD4684	Phase 3
0.6405	Remote Similarity	NPD4685	Phase 3
0.64	Remote Similarity	NPD4620	Approved
0.64	Remote Similarity	NPD600	Approved
0.64	Remote Similarity	NPD596	Approved
0.64	Remote Similarity	NPD5201	Approved
0.64	Remote Similarity	NPD4617	Approved
0.64	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5203	Approved
0.6398	Remote Similarity	NPD7613	Discontinued
0.6395	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD1669	Approved
0.6392	Remote Similarity	NPD2575	Approved
0.6382	Remote Similarity	NPD6663	Approved
0.638	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD2489	Approved
0.6374	Remote Similarity	NPD27	Approved
0.6364	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4097	Suspended
0.6364	Remote Similarity	NPD7312	Approved
0.6364	Remote Similarity	NPD7311	Approved
0.6364	Remote Similarity	NPD7313	Approved
0.6364	Remote Similarity	NPD7310	Approved
0.6357	Remote Similarity	NPD6690	Approved
0.6353	Remote Similarity	NPD3051	Approved
0.6352	Remote Similarity	NPD7740	Clinical (unspecified phase)
0.6352	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.635	Remote Similarity	NPD6038	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD2668	Approved
0.6345	Remote Similarity	NPD2667	Approved
0.6345	Remote Similarity	NPD5126	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