NPASS Compound

Structure

CID313921 OpenBabel06191716122D 36 40 0 0 1 0 0 0 0 0999 V2000 2.9170 1.1492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1891 3.0328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1244 -1.5990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3642 1.7001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4743 1.1241 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0730 2.2092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3914 0.5435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1123 -0.2566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0605 2.6964 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2972 -0.7271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5044 2.8537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2972 1.1552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5796 0.2139 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8532 0.1977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0351 0.4693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1123 0.6846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5438 2.3642 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.1711 -0.6341 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.4822 0.6846 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.1713 1.0620 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.6323 2.5962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1245 0.0213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8931 1.8930 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.0704 1.3340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2536 -0.8434 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.4822 -0.2566 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.3888 0.2651 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.1221 3.3858 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8710 -0.5320 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7205 2.3160 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9903 1.4654 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0899 2.8191 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0566 0.7477 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 -0.2537 1.2713 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7025 -0.3859 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 17 1 0 0 0 0 3 25 1 0 0 0 0 4 5 1 0 0 0 0 4 6 2 3 0 0 0 5 7 2 3 0 0 0 6 21 1 0 0 0 0 7 22 1 0 0 0 0 8 10 1 0 0 0 0 8 16 1 0 0 0 0 9 11 1 0 0 0 0 9 17 1 0 0 0 0 10 26 1 0 0 0 0 11 32 1 0 0 0 0 12 16 2 0 0 0 0 12 19 1 0 0 0 0 13 18 1 0 0 0 0 13 20 1 0 0 0 0 14 26 1 0 0 0 0 14 33 1 0 0 0 0 15 27 1 0 0 0 0 15 34 1 0 0 0 0 17 23 1 0 0 0 0 18 25 1 0 0 0 0 18 36 1 0 0 0 0 19 26 1 0 0 0 0 19 35 1 0 0 0 0 20 27 1 0 0 0 0 20 35 1 0 0 0 0 21 28 2 0 0 0 0 21 32 1 0 0 0 0 22 29 2 0 0 0 0 22 36 1 0 0 0 0 23 24 1 0 0 0 0 23 30 1 0 0 0 0 24 31 2 0 0 0 0 24 33 1 0 0 0 0 25 26 1 0 0 0 0 25 27 1 0 0 0 0 27 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	502.22
Volume:	496.059
LogP:	2.594
LogD:	1.231
LogS:	-2.989
# Rotatable Bonds:	0
TPSA:	120.89
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.302
Synthetic Accessibility Score:	7.162
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.24
MDCK Permeability:	1.1777536201407202e-05
Pgp-inhibitor:	0.169
Pgp-substrate:	0.884
Human Intestinal Absorption (HIA):	0.029
20% Bioavailability (F20%):	0.847
30% Bioavailability (F30%):	0.85

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.946
Plasma Protein Binding (PPB):	91.76879119873047%
Volume Distribution (VD):	2.211
Pgp-substrate:	6.08195686340332%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.196
CYP2C19-inhibitor:	0.097
CYP2C19-substrate:	0.789
CYP2C9-inhibitor:	0.127
CYP2C9-substrate:	0.033
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.167
CYP3A4-inhibitor:	0.472
CYP3A4-substrate:	0.43

ADMET: Excretion

Clearance (CL):	4.03
Half-life (T1/2):	0.341

ADMET: Toxicity

hERG Blockers:	0.5
Human Hepatotoxicity (H-HT):	0.246
Drug-inuced Liver Injury (DILI):	0.133
AMES Toxicity:	0.024
Rat Oral Acute Toxicity:	0.977
Maximum Recommended Daily Dose:	0.947
Skin Sensitization:	0.871
Carcinogencity:	0.134
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.836

Download Data

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

Natural Product: NPC313921

Natural Product ID:	NPC313921
*Common Name:**	NLUGUZJQJYVUHS-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NLUGUZJQJYVUHS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C27H34O9/c1-16-8-10-26-14-33-24(31)23(30)17(2)9-11-32-21(28)6-4-5-7-22(29)36-18-13-20(35-19(26)12-16)27(15-34-27)25(18,26)3/h4-7,12,17-20,23,30H,8-11,13-15H2,1-3H3
SMILES:	O=C1C=CC=CC(=O)OCCC(C(C(=O)OCC23C4(C(O1)CC(C14CO1)OC3C=C(CC2)C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1733059
PubChem CID:	104830
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0001789] Trichothecenes

*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
NPO5482	Gymnanthemum amygdalinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7524	Albifimbria verrucaria	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7524	Albifimbria verrucaria	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5482	Gymnanthemum amygdalinum	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
AC50	2
Potency	15

Activity Type	# Activity
Cell Line	1
Individual Protein	11
Others	5

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.	4.6	nM	PMID[570243]
NPT65	Cell Line	HepG2	Homo sapiens	Potency	n.a.	14125.4	nM	PMID[570243]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	65.1	nM	PMID[570243]
NPT478	Individual Protein	Ataxin-2	Homo sapiens	Potency	n.a.	84.4	nM	PMID[570243]
NPT159	Individual Protein	Aberrant vpr protein	Human immunodeficiency virus 1	Potency	n.a.	1778.3	nM	PMID[570243]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	163.6	nM	PMID[570243]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	23.1	nM	PMID[570243]
NPT160	Individual Protein	TAR DNA-binding protein 43	Homo sapiens	Potency	n.a.	891.3	nM	PMID[570243]
NPT2	Others	Unspecified		Potency	n.a.	183.6	nM	PMID[570243]
NPT918	Individual Protein	Heat shock protein HSP 90-alpha	Homo sapiens	AC50	<	195.0	nM	PMID[570243]
NPT919	Individual Protein	HSP90	Plasmodium falciparum 3D7	AC50	=	221.0	nM	PMID[570243]
NPT2	Others	Unspecified		Potency	n.a.	316.2	nM	PMID[570243]
NPT2	Others	Unspecified		Potency	n.a.	8.2	nM	PMID[570243]
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Potency	n.a.	163.6	nM	PMID[570243]
NPT920	Individual Protein	Alpha-synuclein	Homo sapiens	Potency	n.a.	1000.0	nM	PMID[570243]
NPT2	Others	Unspecified		Potency	n.a.	281.8	nM	PMID[570243]
NPT2	Others	Unspecified		Potency	n.a.	8912.5	nM	PMID[570243]

☑ 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 NPC313921 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	207
0.1-0.2	1075
0.2-0.3	4251
0.3-0.4	8459
0.4-0.5	13748
0.5-0.6	7898
0.6-0.7	5772
0.7-0.8	1206
0.8-0.85	25
0.85-0.9	31
0.9-0.95	18
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC98038
0.9904	High Similarity	NPC101400
0.9904	High Similarity	NPC101965
0.9439	High Similarity	NPC265290
0.9439	High Similarity	NPC305044
0.9231	High Similarity	NPC93026
0.9231	High Similarity	NPC265502
0.9231	High Similarity	NPC29389
0.9231	High Similarity	NPC469960
0.9143	High Similarity	NPC469959
0.9143	High Similarity	NPC469957
0.9143	High Similarity	NPC108682
0.9143	High Similarity	NPC472263
0.8942	High Similarity	NPC214714
0.8942	High Similarity	NPC252242
0.8942	High Similarity	NPC475956
0.8942	High Similarity	NPC200672
0.8932	High Similarity	NPC79631
0.8889	High Similarity	NPC41551
0.8889	High Similarity	NPC50223
0.8857	High Similarity	NPC260809
0.8857	High Similarity	NPC474783
0.8846	High Similarity	NPC26557
0.8839	High Similarity	NPC475130
0.8839	High Similarity	NPC474286
0.875	High Similarity	NPC98813
0.875	High Similarity	NPC13743
0.8679	High Similarity	NPC232515
0.8654	High Similarity	NPC79449
0.8654	High Similarity	NPC65700
0.8654	High Similarity	NPC474957
0.8649	High Similarity	NPC287075
0.8585	High Similarity	NPC475986
0.8558	High Similarity	NPC347923
0.8558	High Similarity	NPC476057
0.8544	High Similarity	NPC240838
0.8476	Intermediate Similarity	NPC274458
0.8468	Intermediate Similarity	NPC71680
0.8455	Intermediate Similarity	NPC77089
0.8426	Intermediate Similarity	NPC169843
0.8393	Intermediate Similarity	NPC241477
0.8381	Intermediate Similarity	NPC182811
0.8378	Intermediate Similarity	NPC15551
0.8333	Intermediate Similarity	NPC123505
0.8208	Intermediate Similarity	NPC120299
0.819	Intermediate Similarity	NPC475401
0.8158	Intermediate Similarity	NPC469463
0.8158	Intermediate Similarity	NPC469454
0.8158	Intermediate Similarity	NPC469496
0.8131	Intermediate Similarity	NPC475653
0.812	Intermediate Similarity	NPC477092
0.8113	Intermediate Similarity	NPC255410
0.8108	Intermediate Similarity	NPC470192
0.8103	Intermediate Similarity	NPC475305
0.8073	Intermediate Similarity	NPC473596
0.8051	Intermediate Similarity	NPC79579
0.8034	Intermediate Similarity	NPC13710
0.8019	Intermediate Similarity	NPC300710
0.7982	Intermediate Similarity	NPC179798
0.7982	Intermediate Similarity	NPC304180
0.7966	Intermediate Similarity	NPC270850
0.7966	Intermediate Similarity	NPC5292
0.7966	Intermediate Similarity	NPC278681
0.7966	Intermediate Similarity	NPC305260
0.7931	Intermediate Similarity	NPC216665
0.7931	Intermediate Similarity	NPC178289
0.7899	Intermediate Similarity	NPC112936
0.7895	Intermediate Similarity	NPC5103
0.7895	Intermediate Similarity	NPC181298
0.789	Intermediate Similarity	NPC475053
0.7881	Intermediate Similarity	NPC16701
0.7881	Intermediate Similarity	NPC153440
0.7857	Intermediate Similarity	NPC471234
0.7857	Intermediate Similarity	NPC470980
0.7851	Intermediate Similarity	NPC6193
0.7845	Intermediate Similarity	NPC56448
0.7833	Intermediate Similarity	NPC473228
0.7833	Intermediate Similarity	NPC470829
0.7833	Intermediate Similarity	NPC312481
0.7826	Intermediate Similarity	NPC475495
0.7826	Intermediate Similarity	NPC474750
0.7823	Intermediate Similarity	NPC470880
0.7815	Intermediate Similarity	NPC213761
0.7815	Intermediate Similarity	NPC35171
0.781	Intermediate Similarity	NPC197107
0.7807	Intermediate Similarity	NPC475274
0.7798	Intermediate Similarity	NPC222303
0.7797	Intermediate Similarity	NPC23046
0.7797	Intermediate Similarity	NPC157380
0.7797	Intermediate Similarity	NPC185287
0.7788	Intermediate Similarity	NPC474421
0.7788	Intermediate Similarity	NPC326994
0.7788	Intermediate Similarity	NPC324327
0.7788	Intermediate Similarity	NPC72813
0.7788	Intermediate Similarity	NPC194620
0.7778	Intermediate Similarity	NPC43213
0.7769	Intermediate Similarity	NPC107493
0.7769	Intermediate Similarity	NPC471082
0.7768	Intermediate Similarity	NPC472748
0.776	Intermediate Similarity	NPC213634
0.7759	Intermediate Similarity	NPC317687
0.7759	Intermediate Similarity	NPC473522
0.7759	Intermediate Similarity	NPC477093
0.7759	Intermediate Similarity	NPC475277
0.775	Intermediate Similarity	NPC474585
0.775	Intermediate Similarity	NPC472004
0.7724	Intermediate Similarity	NPC159499
0.7719	Intermediate Similarity	NPC14862
0.7719	Intermediate Similarity	NPC472825
0.7719	Intermediate Similarity	NPC55972
0.7719	Intermediate Similarity	NPC327286
0.7719	Intermediate Similarity	NPC233379
0.7719	Intermediate Similarity	NPC169888
0.7719	Intermediate Similarity	NPC474664
0.7712	Intermediate Similarity	NPC190286
0.7712	Intermediate Similarity	NPC148458
0.7699	Intermediate Similarity	NPC472749
0.7699	Intermediate Similarity	NPC16313
0.7699	Intermediate Similarity	NPC54737
0.7699	Intermediate Similarity	NPC9303
0.7699	Intermediate Similarity	NPC472751
0.7699	Intermediate Similarity	NPC477125
0.7698	Intermediate Similarity	NPC155529
0.7698	Intermediate Similarity	NPC471855
0.7686	Intermediate Similarity	NPC46570
0.7686	Intermediate Similarity	NPC472000
0.7686	Intermediate Similarity	NPC310511
0.7686	Intermediate Similarity	NPC471999
0.768	Intermediate Similarity	NPC471407
0.7679	Intermediate Similarity	NPC4620
0.7679	Intermediate Similarity	NPC183570
0.7679	Intermediate Similarity	NPC472747
0.7679	Intermediate Similarity	NPC472750
0.7672	Intermediate Similarity	NPC317107
0.7667	Intermediate Similarity	NPC19028
0.7667	Intermediate Similarity	NPC9674
0.7667	Intermediate Similarity	NPC472667
0.7661	Intermediate Similarity	NPC473253
0.7661	Intermediate Similarity	NPC473265
0.7658	Intermediate Similarity	NPC146822
0.7656	Intermediate Similarity	NPC158350
0.7652	Intermediate Similarity	NPC187876
0.7652	Intermediate Similarity	NPC139838
0.7652	Intermediate Similarity	NPC59489
0.7652	Intermediate Similarity	NPC15218
0.7647	Intermediate Similarity	NPC239273
0.7636	Intermediate Similarity	NPC161855
0.7627	Intermediate Similarity	NPC106446
0.7623	Intermediate Similarity	NPC23786
0.7623	Intermediate Similarity	NPC470265
0.7615	Intermediate Similarity	NPC57664
0.7611	Intermediate Similarity	NPC220964
0.7611	Intermediate Similarity	NPC475676
0.7611	Intermediate Similarity	NPC472822
0.7607	Intermediate Similarity	NPC236217
0.7607	Intermediate Similarity	NPC221144
0.7607	Intermediate Similarity	NPC126691
0.7607	Intermediate Similarity	NPC100267
0.7607	Intermediate Similarity	NPC475524
0.76	Intermediate Similarity	NPC236999
0.7593	Intermediate Similarity	NPC469491
0.7593	Intermediate Similarity	NPC281775
0.7589	Intermediate Similarity	NPC470972
0.7589	Intermediate Similarity	NPC78127
0.7589	Intermediate Similarity	NPC49393
0.7589	Intermediate Similarity	NPC66110
0.7589	Intermediate Similarity	NPC472754
0.7589	Intermediate Similarity	NPC471757
0.7586	Intermediate Similarity	NPC206595
0.7583	Intermediate Similarity	NPC257457
0.7583	Intermediate Similarity	NPC311554
0.7565	Intermediate Similarity	NPC10150
0.7565	Intermediate Similarity	NPC88701
0.7561	Intermediate Similarity	NPC469789
0.7545	Intermediate Similarity	NPC205143
0.7545	Intermediate Similarity	NPC40812
0.7544	Intermediate Similarity	NPC475290
0.7544	Intermediate Similarity	NPC82251
0.7544	Intermediate Similarity	NPC475802
0.7542	Intermediate Similarity	NPC171126
0.7542	Intermediate Similarity	NPC106395
0.7542	Intermediate Similarity	NPC46269
0.7542	Intermediate Similarity	NPC194100
0.7541	Intermediate Similarity	NPC472001
0.7541	Intermediate Similarity	NPC67569
0.754	Intermediate Similarity	NPC221414
0.754	Intermediate Similarity	NPC104382
0.7523	Intermediate Similarity	NPC272050
0.7522	Intermediate Similarity	NPC23584
0.7522	Intermediate Similarity	NPC474775
0.7522	Intermediate Similarity	NPC280566
0.7522	Intermediate Similarity	NPC472755
0.7521	Intermediate Similarity	NPC470076
0.7521	Intermediate Similarity	NPC219656
0.7521	Intermediate Similarity	NPC473203
0.7521	Intermediate Similarity	NPC476529
0.7521	Intermediate Similarity	NPC475775
0.752	Intermediate Similarity	NPC287423
0.752	Intermediate Similarity	NPC470882
0.75	Intermediate Similarity	NPC62670

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 NPC313921 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	178
0.1-0.2	1304
0.2-0.3	3778
0.3-0.4	2616
0.4-0.5	776
0.5-0.6	261
0.6-0.7	221
0.7-0.8	16
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.781	Intermediate Similarity	NPD7838	Discovery
0.7686	Intermediate Similarity	NPD7503	Approved
0.7642	Intermediate Similarity	NPD6698	Approved
0.7642	Intermediate Similarity	NPD46	Approved
0.7603	Intermediate Similarity	NPD6319	Approved
0.7478	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD8297	Approved
0.7414	Intermediate Similarity	NPD6686	Approved
0.7395	Intermediate Similarity	NPD4632	Approved
0.7321	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7638	Approved
0.7311	Intermediate Similarity	NPD6053	Discontinued
0.7302	Intermediate Similarity	NPD7507	Approved
0.7288	Intermediate Similarity	NPD6371	Approved
0.7265	Intermediate Similarity	NPD6899	Approved
0.7265	Intermediate Similarity	NPD6881	Approved
0.7257	Intermediate Similarity	NPD7639	Approved
0.7257	Intermediate Similarity	NPD7640	Approved
0.7227	Intermediate Similarity	NPD6650	Approved
0.7227	Intermediate Similarity	NPD6649	Approved
0.7222	Intermediate Similarity	NPD7492	Approved
0.7213	Intermediate Similarity	NPD7115	Discovery
0.7179	Intermediate Similarity	NPD6412	Phase 2
0.7179	Intermediate Similarity	NPD5697	Approved
0.7177	Intermediate Similarity	NPD6054	Approved
0.7167	Intermediate Similarity	NPD6882	Approved
0.7165	Intermediate Similarity	NPD6616	Approved
0.7154	Intermediate Similarity	NPD7260	Phase 2
0.7154	Intermediate Similarity	NPD7328	Approved
0.7154	Intermediate Similarity	NPD7327	Approved
0.7143	Intermediate Similarity	NPD7102	Approved
0.7143	Intermediate Similarity	NPD6883	Approved
0.7143	Intermediate Similarity	NPD7604	Phase 2
0.7143	Intermediate Similarity	NPD7290	Approved
0.7132	Intermediate Similarity	NPD7319	Approved
0.712	Intermediate Similarity	NPD8033	Approved
0.7109	Intermediate Similarity	NPD7078	Approved
0.7097	Intermediate Similarity	NPD7516	Approved
0.7094	Intermediate Similarity	NPD6675	Approved
0.7094	Intermediate Similarity	NPD6402	Approved
0.7094	Intermediate Similarity	NPD5739	Approved
0.7094	Intermediate Similarity	NPD7128	Approved
0.7083	Intermediate Similarity	NPD8130	Phase 1
0.7083	Intermediate Similarity	NPD6847	Approved
0.7083	Intermediate Similarity	NPD6617	Approved
0.7083	Intermediate Similarity	NPD6869	Approved
0.708	Intermediate Similarity	NPD6084	Phase 2
0.708	Intermediate Similarity	NPD6083	Phase 2
0.7073	Intermediate Similarity	NPD6009	Approved
0.7063	Intermediate Similarity	NPD6370	Approved
0.7059	Intermediate Similarity	NPD6014	Approved
0.7059	Intermediate Similarity	NPD6373	Approved
0.7059	Intermediate Similarity	NPD6372	Approved
0.7059	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6013	Approved
0.7059	Intermediate Similarity	NPD6012	Approved
0.7054	Intermediate Similarity	NPD7736	Approved
0.7043	Intermediate Similarity	NPD5344	Discontinued
0.704	Intermediate Similarity	NPD8294	Approved
0.704	Intermediate Similarity	NPD8377	Approved
0.7	Intermediate Similarity	NPD4634	Approved
0.6984	Remote Similarity	NPD6015	Approved
0.6984	Remote Similarity	NPD8335	Approved
0.6984	Remote Similarity	NPD6016	Approved
0.6984	Remote Similarity	NPD8378	Approved
0.6984	Remote Similarity	NPD5983	Phase 2
0.6984	Remote Similarity	NPD8296	Approved
0.6984	Remote Similarity	NPD8380	Approved
0.6984	Remote Similarity	NPD8379	Approved
0.6975	Remote Similarity	NPD6011	Approved
0.6975	Remote Similarity	NPD7320	Approved
0.6957	Remote Similarity	NPD6648	Approved
0.6942	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD7983	Approved
0.6929	Remote Similarity	NPD5988	Approved
0.6905	Remote Similarity	NPD6059	Approved
0.6903	Remote Similarity	NPD5695	Phase 3
0.6899	Remote Similarity	NPD6336	Discontinued
0.6891	Remote Similarity	NPD5701	Approved
0.6881	Remote Similarity	NPD4250	Approved
0.6881	Remote Similarity	NPD4251	Approved
0.686	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD4820	Approved
0.6857	Remote Similarity	NPD4819	Approved
0.6857	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD4822	Approved
0.6857	Remote Similarity	NPD4821	Approved
0.685	Remote Similarity	NPD8517	Approved
0.685	Remote Similarity	NPD8516	Approved
0.685	Remote Similarity	NPD8515	Approved
0.685	Remote Similarity	NPD8513	Phase 3
0.6847	Remote Similarity	NPD5785	Approved
0.6846	Remote Similarity	NPD8293	Discontinued
0.6838	Remote Similarity	NPD5211	Phase 2
0.681	Remote Similarity	NPD5286	Approved
0.681	Remote Similarity	NPD5285	Approved
0.681	Remote Similarity	NPD4696	Approved
0.6789	Remote Similarity	NPD4249	Approved
0.6786	Remote Similarity	NPD7637	Suspended
0.6729	Remote Similarity	NPD6435	Approved
0.6726	Remote Similarity	NPD5779	Approved
0.6726	Remote Similarity	NPD5778	Approved
0.6724	Remote Similarity	NPD5696	Approved
0.6724	Remote Similarity	NPD4225	Approved
0.6723	Remote Similarity	NPD5141	Approved
0.6716	Remote Similarity	NPD6845	Suspended
0.6695	Remote Similarity	NPD5225	Approved
0.6695	Remote Similarity	NPD5224	Approved
0.6695	Remote Similarity	NPD5226	Approved
0.6695	Remote Similarity	NPD4633	Approved
0.6695	Remote Similarity	NPD7632	Discontinued
0.6694	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD7100	Approved
0.6693	Remote Similarity	NPD7101	Approved
0.6667	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6008	Approved
0.6667	Remote Similarity	NPD4271	Approved
0.6667	Remote Similarity	NPD4268	Approved
0.6642	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD5174	Approved
0.6639	Remote Similarity	NPD5175	Approved
0.6638	Remote Similarity	NPD4755	Approved
0.6637	Remote Similarity	NPD5693	Phase 1
0.6637	Remote Similarity	NPD6411	Approved
0.6637	Remote Similarity	NPD5694	Approved
0.6637	Remote Similarity	NPD5281	Approved
0.6637	Remote Similarity	NPD5284	Approved
0.6637	Remote Similarity	NPD6050	Approved
0.6615	Remote Similarity	NPD7829	Approved
0.6615	Remote Similarity	NPD7830	Approved
0.6614	Remote Similarity	NPD6335	Approved
0.6612	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.661	Remote Similarity	NPD5223	Approved
0.6609	Remote Similarity	NPD5210	Approved
0.6609	Remote Similarity	NPD4629	Approved
0.6607	Remote Similarity	NPD4753	Phase 2
0.6591	Remote Similarity	NPD8074	Phase 3
0.6587	Remote Similarity	NPD6274	Approved
0.6577	Remote Similarity	NPD7524	Approved
0.6574	Remote Similarity	NPD5209	Approved
0.656	Remote Similarity	NPD8133	Approved
0.6557	Remote Similarity	NPD4729	Approved
0.6557	Remote Similarity	NPD4730	Approved
0.6549	Remote Similarity	NPD5692	Phase 3
0.6545	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD5368	Approved
0.6535	Remote Similarity	NPD6317	Approved
0.6525	Remote Similarity	NPD4700	Approved
0.6522	Remote Similarity	NPD5282	Discontinued
0.6489	Remote Similarity	NPD8328	Phase 3
0.6486	Remote Similarity	NPD7334	Approved
0.6486	Remote Similarity	NPD5330	Approved
0.6486	Remote Similarity	NPD7146	Approved
0.6486	Remote Similarity	NPD7521	Approved
0.6486	Remote Similarity	NPD6684	Approved
0.6486	Remote Similarity	NPD6409	Approved
0.6484	Remote Similarity	NPD6313	Approved
0.6484	Remote Similarity	NPD6314	Approved
0.6466	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.646	Remote Similarity	NPD6101	Approved
0.646	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.646	Remote Similarity	NPD6080	Approved
0.646	Remote Similarity	NPD6904	Approved
0.646	Remote Similarity	NPD6051	Approved
0.646	Remote Similarity	NPD1695	Approved
0.646	Remote Similarity	NPD6673	Approved
0.6455	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD5247	Approved
0.6452	Remote Similarity	NPD5248	Approved
0.6452	Remote Similarity	NPD5249	Phase 3
0.6452	Remote Similarity	NPD5250	Approved
0.6452	Remote Similarity	NPD5251	Approved
0.6444	Remote Similarity	NPD5956	Approved
0.6434	Remote Similarity	NPD4522	Approved
0.6418	Remote Similarity	NPD6033	Approved
0.6396	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD5363	Approved
0.6396	Remote Similarity	NPD1694	Approved
0.6393	Remote Similarity	NPD4767	Approved
0.6393	Remote Similarity	NPD4768	Approved
0.6372	Remote Similarity	NPD6672	Approved
0.6372	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD5737	Approved
0.6372	Remote Similarity	NPD6903	Approved
0.6364	Remote Similarity	NPD5362	Discontinued
0.6364	Remote Similarity	NPD6110	Phase 1
0.6364	Remote Similarity	NPD6695	Phase 3
0.6364	Remote Similarity	NPD7154	Phase 3
0.6341	Remote Similarity	NPD6685	Approved
0.6339	Remote Similarity	NPD5690	Phase 2
0.6339	Remote Similarity	NPD5279	Phase 3
0.6339	Remote Similarity	NPD5280	Approved
0.6339	Remote Similarity	NPD4694	Approved
0.6336	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD6908	Approved
0.6336	Remote Similarity	NPD6909	Approved
0.6306	Remote Similarity	NPD3666	Approved
0.6306	Remote Similarity	NPD3133	Approved
0.6306	Remote Similarity	NPD3665	Phase 1
0.6293	Remote Similarity	NPD6399	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