NPASS Compound

Structure

NPC192309 OpenBabel07101719252D 42 48 0 0 1 0 0 0 0 0999 V2000 -5.4993 -0.4139 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0417 -3.1642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5967 2.9852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0488 1.7098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0978 2.0188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3138 -1.9300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3349 -2.2219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0151 -1.4888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9365 -1.2700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7444 1.3240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3057 -1.3181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7444 -0.7005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4998 -0.4438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2154 -2.6009 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6079 2.8362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9766 -0.9896 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.1235 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4488 0.7622 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3057 -0.4172 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4488 -1.5965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1855 -1.6013 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4751 0.3117 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2256 -1.3209 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2740 -2.9382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4233 0.3791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8880 0.3473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3057 1.0406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6623 -2.1472 0.0000 C 0 0 2 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 2.4488 -0.1387 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9309 -0.3653 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0156 3.6180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1398 -2.5476 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9936 -3.8981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8572 1.2800 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1685 1.3071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9219 -0.4989 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2425 1.9053 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9467 0.0099 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8353 0.3117 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9192 -0.8676 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 13 1 0 0 0 0 3 15 1 0 0 0 0 4 27 1 0 0 0 0 5 27 1 0 0 0 0 7 8 1 0 0 0 0 7 28 1 0 0 0 0 9 13 2 0 0 0 0 10 17 1 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 11 20 1 0 0 0 0 12 29 1 0 0 0 0 13 26 1 0 0 0 0 14 2 1 1 0 0 0 14 21 1 0 0 0 0 14 24 1 0 0 0 0 15 32 2 0 0 0 0 15 38 1 0 0 0 0 16 9 1 6 0 0 0 16 39 1 0 0 0 0 17 22 1 0 0 0 0 17 38 1 1 0 0 0 18 27 1 0 0 0 0 18 30 1 1 0 0 0 19 30 1 6 0 0 0 19 40 1 0 0 0 0 20 33 2 0 0 0 0 20 41 1 0 0 0 0 21 16 1 6 0 0 0 21 23 1 0 0 0 0 22 25 1 0 0 0 0 22 29 1 6 0 0 0 23 28 1 6 0 0 0 23 31 1 0 0 0 0 24 28 1 0 0 0 0 24 34 2 0 0 0 0 25 31 1 0 0 0 0 25 35 2 0 0 0 0 26 36 2 0 0 0 0 26 39 1 0 0 0 0 27 40 1 0 0 0 0 28 6 1 1 0 0 0 29 8 1 1 0 0 0 29 42 1 0 0 0 0 30 12 1 1 0 0 0 30 41 1 0 0 0 0 31 37 1 6 0 0 0 31 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	586.24
Volume:	565.711
LogP:	2.783
LogD:	1.833
LogS:	-4.374
# Rotatable Bonds:	3
TPSA:	158.8
# H-Bond Aceptor:	11
# H-Bond Donor:	2
# Rings:	7
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.491
Synthetic Accessibility Score:	7.339
Fsp3:	0.742
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:	-5.38
MDCK Permeability:	5.882691402803175e-05
Pgp-inhibitor:	0.623
Pgp-substrate:	0.921
Human Intestinal Absorption (HIA):	0.124
20% Bioavailability (F20%):	0.841
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.936
Plasma Protein Binding (PPB):	79.1929702758789%
Volume Distribution (VD):	1.06
Pgp-substrate:	18.465621948242188%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.762
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.251
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.014
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.073
CYP3A4-inhibitor:	0.594
CYP3A4-substrate:	0.627

ADMET: Excretion

Clearance (CL):	14.176
Half-life (T1/2):	0.123

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.317
Drug-inuced Liver Injury (DILI):	0.919
AMES Toxicity:	0.039
Rat Oral Acute Toxicity:	0.988
Maximum Recommended Daily Dose:	0.915
Skin Sensitization:	0.222
Carcinogencity:	0.86
Eye Corrosion:	0.021
Eye Irritation:	0.014
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC192309

Natural Product ID:	NPC192309
*Common Name:**	Lancifodilactone J
IUPAC Name:	n.a.
Synonyms:	Lancifodilactone J
Standard InCHIKey:	RXNQFRVLPNMCHU-VJZLCUFQSA-N
Standard InCHI:	InChI=1S/C31H38O11/c1-13-9-16(39-26(13)36)21-14(2)24(34)28(6)7-8-29-12-30-18(27(4,5)40-19(30)11-20(33)41-30)10-17(38-15(3)32)22(29)25(35)31(37,42-29)23(21)28/h9,14,16-19,21-23,37H,7-8,10-12H2,1-6H3/t14-,16-,17-,18-,19+,21+,22-,23-,28-,29-,30+,31-/m0/s1
SMILES:	CC1=C[C@@H]([C@H]2[C@H](C)C(=O)[C@@]3(C)CC[C@]45C[C@@]67[C@@H](C[C@@H]([C@H]4C(=O)[C@@]([C@@H]23)(O)O5)OC(=O)C)C(C)(C)O[C@@H]6CC(=O)O7)OC1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL510575
PubChem CID:	11657186
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000513] Eicosanoids [CHEMONTID:0000514] Prostaglandins and related compounds

*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
NPO19507	Schisandra lancifolia	Species	Schisandraceae	Eukaryota	n.a.	leaf	n.a.	PMID[15787482]
NPO19507	Schisandra lancifolia	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[15787482]
NPO19507	Schisandra lancifolia	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[15901155]
NPO19507	Schisandra lancifolia	Species	Schisandraceae	Eukaryota	n.a.	leaf	n.a.	PMID[15901155]
NPO19507	Schisandra lancifolia	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499331]
NPO19507	Schisandra lancifolia	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16643044]
NPO19507	Schisandra lancifolia	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19507	Schisandra lancifolia	Species	Schisandraceae	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
Others	2

Activity Type	# Activity
Cell Line	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1452	Cell Line	C8166	Homo sapiens	CC50	>	200.0	ug.mL-1	PMID[573306]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	88.3	ug.mL-1	PMID[573306]
NPT2	Others	Unspecified		Ratio CC50/EC50	>	2.26	n.a.	PMID[573306]

☑ 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 NPC192309 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	339
0.1-0.2	2166
0.2-0.3	7245
0.3-0.4	13715
0.4-0.5	11063
0.5-0.6	6290
0.6-0.7	1725
0.7-0.8	127
0.8-0.85	14
0.85-0.9	7
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9912	High Similarity	NPC1538
0.9737	High Similarity	NPC42747
0.9492	High Similarity	NPC13071
0.9316	High Similarity	NPC144625
0.9244	High Similarity	NPC172823
0.916	High Similarity	NPC11732
0.9098	High Similarity	NPC224623
0.8974	High Similarity	NPC147635
0.8974	High Similarity	NPC163693
0.8934	High Similarity	NPC469351
0.8908	High Similarity	NPC186339
0.8151	Intermediate Similarity	NPC209058
0.8051	Intermediate Similarity	NPC471884
0.8	Intermediate Similarity	NPC129992
0.7951	Intermediate Similarity	NPC471145
0.7951	Intermediate Similarity	NPC471146
0.7931	Intermediate Similarity	NPC472756
0.7863	Intermediate Similarity	NPC228311
0.7863	Intermediate Similarity	NPC41674
0.7863	Intermediate Similarity	NPC469441
0.7845	Intermediate Similarity	NPC475873
0.7845	Intermediate Similarity	NPC475871
0.7845	Intermediate Similarity	NPC472755
0.7845	Intermediate Similarity	NPC475945
0.7845	Intermediate Similarity	NPC110989
0.7826	Intermediate Similarity	NPC474742
0.7805	Intermediate Similarity	NPC475305
0.7805	Intermediate Similarity	NPC36754
0.7805	Intermediate Similarity	NPC475323
0.7797	Intermediate Similarity	NPC469787
0.7797	Intermediate Similarity	NPC469788
0.7797	Intermediate Similarity	NPC290247
0.7797	Intermediate Similarity	NPC26617
0.7778	Intermediate Similarity	NPC203659
0.7778	Intermediate Similarity	NPC474741
0.7769	Intermediate Similarity	NPC471570
0.7759	Intermediate Similarity	NPC472754
0.7759	Intermediate Similarity	NPC474747
0.7759	Intermediate Similarity	NPC225353
0.775	Intermediate Similarity	NPC477103
0.7742	Intermediate Similarity	NPC475401
0.7742	Intermediate Similarity	NPC161060
0.7731	Intermediate Similarity	NPC329876
0.7731	Intermediate Similarity	NPC278693
0.7731	Intermediate Similarity	NPC220773
0.7719	Intermediate Similarity	NPC213947
0.7719	Intermediate Similarity	NPC170143
0.7719	Intermediate Similarity	NPC108475
0.7692	Intermediate Similarity	NPC472770
0.7686	Intermediate Similarity	NPC474750
0.7686	Intermediate Similarity	NPC475495
0.768	Intermediate Similarity	NPC477092
0.7672	Intermediate Similarity	NPC171759
0.7672	Intermediate Similarity	NPC477950
0.7672	Intermediate Similarity	NPC472753
0.7672	Intermediate Similarity	NPC15993
0.7667	Intermediate Similarity	NPC477102
0.7667	Intermediate Similarity	NPC217041
0.7661	Intermediate Similarity	NPC473656
0.7652	Intermediate Similarity	NPC54843
0.7634	Intermediate Similarity	NPC476852
0.7634	Intermediate Similarity	NPC476855
0.7627	Intermediate Similarity	NPC472748
0.7623	Intermediate Similarity	NPC473522
0.7623	Intermediate Similarity	NPC477093
0.7623	Intermediate Similarity	NPC475277
0.7607	Intermediate Similarity	NPC86077
0.7607	Intermediate Similarity	NPC320019
0.7607	Intermediate Similarity	NPC324017
0.7607	Intermediate Similarity	NPC105725
0.7607	Intermediate Similarity	NPC49393
0.7607	Intermediate Similarity	NPC149371
0.7603	Intermediate Similarity	NPC182185
0.76	Intermediate Similarity	NPC475372
0.7594	Intermediate Similarity	NPC471234
0.7586	Intermediate Similarity	NPC280963
0.7581	Intermediate Similarity	NPC277583
0.7578	Intermediate Similarity	NPC469352
0.7578	Intermediate Similarity	NPC472768
0.7576	Intermediate Similarity	NPC472769
0.7565	Intermediate Similarity	NPC477949
0.7563	Intermediate Similarity	NPC472751
0.7563	Intermediate Similarity	NPC252234
0.7563	Intermediate Similarity	NPC223450
0.7563	Intermediate Similarity	NPC168890
0.7563	Intermediate Similarity	NPC472749
0.7563	Intermediate Similarity	NPC475217
0.7559	Intermediate Similarity	NPC471999
0.7559	Intermediate Similarity	NPC472001
0.7559	Intermediate Similarity	NPC472000
0.7557	Intermediate Similarity	NPC476851
0.7557	Intermediate Similarity	NPC476854
0.7544	Intermediate Similarity	NPC475900
0.7542	Intermediate Similarity	NPC469350
0.7542	Intermediate Similarity	NPC472747
0.7542	Intermediate Similarity	NPC472750
0.754	Intermediate Similarity	NPC312536
0.7521	Intermediate Similarity	NPC38154
0.7521	Intermediate Similarity	NPC47880
0.7521	Intermediate Similarity	NPC128733
0.7521	Intermediate Similarity	NPC133907
0.7521	Intermediate Similarity	NPC476270
0.7521	Intermediate Similarity	NPC185141
0.7521	Intermediate Similarity	NPC110443
0.7521	Intermediate Similarity	NPC46998
0.75	Intermediate Similarity	NPC470188
0.75	Intermediate Similarity	NPC471382
0.75	Intermediate Similarity	NPC471380
0.75	Intermediate Similarity	NPC470192
0.7481	Intermediate Similarity	NPC476859
0.748	Intermediate Similarity	NPC98870
0.7479	Intermediate Similarity	NPC100487
0.7478	Intermediate Similarity	NPC126156
0.7478	Intermediate Similarity	NPC476009
0.746	Intermediate Similarity	NPC13710
0.7459	Intermediate Similarity	NPC257240
0.7456	Intermediate Similarity	NPC477131
0.7456	Intermediate Similarity	NPC289004
0.7438	Intermediate Similarity	NPC10150
0.7438	Intermediate Similarity	NPC475960
0.7424	Intermediate Similarity	NPC475371
0.7422	Intermediate Similarity	NPC470829
0.7422	Intermediate Similarity	NPC473228
0.7417	Intermediate Similarity	NPC314244
0.7417	Intermediate Similarity	NPC291643
0.7417	Intermediate Similarity	NPC469401
0.7417	Intermediate Similarity	NPC243998
0.7402	Intermediate Similarity	NPC9674
0.7402	Intermediate Similarity	NPC19028
0.7398	Intermediate Similarity	NPC287311
0.7391	Intermediate Similarity	NPC474490
0.7391	Intermediate Similarity	NPC163228
0.7388	Intermediate Similarity	NPC168879
0.7388	Intermediate Similarity	NPC88668
0.7377	Intermediate Similarity	NPC475588
0.7377	Intermediate Similarity	NPC187876
0.7373	Intermediate Similarity	NPC201718
0.7373	Intermediate Similarity	NPC474339
0.7373	Intermediate Similarity	NPC162024
0.7373	Intermediate Similarity	NPC164598
0.7373	Intermediate Similarity	NPC475099
0.7368	Intermediate Similarity	NPC473234
0.7368	Intermediate Similarity	NPC476863
0.7368	Intermediate Similarity	NPC60386
0.7368	Intermediate Similarity	NPC476300
0.7368	Intermediate Similarity	NPC476862
0.7368	Intermediate Similarity	NPC135776
0.7368	Intermediate Similarity	NPC473273
0.7368	Intermediate Similarity	NPC308656
0.7368	Intermediate Similarity	NPC153590
0.7368	Intermediate Similarity	NPC473263
0.7355	Intermediate Similarity	NPC176756
0.7355	Intermediate Similarity	NPC477513
0.735	Intermediate Similarity	NPC274695
0.735	Intermediate Similarity	NPC471144
0.735	Intermediate Similarity	NPC141191
0.7328	Intermediate Similarity	NPC91771
0.7328	Intermediate Similarity	NPC31645
0.7328	Intermediate Similarity	NPC142529
0.7328	Intermediate Similarity	NPC185553
0.7323	Intermediate Similarity	NPC288679
0.7317	Intermediate Similarity	NPC475463
0.7313	Intermediate Similarity	NPC102316
0.7311	Intermediate Similarity	NPC78127
0.7311	Intermediate Similarity	NPC471757
0.7304	Intermediate Similarity	NPC469632
0.7304	Intermediate Similarity	NPC473331
0.7302	Intermediate Similarity	NPC54739
0.7295	Intermediate Similarity	NPC167044
0.7295	Intermediate Similarity	NPC117604
0.7293	Intermediate Similarity	NPC264192
0.7281	Intermediate Similarity	NPC133698
0.7281	Intermediate Similarity	NPC284185
0.728	Intermediate Similarity	NPC46269
0.728	Intermediate Similarity	NPC473535
0.728	Intermediate Similarity	NPC106395
0.7273	Intermediate Similarity	NPC287423
0.7273	Intermediate Similarity	NPC9303
0.7273	Intermediate Similarity	NPC16313
0.7273	Intermediate Similarity	NPC42399
0.7273	Intermediate Similarity	NPC475802
0.7273	Intermediate Similarity	NPC54737
0.7266	Intermediate Similarity	NPC25887
0.7266	Intermediate Similarity	NPC472933
0.7265	Intermediate Similarity	NPC328562
0.7265	Intermediate Similarity	NPC471462
0.7265	Intermediate Similarity	NPC169205
0.7265	Intermediate Similarity	NPC474313
0.7265	Intermediate Similarity	NPC323421
0.7257	Intermediate Similarity	NPC474951
0.7252	Intermediate Similarity	NPC470922
0.725	Intermediate Similarity	NPC4620
0.725	Intermediate Similarity	NPC475321
0.7241	Intermediate Similarity	NPC48803
0.7241	Intermediate Similarity	NPC90121
0.7241	Intermediate Similarity	NPC193645
0.7241	Intermediate Similarity	NPC275960
0.7241	Intermediate Similarity	NPC67584
0.7241	Intermediate Similarity	NPC36954
0.7236	Intermediate Similarity	NPC139838

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 NPC192309 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	367
0.1-0.2	2789
0.2-0.3	3918
0.3-0.4	1463
0.4-0.5	384
0.5-0.6	199
0.6-0.7	29
0.7-0.8	1
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
0.7797	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD6371	Approved
0.7241	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7078	Approved
0.7121	Intermediate Similarity	NPD7492	Approved
0.7077	Intermediate Similarity	NPD6054	Approved
0.7068	Intermediate Similarity	NPD6616	Approved
0.697	Remote Similarity	NPD6370	Approved
0.6963	Remote Similarity	NPD7736	Approved
0.6947	Remote Similarity	NPD6059	Approved
0.6912	Remote Similarity	NPD7319	Approved
0.6911	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD6015	Approved
0.6894	Remote Similarity	NPD6016	Approved
0.6889	Remote Similarity	NPD8293	Discontinued
0.688	Remote Similarity	NPD6686	Approved
0.6842	Remote Similarity	NPD5988	Approved
0.6818	Remote Similarity	NPD6319	Approved
0.6815	Remote Similarity	NPD7507	Approved
0.6723	Remote Similarity	NPD5282	Discontinued
0.6667	Remote Similarity	NPD1695	Approved
0.6667	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD6053	Discontinued
0.6667	Remote Similarity	NPD6882	Approved
0.661	Remote Similarity	NPD5785	Approved
0.6591	Remote Similarity	NPD6009	Approved
0.6589	Remote Similarity	NPD6649	Approved
0.6589	Remote Similarity	NPD6650	Approved
0.6573	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD7260	Phase 2
0.6562	Remote Similarity	NPD6373	Approved
0.6562	Remote Similarity	NPD6372	Approved
0.6525	Remote Similarity	NPD6845	Suspended
0.6504	Remote Similarity	NPD5696	Approved
0.6484	Remote Similarity	NPD6899	Approved
0.6484	Remote Similarity	NPD6881	Approved
0.6484	Remote Similarity	NPD7320	Approved
0.6475	Remote Similarity	NPD6033	Approved
0.6471	Remote Similarity	NPD46	Approved
0.6471	Remote Similarity	NPD6698	Approved
0.6466	Remote Similarity	NPD7115	Discovery
0.6462	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD6675	Approved
0.6457	Remote Similarity	NPD6402	Approved
0.6457	Remote Similarity	NPD7128	Approved
0.6457	Remote Similarity	NPD5739	Approved
0.6423	Remote Similarity	NPD8328	Phase 3
0.6417	Remote Similarity	NPD7983	Approved
0.6406	Remote Similarity	NPD5697	Approved
0.6385	Remote Similarity	NPD7102	Approved
0.6385	Remote Similarity	NPD6883	Approved
0.6385	Remote Similarity	NPD7290	Approved
0.6364	Remote Similarity	NPD4632	Approved
0.6336	Remote Similarity	NPD6617	Approved
0.6336	Remote Similarity	NPD8130	Phase 1
0.6336	Remote Similarity	NPD6869	Approved
0.6336	Remote Similarity	NPD6847	Approved
0.6325	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD6012	Approved
0.6308	Remote Similarity	NPD6013	Approved
0.6308	Remote Similarity	NPD6014	Approved
0.6304	Remote Similarity	NPD7604	Phase 2
0.6296	Remote Similarity	NPD7328	Approved
0.6296	Remote Similarity	NPD7327	Approved
0.629	Remote Similarity	NPD6083	Phase 2
0.629	Remote Similarity	NPD6084	Phase 2
0.6279	Remote Similarity	NPD5701	Approved
0.6277	Remote Similarity	NPD8515	Approved
0.6277	Remote Similarity	NPD8513	Phase 3
0.6277	Remote Similarity	NPD8266	Approved
0.6277	Remote Similarity	NPD8267	Approved
0.6277	Remote Similarity	NPD8269	Approved
0.6277	Remote Similarity	NPD8268	Approved
0.6277	Remote Similarity	NPD8516	Approved
0.6277	Remote Similarity	NPD5983	Phase 2
0.6277	Remote Similarity	NPD8517	Approved
0.6268	Remote Similarity	NPD5956	Approved
0.626	Remote Similarity	NPD5695	Phase 3
0.625	Remote Similarity	NPD7516	Approved
0.624	Remote Similarity	NPD4225	Approved
0.624	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD6011	Approved
0.6214	Remote Similarity	NPD6336	Discontinued
0.6204	Remote Similarity	NPD8377	Approved
0.6204	Remote Similarity	NPD8294	Approved
0.6202	Remote Similarity	NPD6008	Approved
0.6198	Remote Similarity	NPD7838	Discovery
0.6186	Remote Similarity	NPD5363	Approved
0.6159	Remote Similarity	NPD8380	Approved
0.6159	Remote Similarity	NPD8335	Approved
0.6159	Remote Similarity	NPD8379	Approved
0.6159	Remote Similarity	NPD8296	Approved
0.6159	Remote Similarity	NPD8033	Approved
0.6159	Remote Similarity	NPD8378	Approved
0.6154	Remote Similarity	NPD6412	Phase 2
0.6136	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD4634	Approved
0.6134	Remote Similarity	NPD5786	Approved
0.6111	Remote Similarity	NPD7638	Approved
0.609	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD7642	Approved
0.6068	Remote Similarity	NPD6435	Approved
0.6063	Remote Similarity	NPD7639	Approved
0.6063	Remote Similarity	NPD7640	Approved
0.6056	Remote Similarity	NPD8074	Phase 3
0.605	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6043	Remote Similarity	NPD7503	Approved
0.6033	Remote Similarity	NPD5737	Approved
0.6033	Remote Similarity	NPD6672	Approved
0.6029	Remote Similarity	NPD6274	Approved
0.6016	Remote Similarity	NPD5693	Phase 1
0.6016	Remote Similarity	NPD1700	Approved
0.6014	Remote Similarity	NPD7100	Approved
0.6014	Remote Similarity	NPD7101	Approved
0.6014	Remote Similarity	NPD8336	Approved
0.6014	Remote Similarity	NPD8337	Approved
0.6	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5210	Approved
0.6	Remote Similarity	NPD4629	Approved
0.6	Remote Similarity	NPD8080	Discontinued
0.5985	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD5369	Approved
0.5969	Remote Similarity	NPD5211	Phase 2
0.5968	Remote Similarity	NPD5779	Approved
0.5968	Remote Similarity	NPD5778	Approved
0.5968	Remote Similarity	NPD6399	Phase 3
0.5952	Remote Similarity	NPD7839	Suspended
0.595	Remote Similarity	NPD4250	Approved
0.595	Remote Similarity	NPD4251	Approved
0.5942	Remote Similarity	NPD6335	Approved
0.594	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD5285	Approved
0.5938	Remote Similarity	NPD5286	Approved
0.5938	Remote Similarity	NPD4696	Approved
0.5932	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD4270	Approved
0.5932	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD4269	Approved
0.5929	Remote Similarity	NPD8444	Approved
0.5929	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD1694	Approved
0.5909	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5906	Remote Similarity	NPD4755	Approved
0.5897	Remote Similarity	NPD5368	Approved
0.5887	Remote Similarity	NPD7637	Suspended
0.5882	Remote Similarity	NPD5362	Discontinued
0.5882	Remote Similarity	NPD8133	Approved
0.5878	Remote Similarity	NPD5141	Approved
0.587	Remote Similarity	NPD6317	Approved
0.5868	Remote Similarity	NPD4249	Approved
0.5854	Remote Similarity	NPD6080	Approved
0.5854	Remote Similarity	NPD6673	Approved
0.5854	Remote Similarity	NPD6904	Approved
0.5852	Remote Similarity	NPD2204	Approved
0.585	Remote Similarity	NPD8338	Approved
0.5846	Remote Similarity	NPD5226	Approved
0.5846	Remote Similarity	NPD4633	Approved
0.5846	Remote Similarity	NPD5225	Approved
0.5846	Remote Similarity	NPD5224	Approved
0.5845	Remote Similarity	NPD7830	Approved
0.5845	Remote Similarity	NPD7829	Approved
0.5827	Remote Similarity	NPD6313	Approved
0.5827	Remote Similarity	NPD6314	Approved
0.5824	Remote Similarity	NPD7799	Discontinued
0.5816	Remote Similarity	NPD6908	Approved
0.5816	Remote Similarity	NPD6921	Approved
0.5816	Remote Similarity	NPD6909	Approved
0.5816	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD4700	Approved
0.5802	Remote Similarity	NPD5174	Approved
0.5802	Remote Similarity	NPD5175	Approved
0.5798	Remote Similarity	NPD5209	Approved
0.5797	Remote Similarity	NPD6868	Approved
0.5769	Remote Similarity	NPD5344	Discontinued
0.5769	Remote Similarity	NPD5223	Approved
0.5764	Remote Similarity	NPD8451	Approved
0.5763	Remote Similarity	NPD4252	Approved
0.5762	Remote Similarity	NPD6333	Approved
0.5762	Remote Similarity	NPD6334	Approved
0.576	Remote Similarity	NPD6411	Approved
0.576	Remote Similarity	NPD6050	Approved
0.575	Remote Similarity	NPD6110	Phase 1
0.5748	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5746	Remote Similarity	NPD4729	Approved
0.5746	Remote Similarity	NPD4730	Approved
0.5733	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD4753	Phase 2
0.5724	Remote Similarity	NPD8448	Approved
0.5714	Remote Similarity	NPD4767	Approved
0.5714	Remote Similarity	NPD4768	Approved
0.5714	Remote Similarity	NPD7641	Discontinued
0.5703	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5703	Remote Similarity	NPD5222	Approved
0.5703	Remote Similarity	NPD4697	Phase 3
0.5703	Remote Similarity	NPD5221	Approved
0.5692	Remote Similarity	NPD6648	Approved
0.568	Remote Similarity	NPD5692	Phase 3
0.5672	Remote Similarity	NPD6614	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