NPASS Compound

Structure

NPC42747 OpenBabel07101718222D 38 44 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 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 0.8660 1.1235 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 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 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 0.4751 0.3117 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 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 -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 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 -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 25 1 0 0 0 0 4 25 1 0 0 0 0 6 7 1 0 0 0 0 6 15 2 0 0 0 0 7 17 1 0 0 0 0 8 9 1 0 0 0 0 8 26 1 0 0 0 0 10 13 2 0 0 0 0 11 18 1 0 0 0 0 11 19 1 0 0 0 0 12 27 1 0 0 0 0 13 24 1 0 0 0 0 14 2 1 1 0 0 0 14 20 1 0 0 0 0 14 22 1 0 0 0 0 15 23 1 0 0 0 0 15 27 1 0 0 0 0 16 10 1 6 0 0 0 16 35 1 0 0 0 0 17 25 1 0 0 0 0 17 28 1 1 0 0 0 18 28 1 6 0 0 0 18 36 1 0 0 0 0 19 30 2 0 0 0 0 19 37 1 0 0 0 0 20 16 1 6 0 0 0 20 21 1 0 0 0 0 21 26 1 6 0 0 0 21 29 1 0 0 0 0 22 26 1 0 0 0 0 22 31 2 0 0 0 0 23 29 1 0 0 0 0 23 32 2 0 0 0 0 24 33 2 0 0 0 0 24 35 1 0 0 0 0 25 36 1 0 0 0 0 26 5 1 1 0 0 0 27 9 1 1 0 0 0 27 38 1 0 0 0 0 28 12 1 1 0 0 0 28 37 1 0 0 0 0 29 34 1 6 0 0 0 29 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	526.22
Volume:	513.538
LogP:	2.988
LogD:	1.807
LogS:	-4.396
# Rotatable Bonds:	1
TPSA:	132.5
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	7
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.418
Synthetic Accessibility Score:	7.38
Fsp3:	0.69
Lipinski Rule-of-5:	Accepted
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:	-5.433
MDCK Permeability:	8.181487646652386e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.831
Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.954

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.956
Plasma Protein Binding (PPB):	88.8144760131836%
Volume Distribution (VD):	1.518
Pgp-substrate:	10.244464874267578%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.976
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.323
CYP2C9-inhibitor:	0.017
CYP2C9-substrate:	0.018
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.089
CYP3A4-inhibitor:	0.819
CYP3A4-substrate:	0.601

ADMET: Excretion

Clearance (CL):	16.237
Half-life (T1/2):	0.122

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.365
Drug-inuced Liver Injury (DILI):	0.907
AMES Toxicity:	0.13
Rat Oral Acute Toxicity:	0.971
Maximum Recommended Daily Dose:	0.549
Skin Sensitization:	0.214
Carcinogencity:	0.876
Eye Corrosion:	0.025
Eye Irritation:	0.012
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC42747

Natural Product ID:	NPC42747
*Common Name:**	Lancifodilactone K
IUPAC Name:	n.a.
Synonyms:	Lancifodilactone K
Standard InCHIKey:	VLKJPGBRNPVIQC-OTFBPMOZSA-N
Standard InCHI:	InChI=1S/C29H34O9/c1-13-10-16(35-24(13)33)20-14(2)22(31)26(5)8-9-27-12-28-17(25(3,4)36-18(28)11-19(30)37-28)7-6-15(27)23(32)29(34,38-27)21(20)26/h6,10,14,16-18,20-21,34H,7-9,11-12H2,1-5H3/t14-,16-,17-,18+,20+,21-,26-,27-,28+,29-/m0/s1
SMILES:	O=C1C[C@@H]2[C@@]3(O1)C[C@]14CC[C@]5([C@@H]([C@](O1)(C(=O)C4=CC[C@H]3C(O2)(C)C)O)[C@H]([C@@H](C5=O)C)[C@@H]1C=C(C(=O)O1)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL446803
PubChem CID:	11598937
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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.	stem	n.a.	PMID[15787482]
NPO19507	Schisandra lancifolia	Species	Schisandraceae	Eukaryota	n.a.	leaf	n.a.	PMID[15787482]
NPO19507	Schisandra lancifolia	Species	Schisandraceae	Eukaryota	n.a.	leaf	n.a.	PMID[15901155]
NPO19507	Schisandra lancifolia	Species	Schisandraceae	Eukaryota	n.a.	stem	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[575604]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	78.5	ug.mL-1	PMID[575604]
NPT2	Others	Unspecified		Ratio CC50/EC50	>	2.55	n.a.	PMID[575604]

☑ 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 NPC42747 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	326
0.1-0.2	2037
0.2-0.3	6828
0.3-0.4	12543
0.4-0.5	11990
0.5-0.6	6501
0.6-0.7	2225
0.7-0.8	223
0.8-0.85	11
0.85-0.9	7
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9737	High Similarity	NPC192309
0.9652	High Similarity	NPC1538
0.9492	High Similarity	NPC172823
0.9412	High Similarity	NPC13071
0.9407	High Similarity	NPC11732
0.9224	High Similarity	NPC147635
0.9224	High Similarity	NPC163693
0.9174	High Similarity	NPC469351
0.9076	High Similarity	NPC144625
0.9024	High Similarity	NPC224623
0.8833	High Similarity	NPC186339
0.8235	Intermediate Similarity	NPC209058
0.8033	Intermediate Similarity	NPC471145
0.8017	Intermediate Similarity	NPC472756
0.7983	Intermediate Similarity	NPC471884
0.7937	Intermediate Similarity	NPC129992
0.7931	Intermediate Similarity	NPC472755
0.7886	Intermediate Similarity	NPC471146
0.7886	Intermediate Similarity	NPC36754
0.7886	Intermediate Similarity	NPC475305
0.7845	Intermediate Similarity	NPC472754
0.7833	Intermediate Similarity	NPC477103
0.7823	Intermediate Similarity	NPC475401
0.7823	Intermediate Similarity	NPC161060
0.7778	Intermediate Similarity	NPC475871
0.7778	Intermediate Similarity	NPC475873
0.7778	Intermediate Similarity	NPC475945
0.7769	Intermediate Similarity	NPC475495
0.7769	Intermediate Similarity	NPC472770
0.776	Intermediate Similarity	NPC477092
0.7759	Intermediate Similarity	NPC15993
0.7759	Intermediate Similarity	NPC472753
0.7759	Intermediate Similarity	NPC474742
0.775	Intermediate Similarity	NPC477102
0.7742	Intermediate Similarity	NPC475323
0.7731	Intermediate Similarity	NPC26617
0.7712	Intermediate Similarity	NPC203659
0.7712	Intermediate Similarity	NPC474741
0.7712	Intermediate Similarity	NPC472748
0.7712	Intermediate Similarity	NPC100487
0.7705	Intermediate Similarity	NPC477093
0.7705	Intermediate Similarity	NPC471570
0.7705	Intermediate Similarity	NPC473522
0.7705	Intermediate Similarity	NPC475277
0.7692	Intermediate Similarity	NPC149371
0.7692	Intermediate Similarity	NPC320019
0.7692	Intermediate Similarity	NPC324017
0.7692	Intermediate Similarity	NPC474747
0.7692	Intermediate Similarity	NPC105725
0.7672	Intermediate Similarity	NPC280963
0.7669	Intermediate Similarity	NPC471234
0.7661	Intermediate Similarity	NPC277583
0.7652	Intermediate Similarity	NPC213947
0.7652	Intermediate Similarity	NPC108475
0.7652	Intermediate Similarity	NPC472769
0.7652	Intermediate Similarity	NPC170143
0.7647	Intermediate Similarity	NPC472751
0.7647	Intermediate Similarity	NPC472749
0.7647	Intermediate Similarity	NPC41674
0.7647	Intermediate Similarity	NPC469441
0.7647	Intermediate Similarity	NPC228311
0.7638	Intermediate Similarity	NPC471999
0.7638	Intermediate Similarity	NPC470829
0.7638	Intermediate Similarity	NPC473228
0.7638	Intermediate Similarity	NPC472000
0.7638	Intermediate Similarity	NPC472001
0.7627	Intermediate Similarity	NPC472747
0.7627	Intermediate Similarity	NPC472750
0.7627	Intermediate Similarity	NPC110989
0.7623	Intermediate Similarity	NPC474750
0.7607	Intermediate Similarity	NPC110443
0.7607	Intermediate Similarity	NPC47880
0.7607	Intermediate Similarity	NPC476270
0.7607	Intermediate Similarity	NPC46998
0.7607	Intermediate Similarity	NPC185141
0.7607	Intermediate Similarity	NPC171759
0.7607	Intermediate Similarity	NPC128733
0.7607	Intermediate Similarity	NPC133907
0.7603	Intermediate Similarity	NPC38154
0.76	Intermediate Similarity	NPC473656
0.7586	Intermediate Similarity	NPC54843
0.7583	Intermediate Similarity	NPC290247
0.7583	Intermediate Similarity	NPC469787
0.7583	Intermediate Similarity	NPC470192
0.7583	Intermediate Similarity	NPC469788
0.7576	Intermediate Similarity	NPC476852
0.7576	Intermediate Similarity	NPC476855
0.7542	Intermediate Similarity	NPC49393
0.7542	Intermediate Similarity	NPC86077
0.7542	Intermediate Similarity	NPC225353
0.7541	Intermediate Similarity	NPC257240
0.754	Intermediate Similarity	NPC13710
0.754	Intermediate Similarity	NPC475372
0.7521	Intermediate Similarity	NPC329876
0.7521	Intermediate Similarity	NPC117604
0.7521	Intermediate Similarity	NPC220773
0.7521	Intermediate Similarity	NPC475960
0.7521	Intermediate Similarity	NPC278693
0.752	Intermediate Similarity	NPC54739
0.7519	Intermediate Similarity	NPC469352
0.7519	Intermediate Similarity	NPC472768
0.75	Intermediate Similarity	NPC469401
0.75	Intermediate Similarity	NPC223450
0.75	Intermediate Similarity	NPC476854
0.75	Intermediate Similarity	NPC314244
0.75	Intermediate Similarity	NPC475217
0.75	Intermediate Similarity	NPC476851
0.75	Intermediate Similarity	NPC252234
0.748	Intermediate Similarity	NPC312536
0.748	Intermediate Similarity	NPC287311
0.7478	Intermediate Similarity	NPC475900
0.7478	Intermediate Similarity	NPC67584
0.7459	Intermediate Similarity	NPC217041
0.7459	Intermediate Similarity	NPC475588
0.7458	Intermediate Similarity	NPC477950
0.7458	Intermediate Similarity	NPC164598
0.7458	Intermediate Similarity	NPC474339
0.7458	Intermediate Similarity	NPC201718
0.7456	Intermediate Similarity	NPC476300
0.744	Intermediate Similarity	NPC471380
0.744	Intermediate Similarity	NPC471382
0.7438	Intermediate Similarity	NPC477513
0.7436	Intermediate Similarity	NPC471144
0.7436	Intermediate Similarity	NPC470188
0.7424	Intermediate Similarity	NPC476859
0.7414	Intermediate Similarity	NPC476009
0.7414	Intermediate Similarity	NPC31645
0.7414	Intermediate Similarity	NPC213078
0.7398	Intermediate Similarity	NPC182185
0.7395	Intermediate Similarity	NPC471757
0.7395	Intermediate Similarity	NPC78127
0.7391	Intermediate Similarity	NPC477131
0.7385	Intermediate Similarity	NPC472399
0.7377	Intermediate Similarity	NPC10150
0.7368	Intermediate Similarity	NPC475371
0.736	Intermediate Similarity	NPC106395
0.736	Intermediate Similarity	NPC46269
0.7355	Intermediate Similarity	NPC9303
0.7355	Intermediate Similarity	NPC168890
0.7355	Intermediate Similarity	NPC243998
0.7355	Intermediate Similarity	NPC475802
0.7355	Intermediate Similarity	NPC291643
0.7355	Intermediate Similarity	NPC16313
0.735	Intermediate Similarity	NPC323421
0.735	Intermediate Similarity	NPC477949
0.735	Intermediate Similarity	NPC161493
0.735	Intermediate Similarity	NPC471462
0.735	Intermediate Similarity	NPC328562
0.7348	Intermediate Similarity	NPC287423
0.7348	Intermediate Similarity	NPC42399
0.7344	Intermediate Similarity	NPC9674
0.7344	Intermediate Similarity	NPC472933
0.7344	Intermediate Similarity	NPC19028
0.7338	Intermediate Similarity	NPC25887
0.7333	Intermediate Similarity	NPC469350
0.7333	Intermediate Similarity	NPC168879
0.7333	Intermediate Similarity	NPC4620
0.7333	Intermediate Similarity	NPC88668
0.7328	Intermediate Similarity	NPC52044
0.7328	Intermediate Similarity	NPC36954
0.7328	Intermediate Similarity	NPC470922
0.7328	Intermediate Similarity	NPC163228
0.7317	Intermediate Similarity	NPC187876
0.7313	Intermediate Similarity	NPC476862
0.7313	Intermediate Similarity	NPC476863
0.7311	Intermediate Similarity	NPC264477
0.7311	Intermediate Similarity	NPC150923
0.7311	Intermediate Similarity	NPC475099
0.7311	Intermediate Similarity	NPC477511
0.7311	Intermediate Similarity	NPC162024
0.7308	Intermediate Similarity	NPC287236
0.7304	Intermediate Similarity	NPC153590
0.7304	Intermediate Similarity	NPC60386
0.7304	Intermediate Similarity	NPC473273
0.7304	Intermediate Similarity	NPC179746
0.7304	Intermediate Similarity	NPC81419
0.7304	Intermediate Similarity	NPC473234
0.7304	Intermediate Similarity	NPC135776
0.7304	Intermediate Similarity	NPC308656
0.7304	Intermediate Similarity	NPC473263
0.7302	Intermediate Similarity	NPC67290
0.7302	Intermediate Similarity	NPC138303
0.7302	Intermediate Similarity	NPC133677
0.7295	Intermediate Similarity	NPC326994
0.7295	Intermediate Similarity	NPC194620
0.7295	Intermediate Similarity	NPC324327
0.7295	Intermediate Similarity	NPC72813
0.7295	Intermediate Similarity	NPC474421
0.7293	Intermediate Similarity	NPC473620
0.7288	Intermediate Similarity	NPC187268
0.7288	Intermediate Similarity	NPC141191
0.7288	Intermediate Similarity	NPC471610
0.7286	Intermediate Similarity	NPC470426
0.7281	Intermediate Similarity	NPC51004
0.728	Intermediate Similarity	NPC66108
0.728	Intermediate Similarity	NPC123855
0.728	Intermediate Similarity	NPC138757
0.728	Intermediate Similarity	NPC76550
0.728	Intermediate Similarity	NPC98870
0.7273	Intermediate Similarity	NPC220964

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 NPC42747 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	361
0.1-0.2	2643
0.2-0.3	3926
0.3-0.4	1529
0.4-0.5	436
0.5-0.6	221
0.6-0.7	31
0.7-0.8	3
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
0.7731	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD6371	Approved
0.7179	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD7078	Approved
0.7068	Intermediate Similarity	NPD7492	Approved
0.7023	Intermediate Similarity	NPD6054	Approved
0.7015	Intermediate Similarity	NPD6616	Approved
0.6917	Remote Similarity	NPD6370	Approved
0.6912	Remote Similarity	NPD7736	Approved
0.6894	Remote Similarity	NPD6059	Approved
0.6861	Remote Similarity	NPD7319	Approved
0.6855	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6015	Approved
0.6842	Remote Similarity	NPD6016	Approved
0.6838	Remote Similarity	NPD8293	Discontinued
0.6825	Remote Similarity	NPD6686	Approved
0.6807	Remote Similarity	NPD5282	Discontinued
0.6791	Remote Similarity	NPD5988	Approved
0.6767	Remote Similarity	NPD6319	Approved
0.6765	Remote Similarity	NPD7507	Approved
0.6744	Remote Similarity	NPD6053	Discontinued
0.6695	Remote Similarity	NPD5785	Approved
0.6643	Remote Similarity	NPD7260	Phase 2
0.6615	Remote Similarity	NPD8297	Approved
0.6615	Remote Similarity	NPD6882	Approved
0.661	Remote Similarity	NPD1695	Approved
0.6596	Remote Similarity	NPD6845	Suspended
0.6555	Remote Similarity	NPD6698	Approved
0.6555	Remote Similarity	NPD46	Approved
0.6541	Remote Similarity	NPD6009	Approved
0.6541	Remote Similarity	NPD7115	Discovery
0.6538	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6650	Approved
0.6538	Remote Similarity	NPD6649	Approved
0.6528	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD6372	Approved
0.6512	Remote Similarity	NPD6373	Approved
0.65	Remote Similarity	NPD7983	Approved
0.6452	Remote Similarity	NPD5696	Approved
0.6434	Remote Similarity	NPD6881	Approved
0.6434	Remote Similarity	NPD6899	Approved
0.6434	Remote Similarity	NPD7320	Approved
0.6429	Remote Similarity	NPD6033	Approved
0.641	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD6402	Approved
0.6406	Remote Similarity	NPD5739	Approved
0.6406	Remote Similarity	NPD7128	Approved
0.6406	Remote Similarity	NPD6675	Approved
0.6377	Remote Similarity	NPD8328	Phase 3
0.6357	Remote Similarity	NPD5697	Approved
0.635	Remote Similarity	NPD8513	Phase 3
0.635	Remote Similarity	NPD8515	Approved
0.635	Remote Similarity	NPD8267	Approved
0.635	Remote Similarity	NPD8268	Approved
0.635	Remote Similarity	NPD8266	Approved
0.635	Remote Similarity	NPD8269	Approved
0.635	Remote Similarity	NPD8516	Approved
0.635	Remote Similarity	NPD8517	Approved
0.6336	Remote Similarity	NPD7290	Approved
0.6336	Remote Similarity	NPD6883	Approved
0.6336	Remote Similarity	NPD7102	Approved
0.632	Remote Similarity	NPD4225	Approved
0.632	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD4632	Approved
0.6288	Remote Similarity	NPD6847	Approved
0.6288	Remote Similarity	NPD6869	Approved
0.6288	Remote Similarity	NPD6617	Approved
0.6288	Remote Similarity	NPD8130	Phase 1
0.6281	Remote Similarity	NPD7838	Discovery
0.6279	Remote Similarity	NPD6008	Approved
0.6271	Remote Similarity	NPD5363	Approved
0.626	Remote Similarity	NPD6012	Approved
0.626	Remote Similarity	NPD6013	Approved
0.626	Remote Similarity	NPD6014	Approved
0.6259	Remote Similarity	NPD7604	Phase 2
0.625	Remote Similarity	NPD7328	Approved
0.625	Remote Similarity	NPD7327	Approved
0.624	Remote Similarity	NPD6084	Phase 2
0.624	Remote Similarity	NPD6083	Phase 2
0.6232	Remote Similarity	NPD5983	Phase 2
0.6232	Remote Similarity	NPD8033	Approved
0.6231	Remote Similarity	NPD5701	Approved
0.6224	Remote Similarity	NPD5956	Approved
0.6218	Remote Similarity	NPD5786	Approved
0.621	Remote Similarity	NPD5695	Phase 3
0.6204	Remote Similarity	NPD7516	Approved
0.6183	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD6011	Approved
0.617	Remote Similarity	NPD6336	Discontinued
0.6159	Remote Similarity	NPD8294	Approved
0.6159	Remote Similarity	NPD8377	Approved
0.6143	Remote Similarity	NPD7642	Approved
0.6127	Remote Similarity	NPD8074	Phase 3
0.6115	Remote Similarity	NPD8378	Approved
0.6115	Remote Similarity	NPD8380	Approved
0.6115	Remote Similarity	NPD8335	Approved
0.6115	Remote Similarity	NPD8296	Approved
0.6115	Remote Similarity	NPD8379	Approved
0.6107	Remote Similarity	NPD6412	Phase 2
0.609	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.609	Remote Similarity	NPD4634	Approved
0.6071	Remote Similarity	NPD8080	Discontinued
0.6068	Remote Similarity	NPD5369	Approved
0.6063	Remote Similarity	NPD7638	Approved
0.6058	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD5778	Approved
0.6048	Remote Similarity	NPD5779	Approved
0.6048	Remote Similarity	NPD6399	Phase 3
0.6045	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD4250	Approved
0.6033	Remote Similarity	NPD4251	Approved
0.6032	Remote Similarity	NPD7839	Suspended
0.6017	Remote Similarity	NPD4270	Approved
0.6017	Remote Similarity	NPD6435	Approved
0.6017	Remote Similarity	NPD4269	Approved
0.6016	Remote Similarity	NPD7639	Approved
0.6016	Remote Similarity	NPD7640	Approved
0.6	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8444	Approved
0.6	Remote Similarity	NPD7503	Approved
0.5985	Remote Similarity	NPD6274	Approved
0.5984	Remote Similarity	NPD6672	Approved
0.5984	Remote Similarity	NPD5737	Approved
0.5972	Remote Similarity	NPD8336	Approved
0.5972	Remote Similarity	NPD8337	Approved
0.5971	Remote Similarity	NPD7101	Approved
0.5971	Remote Similarity	NPD7100	Approved
0.5969	Remote Similarity	NPD1700	Approved
0.5968	Remote Similarity	NPD5693	Phase 1
0.5968	Remote Similarity	NPD7637	Suspended
0.5966	Remote Similarity	NPD5362	Discontinued
0.5952	Remote Similarity	NPD5210	Approved
0.5952	Remote Similarity	NPD4629	Approved
0.595	Remote Similarity	NPD4249	Approved
0.5948	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD2204	Approved
0.5923	Remote Similarity	NPD5211	Phase 2
0.5915	Remote Similarity	NPD7830	Approved
0.5915	Remote Similarity	NPD7829	Approved
0.5899	Remote Similarity	NPD6335	Approved
0.5896	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5891	Remote Similarity	NPD4696	Approved
0.5891	Remote Similarity	NPD5285	Approved
0.5891	Remote Similarity	NPD5286	Approved
0.5887	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD7799	Discontinued
0.5868	Remote Similarity	NPD1694	Approved
0.5865	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD4755	Approved
0.5847	Remote Similarity	NPD4252	Approved
0.5847	Remote Similarity	NPD5368	Approved
0.5846	Remote Similarity	NPD5344	Discontinued
0.584	Remote Similarity	NPD6411	Approved
0.5839	Remote Similarity	NPD8133	Approved
0.5833	Remote Similarity	NPD8451	Approved
0.5833	Remote Similarity	NPD5141	Approved
0.5827	Remote Similarity	NPD6317	Approved
0.5811	Remote Similarity	NPD8338	Approved
0.5806	Remote Similarity	NPD6673	Approved
0.5806	Remote Similarity	NPD6904	Approved
0.5806	Remote Similarity	NPD6080	Approved
0.5802	Remote Similarity	NPD5225	Approved
0.5802	Remote Similarity	NPD5224	Approved
0.5802	Remote Similarity	NPD5226	Approved
0.5802	Remote Similarity	NPD4633	Approved
0.5793	Remote Similarity	NPD8448	Approved
0.5786	Remote Similarity	NPD7641	Discontinued
0.5786	Remote Similarity	NPD6313	Approved
0.5786	Remote Similarity	NPD6314	Approved
0.5775	Remote Similarity	NPD6908	Approved
0.5775	Remote Similarity	NPD6909	Approved
0.5775	Remote Similarity	NPD6921	Approved
0.5769	Remote Similarity	NPD4700	Approved
0.5769	Remote Similarity	NPD6648	Approved
0.5758	Remote Similarity	NPD5175	Approved
0.5758	Remote Similarity	NPD5174	Approved
0.5755	Remote Similarity	NPD6868	Approved
0.575	Remote Similarity	NPD5209	Approved
0.5725	Remote Similarity	NPD5223	Approved
0.5724	Remote Similarity	NPD6334	Approved
0.5724	Remote Similarity	NPD6333	Approved
0.5714	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6050	Approved
0.5714	Remote Similarity	NPD4819	Approved
0.5714	Remote Similarity	NPD4822	Approved
0.5714	Remote Similarity	NPD4820	Approved
0.5714	Remote Similarity	NPD4821	Approved
0.5714	Remote Similarity	NPD7500	Approved
0.5704	Remote Similarity	NPD4730	Approved
0.5704	Remote Similarity	NPD4729	Approved
0.5703	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD6110	Phase 1
0.5702	Remote Similarity	NPD7154	Phase 3
0.5695	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.568	Remote Similarity	NPD6101	Approved
0.568	Remote Similarity	NPD5764	Clinical (unspecified phase)

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