NPASS Compound

Structure

NPC11732 OpenBabel07101719512D 39 46 0 0 1 0 0 0 0 0999 V2000 -2.0084 2.9313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6471 2.9160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5481 2.4821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3238 0.9797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8786 -0.4567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0509 2.3734 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0469 2.4631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3351 1.7319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 1.2580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3704 -0.6755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7453 0.2364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3013 2.2242 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7379 1.7403 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5047 0.3154 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3865 -0.8541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4062 1.5623 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7699 1.2067 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8090 1.2580 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6394 2.3291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7186 0.7006 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5229 0.8747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7219 1.9188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3351 1.7319 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1840 0.4955 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8090 0.5878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6037 0.7493 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8090 0.5878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9526 -1.7550 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1854 3.2201 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0878 2.3479 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5178 0.7739 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8559 -0.2452 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2670 1.3143 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1957 1.0382 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9126 0.0265 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2910 0.4252 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 2 24 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 6 7 1 0 0 0 0 6 13 2 0 0 0 0 7 14 1 0 0 0 0 8 9 1 0 0 0 0 8 25 1 0 0 0 0 9 27 1 0 0 0 0 10 15 1 0 0 0 0 10 16 1 0 0 0 0 11 27 1 0 0 0 0 11 28 1 0 0 0 0 12 1 1 6 0 0 0 12 17 1 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 13 27 1 0 0 0 0 14 24 1 0 0 0 0 14 28 1 1 0 0 0 15 28 1 6 0 0 0 15 36 1 0 0 0 0 16 30 2 0 0 0 0 16 37 1 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 18 22 1 0 0 0 0 18 35 1 0 0 0 0 19 25 1 0 0 0 0 19 29 1 0 0 0 0 20 25 1 0 0 0 0 20 31 2 0 0 0 0 21 29 1 0 0 0 0 21 32 2 0 0 0 0 22 26 1 0 0 0 0 22 38 1 0 0 0 0 23 26 1 0 0 0 0 23 33 2 0 0 0 0 23 35 1 0 0 0 0 24 36 1 0 0 0 0 26 34 1 0 0 0 0 27 39 1 0 0 0 0 28 37 1 0 0 0 0 29 38 1 0 0 0 0 29 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	542.22
Volume:	516.408
LogP:	2.316
LogD:	1.271
LogS:	-4.603
# Rotatable Bonds:	0
TPSA:	134.66
# H-Bond Aceptor:	10
# H-Bond Donor:	1
# Rings:	8
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.354
Synthetic Accessibility Score:	7.747
Fsp3:	0.793
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:	-5.388
MDCK Permeability:	7.072037260513753e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.028
Human Intestinal Absorption (HIA):	0.105
20% Bioavailability (F20%):	0.973
30% Bioavailability (F30%):	0.969

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.741
Plasma Protein Binding (PPB):	53.5919189453125%
Volume Distribution (VD):	1.384
Pgp-substrate:	35.98616027832031%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.971
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.395
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.047
CYP3A4-inhibitor:	0.896
CYP3A4-substrate:	0.451

ADMET: Excretion

Clearance (CL):	13.423
Half-life (T1/2):	0.183

ADMET: Toxicity

hERG Blockers:	0.072
Human Hepatotoxicity (H-HT):	0.254
Drug-inuced Liver Injury (DILI):	0.866
AMES Toxicity:	0.676
Rat Oral Acute Toxicity:	0.932
Maximum Recommended Daily Dose:	0.199
Skin Sensitization:	0.373
Carcinogencity:	0.498
Eye Corrosion:	0.069
Eye Irritation:	0.013
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC11732

Natural Product ID:	NPC11732
*Common Name:**	Lancifodilactone N
IUPAC Name:	n.a.
Synonyms:	Lancifodilactone N
Standard InCHIKey:	XDISQVVKDHLTOE-LGYFHCBISA-N
Standard InCHI:	InChI=1S/C29H34O10/c1-12-17-18-22(26(5,34)23(33)35-18)38-29-19(17)25(4,20(12)31)8-9-27(39-29)11-28-14(7-6-13(27)21(29)32)24(2,3)36-15(28)10-16(30)37-28/h6,12,14-15,17-19,22,34H,7-11H2,1-5H3/t12-,14-,15+,17+,18+,19-,22-,25-,26+,27-,28+,29-/m0/s1
SMILES:	C[C@H]1[C@@H]2[C@@H]3[C@@H]([C@](C)(C(=O)O3)O)O[C@]34[C@@H]2[C@](C)(CC[C@@]2(C[C@@]56[C@@H](CC=C2C3=O)C(C)(C)O[C@@H]5CC(=O)O6)O4)C1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL445713
PubChem CID:	11649593
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001818] Furopyrans

*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	=	186.3	ug.mL-1	PMID[475802]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	77.6	ug.mL-1	PMID[475802]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	2.4	n.a.	PMID[475802]

☑ 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 NPC11732 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	335
0.1-0.2	2021
0.2-0.3	6788
0.3-0.4	11792
0.4-0.5	11987
0.5-0.6	7332
0.6-0.7	2290
0.7-0.8	134
0.8-0.85	7
0.85-0.9	4
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9748	High Similarity	NPC469351
0.9417	High Similarity	NPC172823
0.9407	High Similarity	NPC42747
0.9316	High Similarity	NPC147635
0.9316	High Similarity	NPC163693
0.9268	High Similarity	NPC224623
0.9244	High Similarity	NPC186339
0.916	High Similarity	NPC192309
0.9083	High Similarity	NPC1538
0.9024	High Similarity	NPC13071
0.8699	High Similarity	NPC144625
0.8136	Intermediate Similarity	NPC469787
0.8136	Intermediate Similarity	NPC290247
0.8136	Intermediate Similarity	NPC469788
0.8	Intermediate Similarity	NPC217041
0.7984	Intermediate Similarity	NPC471145
0.7951	Intermediate Similarity	NPC471570
0.7934	Intermediate Similarity	NPC182185
0.7903	Intermediate Similarity	NPC277583
0.7899	Intermediate Similarity	NPC469441
0.7899	Intermediate Similarity	NPC228311
0.7899	Intermediate Similarity	NPC41674
0.7886	Intermediate Similarity	NPC209058
0.7874	Intermediate Similarity	NPC473228
0.7874	Intermediate Similarity	NPC470829
0.784	Intermediate Similarity	NPC471146
0.7815	Intermediate Similarity	NPC472748
0.7815	Intermediate Similarity	NPC472756
0.7805	Intermediate Similarity	NPC98870
0.7778	Intermediate Similarity	NPC13710
0.7769	Intermediate Similarity	NPC329876
0.7752	Intermediate Similarity	NPC129992
0.775	Intermediate Similarity	NPC472749
0.775	Intermediate Similarity	NPC472751
0.7731	Intermediate Similarity	NPC469350
0.7731	Intermediate Similarity	NPC472747
0.7731	Intermediate Similarity	NPC472750
0.7731	Intermediate Similarity	NPC472755
0.7712	Intermediate Similarity	NPC162024
0.7686	Intermediate Similarity	NPC176756
0.7647	Intermediate Similarity	NPC472754
0.7642	Intermediate Similarity	NPC471884
0.7642	Intermediate Similarity	NPC477103
0.7638	Intermediate Similarity	NPC475401
0.763	Intermediate Similarity	NPC471234
0.7627	Intermediate Similarity	NPC280963
0.7623	Intermediate Similarity	NPC167044
0.7623	Intermediate Similarity	NPC278693
0.7623	Intermediate Similarity	NPC220773
0.7623	Intermediate Similarity	NPC475960
0.7597	Intermediate Similarity	NPC471999
0.7597	Intermediate Similarity	NPC472001
0.7597	Intermediate Similarity	NPC472000
0.7594	Intermediate Similarity	NPC472770
0.7583	Intermediate Similarity	NPC475945
0.7583	Intermediate Similarity	NPC475873
0.7583	Intermediate Similarity	NPC475871
0.7581	Intermediate Similarity	NPC474750
0.7578	Intermediate Similarity	NPC477092
0.7563	Intermediate Similarity	NPC15993
0.7563	Intermediate Similarity	NPC474742
0.7563	Intermediate Similarity	NPC472753
0.7561	Intermediate Similarity	NPC477102
0.7559	Intermediate Similarity	NPC475323
0.7559	Intermediate Similarity	NPC36754
0.7559	Intermediate Similarity	NPC475305
0.7541	Intermediate Similarity	NPC26617
0.7521	Intermediate Similarity	NPC100487
0.7521	Intermediate Similarity	NPC474741
0.7521	Intermediate Similarity	NPC203659
0.75	Intermediate Similarity	NPC320019
0.75	Intermediate Similarity	NPC161060
0.75	Intermediate Similarity	NPC475309
0.75	Intermediate Similarity	NPC474747
0.75	Intermediate Similarity	NPC149371
0.75	Intermediate Similarity	NPC324017
0.7481	Intermediate Similarity	NPC100390
0.7481	Intermediate Similarity	NPC472769
0.7481	Intermediate Similarity	NPC254614
0.748	Intermediate Similarity	NPC54739
0.748	Intermediate Similarity	NPC10150
0.7463	Intermediate Similarity	NPC264192
0.7459	Intermediate Similarity	NPC168890
0.7459	Intermediate Similarity	NPC314244
0.7459	Intermediate Similarity	NPC469401
0.744	Intermediate Similarity	NPC475495
0.7438	Intermediate Similarity	NPC110989
0.7426	Intermediate Similarity	NPC168879
0.7424	Intermediate Similarity	NPC470922
0.7422	Intermediate Similarity	NPC473656
0.7419	Intermediate Similarity	NPC187876
0.7417	Intermediate Similarity	NPC46998
0.7417	Intermediate Similarity	NPC110443
0.7417	Intermediate Similarity	NPC133907
0.7417	Intermediate Similarity	NPC476270
0.7417	Intermediate Similarity	NPC185141
0.7417	Intermediate Similarity	NPC128733
0.7417	Intermediate Similarity	NPC47880
0.7407	Intermediate Similarity	NPC213634
0.7407	Intermediate Similarity	NPC476855
0.7407	Intermediate Similarity	NPC476852
0.7391	Intermediate Similarity	NPC243014
0.7388	Intermediate Similarity	NPC188291
0.7381	Intermediate Similarity	NPC473522
0.7381	Intermediate Similarity	NPC477093
0.7381	Intermediate Similarity	NPC475277
0.7377	Intermediate Similarity	NPC474917
0.7368	Intermediate Similarity	NPC222307
0.7364	Intermediate Similarity	NPC475372
0.7364	Intermediate Similarity	NPC288679
0.736	Intermediate Similarity	NPC257240
0.736	Intermediate Similarity	NPC475463
0.7355	Intermediate Similarity	NPC105725
0.7355	Intermediate Similarity	NPC86077
0.7355	Intermediate Similarity	NPC225353
0.7353	Intermediate Similarity	NPC254146
0.7353	Intermediate Similarity	NPC102316
0.7353	Intermediate Similarity	NPC475139
0.7353	Intermediate Similarity	NPC6274
0.7353	Intermediate Similarity	NPC180902
0.7353	Intermediate Similarity	NPC33378
0.7348	Intermediate Similarity	NPC471392
0.7348	Intermediate Similarity	NPC469352
0.7348	Intermediate Similarity	NPC472768
0.7339	Intermediate Similarity	NPC117604
0.7333	Intermediate Similarity	NPC476851
0.7333	Intermediate Similarity	NPC476854
0.7324	Intermediate Similarity	NPC471171
0.7317	Intermediate Similarity	NPC223450
0.7317	Intermediate Similarity	NPC252234
0.7317	Intermediate Similarity	NPC16313
0.7317	Intermediate Similarity	NPC9303
0.7313	Intermediate Similarity	NPC42399
0.7311	Intermediate Similarity	NPC213947
0.7311	Intermediate Similarity	NPC108475
0.7311	Intermediate Similarity	NPC170143
0.7308	Intermediate Similarity	NPC312536
0.7308	Intermediate Similarity	NPC19028
0.7308	Intermediate Similarity	NPC158963
0.7308	Intermediate Similarity	NPC268958
0.7308	Intermediate Similarity	NPC9674
0.7302	Intermediate Similarity	NPC287311
0.7299	Intermediate Similarity	NPC88668
0.7295	Intermediate Similarity	NPC473148
0.7295	Intermediate Similarity	NPC4620
0.7293	Intermediate Similarity	NPC24651
0.7288	Intermediate Similarity	NPC475900
0.728	Intermediate Similarity	NPC475588
0.728	Intermediate Similarity	NPC38154
0.7279	Intermediate Similarity	NPC473838
0.7279	Intermediate Similarity	NPC475389
0.7273	Intermediate Similarity	NPC474339
0.7273	Intermediate Similarity	NPC171759
0.7273	Intermediate Similarity	NPC164598
0.7265	Intermediate Similarity	NPC476300
0.7259	Intermediate Similarity	NPC476859
0.7259	Intermediate Similarity	NPC311534
0.7259	Intermediate Similarity	NPC270109
0.7259	Intermediate Similarity	NPC473620
0.7258	Intermediate Similarity	NPC474421
0.7258	Intermediate Similarity	NPC326994
0.7258	Intermediate Similarity	NPC72813
0.7258	Intermediate Similarity	NPC324327
0.7258	Intermediate Similarity	NPC194620
0.7258	Intermediate Similarity	NPC470192
0.7258	Intermediate Similarity	NPC477513
0.7254	Intermediate Similarity	NPC470426
0.7252	Intermediate Similarity	NPC107338
0.7252	Intermediate Similarity	NPC109607
0.725	Intermediate Similarity	NPC54843
0.725	Intermediate Similarity	NPC274695
0.725	Intermediate Similarity	NPC471144
0.7246	Intermediate Similarity	NPC182266
0.7246	Intermediate Similarity	NPC471137
0.7246	Intermediate Similarity	NPC475154
0.7246	Intermediate Similarity	NPC475500
0.7246	Intermediate Similarity	NPC471136
0.7246	Intermediate Similarity	NPC100017
0.7246	Intermediate Similarity	NPC223356
0.7246	Intermediate Similarity	NPC242486
0.7246	Intermediate Similarity	NPC15215
0.7246	Intermediate Similarity	NPC473548
0.7239	Intermediate Similarity	NPC217901
0.7239	Intermediate Similarity	NPC198714
0.7236	Intermediate Similarity	NPC220964
0.7236	Intermediate Similarity	NPC309190
0.7236	Intermediate Similarity	NPC475676
0.7227	Intermediate Similarity	NPC31645
0.7227	Intermediate Similarity	NPC476009
0.7226	Intermediate Similarity	NPC471855
0.7222	Intermediate Similarity	NPC194854
0.7222	Intermediate Similarity	NPC48813
0.7218	Intermediate Similarity	NPC105926
0.7218	Intermediate Similarity	NPC91693
0.7218	Intermediate Similarity	NPC472399
0.7218	Intermediate Similarity	NPC67251
0.7218	Intermediate Similarity	NPC265557
0.7218	Intermediate Similarity	NPC18945
0.7214	Intermediate Similarity	NPC596
0.7213	Intermediate Similarity	NPC66110

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 NPC11732 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	320
0.1-0.2	2513
0.2-0.3	3989
0.3-0.4	1580
0.4-0.5	479
0.5-0.6	228
0.6-0.7	38
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
0.7541	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD6371	Approved
0.7097	Intermediate Similarity	NPD4056	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4057	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7078	Approved
0.7037	Intermediate Similarity	NPD7492	Approved
0.6992	Remote Similarity	NPD6054	Approved
0.6985	Remote Similarity	NPD6616	Approved
0.6957	Remote Similarity	NPD7319	Approved
0.6929	Remote Similarity	NPD6686	Approved
0.6889	Remote Similarity	NPD6370	Approved
0.6884	Remote Similarity	NPD7736	Approved
0.6866	Remote Similarity	NPD6059	Approved
0.6861	Remote Similarity	NPD7507	Approved
0.686	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD6016	Approved
0.6815	Remote Similarity	NPD6015	Approved
0.6812	Remote Similarity	NPD8293	Discontinued
0.6777	Remote Similarity	NPD5282	Discontinued
0.6769	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5988	Approved
0.6741	Remote Similarity	NPD6319	Approved
0.6736	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.669	Remote Similarity	NPD6845	Suspended
0.6667	Remote Similarity	NPD46	Approved
0.6667	Remote Similarity	NPD6698	Approved
0.662	Remote Similarity	NPD7260	Phase 2
0.6594	Remote Similarity	NPD8328	Phase 3
0.6591	Remote Similarity	NPD6882	Approved
0.6591	Remote Similarity	NPD6053	Discontinued
0.6569	Remote Similarity	NPD8266	Approved
0.6569	Remote Similarity	NPD8513	Phase 3
0.6569	Remote Similarity	NPD8267	Approved
0.6569	Remote Similarity	NPD8516	Approved
0.6569	Remote Similarity	NPD8268	Approved
0.6569	Remote Similarity	NPD8269	Approved
0.6569	Remote Similarity	NPD8515	Approved
0.6569	Remote Similarity	NPD8517	Approved
0.6519	Remote Similarity	NPD7115	Discovery
0.6519	Remote Similarity	NPD6009	Approved
0.6475	Remote Similarity	NPD7642	Approved
0.6466	Remote Similarity	NPD8297	Approved
0.6429	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD6033	Approved
0.6397	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD5785	Approved
0.6391	Remote Similarity	NPD6650	Approved
0.6391	Remote Similarity	NPD6649	Approved
0.6364	Remote Similarity	NPD6373	Approved
0.6364	Remote Similarity	NPD6372	Approved
0.635	Remote Similarity	NPD7328	Approved
0.635	Remote Similarity	NPD7327	Approved
0.6341	Remote Similarity	NPD7983	Approved
0.6338	Remote Similarity	NPD8074	Phase 3
0.6336	Remote Similarity	NPD6412	Phase 2
0.6331	Remote Similarity	NPD8033	Approved
0.6311	Remote Similarity	NPD1695	Approved
0.6304	Remote Similarity	NPD7516	Approved
0.6299	Remote Similarity	NPD4225	Approved
0.6299	Remote Similarity	NPD5696	Approved
0.6296	Remote Similarity	NPD4632	Approved
0.6288	Remote Similarity	NPD6881	Approved
0.6288	Remote Similarity	NPD7320	Approved
0.6288	Remote Similarity	NPD6899	Approved
0.6286	Remote Similarity	NPD8080	Discontinued
0.626	Remote Similarity	NPD6675	Approved
0.626	Remote Similarity	NPD6402	Approved
0.626	Remote Similarity	NPD7128	Approved
0.626	Remote Similarity	NPD5739	Approved
0.6259	Remote Similarity	NPD8294	Approved
0.6259	Remote Similarity	NPD8377	Approved
0.6214	Remote Similarity	NPD8444	Approved
0.6214	Remote Similarity	NPD8296	Approved
0.6214	Remote Similarity	NPD8380	Approved
0.6214	Remote Similarity	NPD7503	Approved
0.6214	Remote Similarity	NPD8335	Approved
0.6214	Remote Similarity	NPD8379	Approved
0.6214	Remote Similarity	NPD8378	Approved
0.6212	Remote Similarity	NPD5697	Approved
0.6207	Remote Similarity	NPD5956	Approved
0.6194	Remote Similarity	NPD7290	Approved
0.6194	Remote Similarity	NPD6883	Approved
0.6194	Remote Similarity	NPD7102	Approved
0.6148	Remote Similarity	NPD6617	Approved
0.6148	Remote Similarity	NPD6869	Approved
0.6148	Remote Similarity	NPD8130	Phase 1
0.6148	Remote Similarity	NPD6847	Approved
0.6136	Remote Similarity	NPD6008	Approved
0.6129	Remote Similarity	NPD7838	Discovery
0.6127	Remote Similarity	NPD7604	Phase 2
0.6127	Remote Similarity	NPD7830	Approved
0.6127	Remote Similarity	NPD7829	Approved
0.6119	Remote Similarity	NPD6013	Approved
0.6119	Remote Similarity	NPD6014	Approved
0.6119	Remote Similarity	NPD6012	Approved
0.6116	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6099	Remote Similarity	NPD5983	Phase 2
0.6099	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD6083	Phase 2
0.6094	Remote Similarity	NPD6084	Phase 2
0.609	Remote Similarity	NPD5701	Approved
0.6074	Remote Similarity	NPD4634	Approved
0.6069	Remote Similarity	NPD8337	Approved
0.6069	Remote Similarity	NPD8336	Approved
0.6063	Remote Similarity	NPD5695	Phase 3
0.6058	Remote Similarity	NPD8133	Approved
0.6045	Remote Similarity	NPD6011	Approved
0.6042	Remote Similarity	NPD8451	Approved
0.6042	Remote Similarity	NPD6336	Discontinued
0.6016	Remote Similarity	NPD7839	Suspended
0.6	Remote Similarity	NPD8448	Approved
0.6	Remote Similarity	NPD7641	Discontinued
0.5986	Remote Similarity	NPD6921	Approved
0.5984	Remote Similarity	NPD5363	Approved
0.5956	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5954	Remote Similarity	NPD1700	Approved
0.5935	Remote Similarity	NPD5786	Approved
0.5923	Remote Similarity	NPD7638	Approved
0.5912	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5906	Remote Similarity	NPD6399	Phase 3
0.5906	Remote Similarity	NPD8338	Approved
0.5906	Remote Similarity	NPD5778	Approved
0.5906	Remote Similarity	NPD5779	Approved
0.5882	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5878	Remote Similarity	NPD8391	Approved
0.5878	Remote Similarity	NPD8392	Approved
0.5878	Remote Similarity	NPD7639	Approved
0.5878	Remote Similarity	NPD8390	Approved
0.5878	Remote Similarity	NPD7640	Approved
0.5872	Remote Similarity	NPD7799	Discontinued
0.5868	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD8341	Approved
0.5862	Remote Similarity	NPD8340	Approved
0.5862	Remote Similarity	NPD8299	Approved
0.5862	Remote Similarity	NPD8342	Approved
0.5857	Remote Similarity	NPD6274	Approved
0.5854	Remote Similarity	NPD1694	Approved
0.5845	Remote Similarity	NPD7101	Approved
0.5845	Remote Similarity	NPD7100	Approved
0.584	Remote Similarity	NPD5737	Approved
0.584	Remote Similarity	NPD6672	Approved
0.5833	Remote Similarity	NPD5344	Discontinued
0.5827	Remote Similarity	NPD5693	Phase 1
0.5827	Remote Similarity	NPD7637	Suspended
0.5827	Remote Similarity	NPD6411	Approved
0.5816	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD5210	Approved
0.5814	Remote Similarity	NPD4629	Approved
0.5789	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD5211	Phase 2
0.5785	Remote Similarity	NPD5369	Approved
0.5775	Remote Similarity	NPD6335	Approved
0.5764	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.576	Remote Similarity	NPD4250	Approved
0.576	Remote Similarity	NPD4251	Approved
0.5758	Remote Similarity	NPD4696	Approved
0.5758	Remote Similarity	NPD5286	Approved
0.5758	Remote Similarity	NPD5285	Approved
0.5738	Remote Similarity	NPD6435	Approved
0.5738	Remote Similarity	NPD4269	Approved
0.5738	Remote Similarity	NPD4270	Approved
0.5735	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5725	Remote Similarity	NPD4755	Approved
0.5724	Remote Similarity	NPD8415	Approved
0.5704	Remote Similarity	NPD5141	Approved
0.5704	Remote Similarity	NPD6317	Approved
0.5691	Remote Similarity	NPD5362	Discontinued
0.5691	Remote Similarity	NPD6110	Phase 1
0.5683	Remote Similarity	NPD2204	Approved
0.568	Remote Similarity	NPD4249	Approved
0.5672	Remote Similarity	NPD5224	Approved
0.5672	Remote Similarity	NPD5225	Approved
0.5672	Remote Similarity	NPD4633	Approved
0.5672	Remote Similarity	NPD5226	Approved
0.5669	Remote Similarity	NPD6101	Approved
0.5669	Remote Similarity	NPD6080	Approved
0.5669	Remote Similarity	NPD6673	Approved
0.5669	Remote Similarity	NPD6904	Approved
0.5669	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD6313	Approved
0.5664	Remote Similarity	NPD6314	Approved
0.5655	Remote Similarity	NPD6908	Approved
0.5655	Remote Similarity	NPD6909	Approved
0.5639	Remote Similarity	NPD6648	Approved
0.5639	Remote Similarity	NPD4700	Approved
0.5634	Remote Similarity	NPD6868	Approved
0.563	Remote Similarity	NPD5175	Approved
0.563	Remote Similarity	NPD5174	Approved
0.561	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5608	Remote Similarity	NPD8273	Phase 1

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