NPASS Compound

Structure

NPC47190 OpenBabel07101718182D 36 40 0 0 1 0 0 0 0 0999 V2000 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1305 -0.9914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0406 3.7217 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5852 4.5604 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4946 2.8307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5839 4.5080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8637 1.0353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5708 0.3282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0872 -1.8625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9659 0.2588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0561 2.3596 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1225 2.0012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4932 2.7783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6730 -0.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0378 3.6170 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3461 -0.8966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1213 -2.1213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6390 -0.1895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4142 -1.4142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3120 -0.6378 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.0038 3.3582 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.8625 -3.0872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8978 0.7765 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4483 -1.6730 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 20 1 0 0 0 0 5 6 2 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 7 8 1 0 0 0 0 7 11 1 0 0 0 0 8 19 2 0 0 0 0 9 22 2 0 0 0 0 10 24 2 0 0 0 0 11 27 1 0 0 0 0 12 14 1 0 0 0 0 12 20 1 0 0 0 0 13 15 1 0 0 0 0 13 21 1 0 0 0 0 14 30 1 0 0 0 0 15 32 1 0 0 0 0 16 25 2 0 0 0 0 16 26 1 0 0 0 0 17 23 1 0 0 0 0 17 31 1 0 0 0 0 18 21 2 0 0 0 0 18 33 1 0 0 0 0 19 30 1 0 0 0 0 20 31 1 1 0 0 0 21 22 1 0 0 0 0 22 24 1 0 0 0 0 23 28 1 0 0 0 0 23 29 2 0 0 0 0 24 33 1 0 0 0 0 25 28 1 0 0 0 0 25 32 1 0 0 0 0 26 29 1 0 0 0 0 26 34 2 0 0 0 0 27 30 1 1 0 0 0 27 31 1 0 0 0 0 28 35 2 0 0 0 0 29 36 1 0 0 0 0 30 3 1 6 0 0 0 31 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.29
Volume:	526.586
LogP:	6.201
LogD:	4.435
LogS:	-4.543
# Rotatable Bonds:	5
TPSA:	88.84
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.13
Synthetic Accessibility Score:	4.554
Fsp3:	0.452
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	2

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.155
MDCK Permeability:	2.006614704441745e-05
Pgp-inhibitor:	0.985
Pgp-substrate:	0.532
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.073
Plasma Protein Binding (PPB):	99.37909698486328%
Volume Distribution (VD):	3.716
Pgp-substrate:	1.6446348428726196%

ADMET: Metabolism

CYP1A2-inhibitor:	0.31
CYP1A2-substrate:	0.57
CYP2C19-inhibitor:	0.631
CYP2C19-substrate:	0.155
CYP2C9-inhibitor:	0.328
CYP2C9-substrate:	0.803
CYP2D6-inhibitor:	0.918
CYP2D6-substrate:	0.914
CYP3A4-inhibitor:	0.419
CYP3A4-substrate:	0.269

ADMET: Excretion

Clearance (CL):	5.59
Half-life (T1/2):	0.489

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.181
Drug-inuced Liver Injury (DILI):	0.271
AMES Toxicity:	0.075
Rat Oral Acute Toxicity:	0.298
Maximum Recommended Daily Dose:	0.92
Skin Sensitization:	0.971
Carcinogencity:	0.299
Eye Corrosion:	0.003
Eye Irritation:	0.883
Respiratory Toxicity:	0.911

Download Data

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

Natural Product: NPC47190

Natural Product ID:	NPC47190
*Common Name:**	KMDGCQCDKFMKAD-WORHRAFRSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KMDGCQCDKFMKAD-WORHRAFRSA-N
Standard InCHI:	InChI=1S/C31H38N2O3/c1-19-8-7-11-27-30(19,3)14-12-20(2)31(27,4)17-23-28(35)25(16-26(34)29(23)36)32-15-13-21-18-33-24-10-6-5-9-22(21)24/h5-6,8-10,16,18,20,27,32-33,36H,7,11-15,17H2,1-4H3/t20-,27+,30-,31+/m0/s1
SMILES:	O=C1C=C(NCCc2c[nH]c3c2cccc3)C(=O)C(=C1O)C[C@]1(C)[C@@H](C)CC[C@@]2([C@H]1CCC=C2C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3109400
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001534] Quinone and hydroquinone lipids [CHEMONTID:0002802] Prenylquinones

*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
NPO13603	Dactylospongia metachromia	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24479418]
NPO13603	Dactylospongia metachromia	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[33387695]
NPO13603	Dactylospongia metachromia	Species	Thorectidae	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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1864	Cell Line	L5178Y	Mus musculus	IC50	=	3700.0	nM	PMID[450013]

☑ 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 NPC47190 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	355
0.1-0.2	2076
0.2-0.3	10710
0.3-0.4	21076
0.4-0.5	4232
0.5-0.6	1879
0.6-0.7	1761
0.7-0.8	591
0.8-0.85	16
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8689	High Similarity	NPC157828
0.8689	High Similarity	NPC195239
0.8641	High Similarity	NPC11445
0.8483	Intermediate Similarity	NPC213468
0.8482	Intermediate Similarity	NPC225821
0.8457	Intermediate Similarity	NPC252338
0.8438	Intermediate Similarity	NPC258062
0.8436	Intermediate Similarity	NPC477042
0.8421	Intermediate Similarity	NPC98715
0.8396	Intermediate Similarity	NPC227582
0.8324	Intermediate Similarity	NPC284775
0.8316	Intermediate Similarity	NPC300183
0.829	Intermediate Similarity	NPC46225
0.8265	Intermediate Similarity	NPC87856
0.8247	Intermediate Similarity	NPC127677
0.8222	Intermediate Similarity	NPC151939
0.8141	Intermediate Similarity	NPC203614
0.8141	Intermediate Similarity	NPC132211
0.8112	Intermediate Similarity	NPC271862
0.8103	Intermediate Similarity	NPC286427
0.8098	Intermediate Similarity	NPC477003
0.8093	Intermediate Similarity	NPC477043
0.809	Intermediate Similarity	NPC201700
0.8083	Intermediate Similarity	NPC260900
0.8081	Intermediate Similarity	NPC151976
0.8063	Intermediate Similarity	NPC477041
0.8063	Intermediate Similarity	NPC477044
0.8045	Intermediate Similarity	NPC194411
0.8042	Intermediate Similarity	NPC267343
0.804	Intermediate Similarity	NPC267965
0.8033	Intermediate Similarity	NPC300688
0.8032	Intermediate Similarity	NPC476460
0.8021	Intermediate Similarity	NPC74413
0.8011	Intermediate Similarity	NPC94752
0.8	Intermediate Similarity	NPC228835
0.8	Intermediate Similarity	NPC314372
0.7979	Intermediate Similarity	NPC154339
0.7978	Intermediate Similarity	NPC11126
0.796	Intermediate Similarity	NPC204491
0.7955	Intermediate Similarity	NPC41257
0.7947	Intermediate Similarity	NPC304203
0.7941	Intermediate Similarity	NPC2395
0.7931	Intermediate Similarity	NPC469786
0.7931	Intermediate Similarity	NPC73952
0.7931	Intermediate Similarity	NPC469763
0.7931	Intermediate Similarity	NPC259644
0.7931	Intermediate Similarity	NPC469765
0.7931	Intermediate Similarity	NPC25008
0.7931	Intermediate Similarity	NPC469760
0.7927	Intermediate Similarity	NPC477045
0.7923	Intermediate Similarity	NPC68354
0.7921	Intermediate Similarity	NPC311276
0.7919	Intermediate Similarity	NPC24678
0.7919	Intermediate Similarity	NPC105818
0.7917	Intermediate Similarity	NPC167710
0.7912	Intermediate Similarity	NPC275305
0.7912	Intermediate Similarity	NPC37423
0.7901	Intermediate Similarity	NPC6982
0.7892	Intermediate Similarity	NPC191415
0.7886	Intermediate Similarity	NPC70922
0.7886	Intermediate Similarity	NPC211572
0.7886	Intermediate Similarity	NPC80597
0.7886	Intermediate Similarity	NPC75540
0.7886	Intermediate Similarity	NPC212376
0.7882	Intermediate Similarity	NPC190296
0.788	Intermediate Similarity	NPC126709
0.788	Intermediate Similarity	NPC55772
0.788	Intermediate Similarity	NPC248041
0.7869	Intermediate Similarity	NPC267885
0.7864	Intermediate Similarity	NPC147446
0.7861	Intermediate Similarity	NPC280290
0.7853	Intermediate Similarity	NPC326422
0.7826	Intermediate Similarity	NPC141428
0.7826	Intermediate Similarity	NPC235885
0.7819	Intermediate Similarity	NPC235684
0.7814	Intermediate Similarity	NPC293216
0.7814	Intermediate Similarity	NPC110500
0.7814	Intermediate Similarity	NPC149155
0.7814	Intermediate Similarity	NPC203468
0.7802	Intermediate Similarity	NPC262338
0.7797	Intermediate Similarity	NPC469762
0.779	Intermediate Similarity	NPC78020
0.7788	Intermediate Similarity	NPC267926
0.7784	Intermediate Similarity	NPC176199
0.7784	Intermediate Similarity	NPC215795
0.7784	Intermediate Similarity	NPC283219
0.7778	Intermediate Similarity	NPC42372
0.7766	Intermediate Similarity	NPC317701
0.7765	Intermediate Similarity	NPC469768
0.7765	Intermediate Similarity	NPC469779
0.7765	Intermediate Similarity	NPC469761
0.7765	Intermediate Similarity	NPC469784
0.7765	Intermediate Similarity	NPC469783
0.7765	Intermediate Similarity	NPC469780
0.7765	Intermediate Similarity	NPC469767
0.7753	Intermediate Similarity	NPC56765
0.7753	Intermediate Similarity	NPC206819
0.7753	Intermediate Similarity	NPC318065
0.7751	Intermediate Similarity	NPC57690
0.774	Intermediate Similarity	NPC469785
0.7737	Intermediate Similarity	NPC321708
0.7735	Intermediate Similarity	NPC160105
0.7735	Intermediate Similarity	NPC474561
0.7735	Intermediate Similarity	NPC49954
0.773	Intermediate Similarity	NPC84827
0.773	Intermediate Similarity	NPC145885
0.773	Intermediate Similarity	NPC157583
0.773	Intermediate Similarity	NPC14113
0.7722	Intermediate Similarity	NPC40779
0.7719	Intermediate Similarity	NPC469766
0.7692	Intermediate Similarity	NPC266192
0.7692	Intermediate Similarity	NPC63751
0.7688	Intermediate Similarity	NPC159856
0.7684	Intermediate Similarity	NPC17059
0.768	Intermediate Similarity	NPC115232
0.768	Intermediate Similarity	NPC71132
0.7654	Intermediate Similarity	NPC135141
0.7654	Intermediate Similarity	NPC92796
0.7642	Intermediate Similarity	NPC290529
0.7634	Intermediate Similarity	NPC111275
0.7632	Intermediate Similarity	NPC315555
0.7624	Intermediate Similarity	NPC271797
0.7624	Intermediate Similarity	NPC21174
0.7614	Intermediate Similarity	NPC53947
0.7606	Intermediate Similarity	NPC470677
0.7604	Intermediate Similarity	NPC324091
0.7604	Intermediate Similarity	NPC95783
0.7602	Intermediate Similarity	NPC73767
0.7602	Intermediate Similarity	NPC34837
0.76	Intermediate Similarity	NPC471957
0.7596	Intermediate Similarity	NPC154293
0.7592	Intermediate Similarity	NPC278434
0.7588	Intermediate Similarity	NPC84911
0.7579	Intermediate Similarity	NPC133003
0.7571	Intermediate Similarity	NPC476818
0.757	Intermediate Similarity	NPC70155
0.7569	Intermediate Similarity	NPC282231
0.7568	Intermediate Similarity	NPC314603
0.7566	Intermediate Similarity	NPC102755
0.7563	Intermediate Similarity	NPC477004
0.7553	Intermediate Similarity	NPC79777
0.7553	Intermediate Similarity	NPC471997
0.7552	Intermediate Similarity	NPC213629
0.7539	Intermediate Similarity	NPC99428
0.7538	Intermediate Similarity	NPC476874
0.7538	Intermediate Similarity	NPC294693
0.7529	Intermediate Similarity	NPC261195
0.7529	Intermediate Similarity	NPC29886
0.7529	Intermediate Similarity	NPC96102
0.7527	Intermediate Similarity	NPC194640
0.7526	Intermediate Similarity	NPC467063
0.7526	Intermediate Similarity	NPC216550
0.7514	Intermediate Similarity	NPC279918
0.7513	Intermediate Similarity	NPC131887
0.75	Intermediate Similarity	NPC110126
0.75	Intermediate Similarity	NPC70949
0.7488	Intermediate Similarity	NPC27041
0.7487	Intermediate Similarity	NPC308931
0.7487	Intermediate Similarity	NPC99939
0.7485	Intermediate Similarity	NPC105127
0.7476	Intermediate Similarity	NPC155444
0.7476	Intermediate Similarity	NPC474412
0.7475	Intermediate Similarity	NPC237414
0.7474	Intermediate Similarity	NPC117027
0.7465	Intermediate Similarity	NPC191382
0.7465	Intermediate Similarity	NPC56109
0.7463	Intermediate Similarity	NPC153980
0.7463	Intermediate Similarity	NPC88115
0.7463	Intermediate Similarity	NPC6865
0.7463	Intermediate Similarity	NPC471193
0.7463	Intermediate Similarity	NPC471194
0.7462	Intermediate Similarity	NPC74153
0.7461	Intermediate Similarity	NPC255909
0.7461	Intermediate Similarity	NPC103119
0.746	Intermediate Similarity	NPC234403
0.746	Intermediate Similarity	NPC73994
0.746	Intermediate Similarity	NPC16659
0.7459	Intermediate Similarity	NPC474492
0.7459	Intermediate Similarity	NPC471943
0.7458	Intermediate Similarity	NPC37548
0.7452	Intermediate Similarity	NPC477714
0.7452	Intermediate Similarity	NPC473310
0.7447	Intermediate Similarity	NPC237188
0.7447	Intermediate Similarity	NPC59269
0.7443	Intermediate Similarity	NPC288838
0.7432	Intermediate Similarity	NPC90723
0.743	Intermediate Similarity	NPC200214
0.743	Intermediate Similarity	NPC200743
0.7424	Intermediate Similarity	NPC265576
0.7424	Intermediate Similarity	NPC171317
0.7423	Intermediate Similarity	NPC83111
0.7421	Intermediate Similarity	NPC71037
0.7419	Intermediate Similarity	NPC470498
0.7418	Intermediate Similarity	NPC470680
0.7418	Intermediate Similarity	NPC131718
0.7418	Intermediate Similarity	NPC215584
0.7418	Intermediate Similarity	NPC100104
0.7418	Intermediate Similarity	NPC44773
0.7416	Intermediate Similarity	NPC33421
0.7415	Intermediate Similarity	NPC72956

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 NPC47190 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	211
0.1-0.2	573
0.2-0.3	699
0.3-0.4	2018
0.4-0.5	2587
0.5-0.6	2092
0.6-0.7	824
0.7-0.8	145
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8197	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.8073	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.8043	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7618	Phase 3
0.8	Intermediate Similarity	NPD7619	Phase 3
0.7923	Intermediate Similarity	NPD3505	Approved
0.7923	Intermediate Similarity	NPD3506	Approved
0.7917	Intermediate Similarity	NPD6664	Approved
0.7914	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.788	Intermediate Similarity	NPD4079	Approved
0.788	Intermediate Similarity	NPD4076	Approved
0.7872	Intermediate Similarity	NPD3961	Discontinued
0.7869	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7814	Intermediate Similarity	NPD482	Approved
0.78	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7772	Intermediate Similarity	NPD4075	Phase 2
0.7754	Intermediate Similarity	NPD2095	Phase 2
0.7754	Intermediate Similarity	NPD2094	Phase 2
0.7754	Intermediate Similarity	NPD2092	Phase 2
0.7749	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7749	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD3323	Discontinued
0.7713	Intermediate Similarity	NPD2096	Phase 2
0.7713	Intermediate Similarity	NPD2091	Phase 2
0.7684	Intermediate Similarity	NPD8431	Approved
0.768	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD5473	Discontinued
0.7638	Intermediate Similarity	NPD6987	Phase 1
0.7638	Intermediate Similarity	NPD5901	Discontinued
0.7634	Intermediate Similarity	NPD4181	Approved
0.7619	Intermediate Similarity	NPD7564	Discontinued
0.7616	Intermediate Similarity	NPD1722	Approved
0.7614	Intermediate Similarity	NPD2172	Phase 1
0.7602	Intermediate Similarity	NPD786	Approved
0.7598	Intermediate Similarity	NPD8094	Discontinued
0.7596	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7592	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD750	Phase 2
0.7562	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD3100	Discontinued
0.7554	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD2479	Phase 3
0.7553	Intermediate Similarity	NPD2481	Approved
0.7549	Intermediate Similarity	NPD8093	Discontinued
0.754	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD5065	Approved
0.7527	Intermediate Similarity	NPD4128	Approved
0.7514	Intermediate Similarity	NPD4462	Approved
0.7514	Intermediate Similarity	NPD4463	Approved
0.75	Intermediate Similarity	NPD4848	Phase 1
0.7465	Intermediate Similarity	NPD7781	Approved
0.7465	Intermediate Similarity	NPD7780	Approved
0.7463	Intermediate Similarity	NPD5426	Phase 3
0.7451	Intermediate Similarity	NPD4051	Discontinued
0.744	Intermediate Similarity	NPD3389	Approved
0.744	Intermediate Similarity	NPD3393	Approved
0.744	Intermediate Similarity	NPD3394	Approved
0.7438	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD3583	Phase 2
0.743	Intermediate Similarity	NPD7824	Approved
0.7426	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD7957	Phase 1
0.7419	Intermediate Similarity	NPD3610	Approved
0.7419	Intermediate Similarity	NPD3609	Approved
0.7415	Intermediate Similarity	NPD4614	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD4640	Approved
0.7405	Intermediate Similarity	NPD4639	Approved
0.7405	Intermediate Similarity	NPD4638	Approved
0.7405	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD3318	Approved
0.7382	Intermediate Similarity	NPD3320	Approved
0.7382	Intermediate Similarity	NPD3319	Phase 1
0.7368	Intermediate Similarity	NPD6595	Phase 3
0.7368	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD7187	Phase 2
0.736	Intermediate Similarity	NPD7024	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD4922	Phase 2
0.7344	Intermediate Similarity	NPD6178	Phase 3
0.734	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7336	Intermediate Similarity	NPD7731	Approved
0.7336	Intermediate Similarity	NPD7730	Approved
0.733	Intermediate Similarity	NPD7470	Discontinued
0.7327	Intermediate Similarity	NPD7951	Approved
0.7327	Intermediate Similarity	NPD7950	Approved
0.7327	Intermediate Similarity	NPD7789	Approved
0.7327	Intermediate Similarity	NPD7790	Approved
0.7327	Intermediate Similarity	NPD7953	Approved
0.7327	Intermediate Similarity	NPD7791	Approved
0.7327	Intermediate Similarity	NPD7952	Approved
0.7324	Intermediate Similarity	NPD7271	Approved
0.7322	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD2640	Approved
0.7312	Intermediate Similarity	NPD2641	Approved
0.7306	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD2510	Approved
0.7268	Intermediate Similarity	NPD2509	Approved
0.7264	Intermediate Similarity	NPD484	Approved
0.7263	Intermediate Similarity	NPD2753	Discontinued
0.7263	Intermediate Similarity	NPD2144	Approved
0.7246	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD3870	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD3871	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD3038	Discontinued
0.724	Intermediate Similarity	NPD3178	Discontinued
0.7238	Intermediate Similarity	NPD2837	Discontinued
0.7232	Intermediate Similarity	NPD5254	Discontinued
0.7228	Intermediate Similarity	NPD1403	Approved
0.7228	Intermediate Similarity	NPD1404	Approved
0.7214	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7455	Approved
0.7212	Intermediate Similarity	NPD7454	Approved
0.7212	Intermediate Similarity	NPD2411	Approved
0.7211	Intermediate Similarity	NPD3238	Discontinued
0.72	Intermediate Similarity	NPD7948	Phase 1
0.7198	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD7233	Approved
0.7194	Intermediate Similarity	NPD7234	Approved
0.7192	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD8073	Approved
0.7188	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7944	Discontinued
0.7179	Intermediate Similarity	NPD6217	Discontinued
0.7179	Intermediate Similarity	NPD5809	Phase 3
0.7179	Intermediate Similarity	NPD7026	Phase 2
0.7179	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD4601	Approved
0.7178	Intermediate Similarity	NPD4600	Approved
0.7171	Intermediate Similarity	NPD2008	Discontinued
0.7166	Intermediate Similarity	NPD6446	Discontinued
0.7166	Intermediate Similarity	NPD2639	Approved
0.7166	Intermediate Similarity	NPD2642	Approved
0.7159	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD8072	Approved
0.7157	Intermediate Similarity	NPD4499	Approved
0.7156	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4988	Discontinued
0.7136	Intermediate Similarity	NPD6242	Discontinued
0.7136	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD6999	Discontinued
0.7129	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD5021	Discontinued
0.7128	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6376	Discontinued
0.7098	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD6479	Discontinued
0.7073	Intermediate Similarity	NPD6176	Phase 1
0.7068	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD2580	Discontinued
0.7059	Intermediate Similarity	NPD5088	Discontinued
0.7056	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD7603	Discontinued
0.7039	Intermediate Similarity	NPD8272	Phase 2
0.7039	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD1343	Approved
0.7027	Intermediate Similarity	NPD4326	Phase 2
0.7021	Intermediate Similarity	NPD1568	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD7175	Phase 1
0.7019	Intermediate Similarity	NPD7191	Phase 2
0.7017	Intermediate Similarity	NPD4702	Approved
0.7017	Intermediate Similarity	NPD4703	Approved
0.7015	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD5497	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD5315	Discontinued
0.7005	Intermediate Similarity	NPD5400	Approved
0.7	Intermediate Similarity	NPD1326	Approved
0.7	Intermediate Similarity	NPD7927	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1325	Approved
0.6995	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7707	Approved
0.698	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD4883	Approved
0.6974	Remote Similarity	NPD4011	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD6026	Approved
0.697	Remote Similarity	NPD4948	Discontinued
0.6963	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7308	Discontinued
0.6959	Remote Similarity	NPD8386	Phase 2
0.6957	Remote Similarity	NPD8115	Approved
0.6957	Remote Similarity	NPD8114	Approved
0.695	Remote Similarity	NPD2336	Approved
0.6942	Remote Similarity	NPD4924	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD6164	Phase 2
0.6941	Remote Similarity	NPD6165	Phase 2
0.6939	Remote Similarity	NPD7401	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