NPASS Compound

Structure

NPC8590 OpenBabel07101719242D 22 23 0 0 1 0 0 0 0 0999 V2000 -2.0253 -1.2450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6977 -0.6770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3887 -1.6280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9764 -1.5540 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 -3.6808 1.7024 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 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5116 0.0933 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7195 -0.8849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 1.4945 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.1808 0.8364 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 2 9 1 0 0 0 0 3 9 1 0 0 0 0 4 16 1 0 0 0 0 5 16 1 0 0 0 0 6 16 1 0 0 0 0 7 10 1 0 0 0 0 7 11 2 0 0 0 0 8 17 2 0 0 0 0 8 18 1 0 0 0 0 10 13 2 0 0 0 0 10 17 1 0 0 0 0 11 14 1 0 0 0 0 11 19 1 0 0 0 0 12 9 1 1 0 0 0 12 15 1 0 0 0 0 12 20 1 0 0 0 0 13 16 1 0 0 0 0 13 18 1 0 0 0 0 14 20 2 0 0 0 0 14 21 1 0 0 0 0 15 19 2 0 0 0 0 15 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.17
Volume:	313.928
LogP:	1.919
LogD:	2.066
LogS:	-3.257
# Rotatable Bonds:	5
TPSA:	94.66
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.739
Synthetic Accessibility Score:	3.65
Fsp3:	0.438
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.057
MDCK Permeability:	1.1031727808585856e-05
Pgp-inhibitor:	0.348
Pgp-substrate:	0.152
Human Intestinal Absorption (HIA):	0.063
20% Bioavailability (F20%):	0.891
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.032
Plasma Protein Binding (PPB):	95.686767578125%
Volume Distribution (VD):	0.76
Pgp-substrate:	2.7106564044952393%

ADMET: Metabolism

CYP1A2-inhibitor:	0.055
CYP1A2-substrate:	0.414
CYP2C19-inhibitor:	0.152
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.247
CYP2C9-substrate:	0.933
CYP2D6-inhibitor:	0.491
CYP2D6-substrate:	0.066
CYP3A4-inhibitor:	0.708
CYP3A4-substrate:	0.631

ADMET: Excretion

Clearance (CL):	3.287
Half-life (T1/2):	0.904

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.219
Drug-inuced Liver Injury (DILI):	0.981
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.828
Maximum Recommended Daily Dose:	0.021
Skin Sensitization:	0.333
Carcinogencity:	0.064
Eye Corrosion:	0.003
Eye Irritation:	0.027
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC8590

Natural Product ID:	NPC8590
*Common Name:**	Aurantiamine
IUPAC Name:	(3E,6S)-3-[[5-(2-methylbut-3-en-2-yl)-1H-imidazol-4-yl]methylidene]-6-propan-2-ylpiperazine-2,5-dione
Synonyms:	Aurantiamine
Standard InCHIKey:	RSGRSUVVCYUKLM-VNKGSWCUSA-N
Standard InCHI:	InChI=1S/C16H22N4O2/c1-6-16(4,5)13-10(17-8-18-13)7-11-14(21)20-12(9(2)3)15(22)19-11/h6-9,12H,1H2,2-5H3,(H,17,18)(H,19,22)(H,20,21)/b11-7+/t12-/m0/s1
SMILES:	C=CC(c1[nH]cnc1/C=C1/N=C(O)[C@@H](N=C1O)C(C)C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL570312
PubChem CID:	15487888
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids and derivatives

*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
NPO20001	Aspergillus insuetus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19719247]
NPO20001	Aspergillus insuetus	Species	Aspergillaceae	Eukaryota	Mediterranean sponge Psammocinia sp.	coast of Israel	n.a.	PMID[21676619]
NPO20001	Aspergillus insuetus	Species	Aspergillaceae	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
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	15100.0	nM	PMID[543192]

☑ 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 NPC8590 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	386
0.1-0.2	12436
0.2-0.3	22590
0.3-0.4	4156
0.4-0.5	2495
0.5-0.6	579
0.6-0.7	50
0.7-0.8	3
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.7468	Intermediate Similarity	NPC282531
0.7172	Intermediate Similarity	NPC243319
0.6832	Remote Similarity	NPC469975
0.6714	Remote Similarity	NPC327613
0.6702	Remote Similarity	NPC71238
0.6597	Remote Similarity	NPC54981
0.6544	Remote Similarity	NPC59314
0.651	Remote Similarity	NPC180462
0.6433	Remote Similarity	NPC286696
0.6408	Remote Similarity	NPC41958
0.6398	Remote Similarity	NPC42483
0.6331	Remote Similarity	NPC300238
0.6329	Remote Similarity	NPC185903
0.6324	Remote Similarity	NPC293163
0.6299	Remote Similarity	NPC57279
0.625	Remote Similarity	NPC313547
0.625	Remote Similarity	NPC120070
0.6242	Remote Similarity	NPC237812
0.6242	Remote Similarity	NPC18223
0.6235	Remote Similarity	NPC327477
0.6234	Remote Similarity	NPC235501
0.6221	Remote Similarity	NPC162268
0.6214	Remote Similarity	NPC155498
0.6187	Remote Similarity	NPC111132
0.618	Remote Similarity	NPC477119
0.6175	Remote Similarity	NPC313514
0.6159	Remote Similarity	NPC15566
0.6125	Remote Similarity	NPC216159
0.6101	Remote Similarity	NPC62151
0.6082	Remote Similarity	NPC124276
0.6062	Remote Similarity	NPC210947
0.6057	Remote Similarity	NPC49217
0.6043	Remote Similarity	NPC477166
0.6043	Remote Similarity	NPC304187
0.6043	Remote Similarity	NPC201900
0.6041	Remote Similarity	NPC113369
0.6038	Remote Similarity	NPC314646
0.6036	Remote Similarity	NPC472834
0.6036	Remote Similarity	NPC60537
0.603	Remote Similarity	NPC282247
0.6026	Remote Similarity	NPC25465
0.602	Remote Similarity	NPC238945
0.6012	Remote Similarity	NPC187951
0.6012	Remote Similarity	NPC37548
0.6	Remote Similarity	NPC273327
0.599	Remote Similarity	NPC323244
0.5988	Remote Similarity	NPC212742
0.5978	Remote Similarity	NPC101676
0.5978	Remote Similarity	NPC477118
0.5952	Remote Similarity	NPC114209
0.5946	Remote Similarity	NPC477120
0.5942	Remote Similarity	NPC320256
0.5939	Remote Similarity	NPC197068
0.5933	Remote Similarity	NPC327579
0.5914	Remote Similarity	NPC527
0.5914	Remote Similarity	NPC133782
0.5914	Remote Similarity	NPC144474
0.5912	Remote Similarity	NPC9639
0.5912	Remote Similarity	NPC126634
0.59	Remote Similarity	NPC471603
0.5889	Remote Similarity	NPC317054
0.5886	Remote Similarity	NPC470203
0.5877	Remote Similarity	NPC328924
0.5876	Remote Similarity	NPC49954
0.5876	Remote Similarity	NPC474561
0.5874	Remote Similarity	NPC119133
0.5872	Remote Similarity	NPC470507
0.5872	Remote Similarity	NPC38736
0.5864	Remote Similarity	NPC296437
0.5857	Remote Similarity	NPC69843
0.5839	Remote Similarity	NPC51000
0.5829	Remote Similarity	NPC470204
0.5828	Remote Similarity	NPC470266
0.5823	Remote Similarity	NPC470138
0.5816	Remote Similarity	NPC187191
0.5816	Remote Similarity	NPC326248
0.5813	Remote Similarity	NPC327941
0.5813	Remote Similarity	NPC262926
0.5804	Remote Similarity	NPC476099
0.58	Remote Similarity	NPC278549
0.5795	Remote Similarity	NPC54537
0.5789	Remote Similarity	NPC24678
0.5789	Remote Similarity	NPC477167
0.5789	Remote Similarity	NPC473342
0.5789	Remote Similarity	NPC105818
0.5787	Remote Similarity	NPC160105
0.5783	Remote Similarity	NPC476521
0.5783	Remote Similarity	NPC174020
0.5776	Remote Similarity	NPC61198
0.5774	Remote Similarity	NPC242556
0.5763	Remote Similarity	NPC194640
0.5761	Remote Similarity	NPC473585
0.5758	Remote Similarity	NPC476433
0.5758	Remote Similarity	NPC315642
0.5758	Remote Similarity	NPC476528
0.5758	Remote Similarity	NPC74306
0.5739	Remote Similarity	NPC122141
0.5732	Remote Similarity	NPC226184
0.5732	Remote Similarity	NPC167285
0.5732	Remote Similarity	NPC76544
0.573	Remote Similarity	NPC41333
0.5723	Remote Similarity	NPC474986
0.5723	Remote Similarity	NPC476520
0.5723	Remote Similarity	NPC476522
0.5723	Remote Similarity	NPC476013
0.5722	Remote Similarity	NPC265576
0.5714	Remote Similarity	NPC476408
0.5706	Remote Similarity	NPC282231
0.5693	Remote Similarity	NPC477417
0.5693	Remote Similarity	NPC477419
0.5679	Remote Similarity	NPC320818
0.5676	Remote Similarity	NPC16659
0.5674	Remote Similarity	NPC472587
0.5668	Remote Similarity	NPC228835
0.5667	Remote Similarity	NPC63433
0.5667	Remote Similarity	NPC63751
0.5663	Remote Similarity	NPC104049
0.5662	Remote Similarity	NPC171393
0.5662	Remote Similarity	NPC295452
0.566	Remote Similarity	NPC156003
0.566	Remote Similarity	NPC246193
0.5659	Remote Similarity	NPC177996
0.5659	Remote Similarity	NPC314557
0.5659	Remote Similarity	NPC314603
0.5659	Remote Similarity	NPC147983
0.5657	Remote Similarity	NPC285469
0.565	Remote Similarity	NPC279918
0.5647	Remote Similarity	NPC204141
0.5647	Remote Similarity	NPC159856
0.5647	Remote Similarity	NPC314372
0.5644	Remote Similarity	NPC470141
0.564	Remote Similarity	NPC314440
0.564	Remote Similarity	NPC124005
0.564	Remote Similarity	NPC118135
0.5638	Remote Similarity	NPC265111
0.5635	Remote Similarity	NPC469308
0.5632	Remote Similarity	NPC25008
0.5632	Remote Similarity	NPC469763
0.5632	Remote Similarity	NPC472833
0.5632	Remote Similarity	NPC73952
0.5632	Remote Similarity	NPC469786
0.5632	Remote Similarity	NPC469760
0.5632	Remote Similarity	NPC259644
0.5632	Remote Similarity	NPC469765
0.5628	Remote Similarity	NPC313897
0.5628	Remote Similarity	NPC473376
0.5625	Remote Similarity	NPC299594
0.5625	Remote Similarity	NPC475870
0.5625	Remote Similarity	NPC10466
0.5622	Remote Similarity	NPC176199
0.5622	Remote Similarity	NPC215795
0.5622	Remote Similarity	NPC265710
0.5619	Remote Similarity	NPC300139
0.5619	Remote Similarity	NPC233431
0.5618	Remote Similarity	NPC225018
0.5616	Remote Similarity	NPC242923
0.5614	Remote Similarity	NPC143872
0.5614	Remote Similarity	NPC129042
0.5604	Remote Similarity	NPC6982
0.5604	Remote Similarity	NPC470498
0.5602	Remote Similarity	NPC186619
0.56	Remote Similarity	NPC471458
0.56	Remote Similarity	NPC475288
0.56	Remote Similarity	NPC212376
0.56	Remote Similarity	NPC207726
0.56	Remote Similarity	NPC80597
0.56	Remote Similarity	NPC75540
0.56	Remote Similarity	NPC211572
0.56	Remote Similarity	NPC70922

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 NPC8590 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	194
0.1-0.2	797
0.2-0.3	2215
0.3-0.4	2991
0.4-0.5	2169
0.5-0.6	709
0.6-0.7	73
0.7-0.8	2
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
0.8446	Intermediate Similarity	NPD3405	Phase 3
0.7172	Intermediate Similarity	NPD9081	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD5342	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD3612	Phase 2
0.6803	Remote Similarity	NPD1354	Approved
0.6803	Remote Similarity	NPD1356	Approved
0.6803	Remote Similarity	NPD1355	Clinical (unspecified phase)
0.679	Remote Similarity	NPD1303	Phase 1
0.677	Remote Similarity	NPD1030	Approved
0.677	Remote Similarity	NPD1029	Clinical (unspecified phase)
0.677	Remote Similarity	NPD1027	Approved
0.6706	Remote Similarity	NPD3347	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD705	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD9360	Approved
0.6629	Remote Similarity	NPD2523	Phase 2
0.6629	Remote Similarity	NPD2526	Phase 2
0.6625	Remote Similarity	NPD1690	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD515	Phase 1
0.6606	Remote Similarity	NPD1290	Phase 2
0.6599	Remote Similarity	NPD1389	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD1390	Phase 1
0.6599	Remote Similarity	NPD1388	Phase 1
0.6597	Remote Similarity	NPD307	Approved
0.6593	Remote Similarity	NPD8641	Approved
0.6593	Remote Similarity	NPD8113	Phase 2
0.6544	Remote Similarity	NPD8837	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD459	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD545	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD536	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD695	Discontinued
0.6474	Remote Similarity	NPD8410	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD8629	Discontinued
0.6464	Remote Similarity	NPD1043	Phase 3
0.6453	Remote Similarity	NPD2875	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD4213	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD1042	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD6545	Clinical (unspecified phase)
0.64	Remote Similarity	NPD300	Approved
0.6398	Remote Similarity	NPD9724	Phase 1
0.6393	Remote Similarity	NPD994	Phase 2
0.6393	Remote Similarity	NPD996	Phase 2
0.6389	Remote Similarity	NPD9132	Discontinued
0.6364	Remote Similarity	NPD1272	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD775	Approved
0.6352	Remote Similarity	NPD1451	Approved
0.6347	Remote Similarity	NPD2604	Approved
0.6347	Remote Similarity	NPD3697	Discontinued
0.6328	Remote Similarity	NPD1327	Discontinued
0.6319	Remote Similarity	NPD2152	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD1807	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD1808	Phase 1
0.6302	Remote Similarity	NPD7834	Approved
0.6301	Remote Similarity	NPD237	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD547	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD706	Phase 1
0.6294	Remote Similarity	NPD2593	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD3130	Discontinued
0.6286	Remote Similarity	NPD5996	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD966	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD1120	Approved
0.6282	Remote Similarity	NPD1121	Approved
0.6269	Remote Similarity	NPD7981	Discontinued
0.6259	Remote Similarity	NPD9626	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD209	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD4649	Clinical (unspecified phase)
0.625	Remote Similarity	NPD9183	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD9133	Approved
0.6224	Remote Similarity	NPD9375	Discontinued
0.6224	Remote Similarity	NPD8458	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD4441	Phase 2
0.6216	Remote Similarity	NPD2127	Suspended
0.6205	Remote Similarity	NPD7465	Suspended
0.6193	Remote Similarity	NPD8488	Clinical (unspecified phase)
0.6187	Remote Similarity	NPD8861	Approved
0.6187	Remote Similarity	NPD8862	Approved
0.6187	Remote Similarity	NPD8859	Approved
0.6186	Remote Similarity	NPD4612	Discontinued
0.6185	Remote Similarity	NPD509	Phase 3
0.6185	Remote Similarity	NPD1313	Approved
0.6185	Remote Similarity	NPD5269	Clinical (unspecified phase)
0.6181	Remote Similarity	NPD7980	Clinical (unspecified phase)
0.6175	Remote Similarity	NPD7138	Phase 2
0.6175	Remote Similarity	NPD2009	Clinical (unspecified phase)
0.6166	Remote Similarity	NPD6403	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD6850	Phase 2
0.6158	Remote Similarity	NPD2928	Phase 2
0.6158	Remote Similarity	NPD6849	Phase 2
0.6149	Remote Similarity	NPD2478	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD5730	Phase 2
0.6145	Remote Similarity	NPD40	Phase 2
0.6145	Remote Similarity	NPD2930	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD9628	Approved
0.6138	Remote Similarity	NPD6468	Clinical (unspecified phase)
0.6138	Remote Similarity	NPD6469	Phase 3
0.6136	Remote Similarity	NPD1567	Clinical (unspecified phase)
0.6131	Remote Similarity	NPD2128	Phase 1
0.6125	Remote Similarity	NPD875	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD5943	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD8261	Discontinued
0.612	Remote Similarity	NPD2872	Phase 2
0.612	Remote Similarity	NPD2591	Phase 2
0.612	Remote Similarity	NPD2793	Discontinued
0.6118	Remote Similarity	NPD2927	Phase 3
0.6114	Remote Similarity	NPD6906	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD3706	Clinical (unspecified phase)
0.6096	Remote Similarity	NPD9374	Approved
0.6096	Remote Similarity	NPD460	Discontinued
0.6095	Remote Similarity	NPD3906	Approved
0.6092	Remote Similarity	NPD1333	Phase 3
0.6091	Remote Similarity	NPD949	Phase 1
0.6089	Remote Similarity	NPD3041	Approved
0.6087	Remote Similarity	NPD1431	Approved
0.6087	Remote Similarity	NPD1430	Approved
0.6085	Remote Similarity	NPD3830	Phase 1
0.6075	Remote Similarity	NPD7709	Discontinued
0.6069	Remote Similarity	NPD1015	Phase 2
0.6069	Remote Similarity	NPD1016	Phase 2
0.6051	Remote Similarity	NPD796	Phase 2
0.6048	Remote Similarity	NPD7842	Phase 2
0.6045	Remote Similarity	NPD3105	Discontinued
0.6043	Remote Similarity	NPD4615	Phase 2
0.604	Remote Similarity	NPD8105	Discontinued
0.6036	Remote Similarity	NPD2662	Approved
0.6036	Remote Similarity	NPD2180	Approved
0.6036	Remote Similarity	NPD2660	Approved
0.6033	Remote Similarity	NPD3378	Clinical (unspecified phase)
0.602	Remote Similarity	NPD8271	Discontinued
0.6014	Remote Similarity	NPD1368	Approved
0.6012	Remote Similarity	NPD174	Discontinued
0.6011	Remote Similarity	NPD3485	Clinical (unspecified phase)
0.6011	Remote Similarity	NPD2456	Phase 2
0.6011	Remote Similarity	NPD2457	Phase 2
0.601	Remote Similarity	NPD3497	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3002	Clinical (unspecified phase)
0.6	Remote Similarity	NPD9409	Discontinued
0.6	Remote Similarity	NPD2880	Discontinued
0.599	Remote Similarity	NPD8292	Phase 2
0.5989	Remote Similarity	NPD1895	Discontinued
0.5978	Remote Similarity	NPD7297	Phase 2
0.5976	Remote Similarity	NPD1731	Clinical (unspecified phase)
0.5967	Remote Similarity	NPD3341	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD6794	Approved
0.5959	Remote Similarity	NPD9373	Approved
0.5957	Remote Similarity	NPD341	Approved
0.5957	Remote Similarity	NPD340	Approved
0.5957	Remote Similarity	NPD6619	Phase 3
0.5955	Remote Similarity	NPD6827	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD6828	Phase 2
0.5951	Remote Similarity	NPD1117	Clinical (unspecified phase)
0.5949	Remote Similarity	NPD1915	Phase 1
0.5941	Remote Similarity	NPD7471	Discontinued
0.5938	Remote Similarity	NPD3814	Phase 1
0.5934	Remote Similarity	NPD5962	Phase 2
0.5933	Remote Similarity	NPD9607	Approved
0.5932	Remote Similarity	NPD9582	Phase 3
0.593	Remote Similarity	NPD4863	Approved
0.5922	Remote Similarity	NPD1037	Clinical (unspecified phase)
0.592	Remote Similarity	NPD5768	Phase 2
0.5909	Remote Similarity	NPD2786	Discontinued
0.5909	Remote Similarity	NPD3889	Approved
0.5904	Remote Similarity	NPD2892	Phase 1
0.5904	Remote Similarity	NPD3419	Clinical (unspecified phase)
0.5904	Remote Similarity	NPD1286	Suspended
0.5902	Remote Similarity	NPD4414	Discontinued
0.59	Remote Similarity	NPD2794	Discontinued
0.5897	Remote Similarity	NPD2364	Suspended
0.5895	Remote Similarity	NPD978	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD3108	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD4128	Approved
0.5885	Remote Similarity	NPD5885	Approved
0.5882	Remote Similarity	NPD7884	Discontinued
0.5879	Remote Similarity	NPD9627	Approved
0.5879	Remote Similarity	NPD3013	Phase 3
0.5879	Remote Similarity	NPD3014	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD1215	Discontinued
0.5875	Remote Similarity	NPD809	Discontinued
0.5874	Remote Similarity	NPD9291	Approved
0.587	Remote Similarity	NPD3512	Clinical (unspecified phase)
0.5867	Remote Similarity	NPD9606	Approved
0.5862	Remote Similarity	NPD8258	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD8257	Approved
0.5862	Remote Similarity	NPD8256	Approved
0.586	Remote Similarity	NPD3913	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD7415	Suspended
0.5848	Remote Similarity	NPD2524	Discontinued
0.5848	Remote Similarity	NPD1257	Approved
0.5842	Remote Similarity	NPD3403	Clinical (unspecified phase)
0.5839	Remote Similarity	NPD8838	Approved
0.5838	Remote Similarity	NPD2877	Clinical (unspecified phase)
0.5838	Remote Similarity	NPD2876	Phase 3
0.5838	Remote Similarity	NPD1709	Phase 1
0.5825	Remote Similarity	NPD6381	Phase 2
0.5824	Remote Similarity	NPD2293	Phase 2
0.5822	Remote Similarity	NPD7502	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD724	Approved
0.5813	Remote Similarity	NPD194	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD415	Discontinued
0.5805	Remote Similarity	NPD4555	Clinical (unspecified phase)
0.5805	Remote Similarity	NPD5300	Clinical (unspecified phase)
0.5803	Remote Similarity	NPD3287	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