NPASS Compound

Structure

NPC175916 OpenBabel07101718282D 25 29 0 0 0 0 0 0 0 0999 V2000 5.4745 1.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4745 0.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6085 1.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6085 -0.2728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1247 -0.9888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8764 2.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1939 -1.3542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0104 3.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6945 0.3345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7424 1.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8764 1.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2738 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7424 0.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7521 1.1031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0104 1.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0104 0.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1444 1.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5793 1.2029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6369 0.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5880 -0.7307 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.1444 2.7272 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.8764 -0.2728 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.1152 1.5374 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.6531 1.5370 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 10 2 0 0 0 0 4 13 2 0 0 0 0 5 7 1 0 0 0 0 5 12 1 0 0 0 0 6 8 2 0 0 0 0 6 11 1 0 0 0 0 7 20 1 0 0 0 0 8 21 1 0 0 0 0 9 14 1 0 0 0 0 9 25 1 0 0 0 0 10 11 1 0 0 0 0 10 13 1 0 0 0 0 11 15 2 0 0 0 0 12 16 2 0 0 0 0 12 19 1 0 0 0 0 13 22 1 0 0 0 0 14 23 2 0 0 0 0 14 24 1 0 0 0 0 15 16 1 0 0 0 0 15 17 1 0 0 0 0 16 22 1 0 0 0 0 17 18 1 0 0 0 0 17 21 2 0 0 0 0 18 19 2 0 0 0 0 18 23 1 0 0 0 0 19 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	348.1
Volume:	341.956
LogP:	1.717
LogD:	1.742
LogS:	-3.711
# Rotatable Bonds:	2
TPSA:	84.39
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.428
Synthetic Accessibility Score:	3.769
Fsp3:	0.211
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:	-5.423
MDCK Permeability:	2.6741779493022477e-06
Pgp-inhibitor:	0.008
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.91
20% Bioavailability (F20%):	0.197
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.518
Plasma Protein Binding (PPB):	94.1551742553711%
Volume Distribution (VD):	1.248
Pgp-substrate:	4.108364105224609%

ADMET: Metabolism

CYP1A2-inhibitor:	0.984
CYP1A2-substrate:	0.797
CYP2C19-inhibitor:	0.047
CYP2C19-substrate:	0.127
CYP2C9-inhibitor:	0.018
CYP2C9-substrate:	0.463
CYP2D6-inhibitor:	0.436
CYP2D6-substrate:	0.89
CYP3A4-inhibitor:	0.213
CYP3A4-substrate:	0.198

ADMET: Excretion

Clearance (CL):	3.028
Half-life (T1/2):	0.109

ADMET: Toxicity

hERG Blockers:	0.545
Human Hepatotoxicity (H-HT):	0.823
Drug-inuced Liver Injury (DILI):	0.966
AMES Toxicity:	0.919
Rat Oral Acute Toxicity:	0.698
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.872
Carcinogencity:	0.207
Eye Corrosion:	0.004
Eye Irritation:	0.014
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC175916

Natural Product ID:	NPC175916
*Common Name:**	N-Deacetylshermilamine B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	LHOMOJRZMZIBEM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H16N4OS/c20-7-5-12-16-15-11(10-3-1-2-4-13(10)22-16)6-8-21-17(15)18-19(12)25-9-14(24)23-18/h1-4,6,8,22H,5,7,9,20H2,(H,23,24)
SMILES:	c1ccc2c(-c3ccnc4c3c(c(CCN)c3c4N=C(CS3)O)N2)c1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1163670
PubChem CID:	46849171
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0001908] Benzoquinolines [CHEMONTID:0000274] Acridines [CHEMONTID:0001763] Pyridoacridines [CHEMONTID:0002827] Pyrido[2,3,4-kl]acridines

*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
NPO9248	Cystodytes dellechiajei	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1812214]
NPO9248	Cystodytes dellechiajei	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20491501]
NPO9248	Cystodytes dellechiajei	Species	Polycitoridae	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
MIC	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	1100.0	nM	PMID[534487]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	4500.0	nM	PMID[534487]

☑ 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 NPC175916 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	1065
0.1-0.2	15355
0.2-0.3	18101
0.3-0.4	3742
0.4-0.5	2303
0.5-0.6	1742
0.6-0.7	375
0.7-0.8	5
0.8-0.85	0
0.85-0.9	5
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9838	High Similarity	NPC66699
0.9681	High Similarity	NPC124636
0.963	High Similarity	NPC193370
0.8939	High Similarity	NPC173344
0.8894	High Similarity	NPC149014
0.8806	High Similarity	NPC77022
0.8762	High Similarity	NPC216221
0.8731	High Similarity	NPC147810
0.7385	Intermediate Similarity	NPC297034
0.73	Intermediate Similarity	NPC467063
0.7157	Intermediate Similarity	NPC103119
0.7107	Intermediate Similarity	NPC201634
0.7073	Intermediate Similarity	NPC255909
0.7053	Intermediate Similarity	NPC272458
0.7053	Intermediate Similarity	NPC216713
0.7031	Intermediate Similarity	NPC24802
0.697	Remote Similarity	NPC91895
0.697	Remote Similarity	NPC194411
0.6939	Remote Similarity	NPC317105
0.6927	Remote Similarity	NPC325903
0.6919	Remote Similarity	NPC169433
0.6897	Remote Similarity	NPC164228
0.689	Remote Similarity	NPC216550
0.6888	Remote Similarity	NPC225018
0.6881	Remote Similarity	NPC248454
0.6866	Remote Similarity	NPC275305
0.6866	Remote Similarity	NPC37423
0.6865	Remote Similarity	NPC314102
0.6865	Remote Similarity	NPC251722
0.684	Remote Similarity	NPC272483
0.6837	Remote Similarity	NPC122141
0.6837	Remote Similarity	NPC215584
0.6837	Remote Similarity	NPC44773
0.6832	Remote Similarity	NPC280852
0.6821	Remote Similarity	NPC193740
0.6808	Remote Similarity	NPC265576
0.6806	Remote Similarity	NPC471957
0.6806	Remote Similarity	NPC469811
0.6798	Remote Similarity	NPC68354
0.6786	Remote Similarity	NPC56765
0.6786	Remote Similarity	NPC474791
0.6786	Remote Similarity	NPC206819
0.6786	Remote Similarity	NPC318065
0.6771	Remote Similarity	NPC321911
0.6768	Remote Similarity	NPC478184
0.6765	Remote Similarity	NPC215795
0.6765	Remote Similarity	NPC176199
0.6754	Remote Similarity	NPC63545
0.675	Remote Similarity	NPC63751
0.6748	Remote Similarity	NPC163055
0.6719	Remote Similarity	NPC201380
0.6719	Remote Similarity	NPC179787
0.6717	Remote Similarity	NPC470203
0.6702	Remote Similarity	NPC314372
0.6701	Remote Similarity	NPC135141
0.6701	Remote Similarity	NPC475990
0.6701	Remote Similarity	NPC470823
0.6701	Remote Similarity	NPC92796
0.67	Remote Similarity	NPC471579
0.6684	Remote Similarity	NPC190296
0.6683	Remote Similarity	NPC478182
0.6683	Remote Similarity	NPC90723
0.6683	Remote Similarity	NPC15102
0.6667	Remote Similarity	NPC477113
0.6667	Remote Similarity	NPC470204
0.6651	Remote Similarity	NPC34837
0.665	Remote Similarity	NPC167635
0.665	Remote Similarity	NPC469897
0.6649	Remote Similarity	NPC24678
0.6649	Remote Similarity	NPC40070
0.6649	Remote Similarity	NPC105818
0.6636	Remote Similarity	NPC128244
0.6634	Remote Similarity	NPC59269
0.6634	Remote Similarity	NPC157583
0.6633	Remote Similarity	NPC476219
0.6632	Remote Similarity	NPC470111
0.6616	Remote Similarity	NPC293487
0.6615	Remote Similarity	NPC159856
0.6606	Remote Similarity	NPC477111
0.6605	Remote Similarity	NPC167710
0.6599	Remote Similarity	NPC51054
0.6597	Remote Similarity	NPC320863
0.6591	Remote Similarity	NPC475288
0.6589	Remote Similarity	NPC294693
0.6582	Remote Similarity	NPC73952
0.6582	Remote Similarity	NPC469763
0.6582	Remote Similarity	NPC469765
0.6582	Remote Similarity	NPC200214
0.6582	Remote Similarity	NPC469786
0.6582	Remote Similarity	NPC469760
0.6582	Remote Similarity	NPC259644
0.6582	Remote Similarity	NPC25008
0.6566	Remote Similarity	NPC286427
0.6566	Remote Similarity	NPC236711
0.6553	Remote Similarity	NPC237188
0.6548	Remote Similarity	NPC212376
0.6548	Remote Similarity	NPC75540
0.6548	Remote Similarity	NPC80597
0.6548	Remote Similarity	NPC70922
0.6548	Remote Similarity	NPC211572
0.6541	Remote Similarity	NPC282398
0.654	Remote Similarity	NPC317030
0.6535	Remote Similarity	NPC478183
0.6535	Remote Similarity	NPC49954
0.6535	Remote Similarity	NPC474561
0.6533	Remote Similarity	NPC41257
0.6533	Remote Similarity	NPC474880
0.6533	Remote Similarity	NPC221786
0.6531	Remote Similarity	NPC470233
0.6524	Remote Similarity	NPC99939
0.6524	Remote Similarity	NPC308931
0.652	Remote Similarity	NPC469727
0.6517	Remote Similarity	NPC194640
0.6515	Remote Similarity	NPC469785
0.651	Remote Similarity	NPC20144
0.6508	Remote Similarity	NPC105127
0.65	Remote Similarity	NPC279918
0.6497	Remote Similarity	NPC161108
0.6495	Remote Similarity	NPC143872
0.6495	Remote Similarity	NPC288838
0.6493	Remote Similarity	NPC474707
0.6492	Remote Similarity	NPC469761
0.6492	Remote Similarity	NPC469784
0.6492	Remote Similarity	NPC469767
0.6492	Remote Similarity	NPC469783
0.6492	Remote Similarity	NPC469779
0.6492	Remote Similarity	NPC469780
0.6492	Remote Similarity	NPC469768
0.6486	Remote Similarity	NPC473362
0.6486	Remote Similarity	NPC166492
0.6484	Remote Similarity	NPC469308
0.6482	Remote Similarity	NPC469762
0.648	Remote Similarity	NPC53947
0.648	Remote Similarity	NPC148592
0.6479	Remote Similarity	NPC231536
0.6479	Remote Similarity	NPC95783
0.6471	Remote Similarity	NPC88115
0.6468	Remote Similarity	NPC282231
0.6468	Remote Similarity	NPC478185
0.6462	Remote Similarity	NPC204565
0.6458	Remote Similarity	NPC469766
0.6455	Remote Similarity	NPC96102
0.6453	Remote Similarity	NPC56233
0.6452	Remote Similarity	NPC229332
0.6443	Remote Similarity	NPC86288
0.644	Remote Similarity	NPC110126
0.644	Remote Similarity	NPC88097
0.644	Remote Similarity	NPC73767
0.6432	Remote Similarity	NPC476464
0.6432	Remote Similarity	NPC65215
0.6432	Remote Similarity	NPC173028
0.6425	Remote Similarity	NPC474958
0.6422	Remote Similarity	NPC201700
0.6421	Remote Similarity	NPC84911
0.6419	Remote Similarity	NPC324149
0.6418	Remote Similarity	NPC229173
0.6406	Remote Similarity	NPC284635
0.6406	Remote Similarity	NPC115611
0.6404	Remote Similarity	NPC477110
0.64	Remote Similarity	NPC216643
0.6398	Remote Similarity	NPC108011
0.6395	Remote Similarity	NPC19170
0.639	Remote Similarity	NPC32534
0.6383	Remote Similarity	NPC297862
0.6382	Remote Similarity	NPC38736
0.6382	Remote Similarity	NPC476297
0.6381	Remote Similarity	NPC233936
0.638	Remote Similarity	NPC106757
0.6378	Remote Similarity	NPC21605
0.6373	Remote Similarity	NPC160105
0.6373	Remote Similarity	NPC54988
0.6373	Remote Similarity	NPC88121
0.6368	Remote Similarity	NPC29886
0.6368	Remote Similarity	NPC261195
0.6364	Remote Similarity	NPC11126
0.6359	Remote Similarity	NPC146373
0.6359	Remote Similarity	NPC285731
0.6359	Remote Similarity	NPC82331
0.6359	Remote Similarity	NPC166424
0.6359	Remote Similarity	NPC245244
0.6355	Remote Similarity	NPC311276
0.6351	Remote Similarity	NPC48938
0.635	Remote Similarity	NPC184476
0.6345	Remote Similarity	NPC124005
0.6344	Remote Similarity	NPC31385
0.6344	Remote Similarity	NPC75726
0.6344	Remote Similarity	NPC110602
0.6339	Remote Similarity	NPC46358
0.6338	Remote Similarity	NPC94752
0.6333	Remote Similarity	NPC24864
0.6332	Remote Similarity	NPC138842
0.6332	Remote Similarity	NPC251936
0.633	Remote Similarity	NPC101165
0.6324	Remote Similarity	NPC274229
0.6321	Remote Similarity	NPC279081
0.6321	Remote Similarity	NPC472294
0.6321	Remote Similarity	NPC228835
0.6316	Remote Similarity	NPC151939
0.6316	Remote Similarity	NPC471741
0.6313	Remote Similarity	NPC33421

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 NPC175916 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	406
0.1-0.2	1034
0.2-0.3	1113
0.3-0.4	2498
0.4-0.5	2229
0.5-0.6	1561
0.6-0.7	298
0.7-0.8	11
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
0.7941	Intermediate Similarity	NPD2815	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD3348	Phase 2
0.7474	Intermediate Similarity	NPD3859	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD3610	Approved
0.7194	Intermediate Similarity	NPD3609	Approved
0.7173	Intermediate Similarity	NPD1647	Phase 1
0.7173	Intermediate Similarity	NPD1648	Phase 1
0.7165	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD2720	Phase 1
0.7164	Intermediate Similarity	NPD5105	Approved
0.7164	Intermediate Similarity	NPD5106	Approved
0.715	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD4865	Approved
0.7087	Intermediate Similarity	NPD1235	Phase 3
0.7074	Intermediate Similarity	NPD1661	Suspended
0.7068	Intermediate Similarity	NPD975	Approved
0.7068	Intermediate Similarity	NPD977	Approved
0.7068	Intermediate Similarity	NPD976	Approved
0.7037	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD4128	Approved
0.7005	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6224	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD5315	Discontinued
0.6965	Remote Similarity	NPD4181	Approved
0.6942	Remote Similarity	NPD7394	Phase 2
0.6942	Remote Similarity	NPD3961	Discontinued
0.6919	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD2641	Approved
0.6919	Remote Similarity	NPD2640	Approved
0.6915	Remote Similarity	NPD3401	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD2771	Approved
0.6897	Remote Similarity	NPD4050	Phase 1
0.6895	Remote Similarity	NPD4547	Phase 3
0.6891	Remote Similarity	NPD6285	Phase 2
0.686	Remote Similarity	NPD2310	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD3100	Discontinued
0.6853	Remote Similarity	NPD3323	Discontinued
0.6845	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1683	Approved
0.6842	Remote Similarity	NPD1528	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7469	Discontinued
0.6832	Remote Similarity	NPD6044	Discontinued
0.6827	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD4509	Discontinued
0.681	Remote Similarity	NPD3404	Approved
0.6802	Remote Similarity	NPD1853	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD3506	Approved
0.6798	Remote Similarity	NPD3505	Approved
0.6796	Remote Similarity	NPD7564	Discontinued
0.6786	Remote Similarity	NPD3433	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD4079	Approved
0.6765	Remote Similarity	NPD4076	Approved
0.6753	Remote Similarity	NPD2837	Discontinued
0.6751	Remote Similarity	NPD1403	Approved
0.6751	Remote Similarity	NPD1404	Approved
0.675	Remote Similarity	NPD2390	Clinical (unspecified phase)
0.6749	Remote Similarity	NPD4075	Phase 2
0.672	Remote Similarity	NPD1253	Approved
0.672	Remote Similarity	NPD1255	Approved
0.672	Remote Similarity	NPD1256	Approved
0.672	Remote Similarity	NPD1254	Approved
0.6717	Remote Similarity	NPD6771	Discontinued
0.6716	Remote Similarity	NPD5412	Discontinued
0.6715	Remote Similarity	NPD6178	Phase 3
0.6714	Remote Similarity	NPD7027	Phase 3
0.6712	Remote Similarity	NPD5864	Phase 2
0.6712	Remote Similarity	NPD7195	Clinical (unspecified phase)
0.67	Remote Similarity	NPD5065	Approved
0.67	Remote Similarity	NPD2639	Approved
0.67	Remote Similarity	NPD2642	Approved
0.6699	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD5428	Discontinued
0.6698	Remote Similarity	NPD6239	Discontinued
0.6684	Remote Similarity	NPD4510	Discontinued
0.6684	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD4298	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD6132	Phase 1
0.6667	Remote Similarity	NPD947	Approved
0.6667	Remote Similarity	NPD2185	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2012	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD4886	Phase 2
0.6651	Remote Similarity	NPD7026	Phase 2
0.6636	Remote Similarity	NPD917	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD5145	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD5436	Phase 1
0.6634	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD2385	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD1722	Approved
0.6618	Remote Similarity	NPD7867	Phase 1
0.6606	Remote Similarity	NPD3015	Discontinued
0.6605	Remote Similarity	NPD4473	Clinical (unspecified phase)
0.66	Remote Similarity	NPD3583	Phase 2
0.6599	Remote Similarity	NPD2748	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD5409	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD6156	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD5021	Discontinued
0.6584	Remote Similarity	NPD4640	Approved
0.6584	Remote Similarity	NPD4638	Approved
0.6584	Remote Similarity	NPD4639	Approved
0.6577	Remote Similarity	NPD4472	Approved
0.6577	Remote Similarity	NPD4471	Approved
0.6573	Remote Similarity	NPD4615	Phase 2
0.6567	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD6969	Phase 2
0.6567	Remote Similarity	NPD6968	Phase 2
0.6565	Remote Similarity	NPD5046	Discontinued
0.6564	Remote Similarity	NPD2172	Phase 1
0.6562	Remote Similarity	NPD6749	Phase 1
0.6552	Remote Similarity	NPD4024	Phase 3
0.6547	Remote Similarity	NPD3843	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD5270	Discontinued
0.6528	Remote Similarity	NPD5462	Discontinued
0.652	Remote Similarity	NPD3116	Approved
0.652	Remote Similarity	NPD3117	Approved
0.652	Remote Similarity	NPD7423	Phase 2
0.6514	Remote Similarity	NPD6149	Phase 2
0.6509	Remote Similarity	NPD7540	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD2751	Phase 1
0.6505	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD5862	Discovery
0.6502	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD7127	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD3378	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD4902	Discontinued
0.649	Remote Similarity	NPD2479	Phase 3
0.649	Remote Similarity	NPD2481	Approved
0.6488	Remote Similarity	NPD7217	Approved
0.6488	Remote Similarity	NPD7216	Approved
0.6484	Remote Similarity	NPD4318	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD4957	Phase 2
0.6473	Remote Similarity	NPD4051	Discontinued
0.6473	Remote Similarity	NPD7111	Discontinued
0.6471	Remote Similarity	NPD7209	Approved
0.6471	Remote Similarity	NPD7208	Approved
0.6471	Remote Similarity	NPD7207	Approved
0.6468	Remote Similarity	NPD1315	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD992	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD991	Phase 2
0.6465	Remote Similarity	NPD1328	Approved
0.6465	Remote Similarity	NPD2165	Phase 1
0.6465	Remote Similarity	NPD2717	Phase 2
0.6462	Remote Similarity	NPD8431	Approved
0.6455	Remote Similarity	NPD198	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD5446	Phase 2
0.6452	Remote Similarity	NPD3830	Phase 1
0.6452	Remote Similarity	NPD715	Phase 3
0.6452	Remote Similarity	NPD6664	Approved
0.6445	Remote Similarity	NPD3279	Phase 2
0.6445	Remote Similarity	NPD3082	Discontinued
0.6445	Remote Similarity	NPD1227	Phase 2
0.6444	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD3341	Clinical (unspecified phase)
0.644	Remote Similarity	NPD786	Approved
0.6439	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD6816	Phase 3
0.6435	Remote Similarity	NPD7618	Phase 3
0.6435	Remote Similarity	NPD7619	Phase 3
0.6435	Remote Similarity	NPD4998	Phase 3
0.6435	Remote Similarity	NPD4999	Phase 3
0.6432	Remote Similarity	NPD3113	Approved
0.6432	Remote Similarity	NPD3112	Approved
0.6432	Remote Similarity	NPD3115	Approved
0.6432	Remote Similarity	NPD3114	Approved
0.6432	Remote Similarity	NPD4992	Phase 1
0.6429	Remote Similarity	NPD725	Discontinued
0.6429	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD2430	Phase 2
0.6425	Remote Similarity	NPD2007	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD2006	Phase 2
0.6422	Remote Similarity	NPD3231	Approved
0.6413	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6411	Remote Similarity	NPD7063	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD4112	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD7135	Phase 2
0.6404	Remote Similarity	NPD6958	Approved
0.6404	Remote Similarity	NPD6957	Approved
0.6402	Remote Similarity	NPD2818	Discontinued
0.64	Remote Similarity	NPD2145	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5300	Clinical (unspecified phase)
0.64	Remote Similarity	NPD2865	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6394	Remote Similarity	NPD2144	Approved
0.6393	Remote Similarity	NPD5828	Phase 2
0.6393	Remote Similarity	NPD7049	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD2059	Approved
0.6387	Remote Similarity	NPD2058	Phase 2
0.6387	Remote Similarity	NPD2057	Approved
0.6386	Remote Similarity	NPD2480	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD1597	Phase 1
0.6381	Remote Similarity	NPD5806	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD4649	Clinical (unspecified phase)
0.638	Remote Similarity	NPD8073	Approved
0.638	Remote Similarity	NPD6268	Phase 1
0.638	Remote Similarity	NPD6269	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD6492	Phase 2
0.6377	Remote Similarity	NPD3799	Suspended
0.6372	Remote Similarity	NPD3419	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