NPASS Compound

Structure

NPC187558 OpenBabel07101718282D 25 28 0 0 0 0 0 0 0 0999 V2000 3.4424 3.4738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6884 -1.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7934 -1.4262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7306 -1.5540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8424 -1.1172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9875 -0.8849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3812 -0.6172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3239 -2.4676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4945 0.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0334 1.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8424 -0.1172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1215 -1.3849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0334 0.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4945 0.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0823 1.7796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7934 0.1918 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.3294 -2.3630 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.0823 0.1615 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 2.7733 2.7306 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3794 -1.0169 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 25 1 0 0 0 0 3 5 1 0 0 0 0 3 7 2 0 0 0 0 4 6 1 0 0 0 0 4 8 2 0 0 0 0 5 12 2 0 0 0 0 6 13 2 0 0 0 0 7 20 1 0 0 0 0 8 21 1 0 0 0 0 9 16 1 0 0 0 0 9 17 2 0 0 0 0 10 14 2 0 0 0 0 10 18 1 0 0 0 0 11 15 1 0 0 0 0 11 19 2 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 22 1 0 0 0 0 15 23 2 0 0 0 0 16 18 2 0 0 0 0 16 22 1 0 0 0 0 17 19 1 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 19 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	334.14
Volume:	340.794
LogP:	2.964
LogD:	3.139
LogS:	-4.675
# Rotatable Bonds:	5
TPSA:	78.19
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.665
Synthetic Accessibility Score:	3.519
Fsp3:	0.105
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:	-5.538
MDCK Permeability:	1.809898458304815e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.944
30% Bioavailability (F30%):	0.08

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.538
Plasma Protein Binding (PPB):	96.17242431640625%
Volume Distribution (VD):	0.532
Pgp-substrate:	4.045029163360596%

ADMET: Metabolism

CYP1A2-inhibitor:	0.981
CYP1A2-substrate:	0.975
CYP2C19-inhibitor:	0.888
CYP2C19-substrate:	0.364
CYP2C9-inhibitor:	0.702
CYP2C9-substrate:	0.817
CYP2D6-inhibitor:	0.038
CYP2D6-substrate:	0.885
CYP3A4-inhibitor:	0.875
CYP3A4-substrate:	0.342

ADMET: Excretion

Clearance (CL):	4.414
Half-life (T1/2):	0.865

ADMET: Toxicity

hERG Blockers:	0.319
Human Hepatotoxicity (H-HT):	0.969
Drug-inuced Liver Injury (DILI):	0.38
AMES Toxicity:	0.36
Rat Oral Acute Toxicity:	0.976
Maximum Recommended Daily Dose:	0.949
Skin Sensitization:	0.899
Carcinogencity:	0.09
Eye Corrosion:	0.009
Eye Irritation:	0.164
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: NPC187558

Natural Product ID:	NPC187558
*Common Name:**	QEVDCWRFEOZGOP-RQZCQDPDSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QEVDCWRFEOZGOP-RQZCQDPDSA-N
Standard InCHI:	InChI=1S/C19H18N4O2/c1-24-18-10-14(12-5-3-7-20-12)22-16(18)9-17-19(25-2)11-15(23-17)13-6-4-8-21-13/h3-11,20-22H,1-2H3/b17-9+
SMILES:	COC1=CC(=N/C/1=C/c1[nH]c(cc1OC)c1ccc[nH]1)c1ccc[nH]1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1091177
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000090] Pyrroles [CHEMONTID:0002257] Substituted pyrroles [CHEMONTID:0002028] Dipyrrins

*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
NPO958	Tambja ceutae	Species	Polyceridae	Eukaryota	n.a.	Azorean	n.a.	PMID[20227875]
NPO958	Tambja ceutae	Species	Polyceridae	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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT492	Cell Line	Caco-2	Homo sapiens	IC50	=	91000.0	nM	PMID[491951]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	70000.0	nM	PMID[491951]
NPT76	Cell Line	C6	Rattus norvegicus	IC50	=	7000.0	nM	PMID[491951]
NPT1635	Cell Line	H9c2	Rattus norvegicus	IC50	=	107000.0	nM	PMID[491951]
NPT520	Cell Line	3T3-L1	Mus musculus	IC50	=	24000.0	nM	PMID[491951]

☑ 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 NPC187558 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	736
0.1-0.2	13624
0.2-0.3	7469
0.3-0.4	13976
0.4-0.5	3556
0.5-0.6	2498
0.6-0.7	764
0.7-0.8	67
0.8-0.85	2
0.85-0.9	0
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9494	High Similarity	NPC84853
0.8385	Intermediate Similarity	NPC19872
0.8333	Intermediate Similarity	NPC18487
0.8086	Intermediate Similarity	NPC314954
0.8021	Intermediate Similarity	NPC161887
0.7989	Intermediate Similarity	NPC20249
0.7972	Intermediate Similarity	NPC101543
0.7972	Intermediate Similarity	NPC469554
0.7949	Intermediate Similarity	NPC267928
0.7931	Intermediate Similarity	NPC26679
0.7889	Intermediate Similarity	NPC476138
0.7889	Intermediate Similarity	NPC245816
0.788	Intermediate Similarity	NPC476518
0.7871	Intermediate Similarity	NPC185782
0.7838	Intermediate Similarity	NPC121658
0.7838	Intermediate Similarity	NPC14651
0.7831	Intermediate Similarity	NPC219963
0.7831	Intermediate Similarity	NPC266551
0.7704	Intermediate Similarity	NPC226202
0.7701	Intermediate Similarity	NPC111624
0.77	Intermediate Similarity	NPC232727
0.765	Intermediate Similarity	NPC176538
0.765	Intermediate Similarity	NPC121772
0.7644	Intermediate Similarity	NPC8022
0.7644	Intermediate Similarity	NPC470799
0.7641	Intermediate Similarity	NPC134079
0.7573	Intermediate Similarity	NPC167860
0.7573	Intermediate Similarity	NPC123976
0.7561	Intermediate Similarity	NPC287208
0.756	Intermediate Similarity	NPC170114
0.7551	Intermediate Similarity	NPC76748
0.7548	Intermediate Similarity	NPC476287
0.7525	Intermediate Similarity	NPC307963
0.7513	Intermediate Similarity	NPC92111
0.7512	Intermediate Similarity	NPC470549
0.75	Intermediate Similarity	NPC296527
0.7474	Intermediate Similarity	NPC284678
0.7465	Intermediate Similarity	NPC310118
0.7453	Intermediate Similarity	NPC213530
0.7453	Intermediate Similarity	NPC193267
0.7451	Intermediate Similarity	NPC475774
0.745	Intermediate Similarity	NPC13880
0.7435	Intermediate Similarity	NPC224764
0.7432	Intermediate Similarity	NPC477815
0.7401	Intermediate Similarity	NPC26543
0.7364	Intermediate Similarity	NPC141053
0.7364	Intermediate Similarity	NPC180504
0.736	Intermediate Similarity	NPC206251
0.736	Intermediate Similarity	NPC74382
0.7358	Intermediate Similarity	NPC42979
0.7333	Intermediate Similarity	NPC94157
0.733	Intermediate Similarity	NPC285558
0.7318	Intermediate Similarity	NPC196718
0.7316	Intermediate Similarity	NPC53534
0.7294	Intermediate Similarity	NPC110151
0.729	Intermediate Similarity	NPC292958
0.7277	Intermediate Similarity	NPC251090
0.7273	Intermediate Similarity	NPC25899
0.724	Intermediate Similarity	NPC102593
0.7236	Intermediate Similarity	NPC224327
0.7232	Intermediate Similarity	NPC101350
0.723	Intermediate Similarity	NPC288349
0.7222	Intermediate Similarity	NPC60621
0.722	Intermediate Similarity	NPC315957
0.72	Intermediate Similarity	NPC477861
0.7195	Intermediate Similarity	NPC260434
0.7188	Intermediate Similarity	NPC235685
0.7171	Intermediate Similarity	NPC476167
0.7163	Intermediate Similarity	NPC470500
0.7162	Intermediate Similarity	NPC471891
0.7156	Intermediate Similarity	NPC5145
0.7143	Intermediate Similarity	NPC476465
0.7143	Intermediate Similarity	NPC48192
0.7131	Intermediate Similarity	NPC152620
0.7129	Intermediate Similarity	NPC324149
0.7122	Intermediate Similarity	NPC192315
0.7097	Intermediate Similarity	NPC132642
0.7095	Intermediate Similarity	NPC104049
0.7092	Intermediate Similarity	NPC141377
0.7083	Intermediate Similarity	NPC1527
0.7078	Intermediate Similarity	NPC122436
0.7059	Intermediate Similarity	NPC473185
0.7056	Intermediate Similarity	NPC471080
0.7056	Intermediate Similarity	NPC469592
0.7056	Intermediate Similarity	NPC266931
0.7042	Intermediate Similarity	NPC208284
0.7035	Intermediate Similarity	NPC15801
0.7028	Intermediate Similarity	NPC174672
0.7022	Intermediate Similarity	NPC182222
0.702	Intermediate Similarity	NPC118776
0.7018	Intermediate Similarity	NPC148889
0.7009	Intermediate Similarity	NPC316981
0.6995	Remote Similarity	NPC199667
0.6995	Remote Similarity	NPC11464
0.699	Remote Similarity	NPC77555
0.6985	Remote Similarity	NPC48938
0.698	Remote Similarity	NPC242928
0.6964	Remote Similarity	NPC475253
0.6959	Remote Similarity	NPC476041
0.6959	Remote Similarity	NPC304926
0.6957	Remote Similarity	NPC316756
0.6952	Remote Similarity	NPC223427
0.695	Remote Similarity	NPC84478
0.6948	Remote Similarity	NPC473181
0.6948	Remote Similarity	NPC174758
0.6931	Remote Similarity	NPC46580
0.693	Remote Similarity	NPC473180
0.6927	Remote Similarity	NPC198673
0.6927	Remote Similarity	NPC469594
0.6927	Remote Similarity	NPC106937
0.692	Remote Similarity	NPC258048
0.6919	Remote Similarity	NPC475070
0.6915	Remote Similarity	NPC314002
0.6912	Remote Similarity	NPC36405
0.691	Remote Similarity	NPC63971
0.691	Remote Similarity	NPC91868
0.6901	Remote Similarity	NPC82548
0.69	Remote Similarity	NPC176127
0.6895	Remote Similarity	NPC473179
0.6886	Remote Similarity	NPC240384
0.6881	Remote Similarity	NPC171171
0.6878	Remote Similarity	NPC99666
0.6875	Remote Similarity	NPC177404
0.6875	Remote Similarity	NPC168911
0.6866	Remote Similarity	NPC204717
0.685	Remote Similarity	NPC474798
0.6849	Remote Similarity	NPC303658
0.6842	Remote Similarity	NPC295228
0.6835	Remote Similarity	NPC472027
0.6825	Remote Similarity	NPC473761
0.6823	Remote Similarity	NPC285635
0.6822	Remote Similarity	NPC266249
0.6816	Remote Similarity	NPC220765
0.6814	Remote Similarity	NPC110741
0.6814	Remote Similarity	NPC476451
0.6812	Remote Similarity	NPC473183
0.6798	Remote Similarity	NPC325976
0.6794	Remote Similarity	NPC239954
0.6786	Remote Similarity	NPC153467
0.6784	Remote Similarity	NPC96890
0.6784	Remote Similarity	NPC473186
0.6784	Remote Similarity	NPC184964
0.6781	Remote Similarity	NPC472434
0.6773	Remote Similarity	NPC264285
0.6762	Remote Similarity	NPC128823
0.6759	Remote Similarity	NPC123839
0.6758	Remote Similarity	NPC274982
0.6756	Remote Similarity	NPC6215
0.6749	Remote Similarity	NPC15102
0.6743	Remote Similarity	NPC473757
0.6742	Remote Similarity	NPC168209
0.6736	Remote Similarity	NPC131718
0.673	Remote Similarity	NPC329747
0.6727	Remote Similarity	NPC305984
0.6725	Remote Similarity	NPC39370
0.6725	Remote Similarity	NPC473184
0.6724	Remote Similarity	NPC81175
0.6713	Remote Similarity	NPC469589
0.6711	Remote Similarity	NPC227908
0.6709	Remote Similarity	NPC78609
0.6699	Remote Similarity	NPC242209
0.6667	Remote Similarity	NPC70956
0.6667	Remote Similarity	NPC476118
0.6667	Remote Similarity	NPC258773
0.6667	Remote Similarity	NPC162530
0.6667	Remote Similarity	NPC102423
0.6667	Remote Similarity	NPC311276
0.6667	Remote Similarity	NPC243834
0.6667	Remote Similarity	NPC118511
0.6652	Remote Similarity	NPC243633
0.6652	Remote Similarity	NPC16352
0.6652	Remote Similarity	NPC175150
0.6652	Remote Similarity	NPC470501
0.6651	Remote Similarity	NPC329793
0.6651	Remote Similarity	NPC131017
0.665	Remote Similarity	NPC32771
0.6649	Remote Similarity	NPC26872
0.6638	Remote Similarity	NPC11408
0.6637	Remote Similarity	NPC477533
0.6637	Remote Similarity	NPC86078
0.6637	Remote Similarity	NPC323969
0.6635	Remote Similarity	NPC72211
0.6633	Remote Similarity	NPC313791
0.6632	Remote Similarity	NPC212742
0.6632	Remote Similarity	NPC26850
0.6623	Remote Similarity	NPC326363
0.6621	Remote Similarity	NPC118940
0.6621	Remote Similarity	NPC294620
0.6607	Remote Similarity	NPC470502
0.6606	Remote Similarity	NPC148183
0.6606	Remote Similarity	NPC152768
0.6605	Remote Similarity	NPC470930
0.6603	Remote Similarity	NPC475190
0.6591	Remote Similarity	NPC477610
0.6591	Remote Similarity	NPC478074
0.659	Remote Similarity	NPC475910
0.6588	Remote Similarity	NPC156704
0.6581	Remote Similarity	NPC217554
0.6579	Remote Similarity	NPC194740
0.6575	Remote Similarity	NPC242923

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 NPC187558 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	311
0.1-0.2	1072
0.2-0.3	639
0.3-0.4	2292
0.4-0.5	2558
0.5-0.6	1878
0.6-0.7	377
0.7-0.8	22
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
0.7784	Intermediate Similarity	NPD565	Phase 2
0.7525	Intermediate Similarity	NPD1038	Approved
0.7463	Intermediate Similarity	NPD8403	Phase 1
0.7437	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD1392	Approved
0.7385	Intermediate Similarity	NPD8512	Phase 3
0.7358	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD5066	Phase 2
0.7286	Intermediate Similarity	NPD5067	Phase 2
0.7255	Intermediate Similarity	NPD3825	Phase 3
0.722	Intermediate Similarity	NPD1739	Approved
0.722	Intermediate Similarity	NPD1740	Approved
0.7219	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD4372	Phase 1
0.72	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD1034	Phase 3
0.7186	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD4548	Discontinued
0.7166	Intermediate Similarity	NPD9574	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD4795	Phase 2
0.715	Intermediate Similarity	NPD5612	Discontinued
0.7143	Intermediate Similarity	NPD2187	Approved
0.7143	Intermediate Similarity	NPD2189	Approved
0.7105	Intermediate Similarity	NPD4440	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD3343	Phase 3
0.7087	Intermediate Similarity	NPD1768	Approved
0.7059	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD3402	Phase 1
0.7048	Intermediate Similarity	NPD3003	Approved
0.7042	Intermediate Similarity	NPD949	Phase 1
0.7042	Intermediate Similarity	NPD4131	Phase 3
0.7035	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD5559	Phase 2
0.7024	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD3477	Phase 2
0.7	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1418	Phase 2
0.6996	Remote Similarity	NPD5018	Phase 3
0.6978	Remote Similarity	NPD7558	Phase 2
0.6972	Remote Similarity	NPD3514	Clinical (unspecified phase)
0.6965	Remote Similarity	NPD5256	Discontinued
0.6963	Remote Similarity	NPD3570	Phase 2
0.6959	Remote Similarity	NPD5319	Approved
0.6959	Remote Similarity	NPD5320	Approved
0.6958	Remote Similarity	NPD8284	Discontinued
0.6957	Remote Similarity	NPD5802	Phase 2
0.6957	Remote Similarity	NPD1941	Approved
0.6953	Remote Similarity	NPD5482	Discontinued
0.6927	Remote Similarity	NPD802	Phase 2
0.6923	Remote Similarity	NPD5999	Phase 2
0.6923	Remote Similarity	NPD6306	Phase 2
0.6901	Remote Similarity	NPD5658	Approved
0.6898	Remote Similarity	NPD3835	Phase 3
0.6898	Remote Similarity	NPD3833	Phase 3
0.6893	Remote Similarity	NPD1951	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD2062	Phase 2
0.6866	Remote Similarity	NPD5902	Approved
0.6866	Remote Similarity	NPD5903	Approved
0.6864	Remote Similarity	NPD6242	Discontinued
0.6862	Remote Similarity	NPD9595	Approved
0.6862	Remote Similarity	NPD9596	Approved
0.6861	Remote Similarity	NPD1273	Discontinued
0.6849	Remote Similarity	NPD5948	Phase 2
0.6842	Remote Similarity	NPD4654	Phase 1
0.6842	Remote Similarity	NPD3006	Discontinued
0.6837	Remote Similarity	NPD9548	Phase 2
0.6835	Remote Similarity	NPD6643	Discontinued
0.6833	Remote Similarity	NPD4881	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD2471	Approved
0.6828	Remote Similarity	NPD2472	Approved
0.6827	Remote Similarity	NPD7948	Phase 1
0.6821	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.682	Remote Similarity	NPD1322	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD4344	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD4343	Phase 1
0.6806	Remote Similarity	NPD3939	Suspended
0.6796	Remote Similarity	NPD6569	Phase 2
0.6789	Remote Similarity	NPD6140	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7603	Discontinued
0.6784	Remote Similarity	NPD4072	Approved
0.6784	Remote Similarity	NPD4071	Approved
0.6774	Remote Similarity	NPD6202	Discontinued
0.6773	Remote Similarity	NPD4429	Discontinued
0.6773	Remote Similarity	NPD5632	Approved
0.6771	Remote Similarity	NPD5045	Phase 2
0.6765	Remote Similarity	NPD6393	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD7194	Discontinued
0.6741	Remote Similarity	NPD4890	Phase 2
0.6741	Remote Similarity	NPD1258	Discontinued
0.6738	Remote Similarity	NPD7068	Approved
0.6738	Remote Similarity	NPD7067	Approved
0.6731	Remote Similarity	NPD3396	Approved
0.6731	Remote Similarity	NPD3395	Approved
0.6726	Remote Similarity	NPD1856	Discontinued
0.6712	Remote Similarity	NPD2547	Discontinued
0.671	Remote Similarity	NPD3331	Phase 3
0.6708	Remote Similarity	NPD5949	Phase 3
0.67	Remote Similarity	NPD1334	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD3330	Phase 1
0.6696	Remote Similarity	NPD1259	Discontinued
0.6694	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD8510	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD8396	Approved
0.6682	Remote Similarity	NPD8395	Approved
0.6682	Remote Similarity	NPD3397	Phase 2
0.6667	Remote Similarity	NPD862	Approved
0.6667	Remote Similarity	NPD5140	Approved
0.6667	Remote Similarity	NPD2772	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD863	Approved
0.6667	Remote Similarity	NPD2954	Approved
0.6667	Remote Similarity	NPD2314	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5138	Approved
0.6667	Remote Similarity	NPD537	Phase 2
0.6667	Remote Similarity	NPD2955	Approved
0.6667	Remote Similarity	NPD2952	Discontinued
0.6667	Remote Similarity	NPD534	Phase 2
0.6667	Remote Similarity	NPD6961	Discontinued
0.6667	Remote Similarity	NPD861	Approved
0.6652	Remote Similarity	NPD1744	Approved
0.6637	Remote Similarity	NPD6856	Discontinued
0.6634	Remote Similarity	NPD4921	Phase 3
0.6634	Remote Similarity	NPD6595	Phase 3
0.6634	Remote Similarity	NPD4919	Phase 3
0.6634	Remote Similarity	NPD706	Phase 1
0.6634	Remote Similarity	NPD4920	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD2581	Approved
0.6632	Remote Similarity	NPD2582	Approved
0.6625	Remote Similarity	NPD8442	Discontinued
0.6624	Remote Similarity	NPD4558	Phase 2
0.6624	Remote Similarity	NPD6473	Phase 1
0.6624	Remote Similarity	NPD5644	Phase 1
0.6623	Remote Similarity	NPD6968	Phase 2
0.6623	Remote Similarity	NPD6969	Phase 2
0.6623	Remote Similarity	NPD4454	Phase 2
0.6622	Remote Similarity	NPD6985	Discontinued
0.662	Remote Similarity	NPD796	Phase 2
0.662	Remote Similarity	NPD5259	Phase 3
0.6619	Remote Similarity	NPD774	Phase 3
0.6617	Remote Similarity	NPD2144	Approved
0.6613	Remote Similarity	NPD3834	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD5450	Discontinued
0.6609	Remote Similarity	NPD1927	Discontinued
0.6609	Remote Similarity	NPD6223	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD2151	Approved
0.6601	Remote Similarity	NPD3386	Phase 2
0.6592	Remote Similarity	NPD3875	Discontinued
0.659	Remote Similarity	NPD5529	Phase 1
0.659	Remote Similarity	NPD2509	Approved
0.659	Remote Similarity	NPD2510	Approved
0.659	Remote Similarity	NPD5528	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD4889	Approved
0.6585	Remote Similarity	NPD4442	Phase 2
0.6578	Remote Similarity	NPD7219	Approved
0.6578	Remote Similarity	NPD7221	Approved
0.6577	Remote Similarity	NPD7980	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD7470	Discontinued
0.6569	Remote Similarity	NPD5596	Phase 2
0.6564	Remote Similarity	NPD7051	Phase 3
0.6564	Remote Similarity	NPD112	Approved
0.6564	Remote Similarity	NPD9705	Discontinued
0.6564	Remote Similarity	NPD7050	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD1603	Discontinued
0.6558	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD3921	Approved
0.6555	Remote Similarity	NPD3923	Approved
0.6555	Remote Similarity	NPD3924	Approved
0.6555	Remote Similarity	NPD3922	Approved
0.6547	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD1911	Approved
0.6535	Remote Similarity	NPD1910	Approved
0.6528	Remote Similarity	NPD4038	Approved
0.6528	Remote Similarity	NPD4122	Approved
0.6528	Remote Similarity	NPD4034	Approved
0.6528	Remote Similarity	NPD31	Approved
0.6528	Remote Similarity	NPD4036	Approved
0.6528	Remote Similarity	NPD32	Approved
0.6528	Remote Similarity	NPD4037	Approved
0.6528	Remote Similarity	NPD4039	Approved
0.6528	Remote Similarity	NPD4033	Approved
0.6528	Remote Similarity	NPD4035	Approved
0.6526	Remote Similarity	NPD2958	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD1504	Discontinued
0.652	Remote Similarity	NPD3938	Phase 1
0.652	Remote Similarity	NPD3038	Discontinued
0.652	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD5065	Approved
0.6516	Remote Similarity	NPD2894	Phase 2
0.6514	Remote Similarity	NPD2816	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD6769	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4502	Phase 2
0.65	Remote Similarity	NPD2540	Clinical (unspecified phase)
0.6498	Remote Similarity	NPD8525	Approved
0.6498	Remote Similarity	NPD5601	Phase 2
0.6495	Remote Similarity	NPD484	Approved
0.6493	Remote Similarity	NPD1602	Discontinued
0.6491	Remote Similarity	NPD1907	Phase 3
0.649	Remote Similarity	NPD4021	Phase 2

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