NPASS Compound

Structure

CID167710 OpenBabel06191715542D 22 26 0 0 0 0 0 0 0 0999 V2000 3.9264 1.3612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9263 2.2680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1412 0.9077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1409 2.7212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5714 3.6274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7860 4.0810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5707 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3559 1.3609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5705 0.9071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3557 2.2677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5714 2.7205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7849 1.3606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7859 2.2671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0005 2.7206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7847 2.2674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0002 0.9068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7857 1.3603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 3.6275 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 1.5701 2.7209 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.3978 2.2433 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5957 0.8926 0.0000 O 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 8 2 0 0 0 0 4 10 2 0 0 0 0 5 6 1 0 0 0 0 5 11 1 0 0 0 0 6 18 1 0 0 0 0 7 9 2 0 0 0 0 7 19 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 9 12 1 0 0 0 0 10 20 1 0 0 0 0 11 13 1 0 0 0 0 11 21 2 0 0 0 0 12 15 1 0 0 0 0 12 16 2 0 0 0 0 13 14 2 0 0 0 0 13 17 1 0 0 0 0 14 15 1 0 0 0 0 14 18 1 0 0 0 0 15 20 2 0 0 0 0 16 17 1 0 0 0 0 16 19 1 0 0 0 0 17 22 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	289.09
Volume:	286.649
LogP:	3.505
LogD:	2.347
LogS:	-5.461
# Rotatable Bonds:	0
TPSA:	84.67
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.26
Synthetic Accessibility Score:	3.082
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.175
MDCK Permeability:	5.275878720567562e-06
Pgp-inhibitor:	0.004
Pgp-substrate:	0.3
Human Intestinal Absorption (HIA):	0.785
20% Bioavailability (F20%):	0.024
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.083
Plasma Protein Binding (PPB):	88.8453598022461%
Volume Distribution (VD):	0.565
Pgp-substrate:	8.707954406738281%

ADMET: Metabolism

CYP1A2-inhibitor:	0.989
CYP1A2-substrate:	0.665
CYP2C19-inhibitor:	0.868
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.869
CYP2C9-substrate:	0.913
CYP2D6-inhibitor:	0.793
CYP2D6-substrate:	0.853
CYP3A4-inhibitor:	0.325
CYP3A4-substrate:	0.086

ADMET: Excretion

Clearance (CL):	3.27
Half-life (T1/2):	0.67

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.556
Drug-inuced Liver Injury (DILI):	0.979
AMES Toxicity:	0.55
Rat Oral Acute Toxicity:	0.905
Maximum Recommended Daily Dose:	0.925
Skin Sensitization:	0.966
Carcinogencity:	0.113
Eye Corrosion:	0.079
Eye Irritation:	0.983
Respiratory Toxicity:	0.987

Download Data

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

Natural Product: NPC167710

Natural Product ID:	NPC167710
*Common Name:**	Plakinidine E
IUPAC Name:	n.a.
Synonyms:	Plakinidine E
Standard InCHIKey:	IIXLAGITHYGCPA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H11N3O2/c21-11-5-6-18-14-13(11)17(22)16-12-9(7-19-16)8-3-1-2-4-10(8)20-15(12)14/h1-4,7,18-19H,5-6H2
SMILES:	O=C1CCNc2c1c(=O)c1c3c2nc2ccccc2c3c[nH]1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL385861
PubChem CID:	16104902
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001626] Phenanthrolines

*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
NPO4575	Melampodium camphoratum	Species	Asteraceae	Eukaryota	n.a.	Suriname rainforest	n.a.	PMID[15620250]
NPO4575	Melampodium camphoratum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15620250]
NPO6438	Plakortis quasiamphiaster	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17253856]
NPO1819	Conus magus	Species	Conidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5492	Malacosoma disstria	Species	Lasiocampidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6438	Plakortis quasiamphiaster	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3674	Carpinus betulus	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4575	Melampodium camphoratum	Species	Asteraceae	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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	LC50	=	33000.0	nM	PMID[564751]

☑ 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 NPC167710 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	606
0.1-0.2	6537
0.2-0.3	16346
0.3-0.4	13346
0.4-0.5	2069
0.5-0.6	1879
0.6-0.7	1380
0.7-0.8	485
0.8-0.85	36
0.85-0.9	12
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9326	High Similarity	NPC216550
0.8933	High Similarity	NPC467063
0.8715	High Similarity	NPC191415
0.8649	High Similarity	NPC326422
0.8462	Intermediate Similarity	NPC102755
0.8444	Intermediate Similarity	NPC284775
0.8415	Intermediate Similarity	NPC477003
0.836	Intermediate Similarity	NPC128244
0.8351	Intermediate Similarity	NPC304203
0.8343	Intermediate Similarity	NPC157583
0.8342	Intermediate Similarity	NPC317701
0.8342	Intermediate Similarity	NPC476460
0.8286	Intermediate Similarity	NPC474492
0.8278	Intermediate Similarity	NPC252572
0.8235	Intermediate Similarity	NPC103119
0.8191	Intermediate Similarity	NPC324091
0.8172	Intermediate Similarity	NPC133003
0.8142	Intermediate Similarity	NPC237188
0.8136	Intermediate Similarity	NPC100104
0.8136	Intermediate Similarity	NPC470680
0.8135	Intermediate Similarity	NPC237414
0.8105	Intermediate Similarity	NPC272458
0.8087	Intermediate Similarity	NPC151635
0.8075	Intermediate Similarity	NPC99939
0.8075	Intermediate Similarity	NPC308931
0.8	Intermediate Similarity	NPC42372
0.7979	Intermediate Similarity	NPC102592
0.7979	Intermediate Similarity	NPC79356
0.7947	Intermediate Similarity	NPC255909
0.7935	Intermediate Similarity	NPC293216
0.7929	Intermediate Similarity	NPC88115
0.7926	Intermediate Similarity	NPC21429
0.7923	Intermediate Similarity	NPC262338
0.7919	Intermediate Similarity	NPC106757
0.7917	Intermediate Similarity	NPC47190
0.7901	Intermediate Similarity	NPC115232
0.79	Intermediate Similarity	NPC116555
0.7897	Intermediate Similarity	NPC34837
0.7861	Intermediate Similarity	NPC73994
0.7857	Intermediate Similarity	NPC477004
0.7845	Intermediate Similarity	NPC274981
0.7841	Intermediate Similarity	NPC471655
0.7807	Intermediate Similarity	NPC11126
0.7772	Intermediate Similarity	NPC471943
0.7767	Intermediate Similarity	NPC469727
0.7767	Intermediate Similarity	NPC267811
0.7766	Intermediate Similarity	NPC477042
0.7766	Intermediate Similarity	NPC81535
0.7755	Intermediate Similarity	NPC227582
0.7747	Intermediate Similarity	NPC21174
0.7747	Intermediate Similarity	NPC271797
0.7747	Intermediate Similarity	NPC478184
0.7745	Intermediate Similarity	NPC471194
0.7745	Intermediate Similarity	NPC471193
0.7744	Intermediate Similarity	NPC202812
0.7737	Intermediate Similarity	NPC228835
0.7725	Intermediate Similarity	NPC470677
0.7717	Intermediate Similarity	NPC70949
0.7714	Intermediate Similarity	NPC229893
0.7711	Intermediate Similarity	NPC472064
0.7697	Intermediate Similarity	NPC217021
0.7697	Intermediate Similarity	NPC470679
0.7684	Intermediate Similarity	NPC470205
0.7681	Intermediate Similarity	NPC27041
0.7677	Intermediate Similarity	NPC74413
0.7672	Intermediate Similarity	NPC79777
0.7672	Intermediate Similarity	NPC88110
0.7659	Intermediate Similarity	NPC473218
0.7659	Intermediate Similarity	NPC470702
0.7656	Intermediate Similarity	NPC141612
0.7656	Intermediate Similarity	NPC62749
0.7656	Intermediate Similarity	NPC135601
0.7656	Intermediate Similarity	NPC17273
0.7654	Intermediate Similarity	NPC251391
0.7654	Intermediate Similarity	NPC325903
0.765	Intermediate Similarity	NPC317105
0.7647	Intermediate Similarity	NPC469529
0.764	Intermediate Similarity	NPC473878
0.7638	Intermediate Similarity	NPC252338
0.7635	Intermediate Similarity	NPC266249
0.7629	Intermediate Similarity	NPC154339
0.7627	Intermediate Similarity	NPC469811
0.7624	Intermediate Similarity	NPC472065
0.7621	Intermediate Similarity	NPC470703
0.7617	Intermediate Similarity	NPC17059
0.761	Intermediate Similarity	NPC72956
0.7609	Intermediate Similarity	NPC233380
0.7598	Intermediate Similarity	NPC70406
0.7588	Intermediate Similarity	NPC201266
0.7588	Intermediate Similarity	NPC220797
0.7588	Intermediate Similarity	NPC474318
0.7588	Intermediate Similarity	NPC268744
0.7588	Intermediate Similarity	NPC153123
0.7588	Intermediate Similarity	NPC475914
0.7584	Intermediate Similarity	NPC321911
0.7579	Intermediate Similarity	NPC234403
0.7573	Intermediate Similarity	NPC6865
0.7573	Intermediate Similarity	NPC153980
0.7571	Intermediate Similarity	NPC63545
0.7568	Intermediate Similarity	NPC56233
0.7566	Intermediate Similarity	NPC83774
0.7562	Intermediate Similarity	NPC260900
0.7561	Intermediate Similarity	NPC123839
0.7554	Intermediate Similarity	NPC265100
0.7551	Intermediate Similarity	NPC472292
0.755	Intermediate Similarity	NPC269203
0.755	Intermediate Similarity	NPC166209
0.755	Intermediate Similarity	NPC77241
0.755	Intermediate Similarity	NPC13456
0.7541	Intermediate Similarity	NPC122141
0.7528	Intermediate Similarity	NPC105811
0.7528	Intermediate Similarity	NPC201380
0.7528	Intermediate Similarity	NPC179787
0.7526	Intermediate Similarity	NPC55772
0.7525	Intermediate Similarity	NPC472293
0.7514	Intermediate Similarity	NPC467188
0.7513	Intermediate Similarity	NPC267343
0.7512	Intermediate Similarity	NPC471944
0.75	Intermediate Similarity	NPC284338
0.75	Intermediate Similarity	NPC117027
0.75	Intermediate Similarity	NPC214106
0.75	Intermediate Similarity	NPC242116
0.75	Intermediate Similarity	NPC161861
0.7488	Intermediate Similarity	NPC477413
0.7487	Intermediate Similarity	NPC61011
0.7486	Intermediate Similarity	NPC293487
0.7486	Intermediate Similarity	NPC80681
0.7486	Intermediate Similarity	NPC123906
0.7475	Intermediate Similarity	NPC328318
0.7475	Intermediate Similarity	NPC472063
0.7475	Intermediate Similarity	NPC472069
0.7475	Intermediate Similarity	NPC157828
0.7475	Intermediate Similarity	NPC328596
0.7475	Intermediate Similarity	NPC195239
0.7475	Intermediate Similarity	NPC472062
0.7474	Intermediate Similarity	NPC84827
0.7474	Intermediate Similarity	NPC145885
0.7474	Intermediate Similarity	NPC14113
0.7464	Intermediate Similarity	NPC471192
0.7461	Intermediate Similarity	NPC110158
0.746	Intermediate Similarity	NPC203468
0.746	Intermediate Similarity	NPC110500
0.746	Intermediate Similarity	NPC149155
0.7459	Intermediate Similarity	NPC478182
0.7437	Intermediate Similarity	NPC11445
0.7436	Intermediate Similarity	NPC23476
0.7436	Intermediate Similarity	NPC474259
0.7436	Intermediate Similarity	NPC278434
0.7436	Intermediate Similarity	NPC477415
0.7435	Intermediate Similarity	NPC126709
0.7435	Intermediate Similarity	NPC283219
0.7435	Intermediate Similarity	NPC248041
0.7433	Intermediate Similarity	NPC78020
0.743	Intermediate Similarity	NPC100726
0.7424	Intermediate Similarity	NPC472295
0.7424	Intermediate Similarity	NPC269886
0.7424	Intermediate Similarity	NPC472210
0.7424	Intermediate Similarity	NPC81802
0.7424	Intermediate Similarity	NPC247735
0.7421	Intermediate Similarity	NPC267885
0.7414	Intermediate Similarity	NPC105127
0.7413	Intermediate Similarity	NPC472297
0.7413	Intermediate Similarity	NPC472296
0.7411	Intermediate Similarity	NPC138370
0.7404	Intermediate Similarity	NPC118940
0.7402	Intermediate Similarity	NPC327592
0.7401	Intermediate Similarity	NPC190296
0.74	Intermediate Similarity	NPC106824
0.74	Intermediate Similarity	NPC74153
0.7398	Intermediate Similarity	NPC321708
0.7387	Intermediate Similarity	NPC294693
0.7385	Intermediate Similarity	NPC207686
0.7385	Intermediate Similarity	NPC94752
0.7382	Intermediate Similarity	NPC111275
0.738	Intermediate Similarity	NPC114637
0.738	Intermediate Similarity	NPC478183
0.7374	Intermediate Similarity	NPC288838
0.7371	Intermediate Similarity	NPC46895
0.7366	Intermediate Similarity	NPC317373
0.7363	Intermediate Similarity	NPC67288
0.7363	Intermediate Similarity	NPC131887
0.7363	Intermediate Similarity	NPC281094
0.736	Intermediate Similarity	NPC475874
0.7356	Intermediate Similarity	NPC96102
0.7351	Intermediate Similarity	NPC44773
0.7351	Intermediate Similarity	NPC215584
0.7348	Intermediate Similarity	NPC313889
0.734	Intermediate Similarity	NPC63751
0.7339	Intermediate Similarity	NPC470323
0.7337	Intermediate Similarity	NPC213914
0.7337	Intermediate Similarity	NPC473821
0.7337	Intermediate Similarity	NPC236711
0.733	Intermediate Similarity	NPC110126
0.7322	Intermediate Similarity	NPC209362
0.7318	Intermediate Similarity	NPC159856
0.7318	Intermediate Similarity	NPC314372
0.7314	Intermediate Similarity	NPC84911
0.7312	Intermediate Similarity	NPC478185
0.7312	Intermediate Similarity	NPC470203
0.731	Intermediate Similarity	NPC473628

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 NPC167710 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	301
0.1-0.2	723
0.2-0.3	987
0.3-0.4	2242
0.4-0.5	2052
0.5-0.6	1881
0.6-0.7	827
0.7-0.8	134
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8054	Intermediate Similarity	NPD2479	Phase 3
0.8054	Intermediate Similarity	NPD2481	Approved
0.8054	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.8032	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4051	Discontinued
0.796	Intermediate Similarity	NPD4614	Clinical (unspecified phase)
0.7926	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7887	Intermediate Similarity	NPD4848	Phase 1
0.7865	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7766	Intermediate Similarity	NPD5473	Discontinued
0.7744	Intermediate Similarity	NPD7619	Phase 3
0.7744	Intermediate Similarity	NPD7618	Phase 3
0.7732	Intermediate Similarity	NPD4922	Phase 2
0.7727	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD4988	Discontinued
0.7659	Intermediate Similarity	NPD2411	Approved
0.7624	Intermediate Similarity	NPD2008	Discontinued
0.7596	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD1506	Discontinued
0.7584	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD7564	Discontinued
0.7548	Intermediate Similarity	NPD3389	Approved
0.7548	Intermediate Similarity	NPD3393	Approved
0.7548	Intermediate Similarity	NPD3394	Approved
0.7527	Intermediate Similarity	NPD1343	Approved
0.7526	Intermediate Similarity	NPD3961	Discontinued
0.7513	Intermediate Similarity	NPD4075	Phase 2
0.75	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD6664	Approved
0.7463	Intermediate Similarity	NPD2443	Approved
0.7463	Intermediate Similarity	NPD2442	Approved
0.7463	Intermediate Similarity	NPD6459	Phase 2
0.746	Intermediate Similarity	NPD482	Approved
0.7459	Intermediate Similarity	NPD2837	Discontinued
0.7448	Intermediate Similarity	NPD4011	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD1722	Approved
0.7441	Intermediate Similarity	NPD5198	Approved
0.7441	Intermediate Similarity	NPD5199	Approved
0.7438	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7437	Intermediate Similarity	NPD1851	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD3320	Approved
0.7409	Intermediate Similarity	NPD3318	Approved
0.7409	Intermediate Similarity	NPD3319	Phase 1
0.7402	Intermediate Similarity	NPD5901	Discontinued
0.7389	Intermediate Similarity	NPD4924	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD2509	Approved
0.7379	Intermediate Similarity	NPD2510	Approved
0.7371	Intermediate Similarity	NPD2091	Phase 2
0.7371	Intermediate Similarity	NPD2096	Phase 2
0.7366	Intermediate Similarity	NPD3323	Discontinued
0.7356	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD6152	Phase 1
0.7351	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD460	Discontinued
0.7323	Intermediate Similarity	NPD2336	Approved
0.732	Intermediate Similarity	NPD2092	Phase 2
0.732	Intermediate Similarity	NPD2094	Phase 2
0.732	Intermediate Similarity	NPD2095	Phase 2
0.732	Intermediate Similarity	NPD7401	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD5446	Phase 2
0.7308	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD7024	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD4851	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD3100	Discontinued
0.7286	Intermediate Similarity	NPD5888	Phase 2
0.7277	Intermediate Similarity	NPD1982	Phase 1
0.7273	Intermediate Similarity	NPD3583	Phase 2
0.7273	Intermediate Similarity	NPD5475	Discontinued
0.726	Intermediate Similarity	NPD2408	Discontinued
0.7254	Intermediate Similarity	NPD3076	Approved
0.7254	Intermediate Similarity	NPD3079	Approved
0.7254	Intermediate Similarity	NPD3078	Approved
0.7254	Intermediate Similarity	NPD3077	Approved
0.7246	Intermediate Similarity	NPD3905	Phase 3
0.7238	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD1270	Approved
0.7238	Intermediate Similarity	NPD7454	Approved
0.7238	Intermediate Similarity	NPD7455	Approved
0.7233	Intermediate Similarity	NPD5426	Phase 3
0.7232	Intermediate Similarity	NPD786	Approved
0.7204	Intermediate Similarity	NPD6787	Phase 2
0.7202	Intermediate Similarity	NPD6165	Phase 2
0.7202	Intermediate Similarity	NPD6164	Phase 2
0.7202	Intermediate Similarity	NPD4181	Approved
0.7194	Intermediate Similarity	NPD6178	Phase 3
0.719	Intermediate Similarity	NPD4863	Approved
0.7188	Intermediate Similarity	NPD4128	Approved
0.7188	Intermediate Similarity	NPD5065	Approved
0.7188	Intermediate Similarity	NPD4883	Approved
0.7186	Intermediate Similarity	NPD1905	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD2307	Discontinued
0.7177	Intermediate Similarity	NPD1600	Suspended
0.7165	Intermediate Similarity	NPD2590	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD1292	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD6954	Phase 2
0.715	Intermediate Similarity	NPD4299	Phase 1
0.7136	Intermediate Similarity	NPD2879	Approved
0.7136	Intermediate Similarity	NPD2881	Approved
0.7135	Intermediate Similarity	NPD750	Phase 2
0.7128	Intermediate Similarity	NPD5400	Approved
0.7113	Intermediate Similarity	NPD3505	Approved
0.7113	Intermediate Similarity	NPD3506	Approved
0.7113	Intermediate Similarity	NPD2753	Discontinued
0.7111	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7204	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD4499	Approved
0.7087	Intermediate Similarity	NPD5017	Discontinued
0.7086	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6242	Discontinued
0.7077	Intermediate Similarity	NPD4079	Approved
0.7077	Intermediate Similarity	NPD4076	Approved
0.7071	Intermediate Similarity	NPD4336	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD7207	Approved
0.7067	Intermediate Similarity	NPD7209	Approved
0.7067	Intermediate Similarity	NPD7208	Approved
0.7065	Intermediate Similarity	NPD1658	Discontinued
0.7062	Intermediate Similarity	NPD3238	Discontinued
0.7059	Intermediate Similarity	NPD2880	Discontinued
0.705	Intermediate Similarity	NPD7175	Phase 1
0.7039	Intermediate Similarity	NPD6479	Discontinued
0.7037	Intermediate Similarity	NPD7404	Approved
0.7035	Intermediate Similarity	NPD5809	Phase 3
0.7035	Intermediate Similarity	NPD7026	Phase 2
0.7017	Intermediate Similarity	NPD2006	Phase 2
0.7016	Intermediate Similarity	NPD6446	Discontinued
0.7016	Intermediate Similarity	NPD4643	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD2430	Phase 2
0.7	Intermediate Similarity	NPD3246	Discontinued
0.6995	Remote Similarity	NPD3609	Approved
0.6995	Remote Similarity	NPD3610	Approved
0.6986	Remote Similarity	NPD6987	Phase 1
0.6985	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.698	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD2641	Approved
0.6979	Remote Similarity	NPD2640	Approved
0.6973	Remote Similarity	NPD2172	Phase 1
0.6973	Remote Similarity	NPD4462	Approved
0.6973	Remote Similarity	NPD4463	Approved
0.6971	Remote Similarity	NPD6269	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD6268	Phase 1
0.6968	Remote Similarity	NPD1192	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD7666	Phase 3
0.6967	Remote Similarity	NPD7665	Phase 2
0.6964	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4524	Discontinued
0.6959	Remote Similarity	NPD3868	Phase 1
0.6957	Remote Similarity	NPD4547	Phase 3
0.6952	Remote Similarity	NPD5491	Phase 3
0.6952	Remote Similarity	NPD5489	Phase 1
0.695	Remote Similarity	NPD6217	Discontinued
0.6947	Remote Similarity	NPD6771	Discontinued
0.6946	Remote Similarity	NPD5505	Discontinued
0.6944	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD7780	Approved
0.6937	Remote Similarity	NPD7781	Approved
0.6934	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD2295	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD2213	Approved
0.6931	Remote Similarity	NPD2214	Approved
0.6927	Remote Similarity	NPD7027	Phase 3
0.6927	Remote Similarity	NPD1996	Discontinued
0.6923	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD3178	Discontinued
0.6916	Remote Similarity	NPD8093	Discontinued
0.6915	Remote Similarity	NPD5590	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD2770	Discontinued
0.6912	Remote Similarity	NPD4348	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD6470	Phase 3
0.6908	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD7308	Discontinued
0.6908	Remote Similarity	NPD6999	Discontinued
0.6908	Remote Similarity	NPD2405	Phase 3
0.6903	Remote Similarity	NPD6986	Phase 1
0.6902	Remote Similarity	NPD1683	Approved
0.6901	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD4845	Discontinued
0.689	Remote Similarity	NPD7187	Phase 2
0.6884	Remote Similarity	NPD3794	Approved
0.6884	Remote Similarity	NPD3795	Approved
0.6878	Remote Similarity	NPD7406	Phase 2
0.6878	Remote Similarity	NPD5855	Phase 3
0.6878	Remote Similarity	NPD5853	Phase 3
0.6875	Remote Similarity	NPD4501	Approved
0.6875	Remote Similarity	NPD2915	Discontinued
0.6875	Remote Similarity	NPD4500	Approved
0.6875	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7010	Phase 3

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