NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	351.23
Volume:	386.724
LogP:	6.151
LogD:	5.037
LogS:	-4.658
# Rotatable Bonds:	9
TPSA:	56.6
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.5
Synthetic Accessibility Score:	3.333
Fsp3:	0.364
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.348
MDCK Permeability:	1.027330472425092e-05
Pgp-inhibitor:	0.82
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.656
30% Bioavailability (F30%):	0.52

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.225
Plasma Protein Binding (PPB):	97.2787094116211%
Volume Distribution (VD):	2.53
Pgp-substrate:	2.4830238819122314%

ADMET: Metabolism

CYP1A2-inhibitor:	0.966
CYP1A2-substrate:	0.921
CYP2C19-inhibitor:	0.895
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.865
CYP2C9-substrate:	0.959
CYP2D6-inhibitor:	0.654
CYP2D6-substrate:	0.888
CYP3A4-inhibitor:	0.923
CYP3A4-substrate:	0.178

ADMET: Excretion

Clearance (CL):	4.825
Half-life (T1/2):	0.34

ADMET: Toxicity

hERG Blockers:	0.836
Human Hepatotoxicity (H-HT):	0.792
Drug-inuced Liver Injury (DILI):	0.911
AMES Toxicity:	0.498
Rat Oral Acute Toxicity:	0.938
Maximum Recommended Daily Dose:	0.965
Skin Sensitization:	0.872
Carcinogencity:	0.202
Eye Corrosion:	0.009
Eye Irritation:	0.425
Respiratory Toxicity:	0.988

Download Data

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

Natural Product: NPC477815

Natural Product ID:	NPC477815
*Common Name:**	Heptyl Prodigiosin
IUPAC Name:	(2Z)-2-[(4-heptyl-5-methyl-1H-pyrrol-2-yl)methylidene]-3-methoxy-5-(1H-pyrrol-2-yl)pyrrole
Synonyms:	Heptyl Prodigiosin
Standard InCHIKey:	RSQIMZJGVPOAIK-STZFKDTASA-N
Standard InCHI:	InChI=1S/C22H29N3O/c1-4-5-6-7-8-10-17-13-18(24-16(17)2)14-21-22(26-3)15-20(25-21)19-11-9-12-23-19/h9,11-15,23-24H,4-8,10H2,1-3H3/b21-14-
SMILES:	CCCCCCCC1=C(NC(=C1)/C=C\2/C(=CC(=N2)C3=CC=CN3)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	136016524
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
NPO33587	proteobacteria from a marine tunicate	Species		Bacteria	n.a.	Philippines	n.a.	PMID[19299148]

☑ 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
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	70	nM	PMID[19299148]

☑ 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 NPC477815 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	583
0.1-0.2	7928
0.2-0.3	18301
0.3-0.4	9317
0.4-0.5	3142
0.5-0.6	2021
0.6-0.7	1196
0.7-0.8	197
0.8-0.85	10
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8958	High Similarity	NPC104049
0.8176	Intermediate Similarity	NPC92796
0.8176	Intermediate Similarity	NPC135141
0.8141	Intermediate Similarity	NPC24678
0.8141	Intermediate Similarity	NPC105818
0.8084	Intermediate Similarity	NPC141377
0.8025	Intermediate Similarity	NPC53947
0.8	Intermediate Similarity	NPC159856
0.8	Intermediate Similarity	NPC314372
0.7987	Intermediate Similarity	NPC190296
0.7974	Intermediate Similarity	NPC469768
0.7974	Intermediate Similarity	NPC469779
0.7974	Intermediate Similarity	NPC469767
0.7974	Intermediate Similarity	NPC469784
0.7974	Intermediate Similarity	NPC469783
0.7974	Intermediate Similarity	NPC469761
0.7974	Intermediate Similarity	NPC469780
0.7949	Intermediate Similarity	NPC288838
0.7922	Intermediate Similarity	NPC469766
0.7908	Intermediate Similarity	NPC73767
0.7895	Intermediate Similarity	NPC84911
0.7841	Intermediate Similarity	NPC84853
0.7829	Intermediate Similarity	NPC261195
0.7829	Intermediate Similarity	NPC96102
0.7829	Intermediate Similarity	NPC29886
0.7818	Intermediate Similarity	NPC49217
0.7812	Intermediate Similarity	NPC259644
0.7812	Intermediate Similarity	NPC469760
0.7812	Intermediate Similarity	NPC469763
0.7812	Intermediate Similarity	NPC73952
0.7812	Intermediate Similarity	NPC469765
0.7812	Intermediate Similarity	NPC25008
0.7812	Intermediate Similarity	NPC469786
0.7805	Intermediate Similarity	NPC311276
0.7792	Intermediate Similarity	NPC110126
0.7778	Intermediate Similarity	NPC216643
0.7778	Intermediate Similarity	NPC105127
0.7764	Intermediate Similarity	NPC211572
0.7764	Intermediate Similarity	NPC80597
0.7764	Intermediate Similarity	NPC70922
0.7764	Intermediate Similarity	NPC212376
0.7764	Intermediate Similarity	NPC75540
0.7716	Intermediate Similarity	NPC469785
0.7682	Intermediate Similarity	NPC82295
0.7679	Intermediate Similarity	NPC470498
0.7673	Intermediate Similarity	NPC471957
0.7669	Intermediate Similarity	NPC469762
0.7654	Intermediate Similarity	NPC75135
0.7628	Intermediate Similarity	NPC279081
0.7607	Intermediate Similarity	NPC169586
0.7593	Intermediate Similarity	NPC200214
0.759	Intermediate Similarity	NPC40779
0.7543	Intermediate Similarity	NPC280290
0.7531	Intermediate Similarity	NPC470233
0.7516	Intermediate Similarity	NPC230002
0.7516	Intermediate Similarity	NPC321911
0.75	Intermediate Similarity	NPC474561
0.75	Intermediate Similarity	NPC49954
0.75	Intermediate Similarity	NPC160105
0.75	Intermediate Similarity	NPC59269
0.7486	Intermediate Similarity	NPC284678
0.7483	Intermediate Similarity	NPC89490
0.7472	Intermediate Similarity	NPC76748
0.747	Intermediate Similarity	NPC131718
0.7455	Intermediate Similarity	NPC212742
0.7453	Intermediate Similarity	NPC201380
0.7453	Intermediate Similarity	NPC469811
0.7453	Intermediate Similarity	NPC179787
0.745	Intermediate Similarity	NPC27740
0.7434	Intermediate Similarity	NPC475105
0.7434	Intermediate Similarity	NPC329896
0.7434	Intermediate Similarity	NPC475090
0.7432	Intermediate Similarity	NPC187558
0.743	Intermediate Similarity	NPC92111
0.7425	Intermediate Similarity	NPC282231
0.7423	Intermediate Similarity	NPC216713
0.7416	Intermediate Similarity	NPC296527
0.7391	Intermediate Similarity	NPC143872
0.7391	Intermediate Similarity	NPC63545
0.7381	Intermediate Similarity	NPC317105
0.7381	Intermediate Similarity	NPC102423
0.7378	Intermediate Similarity	NPC325903
0.7365	Intermediate Similarity	NPC279918
0.7356	Intermediate Similarity	NPC276540
0.7356	Intermediate Similarity	NPC176199
0.7356	Intermediate Similarity	NPC215795
0.7356	Intermediate Similarity	NPC233050
0.7353	Intermediate Similarity	NPC201700
0.7353	Intermediate Similarity	NPC63751
0.7349	Intermediate Similarity	NPC286427
0.7348	Intermediate Similarity	NPC307963
0.7338	Intermediate Similarity	NPC256893
0.7326	Intermediate Similarity	NPC314603
0.7326	Intermediate Similarity	NPC313791
0.7317	Intermediate Similarity	NPC470823
0.7314	Intermediate Similarity	NPC16659
0.731	Intermediate Similarity	NPC194411
0.7305	Intermediate Similarity	NPC56765
0.7305	Intermediate Similarity	NPC318065
0.7305	Intermediate Similarity	NPC206819
0.7305	Intermediate Similarity	NPC41257
0.7305	Intermediate Similarity	NPC230869
0.7301	Intermediate Similarity	NPC37548
0.7299	Intermediate Similarity	NPC284775
0.7299	Intermediate Similarity	NPC68354
0.7294	Intermediate Similarity	NPC54988
0.7283	Intermediate Similarity	NPC275305
0.7283	Intermediate Similarity	NPC67288
0.7283	Intermediate Similarity	NPC37423
0.7278	Intermediate Similarity	NPC194640
0.7278	Intermediate Similarity	NPC162268
0.7278	Intermediate Similarity	NPC8104
0.7273	Intermediate Similarity	NPC243381
0.7273	Intermediate Similarity	NPC141926
0.7273	Intermediate Similarity	NPC275292
0.7267	Intermediate Similarity	NPC242556
0.7257	Intermediate Similarity	NPC265710
0.7247	Intermediate Similarity	NPC188387
0.7247	Intermediate Similarity	NPC15102
0.7247	Intermediate Similarity	NPC163421
0.7246	Intermediate Similarity	NPC236711
0.7243	Intermediate Similarity	NPC74413
0.7229	Intermediate Similarity	NPC34844
0.7229	Intermediate Similarity	NPC471458
0.7229	Intermediate Similarity	NPC470507
0.7225	Intermediate Similarity	NPC477611
0.7219	Intermediate Similarity	NPC470203
0.7216	Intermediate Similarity	NPC314919
0.7215	Intermediate Similarity	NPC150259
0.7204	Intermediate Similarity	NPC19872
0.72	Intermediate Similarity	NPC473380
0.72	Intermediate Similarity	NPC151939
0.72	Intermediate Similarity	NPC248454
0.72	Intermediate Similarity	NPC240088
0.7176	Intermediate Similarity	NPC90723
0.7175	Intermediate Similarity	NPC233936
0.7174	Intermediate Similarity	NPC13880
0.7171	Intermediate Similarity	NPC245244
0.7171	Intermediate Similarity	NPC146373
0.7171	Intermediate Similarity	NPC166424
0.7161	Intermediate Similarity	NPC22079
0.716	Intermediate Similarity	NPC215584
0.716	Intermediate Similarity	NPC44773
0.716	Intermediate Similarity	NPC470204
0.7152	Intermediate Similarity	NPC325252
0.7152	Intermediate Similarity	NPC218268
0.7151	Intermediate Similarity	NPC308931
0.7151	Intermediate Similarity	NPC99939
0.7143	Intermediate Similarity	NPC280852
0.7143	Intermediate Similarity	NPC476454
0.7135	Intermediate Similarity	NPC163055
0.7133	Intermediate Similarity	NPC265605
0.7133	Intermediate Similarity	NPC48564
0.7133	Intermediate Similarity	NPC182570
0.7128	Intermediate Similarity	NPC193761
0.7128	Intermediate Similarity	NPC260900
0.7127	Intermediate Similarity	NPC213629
0.7127	Intermediate Similarity	NPC209917
0.7127	Intermediate Similarity	NPC321708
0.7126	Intermediate Similarity	NPC38736
0.7119	Intermediate Similarity	NPC300688
0.7111	Intermediate Similarity	NPC235684
0.7111	Intermediate Similarity	NPC171171
0.7102	Intermediate Similarity	NPC84827
0.7102	Intermediate Similarity	NPC14113
0.7102	Intermediate Similarity	NPC145885
0.7097	Intermediate Similarity	NPC131887
0.7095	Intermediate Similarity	NPC204717
0.7093	Intermediate Similarity	NPC470509
0.7091	Intermediate Similarity	NPC187951
0.7091	Intermediate Similarity	NPC124005
0.7089	Intermediate Similarity	NPC198988
0.7086	Intermediate Similarity	NPC41174
0.7081	Intermediate Similarity	NPC251090
0.7081	Intermediate Similarity	NPC59084
0.7081	Intermediate Similarity	NPC2949
0.7077	Intermediate Similarity	NPC470549
0.7076	Intermediate Similarity	NPC78375
0.7076	Intermediate Similarity	NPC469813
0.7076	Intermediate Similarity	NPC476446
0.7073	Intermediate Similarity	NPC316069
0.7072	Intermediate Similarity	NPC17059
0.7065	Intermediate Similarity	NPC304203
0.7062	Intermediate Similarity	NPC11126
0.7059	Intermediate Similarity	NPC473320
0.7059	Intermediate Similarity	NPC122141
0.7059	Intermediate Similarity	NPC18487
0.7056	Intermediate Similarity	NPC314002
0.7053	Intermediate Similarity	NPC285558
0.7049	Intermediate Similarity	NPC476460
0.7045	Intermediate Similarity	NPC267885
0.7045	Intermediate Similarity	NPC224764
0.7043	Intermediate Similarity	NPC227582
0.7043	Intermediate Similarity	NPC77555
0.7041	Intermediate Similarity	NPC170114
0.7041	Intermediate Similarity	NPC36405
0.7041	Intermediate Similarity	NPC472027
0.7039	Intermediate Similarity	NPC290094
0.7039	Intermediate Similarity	NPC220765
0.7039	Intermediate Similarity	NPC48938

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 NPC477815 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	289
0.1-0.2	832
0.2-0.3	860
0.3-0.4	1807
0.4-0.5	2836
0.5-0.6	1908
0.6-0.7	568
0.7-0.8	49
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
0.8618	High Similarity	NPD3835	Phase 3
0.8618	High Similarity	NPD3833	Phase 3
0.84	Intermediate Similarity	NPD3834	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD2172	Phase 1
0.7908	Intermediate Similarity	NPD786	Approved
0.7829	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD2144	Approved
0.7692	Intermediate Similarity	NPD1722	Approved
0.7674	Intermediate Similarity	NPD3038	Discontinued
0.7665	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD3100	Discontinued
0.7616	Intermediate Similarity	NPD6595	Phase 3
0.7516	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3476	Approved
0.75	Intermediate Similarity	NPD2639	Approved
0.75	Intermediate Similarity	NPD3475	Approved
0.75	Intermediate Similarity	NPD2642	Approved
0.7456	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD2582	Approved
0.7455	Intermediate Similarity	NPD2581	Approved
0.7421	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD991	Phase 2
0.7412	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD2837	Discontinued
0.7362	Intermediate Similarity	NPD4462	Approved
0.7362	Intermediate Similarity	NPD4463	Approved
0.7348	Intermediate Similarity	NPD1038	Approved
0.7348	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD2118	Approved
0.7303	Intermediate Similarity	NPD2119	Approved
0.7299	Intermediate Similarity	NPD3505	Approved
0.7299	Intermediate Similarity	NPD3506	Approved
0.7283	Intermediate Similarity	NPD5065	Approved
0.7262	Intermediate Similarity	NPD1404	Approved
0.7262	Intermediate Similarity	NPD1403	Approved
0.7257	Intermediate Similarity	NPD4079	Approved
0.7257	Intermediate Similarity	NPD4076	Approved
0.725	Intermediate Similarity	NPD1592	Phase 3
0.7237	Intermediate Similarity	NPD9583	Approved
0.7226	Intermediate Similarity	NPD803	Phase 1
0.7176	Intermediate Similarity	NPD8129	Discovery
0.7176	Intermediate Similarity	NPD3323	Discontinued
0.7167	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD3825	Phase 3
0.7151	Intermediate Similarity	NPD2640	Approved
0.7151	Intermediate Similarity	NPD2641	Approved
0.7143	Intermediate Similarity	NPD4075	Phase 2
0.7134	Intermediate Similarity	NPD4030	Approved
0.7134	Intermediate Similarity	NPD4029	Approved
0.7134	Intermediate Similarity	NPD4028	Approved
0.7133	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD271	Approved
0.7133	Intermediate Similarity	NPD268	Approved
0.7111	Intermediate Similarity	NPD6217	Discontinued
0.7105	Intermediate Similarity	NPD9357	Approved
0.7095	Intermediate Similarity	NPD9396	Approved
0.7095	Intermediate Similarity	NPD9392	Approved
0.7086	Intermediate Similarity	NPD4128	Approved
0.7083	Intermediate Similarity	NPD2580	Discontinued
0.7081	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD269	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7469	Discontinued
0.7072	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5106	Approved
0.7039	Intermediate Similarity	NPD5105	Approved
0.7031	Intermediate Similarity	NPD2510	Approved
0.7031	Intermediate Similarity	NPD2509	Approved
0.703	Intermediate Similarity	NPD4702	Approved
0.703	Intermediate Similarity	NPD4703	Approved
0.7029	Intermediate Similarity	NPD2077	Approved
0.7029	Intermediate Similarity	NPD2076	Approved
0.7025	Intermediate Similarity	NPD3942	Approved
0.7025	Intermediate Similarity	NPD3944	Approved
0.7022	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD565	Phase 2
0.7006	Intermediate Similarity	NPD4181	Approved
0.7	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD2006	Phase 2
0.6989	Remote Similarity	NPD482	Approved
0.6983	Remote Similarity	NPD1707	Approved
0.6983	Remote Similarity	NPD3178	Discontinued
0.6983	Remote Similarity	NPD1708	Approved
0.6977	Remote Similarity	NPD5138	Approved
0.6977	Remote Similarity	NPD5140	Approved
0.6971	Remote Similarity	NPD3609	Approved
0.6971	Remote Similarity	NPD3610	Approved
0.6968	Remote Similarity	NPD4548	Discontinued
0.6951	Remote Similarity	NPD5254	Discontinued
0.6944	Remote Similarity	NPD2095	Phase 2
0.6944	Remote Similarity	NPD2092	Phase 2
0.6944	Remote Similarity	NPD2094	Phase 2
0.6944	Remote Similarity	NPD5596	Phase 2
0.6944	Remote Similarity	NPD1332	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD715	Phase 3
0.6943	Remote Similarity	NPD2187	Approved
0.6943	Remote Similarity	NPD2189	Approved
0.6928	Remote Similarity	NPD4547	Phase 3
0.6927	Remote Similarity	NPD8403	Phase 1
0.6927	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1031	Discontinued
0.6923	Remote Similarity	NPD5067	Phase 2
0.6923	Remote Similarity	NPD7470	Discontinued
0.6923	Remote Similarity	NPD5066	Phase 2
0.6914	Remote Similarity	NPD5436	Phase 1
0.6914	Remote Similarity	NPD768	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.691	Remote Similarity	NPD4071	Approved
0.691	Remote Similarity	NPD4072	Approved
0.6907	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD2091	Phase 2
0.6906	Remote Similarity	NPD2096	Phase 2
0.6901	Remote Similarity	NPD704	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD5255	Approved
0.6897	Remote Similarity	NPD1248	Discontinued
0.6891	Remote Similarity	NPD1392	Approved
0.689	Remote Similarity	NPD3717	Discontinued
0.689	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD1895	Discontinued
0.6886	Remote Similarity	NPD2430	Phase 2
0.6885	Remote Similarity	NPD8431	Approved
0.6885	Remote Similarity	NPD3961	Discontinued
0.6882	Remote Similarity	NPD802	Phase 2
0.6882	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD3654	Approved
0.6868	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD7948	Phase 1
0.686	Remote Similarity	NPD687	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD2390	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1192	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD4023	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD706	Phase 1
0.6831	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD5020	Approved
0.6821	Remote Similarity	NPD6771	Discontinued
0.681	Remote Similarity	NPD2075	Approved
0.681	Remote Similarity	NPD2069	Approved
0.681	Remote Similarity	NPD2071	Approved
0.681	Remote Similarity	NPD2072	Approved
0.681	Remote Similarity	NPD2070	Approved
0.681	Remote Similarity	NPD2068	Approved
0.681	Remote Similarity	NPD2074	Approved
0.681	Remote Similarity	NPD2073	Approved
0.6798	Remote Similarity	NPD2928	Phase 2
0.679	Remote Similarity	NPD200	Phase 2
0.679	Remote Similarity	NPD201	Phase 2
0.6789	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD5426	Phase 3
0.678	Remote Similarity	NPD3117	Approved
0.678	Remote Similarity	NPD3116	Approved
0.6766	Remote Similarity	NPD3402	Phase 1
0.6765	Remote Similarity	NPD3339	Approved
0.6763	Remote Similarity	NPD1741	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD1418	Phase 2
0.6761	Remote Similarity	NPD4640	Approved
0.6761	Remote Similarity	NPD4639	Approved
0.6761	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD4638	Approved
0.6753	Remote Similarity	NPD7001	Phase 3
0.6753	Remote Similarity	NPD748	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD1598	Discontinued
0.675	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD3813	Approved
0.6744	Remote Similarity	NPD2865	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD2720	Phase 1
0.6743	Remote Similarity	NPD2915	Discontinued
0.6743	Remote Similarity	NPD2719	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD750	Phase 2
0.674	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD2793	Discontinued
0.6726	Remote Similarity	NPD2089	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD2165	Phase 1
0.6723	Remote Similarity	NPD1325	Approved
0.6723	Remote Similarity	NPD1326	Approved
0.672	Remote Similarity	NPD3870	Clinical (unspecified phase)
0.672	Remote Similarity	NPD3871	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD5259	Phase 3
0.6708	Remote Similarity	NPD3385	Approved
0.6705	Remote Similarity	NPD1554	Clinical (unspecified phase)
0.67	Remote Similarity	NPD5612	Discontinued
0.6686	Remote Similarity	NPD3113	Approved
0.6686	Remote Similarity	NPD3114	Approved
0.6686	Remote Similarity	NPD3115	Approved
0.6686	Remote Similarity	NPD473	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD3112	Approved
0.6685	Remote Similarity	NPD3347	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD5913	Phase 3
0.6684	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3396	Approved

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