NPASS Compound

Structure

NPC469762 OpenBabel07101718322D 29 30 0 0 0 0 0 0 0 0999 V2000 -0.1557 10.5049 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5134 11.2480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1533 9.5538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2044 12.1991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5158 8.8107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8735 12.9422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2068 7.8596 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5645 13.8933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8760 7.1165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2336 14.6364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5669 6.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9246 15.5875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2361 5.4223 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 2.7770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5937 16.3306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9271 4.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5962 3.7281 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 1.2847 17.2817 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0511 4.2633 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 14 1 0 0 0 0 11 17 1 0 0 0 0 12 13 2 0 0 0 0 12 15 1 0 0 0 0 13 16 1 0 0 0 0 14 20 1 0 0 0 0 15 23 2 0 0 0 0 16 24 2 0 0 0 0 17 25 1 0 0 0 0 18 19 1 0 0 0 0 18 22 1 0 0 0 0 19 26 1 0 0 0 0 20 28 1 0 0 0 0 21 22 2 0 0 0 0 21 27 1 0 0 0 0 22 23 1 0 0 0 0 23 24 1 0 0 0 0 24 27 1 0 0 0 0 25 26 2 3 0 0 0 25 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	400.31
Volume:	450.235
LogP:	5.826
LogD:	4.21
LogS:	-3.294
# Rotatable Bonds:	18
TPSA:	65.12
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.29
Synthetic Accessibility Score:	2.126
Fsp3:	0.64
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.072
MDCK Permeability:	1.715309736027848e-05
Pgp-inhibitor:	0.034
Pgp-substrate:	0.035
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.174
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.222
Plasma Protein Binding (PPB):	96.87479400634766%
Volume Distribution (VD):	1.512
Pgp-substrate:	0.9352315068244934%

ADMET: Metabolism

CYP1A2-inhibitor:	0.372
CYP1A2-substrate:	0.21
CYP2C19-inhibitor:	0.713
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.414
CYP2C9-substrate:	0.948
CYP2D6-inhibitor:	0.873
CYP2D6-substrate:	0.225
CYP3A4-inhibitor:	0.85
CYP3A4-substrate:	0.11

ADMET: Excretion

Clearance (CL):	6.031
Half-life (T1/2):	0.684

ADMET: Toxicity

hERG Blockers:	0.237
Human Hepatotoxicity (H-HT):	0.403
Drug-inuced Liver Injury (DILI):	0.04
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.086
Maximum Recommended Daily Dose:	0.315
Skin Sensitization:	0.958
Carcinogencity:	0.052
Eye Corrosion:	0.003
Eye Irritation:	0.113
Respiratory Toxicity:	0.18

Download Data

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

Natural Product: NPC469762

Natural Product ID:	NPC469762
*Common Name:**	15-Hydroxy-N-[2-(1H-Indol-3-Yl)Ethyl]Pentadecanamide
IUPAC Name:	15-hydroxy-N-[2-(1H-indol-3-yl)ethyl]pentadecanamide
Synonyms:
Standard InCHIKey:	PZHSASCBYIIZLV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H40N2O2/c28-20-14-10-8-6-4-2-1-3-5-7-9-11-17-25(29)26-19-18-22-21-27-24-16-13-12-15-23(22)24/h12-13,15-16,21,27-28H,1-11,14,17-20H2,(H,26,29)
SMILES:	C1=CC=C2C(=C1)C(=CN2)CCNC(=O)CCCCCCCCCCCCCCO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1170477
PubChem CID:	46897205
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002497] Indoles [CHEMONTID:0004196] 3-alkylindoles

*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
NPO31161	Annonaceae	Genus	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20579892]
NPO31161	Annonaceae	Genus	Annonaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23513739]
NPO31161	Annonaceae	Genus	Annonaceae	Eukaryota	n.a.	fruit	n.a.	PMID[26920282]

☑ 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
Others	3

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4564	Cell Line	Neurons		Activity	=	108.0	%	PMID[533650]
NPT4564	Cell Line	Neurons		Activity	=	159.3	%	PMID[533650]
NPT4564	Cell Line	Neurons		Activity	=	60.9	%	PMID[533650]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	1000000.0	nM	PMID[533650]

☑ 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 NPC469762 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	300
0.1-0.2	2735
0.2-0.3	18287
0.3-0.4	13966
0.4-0.5	3169
0.5-0.6	2068
0.6-0.7	1339
0.7-0.8	640
0.8-0.85	107
0.85-0.9	54
0.9-0.95	17
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
0.9931	High Similarity	NPC469785
0.9658	High Similarity	NPC469765
0.9658	High Similarity	NPC259644
0.9658	High Similarity	NPC469763
0.9658	High Similarity	NPC73952
0.9658	High Similarity	NPC469760
0.9658	High Similarity	NPC25008
0.9658	High Similarity	NPC469786
0.96	High Similarity	NPC311276
0.9592	High Similarity	NPC80597
0.9592	High Similarity	NPC211572
0.9592	High Similarity	NPC70922
0.9592	High Similarity	NPC212376
0.9592	High Similarity	NPC75540
0.947	High Similarity	NPC40779
0.9286	High Similarity	NPC201700
0.9272	High Similarity	NPC230869
0.9247	High Similarity	NPC314372
0.9221	High Similarity	NPC160105
0.9221	High Similarity	NPC54988
0.9128	High Similarity	NPC105818
0.9128	High Similarity	NPC24678
0.911	High Similarity	NPC190296
0.9097	High Similarity	NPC474561
0.9097	High Similarity	NPC49954
0.9091	High Similarity	NPC102423
0.9085	High Similarity	NPC279918
0.9038	High Similarity	NPC63751
0.9026	High Similarity	NPC282231
0.8987	High Similarity	NPC314603
0.8986	High Similarity	NPC159856
0.8973	High Similarity	NPC469780
0.8973	High Similarity	NPC469779
0.8973	High Similarity	NPC469767
0.8973	High Similarity	NPC469783
0.8973	High Similarity	NPC469761
0.8973	High Similarity	NPC469768
0.8973	High Similarity	NPC469784
0.8961	High Similarity	NPC131718
0.8912	High Similarity	NPC469766
0.8889	High Similarity	NPC233936
0.8868	High Similarity	NPC313791
0.8846	High Similarity	NPC194640
0.8834	High Similarity	NPC163055
0.8828	High Similarity	NPC96102
0.8827	High Similarity	NPC300688
0.882	High Similarity	NPC151939
0.8776	High Similarity	NPC73767
0.8767	High Similarity	NPC105127
0.8767	High Similarity	NPC84911
0.8742	High Similarity	NPC471957
0.8704	High Similarity	NPC59269
0.8704	High Similarity	NPC248454
0.8699	High Similarity	NPC261195
0.8699	High Similarity	NPC29886
0.8679	High Similarity	NPC78020
0.8675	High Similarity	NPC474707
0.8659	High Similarity	NPC71037
0.8654	High Similarity	NPC92796
0.8654	High Similarity	NPC135141
0.8649	High Similarity	NPC110126
0.8623	High Similarity	NPC317030
0.8591	High Similarity	NPC279081
0.8589	High Similarity	NPC68354
0.858	High Similarity	NPC37423
0.858	High Similarity	NPC203468
0.858	High Similarity	NPC149155
0.858	High Similarity	NPC275305
0.858	High Similarity	NPC110500
0.8571	High Similarity	NPC65215
0.8571	High Similarity	NPC173028
0.8571	High Similarity	NPC216713
0.8571	High Similarity	NPC470498
0.8552	High Similarity	NPC82295
0.8537	High Similarity	NPC213468
0.8528	High Similarity	NPC267885
0.8512	High Similarity	NPC204565
0.8467	Intermediate Similarity	NPC230002
0.8452	Intermediate Similarity	NPC94752
0.8431	Intermediate Similarity	NPC288838
0.8424	Intermediate Similarity	NPC126709
0.8424	Intermediate Similarity	NPC176199
0.8424	Intermediate Similarity	NPC248041
0.8424	Intermediate Similarity	NPC283219
0.8424	Intermediate Similarity	NPC215795
0.8412	Intermediate Similarity	NPC95783
0.8408	Intermediate Similarity	NPC285469
0.8397	Intermediate Similarity	NPC200214
0.8395	Intermediate Similarity	NPC194411
0.8393	Intermediate Similarity	NPC163421
0.8393	Intermediate Similarity	NPC188387
0.8393	Intermediate Similarity	NPC280290
0.8387	Intermediate Similarity	NPC53947
0.8383	Intermediate Similarity	NPC48938
0.8383	Intermediate Similarity	NPC469358
0.8372	Intermediate Similarity	NPC474177
0.8364	Intermediate Similarity	NPC111275
0.8353	Intermediate Similarity	NPC213629
0.8344	Intermediate Similarity	NPC470507
0.8343	Intermediate Similarity	NPC315555
0.8343	Intermediate Similarity	NPC235684
0.8333	Intermediate Similarity	NPC317430
0.8324	Intermediate Similarity	NPC133366
0.8313	Intermediate Similarity	NPC55772
0.8312	Intermediate Similarity	NPC143872
0.8286	Intermediate Similarity	NPC473640
0.8284	Intermediate Similarity	NPC15102
0.8258	Intermediate Similarity	NPC469811
0.8253	Intermediate Similarity	NPC145885
0.8253	Intermediate Similarity	NPC84827
0.8253	Intermediate Similarity	NPC14113
0.8246	Intermediate Similarity	NPC321708
0.8239	Intermediate Similarity	NPC129721
0.8239	Intermediate Similarity	NPC100321
0.8225	Intermediate Similarity	NPC228835
0.821	Intermediate Similarity	NPC470508
0.8205	Intermediate Similarity	NPC321911
0.8205	Intermediate Similarity	NPC37548
0.8199	Intermediate Similarity	NPC16667
0.8198	Intermediate Similarity	NPC154339
0.8194	Intermediate Similarity	NPC63545
0.8182	Intermediate Similarity	NPC472123
0.8182	Intermediate Similarity	NPC34508
0.8176	Intermediate Similarity	NPC314002
0.8166	Intermediate Similarity	NPC220765
0.8165	Intermediate Similarity	NPC325903
0.816	Intermediate Similarity	NPC49217
0.8146	Intermediate Similarity	NPC475506
0.8146	Intermediate Similarity	NPC300183
0.8141	Intermediate Similarity	NPC201380
0.8141	Intermediate Similarity	NPC179787
0.8133	Intermediate Similarity	NPC189812
0.8133	Intermediate Similarity	NPC329688
0.8129	Intermediate Similarity	NPC171171
0.8125	Intermediate Similarity	NPC216643
0.8125	Intermediate Similarity	NPC229332
0.8125	Intermediate Similarity	NPC286427
0.8118	Intermediate Similarity	NPC204717
0.8118	Intermediate Similarity	NPC165495
0.8114	Intermediate Similarity	NPC195239
0.8114	Intermediate Similarity	NPC157828
0.8113	Intermediate Similarity	NPC207726
0.8103	Intermediate Similarity	NPC99666
0.8103	Intermediate Similarity	NPC473342
0.8103	Intermediate Similarity	NPC477167
0.8101	Intermediate Similarity	NPC476874
0.8101	Intermediate Similarity	NPC470823
0.8101	Intermediate Similarity	NPC155143
0.8095	Intermediate Similarity	NPC11126
0.8081	Intermediate Similarity	NPC46580
0.8081	Intermediate Similarity	NPC17059
0.8079	Intermediate Similarity	NPC218268
0.8075	Intermediate Similarity	NPC206819
0.8075	Intermediate Similarity	NPC318065
0.8075	Intermediate Similarity	NPC67056
0.8075	Intermediate Similarity	NPC56765
0.8075	Intermediate Similarity	NPC41257
0.8068	Intermediate Similarity	NPC11445
0.8065	Intermediate Similarity	NPC242556
0.8063	Intermediate Similarity	NPC141353
0.8061	Intermediate Similarity	NPC280548
0.8057	Intermediate Similarity	NPC267343
0.8056	Intermediate Similarity	NPC98715
0.805	Intermediate Similarity	NPC141926
0.8037	Intermediate Similarity	NPC78375
0.8037	Intermediate Similarity	NPC469813
0.8037	Intermediate Similarity	NPC476446
0.8026	Intermediate Similarity	NPC150259
0.8023	Intermediate Similarity	NPC62749
0.8	Intermediate Similarity	NPC34844
0.8	Intermediate Similarity	NPC38736
0.8	Intermediate Similarity	NPC193761
0.7989	Intermediate Similarity	NPC470497
0.7988	Intermediate Similarity	NPC42372
0.7988	Intermediate Similarity	NPC270009
0.7987	Intermediate Similarity	NPC470233
0.7987	Intermediate Similarity	NPC22079
0.7978	Intermediate Similarity	NPC171317
0.7978	Intermediate Similarity	NPC470499
0.7975	Intermediate Similarity	NPC470203
0.7975	Intermediate Similarity	NPC187951
0.7966	Intermediate Similarity	NPC251090
0.7961	Intermediate Similarity	NPC325252
0.7955	Intermediate Similarity	NPC307963
0.7953	Intermediate Similarity	NPC139291
0.7953	Intermediate Similarity	NPC472108
0.7939	Intermediate Similarity	NPC109447
0.7933	Intermediate Similarity	NPC293917
0.7929	Intermediate Similarity	NPC184964
0.7927	Intermediate Similarity	NPC90723
0.7923	Intermediate Similarity	NPC225821
0.7923	Intermediate Similarity	NPC54420
0.7923	Intermediate Similarity	NPC46225
0.7923	Intermediate Similarity	NPC323927
0.7921	Intermediate Similarity	NPC227582
0.7917	Intermediate Similarity	NPC472586
0.7914	Intermediate Similarity	NPC470204
0.791	Intermediate Similarity	NPC294693
0.7907	Intermediate Similarity	NPC284678
0.7901	Intermediate Similarity	NPC236711

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 NPC469762 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	179
0.1-0.2	567
0.2-0.3	981
0.3-0.4	1499
0.4-0.5	2710
0.5-0.6	2041
0.6-0.7	919
0.7-0.8	224
0.8-0.85	21
0.85-0.9	9
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8981	High Similarity	NPD4184	Clinical (unspecified phase)
0.8828	High Similarity	NPD198	Clinical (unspecified phase)
0.8827	High Similarity	NPD6595	Phase 3
0.882	High Similarity	NPD2144	Approved
0.8797	High Similarity	NPD5069	Clinical (unspecified phase)
0.8776	High Similarity	NPD786	Approved
0.8696	High Similarity	NPD5065	Approved
0.8659	High Similarity	NPD3038	Discontinued
0.8658	High Similarity	NPD1722	Approved
0.865	High Similarity	NPD4079	Approved
0.865	High Similarity	NPD4076	Approved
0.8606	High Similarity	NPD5728	Clinical (unspecified phase)
0.8589	High Similarity	NPD3506	Approved
0.8589	High Similarity	NPD3505	Approved
0.858	High Similarity	NPD482	Approved
0.8528	High Similarity	NPD749	Clinical (unspecified phase)
0.8494	Intermediate Similarity	NPD2094	Phase 2
0.8494	Intermediate Similarity	NPD2092	Phase 2
0.8494	Intermediate Similarity	NPD2095	Phase 2
0.8443	Intermediate Similarity	NPD2091	Phase 2
0.8443	Intermediate Similarity	NPD2096	Phase 2
0.8442	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.8442	Intermediate Similarity	NPD3100	Discontinued
0.8402	Intermediate Similarity	NPD8431	Approved
0.8387	Intermediate Similarity	NPD2172	Phase 1
0.8364	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.8353	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD4462	Approved
0.8269	Intermediate Similarity	NPD4463	Approved
0.8182	Intermediate Similarity	NPD750	Phase 2
0.8165	Intermediate Similarity	NPD2837	Discontinued
0.8137	Intermediate Similarity	NPD1404	Approved
0.8137	Intermediate Similarity	NPD1403	Approved
0.811	Intermediate Similarity	NPD4640	Approved
0.811	Intermediate Similarity	NPD4639	Approved
0.811	Intermediate Similarity	NPD4638	Approved
0.8049	Intermediate Similarity	NPD2642	Approved
0.8049	Intermediate Similarity	NPD2639	Approved
0.8025	Intermediate Similarity	NPD4703	Approved
0.8025	Intermediate Similarity	NPD4702	Approved
0.8024	Intermediate Similarity	NPD4128	Approved
0.8023	Intermediate Similarity	NPD7948	Phase 1
0.8011	Intermediate Similarity	NPD8272	Phase 2
0.8	Intermediate Similarity	NPD2640	Approved
0.8	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2641	Approved
0.7956	Intermediate Similarity	NPD8072	Approved
0.7955	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD1038	Approved
0.7952	Intermediate Similarity	NPD1325	Approved
0.7952	Intermediate Similarity	NPD1326	Approved
0.7935	Intermediate Similarity	NPD1592	Phase 3
0.7933	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD4181	Approved
0.7927	Intermediate Similarity	NPD3323	Discontinued
0.7892	Intermediate Similarity	NPD5021	Discontinued
0.7879	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD4075	Phase 2
0.787	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7869	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7869	Intermediate Similarity	NPD7957	Phase 1
0.7836	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD5138	Approved
0.7818	Intermediate Similarity	NPD5140	Approved
0.7802	Intermediate Similarity	NPD8073	Approved
0.7799	Intermediate Similarity	NPD1661	Suspended
0.7798	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7796	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD8386	Phase 2
0.7771	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD3961	Discontinued
0.7771	Intermediate Similarity	NPD3717	Discontinued
0.7758	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD802	Phase 2
0.7722	Intermediate Similarity	NPD5254	Discontinued
0.7709	Intermediate Similarity	NPD7619	Phase 3
0.7709	Intermediate Similarity	NPD7618	Phase 3
0.7706	Intermediate Similarity	NPD2928	Phase 2
0.7697	Intermediate Similarity	NPD3404	Approved
0.7692	Intermediate Similarity	NPD3117	Approved
0.7692	Intermediate Similarity	NPD3610	Approved
0.7692	Intermediate Similarity	NPD3609	Approved
0.7692	Intermediate Similarity	NPD3116	Approved
0.7682	Intermediate Similarity	NPD3654	Approved
0.7679	Intermediate Similarity	NPD5862	Discovery
0.7679	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD991	Phase 2
0.766	Intermediate Similarity	NPD7470	Discontinued
0.7658	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD3475	Approved
0.7632	Intermediate Similarity	NPD3476	Approved
0.763	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD5901	Discontinued
0.7622	Intermediate Similarity	NPD5426	Phase 3
0.7616	Intermediate Similarity	NPD8122	Approved
0.7616	Intermediate Similarity	NPD8123	Approved
0.7611	Intermediate Similarity	NPD7944	Discontinued
0.7607	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD8129	Discovery
0.76	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD484	Approved
0.7578	Intermediate Similarity	NPD4547	Phase 3
0.7572	Intermediate Similarity	NPD8036	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD8037	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD5066	Phase 2
0.7566	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD5067	Phase 2
0.7558	Intermediate Similarity	NPD2382	Approved
0.7558	Intermediate Similarity	NPD2381	Approved
0.7558	Intermediate Similarity	NPD2380	Approved
0.7557	Intermediate Similarity	NPD5555	Phase 1
0.755	Intermediate Similarity	NPD2119	Approved
0.755	Intermediate Similarity	NPD2118	Approved
0.7547	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD2006	Phase 2
0.7545	Intermediate Similarity	NPD8026	Phase 1
0.7543	Intermediate Similarity	NPD5106	Approved
0.7543	Intermediate Similarity	NPD5596	Phase 2
0.7543	Intermediate Similarity	NPD5105	Approved
0.7541	Intermediate Similarity	NPD3825	Phase 3
0.754	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7539	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD2430	Phase 2
0.7527	Intermediate Similarity	NPD6664	Approved
0.7516	Intermediate Similarity	NPD2896	Discontinued
0.7515	Intermediate Similarity	NPD2580	Discontinued
0.7514	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD6217	Discontinued
0.7513	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6178	Phase 3
0.7486	Intermediate Similarity	NPD6281	Approved
0.7484	Intermediate Similarity	NPD3385	Approved
0.7459	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD1262	Discovery
0.7447	Intermediate Similarity	NPD1392	Approved
0.7444	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD2391	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7435	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7435	Intermediate Similarity	NPD8093	Discontinued
0.7435	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7435	Intermediate Similarity	NPD3330	Phase 1
0.7425	Intermediate Similarity	NPD5255	Approved
0.7409	Intermediate Similarity	NPD5612	Discontinued
0.7407	Intermediate Similarity	NPD2509	Approved
0.7407	Intermediate Similarity	NPD1683	Approved
0.7407	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD2510	Approved
0.7403	Intermediate Similarity	NPD4615	Phase 2
0.7396	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD8094	Discontinued
0.7386	Intermediate Similarity	NPD1095	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD2511	Approved
0.7378	Intermediate Similarity	NPD3835	Phase 3
0.7378	Intermediate Similarity	NPD3833	Phase 3
0.7374	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD3002	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD4029	Approved
0.7372	Intermediate Similarity	NPD4028	Approved
0.7372	Intermediate Similarity	NPD4030	Approved
0.7368	Intermediate Similarity	NPD2844	Phase 3
0.7365	Intermediate Similarity	NPD2582	Approved
0.7365	Intermediate Similarity	NPD2581	Approved
0.7365	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD5100	Phase 3
0.7354	Intermediate Similarity	NPD8410	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD2720	Phase 1
0.7349	Intermediate Similarity	NPD2809	Approved
0.7349	Intermediate Similarity	NPD2165	Phase 1
0.7333	Intermediate Similarity	NPD6158	Phase 2
0.7333	Intermediate Similarity	NPD2882	Phase 1
0.7333	Intermediate Similarity	NPD3262	Approved
0.7333	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD1554	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD706	Phase 1
0.7312	Intermediate Similarity	NPD4600	Approved
0.7312	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD4601	Approved
0.731	Intermediate Similarity	NPD1248	Discontinued
0.731	Intermediate Similarity	NPD5611	Phase 2
0.7305	Intermediate Similarity	NPD3114	Approved
0.7305	Intermediate Similarity	NPD3113	Approved
0.7305	Intermediate Similarity	NPD473	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