NPASS Compound

Structure

NPC25008 OpenBabel07101718312D 31 32 0 0 0 0 0 0 0 0999 V2000 1.6448 18.9759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9539 18.0248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2847 17.2817 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 0.9246 15.5875 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 0.5645 13.8933 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 0.2044 12.1991 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 -0.1557 10.5049 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 -0.5158 8.8107 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 -0.8760 7.1165 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 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 -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 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 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 21 1 0 0 0 0 17 18 2 0 0 0 0 17 19 1 0 0 0 0 18 20 1 0 0 0 0 19 26 2 0 0 0 0 20 27 2 0 0 0 0 21 28 1 0 0 0 0 22 23 1 0 0 0 0 22 25 1 0 0 0 0 23 29 1 0 0 0 0 24 25 2 0 0 0 0 24 30 1 0 0 0 0 25 26 1 0 0 0 0 26 27 1 0 0 0 0 27 30 1 0 0 0 0 28 29 2 3 0 0 0 28 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	426.36
Volume:	493.333
LogP:	8.841
LogD:	5.007
LogS:	-3.318
# Rotatable Bonds:	20
TPSA:	44.89
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.219
Synthetic Accessibility Score:	2.118
Fsp3:	0.679
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.181
MDCK Permeability:	8.233447260863613e-06
Pgp-inhibitor:	0.003
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.175
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.092
Plasma Protein Binding (PPB):	98.42798614501953%
Volume Distribution (VD):	3.019
Pgp-substrate:	0.7997453212738037%

ADMET: Metabolism

CYP1A2-inhibitor:	0.145
CYP1A2-substrate:	0.197
CYP2C19-inhibitor:	0.516
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.166
CYP2C9-substrate:	0.968
CYP2D6-inhibitor:	0.83
CYP2D6-substrate:	0.291
CYP3A4-inhibitor:	0.75
CYP3A4-substrate:	0.087

ADMET: Excretion

Clearance (CL):	4.73
Half-life (T1/2):	0.253

ADMET: Toxicity

hERG Blockers:	0.751
Human Hepatotoxicity (H-HT):	0.33
Drug-inuced Liver Injury (DILI):	0.194
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.058
Maximum Recommended Daily Dose:	0.408
Skin Sensitization:	0.965
Carcinogencity:	0.038
Eye Corrosion:	0.004
Eye Irritation:	0.143
Respiratory Toxicity:	0.767

Download Data

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

Natural Product: NPC25008

Natural Product ID:	NPC25008
*Common Name:**	N-Stearoyltryptamine
IUPAC Name:	N-[2-(1H-indol-3-yl)ethyl]octadecanamide
Synonyms:	N-Stearoyltryptamine
Standard InCHIKey:	AIIVCXFBTONHDU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C28H46N2O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-21-28(31)29-23-22-25-24-30-27-20-18-17-19-26(25)27/h17-20,24,30H,2-16,21-23H2,1H3,(H,29,31)
SMILES:	CCCCCCCCCCCCCCCCCC(=NCCc1c[nH]c2c1cccc2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL491707
PubChem CID:	11796710
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
NPO32731	rollinia mucosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[10479316]
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
ED50	6
Others	3

Activity Type	# Activity
Cell Line	7
NON-MOLECULAR	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[524039]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[524039]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[524039]
NPT306	Cell Line	PC-3	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[524039]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[524039]
NPT4564	Cell Line	Neurons		Activity	=	110.0	%	PMID[524040]
NPT4564	Cell Line	Neurons		Activity	=	149.9	%	PMID[524040]
NPT176	Organism	Artemia salina	Artemia salina	LC50	>	500.0	ug.mL-1	PMID[524039]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>	10.0	ug ml-1	PMID[524039]

☑ 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 NPC25008 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	360
0.1-0.2	3461
0.2-0.3	19625
0.3-0.4	12166
0.4-0.5	2963
0.5-0.6	1995
0.6-0.7	1253
0.7-0.8	654
0.8-0.85	130
0.85-0.9	48
0.9-0.95	26
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC469760
1.0	High Similarity	NPC73952
1.0	High Similarity	NPC469786
1.0	High Similarity	NPC469765
1.0	High Similarity	NPC259644
1.0	High Similarity	NPC469763
0.993	High Similarity	NPC75540
0.993	High Similarity	NPC211572
0.993	High Similarity	NPC212376
0.993	High Similarity	NPC70922
0.993	High Similarity	NPC80597
0.9724	High Similarity	NPC469785
0.9658	High Similarity	NPC469762
0.9577	High Similarity	NPC314372
0.953	High Similarity	NPC311276
0.9448	High Similarity	NPC105818
0.9448	High Similarity	NPC24678
0.9437	High Similarity	NPC190296
0.9404	High Similarity	NPC160105
0.9296	High Similarity	NPC469761
0.9296	High Similarity	NPC469767
0.9296	High Similarity	NPC469783
0.9296	High Similarity	NPC469780
0.9296	High Similarity	NPC469768
0.9296	High Similarity	NPC469784
0.9296	High Similarity	NPC469779
0.9276	High Similarity	NPC474561
0.9276	High Similarity	NPC49954
0.9272	High Similarity	NPC40779
0.9231	High Similarity	NPC469766
0.9216	High Similarity	NPC201700
0.9205	High Similarity	NPC282231
0.9172	High Similarity	NPC159856
0.9161	High Similarity	NPC314603
0.9139	High Similarity	NPC279918
0.9139	High Similarity	NPC131718
0.9091	High Similarity	NPC73767
0.9091	High Similarity	NPC63751
0.9085	High Similarity	NPC84911
0.9073	High Similarity	NPC230869
0.9048	High Similarity	NPC471957
0.902	High Similarity	NPC194640
0.9014	High Similarity	NPC261195
0.9014	High Similarity	NPC96102
0.9014	High Similarity	NPC29886
0.8958	High Similarity	NPC110126
0.8951	High Similarity	NPC105127
0.8903	High Similarity	NPC54988
0.8896	High Similarity	NPC102423
0.8868	High Similarity	NPC248454
0.8824	High Similarity	NPC92796
0.8824	High Similarity	NPC135141
0.8797	High Similarity	NPC313791
0.8767	High Similarity	NPC279081
0.8758	High Similarity	NPC300688
0.875	High Similarity	NPC151939
0.875	High Similarity	NPC59269
0.8742	High Similarity	NPC216713
0.8732	High Similarity	NPC82295
0.8726	High Similarity	NPC78020
0.8704	High Similarity	NPC233936
0.8696	High Similarity	NPC213468
0.8688	High Similarity	NPC267885
0.8684	High Similarity	NPC200214
0.8675	High Similarity	NPC53947
0.8671	High Similarity	NPC194411
0.865	High Similarity	NPC163055
0.8639	High Similarity	NPC230002
0.8625	High Similarity	NPC110500
0.8625	High Similarity	NPC149155
0.8625	High Similarity	NPC203468
0.8606	High Similarity	NPC94752
0.86	High Similarity	NPC288838
0.858	High Similarity	NPC248041
0.858	High Similarity	NPC126709
0.8571	High Similarity	NPC285469
0.8516	High Similarity	NPC129721
0.8509	High Similarity	NPC37423
0.8509	High Similarity	NPC275305
0.8503	High Similarity	NPC213629
0.8494	Intermediate Similarity	NPC235684
0.8494	Intermediate Similarity	NPC474707
0.8487	Intermediate Similarity	NPC321911
0.8477	Intermediate Similarity	NPC143872
0.8466	Intermediate Similarity	NPC283219
0.8443	Intermediate Similarity	NPC317030
0.8434	Intermediate Similarity	NPC280290
0.8434	Intermediate Similarity	NPC15102
0.8428	Intermediate Similarity	NPC49217
0.8421	Intermediate Similarity	NPC469811
0.8421	Intermediate Similarity	NPC201380
0.8421	Intermediate Similarity	NPC179787
0.8405	Intermediate Similarity	NPC145885
0.8405	Intermediate Similarity	NPC14113
0.8405	Intermediate Similarity	NPC84827
0.8405	Intermediate Similarity	NPC111275
0.8405	Intermediate Similarity	NPC68354
0.8397	Intermediate Similarity	NPC286427
0.8393	Intermediate Similarity	NPC65215
0.8393	Intermediate Similarity	NPC173028
0.8385	Intermediate Similarity	NPC470498
0.8383	Intermediate Similarity	NPC171171
0.8377	Intermediate Similarity	NPC470823
0.8373	Intermediate Similarity	NPC204717
0.8373	Intermediate Similarity	NPC228835
0.8366	Intermediate Similarity	NPC37548
0.8364	Intermediate Similarity	NPC71037
0.8355	Intermediate Similarity	NPC63545
0.8354	Intermediate Similarity	NPC55772
0.8354	Intermediate Similarity	NPC16667
0.8354	Intermediate Similarity	NPC215795
0.8354	Intermediate Similarity	NPC176199
0.8344	Intermediate Similarity	NPC56765
0.8344	Intermediate Similarity	NPC206819
0.8344	Intermediate Similarity	NPC41257
0.8344	Intermediate Similarity	NPC318065
0.8343	Intermediate Similarity	NPC95783
0.8333	Intermediate Similarity	NPC204565
0.8323	Intermediate Similarity	NPC188387
0.8323	Intermediate Similarity	NPC141926
0.8323	Intermediate Similarity	NPC314002
0.8323	Intermediate Similarity	NPC325903
0.8323	Intermediate Similarity	NPC163421
0.8313	Intermediate Similarity	NPC220765
0.8311	Intermediate Similarity	NPC150259
0.8284	Intermediate Similarity	NPC321708
0.828	Intermediate Similarity	NPC216643
0.8276	Intermediate Similarity	NPC22079
0.8269	Intermediate Similarity	NPC34844
0.8269	Intermediate Similarity	NPC207726
0.8263	Intermediate Similarity	NPC165495
0.8258	Intermediate Similarity	NPC470233
0.8256	Intermediate Similarity	NPC195239
0.8256	Intermediate Similarity	NPC157828
0.8243	Intermediate Similarity	NPC218268
0.8243	Intermediate Similarity	NPC325252
0.8242	Intermediate Similarity	NPC11126
0.8228	Intermediate Similarity	NPC67056
0.8224	Intermediate Similarity	NPC242556
0.8217	Intermediate Similarity	NPC141353
0.821	Intermediate Similarity	NPC280548
0.8208	Intermediate Similarity	NPC11445
0.8204	Intermediate Similarity	NPC48938
0.8204	Intermediate Similarity	NPC469358
0.8199	Intermediate Similarity	NPC109447
0.8198	Intermediate Similarity	NPC474177
0.8187	Intermediate Similarity	NPC90723
0.8176	Intermediate Similarity	NPC198988
0.8165	Intermediate Similarity	NPC236711
0.8153	Intermediate Similarity	NPC38736
0.8153	Intermediate Similarity	NPC470507
0.815	Intermediate Similarity	NPC133366
0.8148	Intermediate Similarity	NPC317430
0.8146	Intermediate Similarity	NPC59084
0.8146	Intermediate Similarity	NPC2949
0.814	Intermediate Similarity	NPC477167
0.814	Intermediate Similarity	NPC99666
0.814	Intermediate Similarity	NPC473342
0.8129	Intermediate Similarity	NPC187951
0.8125	Intermediate Similarity	NPC470203
0.8118	Intermediate Similarity	NPC46580
0.8118	Intermediate Similarity	NPC17059
0.8114	Intermediate Similarity	NPC473640
0.8114	Intermediate Similarity	NPC171317
0.811	Intermediate Similarity	NPC472123
0.8099	Intermediate Similarity	NPC41174
0.8095	Intermediate Similarity	NPC475450
0.8092	Intermediate Similarity	NPC473868
0.8092	Intermediate Similarity	NPC63157
0.8072	Intermediate Similarity	NPC184964
0.8069	Intermediate Similarity	NPC471311
0.8069	Intermediate Similarity	NPC471313
0.8068	Intermediate Similarity	NPC100321
0.8068	Intermediate Similarity	NPC293917
0.8063	Intermediate Similarity	NPC215584
0.8063	Intermediate Similarity	NPC44773
0.8063	Intermediate Similarity	NPC470204
0.8061	Intermediate Similarity	NPC189812
0.8061	Intermediate Similarity	NPC329688
0.8059	Intermediate Similarity	NPC315555
0.8059	Intermediate Similarity	NPC62749
0.8057	Intermediate Similarity	NPC227582
0.8052	Intermediate Similarity	NPC470440
0.8035	Intermediate Similarity	NPC324149
0.8025	Intermediate Similarity	NPC470508
0.8013	Intermediate Similarity	NPC124005
0.8011	Intermediate Similarity	NPC470499
0.8011	Intermediate Similarity	NPC265576
0.8	Intermediate Similarity	NPC34508
0.8	Intermediate Similarity	NPC316069
0.8	Intermediate Similarity	NPC250361
0.7989	Intermediate Similarity	NPC307963
0.7978	Intermediate Similarity	NPC300183
0.7978	Intermediate Similarity	NPC475506
0.7976	Intermediate Similarity	NPC16659
0.7964	Intermediate Similarity	NPC96890
0.7963	Intermediate Similarity	NPC476118
0.7963	Intermediate Similarity	NPC317105
0.7961	Intermediate Similarity	NPC88097
0.7959	Intermediate Similarity	NPC473587

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 NPC25008 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	196
0.1-0.2	605
0.2-0.3	1019
0.3-0.4	1487
0.4-0.5	2650
0.5-0.6	1966
0.6-0.7	946
0.7-0.8	241
0.8-0.85	29
0.85-0.9	9
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9156	High Similarity	NPD4184	Clinical (unspecified phase)
0.9091	High Similarity	NPD786	Approved
0.9014	High Similarity	NPD198	Clinical (unspecified phase)
0.8861	High Similarity	NPD5065	Approved
0.8836	High Similarity	NPD1722	Approved
0.8758	High Similarity	NPD6595	Phase 3
0.875	High Similarity	NPD2144	Approved
0.8733	High Similarity	NPD3100	Discontinued
0.8688	High Similarity	NPD749	Clinical (unspecified phase)
0.8675	High Similarity	NPD2172	Phase 1
0.865	High Similarity	NPD5728	Clinical (unspecified phase)
0.8625	High Similarity	NPD482	Approved
0.8609	High Similarity	NPD4374	Clinical (unspecified phase)
0.8589	High Similarity	NPD3038	Discontinued
0.8554	High Similarity	NPD8431	Approved
0.8545	High Similarity	NPD6610	Clinical (unspecified phase)
0.8537	High Similarity	NPD2094	Phase 2
0.8537	High Similarity	NPD2095	Phase 2
0.8537	High Similarity	NPD2092	Phase 2
0.8519	High Similarity	NPD6203	Clinical (unspecified phase)
0.8503	High Similarity	NPD8110	Clinical (unspecified phase)
0.8491	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.8485	Intermediate Similarity	NPD2091	Phase 2
0.8485	Intermediate Similarity	NPD2096	Phase 2
0.8466	Intermediate Similarity	NPD4076	Approved
0.8466	Intermediate Similarity	NPD4079	Approved
0.8431	Intermediate Similarity	NPD4462	Approved
0.8431	Intermediate Similarity	NPD4463	Approved
0.8405	Intermediate Similarity	NPD3506	Approved
0.8405	Intermediate Similarity	NPD3505	Approved
0.8333	Intermediate Similarity	NPD750	Phase 2
0.8323	Intermediate Similarity	NPD2837	Discontinued
0.8301	Intermediate Similarity	NPD4703	Approved
0.8301	Intermediate Similarity	NPD4702	Approved
0.8291	Intermediate Similarity	NPD1404	Approved
0.8291	Intermediate Similarity	NPD1403	Approved
0.8282	Intermediate Similarity	NPD4128	Approved
0.8212	Intermediate Similarity	NPD1592	Phase 3
0.821	Intermediate Similarity	NPD1325	Approved
0.821	Intermediate Similarity	NPD1326	Approved
0.8199	Intermediate Similarity	NPD2639	Approved
0.8199	Intermediate Similarity	NPD2642	Approved
0.8187	Intermediate Similarity	NPD3323	Discontinued
0.8182	Intermediate Similarity	NPD4181	Approved
0.8148	Intermediate Similarity	NPD2640	Approved
0.8148	Intermediate Similarity	NPD2641	Approved
0.8148	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD4075	Phase 2
0.8121	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.8068	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.8057	Intermediate Similarity	NPD7948	Phase 1
0.8049	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD3717	Discontinued
0.7989	Intermediate Similarity	NPD1038	Approved
0.7987	Intermediate Similarity	NPD5254	Discontinued
0.7976	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD5138	Approved
0.7963	Intermediate Similarity	NPD5140	Approved
0.7959	Intermediate Similarity	NPD3654	Approved
0.7939	Intermediate Similarity	NPD3609	Approved
0.7939	Intermediate Similarity	NPD3610	Approved
0.7933	Intermediate Similarity	NPD8073	Approved
0.7927	Intermediate Similarity	NPD4640	Approved
0.7927	Intermediate Similarity	NPD4639	Approved
0.7927	Intermediate Similarity	NPD4638	Approved
0.7922	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD8386	Phase 2
0.7907	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD3961	Discontinued
0.7905	Intermediate Similarity	NPD3476	Approved
0.7905	Intermediate Similarity	NPD3475	Approved
0.7901	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7889	Intermediate Similarity	NPD8072	Approved
0.7886	Intermediate Similarity	NPD802	Phase 2
0.7845	Intermediate Similarity	NPD8272	Phase 2
0.7841	Intermediate Similarity	NPD7618	Phase 3
0.7841	Intermediate Similarity	NPD7619	Phase 3
0.7836	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD1661	Suspended
0.7834	Intermediate Similarity	NPD4547	Phase 3
0.7829	Intermediate Similarity	NPD3404	Approved
0.7823	Intermediate Similarity	NPD991	Phase 2
0.7823	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD2119	Approved
0.7823	Intermediate Similarity	NPD2118	Approved
0.7818	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD2006	Phase 2
0.7802	Intermediate Similarity	NPD7957	Phase 1
0.7802	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD2430	Phase 2
0.7784	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD2580	Discontinued
0.776	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD3385	Approved
0.7746	Intermediate Similarity	NPD6217	Discontinued
0.7746	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD5021	Discontinued
0.7701	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD8026	Phase 1
0.7679	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD5106	Approved
0.7674	Intermediate Similarity	NPD5105	Approved
0.7669	Intermediate Similarity	NPD5255	Approved
0.7663	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD1683	Approved
0.7654	Intermediate Similarity	NPD6664	Approved
0.765	Intermediate Similarity	NPD5426	Phase 3
0.765	Intermediate Similarity	NPD5901	Discontinued
0.7634	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD4030	Approved
0.7632	Intermediate Similarity	NPD4029	Approved
0.7632	Intermediate Similarity	NPD4028	Approved
0.7624	Intermediate Similarity	NPD484	Approved
0.7619	Intermediate Similarity	NPD3116	Approved
0.7619	Intermediate Similarity	NPD3117	Approved
0.7609	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD1262	Discovery
0.7594	Intermediate Similarity	NPD7470	Discontinued
0.7594	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD2165	Phase 1
0.7578	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD6158	Phase 2
0.7578	Intermediate Similarity	NPD2882	Phase 1
0.7576	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD2391	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD1554	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD8093	Discontinued
0.7553	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD2896	Discontinued
0.7547	Intermediate Similarity	NPD7469	Discontinued
0.7546	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD3113	Approved
0.7546	Intermediate Similarity	NPD3112	Approved
0.7546	Intermediate Similarity	NPD3114	Approved
0.7546	Intermediate Similarity	NPD3115	Approved
0.7545	Intermediate Similarity	NPD1248	Discontinued
0.754	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD8129	Discovery
0.7529	Intermediate Similarity	NPD2928	Phase 2
0.7529	Intermediate Similarity	NPD6178	Phase 3
0.7528	Intermediate Similarity	NPD4615	Phase 2
0.7517	Intermediate Similarity	NPD9583	Approved
0.7516	Intermediate Similarity	NPD3833	Phase 3
0.7516	Intermediate Similarity	NPD3944	Approved
0.7516	Intermediate Similarity	NPD3835	Phase 3
0.7516	Intermediate Similarity	NPD3942	Approved
0.7514	Intermediate Similarity	NPD1707	Approved
0.7514	Intermediate Similarity	NPD1708	Approved
0.7513	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD8094	Discontinued
0.75	Intermediate Similarity	NPD8036	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5862	Discovery
0.75	Intermediate Similarity	NPD8037	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2844	Phase 3
0.7486	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD5100	Phase 3
0.7474	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD3825	Phase 3
0.7472	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD5315	Discontinued
0.7469	Intermediate Similarity	NPD3262	Approved
0.7456	Intermediate Similarity	NPD5436	Phase 1
0.7444	Intermediate Similarity	NPD7944	Discontinued
0.7443	Intermediate Similarity	NPD706	Phase 1
0.7442	Intermediate Similarity	NPD8123	Approved
0.7442	Intermediate Similarity	NPD8122	Approved
0.744	Intermediate Similarity	NPD5611	Phase 2
0.7439	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD3813	Approved
0.7417	Intermediate Similarity	NPD1095	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD6281	Approved
0.7415	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD271	Approved
0.7415	Intermediate Similarity	NPD268	Approved
0.7414	Intermediate Similarity	NPD3178	Discontinued
0.7414	Intermediate Similarity	NPD1895	Discontinued
0.7407	Intermediate Similarity	NPD5066	Phase 2
0.7407	Intermediate Similarity	NPD5067	Phase 2
0.7405	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD2581	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