NPASS Compound

Structure

NPC469784 OpenBabel07101719252D 30 31 0 0 0 0 0 0 0 0999 V2000 -5.1973 -13.2140 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5282 -12.4708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8372 -11.5198 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1681 -10.7766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4771 -9.8256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8080 -9.0824 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1170 -8.1314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4478 -7.3882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7569 -6.4371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0877 -5.6940 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3967 -4.7429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7276 -3.9998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0366 -3.0487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3675 -2.3056 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6765 -1.3545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0074 -0.6114 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 -2.3164 0.3397 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 -0.3090 2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6473 1.0828 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 -1.9563 2.0339 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 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 19 1 0 0 0 0 17 18 2 0 0 0 0 17 20 1 0 0 0 0 18 21 1 0 0 0 0 19 23 1 0 0 0 0 20 27 2 0 0 0 0 21 28 2 0 0 0 0 22 24 1 0 0 0 0 22 26 1 0 0 0 0 23 29 1 0 0 0 0 24 29 1 0 0 0 0 25 26 2 0 0 0 0 25 30 1 0 0 0 0 26 27 1 0 0 0 0 27 28 1 0 0 0 0 28 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	412.38
Volume:	487.179
LogP:	9.284
LogD:	4.839
LogS:	-6.23
# Rotatable Bonds:	20
TPSA:	27.82
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.209
Synthetic Accessibility Score:	2.144
Fsp3:	0.714
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:	-5.328
MDCK Permeability:	6.123049388406798e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.913
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.039
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.356
Plasma Protein Binding (PPB):	96.9891586303711%
Volume Distribution (VD):	3.532
Pgp-substrate:	1.0624459981918335%

ADMET: Metabolism

CYP1A2-inhibitor:	0.155
CYP1A2-substrate:	0.197
CYP2C19-inhibitor:	0.491
CYP2C19-substrate:	0.093
CYP2C9-inhibitor:	0.073
CYP2C9-substrate:	0.83
CYP2D6-inhibitor:	0.988
CYP2D6-substrate:	0.878
CYP3A4-inhibitor:	0.745
CYP3A4-substrate:	0.124

ADMET: Excretion

Clearance (CL):	4.443
Half-life (T1/2):	0.05

ADMET: Toxicity

hERG Blockers:	0.981
Human Hepatotoxicity (H-HT):	0.541
Drug-inuced Liver Injury (DILI):	0.118
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.301
Maximum Recommended Daily Dose:	0.862
Skin Sensitization:	0.975
Carcinogencity:	0.017
Eye Corrosion:	0.064
Eye Irritation:	0.246
Respiratory Toxicity:	0.943

Download Data

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

Natural Product: NPC469784

Natural Product ID:	NPC469784
*Common Name:**	N-[2-(1H-Indol-3-Yl)Ethyl]Octadecan-1-Amine
IUPAC Name:	N-[2-(1H-indol-3-yl)ethyl]octadecan-1-amine
Synonyms:
Standard InCHIKey:	VOBCHHSFSHYHIA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C28H48N2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-19-23-29-24-22-26-25-30-28-21-18-17-20-27(26)28/h17-18,20-21,25,29-30H,2-16,19,22-24H2,1H3
SMILES:	CCCCCCCCCCCCCCCCCCNCCC1=CNC2=CC=CC=C21
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1171482
PubChem CID:	46897208
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0000183] Tryptamines and derivatives

*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
Others	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4564	Cell Line	Neurons		Activity	=	129.9	%	PMID[554379]
NPT4564	Cell Line	Neurons		Activity	=	157.3	%	PMID[554379]

☑ 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 NPC469784 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	935
0.1-0.2	12840
0.2-0.3	18516
0.3-0.4	4832
0.4-0.5	2181
0.5-0.6	1705
0.6-0.7	995
0.7-0.8	501
0.8-0.85	103
0.85-0.9	47
0.9-0.95	27
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC469780
1.0	High Similarity	NPC469779
1.0	High Similarity	NPC469767
1.0	High Similarity	NPC469761
1.0	High Similarity	NPC469783
1.0	High Similarity	NPC469768
0.9925	High Similarity	NPC469766
0.9774	High Similarity	NPC73767
0.9773	High Similarity	NPC84911
0.9697	High Similarity	NPC96102
0.9697	High Similarity	NPC29886
0.9697	High Similarity	NPC261195
0.9627	High Similarity	NPC110126
0.9624	High Similarity	NPC105127
0.9429	High Similarity	NPC105818
0.9429	High Similarity	NPC24678
0.942	High Similarity	NPC314372
0.9416	High Similarity	NPC190296
0.9412	High Similarity	NPC279081
0.9394	High Similarity	NPC82295
0.9296	High Similarity	NPC73952
0.9296	High Similarity	NPC469786
0.9296	High Similarity	NPC469763
0.9296	High Similarity	NPC469765
0.9296	High Similarity	NPC25008
0.9296	High Similarity	NPC469760
0.9296	High Similarity	NPC259644
0.9291	High Similarity	NPC53947
0.927	High Similarity	NPC230002
0.9231	High Similarity	NPC211572
0.9231	High Similarity	NPC80597
0.9231	High Similarity	NPC212376
0.9231	High Similarity	NPC75540
0.9231	High Similarity	NPC70922
0.9214	High Similarity	NPC288838
0.9149	High Similarity	NPC471957
0.9143	High Similarity	NPC159856
0.9085	High Similarity	NPC321911
0.9078	High Similarity	NPC143872
0.9034	High Similarity	NPC469785
0.9028	High Similarity	NPC200214
0.9014	High Similarity	NPC201380
0.9014	High Similarity	NPC179787
0.9014	High Similarity	NPC469811
0.8973	High Similarity	NPC469762
0.8973	High Similarity	NPC286427
0.8958	High Similarity	NPC470823
0.8944	High Similarity	NPC63545
0.8913	High Similarity	NPC150259
0.8912	High Similarity	NPC206819
0.8912	High Similarity	NPC318065
0.8912	High Similarity	NPC41257
0.8912	High Similarity	NPC56765
0.8897	High Similarity	NPC325903
0.8897	High Similarity	NPC141926
0.8889	High Similarity	NPC22079
0.8859	High Similarity	NPC311276
0.8844	High Similarity	NPC216643
0.8841	High Similarity	NPC325252
0.8841	High Similarity	NPC218268
0.8836	High Similarity	NPC34844
0.8828	High Similarity	NPC216713
0.8828	High Similarity	NPC470233
0.8784	High Similarity	NPC92796
0.8784	High Similarity	NPC135141
0.8768	High Similarity	NPC198988
0.8742	High Similarity	NPC160105
0.8733	High Similarity	NPC40779
0.8733	High Similarity	NPC90723
0.8723	High Similarity	NPC59084
0.8723	High Similarity	NPC2949
0.8712	High Similarity	NPC41174
0.8686	High Similarity	NPC475450
0.8667	High Similarity	NPC470203
0.8662	High Similarity	NPC473868
0.8662	High Similarity	NPC63157
0.8618	High Similarity	NPC474561
0.8618	High Similarity	NPC49954
0.86	High Similarity	NPC470204
0.86	High Similarity	NPC215584
0.86	High Similarity	NPC44773
0.8593	High Similarity	NPC250361
0.8591	High Similarity	NPC236711
0.8562	High Similarity	NPC201700
0.8552	High Similarity	NPC316069
0.8543	High Similarity	NPC282231
0.854	High Similarity	NPC473587
0.8521	High Similarity	NPC88097
0.8516	High Similarity	NPC314603
0.8511	High Similarity	NPC251722
0.8511	High Similarity	NPC125746
0.8511	High Similarity	NPC314102
0.8506	High Similarity	NPC194411
0.8487	Intermediate Similarity	NPC317105
0.8478	Intermediate Similarity	NPC475428
0.8477	Intermediate Similarity	NPC279918
0.8477	Intermediate Similarity	NPC122141
0.8477	Intermediate Similarity	NPC131718
0.8467	Intermediate Similarity	NPC473762
0.8462	Intermediate Similarity	NPC115611
0.8442	Intermediate Similarity	NPC63751
0.8435	Intermediate Similarity	NPC2272
0.8417	Intermediate Similarity	NPC179365
0.8411	Intermediate Similarity	NPC230869
0.8377	Intermediate Similarity	NPC49217
0.837	Intermediate Similarity	NPC46358
0.8367	Intermediate Similarity	NPC21605
0.8366	Intermediate Similarity	NPC149265
0.8366	Intermediate Similarity	NPC194640
0.8357	Intermediate Similarity	NPC473930
0.8356	Intermediate Similarity	NPC204141
0.8344	Intermediate Similarity	NPC275305
0.8344	Intermediate Similarity	NPC37423
0.8312	Intermediate Similarity	NPC280864
0.8312	Intermediate Similarity	NPC17751
0.8309	Intermediate Similarity	NPC27740
0.8291	Intermediate Similarity	NPC474958
0.828	Intermediate Similarity	NPC477611
0.8258	Intermediate Similarity	NPC54988
0.8255	Intermediate Similarity	NPC33421
0.8255	Intermediate Similarity	NPC40070
0.8247	Intermediate Similarity	NPC102423
0.8243	Intermediate Similarity	NPC470111
0.8239	Intermediate Similarity	NPC68354
0.8239	Intermediate Similarity	NPC248454
0.8231	Intermediate Similarity	NPC470440
0.8231	Intermediate Similarity	NPC285731
0.8217	Intermediate Similarity	NPC470498
0.8217	Intermediate Similarity	NPC82331
0.8194	Intermediate Similarity	NPC274229
0.8188	Intermediate Similarity	NPC37548
0.8187	Intermediate Similarity	NPC176199
0.8187	Intermediate Similarity	NPC215795
0.8176	Intermediate Similarity	NPC280852
0.817	Intermediate Similarity	NPC475990
0.817	Intermediate Similarity	NPC221786
0.817	Intermediate Similarity	NPC474880
0.8165	Intermediate Similarity	NPC313791
0.8163	Intermediate Similarity	NPC242556
0.8137	Intermediate Similarity	NPC314919
0.8137	Intermediate Similarity	NPC300688
0.8137	Intermediate Similarity	NPC16659
0.8125	Intermediate Similarity	NPC59269
0.8125	Intermediate Similarity	NPC84827
0.8125	Intermediate Similarity	NPC151939
0.8125	Intermediate Similarity	NPC14113
0.8125	Intermediate Similarity	NPC145885
0.8121	Intermediate Similarity	NPC477134
0.8089	Intermediate Similarity	NPC78020
0.8086	Intermediate Similarity	NPC233936
0.8085	Intermediate Similarity	NPC282398
0.8077	Intermediate Similarity	NPC42372
0.8075	Intermediate Similarity	NPC11126
0.8075	Intermediate Similarity	NPC213468
0.8075	Intermediate Similarity	NPC265710
0.8071	Intermediate Similarity	NPC89490
0.8063	Intermediate Similarity	NPC267885
0.8049	Intermediate Similarity	NPC280290
0.8039	Intermediate Similarity	NPC51054
0.8039	Intermediate Similarity	NPC476464
0.8038	Intermediate Similarity	NPC97343
0.8037	Intermediate Similarity	NPC163055
0.8014	Intermediate Similarity	NPC475105
0.8014	Intermediate Similarity	NPC312092
0.8014	Intermediate Similarity	NPC329896
0.8014	Intermediate Similarity	NPC475090
0.8014	Intermediate Similarity	NPC104483
0.8012	Intermediate Similarity	NPC240088
0.8012	Intermediate Similarity	NPC284775
0.8012	Intermediate Similarity	NPC473380
0.8	Intermediate Similarity	NPC91958
0.8	Intermediate Similarity	NPC229173
0.8	Intermediate Similarity	NPC110500
0.8	Intermediate Similarity	NPC293216
0.8	Intermediate Similarity	NPC149155
0.8	Intermediate Similarity	NPC203468
0.8	Intermediate Similarity	NPC94752
0.7988	Intermediate Similarity	NPC228835
0.7986	Intermediate Similarity	NPC146373
0.7986	Intermediate Similarity	NPC245244
0.7986	Intermediate Similarity	NPC166424
0.7975	Intermediate Similarity	NPC307191
0.7974	Intermediate Similarity	NPC470507
0.7974	Intermediate Similarity	NPC476219
0.7974	Intermediate Similarity	NPC476297
0.7974	Intermediate Similarity	NPC477815
0.7974	Intermediate Similarity	NPC38736
0.7973	Intermediate Similarity	NPC20144
0.7963	Intermediate Similarity	NPC126709
0.7963	Intermediate Similarity	NPC248041
0.7956	Intermediate Similarity	NPC182570
0.7956	Intermediate Similarity	NPC48564
0.7956	Intermediate Similarity	NPC265605
0.7949	Intermediate Similarity	NPC225018
0.7947	Intermediate Similarity	NPC124005
0.7947	Intermediate Similarity	NPC187951
0.7945	Intermediate Similarity	NPC169433
0.7926	Intermediate Similarity	NPC81561
0.7922	Intermediate Similarity	NPC285469
0.7904	Intermediate Similarity	NPC213629

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 NPC469784 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	384
0.1-0.2	867
0.2-0.3	985
0.3-0.4	1966
0.4-0.5	2321
0.5-0.6	1674
0.6-0.7	721
0.7-0.8	183
0.8-0.85	38
0.85-0.9	6
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9774	High Similarity	NPD786	Approved
0.9697	High Similarity	NPD198	Clinical (unspecified phase)
0.9485	High Similarity	NPD1722	Approved
0.9357	High Similarity	NPD3100	Discontinued
0.9291	High Similarity	NPD2172	Phase 1
0.922	High Similarity	NPD4374	Clinical (unspecified phase)
0.8897	High Similarity	NPD2837	Discontinued
0.8733	High Similarity	NPD3323	Discontinued
0.8725	High Similarity	NPD1404	Approved
0.8725	High Similarity	NPD1403	Approved
0.8723	High Similarity	NPD3943	Clinical (unspecified phase)
0.8618	High Similarity	NPD2642	Approved
0.8618	High Similarity	NPD2639	Approved
0.8562	High Similarity	NPD2185	Clinical (unspecified phase)
0.8562	High Similarity	NPD2641	Approved
0.8562	High Similarity	NPD2640	Approved
0.8542	High Similarity	NPD5254	Discontinued
0.854	High Similarity	NPD3654	Approved
0.8506	High Similarity	NPD4184	Clinical (unspecified phase)
0.8478	Intermediate Similarity	NPD3476	Approved
0.8478	Intermediate Similarity	NPD3475	Approved
0.8472	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD3610	Approved
0.8452	Intermediate Similarity	NPD3609	Approved
0.8442	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.8394	Intermediate Similarity	NPD2119	Approved
0.8394	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.8394	Intermediate Similarity	NPD991	Phase 2
0.8394	Intermediate Similarity	NPD2118	Approved
0.8378	Intermediate Similarity	NPD4462	Approved
0.8378	Intermediate Similarity	NPD4463	Approved
0.8367	Intermediate Similarity	NPD4547	Phase 3
0.8345	Intermediate Similarity	NPD2006	Phase 2
0.8344	Intermediate Similarity	NPD4128	Approved
0.8311	Intermediate Similarity	NPD2430	Phase 2
0.8298	Intermediate Similarity	NPD3385	Approved
0.8291	Intermediate Similarity	NPD4075	Phase 2
0.8278	Intermediate Similarity	NPD2580	Discontinued
0.8239	Intermediate Similarity	NPD3505	Approved
0.8239	Intermediate Similarity	NPD3506	Approved
0.8239	Intermediate Similarity	NPD4181	Approved
0.8239	Intermediate Similarity	NPD2144	Approved
0.8228	Intermediate Similarity	NPD5065	Approved
0.8219	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD4079	Approved
0.8187	Intermediate Similarity	NPD4076	Approved
0.8176	Intermediate Similarity	NPD1683	Approved
0.8169	Intermediate Similarity	NPD4028	Approved
0.8169	Intermediate Similarity	NPD4030	Approved
0.8169	Intermediate Similarity	NPD4029	Approved
0.8137	Intermediate Similarity	NPD6595	Phase 3
0.8125	Intermediate Similarity	NPD1262	Discovery
0.8125	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD2165	Phase 1
0.8086	Intermediate Similarity	NPD3038	Discontinued
0.8063	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.8058	Intermediate Similarity	NPD9583	Approved
0.8042	Intermediate Similarity	NPD3942	Approved
0.8042	Intermediate Similarity	NPD3944	Approved
0.8039	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD3113	Approved
0.8039	Intermediate Similarity	NPD3115	Approved
0.8039	Intermediate Similarity	NPD3112	Approved
0.8039	Intermediate Similarity	NPD3114	Approved
0.8037	Intermediate Similarity	NPD5106	Approved
0.8037	Intermediate Similarity	NPD5105	Approved
0.8037	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD1248	Discontinued
0.8025	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD482	Approved
0.7988	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD1707	Approved
0.7975	Intermediate Similarity	NPD1708	Approved
0.7956	Intermediate Similarity	NPD271	Approved
0.7956	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD268	Approved
0.7952	Intermediate Similarity	NPD8431	Approved
0.7949	Intermediate Similarity	NPD5315	Discontinued
0.7949	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD2094	Phase 2
0.7927	Intermediate Similarity	NPD2092	Phase 2
0.7927	Intermediate Similarity	NPD2095	Phase 2
0.7926	Intermediate Similarity	NPD9392	Approved
0.7926	Intermediate Similarity	NPD9396	Approved
0.7925	Intermediate Similarity	NPD5436	Phase 1
0.7914	Intermediate Similarity	NPD9357	Approved
0.791	Intermediate Similarity	NPD269	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD6217	Discontinued
0.7879	Intermediate Similarity	NPD2091	Phase 2
0.7879	Intermediate Similarity	NPD2096	Phase 2
0.7866	Intermediate Similarity	NPD1895	Discontinued
0.7848	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD3961	Discontinued
0.7844	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD715	Phase 3
0.7778	Intermediate Similarity	NPD803	Phase 1
0.777	Intermediate Similarity	NPD2069	Approved
0.777	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD2068	Approved
0.777	Intermediate Similarity	NPD2071	Approved
0.777	Intermediate Similarity	NPD2075	Approved
0.777	Intermediate Similarity	NPD2072	Approved
0.777	Intermediate Similarity	NPD2070	Approved
0.777	Intermediate Similarity	NPD2073	Approved
0.777	Intermediate Similarity	NPD2074	Approved
0.7755	Intermediate Similarity	NPD6554	Approved
0.7755	Intermediate Similarity	NPD45	Approved
0.7742	Intermediate Similarity	NPD977	Approved
0.7742	Intermediate Similarity	NPD976	Approved
0.7742	Intermediate Similarity	NPD975	Approved
0.7716	Intermediate Similarity	NPD750	Phase 2
0.7692	Intermediate Similarity	NPD2150	Discontinued
0.7687	Intermediate Similarity	NPD1254	Approved
0.7687	Intermediate Similarity	NPD1255	Approved
0.7687	Intermediate Similarity	NPD1253	Approved
0.7687	Intermediate Similarity	NPD1256	Approved
0.7682	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD3339	Approved
0.7674	Intermediate Similarity	NPD7619	Phase 3
0.7674	Intermediate Similarity	NPD7618	Phase 3
0.7662	Intermediate Similarity	NPD3835	Phase 3
0.7662	Intermediate Similarity	NPD3833	Phase 3
0.7647	Intermediate Similarity	NPD5145	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD4702	Approved
0.7647	Intermediate Similarity	NPD4703	Approved
0.764	Intermediate Similarity	NPD4638	Approved
0.764	Intermediate Similarity	NPD4639	Approved
0.764	Intermediate Similarity	NPD4640	Approved
0.7633	Intermediate Similarity	NPD2310	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD1598	Discontinued
0.7619	Intermediate Similarity	NPD4880	Discontinued
0.7616	Intermediate Similarity	NPD4047	Discontinued
0.7602	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD1325	Approved
0.7593	Intermediate Similarity	NPD1326	Approved
0.7586	Intermediate Similarity	NPD6664	Approved
0.7582	Intermediate Similarity	NPD1528	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD1592	Phase 3
0.7546	Intermediate Similarity	NPD6827	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD6828	Phase 2
0.7546	Intermediate Similarity	NPD3117	Approved
0.7546	Intermediate Similarity	NPD3116	Approved
0.7545	Intermediate Similarity	NPD4649	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD1661	Suspended
0.7531	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD5021	Discontinued
0.7529	Intermediate Similarity	NPD2960	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD748	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD947	Approved
0.7515	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD802	Phase 2
0.7514	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD1038	Approved
0.75	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD7948	Phase 1
0.7483	Intermediate Similarity	NPD1994	Approved
0.7483	Intermediate Similarity	NPD1993	Approved
0.7483	Intermediate Similarity	NPD1995	Approved
0.747	Intermediate Similarity	NPD7111	Discontinued
0.7468	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD7469	Discontinued
0.7456	Intermediate Similarity	NPD7564	Discontinued
0.7452	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD9598	Discontinued
0.7439	Intermediate Similarity	NPD1567	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6278	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD4823	Approved
0.7426	Intermediate Similarity	NPD4824	Approved
0.7425	Intermediate Similarity	NPD3341	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD680	Discontinued
0.7394	Intermediate Similarity	NPD5787	Discontinued
0.7386	Intermediate Similarity	NPD3717	Discontinued
0.7381	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD8073	Approved
0.7356	Intermediate Similarity	NPD4615	Phase 2
0.7346	Intermediate Similarity	NPD3583	Phase 2
0.7346	Intermediate Similarity	NPD5138	Approved
0.7346	Intermediate Similarity	NPD5140	Approved
0.7338	Intermediate Similarity	NPD3401	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD8072	Approved
0.7329	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD1030	Approved
0.7325	Intermediate Similarity	NPD1027	Approved
0.7325	Intermediate Similarity	NPD1029	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD8386	Phase 2
0.732	Intermediate Similarity	NPD3834	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD9099	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD9098	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