NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	343.95
Volume:	249.01
LogP:	3.854
LogD:	3.133
LogS:	-4.779
# Rotatable Bonds:	3
TPSA:	19.03
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.896
Synthetic Accessibility Score:	2.452
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.628
MDCK Permeability:	1.3243668945506215e-05
Pgp-inhibitor:	0.053
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.062
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.994
Plasma Protein Binding (PPB):	93.35748291015625%
Volume Distribution (VD):	2.667
Pgp-substrate:	9.674230575561523%

ADMET: Metabolism

CYP1A2-inhibitor:	0.934
CYP1A2-substrate:	0.957
CYP2C19-inhibitor:	0.114
CYP2C19-substrate:	0.929
CYP2C9-inhibitor:	0.016
CYP2C9-substrate:	0.727
CYP2D6-inhibitor:	0.968
CYP2D6-substrate:	0.935
CYP3A4-inhibitor:	0.035
CYP3A4-substrate:	0.292

ADMET: Excretion

Clearance (CL):	4.661
Half-life (T1/2):	0.319

ADMET: Toxicity

hERG Blockers:	0.512
Human Hepatotoxicity (H-HT):	0.25
Drug-inuced Liver Injury (DILI):	0.854
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.895
Maximum Recommended Daily Dose:	0.946
Skin Sensitization:	0.87
Carcinogencity:	0.073
Eye Corrosion:	0.038
Eye Irritation:	0.076
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC149265

Natural Product ID:	NPC149265
*Common Name:**	5,6-Dibromo-N,N-Dimethyltryptamine
IUPAC Name:	2-(5,6-dibromo-1H-indol-3-yl)-N,N-dimethylethanamine
Synonyms:
Standard InCHIKey:	FQUXASLSQLXGHJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H14Br2N2/c1-16(2)4-3-8-7-15-12-6-11(14)10(13)5-9(8)12/h5-7,15H,3-4H2,1-2H3
SMILES:	CN(C)CCc1c[nH]c2cc(c(cc12)Br)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL256339
PubChem CID:	360251
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
NPO33044	florida sponges	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[18217716]
NPO13341	Bryopsis pennata	Species	Bryopsidaceae	Eukaryota	n.a.	Hawaiian	n.a.	PMID[19916528]
NPO13341	Bryopsis pennata	Species	Bryopsidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	4

Activity Type	# Activity
Individual Protein	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT267	Individual Protein	Neuropeptide Y receptor type 1	Homo sapiens	Activity	=	100.0	%	PMID[527125]
NPT267	Individual Protein	Neuropeptide Y receptor type 1	Homo sapiens	Activity	=	17.0	%	PMID[527125]
NPT247	Individual Protein	Endothelin receptor ET-A	Homo sapiens	Activity	=	100.0	%	PMID[527125]
NPT247	Individual Protein	Endothelin receptor ET-A	Homo sapiens	Activity	=	62.0	%	PMID[527125]

☑ 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 NPC149265 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	1569
0.1-0.2	15669
0.2-0.3	17269
0.3-0.4	3819
0.4-0.5	1983
0.5-0.6	1432
0.6-0.7	675
0.7-0.8	232
0.8-0.85	35
0.85-0.9	9
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9467	High Similarity	NPC34844
0.94	High Similarity	NPC141926
0.9182	High Similarity	NPC280297
0.9067	High Similarity	NPC316069
0.8805	High Similarity	NPC280864
0.8805	High Similarity	NPC17751
0.8704	High Similarity	NPC82331
0.8701	High Similarity	NPC2272
0.8688	High Similarity	NPC274229
0.865	High Similarity	NPC477611
0.8545	High Similarity	NPC474958
0.8543	High Similarity	NPC110126
0.8543	High Similarity	NPC73767
0.8537	High Similarity	NPC64055
0.8533	High Similarity	NPC84911
0.8528	High Similarity	NPC97343
0.8467	Intermediate Similarity	NPC96102
0.8467	Intermediate Similarity	NPC29886
0.8467	Intermediate Similarity	NPC261195
0.8424	Intermediate Similarity	NPC288074
0.8411	Intermediate Similarity	NPC105127
0.8366	Intermediate Similarity	NPC469761
0.8366	Intermediate Similarity	NPC469779
0.8366	Intermediate Similarity	NPC469767
0.8366	Intermediate Similarity	NPC469783
0.8366	Intermediate Similarity	NPC469780
0.8366	Intermediate Similarity	NPC469768
0.8366	Intermediate Similarity	NPC469784
0.8333	Intermediate Similarity	NPC233050
0.8333	Intermediate Similarity	NPC276540
0.8312	Intermediate Similarity	NPC469766
0.8302	Intermediate Similarity	NPC232798
0.8258	Intermediate Similarity	NPC190296
0.8247	Intermediate Similarity	NPC279081
0.8235	Intermediate Similarity	NPC307191
0.8235	Intermediate Similarity	NPC275292
0.8235	Intermediate Similarity	NPC243381
0.82	Intermediate Similarity	NPC82295
0.8182	Intermediate Similarity	NPC109447
0.8153	Intermediate Similarity	NPC314372
0.8129	Intermediate Similarity	NPC230002
0.8114	Intermediate Similarity	NPC231536
0.8061	Intermediate Similarity	NPC247987
0.805	Intermediate Similarity	NPC471957
0.8038	Intermediate Similarity	NPC159856
0.8	Intermediate Similarity	NPC321911
0.7987	Intermediate Similarity	NPC288838
0.7987	Intermediate Similarity	NPC143872
0.7978	Intermediate Similarity	NPC474180
0.7978	Intermediate Similarity	NPC188821
0.7963	Intermediate Similarity	NPC200214
0.795	Intermediate Similarity	NPC24678
0.795	Intermediate Similarity	NPC105818
0.795	Intermediate Similarity	NPC53947
0.7949	Intermediate Similarity	NPC316811
0.7937	Intermediate Similarity	NPC201380
0.7937	Intermediate Similarity	NPC469811
0.7937	Intermediate Similarity	NPC179787
0.7931	Intermediate Similarity	NPC110158
0.7901	Intermediate Similarity	NPC470823
0.7889	Intermediate Similarity	NPC179701
0.7875	Intermediate Similarity	NPC63545
0.7853	Intermediate Similarity	NPC25008
0.7853	Intermediate Similarity	NPC469786
0.7853	Intermediate Similarity	NPC469760
0.7853	Intermediate Similarity	NPC259644
0.7853	Intermediate Similarity	NPC469763
0.7853	Intermediate Similarity	NPC469765
0.7853	Intermediate Similarity	NPC73952
0.7845	Intermediate Similarity	NPC262898
0.7829	Intermediate Similarity	NPC108011
0.7821	Intermediate Similarity	NPC477166
0.7821	Intermediate Similarity	NPC477167
0.7821	Intermediate Similarity	NPC304187
0.7821	Intermediate Similarity	NPC473342
0.7806	Intermediate Similarity	NPC198988
0.7805	Intermediate Similarity	NPC75540
0.7805	Intermediate Similarity	NPC211572
0.7805	Intermediate Similarity	NPC212376
0.7805	Intermediate Similarity	NPC70922
0.7805	Intermediate Similarity	NPC80597
0.7802	Intermediate Similarity	NPC474389
0.7791	Intermediate Similarity	NPC216713
0.7778	Intermediate Similarity	NPC88315
0.7778	Intermediate Similarity	NPC22079
0.7771	Intermediate Similarity	NPC318065
0.7771	Intermediate Similarity	NPC206819
0.7771	Intermediate Similarity	NPC56765
0.7756	Intermediate Similarity	NPC325252
0.7744	Intermediate Similarity	NPC325903
0.7711	Intermediate Similarity	NPC286427
0.7707	Intermediate Similarity	NPC150259
0.7683	Intermediate Similarity	NPC470233
0.7665	Intermediate Similarity	NPC41257
0.7651	Intermediate Similarity	NPC469785
0.7643	Intermediate Similarity	NPC218268
0.7633	Intermediate Similarity	NPC90723
0.7622	Intermediate Similarity	NPC269203
0.7622	Intermediate Similarity	NPC77241
0.7622	Intermediate Similarity	NPC13456
0.7622	Intermediate Similarity	NPC166209
0.7605	Intermediate Similarity	NPC216643
0.7605	Intermediate Similarity	NPC469762
0.7605	Intermediate Similarity	NPC236711
0.76	Intermediate Similarity	NPC41174
0.7581	Intermediate Similarity	NPC475935
0.7581	Intermediate Similarity	NPC94211
0.7581	Intermediate Similarity	NPC52909
0.7574	Intermediate Similarity	NPC282231
0.7568	Intermediate Similarity	NPC153123
0.7568	Intermediate Similarity	NPC237414
0.7568	Intermediate Similarity	NPC268744
0.7568	Intermediate Similarity	NPC201266
0.7568	Intermediate Similarity	NPC475914
0.7568	Intermediate Similarity	NPC220797
0.7568	Intermediate Similarity	NPC474318
0.7568	Intermediate Similarity	NPC477004
0.7562	Intermediate Similarity	NPC59084
0.7562	Intermediate Similarity	NPC2949
0.756	Intermediate Similarity	NPC135141
0.756	Intermediate Similarity	NPC92796
0.7544	Intermediate Similarity	NPC49217
0.7529	Intermediate Similarity	NPC311276
0.7527	Intermediate Similarity	NPC205254
0.7527	Intermediate Similarity	NPC23420
0.7527	Intermediate Similarity	NPC303820
0.7527	Intermediate Similarity	NPC106771
0.7516	Intermediate Similarity	NPC473868
0.7516	Intermediate Similarity	NPC63157
0.7516	Intermediate Similarity	NPC250361
0.7515	Intermediate Similarity	NPC131718
0.7515	Intermediate Similarity	NPC470204
0.7515	Intermediate Similarity	NPC215584
0.7515	Intermediate Similarity	NPC44773
0.7515	Intermediate Similarity	NPC279918
0.7515	Intermediate Similarity	NPC122141
0.75	Intermediate Similarity	NPC88097
0.7485	Intermediate Similarity	NPC2165
0.7485	Intermediate Similarity	NPC195507
0.7484	Intermediate Similarity	NPC125746
0.7484	Intermediate Similarity	NPC473587
0.7471	Intermediate Similarity	NPC470203
0.7457	Intermediate Similarity	NPC194411
0.7456	Intermediate Similarity	NPC230869
0.7453	Intermediate Similarity	NPC115611
0.7447	Intermediate Similarity	NPC473761
0.7442	Intermediate Similarity	NPC160105
0.7442	Intermediate Similarity	NPC474561
0.7442	Intermediate Similarity	NPC49954
0.7436	Intermediate Similarity	NPC475428
0.7427	Intermediate Similarity	NPC317105
0.7427	Intermediate Similarity	NPC40779
0.7419	Intermediate Similarity	NPC473762
0.7389	Intermediate Similarity	NPC179365
0.7389	Intermediate Similarity	NPC475450
0.7378	Intermediate Similarity	NPC470440
0.7375	Intermediate Similarity	NPC314102
0.7375	Intermediate Similarity	NPC251722
0.7341	Intermediate Similarity	NPC54988
0.733	Intermediate Similarity	NPC275305
0.733	Intermediate Similarity	NPC82053
0.733	Intermediate Similarity	NPC37423
0.7326	Intermediate Similarity	NPC102423
0.732	Intermediate Similarity	NPC46358
0.7314	Intermediate Similarity	NPC470498
0.7312	Intermediate Similarity	NPC222018
0.7299	Intermediate Similarity	NPC201700
0.7299	Intermediate Similarity	NPC63751
0.7289	Intermediate Similarity	NPC21605
0.7277	Intermediate Similarity	NPC470505
0.7273	Intermediate Similarity	NPC204141
0.7273	Intermediate Similarity	NPC27740
0.7273	Intermediate Similarity	NPC314603
0.7273	Intermediate Similarity	NPC285731
0.7257	Intermediate Similarity	NPC474168
0.7247	Intermediate Similarity	NPC240088
0.7247	Intermediate Similarity	NPC68354
0.7247	Intermediate Similarity	NPC84827
0.7247	Intermediate Similarity	NPC145885
0.7247	Intermediate Similarity	NPC14113
0.7247	Intermediate Similarity	NPC473380
0.7233	Intermediate Similarity	NPC473930
0.7225	Intermediate Similarity	NPC194640
0.7207	Intermediate Similarity	NPC215795
0.7207	Intermediate Similarity	NPC176199
0.7207	Intermediate Similarity	NPC265710
0.7207	Intermediate Similarity	NPC11126
0.7202	Intermediate Similarity	NPC40070
0.7202	Intermediate Similarity	NPC33421
0.72	Intermediate Similarity	NPC78020
0.7194	Intermediate Similarity	NPC207020
0.7191	Intermediate Similarity	NPC280852
0.7191	Intermediate Similarity	NPC267885
0.7191	Intermediate Similarity	NPC121903
0.7186	Intermediate Similarity	NPC470111
0.7184	Intermediate Similarity	NPC42372
0.7175	Intermediate Similarity	NPC313791
0.7167	Intermediate Similarity	NPC314919
0.7167	Intermediate Similarity	NPC16659
0.7157	Intermediate Similarity	NPC470703

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 NPC149265 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	477
0.1-0.2	1080
0.2-0.3	1227
0.3-0.4	2496
0.4-0.5	2240
0.5-0.6	1251
0.6-0.7	312
0.7-0.8	64
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8467	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD786	Approved
0.8194	Intermediate Similarity	NPD1722	Approved
0.8113	Intermediate Similarity	NPD3100	Discontinued
0.795	Intermediate Similarity	NPD2172	Phase 1
0.7949	Intermediate Similarity	NPD2071	Approved
0.7949	Intermediate Similarity	NPD2069	Approved
0.7949	Intermediate Similarity	NPD2068	Approved
0.7949	Intermediate Similarity	NPD2070	Approved
0.7888	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1183	Approved
0.7744	Intermediate Similarity	NPD2837	Discontinued
0.7725	Intermediate Similarity	NPD1403	Approved
0.7725	Intermediate Similarity	NPD1404	Approved
0.7677	Intermediate Similarity	NPD1995	Approved
0.7677	Intermediate Similarity	NPD1994	Approved
0.7677	Intermediate Similarity	NPD1993	Approved
0.7633	Intermediate Similarity	NPD3323	Discontinued
0.7562	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD2642	Approved
0.7544	Intermediate Similarity	NPD2639	Approved
0.75	Intermediate Similarity	NPD2640	Approved
0.75	Intermediate Similarity	NPD2641	Approved
0.75	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD5254	Discontinued
0.7414	Intermediate Similarity	NPD3610	Approved
0.7414	Intermediate Similarity	NPD3609	Approved
0.7399	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD3654	Approved
0.7368	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD991	Phase 2
0.733	Intermediate Similarity	NPD4128	Approved
0.7325	Intermediate Similarity	NPD3475	Approved
0.7325	Intermediate Similarity	NPD3476	Approved
0.7289	Intermediate Similarity	NPD4547	Phase 3
0.7288	Intermediate Similarity	NPD4075	Phase 2
0.7247	Intermediate Similarity	NPD3505	Approved
0.7247	Intermediate Similarity	NPD3506	Approved
0.7247	Intermediate Similarity	NPD4181	Approved
0.7247	Intermediate Similarity	NPD2144	Approved
0.7244	Intermediate Similarity	NPD2119	Approved
0.7244	Intermediate Similarity	NPD2118	Approved
0.7235	Intermediate Similarity	NPD2580	Discontinued
0.7235	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD5065	Approved
0.7229	Intermediate Similarity	NPD1683	Approved
0.7207	Intermediate Similarity	NPD4079	Approved
0.7207	Intermediate Similarity	NPD4076	Approved
0.7202	Intermediate Similarity	NPD4462	Approved
0.7202	Intermediate Similarity	NPD4463	Approved
0.7191	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD3385	Approved
0.716	Intermediate Similarity	NPD1262	Discovery
0.7152	Intermediate Similarity	NPD2006	Phase 2
0.7151	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1248	Discontinued
0.7143	Intermediate Similarity	NPD2430	Phase 2
0.7135	Intermediate Similarity	NPD482	Approved
0.7127	Intermediate Similarity	NPD3038	Discontinued
0.7127	Intermediate Similarity	NPD1707	Approved
0.7127	Intermediate Similarity	NPD1708	Approved
0.7102	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD5105	Approved
0.7088	Intermediate Similarity	NPD5106	Approved
0.7088	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4028	Approved
0.7081	Intermediate Similarity	NPD4029	Approved
0.7081	Intermediate Similarity	NPD4030	Approved
0.7078	Intermediate Similarity	NPD271	Approved
0.7078	Intermediate Similarity	NPD268	Approved
0.7078	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD2165	Phase 1
0.7072	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD6595	Phase 3
0.707	Intermediate Similarity	NPD9583	Approved
0.7049	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD3115	Approved
0.7035	Intermediate Similarity	NPD3113	Approved
0.7035	Intermediate Similarity	NPD3114	Approved
0.7035	Intermediate Similarity	NPD3112	Approved
0.7011	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7287	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD750	Phase 2
0.6975	Remote Similarity	NPD3942	Approved
0.6975	Remote Similarity	NPD3944	Approved
0.6973	Remote Similarity	NPD6217	Discontinued
0.6973	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD9357	Approved
0.694	Remote Similarity	NPD1895	Discontinued
0.6935	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD5590	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD3961	Discontinued
0.6928	Remote Similarity	NPD9392	Approved
0.6928	Remote Similarity	NPD9396	Approved
0.6908	Remote Similarity	NPD269	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD2095	Phase 2
0.6902	Remote Similarity	NPD2092	Phase 2
0.6902	Remote Similarity	NPD2094	Phase 2
0.6902	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD715	Phase 3
0.689	Remote Similarity	NPD1254	Approved
0.689	Remote Similarity	NPD1256	Approved
0.689	Remote Similarity	NPD1255	Approved
0.689	Remote Similarity	NPD1253	Approved
0.6879	Remote Similarity	NPD975	Approved
0.6879	Remote Similarity	NPD977	Approved
0.6879	Remote Similarity	NPD976	Approved
0.6875	Remote Similarity	NPD5315	Discontinued
0.6875	Remote Similarity	NPD2385	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD5436	Phase 1
0.6867	Remote Similarity	NPD768	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD2091	Phase 2
0.6865	Remote Similarity	NPD2096	Phase 2
0.6852	Remote Similarity	NPD803	Phase 1
0.6845	Remote Similarity	NPD8431	Approved
0.6815	Remote Similarity	NPD748	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD5145	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD2074	Approved
0.6766	Remote Similarity	NPD2075	Approved
0.6766	Remote Similarity	NPD2072	Approved
0.6766	Remote Similarity	NPD2073	Approved
0.6755	Remote Similarity	NPD2310	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD802	Phase 2
0.6747	Remote Similarity	NPD6554	Approved
0.6747	Remote Similarity	NPD45	Approved
0.6743	Remote Similarity	NPD2150	Discontinued
0.6737	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD1528	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD4639	Approved
0.6722	Remote Similarity	NPD4640	Approved
0.6722	Remote Similarity	NPD4638	Approved
0.6719	Remote Similarity	NPD7619	Phase 3
0.6719	Remote Similarity	NPD7618	Phase 3
0.6708	Remote Similarity	NPD1598	Discontinued
0.6706	Remote Similarity	NPD1918	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD4702	Approved
0.6686	Remote Similarity	NPD1592	Phase 3
0.6686	Remote Similarity	NPD4703	Approved
0.6685	Remote Similarity	NPD1326	Approved
0.6685	Remote Similarity	NPD1325	Approved
0.6684	Remote Similarity	NPD2960	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4649	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1038	Approved
0.6667	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD6664	Approved
0.6648	Remote Similarity	NPD3116	Approved
0.6648	Remote Similarity	NPD3117	Approved
0.6648	Remote Similarity	NPD1567	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD4047	Discontinued
0.6646	Remote Similarity	NPD9598	Discontinued
0.663	Remote Similarity	NPD2390	Clinical (unspecified phase)
0.663	Remote Similarity	NPD5021	Discontinued
0.663	Remote Similarity	NPD2367	Phase 2
0.6629	Remote Similarity	NPD3339	Approved
0.6626	Remote Similarity	NPD947	Approved
0.6612	Remote Similarity	NPD4112	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD3833	Phase 3
0.6609	Remote Similarity	NPD3835	Phase 3
0.6598	Remote Similarity	NPD6278	Clinical (unspecified phase)
0.659	Remote Similarity	NPD1661	Suspended
0.6587	Remote Similarity	NPD490	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD439	Approved
0.6575	Remote Similarity	NPD438	Approved
0.6568	Remote Similarity	NPD680	Discontinued
0.6561	Remote Similarity	NPD1227	Phase 2
0.6559	Remote Similarity	NPD3341	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD6828	Phase 2
0.6557	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD6827	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD2748	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD1284	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD4615	Phase 2
0.6527	Remote Similarity	NPD4880	Discontinued
0.6519	Remote Similarity	NPD1313	Approved
0.6514	Remote Similarity	NPD971	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD2323	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD7564	Discontinued
0.6505	Remote Similarity	NPD7111	Discontinued
0.6482	Remote Similarity	NPD3015	Discontinued
0.648	Remote Similarity	NPD7948	Phase 1
0.6464	Remote Similarity	NPD5138	Approved
0.6464	Remote Similarity	NPD5140	Approved
0.645	Remote Similarity	NPD201	Phase 2
0.645	Remote Similarity	NPD200	Phase 2
0.6446	Remote Similarity	NPD1251	Discontinued
0.6444	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD2012	Clinical (unspecified phase)
0.644	Remote Similarity	NPD2793	Discontinued
0.6437	Remote Similarity	NPD7469	Discontinued

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