NPASS Compound

Structure

NPC41501 OpenBabel07101719242D 24 27 0 0 0 0 0 0 0 0999 V2000 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7036 1.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8376 0.7930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7036 2.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9716 1.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8376 2.7930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6026 2.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9716 2.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2395 2.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1055 2.7930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 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 2.2971 1.5243 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.1055 3.7930 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 2 0 0 0 0 5 11 2 0 0 0 0 6 11 1 0 0 0 0 7 8 2 0 0 0 0 7 13 1 0 0 0 0 8 20 1 0 0 0 0 9 12 2 0 0 0 0 9 14 1 0 0 0 0 10 12 1 0 0 0 0 10 15 2 0 0 0 0 11 18 1 0 0 0 0 12 16 1 0 0 0 0 13 16 2 0 0 0 0 13 21 1 0 0 0 0 14 18 1 0 0 0 0 14 21 2 0 0 0 0 15 19 1 0 0 0 0 15 24 1 0 0 0 0 16 17 1 0 0 0 0 17 19 2 0 0 0 0 17 20 1 0 0 0 0 18 22 2 0 0 0 0 19 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.1
Volume:	324.954
LogP:	2.673
LogD:	2.576
LogS:	-4.305
# Rotatable Bonds:	3
TPSA:	71.78
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.751
Synthetic Accessibility Score:	2.744
Fsp3:	0.105
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.787
MDCK Permeability:	1.9568811694625765e-05
Pgp-inhibitor:	0.042
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.143

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.048
Plasma Protein Binding (PPB):	99.13807678222656%
Volume Distribution (VD):	0.521
Pgp-substrate:	2.354874610900879%

ADMET: Metabolism

CYP1A2-inhibitor:	0.944
CYP1A2-substrate:	0.725
CYP2C19-inhibitor:	0.781
CYP2C19-substrate:	0.168
CYP2C9-inhibitor:	0.865
CYP2C9-substrate:	0.772
CYP2D6-inhibitor:	0.578
CYP2D6-substrate:	0.647
CYP3A4-inhibitor:	0.431
CYP3A4-substrate:	0.247

ADMET: Excretion

Clearance (CL):	0.829
Half-life (T1/2):	0.666

ADMET: Toxicity

hERG Blockers:	0.043
Human Hepatotoxicity (H-HT):	0.53
Drug-inuced Liver Injury (DILI):	0.973
AMES Toxicity:	0.827
Rat Oral Acute Toxicity:	0.155
Maximum Recommended Daily Dose:	0.636
Skin Sensitization:	0.73
Carcinogencity:	0.859
Eye Corrosion:	0.003
Eye Irritation:	0.225
Respiratory Toxicity:	0.916

Download Data

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

Natural Product: NPC41501

Natural Product ID:	NPC41501
*Common Name:**	DKIUYQSXDHVEST-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:	5-Benzoyldemethylaaptamine
Standard InCHIKey:	DKIUYQSXDHVEST-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H14N2O3/c1-24-15-10-12-9-14(18(22)11-5-3-2-4-6-11)21-13-7-8-20-17(16(12)13)19(15)23/h2-10,20,23H,1H3
SMILES:	COc1cc2cc(nc3c2c(c1O)[nH]cc3)C(=O)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2337111
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004297] Aryl-phenylketones

*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
NPO13586	Aaptos suberitoides	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20451377]
NPO13586	Aaptos suberitoides	Species	Suberitidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[23282083]
NPO13586	Aaptos suberitoides	Species	Suberitidae	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
IC50	1
Others	1

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1864	Cell Line	L5178Y	Mus musculus	IC50	=	5500.0	nM	PMID[512140]
NPT1864	Cell Line	L5178Y	Mus musculus	GI	=	93.7	%	PMID[512140]

☑ 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 NPC41501 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	453
0.1-0.2	3199
0.2-0.3	13203
0.3-0.4	3935
0.4-0.5	13556
0.5-0.6	6077
0.6-0.7	1893
0.7-0.8	368
0.8-0.85	12
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8447	Intermediate Similarity	NPC173080
0.8299	Intermediate Similarity	NPC132385
0.8265	Intermediate Similarity	NPC162530
0.8119	Intermediate Similarity	NPC18348
0.8101	Intermediate Similarity	NPC270515
0.8026	Intermediate Similarity	NPC472061
0.8018	Intermediate Similarity	NPC236668
0.7982	Intermediate Similarity	NPC146976
0.7975	Intermediate Similarity	NPC208522
0.7974	Intermediate Similarity	NPC210434
0.7932	Intermediate Similarity	NPC15406
0.7931	Intermediate Similarity	NPC49547
0.787	Intermediate Similarity	NPC470018
0.7835	Intermediate Similarity	NPC74575
0.7832	Intermediate Similarity	NPC473513
0.7783	Intermediate Similarity	NPC322482
0.7773	Intermediate Similarity	NPC210296
0.7768	Intermediate Similarity	NPC24019
0.7692	Intermediate Similarity	NPC278525
0.7672	Intermediate Similarity	NPC179287
0.7669	Intermediate Similarity	NPC172222
0.7669	Intermediate Similarity	NPC22481
0.7664	Intermediate Similarity	NPC77878
0.7644	Intermediate Similarity	NPC470020
0.7637	Intermediate Similarity	NPC208898
0.7627	Intermediate Similarity	NPC233334
0.7605	Intermediate Similarity	NPC108342
0.7595	Intermediate Similarity	NPC473182
0.7592	Intermediate Similarity	NPC183537
0.759	Intermediate Similarity	NPC89549
0.7586	Intermediate Similarity	NPC216612
0.7582	Intermediate Similarity	NPC9729
0.7577	Intermediate Similarity	NPC112206
0.7577	Intermediate Similarity	NPC202605
0.7574	Intermediate Similarity	NPC194740
0.7574	Intermediate Similarity	NPC246381
0.7573	Intermediate Similarity	NPC189903
0.7573	Intermediate Similarity	NPC182907
0.7568	Intermediate Similarity	NPC135887
0.7568	Intermediate Similarity	NPC199277
0.7563	Intermediate Similarity	NPC90875
0.7562	Intermediate Similarity	NPC142385
0.7559	Intermediate Similarity	NPC473639
0.7554	Intermediate Similarity	NPC94842
0.7551	Intermediate Similarity	NPC51854
0.7544	Intermediate Similarity	NPC232225
0.75	Intermediate Similarity	NPC303374
0.75	Intermediate Similarity	NPC473183
0.75	Intermediate Similarity	NPC471762
0.75	Intermediate Similarity	NPC6786
0.7489	Intermediate Similarity	NPC200888
0.748	Intermediate Similarity	NPC472031
0.748	Intermediate Similarity	NPC472066
0.748	Intermediate Similarity	NPC472067
0.7479	Intermediate Similarity	NPC475844
0.7479	Intermediate Similarity	NPC51388
0.7469	Intermediate Similarity	NPC472068
0.7469	Intermediate Similarity	NPC166722
0.7458	Intermediate Similarity	NPC470017
0.7449	Intermediate Similarity	NPC473188
0.7443	Intermediate Similarity	NPC230403
0.7439	Intermediate Similarity	NPC91868
0.7439	Intermediate Similarity	NPC63971
0.7437	Intermediate Similarity	NPC474701
0.7436	Intermediate Similarity	NPC280272
0.7427	Intermediate Similarity	NPC470022
0.7427	Intermediate Similarity	NPC235685
0.7426	Intermediate Similarity	NPC274640
0.7424	Intermediate Similarity	NPC316981
0.7421	Intermediate Similarity	NPC215837
0.7417	Intermediate Similarity	NPC473184
0.741	Intermediate Similarity	NPC129897
0.7407	Intermediate Similarity	NPC119134
0.7404	Intermediate Similarity	NPC122436
0.7397	Intermediate Similarity	NPC101350
0.7391	Intermediate Similarity	NPC266931
0.7388	Intermediate Similarity	NPC124313
0.7382	Intermediate Similarity	NPC17565
0.7382	Intermediate Similarity	NPC208084
0.738	Intermediate Similarity	NPC220337
0.738	Intermediate Similarity	NPC87413
0.7379	Intermediate Similarity	NPC137353
0.7377	Intermediate Similarity	NPC72905
0.7377	Intermediate Similarity	NPC207283
0.7377	Intermediate Similarity	NPC84164
0.7362	Intermediate Similarity	NPC118121
0.7362	Intermediate Similarity	NPC144452
0.7359	Intermediate Similarity	NPC298449
0.7353	Intermediate Similarity	NPC66777
0.735	Intermediate Similarity	NPC225279
0.7339	Intermediate Similarity	NPC204446
0.7331	Intermediate Similarity	NPC65277
0.7326	Intermediate Similarity	NPC315499
0.7318	Intermediate Similarity	NPC133140
0.7318	Intermediate Similarity	NPC195268
0.7313	Intermediate Similarity	NPC304183
0.7311	Intermediate Similarity	NPC157931
0.7311	Intermediate Similarity	NPC257851
0.7296	Intermediate Similarity	NPC293151
0.7293	Intermediate Similarity	NPC325297
0.7292	Intermediate Similarity	NPC474688
0.7292	Intermediate Similarity	NPC260434
0.7284	Intermediate Similarity	NPC237740
0.7281	Intermediate Similarity	NPC321428
0.7277	Intermediate Similarity	NPC150239
0.7276	Intermediate Similarity	NPC160100
0.7273	Intermediate Similarity	NPC253675
0.7269	Intermediate Similarity	NPC36229
0.7269	Intermediate Similarity	NPC16452
0.7269	Intermediate Similarity	NPC476581
0.7265	Intermediate Similarity	NPC182853
0.7265	Intermediate Similarity	NPC184408
0.7265	Intermediate Similarity	NPC303658
0.7265	Intermediate Similarity	NPC473822
0.7265	Intermediate Similarity	NPC247803
0.7258	Intermediate Similarity	NPC161801
0.7257	Intermediate Similarity	NPC295898
0.7257	Intermediate Similarity	NPC66815
0.7249	Intermediate Similarity	NPC39679
0.7243	Intermediate Similarity	NPC207620
0.7234	Intermediate Similarity	NPC148409
0.7229	Intermediate Similarity	NPC146418
0.722	Intermediate Similarity	NPC477112
0.722	Intermediate Similarity	NPC101312
0.7216	Intermediate Similarity	NPC169716
0.7215	Intermediate Similarity	NPC122463
0.7213	Intermediate Similarity	NPC184680
0.721	Intermediate Similarity	NPC118228
0.7206	Intermediate Similarity	NPC316224
0.7205	Intermediate Similarity	NPC4687
0.7205	Intermediate Similarity	NPC193777
0.7205	Intermediate Similarity	NPC249583
0.7203	Intermediate Similarity	NPC469439
0.72	Intermediate Similarity	NPC476578
0.72	Intermediate Similarity	NPC4071
0.72	Intermediate Similarity	NPC476582
0.72	Intermediate Similarity	NPC134637
0.7188	Intermediate Similarity	NPC209981
0.7184	Intermediate Similarity	NPC470785
0.7184	Intermediate Similarity	NPC470784
0.7171	Intermediate Similarity	NPC67401
0.7168	Intermediate Similarity	NPC234197
0.7167	Intermediate Similarity	NPC473185
0.7167	Intermediate Similarity	NPC471080
0.7167	Intermediate Similarity	NPC469592
0.716	Intermediate Similarity	NPC329631
0.7156	Intermediate Similarity	NPC17677
0.715	Intermediate Similarity	NPC312872
0.7149	Intermediate Similarity	NPC144381
0.7148	Intermediate Similarity	NPC282346
0.7143	Intermediate Similarity	NPC220851
0.7137	Intermediate Similarity	NPC31930
0.7132	Intermediate Similarity	NPC100734
0.7132	Intermediate Similarity	NPC315634
0.7132	Intermediate Similarity	NPC88923
0.7131	Intermediate Similarity	NPC39370
0.7131	Intermediate Similarity	NPC323969
0.7131	Intermediate Similarity	NPC174760
0.713	Intermediate Similarity	NPC193238
0.713	Intermediate Similarity	NPC270918
0.7126	Intermediate Similarity	NPC148889
0.7126	Intermediate Similarity	NPC53534
0.7125	Intermediate Similarity	NPC285254
0.7124	Intermediate Similarity	NPC264176
0.7124	Intermediate Similarity	NPC48353
0.7119	Intermediate Similarity	NPC473041
0.7119	Intermediate Similarity	NPC134702
0.7119	Intermediate Similarity	NPC46561
0.7119	Intermediate Similarity	NPC473186
0.7118	Intermediate Similarity	NPC285558
0.7112	Intermediate Similarity	NPC471304
0.7104	Intermediate Similarity	NPC227824
0.7103	Intermediate Similarity	NPC302807
0.7102	Intermediate Similarity	NPC473187
0.7102	Intermediate Similarity	NPC295228
0.7101	Intermediate Similarity	NPC280799
0.7101	Intermediate Similarity	NPC60621
0.7098	Intermediate Similarity	NPC258048
0.7095	Intermediate Similarity	NPC478078
0.7094	Intermediate Similarity	NPC250448
0.7094	Intermediate Similarity	NPC39500
0.7093	Intermediate Similarity	NPC477019
0.7089	Intermediate Similarity	NPC473179
0.7089	Intermediate Similarity	NPC193267
0.7089	Intermediate Similarity	NPC213530
0.7087	Intermediate Similarity	NPC472286
0.7087	Intermediate Similarity	NPC317373
0.7087	Intermediate Similarity	NPC472287
0.7085	Intermediate Similarity	NPC141915
0.7085	Intermediate Similarity	NPC114335
0.7085	Intermediate Similarity	NPC280964
0.7083	Intermediate Similarity	NPC473449
0.7082	Intermediate Similarity	NPC187501
0.708	Intermediate Similarity	NPC306376
0.708	Intermediate Similarity	NPC58209
0.708	Intermediate Similarity	NPC107123
0.7078	Intermediate Similarity	NPC201508
0.7076	Intermediate Similarity	NPC305984
0.7076	Intermediate Similarity	NPC469727
0.7073	Intermediate Similarity	NPC15801

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 NPC41501 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	253
0.1-0.2	682
0.2-0.3	966
0.3-0.4	1431
0.4-0.5	2606
0.5-0.6	2267
0.6-0.7	861
0.7-0.8	84
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7796	Intermediate Similarity	NPD8091	Phase 3
0.7692	Intermediate Similarity	NPD5022	Discontinued
0.7689	Intermediate Similarity	NPD4502	Phase 2
0.7673	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD4429	Discontinued
0.7586	Intermediate Similarity	NPD2285	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD3263	Phase 3
0.7521	Intermediate Similarity	NPD6716	Phase 1
0.7511	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7478	Intermediate Similarity	NPD5658	Approved
0.7417	Intermediate Similarity	NPD2951	Discontinued
0.7414	Intermediate Similarity	NPD7395	Discontinued
0.7375	Intermediate Similarity	NPD6494	Phase 2
0.7371	Intermediate Similarity	NPD3920	Phase 2
0.735	Intermediate Similarity	NPD5070	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD6242	Discontinued
0.7339	Intermediate Similarity	NPD5632	Approved
0.7328	Intermediate Similarity	NPD8149	Discontinued
0.7318	Intermediate Similarity	NPD3923	Approved
0.7318	Intermediate Similarity	NPD3921	Approved
0.7318	Intermediate Similarity	NPD3924	Approved
0.7318	Intermediate Similarity	NPD3922	Approved
0.7288	Intermediate Similarity	NPD1954	Phase 1
0.7287	Intermediate Similarity	NPD5488	Discontinued
0.7277	Intermediate Similarity	NPD2175	Phase 3
0.7277	Intermediate Similarity	NPD2177	Approved
0.7277	Intermediate Similarity	NPD2176	Approved
0.7261	Intermediate Similarity	NPD4885	Approved
0.7238	Intermediate Similarity	NPD3259	Approved
0.7229	Intermediate Similarity	NPD5416	Discontinued
0.7227	Intermediate Similarity	NPD6247	Clinical (unspecified phase)
0.7224	Intermediate Similarity	NPD7025	Clinical (unspecified phase)
0.721	Intermediate Similarity	NPD5903	Approved
0.721	Intermediate Similarity	NPD5902	Approved
0.7205	Intermediate Similarity	NPD6290	Phase 2
0.7203	Intermediate Similarity	NPD5930	Phase 3
0.7198	Intermediate Similarity	NPD5866	Approved
0.7177	Intermediate Similarity	NPD6230	Discontinued
0.7172	Intermediate Similarity	NPD7853	Phase 2
0.7166	Intermediate Similarity	NPD6517	Phase 3
0.716	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD7586	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD5939	Approved
0.7155	Intermediate Similarity	NPD5936	Approved
0.7149	Intermediate Similarity	NPD1505	Phase 2
0.7143	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7924	Phase 2
0.7143	Intermediate Similarity	NPD7925	Phase 2
0.7132	Intermediate Similarity	NPD7803	Approved
0.7131	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD6964	Approved
0.7131	Intermediate Similarity	NPD6963	Approved
0.713	Intermediate Similarity	NPD7222	Phase 2
0.713	Intermediate Similarity	NPD5429	Discontinued
0.7119	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7106	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD4373	Phase 2
0.7087	Intermediate Similarity	NPD3003	Approved
0.7087	Intermediate Similarity	NPD5530	Phase 1
0.7085	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD7955	Approved
0.707	Intermediate Similarity	NPD7956	Approved
0.7066	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD7426	Phase 1
0.7051	Intermediate Similarity	NPD3815	Phase 1
0.7051	Intermediate Similarity	NPD3816	Phase 1
0.7042	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD5479	Discontinued
0.7037	Intermediate Similarity	NPD7589	Clinical (unspecified phase)
0.7036	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD3243	Approved
0.702	Intermediate Similarity	NPD7558	Phase 2
0.7008	Intermediate Similarity	NPD6962	Phase 2
0.7008	Intermediate Similarity	NPD7859	Phase 2
0.7	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD5482	Discontinued
0.6996	Remote Similarity	NPD3986	Discontinued
0.6993	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD8244	Phase 2
0.6991	Remote Similarity	NPD5512	Phase 3
0.6988	Remote Similarity	NPD6790	Phase 1
0.6988	Remote Similarity	NPD7417	Discontinued
0.6987	Remote Similarity	NPD5850	Phase 3
0.6985	Remote Similarity	NPD8364	Approved
0.6985	Remote Similarity	NPD8363	Approved
0.6979	Remote Similarity	NPD7069	Discontinued
0.6979	Remote Similarity	NPD7225	Discontinued
0.6977	Remote Similarity	NPD7708	Approved
0.6977	Remote Similarity	NPD4083	Discontinued
0.6976	Remote Similarity	NPD7729	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD7279	Phase 2
0.6971	Remote Similarity	NPD7278	Phase 2
0.697	Remote Similarity	NPD4795	Phase 2
0.6967	Remote Similarity	NPD4952	Phase 3
0.6962	Remote Similarity	NPD5612	Discontinued
0.696	Remote Similarity	NPD1483	Discontinued
0.6958	Remote Similarity	NPD5506	Approved
0.6958	Remote Similarity	NPD5507	Approved
0.6955	Remote Similarity	NPD7994	Phase 2
0.6953	Remote Similarity	NPD2916	Discontinued
0.6949	Remote Similarity	NPD3945	Discontinued
0.6948	Remote Similarity	NPD5905	Phase 1
0.6948	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD8016	Phase 3
0.6947	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD3763	Approved
0.6946	Remote Similarity	NPD2899	Discontinued
0.6943	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD3925	Approved
0.6939	Remote Similarity	NPD1867	Approved
0.6935	Remote Similarity	NPD4368	Phase 2
0.6935	Remote Similarity	NPD5805	Approved
0.6932	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.692	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.691	Remote Similarity	NPD7452	Approved
0.691	Remote Similarity	NPD7453	Approved
0.69	Remote Similarity	NPD5547	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD8466	Approved
0.6891	Remote Similarity	NPD8467	Approved
0.6891	Remote Similarity	NPD8465	Approved
0.6885	Remote Similarity	NPD4845	Discontinued
0.688	Remote Similarity	NPD5863	Clinical (unspecified phase)
0.687	Remote Similarity	NPD1740	Approved
0.687	Remote Similarity	NPD4995	Approved
0.687	Remote Similarity	NPD4996	Approved
0.687	Remote Similarity	NPD1739	Approved
0.6864	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6858	Remote Similarity	NPD5937	Approved
0.685	Remote Similarity	NPD3328	Phase 2
0.6849	Remote Similarity	NPD4897	Phase 2
0.6848	Remote Similarity	NPD8463	Approved
0.6846	Remote Similarity	NPD6228	Discontinued
0.6844	Remote Similarity	NPD7603	Discontinued
0.6842	Remote Similarity	NPD5151	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD7548	Discontinued
0.6829	Remote Similarity	NPD4925	Approved
0.6827	Remote Similarity	NPD3006	Discontinued
0.6826	Remote Similarity	NPD1768	Approved
0.6824	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD7886	Phase 2
0.6813	Remote Similarity	NPD4561	Discontinued
0.6813	Remote Similarity	NPD7885	Phase 2
0.6809	Remote Similarity	NPD6376	Discontinued
0.6805	Remote Similarity	NPD7194	Discontinued
0.6798	Remote Similarity	NPD7413	Phase 3
0.6793	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD4131	Phase 3
0.6792	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.679	Remote Similarity	NPD8459	Approved
0.679	Remote Similarity	NPD1856	Discontinued
0.679	Remote Similarity	NPD8425	Approved
0.679	Remote Similarity	NPD8460	Approved
0.679	Remote Similarity	NPD6209	Approved
0.679	Remote Similarity	NPD8426	Approved
0.6784	Remote Similarity	NPD6569	Phase 2
0.6783	Remote Similarity	NPD5071	Phase 2
0.6782	Remote Similarity	NPD6531	Approved
0.6782	Remote Similarity	NPD6530	Approved
0.678	Remote Similarity	NPD6773	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD7180	Phase 3
0.6771	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD4511	Phase 1
0.6766	Remote Similarity	NPD8428	Approved
0.6766	Remote Similarity	NPD8427	Approved
0.6766	Remote Similarity	NPD8429	Approved
0.6761	Remote Similarity	NPD1900	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD6199	Discontinued
0.6761	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD7479	Phase 2
0.6739	Remote Similarity	NPD4605	Approved
0.6739	Remote Similarity	NPD4604	Approved
0.6737	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD4859	Phase 1
0.6736	Remote Similarity	NPD3258	Approved
0.6736	Remote Similarity	NPD3794	Approved
0.6736	Remote Similarity	NPD3795	Approved
0.6732	Remote Similarity	NPD3809	Discontinued
0.6731	Remote Similarity	NPD6961	Discontinued
0.6725	Remote Similarity	NPD3810	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD3507	Phase 2
0.671	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD5293	Phase 2
0.6707	Remote Similarity	NPD7797	Approved
0.6707	Remote Similarity	NPD7796	Approved
0.6707	Remote Similarity	NPD7031	Phase 1
0.6707	Remote Similarity	NPD5640	Discontinued
0.6705	Remote Similarity	NPD6456	Discontinued
0.6697	Remote Similarity	NPD6159	Phase 2

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