NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	334.07
Volume:	290.588
LogP:	3.417
LogD:	2.997
LogS:	-3.55
# Rotatable Bonds:	0
TPSA:	28.4
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.797
Synthetic Accessibility Score:	3.58
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.794
MDCK Permeability:	1.8605889636091888e-05
Pgp-inhibitor:	0.897
Pgp-substrate:	0.364
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.993
Plasma Protein Binding (PPB):	87.2713851928711%
Volume Distribution (VD):	3.081
Pgp-substrate:	13.551958084106445%

ADMET: Metabolism

CYP1A2-inhibitor:	0.57
CYP1A2-substrate:	0.948
CYP2C19-inhibitor:	0.505
CYP2C19-substrate:	0.956
CYP2C9-inhibitor:	0.032
CYP2C9-substrate:	0.54
CYP2D6-inhibitor:	0.96
CYP2D6-substrate:	0.902
CYP3A4-inhibitor:	0.016
CYP3A4-substrate:	0.909

ADMET: Excretion

Clearance (CL):	8.158
Half-life (T1/2):	0.115

ADMET: Toxicity

hERG Blockers:	0.627
Human Hepatotoxicity (H-HT):	0.412
Drug-inuced Liver Injury (DILI):	0.388
AMES Toxicity:	0.142
Rat Oral Acute Toxicity:	0.505
Maximum Recommended Daily Dose:	0.99
Skin Sensitization:	0.408
Carcinogencity:	0.708
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.878

Download Data

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

Natural Product: NPC121903

Natural Product ID:	NPC121903
*Common Name:**	Arborescidine D
IUPAC Name:	n.a.
Synonyms:	Arborescidine D
Standard InCHIKey:	SEKCREXSGCGPFK-DZGCQCFKSA-N
Standard InCHI:	InChI=1S/C16H19BrN2O/c1-18-8-7-12-11-6-5-10(17)9-14(11)19-15(20)4-2-3-13(18)16(12)19/h5-6,9,13,15,20H,2-4,7-8H2,1H3/t13-,15+/m0/s1
SMILES:	CN1CCc2c3[C@@H]1CCC[C@H](n3c1c2ccc(c1)Br)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL483416
PubChem CID:	10019829
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001213] Pyridoindoles [CHEMONTID:0001914] Beta carbolines

*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
NPO1831	Pseudodistoma arborescens	Species	Pseudodistomidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8450325]
NPO1831	Pseudodistoma arborescens	Species	Pseudodistomidae	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	3.0	ug.mL-1	PMID[447997]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	3.0	ug.mL-1	PMID[447998]

☑ 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 NPC121903 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	367
0.1-0.2	3293
0.2-0.3	19576
0.3-0.4	12224
0.4-0.5	3392
0.5-0.6	2440
0.6-0.7	1131
0.7-0.8	256
0.8-0.85	16
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8276	Intermediate Similarity	NPC113626
0.8204	Intermediate Similarity	NPC255229
0.8204	Intermediate Similarity	NPC81229
0.8166	Intermediate Similarity	NPC2165
0.815	Intermediate Similarity	NPC472122
0.815	Intermediate Similarity	NPC24594
0.8103	Intermediate Similarity	NPC326575
0.8092	Intermediate Similarity	NPC329688
0.8092	Intermediate Similarity	NPC189812
0.807	Intermediate Similarity	NPC317430
0.8057	Intermediate Similarity	NPC133261
0.8035	Intermediate Similarity	NPC288074
0.8035	Intermediate Similarity	NPC472123
0.8011	Intermediate Similarity	NPC472105
0.8011	Intermediate Similarity	NPC187827
0.8011	Intermediate Similarity	NPC15840
0.8	Intermediate Similarity	NPC234987
0.7976	Intermediate Similarity	NPC129721
0.7921	Intermediate Similarity	NPC472109
0.7921	Intermediate Similarity	NPC472110
0.7874	Intermediate Similarity	NPC158129
0.7814	Intermediate Similarity	NPC243716
0.7772	Intermediate Similarity	NPC477167
0.7772	Intermediate Similarity	NPC473342
0.7766	Intermediate Similarity	NPC23420
0.7766	Intermediate Similarity	NPC303820
0.7766	Intermediate Similarity	NPC205254
0.7766	Intermediate Similarity	NPC106771
0.7747	Intermediate Similarity	NPC472323
0.7746	Intermediate Similarity	NPC195507
0.7727	Intermediate Similarity	NPC64055
0.7725	Intermediate Similarity	NPC52909
0.7725	Intermediate Similarity	NPC94211
0.7725	Intermediate Similarity	NPC475935
0.7725	Intermediate Similarity	NPC2272
0.7722	Intermediate Similarity	NPC139291
0.7722	Intermediate Similarity	NPC472108
0.7719	Intermediate Similarity	NPC6436
0.7701	Intermediate Similarity	NPC109447
0.7688	Intermediate Similarity	NPC247987
0.767	Intermediate Similarity	NPC82331
0.7669	Intermediate Similarity	NPC104483
0.7656	Intermediate Similarity	NPC476121
0.764	Intermediate Similarity	NPC474958
0.764	Intermediate Similarity	NPC134586
0.7602	Intermediate Similarity	NPC285469
0.7598	Intermediate Similarity	NPC211997
0.7581	Intermediate Similarity	NPC477166
0.7581	Intermediate Similarity	NPC304187
0.7561	Intermediate Similarity	NPC316811
0.7543	Intermediate Similarity	NPC274229
0.753	Intermediate Similarity	NPC20144
0.7527	Intermediate Similarity	NPC19679
0.7527	Intermediate Similarity	NPC472104
0.7514	Intermediate Similarity	NPC175474
0.75	Intermediate Similarity	NPC469785
0.7486	Intermediate Similarity	NPC472119
0.7486	Intermediate Similarity	NPC469541
0.7486	Intermediate Similarity	NPC258480
0.7485	Intermediate Similarity	NPC141926
0.7474	Intermediate Similarity	NPC476124
0.7473	Intermediate Similarity	NPC469501
0.7473	Intermediate Similarity	NPC469470
0.747	Intermediate Similarity	NPC473868
0.747	Intermediate Similarity	NPC63157
0.7457	Intermediate Similarity	NPC469762
0.7446	Intermediate Similarity	NPC79062
0.7446	Intermediate Similarity	NPC472107
0.7443	Intermediate Similarity	NPC470508
0.7442	Intermediate Similarity	NPC207726
0.7432	Intermediate Similarity	NPC159125
0.7432	Intermediate Similarity	NPC143533
0.7429	Intermediate Similarity	NPC16667
0.7414	Intermediate Similarity	NPC230869
0.7405	Intermediate Similarity	NPC66210
0.7405	Intermediate Similarity	NPC478077
0.7401	Intermediate Similarity	NPC54988
0.7401	Intermediate Similarity	NPC49954
0.7401	Intermediate Similarity	NPC474561
0.7391	Intermediate Similarity	NPC108011
0.7384	Intermediate Similarity	NPC73952
0.7384	Intermediate Similarity	NPC469760
0.7384	Intermediate Similarity	NPC259644
0.7384	Intermediate Similarity	NPC469765
0.7384	Intermediate Similarity	NPC25008
0.7384	Intermediate Similarity	NPC469763
0.7384	Intermediate Similarity	NPC469786
0.738	Intermediate Similarity	NPC95783
0.7368	Intermediate Similarity	NPC40070
0.7363	Intermediate Similarity	NPC248462
0.7351	Intermediate Similarity	NPC62510
0.7341	Intermediate Similarity	NPC80597
0.7341	Intermediate Similarity	NPC211572
0.7341	Intermediate Similarity	NPC70922
0.7341	Intermediate Similarity	NPC75540
0.7341	Intermediate Similarity	NPC476297
0.7341	Intermediate Similarity	NPC212376
0.733	Intermediate Similarity	NPC282231
0.732	Intermediate Similarity	NPC473761
0.7317	Intermediate Similarity	NPC198988
0.7314	Intermediate Similarity	NPC67056
0.7303	Intermediate Similarity	NPC160105
0.7296	Intermediate Similarity	NPC474145
0.7296	Intermediate Similarity	NPC475841
0.7288	Intermediate Similarity	NPC194640
0.7288	Intermediate Similarity	NPC311276
0.7283	Intermediate Similarity	NPC233936
0.7283	Intermediate Similarity	NPC307191
0.7273	Intermediate Similarity	NPC279918
0.7273	Intermediate Similarity	NPC325252
0.7268	Intermediate Similarity	NPC219336
0.7263	Intermediate Similarity	NPC88315
0.7263	Intermediate Similarity	NPC201700
0.7263	Intermediate Similarity	NPC63751
0.7259	Intermediate Similarity	NPC53344
0.7251	Intermediate Similarity	NPC21605
0.725	Intermediate Similarity	NPC207020
0.7249	Intermediate Similarity	NPC472097
0.7249	Intermediate Similarity	NPC117244
0.7249	Intermediate Similarity	NPC473763
0.7246	Intermediate Similarity	NPC88097
0.7245	Intermediate Similarity	NPC470505
0.7241	Intermediate Similarity	NPC470507
0.724	Intermediate Similarity	NPC262898
0.7235	Intermediate Similarity	NPC470440
0.7225	Intermediate Similarity	NPC289299
0.7225	Intermediate Similarity	NPC57994
0.7222	Intermediate Similarity	NPC280548
0.7213	Intermediate Similarity	NPC217372
0.7213	Intermediate Similarity	NPC15573
0.7213	Intermediate Similarity	NPC183662
0.7206	Intermediate Similarity	NPC255110
0.7202	Intermediate Similarity	NPC52557
0.7198	Intermediate Similarity	NPC472586
0.7198	Intermediate Similarity	NPC469938
0.7196	Intermediate Similarity	NPC231536
0.7191	Intermediate Similarity	NPC40779
0.7191	Intermediate Similarity	NPC149265
0.7188	Intermediate Similarity	NPC179701
0.7174	Intermediate Similarity	NPC472443
0.7158	Intermediate Similarity	NPC150048
0.7158	Intermediate Similarity	NPC203754
0.7151	Intermediate Similarity	NPC163055
0.7151	Intermediate Similarity	NPC17751
0.7151	Intermediate Similarity	NPC470111
0.7143	Intermediate Similarity	NPC102338
0.7143	Intermediate Similarity	NPC63199
0.7143	Intermediate Similarity	NPC111602
0.7143	Intermediate Similarity	NPC34508
0.7143	Intermediate Similarity	NPC34844
0.7143	Intermediate Similarity	NPC314603
0.7143	Intermediate Similarity	NPC196251
0.7143	Intermediate Similarity	NPC477611
0.7135	Intermediate Similarity	NPC314372
0.7135	Intermediate Similarity	NPC469896
0.7135	Intermediate Similarity	NPC194881
0.7128	Intermediate Similarity	NPC249150
0.7128	Intermediate Similarity	NPC49196
0.7128	Intermediate Similarity	NPC81654
0.7128	Intermediate Similarity	NPC79129
0.7128	Intermediate Similarity	NPC474707
0.7128	Intermediate Similarity	NPC313985
0.7128	Intermediate Similarity	NPC249040
0.7128	Intermediate Similarity	NPC195461
0.7126	Intermediate Similarity	NPC150259
0.7121	Intermediate Similarity	NPC472111
0.712	Intermediate Similarity	NPC64436
0.7113	Intermediate Similarity	NPC50503
0.7112	Intermediate Similarity	NPC472294
0.7111	Intermediate Similarity	NPC478183
0.711	Intermediate Similarity	NPC37548
0.7105	Intermediate Similarity	NPC472112
0.7102	Intermediate Similarity	NPC141353
0.7101	Intermediate Similarity	NPC59084
0.7101	Intermediate Similarity	NPC2949
0.7098	Intermediate Similarity	NPC245916
0.7097	Intermediate Similarity	NPC243381
0.7097	Intermediate Similarity	NPC275292
0.7095	Intermediate Similarity	NPC478182
0.709	Intermediate Similarity	NPC204565
0.7081	Intermediate Similarity	NPC233050
0.7081	Intermediate Similarity	NPC276540
0.7074	Intermediate Similarity	NPC15102
0.7059	Intermediate Similarity	NPC472444
0.7059	Intermediate Similarity	NPC48938
0.7053	Intermediate Similarity	NPC65215
0.7053	Intermediate Similarity	NPC173028
0.7045	Intermediate Similarity	NPC476219
0.7044	Intermediate Similarity	NPC477610
0.7043	Intermediate Similarity	NPC91179
0.7033	Intermediate Similarity	NPC97343
0.7031	Intermediate Similarity	NPC472113
0.7027	Intermediate Similarity	NPC248454
0.7027	Intermediate Similarity	NPC151939
0.7027	Intermediate Similarity	NPC59269
0.7024	Intermediate Similarity	NPC314102
0.7024	Intermediate Similarity	NPC251722
0.7018	Intermediate Similarity	NPC190296
0.7016	Intermediate Similarity	NPC329858
0.7016	Intermediate Similarity	NPC314333

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 NPC121903 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	208
0.1-0.2	623
0.2-0.3	1083
0.3-0.4	1677
0.4-0.5	2953
0.5-0.6	2064
0.6-0.7	495
0.7-0.8	47
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
0.7906	Intermediate Similarity	NPD4520	Approved
0.767	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD3385	Approved
0.7561	Intermediate Similarity	NPD2068	Approved
0.7561	Intermediate Similarity	NPD2071	Approved
0.7561	Intermediate Similarity	NPD2069	Approved
0.7561	Intermediate Similarity	NPD2070	Approved
0.753	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD2882	Phase 1
0.7438	Intermediate Similarity	NPD3654	Approved
0.7412	Intermediate Similarity	NPD1183	Approved
0.7394	Intermediate Similarity	NPD2323	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD2383	Phase 1
0.736	Intermediate Similarity	NPD4638	Approved
0.736	Intermediate Similarity	NPD4639	Approved
0.736	Intermediate Similarity	NPD4640	Approved
0.7345	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD6158	Phase 2
0.7326	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD1995	Approved
0.7301	Intermediate Similarity	NPD1993	Approved
0.7301	Intermediate Similarity	NPD1994	Approved
0.7294	Intermediate Similarity	NPD1683	Approved
0.7257	Intermediate Similarity	NPD4326	Phase 2
0.7251	Intermediate Similarity	NPD4702	Approved
0.7251	Intermediate Similarity	NPD4703	Approved
0.7228	Intermediate Similarity	NPD6595	Phase 3
0.7225	Intermediate Similarity	NPD4602	Approved
0.7225	Intermediate Similarity	NPD7944	Discontinued
0.7222	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1325	Approved
0.7222	Intermediate Similarity	NPD1326	Approved
0.7198	Intermediate Similarity	NPD5065	Approved
0.7189	Intermediate Similarity	NPD4203	Approved
0.7189	Intermediate Similarity	NPD4204	Approved
0.7188	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD7287	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD5021	Discontinued
0.7166	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD2915	Discontinued
0.7143	Intermediate Similarity	NPD750	Phase 2
0.7135	Intermediate Similarity	NPD5899	Approved
0.7135	Intermediate Similarity	NPD5898	Approved
0.7135	Intermediate Similarity	NPD6452	Discontinued
0.7135	Intermediate Similarity	NPD5897	Approved
0.7128	Intermediate Similarity	NPD4601	Approved
0.7128	Intermediate Similarity	NPD4600	Approved
0.7126	Intermediate Similarity	NPD45	Approved
0.7126	Intermediate Similarity	NPD6554	Approved
0.7118	Intermediate Similarity	NPD4047	Discontinued
0.7113	Intermediate Similarity	NPD4397	Phase 1
0.7113	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD1661	Suspended
0.7052	Intermediate Similarity	NPD4547	Phase 3
0.7049	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD2144	Approved
0.7021	Intermediate Similarity	NPD4957	Phase 2
0.702	Intermediate Similarity	NPD6991	Approved
0.7016	Intermediate Similarity	NPD4499	Approved
0.7016	Intermediate Similarity	NPD6281	Approved
0.701	Intermediate Similarity	NPD7935	Phase 2
0.6989	Remote Similarity	NPD4079	Approved
0.6989	Remote Similarity	NPD4076	Approved
0.6984	Remote Similarity	NPD6227	Discontinued
0.6978	Remote Similarity	NPD2390	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD5100	Phase 3
0.6973	Remote Similarity	NPD5104	Approved
0.6973	Remote Similarity	NPD2381	Approved
0.6973	Remote Similarity	NPD2380	Approved
0.6973	Remote Similarity	NPD2382	Approved
0.6971	Remote Similarity	NPD4462	Approved
0.6971	Remote Similarity	NPD4463	Approved
0.697	Remote Similarity	NPD3475	Approved
0.697	Remote Similarity	NPD3476	Approved
0.6959	Remote Similarity	NPD5020	Approved
0.6952	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD3505	Approved
0.6935	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD3506	Approved
0.6927	Remote Similarity	NPD5255	Approved
0.6919	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6492	Phase 2
0.6915	Remote Similarity	NPD3038	Discontinued
0.6911	Remote Similarity	NPD3002	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD5140	Approved
0.6906	Remote Similarity	NPD5138	Approved
0.6901	Remote Similarity	NPD3943	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD8386	Phase 2
0.6898	Remote Similarity	NPD8036	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD8037	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7469	Discontinued
0.6895	Remote Similarity	NPD5555	Phase 1
0.689	Remote Similarity	NPD2119	Approved
0.689	Remote Similarity	NPD2118	Approved
0.6885	Remote Similarity	NPD5862	Discovery
0.6885	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD5495	Phase 2
0.6881	Remote Similarity	NPD7671	Approved
0.6881	Remote Similarity	NPD7672	Approved
0.6878	Remote Similarity	NPD4341	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4334	Discontinued
0.686	Remote Similarity	NPD1722	Approved
0.6854	Remote Similarity	NPD6285	Phase 2
0.6845	Remote Similarity	NPD8123	Approved
0.6845	Remote Similarity	NPD4181	Approved
0.6845	Remote Similarity	NPD8122	Approved
0.6842	Remote Similarity	NPD786	Approved
0.6832	Remote Similarity	NPD7453	Approved
0.6832	Remote Similarity	NPD7452	Approved
0.6828	Remote Similarity	NPD482	Approved
0.6825	Remote Similarity	NPD4383	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD8431	Approved
0.6821	Remote Similarity	NPD3717	Discontinued
0.6821	Remote Similarity	NPD3525	Discontinued
0.6821	Remote Similarity	NPD2006	Phase 2
0.6818	Remote Similarity	NPD5538	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD2430	Phase 2
0.6818	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6999	Discontinued
0.6816	Remote Similarity	NPD2150	Discontinued
0.6806	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD7666	Phase 3
0.6798	Remote Similarity	NPD7665	Phase 2
0.6798	Remote Similarity	NPD2012	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD2092	Phase 2
0.6789	Remote Similarity	NPD2094	Phase 2
0.6789	Remote Similarity	NPD5596	Phase 2
0.6789	Remote Similarity	NPD2095	Phase 2
0.6784	Remote Similarity	NPD4501	Approved
0.6784	Remote Similarity	NPD4500	Approved
0.6782	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD3813	Approved
0.6782	Remote Similarity	NPD5254	Discontinued
0.6778	Remote Similarity	NPD2581	Approved
0.6778	Remote Similarity	NPD2582	Approved
0.6765	Remote Similarity	NPD1255	Approved
0.6765	Remote Similarity	NPD1254	Approved
0.6765	Remote Similarity	NPD1253	Approved
0.6765	Remote Similarity	NPD1256	Approved
0.6763	Remote Similarity	NPD1592	Phase 3
0.6758	Remote Similarity	NPD5315	Discontinued
0.6754	Remote Similarity	NPD2091	Phase 2
0.6754	Remote Similarity	NPD2096	Phase 2
0.675	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6749	Remote Similarity	NPD7222	Phase 2
0.6746	Remote Similarity	NPD4028	Approved
0.6746	Remote Similarity	NPD3944	Approved
0.6746	Remote Similarity	NPD4029	Approved
0.6746	Remote Similarity	NPD3942	Approved
0.6746	Remote Similarity	NPD4030	Approved
0.6738	Remote Similarity	NPD4128	Approved
0.6737	Remote Similarity	NPD8408	Discontinued
0.6736	Remote Similarity	NPD4948	Discontinued
0.6733	Remote Similarity	NPD8272	Phase 2
0.6723	Remote Similarity	NPD3100	Discontinued
0.672	Remote Similarity	NPD3117	Approved
0.672	Remote Similarity	NPD3116	Approved
0.6719	Remote Similarity	NPD5075	Discontinued
0.6714	Remote Similarity	NPD6455	Phase 3
0.6705	Remote Similarity	NPD6148	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD2837	Discontinued
0.6703	Remote Similarity	NPD2511	Approved
0.6702	Remote Similarity	NPD4345	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD5409	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD3401	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD509	Phase 3
0.6684	Remote Similarity	NPD6721	Phase 1
0.6684	Remote Similarity	NPD3404	Approved
0.6684	Remote Similarity	NPD4315	Phase 2
0.6683	Remote Similarity	NPD4886	Phase 2
0.6683	Remote Similarity	NPD7777	Approved
0.6683	Remote Similarity	NPD7778	Approved
0.6683	Remote Similarity	NPD53	Approved
0.6682	Remote Similarity	NPD6717	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1272	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD198	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6159	Phase 2
0.6667	Remote Similarity	NPD2290	Phase 3
0.6667	Remote Similarity	NPD2289	Phase 3
0.6651	Remote Similarity	NPD6978	Phase 2
0.6651	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.665	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.665	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD8020	Approved
0.6649	Remote Similarity	NPD8021	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