NPASS Compound

Structure

NPC473825 OpenBabel07101718192D 21 23 0 0 1 0 0 0 0 0999 V2000 -0.3090 2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 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 3.5491 2.8090 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 5.2812 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 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 2.6831 1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.1472 3.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 3.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 11 1 0 0 0 0 4 5 1 0 0 0 0 4 6 2 0 0 0 0 5 12 2 0 0 0 0 6 17 1 0 0 0 0 7 13 1 0 0 0 0 7 14 1 0 0 0 0 8 15 2 0 0 0 0 8 17 1 0 0 0 0 9 12 1 0 0 0 0 9 20 1 0 0 0 0 10 13 2 0 0 0 0 10 16 1 0 0 0 0 11 18 2 0 0 0 0 11 20 1 0 0 0 0 12 14 1 0 0 0 0 13 15 1 0 0 0 0 14 17 1 1 0 0 0 15 21 1 0 0 0 0 16 19 2 0 0 0 0 16 21 1 0 0 0 0 17 3 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.12
Volume:	296.261
LogP:	2.456
LogD:	1.953
LogS:	-2.38
# Rotatable Bonds:	3
TPSA:	59.67
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.838
Synthetic Accessibility Score:	4.777
Fsp3:	0.353
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.77
MDCK Permeability:	1.921670809679199e-05
Pgp-inhibitor:	0.037
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.156
Plasma Protein Binding (PPB):	87.25668334960938%
Volume Distribution (VD):	2.216
Pgp-substrate:	18.562410354614258%

ADMET: Metabolism

CYP1A2-inhibitor:	0.42
CYP1A2-substrate:	0.105
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.152
CYP2C9-inhibitor:	0.08
CYP2C9-substrate:	0.09
CYP2D6-inhibitor:	0.104
CYP2D6-substrate:	0.101
CYP3A4-inhibitor:	0.344
CYP3A4-substrate:	0.376

ADMET: Excretion

Clearance (CL):	2.228
Half-life (T1/2):	0.848

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.415
Drug-inuced Liver Injury (DILI):	0.235
AMES Toxicity:	0.802
Rat Oral Acute Toxicity:	0.989
Maximum Recommended Daily Dose:	0.951
Skin Sensitization:	0.896
Carcinogencity:	0.818
Eye Corrosion:	0.023
Eye Irritation:	0.141
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC473825

Natural Product ID:	NPC473825
*Common Name:**	Tubipolide G
IUPAC Name:	[(4aR,8aR)-3,8a-dimethyl-2-oxo-4,4a-dihydrobenzo[f][1]benzofuran-5-yl]methyl acetate
Synonyms:	Tubipolide G
Standard InCHIKey:	MLJSUGCNCCUCNK-YOEHRIQHSA-N
Standard InCHI:	InChI=1S/C17H18O4/c1-10-13-7-14-12(9-20-11(2)18)5-4-6-17(14,3)8-15(13)21-16(10)19/h4-6,8,14H,7,9H2,1-3H3/t14-,17-/m0/s1
SMILES:	CC(=O)OCC1=CC=C[C@@]2([C@H]1CC1=C(C)C(=O)OC1=C2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL452880
PubChem CID:	10379244
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO6309	Tubipora musica	Species	Tubiporidae	Eukaryota	n.a.	Formosan stolonifer	n.a.	PMID[11720526]
NPO6309	Tubipora musica	Species	Tubiporidae	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
ED50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	4.01	ug ml-1	PMID[529597]

☑ 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 NPC473825 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	177
0.1-0.2	1251
0.2-0.3	5910
0.3-0.4	17129
0.4-0.5	10619
0.5-0.6	5937
0.6-0.7	1506
0.7-0.8	151
0.8-0.85	16
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8442	Intermediate Similarity	NPC54996
0.8354	Intermediate Similarity	NPC268827
0.8194	Intermediate Similarity	NPC220766
0.8082	Intermediate Similarity	NPC191233
0.8	Intermediate Similarity	NPC471956
0.8	Intermediate Similarity	NPC470693
0.8	Intermediate Similarity	NPC472302
0.7882	Intermediate Similarity	NPC125925
0.7821	Intermediate Similarity	NPC470686
0.7816	Intermediate Similarity	NPC469372
0.7792	Intermediate Similarity	NPC181587
0.7763	Intermediate Similarity	NPC232812
0.7667	Intermediate Similarity	NPC295347
0.7662	Intermediate Similarity	NPC37929
0.7662	Intermediate Similarity	NPC64234
0.7654	Intermediate Similarity	NPC184737
0.7647	Intermediate Similarity	NPC189311
0.7625	Intermediate Similarity	NPC4509
0.7619	Intermediate Similarity	NPC474193
0.7619	Intermediate Similarity	NPC12283
0.76	Intermediate Similarity	NPC315115
0.759	Intermediate Similarity	NPC42470
0.7582	Intermediate Similarity	NPC16967
0.7558	Intermediate Similarity	NPC291712
0.7556	Intermediate Similarity	NPC191521
0.7531	Intermediate Similarity	NPC189206
0.75	Intermediate Similarity	NPC471218
0.75	Intermediate Similarity	NPC16321
0.75	Intermediate Similarity	NPC208094
0.75	Intermediate Similarity	NPC200513
0.75	Intermediate Similarity	NPC268122
0.75	Intermediate Similarity	NPC284561
0.75	Intermediate Similarity	NPC133600
0.7468	Intermediate Similarity	NPC16349
0.7468	Intermediate Similarity	NPC222244
0.7467	Intermediate Similarity	NPC182794
0.7444	Intermediate Similarity	NPC162615
0.7444	Intermediate Similarity	NPC152778
0.7444	Intermediate Similarity	NPC205034
0.7444	Intermediate Similarity	NPC1108
0.7442	Intermediate Similarity	NPC472442
0.7439	Intermediate Similarity	NPC474005
0.7439	Intermediate Similarity	NPC471220
0.7416	Intermediate Similarity	NPC310479
0.7416	Intermediate Similarity	NPC212679
0.7416	Intermediate Similarity	NPC182136
0.7416	Intermediate Similarity	NPC280149
0.7416	Intermediate Similarity	NPC469595
0.7416	Intermediate Similarity	NPC220454
0.7416	Intermediate Similarity	NPC221111
0.7412	Intermediate Similarity	NPC477124
0.7412	Intermediate Similarity	NPC193198
0.7412	Intermediate Similarity	NPC118423
0.7412	Intermediate Similarity	NPC472440
0.7386	Intermediate Similarity	NPC226863
0.7375	Intermediate Similarity	NPC259599
0.7375	Intermediate Similarity	NPC15499
0.7375	Intermediate Similarity	NPC474758
0.7375	Intermediate Similarity	NPC117746
0.7375	Intermediate Similarity	NPC294434
0.7363	Intermediate Similarity	NPC477129
0.7363	Intermediate Similarity	NPC477130
0.7363	Intermediate Similarity	NPC471994
0.7363	Intermediate Similarity	NPC120351
0.7363	Intermediate Similarity	NPC166143
0.7356	Intermediate Similarity	NPC168248
0.7342	Intermediate Similarity	NPC257618
0.7333	Intermediate Similarity	NPC2882
0.7326	Intermediate Similarity	NPC318515
0.7317	Intermediate Similarity	NPC68156
0.7317	Intermediate Similarity	NPC471225
0.7317	Intermediate Similarity	NPC315394
0.7308	Intermediate Similarity	NPC265574
0.7303	Intermediate Similarity	NPC5509
0.7303	Intermediate Similarity	NPC177141
0.7294	Intermediate Similarity	NPC94200
0.7283	Intermediate Similarity	NPC474909
0.7283	Intermediate Similarity	NPC209355
0.7273	Intermediate Similarity	NPC475678
0.7273	Intermediate Similarity	NPC472266
0.7273	Intermediate Similarity	NPC476600
0.7253	Intermediate Similarity	NPC472954
0.725	Intermediate Similarity	NPC276336
0.7241	Intermediate Similarity	NPC65661
0.7241	Intermediate Similarity	NPC281172
0.7241	Intermediate Similarity	NPC474013
0.7241	Intermediate Similarity	NPC30984
0.7237	Intermediate Similarity	NPC470688
0.7234	Intermediate Similarity	NPC181147
0.7229	Intermediate Similarity	NPC253749
0.7215	Intermediate Similarity	NPC315285
0.7215	Intermediate Similarity	NPC59558
0.7215	Intermediate Similarity	NPC316029
0.7215	Intermediate Similarity	NPC469660
0.7209	Intermediate Similarity	NPC288281
0.7209	Intermediate Similarity	NPC311070
0.7209	Intermediate Similarity	NPC474809
0.7204	Intermediate Similarity	NPC473153
0.7204	Intermediate Similarity	NPC260796
0.7195	Intermediate Similarity	NPC27205
0.7191	Intermediate Similarity	NPC196407
0.7179	Intermediate Similarity	NPC313444
0.7179	Intermediate Similarity	NPC276290
0.7176	Intermediate Similarity	NPC275507
0.7174	Intermediate Similarity	NPC470255
0.7174	Intermediate Similarity	NPC38830
0.7159	Intermediate Similarity	NPC471219
0.7159	Intermediate Similarity	NPC131813
0.7158	Intermediate Similarity	NPC54705
0.7143	Intermediate Similarity	NPC166110
0.7143	Intermediate Similarity	NPC150646
0.7143	Intermediate Similarity	NPC32944
0.7143	Intermediate Similarity	NPC193396
0.7143	Intermediate Similarity	NPC271632
0.7143	Intermediate Similarity	NPC116013
0.7143	Intermediate Similarity	NPC471299
0.7128	Intermediate Similarity	NPC53844
0.7128	Intermediate Similarity	NPC202705
0.7126	Intermediate Similarity	NPC149869
0.7126	Intermediate Similarity	NPC96055
0.7126	Intermediate Similarity	NPC471301
0.7111	Intermediate Similarity	NPC173042
0.7111	Intermediate Similarity	NPC280833
0.7111	Intermediate Similarity	NPC95364
0.7111	Intermediate Similarity	NPC142159
0.7111	Intermediate Similarity	NPC470734
0.7108	Intermediate Similarity	NPC316500
0.7108	Intermediate Similarity	NPC57744
0.7105	Intermediate Similarity	NPC226066
0.7093	Intermediate Similarity	NPC324170
0.7089	Intermediate Similarity	NPC473603
0.7089	Intermediate Similarity	NPC476059
0.7083	Intermediate Similarity	NPC469657
0.7083	Intermediate Similarity	NPC244456
0.7083	Intermediate Similarity	NPC168319
0.7083	Intermediate Similarity	NPC194028
0.7079	Intermediate Similarity	NPC478145
0.7079	Intermediate Similarity	NPC478144
0.7079	Intermediate Similarity	NPC312561
0.7073	Intermediate Similarity	NPC228978
0.7073	Intermediate Similarity	NPC68624
0.7073	Intermediate Similarity	NPC329852
0.7065	Intermediate Similarity	NPC282644
0.7065	Intermediate Similarity	NPC29798
0.7065	Intermediate Similarity	NPC475657
0.7065	Intermediate Similarity	NPC248193
0.7059	Intermediate Similarity	NPC160582
0.7053	Intermediate Similarity	NPC474440
0.7053	Intermediate Similarity	NPC278673
0.7053	Intermediate Similarity	NPC92275
0.7051	Intermediate Similarity	NPC203335
0.7045	Intermediate Similarity	NPC42586
0.7045	Intermediate Similarity	NPC471795
0.7045	Intermediate Similarity	NPC106416
0.7045	Intermediate Similarity	NPC473251
0.7045	Intermediate Similarity	NPC177932
0.7045	Intermediate Similarity	NPC130030
0.7045	Intermediate Similarity	NPC86316
0.7037	Intermediate Similarity	NPC476489
0.7037	Intermediate Similarity	NPC287878
0.7037	Intermediate Similarity	NPC476490
0.7033	Intermediate Similarity	NPC273199
0.7033	Intermediate Similarity	NPC51486
0.7033	Intermediate Similarity	NPC232426
0.7033	Intermediate Similarity	NPC281942
0.7024	Intermediate Similarity	NPC128276
0.7024	Intermediate Similarity	NPC209135
0.7024	Intermediate Similarity	NPC474816
0.7021	Intermediate Similarity	NPC190713
0.7021	Intermediate Similarity	NPC112654
0.7013	Intermediate Similarity	NPC471565
0.7013	Intermediate Similarity	NPC471566
0.7011	Intermediate Similarity	NPC22611
0.7011	Intermediate Similarity	NPC472377
0.7011	Intermediate Similarity	NPC475714
0.7011	Intermediate Similarity	NPC30502
0.701	Intermediate Similarity	NPC235369
0.7	Intermediate Similarity	NPC473879
0.7	Intermediate Similarity	NPC24816
0.7	Intermediate Similarity	NPC477128
0.7	Intermediate Similarity	NPC106332
0.7	Intermediate Similarity	NPC315597
0.7	Intermediate Similarity	NPC472378
0.7	Intermediate Similarity	NPC260343
0.7	Intermediate Similarity	NPC472810
0.7	Intermediate Similarity	NPC472809
0.7	Intermediate Similarity	NPC93411
0.6989	Remote Similarity	NPC88507
0.6989	Remote Similarity	NPC143210
0.6989	Remote Similarity	NPC475572
0.6988	Remote Similarity	NPC123360
0.6988	Remote Similarity	NPC40353
0.6979	Remote Similarity	NPC290802
0.6979	Remote Similarity	NPC227865
0.6977	Remote Similarity	NPC325031
0.6977	Remote Similarity	NPC475944
0.6977	Remote Similarity	NPC282293
0.6974	Remote Similarity	NPC210303
0.6974	Remote Similarity	NPC179087
0.6974	Remote Similarity	NPC44343

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 NPC473825 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	164
0.1-0.2	1495
0.2-0.3	4215
0.3-0.4	2432
0.4-0.5	612
0.5-0.6	204
0.6-0.7	25
0.7-0.8	3
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
0.75	Intermediate Similarity	NPD5209	Approved
0.75	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5325	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD8039	Approved
0.7045	Intermediate Similarity	NPD1694	Approved
0.6795	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD5694	Approved
0.6559	Remote Similarity	NPD6051	Approved
0.6489	Remote Similarity	NPD5207	Approved
0.6489	Remote Similarity	NPD5692	Phase 3
0.6452	Remote Similarity	NPD6672	Approved
0.6452	Remote Similarity	NPD5737	Approved
0.6421	Remote Similarity	NPD7637	Suspended
0.6421	Remote Similarity	NPD5693	Phase 1
0.6421	Remote Similarity	NPD6411	Approved
0.6421	Remote Similarity	NPD6050	Approved
0.6413	Remote Similarity	NPD7521	Approved
0.6413	Remote Similarity	NPD7334	Approved
0.6413	Remote Similarity	NPD6409	Approved
0.6413	Remote Similarity	NPD7146	Approved
0.6413	Remote Similarity	NPD5330	Approved
0.6413	Remote Similarity	NPD6684	Approved
0.641	Remote Similarity	NPD4194	Approved
0.641	Remote Similarity	NPD4191	Approved
0.641	Remote Similarity	NPD4192	Approved
0.641	Remote Similarity	NPD4193	Approved
0.6364	Remote Similarity	NPD4225	Approved
0.6364	Remote Similarity	NPD7638	Approved
0.6354	Remote Similarity	NPD5778	Approved
0.6354	Remote Similarity	NPD5779	Approved
0.6316	Remote Similarity	NPD7838	Discovery
0.63	Remote Similarity	NPD7640	Approved
0.63	Remote Similarity	NPD7639	Approved
0.6277	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD6903	Approved
0.625	Remote Similarity	NPD5284	Approved
0.625	Remote Similarity	NPD5281	Approved
0.6224	Remote Similarity	NPD5695	Phase 3
0.6211	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD6101	Approved
0.6164	Remote Similarity	NPD6927	Phase 3
0.6146	Remote Similarity	NPD5785	Approved
0.6136	Remote Similarity	NPD4756	Discovery
0.6092	Remote Similarity	NPD8264	Approved
0.6087	Remote Similarity	NPD7154	Phase 3
0.6067	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD5279	Phase 3
0.6061	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD5654	Approved
0.6042	Remote Similarity	NPD6673	Approved
0.6042	Remote Similarity	NPD6080	Approved
0.6042	Remote Similarity	NPD6904	Approved
0.6042	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.604	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD6686	Approved
0.6	Remote Similarity	NPD3573	Approved
0.598	Remote Similarity	NPD6648	Approved
0.5977	Remote Similarity	NPD4687	Approved
0.5965	Remote Similarity	NPD7503	Approved
0.596	Remote Similarity	NPD7748	Approved
0.596	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.596	Remote Similarity	NPD7900	Approved
0.5957	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD6084	Phase 2
0.5941	Remote Similarity	NPD6083	Phase 2
0.5941	Remote Similarity	NPD5959	Approved
0.5938	Remote Similarity	NPD5208	Approved
0.5934	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.593	Remote Similarity	NPD5276	Approved
0.5914	Remote Similarity	NPD6110	Phase 1
0.59	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD4249	Approved
0.5882	Remote Similarity	NPD5696	Approved
0.5859	Remote Similarity	NPD6399	Phase 3
0.5833	Remote Similarity	NPD1282	Approved
0.5833	Remote Similarity	NPD4250	Approved
0.5833	Remote Similarity	NPD4251	Approved
0.5818	Remote Similarity	NPD6053	Discontinued
0.5816	Remote Similarity	NPD6698	Approved
0.5816	Remote Similarity	NPD46	Approved
0.58	Remote Similarity	NPD5282	Discontinued
0.5795	Remote Similarity	NPD4058	Approved
0.5795	Remote Similarity	NPD5733	Approved
0.5794	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD7902	Approved
0.578	Remote Similarity	NPD2067	Discontinued
0.5773	Remote Similarity	NPD4518	Approved
0.5761	Remote Similarity	NPD4695	Discontinued
0.5758	Remote Similarity	NPD7515	Phase 2
0.5755	Remote Similarity	NPD5909	Discontinued
0.5752	Remote Similarity	NPD7115	Discovery
0.5745	Remote Similarity	NPD6695	Phase 3
0.5745	Remote Similarity	NPD5362	Discontinued
0.5729	Remote Similarity	NPD4623	Approved
0.5729	Remote Similarity	NPD5280	Approved
0.5729	Remote Similarity	NPD4694	Approved
0.5729	Remote Similarity	NPD6098	Approved
0.5729	Remote Similarity	NPD4519	Discontinued
0.5728	Remote Similarity	NPD5926	Approved
0.5714	Remote Similarity	NPD4271	Approved
0.5714	Remote Similarity	NPD4268	Approved
0.5714	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7632	Discontinued
0.5696	Remote Similarity	NPD8779	Phase 3
0.5688	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5684	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5684	Remote Similarity	NPD3666	Approved
0.5684	Remote Similarity	NPD3133	Approved
0.5684	Remote Similarity	NPD3665	Phase 1
0.5679	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD4220	Pre-registration
0.5673	Remote Similarity	NPD6404	Discontinued
0.566	Remote Similarity	NPD6647	Phase 2
0.5656	Remote Similarity	NPD7260	Phase 2
0.5652	Remote Similarity	NPD4195	Approved
0.5648	Remote Similarity	NPD5697	Approved
0.5644	Remote Similarity	NPD6001	Approved
0.5636	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5632	Remote Similarity	NPD7144	Approved
0.5632	Remote Similarity	NPD7143	Approved
0.5625	Remote Similarity	NPD5363	Approved
0.5619	Remote Similarity	NPD5344	Discontinued
0.5618	Remote Similarity	NPD6924	Approved
0.5618	Remote Similarity	NPD6926	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