NPASS Compound

Structure

NPC471956 OpenBabel07101718332D 21 24 0 0 1 0 0 0 0 0999 V2000 3.9432 2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9271 4.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2764 -0.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6287 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6342 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5962 3.7281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2219 0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 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 3.6342 0.0000 0.0000 C 0 0 2 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 1 0 0 0 0 0 0 0 0 0 -2.5743 3.9360 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 -1.2872 2.7770 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 8 2 0 0 0 0 2 9 1 0 0 0 0 4 14 1 0 0 0 0 5 11 1 0 0 0 0 5 13 1 0 0 0 0 6 15 2 0 0 0 0 6 17 1 0 0 0 0 7 12 1 0 0 0 0 7 20 1 0 0 0 0 8 10 1 0 0 0 0 8 13 1 0 0 0 0 9 18 2 0 0 0 0 9 20 1 0 0 0 0 10 4 1 1 0 0 0 10 14 1 0 0 0 0 11 12 2 0 0 0 0 11 15 1 0 0 0 0 12 16 1 0 0 0 0 13 17 1 1 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 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.12
Volume:	290.341
LogP:	2.476
LogD:	2.593
LogS:	-2.889
# Rotatable Bonds:	3
TPSA:	59.67
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.66
Synthetic Accessibility Score:	5.104
Fsp3:	0.471
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:	-5.206
MDCK Permeability:	7.354018453042954e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.162
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.023
30% Bioavailability (F30%):	0.066

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.773
Plasma Protein Binding (PPB):	64.96521759033203%
Volume Distribution (VD):	1.68
Pgp-substrate:	46.82291793823242%

ADMET: Metabolism

CYP1A2-inhibitor:	0.685
CYP1A2-substrate:	0.394
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.278
CYP2C9-inhibitor:	0.045
CYP2C9-substrate:	0.124
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.132
CYP3A4-inhibitor:	0.347
CYP3A4-substrate:	0.244

ADMET: Excretion

Clearance (CL):	8.41
Half-life (T1/2):	0.631

ADMET: Toxicity

hERG Blockers:	0.085
Human Hepatotoxicity (H-HT):	0.673
Drug-inuced Liver Injury (DILI):	0.637
AMES Toxicity:	0.717
Rat Oral Acute Toxicity:	0.96
Maximum Recommended Daily Dose:	0.868
Skin Sensitization:	0.474
Carcinogencity:	0.942
Eye Corrosion:	0.029
Eye Irritation:	0.024
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC471956

Natural Product ID:	NPC471956
*Common Name:**	UMDGLGBILDVFOU-KEAXFYSCSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	UMDGLGBILDVFOU-KEAXFYSCSA-N
Standard InCHI:	InChI=1S/C17H18O4/c1-8-10-4-14(10)17(3)6-15-11(5-13(8)17)12(16(19)21-15)7-20-9(2)18/h6,10,13-14H,1,4-5,7H2,2-3H3/t10-,13+,14-,17-/m1/s1
SMILES:	CC(=O)OCC1=C2C[C@H]3C(=C)[C@@H]4[C@H]([C@@]3(C=C2OC1=O)C)C4
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3314202
PubChem CID:	n.a.
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
NPO3657.1	Hyalis argentea	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[25026191]

☑ 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	6

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20	Organism	Candida albicans	Candida albicans	GI	=	50.0	%	PMID[538511]
NPT20	Organism	Candida albicans	Candida albicans	GI	=	80.0	%	PMID[538511]
NPT20	Organism	Candida albicans	Candida albicans	GI	=	100.0	%	PMID[538511]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	GI	=	50.0	%	PMID[538511]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	GI	=	80.0	%	PMID[538511]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	GI	=	100.0	%	PMID[538511]

☑ 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 NPC471956 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	213
0.1-0.2	1328
0.2-0.3	5333
0.3-0.4	15413
0.4-0.5	10741
0.5-0.6	6847
0.6-0.7	2668
0.7-0.8	144
0.8-0.85	3
0.85-0.9	1
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9195	High Similarity	NPC2882
0.8667	High Similarity	NPC472954
0.8214	Intermediate Similarity	NPC54996
0.8	Intermediate Similarity	NPC473825
0.7912	Intermediate Similarity	NPC125925
0.7865	Intermediate Similarity	NPC12283
0.7865	Intermediate Similarity	NPC474193
0.7835	Intermediate Similarity	NPC181147
0.7826	Intermediate Similarity	NPC472302
0.7766	Intermediate Similarity	NPC472953
0.7727	Intermediate Similarity	NPC268827
0.7717	Intermediate Similarity	NPC45957
0.7717	Intermediate Similarity	NPC471657
0.7667	Intermediate Similarity	NPC30502
0.7624	Intermediate Similarity	NPC472822
0.7604	Intermediate Similarity	NPC166143
0.7604	Intermediate Similarity	NPC471994
0.7604	Intermediate Similarity	NPC120351
0.759	Intermediate Similarity	NPC232812
0.7582	Intermediate Similarity	NPC475100
0.7579	Intermediate Similarity	NPC472705
0.7553	Intermediate Similarity	NPC177141
0.7553	Intermediate Similarity	NPC64913
0.7553	Intermediate Similarity	NPC242877
0.7551	Intermediate Similarity	NPC53844
0.7529	Intermediate Similarity	NPC222244
0.7529	Intermediate Similarity	NPC16349
0.7527	Intermediate Similarity	NPC476600
0.75	Intermediate Similarity	NPC471185
0.75	Intermediate Similarity	NPC474005
0.75	Intermediate Similarity	NPC471220
0.75	Intermediate Similarity	NPC189311
0.75	Intermediate Similarity	NPC64234
0.75	Intermediate Similarity	NPC37929
0.75	Intermediate Similarity	NPC184737
0.7473	Intermediate Similarity	NPC193198
0.7473	Intermediate Similarity	NPC321385
0.7451	Intermediate Similarity	NPC121099
0.7451	Intermediate Similarity	NPC200861
0.7449	Intermediate Similarity	NPC260796
0.7449	Intermediate Similarity	NPC16967
0.7447	Intermediate Similarity	NPC260343
0.7447	Intermediate Similarity	NPC226863
0.7423	Intermediate Similarity	NPC191521
0.7412	Intermediate Similarity	NPC181587
0.7404	Intermediate Similarity	NPC220155
0.74	Intermediate Similarity	NPC227865
0.7396	Intermediate Similarity	NPC32494
0.7396	Intermediate Similarity	NPC175842
0.7391	Intermediate Similarity	NPC474693
0.7386	Intermediate Similarity	NPC189206
0.7379	Intermediate Similarity	NPC81630
0.7374	Intermediate Similarity	NPC202705
0.7374	Intermediate Similarity	NPC47834
0.7374	Intermediate Similarity	NPC2049
0.7363	Intermediate Similarity	NPC471218
0.7363	Intermediate Similarity	NPC200513
0.7347	Intermediate Similarity	NPC295347
0.7347	Intermediate Similarity	NPC474909
0.7347	Intermediate Similarity	NPC209355
0.7347	Intermediate Similarity	NPC33473
0.7333	Intermediate Similarity	NPC472470
0.7327	Intermediate Similarity	NPC475099
0.732	Intermediate Similarity	NPC152778
0.732	Intermediate Similarity	NPC59646
0.732	Intermediate Similarity	NPC162615
0.732	Intermediate Similarity	NPC205034
0.732	Intermediate Similarity	NPC115021
0.7315	Intermediate Similarity	NPC106446
0.7312	Intermediate Similarity	NPC475860
0.7312	Intermediate Similarity	NPC473659
0.7312	Intermediate Similarity	NPC474694
0.7312	Intermediate Similarity	NPC472442
0.7303	Intermediate Similarity	NPC253749
0.7292	Intermediate Similarity	NPC220454
0.7292	Intermediate Similarity	NPC3436
0.7292	Intermediate Similarity	NPC273199
0.7292	Intermediate Similarity	NPC280149
0.7292	Intermediate Similarity	NPC51486
0.7292	Intermediate Similarity	NPC221111
0.7292	Intermediate Similarity	NPC469595
0.7292	Intermediate Similarity	NPC212679
0.7283	Intermediate Similarity	NPC311070
0.7283	Intermediate Similarity	NPC477124
0.7283	Intermediate Similarity	NPC472377
0.7283	Intermediate Similarity	NPC474809
0.7283	Intermediate Similarity	NPC472440
0.7273	Intermediate Similarity	NPC9812
0.7273	Intermediate Similarity	NPC476317
0.7263	Intermediate Similarity	NPC472378
0.7263	Intermediate Similarity	NPC93411
0.7253	Intermediate Similarity	NPC59994
0.7253	Intermediate Similarity	NPC475944
0.7253	Intermediate Similarity	NPC78677
0.7253	Intermediate Similarity	NPC282293
0.7245	Intermediate Similarity	NPC470521
0.7245	Intermediate Similarity	NPC124207
0.7245	Intermediate Similarity	NPC53685
0.7234	Intermediate Similarity	NPC474045
0.7234	Intermediate Similarity	NPC131813
0.7234	Intermediate Similarity	NPC261253
0.7228	Intermediate Similarity	NPC469872
0.7228	Intermediate Similarity	NPC469864
0.7228	Intermediate Similarity	NPC54705
0.7222	Intermediate Similarity	NPC471299
0.7222	Intermediate Similarity	NPC150646
0.7222	Intermediate Similarity	NPC170561
0.7216	Intermediate Similarity	NPC177037
0.7216	Intermediate Similarity	NPC478244
0.7216	Intermediate Similarity	NPC478243
0.7216	Intermediate Similarity	NPC470520
0.7216	Intermediate Similarity	NPC166110
0.7216	Intermediate Similarity	NPC472814
0.7212	Intermediate Similarity	NPC127790
0.7209	Intermediate Similarity	NPC257618
0.7209	Intermediate Similarity	NPC5734
0.7204	Intermediate Similarity	NPC318515
0.7204	Intermediate Similarity	NPC96055
0.7204	Intermediate Similarity	NPC149869
0.72	Intermediate Similarity	NPC110937
0.72	Intermediate Similarity	NPC477949
0.72	Intermediate Similarity	NPC208094
0.7191	Intermediate Similarity	NPC315394
0.7188	Intermediate Similarity	NPC470734
0.7188	Intermediate Similarity	NPC225283
0.7188	Intermediate Similarity	NPC284561
0.7188	Intermediate Similarity	NPC288699
0.7188	Intermediate Similarity	NPC5509
0.7184	Intermediate Similarity	NPC475526
0.7184	Intermediate Similarity	NPC473283
0.7184	Intermediate Similarity	NPC329345
0.7174	Intermediate Similarity	NPC35556
0.7172	Intermediate Similarity	NPC281134
0.7172	Intermediate Similarity	NPC293052
0.7158	Intermediate Similarity	NPC478144
0.7158	Intermediate Similarity	NPC191283
0.7158	Intermediate Similarity	NPC312561
0.7158	Intermediate Similarity	NPC478145
0.7157	Intermediate Similarity	NPC298233
0.7157	Intermediate Similarity	NPC168319
0.7157	Intermediate Similarity	NPC477950
0.7157	Intermediate Similarity	NPC194028
0.7157	Intermediate Similarity	NPC116139
0.7143	Intermediate Similarity	NPC476598
0.7143	Intermediate Similarity	NPC475657
0.7143	Intermediate Similarity	NPC248193
0.7143	Intermediate Similarity	NPC476958
0.7143	Intermediate Similarity	NPC472266
0.7143	Intermediate Similarity	NPC1108
0.7143	Intermediate Similarity	NPC476597
0.7129	Intermediate Similarity	NPC98868
0.7129	Intermediate Similarity	NPC244411
0.7129	Intermediate Similarity	NPC278673
0.7129	Intermediate Similarity	NPC64742
0.7129	Intermediate Similarity	NPC92275
0.7129	Intermediate Similarity	NPC252295
0.7128	Intermediate Similarity	NPC474013
0.7128	Intermediate Similarity	NPC65661
0.7128	Intermediate Similarity	NPC30984
0.7115	Intermediate Similarity	NPC165969
0.7115	Intermediate Similarity	NPC309190
0.7115	Intermediate Similarity	NPC161775
0.7113	Intermediate Similarity	NPC8062
0.7113	Intermediate Similarity	NPC310479
0.7113	Intermediate Similarity	NPC161638
0.7113	Intermediate Similarity	NPC469372
0.7113	Intermediate Similarity	NPC182136
0.7113	Intermediate Similarity	NPC281942
0.7113	Intermediate Similarity	NPC302280
0.7113	Intermediate Similarity	NPC232426
0.7111	Intermediate Similarity	NPC209135
0.7111	Intermediate Similarity	NPC474816
0.71	Intermediate Similarity	NPC114743
0.71	Intermediate Similarity	NPC195366
0.71	Intermediate Similarity	NPC190713
0.71	Intermediate Similarity	NPC242848
0.71	Intermediate Similarity	NPC307164
0.7097	Intermediate Similarity	NPC475989
0.7097	Intermediate Similarity	NPC475947
0.7093	Intermediate Similarity	NPC469660
0.7093	Intermediate Similarity	NPC316029
0.7087	Intermediate Similarity	NPC471993
0.7087	Intermediate Similarity	NPC66110
0.7083	Intermediate Similarity	NPC473879
0.7083	Intermediate Similarity	NPC472809
0.7083	Intermediate Similarity	NPC472810
0.7079	Intermediate Similarity	NPC27205
0.7079	Intermediate Similarity	NPC4509
0.7071	Intermediate Similarity	NPC473280
0.7071	Intermediate Similarity	NPC477130
0.7071	Intermediate Similarity	NPC38830
0.7071	Intermediate Similarity	NPC471078
0.7071	Intermediate Similarity	NPC281775
0.7071	Intermediate Similarity	NPC477129
0.7071	Intermediate Similarity	NPC476596
0.7071	Intermediate Similarity	NPC473431
0.7071	Intermediate Similarity	NPC84893
0.7071	Intermediate Similarity	NPC470697
0.7071	Intermediate Similarity	NPC477241
0.7071	Intermediate Similarity	NPC161998

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 NPC471956 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	176
0.1-0.2	1699
0.2-0.3	4108
0.3-0.4	2313
0.4-0.5	526
0.5-0.6	263
0.6-0.7	64
0.7-0.8	1
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
0.7556	Intermediate Similarity	NPD5209	Approved
0.7363	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7637	Suspended
0.701	Intermediate Similarity	NPD6051	Approved
0.6966	Remote Similarity	NPD8039	Approved
0.6907	Remote Similarity	NPD5737	Approved
0.6907	Remote Similarity	NPD6672	Approved
0.6869	Remote Similarity	NPD5693	Phase 1
0.6832	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD4225	Approved
0.6786	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD5692	Phase 3
0.6768	Remote Similarity	NPD5207	Approved
0.6735	Remote Similarity	NPD6903	Approved
0.6706	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD6684	Approved
0.6701	Remote Similarity	NPD7521	Approved
0.6701	Remote Similarity	NPD7334	Approved
0.6701	Remote Similarity	NPD6409	Approved
0.6701	Remote Similarity	NPD7146	Approved
0.6701	Remote Similarity	NPD5330	Approved
0.67	Remote Similarity	NPD6050	Approved
0.67	Remote Similarity	NPD5694	Approved
0.6667	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD7638	Approved
0.66	Remote Similarity	NPD5785	Approved
0.6598	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD1694	Approved
0.6579	Remote Similarity	NPD7115	Discovery
0.6571	Remote Similarity	NPD7639	Approved
0.6571	Remote Similarity	NPD7640	Approved
0.6569	Remote Similarity	NPD6001	Approved
0.6566	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6083	Phase 2
0.6538	Remote Similarity	NPD6084	Phase 2
0.6538	Remote Similarity	NPD5959	Approved
0.6535	Remote Similarity	NPD6411	Approved
0.6518	Remote Similarity	NPD6053	Discontinued
0.6505	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6673	Approved
0.65	Remote Similarity	NPD6904	Approved
0.65	Remote Similarity	NPD6080	Approved
0.6476	Remote Similarity	NPD5696	Approved
0.6471	Remote Similarity	NPD5778	Approved
0.6471	Remote Similarity	NPD5779	Approved
0.6436	Remote Similarity	NPD7838	Discovery
0.64	Remote Similarity	NPD5208	Approved
0.6392	Remote Similarity	NPD6695	Phase 3
0.6373	Remote Similarity	NPD5284	Approved
0.6373	Remote Similarity	NPD5281	Approved
0.6364	Remote Similarity	NPD5279	Phase 3
0.6356	Remote Similarity	NPD7503	Approved
0.6346	Remote Similarity	NPD5654	Approved
0.6339	Remote Similarity	NPD6371	Approved
0.6337	Remote Similarity	NPD6101	Approved
0.6337	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD1695	Approved
0.6327	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD6399	Phase 3
0.6273	Remote Similarity	NPD6008	Approved
0.6262	Remote Similarity	NPD6648	Approved
0.625	Remote Similarity	NPD5282	Discontinued
0.6224	Remote Similarity	NPD5362	Discontinued
0.6224	Remote Similarity	NPD7154	Phase 3
0.6211	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.62	Remote Similarity	NPD4249	Approved
0.62	Remote Similarity	NPD6098	Approved
0.6186	Remote Similarity	NPD6902	Approved
0.6176	Remote Similarity	NPD4753	Phase 2
0.6163	Remote Similarity	NPD4194	Approved
0.6163	Remote Similarity	NPD4192	Approved
0.6163	Remote Similarity	NPD4191	Approved
0.6163	Remote Similarity	NPD4193	Approved
0.6161	Remote Similarity	NPD7320	Approved
0.6161	Remote Similarity	NPD6686	Approved
0.6146	Remote Similarity	NPD6929	Approved
0.6139	Remote Similarity	NPD7750	Discontinued
0.6139	Remote Similarity	NPD7524	Approved
0.6139	Remote Similarity	NPD4250	Approved
0.6139	Remote Similarity	NPD4251	Approved
0.6129	Remote Similarity	NPD6924	Approved
0.6129	Remote Similarity	NPD6926	Approved
0.6126	Remote Similarity	NPD5739	Approved
0.6126	Remote Similarity	NPD7128	Approved
0.6126	Remote Similarity	NPD6402	Approved
0.6126	Remote Similarity	NPD6675	Approved
0.6117	Remote Similarity	NPD6698	Approved
0.6117	Remote Similarity	NPD46	Approved
0.6102	Remote Similarity	NPD7327	Approved
0.6102	Remote Similarity	NPD7328	Approved
0.61	Remote Similarity	NPD5363	Approved
0.6087	Remote Similarity	NPD5276	Approved
0.6082	Remote Similarity	NPD6931	Approved
0.6082	Remote Similarity	NPD6930	Phase 2
0.6082	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD5697	Approved
0.6071	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD5701	Approved
0.6061	Remote Similarity	NPD5331	Approved
0.6061	Remote Similarity	NPD5332	Approved
0.605	Remote Similarity	NPD7516	Approved
0.604	Remote Similarity	NPD5280	Approved
0.604	Remote Similarity	NPD4694	Approved
0.602	Remote Similarity	NPD4790	Discontinued
0.6018	Remote Similarity	NPD6899	Approved
0.6018	Remote Similarity	NPD6881	Approved
0.6	Remote Similarity	NPD8294	Approved
0.6	Remote Similarity	NPD3665	Phase 1
0.6	Remote Similarity	NPD3666	Approved
0.6	Remote Similarity	NPD7319	Approved
0.6	Remote Similarity	NPD3133	Approved
0.6	Remote Similarity	NPD6933	Approved
0.6	Remote Similarity	NPD7632	Discontinued
0.6	Remote Similarity	NPD8377	Approved
0.5979	Remote Similarity	NPD4195	Approved
0.5965	Remote Similarity	NPD6373	Approved
0.5965	Remote Similarity	NPD6013	Approved
0.5965	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD6372	Approved
0.5965	Remote Similarity	NPD6014	Approved
0.5965	Remote Similarity	NPD6012	Approved
0.5963	Remote Similarity	NPD6404	Discontinued
0.596	Remote Similarity	NPD4221	Approved
0.596	Remote Similarity	NPD4223	Phase 3
0.596	Remote Similarity	NPD4270	Approved
0.596	Remote Similarity	NPD4269	Approved
0.5957	Remote Similarity	NPD5733	Approved
0.5957	Remote Similarity	NPD4687	Approved
0.595	Remote Similarity	NPD8033	Approved
0.595	Remote Similarity	NPD8335	Approved
0.595	Remote Similarity	NPD8378	Approved
0.595	Remote Similarity	NPD8379	Approved
0.595	Remote Similarity	NPD8296	Approved
0.595	Remote Similarity	NPD8380	Approved
0.5946	Remote Similarity	NPD6052	Approved
0.5943	Remote Similarity	NPD7900	Approved
0.5943	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD7748	Approved
0.5941	Remote Similarity	NPD1696	Phase 3
0.5938	Remote Similarity	NPD5776	Phase 2
0.5938	Remote Similarity	NPD4756	Discovery
0.5938	Remote Similarity	NPD6925	Approved
0.5922	Remote Similarity	NPD4518	Approved
0.5918	Remote Similarity	NPD4821	Approved
0.5918	Remote Similarity	NPD4820	Approved
0.5918	Remote Similarity	NPD4819	Approved
0.5918	Remote Similarity	NPD4822	Approved
0.5918	Remote Similarity	NPD7514	Phase 3
0.5913	Remote Similarity	NPD6883	Approved
0.5913	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD7102	Approved
0.5913	Remote Similarity	NPD7290	Approved
0.5909	Remote Similarity	NPD5344	Discontinued
0.5905	Remote Similarity	NPD7087	Discontinued
0.5888	Remote Similarity	NPD4629	Approved
0.5888	Remote Similarity	NPD5210	Approved
0.5887	Remote Similarity	NPD7507	Approved
0.5882	Remote Similarity	NPD5786	Approved
0.5882	Remote Similarity	NPD3618	Phase 1
0.5882	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD6011	Approved
0.5876	Remote Similarity	NPD4268	Approved
0.5876	Remote Similarity	NPD4271	Approved
0.5876	Remote Similarity	NPD7145	Approved
0.587	Remote Similarity	NPD6922	Approved
0.587	Remote Similarity	NPD6923	Approved
0.5865	Remote Similarity	NPD5328	Approved
0.5865	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD6650	Approved
0.5862	Remote Similarity	NPD8130	Phase 1
0.5862	Remote Similarity	NPD6617	Approved
0.5862	Remote Similarity	NPD6847	Approved
0.5862	Remote Similarity	NPD6649	Approved
0.5862	Remote Similarity	NPD6869	Approved
0.5859	Remote Similarity	NPD5369	Approved
0.5849	Remote Similarity	NPD5133	Approved
0.5842	Remote Similarity	NPD4786	Approved
0.5842	Remote Similarity	NPD4197	Approved
0.5842	Remote Similarity	NPD3668	Phase 3
0.5825	Remote Similarity	NPD3573	Approved
0.5812	Remote Similarity	NPD6882	Approved
0.5812	Remote Similarity	NPD8297	Approved
0.581	Remote Similarity	NPD4096	Approved
0.5806	Remote Similarity	NPD7144	Approved
0.5806	Remote Similarity	NPD4747	Approved
0.5806	Remote Similarity	NPD7143	Approved
0.58	Remote Similarity	NPD3667	Approved
0.58	Remote Similarity	NPD6435	Approved
0.5789	Remote Similarity	NPD4058	Approved
0.5784	Remote Similarity	NPD6893	Approved
0.5784	Remote Similarity	NPD5329	Approved
0.5784	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.578	Remote Similarity	NPD4755	Approved
0.578	Remote Similarity	NPD7902	Approved
0.5773	Remote Similarity	NPD6932	Approved
0.5758	Remote Similarity	NPD7332	Phase 2
0.5758	Remote Similarity	NPD4695	Discontinued
0.5758	Remote Similarity	NPD4252	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