NPASS Compound

Structure

CID187268 OpenBabel06191715562D 27 29 0 0 1 0 0 0 0 0999 V2000 -0.9499 -4.2541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6269 -3.6542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4158 1.9563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5058 -1.8035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1754 -1.5709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0446 -4.3587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6092 -0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6324 -3.5497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 0.1045 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4013 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2257 -2.6361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8605 -0.3955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 -0.6691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4067 0.9135 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0704 1.5522 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7688 -2.5316 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8387 -0.6034 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4349 1.9131 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8135 -1.8271 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 6 1 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 12 2 0 0 0 0 6 10 2 0 0 0 0 7 11 2 0 0 0 0 8 14 1 0 0 0 0 8 19 1 0 0 0 0 9 15 1 0 0 0 0 9 19 1 0 0 0 0 10 17 1 0 0 0 0 11 20 1 0 0 0 0 12 18 1 0 0 0 0 13 7 1 1 0 0 0 13 16 1 0 0 0 0 13 25 1 0 0 0 0 14 16 1 0 0 0 0 14 26 1 6 0 0 0 15 20 1 6 0 0 0 15 21 1 0 0 0 0 16 12 1 6 0 0 0 17 22 2 0 0 0 0 17 26 1 0 0 0 0 18 23 2 0 0 0 0 18 25 1 0 0 0 0 19 5 1 1 0 0 0 19 27 1 0 0 0 0 20 24 1 1 0 0 0 20 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	378.17
Volume:	377.156
LogP:	1.053
LogD:	0.954
LogS:	-2.532
# Rotatable Bonds:	3
TPSA:	102.29
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.427
Synthetic Accessibility Score:	6.115
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.884
MDCK Permeability:	4.670449925470166e-05
Pgp-inhibitor:	0.107
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.066
20% Bioavailability (F20%):	0.817
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.418
Plasma Protein Binding (PPB):	72.7315673828125%
Volume Distribution (VD):	1.848
Pgp-substrate:	20.906953811645508%

ADMET: Metabolism

CYP1A2-inhibitor:	0.047
CYP1A2-substrate:	0.514
CYP2C19-inhibitor:	0.152
CYP2C19-substrate:	0.825
CYP2C9-inhibitor:	0.246
CYP2C9-substrate:	0.022
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.058
CYP3A4-inhibitor:	0.707
CYP3A4-substrate:	0.457

ADMET: Excretion

Clearance (CL):	7.015
Half-life (T1/2):	0.709

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.581
Drug-inuced Liver Injury (DILI):	0.766
AMES Toxicity:	0.052
Rat Oral Acute Toxicity:	0.732
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.313
Carcinogencity:	0.181
Eye Corrosion:	0.004
Eye Irritation:	0.017
Respiratory Toxicity:	0.944

Download Data

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

Natural Product: NPC187268

Natural Product ID:	NPC187268
*Common Name:**	2Beta-Hydroxy-1-Desoxyniveusin A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YSKMZKDBKXBPFM-HCGNKCLASA-N
Standard InCHI:	InChI=1S/C20H26O7/c1-6-10(2)17(22)26-14-8-19(5)9-15(21)20(24,27-19)11(3)7-13-16(14)12(4)18(23)25-13/h6-7,13-16,21,24H,4,8-9H2,1-3,5H3/b10-6-,11-7-/t13-,14-,15+,16+,19-,20+/m1/s1
SMILES:	C/C=C(C(=O)O[C@@H]1C[C@]2(C)C[C@@H]([C@@](O2)(/C(=C[C@@H]2[C@@H]1C(=C)C(=O)O2)/C)O)O)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL377489
PubChem CID:	44409581
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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
NPO7824	Ticorea pedicellata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
Others	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT721	Individual Protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	IC100	=	50.0	uM	PMID[510264]

☑ 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 NPC187268 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	226
0.1-0.2	1213
0.2-0.3	4614
0.3-0.4	9073
0.4-0.5	14231
0.5-0.6	7739
0.6-0.7	4278
0.7-0.8	1100
0.8-0.85	189
0.85-0.9	29
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.956	High Similarity	NPC474338
0.9032	High Similarity	NPC475912
0.9032	High Similarity	NPC81419
0.9032	High Similarity	NPC179746
0.9022	High Similarity	NPC474323
0.9022	High Similarity	NPC206614
0.8925	High Similarity	NPC208886
0.8925	High Similarity	NPC12172
0.8913	High Similarity	NPC473564
0.8878	High Similarity	NPC86077
0.8854	High Similarity	NPC471462
0.8842	High Similarity	NPC36954
0.8842	High Similarity	NPC14961
0.8842	High Similarity	NPC270013
0.875	High Similarity	NPC279621
0.8737	High Similarity	NPC81386
0.8737	High Similarity	NPC474035
0.8723	High Similarity	NPC184463
0.8723	High Similarity	NPC30515
0.8646	High Similarity	NPC471141
0.8646	High Similarity	NPC304886
0.8632	High Similarity	NPC476300
0.8632	High Similarity	NPC212486
0.8632	High Similarity	NPC125674
0.8632	High Similarity	NPC228451
0.8632	High Similarity	NPC475838
0.8617	High Similarity	NPC474761
0.8617	High Similarity	NPC476004
0.8617	High Similarity	NPC475855
0.8617	High Similarity	NPC51004
0.8602	High Similarity	NPC202672
0.8587	High Similarity	NPC162071
0.8586	High Similarity	NPC150923
0.8586	High Similarity	NPC473332
0.8571	High Similarity	NPC473326
0.8557	High Similarity	NPC476315
0.8542	High Similarity	NPC474247
0.8526	High Similarity	NPC473321
0.8515	High Similarity	NPC100487
0.8511	High Similarity	NPC295312
0.8511	High Similarity	NPC307411
0.85	High Similarity	NPC303653
0.85	High Similarity	NPC140591
0.85	High Similarity	NPC197835
0.85	High Similarity	NPC189609
0.85	High Similarity	NPC291500
0.8495	Intermediate Similarity	NPC160138
0.8495	Intermediate Similarity	NPC186148
0.8485	Intermediate Similarity	NPC288876
0.8438	Intermediate Similarity	NPC273579
0.8438	Intermediate Similarity	NPC295204
0.8438	Intermediate Similarity	NPC162205
0.8438	Intermediate Similarity	NPC288240
0.8431	Intermediate Similarity	NPC243998
0.8421	Intermediate Similarity	NPC473619
0.8421	Intermediate Similarity	NPC144133
0.8421	Intermediate Similarity	NPC473904
0.8421	Intermediate Similarity	NPC80875
0.8421	Intermediate Similarity	NPC473448
0.8421	Intermediate Similarity	NPC179394
0.8404	Intermediate Similarity	NPC177629
0.8404	Intermediate Similarity	NPC58219
0.84	Intermediate Similarity	NPC110443
0.84	Intermediate Similarity	NPC133907
0.84	Intermediate Similarity	NPC46998
0.84	Intermediate Similarity	NPC185141
0.84	Intermediate Similarity	NPC128733
0.8387	Intermediate Similarity	NPC475461
0.8387	Intermediate Similarity	NPC305475
0.8384	Intermediate Similarity	NPC474213
0.8367	Intermediate Similarity	NPC230800
0.8367	Intermediate Similarity	NPC473333
0.8365	Intermediate Similarity	NPC38154
0.8351	Intermediate Similarity	NPC71589
0.8351	Intermediate Similarity	NPC303942
0.8351	Intermediate Similarity	NPC477131
0.8351	Intermediate Similarity	NPC57405
0.8333	Intermediate Similarity	NPC474917
0.8316	Intermediate Similarity	NPC474032
0.8316	Intermediate Similarity	NPC92974
0.8316	Intermediate Similarity	NPC139418
0.83	Intermediate Similarity	NPC70865
0.8283	Intermediate Similarity	NPC2666
0.8283	Intermediate Similarity	NPC471490
0.828	Intermediate Similarity	NPC255307
0.828	Intermediate Similarity	NPC21469
0.8269	Intermediate Similarity	NPC475960
0.8265	Intermediate Similarity	NPC471142
0.8261	Intermediate Similarity	NPC250315
0.8252	Intermediate Similarity	NPC223450
0.8247	Intermediate Similarity	NPC469645
0.8247	Intermediate Similarity	NPC469692
0.8235	Intermediate Similarity	NPC475945
0.8235	Intermediate Similarity	NPC475871
0.8235	Intermediate Similarity	NPC124881
0.8229	Intermediate Similarity	NPC239517
0.8218	Intermediate Similarity	NPC164598
0.8218	Intermediate Similarity	NPC474339
0.8218	Intermediate Similarity	NPC476270
0.8211	Intermediate Similarity	NPC81045
0.8211	Intermediate Similarity	NPC40376
0.8211	Intermediate Similarity	NPC234077
0.8211	Intermediate Similarity	NPC153805
0.8211	Intermediate Similarity	NPC274446
0.8211	Intermediate Similarity	NPC133730
0.8211	Intermediate Similarity	NPC169511
0.8211	Intermediate Similarity	NPC473715
0.8211	Intermediate Similarity	NPC61257
0.8211	Intermediate Similarity	NPC287164
0.8211	Intermediate Similarity	NPC233551
0.8211	Intermediate Similarity	NPC242364
0.8211	Intermediate Similarity	NPC172821
0.8211	Intermediate Similarity	NPC100454
0.8211	Intermediate Similarity	NPC21208
0.8211	Intermediate Similarity	NPC320569
0.8211	Intermediate Similarity	NPC191929
0.8211	Intermediate Similarity	NPC280621
0.8211	Intermediate Similarity	NPC20339
0.8211	Intermediate Similarity	NPC39754
0.8211	Intermediate Similarity	NPC171135
0.8211	Intermediate Similarity	NPC151403
0.8211	Intermediate Similarity	NPC261952
0.8211	Intermediate Similarity	NPC48338
0.82	Intermediate Similarity	NPC471144
0.8191	Intermediate Similarity	NPC114694
0.8191	Intermediate Similarity	NPC475581
0.8191	Intermediate Similarity	NPC240695
0.8191	Intermediate Similarity	NPC231096
0.8191	Intermediate Similarity	NPC171174
0.8191	Intermediate Similarity	NPC232555
0.8191	Intermediate Similarity	NPC142117
0.8191	Intermediate Similarity	NPC107717
0.8191	Intermediate Similarity	NPC62118
0.8182	Intermediate Similarity	NPC477921
0.8182	Intermediate Similarity	NPC473859
0.8182	Intermediate Similarity	NPC306041
0.8172	Intermediate Similarity	NPC191476
0.8172	Intermediate Similarity	NPC114979
0.8163	Intermediate Similarity	NPC121825
0.8163	Intermediate Similarity	NPC198853
0.8163	Intermediate Similarity	NPC262133
0.8163	Intermediate Similarity	NPC473316
0.8163	Intermediate Similarity	NPC323008
0.8163	Intermediate Similarity	NPC473330
0.8163	Intermediate Similarity	NPC470010
0.8163	Intermediate Similarity	NPC470013
0.8155	Intermediate Similarity	NPC203659
0.8144	Intermediate Similarity	NPC470373
0.8144	Intermediate Similarity	NPC475925
0.8144	Intermediate Similarity	NPC133698
0.8144	Intermediate Similarity	NPC470379
0.8144	Intermediate Similarity	NPC131209
0.8137	Intermediate Similarity	NPC471148
0.8137	Intermediate Similarity	NPC474747
0.8137	Intermediate Similarity	NPC149371
0.8125	Intermediate Similarity	NPC93794
0.8125	Intermediate Similarity	NPC20621
0.8125	Intermediate Similarity	NPC81778
0.8125	Intermediate Similarity	NPC42598
0.8125	Intermediate Similarity	NPC318963
0.8125	Intermediate Similarity	NPC91067
0.8125	Intermediate Similarity	NPC473504
0.8125	Intermediate Similarity	NPC40066
0.8119	Intermediate Similarity	NPC475053
0.8113	Intermediate Similarity	NPC235014
0.8105	Intermediate Similarity	NPC231889
0.8105	Intermediate Similarity	NPC178215
0.81	Intermediate Similarity	NPC161493
0.81	Intermediate Similarity	NPC40812
0.8085	Intermediate Similarity	NPC1083
0.8085	Intermediate Similarity	NPC120398
0.8085	Intermediate Similarity	NPC215364
0.8085	Intermediate Similarity	NPC231009
0.8085	Intermediate Similarity	NPC103284
0.8085	Intermediate Similarity	NPC132496
0.8085	Intermediate Similarity	NPC471567
0.8085	Intermediate Similarity	NPC473651
0.8085	Intermediate Similarity	NPC107986
0.8085	Intermediate Similarity	NPC137033
0.8085	Intermediate Similarity	NPC66346
0.8085	Intermediate Similarity	NPC473478
0.8085	Intermediate Similarity	NPC165162
0.8085	Intermediate Similarity	NPC223871
0.8085	Intermediate Similarity	NPC82795
0.8085	Intermediate Similarity	NPC286338
0.8085	Intermediate Similarity	NPC473669
0.8085	Intermediate Similarity	NPC283085
0.8085	Intermediate Similarity	NPC110710
0.8081	Intermediate Similarity	NPC471492
0.8081	Intermediate Similarity	NPC107476
0.8081	Intermediate Similarity	NPC170120
0.8081	Intermediate Similarity	NPC67584
0.8081	Intermediate Similarity	NPC52044
0.8081	Intermediate Similarity	NPC475659
0.8081	Intermediate Similarity	NPC477922
0.8081	Intermediate Similarity	NPC272050
0.8081	Intermediate Similarity	NPC213698
0.8077	Intermediate Similarity	NPC472749
0.8077	Intermediate Similarity	NPC472751
0.8065	Intermediate Similarity	NPC131669

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 NPC187268 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	209
0.1-0.2	1844
0.2-0.3	3709
0.3-0.4	2289
0.4-0.5	716
0.5-0.6	296
0.6-0.7	72
0.7-0.8	15
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
0.8041	Intermediate Similarity	NPD6698	Approved
0.8041	Intermediate Similarity	NPD46	Approved
0.8	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6371	Approved
0.7706	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD7838	Discovery
0.767	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD6686	Approved
0.7526	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD7983	Approved
0.74	Intermediate Similarity	NPD1695	Approved
0.7379	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4225	Approved
0.7196	Intermediate Similarity	NPD5344	Discontinued
0.71	Intermediate Similarity	NPD4249	Approved
0.703	Intermediate Similarity	NPD4250	Approved
0.703	Intermediate Similarity	NPD4251	Approved
0.699	Remote Similarity	NPD5785	Approved
0.6975	Remote Similarity	NPD8516	Approved
0.6975	Remote Similarity	NPD8513	Phase 3
0.6975	Remote Similarity	NPD8517	Approved
0.6975	Remote Similarity	NPD8515	Approved
0.697	Remote Similarity	NPD7154	Phase 3
0.6952	Remote Similarity	NPD5282	Discontinued
0.687	Remote Similarity	NPD6053	Discontinued
0.6832	Remote Similarity	NPD5363	Approved
0.68	Remote Similarity	NPD5362	Discontinued
0.6789	Remote Similarity	NPD6648	Approved
0.678	Remote Similarity	NPD7115	Discovery
0.6754	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7507	Approved
0.6698	Remote Similarity	NPD5779	Approved
0.6698	Remote Similarity	NPD5778	Approved
0.6694	Remote Similarity	NPD8074	Phase 3
0.6667	Remote Similarity	NPD4821	Approved
0.6667	Remote Similarity	NPD7839	Suspended
0.6667	Remote Similarity	NPD4819	Approved
0.6667	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4820	Approved
0.6667	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4822	Approved
0.6636	Remote Similarity	NPD7640	Approved
0.6636	Remote Similarity	NPD7639	Approved
0.6587	Remote Similarity	NPD7319	Approved
0.6585	Remote Similarity	NPD7642	Approved
0.6579	Remote Similarity	NPD6412	Phase 2
0.6569	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD7638	Approved
0.6535	Remote Similarity	NPD4270	Approved
0.6535	Remote Similarity	NPD4269	Approved
0.6535	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD1694	Approved
0.6489	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD4268	Approved
0.6465	Remote Similarity	NPD4271	Approved
0.6452	Remote Similarity	NPD7829	Approved
0.6452	Remote Similarity	NPD7830	Approved
0.6446	Remote Similarity	NPD7328	Approved
0.6446	Remote Similarity	NPD7641	Discontinued
0.6446	Remote Similarity	NPD7327	Approved
0.6442	Remote Similarity	NPD5786	Approved
0.6436	Remote Similarity	NPD5369	Approved
0.6423	Remote Similarity	NPD8033	Approved
0.64	Remote Similarity	NPD7492	Approved
0.6393	Remote Similarity	NPD7516	Approved
0.6373	Remote Similarity	NPD6435	Approved
0.6349	Remote Similarity	NPD6616	Approved
0.6349	Remote Similarity	NPD8451	Approved
0.6341	Remote Similarity	NPD8377	Approved
0.6341	Remote Similarity	NPD8294	Approved
0.6341	Remote Similarity	NPD6054	Approved
0.6337	Remote Similarity	NPD4252	Approved
0.6311	Remote Similarity	NPD5332	Approved
0.6311	Remote Similarity	NPD6110	Phase 1
0.6311	Remote Similarity	NPD5331	Approved
0.63	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD7078	Approved
0.6299	Remote Similarity	NPD8448	Approved
0.6293	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.629	Remote Similarity	NPD6016	Approved
0.629	Remote Similarity	NPD7503	Approved
0.629	Remote Similarity	NPD8380	Approved
0.629	Remote Similarity	NPD8335	Approved
0.629	Remote Similarity	NPD6015	Approved
0.629	Remote Similarity	NPD8378	Approved
0.629	Remote Similarity	NPD8379	Approved
0.629	Remote Similarity	NPD8296	Approved
0.6275	Remote Similarity	NPD4790	Discontinued
0.627	Remote Similarity	NPD8342	Approved
0.627	Remote Similarity	NPD8299	Approved
0.627	Remote Similarity	NPD8341	Approved
0.627	Remote Similarity	NPD8340	Approved
0.625	Remote Similarity	NPD8133	Approved
0.625	Remote Similarity	NPD4632	Approved
0.625	Remote Similarity	NPD7736	Approved
0.624	Remote Similarity	NPD5988	Approved
0.624	Remote Similarity	NPD6370	Approved
0.6237	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.623	Remote Similarity	NPD7500	Approved
0.623	Remote Similarity	NPD6009	Approved
0.622	Remote Similarity	NPD8273	Phase 1
0.6218	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.621	Remote Similarity	NPD6319	Approved
0.621	Remote Similarity	NPD6059	Approved
0.6207	Remote Similarity	NPD6008	Approved
0.6176	Remote Similarity	NPD5368	Approved
0.6172	Remote Similarity	NPD8293	Discontinued
0.616	Remote Similarity	NPD8444	Approved
0.6154	Remote Similarity	NPD8390	Approved
0.6154	Remote Similarity	NPD8391	Approved
0.6154	Remote Similarity	NPD8392	Approved
0.6147	Remote Similarity	NPD7637	Suspended
0.6111	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD6101	Approved
0.6102	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD6399	Phase 3
0.6087	Remote Similarity	NPD7632	Discontinued
0.6083	Remote Similarity	NPD2204	Approved
0.6075	Remote Similarity	NPD7524	Approved
0.6063	Remote Similarity	NPD8328	Phase 3
0.6058	Remote Similarity	NPD5209	Approved
0.605	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.604	Remote Similarity	NPD4756	Discovery
0.6033	Remote Similarity	NPD6882	Approved
0.6033	Remote Similarity	NPD8297	Approved
0.6032	Remote Similarity	NPD8268	Approved
0.6032	Remote Similarity	NPD8269	Approved
0.6032	Remote Similarity	NPD8266	Approved
0.6032	Remote Similarity	NPD8267	Approved
0.6018	Remote Similarity	NPD6083	Phase 2
0.6018	Remote Similarity	NPD6084	Phase 2
0.6017	Remote Similarity	NPD5697	Approved
0.6	Remote Similarity	NPD6421	Discontinued
0.6	Remote Similarity	NPD6411	Approved
0.5985	Remote Similarity	NPD7260	Phase 2
0.5984	Remote Similarity	NPD8080	Discontinued
0.5982	Remote Similarity	NPD5695	Phase 3
0.5968	Remote Similarity	NPD7505	Discontinued
0.5968	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD6899	Approved
0.5966	Remote Similarity	NPD7320	Approved
0.5966	Remote Similarity	NPD6881	Approved
0.5965	Remote Similarity	NPD5696	Approved
0.5963	Remote Similarity	NPD5370	Suspended
0.595	Remote Similarity	NPD6650	Approved
0.595	Remote Similarity	NPD6649	Approved
0.5943	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.594	Remote Similarity	NPD6845	Suspended
0.5932	Remote Similarity	NPD5739	Approved
0.5932	Remote Similarity	NPD6675	Approved
0.5932	Remote Similarity	NPD7128	Approved
0.5932	Remote Similarity	NPD6402	Approved
0.5917	Remote Similarity	NPD6373	Approved
0.5917	Remote Similarity	NPD6014	Approved
0.5917	Remote Similarity	NPD6372	Approved
0.5917	Remote Similarity	NPD6012	Approved
0.5917	Remote Similarity	NPD6013	Approved
0.5909	Remote Similarity	NPD5956	Approved
0.5906	Remote Similarity	NPD5983	Phase 2
0.5882	Remote Similarity	NPD5701	Approved
0.5877	Remote Similarity	NPD7902	Approved
0.5868	Remote Similarity	NPD6883	Approved
0.5868	Remote Similarity	NPD7290	Approved
0.5868	Remote Similarity	NPD7102	Approved
0.5856	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD6695	Phase 3
0.5842	Remote Similarity	NPD8039	Approved
0.584	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD6011	Approved
0.582	Remote Similarity	NPD6847	Approved
0.582	Remote Similarity	NPD8130	Phase 1
0.582	Remote Similarity	NPD6617	Approved
0.582	Remote Similarity	NPD6869	Approved
0.5814	Remote Similarity	NPD6067	Discontinued
0.5814	Remote Similarity	NPD7604	Phase 2
0.5812	Remote Similarity	NPD5211	Phase 2
0.5809	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD3197	Phase 1
0.5789	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.5781	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD3168	Discontinued
0.5758	Remote Similarity	NPD6033	Approved
0.5755	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD7748	Approved
0.5738	Remote Similarity	NPD4634	Approved
0.5738	Remote Similarity	NPD2067	Discontinued
0.5736	Remote Similarity	NPD7623	Phase 3
0.5736	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD6903	Approved
0.5725	Remote Similarity	NPD6336	Discontinued
0.5714	Remote Similarity	NPD5281	Approved
0.5714	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5141	Approved
0.5714	Remote Similarity	NPD5284	Approved
0.5714	Remote Similarity	NPD5693	Phase 1
0.5714	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7515	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