NPASS Compound

Structure

NPC51568 OpenBabel07101719142D 33 38 0 0 1 0 0 0 0 0999 V2000 -3.0186 -1.5921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5058 -2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -3.8974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2654 -0.5781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 -3.4103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9174 -1.3021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 -1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4771 -1.9434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3753 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 -2.4359 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6876 -1.9487 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5315 -3.4103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 -0.4872 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.9487 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5315 -0.4872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8438 0.4872 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6876 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 -2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 -2.4359 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6876 -0.9744 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.9744 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8438 -0.4872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8438 -3.4103 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 -3.8974 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 0.4872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 1.9487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4302 -2.1460 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 0.4872 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 22 1 0 0 0 0 2 22 1 0 0 0 0 4 24 1 0 0 0 0 5 25 1 0 0 0 0 6 8 2 0 0 0 0 6 16 1 0 0 0 0 7 9 2 0 0 0 0 7 13 1 0 0 0 0 8 23 1 0 0 0 0 9 31 1 0 0 0 0 10 15 1 0 0 0 0 10 17 1 0 0 0 0 11 14 1 0 0 0 0 11 24 1 0 0 0 0 12 13 2 0 0 0 0 12 31 1 0 0 0 0 13 19 1 0 0 0 0 14 18 1 0 0 0 0 14 27 1 1 0 0 0 15 22 1 0 0 0 0 15 23 1 6 0 0 0 16 22 1 0 0 0 0 16 28 2 0 0 0 0 17 25 1 1 0 0 0 17 29 1 0 0 0 0 18 23 1 6 0 0 0 18 25 1 0 0 0 0 19 24 1 1 0 0 0 19 32 1 0 0 0 0 20 21 1 0 0 0 0 20 26 1 6 0 0 0 20 33 1 0 0 0 0 21 30 2 0 0 0 0 21 32 1 0 0 0 0 23 3 1 6 0 0 0 24 26 1 1 0 0 0 25 26 1 1 0 0 0 26 33 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1162.58
Volume:	1106.05
LogP:	1.692
LogD:	1.421
LogS:	-3.27
# Rotatable Bonds:	14
TPSA:	378.43
# H-Bond Aceptor:	25
# H-Bond Donor:	12
# Rings:	10
# Heavy Atoms:	25

MedChem Properties

QED Drug-Likeness Score:	0.074
Synthetic Accessibility Score:	6.729
Fsp3:	0.964
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.881
MDCK Permeability:	0.00021788400772493333
Pgp-inhibitor:	0.824
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.996
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.041
Plasma Protein Binding (PPB):	54.003448486328125%
Volume Distribution (VD):	0.066
Pgp-substrate:	16.28968048095703%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.062
CYP2C19-inhibitor:	0.0
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.045
CYP3A4-inhibitor:	0.032
CYP3A4-substrate:	0.012

ADMET: Excretion

Clearance (CL):	0.143
Half-life (T1/2):	0.843

ADMET: Toxicity

hERG Blockers:	0.337
Human Hepatotoxicity (H-HT):	0.159
Drug-inuced Liver Injury (DILI):	0.021
AMES Toxicity:	0.065
Rat Oral Acute Toxicity:	0.138
Maximum Recommended Daily Dose:	0.762
Skin Sensitization:	0.156
Carcinogencity:	0.007
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.107

Download Data

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

Natural Product: NPC51568

Natural Product ID:	NPC51568
*Common Name:**	OLFLLQMUDRRHRK-SCPOPASTSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	OLFLLQMUDRRHRK-SCPOPASTSA-N
Standard InCHI:	InChI=1S/C26H32O7/c1-22(2)15-10-17(29)25(5)18(23(15,3)8-6-16(22)28)14(27)11-24(4)19(13-7-9-31-12-13)32-21(30)20-26(24,25)33-20/h6-9,12,14-15,17-20,27,29H,10-11H2,1-5H3/t14-,15+,17-,18-,19+,20-,23+,24+,25-,26-/m1/s1
SMILES:	CC1(C)[C@@H]2C[C@H]([C@]3(C)[C@H]([C@@H](C[C@@]4(C)[C@H](c5ccoc5)OC(=O)[C@@H]5[C@]34O5)O)[C@@]2(C)C=CC1=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL513222
PubChem CID:	16086557
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

*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
NPO29947	Cedrela sinensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16989525]
NPO29947	Cedrela sinensis	Species	Meliaceae	Eukaryota	n.a.	cortex	n.a.	PMID[16989525]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	1

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	IC50	>	100.0	ug.mL-1	PMID[459042]

☑ 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 NPC51568 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	359
0.1-0.2	1430
0.2-0.3	3185
0.3-0.4	5542
0.4-0.5	9918
0.5-0.6	10474
0.6-0.7	9239
0.7-0.8	2102
0.8-0.85	268
0.85-0.9	108
0.9-0.95	52
0.95-1	20

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC234660
0.9934	High Similarity	NPC5079
0.9739	High Similarity	NPC335761
0.9677	High Similarity	NPC476856
0.9677	High Similarity	NPC476858
0.9677	High Similarity	NPC476857
0.9675	High Similarity	NPC290400
0.9675	High Similarity	NPC96443
0.9673	High Similarity	NPC475295
0.9673	High Similarity	NPC473473
0.9671	High Similarity	NPC209364
0.9613	High Similarity	NPC302369
0.9613	High Similarity	NPC39986
0.9613	High Similarity	NPC134254
0.9608	High Similarity	NPC286722
0.9554	High Similarity	NPC476853
0.9554	High Similarity	NPC476861
0.9554	High Similarity	NPC476850
0.9542	High Similarity	NPC107646
0.9494	High Similarity	NPC471397
0.949	High Similarity	NPC23387
0.9484	High Similarity	NPC472653
0.9484	High Similarity	NPC25255
0.943	High Similarity	NPC472282
0.943	High Similarity	NPC173516
0.9427	High Similarity	NPC276551
0.9427	High Similarity	NPC476860
0.9427	High Similarity	NPC123088
0.9423	High Similarity	NPC149896
0.9423	High Similarity	NPC117986
0.9423	High Similarity	NPC69028
0.9423	High Similarity	NPC193798
0.9416	High Similarity	NPC60973
0.9371	High Similarity	NPC271235
0.9367	High Similarity	NPC470875
0.9363	High Similarity	NPC477405
0.9363	High Similarity	NPC292389
0.9363	High Similarity	NPC469338
0.9359	High Similarity	NPC475381
0.9308	High Similarity	NPC472651
0.9304	High Similarity	NPC271657
0.9304	High Similarity	NPC470940
0.9304	High Similarity	NPC469849
0.9299	High Similarity	NPC18347
0.9299	High Similarity	NPC82851
0.9299	High Similarity	NPC470939
0.9295	High Similarity	NPC477403
0.929	High Similarity	NPC126723
0.9286	High Similarity	NPC178932
0.9286	High Similarity	NPC57998
0.925	High Similarity	NPC160651
0.925	High Similarity	NPC472652
0.9236	High Similarity	NPC477402
0.9231	High Similarity	NPC249021
0.9231	High Similarity	NPC187149
0.9231	High Similarity	NPC472283
0.9226	High Similarity	NPC214541
0.9226	High Similarity	NPC44675
0.9226	High Similarity	NPC469336
0.9221	High Similarity	NPC469503
0.9187	High Similarity	NPC472774
0.9187	High Similarity	NPC472775
0.9187	High Similarity	NPC473753
0.9187	High Similarity	NPC473766
0.9177	High Similarity	NPC263432
0.9177	High Similarity	NPC200782
0.9172	High Similarity	NPC237155
0.9172	High Similarity	NPC475967
0.9167	High Similarity	NPC263265
0.9119	High Similarity	NPC469846
0.9114	High Similarity	NPC305016
0.9108	High Similarity	NPC299038
0.9108	High Similarity	NPC45101
0.9108	High Similarity	NPC261597
0.9103	High Similarity	NPC469850
0.9103	High Similarity	NPC35000
0.9085	High Similarity	NPC262386
0.9074	High Similarity	NPC302392
0.9074	High Similarity	NPC470995
0.9057	High Similarity	NPC472771
0.9057	High Similarity	NPC329938
0.9051	High Similarity	NPC307383
0.9038	High Similarity	NPC30222
0.9038	High Similarity	NPC282445
0.9018	High Similarity	NPC160818
0.9018	High Similarity	NPC169299
0.9006	High Similarity	NPC475779
0.9006	High Similarity	NPC478178
0.9	High Similarity	NPC472773
0.8987	High Similarity	NPC36655
0.8987	High Similarity	NPC472772
0.8981	High Similarity	NPC476262
0.8981	High Similarity	NPC281258
0.8981	High Similarity	NPC264943
0.8974	High Similarity	NPC44577
0.8974	High Similarity	NPC75906
0.8974	High Similarity	NPC476201
0.8968	High Similarity	NPC477404
0.8968	High Similarity	NPC196864
0.8968	High Similarity	NPC159927
0.8968	High Similarity	NPC476122
0.8968	High Similarity	NPC469335
0.8957	High Similarity	NPC82602
0.8947	High Similarity	NPC86935
0.8944	High Similarity	NPC470182
0.8938	High Similarity	NPC207978
0.8938	High Similarity	NPC211777
0.8931	High Similarity	NPC473368
0.8924	High Similarity	NPC469485
0.891	High Similarity	NPC18135
0.8903	High Similarity	NPC69647
0.8903	High Similarity	NPC125182
0.8896	High Similarity	NPC255414
0.8889	High Similarity	NPC97574
0.8889	High Similarity	NPC93172
0.8882	High Similarity	NPC198047
0.8882	High Similarity	NPC663
0.8882	High Similarity	NPC224394
0.8882	High Similarity	NPC476197
0.8868	High Similarity	NPC173544
0.8854	High Similarity	NPC268905
0.8846	High Similarity	NPC46551
0.8834	High Similarity	NPC478179
0.8824	High Similarity	NPC476944
0.882	High Similarity	NPC197596
0.8816	High Similarity	NPC121158
0.8812	High Similarity	NPC262872
0.8812	High Similarity	NPC474611
0.8795	High Similarity	NPC236004
0.8788	High Similarity	NPC159232
0.8782	High Similarity	NPC472654
0.8782	High Similarity	NPC195325
0.8774	High Similarity	NPC250228
0.8774	High Similarity	NPC221809
0.8766	High Similarity	NPC41182
0.8765	High Similarity	NPC247563
0.8765	High Similarity	NPC242068
0.8765	High Similarity	NPC419
0.8758	High Similarity	NPC470789
0.8758	High Similarity	NPC243577
0.8758	High Similarity	NPC191828
0.875	High Similarity	NPC472776
0.875	High Similarity	NPC472777
0.875	High Similarity	NPC472778
0.875	High Similarity	NPC167142
0.872	High Similarity	NPC100333
0.8712	High Similarity	NPC146991
0.871	High Similarity	NPC346
0.871	High Similarity	NPC262198
0.8704	High Similarity	NPC188649
0.8701	High Similarity	NPC251865
0.8701	High Similarity	NPC137295
0.869	High Similarity	NPC478177
0.8684	High Similarity	NPC67003
0.8683	High Similarity	NPC94763
0.8679	High Similarity	NPC114880
0.8667	High Similarity	NPC296558
0.8659	High Similarity	NPC472141
0.8655	High Similarity	NPC105395
0.8654	High Similarity	NPC470941
0.8654	High Similarity	NPC471174
0.865	High Similarity	NPC288602
0.865	High Similarity	NPC88841
0.865	High Similarity	NPC165218
0.865	High Similarity	NPC472139
0.8645	High Similarity	NPC5676
0.8634	High Similarity	NPC194499
0.8634	High Similarity	NPC195954
0.8625	High Similarity	NPC92979
0.8625	High Similarity	NPC141538
0.8625	High Similarity	NPC296807
0.8625	High Similarity	NPC75310
0.8625	High Similarity	NPC155939
0.8616	High Similarity	NPC33938
0.8616	High Similarity	NPC246164
0.8608	High Similarity	NPC470997
0.8598	High Similarity	NPC261184
0.8589	High Similarity	NPC472668
0.8589	High Similarity	NPC18986
0.8588	High Similarity	NPC470938
0.8581	High Similarity	NPC142113
0.858	High Similarity	NPC474932
0.858	High Similarity	NPC475226
0.8571	High Similarity	NPC471437
0.8563	High Similarity	NPC285227
0.8562	High Similarity	NPC90296
0.8554	High Similarity	NPC242334
0.8554	High Similarity	NPC327922
0.8553	High Similarity	NPC272590
0.8553	High Similarity	NPC476943
0.8545	High Similarity	NPC121995
0.8545	High Similarity	NPC214600
0.8544	High Similarity	NPC211625
0.8544	High Similarity	NPC234494
0.8537	High Similarity	NPC472669
0.8535	High Similarity	NPC216755
0.8528	High Similarity	NPC287559
0.8519	High Similarity	NPC470118
0.8519	High Similarity	NPC88007
0.8516	High Similarity	NPC476946

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 NPC51568 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	307
0.1-0.2	1028
0.2-0.3	2169
0.3-0.4	2632
0.4-0.5	1827
0.5-0.6	875
0.6-0.7	271
0.7-0.8	39
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8509	High Similarity	NPD5761	Phase 2
0.8509	High Similarity	NPD5760	Phase 2
0.8488	Intermediate Similarity	NPD8434	Phase 2
0.8084	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD6765	Approved
0.7989	Intermediate Similarity	NPD6764	Approved
0.7809	Intermediate Similarity	NPD6784	Approved
0.7809	Intermediate Similarity	NPD6785	Approved
0.7738	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD7075	Discontinued
0.756	Intermediate Similarity	NPD6599	Discontinued
0.75	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD3751	Discontinued
0.7439	Intermediate Similarity	NPD4628	Phase 3
0.7427	Intermediate Similarity	NPD7819	Suspended
0.7414	Intermediate Similarity	NPD5494	Approved
0.7389	Intermediate Similarity	NPD6559	Discontinued
0.7384	Intermediate Similarity	NPD5402	Approved
0.7374	Intermediate Similarity	NPD8404	Phase 2
0.7368	Intermediate Similarity	NPD6801	Discontinued
0.7349	Intermediate Similarity	NPD7236	Approved
0.733	Intermediate Similarity	NPD3787	Discontinued
0.7322	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD5844	Phase 1
0.7305	Intermediate Similarity	NPD6799	Approved
0.7299	Intermediate Similarity	NPD3749	Approved
0.7283	Intermediate Similarity	NPD8150	Discontinued
0.7263	Intermediate Similarity	NPD7799	Discontinued
0.7262	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD919	Approved
0.7222	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD3817	Phase 2
0.7176	Intermediate Similarity	NPD920	Approved
0.7176	Intermediate Similarity	NPD5403	Approved
0.7175	Intermediate Similarity	NPD1247	Approved
0.716	Intermediate Similarity	NPD5401	Approved
0.7158	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1471	Phase 3
0.7151	Intermediate Similarity	NPD4380	Phase 2
0.7143	Intermediate Similarity	NPD3882	Suspended
0.7135	Intermediate Similarity	NPD7239	Suspended
0.7126	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD8312	Approved
0.712	Intermediate Similarity	NPD8313	Approved
0.7118	Intermediate Similarity	NPD6273	Approved
0.7113	Intermediate Similarity	NPD7435	Discontinued
0.711	Intermediate Similarity	NPD7411	Suspended
0.7102	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD8407	Phase 2
0.7079	Intermediate Similarity	NPD8127	Discontinued
0.7059	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD6166	Phase 2
0.7056	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD2346	Discontinued
0.7045	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD7473	Discontinued
0.7011	Intermediate Similarity	NPD7251	Discontinued
0.7011	Intermediate Similarity	NPD8368	Discontinued
0.6994	Remote Similarity	NPD7458	Discontinued
0.6994	Remote Similarity	NPD3226	Approved
0.6994	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD3818	Discontinued
0.6973	Remote Similarity	NPD7808	Phase 3
0.6971	Remote Similarity	NPD1934	Approved
0.6964	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD4111	Phase 1
0.6959	Remote Similarity	NPD2533	Approved
0.6959	Remote Similarity	NPD2532	Approved
0.6959	Remote Similarity	NPD2534	Approved
0.6957	Remote Similarity	NPD6797	Phase 2
0.6957	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD6355	Discontinued
0.6941	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD2799	Discontinued
0.6923	Remote Similarity	NPD3750	Approved
0.6919	Remote Similarity	NPD7685	Pre-registration
0.6905	Remote Similarity	NPD1549	Phase 2
0.6902	Remote Similarity	NPD7074	Phase 3
0.69	Remote Similarity	NPD7874	Approved
0.69	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7907	Approved
0.6889	Remote Similarity	NPD6959	Discontinued
0.6886	Remote Similarity	NPD6100	Approved
0.6886	Remote Similarity	NPD2796	Approved
0.6886	Remote Similarity	NPD6099	Approved
0.6878	Remote Similarity	NPD4665	Approved
0.6872	Remote Similarity	NPD6778	Approved
0.6872	Remote Similarity	NPD6779	Approved
0.6872	Remote Similarity	NPD6781	Approved
0.6872	Remote Similarity	NPD6782	Approved
0.6872	Remote Similarity	NPD6776	Approved
0.6872	Remote Similarity	NPD6780	Approved
0.6872	Remote Similarity	NPD4107	Approved
0.6872	Remote Similarity	NPD6777	Approved
0.6868	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD2800	Approved
0.6854	Remote Similarity	NPD7768	Phase 2
0.6853	Remote Similarity	NPD7696	Phase 3
0.6853	Remote Similarity	NPD7698	Approved
0.6853	Remote Similarity	NPD7697	Approved
0.6851	Remote Similarity	NPD6232	Discontinued
0.6848	Remote Similarity	NPD7054	Approved
0.6845	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD5763	Approved
0.6845	Remote Similarity	NPD5762	Approved
0.6842	Remote Similarity	NPD8435	Approved
0.6842	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD2801	Approved
0.6827	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD7033	Discontinued
0.6826	Remote Similarity	NPD3748	Approved
0.6818	Remote Similarity	NPD7870	Phase 2
0.6818	Remote Similarity	NPD7871	Phase 2
0.6813	Remote Similarity	NPD3926	Phase 2
0.6811	Remote Similarity	NPD7472	Approved
0.6802	Remote Similarity	NPD3057	Approved
0.6793	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD1551	Phase 2
0.6786	Remote Similarity	NPD2935	Discontinued
0.678	Remote Similarity	NPD37	Approved
0.6768	Remote Similarity	NPD2313	Discontinued
0.6765	Remote Similarity	NPD1243	Approved
0.6763	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.676	Remote Similarity	NPD4966	Approved
0.676	Remote Similarity	NPD7057	Phase 3
0.676	Remote Similarity	NPD4967	Phase 2
0.676	Remote Similarity	NPD7058	Phase 2
0.676	Remote Similarity	NPD4965	Approved
0.6754	Remote Similarity	NPD8361	Approved
0.6754	Remote Similarity	NPD8360	Approved
0.6751	Remote Similarity	NPD4482	Phase 3
0.6746	Remote Similarity	NPD2344	Approved
0.6737	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD8285	Discontinued
0.6734	Remote Similarity	NPD8319	Approved
0.6734	Remote Similarity	NPD8320	Phase 1
0.6727	Remote Similarity	NPD6233	Phase 2
0.6721	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD2972	Approved
0.6717	Remote Similarity	NPD3533	Approved
0.6716	Remote Similarity	NPD7701	Phase 2
0.6707	Remote Similarity	NPD7095	Approved
0.6706	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD7228	Approved
0.67	Remote Similarity	NPD7801	Approved
0.6687	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD3887	Approved
0.6686	Remote Similarity	NPD6190	Approved
0.6683	Remote Similarity	NPD7497	Discontinued
0.6667	Remote Similarity	NPD7097	Phase 1
0.6667	Remote Similarity	NPD6798	Discontinued
0.6667	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7229	Phase 3
0.6667	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD1465	Phase 2
0.6648	Remote Similarity	NPD8455	Phase 2
0.6646	Remote Similarity	NPD6832	Phase 2
0.6633	Remote Similarity	NPD8485	Approved
0.6633	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD1512	Approved
0.6628	Remote Similarity	NPD7003	Approved
0.6627	Remote Similarity	NPD1510	Phase 2
0.6618	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD7783	Phase 2
0.6616	Remote Similarity	NPD4580	Approved
0.6615	Remote Similarity	NPD6535	Approved
0.6615	Remote Similarity	NPD6534	Approved
0.6612	Remote Similarity	NPD7199	Phase 2
0.6599	Remote Similarity	NPD7700	Phase 2
0.6599	Remote Similarity	NPD7699	Phase 2
0.6595	Remote Similarity	NPD2403	Approved
0.6593	Remote Similarity	NPD6234	Discontinued
0.6592	Remote Similarity	NPD6844	Discontinued
0.6591	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.659	Remote Similarity	NPD2309	Approved
0.659	Remote Similarity	NPD2354	Approved
0.6584	Remote Similarity	NPD1608	Approved
0.6576	Remote Similarity	NPD5711	Approved
0.6576	Remote Similarity	NPD5710	Approved
0.6571	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD3268	Approved
0.6566	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD3764	Approved
0.6561	Remote Similarity	NPD7240	Approved
0.655	Remote Similarity	NPD6004	Phase 3
0.655	Remote Similarity	NPD6002	Phase 3
0.655	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.655	Remote Similarity	NPD2491	Approved
0.655	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.655	Remote Similarity	NPD6823	Phase 2
0.655	Remote Similarity	NPD6005	Phase 3
0.6548	Remote Similarity	NPD2974	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