NPASS Compound

Structure

CID312325 OpenBabel06191716122D 27 29 0 0 1 0 0 0 0 0999 V2000 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0622 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 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 2 17 1 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 5 6 2 0 0 0 0 5 10 1 0 0 0 0 7 11 1 0 0 0 0 7 17 1 0 0 0 0 8 11 1 0 0 0 0 8 18 1 0 0 0 0 9 20 1 0 0 0 0 10 1 1 6 0 0 0 10 25 1 0 0 0 0 11 21 1 6 0 0 0 12 9 1 6 0 0 0 12 13 1 0 0 0 0 12 26 1 0 0 0 0 13 14 1 0 0 0 0 13 22 1 1 0 0 0 14 15 1 0 0 0 0 14 23 1 6 0 0 0 15 16 1 0 0 0 0 15 24 1 1 0 0 0 16 25 1 6 0 0 0 16 26 1 0 0 0 0 17 19 1 0 0 0 0 18 19 1 1 0 0 0 18 27 1 0 0 0 0 19 6 1 1 0 0 0 19 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	388.21
Volume:	379.196
LogP:	0.829
LogD:	0.41
LogS:	-2.462
# Rotatable Bonds:	5
TPSA:	132.14
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.313
Synthetic Accessibility Score:	4.946
Fsp3:	0.895
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:	-5.924
MDCK Permeability:	7.524881220888346e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.943
Human Intestinal Absorption (HIA):	0.658
20% Bioavailability (F20%):	0.827
30% Bioavailability (F30%):	0.819

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.084
Plasma Protein Binding (PPB):	70.95311737060547%
Volume Distribution (VD):	0.475
Pgp-substrate:	33.382171630859375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.939
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.843
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.032
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.078
CYP3A4-inhibitor:	0.012
CYP3A4-substrate:	0.354

ADMET: Excretion

Clearance (CL):	1.893
Half-life (T1/2):	0.73

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.166
Drug-inuced Liver Injury (DILI):	0.029
AMES Toxicity:	0.725
Rat Oral Acute Toxicity:	0.133
Maximum Recommended Daily Dose:	0.954
Skin Sensitization:	0.206
Carcinogencity:	0.252
Eye Corrosion:	0.003
Eye Irritation:	0.021
Respiratory Toxicity:	0.88

Download Data

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

Natural Product: NPC312325

Natural Product ID:	NPC312325
*Common Name:**	Phlomuroside
IUPAC Name:	(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(E,2R)-4-[(1S,3S,6R)-3-hydroxy-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-6-yl]but-3-en-2-yl]oxyoxane-3,4,5-triol
Synonyms:	Phlomuroside
Standard InCHIKey:	RIUMIKAUMHZQMP-IQUVFKTMSA-N
Standard InCHI:	InChI=1S/C19H32O8/c1-10(25-16-15(24)14(23)13(22)12(9-20)26-16)5-6-19-17(2,3)7-11(21)8-18(19,4)27-19/h5-6,10-16,20-24H,7-9H2,1-4H3/b6-5+/t10-,11+,12-,13-,14+,15-,16-,18+,19-/m1/s1
SMILES:	C[C@H](/C=C/[C@@]12C(C)(C)C[C@@H](C[C@]1(C)O2)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1814430
PubChem CID:	637144
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001766] Fatty acyl glycosides [CHEMONTID:0003861] Fatty acyl glycosides of mono- and disaccharides

*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
NPO29956	Sanicula lamelligera	Species	Apiaceae	Eukaryota	Whole plants	Mountain Emei, Sichuan Province, China	2008-OCT	PMID[21561060]
NPO29956	Sanicula lamelligera	Species	Apiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21561060]

☑ 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
EC50	1
IC50	6
Others	1

Activity Type	# Activity
Cell Line	7
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	64400.0	nM	PMID[509817]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	64400.0	nM	PMID[509817]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	64400.0	nM	PMID[509817]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	64400.0	nM	PMID[509817]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	64400.0	nM	PMID[509817]
NPT1452	Cell Line	C8166	Homo sapiens	CC50	>	257700.0	nM	PMID[509817]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	64400.0	nM	PMID[509817]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	>	257700.0	nM	PMID[509817]

☑ 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 NPC312325 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	247
0.1-0.2	1836
0.2-0.3	5134
0.3-0.4	10347
0.4-0.5	12944
0.5-0.6	7166
0.6-0.7	4205
0.7-0.8	790
0.8-0.85	26
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9082	High Similarity	NPC194941
0.8557	High Similarity	NPC90583
0.8544	High Similarity	NPC472901
0.85	High Similarity	NPC214277
0.8469	Intermediate Similarity	NPC240372
0.8447	Intermediate Similarity	NPC80210
0.8447	Intermediate Similarity	NPC38376
0.8438	Intermediate Similarity	NPC474792
0.8438	Intermediate Similarity	NPC67398
0.8438	Intermediate Similarity	NPC91654
0.8421	Intermediate Similarity	NPC474249
0.8421	Intermediate Similarity	NPC261990
0.8381	Intermediate Similarity	NPC473021
0.8381	Intermediate Similarity	NPC472987
0.8365	Intermediate Similarity	NPC195116
0.8365	Intermediate Similarity	NPC473318
0.8365	Intermediate Similarity	NPC473328
0.8365	Intermediate Similarity	NPC28844
0.8365	Intermediate Similarity	NPC180459
0.8365	Intermediate Similarity	NPC285253
0.8365	Intermediate Similarity	NPC221110
0.8351	Intermediate Similarity	NPC72817
0.8351	Intermediate Similarity	NPC477927
0.835	Intermediate Similarity	NPC33053
0.8333	Intermediate Similarity	NPC473068
0.8317	Intermediate Similarity	NPC150463
0.83	Intermediate Similarity	NPC64348
0.8286	Intermediate Similarity	NPC170974
0.8286	Intermediate Similarity	NPC191439
0.8286	Intermediate Similarity	NPC103627
0.8286	Intermediate Similarity	NPC65155
0.8269	Intermediate Similarity	NPC473069
0.8235	Intermediate Similarity	NPC473123
0.8235	Intermediate Similarity	NPC473070
0.8235	Intermediate Similarity	NPC473124
0.8218	Intermediate Similarity	NPC280991
0.8218	Intermediate Similarity	NPC154127
0.8208	Intermediate Similarity	NPC110494
0.8208	Intermediate Similarity	NPC157474
0.8173	Intermediate Similarity	NPC472390
0.8163	Intermediate Similarity	NPC305160
0.8155	Intermediate Similarity	NPC473127
0.8155	Intermediate Similarity	NPC203354
0.8155	Intermediate Similarity	NPC110656
0.8155	Intermediate Similarity	NPC93352
0.8152	Intermediate Similarity	NPC259858
0.8144	Intermediate Similarity	NPC289361
0.8144	Intermediate Similarity	NPC302584
0.8131	Intermediate Similarity	NPC476305
0.8131	Intermediate Similarity	NPC475354
0.8131	Intermediate Similarity	NPC216595
0.8131	Intermediate Similarity	NPC473567
0.8131	Intermediate Similarity	NPC473125
0.8131	Intermediate Similarity	NPC231797
0.8125	Intermediate Similarity	NPC309310
0.81	Intermediate Similarity	NPC96597
0.81	Intermediate Similarity	NPC26307
0.81	Intermediate Similarity	NPC155319
0.81	Intermediate Similarity	NPC91197
0.81	Intermediate Similarity	NPC309503
0.81	Intermediate Similarity	NPC125551
0.81	Intermediate Similarity	NPC239547
0.8095	Intermediate Similarity	NPC235824
0.8095	Intermediate Similarity	NPC128795
0.8095	Intermediate Similarity	NPC472897
0.8095	Intermediate Similarity	NPC135015
0.8095	Intermediate Similarity	NPC217921
0.8095	Intermediate Similarity	NPC472896
0.8095	Intermediate Similarity	NPC48548
0.8077	Intermediate Similarity	NPC470763
0.8077	Intermediate Similarity	NPC472898
0.8077	Intermediate Similarity	NPC239961
0.8077	Intermediate Similarity	NPC472900
0.8077	Intermediate Similarity	NPC472899
0.8077	Intermediate Similarity	NPC470767
0.8056	Intermediate Similarity	NPC40133
0.8056	Intermediate Similarity	NPC290608
0.8056	Intermediate Similarity	NPC311592
0.8056	Intermediate Similarity	NPC44298
0.8056	Intermediate Similarity	NPC49413
0.8056	Intermediate Similarity	NPC473128
0.8056	Intermediate Similarity	NPC75167
0.8039	Intermediate Similarity	NPC198992
0.8037	Intermediate Similarity	NPC208189
0.8037	Intermediate Similarity	NPC65034
0.802	Intermediate Similarity	NPC477928
0.8019	Intermediate Similarity	NPC316974
0.8019	Intermediate Similarity	NPC40728
0.8019	Intermediate Similarity	NPC206618
0.8	Intermediate Similarity	NPC125423
0.8	Intermediate Similarity	NPC281939
0.8	Intermediate Similarity	NPC88013
0.7982	Intermediate Similarity	NPC181145
0.7981	Intermediate Similarity	NPC470768
0.7981	Intermediate Similarity	NPC75608
0.7961	Intermediate Similarity	NPC300399
0.7961	Intermediate Similarity	NPC37207
0.7961	Intermediate Similarity	NPC471482
0.7961	Intermediate Similarity	NPC136816
0.7961	Intermediate Similarity	NPC470571
0.7944	Intermediate Similarity	NPC46407
0.7944	Intermediate Similarity	NPC472717
0.7941	Intermediate Similarity	NPC79303
0.7938	Intermediate Similarity	NPC115607
0.7938	Intermediate Similarity	NPC470819
0.7938	Intermediate Similarity	NPC97103
0.7925	Intermediate Similarity	NPC38948
0.7925	Intermediate Similarity	NPC311223
0.7925	Intermediate Similarity	NPC181994
0.7885	Intermediate Similarity	NPC471886
0.7885	Intermediate Similarity	NPC471888
0.7885	Intermediate Similarity	NPC7644
0.7885	Intermediate Similarity	NPC471885
0.7885	Intermediate Similarity	NPC475889
0.7885	Intermediate Similarity	NPC473129
0.7885	Intermediate Similarity	NPC473198
0.7885	Intermediate Similarity	NPC127933
0.7885	Intermediate Similarity	NPC99627
0.7885	Intermediate Similarity	NPC7613
0.7885	Intermediate Similarity	NPC162354
0.7885	Intermediate Similarity	NPC471887
0.7879	Intermediate Similarity	NPC119379
0.7879	Intermediate Similarity	NPC474835
0.787	Intermediate Similarity	NPC472715
0.7864	Intermediate Similarity	NPC88000
0.7864	Intermediate Similarity	NPC476896
0.7864	Intermediate Similarity	NPC472023
0.7864	Intermediate Similarity	NPC21568
0.7864	Intermediate Similarity	NPC285231
0.7864	Intermediate Similarity	NPC129372
0.7864	Intermediate Similarity	NPC4831
0.7864	Intermediate Similarity	NPC309425
0.7864	Intermediate Similarity	NPC47566
0.7864	Intermediate Similarity	NPC160734
0.7857	Intermediate Similarity	NPC470817
0.785	Intermediate Similarity	NPC250089
0.785	Intermediate Similarity	NPC14630
0.785	Intermediate Similarity	NPC157530
0.7849	Intermediate Similarity	NPC16090
0.7835	Intermediate Similarity	NPC248312
0.783	Intermediate Similarity	NPC231340
0.783	Intermediate Similarity	NPC78034
0.7822	Intermediate Similarity	NPC210717
0.7822	Intermediate Similarity	NPC103165
0.7812	Intermediate Similarity	NPC255143
0.7812	Intermediate Similarity	NPC323209
0.781	Intermediate Similarity	NPC57065
0.781	Intermediate Similarity	NPC470321
0.781	Intermediate Similarity	NPC109792
0.781	Intermediate Similarity	NPC187400
0.781	Intermediate Similarity	NPC264867
0.781	Intermediate Similarity	NPC221562
0.781	Intermediate Similarity	NPC473207
0.781	Intermediate Similarity	NPC201880
0.781	Intermediate Similarity	NPC81567
0.781	Intermediate Similarity	NPC54521
0.781	Intermediate Similarity	NPC470885
0.7807	Intermediate Similarity	NPC196130
0.7807	Intermediate Similarity	NPC471082
0.78	Intermediate Similarity	NPC96736
0.78	Intermediate Similarity	NPC178949
0.78	Intermediate Similarity	NPC211238
0.7798	Intermediate Similarity	NPC317460
0.7798	Intermediate Similarity	NPC174836
0.7798	Intermediate Similarity	NPC328074
0.7798	Intermediate Similarity	NPC321272
0.7798	Intermediate Similarity	NPC472716
0.7798	Intermediate Similarity	NPC470025
0.7788	Intermediate Similarity	NPC48692
0.7788	Intermediate Similarity	NPC471363
0.7788	Intermediate Similarity	NPC121423
0.7788	Intermediate Similarity	NPC238397
0.7778	Intermediate Similarity	NPC316708
0.7778	Intermediate Similarity	NPC119550
0.7778	Intermediate Similarity	NPC177047
0.7778	Intermediate Similarity	NPC83005
0.7768	Intermediate Similarity	NPC83287
0.7767	Intermediate Similarity	NPC324598
0.7767	Intermediate Similarity	NPC7341
0.7767	Intermediate Similarity	NPC473200
0.7767	Intermediate Similarity	NPC271295
0.7745	Intermediate Similarity	NPC261807
0.7745	Intermediate Similarity	NPC473244
0.7742	Intermediate Similarity	NPC236707
0.7736	Intermediate Similarity	NPC51719
0.7736	Intermediate Similarity	NPC82251
0.7727	Intermediate Similarity	NPC264153
0.7727	Intermediate Similarity	NPC470027
0.7723	Intermediate Similarity	NPC8774
0.7723	Intermediate Similarity	NPC135224
0.7723	Intermediate Similarity	NPC477970
0.7723	Intermediate Similarity	NPC477969
0.7723	Intermediate Similarity	NPC100892
0.7719	Intermediate Similarity	NPC233500
0.7717	Intermediate Similarity	NPC272841
0.7714	Intermediate Similarity	NPC155010
0.7714	Intermediate Similarity	NPC134270
0.7714	Intermediate Similarity	NPC31907
0.7714	Intermediate Similarity	NPC131479
0.7714	Intermediate Similarity	NPC211879

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 NPC312325 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	208
0.1-0.2	2088
0.2-0.3	3830
0.3-0.4	2026
0.4-0.5	687
0.5-0.6	243
0.6-0.7	61
0.7-0.8	7
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
0.7768	Intermediate Similarity	NPD7327	Approved
0.7768	Intermediate Similarity	NPD7328	Approved
0.7699	Intermediate Similarity	NPD7516	Approved
0.7692	Intermediate Similarity	NPD5344	Discontinued
0.7431	Intermediate Similarity	NPD6686	Approved
0.7414	Intermediate Similarity	NPD8380	Approved
0.7414	Intermediate Similarity	NPD8335	Approved
0.7414	Intermediate Similarity	NPD8378	Approved
0.7414	Intermediate Similarity	NPD8033	Approved
0.7414	Intermediate Similarity	NPD8296	Approved
0.7414	Intermediate Similarity	NPD8379	Approved
0.7328	Intermediate Similarity	NPD8377	Approved
0.7328	Intermediate Similarity	NPD8294	Approved
0.7265	Intermediate Similarity	NPD7503	Approved
0.7264	Intermediate Similarity	NPD6648	Approved
0.7157	Intermediate Similarity	NPD3168	Discontinued
0.7025	Intermediate Similarity	NPD7507	Approved
0.6992	Remote Similarity	NPD7319	Approved
0.6903	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD7524	Approved
0.6827	Remote Similarity	NPD6698	Approved
0.6827	Remote Similarity	NPD46	Approved
0.6827	Remote Similarity	NPD7838	Discovery
0.6814	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.681	Remote Similarity	NPD8133	Approved
0.6754	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6412	Phase 2
0.6697	Remote Similarity	NPD4225	Approved
0.6697	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD8515	Approved
0.6694	Remote Similarity	NPD8516	Approved
0.6694	Remote Similarity	NPD8517	Approved
0.6694	Remote Similarity	NPD8513	Phase 3
0.6637	Remote Similarity	NPD5357	Phase 1
0.6634	Remote Similarity	NPD6695	Phase 3
0.6545	Remote Similarity	NPD7638	Approved
0.65	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7115	Discovery
0.6496	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD7640	Approved
0.6486	Remote Similarity	NPD7639	Approved
0.6452	Remote Similarity	NPD8328	Phase 3
0.6435	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4159	Approved
0.6421	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD7750	Discontinued
0.6371	Remote Similarity	NPD6370	Approved
0.6337	Remote Similarity	NPD7525	Registered
0.6337	Remote Similarity	NPD7332	Phase 2
0.6337	Remote Similarity	NPD6931	Approved
0.6337	Remote Similarity	NPD7514	Phase 3
0.6337	Remote Similarity	NPD6930	Phase 2
0.629	Remote Similarity	NPD6921	Approved
0.6275	Remote Similarity	NPD6902	Approved
0.6239	Remote Similarity	NPD8171	Discontinued
0.6238	Remote Similarity	NPD6929	Approved
0.6238	Remote Similarity	NPD7645	Phase 2
0.6228	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD1811	Approved
0.6224	Remote Similarity	NPD1810	Approved
0.621	Remote Similarity	NPD6054	Approved
0.6204	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.62	Remote Similarity	NPD6932	Approved
0.619	Remote Similarity	NPD7829	Approved
0.619	Remote Similarity	NPD7830	Approved
0.6172	Remote Similarity	NPD8074	Phase 3
0.6162	Remote Similarity	NPD8264	Approved
0.6147	Remote Similarity	NPD7087	Discontinued
0.6147	Remote Similarity	NPD7637	Suspended
0.6139	Remote Similarity	NPD7145	Approved
0.6124	Remote Similarity	NPD7736	Approved
0.6111	Remote Similarity	NPD5125	Phase 3
0.6111	Remote Similarity	NPD5126	Approved
0.61	Remote Similarity	NPD6933	Approved
0.6094	Remote Similarity	NPD8451	Approved
0.608	Remote Similarity	NPD6059	Approved
0.6068	Remote Similarity	NPD6640	Phase 3
0.6063	Remote Similarity	NPD7642	Approved
0.6047	Remote Similarity	NPD8293	Discontinued
0.6047	Remote Similarity	NPD8448	Approved
0.604	Remote Similarity	NPD6925	Approved
0.604	Remote Similarity	NPD5776	Phase 2
0.6038	Remote Similarity	NPD6893	Approved
0.6033	Remote Similarity	NPD6882	Approved
0.6032	Remote Similarity	NPD6015	Approved
0.6032	Remote Similarity	NPD6016	Approved
0.6016	Remote Similarity	NPD7492	Approved
0.6	Remote Similarity	NPD7983	Approved
0.6	Remote Similarity	NPD6371	Approved
0.5984	Remote Similarity	NPD5988	Approved
0.5969	Remote Similarity	NPD6616	Approved
0.5968	Remote Similarity	NPD6009	Approved
0.5962	Remote Similarity	NPD6898	Phase 1
0.5957	Remote Similarity	NPD371	Approved
0.5957	Remote Similarity	NPD7625	Phase 1
0.5952	Remote Similarity	NPD6319	Approved
0.5948	Remote Similarity	NPD7632	Discontinued
0.5946	Remote Similarity	NPD5778	Approved
0.5946	Remote Similarity	NPD5779	Approved
0.594	Remote Similarity	NPD8449	Approved
0.5938	Remote Similarity	NPD6067	Discontinued
0.5926	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5923	Remote Similarity	NPD7078	Approved
0.5922	Remote Similarity	NPD6683	Phase 2
0.5918	Remote Similarity	NPD2687	Approved
0.5918	Remote Similarity	NPD2254	Approved
0.5918	Remote Similarity	NPD2686	Approved
0.5909	Remote Similarity	NPD8391	Approved
0.5909	Remote Similarity	NPD8390	Approved
0.5909	Remote Similarity	NPD8392	Approved
0.5906	Remote Similarity	NPD8444	Approved
0.5902	Remote Similarity	NPD8297	Approved
0.59	Remote Similarity	NPD6926	Approved
0.59	Remote Similarity	NPD6924	Approved
0.5896	Remote Similarity	NPD8450	Suspended
0.5891	Remote Similarity	NPD8299	Approved
0.5891	Remote Similarity	NPD8340	Approved
0.5891	Remote Similarity	NPD8341	Approved
0.5891	Remote Similarity	NPD8342	Approved
0.5865	Remote Similarity	NPD7509	Discontinued
0.5856	Remote Similarity	NPD6411	Approved
0.5854	Remote Similarity	NPD4632	Approved
0.5849	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD3669	Approved
0.5842	Remote Similarity	NPD7339	Approved
0.5842	Remote Similarity	NPD6942	Approved
0.5825	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.58	Remote Similarity	NPD4732	Discontinued
0.5784	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5772	Remote Similarity	NPD6429	Approved
0.5772	Remote Similarity	NPD6430	Approved
0.575	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6928	Phase 2
0.5714	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5703	Remote Similarity	NPD7741	Discontinued
0.5702	Remote Similarity	NPD6881	Approved
0.5702	Remote Similarity	NPD6899	Approved
0.57	Remote Similarity	NPD7151	Approved
0.57	Remote Similarity	NPD7150	Approved
0.57	Remote Similarity	NPD7152	Approved
0.5692	Remote Similarity	NPD7604	Phase 2
0.5691	Remote Similarity	NPD6650	Approved
0.5691	Remote Similarity	NPD6649	Approved
0.5676	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD6101	Approved
0.5676	Remote Similarity	NPD6051	Approved
0.5667	Remote Similarity	NPD6402	Approved
0.5667	Remote Similarity	NPD6008	Approved
0.5667	Remote Similarity	NPD6675	Approved
0.5667	Remote Similarity	NPD5739	Approved
0.5667	Remote Similarity	NPD7128	Approved
0.5664	Remote Similarity	NPD6399	Phase 3
0.5664	Remote Similarity	NPD6674	Discontinued
0.5656	Remote Similarity	NPD6373	Approved
0.5656	Remote Similarity	NPD6372	Approved
0.5652	Remote Similarity	NPD7839	Suspended
0.5652	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5645	Remote Similarity	NPD6053	Discontinued
0.5639	Remote Similarity	NPD6033	Approved
0.5636	Remote Similarity	NPD4250	Approved
0.5636	Remote Similarity	NPD4251	Approved
0.5625	Remote Similarity	NPD7136	Phase 2
0.562	Remote Similarity	NPD5697	Approved
0.5614	Remote Similarity	NPD5282	Discontinued
0.5614	Remote Similarity	NPD7748	Approved
0.561	Remote Similarity	NPD4634	Approved
0.561	Remote Similarity	NPD6883	Approved
0.561	Remote Similarity	NPD7102	Approved
0.561	Remote Similarity	NPD7290	Approved
0.5606	Remote Similarity	NPD8273	Phase 1
0.5603	Remote Similarity	NPD7902	Approved
0.56	Remote Similarity	NPD7143	Approved
0.56	Remote Similarity	NPD7144	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