NPASS Compound

Structure

CID302584 OpenBabel06191716112D 28 30 0 0 1 0 0 0 0 0999 V2000 -1.1340 -2.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5981 0.7679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3301 -0.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3301 -1.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8660 -0.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4641 0.2679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7321 0.2679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7321 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4641 -2.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4641 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8660 -1.2321 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5981 -1.2321 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5000 -0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0000 -1.7321 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.7321 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5981 -0.2321 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.3301 -3.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -2.5981 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 -1.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 4 5 1 0 0 0 0 4 7 1 0 0 0 0 5 12 2 0 0 0 0 6 8 1 0 0 0 0 6 13 1 0 0 0 0 7 21 1 0 0 0 0 8 21 1 0 0 0 0 9 13 1 0 0 0 0 9 14 1 0 0 0 0 10 12 1 0 0 0 0 10 22 1 0 0 0 0 11 23 1 0 0 0 0 12 14 1 0 0 0 0 13 20 1 1 0 0 0 14 21 1 1 0 0 0 15 11 1 6 0 0 0 15 16 1 0 0 0 0 15 27 1 0 0 0 0 16 17 1 0 0 0 0 16 24 1 1 0 0 0 17 18 1 0 0 0 0 17 25 1 6 0 0 0 18 19 1 0 0 0 0 18 26 1 1 0 0 0 19 27 1 0 0 0 0 19 28 1 6 0 0 0 20 28 1 0 0 0 0 21 3 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	400.25
Volume:	404.998
LogP:	1.769
LogD:	2.533
LogS:	-2.513
# Rotatable Bonds:	5
TPSA:	119.61
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.431
Synthetic Accessibility Score:	4.848
Fsp3:	0.905
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.031
MDCK Permeability:	2.2374011678039096e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.024
Human Intestinal Absorption (HIA):	0.255
20% Bioavailability (F20%):	0.943
30% Bioavailability (F30%):	0.478

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.026
Plasma Protein Binding (PPB):	89.74378204345703%
Volume Distribution (VD):	0.794
Pgp-substrate:	6.1064629554748535%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.091
CYP2C19-inhibitor:	0.005
CYP2C19-substrate:	0.369
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.093
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.158
CYP3A4-inhibitor:	0.012
CYP3A4-substrate:	0.087

ADMET: Excretion

Clearance (CL):	1.53
Half-life (T1/2):	0.721

ADMET: Toxicity

hERG Blockers:	0.045
Human Hepatotoxicity (H-HT):	0.063
Drug-inuced Liver Injury (DILI):	0.882
AMES Toxicity:	0.108
Rat Oral Acute Toxicity:	0.092
Maximum Recommended Daily Dose:	0.069
Skin Sensitization:	0.538
Carcinogencity:	0.14
Eye Corrosion:	0.005
Eye Irritation:	0.622
Respiratory Toxicity:	0.199

Download Data

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

Natural Product: NPC302584

Natural Product ID:	NPC302584
*Common Name:**	15-Hydroxy-Alpha-Eudesmol-11-O-Beta-Dglucopyranoside
IUPAC Name:	(2S,3R,4S,5S,6R)-2-[2-[(2R,4aR,8aR)-8-(hydroxymethyl)-4a-methyl-2,3,4,5,6,8a-hexahydro-1H-naphthalen-2-yl]propan-2-yloxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	PXMONFDWFWAIMC-MPSLSGHYSA-N
Standard InCHI:	InChI=1S/C21H36O7/c1-20(2,28-19-18(26)17(25)16(24)15(11-23)27-19)13-6-8-21(3)7-4-5-12(10-22)14(21)9-13/h5,13-19,22-26H,4,6-11H2,1-3H3/t13-,14+,15-,16-,17+,18-,19+,21-/m1/s1
SMILES:	CC(C)([C@@H]1CC[C@@]2(C)CCC=C(CO)[C@@H]2C1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1956943
PubChem CID:	57391287
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0000101] Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids

*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
NPO6515	Juglans sinensis	Species	Juglandaceae	Eukaryota	n.a.	twig	n.a.	PMID[21309591]
NPO6515	Juglans sinensis	Species	Juglandaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21309591]
NPO941	Tiliacora triandra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22418278]
NPO4636	Onopordum anatolicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3731	Salix japonica	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5560	Castor fiber	Species	Castoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26573	Artemisia umbelliformis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28	Cutleria multifida	Species	Cutleriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO941	Tiliacora triandra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26307	Viburnum ayavacense	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6515	Juglans sinensis	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	4

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT169	Cell Line	B16-F10	Mus musculus	IC50	>	10000.0	nM	PMID[453332]
NPT1171	Cell Line	HEp-2	Homo sapiens	IC50	>	10000.0	nM	PMID[453332]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[453332]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[453332]

☑ 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 NPC302584 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	221
0.1-0.2	1523
0.2-0.3	4973
0.3-0.4	11554
0.4-0.5	11012
0.5-0.6	6462
0.6-0.7	5232
0.7-0.8	1621
0.8-0.85	67
0.85-0.9	25
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9432	High Similarity	NPC67398
0.9432	High Similarity	NPC91654
0.9432	High Similarity	NPC474792
0.9333	High Similarity	NPC90583
0.9176	High Similarity	NPC166279
0.9032	High Similarity	NPC64348
0.9032	High Similarity	NPC469942
0.9022	High Similarity	NPC91197
0.9022	High Similarity	NPC239547
0.9022	High Similarity	NPC240372
0.9022	High Similarity	NPC96597
0.9022	High Similarity	NPC309503
0.9022	High Similarity	NPC125551
0.9022	High Similarity	NPC155319
0.8936	High Similarity	NPC470434
0.8901	High Similarity	NPC305160
0.8876	High Similarity	NPC473058
0.8778	High Similarity	NPC159876
0.8764	High Similarity	NPC248312
0.875	High Similarity	NPC470836
0.875	High Similarity	NPC162354
0.8737	High Similarity	NPC280991
0.8737	High Similarity	NPC285231
0.8737	High Similarity	NPC21568
0.8706	High Similarity	NPC100697
0.8696	High Similarity	NPC72817
0.8696	High Similarity	NPC477927
0.8696	High Similarity	NPC178949
0.8696	High Similarity	NPC96736
0.8667	High Similarity	NPC309310
0.866	High Similarity	NPC470768
0.866	High Similarity	NPC75608
0.8646	High Similarity	NPC470571
0.8617	High Similarity	NPC243728
0.8617	High Similarity	NPC473890
0.8571	High Similarity	NPC470767
0.8571	High Similarity	NPC472899
0.8571	High Similarity	NPC472900
0.8571	High Similarity	NPC472898
0.8571	High Similarity	NPC470763
0.8557	High Similarity	NPC473124
0.8557	High Similarity	NPC473123
0.8526	High Similarity	NPC5358
0.8526	High Similarity	NPC158088
0.8526	High Similarity	NPC216260
0.8511	High Similarity	NPC207617
0.8506	High Similarity	NPC20072
0.8495	Intermediate Similarity	NPC211238
0.8485	Intermediate Similarity	NPC33053
0.8485	Intermediate Similarity	NPC231340
0.8469	Intermediate Similarity	NPC110656
0.8469	Intermediate Similarity	NPC203354
0.8469	Intermediate Similarity	NPC473127
0.8469	Intermediate Similarity	NPC93352
0.8438	Intermediate Similarity	NPC282669
0.8404	Intermediate Similarity	NPC230347
0.8404	Intermediate Similarity	NPC286612
0.8404	Intermediate Similarity	NPC275310
0.8387	Intermediate Similarity	NPC474835
0.837	Intermediate Similarity	NPC474249
0.837	Intermediate Similarity	NPC470817
0.837	Intermediate Similarity	NPC261990
0.8367	Intermediate Similarity	NPC473198
0.8351	Intermediate Similarity	NPC129372
0.8351	Intermediate Similarity	NPC472023
0.8351	Intermediate Similarity	NPC4831
0.8351	Intermediate Similarity	NPC263756
0.8351	Intermediate Similarity	NPC160734
0.8351	Intermediate Similarity	NPC309425
0.8351	Intermediate Similarity	NPC267510
0.8351	Intermediate Similarity	NPC88000
0.8351	Intermediate Similarity	NPC117714
0.8351	Intermediate Similarity	NPC47566
0.8333	Intermediate Similarity	NPC234287
0.8333	Intermediate Similarity	NPC476895
0.8333	Intermediate Similarity	NPC280825
0.8333	Intermediate Similarity	NPC477928
0.8315	Intermediate Similarity	NPC83702
0.83	Intermediate Similarity	NPC281939
0.83	Intermediate Similarity	NPC472390
0.8283	Intermediate Similarity	NPC187400
0.8283	Intermediate Similarity	NPC470885
0.8283	Intermediate Similarity	NPC221562
0.8265	Intermediate Similarity	NPC256133
0.8265	Intermediate Similarity	NPC213674
0.8265	Intermediate Similarity	NPC30289
0.8265	Intermediate Similarity	NPC223834
0.8265	Intermediate Similarity	NPC76497
0.8265	Intermediate Similarity	NPC272015
0.8265	Intermediate Similarity	NPC136816
0.8265	Intermediate Similarity	NPC154452
0.8261	Intermediate Similarity	NPC477917
0.8261	Intermediate Similarity	NPC470819
0.8252	Intermediate Similarity	NPC473567
0.8252	Intermediate Similarity	NPC216595
0.8247	Intermediate Similarity	NPC473200
0.8247	Intermediate Similarity	NPC7341
0.8247	Intermediate Similarity	NPC324598
0.8235	Intermediate Similarity	NPC103627
0.8235	Intermediate Similarity	NPC65155
0.8235	Intermediate Similarity	NPC141433
0.8235	Intermediate Similarity	NPC191439
0.8235	Intermediate Similarity	NPC170974
0.8229	Intermediate Similarity	NPC476893
0.8222	Intermediate Similarity	NPC119001
0.8218	Intermediate Similarity	NPC38376
0.8218	Intermediate Similarity	NPC472897
0.8218	Intermediate Similarity	NPC472896
0.8218	Intermediate Similarity	NPC80210
0.8211	Intermediate Similarity	NPC108141
0.82	Intermediate Similarity	NPC309448
0.82	Intermediate Similarity	NPC26798
0.82	Intermediate Similarity	NPC474569
0.8191	Intermediate Similarity	NPC119379
0.8182	Intermediate Similarity	NPC189852
0.8182	Intermediate Similarity	NPC8039
0.8182	Intermediate Similarity	NPC213190
0.8182	Intermediate Similarity	NPC99627
0.8182	Intermediate Similarity	NPC16520
0.8182	Intermediate Similarity	NPC286969
0.8182	Intermediate Similarity	NPC131479
0.8182	Intermediate Similarity	NPC245280
0.8182	Intermediate Similarity	NPC16090
0.8182	Intermediate Similarity	NPC123796
0.8182	Intermediate Similarity	NPC473129
0.8182	Intermediate Similarity	NPC31907
0.8182	Intermediate Similarity	NPC472252
0.8182	Intermediate Similarity	NPC157659
0.8182	Intermediate Similarity	NPC155010
0.8182	Intermediate Similarity	NPC120123
0.8182	Intermediate Similarity	NPC473020
0.8182	Intermediate Similarity	NPC211879
0.8182	Intermediate Similarity	NPC114874
0.8172	Intermediate Similarity	NPC202886
0.8163	Intermediate Similarity	NPC154127
0.8163	Intermediate Similarity	NPC476896
0.8163	Intermediate Similarity	NPC21064
0.8163	Intermediate Similarity	NPC121072
0.8155	Intermediate Similarity	NPC65034
0.8155	Intermediate Similarity	NPC208189
0.8144	Intermediate Similarity	NPC70733
0.8144	Intermediate Similarity	NPC56071
0.8144	Intermediate Similarity	NPC312325
0.8137	Intermediate Similarity	NPC14630
0.8137	Intermediate Similarity	NPC473318
0.8137	Intermediate Similarity	NPC285253
0.8137	Intermediate Similarity	NPC250089
0.8137	Intermediate Similarity	NPC28844
0.8137	Intermediate Similarity	NPC157530
0.8137	Intermediate Similarity	NPC195116
0.8137	Intermediate Similarity	NPC472901
0.8137	Intermediate Similarity	NPC473328
0.8137	Intermediate Similarity	NPC221110
0.8137	Intermediate Similarity	NPC180459
0.8119	Intermediate Similarity	NPC226642
0.8119	Intermediate Similarity	NPC190395
0.81	Intermediate Similarity	NPC473734
0.81	Intermediate Similarity	NPC100955
0.81	Intermediate Similarity	NPC230948
0.81	Intermediate Similarity	NPC85593
0.81	Intermediate Similarity	NPC471434
0.81	Intermediate Similarity	NPC121566
0.81	Intermediate Similarity	NPC148603
0.81	Intermediate Similarity	NPC109792
0.81	Intermediate Similarity	NPC273879
0.81	Intermediate Similarity	NPC57065
0.81	Intermediate Similarity	NPC54521
0.81	Intermediate Similarity	NPC31430
0.81	Intermediate Similarity	NPC165033
0.81	Intermediate Similarity	NPC173583
0.81	Intermediate Similarity	NPC471435
0.809	Intermediate Similarity	NPC109938
0.809	Intermediate Similarity	NPC122945
0.8085	Intermediate Similarity	NPC289361
0.8081	Intermediate Similarity	NPC288694
0.8081	Intermediate Similarity	NPC159036
0.8081	Intermediate Similarity	NPC150463
0.8081	Intermediate Similarity	NPC312553
0.8081	Intermediate Similarity	NPC300399
0.8081	Intermediate Similarity	NPC214277
0.8081	Intermediate Similarity	NPC471482
0.8077	Intermediate Similarity	NPC231797
0.8077	Intermediate Similarity	NPC174836
0.8065	Intermediate Similarity	NPC477748
0.8065	Intermediate Similarity	NPC115607
0.8061	Intermediate Similarity	NPC477716
0.8061	Intermediate Similarity	NPC473790
0.8061	Intermediate Similarity	NPC471242
0.8061	Intermediate Similarity	NPC477721
0.8043	Intermediate Similarity	NPC189777
0.8041	Intermediate Similarity	NPC98112
0.8041	Intermediate Similarity	NPC26307
0.8039	Intermediate Similarity	NPC235824
0.8039	Intermediate Similarity	NPC473288
0.8022	Intermediate Similarity	NPC477747
0.8022	Intermediate Similarity	NPC477746
0.8021	Intermediate Similarity	NPC476894
0.8021	Intermediate Similarity	NPC100892
0.8021	Intermediate Similarity	NPC477969
0.8021	Intermediate Similarity	NPC477970

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 NPC302584 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	187
0.1-0.2	1811
0.2-0.3	3979
0.3-0.4	2087
0.4-0.5	651
0.5-0.6	248
0.6-0.7	176
0.7-0.8	11
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
0.7941	Intermediate Similarity	NPD6412	Phase 2
0.7864	Intermediate Similarity	NPD6686	Approved
0.7545	Intermediate Similarity	NPD7327	Approved
0.7545	Intermediate Similarity	NPD7328	Approved
0.75	Intermediate Similarity	NPD7503	Approved
0.7477	Intermediate Similarity	NPD7516	Approved
0.7474	Intermediate Similarity	NPD7524	Approved
0.7411	Intermediate Similarity	NPD8294	Approved
0.7411	Intermediate Similarity	NPD8377	Approved
0.7345	Intermediate Similarity	NPD8033	Approved
0.7345	Intermediate Similarity	NPD8380	Approved
0.7345	Intermediate Similarity	NPD8379	Approved
0.7345	Intermediate Similarity	NPD8296	Approved
0.7345	Intermediate Similarity	NPD8335	Approved
0.7345	Intermediate Similarity	NPD8378	Approved
0.734	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD6695	Phase 3
0.7094	Intermediate Similarity	NPD7507	Approved
0.7027	Intermediate Similarity	NPD8133	Approved
0.6989	Remote Similarity	NPD7645	Phase 2
0.6939	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7750	Discontinued
0.6923	Remote Similarity	NPD8328	Phase 3
0.6917	Remote Similarity	NPD7319	Approved
0.6915	Remote Similarity	NPD6930	Phase 2
0.6915	Remote Similarity	NPD6931	Approved
0.6915	Remote Similarity	NPD7525	Registered
0.6857	Remote Similarity	NPD7640	Approved
0.6857	Remote Similarity	NPD7639	Approved
0.6842	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD6370	Approved
0.6813	Remote Similarity	NPD1810	Approved
0.6813	Remote Similarity	NPD1811	Approved
0.6809	Remote Similarity	NPD6929	Approved
0.6804	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD5344	Discontinued
0.6762	Remote Similarity	NPD7638	Approved
0.6762	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD8515	Approved
0.6752	Remote Similarity	NPD8516	Approved
0.6752	Remote Similarity	NPD8517	Approved
0.6752	Remote Similarity	NPD8513	Phase 3
0.6739	Remote Similarity	NPD6942	Approved
0.6739	Remote Similarity	NPD7339	Approved
0.6737	Remote Similarity	NPD7332	Phase 2
0.6737	Remote Similarity	NPD7514	Phase 3
0.6696	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6933	Approved
0.6667	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6059	Approved
0.6667	Remote Similarity	NPD7087	Discontinued
0.6667	Remote Similarity	NPD6054	Approved
0.6667	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD8293	Discontinued
0.6604	Remote Similarity	NPD4225	Approved
0.6602	Remote Similarity	NPD8171	Discontinued
0.6596	Remote Similarity	NPD6925	Approved
0.6596	Remote Similarity	NPD5776	Phase 2
0.6569	Remote Similarity	NPD6698	Approved
0.6569	Remote Similarity	NPD3168	Discontinued
0.6569	Remote Similarity	NPD46	Approved
0.6566	Remote Similarity	NPD6893	Approved
0.6559	Remote Similarity	NPD8264	Approved
0.6557	Remote Similarity	NPD7736	Approved
0.6526	Remote Similarity	NPD7145	Approved
0.6512	Remote Similarity	NPD368	Approved
0.6505	Remote Similarity	NPD7637	Suspended
0.65	Remote Similarity	NPD6067	Discontinued
0.6495	Remote Similarity	NPD6902	Approved
0.6495	Remote Similarity	NPD6898	Phase 1
0.6484	Remote Similarity	NPD2687	Approved
0.6484	Remote Similarity	NPD2686	Approved
0.6484	Remote Similarity	NPD2254	Approved
0.648	Remote Similarity	NPD8449	Approved
0.6471	Remote Similarity	NPD6015	Approved
0.6471	Remote Similarity	NPD6016	Approved
0.6471	Remote Similarity	NPD6051	Approved
0.6452	Remote Similarity	NPD6926	Approved
0.6452	Remote Similarity	NPD6924	Approved
0.6446	Remote Similarity	NPD7492	Approved
0.6442	Remote Similarity	NPD5778	Approved
0.6442	Remote Similarity	NPD5779	Approved
0.6442	Remote Similarity	NPD6399	Phase 3
0.6429	Remote Similarity	NPD8450	Suspended
0.6429	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD6932	Approved
0.6417	Remote Similarity	NPD5988	Approved
0.6413	Remote Similarity	NPD4243	Approved
0.641	Remote Similarity	NPD7115	Discovery
0.641	Remote Similarity	NPD6009	Approved
0.6408	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD7838	Discovery
0.6393	Remote Similarity	NPD6616	Approved
0.6389	Remote Similarity	NPD6648	Approved
0.6355	Remote Similarity	NPD6083	Phase 2
0.6355	Remote Similarity	NPD6084	Phase 2
0.6354	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD6882	Approved
0.6346	Remote Similarity	NPD6411	Approved
0.6346	Remote Similarity	NPD7983	Approved
0.6341	Remote Similarity	NPD7078	Approved
0.6316	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.63	Remote Similarity	NPD4786	Approved
0.6293	Remote Similarity	NPD4632	Approved
0.6289	Remote Similarity	NPD6683	Phase 2
0.6281	Remote Similarity	NPD5126	Approved
0.6281	Remote Similarity	NPD5125	Phase 3
0.6277	Remote Similarity	NPD4784	Approved
0.6277	Remote Similarity	NPD4785	Approved
0.6273	Remote Similarity	NPD7632	Discontinued
0.6263	Remote Similarity	NPD3667	Approved
0.625	Remote Similarity	NPD6402	Approved
0.625	Remote Similarity	NPD5739	Approved
0.625	Remote Similarity	NPD6675	Approved
0.625	Remote Similarity	NPD6640	Phase 3
0.625	Remote Similarity	NPD6319	Approved
0.625	Remote Similarity	NPD7128	Approved
0.6226	Remote Similarity	NPD7748	Approved
0.6224	Remote Similarity	NPD6928	Phase 2
0.6224	Remote Similarity	NPD7509	Discontinued
0.621	Remote Similarity	NPD8074	Phase 3
0.6207	Remote Similarity	NPD6053	Discontinued
0.6207	Remote Similarity	NPD8297	Approved
0.6204	Remote Similarity	NPD7902	Approved
0.62	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.62	Remote Similarity	NPD3669	Approved
0.619	Remote Similarity	NPD6914	Discontinued
0.619	Remote Similarity	NPD7515	Phase 2
0.6182	Remote Similarity	NPD4159	Approved
0.6174	Remote Similarity	NPD6371	Approved
0.6168	Remote Similarity	NPD5695	Phase 3
0.616	Remote Similarity	NPD6033	Approved
0.6154	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6101	Approved
0.6154	Remote Similarity	NPD4753	Phase 2
0.614	Remote Similarity	NPD6881	Approved
0.614	Remote Similarity	NPD6899	Approved
0.614	Remote Similarity	NPD7320	Approved
0.6139	Remote Similarity	NPD3665	Phase 1
0.6139	Remote Similarity	NPD3133	Approved
0.6139	Remote Similarity	NPD3666	Approved
0.6126	Remote Similarity	NPD5211	Phase 2
0.6106	Remote Similarity	NPD5357	Phase 1
0.6087	Remote Similarity	NPD6373	Approved
0.6087	Remote Similarity	NPD6372	Approved
0.6063	Remote Similarity	NPD5956	Approved
0.6061	Remote Similarity	NPD4748	Discontinued
0.6055	Remote Similarity	NPD4755	Approved
0.6053	Remote Similarity	NPD5697	Approved
0.6053	Remote Similarity	NPD5701	Approved
0.6053	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD8341	Approved
0.6048	Remote Similarity	NPD8340	Approved
0.6048	Remote Similarity	NPD8299	Approved
0.6048	Remote Similarity	NPD8342	Approved
0.6042	Remote Similarity	NPD5275	Approved
0.6042	Remote Similarity	NPD4190	Phase 3
0.604	Remote Similarity	NPD6110	Phase 1
0.6034	Remote Similarity	NPD6883	Approved
0.6034	Remote Similarity	NPD7290	Approved
0.6034	Remote Similarity	NPD4634	Approved
0.6034	Remote Similarity	NPD7102	Approved
0.6023	Remote Similarity	NPD1145	Discontinued
0.6022	Remote Similarity	NPD6922	Approved
0.6022	Remote Similarity	NPD6923	Approved
0.6019	Remote Similarity	NPD7334	Approved
0.6019	Remote Similarity	NPD7521	Approved
0.6019	Remote Similarity	NPD4623	Approved
0.6019	Remote Similarity	NPD6409	Approved
0.6019	Remote Similarity	NPD4519	Discontinued
0.6019	Remote Similarity	NPD6684	Approved
0.6019	Remote Similarity	NPD7146	Approved
0.6019	Remote Similarity	NPD3618	Phase 1
0.6019	Remote Similarity	NPD5330	Approved
0.6018	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD5141	Approved
0.6	Remote Similarity	NPD342	Phase 1
0.6	Remote Similarity	NPD5328	Approved
0.6	Remote Similarity	NPD5696	Approved
0.6	Remote Similarity	NPD4732	Discontinued
0.6	Remote Similarity	NPD371	Approved
0.5985	Remote Similarity	NPD7625	Phase 1
0.5983	Remote Similarity	NPD8130	Phase 1
0.5983	Remote Similarity	NPD6617	Approved
0.5983	Remote Similarity	NPD6650	Approved
0.5983	Remote Similarity	NPD6847	Approved
0.5983	Remote Similarity	NPD6649	Approved
0.5983	Remote Similarity	NPD6869	Approved
0.5981	Remote Similarity	NPD4202	Approved
0.5968	Remote Similarity	NPD7604	Phase 2
0.5963	Remote Similarity	NPD7839	Suspended
0.5962	Remote Similarity	NPD4251	Approved
0.5962	Remote Similarity	NPD4250	Approved
0.596	Remote Similarity	NPD4195	Approved
0.5957	Remote Similarity	NPD7144	Approved
0.5957	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD7143	Approved
0.5948	Remote Similarity	NPD6012	Approved
0.5948	Remote Similarity	NPD6013	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