NPASS Compound

Structure

NPC91654 OpenBabel07101718272D 31 33 0 0 1 0 0 0 0 0999 V2000 -1.1340 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4641 -1.0000 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 -5.9641 3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1340 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4641 -0.0000 0.0000 C 0 0 0 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 -4.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4641 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5000 0.8660 0.0000 C 0 0 1 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 -5.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5981 1.5000 0.0000 C 0 0 1 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 8 2 0 0 0 0 2 16 1 0 0 0 0 4 24 1 0 0 0 0 5 24 1 0 0 0 0 8 25 1 0 0 0 0 9 13 1 0 0 0 0 9 14 1 0 0 0 0 10 11 1 0 0 0 0 10 16 2 0 0 0 0 11 19 1 0 0 0 0 12 15 1 0 0 0 0 12 18 1 0 0 0 0 13 24 1 0 0 0 0 14 26 1 0 0 0 0 15 25 1 0 0 0 0 16 18 1 0 0 0 0 17 3 1 1 0 0 0 17 20 1 0 0 0 0 17 30 1 0 0 0 0 18 26 1 1 0 0 0 19 24 1 0 0 0 0 19 26 1 1 0 0 0 20 21 1 0 0 0 0 20 27 1 1 0 0 0 21 22 1 0 0 0 0 21 28 1 1 0 0 0 22 23 1 0 0 0 0 22 29 1 6 0 0 0 23 30 1 0 0 0 0 23 31 1 1 0 0 0 25 6 1 6 0 0 0 25 31 1 0 0 0 0 26 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	436.32
Volume:	471.261
LogP:	4.947
LogD:	4.04
LogS:	-4.921
# Rotatable Bonds:	6
TPSA:	79.15
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.539
Synthetic Accessibility Score:	4.943
Fsp3:	0.846
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:	-4.713
MDCK Permeability:	1.7611455405130982e-05
Pgp-inhibitor:	0.981
Pgp-substrate:	0.242
Human Intestinal Absorption (HIA):	0.045
20% Bioavailability (F20%):	0.351
30% Bioavailability (F30%):	0.029

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.027
Plasma Protein Binding (PPB):	93.66151428222656%
Volume Distribution (VD):	2.051
Pgp-substrate:	5.418482303619385%

ADMET: Metabolism

CYP1A2-inhibitor:	0.025
CYP1A2-substrate:	0.704
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.891
CYP2C9-inhibitor:	0.198
CYP2C9-substrate:	0.254
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.686
CYP3A4-inhibitor:	0.519
CYP3A4-substrate:	0.234

ADMET: Excretion

Clearance (CL):	1.99
Half-life (T1/2):	0.213

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.087
Drug-inuced Liver Injury (DILI):	0.019
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.086
Maximum Recommended Daily Dose:	0.024
Skin Sensitization:	0.534
Carcinogencity:	0.044
Eye Corrosion:	0.034
Eye Irritation:	0.12
Respiratory Toxicity:	0.81

Download Data

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

Natural Product: NPC91654

Natural Product ID:	NPC91654
*Common Name:**	(13R)-Labda-7,14-Diene 13-O-Beta-D-Fucopyranoside
IUPAC Name:	(2S,3R,4S,5R,6R)-2-[(3R)-5-[(1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-1-en-3-yl]oxy-6-methyloxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	SHBMAOBNYQEHHP-OGVOCQFYSA-N
Standard InCHI:	InChI=1S/C26H44O5/c1-8-25(6,31-23-22(29)21(28)20(27)17(3)30-23)15-12-18-16(2)10-11-19-24(4,5)13-9-14-26(18,19)7/h8,10,17-23,27-29H,1,9,11-15H2,2-7H3/t17-,18+,19+,20+,21+,22-,23+,25+,26-/m1/s1
SMILES:	C=C[C@](O[C@@H]1O[C@H](C)[C@@H]([C@@H]([C@H]1O)O)O)(CC[C@H]1C(=CC[C@@H]2[C@]1(C)CCCC2(C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL457603
PubChem CID:	44584270
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO3386	Aster spathulifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16252909]
NPO3386	Aster spathulifolius	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[17121178]
NPO3386	Aster spathulifolius	Species	Asteraceae	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
ED50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	3.5	ug ml-1	PMID[449774]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	3.6	ug ml-1	PMID[449774]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	3.5	ug ml-1	PMID[449774]
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	4.2	ug ml-1	PMID[449774]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	3.9	ug ml-1	PMID[449774]

☑ 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 NPC91654 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	219
0.1-0.2	1480
0.2-0.3	4811
0.3-0.4	11396
0.4-0.5	11098
0.5-0.6	7245
0.6-0.7	4883
0.7-0.8	1473
0.8-0.85	60
0.85-0.9	19
0.9-0.95	4
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474792
1.0	High Similarity	NPC67398
0.9556	High Similarity	NPC239547
0.9556	High Similarity	NPC91197
0.9556	High Similarity	NPC96597
0.9556	High Similarity	NPC155319
0.9556	High Similarity	NPC309503
0.9556	High Similarity	NPC125551
0.9432	High Similarity	NPC302584
0.907	High Similarity	NPC166279
0.9043	High Similarity	NPC285231
0.9043	High Similarity	NPC21568
0.9043	High Similarity	NPC280991
0.9011	High Similarity	NPC305160
0.8989	High Similarity	NPC309310
0.8989	High Similarity	NPC473058
0.8901	High Similarity	NPC474835
0.8889	High Similarity	NPC474249
0.8889	High Similarity	NPC159876
0.8889	High Similarity	NPC261990
0.8876	High Similarity	NPC248312
0.8817	High Similarity	NPC90583
0.8776	High Similarity	NPC33053
0.8723	High Similarity	NPC240372
0.866	High Similarity	NPC473123
0.866	High Similarity	NPC473124
0.8652	High Similarity	NPC470836
0.8632	High Similarity	NPC158088
0.8617	High Similarity	NPC207617
0.8605	High Similarity	NPC100697
0.8602	High Similarity	NPC178949
0.8602	High Similarity	NPC96736
0.8602	High Similarity	NPC477927
0.8602	High Similarity	NPC72817
0.8587	High Similarity	NPC289361
0.8571	High Similarity	NPC93352
0.8571	High Similarity	NPC203354
0.8571	High Similarity	NPC473127
0.8571	High Similarity	NPC110656
0.8542	High Similarity	NPC64348
0.8542	High Similarity	NPC469942
0.8526	High Similarity	NPC243728
0.8526	High Similarity	NPC473890
0.8515	High Similarity	NPC103627
0.8515	High Similarity	NPC191439
0.8515	High Similarity	NPC170974
0.8511	High Similarity	NPC286612
0.8511	High Similarity	NPC230347
0.8511	High Similarity	NPC275310
0.85	High Similarity	NPC80210
0.85	High Similarity	NPC38376
0.8485	Intermediate Similarity	NPC470763
0.8485	Intermediate Similarity	NPC470767
0.8454	Intermediate Similarity	NPC470434
0.8454	Intermediate Similarity	NPC267510
0.8438	Intermediate Similarity	NPC216260
0.8438	Intermediate Similarity	NPC312325
0.8438	Intermediate Similarity	NPC5358
0.8431	Intermediate Similarity	NPC208189
0.8431	Intermediate Similarity	NPC65034
0.8416	Intermediate Similarity	NPC221110
0.8416	Intermediate Similarity	NPC180459
0.8416	Intermediate Similarity	NPC195116
0.8416	Intermediate Similarity	NPC473318
0.8416	Intermediate Similarity	NPC285253
0.8416	Intermediate Similarity	NPC473328
0.8416	Intermediate Similarity	NPC28844
0.8409	Intermediate Similarity	NPC20072
0.8404	Intermediate Similarity	NPC211238
0.84	Intermediate Similarity	NPC281939
0.837	Intermediate Similarity	NPC470819
0.8367	Intermediate Similarity	NPC154452
0.8367	Intermediate Similarity	NPC470571
0.8367	Intermediate Similarity	NPC272015
0.8351	Intermediate Similarity	NPC282669
0.835	Intermediate Similarity	NPC231797
0.835	Intermediate Similarity	NPC473567
0.835	Intermediate Similarity	NPC216595
0.8333	Intermediate Similarity	NPC65155
0.8283	Intermediate Similarity	NPC471888
0.8283	Intermediate Similarity	NPC471886
0.8283	Intermediate Similarity	NPC99627
0.8283	Intermediate Similarity	NPC471885
0.8283	Intermediate Similarity	NPC471887
0.8283	Intermediate Similarity	NPC162354
0.8283	Intermediate Similarity	NPC473129
0.828	Intermediate Similarity	NPC470817
0.828	Intermediate Similarity	NPC202886
0.8265	Intermediate Similarity	NPC117714
0.8265	Intermediate Similarity	NPC154127
0.8265	Intermediate Similarity	NPC160734
0.8265	Intermediate Similarity	NPC21064
0.8265	Intermediate Similarity	NPC88000
0.8265	Intermediate Similarity	NPC47566
0.8265	Intermediate Similarity	NPC129372
0.8265	Intermediate Similarity	NPC263756
0.8265	Intermediate Similarity	NPC4831
0.8265	Intermediate Similarity	NPC472023
0.8265	Intermediate Similarity	NPC309425
0.8265	Intermediate Similarity	NPC121072
0.8252	Intermediate Similarity	NPC110494
0.8252	Intermediate Similarity	NPC157474
0.8247	Intermediate Similarity	NPC477928
0.8247	Intermediate Similarity	NPC234287
0.8247	Intermediate Similarity	NPC280825
0.8235	Intermediate Similarity	NPC250089
0.8235	Intermediate Similarity	NPC157530
0.8235	Intermediate Similarity	NPC472901
0.8235	Intermediate Similarity	NPC14630
0.8222	Intermediate Similarity	NPC83702
0.8218	Intermediate Similarity	NPC472390
0.82	Intermediate Similarity	NPC470768
0.82	Intermediate Similarity	NPC75608
0.82	Intermediate Similarity	NPC470885
0.82	Intermediate Similarity	NPC187400
0.82	Intermediate Similarity	NPC109792
0.82	Intermediate Similarity	NPC57065
0.82	Intermediate Similarity	NPC54521
0.82	Intermediate Similarity	NPC221562
0.8182	Intermediate Similarity	NPC76497
0.8182	Intermediate Similarity	NPC256133
0.8182	Intermediate Similarity	NPC300399
0.8182	Intermediate Similarity	NPC136816
0.8182	Intermediate Similarity	NPC37207
0.8182	Intermediate Similarity	NPC213674
0.8182	Intermediate Similarity	NPC30289
0.8182	Intermediate Similarity	NPC471482
0.8173	Intermediate Similarity	NPC476305
0.8173	Intermediate Similarity	NPC473125
0.8172	Intermediate Similarity	NPC477748
0.8163	Intermediate Similarity	NPC473200
0.8163	Intermediate Similarity	NPC324598
0.8163	Intermediate Similarity	NPC7341
0.8144	Intermediate Similarity	NPC26307
0.8144	Intermediate Similarity	NPC98112
0.8137	Intermediate Similarity	NPC128795
0.8137	Intermediate Similarity	NPC217921
0.8137	Intermediate Similarity	NPC135015
0.8137	Intermediate Similarity	NPC48548
0.8132	Intermediate Similarity	NPC119001
0.8125	Intermediate Similarity	NPC100892
0.8125	Intermediate Similarity	NPC477969
0.8125	Intermediate Similarity	NPC477970
0.8125	Intermediate Similarity	NPC108141
0.8125	Intermediate Similarity	NPC135224
0.8119	Intermediate Similarity	NPC472898
0.8119	Intermediate Similarity	NPC474569
0.8119	Intermediate Similarity	NPC239961
0.8119	Intermediate Similarity	NPC472900
0.8119	Intermediate Similarity	NPC309448
0.8119	Intermediate Similarity	NPC26798
0.8119	Intermediate Similarity	NPC82251
0.8119	Intermediate Similarity	NPC472899
0.81	Intermediate Similarity	NPC189852
0.81	Intermediate Similarity	NPC8039
0.81	Intermediate Similarity	NPC473198
0.81	Intermediate Similarity	NPC157659
0.81	Intermediate Similarity	NPC120123
0.81	Intermediate Similarity	NPC31907
0.81	Intermediate Similarity	NPC245280
0.81	Intermediate Similarity	NPC155010
0.81	Intermediate Similarity	NPC211879
0.81	Intermediate Similarity	NPC213190
0.81	Intermediate Similarity	NPC131479
0.81	Intermediate Similarity	NPC473020
0.81	Intermediate Similarity	NPC16520
0.81	Intermediate Similarity	NPC471450
0.81	Intermediate Similarity	NPC286969
0.81	Intermediate Similarity	NPC472252
0.81	Intermediate Similarity	NPC123796
0.81	Intermediate Similarity	NPC114874
0.8095	Intermediate Similarity	NPC44298
0.8095	Intermediate Similarity	NPC473159
0.8095	Intermediate Similarity	NPC473128
0.8095	Intermediate Similarity	NPC290608
0.8095	Intermediate Similarity	NPC469347
0.8095	Intermediate Similarity	NPC469348
0.8095	Intermediate Similarity	NPC40133
0.8095	Intermediate Similarity	NPC49413
0.809	Intermediate Similarity	NPC16090
0.8081	Intermediate Similarity	NPC198992
0.8077	Intermediate Similarity	NPC472987
0.8077	Intermediate Similarity	NPC473021
0.8077	Intermediate Similarity	NPC13190
0.8061	Intermediate Similarity	NPC70733
0.8061	Intermediate Similarity	NPC198422
0.8061	Intermediate Similarity	NPC40182
0.8061	Intermediate Similarity	NPC56071
0.8058	Intermediate Similarity	NPC316974
0.8058	Intermediate Similarity	NPC40728
0.8058	Intermediate Similarity	NPC128133
0.8039	Intermediate Similarity	NPC226642
0.8039	Intermediate Similarity	NPC257964
0.8039	Intermediate Similarity	NPC190395
0.8039	Intermediate Similarity	NPC231340
0.8039	Intermediate Similarity	NPC88013
0.8039	Intermediate Similarity	NPC125423
0.8021	Intermediate Similarity	NPC25701
0.8021	Intermediate Similarity	NPC2003
0.8021	Intermediate Similarity	NPC189513

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 NPC91654 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	189
0.1-0.2	1704
0.2-0.3	3974
0.3-0.4	2158
0.4-0.5	692
0.5-0.6	263
0.6-0.7	160
0.7-0.8	10
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
0.7961	Intermediate Similarity	NPD6686	Approved
0.7864	Intermediate Similarity	NPD6412	Phase 2
0.7748	Intermediate Similarity	NPD7503	Approved
0.7636	Intermediate Similarity	NPD7328	Approved
0.7636	Intermediate Similarity	NPD7327	Approved
0.7568	Intermediate Similarity	NPD7516	Approved
0.75	Intermediate Similarity	NPD8294	Approved
0.75	Intermediate Similarity	NPD8377	Approved
0.7434	Intermediate Similarity	NPD8335	Approved
0.7434	Intermediate Similarity	NPD8378	Approved
0.7434	Intermediate Similarity	NPD8379	Approved
0.7434	Intermediate Similarity	NPD8033	Approved
0.7434	Intermediate Similarity	NPD8296	Approved
0.7434	Intermediate Similarity	NPD8380	Approved
0.7273	Intermediate Similarity	NPD8133	Approved
0.7222	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7524	Approved
0.7179	Intermediate Similarity	NPD7507	Approved
0.7083	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7319	Approved
0.6979	Remote Similarity	NPD6695	Phase 3
0.6923	Remote Similarity	NPD6370	Approved
0.6915	Remote Similarity	NPD7645	Phase 2
0.6887	Remote Similarity	NPD5344	Discontinued
0.6864	Remote Similarity	NPD8328	Phase 3
0.6857	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7638	Approved
0.6842	Remote Similarity	NPD7525	Registered
0.6838	Remote Similarity	NPD8517	Approved
0.6838	Remote Similarity	NPD8515	Approved
0.6838	Remote Similarity	NPD8516	Approved
0.6838	Remote Similarity	NPD8513	Phase 3
0.6818	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD7639	Approved
0.6792	Remote Similarity	NPD7640	Approved
0.6786	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6054	Approved
0.6739	Remote Similarity	NPD1811	Approved
0.6739	Remote Similarity	NPD1810	Approved
0.6735	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.67	Remote Similarity	NPD7750	Discontinued
0.6667	Remote Similarity	NPD6931	Approved
0.6667	Remote Similarity	NPD6930	Phase 2
0.6667	Remote Similarity	NPD46	Approved
0.6667	Remote Similarity	NPD6698	Approved
0.6667	Remote Similarity	NPD6942	Approved
0.6667	Remote Similarity	NPD7339	Approved
0.6667	Remote Similarity	NPD7838	Discovery
0.6639	Remote Similarity	NPD7736	Approved
0.661	Remote Similarity	NPD6059	Approved
0.6596	Remote Similarity	NPD6933	Approved
0.6596	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD6051	Approved
0.6562	Remote Similarity	NPD6929	Approved
0.6557	Remote Similarity	NPD8293	Discontinued
0.6555	Remote Similarity	NPD6015	Approved
0.6555	Remote Similarity	NPD6016	Approved
0.6542	Remote Similarity	NPD4225	Approved
0.6538	Remote Similarity	NPD8171	Discontinued
0.6535	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD7492	Approved
0.6526	Remote Similarity	NPD6932	Approved
0.6505	Remote Similarity	NPD3168	Discontinued
0.65	Remote Similarity	NPD5126	Approved
0.65	Remote Similarity	NPD5988	Approved
0.65	Remote Similarity	NPD5125	Phase 3
0.6496	Remote Similarity	NPD6009	Approved
0.6496	Remote Similarity	NPD7115	Discovery
0.6495	Remote Similarity	NPD7332	Phase 2
0.6495	Remote Similarity	NPD7514	Phase 3
0.6481	Remote Similarity	NPD6648	Approved
0.6475	Remote Similarity	NPD6616	Approved
0.6458	Remote Similarity	NPD7145	Approved
0.6446	Remote Similarity	NPD6067	Discontinued
0.6442	Remote Similarity	NPD6411	Approved
0.6442	Remote Similarity	NPD7087	Discontinued
0.6435	Remote Similarity	NPD6882	Approved
0.6429	Remote Similarity	NPD8449	Approved
0.6423	Remote Similarity	NPD7078	Approved
0.6413	Remote Similarity	NPD2686	Approved
0.6413	Remote Similarity	NPD2687	Approved
0.6413	Remote Similarity	NPD2254	Approved
0.6404	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD6926	Approved
0.6383	Remote Similarity	NPD6924	Approved
0.6383	Remote Similarity	NPD4784	Approved
0.6383	Remote Similarity	NPD4785	Approved
0.6381	Remote Similarity	NPD6399	Phase 3
0.6379	Remote Similarity	NPD4632	Approved
0.6378	Remote Similarity	NPD8450	Suspended
0.6354	Remote Similarity	NPD5776	Phase 2
0.6354	Remote Similarity	NPD6925	Approved
0.6344	Remote Similarity	NPD4243	Approved
0.6337	Remote Similarity	NPD6893	Approved
0.6333	Remote Similarity	NPD6319	Approved
0.6316	Remote Similarity	NPD8264	Approved
0.6296	Remote Similarity	NPD6083	Phase 2
0.6296	Remote Similarity	NPD6084	Phase 2
0.6293	Remote Similarity	NPD8297	Approved
0.6293	Remote Similarity	NPD6053	Discontinued
0.629	Remote Similarity	NPD8074	Phase 3
0.6286	Remote Similarity	NPD7637	Suspended
0.6273	Remote Similarity	NPD4159	Approved
0.6263	Remote Similarity	NPD6902	Approved
0.6263	Remote Similarity	NPD6898	Phase 1
0.625	Remote Similarity	NPD6101	Approved
0.625	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD4786	Approved
0.6228	Remote Similarity	NPD6899	Approved
0.6228	Remote Similarity	NPD6881	Approved
0.6226	Remote Similarity	NPD5779	Approved
0.6226	Remote Similarity	NPD5778	Approved
0.6224	Remote Similarity	NPD6683	Phase 2
0.6216	Remote Similarity	NPD7632	Discontinued
0.62	Remote Similarity	NPD3667	Approved
0.6195	Remote Similarity	NPD6675	Approved
0.6195	Remote Similarity	NPD7128	Approved
0.6195	Remote Similarity	NPD6640	Phase 3
0.6195	Remote Similarity	NPD5739	Approved
0.6195	Remote Similarity	NPD6402	Approved
0.619	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD7748	Approved
0.6162	Remote Similarity	NPD7509	Discontinued
0.6162	Remote Similarity	NPD6928	Phase 2
0.6148	Remote Similarity	NPD6921	Approved
0.6147	Remote Similarity	NPD7902	Approved
0.6142	Remote Similarity	NPD5956	Approved
0.614	Remote Similarity	NPD5697	Approved
0.614	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD3669	Approved
0.6139	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD7515	Phase 2
0.6132	Remote Similarity	NPD7983	Approved
0.6122	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD7102	Approved
0.6121	Remote Similarity	NPD6883	Approved
0.6121	Remote Similarity	NPD6371	Approved
0.6121	Remote Similarity	NPD4634	Approved
0.6121	Remote Similarity	NPD7290	Approved
0.6111	Remote Similarity	NPD5695	Phase 3
0.6111	Remote Similarity	NPD6033	Approved
0.6095	Remote Similarity	NPD4753	Phase 2
0.6087	Remote Similarity	NPD7320	Approved
0.608	Remote Similarity	NPD8451	Approved
0.6078	Remote Similarity	NPD3133	Approved
0.6078	Remote Similarity	NPD3666	Approved
0.6078	Remote Similarity	NPD3665	Phase 1
0.6071	Remote Similarity	NPD5211	Phase 2
0.6068	Remote Similarity	NPD6650	Approved
0.6068	Remote Similarity	NPD8130	Phase 1
0.6068	Remote Similarity	NPD6649	Approved
0.6068	Remote Similarity	NPD6869	Approved
0.6068	Remote Similarity	NPD6847	Approved
0.6068	Remote Similarity	NPD6617	Approved
0.6067	Remote Similarity	NPD368	Approved
0.6064	Remote Similarity	NPD7144	Approved
0.6064	Remote Similarity	NPD7143	Approved
0.6061	Remote Similarity	NPD4195	Approved
0.6058	Remote Similarity	NPD7625	Phase 1
0.6053	Remote Similarity	NPD5357	Phase 1
0.6048	Remote Similarity	NPD7604	Phase 2
0.6036	Remote Similarity	NPD4696	Approved
0.6036	Remote Similarity	NPD5285	Approved
0.6036	Remote Similarity	NPD5286	Approved
0.6034	Remote Similarity	NPD6012	Approved
0.6034	Remote Similarity	NPD6014	Approved
0.6034	Remote Similarity	NPD6013	Approved
0.6034	Remote Similarity	NPD6372	Approved
0.6034	Remote Similarity	NPD6373	Approved
0.6032	Remote Similarity	NPD8448	Approved
0.6019	Remote Similarity	NPD5282	Discontinued
0.6016	Remote Similarity	NPD8392	Approved
0.6016	Remote Similarity	NPD8390	Approved
0.6016	Remote Similarity	NPD8391	Approved
0.6016	Remote Similarity	NPD5983	Phase 2
0.6	Remote Similarity	NPD7150	Approved
0.6	Remote Similarity	NPD4748	Discontinued
0.6	Remote Similarity	NPD7151	Approved
0.6	Remote Similarity	NPD5701	Approved
0.6	Remote Similarity	NPD7152	Approved
0.6	Remote Similarity	NPD4755	Approved
0.5981	Remote Similarity	NPD6079	Approved
0.5979	Remote Similarity	NPD4190	Phase 3
0.5979	Remote Similarity	NPD5275	Approved
0.5965	Remote Similarity	NPD5141	Approved
0.5965	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD5210	Approved
0.5963	Remote Similarity	NPD4629	Approved
0.5962	Remote Similarity	NPD6684	Approved
0.5962	Remote Similarity	NPD7334	Approved
0.5962	Remote Similarity	NPD3618	Phase 1
0.5962	Remote Similarity	NPD7521	Approved
0.5962	Remote Similarity	NPD7146	Approved
0.5962	Remote Similarity	NPD6409	Approved
0.5962	Remote Similarity	NPD5330	Approved
0.5957	Remote Similarity	NPD6922	Approved
0.5957	Remote Similarity	NPD6923	Approved
0.5955	Remote Similarity	NPD1145	Discontinued

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