NPASS Compound

Structure

CID20072 OpenBabel06191715342D 31 33 0 0 1 0 0 0 0 0999 V2000 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 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 4.3301 -2.5000 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 -5.1962 -1.0000 0.0000 C 0 0 1 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 -4.3301 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 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 1 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 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 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 21 1 0 0 0 0 3 21 1 0 0 0 0 4 6 1 0 0 0 0 4 10 2 0 0 0 0 5 7 1 0 0 0 0 5 10 1 0 0 0 0 6 11 1 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 8 28 1 0 0 0 0 9 29 1 0 0 0 0 11 21 1 1 0 0 0 12 14 1 0 0 0 0 12 22 1 1 0 0 0 13 9 1 6 0 0 0 13 15 1 0 0 0 0 13 30 1 0 0 0 0 14 17 1 0 0 0 0 14 23 1 1 0 0 0 15 16 1 0 0 0 0 15 24 1 1 0 0 0 16 18 1 0 0 0 0 16 25 1 6 0 0 0 17 19 1 0 0 0 0 17 26 1 6 0 0 0 18 20 1 0 0 0 0 18 27 1 1 0 0 0 19 28 1 0 0 0 0 19 29 1 1 0 0 0 20 30 1 0 0 0 0 20 31 1 6 0 0 0 21 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	448.23
Volume:	431.369
LogP:	0.474
LogD:	0.781
LogS:	-2.288
# Rotatable Bonds:	6
TPSA:	158.3
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.272
Synthetic Accessibility Score:	4.806
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:	-5.293
MDCK Permeability:	2.8546699468279257e-05
Pgp-inhibitor:	0.985
Pgp-substrate:	0.961
Human Intestinal Absorption (HIA):	0.945
20% Bioavailability (F20%):	0.056
30% Bioavailability (F30%):	0.961

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.122
Plasma Protein Binding (PPB):	61.84237289428711%
Volume Distribution (VD):	0.516
Pgp-substrate:	27.60696029663086%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.069
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.076
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.05
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.117
CYP3A4-inhibitor:	0.007
CYP3A4-substrate:	0.02

ADMET: Excretion

Clearance (CL):	1.029
Half-life (T1/2):	0.7

ADMET: Toxicity

hERG Blockers:	0.072
Human Hepatotoxicity (H-HT):	0.09
Drug-inuced Liver Injury (DILI):	0.018
AMES Toxicity:	0.201
Rat Oral Acute Toxicity:	0.353
Maximum Recommended Daily Dose:	0.05
Skin Sensitization:	0.655
Carcinogencity:	0.385
Eye Corrosion:	0.004
Eye Irritation:	0.098
Respiratory Toxicity:	0.25

Download Data

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

Natural Product: NPC20072

Natural Product ID:	NPC20072
*Common Name:**	(4S)-Alpha-Terpineol 8-O-[Alpha-L-Arabinopyranosyl-(1->6)-Beta-D-Glucopyranoside]
IUPAC Name:	(2S,3R,4S,5S,6R)-2-[2-[(1S)-4-methylcyclohex-3-en-1-yl]propan-2-yloxy]-6-[[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	YBPOIRBPAOCVPU-SRGUVOPWSA-N
Standard InCHI:	InChI=1S/C21H36O10/c1-10-4-6-11(7-5-10)21(2,3)31-20-18(27)16(25)15(24)13(30-20)9-29-19-17(26)14(23)12(22)8-28-19/h4,11-20,22-27H,5-9H2,1-3H3/t11-,12+,13-,14+,15-,16+,17-,18-,19+,20+/m1/s1
SMILES:	CC1=CC[C@H](CC1)C(C)(C)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO[C@H]2[C@@H]([C@H]([C@H](CO2)O)O)O)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3236508
PubChem CID:	90671008
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0002207] O-glycosyl compounds

*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
NPO5731	Euphorbia humifusa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5731	Euphorbia humifusa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5731	Euphorbia humifusa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5731	Euphorbia humifusa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2922	Botryosphaeria berengeriana	Species	Botryosphaeriaceae	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	1
Others	1

Activity Type	# Activity
Cell Line	1
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	50000.0	nM	PMID[482667]
NPT862	Individual Protein	Epoxide hydratase	Homo sapiens	Inhibition	<	40.0	%	PMID[482667]

☑ 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 NPC20072 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	194
0.1-0.2	1670
0.2-0.3	6256
0.3-0.4	14496
0.4-0.5	9561
0.5-0.6	7144
0.6-0.7	2934
0.7-0.8	404
0.8-0.85	27
0.85-0.9	8
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9481	High Similarity	NPC100697
0.9268	High Similarity	NPC248312
0.8902	High Similarity	NPC477746
0.8902	High Similarity	NPC477747
0.8795	High Similarity	NPC470836
0.8554	High Similarity	NPC166279
0.8506	High Similarity	NPC302584
0.8488	Intermediate Similarity	NPC477748
0.8409	Intermediate Similarity	NPC474792
0.8409	Intermediate Similarity	NPC91654
0.8409	Intermediate Similarity	NPC67398
0.8391	Intermediate Similarity	NPC202886
0.8315	Intermediate Similarity	NPC96736
0.8315	Intermediate Similarity	NPC178949
0.8295	Intermediate Similarity	NPC477749
0.8132	Intermediate Similarity	NPC90583
0.8111	Intermediate Similarity	NPC72817
0.8111	Intermediate Similarity	NPC305160
0.8111	Intermediate Similarity	NPC477927
0.8068	Intermediate Similarity	NPC473058
0.8065	Intermediate Similarity	NPC64348
0.8043	Intermediate Similarity	NPC239547
0.8043	Intermediate Similarity	NPC155319
0.8043	Intermediate Similarity	NPC309503
0.8043	Intermediate Similarity	NPC96597
0.8043	Intermediate Similarity	NPC125551
0.8043	Intermediate Similarity	NPC91197
0.7979	Intermediate Similarity	NPC263756
0.7979	Intermediate Similarity	NPC117714
0.7978	Intermediate Similarity	NPC159876
0.7957	Intermediate Similarity	NPC56071
0.7957	Intermediate Similarity	NPC70733
0.7917	Intermediate Similarity	NPC470885
0.7917	Intermediate Similarity	NPC187400
0.7917	Intermediate Similarity	NPC221562
0.7895	Intermediate Similarity	NPC30289
0.7895	Intermediate Similarity	NPC272015
0.7895	Intermediate Similarity	NPC256133
0.7895	Intermediate Similarity	NPC213674
0.7895	Intermediate Similarity	NPC76497
0.7875	Intermediate Similarity	NPC55652
0.7865	Intermediate Similarity	NPC309310
0.7849	Intermediate Similarity	NPC473890
0.7849	Intermediate Similarity	NPC278506
0.7849	Intermediate Similarity	NPC240372
0.7849	Intermediate Similarity	NPC243728
0.7841	Intermediate Similarity	NPC125142
0.7835	Intermediate Similarity	NPC470763
0.7835	Intermediate Similarity	NPC470767
0.7835	Intermediate Similarity	NPC309448
0.7835	Intermediate Similarity	NPC474569
0.7812	Intermediate Similarity	NPC8039
0.7812	Intermediate Similarity	NPC155010
0.7812	Intermediate Similarity	NPC211879
0.7812	Intermediate Similarity	NPC189852
0.7812	Intermediate Similarity	NPC472252
0.7812	Intermediate Similarity	NPC123796
0.7812	Intermediate Similarity	NPC245280
0.7812	Intermediate Similarity	NPC131479
0.7812	Intermediate Similarity	NPC162354
0.7812	Intermediate Similarity	NPC16520
0.7812	Intermediate Similarity	NPC31907
0.7812	Intermediate Similarity	NPC473020
0.7812	Intermediate Similarity	NPC120123
0.7812	Intermediate Similarity	NPC286969
0.7812	Intermediate Similarity	NPC157659
0.7812	Intermediate Similarity	NPC114874
0.7805	Intermediate Similarity	NPC229655
0.7802	Intermediate Similarity	NPC280390
0.7789	Intermediate Similarity	NPC472023
0.7789	Intermediate Similarity	NPC160734
0.7789	Intermediate Similarity	NPC47566
0.7789	Intermediate Similarity	NPC129372
0.7789	Intermediate Similarity	NPC309425
0.7789	Intermediate Similarity	NPC280991
0.7789	Intermediate Similarity	NPC4831
0.7789	Intermediate Similarity	NPC88000
0.7766	Intermediate Similarity	NPC5358
0.7766	Intermediate Similarity	NPC216260
0.7766	Intermediate Similarity	NPC477928
0.7766	Intermediate Similarity	NPC40182
0.7766	Intermediate Similarity	NPC198422
0.7766	Intermediate Similarity	NPC158088
0.7765	Intermediate Similarity	NPC16090
0.7755	Intermediate Similarity	NPC190395
0.7742	Intermediate Similarity	NPC256230
0.7742	Intermediate Similarity	NPC207617
0.7732	Intermediate Similarity	NPC173583
0.7732	Intermediate Similarity	NPC110656
0.7732	Intermediate Similarity	NPC470768
0.7732	Intermediate Similarity	NPC57065
0.7732	Intermediate Similarity	NPC471434
0.7732	Intermediate Similarity	NPC473127
0.7732	Intermediate Similarity	NPC54521
0.7732	Intermediate Similarity	NPC109792
0.7732	Intermediate Similarity	NPC148603
0.7732	Intermediate Similarity	NPC471435
0.7732	Intermediate Similarity	NPC273879
0.7732	Intermediate Similarity	NPC165033
0.7732	Intermediate Similarity	NPC230948
0.7732	Intermediate Similarity	NPC473734
0.7732	Intermediate Similarity	NPC203354
0.7717	Intermediate Similarity	NPC211238
0.7708	Intermediate Similarity	NPC159036
0.7708	Intermediate Similarity	NPC312553
0.7708	Intermediate Similarity	NPC136816
0.7708	Intermediate Similarity	NPC288694
0.7684	Intermediate Similarity	NPC282669
0.7684	Intermediate Similarity	NPC7341
0.7684	Intermediate Similarity	NPC473200
0.7684	Intermediate Similarity	NPC469942
0.7667	Intermediate Similarity	NPC104129
0.7667	Intermediate Similarity	NPC249408
0.7662	Intermediate Similarity	NPC147292
0.7653	Intermediate Similarity	NPC194842
0.7653	Intermediate Similarity	NPC242748
0.7653	Intermediate Similarity	NPC152584
0.7653	Intermediate Similarity	NPC138057
0.7653	Intermediate Similarity	NPC269627
0.7653	Intermediate Similarity	NPC26798
0.7653	Intermediate Similarity	NPC181845
0.7653	Intermediate Similarity	NPC473476
0.7653	Intermediate Similarity	NPC473923
0.7653	Intermediate Similarity	NPC173859
0.7653	Intermediate Similarity	NPC208594
0.7653	Intermediate Similarity	NPC470512
0.7653	Intermediate Similarity	NPC127801
0.7653	Intermediate Similarity	NPC160816
0.7653	Intermediate Similarity	NPC69737
0.7653	Intermediate Similarity	NPC208477
0.7647	Intermediate Similarity	NPC127295
0.7647	Intermediate Similarity	NPC163362
0.7634	Intermediate Similarity	NPC230347
0.7634	Intermediate Similarity	NPC108141
0.7634	Intermediate Similarity	NPC275310
0.7634	Intermediate Similarity	NPC286612
0.7629	Intermediate Similarity	NPC473123
0.7629	Intermediate Similarity	NPC213190
0.7629	Intermediate Similarity	NPC16573
0.7629	Intermediate Similarity	NPC473124
0.7629	Intermediate Similarity	NPC99627
0.7629	Intermediate Similarity	NPC473129
0.7625	Intermediate Similarity	NPC474078
0.7614	Intermediate Similarity	NPC470658
0.7604	Intermediate Similarity	NPC285231
0.7604	Intermediate Similarity	NPC470434
0.7604	Intermediate Similarity	NPC21568
0.7604	Intermediate Similarity	NPC267510
0.76	Intermediate Similarity	NPC40440
0.76	Intermediate Similarity	NPC302057
0.76	Intermediate Similarity	NPC42482
0.7579	Intermediate Similarity	NPC234287
0.7579	Intermediate Similarity	NPC280825
0.7576	Intermediate Similarity	NPC230507
0.7576	Intermediate Similarity	NPC14946
0.7576	Intermediate Similarity	NPC181467
0.7576	Intermediate Similarity	NPC14704
0.7576	Intermediate Similarity	NPC113044
0.7576	Intermediate Similarity	NPC283829
0.7576	Intermediate Similarity	NPC161676
0.7576	Intermediate Similarity	NPC63368
0.7576	Intermediate Similarity	NPC33053
0.7576	Intermediate Similarity	NPC257964
0.7576	Intermediate Similarity	NPC281939
0.7576	Intermediate Similarity	NPC470432
0.7576	Intermediate Similarity	NPC305423
0.7576	Intermediate Similarity	NPC226642
0.7576	Intermediate Similarity	NPC208650
0.7576	Intermediate Similarity	NPC231340
0.7576	Intermediate Similarity	NPC78034
0.7576	Intermediate Similarity	NPC94272
0.7551	Intermediate Similarity	NPC75608
0.7551	Intermediate Similarity	NPC93352
0.7526	Intermediate Similarity	NPC154452
0.75	Intermediate Similarity	NPC180183
0.75	Intermediate Similarity	NPC476538
0.75	Intermediate Similarity	NPC476540
0.75	Intermediate Similarity	NPC38217
0.75	Intermediate Similarity	NPC472199
0.75	Intermediate Similarity	NPC136699
0.75	Intermediate Similarity	NPC159005
0.75	Intermediate Similarity	NPC126147
0.75	Intermediate Similarity	NPC324598
0.75	Intermediate Similarity	NPC246124
0.75	Intermediate Similarity	NPC472197
0.75	Intermediate Similarity	NPC472988
0.75	Intermediate Similarity	NPC266718
0.75	Intermediate Similarity	NPC476541
0.75	Intermediate Similarity	NPC98696
0.75	Intermediate Similarity	NPC220167
0.75	Intermediate Similarity	NPC476539
0.75	Intermediate Similarity	NPC6931
0.75	Intermediate Similarity	NPC473288
0.75	Intermediate Similarity	NPC295980
0.75	Intermediate Similarity	NPC220427
0.7475	Intermediate Similarity	NPC473199
0.7475	Intermediate Similarity	NPC472900
0.7475	Intermediate Similarity	NPC472899
0.7475	Intermediate Similarity	NPC472898
0.7468	Intermediate Similarity	NPC477758

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 NPC20072 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	168
0.1-0.2	1938
0.2-0.3	4293
0.3-0.4	1920
0.4-0.5	454
0.5-0.6	293
0.6-0.7	82
0.7-0.8	2
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
0.7228	Intermediate Similarity	NPD6412	Phase 2
0.699	Remote Similarity	NPD6686	Approved
0.6869	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD8515	Approved
0.6847	Remote Similarity	NPD8517	Approved
0.6847	Remote Similarity	NPD8516	Approved
0.6847	Remote Similarity	NPD8513	Phase 3
0.6762	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD8377	Approved
0.6757	Remote Similarity	NPD8294	Approved
0.6727	Remote Similarity	NPD7327	Approved
0.6727	Remote Similarity	NPD7328	Approved
0.6696	Remote Similarity	NPD8379	Approved
0.6696	Remote Similarity	NPD8033	Approved
0.6696	Remote Similarity	NPD7503	Approved
0.6696	Remote Similarity	NPD8335	Approved
0.6696	Remote Similarity	NPD8380	Approved
0.6696	Remote Similarity	NPD8296	Approved
0.6696	Remote Similarity	NPD8378	Approved
0.6667	Remote Similarity	NPD6698	Approved
0.6667	Remote Similarity	NPD46	Approved
0.6667	Remote Similarity	NPD7516	Approved
0.6636	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD368	Approved
0.6579	Remote Similarity	NPD8328	Phase 3
0.6552	Remote Similarity	NPD1810	Approved
0.6552	Remote Similarity	NPD1811	Approved
0.6526	Remote Similarity	NPD7524	Approved
0.6514	Remote Similarity	NPD8133	Approved
0.65	Remote Similarity	NPD6123	Approved
0.6486	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD891	Phase 3
0.6447	Remote Similarity	NPD892	Phase 3
0.6447	Remote Similarity	NPD893	Approved
0.6447	Remote Similarity	NPD888	Phase 3
0.6447	Remote Similarity	NPD890	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD7838	Discovery
0.6327	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD3168	Discontinued
0.6325	Remote Similarity	NPD7507	Approved
0.6316	Remote Similarity	NPD2269	Approved
0.6277	Remote Similarity	NPD6695	Phase 3
0.6271	Remote Similarity	NPD8074	Phase 3
0.6263	Remote Similarity	NPD7983	Approved
0.6211	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD6370	Approved
0.6207	Remote Similarity	NPD2687	Approved
0.6207	Remote Similarity	NPD2686	Approved
0.6207	Remote Similarity	NPD2254	Approved
0.62	Remote Similarity	NPD8171	Discontinued
0.6196	Remote Similarity	NPD7645	Phase 2
0.6184	Remote Similarity	NPD905	Approved
0.6184	Remote Similarity	NPD904	Phase 3
0.6167	Remote Similarity	NPD7319	Approved
0.6154	Remote Similarity	NPD7346	Approved
0.6154	Remote Similarity	NPD6932	Approved
0.6148	Remote Similarity	NPD8449	Approved
0.6129	Remote Similarity	NPD7525	Registered
0.6126	Remote Similarity	NPD6430	Approved
0.6126	Remote Similarity	NPD6429	Approved
0.6105	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD3669	Approved
0.6105	Remote Similarity	NPD6110	Phase 1
0.6098	Remote Similarity	NPD8450	Suspended
0.6095	Remote Similarity	NPD5344	Discontinued
0.6061	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD6101	Approved
0.6053	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD6933	Approved
0.6034	Remote Similarity	NPD6059	Approved
0.6034	Remote Similarity	NPD6054	Approved
0.6026	Remote Similarity	NPD887	Approved
0.6026	Remote Similarity	NPD895	Approved
0.6026	Remote Similarity	NPD894	Approved
0.6026	Remote Similarity	NPD889	Approved
0.6023	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD6683	Phase 2
0.602	Remote Similarity	NPD7750	Discontinued
0.6	Remote Similarity	NPD8293	Discontinued
0.6	Remote Similarity	NPD7641	Discontinued
0.5978	Remote Similarity	NPD5776	Phase 2
0.5978	Remote Similarity	NPD6925	Approved
0.5966	Remote Similarity	NPD8341	Approved
0.5966	Remote Similarity	NPD8342	Approved
0.5966	Remote Similarity	NPD8299	Approved
0.5966	Remote Similarity	NPD8340	Approved
0.5957	Remote Similarity	NPD6931	Approved
0.5957	Remote Similarity	NPD7514	Phase 3
0.5957	Remote Similarity	NPD6930	Phase 2
0.5957	Remote Similarity	NPD7332	Phase 2
0.595	Remote Similarity	NPD7736	Approved
0.5941	Remote Similarity	NPD6411	Approved
0.5934	Remote Similarity	NPD7339	Approved
0.5934	Remote Similarity	NPD6942	Approved
0.5917	Remote Similarity	NPD8451	Approved
0.5914	Remote Similarity	NPD7145	Approved
0.5904	Remote Similarity	NPD1145	Discontinued
0.5895	Remote Similarity	NPD6898	Phase 1
0.5882	Remote Similarity	NPD7829	Approved
0.5882	Remote Similarity	NPD371	Approved
0.5882	Remote Similarity	NPD6067	Discontinued
0.5882	Remote Similarity	NPD5779	Approved
0.5882	Remote Similarity	NPD5778	Approved
0.5882	Remote Similarity	NPD7830	Approved
0.5872	Remote Similarity	NPD5357	Phase 1
0.587	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5868	Remote Similarity	NPD8448	Approved
0.5865	Remote Similarity	NPD7839	Suspended
0.5854	Remote Similarity	NPD8390	Approved
0.5854	Remote Similarity	NPD8392	Approved
0.5854	Remote Similarity	NPD8391	Approved
0.5851	Remote Similarity	NPD6929	Approved
0.5847	Remote Similarity	NPD6016	Approved
0.5847	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD6015	Approved
0.5841	Remote Similarity	NPD6882	Approved
0.5833	Remote Similarity	NPD7492	Approved
0.5824	Remote Similarity	NPD6924	Approved
0.5824	Remote Similarity	NPD6926	Approved
0.5802	Remote Similarity	NPD2267	Suspended
0.5798	Remote Similarity	NPD5988	Approved
0.5798	Remote Similarity	NPD8080	Discontinued
0.5789	Remote Similarity	NPD3731	Phase 3
0.5785	Remote Similarity	NPD6616	Approved
0.5784	Remote Similarity	NPD7637	Suspended
0.5784	Remote Similarity	NPD7087	Discontinued
0.5776	Remote Similarity	NPD6009	Approved
0.5763	Remote Similarity	NPD6319	Approved
0.5761	Remote Similarity	NPD8264	Approved
0.5755	Remote Similarity	NPD7638	Approved
0.5738	Remote Similarity	NPD7078	Approved
0.573	Remote Similarity	NPD6922	Approved
0.573	Remote Similarity	NPD6923	Approved
0.5729	Remote Similarity	NPD6902	Approved
0.5728	Remote Similarity	NPD6399	Phase 3
0.5714	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD8444	Approved
0.5702	Remote Similarity	NPD6053	Discontinued
0.5702	Remote Similarity	NPD8297	Approved
0.5701	Remote Similarity	NPD7639	Approved
0.5701	Remote Similarity	NPD7640	Approved
0.5701	Remote Similarity	NPD6648	Approved
0.57	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.57	Remote Similarity	NPD4251	Approved
0.57	Remote Similarity	NPD4250	Approved
0.5691	Remote Similarity	NPD8337	Approved
0.5691	Remote Similarity	NPD8336	Approved
0.569	Remote Similarity	NPD4831	Approved
0.569	Remote Similarity	NPD4830	Approved
0.569	Remote Similarity	NPD4832	Approved
0.5679	Remote Similarity	NPD342	Phase 1
0.5676	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD5282	Discontinued
0.567	Remote Similarity	NPD6435	Approved
0.5667	Remote Similarity	NPD7143	Approved
0.5667	Remote Similarity	NPD5125	Phase 3
0.5667	Remote Similarity	NPD7144	Approved
0.5667	Remote Similarity	NPD5126	Approved
0.566	Remote Similarity	NPD6084	Phase 2
0.566	Remote Similarity	NPD6083	Phase 2
0.5657	Remote Similarity	NPD6893	Approved
0.5652	Remote Similarity	NPD4632	Approved
0.5636	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD4822	Approved
0.5625	Remote Similarity	NPD4819	Approved
0.5625	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD4821	Approved
0.5625	Remote Similarity	NPD7509	Discontinued
0.5625	Remote Similarity	NPD4820	Approved
0.562	Remote Similarity	NPD7642	Approved
0.5604	Remote Similarity	NPD7152	Approved
0.5604	Remote Similarity	NPD7151	Approved
0.5604	Remote Similarity	NPD7150	Approved
0.5604	Remote Similarity	NPD4243	Approved
0.56	Remote Similarity	NPD4249	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