NPASS Compound

Structure

NPC476119 OpenBabel07101719242D 23 24 0 0 0 0 0 0 0 0999 V2000 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 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 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 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 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -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 0.8660 -0.5000 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 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 3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 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 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 2 0 0 0 0 5 10 2 0 0 0 0 6 10 1 0 0 0 0 7 12 1 0 0 0 0 7 13 2 0 0 0 0 8 11 1 0 0 0 0 8 18 2 0 0 0 0 9 15 2 0 0 0 0 9 16 1 0 0 0 0 10 12 1 0 0 0 0 11 15 1 0 0 0 0 11 17 2 0 0 0 0 12 19 2 0 0 0 0 13 14 1 0 0 0 0 13 20 1 0 0 0 0 14 16 2 0 0 0 0 14 17 1 0 0 0 0 15 21 1 0 0 0 0 16 22 1 0 0 0 0 17 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.08
Volume:	314.489
LogP:	3.629
LogD:	1.553
LogS:	-3.843
# Rotatable Bonds:	5
TPSA:	111.9
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.444
Synthetic Accessibility Score:	2.571
Fsp3:	0.118
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.066
MDCK Permeability:	1.353348488919437e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.308
30% Bioavailability (F30%):	0.051

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	97.93034362792969%
Volume Distribution (VD):	0.877
Pgp-substrate:	2.098337411880493%

ADMET: Metabolism

CYP1A2-inhibitor:	0.744
CYP1A2-substrate:	0.076
CYP2C19-inhibitor:	0.25
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.727
CYP2C9-substrate:	0.67
CYP2D6-inhibitor:	0.312
CYP2D6-substrate:	0.164
CYP3A4-inhibitor:	0.405
CYP3A4-substrate:	0.137

ADMET: Excretion

Clearance (CL):	3.205
Half-life (T1/2):	0.67

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.059
Drug-inuced Liver Injury (DILI):	0.937
AMES Toxicity:	0.365
Rat Oral Acute Toxicity:	0.092
Maximum Recommended Daily Dose:	0.112
Skin Sensitization:	0.818
Carcinogencity:	0.239
Eye Corrosion:	0.034
Eye Irritation:	0.931
Respiratory Toxicity:	0.787

Download Data

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

Natural Product: NPC476119

Natural Product ID:	NPC476119
*Common Name:**	VVXYWOPOZYQNHU-QPEQYQDCSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VVXYWOPOZYQNHU-QPEQYQDCSA-N
Standard InCHI:	InChI=1S/C17H14O6/c1-9-15(21)11(8-18)17(23)14(16(9)22)13(20)7-12(19)10-5-3-2-4-6-10/h2-8,20-23H,1H3/b13-7-
SMILES:	O=Cc1c(O)c(/C(=C/C(=O)c2ccccc2)/O)c(c(c1O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL53593
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003474] Retrochalcones

*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
NPO33071	desmos spp.	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12729671]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT759	Cell Line	H9	Homo sapiens	IC50	=	18.8	ug.mL-1	PMID[531567]

☑ 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 NPC476119 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	297
0.1-0.2	1470
0.2-0.3	3800
0.3-0.4	11149
0.4-0.5	8256
0.5-0.6	5085
0.6-0.7	6889
0.7-0.8	4457
0.8-0.85	878
0.85-0.9	343
0.9-0.95	55
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
0.968	High Similarity	NPC275504
0.9524	High Similarity	NPC475042
0.9516	High Similarity	NPC103356
0.9516	High Similarity	NPC162612
0.9516	High Similarity	NPC105157
0.9516	High Similarity	NPC98254
0.9516	High Similarity	NPC100067
0.9516	High Similarity	NPC190043
0.9516	High Similarity	NPC23126
0.9516	High Similarity	NPC72158
0.9516	High Similarity	NPC30501
0.9516	High Similarity	NPC266689
0.9516	High Similarity	NPC169250
0.944	High Similarity	NPC473017
0.944	High Similarity	NPC21305
0.944	High Similarity	NPC221777
0.9435	High Similarity	NPC267846
0.9435	High Similarity	NPC62952
0.9375	High Similarity	NPC213485
0.9375	High Similarity	NPC40524
0.9375	High Similarity	NPC139074
0.9365	High Similarity	NPC474998
0.936	High Similarity	NPC116513
0.9268	High Similarity	NPC133909
0.9268	High Similarity	NPC32032
0.9242	High Similarity	NPC471620
0.9231	High Similarity	NPC61153
0.9231	High Similarity	NPC70859
0.9231	High Similarity	NPC470210
0.9231	High Similarity	NPC130899
0.9231	High Similarity	NPC283590
0.9187	High Similarity	NPC303737
0.9187	High Similarity	NPC156139
0.9187	High Similarity	NPC45438
0.9187	High Similarity	NPC19174
0.9187	High Similarity	NPC267552
0.9187	High Similarity	NPC224273
0.9187	High Similarity	NPC115159
0.9187	High Similarity	NPC73532
0.9187	High Similarity	NPC143427
0.9187	High Similarity	NPC242895
0.9113	High Similarity	NPC91105
0.9113	High Similarity	NPC309765
0.9106	High Similarity	NPC297186
0.9062	High Similarity	NPC120488
0.9062	High Similarity	NPC102829
0.904	High Similarity	NPC65761
0.904	High Similarity	NPC472029
0.9032	High Similarity	NPC215392
0.9032	High Similarity	NPC196976
0.9024	High Similarity	NPC159525
0.9015	High Similarity	NPC156092
0.9015	High Similarity	NPC131039
0.9008	High Similarity	NPC282780
0.9008	High Similarity	NPC166480
0.8976	High Similarity	NPC8745
0.8968	High Similarity	NPC13238
0.8955	High Similarity	NPC112789
0.8955	High Similarity	NPC19622
0.8952	High Similarity	NPC149246
0.8952	High Similarity	NPC229649
0.8947	High Similarity	NPC41461
0.8947	High Similarity	NPC477242
0.8947	High Similarity	NPC477243
0.8947	High Similarity	NPC477244
0.8947	High Similarity	NPC25287
0.8947	High Similarity	NPC249606
0.8947	High Similarity	NPC12165
0.8947	High Similarity	NPC168105
0.8947	High Similarity	NPC98115
0.8947	High Similarity	NPC1486
0.8947	High Similarity	NPC186838
0.8947	High Similarity	NPC66349
0.8947	High Similarity	NPC274109
0.8947	High Similarity	NPC150399
0.8943	High Similarity	NPC161617
0.8943	High Similarity	NPC158222
0.8939	High Similarity	NPC103842
0.8898	High Similarity	NPC10926
0.8898	High Similarity	NPC475733
0.8889	High Similarity	NPC275903
0.8889	High Similarity	NPC470211
0.8889	High Similarity	NPC295384
0.8889	High Similarity	NPC283429
0.8881	High Similarity	NPC317119
0.8881	High Similarity	NPC153979
0.8881	High Similarity	NPC472419
0.888	High Similarity	NPC226275
0.8872	High Similarity	NPC194764
0.8872	High Similarity	NPC13575
0.8872	High Similarity	NPC65005
0.8872	High Similarity	NPC264112
0.8871	High Similarity	NPC294037
0.8864	High Similarity	NPC475088
0.8862	High Similarity	NPC184527
0.8862	High Similarity	NPC283844
0.8862	High Similarity	NPC40649
0.8862	High Similarity	NPC209486
0.8855	High Similarity	NPC175738
0.8855	High Similarity	NPC262359
0.8824	High Similarity	NPC144118
0.8824	High Similarity	NPC80962
0.8824	High Similarity	NPC326109
0.8824	High Similarity	NPC48624
0.8824	High Similarity	NPC213659
0.8824	High Similarity	NPC219917
0.8824	High Similarity	NPC204985
0.8824	High Similarity	NPC172250
0.8824	High Similarity	NPC259166
0.8824	High Similarity	NPC101366
0.8824	High Similarity	NPC215311
0.8815	High Similarity	NPC21350
0.8815	High Similarity	NPC162939
0.881	High Similarity	NPC218333
0.881	High Similarity	NPC232708
0.8806	High Similarity	NPC222633
0.88	High Similarity	NPC146642
0.8797	High Similarity	NPC286336
0.879	High Similarity	NPC195262
0.879	High Similarity	NPC188814
0.8788	High Similarity	NPC87231
0.8788	High Similarity	NPC129132
0.8788	High Similarity	NPC212631
0.8788	High Similarity	NPC257756
0.8788	High Similarity	NPC205468
0.878	High Similarity	NPC230349
0.8769	High Similarity	NPC109123
0.8769	High Similarity	NPC92624
0.8759	High Similarity	NPC268204
0.8759	High Similarity	NPC73061
0.8759	High Similarity	NPC321980
0.8759	High Similarity	NPC55832
0.8759	High Similarity	NPC3188
0.8759	High Similarity	NPC26051
0.8759	High Similarity	NPC469404
0.8759	High Similarity	NPC470089
0.8759	High Similarity	NPC52789
0.8759	High Similarity	NPC470087
0.875	High Similarity	NPC477956
0.875	High Similarity	NPC472366
0.8741	High Similarity	NPC209560
0.8741	High Similarity	NPC294409
0.8741	High Similarity	NPC303644
0.8741	High Similarity	NPC116632
0.8741	High Similarity	NPC181124
0.8741	High Similarity	NPC7013
0.8741	High Similarity	NPC162680
0.874	High Similarity	NPC306288
0.8722	High Similarity	NPC144051
0.8722	High Similarity	NPC20560
0.8722	High Similarity	NPC242294
0.8722	High Similarity	NPC18877
0.8722	High Similarity	NPC188646
0.8722	High Similarity	NPC204960
0.8722	High Similarity	NPC472365
0.8722	High Similarity	NPC474519
0.8722	High Similarity	NPC139813
0.8722	High Similarity	NPC27643
0.8722	High Similarity	NPC192304
0.8722	High Similarity	NPC312318
0.8722	High Similarity	NPC159623
0.8722	High Similarity	NPC337373
0.8722	High Similarity	NPC175098
0.8722	High Similarity	NPC28753
0.8722	High Similarity	NPC263670
0.8722	High Similarity	NPC82225
0.8722	High Similarity	NPC56031
0.8722	High Similarity	NPC294593
0.8712	High Similarity	NPC308037
0.8712	High Similarity	NPC313618
0.8712	High Similarity	NPC64359
0.8705	High Similarity	NPC110776
0.8705	High Similarity	NPC271590
0.8702	High Similarity	NPC259942
0.8702	High Similarity	NPC62219
0.8696	High Similarity	NPC148545
0.8692	High Similarity	NPC470981
0.8686	High Similarity	NPC253822
0.8686	High Similarity	NPC11056
0.8686	High Similarity	NPC187843
0.8686	High Similarity	NPC204045
0.8686	High Similarity	NPC305845
0.8682	High Similarity	NPC328983
0.8676	High Similarity	NPC251681
0.8676	High Similarity	NPC124269
0.8676	High Similarity	NPC55162
0.8676	High Similarity	NPC12175
0.8676	High Similarity	NPC243528
0.8676	High Similarity	NPC278323
0.8676	High Similarity	NPC138099
0.8676	High Similarity	NPC90665
0.8676	High Similarity	NPC309154
0.8676	High Similarity	NPC279668
0.8676	High Similarity	NPC242994
0.8667	High Similarity	NPC53414
0.8667	High Similarity	NPC44960
0.8667	High Similarity	NPC471905
0.8667	High Similarity	NPC474110
0.8667	High Similarity	NPC213603
0.8667	High Similarity	NPC53206

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 NPC476119 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	280
0.1-0.2	964
0.2-0.3	1413
0.3-0.4	2814
0.4-0.5	2127
0.5-0.6	1105
0.6-0.7	335
0.7-0.8	101
0.8-0.85	8
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8712	High Similarity	NPD1240	Approved
0.8593	High Similarity	NPD1510	Phase 2
0.8593	High Similarity	NPD1509	Clinical (unspecified phase)
0.8582	High Similarity	NPD1607	Approved
0.8571	High Similarity	NPD943	Approved
0.8406	Intermediate Similarity	NPD1549	Phase 2
0.8333	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.831	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.831	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8151	Intermediate Similarity	NPD4380	Phase 2
0.8112	Intermediate Similarity	NPD7390	Discontinued
0.8095	Intermediate Similarity	NPD7411	Suspended
0.8045	Intermediate Similarity	NPD1164	Approved
0.8	Intermediate Similarity	NPD2796	Approved
0.7987	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD7075	Discontinued
0.7933	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7923	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD6651	Approved
0.791	Intermediate Similarity	NPD1470	Approved
0.7879	Intermediate Similarity	NPD1201	Approved
0.7872	Intermediate Similarity	NPD2935	Discontinued
0.7872	Intermediate Similarity	NPD5404	Approved
0.7872	Intermediate Similarity	NPD5406	Approved
0.7872	Intermediate Similarity	NPD5408	Approved
0.7872	Intermediate Similarity	NPD1551	Phase 2
0.7872	Intermediate Similarity	NPD5405	Approved
0.7867	Intermediate Similarity	NPD7819	Suspended
0.7867	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD6799	Approved
0.7801	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD6801	Discontinued
0.78	Intermediate Similarity	NPD1934	Approved
0.7708	Intermediate Similarity	NPD2800	Approved
0.7708	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD920	Approved
0.7692	Intermediate Similarity	NPD9493	Approved
0.7671	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD6599	Discontinued
0.7655	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7768	Phase 2
0.7647	Intermediate Similarity	NPD3882	Suspended
0.7643	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD74	Approved
0.7619	Intermediate Similarity	NPD1511	Approved
0.7619	Intermediate Similarity	NPD9266	Approved
0.7597	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD9545	Approved
0.7568	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD2533	Approved
0.7568	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD2534	Approved
0.7568	Intermediate Similarity	NPD2532	Approved
0.754	Intermediate Similarity	NPD9267	Approved
0.754	Intermediate Similarity	NPD9264	Approved
0.754	Intermediate Similarity	NPD9263	Approved
0.754	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD3750	Approved
0.7517	Intermediate Similarity	NPD1512	Approved
0.7516	Intermediate Similarity	NPD2801	Approved
0.75	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD1243	Approved
0.7452	Intermediate Similarity	NPD6959	Discontinued
0.7448	Intermediate Similarity	NPD2344	Approved
0.7431	Intermediate Similarity	NPD2799	Discontinued
0.7424	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD940	Approved
0.7419	Intermediate Similarity	NPD846	Approved
0.7407	Intermediate Similarity	NPD5953	Discontinued
0.7405	Intermediate Similarity	NPD6232	Discontinued
0.7391	Intermediate Similarity	NPD1203	Approved
0.7391	Intermediate Similarity	NPD7286	Phase 2
0.7391	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD2313	Discontinued
0.7375	Intermediate Similarity	NPD7473	Discontinued
0.7372	Intermediate Similarity	NPD3749	Approved
0.7362	Intermediate Similarity	NPD6559	Discontinued
0.7343	Intermediate Similarity	NPD230	Phase 1
0.7325	Intermediate Similarity	NPD919	Approved
0.7312	Intermediate Similarity	NPD6166	Phase 2
0.7312	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD1237	Approved
0.7299	Intermediate Similarity	NPD9269	Phase 2
0.7278	Intermediate Similarity	NPD5494	Approved
0.7273	Intermediate Similarity	NPD9281	Approved
0.7259	Intermediate Similarity	NPD9268	Approved
0.7248	Intermediate Similarity	NPD2309	Approved
0.7244	Intermediate Similarity	NPD3817	Phase 2
0.7237	Intermediate Similarity	NPD5403	Approved
0.7234	Intermediate Similarity	NPD6832	Phase 2
0.7233	Intermediate Similarity	NPD1247	Approved
0.7226	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD9261	Approved
0.7222	Intermediate Similarity	NPD3818	Discontinued
0.7219	Intermediate Similarity	NPD5401	Approved
0.7214	Intermediate Similarity	NPD2798	Approved
0.7212	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD3748	Approved
0.7174	Intermediate Similarity	NPD3972	Approved
0.7174	Intermediate Similarity	NPD9717	Approved
0.7134	Intermediate Similarity	NPD7074	Phase 3
0.7133	Intermediate Similarity	NPD3764	Approved
0.7114	Intermediate Similarity	NPD2654	Approved
0.7095	Intermediate Similarity	NPD2346	Discontinued
0.7095	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD520	Approved
0.7073	Intermediate Similarity	NPD6020	Phase 2
0.7073	Intermediate Similarity	NPD7054	Approved
0.7067	Intermediate Similarity	NPD4628	Phase 3
0.7063	Intermediate Similarity	NPD1242	Phase 1
0.7032	Intermediate Similarity	NPD7458	Discontinued
0.7032	Intermediate Similarity	NPD3226	Approved
0.703	Intermediate Similarity	NPD7472	Approved
0.7016	Intermediate Similarity	NPD2859	Approved
0.7016	Intermediate Similarity	NPD2860	Approved
0.7014	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD6797	Phase 2
0.6975	Remote Similarity	NPD5710	Approved
0.6975	Remote Similarity	NPD5711	Approved
0.697	Remote Similarity	NPD5844	Phase 1
0.6954	Remote Similarity	NPD3400	Discontinued
0.6953	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD1930	Approved
0.6953	Remote Similarity	NPD1929	Approved
0.6947	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7251	Discontinued
0.6935	Remote Similarity	NPD2933	Approved
0.6935	Remote Similarity	NPD2934	Approved
0.6934	Remote Similarity	NPD1548	Phase 1
0.6928	Remote Similarity	NPD1729	Discontinued
0.6923	Remote Similarity	NPD9494	Approved
0.6918	Remote Similarity	NPD5402	Approved
0.6905	Remote Similarity	NPD7808	Phase 3
0.6903	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD3268	Approved
0.6894	Remote Similarity	NPD4750	Phase 3
0.6875	Remote Similarity	NPD4908	Phase 1
0.6871	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD3300	Phase 2
0.6857	Remote Similarity	NPD1610	Phase 2
0.6857	Remote Similarity	NPD422	Phase 1
0.6853	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.685	Remote Similarity	NPD3020	Approved
0.6846	Remote Similarity	NPD4308	Phase 3
0.6846	Remote Similarity	NPD5048	Discontinued
0.6846	Remote Similarity	NPD7033	Discontinued
0.6842	Remote Similarity	NPD7003	Approved
0.6835	Remote Similarity	NPD3019	Approved
0.6835	Remote Similarity	NPD2932	Approved
0.6831	Remote Similarity	NPD1876	Approved
0.6829	Remote Similarity	NPD3926	Phase 2
0.6818	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD1241	Discontinued
0.6813	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6100	Approved
0.68	Remote Similarity	NPD4360	Phase 2
0.68	Remote Similarity	NPD6099	Approved
0.68	Remote Similarity	NPD4363	Phase 3
0.6783	Remote Similarity	NPD2797	Approved
0.6765	Remote Similarity	NPD5951	Approved
0.6761	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD4361	Phase 2
0.6757	Remote Similarity	NPD5124	Phase 1
0.6757	Remote Similarity	NPD1933	Approved
0.6757	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD1809	Phase 2
0.6736	Remote Similarity	NPD1019	Discontinued
0.6732	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.673	Remote Similarity	NPD5890	Approved
0.673	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.673	Remote Similarity	NPD5889	Approved
0.672	Remote Similarity	NPD845	Approved
0.6708	Remote Similarity	NPD2296	Approved
0.6704	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.669	Remote Similarity	NPD4208	Discontinued
0.6688	Remote Similarity	NPD6190	Approved
0.6686	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3266	Approved
0.6667	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3267	Approved
0.6667	Remote Similarity	NPD411	Approved
0.6647	Remote Similarity	NPD6104	Discontinued
0.6647	Remote Similarity	NPD8150	Discontinued
0.6646	Remote Similarity	NPD1465	Phase 2
0.6645	Remote Similarity	NPD1471	Phase 3
0.6644	Remote Similarity	NPD447	Suspended
0.6624	Remote Similarity	NPD5049	Phase 3
0.6623	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD1196	Approved
0.661	Remote Similarity	NPD6535	Approved
0.661	Remote Similarity	NPD6534	Approved
0.6605	Remote Similarity	NPD4288	Approved
0.6604	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD1543	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