NPASS Compound

Structure

NPC474803 OpenBabel07101718242D 27 29 0 0 1 0 0 0 0 0999 V2000 -1.7948 0.4118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7194 -0.2088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2959 1.8996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6890 1.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9028 1.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2211 1.3355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5170 0.1305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1619 -1.3839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5924 0.7510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2959 -1.8839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2959 0.1161 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1619 -0.3839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3707 1.3355 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.9994 0.7510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4299 -0.3839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4299 -1.3839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0748 0.1305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4244 0.9960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5751 -0.2450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0753 0.6205 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 4.1937 1.9036 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5638 -1.8839 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3038 1.9887 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6956 -1.2377 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9953 1.0125 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7994 -0.6007 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 26 1 0 0 0 0 2 27 1 0 0 0 0 3 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 13 1 0 0 0 0 6 14 1 0 0 0 0 7 9 1 0 0 0 0 7 12 1 0 0 0 0 8 10 2 0 0 0 0 8 12 1 0 0 0 0 9 13 1 0 0 0 0 10 16 1 0 0 0 0 11 12 2 0 0 0 0 11 15 1 0 0 0 0 13 22 1 0 0 0 0 14 17 2 0 0 0 0 14 18 1 0 0 0 0 15 16 2 0 0 0 0 15 17 1 0 0 0 0 16 23 1 0 0 0 0 17 19 1 0 0 0 0 18 20 1 0 0 0 0 18 24 2 0 0 0 0 19 21 1 0 0 0 0 19 25 2 0 0 0 0 20 21 2 0 0 0 0 20 26 1 0 0 0 0 21 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	372.16
Volume:	380.389
LogP:	3.59
LogD:	2.717
LogS:	-3.857
# Rotatable Bonds:	2
TPSA:	99.38
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.601
Synthetic Accessibility Score:	4.608
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.025
MDCK Permeability:	1.608704224054236e-05
Pgp-inhibitor:	0.02
Pgp-substrate:	0.071
Human Intestinal Absorption (HIA):	0.025
20% Bioavailability (F20%):	0.028
30% Bioavailability (F30%):	0.018

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	99.59197235107422%
Volume Distribution (VD):	0.303
Pgp-substrate:	2.034334182739258%

ADMET: Metabolism

CYP1A2-inhibitor:	0.568
CYP1A2-substrate:	0.93
CYP2C19-inhibitor:	0.068
CYP2C19-substrate:	0.256
CYP2C9-inhibitor:	0.417
CYP2C9-substrate:	0.853
CYP2D6-inhibitor:	0.227
CYP2D6-substrate:	0.524
CYP3A4-inhibitor:	0.157
CYP3A4-substrate:	0.238

ADMET: Excretion

Clearance (CL):	6.949
Half-life (T1/2):	0.671

ADMET: Toxicity

hERG Blockers:	0.215
Human Hepatotoxicity (H-HT):	0.391
Drug-inuced Liver Injury (DILI):	0.033
AMES Toxicity:	0.068
Rat Oral Acute Toxicity:	0.201
Maximum Recommended Daily Dose:	0.865
Skin Sensitization:	0.951
Carcinogencity:	0.104
Eye Corrosion:	0.003
Eye Irritation:	0.04
Respiratory Toxicity:	0.624

Download Data

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

Natural Product: NPC474803

Natural Product ID:	NPC474803
*Common Name:**	Actinidione
IUPAC Name:	n.a.
Synonyms:	Actinidione
Standard InCHIKey:	BYPFMKISMDPPHB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H24O6/c1-26-20-18(24)14-6-4-3-5-13(22)9-7-12-8-10-16(23)15(11-12)17(14)19(25)21(20)27-2/h8,10-11,13,22-23H,3-7,9H2,1-2H3
SMILES:	COC1=C(C(=O)C2=C(C1=O)CCCCC(CCC3=CC2=C(C=C3)O)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL483238
PubChem CID:	11559771
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0004646] 1-hydroxy-2-unsubstituted benzenoids

*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
NPO15146	Myrica nana	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18723353]
NPO31026	Myrica rubra	Species	Myricaceae	Eukaryota	barks	n.a.	n.a.	PMID[23066712]
NPO31026	Myrica rubra	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31026	Myrica rubra	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15146	Myrica nana	Species	Myricaceae	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	5

Activity Type	# Activity
NON-MOLECULAR	1
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Inhibition	=	9.52	%	PMID[554007]
NPT2	Others	Unspecified		Inhibition	=	21.08	%	PMID[554007]
NPT2	Others	Unspecified		Inhibition	=	22.92	%	PMID[554007]
NPT2	Others	Unspecified		Inhibition	=	31.43	%	PMID[554007]
NPT2	Others	Unspecified		Inhibition	=	38.72	%	PMID[554007]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	7.9	ug.mL-1	PMID[554008]

☑ 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 NPC474803 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	244
0.1-0.2	1170
0.2-0.3	3086
0.3-0.4	7929
0.4-0.5	11323
0.5-0.6	5147
0.6-0.7	10190
0.7-0.8	3503
0.8-0.85	97
0.85-0.9	7
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.878	High Similarity	NPC31936
0.8595	High Similarity	NPC325646
0.8595	High Similarity	NPC28951
0.8504	High Similarity	NPC127975
0.8468	Intermediate Similarity	NPC473136
0.8462	Intermediate Similarity	NPC123
0.8462	Intermediate Similarity	NPC163169
0.8425	Intermediate Similarity	NPC474766
0.8387	Intermediate Similarity	NPC473767
0.8361	Intermediate Similarity	NPC23402
0.8346	Intermediate Similarity	NPC135062
0.8308	Intermediate Similarity	NPC24869
0.8308	Intermediate Similarity	NPC476024
0.8308	Intermediate Similarity	NPC473744
0.8296	Intermediate Similarity	NPC309452
0.8284	Intermediate Similarity	NPC283590
0.8284	Intermediate Similarity	NPC70859
0.8284	Intermediate Similarity	NPC61153
0.8284	Intermediate Similarity	NPC130899
0.8281	Intermediate Similarity	NPC231767
0.8279	Intermediate Similarity	NPC285350
0.8271	Intermediate Similarity	NPC477280
0.8271	Intermediate Similarity	NPC19719
0.8271	Intermediate Similarity	NPC477281
0.8268	Intermediate Similarity	NPC475192
0.8268	Intermediate Similarity	NPC164947
0.8258	Intermediate Similarity	NPC475042
0.825	Intermediate Similarity	NPC21162
0.824	Intermediate Similarity	NPC182240
0.8235	Intermediate Similarity	NPC317305
0.8222	Intermediate Similarity	NPC38158
0.8222	Intermediate Similarity	NPC266245
0.8197	Intermediate Similarity	NPC242136
0.8197	Intermediate Similarity	NPC11824
0.8195	Intermediate Similarity	NPC309430
0.8195	Intermediate Similarity	NPC323379
0.8195	Intermediate Similarity	NPC327204
0.8182	Intermediate Similarity	NPC177576
0.8175	Intermediate Similarity	NPC322021
0.8168	Intermediate Similarity	NPC165257
0.816	Intermediate Similarity	NPC273282
0.816	Intermediate Similarity	NPC474890
0.816	Intermediate Similarity	NPC161943
0.8154	Intermediate Similarity	NPC474944
0.8151	Intermediate Similarity	NPC228737
0.8143	Intermediate Similarity	NPC477409
0.8143	Intermediate Similarity	NPC245482
0.8143	Intermediate Similarity	NPC301751
0.8143	Intermediate Similarity	NPC29932
0.814	Intermediate Similarity	NPC184219
0.8134	Intermediate Similarity	NPC213485
0.8134	Intermediate Similarity	NPC139074
0.8134	Intermediate Similarity	NPC40524
0.8129	Intermediate Similarity	NPC229916
0.8125	Intermediate Similarity	NPC67300
0.8125	Intermediate Similarity	NPC139171
0.812	Intermediate Similarity	NPC473777
0.8116	Intermediate Similarity	NPC470211
0.8099	Intermediate Similarity	NPC321252
0.8099	Intermediate Similarity	NPC252544
0.8095	Intermediate Similarity	NPC476020
0.8092	Intermediate Similarity	NPC477212
0.8092	Intermediate Similarity	NPC477211
0.8092	Intermediate Similarity	NPC319422
0.8092	Intermediate Similarity	NPC477214
0.8077	Intermediate Similarity	NPC87985
0.8074	Intermediate Similarity	NPC27643
0.8071	Intermediate Similarity	NPC148545
0.8067	Intermediate Similarity	NPC70843
0.8062	Intermediate Similarity	NPC174991
0.806	Intermediate Similarity	NPC110609
0.806	Intermediate Similarity	NPC242358
0.806	Intermediate Similarity	NPC302844
0.806	Intermediate Similarity	NPC165612
0.806	Intermediate Similarity	NPC246693
0.8045	Intermediate Similarity	NPC146615
0.8045	Intermediate Similarity	NPC469929
0.8045	Intermediate Similarity	NPC253488
0.8033	Intermediate Similarity	NPC212718
0.803	Intermediate Similarity	NPC469930
0.803	Intermediate Similarity	NPC217431
0.8029	Intermediate Similarity	NPC119542
0.8017	Intermediate Similarity	NPC88141
0.8016	Intermediate Similarity	NPC249435
0.8015	Intermediate Similarity	NPC267846
0.8015	Intermediate Similarity	NPC110211
0.8015	Intermediate Similarity	NPC474945
0.8015	Intermediate Similarity	NPC164136
0.8015	Intermediate Similarity	NPC476022
0.8	Intermediate Similarity	NPC83718
0.8	Intermediate Similarity	NPC321980
0.8	Intermediate Similarity	NPC201297
0.8	Intermediate Similarity	NPC470087
0.8	Intermediate Similarity	NPC254603
0.7986	Intermediate Similarity	NPC49242
0.7986	Intermediate Similarity	NPC139554
0.7984	Intermediate Similarity	NPC473931
0.7984	Intermediate Similarity	NPC474114
0.7984	Intermediate Similarity	NPC91105
0.7984	Intermediate Similarity	NPC474050
0.7971	Intermediate Similarity	NPC472419
0.797	Intermediate Similarity	NPC102829
0.797	Intermediate Similarity	NPC120488
0.7967	Intermediate Similarity	NPC48525
0.7967	Intermediate Similarity	NPC286222
0.7956	Intermediate Similarity	NPC64230
0.7956	Intermediate Similarity	NPC84699
0.7956	Intermediate Similarity	NPC71638
0.7956	Intermediate Similarity	NPC13575
0.7955	Intermediate Similarity	NPC190043
0.7955	Intermediate Similarity	NPC23126
0.7955	Intermediate Similarity	NPC105157
0.7955	Intermediate Similarity	NPC98254
0.7955	Intermediate Similarity	NPC30501
0.7955	Intermediate Similarity	NPC266689
0.7955	Intermediate Similarity	NPC169250
0.7955	Intermediate Similarity	NPC103356
0.7955	Intermediate Similarity	NPC162612
0.7955	Intermediate Similarity	NPC121104
0.7955	Intermediate Similarity	NPC116513
0.7955	Intermediate Similarity	NPC72158
0.7955	Intermediate Similarity	NPC100067
0.7951	Intermediate Similarity	NPC222905
0.7943	Intermediate Similarity	NPC478164
0.7939	Intermediate Similarity	NPC477213
0.7926	Intermediate Similarity	NPC66384
0.7926	Intermediate Similarity	NPC164236
0.7926	Intermediate Similarity	NPC477407
0.7926	Intermediate Similarity	NPC475008
0.7926	Intermediate Similarity	NPC186097
0.7926	Intermediate Similarity	NPC475009
0.7926	Intermediate Similarity	NPC112192
0.7926	Intermediate Similarity	NPC280476
0.7926	Intermediate Similarity	NPC128348
0.7926	Intermediate Similarity	NPC119985
0.7926	Intermediate Similarity	NPC189106
0.7926	Intermediate Similarity	NPC309717
0.7923	Intermediate Similarity	NPC472029
0.7923	Intermediate Similarity	NPC65761
0.7923	Intermediate Similarity	NPC273683
0.7917	Intermediate Similarity	NPC95178
0.7917	Intermediate Similarity	NPC29989
0.7917	Intermediate Similarity	NPC69332
0.7917	Intermediate Similarity	NPC188677
0.7914	Intermediate Similarity	NPC25427
0.7914	Intermediate Similarity	NPC477408
0.7914	Intermediate Similarity	NPC114620
0.7914	Intermediate Similarity	NPC103337
0.791	Intermediate Similarity	NPC27659
0.791	Intermediate Similarity	NPC198305
0.7907	Intermediate Similarity	NPC196976
0.7907	Intermediate Similarity	NPC215392
0.7903	Intermediate Similarity	NPC296144
0.7903	Intermediate Similarity	NPC28784
0.7902	Intermediate Similarity	NPC470458
0.7902	Intermediate Similarity	NPC136878
0.7899	Intermediate Similarity	NPC477244
0.7899	Intermediate Similarity	NPC12165
0.7899	Intermediate Similarity	NPC98115
0.7899	Intermediate Similarity	NPC186838
0.7899	Intermediate Similarity	NPC41461
0.7899	Intermediate Similarity	NPC25287
0.7899	Intermediate Similarity	NPC274109
0.7899	Intermediate Similarity	NPC24394
0.7899	Intermediate Similarity	NPC261573
0.7899	Intermediate Similarity	NPC66349
0.7899	Intermediate Similarity	NPC1486
0.7899	Intermediate Similarity	NPC249606
0.7899	Intermediate Similarity	NPC8931
0.7899	Intermediate Similarity	NPC120693
0.7899	Intermediate Similarity	NPC150399
0.7899	Intermediate Similarity	NPC475957
0.7899	Intermediate Similarity	NPC477242
0.7899	Intermediate Similarity	NPC477243
0.7899	Intermediate Similarity	NPC168105
0.7895	Intermediate Similarity	NPC237225
0.7895	Intermediate Similarity	NPC221777
0.7895	Intermediate Similarity	NPC21305
0.7895	Intermediate Similarity	NPC473017
0.7887	Intermediate Similarity	NPC475705
0.7887	Intermediate Similarity	NPC476178
0.7887	Intermediate Similarity	NPC51887
0.7887	Intermediate Similarity	NPC117836
0.7886	Intermediate Similarity	NPC470355
0.7883	Intermediate Similarity	NPC470210
0.7883	Intermediate Similarity	NPC103842
0.7879	Intermediate Similarity	NPC15837
0.7879	Intermediate Similarity	NPC51037
0.7879	Intermediate Similarity	NPC204579
0.7879	Intermediate Similarity	NPC71610
0.7879	Intermediate Similarity	NPC62952
0.7879	Intermediate Similarity	NPC231774
0.7879	Intermediate Similarity	NPC473751
0.7874	Intermediate Similarity	NPC184527
0.7872	Intermediate Similarity	NPC308572
0.7872	Intermediate Similarity	NPC26051
0.7872	Intermediate Similarity	NPC470089
0.7872	Intermediate Similarity	NPC268204
0.7872	Intermediate Similarity	NPC52789
0.7872	Intermediate Similarity	NPC55832

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 NPC474803 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	247
0.1-0.2	842
0.2-0.3	1449
0.3-0.4	2623
0.4-0.5	2148
0.5-0.6	1234
0.6-0.7	553
0.7-0.8	54
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
0.773	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD9545	Approved
0.7536	Intermediate Similarity	NPD1240	Approved
0.7518	Intermediate Similarity	NPD6798	Discontinued
0.75	Intermediate Similarity	NPD7075	Discontinued
0.748	Intermediate Similarity	NPD1241	Discontinued
0.7467	Intermediate Similarity	NPD6801	Discontinued
0.7465	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD1237	Approved
0.745	Intermediate Similarity	NPD4380	Phase 2
0.7447	Intermediate Similarity	NPD1510	Phase 2
0.7429	Intermediate Similarity	NPD1607	Approved
0.7417	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD1549	Phase 2
0.7407	Intermediate Similarity	NPD1470	Approved
0.7394	Intermediate Similarity	NPD2935	Discontinued
0.7368	Intermediate Similarity	NPD1201	Approved
0.7357	Intermediate Similarity	NPD6355	Discontinued
0.7348	Intermediate Similarity	NPD2932	Approved
0.7324	Intermediate Similarity	NPD2799	Discontinued
0.7311	Intermediate Similarity	NPD2860	Approved
0.7311	Intermediate Similarity	NPD2859	Approved
0.731	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD4628	Phase 3
0.7308	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD6651	Approved
0.7303	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD846	Approved
0.7295	Intermediate Similarity	NPD940	Approved
0.728	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD6799	Approved
0.7266	Intermediate Similarity	NPD3764	Approved
0.7266	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD6190	Approved
0.7255	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD2933	Approved
0.7227	Intermediate Similarity	NPD2934	Approved
0.7226	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD3019	Approved
0.7208	Intermediate Similarity	NPD3882	Suspended
0.7203	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD3750	Approved
0.7188	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD9493	Approved
0.7172	Intermediate Similarity	NPD2424	Discontinued
0.7171	Intermediate Similarity	NPD7411	Suspended
0.7167	Intermediate Similarity	NPD1809	Phase 2
0.7163	Intermediate Similarity	NPD943	Approved
0.7163	Intermediate Similarity	NPD4060	Phase 1
0.7154	Intermediate Similarity	NPD2629	Approved
0.7153	Intermediate Similarity	NPD2796	Approved
0.7153	Intermediate Similarity	NPD1164	Approved
0.7143	Intermediate Similarity	NPD845	Approved
0.7133	Intermediate Similarity	NPD5403	Approved
0.7131	Intermediate Similarity	NPD3020	Approved
0.7123	Intermediate Similarity	NPD2800	Approved
0.7113	Intermediate Similarity	NPD5124	Phase 1
0.7113	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6599	Discontinued
0.7103	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6004	Phase 3
0.7103	Intermediate Similarity	NPD6005	Phase 3
0.7103	Intermediate Similarity	NPD6002	Phase 3
0.7092	Intermediate Similarity	NPD6233	Phase 2
0.7092	Intermediate Similarity	NPD4062	Phase 3
0.709	Intermediate Similarity	NPD4626	Approved
0.7087	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7033	Discontinued
0.7077	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD3400	Discontinued
0.7059	Intermediate Similarity	NPD3972	Approved
0.7054	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD4208	Discontinued
0.7049	Intermediate Similarity	NPD9495	Approved
0.7034	Intermediate Similarity	NPD5404	Approved
0.7034	Intermediate Similarity	NPD5408	Approved
0.7034	Intermediate Similarity	NPD5405	Approved
0.7034	Intermediate Similarity	NPD5406	Approved
0.7031	Intermediate Similarity	NPD2067	Discontinued
0.7029	Intermediate Similarity	NPD2797	Approved
0.7021	Intermediate Similarity	NPD2313	Discontinued
0.7021	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD3268	Approved
0.7015	Intermediate Similarity	NPD1651	Approved
0.7013	Intermediate Similarity	NPD1934	Approved
0.7	Intermediate Similarity	NPD2533	Approved
0.7	Intermediate Similarity	NPD6166	Phase 2
0.7	Intermediate Similarity	NPD2534	Approved
0.7	Intermediate Similarity	NPD5401	Approved
0.7	Intermediate Similarity	NPD2532	Approved
0.7	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD7768	Phase 2
0.6986	Remote Similarity	NPD2344	Approved
0.6985	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD422	Phase 1
0.6978	Remote Similarity	NPD2798	Approved
0.6972	Remote Similarity	NPD6663	Approved
0.6968	Remote Similarity	NPD7819	Suspended
0.6966	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD8166	Discontinued
0.6959	Remote Similarity	NPD7003	Approved
0.6957	Remote Similarity	NPD1283	Approved
0.6957	Remote Similarity	NPD8651	Approved
0.6954	Remote Similarity	NPD5049	Phase 3
0.6953	Remote Similarity	NPD9266	Approved
0.6953	Remote Similarity	NPD74	Approved
0.6948	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7390	Discontinued
0.6929	Remote Similarity	NPD5736	Approved
0.6928	Remote Similarity	NPD7458	Discontinued
0.6923	Remote Similarity	NPD5402	Approved
0.6918	Remote Similarity	NPD4477	Approved
0.6918	Remote Similarity	NPD4476	Approved
0.6912	Remote Similarity	NPD3847	Discontinued
0.6899	Remote Similarity	NPD4750	Phase 3
0.6894	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD5691	Approved
0.6885	Remote Similarity	NPD844	Approved
0.6884	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4908	Phase 1
0.6875	Remote Similarity	NPD230	Phase 1
0.6875	Remote Similarity	NPD9267	Approved
0.6875	Remote Similarity	NPD9263	Approved
0.6875	Remote Similarity	NPD9264	Approved
0.6871	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD3300	Phase 2
0.6859	Remote Similarity	NPD2801	Approved
0.6853	Remote Similarity	NPD6405	Approved
0.6853	Remote Similarity	NPD6407	Approved
0.685	Remote Similarity	NPD5048	Discontinued
0.6849	Remote Similarity	NPD3748	Approved
0.6846	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD255	Approved
0.6842	Remote Similarity	NPD256	Approved
0.6842	Remote Similarity	NPD1512	Approved
0.6838	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD1876	Approved
0.6831	Remote Similarity	NPD3027	Phase 3
0.6822	Remote Similarity	NPD2684	Approved
0.6821	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD3226	Approved
0.6815	Remote Similarity	NPD3817	Phase 2
0.6815	Remote Similarity	NPD1894	Discontinued
0.6815	Remote Similarity	NPD1548	Phase 1
0.6815	Remote Similarity	NPD3091	Approved
0.6813	Remote Similarity	NPD6959	Discontinued
0.6812	Remote Similarity	NPD1608	Approved
0.6812	Remote Similarity	NPD1481	Phase 2
0.6812	Remote Similarity	NPD9717	Approved
0.6809	Remote Similarity	NPD9494	Approved
0.6809	Remote Similarity	NPD2861	Phase 2
0.6803	Remote Similarity	NPD1551	Phase 2
0.68	Remote Similarity	NPD2309	Approved
0.68	Remote Similarity	NPD3887	Approved
0.679	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD3023	Approved
0.6788	Remote Similarity	NPD6797	Phase 2
0.6788	Remote Similarity	NPD3026	Approved
0.6786	Remote Similarity	NPD1129	Approved
0.6786	Remote Similarity	NPD1131	Approved
0.6786	Remote Similarity	NPD1134	Approved
0.6786	Remote Similarity	NPD1133	Approved
0.6786	Remote Similarity	NPD1135	Approved
0.6786	Remote Similarity	NPD1203	Approved
0.6776	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.677	Remote Similarity	NPD6232	Discontinued
0.6769	Remote Similarity	NPD3022	Approved
0.6769	Remote Similarity	NPD3021	Approved
0.6769	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD3024	Approved
0.6765	Remote Similarity	NPD3025	Approved
0.6761	Remote Similarity	NPD6832	Phase 2
0.6759	Remote Similarity	NPD4340	Discontinued
0.6757	Remote Similarity	NPD2346	Discontinued
0.6757	Remote Similarity	NPD5763	Approved
0.6757	Remote Similarity	NPD5762	Approved
0.6752	Remote Similarity	NPD111	Approved
0.6752	Remote Similarity	NPD8455	Phase 2
0.6748	Remote Similarity	NPD7473	Discontinued
0.6747	Remote Similarity	NPD7251	Discontinued
0.6747	Remote Similarity	NPD6559	Discontinued
0.6742	Remote Similarity	NPD7843	Approved
0.6739	Remote Similarity	NPD1281	Approved
0.6739	Remote Similarity	NPD1610	Phase 2
0.6739	Remote Similarity	NPD1535	Discovery
0.6739	Remote Similarity	NPD3092	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