NPASS Compound

Structure

CID87295 OpenBabel06191715422D 30 33 0 0 0 0 0 0 0 0999 V2000 3.5491 -3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8200 -0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -3.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 3.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2322 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2322 0.1180 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 11 1 0 0 0 0 2 12 1 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 5 11 1 0 0 0 0 5 13 1 0 0 0 0 6 12 1 0 0 0 0 6 14 1 0 0 0 0 7 13 2 0 0 0 0 7 15 1 0 0 0 0 8 14 2 0 0 0 0 8 16 1 0 0 0 0 9 27 1 0 0 0 0 9 29 1 0 0 0 0 10 28 1 0 0 0 0 10 30 1 0 0 0 0 11 23 2 0 0 0 0 12 24 2 0 0 0 0 13 17 1 0 0 0 0 14 18 1 0 0 0 0 15 19 2 0 0 0 0 15 27 1 0 0 0 0 16 20 2 0 0 0 0 16 28 1 0 0 0 0 17 18 1 0 0 0 0 17 21 2 0 0 0 0 18 22 2 0 0 0 0 19 21 1 0 0 0 0 19 29 1 0 0 0 0 20 22 1 0 0 0 0 20 30 1 0 0 0 0 21 25 1 0 0 0 0 22 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	414.13
Volume:	404.072
LogP:	1.655
LogD:	1.985
LogS:	-4.409
# Rotatable Bonds:	7
TPSA:	89.52
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.683
Synthetic Accessibility Score:	3.035
Fsp3:	0.364
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:	-4.784
MDCK Permeability:	3.2284431654261425e-05
Pgp-inhibitor:	0.03
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.093

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.029
Plasma Protein Binding (PPB):	95.41593170166016%
Volume Distribution (VD):	0.688
Pgp-substrate:	3.802323341369629%

ADMET: Metabolism

CYP1A2-inhibitor:	0.275
CYP1A2-substrate:	0.926
CYP2C19-inhibitor:	0.951
CYP2C19-substrate:	0.825
CYP2C9-inhibitor:	0.428
CYP2C9-substrate:	0.916
CYP2D6-inhibitor:	0.27
CYP2D6-substrate:	0.889
CYP3A4-inhibitor:	0.933
CYP3A4-substrate:	0.797

ADMET: Excretion

Clearance (CL):	10.313
Half-life (T1/2):	0.27

ADMET: Toxicity

hERG Blockers:	0.353
Human Hepatotoxicity (H-HT):	0.551
Drug-inuced Liver Injury (DILI):	0.823
AMES Toxicity:	0.024
Rat Oral Acute Toxicity:	0.042
Maximum Recommended Daily Dose:	0.029
Skin Sensitization:	0.126
Carcinogencity:	0.929
Eye Corrosion:	0.003
Eye Irritation:	0.191
Respiratory Toxicity:	0.032

Download Data

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

Natural Product: NPC87295

Natural Product ID:	NPC87295
*Common Name:**	Neglignan C
IUPAC Name:	1-[7-methoxy-6-[4-methoxy-6-(2-oxopropyl)-1,3-benzodioxol-5-yl]-1,3-benzodioxol-5-yl]propan-2-one
Synonyms:
Standard InCHIKey:	VSTIJDYPLCUJNX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C22H22O8/c1-11(23)5-13-7-15-19(29-9-27-15)21(25-3)17(13)18-14(6-12(2)24)8-16-20(22(18)26-4)30-10-28-16/h7-8H,5-6,9-10H2,1-4H3
SMILES:	COc1c(c(CC(=O)C)cc2c1OCO2)c1c(CC(=O)C)cc2c(c1OC)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2386331
PubChem CID:	71726088
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

*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
NPO29191	Schisandra neglecta	Species	Schisandraceae	Eukaryota	Stems	Luoji Mountain Village, Xichang County, Sicuan Province, China	2011-Sep	PMID[23738539]
NPO29191	Schisandra neglecta	Species	Schisandraceae	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
EC50	1
IC50	5
Others	2

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1452	Cell Line	C8166	Homo sapiens	CC50	=	54500.0	nM	PMID[463264]
NPT2678	Cell Line	NB-4	Homo sapiens	IC50	=	7300.0	nM	PMID[463264]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	6500.0	nM	PMID[463264]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[463264]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	>	10000.0	nM	PMID[463264]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	8200.0	nM	PMID[463264]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	3900.0	nM	PMID[463264]
NPT27	Others	Unspecified		Ratio CC50/EC50	=	14.1	n.a.	PMID[463264]

☑ 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 NPC87295 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	436
0.1-0.2	1679
0.2-0.3	4065
0.3-0.4	11476
0.4-0.5	7196
0.5-0.6	3945
0.6-0.7	7037
0.7-0.8	6453
0.8-0.85	330
0.85-0.9	73
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9348	High Similarity	NPC471182
0.9315	High Similarity	NPC104353
0.9184	High Similarity	NPC220577
0.9172	High Similarity	NPC304821
0.9116	High Similarity	NPC303519
0.9067	High Similarity	NPC477380
0.906	High Similarity	NPC273578
0.9013	High Similarity	NPC474770
0.9007	High Similarity	NPC477885
0.8993	High Similarity	NPC474514
0.8961	High Similarity	NPC475865
0.8958	High Similarity	NPC474288
0.8947	High Similarity	NPC325122
0.8936	High Similarity	NPC32189
0.8933	High Similarity	NPC178195
0.8933	High Similarity	NPC348849
0.8919	High Similarity	NPC149505
0.8896	High Similarity	NPC61141
0.8889	High Similarity	NPC40237
0.8889	High Similarity	NPC151423
0.8859	High Similarity	NPC474975
0.8859	High Similarity	NPC13985
0.8859	High Similarity	NPC210642
0.8794	High Similarity	NPC185680
0.8794	High Similarity	NPC145722
0.8794	High Similarity	NPC256776
0.8776	High Similarity	NPC296575
0.8776	High Similarity	NPC321696
0.8776	High Similarity	NPC321958
0.8774	High Similarity	NPC469512
0.8767	High Similarity	NPC92693
0.8767	High Similarity	NPC18211
0.8767	High Similarity	NPC143092
0.8767	High Similarity	NPC218841
0.8767	High Similarity	NPC475000
0.8759	High Similarity	NPC176586
0.8759	High Similarity	NPC210354
0.8758	High Similarity	NPC474990
0.875	High Similarity	NPC216434
0.875	High Similarity	NPC103448
0.8725	High Similarity	NPC85141
0.8718	High Similarity	NPC469475
0.8718	High Similarity	NPC469518
0.8716	High Similarity	NPC80230
0.8716	High Similarity	NPC304687
0.8716	High Similarity	NPC101755
0.8716	High Similarity	NPC104024
0.8716	High Similarity	NPC65574
0.871	High Similarity	NPC258322
0.871	High Similarity	NPC191352
0.8707	High Similarity	NPC318286
0.8707	High Similarity	NPC474158
0.8707	High Similarity	NPC327651
0.8701	High Similarity	NPC474043
0.8701	High Similarity	NPC125713
0.8699	High Similarity	NPC218510
0.8699	High Similarity	NPC76415
0.8684	High Similarity	NPC57211
0.8671	High Similarity	NPC11453
0.8662	High Similarity	NPC477884
0.8649	High Similarity	NPC224687
0.8649	High Similarity	NPC193779
0.8643	High Similarity	NPC258483
0.8639	High Similarity	NPC177644
0.8639	High Similarity	NPC326144
0.8639	High Similarity	NPC191158
0.8636	High Similarity	NPC19947
0.8636	High Similarity	NPC207584
0.863	High Similarity	NPC474295
0.8627	High Similarity	NPC202249
0.8627	High Similarity	NPC42871
0.8627	High Similarity	NPC188962
0.8618	High Similarity	NPC52623
0.8609	High Similarity	NPC234152
0.86	High Similarity	NPC477698
0.86	High Similarity	NPC262455
0.86	High Similarity	NPC177476
0.859	High Similarity	NPC209411
0.859	High Similarity	NPC239890
0.8581	High Similarity	NPC475868
0.8571	High Similarity	NPC32373
0.8571	High Similarity	NPC237946
0.8571	High Similarity	NPC301897
0.8562	High Similarity	NPC478213
0.8553	High Similarity	NPC279061
0.8552	High Similarity	NPC201404
0.8552	High Similarity	NPC290714
0.8552	High Similarity	NPC53722
0.8552	High Similarity	NPC470962
0.8543	High Similarity	NPC473989
0.8543	High Similarity	NPC316989
0.8533	High Similarity	NPC262804
0.8533	High Similarity	NPC40654
0.8533	High Similarity	NPC327352
0.8533	High Similarity	NPC198129
0.8533	High Similarity	NPC477375
0.8533	High Similarity	NPC252281
0.8526	High Similarity	NPC96593
0.8521	High Similarity	NPC65183
0.8521	High Similarity	NPC261812
0.8521	High Similarity	NPC72046
0.8516	High Similarity	NPC181168
0.8516	High Similarity	NPC163527
0.8516	High Similarity	NPC115281
0.8514	High Similarity	NPC474036
0.8514	High Similarity	NPC172171
0.8514	High Similarity	NPC239254
0.8509	High Similarity	NPC178737
0.8506	High Similarity	NPC238834
0.8506	High Similarity	NPC478238
0.8506	High Similarity	NPC234730
0.8497	Intermediate Similarity	NPC153008
0.8497	Intermediate Similarity	NPC148497
0.8497	Intermediate Similarity	NPC68882
0.8497	Intermediate Similarity	NPC245948
0.8491	Intermediate Similarity	NPC474042
0.8491	Intermediate Similarity	NPC174734
0.8487	Intermediate Similarity	NPC164082
0.8483	Intermediate Similarity	NPC196420
0.8477	Intermediate Similarity	NPC322426
0.8477	Intermediate Similarity	NPC293757
0.8477	Intermediate Similarity	NPC477374
0.8477	Intermediate Similarity	NPC668
0.8477	Intermediate Similarity	NPC474965
0.8477	Intermediate Similarity	NPC477695
0.8477	Intermediate Similarity	NPC477376
0.8477	Intermediate Similarity	NPC174512
0.8472	Intermediate Similarity	NPC148893
0.8472	Intermediate Similarity	NPC49235
0.8472	Intermediate Similarity	NPC72796
0.8472	Intermediate Similarity	NPC150534
0.8472	Intermediate Similarity	NPC44245
0.8472	Intermediate Similarity	NPC25333
0.8471	Intermediate Similarity	NPC288149
0.8471	Intermediate Similarity	NPC319749
0.8462	Intermediate Similarity	NPC266848
0.8462	Intermediate Similarity	NPC136750
0.8457	Intermediate Similarity	NPC474568
0.8452	Intermediate Similarity	NPC155063
0.8452	Intermediate Similarity	NPC115123
0.8452	Intermediate Similarity	NPC239113
0.8451	Intermediate Similarity	NPC192255
0.8447	Intermediate Similarity	NPC477883
0.8446	Intermediate Similarity	NPC324962
0.8442	Intermediate Similarity	NPC312763
0.8442	Intermediate Similarity	NPC198461
0.844	Intermediate Similarity	NPC150809
0.8438	Intermediate Similarity	NPC42230
0.8438	Intermediate Similarity	NPC474948
0.8438	Intermediate Similarity	NPC79322
0.8438	Intermediate Similarity	NPC471180
0.8435	Intermediate Similarity	NPC312199
0.8431	Intermediate Similarity	NPC56184
0.8431	Intermediate Similarity	NPC477699
0.8428	Intermediate Similarity	NPC474647
0.8428	Intermediate Similarity	NPC475953
0.8428	Intermediate Similarity	NPC187923
0.8425	Intermediate Similarity	NPC9068
0.8421	Intermediate Similarity	NPC475170
0.8418	Intermediate Similarity	NPC280778
0.8414	Intermediate Similarity	NPC143895
0.8414	Intermediate Similarity	NPC121651
0.8411	Intermediate Similarity	NPC316676
0.8411	Intermediate Similarity	NPC325720
0.8408	Intermediate Similarity	NPC131557
0.8408	Intermediate Similarity	NPC150943
0.8408	Intermediate Similarity	NPC91634
0.8408	Intermediate Similarity	NPC268718
0.8408	Intermediate Similarity	NPC119910
0.8403	Intermediate Similarity	NPC31530
0.84	Intermediate Similarity	NPC154971
0.84	Intermediate Similarity	NPC252286
0.8397	Intermediate Similarity	NPC258644
0.8395	Intermediate Similarity	NPC469506
0.8392	Intermediate Similarity	NPC7744
0.8387	Intermediate Similarity	NPC284353
0.8385	Intermediate Similarity	NPC117911
0.8378	Intermediate Similarity	NPC36531
0.8378	Intermediate Similarity	NPC184641
0.8378	Intermediate Similarity	NPC229172
0.8378	Intermediate Similarity	NPC287124
0.8378	Intermediate Similarity	NPC230538
0.8378	Intermediate Similarity	NPC133934
0.8378	Intermediate Similarity	NPC184684
0.8378	Intermediate Similarity	NPC103637
0.8377	Intermediate Similarity	NPC144162
0.8377	Intermediate Similarity	NPC474606
0.8377	Intermediate Similarity	NPC308555
0.8377	Intermediate Similarity	NPC292460
0.8366	Intermediate Similarity	NPC163002
0.8366	Intermediate Similarity	NPC477700
0.8366	Intermediate Similarity	NPC475756
0.8356	Intermediate Similarity	NPC261714
0.8356	Intermediate Similarity	NPC283949
0.8355	Intermediate Similarity	NPC472567
0.8355	Intermediate Similarity	NPC476058
0.8355	Intermediate Similarity	NPC145569
0.8355	Intermediate Similarity	NPC216223
0.8354	Intermediate Similarity	NPC196771
0.8354	Intermediate Similarity	NPC152424

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 NPC87295 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	363
0.1-0.2	962
0.2-0.3	1757
0.3-0.4	2877
0.4-0.5	1725
0.5-0.6	942
0.6-0.7	417
0.7-0.8	99
0.8-0.85	7
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8658	High Similarity	NPD6980	Clinical (unspecified phase)
0.8571	High Similarity	NPD4967	Phase 2
0.8571	High Similarity	NPD4966	Approved
0.8571	High Similarity	NPD4965	Approved
0.8497	Intermediate Similarity	NPD37	Approved
0.8471	Intermediate Similarity	NPD7199	Phase 2
0.8462	Intermediate Similarity	NPD6234	Discontinued
0.8365	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD7228	Approved
0.8092	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3705	Approved
0.7988	Intermediate Similarity	NPD3818	Discontinued
0.7963	Intermediate Similarity	NPD6232	Discontinued
0.7927	Intermediate Similarity	NPD7473	Discontinued
0.7904	Intermediate Similarity	NPD7240	Approved
0.784	Intermediate Similarity	NPD5494	Approved
0.7812	Intermediate Similarity	NPD3817	Phase 2
0.7805	Intermediate Similarity	NPD3926	Phase 2
0.7784	Intermediate Similarity	NPD7074	Phase 3
0.7725	Intermediate Similarity	NPD7054	Approved
0.7688	Intermediate Similarity	NPD1934	Approved
0.7679	Intermediate Similarity	NPD7472	Approved
0.7654	Intermediate Similarity	NPD3882	Suspended
0.764	Intermediate Similarity	NPD2801	Approved
0.764	Intermediate Similarity	NPD1465	Phase 2
0.7619	Intermediate Similarity	NPD5844	Phase 1
0.7561	Intermediate Similarity	NPD919	Approved
0.7551	Intermediate Similarity	NPD3018	Phase 2
0.7546	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD7808	Phase 3
0.7531	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD7819	Suspended
0.7529	Intermediate Similarity	NPD6797	Phase 2
0.7517	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7251	Discontinued
0.747	Intermediate Similarity	NPD1247	Approved
0.7457	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD3748	Approved
0.745	Intermediate Similarity	NPD3027	Phase 3
0.7448	Intermediate Similarity	NPD2981	Phase 2
0.7442	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD6166	Phase 2
0.744	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD3787	Discontinued
0.7419	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD1651	Approved
0.7405	Intermediate Similarity	NPD1511	Approved
0.7403	Intermediate Similarity	NPD2796	Approved
0.7397	Intermediate Similarity	NPD2982	Phase 2
0.7397	Intermediate Similarity	NPD2983	Phase 2
0.7384	Intermediate Similarity	NPD6559	Discontinued
0.7358	Intermediate Similarity	NPD2533	Approved
0.7358	Intermediate Similarity	NPD2534	Approved
0.7358	Intermediate Similarity	NPD2532	Approved
0.7357	Intermediate Similarity	NPD5283	Phase 1
0.7346	Intermediate Similarity	NPD7028	Phase 2
0.7321	Intermediate Similarity	NPD7229	Phase 3
0.7312	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD1512	Approved
0.7303	Intermediate Similarity	NPD1240	Approved
0.7296	Intermediate Similarity	NPD6799	Approved
0.729	Intermediate Similarity	NPD6100	Approved
0.729	Intermediate Similarity	NPD2438	Suspended
0.729	Intermediate Similarity	NPD6099	Approved
0.7278	Intermediate Similarity	NPD5242	Approved
0.7273	Intermediate Similarity	NPD5536	Phase 2
0.7262	Intermediate Similarity	NPD6959	Discontinued
0.7261	Intermediate Similarity	NPD1243	Approved
0.726	Intermediate Similarity	NPD1281	Approved
0.7253	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD17	Approved
0.7239	Intermediate Similarity	NPD4380	Phase 2
0.7239	Intermediate Similarity	NPD6599	Discontinued
0.7228	Intermediate Similarity	NPD5006	Approved
0.7228	Intermediate Similarity	NPD5005	Approved
0.7226	Intermediate Similarity	NPD1510	Phase 2
0.7215	Intermediate Similarity	NPD3750	Approved
0.7209	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD1607	Approved
0.72	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD2979	Phase 3
0.717	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD920	Approved
0.7152	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD3751	Discontinued
0.7143	Intermediate Similarity	NPD1933	Approved
0.7126	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1283	Approved
0.7108	Intermediate Similarity	NPD8455	Phase 2
0.7108	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD4420	Approved
0.7097	Intermediate Similarity	NPD7680	Approved
0.7095	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD1608	Approved
0.7083	Intermediate Similarity	NPD7075	Discontinued
0.7083	Intermediate Similarity	NPD3749	Approved
0.7078	Intermediate Similarity	NPD1613	Approved
0.7078	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD3539	Phase 1
0.7066	Intermediate Similarity	NPD5353	Approved
0.7048	Intermediate Similarity	NPD6801	Discontinued
0.7044	Intermediate Similarity	NPD6674	Discontinued
0.7044	Intermediate Similarity	NPD2654	Approved
0.7037	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD230	Phase 1
0.7025	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD3540	Phase 1
0.7025	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD1653	Approved
0.7	Intermediate Similarity	NPD1876	Approved
0.6989	Remote Similarity	NPD7685	Pre-registration
0.6988	Remote Similarity	NPD6385	Approved
0.6988	Remote Similarity	NPD7411	Suspended
0.6988	Remote Similarity	NPD6386	Approved
0.6981	Remote Similarity	NPD1549	Phase 2
0.698	Remote Similarity	NPD3972	Approved
0.6975	Remote Similarity	NPD7390	Discontinued
0.697	Remote Similarity	NPD7458	Discontinued
0.6968	Remote Similarity	NPD943	Approved
0.6964	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD2935	Discontinued
0.6957	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD2800	Approved
0.6933	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD6875	Approved
0.6928	Remote Similarity	NPD6876	Approved
0.6923	Remote Similarity	NPD6355	Discontinued
0.6923	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD2798	Approved
0.6894	Remote Similarity	NPD4110	Phase 3
0.6894	Remote Similarity	NPD4628	Phase 3
0.6894	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD5090	Approved
0.6886	Remote Similarity	NPD5089	Approved
0.6883	Remote Similarity	NPD4625	Phase 3
0.6882	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4055	Discovery
0.6871	Remote Similarity	NPD4357	Discontinued
0.6867	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD5402	Approved
0.6864	Remote Similarity	NPD5978	Approved
0.6864	Remote Similarity	NPD5977	Approved
0.6855	Remote Similarity	NPD2531	Phase 2
0.6842	Remote Similarity	NPD3266	Approved
0.6842	Remote Similarity	NPD3267	Approved
0.6839	Remote Similarity	NPD2403	Approved
0.6839	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD3146	Approved
0.6829	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD1357	Approved
0.6823	Remote Similarity	NPD8151	Discontinued
0.6821	Remote Similarity	NPD5711	Approved
0.6821	Remote Similarity	NPD5710	Approved
0.6818	Remote Similarity	NPD4908	Phase 1
0.681	Remote Similarity	NPD7124	Phase 2
0.6805	Remote Similarity	NPD4585	Approved
0.6795	Remote Similarity	NPD8032	Phase 2
0.6792	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD651	Clinical (unspecified phase)
0.679	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7110	Phase 1
0.6772	Remote Similarity	NPD6651	Approved
0.6766	Remote Similarity	NPD4005	Discontinued
0.6766	Remote Similarity	NPD3226	Approved
0.6763	Remote Similarity	NPD8127	Discontinued
0.6758	Remote Similarity	NPD6841	Approved
0.6758	Remote Similarity	NPD6843	Phase 3
0.6758	Remote Similarity	NPD6842	Approved
0.6752	Remote Similarity	NPD4060	Phase 1
0.6748	Remote Similarity	NPD6190	Approved
0.6747	Remote Similarity	NPD5403	Approved
0.6739	Remote Similarity	NPD7296	Approved
0.6731	Remote Similarity	NPD5110	Phase 2
0.6731	Remote Similarity	NPD6798	Discontinued
0.6731	Remote Similarity	NPD5111	Phase 2
0.6731	Remote Similarity	NPD5109	Approved
0.6731	Remote Similarity	NPD3268	Approved
0.6731	Remote Similarity	NPD1296	Phase 2
0.6731	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.673	Remote Similarity	NPD6111	Discontinued
0.6727	Remote Similarity	NPD5401	Approved
0.6725	Remote Similarity	NPD7768	Phase 2
0.6711	Remote Similarity	NPD5691	Approved
0.671	Remote Similarity	NPD6832	Phase 2
0.6709	Remote Similarity	NPD447	Suspended
0.6708	Remote Similarity	NPD2344	Approved
0.6708	Remote Similarity	NPD7266	Discontinued
0.6689	Remote Similarity	NPD1610	Phase 2
0.6689	Remote Similarity	NPD1611	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