NPASS Compound

Structure

NPC475756 OpenBabel07101718332D 33 36 0 0 1 0 0 0 0 0999 V2000 2.2634 5.5073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0464 2.8759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8318 4.0905 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4595 -2.5279 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9730 -1.6852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4324 -0.8426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6711 4.7354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1475 1.5306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9459 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0441 2.9901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3840 2.0171 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1475 2.5036 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4595 3.1916 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4595 0.8426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2015 2.5036 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4595 -0.8426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8867 2.5036 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7065 4.8624 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4865 0.8426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2015 1.5306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0441 1.0441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4865 3.1916 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8867 1.5306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4865 -0.8426 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 0.3341 5.7613 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0441 0.0712 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9459 -1.6852 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6852 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9459 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8121 2.8043 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8121 1.2299 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1141 4.0905 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 4 28 1 0 0 0 0 5 29 1 0 0 0 0 6 30 1 0 0 0 0 7 18 1 0 0 0 0 8 12 1 0 0 0 0 8 14 1 0 0 0 0 9 14 2 0 0 0 0 9 16 1 0 0 0 0 10 15 2 0 0 0 0 10 17 1 0 0 0 0 11 31 1 0 0 0 0 11 32 1 0 0 0 0 12 2 1 6 0 0 0 12 13 1 0 0 0 0 13 3 1 6 0 0 0 13 22 1 0 0 0 0 14 19 1 0 0 0 0 15 20 1 0 0 0 0 15 22 1 0 0 0 0 16 24 2 0 0 0 0 16 28 1 0 0 0 0 17 23 2 0 0 0 0 17 31 1 0 0 0 0 18 26 2 0 0 0 0 18 33 1 0 0 0 0 19 20 1 0 0 0 0 19 25 2 0 0 0 0 20 21 2 0 0 0 0 21 23 1 0 0 0 0 21 27 1 0 0 0 0 22 33 1 1 0 0 0 23 32 1 0 0 0 0 24 25 1 0 0 0 0 24 29 1 0 0 0 0 25 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	458.19
Volume:	458.597
LogP:	4.622
LogD:	4.081
LogS:	-5.224
# Rotatable Bonds:	6
TPSA:	92.68
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.648
Synthetic Accessibility Score:	3.95
Fsp3:	0.48
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.755
MDCK Permeability:	3.214676689822227e-05
Pgp-inhibitor:	0.975
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.038
Plasma Protein Binding (PPB):	86.51941680908203%
Volume Distribution (VD):	0.551
Pgp-substrate:	9.588300704956055%

ADMET: Metabolism

CYP1A2-inhibitor:	0.106
CYP1A2-substrate:	0.97
CYP2C19-inhibitor:	0.885
CYP2C19-substrate:	0.877
CYP2C9-inhibitor:	0.818
CYP2C9-substrate:	0.903
CYP2D6-inhibitor:	0.151
CYP2D6-substrate:	0.708
CYP3A4-inhibitor:	0.827
CYP3A4-substrate:	0.898

ADMET: Excretion

Clearance (CL):	13.435
Half-life (T1/2):	0.159

ADMET: Toxicity

hERG Blockers:	0.326
Human Hepatotoxicity (H-HT):	0.149
Drug-inuced Liver Injury (DILI):	0.918
AMES Toxicity:	0.059
Rat Oral Acute Toxicity:	0.156
Maximum Recommended Daily Dose:	0.126
Skin Sensitization:	0.147
Carcinogencity:	0.059
Eye Corrosion:	0.003
Eye Irritation:	0.053
Respiratory Toxicity:	0.356

Download Data

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

Natural Product: NPC475756

Natural Product ID:	NPC475756
*Common Name:**	Schizarin D
IUPAC Name:	n.a.
Synonyms:	Schizarin D
Standard InCHIKey:	LBAZNSIFWCBNOL-VJBOLBCHSA-N
Standard InCHI:	InChI=1S/C25H30O8/c1-7-18(26)33-22-13(3)12(2)8-14-9-16(28-4)24(29-5)25(30-6)19(14)20-15(22)10-17-23(21(20)27)32-11-31-17/h9-10,12-13,22,27H,7-8,11H2,1-6H3/t12-,13-,22+/m1/s1
SMILES:	CCC(=O)OC1C(C(CC2=CC(=C(C(=C2C3=C(C4=C(C=C13)OCO4)O)OC)OC)OC)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL514529
PubChem CID:	44584760
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
NPO10144	Kadsura matsudai	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[11215493]
NPO10144	Kadsura matsudai	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11325232]
NPO10144	Kadsura matsudai	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10144	Kadsura matsudai	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
Others	4

Activity Type	# Activity
Organism	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	Activity	<	25.0	%	PMID[547710]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	Activity	=	25.8	%	PMID[547710]
NPT27	Others	Unspecified		Activity	=	16.8	IU/L	PMID[547710]
NPT27	Others	Unspecified		Activity	=	47.8	IU/L	PMID[547710]

☑ 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 NPC475756 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	321
0.1-0.2	1413
0.2-0.3	3685
0.3-0.4	9044
0.4-0.5	9638
0.5-0.6	4068
0.6-0.7	7025
0.7-0.8	6073
0.8-0.85	1078
0.85-0.9	267
0.9-0.95	74
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9931	High Similarity	NPC471154
0.9862	High Similarity	NPC474606
0.9728	High Similarity	NPC238834
0.9728	High Similarity	NPC476065
0.9653	High Similarity	NPC325720
0.9653	High Similarity	NPC316676
0.9597	High Similarity	NPC475592
0.9521	High Similarity	NPC473989
0.951	High Similarity	NPC121661
0.951	High Similarity	NPC73467
0.951	High Similarity	NPC87883
0.9459	High Similarity	NPC126405
0.9459	High Similarity	NPC308739
0.9459	High Similarity	NPC53669
0.9459	High Similarity	NPC24562
0.9459	High Similarity	NPC217708
0.9459	High Similarity	NPC297271
0.9459	High Similarity	NPC16791
0.9459	High Similarity	NPC77237
0.9456	High Similarity	NPC224472
0.9444	High Similarity	NPC318286
0.9444	High Similarity	NPC189239
0.9444	High Similarity	NPC327651
0.9444	High Similarity	NPC197352
0.9444	High Similarity	NPC110763
0.9444	High Similarity	NPC166506
0.9441	High Similarity	NPC76415
0.9441	High Similarity	NPC218510
0.9404	High Similarity	NPC230531
0.9404	High Similarity	NPC215400
0.9396	High Similarity	NPC198461
0.9396	High Similarity	NPC473425
0.9396	High Similarity	NPC312763
0.9388	High Similarity	NPC24425
0.9379	High Similarity	NPC154971
0.9379	High Similarity	NPC321958
0.9379	High Similarity	NPC321696
0.9379	High Similarity	NPC474054
0.9379	High Similarity	NPC252286
0.9375	High Similarity	NPC326144
0.9371	High Similarity	NPC184641
0.9371	High Similarity	NPC184684
0.9371	High Similarity	NPC133934
0.932	High Similarity	NPC474347
0.932	High Similarity	NPC474393
0.931	High Similarity	NPC477702
0.9306	High Similarity	NPC324962
0.9272	High Similarity	NPC473323
0.9272	High Similarity	NPC29727
0.9257	High Similarity	NPC470916
0.9252	High Similarity	NPC198129
0.9252	High Similarity	NPC477375
0.9252	High Similarity	NPC327352
0.9252	High Similarity	NPC252281
0.9247	High Similarity	NPC212890
0.9236	High Similarity	NPC36531
0.9236	High Similarity	NPC103637
0.9236	High Similarity	NPC230538
0.9236	High Similarity	NPC229172
0.9189	High Similarity	NPC477376
0.9189	High Similarity	NPC477374
0.9189	High Similarity	NPC322426
0.9189	High Similarity	NPC85141
0.9178	High Similarity	NPC475868
0.9128	High Similarity	NPC316989
0.911	High Similarity	NPC172171
0.911	High Similarity	NPC239254
0.9108	High Similarity	NPC311912
0.9073	High Similarity	NPC149735
0.9067	High Similarity	NPC303519
0.9054	High Similarity	NPC295297
0.9051	High Similarity	NPC88557
0.9028	High Similarity	NPC53722
0.9028	High Similarity	NPC471183
0.9028	High Similarity	NPC290714
0.9028	High Similarity	NPC201404
0.9021	High Similarity	NPC133025
0.8993	High Similarity	NPC304821
0.8993	High Similarity	NPC477879
0.8973	High Similarity	NPC41782
0.8973	High Similarity	NPC287124
0.8968	High Similarity	NPC91634
0.8968	High Similarity	NPC63061
0.8968	High Similarity	NPC150943
0.8968	High Similarity	NPC268718
0.8966	High Similarity	NPC177868
0.8961	High Similarity	NPC163527
0.8961	High Similarity	NPC115281
0.8961	High Similarity	NPC181168
0.8958	High Similarity	NPC86605
0.8958	High Similarity	NPC3072
0.8958	High Similarity	NPC865
0.8958	High Similarity	NPC474039
0.8958	High Similarity	NPC46277
0.8958	High Similarity	NPC301765
0.8958	High Similarity	NPC156948
0.8947	High Similarity	NPC475141
0.8947	High Similarity	NPC477377
0.8933	High Similarity	NPC477695
0.8933	High Similarity	NPC474965
0.8933	High Similarity	NPC293757
0.8933	High Similarity	NPC174512
0.8933	High Similarity	NPC668
0.8917	High Similarity	NPC469518
0.8917	High Similarity	NPC469475
0.8912	High Similarity	NPC12728
0.8912	High Similarity	NPC185071
0.8897	High Similarity	NPC6369
0.8897	High Similarity	NPC30951
0.8889	High Similarity	NPC136757
0.8889	High Similarity	NPC178195
0.8889	High Similarity	NPC348849
0.8889	High Similarity	NPC473736
0.8882	High Similarity	NPC475229
0.8882	High Similarity	NPC477699
0.8882	High Similarity	NPC477378
0.8881	High Similarity	NPC469659
0.8881	High Similarity	NPC289258
0.8881	High Similarity	NPC185680
0.8881	High Similarity	NPC145722
0.8881	High Similarity	NPC276026
0.8881	High Similarity	NPC188378
0.8881	High Similarity	NPC56764
0.8881	High Similarity	NPC256776
0.8881	High Similarity	NPC555
0.8881	High Similarity	NPC7515
0.8881	High Similarity	NPC206737
0.8874	High Similarity	NPC477381
0.8851	High Similarity	NPC187774
0.8851	High Similarity	NPC477701
0.8851	High Similarity	NPC472712
0.8851	High Similarity	NPC141569
0.8851	High Similarity	NPC472713
0.8851	High Similarity	NPC118385
0.8851	High Similarity	NPC166884
0.8851	High Similarity	NPC473046
0.8844	High Similarity	NPC191231
0.8839	High Similarity	NPC207584
0.8839	High Similarity	NPC19947
0.8836	High Similarity	NPC284464
0.8824	High Similarity	NPC245948
0.8824	High Similarity	NPC65591
0.8824	High Similarity	NPC178574
0.8824	High Similarity	NPC474514
0.882	High Similarity	NPC471181
0.8819	High Similarity	NPC55239
0.8819	High Similarity	NPC180602
0.8819	High Similarity	NPC214853
0.8819	High Similarity	NPC240279
0.8816	High Similarity	NPC477379
0.8816	High Similarity	NPC477700
0.8808	High Similarity	NPC145569
0.8808	High Similarity	NPC216223
0.8805	High Similarity	NPC118162
0.8805	High Similarity	NPC83049
0.8805	High Similarity	NPC320471
0.8797	High Similarity	NPC116759
0.8797	High Similarity	NPC14294
0.8792	High Similarity	NPC307466
0.8784	High Similarity	NPC469630
0.8784	High Similarity	NPC470811
0.8784	High Similarity	NPC255566
0.8784	High Similarity	NPC477696
0.8784	High Similarity	NPC477697
0.8784	High Similarity	NPC265154
0.8784	High Similarity	NPC298317
0.8774	High Similarity	NPC477380
0.8774	High Similarity	NPC237946
0.8774	High Similarity	NPC32373
0.8766	High Similarity	NPC30009
0.8766	High Similarity	NPC103197
0.8759	High Similarity	NPC471988
0.8759	High Similarity	NPC32189
0.8759	High Similarity	NPC197166
0.8759	High Similarity	NPC143895
0.8759	High Similarity	NPC11453
0.8758	High Similarity	NPC302610
0.875	High Similarity	NPC218041
0.875	High Similarity	NPC472709
0.875	High Similarity	NPC185955
0.875	High Similarity	NPC469707
0.875	High Similarity	NPC145979
0.875	High Similarity	NPC244983
0.875	High Similarity	NPC225815
0.875	High Similarity	NPC9933
0.875	High Similarity	NPC79322
0.875	High Similarity	NPC214326
0.875	High Similarity	NPC472710
0.875	High Similarity	NPC326095
0.875	High Similarity	NPC469706
0.875	High Similarity	NPC67247
0.875	High Similarity	NPC260781
0.875	High Similarity	NPC182368
0.8741	High Similarity	NPC175067
0.8741	High Similarity	NPC204215
0.8734	High Similarity	NPC469512
0.8733	High Similarity	NPC190714
0.8733	High Similarity	NPC99515
0.8718	High Similarity	NPC477885
0.8716	High Similarity	NPC131971

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 NPC475756 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	277
0.1-0.2	884
0.2-0.3	1896
0.3-0.4	2749
0.4-0.5	1692
0.5-0.6	958
0.6-0.7	580
0.7-0.8	104
0.8-0.85	5
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9026	High Similarity	NPD6234	Discontinued
0.8824	High Similarity	NPD37	Approved
0.8774	High Similarity	NPD4966	Approved
0.8774	High Similarity	NPD4967	Phase 2
0.8774	High Similarity	NPD4965	Approved
0.8634	High Similarity	NPD7228	Approved
0.8438	Intermediate Similarity	NPD7199	Phase 2
0.8333	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD3027	Phase 3
0.8095	Intermediate Similarity	NPD7240	Approved
0.8089	Intermediate Similarity	NPD1653	Approved
0.7987	Intermediate Similarity	NPD1613	Approved
0.7987	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD3705	Approved
0.7964	Intermediate Similarity	NPD3818	Discontinued
0.7891	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD7266	Discontinued
0.7765	Intermediate Similarity	NPD7074	Phase 3
0.7748	Intermediate Similarity	NPD4060	Phase 1
0.773	Intermediate Similarity	NPD1465	Phase 2
0.7725	Intermediate Similarity	NPD6232	Discontinued
0.7722	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD7054	Approved
0.7701	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6674	Discontinued
0.7692	Intermediate Similarity	NPD7473	Discontinued
0.7688	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD1934	Approved
0.7661	Intermediate Similarity	NPD7472	Approved
0.763	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD5844	Phase 1
0.7572	Intermediate Similarity	NPD6559	Discontinued
0.7554	Intermediate Similarity	NPD7680	Approved
0.753	Intermediate Similarity	NPD3882	Suspended
0.7515	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD6797	Phase 2
0.7483	Intermediate Similarity	NPD4908	Phase 1
0.7471	Intermediate Similarity	NPD7251	Discontinued
0.747	Intermediate Similarity	NPD3817	Phase 2
0.7429	Intermediate Similarity	NPD7808	Phase 3
0.7427	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD6166	Phase 2
0.7417	Intermediate Similarity	NPD3018	Phase 2
0.741	Intermediate Similarity	NPD2801	Approved
0.7407	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD3620	Phase 2
0.7386	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7685	Pre-registration
0.7365	Intermediate Similarity	NPD1610	Phase 2
0.7355	Intermediate Similarity	NPD6355	Discontinued
0.7346	Intermediate Similarity	NPD2534	Approved
0.7346	Intermediate Similarity	NPD2532	Approved
0.7346	Intermediate Similarity	NPD2533	Approved
0.7342	Intermediate Similarity	NPD5763	Approved
0.7342	Intermediate Similarity	NPD5762	Approved
0.732	Intermediate Similarity	NPD4625	Phase 3
0.7314	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7229	Phase 3
0.7305	Intermediate Similarity	NPD8455	Phase 2
0.7303	Intermediate Similarity	NPD2861	Phase 2
0.7279	Intermediate Similarity	NPD1357	Approved
0.7278	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2983	Phase 2
0.7267	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2982	Phase 2
0.7248	Intermediate Similarity	NPD1091	Approved
0.7244	Intermediate Similarity	NPD230	Phase 1
0.7222	Intermediate Similarity	NPD5283	Phase 1
0.7209	Intermediate Similarity	NPD3787	Discontinued
0.7205	Intermediate Similarity	NPD4110	Phase 3
0.7205	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD3750	Approved
0.7202	Intermediate Similarity	NPD7819	Suspended
0.72	Intermediate Similarity	NPD2981	Phase 2
0.7193	Intermediate Similarity	NPD5494	Approved
0.7178	Intermediate Similarity	NPD1511	Approved
0.7176	Intermediate Similarity	NPD7075	Discontinued
0.717	Intermediate Similarity	NPD2438	Suspended
0.716	Intermediate Similarity	NPD6190	Approved
0.7152	Intermediate Similarity	NPD4749	Approved
0.7134	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD422	Phase 1
0.7127	Intermediate Similarity	NPD6842	Approved
0.7127	Intermediate Similarity	NPD6841	Approved
0.7127	Intermediate Similarity	NPD6843	Phase 3
0.7126	Intermediate Similarity	NPD4380	Phase 2
0.7124	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD2977	Approved
0.7101	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD2978	Approved
0.7099	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD1548	Phase 1
0.7091	Intermediate Similarity	NPD1512	Approved
0.7083	Intermediate Similarity	NPD228	Approved
0.7063	Intermediate Similarity	NPD6100	Approved
0.7063	Intermediate Similarity	NPD6099	Approved
0.7052	Intermediate Similarity	NPD8127	Discontinued
0.7052	Intermediate Similarity	NPD6959	Discontinued
0.7051	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD6798	Discontinued
0.7045	Intermediate Similarity	NPD3751	Discontinued
0.7044	Intermediate Similarity	NPD7097	Phase 1
0.7044	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7549	Discontinued
0.7037	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD1652	Phase 2
0.7025	Intermediate Similarity	NPD5124	Phase 1
0.7025	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4626	Approved
0.7	Intermediate Similarity	NPD8312	Approved
0.7	Intermediate Similarity	NPD8313	Approved
0.6994	Remote Similarity	NPD4628	Phase 3
0.6993	Remote Similarity	NPD1283	Approved
0.6987	Remote Similarity	NPD7095	Approved
0.6982	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6653	Approved
0.6974	Remote Similarity	NPD7827	Phase 1
0.697	Remote Similarity	NPD4357	Discontinued
0.697	Remote Similarity	NPD6799	Approved
0.6964	Remote Similarity	NPD4005	Discontinued
0.6964	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD4140	Approved
0.6962	Remote Similarity	NPD2979	Phase 3
0.6959	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5402	Approved
0.6957	Remote Similarity	NPD2935	Discontinued
0.6951	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD3022	Approved
0.6944	Remote Similarity	NPD3021	Approved
0.6941	Remote Similarity	NPD6801	Discontinued
0.6936	Remote Similarity	NPD919	Approved
0.6933	Remote Similarity	NPD5691	Approved
0.6923	Remote Similarity	NPD6599	Discontinued
0.6923	Remote Similarity	NPD7028	Phase 2
0.6919	Remote Similarity	NPD7296	Approved
0.6919	Remote Similarity	NPD7768	Phase 2
0.6914	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6005	Phase 3
0.6914	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6002	Phase 3
0.6914	Remote Similarity	NPD3540	Phase 1
0.6914	Remote Similarity	NPD6004	Phase 3
0.6909	Remote Similarity	NPD5058	Phase 3
0.6907	Remote Similarity	NPD8151	Discontinued
0.6899	Remote Similarity	NPD6233	Phase 2
0.6894	Remote Similarity	NPD7033	Discontinued
0.6894	Remote Similarity	NPD3748	Approved
0.6894	Remote Similarity	NPD4108	Discontinued
0.689	Remote Similarity	NPD3892	Phase 2
0.689	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD5126	Approved
0.6887	Remote Similarity	NPD5125	Phase 3
0.6886	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD3749	Approved
0.6879	Remote Similarity	NPD4055	Discovery
0.6875	Remote Similarity	NPD3926	Phase 2
0.6863	Remote Similarity	NPD1608	Approved
0.686	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD5005	Approved
0.6859	Remote Similarity	NPD5006	Approved
0.6852	Remote Similarity	NPD6032	Approved
0.6852	Remote Similarity	NPD3539	Phase 1
0.6848	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD5403	Approved
0.6839	Remote Similarity	NPD2797	Approved
0.6835	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5711	Approved
0.6818	Remote Similarity	NPD5710	Approved
0.681	Remote Similarity	NPD1375	Discontinued
0.681	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.681	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD3686	Approved
0.6805	Remote Similarity	NPD3687	Approved
0.68	Remote Similarity	NPD4666	Phase 3
0.68	Remote Similarity	NPD5536	Phase 2
0.68	Remote Similarity	NPD6746	Phase 2
0.6797	Remote Similarity	NPD1281	Approved
0.6797	Remote Similarity	NPD1611	Approved
0.6793	Remote Similarity	NPD8434	Phase 2
0.679	Remote Similarity	NPD1510	Phase 2
0.6788	Remote Similarity	NPD8166	Discontinued
0.6784	Remote Similarity	NPD5089	Approved
0.6784	Remote Similarity	NPD7411	Suspended
0.6784	Remote Similarity	NPD5090	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