NPASS Compound

Structure

CID324962 OpenBabel06191716182D 31 34 0 0 1 0 0 0 0 0999 V2000 5.6867 1.5977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5077 2.7767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1463 -3.6476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7852 -2.8297 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3685 -2.0118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8982 -2.5415 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6185 -1.1939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7161 1.7085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5551 0.7641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8141 1.2363 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1463 1.9041 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1463 -0.3760 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5340 1.2363 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1463 -2.0118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8982 1.2363 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2019 -0.3760 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5340 0.2918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8141 0.2918 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2019 1.9041 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2019 -2.0118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8982 0.2918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7296 -1.1939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7161 -0.1804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6867 -0.0696 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8404 2.7767 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6185 -2.8297 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7296 -2.8297 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8408 -1.1939 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7161 -2.0693 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.5281 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 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 28 1 0 0 0 0 6 29 1 0 0 0 0 7 12 2 0 0 0 0 7 14 1 0 0 0 0 8 13 2 0 0 0 0 8 15 1 0 0 0 0 9 30 1 0 0 0 0 9 31 1 0 0 0 0 10 1 1 6 0 0 0 10 11 1 0 0 0 0 10 18 1 0 0 0 0 11 2 1 6 0 0 0 11 19 1 0 0 0 0 12 16 1 0 0 0 0 12 18 1 0 0 0 0 13 17 1 0 0 0 0 13 19 1 0 0 0 0 14 20 2 0 0 0 0 14 26 1 0 0 0 0 15 21 2 0 0 0 0 15 30 1 0 0 0 0 16 17 1 0 0 0 0 16 22 2 0 0 0 0 17 23 2 0 0 0 0 18 24 1 6 0 0 0 19 25 1 6 0 0 0 20 22 1 0 0 0 0 20 27 1 0 0 0 0 21 23 1 0 0 0 0 21 31 1 0 0 0 0 22 28 1 0 0 0 0 23 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	432.18
Volume:	426.641
LogP:	2.335
LogD:	2.741
LogS:	-3.431
# Rotatable Bonds:	4
TPSA:	95.84
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.758
Synthetic Accessibility Score:	3.97
Fsp3:	0.478
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:	-4.83
MDCK Permeability:	2.9509841624530964e-05
Pgp-inhibitor:	0.117
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.217
Plasma Protein Binding (PPB):	76.25872039794922%
Volume Distribution (VD):	0.976
Pgp-substrate:	15.722365379333496%

ADMET: Metabolism

CYP1A2-inhibitor:	0.063
CYP1A2-substrate:	0.983
CYP2C19-inhibitor:	0.152
CYP2C19-substrate:	0.927
CYP2C9-inhibitor:	0.017
CYP2C9-substrate:	0.885
CYP2D6-inhibitor:	0.055
CYP2D6-substrate:	0.668
CYP3A4-inhibitor:	0.771
CYP3A4-substrate:	0.847

ADMET: Excretion

Clearance (CL):	5.56
Half-life (T1/2):	0.142

ADMET: Toxicity

hERG Blockers:	0.299
Human Hepatotoxicity (H-HT):	0.063
Drug-inuced Liver Injury (DILI):	0.228
AMES Toxicity:	0.054
Rat Oral Acute Toxicity:	0.056
Maximum Recommended Daily Dose:	0.022
Skin Sensitization:	0.097
Carcinogencity:	0.153
Eye Corrosion:	0.003
Eye Irritation:	0.023
Respiratory Toxicity:	0.189

Download Data

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

Natural Product: NPC324962

Natural Product ID:	NPC324962
*Common Name:**	Ananolignan C
IUPAC Name:	n.a.
Synonyms:	Ananolignan C
Standard InCHIKey:	RGJPPASWKJBDTJ-XJSVZPCESA-N
Standard InCHI:	InChI=1S/C23H28O8/c1-10-11(2)19(25)13-8-15-21(31-9-30-15)23(29-6)17(13)16-12(18(10)24)7-14(26-3)20(27-4)22(16)28-5/h7-8,10-11,18-19,24-25H,9H2,1-6H3/t10-,11+,18-,19+/m0/s1
SMILES:	COc1cc2[C@@H](O)[C@@H](C)[C@@H](C)[C@H](c3c(c2c(c1OC)OC)c(OC)c1c(c3)OCO1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1782111
PubChem CID:	53355340
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
NPO27599	Kadsura ananosma	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165154]
NPO27599	Kadsura ananosma	Species	Schisandraceae	Eukaryota	Stems	n.a.	n.a.	PMID[20025236]
NPO27599	Kadsura ananosma	Species	Schisandraceae	Eukaryota	n.a.	seed	n.a.	PMID[21381710]
NPO27599	Kadsura ananosma	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27599	Kadsura ananosma	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT519	Cell Line	SH-SY5Y	Homo sapiens	Activity	=	57.7	%	PMID[568180]
NPT519	Cell Line	SH-SY5Y	Homo sapiens	Activity	=	59.6	%	PMID[568180]

☑ 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 NPC324962 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	397
0.1-0.2	1503
0.2-0.3	4031
0.3-0.4	10446
0.4-0.5	8356
0.5-0.6	4358
0.6-0.7	8399
0.7-0.8	3800
0.8-0.85	1022
0.85-0.9	289
0.9-0.95	76
0.95-1	20

Similarity Score	Similarity Level	Natural Product ID
0.9926	High Similarity	NPC103637
0.9926	High Similarity	NPC229172
0.9926	High Similarity	NPC36531
0.9926	High Similarity	NPC230538
0.9854	High Similarity	NPC475868
0.9781	High Similarity	NPC239254
0.9781	High Similarity	NPC172171
0.971	High Similarity	NPC166506
0.971	High Similarity	NPC189239
0.971	High Similarity	NPC110763
0.971	High Similarity	NPC197352
0.9643	High Similarity	NPC325720
0.9643	High Similarity	NPC316676
0.9638	High Similarity	NPC121661
0.9638	High Similarity	NPC73467
0.9559	High Similarity	NPC53722
0.9559	High Similarity	NPC201404
0.9559	High Similarity	NPC290714
0.9507	High Similarity	NPC473989
0.95	High Similarity	NPC252286
0.95	High Similarity	NPC154971
0.9493	High Similarity	NPC184684
0.9493	High Similarity	NPC184641
0.9493	High Similarity	NPC133934
0.9407	High Similarity	NPC185680
0.9407	High Similarity	NPC145722
0.9407	High Similarity	NPC256776
0.931	High Similarity	NPC24562
0.9306	High Similarity	NPC475756
0.9286	High Similarity	NPC76415
0.9286	High Similarity	NPC218510
0.927	High Similarity	NPC32189
0.9247	High Similarity	NPC312763
0.9247	High Similarity	NPC473425
0.9241	High Similarity	NPC471154
0.9231	High Similarity	NPC304821
0.922	High Similarity	NPC326144
0.9203	High Similarity	NPC86605
0.9203	High Similarity	NPC46277
0.9203	High Similarity	NPC3072
0.9203	High Similarity	NPC301765
0.9203	High Similarity	NPC156948
0.9203	High Similarity	NPC474039
0.9197	High Similarity	NPC150534
0.9191	High Similarity	NPC196937
0.9191	High Similarity	NPC58585
0.9178	High Similarity	NPC474606
0.9172	High Similarity	NPC224472
0.9155	High Similarity	NPC318286
0.9155	High Similarity	NPC327651
0.9149	High Similarity	NPC474808
0.913	High Similarity	NPC133025
0.913	High Similarity	NPC197166
0.9122	High Similarity	NPC473323
0.9091	High Similarity	NPC321958
0.9091	High Similarity	NPC321696
0.9071	High Similarity	NPC216434
0.9071	High Similarity	NPC46591
0.9071	High Similarity	NPC103448
0.9065	High Similarity	NPC283949
0.9058	High Similarity	NPC236522
0.9054	High Similarity	NPC476065
0.9054	High Similarity	NPC238834
0.9051	High Similarity	NPC112237
0.9048	High Similarity	NPC53669
0.9048	High Similarity	NPC77237
0.9048	High Similarity	NPC217708
0.9048	High Similarity	NPC297271
0.9048	High Similarity	NPC126405
0.9048	High Similarity	NPC16791
0.9048	High Similarity	NPC308739
0.9	High Similarity	NPC30951
0.9	High Similarity	NPC9068
0.9	High Similarity	NPC471183
0.9	High Similarity	NPC6369
0.8986	High Similarity	NPC198461
0.8986	High Similarity	NPC555
0.8986	High Similarity	NPC56764
0.8986	High Similarity	NPC469659
0.8986	High Similarity	NPC188378
0.8986	High Similarity	NPC276026
0.8986	High Similarity	NPC289258
0.8986	High Similarity	NPC206737
0.8986	High Similarity	NPC7515
0.8978	High Similarity	NPC102256
0.8966	High Similarity	NPC252281
0.8966	High Similarity	NPC198129
0.8966	High Similarity	NPC327352
0.8966	High Similarity	NPC477375
0.8958	High Similarity	NPC474054
0.8951	High Similarity	NPC87883
0.8951	High Similarity	NPC472713
0.8951	High Similarity	NPC118385
0.8951	High Similarity	NPC472712
0.8951	High Similarity	NPC473046
0.8951	High Similarity	NPC187774
0.8944	High Similarity	NPC191231
0.8944	High Similarity	NPC41782
0.8944	High Similarity	NPC474295
0.8944	High Similarity	NPC287124
0.8936	High Similarity	NPC177868
0.8936	High Similarity	NPC56091
0.8936	High Similarity	NPC284464
0.8936	High Similarity	NPC226547
0.8933	High Similarity	NPC475592
0.8929	High Similarity	NPC196420
0.8929	High Similarity	NPC185908
0.8921	High Similarity	NPC240279
0.8921	High Similarity	NPC55239
0.8921	High Similarity	NPC180602
0.8921	High Similarity	NPC214853
0.8905	High Similarity	NPC184928
0.8905	High Similarity	NPC141493
0.8904	High Similarity	NPC322426
0.8904	High Similarity	NPC477374
0.8904	High Similarity	NPC85141
0.8904	High Similarity	NPC477376
0.8897	High Similarity	NPC116019
0.8889	High Similarity	NPC180953
0.8881	High Similarity	NPC12728
0.8881	High Similarity	NPC185071
0.8874	High Similarity	NPC215400
0.8874	High Similarity	NPC230531
0.8867	High Similarity	NPC29727
0.8857	High Similarity	NPC172818
0.8857	High Similarity	NPC25695
0.8849	High Similarity	NPC326095
0.8849	High Similarity	NPC244983
0.8844	High Similarity	NPC469706
0.8844	High Similarity	NPC218041
0.8844	High Similarity	NPC214326
0.8844	High Similarity	NPC260781
0.8844	High Similarity	NPC24425
0.8844	High Similarity	NPC9933
0.8844	High Similarity	NPC472709
0.8844	High Similarity	NPC182368
0.8844	High Similarity	NPC145979
0.8844	High Similarity	NPC469707
0.8844	High Similarity	NPC316989
0.8844	High Similarity	NPC185955
0.8844	High Similarity	NPC225815
0.8844	High Similarity	NPC472710
0.8841	High Similarity	NPC104077
0.8841	High Similarity	NPC219671
0.8841	High Similarity	NPC147616
0.8841	High Similarity	NPC475856
0.8841	High Similarity	NPC259742
0.8841	High Similarity	NPC97316
0.8841	High Similarity	NPC261812
0.8841	High Similarity	NPC72046
0.8841	High Similarity	NPC65183
0.8836	High Similarity	NPC477879
0.8836	High Similarity	NPC270751
0.8832	High Similarity	NPC63574
0.8832	High Similarity	NPC184814
0.8828	High Similarity	NPC190714
0.8828	High Similarity	NPC99515
0.8828	High Similarity	NPC212890
0.8828	High Similarity	NPC33832
0.8824	High Similarity	NPC149008
0.8824	High Similarity	NPC283114
0.8824	High Similarity	NPC207702
0.8819	High Similarity	NPC166884
0.8819	High Similarity	NPC477701
0.8819	High Similarity	NPC141569
0.8816	High Similarity	NPC63061
0.8815	High Similarity	NPC473960
0.8811	High Similarity	NPC5262
0.8811	High Similarity	NPC472714
0.8794	High Similarity	NPC477938
0.8794	High Similarity	NPC865
0.8792	High Similarity	NPC245948
0.8786	High Similarity	NPC49235
0.8786	High Similarity	NPC148893
0.8786	High Similarity	NPC25333
0.8784	High Similarity	NPC303519
0.8777	High Similarity	NPC1474
0.8777	High Similarity	NPC266848
0.8777	High Similarity	NPC471391
0.8777	High Similarity	NPC136750
0.8777	High Similarity	NPC471390
0.8767	High Similarity	NPC39657
0.8766	High Similarity	NPC469475
0.8766	High Similarity	NPC475865
0.8766	High Similarity	NPC469518
0.8759	High Similarity	NPC477702
0.8759	High Similarity	NPC307466
0.875	High Similarity	NPC242032
0.875	High Similarity	NPC298317
0.875	High Similarity	NPC469630
0.875	High Similarity	NPC255566
0.875	High Similarity	NPC265154
0.8741	High Similarity	NPC311530
0.8741	High Similarity	NPC312199
0.8732	High Similarity	NPC6300
0.8732	High Similarity	NPC114171
0.8732	High Similarity	NPC292487
0.8732	High Similarity	NPC230124
0.8725	High Similarity	NPC475229
0.8725	High Similarity	NPC21902

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 NPC324962 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	322
0.1-0.2	917
0.2-0.3	1905
0.3-0.4	2811
0.4-0.5	1630
0.5-0.6	928
0.6-0.7	547
0.7-0.8	79
0.8-0.85	7
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8792	High Similarity	NPD37	Approved
0.8618	High Similarity	NPD4965	Approved
0.8618	High Similarity	NPD4967	Phase 2
0.8618	High Similarity	NPD4966	Approved
0.8489	Intermediate Similarity	NPD3027	Phase 3
0.8387	Intermediate Similarity	NPD6234	Discontinued
0.8309	Intermediate Similarity	NPD3705	Approved
0.8165	Intermediate Similarity	NPD7199	Phase 2
0.8137	Intermediate Similarity	NPD7228	Approved
0.8056	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD1613	Approved
0.7987	Intermediate Similarity	NPD6674	Discontinued
0.795	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD3018	Phase 2
0.7832	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD7240	Approved
0.7826	Intermediate Similarity	NPD1357	Approved
0.7778	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD3818	Discontinued
0.7692	Intermediate Similarity	NPD1653	Approved
0.7676	Intermediate Similarity	NPD2982	Phase 2
0.7676	Intermediate Similarity	NPD2983	Phase 2
0.7655	Intermediate Similarity	NPD4908	Phase 1
0.7647	Intermediate Similarity	NPD5283	Phase 1
0.7639	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD2981	Phase 2
0.7568	Intermediate Similarity	NPD3620	Phase 2
0.7568	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD1091	Approved
0.7535	Intermediate Similarity	NPD1610	Phase 2
0.7516	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7074	Phase 3
0.7483	Intermediate Similarity	NPD4625	Phase 3
0.7466	Intermediate Similarity	NPD2861	Phase 2
0.7455	Intermediate Similarity	NPD6232	Discontinued
0.744	Intermediate Similarity	NPD7054	Approved
0.744	Intermediate Similarity	NPD5844	Phase 1
0.7436	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD7473	Discontinued
0.7421	Intermediate Similarity	NPD4005	Discontinued
0.7396	Intermediate Similarity	NPD7472	Approved
0.7386	Intermediate Similarity	NPD7266	Discontinued
0.7333	Intermediate Similarity	NPD4060	Phase 1
0.7315	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD4749	Approved
0.731	Intermediate Similarity	NPD6559	Discontinued
0.7301	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD1934	Approved
0.7283	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3540	Phase 1
0.7267	Intermediate Similarity	NPD7808	Phase 3
0.7256	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD1548	Phase 1
0.7251	Intermediate Similarity	NPD6797	Phase 2
0.7244	Intermediate Similarity	NPD3892	Phase 2
0.7239	Intermediate Similarity	NPD2977	Approved
0.7239	Intermediate Similarity	NPD2978	Approved
0.7233	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD2238	Phase 2
0.7212	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD4055	Discovery
0.7209	Intermediate Similarity	NPD7251	Discontinued
0.7208	Intermediate Similarity	NPD3539	Phase 1
0.7205	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD5177	Phase 3
0.7168	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD5763	Approved
0.7161	Intermediate Similarity	NPD5762	Approved
0.716	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6166	Phase 2
0.716	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD6843	Phase 3
0.7159	Intermediate Similarity	NPD6842	Approved
0.7159	Intermediate Similarity	NPD6841	Approved
0.7153	Intermediate Similarity	NPD5125	Phase 3
0.7153	Intermediate Similarity	NPD5126	Approved
0.7152	Intermediate Similarity	NPD3882	Suspended
0.7152	Intermediate Similarity	NPD5058	Phase 3
0.7143	Intermediate Similarity	NPD3787	Discontinued
0.7143	Intermediate Similarity	NPD4108	Discontinued
0.7143	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1465	Phase 2
0.7126	Intermediate Similarity	NPD5494	Approved
0.7122	Intermediate Similarity	NPD228	Approved
0.712	Intermediate Similarity	NPD7680	Approved
0.7091	Intermediate Similarity	NPD3817	Phase 2
0.7091	Intermediate Similarity	NPD2563	Approved
0.7091	Intermediate Similarity	NPD2560	Approved
0.7086	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD4236	Phase 3
0.707	Intermediate Similarity	NPD4237	Approved
0.7059	Intermediate Similarity	NPD3657	Discovery
0.7051	Intermediate Similarity	NPD1375	Discontinued
0.7044	Intermediate Similarity	NPD7124	Phase 2
0.7042	Intermediate Similarity	NPD709	Approved
0.7041	Intermediate Similarity	NPD7229	Phase 3
0.703	Intermediate Similarity	NPD8455	Phase 2
0.703	Intermediate Similarity	NPD2801	Approved
0.7006	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4357	Discontinued
0.6981	Remote Similarity	NPD2677	Approved
0.6978	Remote Similarity	NPD3021	Approved
0.6978	Remote Similarity	NPD4750	Phase 3
0.6978	Remote Similarity	NPD3022	Approved
0.6977	Remote Similarity	NPD3751	Discontinued
0.6974	Remote Similarity	NPD5110	Phase 2
0.6974	Remote Similarity	NPD5111	Phase 2
0.6974	Remote Similarity	NPD5109	Approved
0.6968	Remote Similarity	NPD6111	Discontinued
0.6962	Remote Similarity	NPD3060	Approved
0.6959	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2533	Approved
0.6957	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2532	Approved
0.6957	Remote Similarity	NPD2534	Approved
0.6951	Remote Similarity	NPD4678	Approved
0.6951	Remote Similarity	NPD7028	Phase 2
0.6951	Remote Similarity	NPD4380	Phase 2
0.6951	Remote Similarity	NPD4675	Approved
0.6948	Remote Similarity	NPD5124	Phase 1
0.6948	Remote Similarity	NPD6355	Discontinued
0.6948	Remote Similarity	NPD5735	Approved
0.6948	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD7819	Suspended
0.6923	Remote Similarity	NPD7157	Approved
0.6918	Remote Similarity	NPD4110	Phase 3
0.6918	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD4626	Approved
0.6914	Remote Similarity	NPD7685	Pre-registration
0.6913	Remote Similarity	NPD6696	Suspended
0.6909	Remote Similarity	NPD5090	Approved
0.6909	Remote Similarity	NPD5089	Approved
0.6903	Remote Similarity	NPD4097	Suspended
0.6901	Remote Similarity	NPD2970	Approved
0.6901	Remote Similarity	NPD2969	Approved
0.6883	Remote Similarity	NPD4140	Approved
0.6882	Remote Similarity	NPD6959	Discontinued
0.6882	Remote Similarity	NPD8127	Discontinued
0.6879	Remote Similarity	NPD2438	Suspended
0.6879	Remote Similarity	NPD6100	Approved
0.6879	Remote Similarity	NPD6099	Approved
0.6875	Remote Similarity	NPD5241	Discontinued
0.6875	Remote Similarity	NPD7549	Discontinued
0.6875	Remote Similarity	NPD2219	Phase 1
0.6867	Remote Similarity	NPD3383	Approved
0.6867	Remote Similarity	NPD3384	Approved
0.6867	Remote Similarity	NPD3382	Approved
0.6867	Remote Similarity	NPD3094	Phase 2
0.6857	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD1652	Phase 2
0.6842	Remote Similarity	NPD6071	Discontinued
0.6842	Remote Similarity	NPD3051	Approved
0.6833	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD7843	Approved
0.6828	Remote Similarity	NPD5536	Phase 2
0.6826	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD422	Phase 1
0.6815	Remote Similarity	NPD5588	Approved
0.6813	Remote Similarity	NPD6331	Phase 2
0.6813	Remote Similarity	NPD3750	Approved
0.681	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD3926	Phase 2
0.68	Remote Similarity	NPD1283	Approved
0.68	Remote Similarity	NPD8651	Approved
0.679	Remote Similarity	NPD1511	Approved
0.6786	Remote Similarity	NPD2684	Approved
0.6779	Remote Similarity	NPD2230	Approved
0.6779	Remote Similarity	NPD2233	Approved
0.6779	Remote Similarity	NPD2232	Approved
0.6763	Remote Similarity	NPD2489	Approved
0.6763	Remote Similarity	NPD27	Approved
0.6752	Remote Similarity	NPD4538	Approved
0.6752	Remote Similarity	NPD4536	Approved
0.6752	Remote Similarity	NPD7097	Phase 1
0.6752	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5691	Approved
0.6733	Remote Similarity	NPD5327	Phase 3
0.673	Remote Similarity	NPD6002	Phase 3
0.673	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.673	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.673	Remote Similarity	NPD6004	Phase 3
0.673	Remote Similarity	NPD6005	Phase 3
0.6728	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD4663	Approved
0.6715	Remote Similarity	NPD940	Approved
0.6715	Remote Similarity	NPD846	Approved
0.6714	Remote Similarity	NPD290	Approved
0.6711	Remote Similarity	NPD3092	Approved
0.6711	Remote Similarity	NPD4624	Approved
0.6709	Remote Similarity	NPD6028	Clinical (unspecified phase)

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