NPASS Compound

Structure

CID320223 OpenBabel06191716152D 24 28 0 0 1 0 0 0 0 0999 V2000 2.5935 4.1441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0305 -1.4392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4162 0.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4285 -0.0189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1978 3.6777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9956 4.1374 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6067 2.2869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6075 2.2829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9166 -0.0963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6027 1.3689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1931 2.7474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8038 2.7505 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.6273 -0.4957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6066 1.3624 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9913 2.2865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8014 0.8921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9985 1.3557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8137 -0.0402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1916 0.9015 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7938 3.6766 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.6395 -1.4213 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0182 -0.5136 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2915 0.7457 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 20 1 0 0 0 0 2 22 1 0 0 0 0 3 4 2 0 0 0 0 3 10 1 0 0 0 0 4 13 1 0 0 0 0 5 6 1 0 0 0 0 5 11 1 0 0 0 0 6 20 1 0 0 0 0 7 10 1 0 0 0 0 7 12 1 0 0 0 0 8 11 2 0 0 0 0 8 14 1 0 0 0 0 9 23 1 0 0 0 0 9 24 1 0 0 0 0 10 16 2 0 0 0 0 11 15 1 0 0 0 0 12 15 1 0 0 0 0 12 20 1 0 0 0 0 13 18 2 0 0 0 0 13 21 1 0 0 0 0 14 19 2 0 0 0 0 14 23 1 0 0 0 0 15 17 2 0 0 0 0 16 17 1 0 0 0 0 16 18 1 0 0 0 0 17 19 1 0 0 0 0 18 22 1 0 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	325.13
Volume:	324.737
LogP:	2.49
LogD:	2.651
LogS:	-1.942
# Rotatable Bonds:	1
TPSA:	51.16
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.874
Synthetic Accessibility Score:	3.3
Fsp3:	0.368
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:	-4.77
MDCK Permeability:	2.330751703993883e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.341
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.972
Plasma Protein Binding (PPB):	93.43500518798828%
Volume Distribution (VD):	1.592
Pgp-substrate:	6.196472644805908%

ADMET: Metabolism

CYP1A2-inhibitor:	0.747
CYP1A2-substrate:	0.88
CYP2C19-inhibitor:	0.232
CYP2C19-substrate:	0.833
CYP2C9-inhibitor:	0.019
CYP2C9-substrate:	0.665
CYP2D6-inhibitor:	0.595
CYP2D6-substrate:	0.921
CYP3A4-inhibitor:	0.39
CYP3A4-substrate:	0.903

ADMET: Excretion

Clearance (CL):	16.264
Half-life (T1/2):	0.231

ADMET: Toxicity

hERG Blockers:	0.612
Human Hepatotoxicity (H-HT):	0.101
Drug-inuced Liver Injury (DILI):	0.24
AMES Toxicity:	0.798
Rat Oral Acute Toxicity:	0.741
Maximum Recommended Daily Dose:	0.902
Skin Sensitization:	0.321
Carcinogencity:	0.64
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.849

Download Data

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

Natural Product: NPC320223

Natural Product ID:	NPC320223
*Common Name:**	WOIZHRXESCUSGM-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WOIZHRXESCUSGM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H19NO4/c1-20-6-5-11-8-14-19(24-9-23-14)17-15(11)12(20)7-10-3-4-13(21)18(22-2)16(10)17/h3-4,8,12,21H,5-7,9H2,1-2H3
SMILES:	CN1CCC2=CC3=C(C4=C2C1CC5=C4C(=C(C=C5)O)OC)OCO3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3194830
PubChem CID:	3083908
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0000381] Aporphines

*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
NPO2204	Lindera megaphylla	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2204	Lindera megaphylla	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2204	Lindera megaphylla	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2204	Lindera megaphylla	Species	Lauraceae	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
Potency	10

Activity Type	# Activity
Individual Protein	9
PROTEIN-PROTEIN INTERACTION	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT483	Individual Protein	Prelamin-A/C	Homo sapiens	Potency	=	12589.3	nM	PMID[476211]
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	35481.3	nM	PMID[476211]
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[476211]
NPT1474	Individual Protein	ATP-dependent Clp protease proteolytic subunit	Bacillus subtilis (strain 168)	Potency	n.a.	31622.8	nM	PMID[476211]
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	316.2	nM	PMID[476211]
NPT446	Individual Protein	Rap guanine nucleotide exchange factor 3	Homo sapiens	Potency	n.a.	5623.4	nM	PMID[476211]
NPT21702	PROTEIN-PROTEIN INTERACTION	Importin subunit beta-1/Snurportin-1	Homo sapiens	Potency	n.a.	112201.8	nM	PMID[476211]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	79432.8	nM	PMID[476211]
NPT755	Individual Protein	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[476211]
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Potency	n.a.	32642.7	nM	PMID[476211]

☑ 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 NPC320223 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	341
0.1-0.2	1652
0.2-0.3	7314
0.3-0.4	10671
0.4-0.5	5702
0.5-0.6	11100
0.6-0.7	4705
0.7-0.8	823
0.8-0.85	211
0.85-0.9	107
0.9-0.95	64
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC114364
0.9876	High Similarity	NPC229166
0.9876	High Similarity	NPC128560
0.9876	High Similarity	NPC199465
0.9639	High Similarity	NPC135772
0.9578	High Similarity	NPC116284
0.9565	High Similarity	NPC81218
0.9565	High Similarity	NPC474931
0.9565	High Similarity	NPC145832
0.9565	High Similarity	NPC306555
0.9565	High Similarity	NPC298979
0.9565	High Similarity	NPC158376
0.9565	High Similarity	NPC247389
0.9565	High Similarity	NPC117188
0.9565	High Similarity	NPC205421
0.9565	High Similarity	NPC12053
0.9518	High Similarity	NPC312918
0.9518	High Similarity	NPC477561
0.9518	High Similarity	NPC476574
0.9518	High Similarity	NPC155442
0.9503	High Similarity	NPC24264
0.9503	High Similarity	NPC476432
0.9503	High Similarity	NPC219341
0.9461	High Similarity	NPC248642
0.9441	High Similarity	NPC167546
0.9441	High Similarity	NPC16805
0.9441	High Similarity	NPC196447
0.9441	High Similarity	NPC78222
0.9441	High Similarity	NPC96603
0.9441	High Similarity	NPC306843
0.9441	High Similarity	NPC212794
0.9441	High Similarity	NPC302527
0.9441	High Similarity	NPC477563
0.9441	High Similarity	NPC225774
0.9441	High Similarity	NPC13504
0.9441	High Similarity	NPC253043
0.9441	High Similarity	NPC136508
0.9405	High Similarity	NPC156576
0.9379	High Similarity	NPC1229
0.9379	High Similarity	NPC324144
0.9341	High Similarity	NPC126284
0.9325	High Similarity	NPC210918
0.9298	High Similarity	NPC82763
0.9277	High Similarity	NPC477558
0.9255	High Similarity	NPC477559
0.9255	High Similarity	NPC266753
0.9255	High Similarity	NPC166014
0.9255	High Similarity	NPC160298
0.9255	High Similarity	NPC306902
0.9255	High Similarity	NPC27410
0.9255	High Similarity	NPC232924
0.924	High Similarity	NPC476576
0.924	High Similarity	NPC186546
0.9217	High Similarity	NPC477020
0.9217	High Similarity	NPC192135
0.9217	High Similarity	NPC66341
0.9181	High Similarity	NPC57036
0.9157	High Similarity	NPC149090
0.9157	High Similarity	NPC239775
0.9157	High Similarity	NPC19520
0.913	High Similarity	NPC476572
0.9096	High Similarity	NPC26240
0.9096	High Similarity	NPC69712
0.9096	High Similarity	NPC6152
0.9096	High Similarity	NPC118274
0.9096	High Similarity	NPC477562
0.9096	High Similarity	NPC152212
0.9096	High Similarity	NPC168753
0.9085	High Similarity	NPC276944
0.9085	High Similarity	NPC238530
0.9085	High Similarity	NPC232514
0.907	High Similarity	NPC214116
0.9053	High Similarity	NPC294790
0.9053	High Similarity	NPC118633
0.9053	High Similarity	NPC148693
0.9006	High Similarity	NPC325871
0.9006	High Similarity	NPC99659
0.8963	High Similarity	NPC60186
0.8957	High Similarity	NPC111485
0.8947	High Similarity	NPC474506
0.8947	High Similarity	NPC32413
0.8922	High Similarity	NPC241055
0.8916	High Similarity	NPC304659
0.8916	High Similarity	NPC35627
0.8916	High Similarity	NPC86144
0.8916	High Similarity	NPC476573
0.8916	High Similarity	NPC81247
0.8895	High Similarity	NPC476575
0.8889	High Similarity	NPC470879
0.8889	High Similarity	NPC474507
0.8889	High Similarity	NPC258695
0.8876	High Similarity	NPC2314
0.8855	High Similarity	NPC168409
0.883	High Similarity	NPC23219
0.882	High Similarity	NPC81733
0.882	High Similarity	NPC326316
0.8807	High Similarity	NPC475754
0.8795	High Similarity	NPC189470
0.8779	High Similarity	NPC267408
0.8772	High Similarity	NPC173416
0.8772	High Similarity	NPC148709
0.8772	High Similarity	NPC476577
0.8772	High Similarity	NPC112575
0.8757	High Similarity	NPC117717
0.872	High Similarity	NPC186063
0.8693	High Similarity	NPC237579
0.8693	High Similarity	NPC474904
0.8678	High Similarity	NPC275132
0.8659	High Similarity	NPC216459
0.8659	High Similarity	NPC244112
0.8659	High Similarity	NPC207757
0.8659	High Similarity	NPC110416
0.8659	High Similarity	NPC249797
0.8659	High Similarity	NPC172765
0.8659	High Similarity	NPC54379
0.8659	High Similarity	NPC41178
0.8659	High Similarity	NPC204828
0.8659	High Similarity	NPC127674
0.8659	High Similarity	NPC138487
0.8659	High Similarity	NPC5238
0.8659	High Similarity	NPC2413
0.8659	High Similarity	NPC469817
0.8659	High Similarity	NPC278799
0.8659	High Similarity	NPC39701
0.8659	High Similarity	NPC276588
0.8659	High Similarity	NPC295691
0.8659	High Similarity	NPC193949
0.8659	High Similarity	NPC189266
0.8659	High Similarity	NPC184026
0.8639	High Similarity	NPC210140
0.8639	High Similarity	NPC150879
0.8634	High Similarity	NPC135538
0.8634	High Similarity	NPC475959
0.8634	High Similarity	NPC24233
0.8634	High Similarity	NPC147390
0.8634	High Similarity	NPC476571
0.8634	High Similarity	NPC246587
0.8634	High Similarity	NPC428
0.8606	High Similarity	NPC146288
0.858	High Similarity	NPC264850
0.858	High Similarity	NPC124657
0.858	High Similarity	NPC13916
0.858	High Similarity	NPC103379
0.858	High Similarity	NPC477565
0.8571	High Similarity	NPC233718
0.8571	High Similarity	NPC191376
0.8571	High Similarity	NPC321505
0.8571	High Similarity	NPC179825
0.8563	High Similarity	NPC32154
0.8547	High Similarity	NPC24260
0.8547	High Similarity	NPC478093
0.8537	High Similarity	NPC26601
0.8529	High Similarity	NPC181653
0.8529	High Similarity	NPC190332
0.8528	High Similarity	NPC151895
0.8528	High Similarity	NPC192768
0.8528	High Similarity	NPC88249
0.8528	High Similarity	NPC97221
0.8528	High Similarity	NPC220858
0.8521	High Similarity	NPC24465
0.8521	High Similarity	NPC134858
0.85	High Similarity	NPC478092
0.85	High Similarity	NPC478091
0.85	High Similarity	NPC30182
0.85	High Similarity	NPC473589
0.8497	Intermediate Similarity	NPC187678
0.8494	Intermediate Similarity	NPC31311
0.8494	Intermediate Similarity	NPC170503
0.8494	Intermediate Similarity	NPC126519
0.8494	Intermediate Similarity	NPC234392
0.8494	Intermediate Similarity	NPC203784
0.8483	Intermediate Similarity	NPC312531
0.8466	Intermediate Similarity	NPC211296
0.8462	Intermediate Similarity	NPC233650
0.8457	Intermediate Similarity	NPC476151
0.8452	Intermediate Similarity	NPC205167
0.8452	Intermediate Similarity	NPC249274
0.8448	Intermediate Similarity	NPC241704
0.8447	Intermediate Similarity	NPC185838
0.8434	Intermediate Similarity	NPC76079
0.843	Intermediate Similarity	NPC311991
0.8427	Intermediate Similarity	NPC320088
0.8424	Intermediate Similarity	NPC233029
0.8424	Intermediate Similarity	NPC210148
0.8421	Intermediate Similarity	NPC204947
0.8421	Intermediate Similarity	NPC100566
0.8409	Intermediate Similarity	NPC179704
0.8402	Intermediate Similarity	NPC80759
0.8402	Intermediate Similarity	NPC79402
0.8393	Intermediate Similarity	NPC477080
0.8382	Intermediate Similarity	NPC470739
0.8382	Intermediate Similarity	NPC231371
0.8382	Intermediate Similarity	NPC477640
0.8382	Intermediate Similarity	NPC225597
0.838	Intermediate Similarity	NPC275680
0.838	Intermediate Similarity	NPC22115
0.8372	Intermediate Similarity	NPC83198
0.8372	Intermediate Similarity	NPC204908
0.8354	Intermediate Similarity	NPC219162
0.8353	Intermediate Similarity	NPC320104

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 NPC320223 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	198
0.1-0.2	774
0.2-0.3	1068
0.3-0.4	2175
0.4-0.5	2628
0.5-0.6	1599
0.6-0.7	567
0.7-0.8	126
0.8-0.85	15
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8509	High Similarity	NPD2421	Approved
0.8509	High Similarity	NPD2420	Approved
0.848	Intermediate Similarity	NPD2489	Approved
0.848	Intermediate Similarity	NPD27	Approved
0.8471	Intermediate Similarity	NPD3051	Approved
0.8427	Intermediate Similarity	NPD7906	Approved
0.8421	Intermediate Similarity	NPD2970	Approved
0.8421	Intermediate Similarity	NPD2969	Approved
0.8305	Intermediate Similarity	NPD4577	Approved
0.8305	Intermediate Similarity	NPD7310	Approved
0.8305	Intermediate Similarity	NPD7312	Approved
0.8305	Intermediate Similarity	NPD4578	Approved
0.8305	Intermediate Similarity	NPD7311	Approved
0.8305	Intermediate Similarity	NPD7313	Approved
0.8268	Intermediate Similarity	NPD4663	Approved
0.8258	Intermediate Similarity	NPD7309	Approved
0.8232	Intermediate Similarity	NPD4584	Approved
0.8199	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8156	Intermediate Similarity	NPD8053	Approved
0.8156	Intermediate Similarity	NPD8054	Approved
0.8057	Intermediate Similarity	NPD4481	Phase 3
0.8057	Intermediate Similarity	NPD2898	Approved
0.7953	Intermediate Similarity	NPD2978	Approved
0.7953	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD2977	Approved
0.7939	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD2488	Approved
0.7935	Intermediate Similarity	NPD2490	Approved
0.7842	Intermediate Similarity	NPD3452	Approved
0.7842	Intermediate Similarity	NPD2493	Approved
0.7842	Intermediate Similarity	NPD3450	Approved
0.7842	Intermediate Similarity	NPD2494	Approved
0.7841	Intermediate Similarity	NPD4010	Discontinued
0.7831	Intermediate Similarity	NPD5241	Discontinued
0.7829	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD7831	Phase 2
0.7816	Intermediate Similarity	NPD7833	Phase 2
0.7784	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD3845	Phase 1
0.7765	Intermediate Similarity	NPD8099	Discontinued
0.7765	Intermediate Similarity	NPD8252	Approved
0.7765	Intermediate Similarity	NPD8251	Approved
0.774	Intermediate Similarity	NPD6071	Discontinued
0.7722	Intermediate Similarity	NPD8156	Discontinued
0.772	Intermediate Similarity	NPD4582	Approved
0.772	Intermediate Similarity	NPD4583	Approved
0.7705	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD2563	Approved
0.7701	Intermediate Similarity	NPD2560	Approved
0.7679	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7668	Intermediate Similarity	NPD4002	Approved
0.7668	Intermediate Similarity	NPD4004	Approved
0.7657	Intermediate Similarity	NPD6788	Approved
0.7632	Intermediate Similarity	NPD2973	Approved
0.7632	Intermediate Similarity	NPD2975	Approved
0.7632	Intermediate Similarity	NPD2974	Approved
0.7616	Intermediate Similarity	NPD4017	Approved
0.7614	Intermediate Similarity	NPD5604	Discontinued
0.7609	Intermediate Similarity	NPD2968	Approved
0.7609	Intermediate Similarity	NPD2971	Approved
0.7592	Intermediate Similarity	NPD4420	Approved
0.7588	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7298	Approved
0.7568	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD4772	Phase 2
0.7529	Intermediate Similarity	NPD4773	Phase 2
0.7513	Intermediate Similarity	NPD4580	Approved
0.7512	Intermediate Similarity	NPD7047	Phase 3
0.7487	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD6997	Phase 2
0.7458	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD7827	Phase 1
0.7439	Intermediate Similarity	NPD3110	Approved
0.7439	Intermediate Similarity	NPD3109	Approved
0.7436	Intermediate Similarity	NPD5006	Approved
0.7436	Intermediate Similarity	NPD5005	Approved
0.7399	Intermediate Similarity	NPD6031	Approved
0.7399	Intermediate Similarity	NPD6030	Approved
0.7399	Intermediate Similarity	NPD3641	Approved
0.7399	Intermediate Similarity	NPD3640	Phase 3
0.7399	Intermediate Similarity	NPD4727	Phase 1
0.7399	Intermediate Similarity	NPD3639	Approved
0.7365	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD4040	Phase 1
0.7354	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7281	Phase 3
0.7326	Intermediate Similarity	NPD7280	Phase 3
0.7321	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD4055	Discovery
0.7306	Intermediate Similarity	NPD5582	Discontinued
0.7294	Intermediate Similarity	NPD5177	Phase 3
0.7282	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD1753	Discontinued
0.726	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD2491	Approved
0.7259	Intermediate Similarity	NPD3057	Approved
0.7259	Intermediate Similarity	NPD3448	Approved
0.7258	Intermediate Similarity	NPD6297	Approved
0.7256	Intermediate Similarity	NPD5156	Approved
0.7256	Intermediate Similarity	NPD5155	Approved
0.7256	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD5754	Discontinued
0.7243	Intermediate Similarity	NPD6042	Phase 2
0.7243	Intermediate Similarity	NPD42	Phase 2
0.7241	Intermediate Similarity	NPD6090	Discontinued
0.7228	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD5718	Phase 2
0.7209	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD7802	Discontinued
0.7195	Intermediate Similarity	NPD2606	Approved
0.7195	Intermediate Similarity	NPD2605	Approved
0.7195	Intermediate Similarity	NPD3595	Approved
0.7195	Intermediate Similarity	NPD3594	Approved
0.7193	Intermediate Similarity	NPD3060	Approved
0.7193	Intermediate Similarity	NPD4237	Approved
0.7193	Intermediate Similarity	NPD4236	Phase 3
0.7176	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD4726	Approved
0.7176	Intermediate Similarity	NPD4725	Approved
0.7176	Intermediate Similarity	NPD4721	Approved
0.7172	Intermediate Similarity	NPD2972	Approved
0.7172	Intermediate Similarity	NPD3533	Approved
0.7169	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD2674	Phase 3
0.7151	Intermediate Similarity	NPD5772	Approved
0.7151	Intermediate Similarity	NPD5773	Approved
0.715	Intermediate Similarity	NPD6723	Discontinued
0.7143	Intermediate Similarity	NPD4666	Phase 3
0.7134	Intermediate Similarity	NPD3637	Approved
0.7134	Intermediate Similarity	NPD3636	Approved
0.7134	Intermediate Similarity	NPD3635	Approved
0.7119	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6853	Approved
0.7105	Intermediate Similarity	NPD6851	Approved
0.7104	Intermediate Similarity	NPD6107	Approved
0.7102	Intermediate Similarity	NPD5976	Discontinued
0.7095	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD6674	Discontinued
0.7088	Intermediate Similarity	NPD5709	Phase 3
0.7088	Intermediate Similarity	NPD7400	Phase 3
0.7086	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD1424	Approved
0.7086	Intermediate Similarity	NPD4123	Phase 3
0.7081	Intermediate Similarity	NPD7907	Approved
0.7079	Intermediate Similarity	NPD4859	Phase 1
0.7071	Intermediate Similarity	NPD4107	Approved
0.7069	Intermediate Similarity	NPD6666	Approved
0.7069	Intermediate Similarity	NPD6667	Approved
0.7068	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD3763	Approved
0.7066	Intermediate Similarity	NPD4475	Approved
0.7066	Intermediate Similarity	NPD4474	Approved
0.7065	Intermediate Similarity	NPD4166	Phase 2
0.7059	Intermediate Similarity	NPD4873	Discontinued
0.7059	Intermediate Similarity	NPD4108	Discontinued
0.7045	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7037	Approved
0.7033	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD3124	Discontinued
0.7022	Intermediate Similarity	NPD4005	Discontinued
0.702	Intermediate Similarity	NPD8095	Phase 1
0.7006	Intermediate Similarity	NPD3144	Approved
0.7006	Intermediate Similarity	NPD3145	Approved
0.7	Intermediate Similarity	NPD6896	Approved
0.7	Intermediate Similarity	NPD6895	Approved
0.7	Intermediate Similarity	NPD7549	Discontinued
0.6995	Remote Similarity	NPD6234	Discontinued
0.6988	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD4111	Phase 1
0.6986	Remote Similarity	NPD4665	Approved
0.6977	Remote Similarity	NPD1375	Discontinued
0.6976	Remote Similarity	NPD5676	Approved
0.6974	Remote Similarity	NPD7296	Approved
0.6973	Remote Similarity	NPD6747	Phase 1
0.6971	Remote Similarity	NPD7124	Phase 2
0.6964	Remote Similarity	NPD8153	Approved
0.6964	Remote Similarity	NPD8152	Approved
0.6963	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5677	Discontinued
0.695	Remote Similarity	NPD4482	Phase 3
0.6944	Remote Similarity	NPD6072	Discontinued
0.6941	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD2492	Phase 1
0.6936	Remote Similarity	NPD4257	Approved
0.6936	Remote Similarity	NPD4256	Phase 2
0.6932	Remote Similarity	NPD7598	Phase 2
0.6931	Remote Similarity	NPD7479	Phase 2
0.6923	Remote Similarity	NPD2238	Phase 2
0.6923	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5978	Approved
0.6923	Remote Similarity	NPD5977	Approved
0.6915	Remote Similarity	NPD7228	Approved
0.6914	Remote Similarity	NPD3692	Discontinued
0.6914	Remote Similarity	NPD5160	Discontinued
0.691	Remote Similarity	NPD1914	Approved
0.691	Remote Similarity	NPD2122	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data