NPASS Compound

Structure

NPC472623 OpenBabel07101718292D 29 32 0 0 1 0 0 0 0 0999 V2000 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9282 -4.0000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 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 12 2 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 5 7 2 0 0 0 0 5 14 1 0 0 0 0 6 8 1 0 0 0 0 6 15 1 0 0 0 0 7 17 1 0 0 0 0 8 18 1 0 0 0 0 9 14 2 0 0 0 0 9 16 1 0 0 0 0 10 14 1 0 0 0 0 10 20 1 0 0 0 0 11 15 2 0 0 0 0 11 19 1 0 0 0 0 13 18 1 0 0 0 0 13 22 1 6 0 0 0 15 22 1 0 0 0 0 16 17 2 0 0 0 0 16 24 1 0 0 0 0 17 25 1 0 0 0 0 18 28 1 1 0 0 0 19 23 1 0 0 0 0 19 26 2 0 0 0 0 20 27 2 0 0 0 0 20 28 1 0 0 0 0 21 22 1 1 0 0 0 21 23 1 0 0 0 0 21 29 1 0 0 0 0 22 4 1 6 0 0 0 23 12 1 6 0 0 0 23 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.14
Volume:	412.845
LogP:	3.665
LogD:	3.382
LogS:	-4.773
# Rotatable Bonds:	5
TPSA:	76.13
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.453
Synthetic Accessibility Score:	4.604
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:	-5.071
MDCK Permeability:	3.402195579838008e-05
Pgp-inhibitor:	0.727
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.101
Plasma Protein Binding (PPB):	90.51238250732422%
Volume Distribution (VD):	0.683
Pgp-substrate:	4.335345268249512%

ADMET: Metabolism

CYP1A2-inhibitor:	0.05
CYP1A2-substrate:	0.468
CYP2C19-inhibitor:	0.646
CYP2C19-substrate:	0.873
CYP2C9-inhibitor:	0.407
CYP2C9-substrate:	0.196
CYP2D6-inhibitor:	0.129
CYP2D6-substrate:	0.232
CYP3A4-inhibitor:	0.661
CYP3A4-substrate:	0.734

ADMET: Excretion

Clearance (CL):	3.02
Half-life (T1/2):	0.879

ADMET: Toxicity

hERG Blockers:	0.09
Human Hepatotoxicity (H-HT):	0.66
Drug-inuced Liver Injury (DILI):	0.504
AMES Toxicity:	0.309
Rat Oral Acute Toxicity:	0.101
Maximum Recommended Daily Dose:	0.863
Skin Sensitization:	0.614
Carcinogencity:	0.107
Eye Corrosion:	0.004
Eye Irritation:	0.051
Respiratory Toxicity:	0.22

Download Data

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

Natural Product: NPC472623

Natural Product ID:	NPC472623
*Common Name:**	BZEFQUTWHGLKRU-GAGXKEPLSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BZEFQUTWHGLKRU-GAGXKEPLSA-N
Standard InCHI:	InChI=1S/C23H25ClO5/c1-12(2)23-19(26)11-15-6-8-18(13(3)22(15,4)21(23)29-23)28-20(27)10-14-5-7-17(25)16(24)9-14/h5,7,9,11,13,18,21,25H,1,6,8,10H2,2-4H3/t13-,18+,21+,22+,23-/m0/s1
SMILES:	CC1C(CCC2=CC(=O)C3(C(C12C)O3)C(=C)C)OC(=O)CC4=CC(=C(C=C4)O)Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581338
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO32481	Penicillium copticola	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[25734623]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	4
MIC	1

Activity Type	# Activity
Cell Line	3
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	56950.0	nM	PMID[550398]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	39550.0	nM	PMID[550398]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	21080.0	nM	PMID[550398]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	3450.0	nM	PMID[550398]
NPT115	Organism	Mycobacterium tuberculosis H37Ra	Mycobacterium tuberculosis H37Ra	MIC	=	50.0	ug.mL-1	PMID[550398]

☑ 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 NPC472623 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	349
0.1-0.2	1467
0.2-0.3	2973
0.3-0.4	7371
0.4-0.5	11880
0.5-0.6	8860
0.6-0.7	9486
0.7-0.8	310
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7929	Intermediate Similarity	NPC173352
0.7929	Intermediate Similarity	NPC58653
0.7917	Intermediate Similarity	NPC474096
0.7882	Intermediate Similarity	NPC28669
0.7829	Intermediate Similarity	NPC30390
0.7765	Intermediate Similarity	NPC470081
0.7751	Intermediate Similarity	NPC298401
0.773	Intermediate Similarity	NPC473719
0.7709	Intermediate Similarity	NPC470103
0.7706	Intermediate Similarity	NPC473696
0.7688	Intermediate Similarity	NPC308572
0.7683	Intermediate Similarity	NPC120171
0.7679	Intermediate Similarity	NPC472404
0.7673	Intermediate Similarity	NPC172311
0.7628	Intermediate Similarity	NPC194970
0.7613	Intermediate Similarity	NPC76453
0.7613	Intermediate Similarity	NPC165612
0.759	Intermediate Similarity	NPC205918
0.7582	Intermediate Similarity	NPC470100
0.758	Intermediate Similarity	NPC477874
0.758	Intermediate Similarity	NPC173569
0.7578	Intermediate Similarity	NPC474300
0.7572	Intermediate Similarity	NPC474061
0.7562	Intermediate Similarity	NPC472801
0.7562	Intermediate Similarity	NPC37992
0.7562	Intermediate Similarity	NPC220496
0.7562	Intermediate Similarity	NPC32749
0.7562	Intermediate Similarity	NPC147542
0.7562	Intermediate Similarity	NPC327916
0.7562	Intermediate Similarity	NPC241349
0.7562	Intermediate Similarity	NPC42262
0.756	Intermediate Similarity	NPC170189
0.756	Intermediate Similarity	NPC208173
0.7558	Intermediate Similarity	NPC470563
0.7545	Intermediate Similarity	NPC184284
0.7545	Intermediate Similarity	NPC76041
0.7544	Intermediate Similarity	NPC472405
0.7532	Intermediate Similarity	NPC249817
0.7532	Intermediate Similarity	NPC473247
0.7531	Intermediate Similarity	NPC476473
0.7529	Intermediate Similarity	NPC472032
0.7516	Intermediate Similarity	NPC257003
0.7515	Intermediate Similarity	NPC471968
0.7515	Intermediate Similarity	NPC94781
0.75	Intermediate Similarity	NPC471602
0.75	Intermediate Similarity	NPC245122
0.75	Intermediate Similarity	NPC137416
0.75	Intermediate Similarity	NPC299405
0.75	Intermediate Similarity	NPC103337
0.75	Intermediate Similarity	NPC221185
0.75	Intermediate Similarity	NPC111422
0.75	Intermediate Similarity	NPC295339
0.75	Intermediate Similarity	NPC114620
0.75	Intermediate Similarity	NPC476477
0.75	Intermediate Similarity	NPC29771
0.75	Intermediate Similarity	NPC306835
0.75	Intermediate Similarity	NPC470561
0.75	Intermediate Similarity	NPC256463
0.75	Intermediate Similarity	NPC216312
0.7486	Intermediate Similarity	NPC470099
0.7485	Intermediate Similarity	NPC169942
0.7484	Intermediate Similarity	NPC22676
0.7484	Intermediate Similarity	NPC198621
0.7484	Intermediate Similarity	NPC475482
0.7484	Intermediate Similarity	NPC216940
0.747	Intermediate Similarity	NPC87630
0.747	Intermediate Similarity	NPC162569
0.747	Intermediate Similarity	NPC179128
0.747	Intermediate Similarity	NPC84142
0.747	Intermediate Similarity	NPC116292
0.747	Intermediate Similarity	NPC267469
0.747	Intermediate Similarity	NPC35160
0.7459	Intermediate Similarity	NPC247104
0.7459	Intermediate Similarity	NPC99937
0.7456	Intermediate Similarity	NPC478230
0.7456	Intermediate Similarity	NPC478221
0.7456	Intermediate Similarity	NPC69043
0.7456	Intermediate Similarity	NPC472890
0.7455	Intermediate Similarity	NPC325032
0.7455	Intermediate Similarity	NPC472135
0.7455	Intermediate Similarity	NPC477483
0.7455	Intermediate Similarity	NPC5568
0.7453	Intermediate Similarity	NPC136649
0.744	Intermediate Similarity	NPC115249
0.7439	Intermediate Similarity	NPC208293
0.7438	Intermediate Similarity	NPC86087
0.7438	Intermediate Similarity	NPC61590
0.7434	Intermediate Similarity	NPC265413
0.7434	Intermediate Similarity	NPC10154
0.7432	Intermediate Similarity	NPC316091
0.7425	Intermediate Similarity	NPC472891
0.7425	Intermediate Similarity	NPC164762
0.7423	Intermediate Similarity	NPC25491
0.7423	Intermediate Similarity	NPC354984
0.7419	Intermediate Similarity	NPC48822
0.7414	Intermediate Similarity	NPC73544
0.7412	Intermediate Similarity	NPC280497
0.741	Intermediate Similarity	NPC17600
0.7407	Intermediate Similarity	NPC471444
0.7401	Intermediate Similarity	NPC474857
0.7396	Intermediate Similarity	NPC478231
0.7396	Intermediate Similarity	NPC137301
0.7394	Intermediate Similarity	NPC51513
0.7394	Intermediate Similarity	NPC202112
0.7389	Intermediate Similarity	NPC323379
0.7389	Intermediate Similarity	NPC306240
0.7389	Intermediate Similarity	NPC327204
0.7381	Intermediate Similarity	NPC91809
0.738	Intermediate Similarity	NPC313541
0.7378	Intermediate Similarity	NPC103910
0.7375	Intermediate Similarity	NPC471152
0.7371	Intermediate Similarity	NPC131078
0.7368	Intermediate Similarity	NPC478225
0.7368	Intermediate Similarity	NPC472889
0.7365	Intermediate Similarity	NPC280753
0.7365	Intermediate Similarity	NPC327962
0.7365	Intermediate Similarity	NPC44378
0.7365	Intermediate Similarity	NPC52931
0.736	Intermediate Similarity	NPC470422
0.7358	Intermediate Similarity	NPC472804
0.7356	Intermediate Similarity	NPC161151
0.7355	Intermediate Similarity	NPC469930
0.7353	Intermediate Similarity	NPC317585
0.7353	Intermediate Similarity	NPC472807
0.7349	Intermediate Similarity	NPC215593
0.7346	Intermediate Similarity	NPC27518
0.7346	Intermediate Similarity	NPC304110
0.7345	Intermediate Similarity	NPC470562
0.7345	Intermediate Similarity	NPC470565
0.7345	Intermediate Similarity	NPC107283
0.7342	Intermediate Similarity	NPC477280
0.7342	Intermediate Similarity	NPC477281
0.7342	Intermediate Similarity	NPC475346
0.7342	Intermediate Similarity	NPC475457
0.7342	Intermediate Similarity	NPC475627
0.7342	Intermediate Similarity	NPC19719
0.7342	Intermediate Similarity	NPC18982
0.7341	Intermediate Similarity	NPC477627
0.7337	Intermediate Similarity	NPC313386
0.7337	Intermediate Similarity	NPC478224
0.7329	Intermediate Similarity	NPC234548
0.7329	Intermediate Similarity	NPC248287
0.7326	Intermediate Similarity	NPC470559
0.7325	Intermediate Similarity	NPC108553
0.7321	Intermediate Similarity	NPC56204
0.732	Intermediate Similarity	NPC474532
0.7318	Intermediate Similarity	NPC471684
0.7317	Intermediate Similarity	NPC21873
0.7314	Intermediate Similarity	NPC68850
0.7312	Intermediate Similarity	NPC475549
0.731	Intermediate Similarity	NPC470564
0.7308	Intermediate Similarity	NPC214246
0.7308	Intermediate Similarity	NPC131684
0.7305	Intermediate Similarity	NPC279442
0.7305	Intermediate Similarity	NPC101043
0.7305	Intermediate Similarity	NPC306799
0.7305	Intermediate Similarity	NPC142846
0.7303	Intermediate Similarity	NPC470560
0.7301	Intermediate Similarity	NPC244923
0.7301	Intermediate Similarity	NPC182475
0.7289	Intermediate Similarity	NPC63918
0.7289	Intermediate Similarity	NPC472134
0.7289	Intermediate Similarity	NPC470330
0.7288	Intermediate Similarity	NPC184518
0.7284	Intermediate Similarity	NPC179505
0.7284	Intermediate Similarity	NPC156709
0.7278	Intermediate Similarity	NPC475093
0.7273	Intermediate Similarity	NPC89664
0.7273	Intermediate Similarity	NPC210966
0.7273	Intermediate Similarity	NPC478203
0.7273	Intermediate Similarity	NPC311679
0.7273	Intermediate Similarity	NPC126882
0.7273	Intermediate Similarity	NPC274085
0.7267	Intermediate Similarity	NPC478226
0.7267	Intermediate Similarity	NPC301915
0.7267	Intermediate Similarity	NPC261292
0.7267	Intermediate Similarity	NPC246466
0.7263	Intermediate Similarity	NPC108744
0.7262	Intermediate Similarity	NPC32197
0.7262	Intermediate Similarity	NPC474310
0.7261	Intermediate Similarity	NPC253488
0.7256	Intermediate Similarity	NPC477873
0.7256	Intermediate Similarity	NPC469447
0.7256	Intermediate Similarity	NPC285550
0.7256	Intermediate Similarity	NPC201297
0.7251	Intermediate Similarity	NPC474501
0.7251	Intermediate Similarity	NPC314257
0.7251	Intermediate Similarity	NPC159692
0.7251	Intermediate Similarity	NPC478133
0.725	Intermediate Similarity	NPC279463
0.725	Intermediate Similarity	NPC27407
0.7239	Intermediate Similarity	NPC477279
0.7239	Intermediate Similarity	NPC38473
0.7233	Intermediate Similarity	NPC49742
0.7233	Intermediate Similarity	NPC168799
0.7233	Intermediate Similarity	NPC155209
0.7229	Intermediate Similarity	NPC320734
0.7229	Intermediate Similarity	NPC258856
0.7229	Intermediate Similarity	NPC83272
0.7229	Intermediate Similarity	NPC257558

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 NPC472623 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	291
0.1-0.2	923
0.2-0.3	1616
0.3-0.4	2724
0.4-0.5	2258
0.5-0.6	1076
0.6-0.7	260
0.7-0.8	2
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7622	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4534	Discontinued
0.7353	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD8166	Discontinued
0.7179	Intermediate Similarity	NPD454	Approved
0.7178	Intermediate Similarity	NPD5958	Discontinued
0.7152	Intermediate Similarity	NPD3887	Approved
0.7143	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD2403	Approved
0.7104	Intermediate Similarity	NPD6785	Approved
0.7104	Intermediate Similarity	NPD6784	Approved
0.7048	Intermediate Similarity	NPD2354	Approved
0.7044	Intermediate Similarity	NPD3764	Approved
0.7	Intermediate Similarity	NPD6663	Approved
0.6988	Remote Similarity	NPD4628	Phase 3
0.6978	Remote Similarity	NPD8014	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD5736	Approved
0.6946	Remote Similarity	NPD6190	Approved
0.6923	Remote Similarity	NPD1578	Phase 2
0.6923	Remote Similarity	NPD7959	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6599	Discontinued
0.6909	Remote Similarity	NPD2353	Approved
0.6909	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7236	Approved
0.6886	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD2932	Approved
0.6875	Remote Similarity	NPD7075	Discontinued
0.6875	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD4972	Discontinued
0.681	Remote Similarity	NPD6355	Discontinued
0.68	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD8434	Phase 2
0.6786	Remote Similarity	NPD3750	Approved
0.6782	Remote Similarity	NPD958	Approved
0.6774	Remote Similarity	NPD3019	Approved
0.6766	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD9545	Approved
0.6747	Remote Similarity	NPD2935	Discontinued
0.6747	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD6798	Discontinued
0.6726	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD1184	Approved
0.6705	Remote Similarity	NPD7819	Suspended
0.6705	Remote Similarity	NPD7239	Suspended
0.6705	Remote Similarity	NPD957	Approved
0.6702	Remote Similarity	NPD8150	Discontinued
0.6688	Remote Similarity	NPD1201	Approved
0.6687	Remote Similarity	NPD2799	Discontinued
0.6686	Remote Similarity	NPD6273	Approved
0.6686	Remote Similarity	NPD7003	Approved
0.6667	Remote Similarity	NPD7095	Approved
0.6667	Remote Similarity	NPD3226	Approved
0.6667	Remote Similarity	NPD3817	Phase 2
0.6667	Remote Similarity	NPD6799	Approved
0.6649	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD6801	Discontinued
0.6647	Remote Similarity	NPD5404	Approved
0.6647	Remote Similarity	NPD5405	Approved
0.6647	Remote Similarity	NPD6100	Approved
0.6647	Remote Similarity	NPD5406	Approved
0.6647	Remote Similarity	NPD5408	Approved
0.6647	Remote Similarity	NPD6099	Approved
0.6646	Remote Similarity	NPD4060	Phase 1
0.6628	Remote Similarity	NPD2532	Approved
0.6628	Remote Similarity	NPD2534	Approved
0.6628	Remote Similarity	NPD2533	Approved
0.6625	Remote Similarity	NPD1470	Approved
0.6612	Remote Similarity	NPD7473	Discontinued
0.661	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD3300	Phase 2
0.6607	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD2346	Discontinued
0.6601	Remote Similarity	NPD2629	Approved
0.6587	Remote Similarity	NPD7033	Discontinued
0.6587	Remote Similarity	NPD1510	Phase 2
0.6585	Remote Similarity	NPD6233	Phase 2
0.658	Remote Similarity	NPD4360	Phase 2
0.658	Remote Similarity	NPD4363	Phase 3
0.6576	Remote Similarity	NPD7799	Discontinued
0.6576	Remote Similarity	NPD3751	Discontinued
0.6575	Remote Similarity	NPD8127	Discontinued
0.6573	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD5402	Approved
0.6573	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD7458	Discontinued
0.657	Remote Similarity	NPD7041	Phase 2
0.657	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD1549	Phase 2
0.6562	Remote Similarity	NPD1283	Approved
0.6562	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD4198	Discontinued
0.6554	Remote Similarity	NPD1934	Approved
0.6552	Remote Similarity	NPD5403	Approved
0.6545	Remote Similarity	NPD2979	Phase 3
0.6541	Remote Similarity	NPD4878	Approved
0.6541	Remote Similarity	NPD1608	Approved
0.6538	Remote Similarity	NPD6232	Discontinued
0.6536	Remote Similarity	NPD7768	Phase 2
0.6534	Remote Similarity	NPD4380	Phase 2
0.6524	Remote Similarity	NPD3268	Approved
0.6524	Remote Similarity	NPD6764	Approved
0.6524	Remote Similarity	NPD6765	Approved
0.6522	Remote Similarity	NPD987	Approved
0.6522	Remote Similarity	NPD2797	Approved
0.65	Remote Similarity	NPD4359	Approved
0.6497	Remote Similarity	NPD3274	Phase 2
0.6497	Remote Similarity	NPD7411	Suspended
0.6497	Remote Similarity	NPD4914	Approved
0.6491	Remote Similarity	NPD4110	Phase 3
0.6491	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD3748	Approved
0.6485	Remote Similarity	NPD8032	Phase 2
0.6484	Remote Similarity	NPD6959	Discontinued
0.6481	Remote Similarity	NPD2798	Approved
0.6474	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD1607	Approved
0.6467	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD6166	Phase 2
0.6464	Remote Similarity	NPD6234	Discontinued
0.6461	Remote Similarity	NPD37	Approved
0.6458	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.645	Remote Similarity	NPD1551	Phase 2
0.645	Remote Similarity	NPD2796	Approved
0.6448	Remote Similarity	NPD3787	Discontinued
0.6446	Remote Similarity	NPD1240	Approved
0.6446	Remote Similarity	NPD4140	Approved
0.6444	Remote Similarity	NPD3882	Suspended
0.6444	Remote Similarity	NPD4967	Phase 2
0.6444	Remote Similarity	NPD7057	Phase 3
0.6444	Remote Similarity	NPD7058	Phase 2
0.6444	Remote Similarity	NPD4966	Approved
0.6444	Remote Similarity	NPD4965	Approved
0.6437	Remote Similarity	NPD5401	Approved
0.6437	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD8368	Discontinued
0.6432	Remote Similarity	NPD4387	Approved
0.6432	Remote Similarity	NPD4386	Approved
0.6429	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4915	Approved
0.6429	Remote Similarity	NPD4388	Approved
0.6429	Remote Similarity	NPD4538	Approved
0.6429	Remote Similarity	NPD4536	Approved
0.6424	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD2313	Discontinued
0.6416	Remote Similarity	NPD5058	Phase 3
0.6415	Remote Similarity	NPD3023	Approved
0.6415	Remote Similarity	NPD3026	Approved
0.6412	Remote Similarity	NPD5763	Approved
0.6412	Remote Similarity	NPD7266	Discontinued
0.6412	Remote Similarity	NPD5762	Approved
0.641	Remote Similarity	NPD9493	Approved
0.6409	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD3749	Approved
0.6407	Remote Similarity	NPD230	Phase 1
0.6402	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.64	Remote Similarity	NPD1512	Approved
0.6395	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD3025	Approved
0.6392	Remote Similarity	NPD3024	Approved
0.6392	Remote Similarity	NPD5585	Approved
0.6391	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD5960	Phase 3
0.6387	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD4062	Phase 3
0.6384	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD6797	Phase 2
0.6379	Remote Similarity	NPD7390	Discontinued
0.6378	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD4361	Phase 2
0.6378	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD1281	Approved
0.6368	Remote Similarity	NPD8312	Approved
0.6368	Remote Similarity	NPD8313	Approved
0.6364	Remote Similarity	NPD5544	Approved
0.6364	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5844	Phase 1
0.6354	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD2438	Suspended
0.6352	Remote Similarity	NPD4589	Approved
0.6352	Remote Similarity	NPD17	Approved
0.6352	Remote Similarity	NPD4626	Approved
0.6352	Remote Similarity	NPD1778	Approved
0.6349	Remote Similarity	NPD6559	Discontinued
0.6349	Remote Similarity	NPD7251	Discontinued
0.6348	Remote Similarity	NPD7028	Phase 2
0.6343	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD2861	Phase 2
0.6337	Remote Similarity	NPD2800	Approved
0.6335	Remote Similarity	NPD8407	Phase 2
0.6335	Remote Similarity	NPD3972	Approved
0.6333	Remote Similarity	NPD2801	Approved
0.6333	Remote Similarity	NPD5761	Phase 2
0.6333	Remote Similarity	NPD5760	Phase 2
0.6329	Remote Similarity	NPD3091	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