NPASS Compound

Structure

NPC470729 OpenBabel07101719152D 33 39 0 0 1 0 0 0 0 0999 V2000 1.7708 1.7413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4600 0.9621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6368 -2.8733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9115 -4.0907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2423 -2.1256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7447 -3.6097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3134 -2.7228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0783 -3.6097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8975 -1.2274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7447 -2.6475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5061 -0.5190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6582 -1.8246 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0783 -2.6475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5564 -1.4798 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0527 -1.0769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9115 -2.1665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4065 -1.9032 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7547 -1.1248 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0397 0.4811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3732 -0.4811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2065 0.9621 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3633 -2.0038 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2065 -0.9621 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5767 -0.2700 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.7115 -1.2254 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.3732 0.4811 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.0397 -0.4811 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.1189 -3.3332 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8729 0.9621 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4600 -0.9621 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3716 0.7716 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 0.3716 -0.7716 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 2 26 1 0 0 0 0 3 5 2 0 0 0 0 3 7 1 0 0 0 0 4 6 2 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 7 12 2 0 0 0 0 8 13 2 0 0 0 0 9 15 2 0 0 0 0 10 16 2 0 0 0 0 11 14 2 0 0 0 0 11 24 1 0 0 0 0 12 14 1 0 0 0 0 12 15 1 0 0 0 0 13 16 1 0 0 0 0 13 22 1 0 0 0 0 15 24 1 0 0 0 0 16 25 1 0 0 0 0 17 22 1 6 0 0 0 17 23 1 0 0 0 0 17 28 1 0 0 0 0 18 22 1 1 0 0 0 18 25 1 0 0 0 0 18 27 1 0 0 0 0 19 21 1 0 0 0 0 19 27 1 0 0 0 0 19 29 2 0 0 0 0 20 26 1 0 0 0 0 20 30 2 0 0 0 0 21 1 1 6 0 0 0 21 26 1 0 0 0 0 21 31 1 0 0 0 0 22 14 1 1 0 0 0 23 20 1 6 0 0 0 23 27 1 0 0 0 0 23 32 1 0 0 0 0 31 33 1 0 0 0 0 32 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	496.07
Volume:	448.626
LogP:	3.204
LogD:	2.252
LogS:	-3.961
# Rotatable Bonds:	1
TPSA:	88.67
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	8
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.446
Synthetic Accessibility Score:	6.123
Fsp3:	0.304
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.488
MDCK Permeability:	7.783582987030968e-06
Pgp-inhibitor:	0.835
Pgp-substrate:	0.226
Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.451

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.142
Plasma Protein Binding (PPB):	78.814453125%
Volume Distribution (VD):	0.831
Pgp-substrate:	23.35904312133789%

ADMET: Metabolism

CYP1A2-inhibitor:	0.157
CYP1A2-substrate:	0.247
CYP2C19-inhibitor:	0.986
CYP2C19-substrate:	0.914
CYP2C9-inhibitor:	0.977
CYP2C9-substrate:	0.763
CYP2D6-inhibitor:	0.86
CYP2D6-substrate:	0.15
CYP3A4-inhibitor:	0.957
CYP3A4-substrate:	0.964

ADMET: Excretion

Clearance (CL):	8.762
Half-life (T1/2):	0.06

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.195
Drug-inuced Liver Injury (DILI):	0.98
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.993
Maximum Recommended Daily Dose:	0.921
Skin Sensitization:	0.906
Carcinogencity:	0.72
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.926

Download Data

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

Natural Product: NPC470729

Natural Product ID:	NPC470729
*Common Name:**	FIIJQUIYIBLWOG-MHYJACLRSA-N
IUPAC Name:	n.a.
Synonyms:	Gliocladine-D
Standard InCHIKey:	FIIJQUIYIBLWOG-MHYJACLRSA-N
Standard InCHI:	InChI=1S/C23H20N4O3S3/c1-21-19(29)27-18-22(13-8-4-6-10-16(13)25-18,14-11-24-15-9-5-3-7-12(14)15)17(28)23(27,32-33-31-21)20(30)26(21)2/h3-11,17-18,24-25,28H,1-2H3/t17-,18+,21-,22-,23-/m0/s1
SMILES:	CC12C(=O)N3C4C(C(C3(C(=O)N1C)SSS2)O)(C5=CC=CC=C5N4)C6=CNC7=CC=CC=C76
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2207536
PubChem CID:	71452521
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001733] Pyrroloindoles

*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
NPO32990	acrostalagmus luteoalbus scsio f457	Species	Plectosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23079524]

☑ 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

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	2030.0	nM	PMID[465772]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	17780.0	nM	PMID[465772]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	650.0	nM	PMID[465772]
NPT395	Cell Line	SF-268	Homo sapiens	IC50	=	2490.0	nM	PMID[465772]

☑ 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 NPC470729 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	377
0.1-0.2	2385
0.2-0.3	17218
0.3-0.4	15770
0.4-0.5	2489
0.5-0.6	2724
0.6-0.7	1414
0.7-0.8	299
0.8-0.85	7
0.85-0.9	1
0.9-0.95	10
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477176
0.9951	High Similarity	NPC474877
0.9709	High Similarity	NPC477175
0.9709	High Similarity	NPC470730
0.9662	High Similarity	NPC475969
0.9662	High Similarity	NPC477177
0.9662	High Similarity	NPC475859
0.9615	High Similarity	NPC165743
0.9569	High Similarity	NPC63279
0.9524	High Similarity	NPC297642
0.9409	High Similarity	NPC470732
0.9126	High Similarity	NPC470731
0.8651	High Similarity	NPC40455
0.8433	Intermediate Similarity	NPC327095
0.8433	Intermediate Similarity	NPC312942
0.8389	Intermediate Similarity	NPC162860
0.8356	Intermediate Similarity	NPC19170
0.8341	Intermediate Similarity	NPC272174
0.8294	Intermediate Similarity	NPC54420
0.8243	Intermediate Similarity	NPC297862
0.8227	Intermediate Similarity	NPC476817
0.8219	Intermediate Similarity	NPC474896
0.8182	Intermediate Similarity	NPC31097
0.8131	Intermediate Similarity	NPC107077
0.8131	Intermediate Similarity	NPC223791
0.8111	Intermediate Similarity	NPC478157
0.8057	Intermediate Similarity	NPC475506
0.8047	Intermediate Similarity	NPC478158
0.8019	Intermediate Similarity	NPC155143
0.8018	Intermediate Similarity	NPC253987
0.8	Intermediate Similarity	NPC477714
0.8	Intermediate Similarity	NPC14812
0.8	Intermediate Similarity	NPC171317
0.8	Intermediate Similarity	NPC281049
0.7955	Intermediate Similarity	NPC477715
0.7948	Intermediate Similarity	NPC478028
0.7915	Intermediate Similarity	NPC473640
0.7913	Intermediate Similarity	NPC17059
0.7907	Intermediate Similarity	NPC477173
0.79	Intermediate Similarity	NPC54744
0.789	Intermediate Similarity	NPC320968
0.7879	Intermediate Similarity	NPC478029
0.787	Intermediate Similarity	NPC470488
0.7864	Intermediate Similarity	NPC94752
0.786	Intermediate Similarity	NPC473376
0.7854	Intermediate Similarity	NPC75634
0.7838	Intermediate Similarity	NPC475736
0.7788	Intermediate Similarity	NPC213629
0.7773	Intermediate Similarity	NPC294693
0.7757	Intermediate Similarity	NPC470497
0.7743	Intermediate Similarity	NPC64216
0.7739	Intermediate Similarity	NPC89987
0.7731	Intermediate Similarity	NPC477179
0.771	Intermediate Similarity	NPC100321
0.7709	Intermediate Similarity	NPC474196
0.7696	Intermediate Similarity	NPC477180
0.7696	Intermediate Similarity	NPC254850
0.7696	Intermediate Similarity	NPC477181
0.7696	Intermediate Similarity	NPC477178
0.7692	Intermediate Similarity	NPC110602
0.7692	Intermediate Similarity	NPC75726
0.7692	Intermediate Similarity	NPC31385
0.7689	Intermediate Similarity	NPC474195
0.7686	Intermediate Similarity	NPC191382
0.7686	Intermediate Similarity	NPC56109
0.7681	Intermediate Similarity	NPC228835
0.7661	Intermediate Similarity	NPC477174
0.7661	Intermediate Similarity	NPC470490
0.7652	Intermediate Similarity	NPC69843
0.7642	Intermediate Similarity	NPC125181
0.7642	Intermediate Similarity	NPC242872
0.7642	Intermediate Similarity	NPC263117
0.7628	Intermediate Similarity	NPC293917
0.7621	Intermediate Similarity	NPC155444
0.7619	Intermediate Similarity	NPC321708
0.7615	Intermediate Similarity	NPC470489
0.7597	Intermediate Similarity	NPC325976
0.7591	Intermediate Similarity	NPC470491
0.7591	Intermediate Similarity	NPC475259
0.7591	Intermediate Similarity	NPC471945
0.7591	Intermediate Similarity	NPC471950
0.7581	Intermediate Similarity	NPC131887
0.7573	Intermediate Similarity	NPC11126
0.757	Intermediate Similarity	NPC321939
0.756	Intermediate Similarity	NPC15102
0.7558	Intermediate Similarity	NPC300183
0.7557	Intermediate Similarity	NPC471951
0.7557	Intermediate Similarity	NPC471946
0.7556	Intermediate Similarity	NPC472285
0.7536	Intermediate Similarity	NPC91179
0.7523	Intermediate Similarity	NPC476874
0.7523	Intermediate Similarity	NPC475359
0.7523	Intermediate Similarity	NPC476073
0.7523	Intermediate Similarity	NPC191817
0.7522	Intermediate Similarity	NPC24370
0.7522	Intermediate Similarity	NPC319232
0.7512	Intermediate Similarity	NPC252338
0.75	Intermediate Similarity	NPC326363
0.75	Intermediate Similarity	NPC314056
0.749	Intermediate Similarity	NPC314882
0.7489	Intermediate Similarity	NPC54981
0.7478	Intermediate Similarity	NPC238945
0.7465	Intermediate Similarity	NPC473763
0.7465	Intermediate Similarity	NPC117244
0.7458	Intermediate Similarity	NPC28945
0.7454	Intermediate Similarity	NPC227582
0.7443	Intermediate Similarity	NPC193761
0.7441	Intermediate Similarity	NPC315555
0.7439	Intermediate Similarity	NPC478006
0.7436	Intermediate Similarity	NPC63031
0.7434	Intermediate Similarity	NPC471192
0.7431	Intermediate Similarity	NPC478012
0.7431	Intermediate Similarity	NPC478011
0.7422	Intermediate Similarity	NPC229348
0.7419	Intermediate Similarity	NPC470499
0.7418	Intermediate Similarity	NPC95783
0.7411	Intermediate Similarity	NPC82370
0.741	Intermediate Similarity	NPC478013
0.7406	Intermediate Similarity	NPC17487
0.7406	Intermediate Similarity	NPC201831
0.7404	Intermediate Similarity	NPC248041
0.7404	Intermediate Similarity	NPC248462
0.7404	Intermediate Similarity	NPC126709
0.7402	Intermediate Similarity	NPC314176
0.74	Intermediate Similarity	NPC315467
0.7399	Intermediate Similarity	NPC469743
0.7387	Intermediate Similarity	NPC323927
0.7378	Intermediate Similarity	NPC475778
0.7378	Intermediate Similarity	NPC153980
0.7378	Intermediate Similarity	NPC471194
0.7378	Intermediate Similarity	NPC471193
0.7378	Intermediate Similarity	NPC6865
0.7375	Intermediate Similarity	NPC477109
0.7375	Intermediate Similarity	NPC477107
0.7375	Intermediate Similarity	NPC477108
0.7371	Intermediate Similarity	NPC478010
0.7371	Intermediate Similarity	NPC175474
0.7371	Intermediate Similarity	NPC478009
0.7368	Intermediate Similarity	NPC473310
0.7366	Intermediate Similarity	NPC234999
0.7364	Intermediate Similarity	NPC260900
0.7358	Intermediate Similarity	NPC62749
0.7356	Intermediate Similarity	NPC145885
0.7356	Intermediate Similarity	NPC14113
0.7356	Intermediate Similarity	NPC84827
0.7356	Intermediate Similarity	NPC64436
0.7354	Intermediate Similarity	NPC71238
0.7348	Intermediate Similarity	NPC471506
0.7342	Intermediate Similarity	NPC277350
0.7339	Intermediate Similarity	NPC476491
0.7339	Intermediate Similarity	NPC52557
0.7333	Intermediate Similarity	NPC72956
0.7331	Intermediate Similarity	NPC220852
0.7331	Intermediate Similarity	NPC323752
0.733	Intermediate Similarity	NPC98715
0.733	Intermediate Similarity	NPC317701
0.7321	Intermediate Similarity	NPC283219
0.7321	Intermediate Similarity	NPC219336
0.7313	Intermediate Similarity	NPC474412
0.7311	Intermediate Similarity	NPC308931
0.7311	Intermediate Similarity	NPC99939
0.7311	Intermediate Similarity	NPC184225
0.7311	Intermediate Similarity	NPC285343
0.7308	Intermediate Similarity	NPC267885
0.7295	Intermediate Similarity	NPC161861
0.7286	Intermediate Similarity	NPC16659
0.7284	Intermediate Similarity	NPC229893
0.7281	Intermediate Similarity	NPC36405
0.728	Intermediate Similarity	NPC470784
0.7277	Intermediate Similarity	NPC235684
0.7277	Intermediate Similarity	NPC314957
0.7273	Intermediate Similarity	NPC15573
0.7273	Intermediate Similarity	NPC217372
0.7273	Intermediate Similarity	NPC195461
0.7273	Intermediate Similarity	NPC81654
0.7273	Intermediate Similarity	NPC79129
0.7273	Intermediate Similarity	NPC249150
0.7273	Intermediate Similarity	NPC59269
0.7273	Intermediate Similarity	NPC111275
0.7273	Intermediate Similarity	NPC214428
0.7273	Intermediate Similarity	NPC313985
0.7273	Intermediate Similarity	NPC49196
0.7273	Intermediate Similarity	NPC183662
0.7269	Intermediate Similarity	NPC475602
0.7265	Intermediate Similarity	NPC475258
0.7264	Intermediate Similarity	NPC165495
0.7264	Intermediate Similarity	NPC472294
0.7261	Intermediate Similarity	NPC171393
0.7261	Intermediate Similarity	NPC295452
0.726	Intermediate Similarity	NPC329688
0.726	Intermediate Similarity	NPC50503
0.726	Intermediate Similarity	NPC203468
0.726	Intermediate Similarity	NPC149155
0.726	Intermediate Similarity	NPC110500
0.726	Intermediate Similarity	NPC189812
0.7257	Intermediate Similarity	NPC70155
0.7256	Intermediate Similarity	NPC329858
0.7251	Intermediate Similarity	NPC71037
0.7249	Intermediate Similarity	NPC79386
0.7238	Intermediate Similarity	NPC184680

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 NPC470729 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	196
0.1-0.2	559
0.2-0.3	981
0.3-0.4	2073
0.4-0.5	2358
0.5-0.6	2215
0.6-0.7	706
0.7-0.8	62
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
0.8009	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7854	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7783	Intermediate Similarity	NPD7970	Approved
0.7783	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD5426	Phase 3
0.7773	Intermediate Similarity	NPD7618	Phase 3
0.7773	Intermediate Similarity	NPD7619	Phase 3
0.7729	Intermediate Similarity	NPD7824	Approved
0.7727	Intermediate Similarity	NPD7470	Discontinued
0.7727	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD7791	Approved
0.7706	Intermediate Similarity	NPD7789	Approved
0.7706	Intermediate Similarity	NPD7950	Approved
0.7706	Intermediate Similarity	NPD7953	Approved
0.7706	Intermediate Similarity	NPD7952	Approved
0.7706	Intermediate Similarity	NPD7951	Approved
0.7706	Intermediate Similarity	NPD7790	Approved
0.7686	Intermediate Similarity	NPD7781	Approved
0.7686	Intermediate Similarity	NPD7780	Approved
0.7642	Intermediate Similarity	NPD7731	Approved
0.7642	Intermediate Similarity	NPD7730	Approved
0.7632	Intermediate Similarity	NPD7271	Approved
0.7628	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD8272	Phase 2
0.7606	Intermediate Similarity	NPD7944	Discontinued
0.758	Intermediate Similarity	NPD7001	Phase 3
0.7565	Intermediate Similarity	NPD6164	Phase 2
0.7565	Intermediate Similarity	NPD6165	Phase 2
0.7558	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD8322	Phase 2
0.7465	Intermediate Similarity	NPD6999	Discontinued
0.7465	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD6595	Phase 3
0.7446	Intermediate Similarity	NPD7711	Discontinued
0.7445	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD8094	Discontinued
0.7378	Intermediate Similarity	NPD8093	Discontinued
0.7371	Intermediate Similarity	NPD7603	Discontinued
0.7354	Intermediate Similarity	NPD7665	Phase 2
0.7354	Intermediate Similarity	NPD7666	Phase 3
0.7342	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD2095	Phase 2
0.7299	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD2092	Phase 2
0.7299	Intermediate Similarity	NPD2094	Phase 2
0.7297	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4601	Approved
0.7273	Intermediate Similarity	NPD4600	Approved
0.7269	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD2091	Phase 2
0.7264	Intermediate Similarity	NPD2096	Phase 2
0.726	Intermediate Similarity	NPD482	Approved
0.7248	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD4499	Approved
0.7174	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD7817	Phase 1
0.7149	Intermediate Similarity	NPD8289	Discontinued
0.7143	Intermediate Similarity	NPD8169	Discontinued
0.7137	Intermediate Similarity	NPD6173	Approved
0.7136	Intermediate Similarity	NPD6664	Approved
0.713	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD750	Phase 2
0.7124	Intermediate Similarity	NPD2510	Approved
0.7124	Intermediate Similarity	NPD2509	Approved
0.7116	Intermediate Similarity	NPD7026	Phase 2
0.7111	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD8271	Discontinued
0.7098	Intermediate Similarity	NPD8072	Approved
0.7095	Intermediate Similarity	NPD5065	Approved
0.7091	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD2511	Approved
0.7067	Intermediate Similarity	NPD8115	Approved
0.7067	Intermediate Similarity	NPD8114	Approved
0.7067	Intermediate Similarity	NPD5901	Discontinued
0.7059	Intermediate Similarity	NPD2880	Discontinued
0.7056	Intermediate Similarity	NPD7543	Phase 2
0.7054	Intermediate Similarity	NPD8073	Approved
0.7051	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD7415	Suspended
0.7037	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7957	Phase 1
0.7035	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD6665	Discontinued
0.7009	Intermediate Similarity	NPD7727	Phase 2
0.7009	Intermediate Similarity	NPD5017	Discontinued
0.7005	Intermediate Similarity	NPD3961	Discontinued
0.7004	Intermediate Similarity	NPD8410	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD4079	Approved
0.6995	Remote Similarity	NPD4076	Approved
0.6992	Remote Similarity	NPD7717	Approved
0.6992	Remote Similarity	NPD7716	Approved
0.6986	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD5003	Discontinued
0.6978	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD4558	Phase 2
0.6974	Remote Similarity	NPD2443	Approved
0.6974	Remote Similarity	NPD2442	Approved
0.6968	Remote Similarity	NPD4602	Approved
0.6966	Remote Similarity	NPD5199	Approved
0.6966	Remote Similarity	NPD7168	Phase 3
0.6966	Remote Similarity	NPD5198	Approved
0.6959	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD6995	Phase 1
0.6948	Remote Similarity	NPD3506	Approved
0.6948	Remote Similarity	NPD3505	Approved
0.6947	Remote Similarity	NPD6176	Phase 1
0.6947	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD6970	Phase 2
0.6929	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD8240	Discontinued
0.6905	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6268	Phase 1
0.6903	Remote Similarity	NPD6269	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD8047	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD484	Approved
0.688	Remote Similarity	NPD8257	Approved
0.688	Remote Similarity	NPD8258	Clinical (unspecified phase)
0.688	Remote Similarity	NPD2787	Clinical (unspecified phase)
0.688	Remote Similarity	NPD8256	Approved
0.6875	Remote Similarity	NPD4397	Phase 1
0.687	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.686	Remote Similarity	NPD8119	Discontinued
0.6853	Remote Similarity	NPD4852	Phase 2
0.6849	Remote Similarity	NPD8431	Approved
0.6842	Remote Similarity	NPD3914	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD3394	Approved
0.6838	Remote Similarity	NPD3393	Approved
0.6838	Remote Similarity	NPD3389	Approved
0.6833	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD7557	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD8284	Discontinued
0.6815	Remote Similarity	NPD8349	Phase 1
0.6814	Remote Similarity	NPD4500	Approved
0.6814	Remote Similarity	NPD4501	Approved
0.6809	Remote Similarity	NPD5818	Discontinued
0.6807	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD5559	Phase 2
0.68	Remote Similarity	NPD8250	Phase 2
0.6798	Remote Similarity	NPD4310	Phase 3
0.6797	Remote Similarity	NPD2408	Discontinued
0.6791	Remote Similarity	NPD2144	Approved
0.679	Remote Similarity	NPD3960	Clinical (unspecified phase)
0.6787	Remote Similarity	NPD3321	Discontinued
0.6771	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.677	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD6987	Phase 1
0.6769	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD6978	Phase 2
0.6761	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD8386	Phase 2
0.6757	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6756	Remote Similarity	NPD7948	Phase 1
0.6753	Remote Similarity	NPD4612	Discontinued
0.6751	Remote Similarity	NPD4555	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.6749	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6749	Remote Similarity	NPD7688	Phase 1
0.6744	Remote Similarity	NPD4075	Phase 2
0.6744	Remote Similarity	NPD6044	Discontinued
0.6743	Remote Similarity	NPD5596	Phase 2
0.674	Remote Similarity	NPD5043	Discontinued
0.674	Remote Similarity	NPD6479	Discontinued
0.6739	Remote Similarity	NPD2008	Discontinued
0.6737	Remote Similarity	NPD2813	Phase 3
0.6737	Remote Similarity	NPD2812	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD6277	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD6217	Discontinued
0.6726	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD4922	Phase 2
0.6725	Remote Similarity	NPD5487	Phase 1
0.6724	Remote Similarity	NPD6545	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD5884	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD8075	Discontinued
0.6722	Remote Similarity	NPD7426	Phase 1
0.6721	Remote Similarity	NPD4885	Approved
0.672	Remote Similarity	NPD7921	Approved
0.672	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD4703	Approved
0.6716	Remote Similarity	NPD4702	Approved
0.6713	Remote Similarity	NPD4181	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