NPASS Compound

Structure

CID237560 OpenBabel06191716042D 22 24 0 0 1 0 0 0 0 0999 V2000 -3.3255 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.8800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4942 -1.4400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6628 -1.9200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4942 -0.4800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4942 -1.4400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6628 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4942 -0.4800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8314 -1.4400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6628 -1.9200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8314 -0.4800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6628 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8314 -1.4400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8314 1.4400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8314 -0.4800 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6628 -2.8800 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6628 0.9600 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.8800 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6628 1.9200 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9200 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 8 1 0 0 0 0 2 21 1 0 0 0 0 3 4 1 0 0 0 0 3 5 2 0 0 0 0 4 9 2 0 0 0 0 5 12 1 0 0 0 0 6 8 2 0 0 0 0 6 10 1 0 0 0 0 7 8 1 0 0 0 0 7 11 2 0 0 0 0 9 14 1 0 0 0 0 9 16 1 0 0 0 0 10 13 2 0 0 0 0 10 17 1 0 0 0 0 11 13 1 0 0 0 0 11 22 1 0 0 0 0 12 16 1 6 0 0 0 12 18 1 0 0 0 0 13 14 1 0 0 0 0 14 19 2 0 0 0 0 15 20 2 0 0 0 0 15 21 1 0 0 0 0 16 15 1 1 0 0 0 16 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.08
Volume:	293.909
LogP:	2.447
LogD:	1.479
LogS:	-3.741
# Rotatable Bonds:	2
TPSA:	89.9
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.624
Synthetic Accessibility Score:	3.695
Fsp3:	0.312
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.686
MDCK Permeability:	2.008340561587829e-05
Pgp-inhibitor:	0.04
Pgp-substrate:	0.022
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.064

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.16
Plasma Protein Binding (PPB):	87.03793334960938%
Volume Distribution (VD):	0.579
Pgp-substrate:	4.846619129180908%

ADMET: Metabolism

CYP1A2-inhibitor:	0.929
CYP1A2-substrate:	0.743
CYP2C19-inhibitor:	0.295
CYP2C19-substrate:	0.665
CYP2C9-inhibitor:	0.291
CYP2C9-substrate:	0.158
CYP2D6-inhibitor:	0.038
CYP2D6-substrate:	0.23
CYP3A4-inhibitor:	0.596
CYP3A4-substrate:	0.653

ADMET: Excretion

Clearance (CL):	11.191
Half-life (T1/2):	0.358

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.687
Drug-inuced Liver Injury (DILI):	0.974
AMES Toxicity:	0.974
Rat Oral Acute Toxicity:	0.325
Maximum Recommended Daily Dose:	0.866
Skin Sensitization:	0.865
Carcinogencity:	0.838
Eye Corrosion:	0.025
Eye Irritation:	0.262
Respiratory Toxicity:	0.735

Download Data

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

Natural Product: NPC237560

Natural Product ID:	NPC237560
*Common Name:**	Methyl (4R,4As)-4,8-Dihydroxy-6-Methyl-9-Oxo-4H-Xanthene-4A-Carboxylate
IUPAC Name:	methyl (4R,4aS)-4,8-dihydroxy-6-methyl-9-oxo-4H-xanthene-4a-carboxylate
Synonyms:
Standard InCHIKey:	BVPTZDRKEDPTOX-WBMJQRKESA-N
Standard InCHI:	InChI=1S/C16H14O6/c1-8-6-10(17)13-11(7-8)22-16(15(20)21-2)9(14(13)19)4-3-5-12(16)18/h3-7,12,17-18H,1-2H3/t12-,16+/m1/s1
SMILES:	Cc1cc(c2c(c1)O[C@]1(C(=CC=C[C@H]1O)C2=O)C(=O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL91382
PubChem CID:	9926413
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones

*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
NPO31059	Penicillium	Genus	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10724005]
NPO31059	Penicillium	Genus	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10724008]
NPO568	Peganum nigellastrum	Species	Nitrariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757727]
NPO31059	Penicillium	Genus	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11099218]
NPO31059	Penicillium	Genus	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350167]
NPO31059	Penicillium	Genus	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15332861]
NPO31059	Penicillium	Genus	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387518]
NPO4291	Laurencia brongniartii	Species	Rhodomelaceae	Eukaryota	n.a.	Formosan red alga	n.a.	PMID[15921441]
NPO31059	Penicillium	Genus	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16568716]
NPO31059	Penicillium	Genus	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7649881]
NPO31059	Penicillium	Genus	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8002401]
NPO31059	Penicillium	Genus	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9711252]
NPO31300.1	Emericella nidulans var. lata	Varieties	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO568	Peganum nigellastrum	Species	Nitrariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO568	Peganum nigellastrum	Species	Nitrariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4291	Laurencia brongniartii	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO568	Peganum nigellastrum	Species	Nitrariaceae	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
IC50	5
Others	1

Activity Type	# Activity
Cell Line	3
Individual Protein	2
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	140.0	nM	PMID[448810]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	320.0	nM	PMID[448810]
NPT168	Cell Line	P388	Mus musculus	IC50	=	24.0	nM	PMID[448810]
NPT4451	Individual Protein	DNA topoisomerase I	Mus musculus	IC50	=	172000.0	nM	PMID[448810]
NPT5376	Individual Protein	DNA topoisomerase II	Drosophila melanogaster	IC50	=	2200.0	nM	PMID[448810]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	24.0	%	PMID[448810]

☑ 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 NPC237560 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	353
0.1-0.2	1426
0.2-0.3	3746
0.3-0.4	8022
0.4-0.5	10261
0.5-0.6	4058
0.6-0.7	5904
0.7-0.8	7221
0.8-0.85	1592
0.85-0.9	101
0.9-0.95	11
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9536	High Similarity	NPC154341
0.9333	High Similarity	NPC475717
0.9216	High Similarity	NPC326910
0.92	High Similarity	NPC228012
0.915	High Similarity	NPC301233
0.9026	High Similarity	NPC198236
0.902	High Similarity	NPC39819
0.8961	High Similarity	NPC275878
0.8961	High Similarity	NPC321363
0.8961	High Similarity	NPC253904
0.8947	High Similarity	NPC191634
0.8874	High Similarity	NPC469764
0.8839	High Similarity	NPC281272
0.8816	High Similarity	NPC469758
0.879	High Similarity	NPC272550
0.879	High Similarity	NPC472050
0.8784	High Similarity	NPC287068
0.878	High Similarity	NPC154986
0.8766	High Similarity	NPC4423
0.8766	High Similarity	NPC477941
0.8766	High Similarity	NPC77325
0.8742	High Similarity	NPC471744
0.8742	High Similarity	NPC130955
0.8735	High Similarity	NPC477682
0.8735	High Similarity	NPC477683
0.8734	High Similarity	NPC476930
0.8734	High Similarity	NPC246466
0.8725	High Similarity	NPC268691
0.8718	High Similarity	NPC256141
0.871	High Similarity	NPC267117
0.8701	High Similarity	NPC218569
0.8688	High Similarity	NPC112418
0.8671	High Similarity	NPC313922
0.8662	High Similarity	NPC203080
0.8654	High Similarity	NPC471229
0.8654	High Similarity	NPC207346
0.8654	High Similarity	NPC295650
0.8654	High Similarity	NPC475076
0.8654	High Similarity	NPC46564
0.8645	High Similarity	NPC70764
0.8645	High Similarity	NPC277032
0.8636	High Similarity	NPC122828
0.8636	High Similarity	NPC44721
0.8636	High Similarity	NPC21835
0.8636	High Similarity	NPC176869
0.8636	High Similarity	NPC40086
0.8636	High Similarity	NPC146884
0.8636	High Similarity	NPC3779
0.8636	High Similarity	NPC211466
0.8636	High Similarity	NPC476182
0.8634	High Similarity	NPC471745
0.8627	High Similarity	NPC316535
0.8616	High Similarity	NPC52530
0.8616	High Similarity	NPC472889
0.8614	High Similarity	NPC232412
0.8614	High Similarity	NPC86809
0.8614	High Similarity	NPC98667
0.8608	High Similarity	NPC208173
0.8608	High Similarity	NPC175192
0.8608	High Similarity	NPC170189
0.8599	High Similarity	NPC226801
0.8599	High Similarity	NPC243171
0.8599	High Similarity	NPC35567
0.8599	High Similarity	NPC478224
0.8599	High Similarity	NPC171651
0.859	High Similarity	NPC472891
0.859	High Similarity	NPC116822
0.859	High Similarity	NPC180351
0.8588	High Similarity	NPC197972
0.8581	High Similarity	NPC211811
0.8581	High Similarity	NPC215711
0.8581	High Similarity	NPC73411
0.8571	High Similarity	NPC308992
0.8571	High Similarity	NPC209278
0.8571	High Similarity	NPC117985
0.8571	High Similarity	NPC1940
0.8571	High Similarity	NPC229190
0.8571	High Similarity	NPC196114
0.8571	High Similarity	NPC148011
0.8563	High Similarity	NPC469345
0.8562	High Similarity	NPC231475
0.8562	High Similarity	NPC57072
0.8562	High Similarity	NPC55738
0.8553	High Similarity	NPC320825
0.8553	High Similarity	NPC474638
0.8553	High Similarity	NPC13858
0.8553	High Similarity	NPC471500
0.8553	High Similarity	NPC150023
0.8553	High Similarity	NPC326037
0.8545	High Similarity	NPC72696
0.8545	High Similarity	NPC313717
0.8545	High Similarity	NPC315306
0.8544	High Similarity	NPC293286
0.8544	High Similarity	NPC27532
0.8544	High Similarity	NPC256346
0.8544	High Similarity	NPC141212
0.8544	High Similarity	NPC325028
0.8544	High Similarity	NPC246328
0.8537	High Similarity	NPC283041
0.8535	High Similarity	NPC215921
0.8535	High Similarity	NPC278476
0.8535	High Similarity	NPC262039
0.8535	High Similarity	NPC319910
0.8535	High Similarity	NPC262038
0.8535	High Similarity	NPC46882
0.8535	High Similarity	NPC471676
0.8535	High Similarity	NPC132990
0.8535	High Similarity	NPC472420
0.8535	High Similarity	NPC263384
0.8535	High Similarity	NPC254412
0.8535	High Similarity	NPC472422
0.8535	High Similarity	NPC70016
0.8535	High Similarity	NPC244577
0.8528	High Similarity	NPC88243
0.8526	High Similarity	NPC237440
0.8526	High Similarity	NPC270160
0.8526	High Similarity	NPC73236
0.8521	High Similarity	NPC208069
0.8516	High Similarity	NPC210320
0.8516	High Similarity	NPC129650
0.8516	High Similarity	NPC71055
0.8516	High Similarity	NPC472918
0.8509	High Similarity	NPC263449
0.8509	High Similarity	NPC471976
0.8509	High Similarity	NPC470183
0.8506	High Similarity	NPC62290
0.8506	High Similarity	NPC142731
0.8506	High Similarity	NPC279417
0.8506	High Similarity	NPC326506
0.8506	High Similarity	NPC49130
0.8506	High Similarity	NPC208176
0.8506	High Similarity	NPC4152
0.8506	High Similarity	NPC306607
0.85	High Similarity	NPC471515
0.85	High Similarity	NPC67876
0.85	High Similarity	NPC471479
0.85	High Similarity	NPC281137
0.85	High Similarity	NPC282390
0.8497	Intermediate Similarity	NPC476310
0.8497	Intermediate Similarity	NPC476164
0.8494	Intermediate Similarity	NPC472620
0.8491	Intermediate Similarity	NPC478221
0.8491	Intermediate Similarity	NPC472890
0.8491	Intermediate Similarity	NPC69043
0.8491	Intermediate Similarity	NPC304207
0.8491	Intermediate Similarity	NPC217706
0.8491	Intermediate Similarity	NPC99381
0.8491	Intermediate Similarity	NPC48579
0.8491	Intermediate Similarity	NPC478230
0.8491	Intermediate Similarity	NPC473241
0.8491	Intermediate Similarity	NPC259710
0.8491	Intermediate Similarity	NPC207809
0.8491	Intermediate Similarity	NPC317585
0.8487	Intermediate Similarity	NPC145673
0.8485	Intermediate Similarity	NPC472619
0.8481	Intermediate Similarity	NPC75069
0.8481	Intermediate Similarity	NPC9743
0.8481	Intermediate Similarity	NPC240476
0.8481	Intermediate Similarity	NPC36835
0.8481	Intermediate Similarity	NPC184284
0.8481	Intermediate Similarity	NPC138288
0.8481	Intermediate Similarity	NPC61506
0.8481	Intermediate Similarity	NPC210597
0.8481	Intermediate Similarity	NPC115249
0.8481	Intermediate Similarity	NPC217149
0.8481	Intermediate Similarity	NPC260491
0.8481	Intermediate Similarity	NPC216035
0.8481	Intermediate Similarity	NPC246162
0.8481	Intermediate Similarity	NPC76041
0.8476	Intermediate Similarity	NPC178173
0.8476	Intermediate Similarity	NPC20237
0.8471	Intermediate Similarity	NPC470107
0.8471	Intermediate Similarity	NPC105136
0.8457	Intermediate Similarity	NPC173137
0.8457	Intermediate Similarity	NPC476929
0.8457	Intermediate Similarity	NPC3629
0.8447	Intermediate Similarity	NPC22192
0.8447	Intermediate Similarity	NPC152904
0.8447	Intermediate Similarity	NPC125969
0.8447	Intermediate Similarity	NPC477410
0.8447	Intermediate Similarity	NPC470339
0.8442	Intermediate Similarity	NPC103910
0.8442	Intermediate Similarity	NPC105381
0.8442	Intermediate Similarity	NPC10302
0.8442	Intermediate Similarity	NPC59551
0.8438	Intermediate Similarity	NPC20530
0.8438	Intermediate Similarity	NPC250922
0.8438	Intermediate Similarity	NPC78492
0.8438	Intermediate Similarity	NPC215917
0.8438	Intermediate Similarity	NPC164427
0.8438	Intermediate Similarity	NPC10754
0.8438	Intermediate Similarity	NPC201837
0.8438	Intermediate Similarity	NPC208152
0.8434	Intermediate Similarity	NPC241874
0.8428	Intermediate Similarity	NPC469405
0.8428	Intermediate Similarity	NPC7989
0.8428	Intermediate Similarity	NPC100134
0.8428	Intermediate Similarity	NPC137301
0.8428	Intermediate Similarity	NPC155686
0.8428	Intermediate Similarity	NPC299435

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 NPC237560 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	314
0.1-0.2	887
0.2-0.3	1825
0.3-0.4	2532
0.4-0.5	1915
0.5-0.6	1075
0.6-0.7	409
0.7-0.8	167
0.8-0.85	23
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8734	High Similarity	NPD7075	Discontinued
0.8726	High Similarity	NPD5402	Approved
0.8662	High Similarity	NPD7096	Clinical (unspecified phase)
0.8636	High Similarity	NPD5403	Approved
0.8627	High Similarity	NPD5401	Approved
0.8481	Intermediate Similarity	NPD6801	Discontinued
0.8471	Intermediate Similarity	NPD6599	Discontinued
0.8442	Intermediate Similarity	NPD6799	Approved
0.8366	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD1934	Approved
0.8344	Intermediate Similarity	NPD1551	Phase 2
0.8323	Intermediate Similarity	NPD3882	Suspended
0.8261	Intermediate Similarity	NPD3817	Phase 2
0.8247	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD1549	Phase 2
0.8225	Intermediate Similarity	NPD6559	Discontinued
0.8199	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD6166	Phase 2
0.8193	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.817	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.817	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD4380	Phase 2
0.8114	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD7819	Suspended
0.8059	Intermediate Similarity	NPD6797	Phase 2
0.8047	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD3750	Approved
0.8012	Intermediate Similarity	NPD7251	Discontinued
0.7988	Intermediate Similarity	NPD3818	Discontinued
0.7988	Intermediate Similarity	NPD3751	Discontinued
0.7987	Intermediate Similarity	NPD1512	Approved
0.7975	Intermediate Similarity	NPD2801	Approved
0.7965	Intermediate Similarity	NPD7808	Phase 3
0.7963	Intermediate Similarity	NPD7411	Suspended
0.7953	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD3226	Approved
0.7935	Intermediate Similarity	NPD2346	Discontinued
0.7922	Intermediate Similarity	NPD1510	Phase 2
0.7908	Intermediate Similarity	NPD1607	Approved
0.7898	Intermediate Similarity	NPD4628	Phase 3
0.7895	Intermediate Similarity	NPD7074	Phase 3
0.7885	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD2796	Approved
0.7862	Intermediate Similarity	NPD1511	Approved
0.7857	Intermediate Similarity	NPD6232	Discontinued
0.7843	Intermediate Similarity	NPD447	Suspended
0.7836	Intermediate Similarity	NPD7054	Approved
0.7836	Intermediate Similarity	NPD5844	Phase 1
0.7831	Intermediate Similarity	NPD3749	Approved
0.7824	Intermediate Similarity	NPD7473	Discontinued
0.7816	Intermediate Similarity	NPD8312	Approved
0.7816	Intermediate Similarity	NPD8313	Approved
0.7812	Intermediate Similarity	NPD2533	Approved
0.7812	Intermediate Similarity	NPD2532	Approved
0.7812	Intermediate Similarity	NPD2534	Approved
0.7791	Intermediate Similarity	NPD7472	Approved
0.7784	Intermediate Similarity	NPD919	Approved
0.7778	Intermediate Similarity	NPD1240	Approved
0.7771	Intermediate Similarity	NPD7768	Phase 2
0.7763	Intermediate Similarity	NPD411	Approved
0.7711	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD9717	Approved
0.7702	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6959	Discontinued
0.7692	Intermediate Similarity	NPD3748	Approved
0.7692	Intermediate Similarity	NPD4308	Phase 3
0.7684	Intermediate Similarity	NPD8434	Phase 2
0.7684	Intermediate Similarity	NPD8150	Discontinued
0.7676	Intermediate Similarity	NPD7435	Discontinued
0.7667	Intermediate Similarity	NPD1203	Approved
0.7661	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD2313	Discontinued
0.7643	Intermediate Similarity	NPD6099	Approved
0.7643	Intermediate Similarity	NPD2935	Discontinued
0.7643	Intermediate Similarity	NPD6100	Approved
0.7633	Intermediate Similarity	NPD5494	Approved
0.7622	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD1465	Phase 2
0.7544	Intermediate Similarity	NPD3787	Discontinued
0.7533	Intermediate Similarity	NPD4749	Approved
0.7532	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6798	Discontinued
0.7517	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6832	Phase 2
0.7514	Intermediate Similarity	NPD6777	Approved
0.7514	Intermediate Similarity	NPD6782	Approved
0.7514	Intermediate Similarity	NPD6779	Approved
0.7514	Intermediate Similarity	NPD6778	Approved
0.7514	Intermediate Similarity	NPD6776	Approved
0.7514	Intermediate Similarity	NPD6780	Approved
0.7514	Intermediate Similarity	NPD6781	Approved
0.75	Intermediate Similarity	NPD920	Approved
0.75	Intermediate Similarity	NPD1933	Approved
0.75	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD230	Phase 1
0.75	Intermediate Similarity	NPD2800	Approved
0.7485	Intermediate Similarity	NPD1247	Approved
0.7468	Intermediate Similarity	NPD2799	Discontinued
0.7468	Intermediate Similarity	NPD7033	Discontinued
0.7457	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD5953	Discontinued
0.7436	Intermediate Similarity	NPD1613	Approved
0.7436	Intermediate Similarity	NPD4307	Phase 2
0.7436	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7435	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7435	Intermediate Similarity	NPD7874	Approved
0.7419	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6190	Approved
0.7399	Intermediate Similarity	NPD3926	Phase 2
0.7391	Intermediate Similarity	NPD1243	Approved
0.7389	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD5124	Phase 1
0.7389	Intermediate Similarity	NPD6355	Discontinued
0.7378	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD1653	Approved
0.7347	Intermediate Similarity	NPD9493	Approved
0.7341	Intermediate Similarity	NPD5710	Approved
0.7341	Intermediate Similarity	NPD5711	Approved
0.7325	Intermediate Similarity	NPD943	Approved
0.7308	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD7697	Approved
0.7302	Intermediate Similarity	NPD7696	Phase 3
0.7302	Intermediate Similarity	NPD7698	Approved
0.7285	Intermediate Similarity	NPD422	Phase 1
0.7284	Intermediate Similarity	NPD1652	Phase 2
0.7273	Intermediate Similarity	NPD1019	Discontinued
0.7267	Intermediate Similarity	NPD2344	Approved
0.7267	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5762	Approved
0.7267	Intermediate Similarity	NPD5763	Approved
0.7263	Intermediate Similarity	NPD7871	Phase 2
0.7263	Intermediate Similarity	NPD8319	Approved
0.7263	Intermediate Similarity	NPD8320	Phase 1
0.7263	Intermediate Similarity	NPD7870	Phase 2
0.7261	Intermediate Similarity	NPD6233	Phase 2
0.7244	Intermediate Similarity	NPD4625	Phase 3
0.7243	Intermediate Similarity	NPD6534	Approved
0.7243	Intermediate Similarity	NPD6535	Approved
0.724	Intermediate Similarity	NPD7701	Phase 2
0.7238	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD7286	Phase 2
0.7215	Intermediate Similarity	NPD4060	Phase 1
0.7208	Intermediate Similarity	NPD1470	Approved
0.7208	Intermediate Similarity	NPD2797	Approved
0.7202	Intermediate Similarity	NPD8151	Discontinued
0.72	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD3268	Approved
0.7195	Intermediate Similarity	NPD2354	Approved
0.7186	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6844	Discontinued
0.7176	Intermediate Similarity	NPD37	Approved
0.7168	Intermediate Similarity	NPD6234	Discontinued
0.7161	Intermediate Similarity	NPD5647	Approved
0.7161	Intermediate Similarity	NPD2798	Approved
0.716	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD6823	Phase 2
0.7152	Intermediate Similarity	NPD1778	Approved
0.7151	Intermediate Similarity	NPD4965	Approved
0.7151	Intermediate Similarity	NPD4967	Phase 2
0.7151	Intermediate Similarity	NPD4966	Approved
0.7143	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7095	Approved
0.7128	Intermediate Similarity	NPD7700	Phase 2
0.7128	Intermediate Similarity	NPD7801	Approved
0.7128	Intermediate Similarity	NPD7699	Phase 2
0.7126	Intermediate Similarity	NPD5049	Phase 3
0.7125	Intermediate Similarity	NPD6651	Approved
0.7124	Intermediate Similarity	NPD1608	Approved
0.7118	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD2424	Discontinued
0.7115	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD4288	Approved
0.7091	Intermediate Similarity	NPD3887	Approved
0.7091	Intermediate Similarity	NPD2309	Approved
0.7089	Intermediate Similarity	NPD3764	Approved
0.7086	Intermediate Similarity	NPD7199	Phase 2
0.7079	Intermediate Similarity	NPD7228	Approved
0.707	Intermediate Similarity	NPD4908	Phase 1
0.7066	Intermediate Similarity	NPD4661	Approved
0.7066	Intermediate Similarity	NPD4662	Approved
0.7065	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD2403	Approved
0.7059	Intermediate Similarity	NPD1610	Phase 2
0.7055	Intermediate Similarity	NPD1471	Phase 3
0.7044	Intermediate Similarity	NPD4062	Phase 3
0.7041	Intermediate Similarity	NPD7783	Phase 2
0.7041	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD3225	Approved
0.7025	Intermediate Similarity	NPD3027	Phase 3

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