NPASS Compound

Structure

NPC473945 OpenBabel07101718182D 29 33 0 0 1 0 0 0 0 0999 V2000 3.9267 -2.7561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0622 -3.0306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6556 -2.3264 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7816 -3.0293 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7656 -2.8508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4359 -4.4390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6228 -3.0306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9567 -5.7245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8425 -3.7348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4359 -3.0306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6228 -4.4390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0909 -4.7335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2162 -3.7348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6556 -3.7348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4443 -3.9707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8425 -2.3264 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0748 -4.5550 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3257 -5.1959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5487 -5.4356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4122 -3.6136 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 7.1556 -4.6008 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 0.4604 -4.1493 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0059 -5.9289 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3425 -0.4604 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3425 -1.4604 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3425 -2.4604 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8576 -6.1584 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3425 -1.4604 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3425 -1.4604 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 3 1 0 0 0 0 2 14 2 0 0 0 0 3 16 2 0 0 0 0 4 5 1 0 0 0 0 4 15 1 0 0 0 0 5 20 1 0 0 0 0 6 9 2 0 0 0 0 6 11 1 0 0 0 0 7 10 2 0 0 0 0 7 13 1 0 0 0 0 8 12 2 0 0 0 0 8 27 1 0 0 0 0 9 10 1 0 0 0 0 9 14 1 0 0 0 0 10 16 1 0 0 0 0 11 13 2 0 0 0 0 11 18 1 0 0 0 0 12 15 1 0 0 0 0 12 17 1 0 0 0 0 13 20 1 0 0 0 0 14 21 1 0 0 0 0 15 22 2 0 0 0 0 16 28 1 0 0 0 0 17 19 2 0 0 0 0 17 20 1 0 0 0 0 18 19 1 0 0 0 0 18 23 2 0 0 0 0 19 27 1 0 0 0 0 24 29 1 0 0 0 0 25 29 2 0 0 0 0 26 29 2 0 0 0 0 28 29 1 0 0 0 0 M CHG 1 21 -1 M END $$$$

Physi-Chem Properties

Molecular Weight:	413.03
Volume:	375.478
LogP:	2.173
LogD:	1.009
LogS:	-5.335
# Rotatable Bonds:	2
TPSA:	133.94
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.501
Synthetic Accessibility Score:	3.917
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.936
MDCK Permeability:	2.0519293684628792e-05
Pgp-inhibitor:	0.091
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.019

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	98.01850891113281%
Volume Distribution (VD):	0.32
Pgp-substrate:	1.7884652614593506%

ADMET: Metabolism

CYP1A2-inhibitor:	0.789
CYP1A2-substrate:	0.856
CYP2C19-inhibitor:	0.096
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.461
CYP2C9-substrate:	0.541
CYP2D6-inhibitor:	0.314
CYP2D6-substrate:	0.218
CYP3A4-inhibitor:	0.145
CYP3A4-substrate:	0.223

ADMET: Excretion

Clearance (CL):	1.204
Half-life (T1/2):	0.095

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.959
Drug-inuced Liver Injury (DILI):	0.931
AMES Toxicity:	0.802
Rat Oral Acute Toxicity:	0.962
Maximum Recommended Daily Dose:	0.972
Skin Sensitization:	0.181
Carcinogencity:	0.969
Eye Corrosion:	0.003
Eye Irritation:	0.165
Respiratory Toxicity:	0.891

Download Data

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

Natural Product: NPC473945

Natural Product ID:	NPC473945
*Common Name:**	Halenaquinol Sulfate Sodium
IUPAC Name:	n.a.
Synonyms:	Halenaquinol Sulfate; Halenaquinol Sulfate Sodium
Standard InCHIKey:	GCVHMYXVBXEDEI-BDQAORGHSA-M
Standard InCHI:	InChI=1S/C20H14O8S.Na/c1-20-5-4-15(22)12-8-27-19(17(12)20)18(23)11-6-9-10(7-13(11)20)16(3-2-14(9)21)28-29(24,25)26;/h2-3,6-8,21H,4-5H2,1H3,(H,24,25,26);/q;+1/p-1/t20-;/m0./s1
SMILES:	O=C1CC[C@@]2(c3c1coc3C(=O)c1c2cc2c(ccc(c2c1)[O-])OS(=O)(=O)O)C.[Na+]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL455880
PubChem CID:	23425708
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives

*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
NPO32714	xestospongia	Genus	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10843588]
NPO32714	xestospongia	Genus	Petrosiidae	Eukaryota	n.a.	South Pacific	n.a.	PMID[20634081]

☑ 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	9
MIC	1
Others	2

Activity Type	# Activity
Cell Line	3
Individual Protein	4
Organism	2
Others	2
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT143	Individual Protein	DNA topoisomerase I	Homo sapiens	MIC	>	50.0	ug.mL-1	PMID[448580]
NPT137	Cell Line	L1210	Mus musculus	Activity	=	22.4	%	PMID[448580]
NPT91	Cell Line	KB	Homo sapiens	Activity	=	12.2	%	PMID[448580]
NPT1119	Individual Protein	Arachidonate 12-lipoxygenase	Homo sapiens	IC50	>	200000.0	nM	PMID[448581]
NPT4422	Individual Protein	Phospholipase A2 (Bee)	Apis mellifera	IC50	=	1000000.0	nM	PMID[448582]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	>	48000.0	nM	PMID[448582]
NPT792	Individual Protein	Arachidonate 15-lipoxygenase	Homo sapiens	IC50	>	200000.0	nM	PMID[448581]
NPT2	Others	Unspecified		IC50	>	200000.0	nM	PMID[448581]
NPT2	Others	Unspecified		IC50	=	16110.0	nM	PMID[448582]
NPT1180	Protein Complex	Protein farnesyltransferase	Homo sapiens	IC50	=	21510.0	nM	PMID[448582]
NPT1225	Organism	Plasmodium falciparum (isolate FcB1 / Columbia)	Plasmodium falciparum FcB1/Columbia	IC50	>	24000.0	nM	PMID[448582]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	>	24000.0	nM	PMID[448582]

☑ 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 NPC473945 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	483
0.1-0.2	2150
0.2-0.3	4693
0.3-0.4	12007
0.4-0.5	6926
0.5-0.6	6461
0.6-0.7	6824
0.7-0.8	3102
0.8-0.85	46
0.85-0.9	4
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8861	High Similarity	NPC192069
0.8704	High Similarity	NPC88958
0.8616	High Similarity	NPC281398
0.8608	High Similarity	NPC93241
0.8608	High Similarity	NPC27798
0.8589	High Similarity	NPC179170
0.858	High Similarity	NPC145830
0.8553	High Similarity	NPC478166
0.8519	High Similarity	NPC144010
0.8485	Intermediate Similarity	NPC221992
0.8428	Intermediate Similarity	NPC117674
0.8375	Intermediate Similarity	NPC114513
0.8375	Intermediate Similarity	NPC245522
0.8333	Intermediate Similarity	NPC252208
0.8256	Intermediate Similarity	NPC44602
0.8253	Intermediate Similarity	NPC290927
0.8253	Intermediate Similarity	NPC23559
0.8232	Intermediate Similarity	NPC472298
0.8228	Intermediate Similarity	NPC265181
0.8214	Intermediate Similarity	NPC10051
0.8214	Intermediate Similarity	NPC299094
0.821	Intermediate Similarity	NPC233763
0.8204	Intermediate Similarity	NPC3898
0.8193	Intermediate Similarity	NPC24232
0.8176	Intermediate Similarity	NPC24761
0.8171	Intermediate Similarity	NPC95526
0.8121	Intermediate Similarity	NPC226578
0.8107	Intermediate Similarity	NPC294300
0.8107	Intermediate Similarity	NPC476404
0.8107	Intermediate Similarity	NPC317900
0.8107	Intermediate Similarity	NPC67197
0.8095	Intermediate Similarity	NPC233776
0.8086	Intermediate Similarity	NPC53016
0.8084	Intermediate Similarity	NPC282793
0.8084	Intermediate Similarity	NPC10429
0.8084	Intermediate Similarity	NPC44606
0.8061	Intermediate Similarity	NPC474107
0.8059	Intermediate Similarity	NPC472299
0.8045	Intermediate Similarity	NPC475996
0.8037	Intermediate Similarity	NPC290038
0.8036	Intermediate Similarity	NPC41719
0.8036	Intermediate Similarity	NPC469966
0.8035	Intermediate Similarity	NPC472784
0.8025	Intermediate Similarity	NPC69755
0.8023	Intermediate Similarity	NPC193998
0.8012	Intermediate Similarity	NPC469840
0.8	Intermediate Similarity	NPC104380
0.8	Intermediate Similarity	NPC478018
0.8	Intermediate Similarity	NPC217602
0.8	Intermediate Similarity	NPC473282
0.7976	Intermediate Similarity	NPC130015
0.7976	Intermediate Similarity	NPC38361
0.7963	Intermediate Similarity	NPC149780
0.7937	Intermediate Similarity	NPC177262
0.7931	Intermediate Similarity	NPC41689
0.7917	Intermediate Similarity	NPC471613
0.7907	Intermediate Similarity	NPC284495
0.7895	Intermediate Similarity	NPC123153
0.7888	Intermediate Similarity	NPC233707
0.7886	Intermediate Similarity	NPC291742
0.7882	Intermediate Similarity	NPC478161
0.7882	Intermediate Similarity	NPC478159
0.788	Intermediate Similarity	NPC295436
0.7874	Intermediate Similarity	NPC308156
0.7865	Intermediate Similarity	NPC277510
0.7857	Intermediate Similarity	NPC135303
0.7857	Intermediate Similarity	NPC148423
0.7849	Intermediate Similarity	NPC472877
0.7844	Intermediate Similarity	NPC472056
0.7844	Intermediate Similarity	NPC280025
0.7841	Intermediate Similarity	NPC186392
0.7841	Intermediate Similarity	NPC472660
0.7838	Intermediate Similarity	NPC60848
0.7836	Intermediate Similarity	NPC81405
0.7831	Intermediate Similarity	NPC224418
0.7829	Intermediate Similarity	NPC270312
0.7826	Intermediate Similarity	NPC186647
0.7826	Intermediate Similarity	NPC284184
0.7816	Intermediate Similarity	NPC56358
0.7811	Intermediate Similarity	NPC472407
0.7809	Intermediate Similarity	NPC478002
0.7803	Intermediate Similarity	NPC472781
0.7803	Intermediate Similarity	NPC472782
0.7802	Intermediate Similarity	NPC228209
0.7799	Intermediate Similarity	NPC470406
0.7791	Intermediate Similarity	NPC140952
0.7791	Intermediate Similarity	NPC164110
0.7791	Intermediate Similarity	NPC96342
0.7791	Intermediate Similarity	NPC246647
0.7791	Intermediate Similarity	NPC212967
0.779	Intermediate Similarity	NPC104682
0.779	Intermediate Similarity	NPC70318
0.7784	Intermediate Similarity	NPC478163
0.7784	Intermediate Similarity	NPC198427
0.7778	Intermediate Similarity	NPC472661
0.7778	Intermediate Similarity	NPC295914
0.7772	Intermediate Similarity	NPC248315
0.7771	Intermediate Similarity	NPC65846
0.7765	Intermediate Similarity	NPC27615
0.7765	Intermediate Similarity	NPC263676
0.7765	Intermediate Similarity	NPC470333
0.7765	Intermediate Similarity	NPC65885
0.7764	Intermediate Similarity	NPC232996
0.7759	Intermediate Similarity	NPC264293
0.7759	Intermediate Similarity	NPC472780
0.7759	Intermediate Similarity	NPC472783
0.7759	Intermediate Similarity	NPC269117
0.7753	Intermediate Similarity	NPC190351
0.7751	Intermediate Similarity	NPC472406
0.7746	Intermediate Similarity	NPC324736
0.7744	Intermediate Similarity	NPC124365
0.774	Intermediate Similarity	NPC95715
0.7738	Intermediate Similarity	NPC472839
0.7738	Intermediate Similarity	NPC306788
0.7735	Intermediate Similarity	NPC246877
0.7735	Intermediate Similarity	NPC478000
0.7735	Intermediate Similarity	NPC23553
0.7735	Intermediate Similarity	NPC77179
0.7733	Intermediate Similarity	NPC180924
0.7733	Intermediate Similarity	NPC160015
0.7733	Intermediate Similarity	NPC247677
0.7727	Intermediate Similarity	NPC314653
0.7727	Intermediate Similarity	NPC316262
0.7727	Intermediate Similarity	NPC279768
0.7725	Intermediate Similarity	NPC300540
0.7722	Intermediate Similarity	NPC186800
0.7719	Intermediate Similarity	NPC84721
0.7719	Intermediate Similarity	NPC25351
0.7719	Intermediate Similarity	NPC208806
0.7716	Intermediate Similarity	NPC301341
0.7714	Intermediate Similarity	NPC472664
0.7709	Intermediate Similarity	NPC91650
0.7705	Intermediate Similarity	NPC478001
0.7705	Intermediate Similarity	NPC471842
0.7705	Intermediate Similarity	NPC470332
0.7705	Intermediate Similarity	NPC8927
0.7705	Intermediate Similarity	NPC240508
0.7702	Intermediate Similarity	NPC217914
0.7701	Intermediate Similarity	NPC476506
0.7701	Intermediate Similarity	NPC313368
0.7697	Intermediate Similarity	NPC202470
0.7688	Intermediate Similarity	NPC260902
0.7688	Intermediate Similarity	NPC296957
0.7684	Intermediate Similarity	NPC191012
0.7684	Intermediate Similarity	NPC472895
0.7684	Intermediate Similarity	NPC255787
0.7684	Intermediate Similarity	NPC298071
0.768	Intermediate Similarity	NPC49667
0.768	Intermediate Similarity	NPC8127
0.7676	Intermediate Similarity	NPC240808
0.7674	Intermediate Similarity	NPC66508
0.7674	Intermediate Similarity	NPC226656
0.7674	Intermediate Similarity	NPC148938
0.767	Intermediate Similarity	NPC38591
0.767	Intermediate Similarity	NPC132054
0.767	Intermediate Similarity	NPC109180
0.767	Intermediate Similarity	NPC475779
0.767	Intermediate Similarity	NPC100849
0.7667	Intermediate Similarity	NPC167340
0.7667	Intermediate Similarity	NPC117450
0.7665	Intermediate Similarity	NPC262198
0.7665	Intermediate Similarity	NPC474261
0.7661	Intermediate Similarity	NPC253872
0.7661	Intermediate Similarity	NPC67654
0.7658	Intermediate Similarity	NPC57552
0.7657	Intermediate Similarity	NPC109238
0.7657	Intermediate Similarity	NPC304387
0.7654	Intermediate Similarity	NPC476641
0.7654	Intermediate Similarity	NPC155211
0.7651	Intermediate Similarity	NPC158871
0.7651	Intermediate Similarity	NPC163948
0.7644	Intermediate Similarity	NPC476349
0.7644	Intermediate Similarity	NPC228501
0.7644	Intermediate Similarity	NPC250076
0.7644	Intermediate Similarity	NPC477692
0.7644	Intermediate Similarity	NPC287559
0.7644	Intermediate Similarity	NPC476350
0.764	Intermediate Similarity	NPC209858
0.764	Intermediate Similarity	NPC1249
0.764	Intermediate Similarity	NPC241820
0.764	Intermediate Similarity	NPC253730
0.764	Intermediate Similarity	NPC286230
0.764	Intermediate Similarity	NPC324117
0.7637	Intermediate Similarity	NPC221820
0.7637	Intermediate Similarity	NPC5671
0.763	Intermediate Similarity	NPC137100
0.763	Intermediate Similarity	NPC469507
0.763	Intermediate Similarity	NPC474360
0.7627	Intermediate Similarity	NPC473753
0.7627	Intermediate Similarity	NPC169471
0.7627	Intermediate Similarity	NPC473766
0.7627	Intermediate Similarity	NPC136641
0.7624	Intermediate Similarity	NPC470667
0.7624	Intermediate Similarity	NPC245975
0.7624	Intermediate Similarity	NPC287243
0.7622	Intermediate Similarity	NPC476191
0.7622	Intermediate Similarity	NPC470407
0.7622	Intermediate Similarity	NPC18904
0.7619	Intermediate Similarity	NPC190572
0.7619	Intermediate Similarity	NPC471346

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 NPC473945 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	427
0.1-0.2	1049
0.2-0.3	1710
0.3-0.4	2869
0.4-0.5	1909
0.5-0.6	847
0.6-0.7	278
0.7-0.8	60
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8228	Intermediate Similarity	NPD1471	Phase 3
0.7798	Intermediate Similarity	NPD3226	Approved
0.7759	Intermediate Similarity	NPD1247	Approved
0.7669	Intermediate Similarity	NPD2344	Approved
0.7561	Intermediate Similarity	NPD2346	Discontinued
0.7561	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD6959	Discontinued
0.7485	Intermediate Similarity	NPD2309	Approved
0.7443	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD920	Approved
0.7366	Intermediate Similarity	NPD8434	Phase 2
0.7348	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD5494	Approved
0.7302	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD3926	Phase 2
0.7273	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD919	Approved
0.7219	Intermediate Similarity	NPD7003	Approved
0.7216	Intermediate Similarity	NPD7819	Suspended
0.72	Intermediate Similarity	NPD7411	Suspended
0.7191	Intermediate Similarity	NPD3749	Approved
0.7189	Intermediate Similarity	NPD6559	Discontinued
0.7175	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD6280	Approved
0.7159	Intermediate Similarity	NPD6279	Approved
0.7151	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6599	Discontinued
0.7127	Intermediate Similarity	NPD6808	Phase 2
0.7127	Intermediate Similarity	NPD6232	Discontinued
0.712	Intermediate Similarity	NPD5844	Phase 1
0.711	Intermediate Similarity	NPD6273	Approved
0.7105	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD7473	Discontinued
0.7086	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD2313	Discontinued
0.7052	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD2799	Discontinued
0.7	Intermediate Similarity	NPD3972	Approved
0.6989	Remote Similarity	NPD7458	Discontinued
0.6983	Remote Similarity	NPD2296	Approved
0.6983	Remote Similarity	NPD5402	Approved
0.6982	Remote Similarity	NPD2935	Discontinued
0.6966	Remote Similarity	NPD6801	Discontinued
0.6959	Remote Similarity	NPD2800	Approved
0.6954	Remote Similarity	NPD6782	Approved
0.6954	Remote Similarity	NPD6780	Approved
0.6954	Remote Similarity	NPD6777	Approved
0.6954	Remote Similarity	NPD6781	Approved
0.6954	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6779	Approved
0.6954	Remote Similarity	NPD6778	Approved
0.6954	Remote Similarity	NPD6776	Approved
0.6954	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD3882	Suspended
0.6937	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7435	Discontinued
0.6931	Remote Similarity	NPD8313	Approved
0.6931	Remote Similarity	NPD8312	Approved
0.6927	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD5761	Phase 2
0.6927	Remote Similarity	NPD5760	Phase 2
0.6915	Remote Similarity	NPD6765	Approved
0.6915	Remote Similarity	NPD6764	Approved
0.6906	Remote Similarity	NPD7075	Discontinued
0.69	Remote Similarity	NPD7870	Phase 2
0.69	Remote Similarity	NPD7871	Phase 2
0.6897	Remote Similarity	NPD7390	Discontinued
0.6889	Remote Similarity	NPD3817	Phase 2
0.6882	Remote Similarity	NPD2796	Approved
0.6882	Remote Similarity	NPD3751	Discontinued
0.6882	Remote Similarity	NPD7177	Discontinued
0.6865	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD6166	Phase 2
0.6865	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.686	Remote Similarity	NPD1243	Approved
0.6857	Remote Similarity	NPD2533	Approved
0.6857	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD2532	Approved
0.6857	Remote Similarity	NPD2534	Approved
0.6851	Remote Similarity	NPD7768	Phase 2
0.685	Remote Similarity	NPD7696	Phase 3
0.685	Remote Similarity	NPD7697	Approved
0.685	Remote Similarity	NPD7698	Approved
0.6833	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.681	Remote Similarity	NPD1876	Approved
0.68	Remote Similarity	NPD6799	Approved
0.6778	Remote Similarity	NPD6844	Discontinued
0.6768	Remote Similarity	NPD1470	Approved
0.676	Remote Similarity	NPD4380	Phase 2
0.6757	Remote Similarity	NPD3787	Discontinued
0.6757	Remote Similarity	NPD7229	Phase 3
0.675	Remote Similarity	NPD1651	Approved
0.6747	Remote Similarity	NPD6832	Phase 2
0.6746	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.674	Remote Similarity	NPD2801	Approved
0.6732	Remote Similarity	NPD7874	Approved
0.6732	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD1611	Approved
0.6727	Remote Similarity	NPD2798	Approved
0.6724	Remote Similarity	NPD4628	Phase 3
0.6716	Remote Similarity	NPD7701	Phase 2
0.6708	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD1549	Phase 2
0.6701	Remote Similarity	NPD6535	Approved
0.6701	Remote Similarity	NPD6534	Approved
0.6686	Remote Similarity	NPD5408	Approved
0.6686	Remote Similarity	NPD5404	Approved
0.6686	Remote Similarity	NPD5405	Approved
0.6686	Remote Similarity	NPD5406	Approved
0.6686	Remote Similarity	NPD2979	Phase 3
0.6685	Remote Similarity	NPD1934	Approved
0.6684	Remote Similarity	NPD6784	Approved
0.6684	Remote Similarity	NPD6785	Approved
0.6667	Remote Similarity	NPD5401	Approved
0.6667	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.665	Remote Similarity	NPD8285	Discontinued
0.6649	Remote Similarity	NPD8150	Discontinued
0.6647	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD1512	Approved
0.6628	Remote Similarity	NPD3748	Approved
0.6628	Remote Similarity	NPD1510	Phase 2
0.6627	Remote Similarity	NPD8032	Phase 2
0.6626	Remote Similarity	NPD1281	Approved
0.6618	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD7801	Approved
0.6615	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD3818	Discontinued
0.6608	Remote Similarity	NPD1607	Approved
0.6606	Remote Similarity	NPD1283	Approved
0.66	Remote Similarity	NPD7700	Phase 2
0.66	Remote Similarity	NPD7699	Phase 2
0.6592	Remote Similarity	NPD5403	Approved
0.659	Remote Similarity	NPD2531	Phase 2
0.659	Remote Similarity	NPD1551	Phase 2
0.6576	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD6798	Discontinued
0.6566	Remote Similarity	NPD3267	Approved
0.6566	Remote Similarity	NPD3266	Approved
0.6564	Remote Similarity	NPD3023	Approved
0.6564	Remote Similarity	NPD3026	Approved
0.6541	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD5890	Approved
0.6538	Remote Similarity	NPD5889	Approved
0.6534	Remote Similarity	NPD3750	Approved
0.6529	Remote Similarity	NPD6233	Phase 2
0.6524	Remote Similarity	NPD1201	Approved
0.6524	Remote Similarity	NPD8127	Discontinued
0.6517	Remote Similarity	NPD1511	Approved
0.6513	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.651	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.651	Remote Similarity	NPD6797	Phase 2
0.651	Remote Similarity	NPD5953	Discontinued
0.6495	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD2438	Suspended
0.6491	Remote Similarity	NPD1240	Approved
0.6491	Remote Similarity	NPD4307	Phase 2
0.6491	Remote Similarity	NPD4060	Phase 1
0.6489	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.6482	Remote Similarity	NPD6212	Phase 3
0.6482	Remote Similarity	NPD6213	Phase 3
0.6482	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD7251	Discontinued
0.6471	Remote Similarity	NPD3764	Approved
0.6471	Remote Similarity	NPD6823	Phase 2
0.6471	Remote Similarity	NPD3268	Approved
0.6467	Remote Similarity	NPD1465	Phase 2
0.6464	Remote Similarity	NPD7239	Suspended
0.6461	Remote Similarity	NPD7236	Approved
0.6459	Remote Similarity	NPD7783	Phase 2
0.6459	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD4107	Approved
0.6453	Remote Similarity	NPD6355	Discontinued
0.6443	Remote Similarity	NPD7808	Phase 3
0.6442	Remote Similarity	NPD3025	Approved
0.6442	Remote Similarity	NPD3024	Approved
0.6442	Remote Similarity	NPD5691	Approved
0.6442	Remote Similarity	NPD8151	Discontinued
0.644	Remote Similarity	NPD2163	Approved
0.6437	Remote Similarity	NPD4308	Phase 3
0.6432	Remote Similarity	NPD3269	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD2403	Approved
0.6421	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.642	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD7907	Approved
0.6414	Remote Similarity	NPD4287	Approved
0.6412	Remote Similarity	NPD7008	Discontinued
0.6412	Remote Similarity	NPD7095	Approved
0.6412	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD8320	Phase 1
0.6408	Remote Similarity	NPD8319	Approved
0.6407	Remote Similarity	NPD6696	Suspended

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