NPASS Compound

Structure

NPC112816 OpenBabel07101719132D 24 26 0 0 1 0 0 0 0 0999 V2000 0.9659 0.2588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 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 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 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 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 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 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 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 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1305 -0.9914 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 24 1 0 0 0 0 3 6 1 0 0 0 0 3 7 2 0 0 0 0 4 5 1 0 0 0 0 4 16 1 0 0 0 0 5 8 1 0 0 0 0 5 11 2 0 0 0 0 6 9 1 0 0 0 0 6 17 2 0 0 0 0 7 12 1 0 0 0 0 7 24 1 0 0 0 0 8 13 2 0 0 0 0 8 14 1 0 0 0 0 9 10 2 0 0 0 0 9 13 1 0 0 0 0 10 11 1 0 0 0 0 10 12 1 0 0 0 0 11 18 1 0 0 0 0 12 19 2 0 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 14 21 1 6 0 0 0 15 16 1 1 0 0 0 15 22 1 0 0 0 0 16 1 1 6 0 0 0 16 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	336.08
Volume:	314.126
LogP:	0.882
LogD:	0.421
LogS:	-2.896
# Rotatable Bonds:	1
TPSA:	147.68
# H-Bond Aceptor:	8
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.414
Synthetic Accessibility Score:	3.972
Fsp3:	0.312
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.929
MDCK Permeability:	3.863473466481082e-06
Pgp-inhibitor:	0.007
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.295
20% Bioavailability (F20%):	0.448
30% Bioavailability (F30%):	0.119

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017
Plasma Protein Binding (PPB):	94.02244567871094%
Volume Distribution (VD):	0.835
Pgp-substrate:	12.244950294494629%

ADMET: Metabolism

CYP1A2-inhibitor:	0.087
CYP1A2-substrate:	0.61
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.026
CYP2C9-substrate:	0.383
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.17
CYP3A4-inhibitor:	0.041
CYP3A4-substrate:	0.12

ADMET: Excretion

Clearance (CL):	9.266
Half-life (T1/2):	0.866

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.199
Drug-inuced Liver Injury (DILI):	0.814
AMES Toxicity:	0.531
Rat Oral Acute Toxicity:	0.027
Maximum Recommended Daily Dose:	0.633
Skin Sensitization:	0.683
Carcinogencity:	0.085
Eye Corrosion:	0.003
Eye Irritation:	0.298
Respiratory Toxicity:	0.242

Download Data

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

Natural Product: NPC112816

Natural Product ID:	NPC112816
*Common Name:**	Bostrycin
IUPAC Name:	(5S,6R,7S)-5,6,7,9,10-pentahydroxy-2-methoxy-7-methyl-6,8-dihydro-5H-anthracene-1,4-dione
Synonyms:	Bostrycin
Standard InCHIKey:	ZQNOLGRKZRDRQO-XHSDSOJGSA-N
Standard InCHI:	InChI=1S/C16H16O8/c1-16(23)4-5-8(14(21)15(16)22)13(20)9-6(17)3-7(24-2)12(19)10(9)11(5)18/h3,14-15,18,20-23H,4H2,1-2H3/t14-,15+,16-/m0/s1
SMILES:	C[C@@]1(Cc2c(c(c3C(=O)C=C(C(=O)c3c2O)OC)O)[C@@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1224807
PubChem CID:	10042612
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones

*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
NPO32910	fusarium spp. psu-f135	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20815366]
NPO33050	nigrospora sp.	Species	Trichosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22545792]

☑ 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
MIC	9
Others	1

Activity Type	# Activity
Cell Line	4
Organism	10
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	900.0	nM	PMID[485832]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	2700.0	nM	PMID[485832]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	4200.0	nM	PMID[485832]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	4780.0	nM	PMID[485834]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	9800.0	nM	PMID[485832]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	3120.0	nM	PMID[485833]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	3120.0	nM	PMID[485833]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	100000.0	nM	PMID[485833]
NPT5776	Organism	Streptomyces albus	Streptomyces albus	MIC	=	3120.0	nM	PMID[485833]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	1560.0	nM	PMID[485833]
NPT3146	Organism	Micrococcus	Micrococcus	MIC	=	3120.0	nM	PMID[485833]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	1560.0	nM	PMID[485833]
NPT1311	Organism	Listonella anguillarum	Listonella anguillarum	MIC	=	390.0	nM	PMID[485833]
NPT565	Organism	Vibrio parahaemolyticus	Vibrio parahaemolyticus	MIC	=	3120.0	nM	PMID[485833]
NPT22768	SINGLE PROTEIN	Phosphotyrosine protein phosphatase	Mycobacterium tuberculosis	Inhibition	=	37.0	%	PMID[485835]

☑ 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 NPC112816 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	376
0.1-0.2	1425
0.2-0.3	3413
0.3-0.4	8643
0.4-0.5	10734
0.5-0.6	5863
0.6-0.7	6993
0.7-0.8	5006
0.8-0.85	213
0.85-0.9	24
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9658	High Similarity	NPC312482
0.9645	High Similarity	NPC143898
0.9444	High Similarity	NPC136878
0.9315	High Similarity	NPC470479
0.9306	High Similarity	NPC29932
0.8865	High Similarity	NPC88864
0.8725	High Similarity	NPC474630
0.8718	High Similarity	NPC284495
0.8707	High Similarity	NPC283292
0.8701	High Similarity	NPC314257
0.8671	High Similarity	NPC193169
0.8658	High Similarity	NPC475813
0.8636	High Similarity	NPC474824
0.8636	High Similarity	NPC470408
0.8636	High Similarity	NPC182921
0.8636	High Similarity	NPC218870
0.8618	High Similarity	NPC44378
0.8618	High Similarity	NPC280753
0.8616	High Similarity	NPC472049
0.8591	High Similarity	NPC469885
0.858	High Similarity	NPC473113
0.8571	High Similarity	NPC473096
0.8571	High Similarity	NPC473095
0.8533	High Similarity	NPC244691
0.8533	High Similarity	NPC471906
0.8526	High Similarity	NPC474861
0.8519	High Similarity	NPC470580
0.8516	High Similarity	NPC155686
0.8516	High Similarity	NPC472211
0.8516	High Similarity	NPC471695
0.8509	High Similarity	NPC473094
0.8506	High Similarity	NPC205918
0.85	High Similarity	NPC329647
0.85	High Similarity	NPC470735
0.8493	Intermediate Similarity	NPC315275
0.8476	Intermediate Similarity	NPC470583
0.8476	Intermediate Similarity	NPC19056
0.8466	Intermediate Similarity	NPC270027
0.8462	Intermediate Similarity	NPC68727
0.8452	Intermediate Similarity	NPC470340
0.844	Intermediate Similarity	NPC472047
0.8431	Intermediate Similarity	NPC94781
0.8421	Intermediate Similarity	NPC285122
0.8408	Intermediate Similarity	NPC478027
0.84	Intermediate Similarity	NPC135524
0.8387	Intermediate Similarity	NPC46882
0.8387	Intermediate Similarity	NPC132990
0.8385	Intermediate Similarity	NPC472057
0.8385	Intermediate Similarity	NPC472051
0.8378	Intermediate Similarity	NPC173980
0.8377	Intermediate Similarity	NPC120171
0.8373	Intermediate Similarity	NPC266513
0.8373	Intermediate Similarity	NPC115447
0.8373	Intermediate Similarity	NPC470581
0.8373	Intermediate Similarity	NPC470582
0.8354	Intermediate Similarity	NPC472889
0.8345	Intermediate Similarity	NPC309430
0.8333	Intermediate Similarity	NPC204045
0.8333	Intermediate Similarity	NPC110810
0.8333	Intermediate Similarity	NPC470337
0.8333	Intermediate Similarity	NPC113608
0.8333	Intermediate Similarity	NPC470338
0.8333	Intermediate Similarity	NPC268992
0.8333	Intermediate Similarity	NPC51824
0.8333	Intermediate Similarity	NPC305845
0.8333	Intermediate Similarity	NPC180944
0.8323	Intermediate Similarity	NPC187441
0.8323	Intermediate Similarity	NPC283980
0.8323	Intermediate Similarity	NPC280295
0.8322	Intermediate Similarity	NPC114620
0.8322	Intermediate Similarity	NPC103337
0.8313	Intermediate Similarity	NPC117985
0.8313	Intermediate Similarity	NPC87431
0.8313	Intermediate Similarity	NPC318081
0.8313	Intermediate Similarity	NPC316457
0.8302	Intermediate Similarity	NPC477410
0.8299	Intermediate Similarity	NPC14377
0.8293	Intermediate Similarity	NPC313717
0.8293	Intermediate Similarity	NPC315306
0.8289	Intermediate Similarity	NPC79627
0.8289	Intermediate Similarity	NPC477409
0.8288	Intermediate Similarity	NPC254603
0.8282	Intermediate Similarity	NPC324522
0.8282	Intermediate Similarity	NPC470341
0.8282	Intermediate Similarity	NPC472058
0.8282	Intermediate Similarity	NPC105414
0.8282	Intermediate Similarity	NPC234497
0.8278	Intermediate Similarity	NPC474961
0.8272	Intermediate Similarity	NPC146584
0.8272	Intermediate Similarity	NPC21016
0.8269	Intermediate Similarity	NPC470569
0.8263	Intermediate Similarity	NPC83331
0.8261	Intermediate Similarity	NPC472059
0.8255	Intermediate Similarity	NPC123714
0.825	Intermediate Similarity	NPC155302
0.825	Intermediate Similarity	NPC161947
0.8247	Intermediate Similarity	NPC476821
0.8243	Intermediate Similarity	NPC474311
0.8242	Intermediate Similarity	NPC294501
0.8239	Intermediate Similarity	NPC474637
0.8235	Intermediate Similarity	NPC170055
0.8235	Intermediate Similarity	NPC34482
0.8235	Intermediate Similarity	NPC28632
0.8228	Intermediate Similarity	NPC478221
0.8228	Intermediate Similarity	NPC326910
0.8219	Intermediate Similarity	NPC110609
0.8219	Intermediate Similarity	NPC246693
0.8219	Intermediate Similarity	NPC17843
0.8219	Intermediate Similarity	NPC242358
0.8217	Intermediate Similarity	NPC478220
0.8212	Intermediate Similarity	NPC92079
0.821	Intermediate Similarity	NPC208120
0.821	Intermediate Similarity	NPC472053
0.821	Intermediate Similarity	NPC173587
0.8207	Intermediate Similarity	NPC198305
0.8205	Intermediate Similarity	NPC294646
0.8205	Intermediate Similarity	NPC315520
0.8205	Intermediate Similarity	NPC470568
0.8205	Intermediate Similarity	NPC225854
0.8205	Intermediate Similarity	NPC147735
0.82	Intermediate Similarity	NPC190457
0.82	Intermediate Similarity	NPC143438
0.8199	Intermediate Similarity	NPC269117
0.8193	Intermediate Similarity	NPC154986
0.8188	Intermediate Similarity	NPC305060
0.8182	Intermediate Similarity	NPC478021
0.8182	Intermediate Similarity	NPC470570
0.8182	Intermediate Similarity	NPC300540
0.8171	Intermediate Similarity	NPC107009
0.817	Intermediate Similarity	NPC48130
0.817	Intermediate Similarity	NPC300684
0.817	Intermediate Similarity	NPC48762
0.817	Intermediate Similarity	NPC218866
0.817	Intermediate Similarity	NPC84568
0.8166	Intermediate Similarity	NPC208069
0.8165	Intermediate Similarity	NPC137301
0.8165	Intermediate Similarity	NPC478231
0.816	Intermediate Similarity	NPC478020
0.816	Intermediate Similarity	NPC314653
0.816	Intermediate Similarity	NPC316262
0.816	Intermediate Similarity	NPC478022
0.8158	Intermediate Similarity	NPC291078
0.8158	Intermediate Similarity	NPC308572
0.8158	Intermediate Similarity	NPC248068
0.8144	Intermediate Similarity	NPC245975
0.8141	Intermediate Similarity	NPC474310
0.8138	Intermediate Similarity	NPC278928
0.8137	Intermediate Similarity	NPC84571
0.8137	Intermediate Similarity	NPC313368
0.8137	Intermediate Similarity	NPC472055
0.8125	Intermediate Similarity	NPC246466
0.8121	Intermediate Similarity	NPC213416
0.8117	Intermediate Similarity	NPC471683
0.8113	Intermediate Similarity	NPC471456
0.8113	Intermediate Similarity	NPC472890
0.8113	Intermediate Similarity	NPC317585
0.8113	Intermediate Similarity	NPC478230
0.8113	Intermediate Similarity	NPC208173
0.8113	Intermediate Similarity	NPC478133
0.8113	Intermediate Similarity	NPC69043
0.8113	Intermediate Similarity	NPC170189
0.8113	Intermediate Similarity	NPC175192
0.811	Intermediate Similarity	NPC20237
0.8101	Intermediate Similarity	NPC478224
0.8101	Intermediate Similarity	NPC321363
0.8101	Intermediate Similarity	NPC115249
0.8101	Intermediate Similarity	NPC253904
0.8098	Intermediate Similarity	NPC475055
0.8098	Intermediate Similarity	NPC476822
0.8098	Intermediate Similarity	NPC101769
0.8092	Intermediate Similarity	NPC187843
0.8092	Intermediate Similarity	NPC314672
0.8092	Intermediate Similarity	NPC257003
0.8089	Intermediate Similarity	NPC255641
0.8089	Intermediate Similarity	NPC290954
0.8086	Intermediate Similarity	NPC478222
0.8086	Intermediate Similarity	NPC478134
0.8086	Intermediate Similarity	NPC311740
0.8084	Intermediate Similarity	NPC469393
0.8079	Intermediate Similarity	NPC138099
0.8079	Intermediate Similarity	NPC242994
0.8077	Intermediate Similarity	NPC470359
0.8075	Intermediate Similarity	NPC470339
0.8075	Intermediate Similarity	NPC324736
0.8067	Intermediate Similarity	NPC471905
0.8065	Intermediate Similarity	NPC63918
0.8063	Intermediate Similarity	NPC472050
0.8063	Intermediate Similarity	NPC164427
0.8063	Intermediate Similarity	NPC478223
0.8061	Intermediate Similarity	NPC283041
0.8061	Intermediate Similarity	NPC232936
0.8061	Intermediate Similarity	NPC158761
0.8059	Intermediate Similarity	NPC315221
0.8052	Intermediate Similarity	NPC103910
0.8052	Intermediate Similarity	NPC21599
0.8052	Intermediate Similarity	NPC193703
0.805	Intermediate Similarity	NPC273248
0.805	Intermediate Similarity	NPC93552
0.805	Intermediate Similarity	NPC107109
0.805	Intermediate Similarity	NPC478218

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 NPC112816 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	331
0.1-0.2	1002
0.2-0.3	2039
0.3-0.4	2904
0.4-0.5	1779
0.5-0.6	764
0.6-0.7	247
0.7-0.8	83
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
0.8081	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD8150	Discontinued
0.7784	Intermediate Similarity	NPD6535	Approved
0.7784	Intermediate Similarity	NPD6534	Approved
0.7771	Intermediate Similarity	NPD2533	Approved
0.7771	Intermediate Similarity	NPD2534	Approved
0.7771	Intermediate Similarity	NPD2532	Approved
0.7711	Intermediate Similarity	NPD6232	Discontinued
0.7707	Intermediate Similarity	NPD7390	Discontinued
0.7679	Intermediate Similarity	NPD7473	Discontinued
0.7667	Intermediate Similarity	NPD6776	Approved
0.7667	Intermediate Similarity	NPD6780	Approved
0.7667	Intermediate Similarity	NPD6782	Approved
0.7667	Intermediate Similarity	NPD6781	Approved
0.7667	Intermediate Similarity	NPD6777	Approved
0.7667	Intermediate Similarity	NPD6778	Approved
0.7667	Intermediate Similarity	NPD6779	Approved
0.7658	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD7699	Phase 2
0.7654	Intermediate Similarity	NPD7700	Phase 2
0.7651	Intermediate Similarity	NPD6959	Discontinued
0.764	Intermediate Similarity	NPD4380	Phase 2
0.7637	Intermediate Similarity	NPD7435	Discontinued
0.7607	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD7075	Discontinued
0.7546	Intermediate Similarity	NPD6801	Discontinued
0.7532	Intermediate Similarity	NPD3300	Phase 2
0.7532	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1470	Approved
0.7455	Intermediate Similarity	NPD5402	Approved
0.7446	Intermediate Similarity	NPD7696	Phase 3
0.7446	Intermediate Similarity	NPD7697	Approved
0.7446	Intermediate Similarity	NPD7698	Approved
0.7438	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD3751	Discontinued
0.7412	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD6166	Phase 2
0.7412	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD3882	Suspended
0.7405	Intermediate Similarity	NPD7871	Phase 2
0.7405	Intermediate Similarity	NPD7870	Phase 2
0.7394	Intermediate Similarity	NPD2801	Approved
0.7394	Intermediate Similarity	NPD7874	Approved
0.7394	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7819	Suspended
0.7386	Intermediate Similarity	NPD943	Approved
0.7384	Intermediate Similarity	NPD5844	Phase 1
0.738	Intermediate Similarity	NPD7701	Phase 2
0.7372	Intermediate Similarity	NPD5406	Approved
0.7372	Intermediate Similarity	NPD5405	Approved
0.7372	Intermediate Similarity	NPD5408	Approved
0.7372	Intermediate Similarity	NPD5404	Approved
0.7362	Intermediate Similarity	NPD3226	Approved
0.736	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6190	Approved
0.7345	Intermediate Similarity	NPD8434	Phase 2
0.7342	Intermediate Similarity	NPD2800	Approved
0.7333	Intermediate Similarity	NPD1934	Approved
0.7314	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD8320	Phase 1
0.7312	Intermediate Similarity	NPD8319	Approved
0.729	Intermediate Similarity	NPD6651	Approved
0.7283	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD5494	Approved
0.7263	Intermediate Similarity	NPD7801	Approved
0.7261	Intermediate Similarity	NPD2935	Discontinued
0.7246	Intermediate Similarity	NPD3817	Phase 2
0.7238	Intermediate Similarity	NPD6213	Phase 3
0.7238	Intermediate Similarity	NPD6212	Phase 3
0.7238	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD1201	Approved
0.7225	Intermediate Similarity	NPD3818	Discontinued
0.7222	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD4955	Approved
0.7216	Intermediate Similarity	NPD5028	Approved
0.7216	Intermediate Similarity	NPD4954	Approved
0.7216	Intermediate Similarity	NPD36	Approved
0.7216	Intermediate Similarity	NPD5034	Approved
0.7216	Intermediate Similarity	NPD5026	Approved
0.7212	Intermediate Similarity	NPD6599	Discontinued
0.72	Intermediate Similarity	NPD6797	Phase 2
0.7197	Intermediate Similarity	NPD1510	Phase 2
0.7193	Intermediate Similarity	NPD5710	Approved
0.7193	Intermediate Similarity	NPD5711	Approved
0.7181	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1607	Approved
0.7178	Intermediate Similarity	NPD1512	Approved
0.716	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD6559	Discontinued
0.7159	Intermediate Similarity	NPD7251	Discontinued
0.7159	Intermediate Similarity	NPD5030	Phase 2
0.7151	Intermediate Similarity	NPD5037	Approved
0.7151	Intermediate Similarity	NPD5038	Approved
0.7143	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD7808	Phase 3
0.7112	Intermediate Similarity	NPD6823	Phase 2
0.7107	Intermediate Similarity	NPD2346	Discontinued
0.7101	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD5036	Approved
0.7093	Intermediate Similarity	NPD3787	Discontinued
0.7079	Intermediate Similarity	NPD8312	Approved
0.7079	Intermediate Similarity	NPD8313	Approved
0.7079	Intermediate Similarity	NPD5035	Approved
0.7063	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1549	Phase 2
0.7055	Intermediate Similarity	NPD6799	Approved
0.7055	Intermediate Similarity	NPD1511	Approved
0.7055	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD1240	Approved
0.7045	Intermediate Similarity	NPD7074	Phase 3
0.703	Intermediate Similarity	NPD5403	Approved
0.702	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7054	Approved
0.6979	Remote Similarity	NPD8151	Discontinued
0.6964	Remote Similarity	NPD7411	Suspended
0.6949	Remote Similarity	NPD7472	Approved
0.6937	Remote Similarity	NPD2796	Approved
0.6936	Remote Similarity	NPD1247	Approved
0.6923	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD5401	Approved
0.6899	Remote Similarity	NPD230	Phase 1
0.6882	Remote Similarity	NPD1465	Phase 2
0.6875	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD8368	Discontinued
0.6872	Remote Similarity	NPD5029	Approved
0.6872	Remote Similarity	NPD5031	Approved
0.6872	Remote Similarity	NPD5027	Approved
0.6871	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD4628	Phase 3
0.6832	Remote Similarity	NPD6099	Approved
0.6832	Remote Similarity	NPD6100	Approved
0.6824	Remote Similarity	NPD37	Approved
0.6818	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD3750	Approved
0.6763	Remote Similarity	NPD3749	Approved
0.6761	Remote Similarity	NPD3926	Phase 2
0.6758	Remote Similarity	NPD8407	Phase 2
0.6746	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.674	Remote Similarity	NPD5032	Approved
0.6735	Remote Similarity	NPD7783	Phase 2
0.6735	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD6234	Discontinued
0.6707	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD4965	Approved
0.6705	Remote Similarity	NPD4967	Phase 2
0.6705	Remote Similarity	NPD7768	Phase 2
0.6705	Remote Similarity	NPD4966	Approved
0.6689	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7236	Approved
0.6687	Remote Similarity	NPD1471	Phase 3
0.6686	Remote Similarity	NPD7239	Suspended
0.6685	Remote Similarity	NPD5039	Approved
0.6649	Remote Similarity	NPD4914	Approved
0.6648	Remote Similarity	NPD7799	Discontinued
0.6644	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6631	Remote Similarity	NPD5968	Phase 3
0.663	Remote Similarity	NPD5953	Discontinued
0.6629	Remote Similarity	NPD919	Approved
0.6626	Remote Similarity	NPD1551	Phase 2
0.6623	Remote Similarity	NPD9269	Phase 2
0.6613	Remote Similarity	NPD6836	Approved
0.6613	Remote Similarity	NPD8360	Approved
0.6613	Remote Similarity	NPD8435	Approved
0.6613	Remote Similarity	NPD8361	Approved
0.6604	Remote Similarity	NPD2313	Discontinued
0.6604	Remote Similarity	NPD7985	Registered
0.6604	Remote Similarity	NPD3764	Approved
0.6603	Remote Similarity	NPD1164	Approved
0.6602	Remote Similarity	NPD8059	Phase 3
0.6602	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD8366	Approved
0.659	Remote Similarity	NPD5761	Phase 2
0.659	Remote Similarity	NPD5760	Phase 2
0.6585	Remote Similarity	NPD2344	Approved
0.658	Remote Similarity	NPD4387	Approved
0.658	Remote Similarity	NPD4386	Approved
0.6579	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD4956	Approved
0.6566	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD8166	Discontinued
0.6564	Remote Similarity	NPD2799	Discontinued
0.6562	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD7228	Approved
0.655	Remote Similarity	NPD7458	Discontinued
0.6536	Remote Similarity	NPD2932	Approved
0.6536	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD2403	Approved
0.6529	Remote Similarity	NPD920	Approved
0.652	Remote Similarity	NPD7907	Approved
0.6519	Remote Similarity	NPD7286	Phase 2
0.651	Remote Similarity	NPD5544	Approved
0.651	Remote Similarity	NPD8285	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data