NPASS Compound

Structure

NPC143898 OpenBabel07101719122D 23 25 0 0 1 0 0 0 0 0999 V2000 4.5889 0.4659 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 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 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 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 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 4.3301 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1235 -1.1088 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 23 1 0 0 0 0 3 6 1 0 0 0 0 3 10 1 0 0 0 0 4 8 1 0 0 0 0 4 9 2 0 0 0 0 5 7 1 0 0 0 0 5 16 1 0 0 0 0 6 7 1 0 0 0 0 6 13 2 0 0 0 0 7 14 2 0 0 0 0 8 11 1 0 0 0 0 8 17 2 0 0 0 0 9 15 1 0 0 0 0 9 23 1 0 0 0 0 10 16 1 6 0 0 0 10 18 1 0 0 0 0 11 12 2 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 12 15 1 0 0 0 0 13 19 1 0 0 0 0 14 20 1 0 0 0 0 15 21 2 0 0 0 0 16 1 1 1 0 0 0 16 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	320.09
Volume:	305.336
LogP:	2.027
LogD:	1.066
LogS:	-2.543
# Rotatable Bonds:	1
TPSA:	127.45
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.498
Synthetic Accessibility Score:	3.7
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:	-5.43
MDCK Permeability:	5.451140623335959e-06
Pgp-inhibitor:	0.037
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.077
20% Bioavailability (F20%):	0.475
30% Bioavailability (F30%):	0.072

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	94.0284194946289%
Volume Distribution (VD):	0.73
Pgp-substrate:	12.017483711242676%

ADMET: Metabolism

CYP1A2-inhibitor:	0.312
CYP1A2-substrate:	0.923
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.071
CYP2C9-inhibitor:	0.12
CYP2C9-substrate:	0.551
CYP2D6-inhibitor:	0.025
CYP2D6-substrate:	0.182
CYP3A4-inhibitor:	0.101
CYP3A4-substrate:	0.194

ADMET: Excretion

Clearance (CL):	16.443
Half-life (T1/2):	0.911

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.231
Drug-inuced Liver Injury (DILI):	0.697
AMES Toxicity:	0.504
Rat Oral Acute Toxicity:	0.024
Maximum Recommended Daily Dose:	0.026
Skin Sensitization:	0.9
Carcinogencity:	0.03
Eye Corrosion:	0.004
Eye Irritation:	0.572
Respiratory Toxicity:	0.209

Download Data

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

Natural Product: NPC143898

Natural Product ID:	NPC143898
*Common Name:**	4-Deoxybostrycin
IUPAC Name:	(6R,7S)-6,7,9,10-tetrahydroxy-2-methoxy-7-methyl-6,8-dihydro-5H-anthracene-1,4-dione
Synonyms:	4-Deoxybostrycin
Standard InCHIKey:	NCLWGURXHFTQGF-HWPZZCPQSA-N
Standard InCHI:	InChI=1S/C16H16O7/c1-16(22)5-7-6(3-10(16)18)13(19)11-8(17)4-9(23-2)15(21)12(11)14(7)20/h4,10,18-20,22H,3,5H2,1-2H3/t10-,16+/m1/s1
SMILES:	COC1=CC(=O)c2c(C1=O)c(O)c1c(c2O)C[C@H]([C@@](C1)(C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2047316
PubChem CID:	193579
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
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	2
MIC	9
Others	1

Activity Type	# Activity
Cell Line	2
Organism	9
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	9990.0	nM	PMID[524091]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	2690.0	nM	PMID[524091]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	3120.0	nM	PMID[524090]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	3120.0	nM	PMID[524090]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	200000.0	nM	PMID[524090]
NPT5776	Organism	Streptomyces albus	Streptomyces albus	MIC	=	3120.0	nM	PMID[524090]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	3120.0	nM	PMID[524090]
NPT3146	Organism	Micrococcus	Micrococcus	MIC	=	3120.0	nM	PMID[524090]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	1560.0	nM	PMID[524090]
NPT1311	Organism	Listonella anguillarum	Listonella anguillarum	MIC	=	3120.0	nM	PMID[524090]
NPT565	Organism	Vibrio parahaemolyticus	Vibrio parahaemolyticus	MIC	=	3120.0	nM	PMID[524090]
NPT22768	SINGLE PROTEIN	Phosphotyrosine protein phosphatase	Mycobacterium tuberculosis	Inhibition	=	17.5	%	PMID[524092]

☑ 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 NPC143898 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	361
0.1-0.2	1364
0.2-0.3	3247
0.3-0.4	8434
0.4-0.5	11126
0.5-0.6	6122
0.6-0.7	8260
0.7-0.8	3602
0.8-0.85	157
0.85-0.9	16
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9645	High Similarity	NPC112816
0.964	High Similarity	NPC29932
0.9507	High Similarity	NPC470479
0.9366	High Similarity	NPC136878
0.9315	High Similarity	NPC312482
0.9051	High Similarity	NPC88864
0.8986	High Similarity	NPC193169
0.875	High Similarity	NPC283292
0.8643	High Similarity	NPC309430
0.8639	High Similarity	NPC474630
0.863	High Similarity	NPC469885
0.8582	High Similarity	NPC254603
0.8571	High Similarity	NPC477409
0.8571	High Similarity	NPC475813
0.8533	High Similarity	NPC280753
0.8533	High Similarity	NPC44378
0.8531	High Similarity	NPC315275
0.8511	High Similarity	NPC242358
0.8511	High Similarity	NPC246693
0.8511	High Similarity	NPC110609
0.85	High Similarity	NPC198305
0.8483	Intermediate Similarity	NPC114620
0.8483	Intermediate Similarity	NPC103337
0.8472	Intermediate Similarity	NPC305060
0.8467	Intermediate Similarity	NPC94781
0.8446	Intermediate Similarity	NPC79627
0.8429	Intermediate Similarity	NPC278928
0.8421	Intermediate Similarity	NPC205918
0.8414	Intermediate Similarity	NPC173980
0.8411	Intermediate Similarity	NPC120171
0.8403	Intermediate Similarity	NPC474311
0.84	Intermediate Similarity	NPC476821
0.8397	Intermediate Similarity	NPC284495
0.8377	Intermediate Similarity	NPC314257
0.8345	Intermediate Similarity	NPC472047
0.8344	Intermediate Similarity	NPC318081
0.8333	Intermediate Similarity	NPC285122
0.8322	Intermediate Similarity	NPC244691
0.8322	Intermediate Similarity	NPC471906
0.8312	Intermediate Similarity	NPC182921
0.8312	Intermediate Similarity	NPC474824
0.8312	Intermediate Similarity	NPC218870
0.8312	Intermediate Similarity	NPC470408
0.8311	Intermediate Similarity	NPC308572
0.8311	Intermediate Similarity	NPC474300
0.8311	Intermediate Similarity	NPC248068
0.8302	Intermediate Similarity	NPC472049
0.8302	Intermediate Similarity	NPC470735
0.8302	Intermediate Similarity	NPC329647
0.8289	Intermediate Similarity	NPC474310
0.8272	Intermediate Similarity	NPC473113
0.8267	Intermediate Similarity	NPC474309
0.8261	Intermediate Similarity	NPC473095
0.8261	Intermediate Similarity	NPC473096
0.8255	Intermediate Similarity	NPC476473
0.8252	Intermediate Similarity	NPC70622
0.8247	Intermediate Similarity	NPC470340
0.8243	Intermediate Similarity	NPC257003
0.8231	Intermediate Similarity	NPC256463
0.8231	Intermediate Similarity	NPC471602
0.8231	Intermediate Similarity	NPC306835
0.8231	Intermediate Similarity	NPC29771
0.8231	Intermediate Similarity	NPC216312
0.8231	Intermediate Similarity	NPC111422
0.8231	Intermediate Similarity	NPC477408
0.8231	Intermediate Similarity	NPC299405
0.8231	Intermediate Similarity	NPC476477
0.8227	Intermediate Similarity	NPC165257
0.8227	Intermediate Similarity	NPC237225
0.8214	Intermediate Similarity	NPC1991
0.8212	Intermediate Similarity	NPC300540
0.821	Intermediate Similarity	NPC470580
0.8205	Intermediate Similarity	NPC478223
0.8205	Intermediate Similarity	NPC474861
0.8205	Intermediate Similarity	NPC478027
0.82	Intermediate Similarity	NPC103910
0.8199	Intermediate Similarity	NPC473094
0.8194	Intermediate Similarity	NPC171968
0.8194	Intermediate Similarity	NPC471695
0.8194	Intermediate Similarity	NPC155686
0.8194	Intermediate Similarity	NPC472211
0.8194	Intermediate Similarity	NPC314048
0.8188	Intermediate Similarity	NPC135524
0.8182	Intermediate Similarity	NPC46882
0.8182	Intermediate Similarity	NPC17083
0.8182	Intermediate Similarity	NPC132990
0.8182	Intermediate Similarity	NPC205992
0.8176	Intermediate Similarity	NPC220496
0.8176	Intermediate Similarity	NPC147542
0.8176	Intermediate Similarity	NPC471853
0.8176	Intermediate Similarity	NPC241349
0.8176	Intermediate Similarity	NPC32749
0.8176	Intermediate Similarity	NPC327916
0.8176	Intermediate Similarity	NPC42262
0.8176	Intermediate Similarity	NPC37992
0.8175	Intermediate Similarity	NPC472046
0.8171	Intermediate Similarity	NPC19056
0.8171	Intermediate Similarity	NPC470583
0.817	Intermediate Similarity	NPC478219
0.8163	Intermediate Similarity	NPC230811
0.816	Intermediate Similarity	NPC270027
0.8151	Intermediate Similarity	NPC272268
0.8146	Intermediate Similarity	NPC170055
0.8146	Intermediate Similarity	NPC475923
0.8141	Intermediate Similarity	NPC326910
0.8141	Intermediate Similarity	NPC68727
0.8129	Intermediate Similarity	NPC180944
0.8129	Intermediate Similarity	NPC470338
0.8129	Intermediate Similarity	NPC470337
0.8129	Intermediate Similarity	NPC478220
0.8129	Intermediate Similarity	NPC180388
0.8129	Intermediate Similarity	NPC113608
0.8129	Intermediate Similarity	NPC268992
0.8129	Intermediate Similarity	NPC51824
0.8125	Intermediate Similarity	NPC58685
0.8125	Intermediate Similarity	NPC17843
0.8121	Intermediate Similarity	NPC204045
0.8121	Intermediate Similarity	NPC110810
0.8121	Intermediate Similarity	NPC471444
0.8121	Intermediate Similarity	NPC124365
0.8121	Intermediate Similarity	NPC305845
0.8117	Intermediate Similarity	NPC315520
0.8113	Intermediate Similarity	NPC269117
0.8113	Intermediate Similarity	NPC117985
0.8112	Intermediate Similarity	NPC199253
0.8112	Intermediate Similarity	NPC136588
0.8101	Intermediate Similarity	NPC477410
0.8099	Intermediate Similarity	NPC767
0.8099	Intermediate Similarity	NPC247250
0.8098	Intermediate Similarity	NPC313717
0.8098	Intermediate Similarity	NPC315306
0.8095	Intermediate Similarity	NPC245923
0.8095	Intermediate Similarity	NPC147418
0.8092	Intermediate Similarity	NPC63918
0.8085	Intermediate Similarity	NPC231774
0.8085	Intermediate Similarity	NPC306765
0.8085	Intermediate Similarity	NPC51037
0.8082	Intermediate Similarity	NPC14377
0.8082	Intermediate Similarity	NPC283088
0.8079	Intermediate Similarity	NPC274085
0.8079	Intermediate Similarity	NPC48130
0.8079	Intermediate Similarity	NPC84568
0.8079	Intermediate Similarity	NPC89664
0.8079	Intermediate Similarity	NPC218866
0.8079	Intermediate Similarity	NPC300684
0.8075	Intermediate Similarity	NPC21016
0.8075	Intermediate Similarity	NPC146584
0.8075	Intermediate Similarity	NPC472057
0.8075	Intermediate Similarity	NPC472051
0.8072	Intermediate Similarity	NPC266513
0.8072	Intermediate Similarity	NPC470581
0.8072	Intermediate Similarity	NPC470582
0.8072	Intermediate Similarity	NPC115447
0.8071	Intermediate Similarity	NPC68756
0.8071	Intermediate Similarity	NPC152525
0.8069	Intermediate Similarity	NPC52407
0.8067	Intermediate Similarity	NPC469520
0.8067	Intermediate Similarity	NPC474961
0.8065	Intermediate Similarity	NPC470569
0.8054	Intermediate Similarity	NPC315578
0.805	Intermediate Similarity	NPC161947
0.805	Intermediate Similarity	NPC155302
0.8041	Intermediate Similarity	NPC123714
0.8041	Intermediate Similarity	NPC61398
0.8041	Intermediate Similarity	NPC206207
0.8041	Intermediate Similarity	NPC416
0.8039	Intermediate Similarity	NPC472135
0.8038	Intermediate Similarity	NPC472889
0.8028	Intermediate Similarity	NPC471530
0.8027	Intermediate Similarity	NPC86524
0.8027	Intermediate Similarity	NPC474813
0.8027	Intermediate Similarity	NPC475549
0.8026	Intermediate Similarity	NPC34482
0.8026	Intermediate Similarity	NPC28632
0.8025	Intermediate Similarity	NPC471456
0.8025	Intermediate Similarity	NPC478133
0.8024	Intermediate Similarity	NPC283980
0.8024	Intermediate Similarity	NPC187441
0.8014	Intermediate Similarity	NPC202225
0.8013	Intermediate Similarity	NPC321363
0.8013	Intermediate Similarity	NPC253904
0.8012	Intermediate Similarity	NPC173587
0.8012	Intermediate Similarity	NPC208120
0.8	Intermediate Similarity	NPC92079
0.8	Intermediate Similarity	NPC294646
0.8	Intermediate Similarity	NPC147735
0.8	Intermediate Similarity	NPC478134
0.8	Intermediate Similarity	NPC31132
0.8	Intermediate Similarity	NPC154986
0.8	Intermediate Similarity	NPC225854
0.8	Intermediate Similarity	NPC87431
0.8	Intermediate Similarity	NPC316457
0.8	Intermediate Similarity	NPC470568
0.8	Intermediate Similarity	NPC187843
0.8	Intermediate Similarity	NPC478222
0.8	Intermediate Similarity	NPC280295
0.7987	Intermediate Similarity	NPC143438
0.7987	Intermediate Similarity	NPC142846
0.7987	Intermediate Similarity	NPC1268
0.7987	Intermediate Similarity	NPC190457

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 NPC143898 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	313
0.1-0.2	986
0.2-0.3	1933
0.3-0.4	2869
0.4-0.5	1833
0.5-0.6	881
0.6-0.7	281
0.7-0.8	54
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
0.7792	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3300	Phase 2
0.7762	Intermediate Similarity	NPD1470	Approved
0.7661	Intermediate Similarity	NPD8150	Discontinued
0.7564	Intermediate Similarity	NPD2534	Approved
0.7564	Intermediate Similarity	NPD2532	Approved
0.7564	Intermediate Similarity	NPD2533	Approved
0.75	Intermediate Similarity	NPD6535	Approved
0.75	Intermediate Similarity	NPD6534	Approved
0.7484	Intermediate Similarity	NPD3226	Approved
0.7483	Intermediate Similarity	NPD1201	Approved
0.7471	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD6232	Discontinued
0.7407	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6781	Approved
0.7389	Intermediate Similarity	NPD6778	Approved
0.7389	Intermediate Similarity	NPD7390	Discontinued
0.7389	Intermediate Similarity	NPD6779	Approved
0.7389	Intermediate Similarity	NPD6780	Approved
0.7389	Intermediate Similarity	NPD6782	Approved
0.7389	Intermediate Similarity	NPD6776	Approved
0.7389	Intermediate Similarity	NPD6777	Approved
0.7386	Intermediate Similarity	NPD5405	Approved
0.7386	Intermediate Similarity	NPD5404	Approved
0.7386	Intermediate Similarity	NPD5406	Approved
0.7386	Intermediate Similarity	NPD5408	Approved
0.7381	Intermediate Similarity	NPD7473	Discontinued
0.7374	Intermediate Similarity	NPD7700	Phase 2
0.7374	Intermediate Similarity	NPD7699	Phase 2
0.7363	Intermediate Similarity	NPD7435	Discontinued
0.7349	Intermediate Similarity	NPD6959	Discontinued
0.7338	Intermediate Similarity	NPD2346	Discontinued
0.7329	Intermediate Similarity	NPD4380	Phase 2
0.732	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2935	Discontinued
0.7273	Intermediate Similarity	NPD7075	Discontinued
0.7256	Intermediate Similarity	NPD5402	Approved
0.7239	Intermediate Similarity	NPD6801	Discontinued
0.7235	Intermediate Similarity	NPD3751	Discontinued
0.7233	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD5034	Approved
0.7225	Intermediate Similarity	NPD5028	Approved
0.7225	Intermediate Similarity	NPD5026	Approved
0.7225	Intermediate Similarity	NPD36	Approved
0.7225	Intermediate Similarity	NPD4955	Approved
0.7225	Intermediate Similarity	NPD4954	Approved
0.7212	Intermediate Similarity	NPD3882	Suspended
0.7195	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD2801	Approved
0.7193	Intermediate Similarity	NPD5844	Phase 1
0.7174	Intermediate Similarity	NPD7697	Approved
0.7174	Intermediate Similarity	NPD7698	Approved
0.7174	Intermediate Similarity	NPD7696	Phase 3
0.7171	Intermediate Similarity	NPD943	Approved
0.7168	Intermediate Similarity	NPD5030	Phase 2
0.7159	Intermediate Similarity	NPD8434	Phase 2
0.7159	Intermediate Similarity	NPD5037	Approved
0.7159	Intermediate Similarity	NPD5038	Approved
0.7152	Intermediate Similarity	NPD6190	Approved
0.7135	Intermediate Similarity	NPD7871	Phase 2
0.7135	Intermediate Similarity	NPD7870	Phase 2
0.7134	Intermediate Similarity	NPD2800	Approved
0.7134	Intermediate Similarity	NPD1934	Approved
0.7128	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7874	Approved
0.7118	Intermediate Similarity	NPD6166	Phase 2
0.7118	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD7701	Phase 2
0.7102	Intermediate Similarity	NPD5036	Approved
0.7091	Intermediate Similarity	NPD7819	Suspended
0.7086	Intermediate Similarity	NPD8312	Approved
0.7086	Intermediate Similarity	NPD8313	Approved
0.7083	Intermediate Similarity	NPD5494	Approved
0.7056	Intermediate Similarity	NPD6213	Phase 3
0.7056	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD6212	Phase 3
0.7043	Intermediate Similarity	NPD8319	Approved
0.7043	Intermediate Similarity	NPD8320	Phase 1
0.7039	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD6599	Discontinued
0.7	Intermediate Similarity	NPD5710	Approved
0.7	Intermediate Similarity	NPD5711	Approved
0.7	Intermediate Similarity	NPD7801	Approved
0.6994	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD1510	Phase 2
0.6981	Remote Similarity	NPD4628	Phase 3
0.6975	Remote Similarity	NPD1512	Approved
0.6971	Remote Similarity	NPD5031	Approved
0.6971	Remote Similarity	NPD6559	Discontinued
0.6971	Remote Similarity	NPD5029	Approved
0.6971	Remote Similarity	NPD5027	Approved
0.6968	Remote Similarity	NPD1607	Approved
0.6968	Remote Similarity	NPD6651	Approved
0.6946	Remote Similarity	NPD3817	Phase 2
0.6936	Remote Similarity	NPD3818	Discontinued
0.6935	Remote Similarity	NPD6823	Phase 2
0.6915	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6797	Phase 2
0.6914	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD3787	Discontinued
0.6893	Remote Similarity	NPD5035	Approved
0.6879	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7251	Discontinued
0.6864	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD1549	Phase 2
0.6855	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD1511	Approved
0.6852	Remote Similarity	NPD6799	Approved
0.6845	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD1240	Approved
0.6836	Remote Similarity	NPD7808	Phase 3
0.6829	Remote Similarity	NPD5403	Approved
0.6818	Remote Similarity	NPD3764	Approved
0.6818	Remote Similarity	NPD2313	Discontinued
0.6818	Remote Similarity	NPD7985	Registered
0.6816	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD1471	Phase 3
0.6772	Remote Similarity	NPD2799	Discontinued
0.677	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.677	Remote Similarity	NPD8166	Discontinued
0.6768	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD7074	Phase 3
0.6757	Remote Similarity	NPD2932	Approved
0.6757	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD1247	Approved
0.673	Remote Similarity	NPD2796	Approved
0.6725	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD5968	Phase 3
0.6719	Remote Similarity	NPD8151	Discontinued
0.6707	Remote Similarity	NPD5401	Approved
0.6705	Remote Similarity	NPD7054	Approved
0.6703	Remote Similarity	NPD6836	Approved
0.6688	Remote Similarity	NPD230	Phase 1
0.6687	Remote Similarity	NPD7236	Approved
0.6687	Remote Similarity	NPD2344	Approved
0.6685	Remote Similarity	NPD8368	Discontinued
0.6667	Remote Similarity	NPD4386	Approved
0.6667	Remote Similarity	NPD7003	Approved
0.6667	Remote Similarity	NPD7472	Approved
0.6667	Remote Similarity	NPD7411	Suspended
0.6667	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7635	Approved
0.6667	Remote Similarity	NPD3750	Approved
0.6667	Remote Similarity	NPD2798	Approved
0.6667	Remote Similarity	NPD4387	Approved
0.6649	Remote Similarity	NPD4914	Approved
0.6648	Remote Similarity	NPD5032	Approved
0.6647	Remote Similarity	NPD7458	Discontinued
0.6644	Remote Similarity	NPD3019	Approved
0.6627	Remote Similarity	NPD6844	Discontinued
0.6627	Remote Similarity	NPD37	Approved
0.6625	Remote Similarity	NPD6100	Approved
0.6625	Remote Similarity	NPD6099	Approved
0.6624	Remote Similarity	NPD4060	Phase 1
0.6608	Remote Similarity	NPD7768	Phase 2
0.6601	Remote Similarity	NPD1164	Approved
0.6596	Remote Similarity	NPD5544	Approved
0.6588	Remote Similarity	NPD1465	Phase 2
0.6587	Remote Similarity	NPD7239	Suspended
0.6575	Remote Similarity	NPD8407	Phase 2
0.657	Remote Similarity	NPD3749	Approved
0.6564	Remote Similarity	NPD7783	Phase 2
0.6564	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD7799	Discontinued
0.6536	Remote Similarity	NPD6696	Suspended
0.6534	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD6234	Discontinued
0.6524	Remote Similarity	NPD2309	Approved
0.6522	Remote Similarity	NPD1551	Phase 2
0.6512	Remote Similarity	NPD4967	Phase 2
0.6512	Remote Similarity	NPD4966	Approved
0.6512	Remote Similarity	NPD4965	Approved
0.6507	Remote Similarity	NPD1398	Phase 1
0.6503	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD6674	Discontinued
0.65	Remote Similarity	NPD5039	Approved
0.6494	Remote Similarity	NPD3094	Phase 2
0.6491	Remote Similarity	NPD5760	Phase 2
0.6491	Remote Similarity	NPD5761	Phase 2
0.6489	Remote Similarity	NPD7282	Approved
0.6486	Remote Similarity	NPD7340	Approved
0.6481	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD5763	Approved
0.6481	Remote Similarity	NPD5762	Approved
0.6477	Remote Similarity	NPD3926	Phase 2

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