NPASS Compound

Structure

NPC136878 OpenBabel07101718322D 23 25 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 -2.5981 1.5000 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 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 -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 -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 -0.8660 1.5000 0.0000 C 0 0 1 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 -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 -0.8660 2.5000 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 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 23 1 0 0 0 0 3 6 2 0 0 0 0 3 7 1 0 0 0 0 4 9 1 0 0 0 0 4 10 2 0 0 0 0 5 8 1 0 0 0 0 5 16 1 0 0 0 0 6 8 1 0 0 0 0 6 13 1 0 0 0 0 7 9 1 0 0 0 0 7 11 2 0 0 0 0 8 12 2 0 0 0 0 9 17 2 0 0 0 0 10 14 1 0 0 0 0 10 23 1 0 0 0 0 11 12 1 0 0 0 0 11 14 1 0 0 0 0 12 18 1 0 0 0 0 13 15 1 0 0 0 0 13 19 1 6 0 0 0 14 20 2 0 0 0 0 15 16 1 1 0 0 0 15 21 1 0 0 0 0 16 1 1 6 0 0 0 16 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	320.09
Volume:	305.336
LogP:	0.757
LogD:	0.699
LogS:	-2.761
# 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:	0.493
Synthetic Accessibility Score:	3.983
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:	-5.625
MDCK Permeability:	4.2147062231379095e-06
Pgp-inhibitor:	0.004
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.194
20% Bioavailability (F20%):	0.432
30% Bioavailability (F30%):	0.105

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.057
Plasma Protein Binding (PPB):	90.67594909667969%
Volume Distribution (VD):	0.896
Pgp-substrate:	14.21922492980957%

ADMET: Metabolism

CYP1A2-inhibitor:	0.081
CYP1A2-substrate:	0.713
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.13
CYP2C9-inhibitor:	0.026
CYP2C9-substrate:	0.319
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.185
CYP3A4-inhibitor:	0.036
CYP3A4-substrate:	0.176

ADMET: Excretion

Clearance (CL):	12.021
Half-life (T1/2):	0.836

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.159
Drug-inuced Liver Injury (DILI):	0.605
AMES Toxicity:	0.372
Rat Oral Acute Toxicity:	0.083
Maximum Recommended Daily Dose:	0.885
Skin Sensitization:	0.776
Carcinogencity:	0.094
Eye Corrosion:	0.003
Eye Irritation:	0.3
Respiratory Toxicity:	0.427

Download Data

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

Natural Product: NPC136878

Natural Product ID:	NPC136878
*Common Name:**	10-Deoxybostrycin
IUPAC Name:	(5S,6R,7S)-5,6,7,9-tetrahydroxy-2-methoxy-7-methyl-6,8-dihydro-5H-anthracene-1,4-dione
Synonyms:	10-Deoxybostrycin
Standard InCHIKey:	NRHMPEJAWNKHLC-IMJJTQAJSA-N
Standard InCHI:	InChI=1S/C16H16O7/c1-16(22)5-8-6(13(19)15(16)21)3-7-9(17)4-10(23-2)14(20)11(7)12(8)18/h3-4,13,15,18-19,21-22H,5H2,1-2H3/t13-,15+,16-/m0/s1
SMILES:	COC1=CC(=O)c2c(C1=O)c(O)c1c(c2)[C@H](O)[C@H]([C@@](C1)(C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2047187
PubChem CID:	59051896
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	1
MIC	9

Activity Type	# Activity
Cell Line	1
Organism	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	4560.0	nM	PMID[505603]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	625.0	nM	PMID[505603]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	10000.0	nM	PMID[505603]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	20000.0	nM	PMID[505603]
NPT5776	Organism	Streptomyces albus	Streptomyces albus	MIC	=	5000.0	nM	PMID[505603]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	2500.0	nM	PMID[505603]
NPT3146	Organism	Micrococcus	Micrococcus	MIC	=	1250.0	nM	PMID[505603]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	2500.0	nM	PMID[505603]
NPT1311	Organism	Listonella anguillarum	Listonella anguillarum	MIC	=	2500.0	nM	PMID[505603]
NPT565	Organism	Vibrio parahaemolyticus	Vibrio parahaemolyticus	MIC	=	1250.0	nM	PMID[505603]

☑ 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 NPC136878 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	1285
0.2-0.3	3147
0.3-0.4	7787
0.4-0.5	11082
0.5-0.6	5383
0.6-0.7	7352
0.7-0.8	5785
0.8-0.85	448
0.85-0.9	57
0.9-0.95	8
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9714	High Similarity	NPC29932
0.9444	High Similarity	NPC112816
0.9366	High Similarity	NPC143898
0.9128	High Similarity	NPC312482
0.9007	High Similarity	NPC315275
0.8973	High Similarity	NPC474630
0.8919	High Similarity	NPC470479
0.8904	High Similarity	NPC471906
0.8904	High Similarity	NPC244691
0.8881	High Similarity	NPC173980
0.8867	High Similarity	NPC205918
0.8859	High Similarity	NPC44378
0.8859	High Similarity	NPC280753
0.8792	High Similarity	NPC94781
0.8776	High Similarity	NPC79627
0.8767	High Similarity	NPC135524
0.875	High Similarity	NPC472211
0.8733	High Similarity	NPC120171
0.8723	High Similarity	NPC309430
0.8723	High Similarity	NPC17843
0.8714	High Similarity	NPC198305
0.8699	High Similarity	NPC204045
0.8699	High Similarity	NPC305845
0.8699	High Similarity	NPC110810
0.8693	High Similarity	NPC314257
0.869	High Similarity	NPC103337
0.869	High Similarity	NPC114620
0.8684	High Similarity	NPC470340
0.8662	High Similarity	NPC254603
0.8658	High Similarity	NPC285122
0.8639	High Similarity	NPC474961
0.8639	High Similarity	NPC248068
0.8627	High Similarity	NPC155686
0.8625	High Similarity	NPC470580
0.8618	High Similarity	NPC46882
0.8618	High Similarity	NPC132990
0.8611	High Similarity	NPC474311
0.8609	High Similarity	NPC474310
0.8608	High Similarity	NPC329647
0.8608	High Similarity	NPC470735
0.8608	High Similarity	NPC472049
0.8592	High Similarity	NPC88864
0.8591	High Similarity	NPC34482
0.859	High Similarity	NPC284495
0.8571	High Similarity	NPC473113
0.8562	High Similarity	NPC113608
0.8562	High Similarity	NPC470338
0.8562	High Similarity	NPC190457
0.8562	High Similarity	NPC473095
0.8562	High Similarity	NPC268992
0.8562	High Similarity	NPC470337
0.8562	High Similarity	NPC180944
0.8562	High Similarity	NPC51824
0.8562	High Similarity	NPC473096
0.8533	High Similarity	NPC470570
0.8531	High Similarity	NPC171968
0.8526	High Similarity	NPC477410
0.8523	High Similarity	NPC48762
0.8516	High Similarity	NPC478027
0.8514	High Similarity	NPC308572
0.8509	High Similarity	NPC313717
0.8509	High Similarity	NPC315306
0.8506	High Similarity	NPC474824
0.8506	High Similarity	NPC182921
0.8506	High Similarity	NPC218870
0.8506	High Similarity	NPC470408
0.8503	High Similarity	NPC471853
0.85	High Similarity	NPC473094
0.8497	Intermediate Similarity	NPC470569
0.8493	Intermediate Similarity	NPC230811
0.8477	Intermediate Similarity	NPC476821
0.8467	Intermediate Similarity	NPC170055
0.8466	Intermediate Similarity	NPC470583
0.8466	Intermediate Similarity	NPC19056
0.8462	Intermediate Similarity	NPC472889
0.8462	Intermediate Similarity	NPC70622
0.8462	Intermediate Similarity	NPC246693
0.8462	Intermediate Similarity	NPC110609
0.8462	Intermediate Similarity	NPC242358
0.8457	Intermediate Similarity	NPC270027
0.8452	Intermediate Similarity	NPC68727
0.8452	Intermediate Similarity	NPC478133
0.8446	Intermediate Similarity	NPC283292
0.844	Intermediate Similarity	NPC767
0.844	Intermediate Similarity	NPC247250
0.844	Intermediate Similarity	NPC237225
0.8435	Intermediate Similarity	NPC138099
0.8435	Intermediate Similarity	NPC242994
0.8435	Intermediate Similarity	NPC477408
0.8431	Intermediate Similarity	NPC470568
0.8431	Intermediate Similarity	NPC280295
0.8431	Intermediate Similarity	NPC225854
0.8431	Intermediate Similarity	NPC147735
0.8425	Intermediate Similarity	NPC305060
0.8425	Intermediate Similarity	NPC471905
0.8418	Intermediate Similarity	NPC117985
0.8418	Intermediate Similarity	NPC478134
0.8403	Intermediate Similarity	NPC52407
0.8403	Intermediate Similarity	NPC314048
0.8403	Intermediate Similarity	NPC193169
0.84	Intermediate Similarity	NPC300684
0.84	Intermediate Similarity	NPC103910
0.84	Intermediate Similarity	NPC48130
0.84	Intermediate Similarity	NPC477409
0.84	Intermediate Similarity	NPC21599
0.84	Intermediate Similarity	NPC84568
0.84	Intermediate Similarity	NPC193703
0.84	Intermediate Similarity	NPC218866
0.8397	Intermediate Similarity	NPC474861
0.8397	Intermediate Similarity	NPC478223
0.8389	Intermediate Similarity	NPC291078
0.8389	Intermediate Similarity	NPC469520
0.8387	Intermediate Similarity	NPC471695
0.8385	Intermediate Similarity	NPC105414
0.8385	Intermediate Similarity	NPC324522
0.8385	Intermediate Similarity	NPC234497
0.8385	Intermediate Similarity	NPC470341
0.8385	Intermediate Similarity	NPC472058
0.838	Intermediate Similarity	NPC278928
0.8378	Intermediate Similarity	NPC181560
0.8378	Intermediate Similarity	NPC169452
0.8375	Intermediate Similarity	NPC472057
0.8375	Intermediate Similarity	NPC472051
0.8375	Intermediate Similarity	NPC316262
0.8375	Intermediate Similarity	NPC314653
0.8367	Intermediate Similarity	NPC61398
0.8367	Intermediate Similarity	NPC416
0.8366	Intermediate Similarity	NPC478219
0.8364	Intermediate Similarity	NPC470581
0.8364	Intermediate Similarity	NPC470582
0.8364	Intermediate Similarity	NPC266513
0.8364	Intermediate Similarity	NPC115447
0.8356	Intermediate Similarity	NPC254847
0.8356	Intermediate Similarity	NPC86524
0.8354	Intermediate Similarity	NPC313368
0.8345	Intermediate Similarity	NPC202225
0.8344	Intermediate Similarity	NPC246466
0.8344	Intermediate Similarity	NPC28632
0.8344	Intermediate Similarity	NPC294501
0.8344	Intermediate Similarity	NPC478160
0.8344	Intermediate Similarity	NPC474309
0.8344	Intermediate Similarity	NPC478019
0.8333	Intermediate Similarity	NPC208173
0.8333	Intermediate Similarity	NPC170189
0.8333	Intermediate Similarity	NPC478221
0.8333	Intermediate Similarity	NPC471456
0.8333	Intermediate Similarity	NPC326910
0.8333	Intermediate Similarity	NPC58685
0.8333	Intermediate Similarity	NPC478190
0.8323	Intermediate Similarity	NPC478220
0.8323	Intermediate Similarity	NPC115249
0.8322	Intermediate Similarity	NPC136588
0.8322	Intermediate Similarity	NPC199253
0.8322	Intermediate Similarity	NPC31799
0.8313	Intermediate Similarity	NPC187441
0.8313	Intermediate Similarity	NPC283980
0.8312	Intermediate Similarity	NPC255641
0.8312	Intermediate Similarity	NPC290954
0.8311	Intermediate Similarity	NPC143438
0.831	Intermediate Similarity	NPC165257
0.8302	Intermediate Similarity	NPC316457
0.8299	Intermediate Similarity	NPC53414
0.8299	Intermediate Similarity	NPC475957
0.8299	Intermediate Similarity	NPC53206
0.8299	Intermediate Similarity	NPC264022
0.8298	Intermediate Similarity	NPC51037
0.8298	Intermediate Similarity	NPC231774
0.8293	Intermediate Similarity	NPC154986
0.8291	Intermediate Similarity	NPC470339
0.8289	Intermediate Similarity	NPC300540
0.8288	Intermediate Similarity	NPC283590
0.8288	Intermediate Similarity	NPC283088
0.8288	Intermediate Similarity	NPC258502
0.8288	Intermediate Similarity	NPC70859
0.8288	Intermediate Similarity	NPC61153
0.8288	Intermediate Similarity	NPC130899
0.8286	Intermediate Similarity	NPC152525
0.8286	Intermediate Similarity	NPC68756
0.8282	Intermediate Similarity	NPC478021
0.828	Intermediate Similarity	NPC472050
0.8278	Intermediate Similarity	NPC475813
0.8276	Intermediate Similarity	NPC78307
0.8276	Intermediate Similarity	NPC114183
0.8269	Intermediate Similarity	NPC93552
0.8269	Intermediate Similarity	NPC137301
0.8269	Intermediate Similarity	NPC107109
0.8269	Intermediate Similarity	NPC478231
0.8267	Intermediate Similarity	NPC85310
0.8267	Intermediate Similarity	NPC193555
0.8264	Intermediate Similarity	NPC17083
0.8261	Intermediate Similarity	NPC478022
0.8261	Intermediate Similarity	NPC478020
0.8258	Intermediate Similarity	NPC230848
0.8255	Intermediate Similarity	NPC156872
0.8255	Intermediate Similarity	NPC315578
0.8253	Intermediate Similarity	NPC83331
0.825	Intermediate Similarity	NPC472059
0.8247	Intermediate Similarity	NPC80370
0.8243	Intermediate Similarity	NPC13715
0.8239	Intermediate Similarity	NPC472055

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 NPC136878 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	317
0.1-0.2	891
0.2-0.3	1701
0.3-0.4	2826
0.4-0.5	1992
0.5-0.6	950
0.6-0.7	364
0.7-0.8	108
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
0.8356	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD1470	Approved
0.7965	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD7390	Discontinued
0.7867	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD3300	Phase 2
0.7836	Intermediate Similarity	NPD8150	Discontinued
0.7812	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD6232	Discontinued
0.7771	Intermediate Similarity	NPD7473	Discontinued
0.7756	Intermediate Similarity	NPD2532	Approved
0.7756	Intermediate Similarity	NPD2534	Approved
0.7756	Intermediate Similarity	NPD2533	Approved
0.7736	Intermediate Similarity	NPD4380	Phase 2
0.7718	Intermediate Similarity	NPD943	Approved
0.7697	Intermediate Similarity	NPD5408	Approved
0.7697	Intermediate Similarity	NPD5405	Approved
0.7697	Intermediate Similarity	NPD5406	Approved
0.7697	Intermediate Similarity	NPD5404	Approved
0.7692	Intermediate Similarity	NPD1201	Approved
0.767	Intermediate Similarity	NPD6534	Approved
0.767	Intermediate Similarity	NPD6535	Approved
0.7669	Intermediate Similarity	NPD7075	Discontinued
0.7643	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD6959	Discontinued
0.7607	Intermediate Similarity	NPD3882	Suspended
0.7593	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD3226	Approved
0.7556	Intermediate Similarity	NPD6776	Approved
0.7556	Intermediate Similarity	NPD6777	Approved
0.7556	Intermediate Similarity	NPD6780	Approved
0.7556	Intermediate Similarity	NPD6779	Approved
0.7556	Intermediate Similarity	NPD6778	Approved
0.7556	Intermediate Similarity	NPD6781	Approved
0.7556	Intermediate Similarity	NPD6782	Approved
0.7542	Intermediate Similarity	NPD7700	Phase 2
0.7542	Intermediate Similarity	NPD7699	Phase 2
0.7532	Intermediate Similarity	NPD2346	Discontinued
0.7531	Intermediate Similarity	NPD1934	Approved
0.7531	Intermediate Similarity	NPD6801	Discontinued
0.7527	Intermediate Similarity	NPD7435	Discontinued
0.7518	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD3751	Discontinued
0.75	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6166	Phase 2
0.7485	Intermediate Similarity	NPD7819	Suspended
0.7452	Intermediate Similarity	NPD6190	Approved
0.7429	Intermediate Similarity	NPD8434	Phase 2
0.7407	Intermediate Similarity	NPD6599	Discontinued
0.7403	Intermediate Similarity	NPD1510	Phase 2
0.7399	Intermediate Similarity	NPD5026	Approved
0.7399	Intermediate Similarity	NPD36	Approved
0.7399	Intermediate Similarity	NPD4954	Approved
0.7399	Intermediate Similarity	NPD5034	Approved
0.7399	Intermediate Similarity	NPD4955	Approved
0.7399	Intermediate Similarity	NPD5028	Approved
0.7391	Intermediate Similarity	NPD8319	Approved
0.7391	Intermediate Similarity	NPD8320	Phase 1
0.7386	Intermediate Similarity	NPD1607	Approved
0.7378	Intermediate Similarity	NPD2801	Approved
0.7375	Intermediate Similarity	NPD1512	Approved
0.7368	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5844	Phase 1
0.7355	Intermediate Similarity	NPD2935	Discontinued
0.7345	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD5030	Phase 2
0.7337	Intermediate Similarity	NPD7696	Phase 3
0.7337	Intermediate Similarity	NPD7697	Approved
0.7337	Intermediate Similarity	NPD7698	Approved
0.7333	Intermediate Similarity	NPD3817	Phase 2
0.7333	Intermediate Similarity	NPD5402	Approved
0.733	Intermediate Similarity	NPD5038	Approved
0.733	Intermediate Similarity	NPD5037	Approved
0.7312	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD3818	Discontinued
0.7297	Intermediate Similarity	NPD7871	Phase 2
0.7297	Intermediate Similarity	NPD7870	Phase 2
0.7287	Intermediate Similarity	NPD7874	Approved
0.7287	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD6797	Phase 2
0.7273	Intermediate Similarity	NPD7701	Phase 2
0.7273	Intermediate Similarity	NPD5036	Approved
0.7262	Intermediate Similarity	NPD5494	Approved
0.7261	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD1549	Phase 2
0.7257	Intermediate Similarity	NPD8312	Approved
0.7257	Intermediate Similarity	NPD5035	Approved
0.7257	Intermediate Similarity	NPD8313	Approved
0.7255	Intermediate Similarity	NPD1240	Approved
0.725	Intermediate Similarity	NPD6799	Approved
0.725	Intermediate Similarity	NPD1511	Approved
0.7246	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7251	Discontinued
0.7241	Intermediate Similarity	NPD6559	Discontinued
0.7229	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD2800	Approved
0.72	Intermediate Similarity	NPD7808	Phase 3
0.72	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD5711	Approved
0.7176	Intermediate Similarity	NPD3787	Discontinued
0.7176	Intermediate Similarity	NPD5710	Approved
0.717	Intermediate Similarity	NPD4628	Phase 3
0.7158	Intermediate Similarity	NPD7801	Approved
0.7134	Intermediate Similarity	NPD2796	Approved
0.7127	Intermediate Similarity	NPD6213	Phase 3
0.7127	Intermediate Similarity	NPD6212	Phase 3
0.7127	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7074	Phase 3
0.7123	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD5403	Approved
0.7097	Intermediate Similarity	NPD230	Phase 1
0.7092	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD1471	Phase 3
0.7086	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7236	Approved
0.7079	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD7054	Approved
0.7063	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD8151	Discontinued
0.7051	Intermediate Similarity	NPD6651	Approved
0.7048	Intermediate Similarity	NPD7411	Suspended
0.7045	Intermediate Similarity	NPD5029	Approved
0.7045	Intermediate Similarity	NPD5027	Approved
0.7045	Intermediate Similarity	NPD5031	Approved
0.703	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD7472	Approved
0.7025	Intermediate Similarity	NPD6100	Approved
0.7025	Intermediate Similarity	NPD6099	Approved
0.7013	Intermediate Similarity	NPD2313	Discontinued
0.7005	Intermediate Similarity	NPD6823	Phase 2
0.7	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD5401	Approved
0.6981	Remote Similarity	NPD2344	Approved
0.697	Remote Similarity	NPD7239	Suspended
0.6962	Remote Similarity	NPD2799	Discontinued
0.6959	Remote Similarity	NPD2932	Approved
0.6957	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD3750	Approved
0.6957	Remote Similarity	NPD8166	Discontinued
0.6949	Remote Similarity	NPD8368	Discontinued
0.6941	Remote Similarity	NPD3749	Approved
0.6933	Remote Similarity	NPD9269	Phase 2
0.6928	Remote Similarity	NPD7458	Discontinued
0.6919	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD1247	Approved
0.6908	Remote Similarity	NPD1164	Approved
0.6905	Remote Similarity	NPD37	Approved
0.6903	Remote Similarity	NPD3764	Approved
0.6897	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD7768	Phase 2
0.6864	Remote Similarity	NPD1465	Phase 2
0.6863	Remote Similarity	NPD2798	Approved
0.6852	Remote Similarity	NPD7003	Approved
0.6846	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD3019	Approved
0.6839	Remote Similarity	NPD3926	Phase 2
0.6833	Remote Similarity	NPD8407	Phase 2
0.6818	Remote Similarity	NPD7799	Discontinued
0.6816	Remote Similarity	NPD5032	Approved
0.6815	Remote Similarity	NPD4060	Phase 1
0.6813	Remote Similarity	NPD1551	Phase 2
0.681	Remote Similarity	NPD2309	Approved
0.6809	Remote Similarity	NPD4914	Approved
0.6802	Remote Similarity	NPD6234	Discontinued
0.6802	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD919	Approved
0.6797	Remote Similarity	NPD3094	Phase 2
0.6793	Remote Similarity	NPD5968	Phase 3
0.6784	Remote Similarity	NPD4967	Phase 2
0.6784	Remote Similarity	NPD4965	Approved
0.6784	Remote Similarity	NPD4966	Approved
0.6779	Remote Similarity	NPD9268	Approved
0.6776	Remote Similarity	NPD6836	Approved
0.6765	Remote Similarity	NPD5761	Phase 2
0.6765	Remote Similarity	NPD5760	Phase 2
0.676	Remote Similarity	NPD5039	Approved
0.6753	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD4956	Approved
0.672	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD3972	Approved
0.671	Remote Similarity	NPD9494	Approved
0.6704	Remote Similarity	NPD5953	Discontinued
0.669	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD9493	Approved
0.6688	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD8360	Approved
0.6685	Remote Similarity	NPD8435	Approved
0.6685	Remote Similarity	NPD8361	Approved
0.6667	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1651	Approved
0.6667	Remote Similarity	NPD1237	Approved

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data