NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	500.17
Volume:	482.28
LogP:	3.262
LogD:	1.407
LogS:	-2.601
# Rotatable Bonds:	3
TPSA:	169.3
# H-Bond Aceptor:	10
# H-Bond Donor:	7
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.208
Synthetic Accessibility Score:	4.799
Fsp3:	0.385
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.321
MDCK Permeability:	5.83788914809702e-06
Pgp-inhibitor:	0.066
Pgp-substrate:	0.983
Human Intestinal Absorption (HIA):	0.901
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.935

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	96.83724975585938%
Volume Distribution (VD):	0.488
Pgp-substrate:	9.451973915100098%

ADMET: Metabolism

CYP1A2-inhibitor:	0.318
CYP1A2-substrate:	0.586
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.169
CYP2C9-substrate:	0.2
CYP2D6-inhibitor:	0.157
CYP2D6-substrate:	0.161
CYP3A4-inhibitor:	0.094
CYP3A4-substrate:	0.052

ADMET: Excretion

Clearance (CL):	2.491
Half-life (T1/2):	0.479

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.388
Drug-inuced Liver Injury (DILI):	0.955
AMES Toxicity:	0.812
Rat Oral Acute Toxicity:	0.082
Maximum Recommended Daily Dose:	0.069
Skin Sensitization:	0.91
Carcinogencity:	0.083
Eye Corrosion:	0.003
Eye Irritation:	0.238
Respiratory Toxicity:	0.152

Download Data

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

Natural Product: NPC478022

Natural Product ID:	NPC478022
*Common Name:**	(8R,10S)-10-[(6-deoxy-2-O-methyl-alpha-L-mannopyranosyl)oxy]-7,8,9,10-tetrahydro-1,8,11-trihydroxy-8-methyl-5,12-naphthacenedione
IUPAC Name:	(7S,9R)-7-[(2R,3R,4R,5R,6S)-4,5-dihydroxy-3-methoxy-6-methyloxan-2-yl]oxy-4,6,9-trihydroxy-9-methyl-8,10-dihydro-7H-tetracene-5,12-dione
Synonyms:
Standard InCHIKey:	DEPMSUJGYKZLRC-ZCUANGBISA-N
Standard InCHI:	InChI=1S/C26H28O10/c1-10-19(28)23(32)24(34-3)25(35-10)36-15-9-26(2,33)8-11-7-13-18(21(30)16(11)15)22(31)17-12(20(13)29)5-4-6-14(17)27/h4-7,10,15,19,23-25,27-28,30,32-33H,8-9H2,1-3H3/t10-,15-,19-,23+,24+,25-,26+/m0/s1
SMILES:	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2C[C@](CC3=CC4=C(C(=C23)O)C(=O)C5=C(C4=O)C=CC=C5O)(C)O)OC)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	122177932
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002106] Anthracyclines

*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
NPO33681	Streptomyces sp. CMB-M0150	Species	Streptomycetaceae	Bacteria	n.a.	Sunshine Coast, Queensland, Australia	2007	PMID[25789410]

☑ 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	12
MIC	8

Activity Type	# Activity
Cell Line	3
Organism	16
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT323	Cell Line	SW-620	Homo sapiens	IC50	>	30000	nM	PMID[25789410]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	30000	nM	PMID[25789410]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	>	30000	nM	PMID[25789410]
NPT1108	Organism	Mycobacterium bovis BCG	Mycobacterium bovis BCG	MIC	=	30000	nM	PMID[25789410]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	7500	nM	PMID[25789410]
NPT3145	Organism	Bacillus subtilis subsp. spizizenii ATCC 6633	Bacillus subtilis subsp. spizizenii ATCC 6633	MIC	=	7500	nM	PMID[25789410]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	30000	nM	PMID[25789410]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	30000	nM	PMID[25789410]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	30000	nM	PMID[25789410]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	30000	nM	PMID[25789410]
NPT2	Others	Unspecified		IC50	>	30000	nM	PMID[25789410]
NPT1108	Organism	Mycobacterium bovis BCG	Mycobacterium bovis BCG	IC50	=	1100	nM	PMID[25789410]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IC50	=	2800	nM	PMID[25789410]
NPT3145	Organism	Bacillus subtilis subsp. spizizenii ATCC 6633	Bacillus subtilis subsp. spizizenii ATCC 6633	IC50	=	2400	nM	PMID[25789410]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	>	30000	nM	PMID[25789410]
NPT19	Organism	Escherichia coli	Escherichia coli	IC50	>	30000	nM	PMID[25789410]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	IC50	>	30000	nM	PMID[25789410]
NPT20	Organism	Candida albicans	Candida albicans	IC50	>	30000	nM	PMID[25789410]

☑ 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 NPC478022 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	388
0.1-0.2	1457
0.2-0.3	3019
0.3-0.4	6942
0.4-0.5	9893
0.5-0.6	6416
0.6-0.7	5945
0.7-0.8	7377
0.8-0.85	1039
0.85-0.9	154
0.9-0.95	63
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC478020
0.9748	High Similarity	NPC478021
0.9688	High Similarity	NPC294501
0.9371	High Similarity	NPC97637
0.9371	High Similarity	NPC187934
0.9363	High Similarity	NPC206641
0.9363	High Similarity	NPC208651
0.9321	High Similarity	NPC175477
0.9304	High Similarity	NPC53139
0.9277	High Similarity	NPC277710
0.9277	High Similarity	NPC153578
0.9277	High Similarity	NPC299149
0.9277	High Similarity	NPC114257
0.9273	High Similarity	NPC475246
0.9268	High Similarity	NPC85368
0.9236	High Similarity	NPC3449
0.9222	High Similarity	NPC315221
0.9212	High Similarity	NPC3718
0.9207	High Similarity	NPC30432
0.9207	High Similarity	NPC5029
0.9207	High Similarity	NPC111536
0.9207	High Similarity	NPC271385
0.9207	High Similarity	NPC76128
0.9207	High Similarity	NPC183441
0.9177	High Similarity	NPC283480
0.9177	High Similarity	NPC148323
0.9167	High Similarity	NPC313452
0.9162	High Similarity	NPC72783
0.9157	High Similarity	NPC475233
0.9157	High Similarity	NPC46958
0.9152	High Similarity	NPC203751
0.9146	High Similarity	NPC470580
0.9136	High Similarity	NPC478026
0.9136	High Similarity	NPC329647
0.9136	High Similarity	NPC470735
0.913	High Similarity	NPC278329
0.913	High Similarity	NPC146837
0.913	High Similarity	NPC101116
0.913	High Similarity	NPC212099
0.9114	High Similarity	NPC82190
0.9114	High Similarity	NPC174599
0.9114	High Similarity	NPC192219
0.9107	High Similarity	NPC477860
0.9107	High Similarity	NPC475161
0.9096	High Similarity	NPC70862
0.9096	High Similarity	NPC68381
0.9096	High Similarity	NPC19056
0.9096	High Similarity	NPC470583
0.9091	High Similarity	NPC270027
0.9085	High Similarity	NPC222455
0.9059	High Similarity	NPC87583
0.9051	High Similarity	NPC209393
0.9051	High Similarity	NPC474621
0.9051	High Similarity	NPC205172
0.9051	High Similarity	NPC474622
0.9042	High Similarity	NPC102053
0.9042	High Similarity	NPC176246
0.9042	High Similarity	NPC289876
0.9036	High Similarity	NPC199357
0.9036	High Similarity	NPC472054
0.9036	High Similarity	NPC98776
0.9018	High Similarity	NPC178281
0.9006	High Similarity	NPC105591
0.8988	High Similarity	NPC115447
0.8988	High Similarity	NPC470581
0.8988	High Similarity	NPC266513
0.8988	High Similarity	NPC470582
0.8968	High Similarity	NPC285122
0.8938	High Similarity	NPC478027
0.8935	High Similarity	NPC58538
0.8935	High Similarity	NPC187441
0.8935	High Similarity	NPC212290
0.8935	High Similarity	NPC283980
0.8922	High Similarity	NPC65118
0.8916	High Similarity	NPC298778
0.8909	High Similarity	NPC63470
0.8896	High Similarity	NPC216752
0.8882	High Similarity	NPC85316
0.8882	High Similarity	NPC197357
0.8876	High Similarity	NPC83331
0.8869	High Similarity	NPC470667
0.8869	High Similarity	NPC186800
0.8869	High Similarity	NPC146803
0.8868	High Similarity	NPC474533
0.8868	High Similarity	NPC474534
0.8857	High Similarity	NPC316412
0.8857	High Similarity	NPC315351
0.8855	High Similarity	NPC259905
0.8848	High Similarity	NPC178851
0.8812	High Similarity	NPC470408
0.8812	High Similarity	NPC474824
0.8812	High Similarity	NPC182921
0.8812	High Similarity	NPC218870
0.881	High Similarity	NPC213052
0.8807	High Similarity	NPC42286
0.8793	High Similarity	NPC314672
0.8782	High Similarity	NPC170055
0.8779	High Similarity	NPC292706
0.8779	High Similarity	NPC224557
0.8773	High Similarity	NPC284495
0.8758	High Similarity	NPC266469
0.8757	High Similarity	NPC109403
0.8757	High Similarity	NPC474345
0.8757	High Similarity	NPC313274
0.8757	High Similarity	NPC314738
0.8757	High Similarity	NPC261012
0.8743	High Similarity	NPC246274
0.8736	High Similarity	NPC205721
0.8721	High Similarity	NPC475662
0.8721	High Similarity	NPC473631
0.8721	High Similarity	NPC293227
0.8721	High Similarity	NPC478001
0.8721	High Similarity	NPC473717
0.8718	High Similarity	NPC48130
0.8718	High Similarity	NPC84568
0.8718	High Similarity	NPC300684
0.8718	High Similarity	NPC218866
0.8704	High Similarity	NPC474861
0.8683	High Similarity	NPC472058
0.8683	High Similarity	NPC234497
0.8683	High Similarity	NPC103633
0.8683	High Similarity	NPC105414
0.8683	High Similarity	NPC470341
0.8683	High Similarity	NPC324522
0.865	High Similarity	NPC257309
0.8647	High Similarity	NPC470454
0.8647	High Similarity	NPC63105
0.8647	High Similarity	NPC223735
0.8647	High Similarity	NPC307754
0.8647	High Similarity	NPC199533
0.8639	High Similarity	NPC315619
0.8634	High Similarity	NPC478220
0.8631	High Similarity	NPC473202
0.8623	High Similarity	NPC469419
0.8621	High Similarity	NPC475352
0.8621	High Similarity	NPC475220
0.8621	High Similarity	NPC221140
0.8621	High Similarity	NPC473686
0.8621	High Similarity	NPC229817
0.8608	High Similarity	NPC470570
0.8605	High Similarity	NPC245059
0.8605	High Similarity	NPC84494
0.8598	High Similarity	NPC324736
0.8596	High Similarity	NPC66820
0.8596	High Similarity	NPC92403
0.8596	High Similarity	NPC170018
0.8596	High Similarity	NPC76112
0.8588	High Similarity	NPC470336
0.8588	High Similarity	NPC470335
0.8571	High Similarity	NPC107009
0.8564	High Similarity	NPC314941
0.8563	High Similarity	NPC297404
0.8563	High Similarity	NPC11608
0.8563	High Similarity	NPC99216
0.8562	High Similarity	NPC280753
0.8562	High Similarity	NPC478219
0.8562	High Similarity	NPC44378
0.8555	High Similarity	NPC470453
0.8555	High Similarity	NPC164047
0.8555	High Similarity	NPC470452
0.8555	High Similarity	NPC470448
0.8554	High Similarity	NPC478229
0.8554	High Similarity	NPC44947
0.8553	High Similarity	NPC119767
0.8547	High Similarity	NPC469418
0.8547	High Similarity	NPC478000
0.8547	High Similarity	NPC470334
0.8545	High Similarity	NPC328093
0.8545	High Similarity	NPC472320
0.8544	High Similarity	NPC34482
0.8537	High Similarity	NPC177742
0.8537	High Similarity	NPC23817
0.8531	High Similarity	NPC264302
0.8528	High Similarity	NPC66029
0.8528	High Similarity	NPC474501
0.8521	High Similarity	NPC191653
0.8514	High Similarity	NPC241847
0.8512	High Similarity	NPC477835
0.8512	High Similarity	NPC178173
0.8509	High Similarity	NPC205766
0.8503	High Similarity	NPC124155
0.8503	High Similarity	NPC183672
0.8503	High Similarity	NPC257566
0.85	High Similarity	NPC94781
0.8494	Intermediate Similarity	NPC472261
0.8494	Intermediate Similarity	NPC477627
0.8494	Intermediate Similarity	NPC303913
0.8494	Intermediate Similarity	NPC47923
0.8491	Intermediate Similarity	NPC147250
0.8488	Intermediate Similarity	NPC314489
0.8488	Intermediate Similarity	NPC198893
0.8488	Intermediate Similarity	NPC232818
0.8485	Intermediate Similarity	NPC73511
0.8485	Intermediate Similarity	NPC314795
0.8483	Intermediate Similarity	NPC314459
0.8483	Intermediate Similarity	NPC470199
0.8481	Intermediate Similarity	NPC193703
0.8481	Intermediate Similarity	NPC21599
0.8481	Intermediate Similarity	NPC244691
0.8481	Intermediate Similarity	NPC48762

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 NPC478022 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	339
0.1-0.2	876
0.2-0.3	1616
0.3-0.4	2752
0.4-0.5	2008
0.5-0.6	1051
0.6-0.7	357
0.7-0.8	107
0.8-0.85	29
0.85-0.9	14
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9118	High Similarity	NPD7879	Clinical (unspecified phase)
0.8902	High Similarity	NPD6534	Approved
0.8902	High Similarity	NPD6535	Approved
0.8757	High Similarity	NPD6778	Approved
0.8757	High Similarity	NPD6779	Approved
0.8757	High Similarity	NPD6781	Approved
0.8757	High Similarity	NPD6777	Approved
0.8757	High Similarity	NPD6780	Approved
0.8757	High Similarity	NPD6776	Approved
0.8757	High Similarity	NPD6782	Approved
0.875	High Similarity	NPD7699	Phase 2
0.875	High Similarity	NPD7700	Phase 2
0.8611	High Similarity	NPD7435	Discontinued
0.8596	High Similarity	NPD8312	Approved
0.8596	High Similarity	NPD8313	Approved
0.8564	High Similarity	NPD8320	Phase 1
0.8564	High Similarity	NPD8319	Approved
0.8523	High Similarity	NPD6213	Phase 3
0.8523	High Similarity	NPD6212	Phase 3
0.8523	High Similarity	NPD6214	Clinical (unspecified phase)
0.8508	High Similarity	NPD7697	Approved
0.8508	High Similarity	NPD7698	Approved
0.8508	High Similarity	NPD7696	Phase 3
0.8462	Intermediate Similarity	NPD7870	Phase 2
0.8462	Intermediate Similarity	NPD7871	Phase 2
0.8424	Intermediate Similarity	NPD7701	Phase 2
0.8424	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8352	Intermediate Similarity	NPD6823	Phase 2
0.8343	Intermediate Similarity	NPD8150	Discontinued
0.8333	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD7874	Approved
0.8304	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD7801	Approved
0.8282	Intermediate Similarity	NPD4380	Phase 2
0.8274	Intermediate Similarity	NPD6959	Discontinued
0.8266	Intermediate Similarity	NPD6559	Discontinued
0.8256	Intermediate Similarity	NPD7074	Phase 3
0.8216	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.8198	Intermediate Similarity	NPD7054	Approved
0.8182	Intermediate Similarity	NPD8151	Discontinued
0.815	Intermediate Similarity	NPD7472	Approved
0.8146	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.814	Intermediate Similarity	NPD3818	Discontinued
0.8118	Intermediate Similarity	NPD6232	Discontinued
0.8103	Intermediate Similarity	NPD6797	Phase 2
0.8081	Intermediate Similarity	NPD7473	Discontinued
0.8057	Intermediate Similarity	NPD7251	Discontinued
0.8035	Intermediate Similarity	NPD3751	Discontinued
0.8025	Intermediate Similarity	NPD7390	Discontinued
0.8011	Intermediate Similarity	NPD7808	Phase 3
0.7975	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD6166	Phase 2
0.7919	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD7819	Suspended
0.791	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD3787	Discontinued
0.7892	Intermediate Similarity	NPD3226	Approved
0.7886	Intermediate Similarity	NPD5844	Phase 1
0.7882	Intermediate Similarity	NPD7075	Discontinued
0.7812	Intermediate Similarity	NPD7783	Phase 2
0.7812	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7458	Discontinued
0.7765	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD1934	Approved
0.7727	Intermediate Similarity	NPD7228	Approved
0.7719	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD8059	Phase 3
0.7706	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD5406	Approved
0.7702	Intermediate Similarity	NPD5408	Approved
0.7702	Intermediate Similarity	NPD5404	Approved
0.7702	Intermediate Similarity	NPD5405	Approved
0.7692	Intermediate Similarity	NPD7411	Suspended
0.768	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD2534	Approved
0.7651	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD2532	Approved
0.7651	Intermediate Similarity	NPD2533	Approved
0.7651	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6801	Discontinued
0.7613	Intermediate Similarity	NPD1470	Approved
0.7602	Intermediate Similarity	NPD8455	Phase 2
0.7598	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD5494	Approved
0.7558	Intermediate Similarity	NPD5402	Approved
0.7546	Intermediate Similarity	NPD2346	Discontinued
0.7545	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD37	Approved
0.7529	Intermediate Similarity	NPD6234	Discontinued
0.7514	Intermediate Similarity	NPD4967	Phase 2
0.7514	Intermediate Similarity	NPD4966	Approved
0.7514	Intermediate Similarity	NPD4965	Approved
0.75	Intermediate Similarity	NPD1549	Phase 2
0.75	Intermediate Similarity	NPD2801	Approved
0.7471	Intermediate Similarity	NPD3749	Approved
0.7471	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD6190	Approved
0.7459	Intermediate Similarity	NPD7685	Pre-registration
0.7439	Intermediate Similarity	NPD7266	Discontinued
0.7439	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD6599	Discontinued
0.7423	Intermediate Similarity	NPD1510	Phase 2
0.7414	Intermediate Similarity	NPD7768	Phase 2
0.7414	Intermediate Similarity	NPD3882	Suspended
0.741	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD4628	Phase 3
0.7407	Intermediate Similarity	NPD1607	Approved
0.7378	Intermediate Similarity	NPD2935	Discontinued
0.7363	Intermediate Similarity	NPD7240	Approved
0.7356	Intermediate Similarity	NPD3817	Phase 2
0.7355	Intermediate Similarity	NPD1201	Approved
0.7353	Intermediate Similarity	NPD5403	Approved
0.7351	Intermediate Similarity	NPD8434	Phase 2
0.7333	Intermediate Similarity	NPD7584	Approved
0.7333	Intermediate Similarity	NPD7799	Discontinued
0.7299	Intermediate Similarity	NPD1465	Phase 2
0.7289	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD1240	Approved
0.7284	Intermediate Similarity	NPD943	Approved
0.7278	Intermediate Similarity	NPD6799	Approved
0.7278	Intermediate Similarity	NPD1511	Approved
0.7273	Intermediate Similarity	NPD2796	Approved
0.7267	Intermediate Similarity	NPD3764	Approved
0.7251	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD7199	Phase 2
0.7246	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD8285	Discontinued
0.7235	Intermediate Similarity	NPD5401	Approved
0.7235	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD5710	Approved
0.7207	Intermediate Similarity	NPD5711	Approved
0.7205	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7003	Approved
0.7202	Intermediate Similarity	NPD3750	Approved
0.7193	Intermediate Similarity	NPD1512	Approved
0.7164	Intermediate Similarity	NPD7930	Approved
0.7143	Intermediate Similarity	NPD6674	Discontinued
0.7134	Intermediate Similarity	NPD230	Phase 1
0.7108	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD8166	Discontinued
0.7076	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD1551	Phase 2
0.7066	Intermediate Similarity	NPD6100	Approved
0.7066	Intermediate Similarity	NPD6099	Approved
0.7049	Intermediate Similarity	NPD7177	Discontinued
0.7027	Intermediate Similarity	NPD5953	Discontinued
0.7019	Intermediate Similarity	NPD2798	Approved
0.7018	Intermediate Similarity	NPD3300	Phase 2
0.7006	Intermediate Similarity	NPD5126	Approved
0.7006	Intermediate Similarity	NPD2799	Discontinued
0.7006	Intermediate Similarity	NPD5125	Phase 3
0.7	Intermediate Similarity	NPD8360	Approved
0.7	Intermediate Similarity	NPD8361	Approved
0.7	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6273	Approved
0.6989	Remote Similarity	NPD8368	Discontinued
0.6974	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD2313	Discontinued
0.695	Remote Similarity	NPD7585	Approved
0.6946	Remote Similarity	NPD7097	Phase 1
0.6941	Remote Similarity	NPD2800	Approved
0.6939	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7999	Approved
0.6923	Remote Similarity	NPD2344	Approved
0.6919	Remote Similarity	NPD7680	Approved
0.6919	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD1653	Approved
0.6911	Remote Similarity	NPD8435	Approved
0.691	Remote Similarity	NPD5760	Phase 2
0.691	Remote Similarity	NPD5761	Phase 2
0.6905	Remote Similarity	NPD3748	Approved
0.69	Remote Similarity	NPD7583	Approved
0.689	Remote Similarity	NPD4625	Phase 3
0.6885	Remote Similarity	NPD3926	Phase 2
0.6878	Remote Similarity	NPD8407	Phase 2
0.6867	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD920	Approved
0.6842	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD7286	Phase 2
0.6826	Remote Similarity	NPD1933	Approved
0.6821	Remote Similarity	NPD7236	Approved
0.6818	Remote Similarity	NPD7239	Suspended
0.6816	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD7033	Discontinued
0.6788	Remote Similarity	NPD7008	Discontinued
0.6786	Remote Similarity	NPD6651	Approved
0.6786	Remote Similarity	NPD8485	Approved
0.6776	Remote Similarity	NPD8127	Discontinued
0.6776	Remote Similarity	NPD1247	Approved
0.6772	Remote Similarity	NPD9545	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