NPASS Compound

Structure

NPC476190 OpenBabel07101719252D 37 39 0 0 1 0 0 0 0 0999 V2000 5.5700 8.4658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4143 -0.7967 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8812 8.4658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0368 -0.7967 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1641 0.1866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3733 -2.0018 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5700 7.4908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0368 6.0283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1925 5.5408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0368 7.0033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1925 4.5658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7256 2.1283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8812 2.6158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7256 -0.7967 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5700 0.6658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3481 3.1033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5700 -0.3092 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.8812 7.4908 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.8812 -0.3092 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.7256 1.1533 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.0368 2.1283 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.3481 4.0783 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.7256 7.0033 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.4056 0.7162 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8812 0.6658 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.5582 -0.2468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0951 1.4056 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4426 0.8687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6894 -0.6894 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.0368 1.1533 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.5037 4.5658 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7256 6.0283 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4269 -0.6894 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8427 2.3474 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.7375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5369 -1.6524 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 19 1 0 0 0 0 5 30 1 0 0 0 0 6 37 1 0 0 0 0 7 23 1 0 0 0 0 8 9 1 0 0 0 0 8 10 2 0 0 0 0 9 11 2 0 0 0 0 10 18 1 0 0 0 0 11 22 1 0 0 0 0 12 13 2 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 14 17 1 0 0 0 0 14 19 1 0 0 0 0 15 17 1 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 16 22 1 0 0 0 0 18 23 1 0 0 0 0 19 25 1 0 0 0 0 20 25 1 0 0 0 0 21 30 1 0 0 0 0 22 32 1 0 0 0 0 23 33 1 0 0 0 0 24 26 2 0 0 0 0 24 27 1 0 0 0 0 24 28 1 0 0 0 0 25 30 1 0 0 0 0 26 29 1 0 0 0 0 26 34 1 0 0 0 0 27 30 1 0 0 0 0 27 35 2 0 0 0 0 28 31 2 0 0 0 0 28 36 1 0 0 0 0 29 31 1 0 0 0 0 29 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	515.32
Volume:	549.686
LogP:	4.176
LogD:	4.185
LogS:	-3.955
# Rotatable Bonds:	10
TPSA:	123.01
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.162
Synthetic Accessibility Score:	5.623
Fsp3:	0.633
Lipinski Rule-of-5:	Accepted
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:	-4.715
MDCK Permeability:	7.6086166700406466e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.095
Human Intestinal Absorption (HIA):	0.043
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.032

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.24
Plasma Protein Binding (PPB):	98.4281234741211%
Volume Distribution (VD):	0.721
Pgp-substrate:	2.6716833114624023%

ADMET: Metabolism

CYP1A2-inhibitor:	0.111
CYP1A2-substrate:	0.954
CYP2C19-inhibitor:	0.159
CYP2C19-substrate:	0.559
CYP2C9-inhibitor:	0.846
CYP2C9-substrate:	0.991
CYP2D6-inhibitor:	0.838
CYP2D6-substrate:	0.905
CYP3A4-inhibitor:	0.898
CYP3A4-substrate:	0.671

ADMET: Excretion

Clearance (CL):	5.314
Half-life (T1/2):	0.072

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.048
Drug-inuced Liver Injury (DILI):	0.956
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.202
Maximum Recommended Daily Dose:	0.157
Skin Sensitization:	0.044
Carcinogencity:	0.036
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.905

Download Data

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

Natural Product: NPC476190

Natural Product ID:	NPC476190
*Common Name:**	Delaminomycin B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XTFVFFOWVOQECG-GFULKKFKSA-N
Standard InCHI:	InChI=1S/C30H45NO6/c1-7-23(33)18(3)10-8-9-11-22(32)16-21-13-12-20-15-17(2)14-19(4)25(20)30(21,5)27(35)24-26(34)29(37-6)31-28(24)36/h8-13,17-23,25,29,32-34H,7,14-16H2,1-6H3,(H,31,36)/b10-8+,11-9+
SMILES:	CCC(C(/C=C/C=C/C(CC1C=CC2C(C1(C)C(=O)C1=C(O)C(N=C1O)OC)C(C)CC(C2)C)O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL552245
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000091] Pyrrolines

*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
NPO33025	streptomyces lucensis ma7349	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19115838]

☑ 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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6465	Organism	Streptomyces albulus	Streptomyces albulus	MIC	=	25.0	ug.mL-1	PMID[517322]

☑ 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 NPC476190 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	89
0.1-0.2	584
0.2-0.3	2346
0.3-0.4	9607
0.4-0.5	18172
0.5-0.6	9444
0.6-0.7	2362
0.7-0.8	81
0.8-0.85	4
0.85-0.9	5
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9626	High Similarity	NPC476269
0.9439	High Similarity	NPC476290
0.8108	Intermediate Similarity	NPC469598
0.807	Intermediate Similarity	NPC140251
0.807	Intermediate Similarity	NPC307903
0.7719	Intermediate Similarity	NPC474563
0.7692	Intermediate Similarity	NPC474725
0.7589	Intermediate Similarity	NPC239895
0.7521	Intermediate Similarity	NPC475800
0.75	Intermediate Similarity	NPC472733
0.75	Intermediate Similarity	NPC472734
0.7477	Intermediate Similarity	NPC477241
0.7477	Intermediate Similarity	NPC473162
0.7434	Intermediate Similarity	NPC472732
0.7434	Intermediate Similarity	NPC472731
0.7434	Intermediate Similarity	NPC208094
0.7422	Intermediate Similarity	NPC204556
0.7417	Intermediate Similarity	NPC324683
0.7373	Intermediate Similarity	NPC330011
0.7373	Intermediate Similarity	NPC329048
0.7368	Intermediate Similarity	NPC177680
0.7368	Intermediate Similarity	NPC472729
0.7368	Intermediate Similarity	NPC472730
0.7368	Intermediate Similarity	NPC153776
0.7304	Intermediate Similarity	NPC472727
0.7304	Intermediate Similarity	NPC472728
0.7288	Intermediate Similarity	NPC478052
0.7281	Intermediate Similarity	NPC53844
0.7257	Intermediate Similarity	NPC295347
0.7257	Intermediate Similarity	NPC209355
0.725	Intermediate Similarity	NPC475065
0.7227	Intermediate Similarity	NPC473169
0.719	Intermediate Similarity	NPC37116
0.719	Intermediate Similarity	NPC122926
0.719	Intermediate Similarity	NPC29133
0.719	Intermediate Similarity	NPC113012
0.7168	Intermediate Similarity	NPC473172
0.7167	Intermediate Similarity	NPC473482
0.7167	Intermediate Similarity	NPC475418
0.7167	Intermediate Similarity	NPC220155
0.7167	Intermediate Similarity	NPC318363
0.7156	Intermediate Similarity	NPC194417
0.7155	Intermediate Similarity	NPC54705
0.7154	Intermediate Similarity	NPC469496
0.7154	Intermediate Similarity	NPC469463
0.7154	Intermediate Similarity	NPC469454
0.7131	Intermediate Similarity	NPC470961
0.713	Intermediate Similarity	NPC4834
0.713	Intermediate Similarity	NPC474785
0.713	Intermediate Similarity	NPC474938
0.713	Intermediate Similarity	NPC27105
0.7119	Intermediate Similarity	NPC475050
0.7119	Intermediate Similarity	NPC473624
0.7107	Intermediate Similarity	NPC228477
0.7107	Intermediate Similarity	NPC137911
0.7107	Intermediate Similarity	NPC218602
0.7097	Intermediate Similarity	NPC476814
0.7097	Intermediate Similarity	NPC476813
0.7094	Intermediate Similarity	NPC473174
0.7083	Intermediate Similarity	NPC473284
0.7083	Intermediate Similarity	NPC251330
0.708	Intermediate Similarity	NPC115021
0.708	Intermediate Similarity	NPC474736
0.7073	Intermediate Similarity	NPC191620
0.7073	Intermediate Similarity	NPC476801
0.7069	Intermediate Similarity	NPC471717
0.7069	Intermediate Similarity	NPC203388
0.7069	Intermediate Similarity	NPC471330
0.7069	Intermediate Similarity	NPC99657
0.7069	Intermediate Similarity	NPC471331
0.7069	Intermediate Similarity	NPC472687
0.7063	Intermediate Similarity	NPC9714
0.7049	Intermediate Similarity	NPC328052
0.7043	Intermediate Similarity	NPC93271
0.7043	Intermediate Similarity	NPC473164
0.7043	Intermediate Similarity	NPC135576
0.7034	Intermediate Similarity	NPC473163
0.7031	Intermediate Similarity	NPC315915
0.7027	Intermediate Similarity	NPC34754
0.7018	Intermediate Similarity	NPC472977
0.7018	Intermediate Similarity	NPC474690
0.7018	Intermediate Similarity	NPC53685
0.7018	Intermediate Similarity	NPC472976
0.7009	Intermediate Similarity	NPC117685
0.7	Intermediate Similarity	NPC271269
0.7	Intermediate Similarity	NPC471332
0.7	Intermediate Similarity	NPC469494
0.7	Intermediate Similarity	NPC471333
0.7	Intermediate Similarity	NPC469852
0.6992	Remote Similarity	NPC304180
0.6992	Remote Similarity	NPC179798
0.6992	Remote Similarity	NPC474315
0.6991	Remote Similarity	NPC19114
0.6983	Remote Similarity	NPC161147
0.6983	Remote Similarity	NPC473161
0.6967	Remote Similarity	NPC24389
0.6964	Remote Similarity	NPC472688
0.6964	Remote Similarity	NPC472676
0.6964	Remote Similarity	NPC5509
0.6964	Remote Similarity	NPC284561
0.6957	Remote Similarity	NPC472932
0.6949	Remote Similarity	NPC77703
0.6949	Remote Similarity	NPC244456
0.6949	Remote Similarity	NPC303559
0.6949	Remote Similarity	NPC469657
0.6949	Remote Similarity	NPC472637
0.6949	Remote Similarity	NPC175531
0.6942	Remote Similarity	NPC91034
0.6942	Remote Similarity	NPC469853
0.694	Remote Similarity	NPC116057
0.6937	Remote Similarity	NPC312561
0.693	Remote Similarity	NPC472930
0.693	Remote Similarity	NPC141447
0.6929	Remote Similarity	NPC284707
0.6923	Remote Similarity	NPC57079
0.6923	Remote Similarity	NPC316598
0.6923	Remote Similarity	NPC108368
0.6911	Remote Similarity	NPC473627
0.6911	Remote Similarity	NPC5103
0.6911	Remote Similarity	NPC46764
0.6909	Remote Similarity	NPC179006
0.6909	Remote Similarity	NPC474853
0.6903	Remote Similarity	NPC232426
0.6903	Remote Similarity	NPC472325
0.6903	Remote Similarity	NPC280592
0.6903	Remote Similarity	NPC51486
0.6903	Remote Similarity	NPC253177
0.6903	Remote Similarity	NPC213636
0.6903	Remote Similarity	NPC113393
0.6903	Remote Similarity	NPC281942
0.6899	Remote Similarity	NPC469515
0.6899	Remote Similarity	NPC46570
0.6897	Remote Similarity	NPC472675
0.6897	Remote Similarity	NPC471463
0.6897	Remote Similarity	NPC21681
0.6897	Remote Similarity	NPC249954
0.6897	Remote Similarity	NPC328371
0.6891	Remote Similarity	NPC114540
0.6891	Remote Similarity	NPC473424
0.6891	Remote Similarity	NPC80781
0.6891	Remote Similarity	NPC295791
0.6891	Remote Similarity	NPC155332
0.6891	Remote Similarity	NPC32577
0.6885	Remote Similarity	NPC89171
0.6885	Remote Similarity	NPC151393
0.6885	Remote Similarity	NPC476802
0.688	Remote Similarity	NPC56448
0.6875	Remote Similarity	NPC307298
0.6875	Remote Similarity	NPC474854
0.687	Remote Similarity	NPC299100
0.687	Remote Similarity	NPC474882
0.687	Remote Similarity	NPC196227
0.6864	Remote Similarity	NPC477720
0.6864	Remote Similarity	NPC472644
0.6864	Remote Similarity	NPC476299
0.6864	Remote Similarity	NPC474012
0.6864	Remote Similarity	NPC266955
0.686	Remote Similarity	NPC477125
0.686	Remote Similarity	NPC32006
0.686	Remote Similarity	NPC85529
0.6855	Remote Similarity	NPC188738
0.685	Remote Similarity	NPC271621
0.685	Remote Similarity	NPC59751
0.685	Remote Similarity	NPC183580
0.685	Remote Similarity	NPC23046
0.685	Remote Similarity	NPC20302
0.685	Remote Similarity	NPC284068
0.685	Remote Similarity	NPC98249
0.685	Remote Similarity	NPC53396
0.685	Remote Similarity	NPC470492
0.685	Remote Similarity	NPC474518
0.685	Remote Similarity	NPC312824
0.685	Remote Similarity	NPC286528
0.685	Remote Similarity	NPC470493
0.685	Remote Similarity	NPC140055
0.685	Remote Similarity	NPC27413
0.685	Remote Similarity	NPC167606
0.6847	Remote Similarity	NPC220478
0.6847	Remote Similarity	NPC470955
0.6846	Remote Similarity	NPC107493
0.6842	Remote Similarity	NPC471586
0.6842	Remote Similarity	NPC471329
0.6842	Remote Similarity	NPC141831
0.6842	Remote Similarity	NPC472814
0.6842	Remote Similarity	NPC296114
0.6842	Remote Similarity	NPC177037
0.6842	Remote Similarity	NPC303697
0.6842	Remote Similarity	NPC472975
0.6842	Remote Similarity	NPC116726
0.6838	Remote Similarity	NPC474977
0.6838	Remote Similarity	NPC474343
0.6835	Remote Similarity	NPC208725
0.6833	Remote Similarity	NPC111323
0.6833	Remote Similarity	NPC329345
0.6833	Remote Similarity	NPC475526
0.6833	Remote Similarity	NPC159533
0.6833	Remote Similarity	NPC99266
0.6833	Remote Similarity	NPC473283
0.6825	Remote Similarity	NPC147912
0.6825	Remote Similarity	NPC67259

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 NPC476190 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	89
0.1-0.2	496
0.2-0.3	2388
0.3-0.4	3856
0.4-0.5	1822
0.5-0.6	442
0.6-0.7	56
0.7-0.8	1
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
0.7519	Intermediate Similarity	NPD6914	Discontinued
0.6992	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.694	Remote Similarity	NPD7260	Phase 2
0.685	Remote Similarity	NPD7115	Discovery
0.6846	Remote Similarity	NPD7623	Phase 3
0.6846	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD7739	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD6404	Discontinued
0.6719	Remote Similarity	NPD7500	Approved
0.6639	Remote Similarity	NPD4225	Approved
0.6638	Remote Similarity	NPD5778	Approved
0.6638	Remote Similarity	NPD5779	Approved
0.6589	Remote Similarity	NPD7505	Discontinued
0.6585	Remote Similarity	NPD6640	Phase 3
0.6552	Remote Similarity	NPD6079	Approved
0.6552	Remote Similarity	NPD6411	Approved
0.6522	Remote Similarity	NPD5328	Approved
0.6519	Remote Similarity	NPD8074	Phase 3
0.6519	Remote Similarity	NPD7747	Phase 1
0.6519	Remote Similarity	NPD7746	Phase 1
0.6508	Remote Similarity	NPD6420	Discontinued
0.6466	Remote Similarity	NPD5785	Approved
0.6404	Remote Similarity	NPD5279	Phase 3
0.6403	Remote Similarity	NPD6845	Suspended
0.6379	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD6101	Approved
0.6372	Remote Similarity	NPD3133	Approved
0.6372	Remote Similarity	NPD3666	Approved
0.6372	Remote Similarity	NPD4786	Approved
0.6372	Remote Similarity	NPD3665	Phase 1
0.6349	Remote Similarity	NPD6686	Approved
0.6341	Remote Similarity	NPD5211	Phase 2
0.6339	Remote Similarity	NPD3667	Approved
0.6333	Remote Similarity	NPD5221	Approved
0.6333	Remote Similarity	NPD5222	Approved
0.6333	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD5173	Approved
0.6271	Remote Similarity	NPD7983	Approved
0.6269	Remote Similarity	NPD6908	Approved
0.6269	Remote Similarity	NPD6909	Approved
0.6261	Remote Similarity	NPD3618	Phase 1
0.6261	Remote Similarity	NPD4519	Discontinued
0.6261	Remote Similarity	NPD4623	Approved
0.625	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4634	Approved
0.624	Remote Similarity	NPD5141	Approved
0.6198	Remote Similarity	NPD7839	Suspended
0.6198	Remote Similarity	NPD4697	Phase 3
0.6195	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6194	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.6181	Remote Similarity	NPD6334	Approved
0.6181	Remote Similarity	NPD6333	Approved
0.6179	Remote Similarity	NPD5285	Approved
0.6179	Remote Similarity	NPD5286	Approved
0.6179	Remote Similarity	NPD7639	Approved
0.6179	Remote Similarity	NPD7640	Approved
0.6179	Remote Similarity	NPD4696	Approved
0.6176	Remote Similarity	NPD7830	Approved
0.6176	Remote Similarity	NPD7829	Approved
0.6172	Remote Similarity	NPD6413	Approved
0.6161	Remote Similarity	NPD4695	Discontinued
0.6154	Remote Similarity	NPD8297	Approved
0.6148	Remote Similarity	NPD4755	Approved
0.6148	Remote Similarity	NPD6921	Approved
0.6142	Remote Similarity	NPD6412	Phase 2
0.6134	Remote Similarity	NPD7515	Phase 2
0.6134	Remote Similarity	NPD7637	Suspended
0.6129	Remote Similarity	NPD5223	Approved
0.6124	Remote Similarity	NPD6371	Approved
0.6124	Remote Similarity	NPD6421	Discontinued
0.6121	Remote Similarity	NPD5786	Approved
0.6107	Remote Similarity	NPD4632	Approved
0.6102	Remote Similarity	NPD4753	Phase 2
0.6102	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD7638	Approved
0.6094	Remote Similarity	NPD6881	Approved
0.6094	Remote Similarity	NPD6899	Approved
0.6087	Remote Similarity	NPD8451	Approved
0.6083	Remote Similarity	NPD6399	Phase 3
0.608	Remote Similarity	NPD5224	Approved
0.608	Remote Similarity	NPD5225	Approved
0.608	Remote Similarity	NPD5226	Approved
0.608	Remote Similarity	NPD4633	Approved
0.6077	Remote Similarity	NPD7601	Clinical (unspecified phase)
0.6074	Remote Similarity	NPD6319	Approved
0.6074	Remote Similarity	NPD6054	Approved
0.6071	Remote Similarity	NPD7319	Approved
0.6063	Remote Similarity	NPD7128	Approved
0.6063	Remote Similarity	NPD5739	Approved
0.6063	Remote Similarity	NPD6675	Approved
0.6063	Remote Similarity	NPD6402	Approved
0.6058	Remote Similarity	NPD7604	Phase 2
0.605	Remote Similarity	NPD4096	Approved
0.6048	Remote Similarity	NPD4700	Approved
0.6047	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6043	Remote Similarity	NPD8448	Approved
0.6034	Remote Similarity	NPD1694	Approved
0.6034	Remote Similarity	NPD1696	Phase 3
0.6034	Remote Similarity	NPD5363	Approved
0.6033	Remote Similarity	NPD7748	Approved
0.6032	Remote Similarity	NPD5175	Approved
0.6032	Remote Similarity	NPD5174	Approved
0.6031	Remote Similarity	NPD6053	Discontinued
0.6029	Remote Similarity	NPD8513	Phase 3
0.6029	Remote Similarity	NPD8517	Approved
0.6029	Remote Similarity	NPD8516	Approved
0.6029	Remote Similarity	NPD8515	Approved
0.6029	Remote Similarity	NPD8444	Approved
0.6018	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD6083	Phase 2
0.6016	Remote Similarity	NPD5697	Approved
0.6016	Remote Similarity	NPD6084	Phase 2
0.6014	Remote Similarity	NPD8342	Approved
0.6014	Remote Similarity	NPD8341	Approved
0.6014	Remote Similarity	NPD8299	Approved
0.6014	Remote Similarity	NPD8340	Approved
0.6	Remote Similarity	NPD7102	Approved
0.6	Remote Similarity	NPD7290	Approved
0.6	Remote Similarity	NPD5284	Approved
0.6	Remote Similarity	NPD5281	Approved
0.6	Remote Similarity	NPD6883	Approved
0.5986	Remote Similarity	NPD7084	Phase 3
0.5985	Remote Similarity	NPD6370	Approved
0.5984	Remote Similarity	NPD5210	Approved
0.5984	Remote Similarity	NPD4629	Approved
0.5983	Remote Similarity	NPD5330	Approved
0.5983	Remote Similarity	NPD4694	Approved
0.5983	Remote Similarity	NPD7521	Approved
0.5983	Remote Similarity	NPD6409	Approved
0.5983	Remote Similarity	NPD7146	Approved
0.5983	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD6684	Approved
0.5983	Remote Similarity	NPD5280	Approved
0.5983	Remote Similarity	NPD7334	Approved
0.5971	Remote Similarity	NPD7507	Approved
0.5969	Remote Similarity	NPD7320	Approved
0.5969	Remote Similarity	NPD6011	Approved
0.5969	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5956	Remote Similarity	NPD6059	Approved
0.5954	Remote Similarity	NPD8130	Phase 1
0.5954	Remote Similarity	NPD6847	Approved
0.5954	Remote Similarity	NPD6649	Approved
0.5954	Remote Similarity	NPD6869	Approved
0.5954	Remote Similarity	NPD6617	Approved
0.5954	Remote Similarity	NPD6650	Approved
0.595	Remote Similarity	NPD4202	Approved
0.5948	Remote Similarity	NPD3668	Phase 3
0.5942	Remote Similarity	NPD7642	Approved
0.5938	Remote Similarity	NPD7333	Discontinued
0.5932	Remote Similarity	NPD7524	Approved
0.5926	Remote Similarity	NPD7641	Discontinued
0.5923	Remote Similarity	NPD6372	Approved
0.5923	Remote Similarity	NPD6014	Approved
0.5923	Remote Similarity	NPD6012	Approved
0.5923	Remote Similarity	NPD6373	Approved
0.5923	Remote Similarity	NPD6013	Approved
0.5921	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD46	Approved
0.5917	Remote Similarity	NPD6698	Approved
0.5915	Remote Similarity	NPD8391	Approved
0.5915	Remote Similarity	NPD8392	Approved
0.5915	Remote Similarity	NPD8390	Approved
0.5913	Remote Similarity	NPD4223	Phase 3
0.5913	Remote Similarity	NPD4270	Approved
0.5913	Remote Similarity	NPD4269	Approved
0.5913	Remote Similarity	NPD4221	Approved
0.5912	Remote Similarity	NPD6015	Approved
0.5912	Remote Similarity	NPD6016	Approved
0.5909	Remote Similarity	NPD6882	Approved
0.5906	Remote Similarity	NPD4754	Approved
0.5902	Remote Similarity	NPD5282	Discontinued
0.5902	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.5899	Remote Similarity	NPD7492	Approved
0.5897	Remote Similarity	NPD5329	Approved
0.5891	Remote Similarity	NPD5701	Approved
0.5887	Remote Similarity	NPD7902	Approved
0.5882	Remote Similarity	NPD6672	Approved
0.5882	Remote Similarity	NPD5737	Approved
0.5882	Remote Similarity	NPD6903	Approved
0.5882	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.587	Remote Similarity	NPD8080	Discontinued
0.587	Remote Similarity	NPD5988	Approved
0.5862	Remote Similarity	NPD6110	Phase 1
0.5857	Remote Similarity	NPD6616	Approved
0.5857	Remote Similarity	NPD8273	Phase 1
0.5856	Remote Similarity	NPD8264	Approved
0.5854	Remote Similarity	NPD5695	Phase 3
0.5852	Remote Similarity	NPD6009	Approved
0.5847	Remote Similarity	NPD5690	Phase 2
0.5846	Remote Similarity	NPD4729	Approved
0.5846	Remote Similarity	NPD4730	Approved
0.5846	Remote Similarity	NPD5168	Approved
0.5841	Remote Similarity	NPD3617	Approved
0.5841	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD1719	Phase 1
0.5833	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5827	Remote Similarity	NPD8328	Phase 3
0.582	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD7078	Approved
0.5814	Remote Similarity	NPD4768	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