NPASS Compound

Structure

CID316186 OpenBabel06191716132D 31 33 0 0 1 0 0 0 0 0999 V2000 2.5981 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3569 -3.3320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6712 1.5731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0981 1.3660 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 -2.2321 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9641 -1.8660 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 -4.0981 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9641 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4641 -1.0000 0.0000 C 0 0 2 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 -1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.1962 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4641 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.3301 0.5000 0.0000 C 0 0 2 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 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -8.0622 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3301 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 1 4 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 5 2 0 0 0 0 5 6 1 0 0 0 0 6 7 2 0 0 0 0 7 10 1 0 0 0 0 8 9 1 0 0 0 0 8 11 2 0 0 0 0 9 19 2 0 0 0 0 12 13 2 0 0 0 0 12 18 1 0 0 0 0 14 15 2 0 0 0 0 15 24 1 0 0 0 0 16 18 2 0 0 0 0 16 21 1 0 0 0 0 17 20 1 0 0 0 0 17 22 1 0 0 0 0 20 13 1 6 0 0 0 20 23 1 0 0 0 0 21 14 1 1 0 0 0 21 25 1 0 0 0 0 22 10 1 6 0 0 0 22 28 1 0 0 0 0 23 11 1 1 0 0 0 23 27 1 0 0 0 0 24 26 1 0 0 0 0 24 29 1 1 0 0 0 25 19 1 6 0 0 0 25 26 1 0 0 0 0 26 30 1 1 0 0 0 27 28 2 0 0 0 0 27 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	421.26
Volume:	466.154
LogP:	1.8
LogD:	2.073
LogS:	-3.307
# Rotatable Bonds:	3
TPSA:	69.56
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.473
Synthetic Accessibility Score:	5.838
Fsp3:	0.444
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.812
MDCK Permeability:	8.735389201319776e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.134
Human Intestinal Absorption (HIA):	0.029
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.206
Plasma Protein Binding (PPB):	92.61151885986328%
Volume Distribution (VD):	0.858
Pgp-substrate:	3.7743513584136963%

ADMET: Metabolism

CYP1A2-inhibitor:	0.254
CYP1A2-substrate:	0.22
CYP2C19-inhibitor:	0.176
CYP2C19-substrate:	0.516
CYP2C9-inhibitor:	0.418
CYP2C9-substrate:	0.846
CYP2D6-inhibitor:	0.468
CYP2D6-substrate:	0.874
CYP3A4-inhibitor:	0.813
CYP3A4-substrate:	0.21

ADMET: Excretion

Clearance (CL):	0.897
Half-life (T1/2):	0.461

ADMET: Toxicity

hERG Blockers:	0.265
Human Hepatotoxicity (H-HT):	0.893
Drug-inuced Liver Injury (DILI):	0.31
AMES Toxicity:	0.776
Rat Oral Acute Toxicity:	0.526
Maximum Recommended Daily Dose:	0.956
Skin Sensitization:	0.773
Carcinogencity:	0.034
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.901

Download Data

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

Natural Product: NPC316186

Natural Product ID:	NPC316186
*Common Name:**	UIBDXMJAGQYGAG-NYBNEGNOSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	UIBDXMJAGQYGAG-NYBNEGNOSA-N
Standard InCHI:	InChI=1S/C27H35NO3/c1-4-5-6-7-10-22-17-20-13-12-18(2)16-21-14-15-24(29)26(30)25(21)19(3)9-8-11-23(20)27(31)28-22/h4-9,11-16,20-26,29-30H,10,17H2,1-3H3,(H,28,31)/b5-4+,7-6+,11-8+,13-12+,18-16+,19-9+/t20-,21+,22+,23+,24+,25+,26+/m0/s1
SMILES:	C/C=C/C=C/C[C@@H]1C[C@@H]2/C=C/C(=C/[C@H]3C=C[C@H]([C@H]([C@@H]3/C(=C/C=C/[C@H]2C(=N1)O)/C)O)O)/C
Synthetic Gene Cluster:	BGC0001349;BGC0001349;
ChEMBL Identifier:	CHEMBL3109453
PubChem CID:	76332081
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000064] Macrolactams

*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
NPO40641	Streptomyces sp. SCSIO 03032	Strain	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24547685]
NPO40641	Streptomyces sp. SCSIO 03032	Strain	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25069084]

☑ 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	3
MIC	5

Activity Type	# Activity
Cell Line	3
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	>	100000.0	nM	PMID[521326]
NPT395	Cell Line	SF-268	Homo sapiens	IC50	>	100000.0	nM	PMID[521326]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	100000.0	nM	PMID[521326]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	128.0	ug.mL-1	PMID[521326]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	128.0	ug.mL-1	PMID[521326]
NPT1261	Organism	Bacillus thuringiensis	Bacillus thuringiensis	MIC	>	128.0	ug.mL-1	PMID[521326]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	128.0	ug.mL-1	PMID[521326]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	128.0	ug.mL-1	PMID[521326]

☑ 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 NPC316186 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	76
0.1-0.2	468
0.2-0.3	7626
0.3-0.4	22000
0.4-0.5	10241
0.5-0.6	2087
0.6-0.7	186
0.7-0.8	11
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7556	Intermediate Similarity	NPC224072
0.7525	Intermediate Similarity	NPC45365
0.7525	Intermediate Similarity	NPC293299
0.7447	Intermediate Similarity	NPC34754
0.7391	Intermediate Similarity	NPC477199
0.7326	Intermediate Similarity	NPC314678
0.7229	Intermediate Similarity	NPC315141
0.7229	Intermediate Similarity	NPC129995
0.7071	Intermediate Similarity	NPC243985
0.7071	Intermediate Similarity	NPC280710
0.7045	Intermediate Similarity	NPC288086
0.703	Intermediate Similarity	NPC240650
0.6989	Remote Similarity	NPC39966
0.6977	Remote Similarity	NPC291196
0.6977	Remote Similarity	NPC103712
0.6931	Remote Similarity	NPC475503
0.6923	Remote Similarity	NPC247060
0.6923	Remote Similarity	NPC50815
0.6916	Remote Similarity	NPC307903
0.6916	Remote Similarity	NPC140251
0.6824	Remote Similarity	NPC267027
0.6789	Remote Similarity	NPC113012
0.6789	Remote Similarity	NPC122926
0.6778	Remote Similarity	NPC264417
0.6778	Remote Similarity	NPC217095
0.6762	Remote Similarity	NPC471083
0.6737	Remote Similarity	NPC228638
0.6727	Remote Similarity	NPC29501
0.6706	Remote Similarity	NPC477525
0.67	Remote Similarity	NPC314500
0.6699	Remote Similarity	NPC4834
0.6699	Remote Similarity	NPC475646
0.6698	Remote Similarity	NPC474563
0.6667	Remote Similarity	NPC251330
0.6628	Remote Similarity	NPC326310
0.6596	Remote Similarity	NPC476560
0.6593	Remote Similarity	NPC69383
0.6593	Remote Similarity	NPC313179
0.6593	Remote Similarity	NPC171148
0.6574	Remote Similarity	NPC271269
0.6574	Remote Similarity	NPC472615
0.6574	Remote Similarity	NPC154601
0.6569	Remote Similarity	NPC473314
0.6559	Remote Similarity	NPC167891
0.6559	Remote Similarity	NPC83351
0.6556	Remote Similarity	NPC130665
0.6529	Remote Similarity	NPC278097
0.6526	Remote Similarity	NPC475724
0.6518	Remote Similarity	NPC476269
0.6512	Remote Similarity	NPC308844
0.6506	Remote Similarity	NPC122239
0.6489	Remote Similarity	NPC471597
0.6481	Remote Similarity	NPC472616
0.6449	Remote Similarity	NPC477198
0.6442	Remote Similarity	NPC45313
0.6442	Remote Similarity	NPC175614
0.6442	Remote Similarity	NPC197294
0.6442	Remote Similarity	NPC183449
0.6442	Remote Similarity	NPC8098
0.6441	Remote Similarity	NPC469943
0.6422	Remote Similarity	NPC55462
0.6404	Remote Similarity	NPC471560
0.6404	Remote Similarity	NPC473893
0.6396	Remote Similarity	NPC133729
0.6395	Remote Similarity	NPC253468
0.6395	Remote Similarity	NPC235311
0.6389	Remote Similarity	NPC473254
0.6389	Remote Similarity	NPC474583
0.6386	Remote Similarity	NPC321030
0.6386	Remote Similarity	NPC226848
0.6381	Remote Similarity	NPC140300
0.6364	Remote Similarity	NPC470365
0.6364	Remote Similarity	NPC315426
0.6364	Remote Similarity	NPC114651
0.6364	Remote Similarity	NPC169375
0.6353	Remote Similarity	NPC29468
0.6339	Remote Similarity	NPC476290
0.6333	Remote Similarity	NPC34834
0.6311	Remote Similarity	NPC472414
0.631	Remote Similarity	NPC329003
0.631	Remote Similarity	NPC326524
0.631	Remote Similarity	NPC475931
0.631	Remote Similarity	NPC325550
0.6293	Remote Similarity	NPC476190
0.6289	Remote Similarity	NPC477390
0.6289	Remote Similarity	NPC477385
0.6279	Remote Similarity	NPC471023
0.6277	Remote Similarity	NPC91594
0.6275	Remote Similarity	NPC477865
0.6275	Remote Similarity	NPC477866
0.6273	Remote Similarity	NPC258130
0.6262	Remote Similarity	NPC316730
0.6261	Remote Similarity	NPC474544
0.6261	Remote Similarity	NPC1986
0.625	Remote Similarity	NPC16709
0.625	Remote Similarity	NPC23454
0.625	Remote Similarity	NPC262312
0.625	Remote Similarity	NPC256570
0.625	Remote Similarity	NPC158445
0.625	Remote Similarity	NPC35269
0.625	Remote Similarity	NPC202017
0.625	Remote Similarity	NPC157353
0.625	Remote Similarity	NPC70323
0.625	Remote Similarity	NPC311736
0.625	Remote Similarity	NPC54961
0.625	Remote Similarity	NPC192066
0.625	Remote Similarity	NPC17290
0.625	Remote Similarity	NPC282088
0.625	Remote Similarity	NPC3568
0.625	Remote Similarity	NPC156782
0.625	Remote Similarity	NPC207657
0.6239	Remote Similarity	NPC90538
0.6239	Remote Similarity	NPC55336
0.6235	Remote Similarity	NPC130807
0.6235	Remote Similarity	NPC99487
0.6235	Remote Similarity	NPC66020
0.6228	Remote Similarity	NPC314550
0.6224	Remote Similarity	NPC470384
0.622	Remote Similarity	NPC329686
0.6216	Remote Similarity	NPC475800
0.6211	Remote Similarity	NPC473695
0.6211	Remote Similarity	NPC473446
0.6211	Remote Similarity	NPC469492
0.6207	Remote Similarity	NPC172197
0.6207	Remote Similarity	NPC274293
0.6204	Remote Similarity	NPC175531
0.6204	Remote Similarity	NPC469457
0.6195	Remote Similarity	NPC472359
0.619	Remote Similarity	NPC58674
0.619	Remote Similarity	NPC189764
0.619	Remote Similarity	NPC272732
0.619	Remote Similarity	NPC155025
0.619	Remote Similarity	NPC311164
0.619	Remote Similarity	NPC181872
0.6186	Remote Similarity	NPC82799
0.6182	Remote Similarity	NPC88267
0.6182	Remote Similarity	NPC224610
0.6182	Remote Similarity	NPC113326
0.6182	Remote Similarity	NPC194390
0.618	Remote Similarity	NPC163290
0.618	Remote Similarity	NPC73603
0.618	Remote Similarity	NPC82337
0.6172	Remote Similarity	NPC228511
0.617	Remote Similarity	NPC236228
0.617	Remote Similarity	NPC256720
0.617	Remote Similarity	NPC315261
0.617	Remote Similarity	NPC265588
0.6163	Remote Similarity	NPC207007
0.6163	Remote Similarity	NPC68679
0.6163	Remote Similarity	NPC321867
0.6163	Remote Similarity	NPC225342
0.6162	Remote Similarity	NPC238485
0.616	Remote Similarity	NPC295478
0.616	Remote Similarity	NPC71271
0.6154	Remote Similarity	NPC271621
0.6154	Remote Similarity	NPC59751
0.6154	Remote Similarity	NPC189745
0.6154	Remote Similarity	NPC27413
0.6146	Remote Similarity	NPC469517
0.6146	Remote Similarity	NPC233295
0.6124	Remote Similarity	NPC279045
0.6124	Remote Similarity	NPC113325
0.6122	Remote Similarity	NPC471408
0.6117	Remote Similarity	NPC209047
0.6117	Remote Similarity	NPC139782
0.6117	Remote Similarity	NPC74672
0.6117	Remote Similarity	NPC242503
0.6117	Remote Similarity	NPC43074
0.6111	Remote Similarity	NPC224532
0.6111	Remote Similarity	NPC275686
0.6111	Remote Similarity	NPC272961
0.6106	Remote Similarity	NPC474725
0.6105	Remote Similarity	NPC40049
0.6092	Remote Similarity	NPC473508
0.6087	Remote Similarity	NPC95863
0.6087	Remote Similarity	NPC242001
0.6082	Remote Similarity	NPC234193
0.6082	Remote Similarity	NPC96362
0.6071	Remote Similarity	NPC25340
0.6067	Remote Similarity	NPC113224
0.6064	Remote Similarity	NPC66566
0.6064	Remote Similarity	NPC477923
0.6061	Remote Similarity	NPC317458
0.6061	Remote Similarity	NPC320548
0.6061	Remote Similarity	NPC57370
0.6061	Remote Similarity	NPC471595
0.6061	Remote Similarity	NPC474634
0.6058	Remote Similarity	NPC15851
0.6058	Remote Similarity	NPC473604
0.6058	Remote Similarity	NPC182632
0.6058	Remote Similarity	NPC473950
0.6058	Remote Similarity	NPC282705
0.6058	Remote Similarity	NPC475125
0.6058	Remote Similarity	NPC111567
0.6058	Remote Similarity	NPC473581
0.6058	Remote Similarity	NPC263545
0.6058	Remote Similarity	NPC186840
0.6058	Remote Similarity	NPC309898
0.6055	Remote Similarity	NPC313234
0.6055	Remote Similarity	NPC77703

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 NPC316186 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	78
0.1-0.2	358
0.2-0.3	3031
0.3-0.4	4159
0.4-0.5	1339
0.5-0.6	176
0.6-0.7	9
0.7-0.8	0
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
0.6593	Remote Similarity	NPD8264	Approved
0.6574	Remote Similarity	NPD6640	Phase 3
0.6569	Remote Similarity	NPD5771	Approved
0.6429	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD6420	Discontinued
0.6339	Remote Similarity	NPD6421	Discontinued
0.6222	Remote Similarity	NPD791	Approved
0.6222	Remote Similarity	NPD15	Approved
0.6211	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.617	Remote Similarity	NPD6933	Approved
0.6167	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD7623	Phase 3
0.6163	Remote Similarity	NPD368	Approved
0.6161	Remote Similarity	NPD6406	Approved
0.6117	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD7739	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD7332	Phase 2
0.6082	Remote Similarity	NPD7514	Phase 3
0.6042	Remote Similarity	NPD7145	Approved
0.6038	Remote Similarity	NPD4814	Discontinued
0.602	Remote Similarity	NPD6902	Approved
0.6	Remote Similarity	NPD1346	Approved
0.5979	Remote Similarity	NPD6929	Approved
0.5978	Remote Similarity	NPD7144	Approved
0.5978	Remote Similarity	NPD7143	Approved
0.5968	Remote Similarity	NPD7747	Phase 1
0.5968	Remote Similarity	NPD7746	Phase 1
0.5957	Remote Similarity	NPD6924	Approved
0.5957	Remote Similarity	NPD6926	Approved
0.5938	Remote Similarity	NPD5776	Phase 2
0.5938	Remote Similarity	NPD6925	Approved
0.5918	Remote Similarity	NPD6930	Phase 2
0.5918	Remote Similarity	NPD6931	Approved
0.5917	Remote Similarity	NPD7522	Discontinued
0.5914	Remote Similarity	NPD7150	Approved
0.5914	Remote Similarity	NPD7152	Approved
0.5914	Remote Similarity	NPD3187	Discontinued
0.5914	Remote Similarity	NPD7151	Approved
0.5882	Remote Similarity	NPD7505	Discontinued
0.5882	Remote Similarity	NPD7500	Approved
0.587	Remote Similarity	NPD6923	Approved
0.587	Remote Similarity	NPD1082	Approved
0.587	Remote Similarity	NPD6922	Approved
0.5862	Remote Similarity	NPD7601	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD244	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD5357	Phase 1
0.5833	Remote Similarity	NPD342	Phase 1
0.5825	Remote Similarity	NPD7524	Approved
0.5818	Remote Similarity	NPD6404	Discontinued
0.581	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD6932	Approved
0.5766	Remote Similarity	NPD4760	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD179	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD6695	Phase 3
0.5739	Remote Similarity	NPD6038	Clinical (unspecified phase)
0.573	Remote Similarity	NPD3210	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD765	Discontinued
0.5714	Remote Similarity	NPD4719	Phase 2
0.5702	Remote Similarity	NPD7333	Discontinued
0.5701	Remote Similarity	NPD5779	Approved
0.5701	Remote Similarity	NPD6690	Approved
0.5701	Remote Similarity	NPD5778	Approved
0.57	Remote Similarity	NPD6898	Phase 1
0.569	Remote Similarity	NPD6413	Approved
0.5686	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5684	Remote Similarity	NPD4732	Discontinued
0.5631	Remote Similarity	NPD6893	Approved
0.5618	Remote Similarity	NPD835	Approved
0.5618	Remote Similarity	NPD834	Approved
0.5612	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.561	Remote Similarity	NPD2217	Approved
0.561	Remote Similarity	NPD2218	Phase 2
0.56	Remote Similarity	NPD7509	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data