NPASS Compound

Structure

NPC473315 OpenBabel07101718302D 40 41 0 0 1 0 0 0 0 0999 V2000 9.3302 3.8647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1874 -0.4677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1874 0.5323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9286 -1.4336 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3505 -2.2997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0576 3.0714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9286 1.4982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4286 -2.2997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0576 -3.0068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8505 -1.4336 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3505 2.3643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9236 3.5714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4286 2.3643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7215 -3.0068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9236 -3.5068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5917 -0.4677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8505 1.4982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8895 3.8302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8895 -3.7656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6002 -0.6628 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7215 3.0714 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.8555 -3.5068 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8895 -3.7656 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5917 0.5323 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6088 -0.7934 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8895 3.8302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2261 -1.7172 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7654 -1.8478 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3741 -1.0544 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9914 -0.1305 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2090 -1.4562 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2381 -4.4306 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7590 -4.7570 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0201 4.8216 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8348 -2.5106 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1481 -2.7716 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3656 -1.1849 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8555 3.5714 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6002 0.6628 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 3 1 0 0 0 0 2 4 2 0 0 0 0 3 7 1 0 0 0 0 4 8 1 0 0 0 0 5 9 2 0 0 0 0 5 10 1 0 0 0 0 6 11 2 0 0 0 0 6 12 1 0 0 0 0 7 13 1 0 0 0 0 8 14 2 0 0 0 0 9 15 1 0 0 0 0 10 16 2 0 0 0 0 11 17 1 0 0 0 0 12 18 2 0 0 0 0 13 21 1 0 0 0 0 14 22 1 0 0 0 0 15 23 1 0 0 0 0 16 24 1 0 0 0 0 17 24 1 0 0 0 0 18 26 1 0 0 0 0 19 22 1 0 0 0 0 19 23 1 0 0 0 0 20 31 1 0 0 0 0 21 1 1 6 0 0 0 21 38 1 0 0 0 0 22 32 1 6 0 0 0 23 33 1 1 0 0 0 24 39 1 1 0 0 0 25 20 1 6 0 0 0 25 27 1 0 0 0 0 25 40 1 0 0 0 0 26 34 2 0 0 0 0 26 38 1 0 0 0 0 27 28 1 0 0 0 0 27 35 1 1 0 0 0 28 29 1 0 0 0 0 28 36 1 6 0 0 0 29 30 1 0 0 0 0 29 37 1 1 0 0 0 30 39 1 6 0 0 0 30 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	564.29
Volume:	579.77
LogP:	-0.371
LogD:	-0.005
LogS:	-3.339
# Rotatable Bonds:	3
TPSA:	166.14
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	2
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.277
Synthetic Accessibility Score:	5.704
Fsp3:	0.567
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:	-5.315
MDCK Permeability:	3.471802483545616e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.988
Human Intestinal Absorption (HIA):	0.195
20% Bioavailability (F20%):	0.981
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.196
Plasma Protein Binding (PPB):	80.11483001708984%
Volume Distribution (VD):	0.614
Pgp-substrate:	5.023828029632568%

ADMET: Metabolism

CYP1A2-inhibitor:	0.105
CYP1A2-substrate:	0.023
CYP2C19-inhibitor:	0.074
CYP2C19-substrate:	0.137
CYP2C9-inhibitor:	0.051
CYP2C9-substrate:	0.992
CYP2D6-inhibitor:	0.075
CYP2D6-substrate:	0.878
CYP3A4-inhibitor:	0.294
CYP3A4-substrate:	0.067

ADMET: Excretion

Clearance (CL):	0.952
Half-life (T1/2):	0.56

ADMET: Toxicity

hERG Blockers:	0.59
Human Hepatotoxicity (H-HT):	0.903
Drug-inuced Liver Injury (DILI):	0.16
AMES Toxicity:	0.803
Rat Oral Acute Toxicity:	0.072
Maximum Recommended Daily Dose:	0.991
Skin Sensitization:	0.956
Carcinogencity:	0.313
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.921

Download Data

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

Natural Product: NPC473315

Natural Product ID:	NPC473315
*Common Name:**	Macrolactin R
IUPAC Name:	(3Z,5E,8S,9E,11E,14S,16R,17E,19E,24R)-14,16-dihydroxy-24-methyl-8-[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-2-one
Synonyms:	Macrolactin R
Standard InCHIKey:	NDMBRILKNZCXKI-FBUUVNIESA-N
Standard InCHI:	InChI=1S/C30H44O10/c1-21-13-7-3-2-4-8-14-22(32)19-23(33)15-9-5-10-16-24(17-11-6-12-18-26(34)38-21)39-30-29(37)28(36)27(35)25(20-31)40-30/h2,4-6,8-12,14,16,18,21-25,27-33,35-37H,3,7,13,15,17,19-20H2,1H3/b4-2+,9-5+,11-6+,14-8+,16-10+,18-12-/t21-,22+,23+,24-,25+,27+,28-,29+,30+/m1/s1
SMILES:	CC1CCCC=CC=CC(CC(CC=CC=CC(CC=CC=CC(=O)O1)OC2C(C(C(C(O2)CO)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL399871
PubChem CID:	44444961
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO32689	bacillus sp. ah159-1	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[17887720]

☑ 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	1
Others	2

Activity Type	# Activity
Individual Protein	1
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6049	Individual Protein	Peptide deformylase	Staphylococcus aureus subsp. aureus Mu50	IC50	=	61500.0	nM	PMID[515200]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MRC	=	100.0	ug ml-1	PMID[515200]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MRC	=	100.0	ug ml-1	PMID[515200]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	100.0	ug.mL-1	PMID[515200]

☑ 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 NPC473315 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	174
0.1-0.2	1889
0.2-0.3	6082
0.3-0.4	15305
0.4-0.5	11963
0.5-0.6	5655
0.6-0.7	1335
0.7-0.8	241
0.8-0.85	30
0.85-0.9	10
0.9-0.95	7
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC142111
0.9872	High Similarity	NPC473308
0.987	High Similarity	NPC251026
0.9625	High Similarity	NPC208473
0.939	High Similarity	NPC470137
0.9241	High Similarity	NPC469469
0.9036	High Similarity	NPC118077
0.9036	High Similarity	NPC475186
0.8941	High Similarity	NPC473311
0.8846	High Similarity	NPC326661
0.8675	High Similarity	NPC475035
0.8675	High Similarity	NPC266718
0.8605	High Similarity	NPC285588
0.8588	High Similarity	NPC475037
0.8571	High Similarity	NPC470124
0.8519	High Similarity	NPC180725
0.8415	Intermediate Similarity	NPC470147
0.8415	Intermediate Similarity	NPC127295
0.8415	Intermediate Similarity	NPC163362
0.8415	Intermediate Similarity	NPC133226
0.8409	Intermediate Similarity	NPC110072
0.8395	Intermediate Similarity	NPC248775
0.8354	Intermediate Similarity	NPC472174
0.8354	Intermediate Similarity	NPC472173
0.8353	Intermediate Similarity	NPC475034
0.8315	Intermediate Similarity	NPC472196
0.8315	Intermediate Similarity	NPC238090
0.8315	Intermediate Similarity	NPC472195
0.8295	Intermediate Similarity	NPC327253
0.8293	Intermediate Similarity	NPC1180
0.8293	Intermediate Similarity	NPC470149
0.8293	Intermediate Similarity	NPC470148
0.8272	Intermediate Similarity	NPC474026
0.8228	Intermediate Similarity	NPC132938
0.8222	Intermediate Similarity	NPC294293
0.8222	Intermediate Similarity	NPC159698
0.8205	Intermediate Similarity	NPC476037
0.8205	Intermediate Similarity	NPC476012
0.8202	Intermediate Similarity	NPC469410
0.8171	Intermediate Similarity	NPC133377
0.8111	Intermediate Similarity	NPC320552
0.809	Intermediate Similarity	NPC118078
0.8085	Intermediate Similarity	NPC2313
0.8085	Intermediate Similarity	NPC471637
0.8085	Intermediate Similarity	NPC154132
0.8085	Intermediate Similarity	NPC57586
0.8085	Intermediate Similarity	NPC475157
0.8085	Intermediate Similarity	NPC475655
0.8049	Intermediate Similarity	NPC110813
0.8049	Intermediate Similarity	NPC233071
0.8	Intermediate Similarity	NPC329890
0.8	Intermediate Similarity	NPC329914
0.7938	Intermediate Similarity	NPC315070
0.7935	Intermediate Similarity	NPC170204
0.7927	Intermediate Similarity	NPC229655
0.7927	Intermediate Similarity	NPC188860
0.7922	Intermediate Similarity	NPC146811
0.7917	Intermediate Similarity	NPC197736
0.7857	Intermediate Similarity	NPC179933
0.7805	Intermediate Similarity	NPC327041
0.7805	Intermediate Similarity	NPC285840
0.7802	Intermediate Similarity	NPC477749
0.7792	Intermediate Similarity	NPC19769
0.7778	Intermediate Similarity	NPC477748
0.7778	Intermediate Similarity	NPC284006
0.7778	Intermediate Similarity	NPC327383
0.7778	Intermediate Similarity	NPC185186
0.7753	Intermediate Similarity	NPC313658
0.7753	Intermediate Similarity	NPC316138
0.775	Intermediate Similarity	NPC474078
0.7738	Intermediate Similarity	NPC477314
0.7727	Intermediate Similarity	NPC471494
0.7722	Intermediate Similarity	NPC63873
0.7717	Intermediate Similarity	NPC61201
0.7692	Intermediate Similarity	NPC303451
0.7692	Intermediate Similarity	NPC6414
0.7692	Intermediate Similarity	NPC202886
0.7692	Intermediate Similarity	NPC201356
0.7684	Intermediate Similarity	NPC203627
0.7683	Intermediate Similarity	NPC107654
0.7683	Intermediate Similarity	NPC315843
0.7674	Intermediate Similarity	NPC21693
0.7674	Intermediate Similarity	NPC236649
0.7662	Intermediate Similarity	NPC13143
0.7662	Intermediate Similarity	NPC294813
0.766	Intermediate Similarity	NPC288350
0.766	Intermediate Similarity	NPC173329
0.7654	Intermediate Similarity	NPC293114
0.7654	Intermediate Similarity	NPC475762
0.764	Intermediate Similarity	NPC311163
0.7634	Intermediate Similarity	NPC256368
0.7629	Intermediate Similarity	NPC201191
0.7619	Intermediate Similarity	NPC475711
0.7564	Intermediate Similarity	NPC96414
0.7553	Intermediate Similarity	NPC469543
0.7525	Intermediate Similarity	NPC133625
0.75	Intermediate Similarity	NPC470313
0.75	Intermediate Similarity	NPC38295
0.75	Intermediate Similarity	NPC315559
0.75	Intermediate Similarity	NPC156089
0.75	Intermediate Similarity	NPC473500
0.7474	Intermediate Similarity	NPC306041
0.7473	Intermediate Similarity	NPC137368
0.7471	Intermediate Similarity	NPC184208
0.7471	Intermediate Similarity	NPC280367
0.7471	Intermediate Similarity	NPC315731
0.7471	Intermediate Similarity	NPC8538
0.7468	Intermediate Similarity	NPC276299
0.7449	Intermediate Similarity	NPC195510
0.7449	Intermediate Similarity	NPC13171
0.7442	Intermediate Similarity	NPC321728
0.7439	Intermediate Similarity	NPC316185
0.7436	Intermediate Similarity	NPC25747
0.7436	Intermediate Similarity	NPC148233
0.7423	Intermediate Similarity	NPC255677
0.7423	Intermediate Similarity	NPC22149
0.7423	Intermediate Similarity	NPC306344
0.7419	Intermediate Similarity	NPC9447
0.7419	Intermediate Similarity	NPC472199
0.7419	Intermediate Similarity	NPC472197
0.7416	Intermediate Similarity	NPC288471
0.7403	Intermediate Similarity	NPC26810
0.7396	Intermediate Similarity	NPC475332
0.7386	Intermediate Similarity	NPC313677
0.7374	Intermediate Similarity	NPC234304
0.7374	Intermediate Similarity	NPC267869
0.7374	Intermediate Similarity	NPC284929
0.7374	Intermediate Similarity	NPC197541
0.7374	Intermediate Similarity	NPC118761
0.7363	Intermediate Similarity	NPC45409
0.7349	Intermediate Similarity	NPC55652
0.7347	Intermediate Similarity	NPC20673
0.7347	Intermediate Similarity	NPC219038
0.7347	Intermediate Similarity	NPC28304
0.7347	Intermediate Similarity	NPC298255
0.734	Intermediate Similarity	NPC320089
0.7333	Intermediate Similarity	NPC73166
0.732	Intermediate Similarity	NPC475653
0.7312	Intermediate Similarity	NPC3952
0.7312	Intermediate Similarity	NPC177668
0.7312	Intermediate Similarity	NPC117596
0.7312	Intermediate Similarity	NPC471569
0.7312	Intermediate Similarity	NPC473904
0.7308	Intermediate Similarity	NPC321272
0.7308	Intermediate Similarity	NPC328074
0.7308	Intermediate Similarity	NPC470025
0.7308	Intermediate Similarity	NPC317460
0.7303	Intermediate Similarity	NPC284472
0.7303	Intermediate Similarity	NPC229799
0.7303	Intermediate Similarity	NPC286770
0.73	Intermediate Similarity	NPC86095
0.7292	Intermediate Similarity	NPC255410
0.7284	Intermediate Similarity	NPC475760
0.7273	Intermediate Similarity	NPC222062
0.7273	Intermediate Similarity	NPC471599
0.7263	Intermediate Similarity	NPC472198
0.7262	Intermediate Similarity	NPC477313
0.7262	Intermediate Similarity	NPC477308
0.7262	Intermediate Similarity	NPC474545
0.7262	Intermediate Similarity	NPC477315
0.7262	Intermediate Similarity	NPC477305
0.7262	Intermediate Similarity	NPC477304
0.7262	Intermediate Similarity	NPC477309
0.7262	Intermediate Similarity	NPC477312
0.7262	Intermediate Similarity	NPC477316
0.7253	Intermediate Similarity	NPC47937
0.7253	Intermediate Similarity	NPC61527
0.725	Intermediate Similarity	NPC124586
0.7245	Intermediate Similarity	NPC244878
0.7241	Intermediate Similarity	NPC139712
0.7238	Intermediate Similarity	NPC287075
0.7238	Intermediate Similarity	NPC470027
0.7234	Intermediate Similarity	NPC472125
0.7234	Intermediate Similarity	NPC472126
0.7234	Intermediate Similarity	NPC472124
0.7228	Intermediate Similarity	NPC82251
0.7222	Intermediate Similarity	NPC161670
0.7216	Intermediate Similarity	NPC120299
0.7215	Intermediate Similarity	NPC31496
0.7212	Intermediate Similarity	NPC17791
0.7204	Intermediate Similarity	NPC139418
0.7204	Intermediate Similarity	NPC133450
0.7195	Intermediate Similarity	NPC475982
0.7191	Intermediate Similarity	NPC474959
0.7191	Intermediate Similarity	NPC11383
0.7191	Intermediate Similarity	NPC475046
0.7191	Intermediate Similarity	NPC310450
0.7188	Intermediate Similarity	NPC300710
0.7176	Intermediate Similarity	NPC477306
0.7176	Intermediate Similarity	NPC260396
0.7174	Intermediate Similarity	NPC125142
0.7174	Intermediate Similarity	NPC199382
0.7172	Intermediate Similarity	NPC198992
0.7158	Intermediate Similarity	NPC109406
0.7158	Intermediate Similarity	NPC475173
0.7158	Intermediate Similarity	NPC473561
0.7158	Intermediate Similarity	NPC473723
0.7158	Intermediate Similarity	NPC473663
0.7157	Intermediate Similarity	NPC474285
0.7157	Intermediate Similarity	NPC254538

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 NPC473315 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	149
0.1-0.2	2186
0.2-0.3	4092
0.3-0.4	1994
0.4-0.5	578
0.5-0.6	128
0.6-0.7	21
0.7-0.8	2
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
0.7684	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7838	Discovery
0.7128	Intermediate Similarity	NPD46	Approved
0.7128	Intermediate Similarity	NPD6698	Approved
0.6923	Remote Similarity	NPD6686	Approved
0.6771	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD7983	Approved
0.6667	Remote Similarity	NPD7830	Approved
0.6667	Remote Similarity	NPD7829	Approved
0.6667	Remote Similarity	NPD5344	Discontinued
0.6667	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD7503	Approved
0.6569	Remote Similarity	NPD6648	Approved
0.6538	Remote Similarity	NPD1407	Approved
0.6491	Remote Similarity	NPD8517	Approved
0.6491	Remote Similarity	NPD8513	Phase 3
0.6491	Remote Similarity	NPD8515	Approved
0.6491	Remote Similarity	NPD8516	Approved
0.6422	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.642	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD7641	Discontinued
0.6348	Remote Similarity	NPD8444	Approved
0.6275	Remote Similarity	NPD7839	Suspended
0.6239	Remote Similarity	NPD7642	Approved
0.6234	Remote Similarity	NPD2269	Approved
0.6228	Remote Similarity	NPD7327	Approved
0.6228	Remote Similarity	NPD7328	Approved
0.6207	Remote Similarity	NPD8033	Approved
0.6174	Remote Similarity	NPD7516	Approved
0.6173	Remote Similarity	NPD585	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD8451	Approved
0.6121	Remote Similarity	NPD8377	Approved
0.6121	Remote Similarity	NPD8294	Approved
0.6104	Remote Similarity	NPD904	Phase 3
0.6104	Remote Similarity	NPD905	Approved
0.6083	Remote Similarity	NPD8448	Approved
0.6068	Remote Similarity	NPD8296	Approved
0.6068	Remote Similarity	NPD8380	Approved
0.6068	Remote Similarity	NPD8335	Approved
0.6068	Remote Similarity	NPD8379	Approved
0.6068	Remote Similarity	NPD8378	Approved
0.605	Remote Similarity	NPD8340	Approved
0.605	Remote Similarity	NPD8342	Approved
0.605	Remote Similarity	NPD8341	Approved
0.605	Remote Similarity	NPD8299	Approved
0.5976	Remote Similarity	NPD9119	Approved
0.5976	Remote Similarity	NPD6109	Phase 1
0.5976	Remote Similarity	NPD69	Approved
0.596	Remote Similarity	NPD4250	Approved
0.596	Remote Similarity	NPD4251	Approved
0.595	Remote Similarity	NPD8074	Phase 3
0.5949	Remote Similarity	NPD889	Approved
0.5949	Remote Similarity	NPD894	Approved
0.5949	Remote Similarity	NPD888	Phase 3
0.5949	Remote Similarity	NPD895	Approved
0.5949	Remote Similarity	NPD892	Phase 3
0.5949	Remote Similarity	NPD893	Approved
0.5949	Remote Similarity	NPD890	Clinical (unspecified phase)
0.5949	Remote Similarity	NPD887	Approved
0.5949	Remote Similarity	NPD891	Phase 3
0.5935	Remote Similarity	NPD8390	Approved
0.5935	Remote Similarity	NPD8391	Approved
0.5935	Remote Similarity	NPD8392	Approved
0.5909	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD6371	Approved
0.5882	Remote Similarity	NPD7637	Suspended
0.5878	Remote Similarity	NPD7266	Discontinued
0.5876	Remote Similarity	NPD6110	Phase 1
0.5868	Remote Similarity	NPD7507	Approved
0.5862	Remote Similarity	NPD7505	Discontinued
0.5859	Remote Similarity	NPD4249	Approved
0.5854	Remote Similarity	NPD9118	Approved
0.5849	Remote Similarity	NPD4225	Approved
0.5833	Remote Similarity	NPD6123	Approved
0.5825	Remote Similarity	NPD5778	Approved
0.5825	Remote Similarity	NPD5779	Approved
0.5795	Remote Similarity	NPD897	Approved
0.5795	Remote Similarity	NPD896	Approved
0.5795	Remote Similarity	NPD898	Approved
0.5766	Remote Similarity	NPD6412	Phase 2
0.5745	Remote Similarity	NPD4756	Discovery
0.5726	Remote Similarity	NPD7319	Approved
0.5726	Remote Similarity	NPD7500	Approved
0.5702	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5684	Remote Similarity	NPD4268	Approved
0.5684	Remote Similarity	NPD4271	Approved
0.566	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5659	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD6430	Approved
0.5652	Remote Similarity	NPD969	Suspended
0.5652	Remote Similarity	NPD6429	Approved
0.5632	Remote Similarity	NPD3197	Phase 1
0.5631	Remote Similarity	NPD5785	Approved
0.5625	Remote Similarity	NPD7329	Approved
0.5614	Remote Similarity	NPD6421	Discontinued
0.561	Remote Similarity	NPD8273	Phase 1

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