NPASS Compound

Structure

CID1180 OpenBabel06191715322D 30 31 0 0 1 0 0 0 0 0999 V2000 4.3653 -0.4368 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4135 0.0444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4926 -3.2037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1211 -3.1211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8425 -0.1742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8908 -3.4743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7406 -3.4162 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1742 -2.8425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9436 0.1495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4162 -2.7406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2037 -0.4926 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3438 -3.6374 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2988 -3.6074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0444 -2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4624 0.1343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6074 -2.2988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1343 -1.4624 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4743 -0.8908 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8232 -3.6827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1495 -1.9436 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 1 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 3.6827 -1.8232 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8546 -4.6823 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1450 -2.0377 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6823 -1.8546 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7071 0.7071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6374 -1.3438 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 5 1 0 0 0 0 2 9 1 0 0 0 0 3 6 1 0 0 0 0 3 8 2 0 0 0 0 4 7 2 0 0 0 0 4 10 1 0 0 0 0 5 11 1 0 0 0 0 6 12 2 0 0 0 0 7 13 1 0 0 0 0 8 14 1 0 0 0 0 9 15 2 0 0 0 0 10 16 2 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 13 19 1 0 0 0 0 14 20 1 0 0 0 0 16 23 1 0 0 0 0 17 20 1 0 0 0 0 18 1 1 1 0 0 0 18 29 1 0 0 0 0 19 25 1 6 0 0 0 20 26 1 6 0 0 0 21 15 1 6 0 0 0 21 24 1 0 0 0 0 21 30 1 0 0 0 0 22 17 1 6 0 0 0 22 24 1 0 0 0 0 22 30 1 0 0 0 0 23 27 2 0 0 0 0 23 29 1 0 0 0 0 24 28 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	418.24
Volume:	443.47
LogP:	2.342
LogD:	2.069
LogS:	-4.368
# Rotatable Bonds:	0
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.414
Synthetic Accessibility Score:	6.021
Fsp3:	0.542
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:	-4.932
MDCK Permeability:	2.8937694878550246e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.967
Human Intestinal Absorption (HIA):	0.362
20% Bioavailability (F20%):	0.994
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.531
Plasma Protein Binding (PPB):	94.45172882080078%
Volume Distribution (VD):	1.011
Pgp-substrate:	3.6738317012786865%

ADMET: Metabolism

CYP1A2-inhibitor:	0.075
CYP1A2-substrate:	0.057
CYP2C19-inhibitor:	0.103
CYP2C19-substrate:	0.362
CYP2C9-inhibitor:	0.179
CYP2C9-substrate:	0.595
CYP2D6-inhibitor:	0.034
CYP2D6-substrate:	0.136
CYP3A4-inhibitor:	0.741
CYP3A4-substrate:	0.148

ADMET: Excretion

Clearance (CL):	1.787
Half-life (T1/2):	0.794

ADMET: Toxicity

hERG Blockers:	0.832
Human Hepatotoxicity (H-HT):	0.96
Drug-inuced Liver Injury (DILI):	0.034
AMES Toxicity:	0.565
Rat Oral Acute Toxicity:	0.349
Maximum Recommended Daily Dose:	0.996
Skin Sensitization:	0.968
Carcinogencity:	0.496
Eye Corrosion:	0.004
Eye Irritation:	0.025
Respiratory Toxicity:	0.954

Download Data

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

Natural Product: NPC1180

Natural Product ID:	NPC1180
*Common Name:**	15,17-Epoxy-16-Hydroxy Macrolactin A
IUPAC Name:	(1R,3S,5Z,7E,9S,11E,13Z,17R,21E,23S,25R)-3,9,25-trihydroxy-17-methyl-16,24-dioxabicyclo[21.1.1]pentacosa-5,7,11,13,21-pentaen-15-one
Synonyms:
Standard InCHIKey:	YWWAYEWLZVNRNN-CUHPGSETSA-N
Standard InCHI:	InChI=1S/C24H34O6/c1-18-11-5-2-9-15-21-24(28)22(30-21)17-20(26)14-8-3-6-12-19(25)13-7-4-10-16-23(27)29-18/h3-4,6-10,12,15-16,18-22,24-26,28H,2,5,11,13-14,17H2,1H3/b7-4+,8-3-,12-6+,15-9+,16-10-/t18-,19-,20+,21+,22-,24+/m1/s1
SMILES:	C[C@@H]1CCC/C=C/[C@H]2[C@@H]([C@@H](C[C@H](C/C=CC=C[C@H](C/C=C/C=CC(=O)O1)O)O)O2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1926996
PubChem CID:	56925801
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
NPO30477	Bacillus sp.	Species	Bacillidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19322840]
NPO30477	Bacillus sp.	Species	Bacillidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21699149]
NPO30477	Bacillus sp.	Species	Bacillidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22133265]
NPO30477	Bacillus sp.	Species	Bacillidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8641995]
NPO30477	Bacillus sp.	Species	Bacillidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9099230]

☑ 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	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	160.0	nM	PMID[493306]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	160.0	nM	PMID[493306]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	=	160.0	nM	PMID[493306]

☑ 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 NPC1180 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	196
0.1-0.2	1797
0.2-0.3	5981
0.3-0.4	16837
0.4-0.5	12135
0.5-0.6	4238
0.6-0.7	1258
0.7-0.8	221
0.8-0.85	20
0.85-0.9	12
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9178	High Similarity	NPC329890
0.9079	High Similarity	NPC248775
0.8961	High Similarity	NPC180725
0.8961	High Similarity	NPC470149
0.8961	High Similarity	NPC470148
0.8947	High Similarity	NPC233071
0.8919	High Similarity	NPC329914
0.8904	High Similarity	NPC476037
0.8846	High Similarity	NPC133226
0.8846	High Similarity	NPC470147
0.8816	High Similarity	NPC188860
0.8701	High Similarity	NPC474026
0.8659	High Similarity	NPC208473
0.8649	High Similarity	NPC476012
0.8421	Intermediate Similarity	NPC185186
0.8421	Intermediate Similarity	NPC327383
0.8415	Intermediate Similarity	NPC473308
0.8356	Intermediate Similarity	NPC146811
0.8293	Intermediate Similarity	NPC473315
0.8293	Intermediate Similarity	NPC142111
0.8272	Intermediate Similarity	NPC315731
0.8228	Intermediate Similarity	NPC475711
0.8219	Intermediate Similarity	NPC19769
0.8205	Intermediate Similarity	NPC285840
0.8205	Intermediate Similarity	NPC327041
0.8171	Intermediate Similarity	NPC251026
0.8133	Intermediate Similarity	NPC63873
0.8077	Intermediate Similarity	NPC315843
0.8077	Intermediate Similarity	NPC107654
0.8052	Intermediate Similarity	NPC475762
0.8049	Intermediate Similarity	NPC8538
0.8049	Intermediate Similarity	NPC469469
0.8049	Intermediate Similarity	NPC184208
0.8	Intermediate Similarity	NPC61527
0.7975	Intermediate Similarity	NPC260396
0.7949	Intermediate Similarity	NPC284006
0.7895	Intermediate Similarity	NPC475760
0.7867	Intermediate Similarity	NPC276299
0.7867	Intermediate Similarity	NPC201356
0.7848	Intermediate Similarity	NPC474321
0.7841	Intermediate Similarity	NPC473311
0.7841	Intermediate Similarity	NPC3952
0.7821	Intermediate Similarity	NPC316185
0.7821	Intermediate Similarity	NPC293114
0.7816	Intermediate Similarity	NPC470137
0.7808	Intermediate Similarity	NPC26810
0.7805	Intermediate Similarity	NPC139712
0.7791	Intermediate Similarity	NPC279267
0.7791	Intermediate Similarity	NPC311163
0.7791	Intermediate Similarity	NPC69082
0.7765	Intermediate Similarity	NPC78673
0.7765	Intermediate Similarity	NPC160517
0.7765	Intermediate Similarity	NPC163093
0.7765	Intermediate Similarity	NPC186155
0.7733	Intermediate Similarity	NPC96414
0.7727	Intermediate Similarity	NPC133450
0.7722	Intermediate Similarity	NPC470435
0.7701	Intermediate Similarity	NPC178215
0.7683	Intermediate Similarity	NPC182292
0.7674	Intermediate Similarity	NPC471567
0.7674	Intermediate Similarity	NPC66346
0.7674	Intermediate Similarity	NPC82795
0.7674	Intermediate Similarity	NPC471494
0.7674	Intermediate Similarity	NPC223871
0.7674	Intermediate Similarity	NPC132496
0.7674	Intermediate Similarity	NPC283085
0.7674	Intermediate Similarity	NPC322529
0.7674	Intermediate Similarity	NPC103284
0.7674	Intermediate Similarity	NPC473669
0.7674	Intermediate Similarity	NPC473478
0.7674	Intermediate Similarity	NPC110710
0.7674	Intermediate Similarity	NPC107986
0.7674	Intermediate Similarity	NPC120398
0.7674	Intermediate Similarity	NPC231009
0.7674	Intermediate Similarity	NPC477013
0.7674	Intermediate Similarity	NPC1083
0.7674	Intermediate Similarity	NPC286338
0.7674	Intermediate Similarity	NPC473651
0.7674	Intermediate Similarity	NPC182383
0.7674	Intermediate Similarity	NPC477014
0.7654	Intermediate Similarity	NPC326661
0.7647	Intermediate Similarity	NPC253801
0.764	Intermediate Similarity	NPC177668
0.7625	Intermediate Similarity	NPC474545
0.7619	Intermediate Similarity	NPC474894
0.7614	Intermediate Similarity	NPC280621
0.7614	Intermediate Similarity	NPC233551
0.7614	Intermediate Similarity	NPC40376
0.7614	Intermediate Similarity	NPC21208
0.7614	Intermediate Similarity	NPC20339
0.7614	Intermediate Similarity	NPC48338
0.759	Intermediate Similarity	NPC471537
0.759	Intermediate Similarity	NPC226226
0.759	Intermediate Similarity	NPC55304
0.7586	Intermediate Similarity	NPC231096
0.7586	Intermediate Similarity	NPC308412
0.7586	Intermediate Similarity	NPC134865
0.7586	Intermediate Similarity	NPC134807
0.7586	Intermediate Similarity	NPC62118
0.7586	Intermediate Similarity	NPC219498
0.7586	Intermediate Similarity	NPC114694
0.7586	Intermediate Similarity	NPC240695
0.7586	Intermediate Similarity	NPC477015
0.7586	Intermediate Similarity	NPC232555
0.7586	Intermediate Similarity	NPC171174
0.7586	Intermediate Similarity	NPC473687
0.7586	Intermediate Similarity	NPC107717
0.7586	Intermediate Similarity	NPC134885
0.7586	Intermediate Similarity	NPC47937
0.7586	Intermediate Similarity	NPC475581
0.7586	Intermediate Similarity	NPC112685
0.7586	Intermediate Similarity	NPC142117
0.7586	Intermediate Similarity	NPC103523
0.7586	Intermediate Similarity	NPC210218
0.7586	Intermediate Similarity	NPC204686
0.7582	Intermediate Similarity	NPC469491
0.7564	Intermediate Similarity	NPC475982
0.7564	Intermediate Similarity	NPC475004
0.7558	Intermediate Similarity	NPC156804
0.7529	Intermediate Similarity	NPC131002
0.7529	Intermediate Similarity	NPC473712
0.7529	Intermediate Similarity	NPC145914
0.7529	Intermediate Similarity	NPC180363
0.7529	Intermediate Similarity	NPC473529
0.7529	Intermediate Similarity	NPC94875
0.7529	Intermediate Similarity	NPC65930
0.7529	Intermediate Similarity	NPC473780
0.7529	Intermediate Similarity	NPC475159
0.7529	Intermediate Similarity	NPC11332
0.7529	Intermediate Similarity	NPC73310
0.7529	Intermediate Similarity	NPC329829
0.7528	Intermediate Similarity	NPC139418
0.7527	Intermediate Similarity	NPC475332
0.75	Intermediate Similarity	NPC477085
0.75	Intermediate Similarity	NPC118077
0.75	Intermediate Similarity	NPC199382
0.75	Intermediate Similarity	NPC325627
0.75	Intermediate Similarity	NPC475186
0.75	Intermediate Similarity	NPC316138
0.75	Intermediate Similarity	NPC476655
0.75	Intermediate Similarity	NPC313658
0.75	Intermediate Similarity	NPC476654
0.75	Intermediate Similarity	NPC476657
0.7473	Intermediate Similarity	NPC472195
0.7473	Intermediate Similarity	NPC238090
0.7473	Intermediate Similarity	NPC472196
0.7471	Intermediate Similarity	NPC329615
0.7471	Intermediate Similarity	NPC329838
0.7471	Intermediate Similarity	NPC11804
0.747	Intermediate Similarity	NPC477314
0.747	Intermediate Similarity	NPC473471
0.7468	Intermediate Similarity	NPC473361
0.7468	Intermediate Similarity	NPC329904
0.7468	Intermediate Similarity	NPC476660
0.7447	Intermediate Similarity	NPC475653
0.7447	Intermediate Similarity	NPC65700
0.7444	Intermediate Similarity	NPC473448
0.7444	Intermediate Similarity	NPC239517
0.7444	Intermediate Similarity	NPC473904
0.7442	Intermediate Similarity	NPC229799
0.7442	Intermediate Similarity	NPC315559
0.7442	Intermediate Similarity	NPC286770
0.7442	Intermediate Similarity	NPC144415
0.7442	Intermediate Similarity	NPC161045
0.7442	Intermediate Similarity	NPC284472
0.7439	Intermediate Similarity	NPC477202
0.7439	Intermediate Similarity	NPC469880
0.7436	Intermediate Similarity	NPC474823
0.7419	Intermediate Similarity	NPC255410
0.7419	Intermediate Similarity	NPC288350
0.7419	Intermediate Similarity	NPC173329
0.7416	Intermediate Similarity	NPC287164
0.7416	Intermediate Similarity	NPC171135
0.7416	Intermediate Similarity	NPC172821
0.7416	Intermediate Similarity	NPC61257
0.7416	Intermediate Similarity	NPC261952
0.7416	Intermediate Similarity	NPC320569
0.7416	Intermediate Similarity	NPC100454
0.7416	Intermediate Similarity	NPC242364
0.7416	Intermediate Similarity	NPC274446
0.7416	Intermediate Similarity	NPC191929
0.7416	Intermediate Similarity	NPC89001
0.7416	Intermediate Similarity	NPC39754
0.7416	Intermediate Similarity	NPC320458
0.7416	Intermediate Similarity	NPC234077
0.7416	Intermediate Similarity	NPC81045
0.7416	Intermediate Similarity	NPC169511
0.7416	Intermediate Similarity	NPC133730
0.7416	Intermediate Similarity	NPC151403
0.7416	Intermediate Similarity	NPC473905
0.7403	Intermediate Similarity	NPC476659
0.7403	Intermediate Similarity	NPC476656
0.7391	Intermediate Similarity	NPC256368
0.7391	Intermediate Similarity	NPC159698
0.7386	Intermediate Similarity	NPC293136
0.7386	Intermediate Similarity	NPC241360
0.7386	Intermediate Similarity	NPC132940
0.7386	Intermediate Similarity	NPC309211
0.7381	Intermediate Similarity	NPC86971
0.7381	Intermediate Similarity	NPC473947

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 NPC1180 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	171
0.1-0.2	2310
0.2-0.3	3800
0.3-0.4	2236
0.4-0.5	500
0.5-0.6	111
0.6-0.7	21
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
0.8046	Intermediate Similarity	NPD7838	Discovery
0.7263	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD6698	Approved
0.7253	Intermediate Similarity	NPD46	Approved
0.7174	Intermediate Similarity	NPD7983	Approved
0.7113	Intermediate Similarity	NPD5344	Discontinued
0.7089	Intermediate Similarity	NPD4247	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD6648	Approved
0.6974	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD4250	Approved
0.6559	Remote Similarity	NPD4251	Approved
0.65	Remote Similarity	NPD3197	Phase 1
0.6494	Remote Similarity	NPD585	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD4271	Approved
0.6477	Remote Similarity	NPD4268	Approved
0.6452	Remote Similarity	NPD4249	Approved
0.6415	Remote Similarity	NPD6371	Approved
0.6413	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4225	Approved
0.6392	Remote Similarity	NPD5779	Approved
0.6392	Remote Similarity	NPD5778	Approved
0.6364	Remote Similarity	NPD4756	Discovery
0.6354	Remote Similarity	NPD5785	Approved
0.6333	Remote Similarity	NPD4822	Approved
0.6333	Remote Similarity	NPD4820	Approved
0.6333	Remote Similarity	NPD4819	Approved
0.6333	Remote Similarity	NPD4821	Approved
0.6304	Remote Similarity	NPD7154	Phase 3
0.6289	Remote Similarity	NPD7637	Suspended
0.6286	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD9119	Approved
0.6282	Remote Similarity	NPD6109	Phase 1
0.6282	Remote Similarity	NPD69	Approved
0.6226	Remote Similarity	NPD6686	Approved
0.622	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.62	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.62	Remote Similarity	NPD7839	Suspended
0.617	Remote Similarity	NPD5363	Approved
0.6154	Remote Similarity	NPD9118	Approved
0.6071	Remote Similarity	NPD7505	Discontinued
0.6055	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD7524	Approved
0.6034	Remote Similarity	NPD7829	Approved
0.6034	Remote Similarity	NPD7830	Approved
0.6022	Remote Similarity	NPD5209	Approved
0.602	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7503	Approved
0.6	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD5362	Discontinued
0.5941	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD7640	Approved
0.5865	Remote Similarity	NPD7639	Approved
0.5862	Remote Similarity	NPD8515	Approved
0.5862	Remote Similarity	NPD8517	Approved
0.5862	Remote Similarity	NPD8513	Phase 3
0.5862	Remote Similarity	NPD8516	Approved
0.5851	Remote Similarity	NPD4270	Approved
0.5851	Remote Similarity	NPD6435	Approved
0.5851	Remote Similarity	NPD4269	Approved
0.5833	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD4252	Approved
0.5789	Remote Similarity	NPD6110	Phase 1
0.5789	Remote Similarity	NPD5331	Approved
0.5789	Remote Similarity	NPD7115	Discovery
0.5789	Remote Similarity	NPD5332	Approved
0.5789	Remote Similarity	NPD6695	Phase 3
0.5778	Remote Similarity	NPD8039	Approved
0.5773	Remote Similarity	NPD5786	Approved
0.5769	Remote Similarity	NPD7638	Approved
0.5769	Remote Similarity	NPD3196	Approved
0.5769	Remote Similarity	NPD3195	Phase 2
0.5769	Remote Similarity	NPD3194	Approved
0.5769	Remote Similarity	NPD4266	Approved
0.5769	Remote Similarity	NPD3730	Approved
0.5769	Remote Similarity	NPD3728	Approved
0.5766	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD6101	Approved
0.5745	Remote Similarity	NPD4790	Discontinued
0.5739	Remote Similarity	NPD7641	Discontinued
0.5733	Remote Similarity	NPD4220	Pre-registration
0.573	Remote Similarity	NPD4732	Discontinued
0.5726	Remote Similarity	NPD8444	Approved
0.5714	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5701	Remote Similarity	NPD6647	Phase 2
0.5676	Remote Similarity	NPD6421	Discontinued
0.5667	Remote Similarity	NPD8273	Phase 1
0.5652	Remote Similarity	NPD7500	Approved
0.5644	Remote Similarity	NPD6411	Approved
0.5641	Remote Similarity	NPD3172	Approved
0.5638	Remote Similarity	NPD7514	Phase 3
0.5638	Remote Similarity	NPD7332	Phase 2
0.5638	Remote Similarity	NPD5368	Approved
0.563	Remote Similarity	NPD7642	Approved
0.562	Remote Similarity	NPD8074	Phase 3
0.5603	Remote Similarity	NPD7327	Approved
0.5603	Remote Similarity	NPD7328	Approved
0.56	Remote Similarity	NPD5370	Suspended

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