NPASS Compound

Structure

NPC471802 OpenBabel07101719242D 25 27 0 0 0 0 0 0 0 0999 V2000 -2.7105 -1.5794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7818 4.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2766 -0.6784 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7818 3.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8399 0.1478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6479 3.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5139 1.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9693 1.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6479 0.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4060 1.0488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6479 2.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5139 0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5355 2.7760 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7818 0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4088 1.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5382 2.8507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7818 1.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9749 2.0245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9749 0.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1044 3.7517 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 3.3799 0.1235 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0988 3.6022 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5984 -0.5593 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 0.0000 2.2470 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 10 1 0 0 0 0 6 11 1 0 0 0 0 7 11 2 0 0 0 0 7 12 1 0 0 0 0 8 10 2 0 0 0 0 8 13 1 0 0 0 0 9 12 2 0 0 0 0 9 14 1 0 0 0 0 10 15 1 0 0 0 0 11 17 1 0 0 0 0 12 21 1 0 0 0 0 13 16 2 0 0 0 0 13 22 1 0 0 0 0 14 17 2 0 0 0 0 14 24 1 0 0 0 0 15 18 2 0 0 0 0 15 19 1 0 0 0 0 16 18 1 0 0 0 0 16 20 1 0 0 0 0 17 25 1 0 0 0 0 18 25 1 0 0 0 0 19 23 2 0 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.09
Volume:	352.218
LogP:	5.781
LogD:	4.568
LogS:	-5.556
# Rotatable Bonds:	4
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.592
Synthetic Accessibility Score:	3.076
Fsp3:	0.316
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:	-5.174
MDCK Permeability:	1.8836846720660105e-05
Pgp-inhibitor:	0.038
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.067
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.051
Plasma Protein Binding (PPB):	99.99324798583984%
Volume Distribution (VD):	0.636
Pgp-substrate:	0.774971604347229%

ADMET: Metabolism

CYP1A2-inhibitor:	0.946
CYP1A2-substrate:	0.202
CYP2C19-inhibitor:	0.912
CYP2C19-substrate:	0.078
CYP2C9-inhibitor:	0.79
CYP2C9-substrate:	0.926
CYP2D6-inhibitor:	0.186
CYP2D6-substrate:	0.77
CYP3A4-inhibitor:	0.251
CYP3A4-substrate:	0.093

ADMET: Excretion

Clearance (CL):	8.316
Half-life (T1/2):	0.372

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.023
Drug-inuced Liver Injury (DILI):	0.184
AMES Toxicity:	0.05
Rat Oral Acute Toxicity:	0.916
Maximum Recommended Daily Dose:	0.958
Skin Sensitization:	0.939
Carcinogencity:	0.252
Eye Corrosion:	0.003
Eye Irritation:	0.922
Respiratory Toxicity:	0.771

Download Data

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

Natural Product: NPC471802

Natural Product ID:	NPC471802
*Common Name:**	Spiromastixone C
IUPAC Name:	10-chloro-3,9-dihydroxy-1,7-dipropylbenzo[b][1,4]benzodioxepin-6-one
Synonyms:
Standard InCHIKey:	NRAMLPPUDKVQNJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H19ClO5/c1-3-5-10-8-13(22)16(20)18-15(10)19(23)24-14-9-12(21)7-11(6-4-2)17(14)25-18/h7-9,21-22H,3-6H2,1-2H3
SMILES:	CCCC1=CC(=C(C2=C1C(=O)OC3=CC(=CC(=C3O2)CCC)O)Cl)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3234393
PubChem CID:	90670408
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001645] Depsides and depsidones

*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
NPO33095	spiromastix sp. mccc 3a00308	Species	n.a.	Eukaryota	n.a.	isolated from the deep-sea sediment that was collected from the South Atlantic Ocean (GPS 13.7501 W, 15.1668 S) at a depth of 2869 m	2011-JUN	PMID[24571273]

☑ 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	24
MIC	4

Activity Type	# Activity
Organism	28

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	8.0	ug.mL-1	PMID[463111]
NPT1261	Organism	Bacillus thuringiensis	Bacillus thuringiensis	MIC	=	8.0	ug.mL-1	PMID[463111]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	16.0	ug.mL-1	PMID[463111]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	128.0	ug.mL-1	PMID[463111]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	32000.0	nM	PMID[463111]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	64000.0	nM	PMID[463111]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	IC50	=	64000.0	nM	PMID[463111]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	IC50	=	32000.0	nM	PMID[463111]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	IC50	=	256000.0	nM	PMID[463111]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	IC50	>	256000.0	nM	PMID[463111]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	IC50	>	256000.0	nM	PMID[463111]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	IC50	=	256000.0	nM	PMID[463111]
NPT19	Organism	Escherichia coli	Escherichia coli	IC50	>	256000.0	nM	PMID[463111]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	IC50	>	256000.0	nM	PMID[463111]

☑ 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 NPC471802 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	462
0.1-0.2	2384
0.2-0.3	6597
0.3-0.4	12438
0.4-0.5	4185
0.5-0.6	5364
0.6-0.7	6619
0.7-0.8	4508
0.8-0.85	103
0.85-0.9	19
0.9-0.95	13
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9591	High Similarity	NPC471804
0.9591	High Similarity	NPC471803
0.9591	High Similarity	NPC471812
0.9583	High Similarity	NPC471801
0.948	High Similarity	NPC471807
0.9422	High Similarity	NPC471813
0.9422	High Similarity	NPC471805
0.9368	High Similarity	NPC471806
0.9368	High Similarity	NPC471810
0.931	High Similarity	NPC121100
0.9091	High Similarity	NPC39409
0.908	High Similarity	NPC471814
0.908	High Similarity	NPC471808
0.9045	High Similarity	NPC214901
0.9029	High Similarity	NPC471811
0.9029	High Similarity	NPC471809
0.9012	High Similarity	NPC108278
0.8989	High Similarity	NPC220369
0.8971	High Similarity	NPC195675
0.8963	High Similarity	NPC471800
0.8802	High Similarity	NPC238381
0.8743	High Similarity	NPC154720
0.8698	High Similarity	NPC303565
0.8686	High Similarity	NPC175804
0.8647	High Similarity	NPC93739
0.8634	High Similarity	NPC198163
0.8621	High Similarity	NPC188618
0.8596	High Similarity	NPC156082
0.8596	High Similarity	NPC284007
0.8596	High Similarity	NPC300984
0.8547	High Similarity	NPC112981
0.8547	High Similarity	NPC8070
0.8547	High Similarity	NPC267153
0.8531	High Similarity	NPC28160
0.8497	Intermediate Similarity	NPC20216
0.8471	Intermediate Similarity	NPC168616
0.8471	Intermediate Similarity	NPC83763
0.8462	Intermediate Similarity	NPC54928
0.8448	Intermediate Similarity	NPC272485
0.8448	Intermediate Similarity	NPC292788
0.8421	Intermediate Similarity	NPC200594
0.8393	Intermediate Similarity	NPC289968
0.8382	Intermediate Similarity	NPC474350
0.8352	Intermediate Similarity	NPC239440
0.8352	Intermediate Similarity	NPC246716
0.8352	Intermediate Similarity	NPC20543
0.8352	Intermediate Similarity	NPC17219
0.8333	Intermediate Similarity	NPC193676
0.8324	Intermediate Similarity	NPC8300
0.8295	Intermediate Similarity	NPC26568
0.8276	Intermediate Similarity	NPC234004
0.8258	Intermediate Similarity	NPC181523
0.8249	Intermediate Similarity	NPC10576
0.8249	Intermediate Similarity	NPC1827
0.8249	Intermediate Similarity	NPC470565
0.8246	Intermediate Similarity	NPC472456
0.8246	Intermediate Similarity	NPC274730
0.8242	Intermediate Similarity	NPC95123
0.8242	Intermediate Similarity	NPC66404
0.8232	Intermediate Similarity	NPC105648
0.8229	Intermediate Similarity	NPC130920
0.8229	Intermediate Similarity	NPC85057
0.8214	Intermediate Similarity	NPC328119
0.8212	Intermediate Similarity	NPC139350
0.8212	Intermediate Similarity	NPC289147
0.8198	Intermediate Similarity	NPC217677
0.8198	Intermediate Similarity	NPC300727
0.8198	Intermediate Similarity	NPC165977
0.8198	Intermediate Similarity	NPC241904
0.8193	Intermediate Similarity	NPC29577
0.8193	Intermediate Similarity	NPC134621
0.8192	Intermediate Similarity	NPC49487
0.8192	Intermediate Similarity	NPC99613
0.8187	Intermediate Similarity	NPC20541
0.8182	Intermediate Similarity	NPC29160
0.8171	Intermediate Similarity	NPC220106
0.8167	Intermediate Similarity	NPC45072
0.8156	Intermediate Similarity	NPC470422
0.815	Intermediate Similarity	NPC476242
0.815	Intermediate Similarity	NPC100123
0.8146	Intermediate Similarity	NPC109827
0.8146	Intermediate Similarity	NPC470562
0.8146	Intermediate Similarity	NPC124470
0.8144	Intermediate Similarity	NPC237208
0.8136	Intermediate Similarity	NPC472032
0.8136	Intermediate Similarity	NPC234331
0.8129	Intermediate Similarity	NPC475895
0.8129	Intermediate Similarity	NPC89474
0.8118	Intermediate Similarity	NPC308451
0.8118	Intermediate Similarity	NPC208043
0.8118	Intermediate Similarity	NPC204350
0.8118	Intermediate Similarity	NPC226973
0.8103	Intermediate Similarity	NPC474287
0.8103	Intermediate Similarity	NPC56085
0.8103	Intermediate Similarity	NPC200746
0.8103	Intermediate Similarity	NPC14353
0.8103	Intermediate Similarity	NPC475886
0.8103	Intermediate Similarity	NPC228785
0.8103	Intermediate Similarity	NPC320359
0.8101	Intermediate Similarity	NPC470560
0.8101	Intermediate Similarity	NPC158226
0.8095	Intermediate Similarity	NPC62536
0.8095	Intermediate Similarity	NPC33265
0.8095	Intermediate Similarity	NPC12305
0.8092	Intermediate Similarity	NPC108456
0.809	Intermediate Similarity	NPC163130
0.809	Intermediate Similarity	NPC165979
0.8079	Intermediate Similarity	NPC472452
0.8077	Intermediate Similarity	NPC113446
0.8059	Intermediate Similarity	NPC306821
0.8057	Intermediate Similarity	NPC474187
0.8057	Intermediate Similarity	NPC66288
0.8057	Intermediate Similarity	NPC474186
0.8057	Intermediate Similarity	NPC475883
0.8057	Intermediate Similarity	NPC278052
0.8057	Intermediate Similarity	NPC40491
0.8057	Intermediate Similarity	NPC474351
0.8057	Intermediate Similarity	NPC61010
0.8047	Intermediate Similarity	NPC105415
0.8047	Intermediate Similarity	NPC195202
0.8035	Intermediate Similarity	NPC227062
0.8035	Intermediate Similarity	NPC142339
0.8023	Intermediate Similarity	NPC255350
0.8023	Intermediate Similarity	NPC274327
0.8023	Intermediate Similarity	NPC276409
0.8023	Intermediate Similarity	NPC69394
0.8023	Intermediate Similarity	NPC86485
0.8023	Intermediate Similarity	NPC250822
0.8023	Intermediate Similarity	NPC280937
0.8023	Intermediate Similarity	NPC231018
0.8023	Intermediate Similarity	NPC246204
0.8023	Intermediate Similarity	NPC75279
0.8023	Intermediate Similarity	NPC160951
0.8023	Intermediate Similarity	NPC472915
0.8023	Intermediate Similarity	NPC47781
0.8023	Intermediate Similarity	NPC145379
0.8023	Intermediate Similarity	NPC22519
0.8023	Intermediate Similarity	NPC183878
0.8023	Intermediate Similarity	NPC176775
0.8012	Intermediate Similarity	NPC117579
0.8012	Intermediate Similarity	NPC474663
0.8012	Intermediate Similarity	NPC202157
0.8011	Intermediate Similarity	NPC229632
0.8011	Intermediate Similarity	NPC25152
0.8	Intermediate Similarity	NPC291049
0.8	Intermediate Similarity	NPC177298
0.8	Intermediate Similarity	NPC139036
0.8	Intermediate Similarity	NPC6923
0.8	Intermediate Similarity	NPC285527
0.8	Intermediate Similarity	NPC48479
0.8	Intermediate Similarity	NPC106334
0.8	Intermediate Similarity	NPC233267
0.8	Intermediate Similarity	NPC47623
0.7989	Intermediate Similarity	NPC181960
0.7989	Intermediate Similarity	NPC469584
0.7989	Intermediate Similarity	NPC236796
0.7988	Intermediate Similarity	NPC12200
0.7988	Intermediate Similarity	NPC119660
0.7988	Intermediate Similarity	NPC93034
0.7978	Intermediate Similarity	NPC329161
0.7978	Intermediate Similarity	NPC240887
0.7978	Intermediate Similarity	NPC470091
0.7977	Intermediate Similarity	NPC4455
0.7977	Intermediate Similarity	NPC256612
0.7977	Intermediate Similarity	NPC50715
0.7977	Intermediate Similarity	NPC227325
0.7977	Intermediate Similarity	NPC128863
0.7977	Intermediate Similarity	NPC208197
0.7977	Intermediate Similarity	NPC472909
0.7977	Intermediate Similarity	NPC201136
0.7977	Intermediate Similarity	NPC20830
0.7977	Intermediate Similarity	NPC16082
0.7977	Intermediate Similarity	NPC167815
0.7977	Intermediate Similarity	NPC213622
0.7977	Intermediate Similarity	NPC280339
0.7977	Intermediate Similarity	NPC92659
0.7977	Intermediate Similarity	NPC183597
0.7977	Intermediate Similarity	NPC189960
0.7977	Intermediate Similarity	NPC146165
0.7977	Intermediate Similarity	NPC138360
0.7977	Intermediate Similarity	NPC82592
0.7977	Intermediate Similarity	NPC2476
0.7977	Intermediate Similarity	NPC163780
0.7977	Intermediate Similarity	NPC32557
0.7977	Intermediate Similarity	NPC37392
0.7977	Intermediate Similarity	NPC196439
0.7976	Intermediate Similarity	NPC287275
0.7976	Intermediate Similarity	NPC32470
0.7968	Intermediate Similarity	NPC470100
0.7968	Intermediate Similarity	NPC470099
0.7966	Intermediate Similarity	NPC152659
0.7966	Intermediate Similarity	NPC248638
0.7966	Intermediate Similarity	NPC236132
0.7966	Intermediate Similarity	NPC23298
0.7966	Intermediate Similarity	NPC270837
0.7966	Intermediate Similarity	NPC197168
0.7966	Intermediate Similarity	NPC475985
0.7966	Intermediate Similarity	NPC189473
0.7966	Intermediate Similarity	NPC220313
0.7966	Intermediate Similarity	NPC7483

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 NPC471802 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	421
0.1-0.2	1140
0.2-0.3	2151
0.3-0.4	2721
0.4-0.5	1596
0.5-0.6	803
0.6-0.7	253
0.7-0.8	64
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8036	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD2801	Approved
0.7836	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7809	Intermediate Similarity	NPD6232	Discontinued
0.779	Intermediate Similarity	NPD5844	Phase 1
0.7771	Intermediate Similarity	NPD3817	Phase 2
0.7759	Intermediate Similarity	NPD1934	Approved
0.7725	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD2403	Approved
0.7714	Intermediate Similarity	NPD1465	Phase 2
0.7706	Intermediate Similarity	NPD1511	Approved
0.768	Intermediate Similarity	NPD7473	Discontinued
0.7627	Intermediate Similarity	NPD3882	Suspended
0.7616	Intermediate Similarity	NPD1512	Approved
0.7614	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7819	Suspended
0.7432	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD6166	Phase 2
0.7432	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD7054	Approved
0.7403	Intermediate Similarity	NPD5494	Approved
0.7399	Intermediate Similarity	NPD6799	Approved
0.7366	Intermediate Similarity	NPD7074	Phase 3
0.7366	Intermediate Similarity	NPD7472	Approved
0.7365	Intermediate Similarity	NPD447	Suspended
0.7356	Intermediate Similarity	NPD2533	Approved
0.7356	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD2534	Approved
0.7356	Intermediate Similarity	NPD2532	Approved
0.7351	Intermediate Similarity	NPD3818	Discontinued
0.7326	Intermediate Similarity	NPD3750	Approved
0.7294	Intermediate Similarity	NPD2935	Discontinued
0.7293	Intermediate Similarity	NPD3749	Approved
0.7293	Intermediate Similarity	NPD7075	Discontinued
0.7249	Intermediate Similarity	NPD7808	Phase 3
0.7247	Intermediate Similarity	NPD6599	Discontinued
0.7234	Intermediate Similarity	NPD6797	Phase 2
0.7222	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD7251	Discontinued
0.7184	Intermediate Similarity	NPD2354	Approved
0.7182	Intermediate Similarity	NPD5402	Approved
0.7174	Intermediate Similarity	NPD6959	Discontinued
0.7158	Intermediate Similarity	NPD919	Approved
0.7151	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD7411	Suspended
0.711	Intermediate Similarity	NPD1549	Phase 2
0.7104	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD1240	Approved
0.7095	Intermediate Similarity	NPD3226	Approved
0.7093	Intermediate Similarity	NPD1551	Phase 2
0.7083	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7199	Phase 2
0.7072	Intermediate Similarity	NPD6801	Discontinued
0.7062	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD230	Phase 1
0.7056	Intermediate Similarity	NPD4380	Phase 2
0.7052	Intermediate Similarity	NPD2353	Approved
0.7052	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD7768	Phase 2
0.7035	Intermediate Similarity	NPD1510	Phase 2
0.7035	Intermediate Similarity	NPD3748	Approved
0.7035	Intermediate Similarity	NPD2799	Discontinued
0.7026	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD1607	Approved
0.7005	Intermediate Similarity	NPD3926	Phase 2
0.7005	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD2796	Approved
0.6989	Remote Similarity	NPD1247	Approved
0.6989	Remote Similarity	NPD3887	Approved
0.6988	Remote Similarity	NPD1203	Approved
0.6983	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD37	Approved
0.6973	Remote Similarity	NPD6234	Discontinued
0.6971	Remote Similarity	NPD2800	Approved
0.6971	Remote Similarity	NPD1243	Approved
0.6968	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4966	Approved
0.6957	Remote Similarity	NPD4965	Approved
0.6957	Remote Similarity	NPD4967	Phase 2
0.6936	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD4628	Phase 3
0.691	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD454	Approved
0.6901	Remote Similarity	NPD943	Approved
0.6889	Remote Similarity	NPD5403	Approved
0.6884	Remote Similarity	NPD4360	Phase 2
0.6884	Remote Similarity	NPD4363	Phase 3
0.6862	Remote Similarity	NPD5711	Approved
0.6862	Remote Similarity	NPD5710	Approved
0.686	Remote Similarity	NPD1933	Approved
0.686	Remote Similarity	NPD1184	Approved
0.6859	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD2346	Discontinued
0.6851	Remote Similarity	NPD1653	Approved
0.6839	Remote Similarity	NPD6559	Discontinued
0.6836	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD958	Approved
0.6818	Remote Similarity	NPD4534	Discontinued
0.6807	Remote Similarity	NPD9717	Approved
0.6805	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6100	Approved
0.68	Remote Similarity	NPD6099	Approved
0.6796	Remote Similarity	NPD920	Approved
0.6784	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.678	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD5401	Approved
0.6766	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD4361	Phase 2
0.6765	Remote Similarity	NPD6832	Phase 2
0.6765	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD957	Approved
0.6747	Remote Similarity	NPD422	Phase 1
0.6743	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD5242	Approved
0.6723	Remote Similarity	NPD5958	Discontinued
0.6722	Remote Similarity	NPD7390	Discontinued
0.672	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD3751	Discontinued
0.6719	Remote Similarity	NPD7228	Approved
0.6716	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD1608	Approved
0.6701	Remote Similarity	NPD5953	Discontinued
0.6701	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD3268	Approved
0.6686	Remote Similarity	NPD2797	Approved
0.6686	Remote Similarity	NPD411	Approved
0.6685	Remote Similarity	NPD4972	Discontinued
0.6685	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD3787	Discontinued
0.6684	Remote Similarity	NPD7286	Phase 2
0.6667	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2344	Approved
0.6631	Remote Similarity	NPD5353	Approved
0.6631	Remote Similarity	NPD4288	Approved
0.6628	Remote Similarity	NPD3027	Phase 3
0.6611	Remote Similarity	NPD6190	Approved
0.661	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD1613	Approved
0.6607	Remote Similarity	NPD9269	Phase 2
0.6597	Remote Similarity	NPD7229	Phase 3
0.659	Remote Similarity	NPD2313	Discontinued
0.6566	Remote Similarity	NPD9268	Approved
0.6559	Remote Similarity	NPD6386	Approved
0.6559	Remote Similarity	NPD6385	Approved
0.6557	Remote Similarity	NPD7783	Phase 2
0.6557	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD4308	Phase 3
0.6552	Remote Similarity	NPD6312	Discontinued
0.6548	Remote Similarity	NPD7549	Discontinued
0.6543	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD6651	Approved
0.6529	Remote Similarity	NPD3225	Approved
0.6527	Remote Similarity	NPD17	Approved
0.6519	Remote Similarity	NPD2309	Approved
0.6517	Remote Similarity	NPD5405	Approved
0.6517	Remote Similarity	NPD5408	Approved
0.6517	Remote Similarity	NPD5406	Approved
0.6517	Remote Similarity	NPD5404	Approved
0.6517	Remote Similarity	NPD4287	Approved
0.6515	Remote Similarity	NPD8312	Approved
0.6515	Remote Similarity	NPD8313	Approved
0.6514	Remote Similarity	NPD4060	Phase 1
0.6509	Remote Similarity	NPD1481	Phase 2
0.6503	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD1578	Phase 2
0.65	Remote Similarity	NPD8434	Phase 2
0.6497	Remote Similarity	NPD7685	Pre-registration
0.6494	Remote Similarity	NPD3764	Approved
0.6494	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD1296	Phase 2
0.6492	Remote Similarity	NPD3365	Discontinued
0.6465	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD8151	Discontinued
0.6461	Remote Similarity	NPD7033	Discontinued
0.6459	Remote Similarity	NPD7435	Discontinued
0.6458	Remote Similarity	NPD8127	Discontinued
0.6457	Remote Similarity	NPD6233	Phase 2
0.6452	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.645	Remote Similarity	NPD1535	Discovery
0.6437	Remote Similarity	NPD4625	Phase 3
0.6425	Remote Similarity	NPD4477	Approved
0.6425	Remote Similarity	NPD4476	Approved
0.6418	Remote Similarity	NPD8150	Discontinued
0.6416	Remote Similarity	NPD9494	Approved
0.6414	Remote Similarity	NPD7240	Approved
0.6414	Remote Similarity	NPD7038	Approved
0.6414	Remote Similarity	NPD7039	Approved
0.6404	Remote Similarity	NPD4536	Approved
0.6404	Remote Similarity	NPD4538	Approved
0.6404	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD3266	Approved
0.6395	Remote Similarity	NPD3267	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