NPASS Compound

Structure

NPC471800 OpenBabel07101719242D 24 26 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 -2.9693 1.8750 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 -1.5382 2.8507 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 -2.5355 2.7760 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 -0.9749 2.0245 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 0.7818 1.6235 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 -3.0988 3.6022 0.0000 O 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 -1.5984 -0.5593 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 0.0000 0.0000 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 11 1 0 0 0 0 6 12 1 0 0 0 0 7 11 2 0 0 0 0 7 13 1 0 0 0 0 8 12 2 0 0 0 0 8 14 1 0 0 0 0 9 13 2 0 0 0 0 9 15 1 0 0 0 0 10 14 2 0 0 0 0 10 16 1 0 0 0 0 11 17 1 0 0 0 0 12 18 1 0 0 0 0 13 20 1 0 0 0 0 14 21 1 0 0 0 0 15 17 2 0 0 0 0 15 23 1 0 0 0 0 16 18 2 0 0 0 0 16 24 1 0 0 0 0 17 19 1 0 0 0 0 18 23 1 0 0 0 0 19 22 2 0 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.13
Volume:	337.007
LogP:	5.027
LogD:	4.367
LogS:	-5.267
# Rotatable Bonds:	4
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.645
Synthetic Accessibility Score:	2.889
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:	-5.262
MDCK Permeability:	2.0424506146810018e-05
Pgp-inhibitor:	0.046
Pgp-substrate:	0.054
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.967
30% Bioavailability (F30%):	0.171

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.09
Plasma Protein Binding (PPB):	98.92436218261719%
Volume Distribution (VD):	0.684
Pgp-substrate:	1.3729101419448853%

ADMET: Metabolism

CYP1A2-inhibitor:	0.973
CYP1A2-substrate:	0.254
CYP2C19-inhibitor:	0.951
CYP2C19-substrate:	0.069
CYP2C9-inhibitor:	0.736
CYP2C9-substrate:	0.947
CYP2D6-inhibitor:	0.455
CYP2D6-substrate:	0.876
CYP3A4-inhibitor:	0.473
CYP3A4-substrate:	0.088

ADMET: Excretion

Clearance (CL):	10.064
Half-life (T1/2):	0.614

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.013
Drug-inuced Liver Injury (DILI):	0.127
AMES Toxicity:	0.131
Rat Oral Acute Toxicity:	0.566
Maximum Recommended Daily Dose:	0.956
Skin Sensitization:	0.944
Carcinogencity:	0.174
Eye Corrosion:	0.005
Eye Irritation:	0.931
Respiratory Toxicity:	0.687

Download Data

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

Natural Product: NPC471800

Natural Product ID:	NPC471800
*Common Name:**	Spiromastixone A
IUPAC Name:	3,9-dihydroxy-1,7-dipropylbenzo[b][1,4]benzodioxepin-6-one
Synonyms:
Standard InCHIKey:	IKKIGBFMFYLXGH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H20O5/c1-3-5-11-7-13(20)9-15-17(11)19(22)24-16-10-14(21)8-12(6-4-2)18(16)23-15/h7-10,20-21H,3-6H2,1-2H3
SMILES:	CCCC1=C2C(=CC(=C1)O)OC3=C(C=C(C=C3OC2=O)O)CCC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3234391
PubChem CID:	90670406
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
MIC	4

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	4.0	ug.mL-1	PMID[506507]
NPT1261	Organism	Bacillus thuringiensis	Bacillus thuringiensis	MIC	=	4.0	ug.mL-1	PMID[506507]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	8.0	ug.mL-1	PMID[506507]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	128.0	ug.mL-1	PMID[506507]

☑ 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 NPC471800 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	388
0.1-0.2	1899
0.2-0.3	4942
0.3-0.4	11105
0.4-0.5	6351
0.5-0.6	3609
0.6-0.7	5274
0.7-0.8	6336
0.8-0.85	2201
0.85-0.9	526
0.9-0.95	60
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.98	High Similarity	NPC238381
0.9671	High Similarity	NPC303565
0.9608	High Similarity	NPC93739
0.9545	High Similarity	NPC284007
0.9545	High Similarity	NPC300984
0.9545	High Similarity	NPC156082
0.9484	High Similarity	NPC8070
0.9484	High Similarity	NPC267153
0.9484	High Similarity	NPC112981
0.9423	High Similarity	NPC20216
0.9412	High Similarity	NPC83763
0.9412	High Similarity	NPC168616
0.9408	High Similarity	NPC54928
0.9363	High Similarity	NPC272485
0.9363	High Similarity	NPC292788
0.9351	High Similarity	NPC200594
0.9338	High Similarity	NPC289968
0.9295	High Similarity	NPC474350
0.9245	High Similarity	NPC17219
0.9245	High Similarity	NPC246716
0.9245	High Similarity	NPC239440
0.9245	High Similarity	NPC20543
0.9231	High Similarity	NPC8300
0.9189	High Similarity	NPC95123
0.9189	High Similarity	NPC66404
0.9184	High Similarity	NPC105648
0.9182	High Similarity	NPC26568
0.9172	High Similarity	NPC234004
0.9156	High Similarity	NPC472456
0.9156	High Similarity	NPC274730
0.9139	High Similarity	NPC328119
0.913	High Similarity	NPC181523
0.9128	High Similarity	NPC134621
0.9128	High Similarity	NPC29577
0.9125	High Similarity	NPC1827
0.9125	High Similarity	NPC10576
0.9116	High Similarity	NPC220106
0.9114	High Similarity	NPC130920
0.9114	High Similarity	NPC85057
0.9097	High Similarity	NPC241904
0.9097	High Similarity	NPC165977
0.9097	High Similarity	NPC300727
0.9097	High Similarity	NPC217677
0.9091	High Similarity	NPC20541
0.9074	High Similarity	NPC139350
0.9074	High Similarity	NPC289147
0.9067	High Similarity	NPC237208
0.9062	High Similarity	NPC49487
0.9062	High Similarity	NPC99613
0.9057	High Similarity	NPC29160
0.9038	High Similarity	NPC476242
0.9038	High Similarity	NPC100123
0.9026	High Similarity	NPC475895
0.9026	High Similarity	NPC89474
0.902	High Similarity	NPC226973
0.902	High Similarity	NPC204350
0.902	High Similarity	NPC308451
0.902	High Similarity	NPC208043
0.9007	High Similarity	NPC12305
0.9007	High Similarity	NPC62536
0.9007	High Similarity	NPC33265
0.9006	High Similarity	NPC124470
0.9006	High Similarity	NPC109827
0.9	High Similarity	NPC234331
0.8981	High Similarity	NPC475886
0.8981	High Similarity	NPC228785
0.8981	High Similarity	NPC14353
0.8981	High Similarity	NPC200746
0.8981	High Similarity	NPC474287
0.8981	High Similarity	NPC56085
0.8981	High Similarity	NPC320359
0.8974	High Similarity	NPC108456
0.8963	High Similarity	NPC471802
0.8954	High Similarity	NPC306821
0.8951	High Similarity	NPC158226
0.8947	High Similarity	NPC105415
0.8947	High Similarity	NPC195202
0.8944	High Similarity	NPC165979
0.8944	High Similarity	NPC163130
0.8938	High Similarity	NPC472452
0.8924	High Similarity	NPC61010
0.8924	High Similarity	NPC278052
0.8924	High Similarity	NPC40491
0.8924	High Similarity	NPC474187
0.8924	High Similarity	NPC66288
0.8924	High Similarity	NPC474186
0.8924	High Similarity	NPC475883
0.8924	High Similarity	NPC474351
0.891	High Similarity	NPC142339
0.891	High Similarity	NPC227062
0.8909	High Similarity	NPC471801
0.8909	High Similarity	NPC113446
0.8903	High Similarity	NPC69394
0.8903	High Similarity	NPC472915
0.8903	High Similarity	NPC231018
0.8903	High Similarity	NPC250822
0.8903	High Similarity	NPC274327
0.8903	High Similarity	NPC183878
0.8903	High Similarity	NPC22519
0.8903	High Similarity	NPC280937
0.8903	High Similarity	NPC276409
0.8903	High Similarity	NPC246204
0.8903	High Similarity	NPC75279
0.8903	High Similarity	NPC255350
0.8903	High Similarity	NPC145379
0.8903	High Similarity	NPC160951
0.8903	High Similarity	NPC47781
0.8903	High Similarity	NPC86485
0.8903	High Similarity	NPC176775
0.8896	High Similarity	NPC117579
0.8896	High Similarity	NPC202157
0.8896	High Similarity	NPC474663
0.8889	High Similarity	NPC233267
0.8889	High Similarity	NPC6923
0.8889	High Similarity	NPC106334
0.8889	High Similarity	NPC48479
0.8889	High Similarity	NPC177298
0.8889	High Similarity	NPC291049
0.8889	High Similarity	NPC285527
0.8882	High Similarity	NPC119660
0.8882	High Similarity	NPC12200
0.8882	High Similarity	NPC93034
0.8874	High Similarity	NPC287275
0.8874	High Similarity	NPC32470
0.8868	High Similarity	NPC229632
0.8868	High Similarity	NPC25152
0.8861	High Similarity	NPC47623
0.8861	High Similarity	NPC139036
0.8854	High Similarity	NPC181960
0.8854	High Similarity	NPC469584
0.8854	High Similarity	NPC236796
0.8846	High Similarity	NPC128863
0.8846	High Similarity	NPC227325
0.8846	High Similarity	NPC196439
0.8846	High Similarity	NPC472909
0.8846	High Similarity	NPC20830
0.8846	High Similarity	NPC4455
0.8846	High Similarity	NPC213622
0.8846	High Similarity	NPC2476
0.8846	High Similarity	NPC167815
0.8846	High Similarity	NPC208197
0.8846	High Similarity	NPC138360
0.8846	High Similarity	NPC280339
0.8846	High Similarity	NPC183597
0.8846	High Similarity	NPC37392
0.8846	High Similarity	NPC201136
0.8846	High Similarity	NPC163780
0.8846	High Similarity	NPC92659
0.8846	High Similarity	NPC32557
0.8846	High Similarity	NPC50715
0.8846	High Similarity	NPC256612
0.8846	High Similarity	NPC189960
0.8846	High Similarity	NPC16082
0.8846	High Similarity	NPC82592
0.8846	High Similarity	NPC146165
0.8839	High Similarity	NPC156222
0.8839	High Similarity	NPC273483
0.8839	High Similarity	NPC120163
0.8839	High Similarity	NPC83508
0.8839	High Similarity	NPC100887
0.8839	High Similarity	NPC198826
0.8839	High Similarity	NPC57030
0.8839	High Similarity	NPC301323
0.8839	High Similarity	NPC131624
0.8839	High Similarity	NPC188203
0.8839	High Similarity	NPC212678
0.8839	High Similarity	NPC71334
0.8839	High Similarity	NPC293183
0.8839	High Similarity	NPC25270
0.8839	High Similarity	NPC222830
0.8839	High Similarity	NPC301123
0.8839	High Similarity	NPC256283
0.8839	High Similarity	NPC275836
0.8839	High Similarity	NPC199773
0.8839	High Similarity	NPC239128
0.8839	High Similarity	NPC187498
0.8839	High Similarity	NPC275722
0.8839	High Similarity	NPC162313
0.8839	High Similarity	NPC241498
0.8831	High Similarity	NPC164527
0.8831	High Similarity	NPC219330
0.8831	High Similarity	NPC50728
0.8831	High Similarity	NPC29056
0.8831	High Similarity	NPC338131
0.8831	High Similarity	NPC166753
0.8831	High Similarity	NPC225129
0.8831	High Similarity	NPC307780
0.8831	High Similarity	NPC213382
0.8831	High Similarity	NPC179183
0.8831	High Similarity	NPC309979
0.8831	High Similarity	NPC60413
0.8831	High Similarity	NPC151473
0.8824	High Similarity	NPC120464
0.8816	High Similarity	NPC138978
0.8816	High Similarity	NPC267509
0.8812	High Similarity	NPC270837
0.8812	High Similarity	NPC236132
0.8812	High Similarity	NPC220313
0.8812	High Similarity	NPC189473
0.8812	High Similarity	NPC133065

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 NPC471800 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	365
0.1-0.2	1008
0.2-0.3	1934
0.3-0.4	2645
0.4-0.5	1666
0.5-0.6	951
0.6-0.7	410
0.7-0.8	138
0.8-0.85	29
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8903	High Similarity	NPD2801	Approved
0.8634	High Similarity	NPD6232	Discontinued
0.8608	High Similarity	NPD3817	Phase 2
0.86	High Similarity	NPD970	Clinical (unspecified phase)
0.8599	High Similarity	NPD1934	Approved
0.8598	High Similarity	NPD5844	Phase 1
0.8562	High Similarity	NPD1511	Approved
0.8544	High Similarity	NPD1465	Phase 2
0.8476	Intermediate Similarity	NPD7473	Discontinued
0.8452	Intermediate Similarity	NPD1512	Approved
0.8438	Intermediate Similarity	NPD3882	Suspended
0.8428	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD7819	Suspended
0.8284	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD6799	Approved
0.82	Intermediate Similarity	NPD447	Suspended
0.8193	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD6166	Phase 2
0.8193	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD5494	Approved
0.8155	Intermediate Similarity	NPD7054	Approved
0.8153	Intermediate Similarity	NPD2532	Approved
0.8153	Intermediate Similarity	NPD2533	Approved
0.8153	Intermediate Similarity	NPD2534	Approved
0.8153	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD3750	Approved
0.8107	Intermediate Similarity	NPD7074	Phase 3
0.8107	Intermediate Similarity	NPD7472	Approved
0.8105	Intermediate Similarity	NPD2935	Discontinued
0.8095	Intermediate Similarity	NPD3818	Discontinued
0.8049	Intermediate Similarity	NPD3749	Approved
0.8049	Intermediate Similarity	NPD7075	Discontinued
0.8012	Intermediate Similarity	NPD6599	Discontinued
0.7975	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD7808	Phase 3
0.7953	Intermediate Similarity	NPD6797	Phase 2
0.7935	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD5402	Approved
0.7907	Intermediate Similarity	NPD7251	Discontinued
0.7904	Intermediate Similarity	NPD6959	Discontinued
0.7895	Intermediate Similarity	NPD1240	Approved
0.7892	Intermediate Similarity	NPD919	Approved
0.7885	Intermediate Similarity	NPD1549	Phase 2
0.7881	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD1551	Phase 2
0.7853	Intermediate Similarity	NPD7411	Suspended
0.7849	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD230	Phase 1
0.784	Intermediate Similarity	NPD3226	Approved
0.7831	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD1510	Phase 2
0.7806	Intermediate Similarity	NPD2799	Discontinued
0.7806	Intermediate Similarity	NPD3748	Approved
0.7805	Intermediate Similarity	NPD6801	Discontinued
0.7798	Intermediate Similarity	NPD7199	Phase 2
0.7792	Intermediate Similarity	NPD1607	Approved
0.7791	Intermediate Similarity	NPD4380	Phase 2
0.7785	Intermediate Similarity	NPD1203	Approved
0.7771	Intermediate Similarity	NPD7768	Phase 2
0.7756	Intermediate Similarity	NPD2796	Approved
0.7722	Intermediate Similarity	NPD2800	Approved
0.7722	Intermediate Similarity	NPD1243	Approved
0.7716	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD3926	Phase 2
0.7706	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD37	Approved
0.7692	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1247	Approved
0.7679	Intermediate Similarity	NPD6234	Discontinued
0.7673	Intermediate Similarity	NPD4628	Phase 3
0.7665	Intermediate Similarity	NPD4965	Approved
0.7665	Intermediate Similarity	NPD4967	Phase 2
0.7665	Intermediate Similarity	NPD4966	Approved
0.7662	Intermediate Similarity	NPD943	Approved
0.7661	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD1933	Approved
0.7607	Intermediate Similarity	NPD5403	Approved
0.7595	Intermediate Similarity	NPD2346	Discontinued
0.7584	Intermediate Similarity	NPD9717	Approved
0.7566	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD1653	Approved
0.7546	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD5710	Approved
0.7544	Intermediate Similarity	NPD5711	Approved
0.7532	Intermediate Similarity	NPD6100	Approved
0.7532	Intermediate Similarity	NPD6099	Approved
0.7529	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD422	Phase 1
0.7516	Intermediate Similarity	NPD6832	Phase 2
0.7516	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6559	Discontinued
0.75	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD920	Approved
0.7485	Intermediate Similarity	NPD5401	Approved
0.7468	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD1608	Approved
0.7434	Intermediate Similarity	NPD2797	Approved
0.7423	Intermediate Similarity	NPD7390	Discontinued
0.7419	Intermediate Similarity	NPD411	Approved
0.7419	Intermediate Similarity	NPD3268	Approved
0.7418	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD5242	Approved
0.7378	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD2344	Approved
0.7371	Intermediate Similarity	NPD7228	Approved
0.7371	Intermediate Similarity	NPD3751	Discontinued
0.7362	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD3027	Phase 3
0.7351	Intermediate Similarity	NPD9269	Phase 2
0.7345	Intermediate Similarity	NPD5953	Discontinued
0.7341	Intermediate Similarity	NPD3787	Discontinued
0.7333	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7286	Phase 2
0.7326	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD1613	Approved
0.7315	Intermediate Similarity	NPD9268	Approved
0.7308	Intermediate Similarity	NPD2313	Discontinued
0.7301	Intermediate Similarity	NPD6190	Approved
0.7294	Intermediate Similarity	NPD4288	Approved
0.7294	Intermediate Similarity	NPD5353	Approved
0.7267	Intermediate Similarity	NPD17	Approved
0.7255	Intermediate Similarity	NPD3225	Approved
0.725	Intermediate Similarity	NPD4308	Phase 3
0.7241	Intermediate Similarity	NPD7229	Phase 3
0.7237	Intermediate Similarity	NPD1481	Phase 2
0.7233	Intermediate Similarity	NPD6651	Approved
0.7219	Intermediate Similarity	NPD6386	Approved
0.7219	Intermediate Similarity	NPD6385	Approved
0.7215	Intermediate Similarity	NPD4060	Phase 1
0.7205	Intermediate Similarity	NPD5406	Approved
0.7205	Intermediate Similarity	NPD5408	Approved
0.7205	Intermediate Similarity	NPD5405	Approved
0.7205	Intermediate Similarity	NPD5404	Approved
0.7197	Intermediate Similarity	NPD3764	Approved
0.7197	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1296	Phase 2
0.7195	Intermediate Similarity	NPD2309	Approved
0.7171	Intermediate Similarity	NPD1535	Discovery
0.7169	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD7549	Discontinued
0.7152	Intermediate Similarity	NPD6233	Phase 2
0.7143	Intermediate Similarity	NPD7033	Discontinued
0.7134	Intermediate Similarity	NPD4625	Phase 3
0.7128	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7783	Phase 2
0.7127	Intermediate Similarity	NPD8312	Approved
0.7127	Intermediate Similarity	NPD8313	Approved
0.712	Intermediate Similarity	NPD4287	Approved
0.7115	Intermediate Similarity	NPD9494	Approved
0.7111	Intermediate Similarity	NPD7685	Pre-registration
0.7105	Intermediate Similarity	NPD3496	Discontinued
0.7104	Intermediate Similarity	NPD8434	Phase 2
0.7101	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD4476	Approved
0.7099	Intermediate Similarity	NPD4477	Approved
0.7097	Intermediate Similarity	NPD3266	Approved
0.7097	Intermediate Similarity	NPD3267	Approved
0.7086	Intermediate Similarity	NPD8127	Discontinued
0.7078	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD4908	Phase 1
0.7063	Intermediate Similarity	NPD6355	Discontinued
0.7051	Intermediate Similarity	NPD1019	Discontinued
0.7051	Intermediate Similarity	NPD2798	Approved
0.7041	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD7435	Discontinued
0.703	Intermediate Similarity	NPD4110	Phase 3
0.703	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD8151	Discontinued
0.7024	Intermediate Similarity	NPD6273	Approved
0.702	Intermediate Similarity	NPD9545	Approved
0.7017	Intermediate Similarity	NPD7038	Approved
0.7017	Intermediate Similarity	NPD7039	Approved
0.7017	Intermediate Similarity	NPD7240	Approved
0.7011	Intermediate Similarity	NPD8150	Discontinued
0.7006	Intermediate Similarity	NPD3018	Phase 2
0.7	Intermediate Similarity	NPD9493	Approved
0.7	Intermediate Similarity	NPD4307	Phase 2
0.6981	Remote Similarity	NPD6798	Discontinued
0.6981	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1652	Phase 2
0.697	Remote Similarity	NPD2654	Approved
0.6968	Remote Similarity	NPD4749	Approved
0.6966	Remote Similarity	NPD2403	Approved
0.6964	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD6777	Approved
0.6963	Remote Similarity	NPD6781	Approved
0.6963	Remote Similarity	NPD6779	Approved
0.6963	Remote Similarity	NPD6778	Approved
0.6963	Remote Similarity	NPD6782	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