NPASS Compound

Structure

NPC471812 OpenBabel07101718192D 26 28 0 0 0 0 0 0 0 0999 V2000 -0.0842 0.8765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7105 1.5794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7818 1.3765 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 1.6479 0.8765 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 2.5139 -0.6235 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 1.6479 -0.1235 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 -2.4060 -1.0488 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 -1.4088 -1.1235 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 -1.5382 -2.8507 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 -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 -3.9665 -1.8003 0.0000 Cl 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 -2.1235 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 -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 9 1 0 0 0 0 6 11 1 0 0 0 0 7 9 2 0 0 0 0 7 10 1 0 0 0 0 8 10 2 0 0 0 0 8 12 1 0 0 0 0 9 17 1 0 0 0 0 10 22 1 0 0 0 0 11 13 2 0 0 0 0 11 14 1 0 0 0 0 12 17 2 0 0 0 0 12 25 1 0 0 0 0 13 18 1 0 0 0 0 13 19 1 0 0 0 0 14 16 2 0 0 0 0 14 20 1 0 0 0 0 15 16 1 0 0 0 0 15 18 2 0 0 0 0 15 21 1 0 0 0 0 16 23 1 0 0 0 0 17 26 1 0 0 0 0 18 25 1 0 0 0 0 19 24 2 0 0 0 0 19 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	396.05
Volume:	367.429
LogP:	6.422
LogD:	4.32
LogS:	-5.047
# Rotatable Bonds:	4
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.516
Synthetic Accessibility Score:	3.178
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:	-5.098
MDCK Permeability:	1.8793918570736423e-05
Pgp-inhibitor:	0.031
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.043
20% Bioavailability (F20%):	0.017
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.041
Plasma Protein Binding (PPB):	100.73908233642578%
Volume Distribution (VD):	1.111
Pgp-substrate:	0.786305844783783%

ADMET: Metabolism

CYP1A2-inhibitor:	0.889
CYP1A2-substrate:	0.22
CYP2C19-inhibitor:	0.696
CYP2C19-substrate:	0.101
CYP2C9-inhibitor:	0.811
CYP2C9-substrate:	0.957
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.57
CYP3A4-inhibitor:	0.148
CYP3A4-substrate:	0.099

ADMET: Excretion

Clearance (CL):	7.316
Half-life (T1/2):	0.332

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.028
Drug-inuced Liver Injury (DILI):	0.153
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.921
Maximum Recommended Daily Dose:	0.955
Skin Sensitization:	0.922
Carcinogencity:	0.333
Eye Corrosion:	0.003
Eye Irritation:	0.907
Respiratory Toxicity:	0.903

Download Data

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

Natural Product: NPC471812

Natural Product ID:	NPC471812
*Common Name:**	Spiromastixone M
IUPAC Name:	8,10-dichloro-2,9-dihydroxy-4,7-dipropylbenzo[b][1,4]benzodioxepin-6-one
Synonyms:
Standard InCHIKey:	LKXWAIQYUYTUSL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H18Cl2O5/c1-3-5-9-7-10(22)8-12-17(9)26-19(24)13-11(6-4-2)14(20)16(23)15(21)18(13)25-12/h7-8,22-23H,3-6H2,1-2H3
SMILES:	CCCC1=C2C(=CC(=C1)O)OC3=C(C(=C(C(=C3C(=O)O2)CCC)Cl)O)Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3234403
PubChem CID:	90670416
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[474641]
NPT1261	Organism	Bacillus thuringiensis	Bacillus thuringiensis	MIC	=	2.0	ug.mL-1	PMID[474641]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	2.0	ug.mL-1	PMID[474641]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	128.0	ug.mL-1	PMID[474641]

☑ 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 NPC471812 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	500
0.1-0.2	2580
0.2-0.3	7470
0.3-0.4	12231
0.4-0.5	4007
0.5-0.6	6042
0.6-0.7	7413
0.7-0.8	2373
0.8-0.85	47
0.85-0.9	11
0.9-0.95	11
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471804
0.9884	High Similarity	NPC471807
0.9827	High Similarity	NPC471813
0.9827	High Similarity	NPC471805
0.977	High Similarity	NPC471810
0.977	High Similarity	NPC471806
0.9769	High Similarity	NPC471803
0.9713	High Similarity	NPC121100
0.9649	High Similarity	NPC471801
0.9591	High Similarity	NPC471802
0.9489	High Similarity	NPC39409
0.9483	High Similarity	NPC471808
0.9483	High Similarity	NPC471814
0.9429	High Similarity	NPC471811
0.9429	High Similarity	NPC471809
0.9371	High Similarity	NPC195675
0.9195	High Similarity	NPC108278
0.9116	High Similarity	NPC214901
0.9086	High Similarity	NPC175804
0.9061	High Similarity	NPC220369
0.8927	High Similarity	NPC28160
0.8817	High Similarity	NPC154720
0.871	High Similarity	NPC198163
0.8701	High Similarity	NPC188618
0.8596	High Similarity	NPC471800
0.8556	High Similarity	NPC45072
0.8547	High Similarity	NPC470422
0.8448	Intermediate Similarity	NPC238381
0.8413	Intermediate Similarity	NPC193676
0.8352	Intermediate Similarity	NPC303565
0.8305	Intermediate Similarity	NPC93739
0.8258	Intermediate Similarity	NPC156082
0.8258	Intermediate Similarity	NPC284007
0.8258	Intermediate Similarity	NPC300984
0.8222	Intermediate Similarity	NPC472032
0.8212	Intermediate Similarity	NPC267153
0.8212	Intermediate Similarity	NPC8070
0.8212	Intermediate Similarity	NPC112981
0.8167	Intermediate Similarity	NPC20216
0.8138	Intermediate Similarity	NPC474499
0.8136	Intermediate Similarity	NPC83763
0.8136	Intermediate Similarity	NPC168616
0.8125	Intermediate Similarity	NPC54928
0.8122	Intermediate Similarity	NPC272485
0.8122	Intermediate Similarity	NPC292788
0.809	Intermediate Similarity	NPC200594
0.8057	Intermediate Similarity	NPC289968
0.8056	Intermediate Similarity	NPC474350
0.8053	Intermediate Similarity	NPC470099
0.8053	Intermediate Similarity	NPC470100
0.8045	Intermediate Similarity	NPC298401
0.8033	Intermediate Similarity	NPC20543
0.8033	Intermediate Similarity	NPC17219
0.8033	Intermediate Similarity	NPC246716
0.8033	Intermediate Similarity	NPC239440
0.8011	Intermediate Similarity	NPC58653
0.8011	Intermediate Similarity	NPC173352
0.8	Intermediate Similarity	NPC8300
0.8	Intermediate Similarity	NPC477568
0.8	Intermediate Similarity	NPC474096
0.8	Intermediate Similarity	NPC473696
0.7989	Intermediate Similarity	NPC474857
0.7978	Intermediate Similarity	NPC26568
0.7969	Intermediate Similarity	NPC221185
0.7967	Intermediate Similarity	NPC474061
0.7967	Intermediate Similarity	NPC28669
0.7956	Intermediate Similarity	NPC470081
0.7956	Intermediate Similarity	NPC234004
0.7946	Intermediate Similarity	NPC181523
0.7944	Intermediate Similarity	NPC472405
0.7935	Intermediate Similarity	NPC10576
0.7935	Intermediate Similarity	NPC277865
0.7935	Intermediate Similarity	NPC1827
0.7935	Intermediate Similarity	NPC470565
0.7927	Intermediate Similarity	NPC247104
0.7921	Intermediate Similarity	NPC274730
0.7921	Intermediate Similarity	NPC472456
0.7912	Intermediate Similarity	NPC130920
0.7912	Intermediate Similarity	NPC85057
0.7907	Intermediate Similarity	NPC66404
0.7907	Intermediate Similarity	NPC95123
0.7903	Intermediate Similarity	NPC139350
0.7903	Intermediate Similarity	NPC264922
0.7903	Intermediate Similarity	NPC289147
0.7895	Intermediate Similarity	NPC105648
0.7887	Intermediate Similarity	NPC48822
0.7886	Intermediate Similarity	NPC328119
0.788	Intermediate Similarity	NPC49487
0.788	Intermediate Similarity	NPC99613
0.7877	Intermediate Similarity	NPC241904
0.7877	Intermediate Similarity	NPC472404
0.7877	Intermediate Similarity	NPC165977
0.7877	Intermediate Similarity	NPC217677
0.7877	Intermediate Similarity	NPC300727
0.7869	Intermediate Similarity	NPC29160
0.7865	Intermediate Similarity	NPC20541
0.7861	Intermediate Similarity	NPC29577
0.7861	Intermediate Similarity	NPC134621
0.7842	Intermediate Similarity	NPC99937
0.7838	Intermediate Similarity	NPC107283
0.7838	Intermediate Similarity	NPC470562
0.7838	Intermediate Similarity	NPC109827
0.7838	Intermediate Similarity	NPC124470
0.7836	Intermediate Similarity	NPC220106
0.7833	Intermediate Similarity	NPC100123
0.7833	Intermediate Similarity	NPC476242
0.7831	Intermediate Similarity	NPC151292
0.7826	Intermediate Similarity	NPC234331
0.7816	Intermediate Similarity	NPC237208
0.7814	Intermediate Similarity	NPC68850
0.7812	Intermediate Similarity	NPC136411
0.7812	Intermediate Similarity	NPC316091
0.7809	Intermediate Similarity	NPC89474
0.7809	Intermediate Similarity	NPC475895
0.7801	Intermediate Similarity	NPC191606
0.7797	Intermediate Similarity	NPC208043
0.7797	Intermediate Similarity	NPC226973
0.7797	Intermediate Similarity	NPC204350
0.7797	Intermediate Similarity	NPC308451
0.7796	Intermediate Similarity	NPC470560
0.7796	Intermediate Similarity	NPC158226
0.779	Intermediate Similarity	NPC228785
0.779	Intermediate Similarity	NPC320359
0.779	Intermediate Similarity	NPC200746
0.779	Intermediate Similarity	NPC474287
0.779	Intermediate Similarity	NPC475886
0.779	Intermediate Similarity	NPC14353
0.779	Intermediate Similarity	NPC56085
0.7784	Intermediate Similarity	NPC165979
0.7784	Intermediate Similarity	NPC163130
0.7778	Intermediate Similarity	NPC108456
0.7778	Intermediate Similarity	NPC113446
0.7778	Intermediate Similarity	NPC306240
0.7772	Intermediate Similarity	NPC472452
0.7771	Intermediate Similarity	NPC62536
0.7771	Intermediate Similarity	NPC12305
0.7771	Intermediate Similarity	NPC33265
0.7755	Intermediate Similarity	NPC313541
0.7747	Intermediate Similarity	NPC61010
0.7747	Intermediate Similarity	NPC40491
0.7747	Intermediate Similarity	NPC278052
0.7747	Intermediate Similarity	NPC66288
0.7747	Intermediate Similarity	NPC474186
0.7747	Intermediate Similarity	NPC475883
0.7747	Intermediate Similarity	NPC474351
0.7747	Intermediate Similarity	NPC474187
0.774	Intermediate Similarity	NPC306821
0.7727	Intermediate Similarity	NPC195202
0.7727	Intermediate Similarity	NPC108744
0.7727	Intermediate Similarity	NPC105415
0.7722	Intermediate Similarity	NPC142339
0.7722	Intermediate Similarity	NPC227062
0.772	Intermediate Similarity	NPC313386
0.7709	Intermediate Similarity	NPC255350
0.7709	Intermediate Similarity	NPC145379
0.7709	Intermediate Similarity	NPC472915
0.7709	Intermediate Similarity	NPC246204
0.7709	Intermediate Similarity	NPC160951
0.7709	Intermediate Similarity	NPC274327
0.7709	Intermediate Similarity	NPC280937
0.7709	Intermediate Similarity	NPC231018
0.7709	Intermediate Similarity	NPC250822
0.7709	Intermediate Similarity	NPC75279
0.7709	Intermediate Similarity	NPC22519
0.7709	Intermediate Similarity	NPC69394
0.7709	Intermediate Similarity	NPC176775
0.7709	Intermediate Similarity	NPC47781
0.7709	Intermediate Similarity	NPC183878
0.7709	Intermediate Similarity	NPC276409
0.7709	Intermediate Similarity	NPC86485
0.7708	Intermediate Similarity	NPC470103
0.7705	Intermediate Similarity	NPC25152
0.7705	Intermediate Similarity	NPC229632
0.7697	Intermediate Similarity	NPC474663
0.7697	Intermediate Similarity	NPC117579
0.7697	Intermediate Similarity	NPC202157
0.7692	Intermediate Similarity	NPC139036
0.7692	Intermediate Similarity	NPC47623
0.7688	Intermediate Similarity	NPC148480
0.7684	Intermediate Similarity	NPC48479
0.7684	Intermediate Similarity	NPC233267
0.7684	Intermediate Similarity	NPC177298
0.7684	Intermediate Similarity	NPC329161
0.7684	Intermediate Similarity	NPC285527
0.7684	Intermediate Similarity	NPC240887
0.7684	Intermediate Similarity	NPC291049
0.7684	Intermediate Similarity	NPC470091
0.7684	Intermediate Similarity	NPC6923
0.7684	Intermediate Similarity	NPC106334
0.768	Intermediate Similarity	NPC236796
0.768	Intermediate Similarity	NPC181960
0.768	Intermediate Similarity	NPC469584
0.767	Intermediate Similarity	NPC119660
0.767	Intermediate Similarity	NPC93034
0.767	Intermediate Similarity	NPC477569
0.767	Intermediate Similarity	NPC12200
0.7667	Intermediate Similarity	NPC256612
0.7667	Intermediate Similarity	NPC163780
0.7667	Intermediate Similarity	NPC167815
0.7667	Intermediate Similarity	NPC92659

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 NPC471812 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	450
0.1-0.2	1201
0.2-0.3	2316
0.3-0.4	2701
0.4-0.5	1546
0.5-0.6	697
0.6-0.7	210
0.7-0.8	29
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
0.7829	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD2801	Approved
0.7622	Intermediate Similarity	NPD2403	Approved
0.7514	Intermediate Similarity	NPD6232	Discontinued
0.75	Intermediate Similarity	NPD5844	Phase 1
0.7473	Intermediate Similarity	NPD3817	Phase 2
0.7459	Intermediate Similarity	NPD1934	Approved
0.7418	Intermediate Similarity	NPD1465	Phase 2
0.7414	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD1511	Approved
0.7394	Intermediate Similarity	NPD7473	Discontinued
0.7337	Intermediate Similarity	NPD3882	Suspended
0.7322	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD1512	Approved
0.7254	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD7819	Suspended
0.7158	Intermediate Similarity	NPD6166	Phase 2
0.7158	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7054	Approved
0.7128	Intermediate Similarity	NPD5494	Approved
0.7111	Intermediate Similarity	NPD6799	Approved
0.7098	Intermediate Similarity	NPD7472	Approved
0.7098	Intermediate Similarity	NPD7074	Phase 3
0.7083	Intermediate Similarity	NPD3818	Discontinued
0.7072	Intermediate Similarity	NPD2534	Approved
0.7072	Intermediate Similarity	NPD2532	Approved
0.7072	Intermediate Similarity	NPD2533	Approved
0.7072	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD1184	Approved
0.7069	Intermediate Similarity	NPD447	Suspended
0.7039	Intermediate Similarity	NPD3750	Approved
0.7021	Intermediate Similarity	NPD3749	Approved
0.7021	Intermediate Similarity	NPD7075	Discontinued
0.7006	Intermediate Similarity	NPD2935	Discontinued
0.699	Remote Similarity	NPD7808	Phase 3
0.6974	Remote Similarity	NPD6797	Phase 2
0.6973	Remote Similarity	NPD6599	Discontinued
0.6952	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7251	Discontinued
0.6915	Remote Similarity	NPD5402	Approved
0.6911	Remote Similarity	NPD6959	Discontinued
0.6906	Remote Similarity	NPD2354	Approved
0.6895	Remote Similarity	NPD919	Approved
0.6888	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD958	Approved
0.6845	Remote Similarity	NPD7411	Suspended
0.6842	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD1549	Phase 2
0.6828	Remote Similarity	NPD3226	Approved
0.6823	Remote Similarity	NPD7199	Phase 2
0.6818	Remote Similarity	NPD1240	Approved
0.6816	Remote Similarity	NPD1551	Phase 2
0.6814	Remote Similarity	NPD4360	Phase 2
0.6814	Remote Similarity	NPD4363	Phase 3
0.6809	Remote Similarity	NPD6801	Discontinued
0.68	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD4380	Phase 2
0.6789	Remote Similarity	NPD7768	Phase 2
0.6782	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.678	Remote Similarity	NPD230	Phase 1
0.6778	Remote Similarity	NPD2353	Approved
0.6778	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD957	Approved
0.676	Remote Similarity	NPD2799	Discontinued
0.676	Remote Similarity	NPD3748	Approved
0.676	Remote Similarity	NPD1510	Phase 2
0.6753	Remote Similarity	NPD3926	Phase 2
0.6753	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD1607	Approved
0.6737	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD1247	Approved
0.6732	Remote Similarity	NPD6312	Discontinued
0.6722	Remote Similarity	NPD2796	Approved
0.6721	Remote Similarity	NPD3887	Approved
0.672	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.672	Remote Similarity	NPD37	Approved
0.6719	Remote Similarity	NPD6234	Discontinued
0.6718	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD1203	Approved
0.6703	Remote Similarity	NPD1243	Approved
0.6703	Remote Similarity	NPD2800	Approved
0.6702	Remote Similarity	NPD4965	Approved
0.6702	Remote Similarity	NPD4967	Phase 2
0.6702	Remote Similarity	NPD4966	Approved
0.6699	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD4361	Phase 2
0.6667	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4628	Phase 3
0.6649	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6631	Remote Similarity	NPD5403	Approved
0.6629	Remote Similarity	NPD943	Approved
0.6629	Remote Similarity	NPD454	Approved
0.6616	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD5711	Approved
0.6615	Remote Similarity	NPD5710	Approved
0.6614	Remote Similarity	NPD4972	Discontinued
0.6613	Remote Similarity	NPD1578	Phase 2
0.66	Remote Similarity	NPD6559	Discontinued
0.6596	Remote Similarity	NPD1653	Approved
0.6593	Remote Similarity	NPD2346	Discontinued
0.6592	Remote Similarity	NPD1933	Approved
0.6576	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6576	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD4534	Discontinued
0.6553	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD920	Approved
0.6538	Remote Similarity	NPD6099	Approved
0.6538	Remote Similarity	NPD6100	Approved
0.6534	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD9717	Approved
0.6524	Remote Similarity	NPD5401	Approved
0.6522	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.65	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD6832	Phase 2
0.6497	Remote Similarity	NPD5242	Approved
0.6497	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6482	Remote Similarity	NPD3751	Discontinued
0.6482	Remote Similarity	NPD7228	Approved
0.6477	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD422	Phase 1
0.6471	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7390	Discontinued
0.6468	Remote Similarity	NPD5953	Discontinued
0.6467	Remote Similarity	NPD5958	Discontinued
0.645	Remote Similarity	NPD7286	Phase 2
0.6447	Remote Similarity	NPD3787	Discontinued
0.6437	Remote Similarity	NPD1608	Approved
0.6436	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD411	Approved
0.6425	Remote Similarity	NPD3268	Approved
0.642	Remote Similarity	NPD2797	Approved
0.6417	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD2344	Approved
0.6392	Remote Similarity	NPD5353	Approved
0.6392	Remote Similarity	NPD4288	Approved
0.6382	Remote Similarity	NPD5822	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD3027	Phase 3
0.6364	Remote Similarity	NPD7229	Phase 3
0.6364	Remote Similarity	NPD6190	Approved
0.6359	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD3303	Discontinued
0.6354	Remote Similarity	NPD1613	Approved
0.6354	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD7783	Phase 2
0.6347	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD9269	Phase 2
0.6339	Remote Similarity	NPD4538	Approved
0.6339	Remote Similarity	NPD4536	Approved
0.6339	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD2313	Discontinued
0.6324	Remote Similarity	NPD7549	Discontinued
0.6321	Remote Similarity	NPD6386	Approved
0.6321	Remote Similarity	NPD6385	Approved
0.6311	Remote Similarity	NPD6785	Approved
0.6311	Remote Similarity	NPD6784	Approved
0.6304	Remote Similarity	NPD4308	Phase 3
0.6301	Remote Similarity	NPD9268	Approved
0.6298	Remote Similarity	NPD4287	Approved
0.6293	Remote Similarity	NPD8313	Approved
0.6293	Remote Similarity	NPD8312	Approved
0.6284	Remote Similarity	NPD6651	Approved
0.628	Remote Similarity	NPD8434	Phase 2
0.6277	Remote Similarity	NPD2309	Approved
0.6275	Remote Similarity	NPD7685	Pre-registration
0.6271	Remote Similarity	NPD3225	Approved
0.627	Remote Similarity	NPD5405	Approved
0.627	Remote Similarity	NPD5408	Approved
0.627	Remote Similarity	NPD5406	Approved
0.627	Remote Similarity	NPD5404	Approved
0.6264	Remote Similarity	NPD17	Approved
0.6264	Remote Similarity	NPD4060	Phase 1
0.6263	Remote Similarity	NPD3365	Discontinued
0.6263	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD8151	Discontinued
0.625	Remote Similarity	NPD1481	Phase 2
0.625	Remote Similarity	NPD7435	Discontinued
0.6244	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD1296	Phase 2
0.6243	Remote Similarity	NPD3764	Approved
0.6243	Remote Similarity	NPD5058	Phase 3
0.6243	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD8127	Discontinued
0.6218	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD5588	Approved
0.6216	Remote Similarity	NPD7033	Discontinued
0.6216	Remote Similarity	NPD5960	Phase 3
0.6209	Remote Similarity	NPD6233	Phase 2
0.6202	Remote Similarity	NPD8150	Discontinued
0.6195	Remote Similarity	NPD7039	Approved
0.6195	Remote Similarity	NPD7240	Approved
0.6195	Remote Similarity	NPD7038	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