NPASS Compound

Structure

NPC148480 OpenBabel07101719122D 29 31 0 0 0 0 0 0 0 0999 V2000 -3.5491 5.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3903 2.8452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 4.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 4.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 2.6361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5823 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 2.5316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9890 1.8271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8080 3.5497 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.1910 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 2.1701 0.1045 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1810 3.3406 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9836 1.9316 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 4 1 0 0 0 0 2 27 1 0 0 0 0 3 28 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 8 24 2 0 0 0 0 9 15 2 0 0 0 0 9 17 1 0 0 0 0 10 11 1 0 0 0 0 10 15 1 0 0 0 0 10 18 2 0 0 0 0 11 16 2 0 0 0 0 11 19 1 0 0 0 0 12 16 1 0 0 0 0 12 20 2 0 0 0 0 12 21 1 0 0 0 0 13 17 2 0 0 0 0 13 18 1 0 0 0 0 13 22 1 0 0 0 0 14 19 2 0 0 0 0 14 20 1 0 0 0 0 14 23 1 0 0 0 0 15 25 1 0 0 0 0 16 26 1 0 0 0 0 17 27 1 0 0 0 0 18 29 1 0 0 0 0 19 29 1 0 0 0 0 20 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	460.02
Volume:	408.726
LogP:	6.626
LogD:	4.153
LogS:	-5.223
# Rotatable Bonds:	7
TPSA:	89.13
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.299
Synthetic Accessibility Score:	3.149
Fsp3:	0.35
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:	-4.776
MDCK Permeability:	1.291727130592335e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.048
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	100.82254028320312%
Volume Distribution (VD):	0.691
Pgp-substrate:	2.2451305389404297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.39
CYP1A2-substrate:	0.823
CYP2C19-inhibitor:	0.637
CYP2C19-substrate:	0.347
CYP2C9-inhibitor:	0.923
CYP2C9-substrate:	0.932
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.214
CYP3A4-inhibitor:	0.062
CYP3A4-substrate:	0.118

ADMET: Excretion

Clearance (CL):	4.873
Half-life (T1/2):	0.116

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.243
Drug-inuced Liver Injury (DILI):	0.986
AMES Toxicity:	0.166
Rat Oral Acute Toxicity:	0.876
Maximum Recommended Daily Dose:	0.14
Skin Sensitization:	0.511
Carcinogencity:	0.267
Eye Corrosion:	0.003
Eye Irritation:	0.782
Respiratory Toxicity:	0.478

Download Data

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

Natural Product: NPC148480

Natural Product ID:	NPC148480
*Common Name:**	1-(4,6,8-Trichloro-1,9-Dihydroxy-3,7-Dimethoxydibenzofuran-2-Yl)Hexan-1-One
IUPAC Name:	1-(4,6,8-trichloro-1,9-dihydroxy-3,7-dimethoxydibenzofuran-2-yl)hexan-1-one
Synonyms:
Standard InCHIKey:	HANVBLRSGDIVGE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H19Cl3O6/c1-4-5-6-7-8(24)9-15(25)10-11-16(26)12(21)20(28-3)14(23)19(11)29-18(10)13(22)17(9)27-2/h25-26H,4-7H2,1-3H3
SMILES:	CCCCCC(=O)c1c(c2c3c(c(c(c(c3oc2c(c1OC)Cl)Cl)OC)Cl)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2409646
PubChem CID:	9868940
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans [CHEMONTID:0000015] Dibenzofurans [CHEMONTID:0001378] Chlorinated dibenzofurans [CHEMONTID:0003029] Polychlorinated dibenzofurans

*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
NPO33123	polysphondylium filamentosum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[23746784]

☑ 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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	0.39	ug.mL-1	PMID[503812]

☑ 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 NPC148480 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	473
0.1-0.2	2317
0.2-0.3	6575
0.3-0.4	13430
0.4-0.5	5363
0.5-0.6	6692
0.6-0.7	5226
0.7-0.8	2588
0.8-0.85	28
0.85-0.9	4
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8608	High Similarity	NPC200207
0.8553	High Similarity	NPC251182
0.8553	High Similarity	NPC172182
0.8553	High Similarity	NPC262935
0.8506	High Similarity	NPC472606
0.843	Intermediate Similarity	NPC107283
0.8375	Intermediate Similarity	NPC226942
0.8375	Intermediate Similarity	NPC96791
0.8375	Intermediate Similarity	NPC470636
0.8343	Intermediate Similarity	NPC45072
0.8304	Intermediate Similarity	NPC68850
0.8198	Intermediate Similarity	NPC234053
0.8122	Intermediate Similarity	NPC474499
0.8107	Intermediate Similarity	NPC474386
0.8079	Intermediate Similarity	NPC477568
0.8072	Intermediate Similarity	NPC37226
0.8072	Intermediate Similarity	NPC226644
0.8036	Intermediate Similarity	NPC5871
0.8023	Intermediate Similarity	NPC470422
0.8012	Intermediate Similarity	NPC135325
0.7988	Intermediate Similarity	NPC1477
0.7988	Intermediate Similarity	NPC213608
0.7976	Intermediate Similarity	NPC170169
0.7966	Intermediate Similarity	NPC474857
0.7964	Intermediate Similarity	NPC178202
0.7952	Intermediate Similarity	NPC12148
0.7952	Intermediate Similarity	NPC130581
0.7941	Intermediate Similarity	NPC148938
0.7929	Intermediate Similarity	NPC263676
0.7919	Intermediate Similarity	NPC472346
0.7917	Intermediate Similarity	NPC78335
0.7917	Intermediate Similarity	NPC230713
0.791	Intermediate Similarity	NPC277865
0.791	Intermediate Similarity	NPC470565
0.791	Intermediate Similarity	NPC470562
0.7895	Intermediate Similarity	NPC160015
0.7895	Intermediate Similarity	NPC247677
0.7895	Intermediate Similarity	NPC180924
0.7892	Intermediate Similarity	NPC300267
0.7892	Intermediate Similarity	NPC210826
0.7892	Intermediate Similarity	NPC51641
0.7882	Intermediate Similarity	NPC235333
0.7882	Intermediate Similarity	NPC183874
0.7877	Intermediate Similarity	NPC264922
0.787	Intermediate Similarity	NPC116604
0.787	Intermediate Similarity	NPC58668
0.787	Intermediate Similarity	NPC106372
0.7869	Intermediate Similarity	NPC471809
0.7869	Intermediate Similarity	NPC471811
0.7865	Intermediate Similarity	NPC470560
0.7857	Intermediate Similarity	NPC39929
0.7857	Intermediate Similarity	NPC296030
0.7849	Intermediate Similarity	NPC296957
0.7849	Intermediate Similarity	NPC212967
0.7849	Intermediate Similarity	NPC96342
0.7849	Intermediate Similarity	NPC164110
0.7849	Intermediate Similarity	NPC65504
0.7849	Intermediate Similarity	NPC246647
0.7849	Intermediate Similarity	NPC260902
0.7848	Intermediate Similarity	NPC320819
0.7844	Intermediate Similarity	NPC17816
0.7836	Intermediate Similarity	NPC297531
0.7836	Intermediate Similarity	NPC198490
0.7836	Intermediate Similarity	NPC213936
0.7831	Intermediate Similarity	NPC230943
0.7824	Intermediate Similarity	NPC253872
0.7824	Intermediate Similarity	NPC207624
0.7814	Intermediate Similarity	NPC471808
0.7814	Intermediate Similarity	NPC471814
0.7814	Intermediate Similarity	NPC195675
0.7805	Intermediate Similarity	NPC289660
0.7805	Intermediate Similarity	NPC164697
0.7805	Intermediate Similarity	NPC82920
0.7803	Intermediate Similarity	NPC476349
0.7803	Intermediate Similarity	NPC40583
0.7803	Intermediate Similarity	NPC476350
0.7802	Intermediate Similarity	NPC151292
0.7797	Intermediate Similarity	NPC472032
0.7784	Intermediate Similarity	NPC313386
0.7778	Intermediate Similarity	NPC472462
0.7772	Intermediate Similarity	NPC191606
0.7771	Intermediate Similarity	NPC225884
0.7771	Intermediate Similarity	NPC219861
0.7771	Intermediate Similarity	NPC302181
0.7765	Intermediate Similarity	NPC115324
0.7765	Intermediate Similarity	NPC23668
0.7765	Intermediate Similarity	NPC193976
0.7759	Intermediate Similarity	NPC115432
0.7759	Intermediate Similarity	NPC260296
0.7758	Intermediate Similarity	NPC111201
0.7751	Intermediate Similarity	NPC221868
0.7751	Intermediate Similarity	NPC37208
0.7746	Intermediate Similarity	NPC268360
0.7744	Intermediate Similarity	NPC270913
0.7742	Intermediate Similarity	NPC39409
0.7727	Intermediate Similarity	NPC109180
0.7727	Intermediate Similarity	NPC472581
0.7725	Intermediate Similarity	NPC198163
0.7725	Intermediate Similarity	NPC193676
0.7719	Intermediate Similarity	NPC67654
0.7719	Intermediate Similarity	NPC142308
0.7711	Intermediate Similarity	NPC53192
0.7706	Intermediate Similarity	NPC472406
0.7706	Intermediate Similarity	NPC167576
0.7701	Intermediate Similarity	NPC471806
0.7701	Intermediate Similarity	NPC244750
0.7701	Intermediate Similarity	NPC471810
0.7697	Intermediate Similarity	NPC28337
0.7692	Intermediate Similarity	NPC272194
0.7688	Intermediate Similarity	NPC316091
0.7688	Intermediate Similarity	NPC471804
0.7688	Intermediate Similarity	NPC471812
0.7674	Intermediate Similarity	NPC122365
0.7673	Intermediate Similarity	NPC186628
0.767	Intermediate Similarity	NPC474096
0.767	Intermediate Similarity	NPC193998
0.7661	Intermediate Similarity	NPC156244
0.7657	Intermediate Similarity	NPC220582
0.7657	Intermediate Similarity	NPC304839
0.7651	Intermediate Similarity	NPC285659
0.7651	Intermediate Similarity	NPC157497
0.7651	Intermediate Similarity	NPC81337
0.765	Intermediate Similarity	NPC306240
0.7647	Intermediate Similarity	NPC471813
0.7647	Intermediate Similarity	NPC121100
0.7647	Intermediate Similarity	NPC471805
0.7647	Intermediate Similarity	NPC317492
0.7644	Intermediate Similarity	NPC154720
0.7633	Intermediate Similarity	NPC198427
0.7633	Intermediate Similarity	NPC308200
0.763	Intermediate Similarity	NPC99199
0.7627	Intermediate Similarity	NPC155640
0.7627	Intermediate Similarity	NPC470563
0.7627	Intermediate Similarity	NPC470081
0.7625	Intermediate Similarity	NPC279566
0.7619	Intermediate Similarity	NPC98926
0.7619	Intermediate Similarity	NPC214901
0.7619	Intermediate Similarity	NPC155144
0.7614	Intermediate Similarity	NPC45124
0.7614	Intermediate Similarity	NPC30655
0.7614	Intermediate Similarity	NPC74854
0.7614	Intermediate Similarity	NPC304387
0.7606	Intermediate Similarity	NPC471807
0.7605	Intermediate Similarity	NPC472344
0.7602	Intermediate Similarity	NPC476509
0.7602	Intermediate Similarity	NPC148423
0.7602	Intermediate Similarity	NPC476185
0.7602	Intermediate Similarity	NPC135303
0.7602	Intermediate Similarity	NPC321896
0.7596	Intermediate Similarity	NPC28160
0.7588	Intermediate Similarity	NPC145467
0.7588	Intermediate Similarity	NPC39195
0.7588	Intermediate Similarity	NPC168085
0.7584	Intermediate Similarity	NPC37183
0.7576	Intermediate Similarity	NPC272844
0.7576	Intermediate Similarity	NPC254168
0.7576	Intermediate Similarity	NPC248995
0.7572	Intermediate Similarity	NPC72370
0.7571	Intermediate Similarity	NPC470561
0.7571	Intermediate Similarity	NPC245122
0.7566	Intermediate Similarity	NPC220369
0.756	Intermediate Similarity	NPC112749
0.7554	Intermediate Similarity	NPC471801
0.7545	Intermediate Similarity	NPC74397
0.7544	Intermediate Similarity	NPC471114
0.7543	Intermediate Similarity	NPC270044
0.7542	Intermediate Similarity	NPC277480
0.7542	Intermediate Similarity	NPC53640
0.7541	Intermediate Similarity	NPC175804
0.7531	Intermediate Similarity	NPC215875
0.7531	Intermediate Similarity	NPC15834
0.7531	Intermediate Similarity	NPC285054
0.753	Intermediate Similarity	NPC217186
0.753	Intermediate Similarity	NPC240305
0.753	Intermediate Similarity	NPC53181
0.7528	Intermediate Similarity	NPC38591
0.7515	Intermediate Similarity	NPC224714
0.7515	Intermediate Similarity	NPC273538
0.7515	Intermediate Similarity	NPC470890
0.7515	Intermediate Similarity	NPC322301
0.7515	Intermediate Similarity	NPC271288
0.7515	Intermediate Similarity	NPC216538
0.7515	Intermediate Similarity	NPC311741
0.7515	Intermediate Similarity	NPC311144
0.7515	Intermediate Similarity	NPC234629
0.7515	Intermediate Similarity	NPC255801
0.7514	Intermediate Similarity	NPC298401
0.7514	Intermediate Similarity	NPC38361
0.7514	Intermediate Similarity	NPC130015
0.75	Intermediate Similarity	NPC13282
0.75	Intermediate Similarity	NPC29777
0.75	Intermediate Similarity	NPC476459
0.75	Intermediate Similarity	NPC101752
0.75	Intermediate Similarity	NPC247973
0.75	Intermediate Similarity	NPC472421
0.75	Intermediate Similarity	NPC471802
0.75	Intermediate Similarity	NPC471803
0.75	Intermediate Similarity	NPC50394
0.75	Intermediate Similarity	NPC471115
0.7486	Intermediate Similarity	NPC58653

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 NPC148480 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	397
0.1-0.2	1207
0.2-0.3	2340
0.3-0.4	2889
0.4-0.5	1646
0.5-0.6	503
0.6-0.7	137
0.7-0.8	30
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
0.8198	Intermediate Similarity	NPD2403	Approved
0.7744	Intermediate Similarity	NPD2800	Approved
0.7515	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD2532	Approved
0.731	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD2533	Approved
0.731	Intermediate Similarity	NPD2534	Approved
0.7273	Intermediate Similarity	NPD6651	Approved
0.7257	Intermediate Similarity	NPD7411	Suspended
0.7247	Intermediate Similarity	NPD3749	Approved
0.7225	Intermediate Similarity	NPD920	Approved
0.7222	Intermediate Similarity	NPD6959	Discontinued
0.7202	Intermediate Similarity	NPD2344	Approved
0.7198	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD1243	Approved
0.7101	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD4361	Phase 2
0.7059	Intermediate Similarity	NPD1549	Phase 2
0.7048	Intermediate Similarity	NPD1240	Approved
0.7035	Intermediate Similarity	NPD2309	Approved
0.7011	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD4360	Phase 2
0.701	Intermediate Similarity	NPD4363	Phase 3
0.7006	Intermediate Similarity	NPD4380	Phase 2
0.7	Intermediate Similarity	NPD3882	Suspended
0.7	Intermediate Similarity	NPD7768	Phase 2
0.6983	Remote Similarity	NPD2801	Approved
0.6983	Remote Similarity	NPD7819	Suspended
0.6982	Remote Similarity	NPD1510	Phase 2
0.6968	Remote Similarity	NPD6559	Discontinued
0.6964	Remote Similarity	NPD1607	Approved
0.6961	Remote Similarity	NPD7075	Discontinued
0.6941	Remote Similarity	NPD2796	Approved
0.694	Remote Similarity	NPD1247	Approved
0.6927	Remote Similarity	NPD1934	Approved
0.6919	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD6232	Discontinued
0.6897	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD5494	Approved
0.6882	Remote Similarity	NPD7473	Discontinued
0.6865	Remote Similarity	NPD3926	Phase 2
0.6857	Remote Similarity	NPD1511	Approved
0.6833	Remote Similarity	NPD6801	Discontinued
0.6811	Remote Similarity	NPD5711	Approved
0.6811	Remote Similarity	NPD5710	Approved
0.6805	Remote Similarity	NPD1184	Approved
0.678	Remote Similarity	NPD1512	Approved
0.6776	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD6799	Approved
0.6755	Remote Similarity	NPD3818	Discontinued
0.6754	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD6166	Phase 2
0.6738	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD6599	Discontinued
0.672	Remote Similarity	NPD7286	Phase 2
0.672	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD2799	Discontinued
0.6686	Remote Similarity	NPD3750	Approved
0.6667	Remote Similarity	NPD3226	Approved
0.6667	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1852	Discontinued
0.6649	Remote Similarity	NPD5953	Discontinued
0.6649	Remote Similarity	NPD919	Approved
0.6647	Remote Similarity	NPD2935	Discontinued
0.663	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD6312	Discontinued
0.6576	Remote Similarity	NPD2296	Approved
0.6576	Remote Similarity	NPD3817	Phase 2
0.6576	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD7390	Discontinued
0.6552	Remote Similarity	NPD1551	Phase 2
0.6548	Remote Similarity	NPD4287	Approved
0.6545	Remote Similarity	NPD5844	Phase 1
0.6529	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD2313	Discontinued
0.6514	Remote Similarity	NPD1471	Phase 3
0.651	Remote Similarity	NPD7074	Phase 3
0.6494	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD7054	Approved
0.6455	Remote Similarity	NPD6808	Phase 2
0.6455	Remote Similarity	NPD7229	Phase 3
0.6433	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD1465	Phase 2
0.6425	Remote Similarity	NPD7472	Approved
0.6425	Remote Similarity	NPD1729	Discontinued
0.642	Remote Similarity	NPD2346	Discontinued
0.6404	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.64	Remote Similarity	NPD3748	Approved
0.6392	Remote Similarity	NPD6797	Phase 2
0.6378	Remote Similarity	NPD6280	Approved
0.6378	Remote Similarity	NPD6279	Approved
0.6369	Remote Similarity	NPD2354	Approved
0.6364	Remote Similarity	NPD6099	Approved
0.6364	Remote Similarity	NPD6100	Approved
0.6359	Remote Similarity	NPD7251	Discontinued
0.6353	Remote Similarity	NPD454	Approved
0.6348	Remote Similarity	NPD2654	Approved
0.6337	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD3268	Approved
0.6327	Remote Similarity	NPD7808	Phase 3
0.6327	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD958	Approved
0.6316	Remote Similarity	NPD4908	Phase 1
0.6313	Remote Similarity	NPD4628	Phase 3
0.6313	Remote Similarity	NPD6785	Approved
0.6313	Remote Similarity	NPD6784	Approved
0.631	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.631	Remote Similarity	NPD5402	Approved
0.6308	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD5403	Approved
0.6281	Remote Similarity	NPD8434	Phase 2
0.6278	Remote Similarity	NPD3887	Approved
0.6264	Remote Similarity	NPD943	Approved
0.6262	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.625	Remote Similarity	NPD957	Approved
0.6236	Remote Similarity	NPD2353	Approved
0.6236	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD1203	Approved
0.623	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD5822	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD1714	Approved
0.6183	Remote Similarity	NPD1715	Phase 1
0.6175	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6175	Remote Similarity	NPD5401	Approved
0.617	Remote Similarity	NPD5760	Phase 2
0.617	Remote Similarity	NPD5761	Phase 2
0.6158	Remote Similarity	NPD3819	Phase 2
0.615	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD3764	Approved
0.6136	Remote Similarity	NPD5124	Phase 1
0.6136	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD6832	Phase 2
0.6124	Remote Similarity	NPD7033	Discontinued
0.6124	Remote Similarity	NPD5588	Approved
0.6117	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD2798	Approved
0.6095	Remote Similarity	NPD1610	Phase 2
0.6092	Remote Similarity	NPD4625	Phase 3
0.6089	Remote Similarity	NPD5405	Approved
0.6089	Remote Similarity	NPD5408	Approved
0.6089	Remote Similarity	NPD5406	Approved
0.6089	Remote Similarity	NPD5404	Approved
0.6087	Remote Similarity	NPD1578	Phase 2
0.6078	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD4536	Approved
0.6067	Remote Similarity	NPD4538	Approved
0.6066	Remote Similarity	NPD5058	Phase 3
0.6062	Remote Similarity	NPD7199	Phase 2
0.6059	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6059	Remote Similarity	NPD9717	Approved
0.6056	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD6004	Phase 3
0.6056	Remote Similarity	NPD6002	Phase 3
0.6056	Remote Similarity	NPD6005	Phase 3
0.6056	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6051	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.605	Remote Similarity	NPD8313	Approved
0.605	Remote Similarity	NPD8312	Approved
0.6047	Remote Similarity	NPD3267	Approved
0.6047	Remote Similarity	NPD2797	Approved
0.6047	Remote Similarity	NPD3266	Approved
0.6045	Remote Similarity	NPD230	Phase 1
0.6044	Remote Similarity	NPD7003	Approved
0.6043	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD6234	Discontinued
0.6033	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD37	Approved
0.6028	Remote Similarity	NPD8151	Discontinued
0.6022	Remote Similarity	NPD5958	Discontinued
0.6022	Remote Similarity	NPD4534	Discontinued
0.6021	Remote Similarity	NPD4966	Approved
0.6021	Remote Similarity	NPD4965	Approved
0.6021	Remote Similarity	NPD4967	Phase 2
0.6011	Remote Similarity	NPD4972	Discontinued
0.601	Remote Similarity	NPD3365	Discontinued
0.6	Remote Similarity	NPD422	Phase 1
0.6	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3269	Clinical (unspecified phase)
0.6	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.599	Remote Similarity	NPD1163	Approved
0.599	Remote Similarity	NPD3751	Discontinued
0.5979	Remote Similarity	NPD5889	Approved
0.5979	Remote Similarity	NPD5890	Approved
0.5969	Remote Similarity	NPD4288	Approved
0.5965	Remote Similarity	NPD1608	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