NPASS Compound

Structure

CID230713 OpenBabel06191716022D 23 25 0 0 0 0 0 0 0 0999 V2000 -3.5491 -3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -1.6910 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 -1.8171 -1.1910 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 2.0878 1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0878 -0.0570 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 3.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -2.6910 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 1.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0878 1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0878 -0.0570 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 -2.6831 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 -0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5878 2.5411 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5878 -0.9230 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 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 11 1 0 0 0 0 3 5 1 0 0 0 0 3 11 2 0 0 0 0 4 6 2 0 0 0 0 4 12 1 0 0 0 0 5 16 1 0 0 0 0 6 17 1 0 0 0 0 7 13 2 0 0 0 0 7 14 1 0 0 0 0 8 13 1 0 0 0 0 8 15 2 0 0 0 0 9 12 1 0 0 0 0 9 18 2 0 0 0 0 10 14 2 0 0 0 0 10 15 1 0 0 0 0 12 19 2 0 0 0 0 13 18 1 0 0 0 0 14 20 1 0 0 0 0 15 21 1 0 0 0 0 16 17 2 0 0 0 0 16 19 1 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 19 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	310.12
Volume:	325.58
LogP:	5.16
LogD:	3.66
LogS:	-3.41
# Rotatable Bonds:	3
TPSA:	73.83
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.612
Synthetic Accessibility Score:	2.717
Fsp3:	0.158
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.973
MDCK Permeability:	1.5035184333100915e-05
Pgp-inhibitor:	0.032
Pgp-substrate:	0.754
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02
Plasma Protein Binding (PPB):	98.4967269897461%
Volume Distribution (VD):	1.047
Pgp-substrate:	2.3984215259552%

ADMET: Metabolism

CYP1A2-inhibitor:	0.982
CYP1A2-substrate:	0.197
CYP2C19-inhibitor:	0.926
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.721
CYP2C9-substrate:	0.942
CYP2D6-inhibitor:	0.916
CYP2D6-substrate:	0.818
CYP3A4-inhibitor:	0.771
CYP3A4-substrate:	0.102

ADMET: Excretion

Clearance (CL):	12.396
Half-life (T1/2):	0.786

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.737
Drug-inuced Liver Injury (DILI):	0.569
AMES Toxicity:	0.082
Rat Oral Acute Toxicity:	0.151
Maximum Recommended Daily Dose:	0.856
Skin Sensitization:	0.935
Carcinogencity:	0.085
Eye Corrosion:	0.003
Eye Irritation:	0.524
Respiratory Toxicity:	0.894

Download Data

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

Natural Product: NPC230713

Natural Product ID:	NPC230713
*Common Name:**	3-(Gamma,Gamma-Dimethylpropenyl)Moracinm
IUPAC Name:	5-[6-hydroxy-7-(3-methylbut-2-enyl)-1-benzofuran-2-yl]benzene-1,3-diol
Synonyms:	3-(Gamma,Gamma-Dimethylpropenyl)Moracinm
Standard InCHIKey:	PMSZSXKBGUQXFG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H18O4/c1-11(2)3-5-16-17(22)6-4-12-9-18(23-19(12)16)13-7-14(20)10-15(21)8-13/h3-4,6-10,20-22H,5H2,1-2H3
SMILES:	CC(=CCc1c(ccc2cc(c3cc(cc(c3)O)O)oc12)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463125
PubChem CID:	42605184
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO9402	Morus mongolica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11429996]
NPO10498	Artocarpus dadah	Species	Moraceae	Eukaryota	bark and twigs	Tewah, Central Kalimantan, Indonesia (N 38 57.003; W 094 44.767)	1999-Oct	PMID[11858749]
NPO9402	Morus mongolica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10498	Artocarpus dadah	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9402	Morus mongolica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10498	Artocarpus dadah	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9402	Morus mongolica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9402	Morus mongolica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10498	Artocarpus dadah	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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
EC50	1
IC50	2
MIC	3
Others	5

Activity Type	# Activity
Individual Protein	2
Organism	3
Others	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	IC50	=	4900.0	nM	PMID[496912]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	IC50	=	31800.0	nM	PMID[496912]
NPT2	Others	Unspecified		Inhibition	=	66.7	%	PMID[496912]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[496913]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	>	100.0	ug.mL-1	PMID[496913]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	100.0	ug.mL-1	PMID[496913]
NPT35	Others	n.a.		Activity	=	55.0	%	PMID[496913]
NPT35	Others	n.a.		Activity	=	62.25	%	PMID[496913]
NPT35	Others	n.a.		Activity	=	67.87	%	PMID[496913]
NPT35	Others	n.a.		Activity	=	69.72	%	PMID[496913]
NPT35	Others	n.a.		EC50	=	5.06	ug.mL-1	PMID[496913]

☑ 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 NPC230713 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	425
0.1-0.2	1812
0.2-0.3	4324
0.3-0.4	11343
0.4-0.5	6628
0.5-0.6	3854
0.6-0.7	5495
0.7-0.8	4839
0.8-0.85	2096
0.85-0.9	1663
0.9-0.95	173
0.95-1	45

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC78335
0.9931	High Similarity	NPC170169
0.993	High Similarity	NPC178202
0.9795	High Similarity	NPC472462
0.9795	High Similarity	NPC235333
0.9792	High Similarity	NPC226644
0.9792	High Similarity	NPC37226
0.9728	High Similarity	NPC198490
0.9728	High Similarity	NPC297531
0.9728	High Similarity	NPC213936
0.9728	High Similarity	NPC148938
0.9724	High Similarity	NPC167576
0.972	High Similarity	NPC210826
0.966	High Similarity	NPC183874
0.9658	High Similarity	NPC23668
0.9658	High Similarity	NPC193976
0.9653	High Similarity	NPC17816
0.9653	High Similarity	NPC130581
0.9653	High Similarity	NPC12148
0.965	High Similarity	NPC155144
0.9597	High Similarity	NPC164110
0.9597	High Similarity	NPC268360
0.9597	High Similarity	NPC96342
0.9597	High Similarity	NPC246647
0.9597	High Similarity	NPC212967
0.9592	High Similarity	NPC142308
0.9592	High Similarity	NPC207624
0.9586	High Similarity	NPC135325
0.9583	High Similarity	NPC51641
0.9583	High Similarity	NPC300267
0.958	High Similarity	NPC225884
0.953	High Similarity	NPC180924
0.9527	High Similarity	NPC213608
0.9527	High Similarity	NPC1477
0.9527	High Similarity	NPC72370
0.9524	High Similarity	NPC115324
0.9524	High Similarity	NPC106372
0.9524	High Similarity	NPC58668
0.9521	High Similarity	NPC37208
0.9521	High Similarity	NPC296030
0.9521	High Similarity	NPC39929
0.9521	High Similarity	NPC221868
0.9514	High Similarity	NPC98926
0.9463	High Similarity	NPC99199
0.9459	High Similarity	NPC5871
0.9452	High Similarity	NPC272194
0.9444	High Similarity	NPC302181
0.94	High Similarity	NPC247677
0.94	High Similarity	NPC160015
0.9379	High Similarity	NPC230943
0.9375	High Similarity	NPC53192
0.9342	High Similarity	NPC304839
0.9342	High Similarity	NPC220582
0.9338	High Similarity	NPC260902
0.9338	High Similarity	NPC65504
0.9338	High Similarity	NPC296957
0.9329	High Similarity	NPC253872
0.9329	High Similarity	NPC263676
0.932	High Similarity	NPC186397
0.932	High Similarity	NPC37135
0.9281	High Similarity	NPC74854
0.9281	High Similarity	NPC30655
0.9281	High Similarity	NPC45124
0.9276	High Similarity	NPC476350
0.9276	High Similarity	NPC476349
0.9276	High Similarity	NPC244750
0.9276	High Similarity	NPC40583
0.9272	High Similarity	NPC137100
0.9267	High Similarity	NPC122365
0.9262	High Similarity	NPC116604
0.9257	High Similarity	NPC317492
0.9257	High Similarity	NPC223988
0.9257	High Similarity	NPC266499
0.9221	High Similarity	NPC193998
0.9216	High Similarity	NPC115432
0.9216	High Similarity	NPC260296
0.92	High Similarity	NPC67654
0.9195	High Similarity	NPC13282
0.9189	High Similarity	NPC168085
0.9167	High Similarity	NPC277480
0.9167	High Similarity	NPC53640
0.9161	High Similarity	NPC159508
0.9156	High Similarity	NPC304387
0.9145	High Similarity	NPC45131
0.9133	High Similarity	NPC156244
0.9128	High Similarity	NPC65775
0.9128	High Similarity	NPC10027
0.9116	High Similarity	NPC311741
0.9116	High Similarity	NPC234629
0.911	High Similarity	NPC226942
0.911	High Similarity	NPC144499
0.911	High Similarity	NPC96791
0.911	High Similarity	NPC470636
0.9108	High Similarity	NPC50394
0.9108	High Similarity	NPC253730
0.9108	High Similarity	NPC247973
0.9108	High Similarity	NPC286230
0.9103	High Similarity	NPC172986
0.9103	High Similarity	NPC37183
0.9103	High Similarity	NPC28337
0.9103	High Similarity	NPC69769
0.9103	High Similarity	NPC270883
0.9103	High Similarity	NPC169471
0.9103	High Similarity	NPC261227
0.9097	High Similarity	NPC272722
0.9097	High Similarity	NPC219861
0.9097	High Similarity	NPC84515
0.9097	High Similarity	NPC312056
0.9073	High Similarity	NPC125300
0.9073	High Similarity	NPC38361
0.9073	High Similarity	NPC130015
0.9067	High Similarity	NPC101957
0.9067	High Similarity	NPC120105
0.9067	High Similarity	NPC227122
0.9067	High Similarity	NPC472421
0.906	High Similarity	NPC39195
0.9054	High Similarity	NPC24136
0.9054	High Similarity	NPC187282
0.9054	High Similarity	NPC290133
0.9048	High Similarity	NPC190637
0.9048	High Similarity	NPC212932
0.9048	High Similarity	NPC166138
0.9048	High Similarity	NPC18585
0.9048	High Similarity	NPC172182
0.9048	High Similarity	NPC17262
0.9048	High Similarity	NPC106985
0.9048	High Similarity	NPC262935
0.9048	High Similarity	NPC9117
0.9048	High Similarity	NPC251182
0.9048	High Similarity	NPC293053
0.9048	High Similarity	NPC24821
0.9041	High Similarity	NPC118840
0.9041	High Similarity	NPC110969
0.9041	High Similarity	NPC64908
0.9041	High Similarity	NPC147688
0.9041	High Similarity	NPC156590
0.9041	High Similarity	NPC205006
0.9038	High Similarity	NPC472581
0.9038	High Similarity	NPC155640
0.9034	High Similarity	NPC220062
0.9034	High Similarity	NPC301217
0.9034	High Similarity	NPC477956
0.9034	High Similarity	NPC303633
0.9034	High Similarity	NPC55018
0.9034	High Similarity	NPC96565
0.9034	High Similarity	NPC216978
0.9032	High Similarity	NPC188486
0.9028	High Similarity	NPC472419
0.9028	High Similarity	NPC62735
0.9026	High Similarity	NPC196879
0.9026	High Similarity	NPC472877
0.9026	High Similarity	NPC16935
0.9021	High Similarity	NPC163029
0.902	High Similarity	NPC472461
0.9013	High Similarity	NPC189130
0.9007	High Similarity	NPC474772
0.9007	High Similarity	NPC474744
0.9007	High Similarity	NPC472423
0.9007	High Similarity	NPC318424
0.9007	High Similarity	NPC258249
0.9	High Similarity	NPC269420
0.8994	High Similarity	NPC131866
0.8993	High Similarity	NPC308200
0.8993	High Similarity	NPC198427
0.8986	High Similarity	NPC216538
0.8986	High Similarity	NPC326500
0.8986	High Similarity	NPC273538
0.8981	High Similarity	NPC259007
0.8981	High Similarity	NPC204088
0.8981	High Similarity	NPC36320
0.8981	High Similarity	NPC38914
0.8981	High Similarity	NPC329215
0.898	High Similarity	NPC473042
0.898	High Similarity	NPC159855
0.898	High Similarity	NPC200694
0.898	High Similarity	NPC169479
0.898	High Similarity	NPC11561
0.898	High Similarity	NPC226636
0.8973	High Similarity	NPC159275
0.8973	High Similarity	NPC305355
0.8973	High Similarity	NPC235239
0.8973	High Similarity	NPC475680
0.8973	High Similarity	NPC241100
0.8966	High Similarity	NPC112757
0.8966	High Similarity	NPC201395
0.8966	High Similarity	NPC124269
0.8966	High Similarity	NPC21350
0.8961	High Similarity	NPC196448
0.8961	High Similarity	NPC269495
0.8958	High Similarity	NPC168105
0.8958	High Similarity	NPC1486
0.8958	High Similarity	NPC477244
0.8958	High Similarity	NPC98115
0.8958	High Similarity	NPC186838
0.8958	High Similarity	NPC66349
0.8958	High Similarity	NPC472364
0.8958	High Similarity	NPC274109
0.8958	High Similarity	NPC150399
0.8958	High Similarity	NPC473391
0.8958	High Similarity	NPC41461

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 NPC230713 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	392
0.1-0.2	985
0.2-0.3	1518
0.3-0.4	2711
0.4-0.5	1832
0.5-0.6	1149
0.6-0.7	378
0.7-0.8	114
0.8-0.85	52
0.85-0.9	19
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8986	High Similarity	NPD4378	Clinical (unspecified phase)
0.8859	High Similarity	NPD7410	Clinical (unspecified phase)
0.8767	High Similarity	NPD2344	Approved
0.8766	High Similarity	NPD2393	Clinical (unspecified phase)
0.8718	High Similarity	NPD3749	Approved
0.8654	High Similarity	NPD3882	Suspended
0.8649	High Similarity	NPD1243	Approved
0.8649	High Similarity	NPD2800	Approved
0.8618	High Similarity	NPD920	Approved
0.8611	High Similarity	NPD1240	Approved
0.8581	High Similarity	NPD1549	Phase 2
0.8543	High Similarity	NPD1511	Approved
0.8537	High Similarity	NPD6559	Discontinued
0.8533	High Similarity	NPD2309	Approved
0.8526	High Similarity	NPD2801	Approved
0.8526	High Similarity	NPD7819	Suspended
0.8516	High Similarity	NPD7411	Suspended
0.8514	High Similarity	NPD1550	Clinical (unspecified phase)
0.8514	High Similarity	NPD1552	Clinical (unspecified phase)
0.8503	High Similarity	NPD1510	Phase 2
0.8493	Intermediate Similarity	NPD1607	Approved
0.8487	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD1934	Approved
0.8452	Intermediate Similarity	NPD4380	Phase 2
0.8446	Intermediate Similarity	NPD2796	Approved
0.8438	Intermediate Similarity	NPD6959	Discontinued
0.8431	Intermediate Similarity	NPD1512	Approved
0.8375	Intermediate Similarity	NPD5494	Approved
0.8366	Intermediate Similarity	NPD2533	Approved
0.8366	Intermediate Similarity	NPD2532	Approved
0.8366	Intermediate Similarity	NPD2534	Approved
0.8365	Intermediate Similarity	NPD7075	Discontinued
0.8355	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD3926	Phase 2
0.8323	Intermediate Similarity	NPD1247	Approved
0.8322	Intermediate Similarity	NPD2935	Discontinued
0.8302	Intermediate Similarity	NPD7768	Phase 2
0.8293	Intermediate Similarity	NPD3818	Discontinued
0.8291	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD6232	Discontinued
0.8232	Intermediate Similarity	NPD7473	Discontinued
0.8199	Intermediate Similarity	NPD919	Approved
0.8182	Intermediate Similarity	NPD6799	Approved
0.8171	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD6166	Phase 2
0.8171	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD2799	Discontinued
0.8113	Intermediate Similarity	NPD6801	Discontinued
0.8105	Intermediate Similarity	NPD3750	Approved
0.8092	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD3226	Approved
0.8013	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD3817	Phase 2
0.7987	Intermediate Similarity	NPD6599	Discontinued
0.7987	Intermediate Similarity	NPD943	Approved
0.7973	Intermediate Similarity	NPD2313	Discontinued
0.7961	Intermediate Similarity	NPD1551	Phase 2
0.7949	Intermediate Similarity	NPD7390	Discontinued
0.7929	Intermediate Similarity	NPD5953	Discontinued
0.7917	Intermediate Similarity	NPD5844	Phase 1
0.7917	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD7286	Phase 2
0.7908	Intermediate Similarity	NPD2346	Discontinued
0.7908	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD2296	Approved
0.7881	Intermediate Similarity	NPD6651	Approved
0.787	Intermediate Similarity	NPD7074	Phase 3
0.7852	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD7054	Approved
0.7792	Intermediate Similarity	NPD1471	Phase 3
0.7791	Intermediate Similarity	NPD5402	Approved
0.7778	Intermediate Similarity	NPD3748	Approved
0.7765	Intermediate Similarity	NPD7472	Approved
0.7756	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD1203	Approved
0.773	Intermediate Similarity	NPD1465	Phase 2
0.7727	Intermediate Similarity	NPD6100	Approved
0.7727	Intermediate Similarity	NPD6099	Approved
0.7725	Intermediate Similarity	NPD5710	Approved
0.7725	Intermediate Similarity	NPD7229	Phase 3
0.7725	Intermediate Similarity	NPD5711	Approved
0.7719	Intermediate Similarity	NPD6797	Phase 2
0.7688	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD7251	Discontinued
0.767	Intermediate Similarity	NPD4287	Approved
0.7647	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD7808	Phase 3
0.763	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD447	Suspended
0.7578	Intermediate Similarity	NPD5403	Approved
0.7561	Intermediate Similarity	NPD6280	Approved
0.7561	Intermediate Similarity	NPD6279	Approved
0.7558	Intermediate Similarity	NPD1729	Discontinued
0.7551	Intermediate Similarity	NPD9717	Approved
0.755	Intermediate Similarity	NPD4625	Phase 3
0.7532	Intermediate Similarity	NPD4628	Phase 3
0.75	Intermediate Similarity	NPD3764	Approved
0.75	Intermediate Similarity	NPD5404	Approved
0.75	Intermediate Similarity	NPD5408	Approved
0.75	Intermediate Similarity	NPD5406	Approved
0.75	Intermediate Similarity	NPD5405	Approved
0.7483	Intermediate Similarity	NPD4908	Phase 1
0.7483	Intermediate Similarity	NPD6832	Phase 2
0.7468	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD230	Phase 1
0.7468	Intermediate Similarity	NPD2654	Approved
0.7467	Intermediate Similarity	NPD2798	Approved
0.7453	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD5401	Approved
0.7436	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD1608	Approved
0.7412	Intermediate Similarity	NPD6808	Phase 2
0.741	Intermediate Similarity	NPD5760	Phase 2
0.741	Intermediate Similarity	NPD5761	Phase 2
0.74	Intermediate Similarity	NPD1470	Approved
0.7391	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD411	Approved
0.7386	Intermediate Similarity	NPD3268	Approved
0.7378	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD422	Phase 1
0.7365	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD4361	Phase 2
0.7363	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD8434	Phase 2
0.7325	Intermediate Similarity	NPD4308	Phase 3
0.7325	Intermediate Similarity	NPD7033	Discontinued
0.7308	Intermediate Similarity	NPD4360	Phase 2
0.7308	Intermediate Similarity	NPD4363	Phase 3
0.7303	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD8312	Approved
0.7288	Intermediate Similarity	NPD8313	Approved
0.7285	Intermediate Similarity	NPD1164	Approved
0.7285	Intermediate Similarity	NPD2797	Approved
0.7278	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD7199	Phase 2
0.7248	Intermediate Similarity	NPD1201	Approved
0.7248	Intermediate Similarity	NPD1610	Phase 2
0.7241	Intermediate Similarity	NPD3751	Discontinued
0.723	Intermediate Similarity	NPD17	Approved
0.7228	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD2403	Approved
0.7211	Intermediate Similarity	NPD1548	Phase 1
0.7205	Intermediate Similarity	NPD7003	Approved
0.72	Intermediate Similarity	NPD3972	Approved
0.7179	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1613	Approved
0.7176	Intermediate Similarity	NPD6971	Discontinued
0.7168	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD4288	Approved
0.7152	Intermediate Similarity	NPD4749	Approved
0.7143	Intermediate Similarity	NPD6844	Discontinued
0.7143	Intermediate Similarity	NPD7177	Discontinued
0.7143	Intermediate Similarity	NPD37	Approved
0.7135	Intermediate Similarity	NPD6234	Discontinued
0.7126	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD1252	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD4966	Approved
0.7118	Intermediate Similarity	NPD4965	Approved
0.7118	Intermediate Similarity	NPD4967	Phase 2
0.711	Intermediate Similarity	NPD3787	Discontinued
0.7105	Intermediate Similarity	NPD3225	Approved
0.7104	Intermediate Similarity	NPD3269	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD3027	Phase 3
0.7095	Intermediate Similarity	NPD9545	Approved
0.7083	Intermediate Similarity	NPD8151	Discontinued
0.7081	Intermediate Similarity	NPD2424	Discontinued
0.7078	Intermediate Similarity	NPD2861	Phase 2
0.7075	Intermediate Similarity	NPD9493	Approved
0.707	Intermediate Similarity	NPD4307	Phase 2
0.7066	Intermediate Similarity	NPD7458	Discontinued
0.7059	Intermediate Similarity	NPD3267	Approved
0.7059	Intermediate Similarity	NPD3266	Approved
0.7051	Intermediate Similarity	NPD1296	Phase 2
0.7047	Intermediate Similarity	NPD1651	Approved
0.703	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD5124	Phase 1
0.7025	Intermediate Similarity	NPD1933	Approved
0.7025	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6779	Approved
0.7021	Intermediate Similarity	NPD6782	Approved
0.7021	Intermediate Similarity	NPD6781	Approved
0.7021	Intermediate Similarity	NPD6780	Approved
0.7021	Intermediate Similarity	NPD6778	Approved
0.7021	Intermediate Similarity	NPD6776	Approved
0.7021	Intermediate Similarity	NPD6777	Approved
0.7019	Intermediate Similarity	NPD6006	Clinical (unspecified phase)

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