NPASS Compound

Structure

CID262282 OpenBabel06191716062D 23 24 0 0 0 0 0 0 0 0999 V2000 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 7 1 0 0 0 0 2 10 1 0 0 0 0 3 7 2 0 0 0 0 3 12 1 0 0 0 0 4 8 2 0 0 0 0 4 11 1 0 0 0 0 5 8 1 0 0 0 0 5 13 2 0 0 0 0 6 9 1 0 0 0 0 6 14 1 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 9 11 2 0 0 0 0 9 13 1 0 0 0 0 10 12 2 0 0 0 0 10 17 1 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 13 23 1 0 0 0 0 14 20 2 0 0 0 0 14 21 1 0 0 0 0 15 22 2 0 0 0 0 15 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	320.05
Volume:	300.113
LogP:	1.468
LogD:	2.228
LogS:	-2.67
# Rotatable Bonds:	5
TPSA:	144.52
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.322
Synthetic Accessibility Score:	2.409
Fsp3:	0.067
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.72
MDCK Permeability:	6.2463682297675405e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.982
30% Bioavailability (F30%):	0.957

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.029
Plasma Protein Binding (PPB):	90.60645294189453%
Volume Distribution (VD):	0.397
Pgp-substrate:	4.8218207359313965%

ADMET: Metabolism

CYP1A2-inhibitor:	0.124
CYP1A2-substrate:	0.047
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.039
CYP2C9-inhibitor:	0.431
CYP2C9-substrate:	0.618
CYP2D6-inhibitor:	0.106
CYP2D6-substrate:	0.166
CYP3A4-inhibitor:	0.085
CYP3A4-substrate:	0.04

ADMET: Excretion

Clearance (CL):	14.658
Half-life (T1/2):	0.968

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.233
Drug-inuced Liver Injury (DILI):	0.814
AMES Toxicity:	0.338
Rat Oral Acute Toxicity:	0.064
Maximum Recommended Daily Dose:	0.015
Skin Sensitization:	0.916
Carcinogencity:	0.033
Eye Corrosion:	0.017
Eye Irritation:	0.906
Respiratory Toxicity:	0.081

Download Data

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

Natural Product: NPC262282

Natural Product ID:	NPC262282
*Common Name:**	2-O-(3,4-Dihydroxybenzoyl)-2,4,6-Trihydroxyphenylacetic Acid
IUPAC Name:	2-[2-(3,4-dihydroxybenzoyl)oxy-4,6-dihydroxyphenyl]acetic acid
Synonyms:
Standard InCHIKey:	YTJJRAWFHJBAMT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H12O8/c16-8-4-11(18)9(6-14(20)21)13(5-8)23-15(22)7-1-2-10(17)12(19)3-7/h1-5,16-19H,6H2,(H,20,21)
SMILES:	OC(=O)Cc1c(cc(cc1O)O)OC(=O)c1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL521876
PubChem CID:	44583925
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
NPO32785	myrciaria cauliflora	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16933884]
NPO18366	Papaver commutatum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18366	Papaver commutatum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18366	Papaver commutatum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18366	Papaver commutatum	Species	Papaveraceae	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
IC50	2
Others	2

Activity Type	# Activity
NON-MOLECULAR	1
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT35	Others	n.a.		IC50	=	61800.0	nM	PMID[528369]
NPT2	Others	Unspecified		Activity	=	74.9	%	PMID[528369]
NPT2	Others	Unspecified		Activity	=	70.3	%	PMID[528369]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	30000.0	nM	PMID[528369]

☑ 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 NPC262282 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	421
0.1-0.2	1975
0.2-0.3	5338
0.3-0.4	10912
0.4-0.5	5902
0.5-0.6	3705
0.6-0.7	5303
0.7-0.8	6800
0.8-0.85	1899
0.85-0.9	409
0.9-0.95	30
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9787	High Similarity	NPC107636
0.9571	High Similarity	NPC134975
0.9195	High Similarity	NPC318432
0.9184	High Similarity	NPC75695
0.9167	High Similarity	NPC70136
0.9139	High Similarity	NPC24164
0.9133	High Similarity	NPC38779
0.9133	High Similarity	NPC289322
0.9133	High Similarity	NPC160512
0.9133	High Similarity	NPC114179
0.9133	High Similarity	NPC68324
0.9133	High Similarity	NPC156818
0.911	High Similarity	NPC12367
0.911	High Similarity	NPC118726
0.9097	High Similarity	NPC279121
0.9078	High Similarity	NPC207516
0.9067	High Similarity	NPC88803
0.9067	High Similarity	NPC250436
0.9067	High Similarity	NPC104983
0.9067	High Similarity	NPC54928
0.9067	High Similarity	NPC291948
0.9067	High Similarity	NPC300845
0.906	High Similarity	NPC178134
0.9048	High Similarity	NPC473091
0.9041	High Similarity	NPC239312
0.9041	High Similarity	NPC275772
0.9041	High Similarity	NPC168803
0.9041	High Similarity	NPC130230
0.9041	High Similarity	NPC74881
0.9041	High Similarity	NPC51443
0.9034	High Similarity	NPC131766
0.9028	High Similarity	NPC175013
0.9013	High Similarity	NPC53889
0.9007	High Similarity	NPC247713
0.8993	High Similarity	NPC289968
0.8986	High Similarity	NPC45873
0.8986	High Similarity	NPC77858
0.898	High Similarity	NPC194856
0.898	High Similarity	NPC272721
0.898	High Similarity	NPC19545
0.898	High Similarity	NPC196277
0.898	High Similarity	NPC276930
0.898	High Similarity	NPC43669
0.8973	High Similarity	NPC20791
0.8973	High Similarity	NPC169749
0.8973	High Similarity	NPC179271
0.8958	High Similarity	NPC312256
0.8951	High Similarity	NPC326065
0.8947	High Similarity	NPC40702
0.8947	High Similarity	NPC267627
0.8947	High Similarity	NPC37502
0.8947	High Similarity	NPC87317
0.8933	High Similarity	NPC475895
0.8926	High Similarity	NPC251110
0.8919	High Similarity	NPC1612
0.8919	High Similarity	NPC195351
0.8919	High Similarity	NPC17286
0.8919	High Similarity	NPC296197
0.8919	High Similarity	NPC183959
0.8919	High Similarity	NPC259713
0.8919	High Similarity	NPC216318
0.8912	High Similarity	NPC140840
0.8912	High Similarity	NPC108406
0.8912	High Similarity	NPC139839
0.8912	High Similarity	NPC77378
0.8912	High Similarity	NPC472969
0.8912	High Similarity	NPC207729
0.8912	High Similarity	NPC95864
0.8912	High Similarity	NPC86847
0.8904	High Similarity	NPC287275
0.8903	High Similarity	NPC142614
0.8897	High Similarity	NPC287722
0.8889	High Similarity	NPC110419
0.8873	High Similarity	NPC95679
0.8873	High Similarity	NPC125417
0.8873	High Similarity	NPC25305
0.8873	High Similarity	NPC110899
0.8873	High Similarity	NPC112068
0.8867	High Similarity	NPC474656
0.8867	High Similarity	NPC27208
0.8867	High Similarity	NPC39732
0.8867	High Similarity	NPC60972
0.8859	High Similarity	NPC62042
0.8859	High Similarity	NPC248102
0.8859	High Similarity	NPC184136
0.8859	High Similarity	NPC260582
0.8859	High Similarity	NPC61620
0.8859	High Similarity	NPC29231
0.8851	High Similarity	NPC321011
0.8851	High Similarity	NPC188679
0.8851	High Similarity	NPC294852
0.8851	High Similarity	NPC119059
0.8844	High Similarity	NPC165389
0.8841	High Similarity	NPC94810
0.8839	High Similarity	NPC67959
0.8836	High Similarity	NPC105213
0.8836	High Similarity	NPC207732
0.8836	High Similarity	NPC257025
0.8828	High Similarity	NPC301178
0.8828	High Similarity	NPC284556
0.8808	High Similarity	NPC292214
0.8808	High Similarity	NPC271779
0.8808	High Similarity	NPC88645
0.8808	High Similarity	NPC167091
0.8808	High Similarity	NPC206238
0.88	High Similarity	NPC225731
0.88	High Similarity	NPC260895
0.88	High Similarity	NPC204515
0.88	High Similarity	NPC99772
0.88	High Similarity	NPC31363
0.8792	High Similarity	NPC183950
0.8792	High Similarity	NPC287101
0.8792	High Similarity	NPC52005
0.8792	High Similarity	NPC87125
0.8792	High Similarity	NPC223579
0.8792	High Similarity	NPC137062
0.8792	High Similarity	NPC105512
0.8792	High Similarity	NPC270465
0.879	High Similarity	NPC473818
0.8786	High Similarity	NPC307289
0.8774	High Similarity	NPC471745
0.8774	High Similarity	NPC476372
0.8774	High Similarity	NPC476371
0.8767	High Similarity	NPC471417
0.8766	High Similarity	NPC239966
0.8766	High Similarity	NPC130955
0.8766	High Similarity	NPC471744
0.8766	High Similarity	NPC203020
0.8766	High Similarity	NPC200594
0.8759	High Similarity	NPC220106
0.875	High Similarity	NPC138360
0.875	High Similarity	NPC2928
0.875	High Similarity	NPC201136
0.875	High Similarity	NPC50715
0.875	High Similarity	NPC214138
0.875	High Similarity	NPC183597
0.875	High Similarity	NPC163780
0.875	High Similarity	NPC20541
0.875	High Similarity	NPC196439
0.875	High Similarity	NPC146165
0.875	High Similarity	NPC128863
0.875	High Similarity	NPC227325
0.875	High Similarity	NPC280339
0.875	High Similarity	NPC167815
0.875	High Similarity	NPC20830
0.875	High Similarity	NPC208197
0.875	High Similarity	NPC2476
0.875	High Similarity	NPC256612
0.875	High Similarity	NPC92659
0.875	High Similarity	NPC4455
0.8742	High Similarity	NPC212678
0.8742	High Similarity	NPC142540
0.8742	High Similarity	NPC199773
0.8742	High Similarity	NPC199100
0.8742	High Similarity	NPC28103
0.8742	High Similarity	NPC120537
0.8742	High Similarity	NPC25270
0.8742	High Similarity	NPC83508
0.8742	High Similarity	NPC477231
0.8742	High Similarity	NPC55205
0.8742	High Similarity	NPC100887
0.8742	High Similarity	NPC156222
0.8742	High Similarity	NPC301323
0.8742	High Similarity	NPC293183
0.8742	High Similarity	NPC239128
0.8742	High Similarity	NPC125300
0.8742	High Similarity	NPC39007
0.8742	High Similarity	NPC187498
0.8742	High Similarity	NPC131624
0.8742	High Similarity	NPC71334
0.8742	High Similarity	NPC222830
0.8742	High Similarity	NPC241498
0.8742	High Similarity	NPC256283
0.8742	High Similarity	NPC162313
0.8742	High Similarity	NPC275722
0.8742	High Similarity	NPC188203
0.8742	High Similarity	NPC257648
0.8742	High Similarity	NPC275836
0.8742	High Similarity	NPC161277
0.8742	High Similarity	NPC57030
0.8742	High Similarity	NPC101996
0.8742	High Similarity	NPC120163
0.8742	High Similarity	NPC198826
0.8742	High Similarity	NPC180234
0.8741	High Similarity	NPC38874
0.8734	High Similarity	NPC280493
0.8733	High Similarity	NPC188871
0.8733	High Similarity	NPC3825
0.8733	High Similarity	NPC88804
0.8733	High Similarity	NPC286342
0.8733	High Similarity	NPC149127
0.8725	High Similarity	NPC3036
0.8725	High Similarity	NPC120464
0.8725	High Similarity	NPC98809
0.8725	High Similarity	NPC476394
0.8725	High Similarity	NPC287395
0.8725	High Similarity	NPC183655
0.8725	High Similarity	NPC218490
0.8723	High Similarity	NPC156124
0.8723	High Similarity	NPC1321

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 NPC262282 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	993
0.2-0.3	1877
0.3-0.4	2642
0.4-0.5	1643
0.5-0.6	1023
0.6-0.7	401
0.7-0.8	138
0.8-0.85	31
0.85-0.9	9
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9097	High Similarity	NPD1511	Approved
0.9067	High Similarity	NPD4868	Clinical (unspecified phase)
0.906	High Similarity	NPD1465	Phase 2
0.8973	High Similarity	NPD1512	Approved
0.8723	High Similarity	NPD230	Phase 1
0.8684	High Similarity	NPD2801	Approved
0.8618	High Similarity	NPD1934	Approved
0.8571	High Similarity	NPD3882	Suspended
0.8562	High Similarity	NPD2393	Clinical (unspecified phase)
0.8506	High Similarity	NPD3817	Phase 2
0.8438	Intermediate Similarity	NPD3818	Discontinued
0.8395	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8392	Intermediate Similarity	NPD943	Approved
0.8378	Intermediate Similarity	NPD3750	Approved
0.8333	Intermediate Similarity	NPD9269	Phase 2
0.8333	Intermediate Similarity	NPD447	Suspended
0.8293	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD1549	Phase 2
0.8239	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD1551	Phase 2
0.8212	Intermediate Similarity	NPD6799	Approved
0.8199	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD6166	Phase 2
0.8187	Intermediate Similarity	NPD6232	Discontinued
0.8176	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8169	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD7075	Discontinued
0.8163	Intermediate Similarity	NPD1510	Phase 2
0.816	Intermediate Similarity	NPD5844	Phase 1
0.816	Intermediate Similarity	NPD7054	Approved
0.8156	Intermediate Similarity	NPD1203	Approved
0.8138	Intermediate Similarity	NPD1240	Approved
0.8125	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD7074	Phase 3
0.811	Intermediate Similarity	NPD7472	Approved
0.8089	Intermediate Similarity	NPD7819	Suspended
0.8061	Intermediate Similarity	NPD6797	Phase 2
0.805	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD3749	Approved
0.8043	Intermediate Similarity	NPD9268	Approved
0.8041	Intermediate Similarity	NPD3748	Approved
0.8039	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD5402	Approved
0.8037	Intermediate Similarity	NPD7473	Discontinued
0.8027	Intermediate Similarity	NPD1607	Approved
0.8014	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD1613	Approved
0.8013	Intermediate Similarity	NPD4380	Phase 2
0.8012	Intermediate Similarity	NPD7251	Discontinued
0.8	Intermediate Similarity	NPD422	Phase 1
0.8	Intermediate Similarity	NPD1653	Approved
0.7975	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD7411	Suspended
0.7961	Intermediate Similarity	NPD6190	Approved
0.7935	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD6801	Discontinued
0.7898	Intermediate Similarity	NPD6599	Discontinued
0.7895	Intermediate Similarity	NPD4628	Phase 3
0.7888	Intermediate Similarity	NPD919	Approved
0.7867	Intermediate Similarity	NPD2935	Discontinued
0.7857	Intermediate Similarity	NPD7808	Phase 3
0.7834	Intermediate Similarity	NPD3226	Approved
0.7829	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD1243	Approved
0.7821	Intermediate Similarity	NPD5403	Approved
0.7821	Intermediate Similarity	NPD920	Approved
0.7817	Intermediate Similarity	NPD1608	Approved
0.7817	Intermediate Similarity	NPD9717	Approved
0.7806	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD5401	Approved
0.7793	Intermediate Similarity	NPD9494	Approved
0.7748	Intermediate Similarity	NPD2796	Approved
0.773	Intermediate Similarity	NPD5494	Approved
0.7708	Intermediate Similarity	NPD3225	Approved
0.7692	Intermediate Similarity	NPD2533	Approved
0.7692	Intermediate Similarity	NPD2534	Approved
0.7692	Intermediate Similarity	NPD2532	Approved
0.7683	Intermediate Similarity	NPD7199	Phase 2
0.7682	Intermediate Similarity	NPD4308	Phase 3
0.7677	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD6234	Discontinued
0.7662	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD7768	Phase 2
0.7651	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD411	Approved
0.7635	Intermediate Similarity	NPD1296	Phase 2
0.7635	Intermediate Similarity	NPD2313	Discontinued
0.7628	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6832	Phase 2
0.7606	Intermediate Similarity	NPD17	Approved
0.76	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD2800	Approved
0.7593	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD3926	Phase 2
0.7589	Intermediate Similarity	NPD9545	Approved
0.7588	Intermediate Similarity	NPD6559	Discontinued
0.7576	Intermediate Similarity	NPD1247	Approved
0.7569	Intermediate Similarity	NPD1481	Phase 2
0.7568	Intermediate Similarity	NPD3027	Phase 3
0.7566	Intermediate Similarity	NPD2799	Discontinued
0.7534	Intermediate Similarity	NPD2797	Approved
0.7529	Intermediate Similarity	NPD5953	Discontinued
0.7517	Intermediate Similarity	NPD3268	Approved
0.7517	Intermediate Similarity	NPD3764	Approved
0.7515	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1535	Discovery
0.7485	Intermediate Similarity	NPD4288	Approved
0.7485	Intermediate Similarity	NPD5242	Approved
0.7485	Intermediate Similarity	NPD7685	Pre-registration
0.7483	Intermediate Similarity	NPD1933	Approved
0.747	Intermediate Similarity	NPD6959	Discontinued
0.7469	Intermediate Similarity	NPD37	Approved
0.7468	Intermediate Similarity	NPD2344	Approved
0.7468	Intermediate Similarity	NPD2346	Discontinued
0.7465	Intermediate Similarity	NPD1548	Phase 1
0.7439	Intermediate Similarity	NPD4966	Approved
0.7439	Intermediate Similarity	NPD4967	Phase 2
0.7439	Intermediate Similarity	NPD4965	Approved
0.7417	Intermediate Similarity	NPD4307	Phase 2
0.7414	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD7286	Phase 2
0.7407	Intermediate Similarity	NPD6385	Approved
0.7407	Intermediate Similarity	NPD6386	Approved
0.7403	Intermediate Similarity	NPD6099	Approved
0.7403	Intermediate Similarity	NPD6100	Approved
0.7397	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD1610	Phase 2
0.7378	Intermediate Similarity	NPD5353	Approved
0.7358	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD3751	Discontinued
0.7353	Intermediate Similarity	NPD7228	Approved
0.7338	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD3267	Approved
0.7297	Intermediate Similarity	NPD3266	Approved
0.7278	Intermediate Similarity	NPD2354	Approved
0.7278	Intermediate Similarity	NPD2309	Approved
0.7267	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD1652	Phase 2
0.7248	Intermediate Similarity	NPD1019	Discontinued
0.7244	Intermediate Similarity	NPD7266	Discontinued
0.7219	Intermediate Similarity	NPD7229	Phase 3
0.7203	Intermediate Similarity	NPD9493	Approved
0.7195	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD6971	Discontinued
0.7178	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD6798	Discontinued
0.7152	Intermediate Similarity	NPD4908	Phase 1
0.7143	Intermediate Similarity	NPD6355	Discontinued
0.7134	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD6233	Phase 2
0.7123	Intermediate Similarity	NPD1778	Approved
0.7118	Intermediate Similarity	NPD5710	Approved
0.7118	Intermediate Similarity	NPD5711	Approved
0.7118	Intermediate Similarity	NPD3787	Discontinued
0.7115	Intermediate Similarity	NPD7033	Discontinued
0.7111	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD1894	Discontinued
0.7102	Intermediate Similarity	NPD8312	Approved
0.7102	Intermediate Similarity	NPD8313	Approved
0.7099	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6651	Approved
0.7095	Intermediate Similarity	NPD4287	Approved
0.7086	Intermediate Similarity	NPD3018	Phase 2
0.7086	Intermediate Similarity	NPD7038	Approved
0.7086	Intermediate Similarity	NPD7039	Approved
0.7081	Intermediate Similarity	NPD4357	Discontinued
0.7079	Intermediate Similarity	NPD8434	Phase 2
0.7078	Intermediate Similarity	NPD4060	Phase 1
0.7073	Intermediate Similarity	NPD3455	Phase 2
0.7067	Intermediate Similarity	NPD1164	Approved
0.7059	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD8127	Discontinued
0.7032	Intermediate Similarity	NPD5124	Phase 1
0.7032	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD2353	Approved
0.7025	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7440	Discontinued
0.7006	Intermediate Similarity	NPD8455	Phase 2
0.7	Intermediate Similarity	NPD1283	Approved
0.6994	Remote Similarity	NPD5049	Phase 3
0.6994	Remote Similarity	NPD6273	Approved
0.6993	Remote Similarity	NPD4625	Phase 3
0.6993	Remote Similarity	NPD1241	Discontinued
0.6993	Remote Similarity	NPD7095	Approved
0.6975	Remote Similarity	NPD7390	Discontinued
0.6972	Remote Similarity	NPD228	Approved
0.697	Remote Similarity	NPD7458	Discontinued
0.6968	Remote Similarity	NPD1558	Phase 1
0.6962	Remote Similarity	NPD5408	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