NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	228.04
Volume:	224.441
LogP:	2.372
LogD:	2.697
LogS:	-3.425
# Rotatable Bonds:	0
TPSA:	70.67
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.457
Synthetic Accessibility Score:	2.123
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.757
MDCK Permeability:	1.2322943803155795e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.984
Human Intestinal Absorption (HIA):	0.059
20% Bioavailability (F20%):	0.934
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.029
Plasma Protein Binding (PPB):	92.56830596923828%
Volume Distribution (VD):	0.564
Pgp-substrate:	8.01443862915039%

ADMET: Metabolism

CYP1A2-inhibitor:	0.987
CYP1A2-substrate:	0.166
CYP2C19-inhibitor:	0.339
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.293
CYP2C9-substrate:	0.958
CYP2D6-inhibitor:	0.756
CYP2D6-substrate:	0.885
CYP3A4-inhibitor:	0.841
CYP3A4-substrate:	0.11

ADMET: Excretion

Clearance (CL):	9.48
Half-life (T1/2):	0.789

ADMET: Toxicity

hERG Blockers:	0.048
Human Hepatotoxicity (H-HT):	0.275
Drug-inuced Liver Injury (DILI):	0.957
AMES Toxicity:	0.087
Rat Oral Acute Toxicity:	0.192
Maximum Recommended Daily Dose:	0.916
Skin Sensitization:	0.93
Carcinogencity:	0.607
Eye Corrosion:	0.12
Eye Irritation:	0.982
Respiratory Toxicity:	0.261

Download Data

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

Natural Product: NPC131766

Natural Product ID:	NPC131766
*Common Name:**	3,8-Dihydroxybenzo[C]Chromen-6-One
IUPAC Name:	3,8-dihydroxybenzo[c]chromen-6-one
Synonyms:
Standard InCHIKey:	RIUPLDUFZCXCHM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H8O4/c14-7-1-3-9-10-4-2-8(15)6-12(10)17-13(16)11(9)5-7/h1-6,14-15H
SMILES:	Oc1ccc2c(c1)oc(=O)c1c2ccc(c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1836264
PubChem CID:	5488186
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives

*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
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1007/s00217-007-0799-1]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	flower	n.a.	DOI[10.1016/j.foodchem.2011.01.077]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520216]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Seeds	n.a.	n.a.	PMID[15620261]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Root Bark	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Stem Bark	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Twig	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO10597	Fructus syzygii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10597	Fructus syzygii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21349	Punica granatum	Species	Lythraceae	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	13

Activity Type	# Activity
Organism	7
Tissue	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	35.0	%	PMID[493319]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	26.0	%	PMID[493319]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	34.0	%	PMID[493319]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	142.0	%	PMID[493319]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	118.0	%	PMID[493319]
NPT624	Tissue	Plasma	Mus musculus	Cp	=	3.88	uM	PMID[493319]
NPT624	Tissue	Plasma	Mus musculus	Cp	=	1.27	uM	PMID[493319]
NPT624	Tissue	Plasma	Mus musculus	Cp(f)	=	2.85	uM	PMID[493319]
NPT624	Tissue	Plasma	Mus musculus	Cp(f)	=	0.83	uM	PMID[493319]
NPT624	Tissue	Plasma	Mus musculus	Cp(f)	=	77.2	%	PMID[493319]
NPT624	Tissue	Plasma	Mus musculus	Cp(f)	=	65.7	%	PMID[493319]
NPT621	Tissue	Plasma	Homo sapiens	Cp	=	0.04	uM	PMID[493319]
NPT621	Tissue	Plasma	Homo sapiens	Cp	=	0.11	uM	PMID[493319]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	PMID[493320]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	PMID[493320]

☑ 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 NPC131766 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	495
0.1-0.2	2185
0.2-0.3	4999
0.3-0.4	11206
0.4-0.5	6078
0.5-0.6	4328
0.6-0.7	5576
0.7-0.8	4756
0.8-0.85	2369
0.85-0.9	630
0.9-0.95	68
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9638	High Similarity	NPC254994
0.9437	High Similarity	NPC32470
0.9379	High Similarity	NPC470107
0.9371	High Similarity	NPC267509
0.9155	High Similarity	NPC220106
0.9116	High Similarity	NPC194379
0.9116	High Similarity	NPC295036
0.9091	High Similarity	NPC105648
0.906	High Similarity	NPC178134
0.9054	High Similarity	NPC227166
0.9034	High Similarity	NPC29577
0.9034	High Similarity	NPC262282
0.9034	High Similarity	NPC134621
0.9028	High Similarity	NPC159855
0.9028	High Similarity	NPC169479
0.9021	High Similarity	NPC275734
0.9007	High Similarity	NPC247713
0.8993	High Similarity	NPC217447
0.8993	High Similarity	NPC41326
0.8973	High Similarity	NPC237208
0.8966	High Similarity	NPC66404
0.8966	High Similarity	NPC95123
0.8947	High Similarity	NPC40702
0.8947	High Similarity	NPC267627
0.8947	High Similarity	NPC37502
0.8921	High Similarity	NPC307289
0.8919	High Similarity	NPC70764
0.8912	High Similarity	NPC12305
0.8912	High Similarity	NPC142863
0.8897	High Similarity	NPC310340
0.8874	High Similarity	NPC20541
0.8859	High Similarity	NPC227122
0.8859	High Similarity	NPC307780
0.8859	High Similarity	NPC309979
0.8851	High Similarity	NPC105415
0.8851	High Similarity	NPC107636
0.8839	High Similarity	NPC67959
0.8828	High Similarity	NPC250755
0.8828	High Similarity	NPC103752
0.8828	High Similarity	NPC18714
0.8819	High Similarity	NPC155205
0.8816	High Similarity	NPC13879
0.8816	High Similarity	NPC146211
0.8803	High Similarity	NPC9985
0.8803	High Similarity	NPC239495
0.88	High Similarity	NPC39819
0.88	High Similarity	NPC23668
0.88	High Similarity	NPC115324
0.88	High Similarity	NPC193976
0.8792	High Similarity	NPC6923
0.8792	High Similarity	NPC291049
0.8792	High Similarity	NPC65775
0.8792	High Similarity	NPC10027
0.8792	High Similarity	NPC233267
0.8784	High Similarity	NPC77903
0.8784	High Similarity	NPC17101
0.8776	High Similarity	NPC184649
0.8776	High Similarity	NPC155144
0.8776	High Similarity	NPC303185
0.8759	High Similarity	NPC182421
0.875	High Similarity	NPC99199
0.875	High Similarity	NPC18457
0.8742	High Similarity	NPC142308
0.8742	High Similarity	NPC474843
0.8742	High Similarity	NPC273483
0.8742	High Similarity	NPC175978
0.8742	High Similarity	NPC207624
0.8733	High Similarity	NPC202595
0.8733	High Similarity	NPC325983
0.8733	High Similarity	NPC119929
0.8733	High Similarity	NPC60413
0.8725	High Similarity	NPC2569
0.8725	High Similarity	NPC37135
0.8725	High Similarity	NPC172329
0.8725	High Similarity	NPC186397
0.8716	High Similarity	NPC299011
0.8716	High Similarity	NPC202112
0.8716	High Similarity	NPC51513
0.8707	High Similarity	NPC113770
0.8707	High Similarity	NPC295696
0.8707	High Similarity	NPC71739
0.8701	High Similarity	NPC474373
0.8701	High Similarity	NPC244750
0.8699	High Similarity	NPC49108
0.8693	High Similarity	NPC318432
0.869	High Similarity	NPC183642
0.869	High Similarity	NPC310370
0.869	High Similarity	NPC316480
0.8684	High Similarity	NPC95842
0.8684	High Similarity	NPC235333
0.8684	High Similarity	NPC178964
0.8684	High Similarity	NPC280530
0.8675	High Similarity	NPC202157
0.8675	High Similarity	NPC133856
0.8675	High Similarity	NPC58668
0.8675	High Similarity	NPC106372
0.8675	High Similarity	NPC258249
0.8671	High Similarity	NPC223616
0.8667	High Similarity	NPC223988
0.8667	High Similarity	NPC266499
0.8658	High Similarity	NPC7943
0.8658	High Similarity	NPC123202
0.8658	High Similarity	NPC81835
0.8658	High Similarity	NPC22005
0.8649	High Similarity	NPC311144
0.8645	High Similarity	NPC260296
0.8645	High Similarity	NPC24164
0.8645	High Similarity	NPC115432
0.8639	High Similarity	NPC134975
0.8639	High Similarity	NPC202981
0.8639	High Similarity	NPC469542
0.8639	High Similarity	NPC73028
0.8636	High Similarity	NPC38779
0.8636	High Similarity	NPC68324
0.8636	High Similarity	NPC114179
0.8636	High Similarity	NPC289322
0.8636	High Similarity	NPC268360
0.8636	High Similarity	NPC160512
0.8636	High Similarity	NPC156818
0.863	High Similarity	NPC145673
0.863	High Similarity	NPC90411
0.8627	High Similarity	NPC297531
0.8627	High Similarity	NPC148938
0.8627	High Similarity	NPC213936
0.8621	High Similarity	NPC329225
0.8621	High Similarity	NPC472460
0.8621	High Similarity	NPC147686
0.8618	High Similarity	NPC28103
0.8618	High Similarity	NPC271681
0.8618	High Similarity	NPC281272
0.8611	High Similarity	NPC261292
0.8611	High Similarity	NPC135837
0.8611	High Similarity	NPC301915
0.8609	High Similarity	NPC101957
0.8609	High Similarity	NPC120105
0.8609	High Similarity	NPC151473
0.8609	High Similarity	NPC150928
0.8601	High Similarity	NPC182496
0.8601	High Similarity	NPC180905
0.8601	High Similarity	NPC172262
0.86	High Similarity	NPC272721
0.86	High Similarity	NPC39195
0.86	High Similarity	NPC37139
0.86	High Similarity	NPC35150
0.86	High Similarity	NPC7025
0.86	High Similarity	NPC27221
0.86	High Similarity	NPC194856
0.86	High Similarity	NPC256672
0.86	High Similarity	NPC106328
0.86	High Similarity	NPC43669
0.86	High Similarity	NPC196277
0.86	High Similarity	NPC216624
0.86	High Similarity	NPC276930
0.8599	High Similarity	NPC474350
0.8591	High Similarity	NPC196114
0.8591	High Similarity	NPC154217
0.8591	High Similarity	NPC163846
0.8591	High Similarity	NPC260946
0.8591	High Similarity	NPC138978
0.8591	High Similarity	NPC225173
0.859	High Similarity	NPC303565
0.8581	High Similarity	NPC19896
0.8581	High Similarity	NPC257025
0.8571	High Similarity	NPC300845
0.8571	High Similarity	NPC250436
0.8571	High Similarity	NPC291948
0.8571	High Similarity	NPC88803
0.8571	High Similarity	NPC54928
0.8571	High Similarity	NPC227062
0.8571	High Similarity	NPC104983
0.8562	High Similarity	NPC89474
0.8562	High Similarity	NPC261234
0.8562	High Similarity	NPC303950
0.8562	High Similarity	NPC477691
0.8553	High Similarity	NPC70016
0.8553	High Similarity	NPC72958
0.8553	High Similarity	NPC215921
0.8553	High Similarity	NPC234331
0.8553	High Similarity	NPC204350
0.8553	High Similarity	NPC230848
0.8553	High Similarity	NPC232645
0.8553	High Similarity	NPC149614
0.8553	High Similarity	NPC251110
0.8552	High Similarity	NPC13768
0.8552	High Similarity	NPC212767
0.8552	High Similarity	NPC299379
0.8552	High Similarity	NPC290291
0.8552	High Similarity	NPC275055
0.8552	High Similarity	NPC84585
0.8552	High Similarity	NPC32441
0.8552	High Similarity	NPC228661
0.8552	High Similarity	NPC12296
0.8552	High Similarity	NPC296490
0.8552	High Similarity	NPC103001
0.8552	High Similarity	NPC79943
0.8552	High Similarity	NPC476480
0.8552	High Similarity	NPC243083
0.8552	High Similarity	NPC107586
0.8552	High Similarity	NPC287246
0.8552	High Similarity	NPC295261

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 NPC131766 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	474
0.1-0.2	1024
0.2-0.3	1743
0.3-0.4	2665
0.4-0.5	1791
0.5-0.6	982
0.6-0.7	307
0.7-0.8	104
0.8-0.85	42
0.85-0.9	15
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.906	High Similarity	NPD1465	Phase 2
0.9021	High Similarity	NPD3750	Approved
0.8882	High Similarity	NPD3749	Approved
0.8684	High Similarity	NPD7819	Suspended
0.8671	High Similarity	NPD3748	Approved
0.8621	High Similarity	NPD970	Clinical (unspecified phase)
0.8621	High Similarity	NPD1549	Phase 2
0.8571	High Similarity	NPD4868	Clinical (unspecified phase)
0.8552	High Similarity	NPD1550	Clinical (unspecified phase)
0.8552	High Similarity	NPD1552	Clinical (unspecified phase)
0.85	High Similarity	NPD5844	Phase 1
0.8456	Intermediate Similarity	NPD1511	Approved
0.8414	Intermediate Similarity	NPD1510	Phase 2
0.8344	Intermediate Similarity	NPD1512	Approved
0.8302	Intermediate Similarity	NPD6232	Discontinued
0.8301	Intermediate Similarity	NPD3226	Approved
0.8278	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8264	Intermediate Similarity	NPD1240	Approved
0.8258	Intermediate Similarity	NPD1934	Approved
0.8231	Intermediate Similarity	NPD1551	Phase 2
0.8205	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD7411	Suspended
0.8176	Intermediate Similarity	NPD2346	Discontinued
0.8165	Intermediate Similarity	NPD7075	Discontinued
0.8158	Intermediate Similarity	NPD2532	Approved
0.8158	Intermediate Similarity	NPD2533	Approved
0.8158	Intermediate Similarity	NPD2534	Approved
0.8156	Intermediate Similarity	NPD1203	Approved
0.8151	Intermediate Similarity	NPD1607	Approved
0.8148	Intermediate Similarity	NPD7473	Discontinued
0.8133	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD6959	Discontinued
0.8125	Intermediate Similarity	NPD3764	Approved
0.8101	Intermediate Similarity	NPD7768	Phase 2
0.8089	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD2801	Approved
0.8086	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8071	Intermediate Similarity	NPD1608	Approved
0.8067	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD1243	Approved
0.8052	Intermediate Similarity	NPD920	Approved
0.805	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD4288	Approved
0.8013	Intermediate Similarity	NPD4380	Phase 2
0.8	Intermediate Similarity	NPD422	Phase 1
0.7987	Intermediate Similarity	NPD2796	Approved
0.7987	Intermediate Similarity	NPD6099	Approved
0.7987	Intermediate Similarity	NPD2935	Discontinued
0.7987	Intermediate Similarity	NPD6100	Approved
0.7974	Intermediate Similarity	NPD6799	Approved
0.7959	Intermediate Similarity	NPD230	Phase 1
0.7952	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD3817	Phase 2
0.7922	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD4308	Phase 3
0.7908	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD2797	Approved
0.7898	Intermediate Similarity	NPD6599	Discontinued
0.7895	Intermediate Similarity	NPD4628	Phase 3
0.7879	Intermediate Similarity	NPD3818	Discontinued
0.7877	Intermediate Similarity	NPD2313	Discontinued
0.7877	Intermediate Similarity	NPD3268	Approved
0.7875	Intermediate Similarity	NPD3882	Suspended
0.7872	Intermediate Similarity	NPD1610	Phase 2
0.7862	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD17	Approved
0.7853	Intermediate Similarity	NPD7229	Phase 3
0.7838	Intermediate Similarity	NPD447	Suspended
0.7832	Intermediate Similarity	NPD3225	Approved
0.7829	Intermediate Similarity	NPD2800	Approved
0.7817	Intermediate Similarity	NPD9717	Approved
0.7815	Intermediate Similarity	NPD2344	Approved
0.7812	Intermediate Similarity	NPD5402	Approved
0.7808	Intermediate Similarity	NPD4625	Phase 3
0.78	Intermediate Similarity	NPD2799	Discontinued
0.7799	Intermediate Similarity	NPD6801	Discontinued
0.7793	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD4287	Approved
0.777	Intermediate Similarity	NPD943	Approved
0.7758	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD6166	Phase 2
0.7755	Intermediate Similarity	NPD1296	Phase 2
0.7751	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD5494	Approved
0.7692	Intermediate Similarity	NPD6559	Discontinued
0.7679	Intermediate Similarity	NPD7074	Phase 3
0.7669	Intermediate Similarity	NPD919	Approved
0.7665	Intermediate Similarity	NPD3751	Discontinued
0.7662	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD3266	Approved
0.7655	Intermediate Similarity	NPD3267	Approved
0.7651	Intermediate Similarity	NPD4307	Phase 2
0.7651	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD1613	Approved
0.7636	Intermediate Similarity	NPD5711	Approved
0.7636	Intermediate Similarity	NPD5710	Approved
0.7635	Intermediate Similarity	NPD411	Approved
0.7632	Intermediate Similarity	NPD5405	Approved
0.7632	Intermediate Similarity	NPD5406	Approved
0.7632	Intermediate Similarity	NPD5404	Approved
0.7632	Intermediate Similarity	NPD5408	Approved
0.7619	Intermediate Similarity	NPD4908	Phase 1
0.7619	Intermediate Similarity	NPD7054	Approved
0.7613	Intermediate Similarity	NPD2309	Approved
0.76	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD5403	Approved
0.7595	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD9545	Approved
0.7589	Intermediate Similarity	NPD1548	Phase 1
0.7586	Intermediate Similarity	NPD1283	Approved
0.758	Intermediate Similarity	NPD5401	Approved
0.7576	Intermediate Similarity	NPD7199	Phase 2
0.7574	Intermediate Similarity	NPD7472	Approved
0.7569	Intermediate Similarity	NPD1481	Phase 2
0.7569	Intermediate Similarity	NPD9269	Phase 2
0.7566	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD7003	Approved
0.7535	Intermediate Similarity	NPD9268	Approved
0.7534	Intermediate Similarity	NPD1470	Approved
0.7532	Intermediate Similarity	NPD6273	Approved
0.7529	Intermediate Similarity	NPD6797	Phase 2
0.7529	Intermediate Similarity	NPD5953	Discontinued
0.7517	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD7390	Discontinued
0.7516	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7286	Phase 2
0.75	Intermediate Similarity	NPD6832	Phase 2
0.75	Intermediate Similarity	NPD1535	Discovery
0.7485	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7251	Discontinued
0.7469	Intermediate Similarity	NPD37	Approved
0.7468	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD7177	Discontinued
0.7455	Intermediate Similarity	NPD6234	Discontinued
0.7442	Intermediate Similarity	NPD7808	Phase 3
0.7439	Intermediate Similarity	NPD4965	Approved
0.7439	Intermediate Similarity	NPD4966	Approved
0.7439	Intermediate Similarity	NPD4967	Phase 2
0.7438	Intermediate Similarity	NPD1653	Approved
0.7425	Intermediate Similarity	NPD3787	Discontinued
0.7415	Intermediate Similarity	NPD1164	Approved
0.7405	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD8313	Approved
0.7399	Intermediate Similarity	NPD8312	Approved
0.7397	Intermediate Similarity	NPD4749	Approved
0.7381	Intermediate Similarity	NPD3926	Phase 2
0.7379	Intermediate Similarity	NPD1201	Approved
0.7379	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD1281	Approved
0.7379	Intermediate Similarity	NPD1611	Approved
0.7368	Intermediate Similarity	NPD5124	Phase 1
0.7368	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD1247	Approved
0.7338	Intermediate Similarity	NPD7033	Discontinued
0.7315	Intermediate Similarity	NPD2861	Phase 2
0.7303	Intermediate Similarity	NPD4060	Phase 1
0.7289	Intermediate Similarity	NPD6971	Discontinued
0.7288	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6190	Approved
0.7278	Intermediate Similarity	NPD5242	Approved
0.7267	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD1652	Phase 2
0.7255	Intermediate Similarity	NPD1933	Approved
0.7251	Intermediate Similarity	NPD7228	Approved
0.7248	Intermediate Similarity	NPD1019	Discontinued
0.7248	Intermediate Similarity	NPD2798	Approved
0.7244	Intermediate Similarity	NPD1471	Phase 3
0.7216	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD8455	Phase 2
0.7203	Intermediate Similarity	NPD9493	Approved
0.719	Intermediate Similarity	NPD2979	Phase 3
0.7179	Intermediate Similarity	NPD4476	Approved
0.7179	Intermediate Similarity	NPD4477	Approved
0.7178	Intermediate Similarity	NPD7458	Discontinued
0.7174	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD6798	Discontinued
0.717	Intermediate Similarity	NPD2354	Approved
0.7143	Intermediate Similarity	NPD6355	Discontinued
0.7143	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD7440	Discontinued
0.7124	Intermediate Similarity	NPD8032	Phase 2
0.7123	Intermediate Similarity	NPD1778	Approved
0.7123	Intermediate Similarity	NPD4626	Approved
0.712	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1876	Approved
0.7105	Intermediate Similarity	NPD7783	Phase 2
0.7105	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD7095	Approved
0.7103	Intermediate Similarity	NPD1894	Discontinued
0.7101	Intermediate Similarity	NPD6746	Phase 2

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