NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	212.05
Volume:	215.65
LogP:	2.7
LogD:	2.889
LogS:	-3.386
# Rotatable Bonds:	0
TPSA:	50.44
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.46
Synthetic Accessibility Score:	1.858
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:	-4.771
MDCK Permeability:	2.1259020286379382e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.906
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.944
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.11
Plasma Protein Binding (PPB):	92.16141510009766%
Volume Distribution (VD):	0.448
Pgp-substrate:	7.283740997314453%

ADMET: Metabolism

CYP1A2-inhibitor:	0.986
CYP1A2-substrate:	0.383
CYP2C19-inhibitor:	0.716
CYP2C19-substrate:	0.106
CYP2C9-inhibitor:	0.365
CYP2C9-substrate:	0.947
CYP2D6-inhibitor:	0.7
CYP2D6-substrate:	0.899
CYP3A4-inhibitor:	0.377
CYP3A4-substrate:	0.126

ADMET: Excretion

Clearance (CL):	4.99
Half-life (T1/2):	0.545

ADMET: Toxicity

hERG Blockers:	0.117
Human Hepatotoxicity (H-HT):	0.462
Drug-inuced Liver Injury (DILI):	0.956
AMES Toxicity:	0.101
Rat Oral Acute Toxicity:	0.255
Maximum Recommended Daily Dose:	0.745
Skin Sensitization:	0.909
Carcinogencity:	0.809
Eye Corrosion:	0.193
Eye Irritation:	0.99
Respiratory Toxicity:	0.356

Download Data

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

Natural Product: NPC254994

Natural Product ID:	NPC254994
*Common Name:**	3-Hydroxybenzo[C]Chromen-6-One
IUPAC Name:	3-hydroxybenzo[c]chromen-6-one
Synonyms:
Standard InCHIKey:	WXUQMTRHPNOXBV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H8O3/c14-8-5-6-10-9-3-1-2-4-11(9)13(15)16-12(10)7-8/h1-7,14H
SMILES:	Oc1ccc2c(c1)oc(=O)c1c2cccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1526978
PubChem CID:	5380406
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	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]
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	n.a.	n.a.	n.a.	Database[HerDing]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	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
EC50	3
IC50	3
Potency	20

Activity Type	# Activity
Individual Protein	17
Others	4
Protein-Protein Interaction	5
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT583	Individual Protein	Inositol monophosphatase 1	Rattus norvegicus	Potency	=	12589.3	nM	PMID[502219]
NPT54	Individual Protein	Nonstructural protein 1	Influenza A virus	Potency	=	11220.2	nM	PMID[502219]
NPT56	Individual Protein	Beta-lactamase AmpC	Escherichia coli K-12	Potency	=	17782.8	nM	PMID[502219]
NPT1416	Individual Protein	Neuropeptide S receptor	Homo sapiens	Potency	=	5011.9	nM	PMID[502219]
NPT2944	Individual Protein	Relaxin receptor 1	Homo sapiens	Potency	=	14125.4	nM	PMID[502219]
NPT4	Individual Protein	Large T antigen	Simian virus 40	IC50	n.a.	38760.0	nM	PMID[502219]
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	Potency	n.a.	1995.3	nM	PMID[502219]
NPT63	Individual Protein	Bromodomain adjacent to zinc finger domain protein 2B	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[502219]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[502219]
NPT1474	Individual Protein	ATP-dependent Clp protease proteolytic subunit	Bacillus subtilis (strain 168)	Potency	n.a.	39810.7	nM	PMID[502220]
NPT478	Individual Protein	Ataxin-2	Homo sapiens	Potency	n.a.	14125.4	nM	PMID[502220]
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	10000.0	nM	PMID[502220]
NPT11	Individual Protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency	n.a.	8912.5	nM	PMID[502220]
NPT160	Individual Protein	TAR DNA-binding protein 43	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[502220]
NPT105	Individual Protein	Muscleblind-like protein 1	Homo sapiens	Potency	n.a.	15848.9	nM	PMID[502219]
NPT2	Others	Unspecified		IC50	=	8470.0	nM	PMID[502219]
NPT5469	Protein-Protein Interaction	Peroxisome proliferator-activated receptor gamma/Nuclear receptor coactivator 2	Homo sapiens	EC50	>	79370.0	nM	PMID[502219]
NPT2	Others	Unspecified		Potency	=	23109.3	nM	PMID[502219]
NPT5470	Protein-Protein Interaction	Peroxisome proliferator-activated receptor gamma/Nuclear receptor coactivator 3	Homo sapiens	EC50	>	79370.0	nM	PMID[502219]
NPT5471	Protein-Protein Interaction	Peroxisome proliferator-activated receptor gamma/Nuclear receptor coactivator 1	Homo sapiens	EC50	>	79370.0	nM	PMID[502219]
NPT21702	PROTEIN-PROTEIN INTERACTION	Importin subunit beta-1/Snurportin-1	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[502220]
NPT9	Individual Protein	DNA polymerase eta	Homo sapiens	Potency	n.a.	28183.8	nM	PMID[502220]
NPT2	Others	Unspecified		Potency	n.a.	3548.1	nM	PMID[502220]
NPT2	Others	Unspecified		Potency	n.a.	22387.2	nM	PMID[502220]
NPT25146	SINGLE PROTEIN	Polypeptide N-acetylgalactosaminyltransferase 2	Homo sapiens	IC50	>	100000.0	nM	PMID[502221]

☑ 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 NPC254994 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	482
0.1-0.2	2117
0.2-0.3	5045
0.3-0.4	11503
0.4-0.5	5906
0.5-0.6	4565
0.6-0.7	5673
0.7-0.8	4693
0.8-0.85	1980
0.85-0.9	623
0.9-0.95	103
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9638	High Similarity	NPC131766
0.9357	High Similarity	NPC32470
0.9291	High Similarity	NPC267509
0.9071	High Similarity	NPC220106
0.9034	High Similarity	NPC194379
0.9034	High Similarity	NPC470107
0.9007	High Similarity	NPC105648
0.8986	High Similarity	NPC9985
0.8986	High Similarity	NPC239495
0.8973	High Similarity	NPC227166
0.8951	High Similarity	NPC29577
0.8951	High Similarity	NPC134621
0.8936	High Similarity	NPC275734
0.8912	High Similarity	NPC41326
0.8889	High Similarity	NPC237208
0.8881	High Similarity	NPC66404
0.8881	High Similarity	NPC95123
0.8865	High Similarity	NPC316480
0.8857	High Similarity	NPC476480
0.8857	High Similarity	NPC228661
0.8857	High Similarity	NPC84585
0.8841	High Similarity	NPC57601
0.8832	High Similarity	NPC307289
0.8828	High Similarity	NPC142863
0.8828	High Similarity	NPC12305
0.8811	High Similarity	NPC310340
0.8811	High Similarity	NPC202981
0.8797	High Similarity	NPC107846
0.8794	High Similarity	NPC472460
0.8794	High Similarity	NPC329225
0.8794	High Similarity	NPC147686
0.8792	High Similarity	NPC20541
0.8784	High Similarity	NPC217447
0.8777	High Similarity	NPC172262
0.8776	High Similarity	NPC307780
0.8776	High Similarity	NPC309979
0.8776	High Similarity	NPC295036
0.8767	High Similarity	NPC105415
0.8759	High Similarity	NPC154217
0.8741	High Similarity	NPC250755
0.8733	High Similarity	NPC13879
0.8732	High Similarity	NPC155205
0.8732	High Similarity	NPC261234
0.8725	High Similarity	NPC178134
0.8723	High Similarity	NPC13768
0.8723	High Similarity	NPC12296
0.8723	High Similarity	NPC287246
0.8723	High Similarity	NPC290291
0.8723	High Similarity	NPC275055
0.8723	High Similarity	NPC32441
0.8723	High Similarity	NPC295261
0.8723	High Similarity	NPC79943
0.8723	High Similarity	NPC103001
0.8723	High Similarity	NPC243083
0.8723	High Similarity	NPC107586
0.8723	High Similarity	NPC296490
0.8707	High Similarity	NPC233267
0.8707	High Similarity	NPC6923
0.8707	High Similarity	NPC291049
0.8705	High Similarity	NPC213216
0.8705	High Similarity	NPC78540
0.8705	High Similarity	NPC50898
0.8705	High Similarity	NPC274121
0.8699	High Similarity	NPC17101
0.8699	High Similarity	NPC140120
0.8699	High Similarity	NPC77903
0.869	High Similarity	NPC1886
0.869	High Similarity	NPC196137
0.869	High Similarity	NPC303185
0.869	High Similarity	NPC184649
0.869	High Similarity	NPC262282
0.8686	High Similarity	NPC109778
0.8681	High Similarity	NPC169479
0.8681	High Similarity	NPC36181
0.8681	High Similarity	NPC144499
0.8681	High Similarity	NPC159855
0.8675	High Similarity	NPC247713
0.8671	High Similarity	NPC69769
0.8662	High Similarity	NPC280284
0.8662	High Similarity	NPC118813
0.8662	High Similarity	NPC99333
0.8662	High Similarity	NPC188947
0.8649	High Similarity	NPC60413
0.8649	High Similarity	NPC325983
0.8639	High Similarity	NPC106328
0.8639	High Similarity	NPC35150
0.863	High Similarity	NPC299011
0.863	High Similarity	NPC477955
0.863	High Similarity	NPC181388
0.863	High Similarity	NPC470322
0.8621	High Similarity	NPC106985
0.8621	High Similarity	NPC295696
0.8621	High Similarity	NPC166138
0.8621	High Similarity	NPC71739
0.8621	High Similarity	NPC87609
0.8621	High Similarity	NPC113770
0.8621	High Similarity	NPC94794
0.8621	High Similarity	NPC188632
0.8621	High Similarity	NPC18585
0.8621	High Similarity	NPC470296
0.8621	High Similarity	NPC196459
0.8621	High Similarity	NPC112791
0.8618	High Similarity	NPC244750
0.8618	High Similarity	NPC37502
0.8618	High Similarity	NPC267627
0.8618	High Similarity	NPC40702
0.8618	High Similarity	NPC474373
0.8611	High Similarity	NPC3188
0.8611	High Similarity	NPC103752
0.8601	High Similarity	NPC225153
0.8601	High Similarity	NPC150648
0.8601	High Similarity	NPC265871
0.8601	High Similarity	NPC329203
0.8601	High Similarity	NPC136095
0.8601	High Similarity	NPC222342
0.8601	High Similarity	NPC183642
0.8601	High Similarity	NPC274784
0.8601	High Similarity	NPC20709
0.8601	High Similarity	NPC310135
0.8601	High Similarity	NPC310370
0.8593	High Similarity	NPC168259
0.8592	High Similarity	NPC299379
0.8592	High Similarity	NPC332594
0.8592	High Similarity	NPC266597
0.8592	High Similarity	NPC250266
0.8591	High Similarity	NPC309512
0.8591	High Similarity	NPC317715
0.8591	High Similarity	NPC316960
0.8591	High Similarity	NPC258249
0.8591	High Similarity	NPC209142
0.8591	High Similarity	NPC148945
0.8591	High Similarity	NPC312549
0.8591	High Similarity	NPC78835
0.8591	High Similarity	NPC204561
0.8591	High Similarity	NPC133856
0.8582	High Similarity	NPC223616
0.8582	High Similarity	NPC242712
0.8582	High Similarity	NPC39426
0.8582	High Similarity	NPC234560
0.8581	High Similarity	NPC70764
0.8581	High Similarity	NPC65775
0.8581	High Similarity	NPC10027
0.8571	High Similarity	NPC7943
0.8571	High Similarity	NPC180477
0.8571	High Similarity	NPC143402
0.8571	High Similarity	NPC123202
0.8571	High Similarity	NPC22005
0.8562	High Similarity	NPC260296
0.8562	High Similarity	NPC178627
0.8562	High Similarity	NPC271288
0.8562	High Similarity	NPC469935
0.8562	High Similarity	NPC115432
0.8562	High Similarity	NPC469953
0.8562	High Similarity	NPC230943
0.8562	High Similarity	NPC311144
0.8561	High Similarity	NPC189106
0.8561	High Similarity	NPC112192
0.8561	High Similarity	NPC164236
0.8561	High Similarity	NPC113006
0.8561	High Similarity	NPC128348
0.8561	High Similarity	NPC313618
0.8561	High Similarity	NPC66384
0.8561	High Similarity	NPC309717
0.8552	High Similarity	NPC53192
0.8552	High Similarity	NPC469542
0.8551	High Similarity	NPC247779
0.8542	High Similarity	NPC172986
0.8542	High Similarity	NPC284550
0.8542	High Similarity	NPC305355
0.8542	High Similarity	NPC6407
0.8542	High Similarity	NPC188243
0.8542	High Similarity	NPC182421
0.8542	High Similarity	NPC76445
0.8542	High Similarity	NPC261227
0.8542	High Similarity	NPC110228
0.8542	High Similarity	NPC129853
0.8542	High Similarity	NPC475680
0.8542	High Similarity	NPC270883
0.8533	High Similarity	NPC273483
0.8531	High Similarity	NPC124269
0.8531	High Similarity	NPC472368
0.8531	High Similarity	NPC201395
0.8523	High Similarity	NPC227122
0.8523	High Similarity	NPC150928
0.8521	High Similarity	NPC281917
0.8521	High Similarity	NPC234133
0.8521	High Similarity	NPC116775
0.8521	High Similarity	NPC13408
0.8521	High Similarity	NPC301915
0.8521	High Similarity	NPC187432
0.8521	High Similarity	NPC235428
0.8521	High Similarity	NPC124784
0.8521	High Similarity	NPC87545
0.8521	High Similarity	NPC194281
0.8521	High Similarity	NPC47815
0.8521	High Similarity	NPC216361
0.8521	High Similarity	NPC127447
0.8521	High Similarity	NPC24394
0.8521	High Similarity	NPC473887
0.8521	High Similarity	NPC135837

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 NPC254994 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	462
0.1-0.2	998
0.2-0.3	1682
0.3-0.4	2687
0.4-0.5	1822
0.5-0.6	1025
0.6-0.7	298
0.7-0.8	114
0.8-0.85	34
0.85-0.9	20
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9209	High Similarity	NPD3750	Approved
0.8926	High Similarity	NPD3749	Approved
0.8849	High Similarity	NPD3748	Approved
0.8794	High Similarity	NPD1549	Phase 2
0.8725	High Similarity	NPD1465	Phase 2
0.8723	High Similarity	NPD1552	Clinical (unspecified phase)
0.8723	High Similarity	NPD1550	Clinical (unspecified phase)
0.86	High Similarity	NPD7819	Suspended
0.8582	High Similarity	NPD1510	Phase 2
0.8561	High Similarity	NPD1240	Approved
0.8531	High Similarity	NPD970	Clinical (unspecified phase)
0.844	Intermediate Similarity	NPD1607	Approved
0.8392	Intermediate Similarity	NPD1551	Phase 2
0.8345	Intermediate Similarity	NPD1243	Approved
0.8344	Intermediate Similarity	NPD7411	Suspended
0.8321	Intermediate Similarity	NPD1203	Approved
0.8312	Intermediate Similarity	NPD7075	Discontinued
0.8311	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD5844	Phase 1
0.8296	Intermediate Similarity	NPD422	Phase 1
0.8286	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8264	Intermediate Similarity	NPD2796	Approved
0.8247	Intermediate Similarity	NPD7768	Phase 2
0.8247	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD1511	Approved
0.8235	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8219	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD2797	Approved
0.8182	Intermediate Similarity	NPD4288	Approved
0.8176	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8162	Intermediate Similarity	NPD1610	Phase 2
0.8156	Intermediate Similarity	NPD3764	Approved
0.8133	Intermediate Similarity	NPD1512	Approved
0.8121	Intermediate Similarity	NPD6799	Approved
0.8102	Intermediate Similarity	NPD1608	Approved
0.8077	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8069	Intermediate Similarity	NPD4308	Phase 3
0.8067	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD1934	Approved
0.8041	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD4628	Phase 3
0.8039	Intermediate Similarity	NPD4380	Phase 2
0.8039	Intermediate Similarity	NPD6599	Discontinued
0.8028	Intermediate Similarity	NPD3268	Approved
0.8014	Intermediate Similarity	NPD6099	Approved
0.8014	Intermediate Similarity	NPD6100	Approved
0.8	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD6232	Discontinued
0.7986	Intermediate Similarity	NPD3225	Approved
0.7974	Intermediate Similarity	NPD3226	Approved
0.7971	Intermediate Similarity	NPD9717	Approved
0.7961	Intermediate Similarity	NPD920	Approved
0.7959	Intermediate Similarity	NPD2344	Approved
0.7935	Intermediate Similarity	NPD6801	Discontinued
0.7925	Intermediate Similarity	NPD6959	Discontinued
0.7902	Intermediate Similarity	NPD1296	Phase 2
0.7883	Intermediate Similarity	NPD17	Approved
0.7868	Intermediate Similarity	NPD9545	Approved
0.7868	Intermediate Similarity	NPD1548	Phase 1
0.7857	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD7473	Discontinued
0.7838	Intermediate Similarity	NPD2346	Discontinued
0.7832	Intermediate Similarity	NPD4625	Phase 3
0.7829	Intermediate Similarity	NPD2533	Approved
0.7829	Intermediate Similarity	NPD2532	Approved
0.7829	Intermediate Similarity	NPD2534	Approved
0.7829	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD2799	Discontinued
0.7811	Intermediate Similarity	NPD4287	Approved
0.7801	Intermediate Similarity	NPD3267	Approved
0.7801	Intermediate Similarity	NPD3266	Approved
0.78	Intermediate Similarity	NPD7003	Approved
0.7793	Intermediate Similarity	NPD4307	Phase 2
0.7778	Intermediate Similarity	NPD2313	Discontinued
0.7771	Intermediate Similarity	NPD2801	Approved
0.777	Intermediate Similarity	NPD2935	Discontinued
0.7762	Intermediate Similarity	NPD4908	Phase 1
0.7748	Intermediate Similarity	NPD2309	Approved
0.7733	Intermediate Similarity	NPD2800	Approved
0.7727	Intermediate Similarity	NPD5403	Approved
0.7722	Intermediate Similarity	NPD3817	Phase 2
0.7712	Intermediate Similarity	NPD5401	Approved
0.7703	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD1164	Approved
0.7673	Intermediate Similarity	NPD3882	Suspended
0.7655	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD6832	Phase 2
0.7619	Intermediate Similarity	NPD230	Phase 1
0.7606	Intermediate Similarity	NPD1283	Approved
0.7589	Intermediate Similarity	NPD1481	Phase 2
0.7578	Intermediate Similarity	NPD919	Approved
0.7576	Intermediate Similarity	NPD3818	Discontinued
0.7569	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD6166	Phase 2
0.7561	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD943	Approved
0.7548	Intermediate Similarity	NPD6273	Approved
0.7546	Intermediate Similarity	NPD7229	Phase 3
0.7545	Intermediate Similarity	NPD5953	Discontinued
0.7534	Intermediate Similarity	NPD411	Approved
0.7533	Intermediate Similarity	NPD5408	Approved
0.7533	Intermediate Similarity	NPD5404	Approved
0.7533	Intermediate Similarity	NPD5405	Approved
0.7533	Intermediate Similarity	NPD5406	Approved
0.753	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD1535	Discovery
0.75	Intermediate Similarity	NPD5124	Phase 1
0.75	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5402	Approved
0.75	Intermediate Similarity	NPD447	Suspended
0.75	Intermediate Similarity	NPD2798	Approved
0.75	Intermediate Similarity	NPD6559	Discontinued
0.75	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7199	Phase 2
0.7485	Intermediate Similarity	NPD7074	Phase 3
0.7483	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD7033	Discontinued
0.7464	Intermediate Similarity	NPD9493	Approved
0.7456	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD1613	Approved
0.7432	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD7286	Phase 2
0.7425	Intermediate Similarity	NPD7054	Approved
0.7423	Intermediate Similarity	NPD5494	Approved
0.7421	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD4476	Approved
0.7417	Intermediate Similarity	NPD4477	Approved
0.7413	Intermediate Similarity	NPD4749	Approved
0.7397	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1201	Approved
0.7394	Intermediate Similarity	NPD1281	Approved
0.7394	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD1933	Approved
0.7381	Intermediate Similarity	NPD7472	Approved
0.7365	Intermediate Similarity	NPD7177	Discontinued
0.7365	Intermediate Similarity	NPD3751	Discontinued
0.7361	Intermediate Similarity	NPD1876	Approved
0.7357	Intermediate Similarity	NPD1894	Discontinued
0.7343	Intermediate Similarity	NPD3972	Approved
0.7337	Intermediate Similarity	NPD6797	Phase 2
0.7333	Intermediate Similarity	NPD5710	Approved
0.7333	Intermediate Similarity	NPD5711	Approved
0.731	Intermediate Similarity	NPD1470	Approved
0.7308	Intermediate Similarity	NPD7390	Discontinued
0.7308	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6798	Discontinued
0.7296	Intermediate Similarity	NPD7458	Discontinued
0.7294	Intermediate Similarity	NPD7251	Discontinued
0.729	Intermediate Similarity	NPD2354	Approved
0.7273	Intermediate Similarity	NPD1652	Phase 2
0.7267	Intermediate Similarity	NPD6355	Discontinued
0.726	Intermediate Similarity	NPD1019	Discontinued
0.7251	Intermediate Similarity	NPD7808	Phase 3
0.7251	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD1241	Discontinued
0.7237	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD1653	Approved
0.7222	Intermediate Similarity	NPD8455	Phase 2
0.7222	Intermediate Similarity	NPD9269	Phase 2
0.7219	Intermediate Similarity	NPD6651	Approved
0.7211	Intermediate Similarity	NPD2861	Phase 2
0.72	Intermediate Similarity	NPD4060	Phase 1
0.7195	Intermediate Similarity	NPD6971	Discontinued
0.7186	Intermediate Similarity	NPD3926	Phase 2
0.7183	Intermediate Similarity	NPD9268	Approved
0.7178	Intermediate Similarity	NPD2296	Approved
0.7174	Intermediate Similarity	NPD5535	Approved
0.717	Intermediate Similarity	NPD7427	Discontinued
0.7164	Intermediate Similarity	NPD9697	Approved
0.716	Intermediate Similarity	NPD37	Approved
0.7153	Intermediate Similarity	NPD1611	Approved
0.7152	Intermediate Similarity	NPD6234	Discontinued
0.7143	Intermediate Similarity	NPD2353	Approved
0.7143	Intermediate Similarity	NPD1471	Phase 3
0.7143	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7440	Discontinued
0.7134	Intermediate Similarity	NPD4965	Approved
0.7134	Intermediate Similarity	NPD4967	Phase 2
0.7134	Intermediate Similarity	NPD4966	Approved
0.7133	Intermediate Similarity	NPD8032	Phase 2
0.7133	Intermediate Similarity	NPD4626	Approved
0.7133	Intermediate Similarity	NPD1778	Approved
0.7132	Intermediate Similarity	NPD74	Approved
0.7132	Intermediate Similarity	NPD9266	Approved
0.7126	Intermediate Similarity	NPD3787	Discontinued
0.7119	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD8313	Approved
0.711	Intermediate Similarity	NPD8312	Approved
0.7097	Intermediate Similarity	NPD2897	Discontinued
0.7067	Intermediate Similarity	NPD6410	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