NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	228.08
Volume:	235.583
LogP:	3.584
LogD:	3.034
LogS:	-5.464
# Rotatable Bonds:	1
TPSA:	43.35
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.597
Synthetic Accessibility Score:	2.411
Fsp3:	0.214
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.782
MDCK Permeability:	1.66421177709708e-05
Pgp-inhibitor:	0.75
Pgp-substrate:	0.982
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.95
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.022
Plasma Protein Binding (PPB):	94.44600677490234%
Volume Distribution (VD):	0.802
Pgp-substrate:	6.0158843994140625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.976
CYP1A2-substrate:	0.918
CYP2C19-inhibitor:	0.508
CYP2C19-substrate:	0.126
CYP2C9-inhibitor:	0.325
CYP2C9-substrate:	0.826
CYP2D6-inhibitor:	0.778
CYP2D6-substrate:	0.817
CYP3A4-inhibitor:	0.518
CYP3A4-substrate:	0.379

ADMET: Excretion

Clearance (CL):	6.976
Half-life (T1/2):	0.388

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.354
Drug-inuced Liver Injury (DILI):	0.928
AMES Toxicity:	0.028
Rat Oral Acute Toxicity:	0.527
Maximum Recommended Daily Dose:	0.903
Skin Sensitization:	0.157
Carcinogencity:	0.854
Eye Corrosion:	0.028
Eye Irritation:	0.943
Respiratory Toxicity:	0.159

Download Data

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

Natural Product: NPC254010

Natural Product ID:	NPC254010
*Common Name:**	2-Propan-2-Ylfuro[3,2-G]Chromen-7-One
IUPAC Name:	2-propan-2-ylfuro[3,2-g]chromen-7-one
Synonyms:
Standard InCHIKey:	KVHBNBMOEQQULB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H12O3/c1-8(2)11-6-10-5-9-3-4-14(15)17-12(9)7-13(10)16-11/h3-8H,1-2H3
SMILES:	O=c1ccc2c(o1)cc1c(c2)cc(o1)C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1586775
PubChem CID:	677576
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0000358] Furanocoumarins [CHEMONTID:0002569] Linear furanocoumarins [CHEMONTID:0000202] Psoralens

*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
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[11374978]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679317]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	roots	purchased from Kiu Shun Trading Ltd., Vancouver, Canada	2000	PMID[16643021]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[17997069]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25538068]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27400088]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2921	Angelica acutiloba	Species	Apiaceae	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
Potency	18

Activity Type	# Activity
Individual Protein	12
Organism	1
Others	3
Uncleic Acid	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT537	Individual Protein	Ras-related protein Rab-9A	Homo sapiens	Potency	=	3548.1	nM	PMID[479476]
NPT538	Individual Protein	Niemann-Pick C1 protein	Homo sapiens	Potency	=	3162.3	nM	PMID[479476]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	4610.9	nM	PMID[479476]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	23099.9	nM	PMID[479476]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	18348.9	nM	PMID[479476]
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[479476]
NPT484	Individual Protein	Luciferin 4-monooxygenase	Photinus pyralis	Potency	n.a.	11995.5	nM	PMID[479476]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[479476]
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	22387.2	nM	PMID[479476]
NPT157	Individual Protein	Breast cancer type 1 susceptibility protein	Homo sapiens	Potency	n.a.	15848.9	nM	PMID[479476]
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	12589.3	nM	PMID[479476]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	14581.0	nM	PMID[479476]
NPT536	Uncleic Acid	microRNA 21	Homo sapiens	Potency	=	3288.5	nM	PMID[479476]
NPT2	Others	Unspecified		Potency	n.a.	2818.4	nM	PMID[479476]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	928.5	nM	PMID[479476]
NPT2	Others	Unspecified		Potency	n.a.	19952.6	nM	PMID[479476]
NPT2	Others	Unspecified		Potency	n.a.	3264.3	nM	PMID[479476]

☑ 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 NPC254010 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	531
0.1-0.2	2081
0.2-0.3	5404
0.3-0.4	11651
0.4-0.5	6070
0.5-0.6	5291
0.6-0.7	5767
0.7-0.8	4557
0.8-0.85	882
0.85-0.9	393
0.9-0.95	67
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9852	High Similarity	NPC262635
0.9781	High Similarity	NPC313036
0.9496	High Similarity	NPC166858
0.9496	High Similarity	NPC51146
0.9437	High Similarity	NPC266743
0.9375	High Similarity	NPC98028
0.9371	High Similarity	NPC88445
0.9366	High Similarity	NPC74539
0.9366	High Similarity	NPC304443
0.9362	High Similarity	NPC246903
0.9348	High Similarity	NPC36414
0.9306	High Similarity	NPC191104
0.9203	High Similarity	NPC472516
0.9203	High Similarity	NPC29638
0.9155	High Similarity	NPC17262
0.9143	High Similarity	NPC472515
0.9143	High Similarity	NPC473209
0.9137	High Similarity	NPC103001
0.9137	High Similarity	NPC253616
0.9116	High Similarity	NPC131725
0.9091	High Similarity	NPC208584
0.9078	High Similarity	NPC470856
0.9065	High Similarity	NPC268081
0.9028	High Similarity	NPC190572
0.9021	High Similarity	NPC225884
0.9007	High Similarity	NPC136095
0.8944	High Similarity	NPC28337
0.8933	High Similarity	NPC269495
0.8926	High Similarity	NPC278010
0.8926	High Similarity	NPC250769
0.8926	High Similarity	NPC295608
0.8913	High Similarity	NPC229646
0.8912	High Similarity	NPC155882
0.8904	High Similarity	NPC272194
0.8897	High Similarity	NPC154217
0.8897	High Similarity	NPC210826
0.8897	High Similarity	NPC51641
0.8897	High Similarity	NPC300267
0.8874	High Similarity	NPC33320
0.8867	High Similarity	NPC19860
0.8865	High Similarity	NPC332594
0.8849	High Similarity	NPC292998
0.8849	High Similarity	NPC247743
0.8844	High Similarity	NPC221868
0.8844	High Similarity	NPC37208
0.8836	High Similarity	NPC12148
0.8836	High Similarity	NPC130581
0.8836	High Similarity	NPC198427
0.8828	High Similarity	NPC1886
0.8828	High Similarity	NPC196137
0.8819	High Similarity	NPC53192
0.8816	High Similarity	NPC169
0.8816	High Similarity	NPC49009
0.8816	High Similarity	NPC243509
0.8808	High Similarity	NPC270044
0.8784	High Similarity	NPC148423
0.8784	High Similarity	NPC135303
0.8784	High Similarity	NPC472406
0.8777	High Similarity	NPC55147
0.8776	High Similarity	NPC306788
0.8776	High Similarity	NPC135325
0.8767	High Similarity	NPC470322
0.8767	High Similarity	NPC181388
0.8759	High Similarity	NPC470296
0.8759	High Similarity	NPC196459
0.8759	High Similarity	NPC302181
0.8759	High Similarity	NPC112791
0.8759	High Similarity	NPC94794
0.8759	High Similarity	NPC87609
0.8759	High Similarity	NPC188632
0.8758	High Similarity	NPC216092
0.8758	High Similarity	NPC14822
0.875	High Similarity	NPC24075
0.875	High Similarity	NPC244750
0.8732	High Similarity	NPC157855
0.8732	High Similarity	NPC38153
0.8725	High Similarity	NPC290671
0.8723	High Similarity	NPC151113
0.8716	High Similarity	NPC39929
0.8716	High Similarity	NPC296030
0.8716	High Similarity	NPC226644
0.8716	High Similarity	NPC37226
0.871	High Similarity	NPC259007
0.871	High Similarity	NPC204088
0.871	High Similarity	NPC329215
0.8705	High Similarity	NPC284424
0.8699	High Similarity	NPC469935
0.8699	High Similarity	NPC230943
0.8699	High Similarity	NPC178627
0.8693	High Similarity	NPC239270
0.8693	High Similarity	NPC115432
0.8693	High Similarity	NPC260296
0.8693	High Similarity	NPC303210
0.8693	High Similarity	NPC95472
0.869	High Similarity	NPC36181
0.8671	High Similarity	NPC199458
0.8671	High Similarity	NPC183639
0.8667	High Similarity	NPC38361
0.8667	High Similarity	NPC130015
0.8667	High Similarity	NPC41326
0.8662	High Similarity	NPC254741
0.8662	High Similarity	NPC161196
0.8658	High Similarity	NPC230713
0.8658	High Similarity	NPC78335
0.8654	High Similarity	NPC323137
0.8652	High Similarity	NPC66705
0.8649	High Similarity	NPC208303
0.8649	High Similarity	NPC161864
0.8645	High Similarity	NPC179464
0.8643	High Similarity	NPC54503
0.8639	High Similarity	NPC473927
0.8623	High Similarity	NPC473894
0.8613	High Similarity	NPC49852
0.8613	High Similarity	NPC475496
0.8611	High Similarity	NPC19476
0.8611	High Similarity	NPC241975
0.8611	High Similarity	NPC137009
0.8609	High Similarity	NPC472462
0.8609	High Similarity	NPC41719
0.8601	High Similarity	NPC474624
0.8601	High Similarity	NPC138047
0.8601	High Similarity	NPC131782
0.8601	High Similarity	NPC228661
0.86	High Similarity	NPC170169
0.86	High Similarity	NPC472407
0.8592	High Similarity	NPC46869
0.8591	High Similarity	NPC178202
0.8591	High Similarity	NPC469932
0.859	High Similarity	NPC173149
0.859	High Similarity	NPC179015
0.8582	High Similarity	NPC93756
0.8582	High Similarity	NPC108113
0.8581	High Similarity	NPC282335
0.8581	High Similarity	NPC140120
0.8581	High Similarity	NPC249942
0.8581	High Similarity	NPC234536
0.8581	High Similarity	NPC78612
0.8581	High Similarity	NPC218300
0.8581	High Similarity	NPC297886
0.8581	High Similarity	NPC180477
0.8571	High Similarity	NPC469953
0.8571	High Similarity	NPC294365
0.8571	High Similarity	NPC155144
0.8571	High Similarity	NPC278556
0.8571	High Similarity	NPC171656
0.8553	High Similarity	NPC233776
0.8553	High Similarity	NPC469934
0.8552	High Similarity	NPC261227
0.8552	High Similarity	NPC475680
0.8552	High Similarity	NPC270883
0.8552	High Similarity	NPC172986
0.8552	High Similarity	NPC305355
0.8552	High Similarity	NPC472409
0.8552	High Similarity	NPC474037
0.8551	High Similarity	NPC473907
0.8543	High Similarity	NPC263676
0.8542	High Similarity	NPC470668
0.8542	High Similarity	NPC470669
0.8542	High Similarity	NPC470083
0.8542	High Similarity	NPC17848
0.8542	High Similarity	NPC201395
0.8542	High Similarity	NPC219584
0.8535	High Similarity	NPC155264
0.8535	High Similarity	NPC193881
0.8535	High Similarity	NPC67450
0.8535	High Similarity	NPC210460
0.8533	High Similarity	NPC474735
0.8526	High Similarity	NPC155640
0.8523	High Similarity	NPC168085
0.8523	High Similarity	NPC469933
0.8521	High Similarity	NPC125920
0.8514	High Similarity	NPC57470
0.8511	High Similarity	NPC101294
0.8511	High Similarity	NPC473655
0.8511	High Similarity	NPC182428
0.8497	Intermediate Similarity	NPC469936
0.8497	Intermediate Similarity	NPC78554
0.8497	Intermediate Similarity	NPC321372
0.8497	Intermediate Similarity	NPC474738
0.8497	Intermediate Similarity	NPC470625
0.8497	Intermediate Similarity	NPC474609
0.8497	Intermediate Similarity	NPC129053
0.8497	Intermediate Similarity	NPC109967
0.8497	Intermediate Similarity	NPC475797
0.8497	Intermediate Similarity	NPC13879
0.8493	Intermediate Similarity	NPC110969
0.8493	Intermediate Similarity	NPC201820
0.8493	Intermediate Similarity	NPC205006
0.8493	Intermediate Similarity	NPC282300
0.8493	Intermediate Similarity	NPC156590
0.8493	Intermediate Similarity	NPC64908
0.8493	Intermediate Similarity	NPC118840
0.8493	Intermediate Similarity	NPC470555
0.8493	Intermediate Similarity	NPC147688
0.8493	Intermediate Similarity	NPC103362
0.8487	Intermediate Similarity	NPC235333
0.8487	Intermediate Similarity	NPC213608
0.8487	Intermediate Similarity	NPC122365
0.8487	Intermediate Similarity	NPC1477
0.8483	Intermediate Similarity	NPC96565

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 NPC254010 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	453
0.1-0.2	1010
0.2-0.3	1703
0.3-0.4	2835
0.4-0.5	1850
0.5-0.6	912
0.6-0.7	259
0.7-0.8	92
0.8-0.85	19
0.85-0.9	13
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9852	High Similarity	NPD1243	Approved
0.9496	High Similarity	NPD643	Clinical (unspecified phase)
0.9366	High Similarity	NPD920	Approved
0.9362	High Similarity	NPD642	Clinical (unspecified phase)
0.8874	High Similarity	NPD919	Approved
0.8662	High Similarity	NPD2796	Approved
0.8442	Intermediate Similarity	NPD3749	Approved
0.8333	Intermediate Similarity	NPD3748	Approved
0.8322	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.831	Intermediate Similarity	NPD1240	Approved
0.828	Intermediate Similarity	NPD1247	Approved
0.8255	Intermediate Similarity	NPD6799	Approved
0.8247	Intermediate Similarity	NPD7819	Suspended
0.8247	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD7411	Suspended
0.8207	Intermediate Similarity	NPD1510	Phase 2
0.82	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD1607	Approved
0.8182	Intermediate Similarity	NPD6801	Discontinued
0.8163	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD1549	Phase 2
0.8095	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD2344	Approved
0.8095	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD7075	Discontinued
0.8082	Intermediate Similarity	NPD2799	Discontinued
0.8054	Intermediate Similarity	NPD3750	Approved
0.8052	Intermediate Similarity	NPD6599	Discontinued
0.7987	Intermediate Similarity	NPD2800	Approved
0.7987	Intermediate Similarity	NPD5494	Approved
0.7917	Intermediate Similarity	NPD1296	Phase 2
0.7917	Intermediate Similarity	NPD2313	Discontinued
0.7911	Intermediate Similarity	NPD7768	Phase 2
0.7905	Intermediate Similarity	NPD1551	Phase 2
0.7902	Intermediate Similarity	NPD6832	Phase 2
0.7901	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD1511	Approved
0.7881	Intermediate Similarity	NPD2309	Approved
0.7867	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD9717	Approved
0.7852	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD3817	Phase 2
0.7848	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD3926	Phase 2
0.7821	Intermediate Similarity	NPD4380	Phase 2
0.7817	Intermediate Similarity	NPD1203	Approved
0.7817	Intermediate Similarity	NPD3266	Approved
0.7817	Intermediate Similarity	NPD3267	Approved
0.7793	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD1512	Approved
0.7786	Intermediate Similarity	NPD422	Phase 1
0.7785	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD17	Approved
0.7733	Intermediate Similarity	NPD1471	Phase 3
0.7727	Intermediate Similarity	NPD2534	Approved
0.7727	Intermediate Similarity	NPD2532	Approved
0.7727	Intermediate Similarity	NPD5401	Approved
0.7727	Intermediate Similarity	NPD2533	Approved
0.7725	Intermediate Similarity	NPD6559	Discontinued
0.7697	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD3882	Suspended
0.7687	Intermediate Similarity	NPD4307	Phase 2
0.7667	Intermediate Similarity	NPD2935	Discontinued
0.766	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD3226	Approved
0.764	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD2798	Approved
0.7639	Intermediate Similarity	NPD1019	Discontinued
0.7635	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD5403	Approved
0.7628	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD1934	Approved
0.7606	Intermediate Similarity	NPD1608	Approved
0.7569	Intermediate Similarity	NPD2797	Approved
0.7562	Intermediate Similarity	NPD2801	Approved
0.756	Intermediate Similarity	NPD5953	Discontinued
0.7551	Intermediate Similarity	NPD3268	Approved
0.7534	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD7473	Discontinued
0.7516	Intermediate Similarity	NPD2654	Approved
0.75	Intermediate Similarity	NPD2346	Discontinued
0.7485	Intermediate Similarity	NPD3818	Discontinued
0.7483	Intermediate Similarity	NPD4308	Phase 3
0.7471	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD6651	Approved
0.7455	Intermediate Similarity	NPD6232	Discontinued
0.7455	Intermediate Similarity	NPD6808	Phase 2
0.744	Intermediate Similarity	NPD7286	Phase 2
0.744	Intermediate Similarity	NPD5844	Phase 1
0.744	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD411	Approved
0.7414	Intermediate Similarity	NPD4287	Approved
0.7407	Intermediate Similarity	NPD5402	Approved
0.74	Intermediate Similarity	NPD1933	Approved
0.74	Intermediate Similarity	NPD447	Suspended
0.7394	Intermediate Similarity	NPD6959	Discontinued
0.7391	Intermediate Similarity	NPD1241	Discontinued
0.7391	Intermediate Similarity	NPD6280	Approved
0.7391	Intermediate Similarity	NPD6279	Approved
0.7355	Intermediate Similarity	NPD4628	Phase 3
0.7355	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD1465	Phase 2
0.7329	Intermediate Similarity	NPD1164	Approved
0.7301	Intermediate Similarity	NPD4288	Approved
0.7301	Intermediate Similarity	NPD2296	Approved
0.7294	Intermediate Similarity	NPD1729	Discontinued
0.7292	Intermediate Similarity	NPD1281	Approved
0.7285	Intermediate Similarity	NPD5124	Phase 1
0.7285	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6585	Discontinued
0.726	Intermediate Similarity	NPD1876	Approved
0.726	Intermediate Similarity	NPD3225	Approved
0.7256	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD7033	Discontinued
0.7254	Intermediate Similarity	NPD9545	Approved
0.7246	Intermediate Similarity	NPD7229	Phase 3
0.7241	Intermediate Similarity	NPD3972	Approved
0.7234	Intermediate Similarity	NPD9493	Approved
0.7222	Intermediate Similarity	NPD5890	Approved
0.7222	Intermediate Similarity	NPD5889	Approved
0.7219	Intermediate Similarity	NPD943	Approved
0.7185	Intermediate Similarity	NPD9697	Approved
0.7161	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD2353	Approved
0.716	Intermediate Similarity	NPD6166	Phase 2
0.716	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD2403	Approved
0.716	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5711	Approved
0.7143	Intermediate Similarity	NPD5710	Approved
0.7143	Intermediate Similarity	NPD1283	Approved
0.7135	Intermediate Similarity	NPD7054	Approved
0.7134	Intermediate Similarity	NPD7003	Approved
0.7097	Intermediate Similarity	NPD6100	Approved
0.7097	Intermediate Similarity	NPD6099	Approved
0.7093	Intermediate Similarity	NPD7472	Approved
0.7093	Intermediate Similarity	NPD7074	Phase 3
0.7086	Intermediate Similarity	NPD3764	Approved
0.7069	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD230	Phase 1
0.7059	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1610	Phase 2
0.7052	Intermediate Similarity	NPD6797	Phase 2
0.7039	Intermediate Similarity	NPD8032	Phase 2
0.7037	Intermediate Similarity	NPD9261	Approved
0.7019	Intermediate Similarity	NPD6273	Approved
0.7017	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD4361	Phase 2
0.7014	Intermediate Similarity	NPD1548	Phase 1
0.7012	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7251	Discontinued
0.7006	Intermediate Similarity	NPD8434	Phase 2
0.6994	Remote Similarity	NPD7458	Discontinued
0.6994	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD7199	Phase 2
0.6981	Remote Similarity	NPD3887	Approved
0.6981	Remote Similarity	NPD2354	Approved
0.6978	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD7808	Phase 3
0.6966	Remote Similarity	NPD1651	Approved
0.6964	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.695	Remote Similarity	NPD5535	Approved
0.6948	Remote Similarity	NPD6355	Discontinued
0.6943	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD6005	Phase 3
0.6943	Remote Similarity	NPD6004	Phase 3
0.6943	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD6002	Phase 3
0.6939	Remote Similarity	NPD1611	Approved
0.6914	Remote Similarity	NPD5049	Phase 3
0.6901	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD7390	Discontinued
0.6883	Remote Similarity	NPD2979	Phase 3
0.6883	Remote Similarity	NPD3142	Approved
0.6883	Remote Similarity	NPD3140	Approved
0.6879	Remote Similarity	NPD5406	Approved
0.6879	Remote Similarity	NPD5404	Approved
0.6879	Remote Similarity	NPD5408	Approved
0.6879	Remote Similarity	NPD4476	Approved
0.6879	Remote Similarity	NPD4477	Approved
0.6879	Remote Similarity	NPD5405	Approved
0.6868	Remote Similarity	NPD4360	Phase 2
0.6868	Remote Similarity	NPD4363	Phase 3
0.6863	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD1652	Phase 2
0.6849	Remote Similarity	NPD5691	Approved
0.6845	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4908	Phase 1
0.6835	Remote Similarity	NPD9264	Approved
0.6835	Remote Similarity	NPD9263	Approved
0.6835	Remote Similarity	NPD9267	Approved
0.6805	Remote Similarity	NPD6971	Discontinued
0.6803	Remote Similarity	NPD1778	Approved
0.6802	Remote Similarity	NPD5242	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