NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	220.11
Volume:	232.116
LogP:	3.298
LogD:	3.412
LogS:	-3.801
# Rotatable Bonds:	2
TPSA:	27.69
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.767
Synthetic Accessibility Score:	2.415
Fsp3:	0.385
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:	-4.644
MDCK Permeability:	2.0918218069709837e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.032
30% Bioavailability (F30%):	0.514

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.738
Plasma Protein Binding (PPB):	91.49425506591797%
Volume Distribution (VD):	2.0
Pgp-substrate:	9.972238540649414%

ADMET: Metabolism

CYP1A2-inhibitor:	0.947
CYP1A2-substrate:	0.915
CYP2C19-inhibitor:	0.527
CYP2C19-substrate:	0.897
CYP2C9-inhibitor:	0.156
CYP2C9-substrate:	0.837
CYP2D6-inhibitor:	0.729
CYP2D6-substrate:	0.902
CYP3A4-inhibitor:	0.25
CYP3A4-substrate:	0.666

ADMET: Excretion

Clearance (CL):	8.155
Half-life (T1/2):	0.611

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.869
Drug-inuced Liver Injury (DILI):	0.578
AMES Toxicity:	0.034
Rat Oral Acute Toxicity:	0.14
Maximum Recommended Daily Dose:	0.058
Skin Sensitization:	0.424
Carcinogencity:	0.844
Eye Corrosion:	0.012
Eye Irritation:	0.383
Respiratory Toxicity:	0.724

Download Data

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

Natural Product: NPC194626

Natural Product ID:	NPC194626
*Common Name:**	Prococene Ii
IUPAC Name:	6,7-dimethoxy-2,2-dimethylchromene
Synonyms:	Prococene II
Standard InCHIKey:	PTIDGSWTMLSGAH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H16O3/c1-13(2)6-5-9-7-11(14-3)12(15-4)8-10(9)16-13/h5-8H,1-4H3
SMILES:	CC1(C)C=Cc2cc(c(cc2O1)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL448964
PubChem CID:	12565
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0003522] 2,2-dimethyl-1-benzopyrans

*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
NPO27786	Eucalyptus dives	Species	Myrtaceae	Eukaryota	essential oils	n.a.	n.a.	PMID[19191669]
NPO33171	matricaria recutita	Species	Asteraceae	Eukaryota	essential oils	n.a.	n.a.	PMID[19191669]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21428416]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22870812]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23435948]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[23743282]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25737008]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9525107]
NPO18681	Artemisia scoparia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22209	Ageratum houstonianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19893	Senecio longifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27786	Eucalyptus dives	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18681	Artemisia scoparia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19893	Senecio longifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27786	Eucalyptus dives	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22209	Ageratum houstonianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18681	Artemisia scoparia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27786	Eucalyptus dives	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18681	Artemisia scoparia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22209	Ageratum houstonianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13558	Mundulea suberosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10631	Gerbera lanuginosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11100	Artemisia capillaris	Species	Asteraceae	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	3
LD50	1
Others	22
Potency	1

Activity Type	# Activity
Individual Protein	1
Organism	26

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	10.0	nM	PMID[494671]
NPT1276	Organism	Gibberella zeae	Gibberella zeae	IC50	=	2.0	ppm	PMID[494668]
NPT1276	Organism	Gibberella zeae	Gibberella zeae	IC50	=	0.36	ppm	PMID[494668]
NPT1276	Organism	Gibberella zeae	Gibberella zeae	IC50	=	1200.0	nM	PMID[494668]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	FDI	=	116.0	n.a.	PMID[494669]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	FDI	=	71.8	n.a.	PMID[494669]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	FDI	=	44.2	n.a.	PMID[494669]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	FDI	=	124.1	n.a.	PMID[494669]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	FDI	=	91.2	n.a.	PMID[494669]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	FDI	=	32.9	n.a.	PMID[494669]
NPT733	Organism	Sitophilus granarius	Sitophilus granarius	FDI	=	194.2	n.a.	PMID[494669]
NPT733	Organism	Sitophilus granarius	Sitophilus granarius	FDI	=	94.2	n.a.	PMID[494669]
NPT733	Organism	Sitophilus granarius	Sitophilus granarius	FDI	=	100.0	n.a.	PMID[494669]
NPT2718	Organism	Trogoderma granarium	Trogoderma granarium	FDI	=	198.6	n.a.	PMID[494669]
NPT2718	Organism	Trogoderma granarium	Trogoderma granarium	FDI	=	100.0	n.a.	PMID[494669]
NPT2718	Organism	Trogoderma granarium	Trogoderma granarium	FDI	=	98.6	n.a.	PMID[494669]
NPT777	Organism	Tribolium confusum	Tribolium confusum	FDI	=	194.2	n.a.	PMID[494669]
NPT777	Organism	Tribolium confusum	Tribolium confusum	FDI	=	94.2	n.a.	PMID[494669]
NPT777	Organism	Tribolium confusum	Tribolium confusum	FDI	=	100.0	n.a.	PMID[494669]
NPT777	Organism	Tribolium confusum	Tribolium confusum	FDI	=	165.7	n.a.	PMID[494669]
NPT777	Organism	Tribolium confusum	Tribolium confusum	FDI	=	97.1	n.a.	PMID[494669]
NPT777	Organism	Tribolium confusum	Tribolium confusum	FDI	=	68.6	n.a.	PMID[494669]
NPT2212	Organism	Oncopeltus fasciatus	Oncopeltus fasciatus	Activity	=	5.0	%	PMID[494670]
NPT2212	Organism	Oncopeltus fasciatus	Oncopeltus fasciatus	Activity	=	27.5	%	PMID[494670]
NPT2212	Organism	Oncopeltus fasciatus	Oncopeltus fasciatus	Activity	=	22.5	%	PMID[494670]
NPT2212	Organism	Oncopeltus fasciatus	Oncopeltus fasciatus	Activity	=	45.0	%	PMID[494670]
NPT785	Organism	Pieris brassicae	Pieris brassicae	LD50	=	39.5	ug	PMID[494670]

☑ 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 NPC194626 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	551
0.1-0.2	2337
0.2-0.3	8702
0.3-0.4	11110
0.4-0.5	3221
0.5-0.6	5492
0.6-0.7	7897
0.7-0.8	2796
0.8-0.85	466
0.85-0.9	117
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9478	High Similarity	NPC52464
0.9478	High Similarity	NPC304208
0.9316	High Similarity	NPC308217
0.918	High Similarity	NPC244364
0.9068	High Similarity	NPC474612
0.9048	High Similarity	NPC137669
0.904	High Similarity	NPC240722
0.904	High Similarity	NPC244799
0.9032	High Similarity	NPC474616
0.9008	High Similarity	NPC270326
0.9	High Similarity	NPC472596
0.8976	High Similarity	NPC36437
0.8976	High Similarity	NPC241341
0.8976	High Similarity	NPC233018
0.8968	High Similarity	NPC82503
0.8966	High Similarity	NPC204120
0.896	High Similarity	NPC27239
0.896	High Similarity	NPC123127
0.896	High Similarity	NPC45824
0.8957	High Similarity	NPC203924
0.8926	High Similarity	NPC285289
0.8906	High Similarity	NPC474600
0.8898	High Similarity	NPC319969
0.8889	High Similarity	NPC214860
0.888	High Similarity	NPC31707
0.8871	High Similarity	NPC476006
0.887	High Similarity	NPC106141
0.8862	High Similarity	NPC183446
0.8852	High Similarity	NPC261661
0.8852	High Similarity	NPC264885
0.88	High Similarity	NPC474670
0.88	High Similarity	NPC216836
0.8783	High Similarity	NPC165386
0.8779	High Similarity	NPC270256
0.8769	High Similarity	NPC167517
0.8769	High Similarity	NPC286843
0.876	High Similarity	NPC309953
0.876	High Similarity	NPC106215
0.876	High Similarity	NPC474478
0.874	High Similarity	NPC19242
0.874	High Similarity	NPC476399
0.8739	High Similarity	NPC123948
0.873	High Similarity	NPC63179
0.873	High Similarity	NPC474651
0.873	High Similarity	NPC474623
0.871	High Similarity	NPC283170
0.871	High Similarity	NPC191768
0.871	High Similarity	NPC92869
0.8699	High Similarity	NPC211231
0.8692	High Similarity	NPC327382
0.8692	High Similarity	NPC195022
0.8692	High Similarity	NPC234865
0.8692	High Similarity	NPC472337
0.8689	High Similarity	NPC199023
0.8682	High Similarity	NPC168059
0.8682	High Similarity	NPC36661
0.8682	High Similarity	NPC229442
0.8678	High Similarity	NPC15805
0.8678	High Similarity	NPC475961
0.8678	High Similarity	NPC254625
0.8661	High Similarity	NPC190144
0.8661	High Similarity	NPC10225
0.8661	High Similarity	NPC474227
0.8661	High Similarity	NPC58164
0.8651	High Similarity	NPC189248
0.8651	High Similarity	NPC474821
0.8651	High Similarity	NPC202904
0.8647	High Similarity	NPC300611
0.8636	High Similarity	NPC43500
0.8636	High Similarity	NPC164148
0.8626	High Similarity	NPC173660
0.8626	High Similarity	NPC472336
0.8626	High Similarity	NPC472334
0.8594	High Similarity	NPC192687
0.8594	High Similarity	NPC237169
0.8594	High Similarity	NPC51840
0.8594	High Similarity	NPC311680
0.8594	High Similarity	NPC474617
0.8594	High Similarity	NPC229231
0.8594	High Similarity	NPC220935
0.8594	High Similarity	NPC224157
0.8594	High Similarity	NPC234488
0.8594	High Similarity	NPC299221
0.8594	High Similarity	NPC470624
0.8583	High Similarity	NPC210674
0.8583	High Similarity	NPC19694
0.8571	High Similarity	NPC474632
0.8561	High Similarity	NPC20796
0.8561	High Similarity	NPC102904
0.8561	High Similarity	NPC474521
0.8561	High Similarity	NPC148835
0.8561	High Similarity	NPC107551
0.8561	High Similarity	NPC276490
0.8561	High Similarity	NPC103976
0.8561	High Similarity	NPC76336
0.8561	High Similarity	NPC326797
0.8561	High Similarity	NPC474282
0.8561	High Similarity	NPC474530
0.8561	High Similarity	NPC139548
0.8561	High Similarity	NPC20511
0.8561	High Similarity	NPC176051
0.8561	High Similarity	NPC474540
0.8561	High Similarity	NPC95162
0.8561	High Similarity	NPC52086
0.855	High Similarity	NPC73071
0.855	High Similarity	NPC240915
0.8538	High Similarity	NPC472522
0.8538	High Similarity	NPC269528
0.8538	High Similarity	NPC263064
0.8538	High Similarity	NPC37196
0.8538	High Similarity	NPC94236
0.8527	High Similarity	NPC45715
0.8527	High Similarity	NPC474238
0.8527	High Similarity	NPC474356
0.8527	High Similarity	NPC12275
0.8516	High Similarity	NPC222004
0.8516	High Similarity	NPC202582
0.8516	High Similarity	NPC285339
0.8516	High Similarity	NPC226788
0.8516	High Similarity	NPC3439
0.8516	High Similarity	NPC210623
0.8516	High Similarity	NPC190629
0.8516	High Similarity	NPC218856
0.8516	High Similarity	NPC273295
0.8516	High Similarity	NPC470258
0.8504	High Similarity	NPC210355
0.8504	High Similarity	NPC242032
0.8504	High Similarity	NPC474119
0.8496	Intermediate Similarity	NPC471388
0.8496	Intermediate Similarity	NPC245207
0.8496	Intermediate Similarity	NPC127218
0.8496	Intermediate Similarity	NPC319647
0.8496	Intermediate Similarity	NPC13067
0.8496	Intermediate Similarity	NPC25966
0.8496	Intermediate Similarity	NPC292882
0.8496	Intermediate Similarity	NPC19869
0.8492	Intermediate Similarity	NPC64391
0.8492	Intermediate Similarity	NPC265483
0.8492	Intermediate Similarity	NPC60885
0.8492	Intermediate Similarity	NPC299584
0.8492	Intermediate Similarity	NPC82483
0.8492	Intermediate Similarity	NPC105925
0.8492	Intermediate Similarity	NPC234400
0.8485	Intermediate Similarity	NPC126682
0.8485	Intermediate Similarity	NPC82271
0.8485	Intermediate Similarity	NPC230734
0.8485	Intermediate Similarity	NPC474639
0.8485	Intermediate Similarity	NPC227503
0.848	Intermediate Similarity	NPC108545
0.8473	Intermediate Similarity	NPC7163
0.8473	Intermediate Similarity	NPC310854
0.8473	Intermediate Similarity	NPC147030
0.8468	Intermediate Similarity	NPC75713
0.8468	Intermediate Similarity	NPC477886
0.8462	Intermediate Similarity	NPC127624
0.8462	Intermediate Similarity	NPC123954
0.8462	Intermediate Similarity	NPC202762
0.8462	Intermediate Similarity	NPC161203
0.8462	Intermediate Similarity	NPC86655
0.8462	Intermediate Similarity	NPC6451
0.845	Intermediate Similarity	NPC79184
0.845	Intermediate Similarity	NPC91291
0.845	Intermediate Similarity	NPC307042
0.845	Intermediate Similarity	NPC474481
0.8448	Intermediate Similarity	NPC258171
0.8444	Intermediate Similarity	NPC174522
0.8443	Intermediate Similarity	NPC63083
0.8438	Intermediate Similarity	NPC266691
0.8438	Intermediate Similarity	NPC474636
0.8433	Intermediate Similarity	NPC160283
0.8433	Intermediate Similarity	NPC27495
0.8433	Intermediate Similarity	NPC254759
0.8425	Intermediate Similarity	NPC50683
0.8425	Intermediate Similarity	NPC18924
0.8425	Intermediate Similarity	NPC44748
0.8425	Intermediate Similarity	NPC112571
0.8425	Intermediate Similarity	NPC103823
0.8425	Intermediate Similarity	NPC78974
0.8425	Intermediate Similarity	NPC214406
0.8425	Intermediate Similarity	NPC112596
0.8425	Intermediate Similarity	NPC285725
0.8425	Intermediate Similarity	NPC223953
0.8425	Intermediate Similarity	NPC223136
0.8425	Intermediate Similarity	NPC28730
0.8421	Intermediate Similarity	NPC476171
0.8413	Intermediate Similarity	NPC228972
0.8413	Intermediate Similarity	NPC270030
0.8413	Intermediate Similarity	NPC122792
0.8409	Intermediate Similarity	NPC472521
0.8409	Intermediate Similarity	NPC94750
0.8409	Intermediate Similarity	NPC61946
0.8409	Intermediate Similarity	NPC121812
0.8409	Intermediate Similarity	NPC134968
0.8409	Intermediate Similarity	NPC112939
0.8409	Intermediate Similarity	NPC151224
0.8409	Intermediate Similarity	NPC281521
0.8409	Intermediate Similarity	NPC112246
0.8409	Intermediate Similarity	NPC201357
0.8409	Intermediate Similarity	NPC470356
0.8409	Intermediate Similarity	NPC255147

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 NPC194626 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	486
0.1-0.2	1037
0.2-0.3	2343
0.3-0.4	2472
0.4-0.5	1418
0.5-0.6	847
0.6-0.7	476
0.7-0.8	65
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8359	Intermediate Similarity	NPD3018	Phase 2
0.8295	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8254	Intermediate Similarity	NPD2981	Phase 2
0.8217	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8189	Intermediate Similarity	NPD2983	Phase 2
0.8189	Intermediate Similarity	NPD2982	Phase 2
0.8182	Intermediate Similarity	NPD1613	Approved
0.8182	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD3027	Phase 3
0.8	Intermediate Similarity	NPD1548	Phase 1
0.7902	Intermediate Similarity	NPD1653	Approved
0.7886	Intermediate Similarity	NPD5283	Phase 1
0.7769	Intermediate Similarity	NPD4749	Approved
0.7762	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD6671	Approved
0.7755	Intermediate Similarity	NPD2801	Approved
0.7754	Intermediate Similarity	NPD3539	Phase 1
0.7752	Intermediate Similarity	NPD3705	Approved
0.7752	Intermediate Similarity	NPD1610	Phase 2
0.7752	Intermediate Similarity	NPD422	Phase 1
0.7724	Intermediate Similarity	NPD228	Approved
0.7698	Intermediate Similarity	NPD3540	Phase 1
0.7612	Intermediate Similarity	NPD4908	Phase 1
0.7556	Intermediate Similarity	NPD4625	Phase 3
0.7541	Intermediate Similarity	NPD290	Approved
0.7537	Intermediate Similarity	NPD2861	Phase 2
0.75	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5536	Phase 2
0.7483	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD1091	Approved
0.748	Intermediate Similarity	NPD2684	Approved
0.7467	Intermediate Similarity	NPD3817	Phase 2
0.7386	Intermediate Similarity	NPD5494	Approved
0.7379	Intermediate Similarity	NPD1511	Approved
0.7372	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD1408	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD6111	Discontinued
0.7353	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD1652	Phase 2
0.7338	Intermediate Similarity	NPD1247	Approved
0.7333	Intermediate Similarity	NPD1934	Approved
0.7329	Intermediate Similarity	NPD1424	Approved
0.7324	Intermediate Similarity	NPD1375	Discontinued
0.7317	Intermediate Similarity	NPD968	Approved
0.7315	Intermediate Similarity	NPD4678	Approved
0.7315	Intermediate Similarity	NPD4675	Approved
0.7279	Intermediate Similarity	NPD1512	Approved
0.7273	Intermediate Similarity	NPD3496	Discontinued
0.7266	Intermediate Similarity	NPD1558	Phase 1
0.7254	Intermediate Similarity	NPD2796	Approved
0.7252	Intermediate Similarity	NPD1357	Approved
0.7248	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD7843	Approved
0.7209	Intermediate Similarity	NPD7157	Approved
0.7206	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1778	Approved
0.7192	Intermediate Similarity	NPD7124	Phase 2
0.719	Intermediate Similarity	NPD3882	Suspended
0.7185	Intermediate Similarity	NPD6696	Suspended
0.7185	Intermediate Similarity	NPD2922	Phase 1
0.7185	Intermediate Similarity	NPD8651	Approved
0.7183	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7534	Approved
0.7176	Intermediate Similarity	NPD7533	Approved
0.7171	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD846	Approved
0.7131	Intermediate Similarity	NPD940	Approved
0.7123	Intermediate Similarity	NPD2219	Phase 1
0.7122	Intermediate Similarity	NPD1296	Phase 2
0.712	Intermediate Similarity	NPD1358	Approved
0.7111	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7549	Discontinued
0.7097	Intermediate Similarity	NPD919	Approved
0.7097	Intermediate Similarity	NPD9697	Approved
0.7092	Intermediate Similarity	NPD5124	Phase 1
0.7092	Intermediate Similarity	NPD447	Suspended
0.7092	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD1611	Approved
0.7071	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5844	Phase 1
0.7055	Intermediate Similarity	NPD7466	Approved
0.7051	Intermediate Similarity	NPD5677	Discontinued
0.7049	Intermediate Similarity	NPD1242	Phase 1
0.7047	Intermediate Similarity	NPD1349	Approved
0.7047	Intermediate Similarity	NPD1351	Approved
0.7047	Intermediate Similarity	NPD1350	Approved
0.7047	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD1182	Approved
0.7032	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD1774	Approved
0.7027	Intermediate Similarity	NPD4357	Discontinued
0.7027	Intermediate Similarity	NPD5297	Approved
0.7014	Intermediate Similarity	NPD6099	Approved
0.7014	Intermediate Similarity	NPD6100	Approved
0.7013	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7199	Phase 2
0.7	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD291	Approved
0.6992	Remote Similarity	NPD5585	Approved
0.6992	Remote Similarity	NPD5691	Approved
0.6986	Remote Similarity	NPD6674	Discontinued
0.6986	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6166	Phase 2
0.6981	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.698	Remote Similarity	NPD4123	Phase 3
0.698	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD5535	Approved
0.6977	Remote Similarity	NPD821	Approved
0.6968	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7054	Approved
0.6944	Remote Similarity	NPD3748	Approved
0.694	Remote Similarity	NPD17	Approved
0.6937	Remote Similarity	NPD3489	Phase 3
0.6923	Remote Similarity	NPD1398	Phase 1
0.6923	Remote Similarity	NPD1241	Discontinued
0.6918	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD3926	Phase 2
0.6914	Remote Similarity	NPD7472	Approved
0.6913	Remote Similarity	NPD6799	Approved
0.6908	Remote Similarity	NPD4005	Discontinued
0.6905	Remote Similarity	NPD3134	Approved
0.6903	Remote Similarity	NPD5402	Approved
0.6901	Remote Similarity	NPD4060	Phase 1
0.6894	Remote Similarity	NPD3818	Discontinued
0.6892	Remote Similarity	NPD2677	Approved
0.689	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD5976	Discontinued
0.6883	Remote Similarity	NPD37	Approved
0.6879	Remote Similarity	NPD5111	Phase 2
0.6879	Remote Similarity	NPD5718	Phase 2
0.6879	Remote Similarity	NPD5110	Phase 2
0.6879	Remote Similarity	NPD5109	Approved
0.6875	Remote Similarity	NPD4750	Phase 3
0.6875	Remote Similarity	NPD2200	Suspended
0.6875	Remote Similarity	NPD5451	Approved
0.6871	Remote Similarity	NPD4237	Approved
0.6871	Remote Similarity	NPD4236	Phase 3
0.6867	Remote Similarity	NPD7447	Phase 1
0.6861	Remote Similarity	NPD5327	Phase 3
0.6859	Remote Similarity	NPD4967	Phase 2
0.6859	Remote Similarity	NPD4966	Approved
0.6859	Remote Similarity	NPD4965	Approved
0.6859	Remote Similarity	NPD6788	Approved
0.6853	Remote Similarity	NPD230	Phase 1
0.6853	Remote Similarity	NPD1933	Approved
0.6831	Remote Similarity	NPD6233	Phase 2
0.6824	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD3892	Phase 2
0.6824	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD6331	Phase 2
0.6821	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5089	Approved
0.6818	Remote Similarity	NPD2557	Approved
0.6818	Remote Similarity	NPD5090	Approved
0.6815	Remote Similarity	NPD4055	Discovery
0.6815	Remote Similarity	NPD5846	Approved
0.6815	Remote Similarity	NPD6516	Phase 2
0.6815	Remote Similarity	NPD4626	Approved
0.681	Remote Similarity	NPD7074	Phase 3
0.6809	Remote Similarity	NPD7095	Approved
0.6806	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD2653	Approved
0.6803	Remote Similarity	NPD2424	Discontinued
0.68	Remote Similarity	NPD7213	Phase 3
0.68	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7212	Phase 2
0.6797	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD2563	Approved
0.6795	Remote Similarity	NPD5353	Approved
0.6795	Remote Similarity	NPD2560	Approved
0.679	Remote Similarity	NPD8252	Approved
0.679	Remote Similarity	NPD8099	Discontinued
0.679	Remote Similarity	NPD8251	Approved
0.6788	Remote Similarity	NPD7808	Phase 3
0.6788	Remote Similarity	NPD1840	Phase 2
0.6788	Remote Similarity	NPD1608	Approved
0.6786	Remote Similarity	NPD2237	Approved
0.6783	Remote Similarity	NPD2238	Phase 2
0.6783	Remote Similarity	NPD1240	Approved
0.6781	Remote Similarity	NPD2161	Phase 2
0.6776	Remote Similarity	NPD2122	Discontinued
0.6774	Remote Similarity	NPD3382	Approved
0.6774	Remote Similarity	NPD3383	Approved
0.6774	Remote Similarity	NPD3384	Approved
0.6772	Remote Similarity	NPD6234	Discontinued
0.6768	Remote Similarity	NPD6797	Phase 2
0.6767	Remote Similarity	NPD3596	Phase 2
0.6767	Remote Similarity	NPD7340	Approved
0.6759	Remote Similarity	NPD4536	Approved
0.6759	Remote Similarity	NPD4538	Approved
0.6759	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5177	Phase 3
0.6757	Remote Similarity	NPD1243	Approved
0.6757	Remote Similarity	NPD4162	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