NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	190.1
Volume:	206.03
LogP:	3.718
LogD:	3.646
LogS:	-4.061
# Rotatable Bonds:	1
TPSA:	18.46
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.678
Synthetic Accessibility Score:	2.407
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.567
MDCK Permeability:	2.106679130520206e-05
Pgp-inhibitor:	0.988
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.109
30% Bioavailability (F30%):	0.674

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.65
Plasma Protein Binding (PPB):	94.92241668701172%
Volume Distribution (VD):	2.617
Pgp-substrate:	4.206867694854736%

ADMET: Metabolism

CYP1A2-inhibitor:	0.979
CYP1A2-substrate:	0.944
CYP2C19-inhibitor:	0.885
CYP2C19-substrate:	0.881
CYP2C9-inhibitor:	0.471
CYP2C9-substrate:	0.915
CYP2D6-inhibitor:	0.923
CYP2D6-substrate:	0.914
CYP3A4-inhibitor:	0.516
CYP3A4-substrate:	0.555

ADMET: Excretion

Clearance (CL):	7.469
Half-life (T1/2):	0.299

ADMET: Toxicity

hERG Blockers:	0.055
Human Hepatotoxicity (H-HT):	0.882
Drug-inuced Liver Injury (DILI):	0.286
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.241
Maximum Recommended Daily Dose:	0.151
Skin Sensitization:	0.734
Carcinogencity:	0.882
Eye Corrosion:	0.041
Eye Irritation:	0.916
Respiratory Toxicity:	0.826

Download Data

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

Natural Product: NPC106141

Natural Product ID:	NPC106141
*Common Name:**	Prococene I
IUPAC Name:	7-methoxy-2,2-dimethylchromene
Synonyms:	Prococene I
Standard InCHIKey:	CPTJXGLQLVPIGP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H14O2/c1-12(2)7-6-9-4-5-10(13-3)8-11(9)14-12/h4-8H,1-3H3
SMILES:	COc1ccc2c(c1)OC(C=C2)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL451866
PubChem CID:	28619
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0003522] 2,2-dimethyl-1-benzopyrans [CHEMONTID:0004763] Precocenes

*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]
NPO2865	Abrus precatorius	Species	Fabaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[19299148]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21428416]
NPO2865	Abrus precatorius	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22210168]
NPO2865	Abrus precatorius	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	PMID[22210168]
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]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25737008]
NPO2865	Abrus precatorius	Species	Fabaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[2691636]
NPO2865	Abrus precatorius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2691636]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2865	Abrus precatorius	Species	Fabaceae	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[TCMID]
NPO27786	Eucalyptus dives	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2865	Abrus precatorius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2865	Abrus precatorius	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]
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]
NPO2865	Abrus precatorius	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	2
Others	20

Activity Type	# Activity
Organism	22

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1276	Organism	Gibberella zeae	Gibberella zeae	Inhibition	=	25.0	%	PMID[524642]
NPT1276	Organism	Gibberella zeae	Gibberella zeae	Inhibition	=	20.0	%	PMID[524642]
NPT1276	Organism	Gibberella zeae	Gibberella zeae	IC50	=	1.3	ppm	PMID[524642]
NPT1276	Organism	Gibberella zeae	Gibberella zeae	IC50	=	16600.0	nM	PMID[524642]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	FDI	=	115.7	n.a.	PMID[524643]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	FDI	=	73.8	n.a.	PMID[524643]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	FDI	=	41.9	n.a.	PMID[524643]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	FDI	=	164.6	n.a.	PMID[524643]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	FDI	=	86.8	n.a.	PMID[524643]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	FDI	=	77.8	n.a.	PMID[524643]
NPT733	Organism	Sitophilus granarius	Sitophilus granarius	FDI	=	139.0	n.a.	PMID[524643]
NPT733	Organism	Sitophilus granarius	Sitophilus granarius	FDI	=	83.8	n.a.	PMID[524643]
NPT733	Organism	Sitophilus granarius	Sitophilus granarius	FDI	=	55.2	n.a.	PMID[524643]
NPT2718	Organism	Trogoderma granarium	Trogoderma granarium	FDI	=	80.1	n.a.	PMID[524643]
NPT2718	Organism	Trogoderma granarium	Trogoderma granarium	FDI	=	38.3	n.a.	PMID[524643]
NPT2718	Organism	Trogoderma granarium	Trogoderma granarium	FDI	=	41.8	n.a.	PMID[524643]
NPT777	Organism	Tribolium confusum	Tribolium confusum	FDI	=	139.0	n.a.	PMID[524643]
NPT777	Organism	Tribolium confusum	Tribolium confusum	FDI	=	83.8	n.a.	PMID[524643]
NPT777	Organism	Tribolium confusum	Tribolium confusum	FDI	=	55.2	n.a.	PMID[524643]
NPT777	Organism	Tribolium confusum	Tribolium confusum	FDI	=	119.2	n.a.	PMID[524643]
NPT777	Organism	Tribolium confusum	Tribolium confusum	FDI	=	64.1	n.a.	PMID[524643]
NPT777	Organism	Tribolium confusum	Tribolium confusum	FDI	=	55.1	n.a.	PMID[524643]

☑ 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 NPC106141 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	464
0.1-0.2	2265
0.2-0.3	8413
0.3-0.4	11256
0.4-0.5	3577
0.5-0.6	6678
0.6-0.7	7413
0.7-0.8	2362
0.8-0.85	217
0.85-0.9	49
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9099	High Similarity	NPC96705
0.9099	High Similarity	NPC265547
0.9018	High Similarity	NPC281356
0.9018	High Similarity	NPC298796
0.8929	High Similarity	NPC152306
0.8929	High Similarity	NPC74821
0.8919	High Similarity	NPC128633
0.887	High Similarity	NPC194626
0.886	High Similarity	NPC235190
0.886	High Similarity	NPC180006
0.886	High Similarity	NPC163200
0.885	High Similarity	NPC295259
0.885	High Similarity	NPC59561
0.885	High Similarity	NPC172253
0.8739	High Similarity	NPC161696
0.8718	High Similarity	NPC270030
0.8707	High Similarity	NPC248429
0.8707	High Similarity	NPC74137
0.8707	High Similarity	NPC96286
0.8707	High Similarity	NPC257188
0.8707	High Similarity	NPC13007
0.8684	High Similarity	NPC85895
0.8684	High Similarity	NPC137294
0.8661	High Similarity	NPC185541
0.8661	High Similarity	NPC464
0.8632	High Similarity	NPC273772
0.8632	High Similarity	NPC173350
0.8632	High Similarity	NPC290605
0.8632	High Similarity	NPC315807
0.8632	High Similarity	NPC472518
0.8632	High Similarity	NPC154176
0.8632	High Similarity	NPC109675
0.8624	High Similarity	NPC82016
0.8621	High Similarity	NPC144418
0.8621	High Similarity	NPC52247
0.8621	High Similarity	NPC212965
0.8609	High Similarity	NPC8283
0.8609	High Similarity	NPC258979
0.8609	High Similarity	NPC93398
0.8584	High Similarity	NPC203113
0.8584	High Similarity	NPC85292
0.8584	High Similarity	NPC229147
0.8584	High Similarity	NPC54507
0.8571	High Similarity	NPC244364
0.8559	High Similarity	NPC201667
0.8559	High Similarity	NPC73413
0.8559	High Similarity	NPC111347
0.8559	High Similarity	NPC27671
0.8559	High Similarity	NPC159132
0.8547	High Similarity	NPC120638
0.8547	High Similarity	NPC100099
0.8547	High Similarity	NPC36016
0.8534	High Similarity	NPC218753
0.85	High Similarity	NPC149796
0.8475	Intermediate Similarity	NPC38761
0.8475	Intermediate Similarity	NPC76465
0.8462	Intermediate Similarity	NPC187868
0.8462	Intermediate Similarity	NPC54972
0.8462	Intermediate Similarity	NPC193364
0.8448	Intermediate Similarity	NPC247553
0.844	Intermediate Similarity	NPC35543
0.8435	Intermediate Similarity	NPC131118
0.843	Intermediate Similarity	NPC185066
0.8426	Intermediate Similarity	NPC8302
0.8417	Intermediate Similarity	NPC234109
0.8417	Intermediate Similarity	NPC188327
0.8417	Intermediate Similarity	NPC471826
0.8403	Intermediate Similarity	NPC106914
0.8403	Intermediate Similarity	NPC291899
0.8403	Intermediate Similarity	NPC134195
0.8403	Intermediate Similarity	NPC86502
0.8403	Intermediate Similarity	NPC294156
0.8403	Intermediate Similarity	NPC197351
0.8403	Intermediate Similarity	NPC246648
0.8403	Intermediate Similarity	NPC256015
0.8393	Intermediate Similarity	NPC280606
0.8378	Intermediate Similarity	NPC2682
0.8378	Intermediate Similarity	NPC303521
0.8376	Intermediate Similarity	NPC319378
0.8376	Intermediate Similarity	NPC302107
0.8376	Intermediate Similarity	NPC472596
0.8364	Intermediate Similarity	NPC291837
0.8364	Intermediate Similarity	NPC245115
0.8361	Intermediate Similarity	NPC134360
0.8348	Intermediate Similarity	NPC304208
0.8348	Intermediate Similarity	NPC52464
0.8347	Intermediate Similarity	NPC121740
0.8347	Intermediate Similarity	NPC224774
0.8347	Intermediate Similarity	NPC258567
0.8347	Intermediate Similarity	NPC46978
0.8333	Intermediate Similarity	NPC244495
0.8333	Intermediate Similarity	NPC285040
0.8333	Intermediate Similarity	NPC471827
0.8333	Intermediate Similarity	NPC131397
0.8333	Intermediate Similarity	NPC471828
0.8333	Intermediate Similarity	NPC93219
0.8333	Intermediate Similarity	NPC17809
0.8333	Intermediate Similarity	NPC188022
0.8333	Intermediate Similarity	NPC102540
0.8333	Intermediate Similarity	NPC103420
0.8333	Intermediate Similarity	NPC476254
0.8319	Intermediate Similarity	NPC50720
0.8319	Intermediate Similarity	NPC90903
0.8319	Intermediate Similarity	NPC204120
0.8305	Intermediate Similarity	NPC97432
0.8305	Intermediate Similarity	NPC190454
0.8304	Intermediate Similarity	NPC296920
0.8304	Intermediate Similarity	NPC255068
0.8304	Intermediate Similarity	NPC203924
0.8304	Intermediate Similarity	NPC90520
0.8293	Intermediate Similarity	NPC113098
0.8293	Intermediate Similarity	NPC474491
0.8293	Intermediate Similarity	NPC80170
0.8288	Intermediate Similarity	NPC165386
0.8288	Intermediate Similarity	NPC149545
0.8279	Intermediate Similarity	NPC472519
0.8279	Intermediate Similarity	NPC222572
0.8279	Intermediate Similarity	NPC469453
0.8279	Intermediate Similarity	NPC87224
0.8279	Intermediate Similarity	NPC157212
0.8279	Intermediate Similarity	NPC199204
0.8264	Intermediate Similarity	NPC283049
0.8264	Intermediate Similarity	NPC276212
0.8264	Intermediate Similarity	NPC50315
0.8264	Intermediate Similarity	NPC101894
0.8264	Intermediate Similarity	NPC230479
0.8264	Intermediate Similarity	NPC26879
0.8261	Intermediate Similarity	NPC150624
0.8261	Intermediate Similarity	NPC141090
0.8257	Intermediate Similarity	NPC238115
0.8252	Intermediate Similarity	NPC321956
0.8246	Intermediate Similarity	NPC180508
0.8246	Intermediate Similarity	NPC228287
0.8241	Intermediate Similarity	NPC305205
0.8235	Intermediate Similarity	NPC259134
0.8235	Intermediate Similarity	NPC302546
0.8235	Intermediate Similarity	NPC8002
0.8235	Intermediate Similarity	NPC99886
0.8235	Intermediate Similarity	NPC150214
0.8235	Intermediate Similarity	NPC177844
0.8235	Intermediate Similarity	NPC261661
0.8226	Intermediate Similarity	NPC272650
0.8226	Intermediate Similarity	NPC244888
0.8226	Intermediate Similarity	NPC211413
0.8226	Intermediate Similarity	NPC164804
0.8226	Intermediate Similarity	NPC29734
0.8226	Intermediate Similarity	NPC267336
0.8226	Intermediate Similarity	NPC118683
0.8226	Intermediate Similarity	NPC68205
0.8226	Intermediate Similarity	NPC293203
0.822	Intermediate Similarity	NPC102639
0.8214	Intermediate Similarity	NPC94045
0.8214	Intermediate Similarity	NPC88868
0.8214	Intermediate Similarity	NPC231251
0.8214	Intermediate Similarity	NPC25067
0.8211	Intermediate Similarity	NPC168710
0.8208	Intermediate Similarity	NPC95755
0.8205	Intermediate Similarity	NPC308217
0.8197	Intermediate Similarity	NPC475496
0.8197	Intermediate Similarity	NPC49852
0.8197	Intermediate Similarity	NPC243688
0.819	Intermediate Similarity	NPC69261
0.819	Intermediate Similarity	NPC50521
0.819	Intermediate Similarity	NPC33270
0.819	Intermediate Similarity	NPC244816
0.819	Intermediate Similarity	NPC474933
0.819	Intermediate Similarity	NPC195466
0.819	Intermediate Similarity	NPC221549
0.8182	Intermediate Similarity	NPC168259
0.8182	Intermediate Similarity	NPC167571
0.8182	Intermediate Similarity	NPC207179
0.8182	Intermediate Similarity	NPC164576
0.8182	Intermediate Similarity	NPC278552
0.8174	Intermediate Similarity	NPC808
0.8167	Intermediate Similarity	NPC474160
0.8165	Intermediate Similarity	NPC108875
0.8165	Intermediate Similarity	NPC38079
0.816	Intermediate Similarity	NPC14248
0.8155	Intermediate Similarity	NPC71853
0.8151	Intermediate Similarity	NPC476633
0.8148	Intermediate Similarity	NPC51633
0.8145	Intermediate Similarity	NPC19242
0.8145	Intermediate Similarity	NPC244799
0.8145	Intermediate Similarity	NPC474481
0.8145	Intermediate Similarity	NPC240722
0.8137	Intermediate Similarity	NPC47422
0.8131	Intermediate Similarity	NPC471576
0.813	Intermediate Similarity	NPC47283
0.813	Intermediate Similarity	NPC53986
0.813	Intermediate Similarity	NPC274717
0.813	Intermediate Similarity	NPC474651
0.813	Intermediate Similarity	NPC31707
0.813	Intermediate Similarity	NPC473907
0.813	Intermediate Similarity	NPC39064
0.813	Intermediate Similarity	NPC474623
0.813	Intermediate Similarity	NPC38664
0.8115	Intermediate Similarity	NPC471215
0.8115	Intermediate Similarity	NPC476006
0.8115	Intermediate Similarity	NPC262573
0.8108	Intermediate Similarity	NPC194034

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 NPC106141 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	408
0.1-0.2	1098
0.2-0.3	1941
0.3-0.4	2564
0.4-0.5	1609
0.5-0.6	932
0.6-0.7	508
0.7-0.8	83
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8929	High Similarity	NPD1548	Phase 1
0.8621	High Similarity	NPD422	Phase 1
0.8462	Intermediate Similarity	NPD1610	Phase 2
0.813	Intermediate Similarity	NPD4908	Phase 1
0.813	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD290	Approved
0.8017	Intermediate Similarity	NPD4749	Approved
0.8	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7928	Intermediate Similarity	NPD9697	Approved
0.7876	Intermediate Similarity	NPD2684	Approved
0.7857	Intermediate Similarity	NPD1296	Phase 2
0.784	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD940	Approved
0.7818	Intermediate Similarity	NPD846	Approved
0.7778	Intermediate Similarity	NPD4625	Phase 3
0.776	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD3018	Phase 2
0.7734	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7734	Intermediate Similarity	NPD1613	Approved
0.7717	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.771	Intermediate Similarity	NPD2796	Approved
0.7705	Intermediate Similarity	NPD1091	Approved
0.7699	Intermediate Similarity	NPD968	Approved
0.7692	Intermediate Similarity	NPD1241	Discontinued
0.7674	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD5124	Phase 1
0.7642	Intermediate Similarity	NPD2981	Phase 2
0.7607	Intermediate Similarity	NPD821	Approved
0.7607	Intermediate Similarity	NPD7843	Approved
0.7607	Intermediate Similarity	NPD5535	Approved
0.7581	Intermediate Similarity	NPD2983	Phase 2
0.7581	Intermediate Similarity	NPD2982	Phase 2
0.7563	Intermediate Similarity	NPD6671	Approved
0.7544	Intermediate Similarity	NPD3134	Approved
0.7537	Intermediate Similarity	NPD1652	Phase 2
0.75	Intermediate Similarity	NPD5451	Approved
0.75	Intermediate Similarity	NPD3748	Approved
0.7481	Intermediate Similarity	NPD7466	Approved
0.7478	Intermediate Similarity	NPD1358	Approved
0.7462	Intermediate Similarity	NPD1240	Approved
0.7424	Intermediate Similarity	NPD2200	Suspended
0.7417	Intermediate Similarity	NPD2557	Approved
0.7417	Intermediate Similarity	NPD7157	Approved
0.7411	Intermediate Similarity	NPD1242	Phase 1
0.7402	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD1778	Approved
0.7388	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD3225	Approved
0.7381	Intermediate Similarity	NPD8651	Approved
0.7364	Intermediate Similarity	NPD3027	Phase 3
0.7355	Intermediate Similarity	NPD3596	Phase 2
0.7348	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD1607	Approved
0.7344	Intermediate Similarity	NPD2861	Phase 2
0.7333	Intermediate Similarity	NPD1549	Phase 2
0.7319	Intermediate Similarity	NPD7213	Phase 3
0.7319	Intermediate Similarity	NPD7212	Phase 2
0.7279	Intermediate Similarity	NPD1243	Approved
0.7266	Intermediate Similarity	NPD7447	Phase 1
0.7266	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD17	Approved
0.725	Intermediate Similarity	NPD594	Approved
0.725	Intermediate Similarity	NPD5283	Phase 1
0.725	Intermediate Similarity	NPD592	Approved
0.7239	Intermediate Similarity	NPD1510	Phase 2
0.7236	Intermediate Similarity	NPD6580	Approved
0.7236	Intermediate Similarity	NPD1182	Approved
0.7236	Intermediate Similarity	NPD6581	Approved
0.7227	Intermediate Similarity	NPD228	Approved
0.7226	Intermediate Similarity	NPD3750	Approved
0.7206	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD6799	Approved
0.7188	Intermediate Similarity	NPD2797	Approved
0.7188	Intermediate Similarity	NPD3266	Approved
0.7188	Intermediate Similarity	NPD3267	Approved
0.7185	Intermediate Similarity	NPD1551	Phase 2
0.7185	Intermediate Similarity	NPD6099	Approved
0.7185	Intermediate Similarity	NPD6100	Approved
0.7185	Intermediate Similarity	NPD3539	Phase 1
0.7177	Intermediate Similarity	NPD5691	Approved
0.7177	Intermediate Similarity	NPD3443	Approved
0.7177	Intermediate Similarity	NPD3049	Approved
0.7177	Intermediate Similarity	NPD3445	Approved
0.7177	Intermediate Similarity	NPD3444	Approved
0.7177	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD9365	Approved
0.7154	Intermediate Similarity	NPD1408	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD3691	Phase 2
0.7132	Intermediate Similarity	NPD3690	Phase 2
0.7132	Intermediate Similarity	NPD3540	Phase 1
0.7122	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD6516	Phase 2
0.712	Intermediate Similarity	NPD5846	Approved
0.712	Intermediate Similarity	NPD2556	Approved
0.712	Intermediate Similarity	NPD2554	Approved
0.7111	Intermediate Similarity	NPD7033	Discontinued
0.7097	Intermediate Similarity	NPD1894	Discontinued
0.7097	Intermediate Similarity	NPD2486	Discontinued
0.7087	Intermediate Similarity	NPD9717	Approved
0.7087	Intermediate Similarity	NPD1608	Approved
0.7083	Intermediate Similarity	NPD1137	Approved
0.7083	Intermediate Similarity	NPD1139	Approved
0.7071	Intermediate Similarity	NPD1511	Approved
0.7063	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD3496	Discontinued
0.7059	Intermediate Similarity	NPD4750	Phase 3
0.7042	Intermediate Similarity	NPD920	Approved
0.704	Intermediate Similarity	NPD5585	Approved
0.7031	Intermediate Similarity	NPD5327	Phase 3
0.7031	Intermediate Similarity	NPD6583	Phase 3
0.7031	Intermediate Similarity	NPD6582	Phase 2
0.7025	Intermediate Similarity	NPD1138	Approved
0.7023	Intermediate Similarity	NPD6832	Phase 2
0.7021	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD3705	Approved
0.7008	Intermediate Similarity	NPD1611	Approved
0.7008	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1019	Discontinued
0.6993	Remote Similarity	NPD1653	Approved
0.6992	Remote Similarity	NPD709	Approved
0.6984	Remote Similarity	NPD2668	Approved
0.6984	Remote Similarity	NPD4626	Approved
0.6984	Remote Similarity	NPD2667	Approved
0.6978	Remote Similarity	NPD3892	Phase 2
0.6978	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6696	Suspended
0.6972	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD1512	Approved
0.697	Remote Similarity	NPD3180	Approved
0.697	Remote Similarity	NPD3179	Approved
0.6964	Remote Similarity	NPD2934	Approved
0.6964	Remote Similarity	NPD2933	Approved
0.696	Remote Similarity	NPD7534	Approved
0.696	Remote Similarity	NPD7533	Approved
0.6953	Remote Similarity	NPD1840	Phase 2
0.695	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.694	Remote Similarity	NPD4307	Phase 2
0.6929	Remote Similarity	NPD3294	Phase 2
0.6923	Remote Similarity	NPD1203	Approved
0.6923	Remote Similarity	NPD3567	Approved
0.6923	Remote Similarity	NPD3568	Approved
0.6917	Remote Similarity	NPD6798	Discontinued
0.6917	Remote Similarity	NPD3268	Approved
0.6916	Remote Similarity	NPD111	Approved
0.6911	Remote Similarity	NPD595	Approved
0.6911	Remote Similarity	NPD593	Approved
0.6906	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD1651	Approved
0.6905	Remote Similarity	NPD6382	Discontinued
0.6903	Remote Similarity	NPD2859	Approved
0.6903	Remote Similarity	NPD2860	Approved
0.6901	Remote Similarity	NPD5401	Approved
0.6899	Remote Similarity	NPD6542	Approved
0.6899	Remote Similarity	NPD3685	Discontinued
0.6899	Remote Similarity	NPD2429	Approved
0.6899	Remote Similarity	NPD2428	Approved
0.6899	Remote Similarity	NPD6539	Approved
0.6899	Remote Similarity	NPD6543	Approved
0.6899	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6540	Phase 3
0.6897	Remote Similarity	NPD6599	Discontinued
0.6897	Remote Similarity	NPD291	Approved
0.6889	Remote Similarity	NPD4340	Discontinued
0.688	Remote Similarity	NPD5536	Phase 2
0.6875	Remote Similarity	NPD1535	Discovery
0.6871	Remote Similarity	NPD2801	Approved
0.687	Remote Similarity	NPD6584	Phase 3
0.6857	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD6387	Discontinued
0.6849	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD7411	Suspended
0.6846	Remote Similarity	NPD6538	Approved
0.6846	Remote Similarity	NPD6541	Approved
0.6835	Remote Similarity	NPD2424	Discontinued
0.6825	Remote Similarity	NPD9545	Approved
0.6824	Remote Similarity	NPD3817	Phase 2
0.6822	Remote Similarity	NPD1481	Phase 2
0.6818	Remote Similarity	NPD4993	Discontinued
0.6818	Remote Similarity	NPD9295	Approved
0.6815	Remote Similarity	NPD1558	Phase 1
0.6815	Remote Similarity	NPD2238	Phase 2
0.6815	Remote Similarity	NPD4060	Phase 1
0.6809	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD5403	Approved
0.6803	Remote Similarity	NPD6801	Discontinued
0.6803	Remote Similarity	NPD1934	Approved
0.6797	Remote Similarity	NPD3847	Discontinued
0.6794	Remote Similarity	NPD1820	Approved
0.6794	Remote Similarity	NPD987	Approved
0.6794	Remote Similarity	NPD1817	Approved
0.6794	Remote Similarity	NPD1819	Approved
0.6794	Remote Similarity	NPD1818	Approved
0.6794	Remote Similarity	NPD1794	Approved
0.6794	Remote Similarity	NPD1770	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD1048	Approved
0.6788	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD6111	Discontinued

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