NPASS Compound

Structure

NPC277394 OpenBabel07101719402D 23 24 0 0 0 0 0 0 0 0999 V2000 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 3 2 0 0 0 0 2 4 2 0 0 0 0 3 15 1 0 0 0 0 4 16 1 0 0 0 0 5 9 1 0 0 0 0 5 14 1 0 0 0 0 6 10 1 0 0 0 0 6 14 2 0 0 0 0 7 11 2 0 0 0 0 7 14 1 0 0 0 0 8 12 2 0 0 0 0 8 15 1 0 0 0 0 9 16 1 0 0 0 0 10 17 2 0 0 0 0 11 17 1 0 0 0 0 12 18 1 0 0 0 0 13 15 2 0 0 0 0 13 19 1 0 0 0 0 16 20 2 0 0 0 0 17 21 1 0 0 0 0 18 19 2 0 0 0 0 18 22 1 0 0 0 0 19 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	310.12
Volume:	331.5
LogP:	3.038
LogD:	3.237
LogS:	-3.238
# Rotatable Bonds:	6
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.433
Synthetic Accessibility Score:	2.42
Fsp3:	0.105
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.989
MDCK Permeability:	1.5577414160361513e-05
Pgp-inhibitor:	0.091
Pgp-substrate:	0.048
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.047
Plasma Protein Binding (PPB):	98.9796371459961%
Volume Distribution (VD):	0.502
Pgp-substrate:	0.8495262861251831%

ADMET: Metabolism

CYP1A2-inhibitor:	0.808
CYP1A2-substrate:	0.135
CYP2C19-inhibitor:	0.513
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.688
CYP2C9-substrate:	0.939
CYP2D6-inhibitor:	0.714
CYP2D6-substrate:	0.917
CYP3A4-inhibitor:	0.705
CYP3A4-substrate:	0.212

ADMET: Excretion

Clearance (CL):	17.227
Half-life (T1/2):	0.937

ADMET: Toxicity

hERG Blockers:	0.399
Human Hepatotoxicity (H-HT):	0.386
Drug-inuced Liver Injury (DILI):	0.093
AMES Toxicity:	0.801
Rat Oral Acute Toxicity:	0.749
Maximum Recommended Daily Dose:	0.922
Skin Sensitization:	0.972
Carcinogencity:	0.521
Eye Corrosion:	0.004
Eye Irritation:	0.928
Respiratory Toxicity:	0.591

Download Data

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

Natural Product: NPC277394

Natural Product ID:	NPC277394
*Common Name:**	(4E,6E)-7-(3,4-Dihydroxyphenyl)-1-(4-Hydroxyphenyl)Hepta-4,6-Dien-3-One
IUPAC Name:	(4E,6E)-7-(3,4-dihydroxyphenyl)-1-(4-hydroxyphenyl)hepta-4,6-dien-3-one
Synonyms:
Standard InCHIKey:	UWTOEMORWLXHJO-ZPUQHVIOSA-N
Standard InCHI:	InChI=1S/C19H18O4/c20-16(9-5-14-6-10-17(21)11-7-14)4-2-1-3-15-8-12-18(22)19(23)13-15/h1-4,6-8,10-13,21-23H,5,9H2/b3-1+,4-2+
SMILES:	C(=Cc1ccc(c(c1)O)O)/C=C/C(=O)CCc1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2398587
PubChem CID:	72164688
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids

*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
NPO22901	Curcuma comosa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/np100392m]
NPO22901	Curcuma comosa	Species	Zingiberaceae	Eukaryota	rhizomes	Kampaengsaen district, Nakhon Pathom province, Thailand	n.a.	PMID[18554915]
NPO22901	Curcuma comosa	Species	Zingiberaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[20196571]
NPO14409	Dioscorea nipponica	Species	Dioscoreaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[23707257]
NPO22901	Curcuma comosa	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[23910596]
NPO22901	Curcuma comosa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8176399]
NPO14409	Dioscorea nipponica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14409	Dioscorea nipponica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14409	Dioscorea nipponica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14409	Dioscorea nipponica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14409	Dioscorea nipponica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22901	Curcuma comosa	Species	Zingiberaceae	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	1
Others	9

Activity Type	# Activity
Cell Line	2
Individual Protein	1
NON-MOLECULAR	5
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT34	Cell Line	BV-2	Mus musculus	Activity	=	103.61	%	PMID[545446]
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	14360.0	nM	PMID[545446]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	<	17.0	%	PMID[545447]
NPT27	Others	Unspecified		Activity	=	92.3	%	PMID[545447]
NPT27	Others	Unspecified		Activity	=	95.2	%	PMID[545447]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	16.3	%	PMID[545447]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	23.4	%	PMID[545447]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	30.5	%	PMID[545447]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	37.8	%	PMID[545447]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	27.8	%	PMID[545447]

☑ 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 NPC277394 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	302
0.1-0.2	1565
0.2-0.3	4212
0.3-0.4	12113
0.4-0.5	6506
0.5-0.6	6292
0.6-0.7	9142
0.7-0.8	2293
0.8-0.85	195
0.85-0.9	62
0.9-0.95	11
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC299252
1.0	High Similarity	NPC61062
0.9537	High Similarity	NPC297657
0.945	High Similarity	NPC51698
0.9391	High Similarity	NPC86900
0.9217	High Similarity	NPC294361
0.9217	High Similarity	NPC236520
0.913	High Similarity	NPC34634
0.913	High Similarity	NPC265454
0.9074	High Similarity	NPC69332
0.9074	High Similarity	NPC70843
0.9074	High Similarity	NPC95178
0.9074	High Similarity	NPC29989
0.9052	High Similarity	NPC98305
0.9	High Similarity	NPC123228
0.9	High Similarity	NPC88141
0.9	High Similarity	NPC5018
0.9	High Similarity	NPC123722
0.9	High Similarity	NPC276466
0.9	High Similarity	NPC151167
0.8919	High Similarity	NPC222084
0.8917	High Similarity	NPC303680
0.8917	High Similarity	NPC90128
0.8917	High Similarity	NPC179777
0.8917	High Similarity	NPC84076
0.887	High Similarity	NPC150919
0.8852	High Similarity	NPC304622
0.8814	High Similarity	NPC472271
0.875	High Similarity	NPC288945
0.8727	High Similarity	NPC188677
0.8718	High Similarity	NPC263386
0.8718	High Similarity	NPC141791
0.8716	High Similarity	NPC261573
0.8716	High Similarity	NPC471511
0.8716	High Similarity	NPC79672
0.8716	High Similarity	NPC52087
0.8716	High Similarity	NPC8931
0.8716	High Similarity	NPC120693
0.8707	High Similarity	NPC278652
0.8689	High Similarity	NPC156539
0.8689	High Similarity	NPC107672
0.8684	High Similarity	NPC148969
0.8678	High Similarity	NPC53305
0.8678	High Similarity	NPC257589
0.8667	High Similarity	NPC242372
0.8667	High Similarity	NPC257976
0.8667	High Similarity	NPC4181
0.8667	High Similarity	NPC164778
0.8661	High Similarity	NPC228343
0.8661	High Similarity	NPC254833
0.8629	High Similarity	NPC244441
0.8624	High Similarity	NPC68269
0.8618	High Similarity	NPC234175
0.8611	High Similarity	NPC223393
0.8609	High Similarity	NPC285350
0.8607	High Similarity	NPC127937
0.8607	High Similarity	NPC276014
0.8607	High Similarity	NPC92207
0.8595	High Similarity	NPC312404
0.8595	High Similarity	NPC273686
0.8595	High Similarity	NPC85565
0.8584	High Similarity	NPC226401
0.8584	High Similarity	NPC79793
0.8584	High Similarity	NPC21162
0.8584	High Similarity	NPC147634
0.8584	High Similarity	NPC174096
0.8584	High Similarity	NPC120982
0.8584	High Similarity	NPC116842
0.8583	High Similarity	NPC114298
0.8571	High Similarity	NPC470849
0.8571	High Similarity	NPC470848
0.856	High Similarity	NPC198388
0.8559	High Similarity	NPC294902
0.8559	High Similarity	NPC1075
0.8559	High Similarity	NPC1786
0.8534	High Similarity	NPC322197
0.8534	High Similarity	NPC4665
0.8534	High Similarity	NPC23402
0.8525	High Similarity	NPC197832
0.8525	High Similarity	NPC3221
0.8519	High Similarity	NPC130193
0.8512	High Similarity	NPC106659
0.8512	High Similarity	NPC160900
0.8512	High Similarity	NPC18984
0.8512	High Similarity	NPC229084
0.8509	High Similarity	NPC257430
0.8509	High Similarity	NPC179002
0.8509	High Similarity	NPC187583
0.85	High Similarity	NPC147654
0.8496	Intermediate Similarity	NPC55617
0.8496	Intermediate Similarity	NPC62258
0.8492	Intermediate Similarity	NPC61
0.8492	Intermediate Similarity	NPC18074
0.8492	Intermediate Similarity	NPC25581
0.8492	Intermediate Similarity	NPC5419
0.848	Intermediate Similarity	NPC172673
0.848	Intermediate Similarity	NPC66905
0.848	Intermediate Similarity	NPC26697
0.8475	Intermediate Similarity	NPC275519
0.8468	Intermediate Similarity	NPC239291
0.8468	Intermediate Similarity	NPC226661
0.8455	Intermediate Similarity	NPC196479
0.8426	Intermediate Similarity	NPC201967
0.8426	Intermediate Similarity	NPC109955
0.8425	Intermediate Similarity	NPC471749
0.8425	Intermediate Similarity	NPC155209
0.8425	Intermediate Similarity	NPC168799
0.8417	Intermediate Similarity	NPC60962
0.8417	Intermediate Similarity	NPC189844
0.8417	Intermediate Similarity	NPC158949
0.8417	Intermediate Similarity	NPC109083
0.8417	Intermediate Similarity	NPC224814
0.8417	Intermediate Similarity	NPC14007
0.8417	Intermediate Similarity	NPC269843
0.8413	Intermediate Similarity	NPC469526
0.8413	Intermediate Similarity	NPC34070
0.8413	Intermediate Similarity	NPC318799
0.8407	Intermediate Similarity	NPC17525
0.8393	Intermediate Similarity	NPC19149
0.839	Intermediate Similarity	NPC175799
0.839	Intermediate Similarity	NPC200988
0.839	Intermediate Similarity	NPC610
0.839	Intermediate Similarity	NPC145023
0.8372	Intermediate Similarity	NPC194764
0.8372	Intermediate Similarity	NPC264112
0.8372	Intermediate Similarity	NPC65005
0.8361	Intermediate Similarity	NPC163083
0.8361	Intermediate Similarity	NPC285345
0.8361	Intermediate Similarity	NPC306100
0.8359	Intermediate Similarity	NPC106406
0.8348	Intermediate Similarity	NPC177576
0.8347	Intermediate Similarity	NPC201777
0.8346	Intermediate Similarity	NPC239302
0.8346	Intermediate Similarity	NPC135801
0.8333	Intermediate Similarity	NPC244246
0.8333	Intermediate Similarity	NPC137427
0.8333	Intermediate Similarity	NPC233056
0.8333	Intermediate Similarity	NPC65935
0.8333	Intermediate Similarity	NPC311419
0.8333	Intermediate Similarity	NPC123196
0.8333	Intermediate Similarity	NPC215941
0.8333	Intermediate Similarity	NPC319282
0.8333	Intermediate Similarity	NPC275724
0.8319	Intermediate Similarity	NPC63126
0.8319	Intermediate Similarity	NPC309434
0.8319	Intermediate Similarity	NPC141523
0.8319	Intermediate Similarity	NPC34715
0.8319	Intermediate Similarity	NPC86198
0.8319	Intermediate Similarity	NPC203124
0.8308	Intermediate Similarity	NPC290030
0.8305	Intermediate Similarity	NPC19290
0.8295	Intermediate Similarity	NPC43353
0.8293	Intermediate Similarity	NPC471927
0.8293	Intermediate Similarity	NPC15127
0.8291	Intermediate Similarity	NPC120280
0.8288	Intermediate Similarity	NPC135784
0.8281	Intermediate Similarity	NPC294226
0.8281	Intermediate Similarity	NPC327410
0.8279	Intermediate Similarity	NPC286573
0.8276	Intermediate Similarity	NPC286222
0.8264	Intermediate Similarity	NPC248363
0.8261	Intermediate Similarity	NPC252544
0.8261	Intermediate Similarity	NPC321252
0.8261	Intermediate Similarity	NPC222905
0.8257	Intermediate Similarity	NPC260000
0.8254	Intermediate Similarity	NPC241354
0.8254	Intermediate Similarity	NPC94810
0.825	Intermediate Similarity	NPC470214
0.825	Intermediate Similarity	NPC156654
0.825	Intermediate Similarity	NPC109371
0.825	Intermediate Similarity	NPC470215
0.825	Intermediate Similarity	NPC70084
0.825	Intermediate Similarity	NPC299406
0.8246	Intermediate Similarity	NPC233835
0.8244	Intermediate Similarity	NPC284409
0.8231	Intermediate Similarity	NPC90431
0.8231	Intermediate Similarity	NPC7464
0.823	Intermediate Similarity	NPC477814
0.8226	Intermediate Similarity	NPC67951
0.822	Intermediate Similarity	NPC278102
0.8211	Intermediate Similarity	NPC212541
0.8198	Intermediate Similarity	NPC110764
0.819	Intermediate Similarity	NPC470355
0.819	Intermediate Similarity	NPC268032
0.819	Intermediate Similarity	NPC226250
0.819	Intermediate Similarity	NPC268388
0.8189	Intermediate Similarity	NPC117609
0.8182	Intermediate Similarity	NPC280869
0.8182	Intermediate Similarity	NPC472903
0.8182	Intermediate Similarity	NPC474784
0.8175	Intermediate Similarity	NPC167463
0.8174	Intermediate Similarity	NPC95172
0.8168	Intermediate Similarity	NPC476393
0.8168	Intermediate Similarity	NPC279676
0.8168	Intermediate Similarity	NPC67349
0.8168	Intermediate Similarity	NPC471152
0.8167	Intermediate Similarity	NPC311091
0.8167	Intermediate Similarity	NPC249435
0.8167	Intermediate Similarity	NPC471033
0.816	Intermediate Similarity	NPC120225

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 NPC277394 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	292
0.1-0.2	956
0.2-0.3	1287
0.3-0.4	2791
0.4-0.5	2057
0.5-0.6	1219
0.6-0.7	458
0.7-0.8	86
0.8-0.85	2
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8661	High Similarity	NPD3021	Approved
0.8661	High Similarity	NPD3022	Approved
0.8512	High Similarity	NPD4379	Clinical (unspecified phase)
0.8346	Intermediate Similarity	NPD943	Approved
0.7982	Intermediate Similarity	NPD2933	Approved
0.7982	Intermediate Similarity	NPD2934	Approved
0.7934	Intermediate Similarity	NPD5536	Phase 2
0.7926	Intermediate Similarity	NPD8166	Discontinued
0.7909	Intermediate Similarity	NPD2859	Approved
0.7909	Intermediate Similarity	NPD2860	Approved
0.7886	Intermediate Similarity	NPD2932	Approved
0.7886	Intermediate Similarity	NPD3019	Approved
0.7857	Intermediate Similarity	NPD3020	Approved
0.784	Intermediate Similarity	NPD9269	Phase 2
0.7737	Intermediate Similarity	NPD6190	Approved
0.7734	Intermediate Similarity	NPD257	Approved
0.7734	Intermediate Similarity	NPD258	Approved
0.7705	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD9494	Approved
0.7674	Intermediate Similarity	NPD9569	Approved
0.7656	Intermediate Similarity	NPD1470	Approved
0.7619	Intermediate Similarity	NPD1201	Approved
0.7583	Intermediate Similarity	NPD228	Approved
0.7542	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD9377	Approved
0.7521	Intermediate Similarity	NPD9379	Approved
0.752	Intermediate Similarity	NPD9268	Approved
0.7519	Intermediate Similarity	NPD825	Approved
0.7519	Intermediate Similarity	NPD826	Approved
0.75	Intermediate Similarity	NPD1511	Approved
0.7483	Intermediate Similarity	NPD3455	Phase 2
0.7478	Intermediate Similarity	NPD1242	Phase 1
0.7463	Intermediate Similarity	NPD230	Phase 1
0.7445	Intermediate Similarity	NPD7266	Discontinued
0.7444	Intermediate Similarity	NPD259	Phase 1
0.7442	Intermediate Similarity	NPD5311	Approved
0.7442	Intermediate Similarity	NPD5310	Approved
0.7424	Intermediate Similarity	NPD9536	Phase 1
0.7424	Intermediate Similarity	NPD9537	Phase 1
0.7402	Intermediate Similarity	NPD3026	Approved
0.7402	Intermediate Similarity	NPD3023	Approved
0.7394	Intermediate Similarity	NPD1512	Approved
0.7385	Intermediate Similarity	NPD1164	Approved
0.7385	Intermediate Similarity	NPD3055	Approved
0.7385	Intermediate Similarity	NPD3053	Approved
0.7381	Intermediate Similarity	NPD3024	Approved
0.7381	Intermediate Similarity	NPD3025	Approved
0.7381	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD2935	Discontinued
0.7368	Intermediate Similarity	NPD3764	Approved
0.7355	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD274	Approved
0.7333	Intermediate Similarity	NPD555	Phase 2
0.7333	Intermediate Similarity	NPD275	Approved
0.7324	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD5283	Phase 1
0.7297	Intermediate Similarity	NPD3882	Suspended
0.7293	Intermediate Similarity	NPD3027	Phase 3
0.7288	Intermediate Similarity	NPD1237	Approved
0.7281	Intermediate Similarity	NPD844	Approved
0.7279	Intermediate Similarity	NPD2801	Approved
0.7279	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD5404	Approved
0.7246	Intermediate Similarity	NPD5406	Approved
0.7246	Intermediate Similarity	NPD5408	Approved
0.7246	Intermediate Similarity	NPD5405	Approved
0.7244	Intermediate Similarity	NPD1651	Approved
0.7211	Intermediate Similarity	NPD1934	Approved
0.7209	Intermediate Similarity	NPD1535	Discovery
0.719	Intermediate Similarity	NPD9266	Approved
0.719	Intermediate Similarity	NPD74	Approved
0.7179	Intermediate Similarity	NPD3028	Approved
0.7177	Intermediate Similarity	NPD1241	Discontinued
0.7174	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD9545	Approved
0.7156	Intermediate Similarity	NPD111	Approved
0.7154	Intermediate Similarity	NPD1481	Phase 2
0.7154	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD3972	Approved
0.7132	Intermediate Similarity	NPD3059	Approved
0.7132	Intermediate Similarity	NPD3061	Approved
0.7132	Intermediate Similarity	NPD3062	Approved
0.7122	Intermediate Similarity	NPD9570	Approved
0.7111	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD9264	Approved
0.7107	Intermediate Similarity	NPD9267	Approved
0.7107	Intermediate Similarity	NPD9263	Approved
0.7099	Intermediate Similarity	NPD1755	Approved
0.709	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD288	Approved
0.7068	Intermediate Similarity	NPD2798	Approved
0.7067	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD255	Approved
0.7063	Intermediate Similarity	NPD3300	Phase 2
0.7063	Intermediate Similarity	NPD256	Approved
0.7059	Intermediate Similarity	NPD6663	Approved
0.7054	Intermediate Similarity	NPD9384	Approved
0.7054	Intermediate Similarity	NPD9381	Approved
0.705	Intermediate Similarity	NPD2799	Discontinued
0.705	Intermediate Similarity	NPD1510	Phase 2
0.7045	Intermediate Similarity	NPD1283	Approved
0.7045	Intermediate Similarity	NPD1876	Approved
0.7042	Intermediate Similarity	NPD4628	Phase 3
0.7037	Intermediate Similarity	NPD7095	Approved
0.7034	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD1894	Discontinued
0.7029	Intermediate Similarity	NPD5314	Approved
0.7015	Intermediate Similarity	NPD5736	Approved
0.7015	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD9493	Approved
0.7008	Intermediate Similarity	NPD9568	Approved
0.7007	Intermediate Similarity	NPD1240	Approved
0.7	Intermediate Similarity	NPD3847	Discontinued
0.6992	Remote Similarity	NPD1203	Approved
0.6992	Remote Similarity	NPD2797	Approved
0.6985	Remote Similarity	NPD6798	Discontinued
0.6985	Remote Similarity	NPD3268	Approved
0.6975	Remote Similarity	NPD846	Approved
0.6975	Remote Similarity	NPD940	Approved
0.6967	Remote Similarity	NPD2342	Discontinued
0.696	Remote Similarity	NPD7635	Approved
0.6957	Remote Similarity	NPD447	Suspended
0.6957	Remote Similarity	NPD6355	Discontinued
0.6957	Remote Similarity	NPD1202	Approved
0.695	Remote Similarity	NPD2344	Approved
0.6949	Remote Similarity	NPD2066	Phase 3
0.6947	Remote Similarity	NPD3092	Approved
0.6934	Remote Similarity	NPD6233	Phase 2
0.6934	Remote Similarity	NPD4062	Phase 3
0.6923	Remote Similarity	NPD4110	Phase 3
0.6923	Remote Similarity	NPD3750	Approved
0.6923	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD1929	Approved
0.6917	Remote Similarity	NPD1930	Approved
0.6917	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD1607	Approved
0.6905	Remote Similarity	NPD2234	Approved
0.6905	Remote Similarity	NPD2228	Approved
0.6905	Remote Similarity	NPD2229	Approved
0.6899	Remote Similarity	NPD3091	Approved
0.6899	Remote Similarity	NPD1759	Phase 1
0.6897	Remote Similarity	NPD7390	Discontinued
0.6894	Remote Similarity	NPD1608	Approved
0.6884	Remote Similarity	NPD1613	Approved
0.6884	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD4060	Phase 1
0.6879	Remote Similarity	NPD3818	Discontinued
0.6871	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD3094	Phase 2
0.6864	Remote Similarity	NPD9495	Approved
0.6861	Remote Similarity	NPD2313	Discontinued
0.6859	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD6166	Phase 2
0.6859	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD1792	Phase 2
0.6855	Remote Similarity	NPD4750	Phase 3
0.6853	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.685	Remote Similarity	NPD5951	Approved
0.685	Remote Similarity	NPD9281	Approved
0.685	Remote Similarity	NPD2629	Approved
0.6846	Remote Similarity	NPD7028	Phase 2
0.6846	Remote Similarity	NPD4093	Discontinued
0.6846	Remote Similarity	NPD4380	Phase 2
0.6842	Remote Similarity	NPD9622	Approved
0.6842	Remote Similarity	NPD9256	Approved
0.6842	Remote Similarity	NPD9258	Approved
0.6842	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD2614	Approved
0.6838	Remote Similarity	NPD1809	Phase 2
0.6822	Remote Similarity	NPD1758	Phase 1
0.6818	Remote Similarity	NPD1281	Approved
0.681	Remote Similarity	NPD845	Approved
0.681	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD2286	Discontinued
0.6794	Remote Similarity	NPD4626	Approved
0.6794	Remote Similarity	NPD4059	Approved
0.6783	Remote Similarity	NPD1549	Phase 2
0.6781	Remote Similarity	NPD4357	Discontinued
0.6777	Remote Similarity	NPD9261	Approved
0.6776	Remote Similarity	NPD3817	Phase 2
0.6763	Remote Similarity	NPD1558	Phase 1
0.6763	Remote Similarity	NPD3620	Phase 2
0.6763	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD2354	Approved
0.6759	Remote Similarity	NPD2309	Approved
0.6752	Remote Similarity	NPD1220	Phase 1
0.6748	Remote Similarity	NPD1445	Approved
0.6748	Remote Similarity	NPD1444	Approved
0.6741	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.673	Remote Similarity	NPD7054	Approved
0.6721	Remote Similarity	NPD5909	Discontinued
0.6719	Remote Similarity	NPD690	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