NPASS Compound

Structure

CID120693 OpenBabel06191715472D 22 23 0 0 0 0 0 0 0 0999 V2000 -5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 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 -3.4641 -4.0000 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 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 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 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 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 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 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 -7.7942 -1.5000 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 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 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 1 0 0 0 0 3 15 1 0 0 0 0 4 17 1 0 0 0 0 5 11 1 0 0 0 0 5 15 2 0 0 0 0 6 12 2 0 0 0 0 6 15 1 0 0 0 0 7 10 1 0 0 0 0 7 16 1 0 0 0 0 8 13 1 0 0 0 0 8 16 2 0 0 0 0 9 14 2 0 0 0 0 9 16 1 0 0 0 0 10 17 1 0 0 0 0 11 18 2 0 0 0 0 12 18 1 0 0 0 0 13 19 2 0 0 0 0 14 19 1 0 0 0 0 17 20 2 0 0 0 0 18 21 1 0 0 0 0 19 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	296.14
Volume:	325.346
LogP:	2.938
LogD:	3.085
LogS:	-2.948
# Rotatable Bonds:	7
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.809
Synthetic Accessibility Score:	2.155
Fsp3:	0.211
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.87
MDCK Permeability:	1.6992154996842146e-05
Pgp-inhibitor:	0.924
Pgp-substrate:	0.913
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.085
Plasma Protein Binding (PPB):	97.56755828857422%
Volume Distribution (VD):	0.76
Pgp-substrate:	1.4205858707427979%

ADMET: Metabolism

CYP1A2-inhibitor:	0.889
CYP1A2-substrate:	0.226
CYP2C19-inhibitor:	0.919
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.787
CYP2C9-substrate:	0.973
CYP2D6-inhibitor:	0.825
CYP2D6-substrate:	0.922
CYP3A4-inhibitor:	0.652
CYP3A4-substrate:	0.287

ADMET: Excretion

Clearance (CL):	17.223
Half-life (T1/2):	0.948

ADMET: Toxicity

hERG Blockers:	0.352
Human Hepatotoxicity (H-HT):	0.212
Drug-inuced Liver Injury (DILI):	0.029
AMES Toxicity:	0.026
Rat Oral Acute Toxicity:	0.164
Maximum Recommended Daily Dose:	0.717
Skin Sensitization:	0.946
Carcinogencity:	0.509
Eye Corrosion:	0.011
Eye Irritation:	0.881
Respiratory Toxicity:	0.464

Download Data

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

Natural Product: NPC120693

Natural Product ID:	NPC120693
*Common Name:**	(E)-1,7-Bis(4-Hydroxyphenyl)Hept-6-En-3-One
IUPAC Name:	(E)-1,7-bis(4-hydroxyphenyl)hept-6-en-3-one
Synonyms:
Standard InCHIKey:	PDFRZPRYDQDKCQ-HNQUOIGGSA-N
Standard InCHI:	InChI=1S/C19H20O3/c20-17(10-7-16-8-13-19(22)14-9-16)4-2-1-3-15-5-11-18(21)12-6-15/h1,3,5-6,8-9,11-14,21-22H,2,4,7,10H2/b3-1+
SMILES:	C(=Cc1ccc(cc1)O)/CCC(=O)CCc1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1270155
PubChem CID:	49831652
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
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	DOI[10.1021/np100392m]
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]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[20879743]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21807513]
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]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	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	2
Others	8

Activity Type	# Activity
Cell Line	1
Individual Protein	1
NON-MOLECULAR	6
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	8930.0	nM	PMID[530460]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	<	17.0	%	PMID[530461]
NPT27	Others	Unspecified		Activity	=	71.6	%	PMID[530461]
NPT27	Others	Unspecified		Activity	>	91.9	%	PMID[530461]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1240.0	nM	PMID[530461]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	57.1	%	PMID[530461]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	61.4	%	PMID[530461]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	44.9	%	PMID[530461]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	29.9	%	PMID[530461]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	21.2	%	PMID[530461]

☑ 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 NPC120693 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	237
0.1-0.2	1473
0.2-0.3	4087
0.3-0.4	12417
0.4-0.5	6903
0.5-0.6	8336
0.6-0.7	7389
0.7-0.8	1632
0.8-0.85	150
0.85-0.9	53
0.9-0.95	12
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC8931
1.0	High Similarity	NPC261573
0.9796	High Similarity	NPC188677
0.9596	High Similarity	NPC69332
0.9596	High Similarity	NPC70843
0.9596	High Similarity	NPC29989
0.9596	High Similarity	NPC95178
0.9505	High Similarity	NPC88141
0.9412	High Similarity	NPC252544
0.9412	High Similarity	NPC321252
0.932	High Similarity	NPC177576
0.9278	High Similarity	NPC260000
0.9231	High Similarity	NPC286222
0.9184	High Similarity	NPC280869
0.9167	High Similarity	NPC151715
0.9072	High Similarity	NPC26244
0.9057	High Similarity	NPC285350
0.9038	High Similarity	NPC21162
0.9038	High Similarity	NPC116842
0.9029	High Similarity	NPC317305
0.899	High Similarity	NPC245561
0.898	High Similarity	NPC473388
0.8972	High Similarity	NPC23402
0.8972	High Similarity	NPC322197
0.8958	High Similarity	NPC45040
0.8932	High Similarity	NPC228737
0.8911	High Similarity	NPC68269
0.8911	High Similarity	NPC135784
0.89	High Similarity	NPC52472
0.8889	High Similarity	NPC201967
0.8846	High Similarity	NPC17525
0.8812	High Similarity	NPC472585
0.88	High Similarity	NPC51333
0.88	High Similarity	NPC216468
0.88	High Similarity	NPC132078
0.88	High Similarity	NPC130193
0.88	High Similarity	NPC78119
0.8788	High Similarity	NPC216520
0.8788	High Similarity	NPC292730
0.8788	High Similarity	NPC132271
0.8788	High Similarity	NPC82664
0.8776	High Similarity	NPC128062
0.8762	High Similarity	NPC95172
0.875	High Similarity	NPC141523
0.8738	High Similarity	NPC13495
0.8727	High Similarity	NPC249435
0.8716	High Similarity	NPC61062
0.8716	High Similarity	NPC277394
0.8716	High Similarity	NPC19290
0.8716	High Similarity	NPC299252
0.8713	High Similarity	NPC213730
0.8687	High Similarity	NPC274678
0.8667	High Similarity	NPC31274
0.8649	High Similarity	NPC182240
0.8627	High Similarity	NPC7686
0.8627	High Similarity	NPC91461
0.8627	High Similarity	NPC40258
0.8614	High Similarity	NPC92730
0.8598	High Similarity	NPC268388
0.8586	High Similarity	NPC76938
0.8571	High Similarity	NPC473136
0.8571	High Similarity	NPC226699
0.8571	High Similarity	NPC265454
0.8571	High Similarity	NPC34634
0.8557	High Similarity	NPC318325
0.8557	High Similarity	NPC123273
0.8557	High Similarity	NPC280347
0.8557	High Similarity	NPC242240
0.8557	High Similarity	NPC177420
0.8544	High Similarity	NPC168829
0.8515	High Similarity	NPC225464
0.8505	High Similarity	NPC222905
0.85	High Similarity	NPC32714
0.8496	Intermediate Similarity	NPC98305
0.8482	Intermediate Similarity	NPC258366
0.8482	Intermediate Similarity	NPC79933
0.8482	Intermediate Similarity	NPC31296
0.8482	Intermediate Similarity	NPC473974
0.8476	Intermediate Similarity	NPC6984
0.8469	Intermediate Similarity	NPC55561
0.8462	Intermediate Similarity	NPC288411
0.8454	Intermediate Similarity	NPC113460
0.8454	Intermediate Similarity	NPC25493
0.844	Intermediate Similarity	NPC242136
0.8421	Intermediate Similarity	NPC31936
0.8421	Intermediate Similarity	NPC196976
0.8407	Intermediate Similarity	NPC318552
0.8407	Intermediate Similarity	NPC190501
0.8381	Intermediate Similarity	NPC138942
0.8381	Intermediate Similarity	NPC154899
0.8381	Intermediate Similarity	NPC474839
0.8381	Intermediate Similarity	NPC233396
0.8378	Intermediate Similarity	NPC471925
0.8378	Intermediate Similarity	NPC471924
0.8378	Intermediate Similarity	NPC325646
0.8378	Intermediate Similarity	NPC471928
0.8378	Intermediate Similarity	NPC28951
0.8378	Intermediate Similarity	NPC128249
0.8367	Intermediate Similarity	NPC258219
0.8365	Intermediate Similarity	NPC13426
0.8351	Intermediate Similarity	NPC23167
0.835	Intermediate Similarity	NPC294741
0.8348	Intermediate Similarity	NPC86900
0.8348	Intermediate Similarity	NPC176208
0.8333	Intermediate Similarity	NPC32322
0.8333	Intermediate Similarity	NPC175313
0.8333	Intermediate Similarity	NPC63345
0.8333	Intermediate Similarity	NPC259703
0.8319	Intermediate Similarity	NPC42657
0.8319	Intermediate Similarity	NPC188814
0.8319	Intermediate Similarity	NPC195262
0.8304	Intermediate Similarity	NPC471926
0.8304	Intermediate Similarity	NPC325295
0.8304	Intermediate Similarity	NPC76308
0.8302	Intermediate Similarity	NPC92623
0.8302	Intermediate Similarity	NPC135464
0.8302	Intermediate Similarity	NPC113457
0.83	Intermediate Similarity	NPC181709
0.83	Intermediate Similarity	NPC271440
0.8288	Intermediate Similarity	NPC51345
0.8286	Intermediate Similarity	NPC119860
0.8283	Intermediate Similarity	NPC192
0.8283	Intermediate Similarity	NPC300017
0.8257	Intermediate Similarity	NPC114682
0.8257	Intermediate Similarity	NPC297657
0.8257	Intermediate Similarity	NPC212718
0.8247	Intermediate Similarity	NPC197783
0.8246	Intermediate Similarity	NPC159525
0.8241	Intermediate Similarity	NPC326187
0.823	Intermediate Similarity	NPC328694
0.823	Intermediate Similarity	NPC311091
0.823	Intermediate Similarity	NPC184527
0.823	Intermediate Similarity	NPC471033
0.8229	Intermediate Similarity	NPC265146
0.8224	Intermediate Similarity	NPC34715
0.8218	Intermediate Similarity	NPC27323
0.8218	Intermediate Similarity	NPC316301
0.8205	Intermediate Similarity	NPC231767
0.82	Intermediate Similarity	NPC270547
0.82	Intermediate Similarity	NPC304541
0.819	Intermediate Similarity	NPC68167
0.8182	Intermediate Similarity	NPC228988
0.8182	Intermediate Similarity	NPC98772
0.8182	Intermediate Similarity	NPC51698
0.8174	Intermediate Similarity	NPC248363
0.8174	Intermediate Similarity	NPC216216
0.8174	Intermediate Similarity	NPC236520
0.8174	Intermediate Similarity	NPC164852
0.8174	Intermediate Similarity	NPC294361
0.8174	Intermediate Similarity	NPC241001
0.8165	Intermediate Similarity	NPC183700
0.8165	Intermediate Similarity	NPC222084
0.8163	Intermediate Similarity	NPC184169
0.8158	Intermediate Similarity	NPC158222
0.8155	Intermediate Similarity	NPC32674
0.8148	Intermediate Similarity	NPC63698
0.8148	Intermediate Similarity	NPC262365
0.8148	Intermediate Similarity	NPC11554
0.8148	Intermediate Similarity	NPC224584
0.8148	Intermediate Similarity	NPC61885
0.8144	Intermediate Similarity	NPC248817
0.8136	Intermediate Similarity	NPC3221
0.8136	Intermediate Similarity	NPC127975
0.8136	Intermediate Similarity	NPC257589
0.8136	Intermediate Similarity	NPC53305
0.8131	Intermediate Similarity	NPC271274
0.8131	Intermediate Similarity	NPC317592
0.812	Intermediate Similarity	NPC14141
0.8119	Intermediate Similarity	NPC306884
0.8119	Intermediate Similarity	NPC210497
0.8119	Intermediate Similarity	NPC162314
0.8119	Intermediate Similarity	NPC138117
0.8119	Intermediate Similarity	NPC94139
0.8119	Intermediate Similarity	NPC3358
0.8119	Intermediate Similarity	NPC147284
0.8119	Intermediate Similarity	NPC325292
0.8113	Intermediate Similarity	NPC241891
0.8113	Intermediate Similarity	NPC323810
0.8113	Intermediate Similarity	NPC471511
0.8113	Intermediate Similarity	NPC30506
0.8108	Intermediate Similarity	NPC62546
0.8108	Intermediate Similarity	NPC162113
0.8108	Intermediate Similarity	NPC11824
0.8103	Intermediate Similarity	NPC295034
0.8103	Intermediate Similarity	NPC242895
0.8103	Intermediate Similarity	NPC154696
0.8103	Intermediate Similarity	NPC120545
0.8103	Intermediate Similarity	NPC156139
0.8103	Intermediate Similarity	NPC472271
0.8091	Intermediate Similarity	NPC470355
0.8087	Intermediate Similarity	NPC478121
0.8081	Intermediate Similarity	NPC104216
0.8077	Intermediate Similarity	NPC128723
0.8073	Intermediate Similarity	NPC265211
0.8073	Intermediate Similarity	NPC306045
0.8073	Intermediate Similarity	NPC62258
0.8073	Intermediate Similarity	NPC79543
0.8073	Intermediate Similarity	NPC254833
0.8073	Intermediate Similarity	NPC228343
0.8073	Intermediate Similarity	NPC55617

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 NPC120693 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	258
0.1-0.2	964
0.2-0.3	1044
0.3-0.4	2674
0.4-0.5	2235
0.5-0.6	1301
0.6-0.7	550
0.7-0.8	113
0.8-0.85	6
0.85-0.9	3
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9072	High Similarity	NPD2860	Approved
0.9072	High Similarity	NPD2859	Approved
0.8969	High Similarity	NPD2934	Approved
0.8969	High Similarity	NPD2933	Approved
0.88	High Similarity	NPD3020	Approved
0.8407	Intermediate Similarity	NPD2932	Approved
0.8407	Intermediate Similarity	NPD3019	Approved
0.8218	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.8073	Intermediate Similarity	NPD3022	Approved
0.8073	Intermediate Similarity	NPD3021	Approved
0.8041	Intermediate Similarity	NPD111	Approved
0.7965	Intermediate Similarity	NPD255	Approved
0.7965	Intermediate Similarity	NPD256	Approved
0.7925	Intermediate Similarity	NPD940	Approved
0.7925	Intermediate Similarity	NPD846	Approved
0.789	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7845	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.783	Intermediate Similarity	NPD3028	Approved
0.783	Intermediate Similarity	NPD1242	Phase 1
0.7797	Intermediate Similarity	NPD1201	Approved
0.7797	Intermediate Similarity	NPD1535	Discovery
0.7788	Intermediate Similarity	NPD1809	Phase 2
0.7788	Intermediate Similarity	NPD844	Approved
0.7778	Intermediate Similarity	NPD1237	Approved
0.7767	Intermediate Similarity	NPD845	Approved
0.7759	Intermediate Similarity	NPD1894	Discontinued
0.7739	Intermediate Similarity	NPD9568	Approved
0.7731	Intermediate Similarity	NPD1481	Phase 2
0.7712	Intermediate Similarity	NPD3023	Approved
0.7712	Intermediate Similarity	NPD3847	Discontinued
0.7712	Intermediate Similarity	NPD3026	Approved
0.7692	Intermediate Similarity	NPD3025	Approved
0.7692	Intermediate Similarity	NPD1651	Approved
0.7692	Intermediate Similarity	NPD3024	Approved
0.7686	Intermediate Similarity	NPD1164	Approved
0.7632	Intermediate Similarity	NPD2229	Approved
0.7632	Intermediate Similarity	NPD2234	Approved
0.7632	Intermediate Similarity	NPD2228	Approved
0.7586	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7583	Intermediate Similarity	NPD3972	Approved
0.7547	Intermediate Similarity	NPD288	Approved
0.7541	Intermediate Similarity	NPD2797	Approved
0.7541	Intermediate Similarity	NPD1470	Approved
0.7521	Intermediate Similarity	NPD1755	Approved
0.752	Intermediate Similarity	NPD3764	Approved
0.75	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD74	Approved
0.75	Intermediate Similarity	NPD9266	Approved
0.7478	Intermediate Similarity	NPD1241	Discontinued
0.746	Intermediate Similarity	NPD6663	Approved
0.7459	Intermediate Similarity	NPD1283	Approved
0.7458	Intermediate Similarity	NPD1759	Phase 1
0.7458	Intermediate Similarity	NPD9545	Approved
0.7419	Intermediate Similarity	NPD5736	Approved
0.7411	Intermediate Similarity	NPD2342	Discontinued
0.7411	Intermediate Similarity	NPD9263	Approved
0.7411	Intermediate Similarity	NPD9264	Approved
0.7411	Intermediate Similarity	NPD9267	Approved
0.7407	Intermediate Similarity	NPD2066	Phase 3
0.7404	Intermediate Similarity	NPD1239	Approved
0.7402	Intermediate Similarity	NPD943	Approved
0.7402	Intermediate Similarity	NPD1240	Approved
0.7391	Intermediate Similarity	NPD5535	Approved
0.7391	Intermediate Similarity	NPD7635	Approved
0.7381	Intermediate Similarity	NPD6798	Discontinued
0.7381	Intermediate Similarity	NPD3268	Approved
0.7377	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD1758	Phase 1
0.7339	Intermediate Similarity	NPD2798	Approved
0.7333	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD968	Approved
0.7317	Intermediate Similarity	NPD1876	Approved
0.7315	Intermediate Similarity	NPD9495	Approved
0.7311	Intermediate Similarity	NPD5304	Approved
0.7311	Intermediate Similarity	NPD3091	Approved
0.7311	Intermediate Similarity	NPD5303	Approved
0.73	Intermediate Similarity	NPD9491	Approved
0.7297	Intermediate Similarity	NPD9608	Approved
0.7297	Intermediate Similarity	NPD9610	Approved
0.7297	Intermediate Similarity	NPD5909	Discontinued
0.7295	Intermediate Similarity	NPD1608	Approved
0.7288	Intermediate Similarity	NPD9493	Approved
0.7287	Intermediate Similarity	NPD1607	Approved
0.7281	Intermediate Similarity	NPD1792	Phase 2
0.7281	Intermediate Similarity	NPD5451	Approved
0.7281	Intermediate Similarity	NPD4750	Phase 3
0.7264	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD2935	Discontinued
0.725	Intermediate Similarity	NPD4093	Discontinued
0.7244	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2614	Approved
0.7213	Intermediate Similarity	NPD1281	Approved
0.7212	Intermediate Similarity	NPD800	Approved
0.7209	Intermediate Similarity	NPD6355	Discontinued
0.7207	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD1930	Approved
0.7207	Intermediate Similarity	NPD1929	Approved
0.72	Intermediate Similarity	NPD257	Approved
0.72	Intermediate Similarity	NPD258	Approved
0.7197	Intermediate Similarity	NPD2344	Approved
0.7196	Intermediate Similarity	NPD1693	Approved
0.7196	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD2684	Approved
0.719	Intermediate Similarity	NPD4589	Approved
0.719	Intermediate Similarity	NPD2286	Discontinued
0.719	Intermediate Similarity	NPD4059	Approved
0.7188	Intermediate Similarity	NPD4062	Phase 3
0.7188	Intermediate Similarity	NPD6233	Phase 2
0.7184	Intermediate Similarity	NPD4793	Discontinued
0.7176	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD1510	Phase 2
0.7176	Intermediate Similarity	NPD2799	Discontinued
0.7168	Intermediate Similarity	NPD1445	Approved
0.7168	Intermediate Similarity	NPD1444	Approved
0.7155	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1089	Approved
0.7143	Intermediate Similarity	NPD9258	Approved
0.7143	Intermediate Similarity	NPD1090	Approved
0.7143	Intermediate Similarity	NPD9256	Approved
0.7143	Intermediate Similarity	NPD1086	Approved
0.713	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD5405	Approved
0.7121	Intermediate Similarity	NPD5406	Approved
0.7121	Intermediate Similarity	NPD5404	Approved
0.7121	Intermediate Similarity	NPD7450	Phase 2
0.7121	Intermediate Similarity	NPD5408	Approved
0.712	Intermediate Similarity	NPD1203	Approved
0.7119	Intermediate Similarity	NPD5951	Approved
0.7119	Intermediate Similarity	NPD2629	Approved
0.7119	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD1202	Approved
0.71	Intermediate Similarity	NPD226	Approved
0.7097	Intermediate Similarity	NPD4659	Approved
0.7097	Intermediate Similarity	NPD6583	Phase 3
0.7097	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6582	Phase 2
0.709	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5536	Phase 2
0.7083	Intermediate Similarity	NPD9087	Approved
0.7073	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD3092	Approved
0.7068	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD1566	Phase 3
0.7064	Intermediate Similarity	NPD1564	Approved
0.7064	Intermediate Similarity	NPD1565	Approved
0.7059	Intermediate Similarity	NPD6671	Approved
0.7054	Intermediate Similarity	NPD9261	Approved
0.7049	Intermediate Similarity	NPD17	Approved
0.7048	Intermediate Similarity	NPD5347	Phase 2
0.7048	Intermediate Similarity	NPD5346	Phase 2
0.7045	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD3750	Approved
0.7037	Intermediate Similarity	NPD3400	Discontinued
0.7037	Intermediate Similarity	NPD8166	Discontinued
0.7034	Intermediate Similarity	NPD5283	Phase 1
0.7034	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD7095	Approved
0.7025	Intermediate Similarity	NPD1548	Phase 1
0.7016	Intermediate Similarity	NPD4878	Approved
0.7016	Intermediate Similarity	NPD2562	Approved
0.7016	Intermediate Similarity	NPD2561	Approved
0.7015	Intermediate Similarity	NPD1549	Phase 2
0.7009	Intermediate Similarity	NPD228	Approved
0.7009	Intermediate Similarity	NPD1088	Approved
0.7008	Intermediate Similarity	NPD9569	Approved
0.7	Intermediate Similarity	NPD826	Approved
0.7	Intermediate Similarity	NPD9273	Approved
0.7	Intermediate Similarity	NPD825	Approved
0.6992	Remote Similarity	NPD4477	Approved
0.6992	Remote Similarity	NPD4476	Approved
0.6992	Remote Similarity	NPD3421	Phase 3
0.6985	Remote Similarity	NPD2309	Approved
0.6984	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD3266	Approved
0.6984	Remote Similarity	NPD4103	Phase 2
0.6984	Remote Similarity	NPD3267	Approved
0.6984	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD2313	Discontinued
0.6975	Remote Similarity	NPD9281	Approved
0.6972	Remote Similarity	NPD1989	Approved
0.6972	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.697	Remote Similarity	NPD9088	Approved
0.6967	Remote Similarity	NPD4105	Approved
0.6967	Remote Similarity	NPD4102	Approved
0.6964	Remote Similarity	NPD1932	Approved
0.6957	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7843	Approved
0.6949	Remote Similarity	NPD9379	Approved
0.6949	Remote Similarity	NPD9377	Approved
0.6935	Remote Similarity	NPD1610	Phase 2
0.693	Remote Similarity	NPD5048	Discontinued
0.6929	Remote Similarity	NPD6584	Phase 3
0.6923	Remote Similarity	NPD8032	Phase 2
0.6912	Remote Similarity	NPD7003	Approved
0.6912	Remote Similarity	NPD4628	Phase 3
0.6911	Remote Similarity	NPD6516	Phase 2
0.6911	Remote Similarity	NPD2668	Approved
0.6911	Remote Similarity	NPD2667	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