NPASS Compound

Structure

CID272260 OpenBabel06191716082D 21 22 0 0 0 0 0 0 0 0999 V2000 -6.0622 3.5000 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 -5.1962 3.0000 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 0.8660 -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 -5.1962 2.0000 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 -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 -6.0622 0.5000 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 -5.1962 0.0000 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 -3.4641 0.0000 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 4 1 0 0 0 0 2 5 2 0 0 0 0 2 6 1 0 0 0 0 3 7 1 0 0 0 0 4 8 2 0 0 0 0 5 9 1 0 0 0 0 6 10 2 0 0 0 0 7 16 2 0 0 0 0 8 16 1 0 0 0 0 9 17 2 0 0 0 0 10 17 1 0 0 0 0 11 13 1 0 0 0 0 11 16 1 0 0 0 0 12 14 1 0 0 0 0 12 17 1 0 0 0 0 13 18 1 0 0 0 0 14 19 1 0 0 0 0 15 18 1 0 0 0 0 15 19 1 0 0 0 0 18 20 2 0 0 0 0 19 21 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	280.15
Volume:	316.556
LogP:	2.848
LogD:	2.908
LogS:	-3.387
# Rotatable Bonds:	8
TPSA:	34.14
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.69
Synthetic Accessibility Score:	1.788
Fsp3:	0.263
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.791
MDCK Permeability:	2.171103005821351e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.969
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.379
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.799
Plasma Protein Binding (PPB):	92.9454116821289%
Volume Distribution (VD):	0.695
Pgp-substrate:	2.088512420654297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.714
CYP1A2-substrate:	0.364
CYP2C19-inhibitor:	0.944
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.901
CYP2C9-substrate:	0.196
CYP2D6-inhibitor:	0.026
CYP2D6-substrate:	0.223
CYP3A4-inhibitor:	0.189
CYP3A4-substrate:	0.46

ADMET: Excretion

Clearance (CL):	8.295
Half-life (T1/2):	0.928

ADMET: Toxicity

hERG Blockers:	0.173
Human Hepatotoxicity (H-HT):	0.225
Drug-inuced Liver Injury (DILI):	0.743
AMES Toxicity:	0.394
Rat Oral Acute Toxicity:	0.029
Maximum Recommended Daily Dose:	0.212
Skin Sensitization:	0.931
Carcinogencity:	0.097
Eye Corrosion:	0.514
Eye Irritation:	0.978
Respiratory Toxicity:	0.71

Download Data

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

Natural Product: NPC272260

Natural Product ID:	NPC272260
*Common Name:**	1,7-Diphenylheptane-3,5-Dione
IUPAC Name:	1,7-diphenylheptane-3,5-dione
Synonyms:
Standard InCHIKey:	JYTREBYXLQXESW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H20O2/c20-18(13-11-16-7-3-1-4-8-16)15-19(21)14-12-17-9-5-2-6-10-17/h1-10H,11-15H2
SMILES:	c1ccc(cc1)CCC(=O)CC(=O)CCc1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL487319
PubChem CID:	10149390
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
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	root	n.a.	PMID[18484537]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[18484537]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[19615910]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29323912]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[731398]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	root	n.a.	PMID[731398]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23911	Alpinia officinarum	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
Others	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	Activity	=	0.6	%	PMID[475580]
NPT248	Individual Protein	Estrogen receptor beta	Homo sapiens	Activity	=	0.3	%	PMID[475580]

☑ 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 NPC272260 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	232
0.1-0.2	2074
0.2-0.3	6207
0.3-0.4	15563
0.4-0.5	14199
0.5-0.6	3675
0.6-0.7	540
0.7-0.8	157
0.8-0.85	28
0.85-0.9	16
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9726	High Similarity	NPC9796
0.9342	High Similarity	NPC477703
0.9211	High Similarity	NPC139901
0.9211	High Similarity	NPC151405
0.8987	High Similarity	NPC273758
0.8947	High Similarity	NPC179726
0.8846	High Similarity	NPC95868
0.8784	High Similarity	NPC74458
0.878	High Similarity	NPC69057
0.8765	High Similarity	NPC123476
0.8734	High Similarity	NPC273033
0.8734	High Similarity	NPC12936
0.8667	High Similarity	NPC285679
0.8608	High Similarity	NPC71664
0.859	High Similarity	NPC103488
0.8571	High Similarity	NPC231591
0.8375	Intermediate Similarity	NPC164086
0.8375	Intermediate Similarity	NPC17408
0.8375	Intermediate Similarity	NPC285716
0.8372	Intermediate Similarity	NPC141607
0.8372	Intermediate Similarity	NPC187725
0.825	Intermediate Similarity	NPC300205
0.8235	Intermediate Similarity	NPC477693
0.8235	Intermediate Similarity	NPC477704
0.8228	Intermediate Similarity	NPC245966
0.8182	Intermediate Similarity	NPC271437
0.8148	Intermediate Similarity	NPC190567
0.814	Intermediate Similarity	NPC298115
0.8125	Intermediate Similarity	NPC36342
0.8125	Intermediate Similarity	NPC285470
0.8125	Intermediate Similarity	NPC2785
0.809	Intermediate Similarity	NPC206764
0.8077	Intermediate Similarity	NPC208075
0.8072	Intermediate Similarity	NPC44830
0.8068	Intermediate Similarity	NPC59677
0.8049	Intermediate Similarity	NPC145053
0.8046	Intermediate Similarity	NPC19256
0.8023	Intermediate Similarity	NPC267262
0.8	Intermediate Similarity	NPC298023
0.7955	Intermediate Similarity	NPC284475
0.7945	Intermediate Similarity	NPC22786
0.7931	Intermediate Similarity	NPC9822
0.7931	Intermediate Similarity	NPC418308
0.7931	Intermediate Similarity	NPC113307
0.7927	Intermediate Similarity	NPC157055
0.7901	Intermediate Similarity	NPC137847
0.7901	Intermediate Similarity	NPC76455
0.7865	Intermediate Similarity	NPC155232
0.7865	Intermediate Similarity	NPC188844
0.7865	Intermediate Similarity	NPC153885
0.7865	Intermediate Similarity	NPC1682
0.7857	Intermediate Similarity	NPC215008
0.7841	Intermediate Similarity	NPC277277
0.7841	Intermediate Similarity	NPC110420
0.7841	Intermediate Similarity	NPC67585
0.7841	Intermediate Similarity	NPC303967
0.7831	Intermediate Similarity	NPC73978
0.7826	Intermediate Similarity	NPC49994
0.7816	Intermediate Similarity	NPC157778
0.7808	Intermediate Similarity	NPC246588
0.7792	Intermediate Similarity	NPC98880
0.7778	Intermediate Similarity	NPC34243
0.7778	Intermediate Similarity	NPC238219
0.7778	Intermediate Similarity	NPC289883
0.7778	Intermediate Similarity	NPC329318
0.7753	Intermediate Similarity	NPC133461
0.7742	Intermediate Similarity	NPC476042
0.7738	Intermediate Similarity	NPC230068
0.7717	Intermediate Similarity	NPC289201
0.7717	Intermediate Similarity	NPC239185
0.7717	Intermediate Similarity	NPC103048
0.7711	Intermediate Similarity	NPC127343
0.7701	Intermediate Similarity	NPC43945
0.7692	Intermediate Similarity	NPC95289
0.7692	Intermediate Similarity	NPC260233
0.7692	Intermediate Similarity	NPC472880
0.7674	Intermediate Similarity	NPC475710
0.7674	Intermediate Similarity	NPC95965
0.7667	Intermediate Similarity	NPC77273
0.7667	Intermediate Similarity	NPC323420
0.7662	Intermediate Similarity	NPC311343
0.764	Intermediate Similarity	NPC173413
0.764	Intermediate Similarity	NPC84288
0.7634	Intermediate Similarity	NPC134882
0.7609	Intermediate Similarity	NPC12695
0.7609	Intermediate Similarity	NPC185208
0.7609	Intermediate Similarity	NPC219573
0.76	Intermediate Similarity	NPC113670
0.7586	Intermediate Similarity	NPC307
0.7586	Intermediate Similarity	NPC160339
0.7568	Intermediate Similarity	NPC210849
0.7556	Intermediate Similarity	NPC125226
0.7553	Intermediate Similarity	NPC54647
0.7534	Intermediate Similarity	NPC36357
0.7534	Intermediate Similarity	NPC114327
0.7529	Intermediate Similarity	NPC73637
0.7529	Intermediate Similarity	NPC121478
0.7528	Intermediate Similarity	NPC325709
0.7527	Intermediate Similarity	NPC240042
0.7527	Intermediate Similarity	NPC265220
0.75	Intermediate Similarity	NPC194326
0.75	Intermediate Similarity	NPC472691
0.75	Intermediate Similarity	NPC471829
0.75	Intermediate Similarity	NPC184030
0.75	Intermediate Similarity	NPC164449
0.75	Intermediate Similarity	NPC474866
0.75	Intermediate Similarity	NPC475939
0.7474	Intermediate Similarity	NPC472879
0.7474	Intermediate Similarity	NPC476993
0.7474	Intermediate Similarity	NPC109514
0.7449	Intermediate Similarity	NPC188677
0.7447	Intermediate Similarity	NPC145052
0.7447	Intermediate Similarity	NPC75724
0.7442	Intermediate Similarity	NPC285773
0.7442	Intermediate Similarity	NPC288903
0.7442	Intermediate Similarity	NPC324624
0.7442	Intermediate Similarity	NPC197581
0.7423	Intermediate Similarity	NPC261573
0.7423	Intermediate Similarity	NPC8931
0.7423	Intermediate Similarity	NPC120693
0.7375	Intermediate Similarity	NPC155429
0.7374	Intermediate Similarity	NPC470007
0.7363	Intermediate Similarity	NPC476484
0.7363	Intermediate Similarity	NPC103346
0.7356	Intermediate Similarity	NPC95429
0.7347	Intermediate Similarity	NPC167336
0.734	Intermediate Similarity	NPC226041
0.734	Intermediate Similarity	NPC477767
0.732	Intermediate Similarity	NPC329556
0.7312	Intermediate Similarity	NPC172925
0.7308	Intermediate Similarity	NPC267443
0.7303	Intermediate Similarity	NPC322387
0.7292	Intermediate Similarity	NPC225079
0.7273	Intermediate Similarity	NPC252067
0.7273	Intermediate Similarity	NPC472700
0.7273	Intermediate Similarity	NPC291066
0.7273	Intermediate Similarity	NPC472699
0.7273	Intermediate Similarity	NPC294134
0.7273	Intermediate Similarity	NPC99482
0.7263	Intermediate Similarity	NPC271475
0.7263	Intermediate Similarity	NPC317280
0.7263	Intermediate Similarity	NPC329387
0.726	Intermediate Similarity	NPC198841
0.7253	Intermediate Similarity	NPC86670
0.7253	Intermediate Similarity	NPC70940
0.7253	Intermediate Similarity	NPC274455
0.7241	Intermediate Similarity	NPC243289
0.7241	Intermediate Similarity	NPC39600
0.7241	Intermediate Similarity	NPC208183
0.7237	Intermediate Similarity	NPC71009
0.7237	Intermediate Similarity	NPC200745
0.7229	Intermediate Similarity	NPC78500
0.7228	Intermediate Similarity	NPC88141
0.7222	Intermediate Similarity	NPC329064
0.7209	Intermediate Similarity	NPC100039
0.72	Intermediate Similarity	NPC472695
0.72	Intermediate Similarity	NPC472696
0.72	Intermediate Similarity	NPC472683
0.72	Intermediate Similarity	NPC472701
0.7188	Intermediate Similarity	NPC221825
0.7174	Intermediate Similarity	NPC86987
0.7172	Intermediate Similarity	NPC474307
0.7172	Intermediate Similarity	NPC471186
0.7162	Intermediate Similarity	NPC300345
0.7162	Intermediate Similarity	NPC120441
0.7162	Intermediate Similarity	NPC65873
0.7162	Intermediate Similarity	NPC212114
0.716	Intermediate Similarity	NPC326200
0.7159	Intermediate Similarity	NPC267704
0.7158	Intermediate Similarity	NPC270654
0.7143	Intermediate Similarity	NPC247976
0.7126	Intermediate Similarity	NPC475199
0.7126	Intermediate Similarity	NPC283012
0.7126	Intermediate Similarity	NPC323103
0.7125	Intermediate Similarity	NPC169222
0.7125	Intermediate Similarity	NPC246822
0.7125	Intermediate Similarity	NPC139416
0.7125	Intermediate Similarity	NPC235059
0.7125	Intermediate Similarity	NPC213570
0.7125	Intermediate Similarity	NPC473206
0.7125	Intermediate Similarity	NPC16190
0.7123	Intermediate Similarity	NPC149436
0.7113	Intermediate Similarity	NPC136810
0.7113	Intermediate Similarity	NPC158623
0.7113	Intermediate Similarity	NPC133809
0.7113	Intermediate Similarity	NPC128248
0.7105	Intermediate Similarity	NPC135924
0.7105	Intermediate Similarity	NPC248705
0.7105	Intermediate Similarity	NPC54368
0.7105	Intermediate Similarity	NPC150196
0.71	Intermediate Similarity	NPC95178
0.71	Intermediate Similarity	NPC69332
0.71	Intermediate Similarity	NPC29989
0.71	Intermediate Similarity	NPC70843
0.71	Intermediate Similarity	NPC475905
0.71	Intermediate Similarity	NPC193640
0.71	Intermediate Similarity	NPC25385
0.7079	Intermediate Similarity	NPC53299
0.7073	Intermediate Similarity	NPC54269
0.7071	Intermediate Similarity	NPC329282

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 NPC272260 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	220
0.1-0.2	1116
0.2-0.3	1408
0.3-0.4	3477
0.4-0.5	1954
0.5-0.6	777
0.6-0.7	151
0.7-0.8	41
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8846	High Similarity	NPD1507	Clinical (unspecified phase)
0.8734	High Similarity	NPD942	Approved
0.8068	Intermediate Similarity	NPD1508	Approved
0.7955	Intermediate Similarity	NPD7609	Phase 3
0.7901	Intermediate Similarity	NPD227	Approved
0.7901	Intermediate Similarity	NPD225	Approved
0.7889	Intermediate Similarity	NPD4094	Approved
0.7865	Intermediate Similarity	NPD7631	Approved
0.7802	Intermediate Similarity	NPD1843	Approved
0.7778	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD4657	Approved
0.7717	Intermediate Similarity	NPD4655	Approved
0.7717	Intermediate Similarity	NPD3495	Discontinued
0.7701	Intermediate Similarity	NPD4793	Discontinued
0.7701	Intermediate Similarity	NPD650	Approved
0.7619	Intermediate Similarity	NPD226	Approved
0.7609	Intermediate Similarity	NPD1989	Approved
0.76	Intermediate Similarity	NPD675	Discontinued
0.759	Intermediate Similarity	NPD9490	Approved
0.7556	Intermediate Similarity	NPD1239	Approved
0.7553	Intermediate Similarity	NPD2066	Phase 3
0.7528	Intermediate Similarity	NPD5346	Phase 2
0.7528	Intermediate Similarity	NPD5347	Phase 2
0.75	Intermediate Similarity	NPD1087	Approved
0.7444	Intermediate Similarity	NPD3672	Approved
0.7444	Intermediate Similarity	NPD3673	Approved
0.7442	Intermediate Similarity	NPD9491	Approved
0.7419	Intermediate Similarity	NPD5206	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD6027	Approved
0.7396	Intermediate Similarity	NPD1932	Approved
0.7396	Intermediate Similarity	NPD6024	Approved
0.7391	Intermediate Similarity	NPD1563	Approved
0.7368	Intermediate Similarity	NPD7798	Approved
0.7333	Intermediate Similarity	NPD800	Approved
0.732	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD1930	Approved
0.732	Intermediate Similarity	NPD1929	Approved
0.7312	Intermediate Similarity	NPD1693	Approved
0.7312	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD506	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD1090	Approved
0.7253	Intermediate Similarity	NPD1086	Approved
0.7253	Intermediate Similarity	NPD1089	Approved
0.7245	Intermediate Similarity	NPD5909	Discontinued
0.7241	Intermediate Similarity	NPD3971	Phase 1
0.7158	Intermediate Similarity	NPD1564	Approved
0.7158	Intermediate Similarity	NPD1565	Approved
0.7158	Intermediate Similarity	NPD1566	Phase 3
0.7113	Intermediate Similarity	NPD3135	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1088	Approved
0.7071	Intermediate Similarity	NPD1237	Approved
0.7041	Intermediate Similarity	NPD2193	Phase 2
0.7041	Intermediate Similarity	NPD2648	Phase 3
0.7021	Intermediate Similarity	NPD1202	Approved
0.7	Intermediate Similarity	NPD5048	Discontinued
0.6961	Remote Similarity	NPD2329	Discontinued
0.6905	Remote Similarity	NPD9716	Approved
0.69	Remote Similarity	NPD2577	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD2196	Discontinued
0.6869	Remote Similarity	NPD2171	Approved
0.6837	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD1099	Approved
0.6804	Remote Similarity	NPD1100	Approved
0.68	Remote Similarity	NPD3357	Discontinued
0.6744	Remote Similarity	NPD4144	Approved
0.6744	Remote Similarity	NPD4147	Approved
0.6735	Remote Similarity	NPD5926	Approved
0.6707	Remote Similarity	NPD9497	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD3904	Approved
0.6705	Remote Similarity	NPD3903	Approved
0.6705	Remote Similarity	NPD3979	Approved
0.6705	Remote Similarity	NPD3981	Approved
0.67	Remote Similarity	NPD4803	Discontinued
0.6698	Remote Similarity	NPD6858	Approved
0.6698	Remote Similarity	NPD7094	Approved
0.6667	Remote Similarity	NPD1238	Approved
0.6667	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2197	Approved
0.6667	Remote Similarity	NPD2192	Approved
0.6632	Remote Similarity	NPD1007	Discontinued
0.663	Remote Similarity	NPD9259	Approved
0.663	Remote Similarity	NPD9257	Approved
0.6629	Remote Similarity	NPD4027	Approved
0.6629	Remote Similarity	NPD4026	Approved
0.6629	Remote Similarity	NPD3035	Approved
0.6625	Remote Similarity	NPD173	Clinical (unspecified phase)
0.66	Remote Similarity	NPD5630	Phase 1
0.6598	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD6049	Phase 2
0.6574	Remote Similarity	NPD3867	Phase 2
0.6571	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD9495	Approved
0.6566	Remote Similarity	NPD466	Approved
0.6566	Remote Similarity	NPD253	Approved
0.6556	Remote Similarity	NPD4701	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD4169	Approved
0.6556	Remote Similarity	NPD4170	Approved
0.6535	Remote Similarity	NPD6588	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD2859	Approved
0.6531	Remote Similarity	NPD2860	Approved
0.6514	Remote Similarity	NPD3317	Approved
0.6509	Remote Similarity	NPD3643	Approved
0.6509	Remote Similarity	NPD3642	Approved
0.6509	Remote Similarity	NPD3644	Approved
0.6506	Remote Similarity	NPD1673	Approved
0.6505	Remote Similarity	NPD1677	Discontinued
0.65	Remote Similarity	NPD742	Approved
0.6484	Remote Similarity	NPD4635	Approved
0.6484	Remote Similarity	NPD2001	Discontinued
0.6476	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6647	Phase 2
0.6471	Remote Similarity	NPD5765	Approved
0.6465	Remote Similarity	NPD9566	Approved
0.6455	Remote Similarity	NPD4576	Approved
0.6455	Remote Similarity	NPD4574	Approved
0.6449	Remote Similarity	NPD2124	Approved
0.6429	Remote Similarity	NPD2933	Approved
0.6429	Remote Similarity	NPD2934	Approved
0.6422	Remote Similarity	NPD1711	Phase 2
0.6422	Remote Similarity	NPD2629	Approved
0.6422	Remote Similarity	NPD5951	Approved
0.6421	Remote Similarity	NPD1628	Approved
0.6421	Remote Similarity	NPD1629	Approved
0.6415	Remote Similarity	NPD1317	Discontinued
0.6415	Remote Similarity	NPD2067	Discontinued
0.6415	Remote Similarity	NPD5278	Discontinued
0.6413	Remote Similarity	NPD5178	Approved
0.6413	Remote Similarity	NPD3429	Approved
0.6413	Remote Similarity	NPD4544	Approved
0.6413	Remote Similarity	NPD3427	Approved
0.6404	Remote Similarity	NPD1475	Approved
0.6396	Remote Similarity	NPD6065	Approved
0.6396	Remote Similarity	NPD7610	Discontinued
0.6383	Remote Similarity	NPD1282	Approved
0.6372	Remote Similarity	NPD5836	Discontinued
0.6355	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD5927	Discontinued
0.6354	Remote Similarity	NPD2811	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD9258	Approved
0.6354	Remote Similarity	NPD9256	Approved
0.6353	Remote Similarity	NPD294	Approved
0.6353	Remote Similarity	NPD292	Approved
0.6348	Remote Similarity	NPD3972	Approved
0.6346	Remote Similarity	NPD1018	Approved
0.6344	Remote Similarity	NPD5916	Discontinued
0.6339	Remote Similarity	NPD7009	Phase 2
0.6337	Remote Similarity	NPD3020	Approved
0.6333	Remote Similarity	NPD1617	Discontinued
0.633	Remote Similarity	NPD7077	Approved
0.633	Remote Similarity	NPD3598	Phase 3
0.633	Remote Similarity	NPD7076	Approved
0.6327	Remote Similarity	NPD1066	Discontinued
0.6316	Remote Similarity	NPD4879	Approved
0.6311	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD5162	Approved
0.6304	Remote Similarity	NPD5288	Clinical (unspecified phase)
0.63	Remote Similarity	NPD1875	Phase 1
0.6296	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD5705	Approved
0.6286	Remote Similarity	NPD6685	Approved
0.6286	Remote Similarity	NPD5704	Approved
0.6286	Remote Similarity	NPD5706	Approved
0.6286	Remote Similarity	NPD467	Phase 1
0.6283	Remote Similarity	NPD4102	Approved
0.6283	Remote Similarity	NPD4105	Approved
0.6283	Remote Similarity	NPD1651	Approved
0.6283	Remote Similarity	NPD3024	Approved
0.6283	Remote Similarity	NPD3025	Approved
0.6277	Remote Similarity	NPD4636	Approved
0.6277	Remote Similarity	NPD4406	Approved
0.6277	Remote Similarity	NPD4409	Approved
0.6273	Remote Similarity	NPD1020	Approved
0.6273	Remote Similarity	NPD1022	Approved
0.6273	Remote Similarity	NPD1021	Approved
0.6273	Remote Similarity	NPD2508	Discontinued
0.6273	Remote Similarity	NPD1023	Approved
0.6262	Remote Similarity	NPD5237	Approved
0.6262	Remote Similarity	NPD3581	Discontinued
0.6262	Remote Similarity	NPD4234	Approved
0.6262	Remote Similarity	NPD5240	Approved
0.6262	Remote Similarity	NPD5239	Approved
0.6262	Remote Similarity	NPD1756	Approved
0.6262	Remote Similarity	NPD664	Approved
0.6262	Remote Similarity	NPD4233	Approved
0.6262	Remote Similarity	NPD5236	Approved
0.6262	Remote Similarity	NPD5235	Approved
0.6262	Remote Similarity	NPD1752	Approved
0.6261	Remote Similarity	NPD6287	Discontinued
0.625	Remote Similarity	NPD5991	Approved
0.625	Remote Similarity	NPD5990	Approved
0.6239	Remote Similarity	NPD2607	Approved
0.6237	Remote Similarity	NPD2539	Approved
0.6237	Remote Similarity	NPD2538	Approved
0.6228	Remote Similarity	NPD3019	Approved
0.6228	Remote Similarity	NPD2932	Approved
0.6228	Remote Similarity	NPD2345	Approved
0.6214	Remote Similarity	NPD813	Approved
0.6211	Remote Similarity	NPD3426	Approved
0.6211	Remote Similarity	NPD2002	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