NPASS Compound

Structure

CID231591 OpenBabel06191716032D 22 23 0 0 1 0 0 0 0 0999 V2000 0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -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 -4.3301 -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 0.8660 -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 -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 0.8660 -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 -3.4641 1.0000 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 -2.5981 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 -1.7321 3.0000 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 0.0000 -0.0000 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 -0.8660 2.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 4 2 0 0 0 0 2 5 1 0 0 0 0 3 6 2 0 0 0 0 3 7 1 0 0 0 0 4 8 1 0 0 0 0 5 9 2 0 0 0 0 6 10 1 0 0 0 0 7 11 2 0 0 0 0 8 17 2 0 0 0 0 9 17 1 0 0 0 0 10 18 2 0 0 0 0 11 18 1 0 0 0 0 12 14 1 0 0 0 0 12 17 1 0 0 0 0 13 15 1 0 0 0 0 13 18 1 0 0 0 0 14 19 1 0 0 0 0 15 20 1 0 0 0 0 16 19 1 0 0 0 0 16 20 1 0 0 0 0 19 21 2 0 0 0 0 20 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	296.18
Volume:	336.488
LogP:	3.322
LogD:	3.347
LogS:	-3.354
# Rotatable Bonds:	9
TPSA:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.692
Synthetic Accessibility Score:	2.353
Fsp3:	0.35
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.615
MDCK Permeability:	1.875248744909186e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.406
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.956
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.807
Plasma Protein Binding (PPB):	96.18498992919922%
Volume Distribution (VD):	0.751
Pgp-substrate:	1.3143751621246338%

ADMET: Metabolism

CYP1A2-inhibitor:	0.343
CYP1A2-substrate:	0.594
CYP2C19-inhibitor:	0.7
CYP2C19-substrate:	0.117
CYP2C9-inhibitor:	0.574
CYP2C9-substrate:	0.091
CYP2D6-inhibitor:	0.03
CYP2D6-substrate:	0.191
CYP3A4-inhibitor:	0.097
CYP3A4-substrate:	0.622

ADMET: Excretion

Clearance (CL):	10.759
Half-life (T1/2):	0.753

ADMET: Toxicity

hERG Blockers:	0.5
Human Hepatotoxicity (H-HT):	0.536
Drug-inuced Liver Injury (DILI):	0.039
AMES Toxicity:	0.095
Rat Oral Acute Toxicity:	0.035
Maximum Recommended Daily Dose:	0.588
Skin Sensitization:	0.705
Carcinogencity:	0.267
Eye Corrosion:	0.011
Eye Irritation:	0.765
Respiratory Toxicity:	0.052

Download Data

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

Natural Product: NPC231591

Natural Product ID:	NPC231591
*Common Name:**	5-Methoxy-1,7-Diphenylheptan-3-One
IUPAC Name:	5-methoxy-1,7-diphenylheptan-3-one
Synonyms:
Standard InCHIKey:	PVYORFBABSDDNC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H24O2/c1-22-20(15-13-18-10-6-3-7-11-18)16-19(21)14-12-17-8-4-2-5-9-17/h2-11,20H,12-16H2,1H3
SMILES:	COC(CC(=O)CCc1ccccc1)CCc1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL240485
PubChem CID:	5319430
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]
NPO17294	Desmodium pulchellum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7804	Desmodium gangeticum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7804	Desmodium gangeticum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17294	Desmodium pulchellum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7804	Desmodium gangeticum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17294	Desmodium pulchellum	Species	Fabaceae	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]
NPO17294	Desmodium pulchellum	Species	Fabaceae	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	2

Activity Type	# Activity
Individual Protein	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	Activity	=	14.5	%	PMID[547051]
NPT248	Individual Protein	Estrogen receptor beta	Homo sapiens	Activity	=	19.5	%	PMID[547051]
NPT2	Others	Unspecified		IC50	=	1600.0	nM	PMID[547050]

☑ 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 NPC231591 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	188
0.1-0.2	1000
0.2-0.3	2558
0.3-0.4	10815
0.4-0.5	16056
0.5-0.6	10266
0.6-0.7	1542
0.7-0.8	245
0.8-0.85	22
0.85-0.9	2
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.931	High Similarity	NPC141607
0.931	High Similarity	NPC187725
0.9	High Similarity	NPC206764
0.8621	High Similarity	NPC475710
0.8617	High Similarity	NPC476042
0.8571	High Similarity	NPC272260
0.8554	High Similarity	NPC9796
0.8444	Intermediate Similarity	NPC9822
0.8333	Intermediate Similarity	NPC158623
0.8283	Intermediate Similarity	NPC475905
0.8283	Intermediate Similarity	NPC25385
0.8283	Intermediate Similarity	NPC193640
0.8211	Intermediate Similarity	NPC289201
0.8211	Intermediate Similarity	NPC103048
0.814	Intermediate Similarity	NPC151405
0.814	Intermediate Similarity	NPC139901
0.8105	Intermediate Similarity	NPC12695
0.8068	Intermediate Similarity	NPC73637
0.8068	Intermediate Similarity	NPC121478
0.8046	Intermediate Similarity	NPC184030
0.8046	Intermediate Similarity	NPC477703
0.8046	Intermediate Similarity	NPC164449
0.8022	Intermediate Similarity	NPC69057
0.802	Intermediate Similarity	NPC470007
0.8	Intermediate Similarity	NPC294134
0.8	Intermediate Similarity	NPC474307
0.7978	Intermediate Similarity	NPC44830
0.7978	Intermediate Similarity	NPC288903
0.7957	Intermediate Similarity	NPC84288
0.7952	Intermediate Similarity	NPC74458
0.7938	Intermediate Similarity	NPC271475
0.7938	Intermediate Similarity	NPC145052
0.7935	Intermediate Similarity	NPC477704
0.7935	Intermediate Similarity	NPC477693
0.7921	Intermediate Similarity	NPC474111
0.7921	Intermediate Similarity	NPC329705
0.79	Intermediate Similarity	NPC19136
0.7872	Intermediate Similarity	NPC476484
0.7865	Intermediate Similarity	NPC323103
0.7857	Intermediate Similarity	NPC285679
0.7857	Intermediate Similarity	NPC54647
0.7841	Intermediate Similarity	NPC95868
0.7835	Intermediate Similarity	NPC477767
0.7835	Intermediate Similarity	NPC226041
0.7816	Intermediate Similarity	NPC103488
0.7802	Intermediate Similarity	NPC123476
0.7802	Intermediate Similarity	NPC99482
0.7788	Intermediate Similarity	NPC321252
0.7788	Intermediate Similarity	NPC252544
0.7778	Intermediate Similarity	NPC270507
0.7778	Intermediate Similarity	NPC273758
0.7757	Intermediate Similarity	NPC23402
0.7755	Intermediate Similarity	NPC329387
0.7755	Intermediate Similarity	NPC317280
0.7753	Intermediate Similarity	NPC273033
0.7753	Intermediate Similarity	NPC12936
0.7714	Intermediate Similarity	NPC177576
0.7708	Intermediate Similarity	NPC34243
0.7701	Intermediate Similarity	NPC298023
0.7701	Intermediate Similarity	NPC179726
0.77	Intermediate Similarity	NPC474112
0.7677	Intermediate Similarity	NPC221825
0.7667	Intermediate Similarity	NPC283012
0.7667	Intermediate Similarity	NPC103387
0.7667	Intermediate Similarity	NPC475199
0.7653	Intermediate Similarity	NPC270654
0.7647	Intermediate Similarity	NPC271437
0.7647	Intermediate Similarity	NPC471186
0.764	Intermediate Similarity	NPC127343
0.764	Intermediate Similarity	NPC121800
0.764	Intermediate Similarity	NPC71664
0.764	Intermediate Similarity	NPC17408
0.764	Intermediate Similarity	NPC157055
0.764	Intermediate Similarity	NPC285716
0.7614	Intermediate Similarity	NPC76455
0.7614	Intermediate Similarity	NPC137847
0.7609	Intermediate Similarity	NPC95965
0.7604	Intermediate Similarity	NPC77273
0.7596	Intermediate Similarity	NPC317305
0.7596	Intermediate Similarity	NPC40178
0.7596	Intermediate Similarity	NPC475282
0.7579	Intermediate Similarity	NPC110420
0.7579	Intermediate Similarity	NPC303967
0.7579	Intermediate Similarity	NPC67585
0.7558	Intermediate Similarity	NPC208075
0.7549	Intermediate Similarity	NPC249067
0.7528	Intermediate Similarity	NPC170484
0.7528	Intermediate Similarity	NPC300205
0.75	Intermediate Similarity	NPC7435
0.75	Intermediate Similarity	NPC95429
0.75	Intermediate Similarity	NPC317645
0.75	Intermediate Similarity	NPC20485
0.75	Intermediate Similarity	NPC285350
0.75	Intermediate Similarity	NPC329318
0.75	Intermediate Similarity	NPC47536
0.7476	Intermediate Similarity	NPC321670
0.7475	Intermediate Similarity	NPC278228
0.7474	Intermediate Similarity	NPC298115
0.7473	Intermediate Similarity	NPC230068
0.7455	Intermediate Similarity	NPC61651
0.7451	Intermediate Similarity	NPC329556
0.7447	Intermediate Similarity	NPC322387
0.7444	Intermediate Similarity	NPC190567
0.7444	Intermediate Similarity	NPC164086
0.7431	Intermediate Similarity	NPC471616
0.7426	Intermediate Similarity	NPC94487
0.7426	Intermediate Similarity	NPC225079
0.7423	Intermediate Similarity	NPC59677
0.7416	Intermediate Similarity	NPC2785
0.7416	Intermediate Similarity	NPC285470
0.7416	Intermediate Similarity	NPC36342
0.74	Intermediate Similarity	NPC476120
0.7396	Intermediate Similarity	NPC274455
0.7396	Intermediate Similarity	NPC240108
0.7396	Intermediate Similarity	NPC213156
0.7396	Intermediate Similarity	NPC70940
0.7396	Intermediate Similarity	NPC86670
0.7391	Intermediate Similarity	NPC285773
0.7387	Intermediate Similarity	NPC64340
0.7383	Intermediate Similarity	NPC471189
0.7383	Intermediate Similarity	NPC471188
0.7379	Intermediate Similarity	NPC120693
0.7379	Intermediate Similarity	NPC261573
0.7379	Intermediate Similarity	NPC8931
0.7368	Intermediate Similarity	NPC329064
0.7363	Intermediate Similarity	NPC145053
0.7363	Intermediate Similarity	NPC73978
0.7353	Intermediate Similarity	NPC475978
0.7353	Intermediate Similarity	NPC474820
0.7347	Intermediate Similarity	NPC23453
0.7345	Intermediate Similarity	NPC98305
0.7339	Intermediate Similarity	NPC215419
0.7333	Intermediate Similarity	NPC203732
0.732	Intermediate Similarity	NPC86987
0.732	Intermediate Similarity	NPC125226
0.732	Intermediate Similarity	NPC284475
0.7315	Intermediate Similarity	NPC469547
0.7315	Intermediate Similarity	NPC128368
0.7303	Intermediate Similarity	NPC245966
0.7297	Intermediate Similarity	NPC471553
0.729	Intermediate Similarity	NPC265513
0.7282	Intermediate Similarity	NPC247976
0.7282	Intermediate Similarity	NPC301943
0.7282	Intermediate Similarity	NPC474365
0.7273	Intermediate Similarity	NPC172925
0.7273	Intermediate Similarity	NPC62138
0.7264	Intermediate Similarity	NPC469636
0.7255	Intermediate Similarity	NPC112552
0.7255	Intermediate Similarity	NPC128248
0.7255	Intermediate Similarity	NPC42211
0.7255	Intermediate Similarity	NPC133809
0.7255	Intermediate Similarity	NPC136810
0.7245	Intermediate Similarity	NPC188844
0.7245	Intermediate Similarity	NPC155232
0.7245	Intermediate Similarity	NPC153885
0.7245	Intermediate Similarity	NPC1682
0.7238	Intermediate Similarity	NPC142326
0.7238	Intermediate Similarity	NPC188677
0.7238	Intermediate Similarity	NPC94751
0.7232	Intermediate Similarity	NPC249435
0.7228	Intermediate Similarity	NPC179411
0.7228	Intermediate Similarity	NPC49994
0.7222	Intermediate Similarity	NPC218855
0.7222	Intermediate Similarity	NPC280789
0.7216	Intermediate Similarity	NPC19256
0.7216	Intermediate Similarity	NPC277277
0.7212	Intermediate Similarity	NPC329282
0.7204	Intermediate Similarity	NPC477770
0.7204	Intermediate Similarity	NPC197581
0.7188	Intermediate Similarity	NPC157778
0.7188	Intermediate Similarity	NPC267262
0.7188	Intermediate Similarity	NPC304760
0.7172	Intermediate Similarity	NPC238219
0.7172	Intermediate Similarity	NPC289883
0.7168	Intermediate Similarity	NPC182240
0.7157	Intermediate Similarity	NPC474308
0.7157	Intermediate Similarity	NPC118343
0.7156	Intermediate Similarity	NPC471481
0.7156	Intermediate Similarity	NPC470253
0.7156	Intermediate Similarity	NPC477476
0.7156	Intermediate Similarity	NPC477475
0.7143	Intermediate Similarity	NPC269457
0.7143	Intermediate Similarity	NPC133461
0.7129	Intermediate Similarity	NPC239185
0.7128	Intermediate Similarity	NPC304538
0.7126	Intermediate Similarity	NPC208302
0.7117	Intermediate Similarity	NPC9274
0.7117	Intermediate Similarity	NPC188010
0.7117	Intermediate Similarity	NPC260886
0.7115	Intermediate Similarity	NPC160382
0.7113	Intermediate Similarity	NPC418308
0.7113	Intermediate Similarity	NPC113307
0.7113	Intermediate Similarity	NPC325709
0.7113	Intermediate Similarity	NPC220893
0.7105	Intermediate Similarity	NPC474223
0.7105	Intermediate Similarity	NPC475804
0.7105	Intermediate Similarity	NPC265454
0.7105	Intermediate Similarity	NPC475827
0.7105	Intermediate Similarity	NPC474222
0.7105	Intermediate Similarity	NPC34634

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 NPC231591 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	166
0.1-0.2	886
0.2-0.3	1102
0.3-0.4	3094
0.4-0.5	2473
0.5-0.6	1115
0.6-0.7	261
0.7-0.8	49
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8298	Intermediate Similarity	NPD1989	Approved
0.8152	Intermediate Similarity	NPD3672	Approved
0.8152	Intermediate Similarity	NPD3673	Approved
0.8041	Intermediate Similarity	NPD7798	Approved
0.8	Intermediate Similarity	NPD5048	Discontinued
0.7895	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD1507	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD227	Approved
0.7816	Intermediate Similarity	NPD225	Approved
0.7753	Intermediate Similarity	NPD942	Approved
0.7677	Intermediate Similarity	NPD2066	Phase 3
0.766	Intermediate Similarity	NPD5346	Phase 2
0.766	Intermediate Similarity	NPD5347	Phase 2
0.7634	Intermediate Similarity	NPD1087	Approved
0.7634	Intermediate Similarity	NPD4793	Discontinued
0.76	Intermediate Similarity	NPD3135	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD226	Approved
0.7549	Intermediate Similarity	NPD5909	Discontinued
0.7549	Intermediate Similarity	NPD1237	Approved
0.7528	Intermediate Similarity	NPD9490	Approved
0.7526	Intermediate Similarity	NPD1563	Approved
0.75	Intermediate Similarity	NPD1239	Approved
0.7477	Intermediate Similarity	NPD7094	Approved
0.7477	Intermediate Similarity	NPD6858	Approved
0.7474	Intermediate Similarity	NPD800	Approved
0.7451	Intermediate Similarity	NPD1930	Approved
0.7451	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD1929	Approved
0.7449	Intermediate Similarity	NPD1693	Approved
0.7431	Intermediate Similarity	NPD3317	Approved
0.7396	Intermediate Similarity	NPD1089	Approved
0.7396	Intermediate Similarity	NPD1090	Approved
0.7396	Intermediate Similarity	NPD1086	Approved
0.7391	Intermediate Similarity	NPD9491	Approved
0.7374	Intermediate Similarity	NPD5206	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD1932	Approved
0.7339	Intermediate Similarity	NPD1711	Phase 2
0.732	Intermediate Similarity	NPD7609	Phase 3
0.73	Intermediate Similarity	NPD1564	Approved
0.73	Intermediate Similarity	NPD1565	Approved
0.73	Intermediate Similarity	NPD1566	Phase 3
0.729	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD6647	Phase 2
0.7273	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4094	Approved
0.7245	Intermediate Similarity	NPD7631	Approved
0.7245	Intermediate Similarity	NPD1088	Approved
0.7228	Intermediate Similarity	NPD5926	Approved
0.7207	Intermediate Similarity	NPD4576	Approved
0.7207	Intermediate Similarity	NPD4574	Approved
0.7196	Intermediate Similarity	NPD2067	Discontinued
0.7182	Intermediate Similarity	NPD2629	Approved
0.7157	Intermediate Similarity	NPD1238	Approved
0.7143	Intermediate Similarity	NPD6065	Approved
0.713	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD3495	Discontinued
0.7129	Intermediate Similarity	NPD4657	Approved
0.7129	Intermediate Similarity	NPD4655	Approved
0.7103	Intermediate Similarity	NPD2329	Discontinued
0.7091	Intermediate Similarity	NPD6010	Discontinued
0.7091	Intermediate Similarity	NPD2652	Approved
0.7091	Intermediate Similarity	NPD2650	Approved
0.7083	Intermediate Similarity	NPD650	Approved
0.7075	Intermediate Similarity	NPD5704	Approved
0.7075	Intermediate Similarity	NPD6685	Approved
0.7075	Intermediate Similarity	NPD467	Phase 1
0.7075	Intermediate Similarity	NPD5706	Approved
0.7075	Intermediate Similarity	NPD5705	Approved
0.7071	Intermediate Similarity	NPD1508	Approved
0.7059	Intermediate Similarity	NPD9495	Approved
0.7037	Intermediate Similarity	NPD3646	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1202	Approved
0.6952	Remote Similarity	NPD5765	Approved
0.6923	Remote Similarity	NPD2549	Approved
0.6923	Remote Similarity	NPD2555	Approved
0.6923	Remote Similarity	NPD2550	Approved
0.6923	Remote Similarity	NPD2552	Approved
0.6923	Remote Similarity	NPD2553	Approved
0.6923	Remote Similarity	NPD2558	Approved
0.6881	Remote Similarity	NPD1752	Approved
0.6881	Remote Similarity	NPD4234	Approved
0.6881	Remote Similarity	NPD4233	Approved
0.6881	Remote Similarity	NPD1756	Approved
0.6863	Remote Similarity	NPD1843	Approved
0.6857	Remote Similarity	NPD4188	Approved
0.6857	Remote Similarity	NPD6027	Approved
0.6857	Remote Similarity	NPD4189	Approved
0.6857	Remote Similarity	NPD6024	Approved
0.6847	Remote Similarity	NPD2607	Approved
0.6838	Remote Similarity	NPD4217	Approved
0.6838	Remote Similarity	NPD3131	Approved
0.6838	Remote Similarity	NPD4216	Approved
0.6838	Remote Similarity	NPD4218	Approved
0.6838	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD2609	Approved
0.6838	Remote Similarity	NPD2608	Approved
0.6838	Remote Similarity	NPD2612	Approved
0.6838	Remote Similarity	NPD2610	Approved
0.6838	Remote Similarity	NPD3132	Approved
0.6838	Remote Similarity	NPD2611	Approved
0.6838	Remote Similarity	NPD4215	Approved
0.6832	Remote Similarity	NPD1066	Discontinued
0.6827	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD2182	Approved
0.6752	Remote Similarity	NPD4135	Approved
0.6752	Remote Similarity	NPD4106	Approved
0.6752	Remote Similarity	NPD4136	Approved
0.6752	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD1282	Approved
0.6729	Remote Similarity	NPD3048	Approved
0.6729	Remote Similarity	NPD3047	Approved
0.6729	Remote Similarity	NPD3046	Approved
0.6724	Remote Similarity	NPD5981	Approved
0.6724	Remote Similarity	NPD1651	Approved
0.6723	Remote Similarity	NPD5157	Phase 1
0.6723	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD5159	Phase 2
0.6706	Remote Similarity	NPD675	Discontinued
0.6699	Remote Similarity	NPD2860	Approved
0.6699	Remote Similarity	NPD2859	Approved
0.6698	Remote Similarity	NPD4719	Phase 2
0.6695	Remote Similarity	NPD6287	Discontinued
0.6667	Remote Similarity	NPD3643	Approved
0.6667	Remote Similarity	NPD5305	Approved
0.6667	Remote Similarity	NPD3971	Phase 1
0.6667	Remote Similarity	NPD3644	Approved
0.6667	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5306	Approved
0.6667	Remote Similarity	NPD3642	Approved
0.6667	Remote Similarity	NPD5667	Approved
0.6639	Remote Similarity	NPD3972	Approved
0.6637	Remote Similarity	NPD1241	Discontinued
0.6636	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD9259	Approved
0.6633	Remote Similarity	NPD9257	Approved
0.6607	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD6912	Phase 3
0.6606	Remote Similarity	NPD3526	Approved
0.6606	Remote Similarity	NPD2551	Approved
0.6606	Remote Similarity	NPD2559	Approved
0.6606	Remote Similarity	NPD3524	Approved
0.6602	Remote Similarity	NPD2934	Approved
0.6602	Remote Similarity	NPD2933	Approved
0.6581	Remote Similarity	NPD4102	Approved
0.6581	Remote Similarity	NPD4105	Approved
0.6579	Remote Similarity	NPD5951	Approved
0.6579	Remote Similarity	NPD4766	Approved
0.6577	Remote Similarity	NPD5278	Discontinued
0.6577	Remote Similarity	NPD1317	Discontinued
0.6577	Remote Similarity	NPD5240	Approved
0.6577	Remote Similarity	NPD5237	Approved
0.6577	Remote Similarity	NPD5239	Approved
0.6577	Remote Similarity	NPD5236	Approved
0.6577	Remote Similarity	NPD5235	Approved
0.6574	Remote Similarity	NPD164	Approved
0.6571	Remote Similarity	NPD253	Approved
0.6557	Remote Similarity	NPD2798	Approved
0.6557	Remote Similarity	NPD6085	Phase 2
0.6557	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD4806	Approved
0.6555	Remote Similarity	NPD4807	Approved
0.6555	Remote Similarity	NPD7436	Approved
0.6555	Remote Similarity	NPD7437	Approved
0.6552	Remote Similarity	NPD2347	Approved
0.6552	Remote Similarity	NPD7610	Discontinued
0.6542	Remote Similarity	NPD2648	Phase 3
0.6542	Remote Similarity	NPD2193	Phase 2
0.6532	Remote Similarity	NPD6039	Approved
0.6514	Remote Similarity	NPD1018	Approved
0.6509	Remote Similarity	NPD3020	Approved
0.6505	Remote Similarity	NPD3719	Approved
0.6505	Remote Similarity	NPD3718	Approved
0.6504	Remote Similarity	NPD5204	Approved
0.65	Remote Similarity	NPD531	Approved
0.6496	Remote Similarity	NPD7009	Phase 2
0.6496	Remote Similarity	NPD4479	Discontinued
0.6496	Remote Similarity	NPD1894	Discontinued
0.6491	Remote Similarity	NPD1374	Approved
0.6491	Remote Similarity	NPD1371	Approved
0.6491	Remote Similarity	NPD1370	Approved
0.6491	Remote Similarity	NPD1373	Approved
0.6476	Remote Similarity	NPD9566	Approved
0.6452	Remote Similarity	NPD2613	Approved
0.6452	Remote Similarity	NPD4620	Approved
0.6452	Remote Similarity	NPD5201	Approved
0.6452	Remote Similarity	NPD6832	Phase 2
0.6452	Remote Similarity	NPD5203	Approved
0.6452	Remote Similarity	NPD4617	Approved
0.6442	Remote Similarity	NPD7344	Phase 1
0.6442	Remote Similarity	NPD4814	Discontinued
0.6442	Remote Similarity	NPD7343	Discovery
0.6441	Remote Similarity	NPD3025	Approved
0.6441	Remote Similarity	NPD3024	Approved
0.6429	Remote Similarity	NPD7713	Phase 3
0.641	Remote Similarity	NPD2117	Pre-registration
0.641	Remote Similarity	NPD2116	Approved
0.641	Remote Similarity	NPD2115	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