NPASS Compound

Structure

CID289201 OpenBabel06191716092D 21 22 0 0 1 0 0 0 0 0999 V2000 -6.9282 -2.0000 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 -6.0622 -1.5000 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 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 -5.1962 -2.0000 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 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 -4.3301 -3.5000 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 -2.5981 -1.5000 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 -5.1962 -3.0000 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 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 3 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 -1.7321 1.0000 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 12 1 0 0 0 0 11 16 1 0 0 0 0 12 18 1 0 0 0 0 13 14 2 0 0 0 0 13 18 1 0 0 0 0 14 19 1 0 0 0 0 15 17 1 0 0 0 0 15 19 1 0 0 0 0 18 20 2 0 0 0 0 19 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	280.15
Volume:	316.556
LogP:	2.515
LogD:	2.444
LogS:	-2.95
# 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:	0.737
Synthetic Accessibility Score:	1.766
Fsp3:	0.263
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:	-4.744
MDCK Permeability:	2.2894628273206763e-05
Pgp-inhibitor:	0.992
Pgp-substrate:	0.966
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.306
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.712
Plasma Protein Binding (PPB):	92.8012466430664%
Volume Distribution (VD):	0.701
Pgp-substrate:	2.314648389816284%

ADMET: Metabolism

CYP1A2-inhibitor:	0.383
CYP1A2-substrate:	0.427
CYP2C19-inhibitor:	0.902
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.836
CYP2C9-substrate:	0.246
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.38
CYP3A4-inhibitor:	0.124
CYP3A4-substrate:	0.536

ADMET: Excretion

Clearance (CL):	9.306
Half-life (T1/2):	0.925

ADMET: Toxicity

hERG Blockers:	0.078
Human Hepatotoxicity (H-HT):	0.392
Drug-inuced Liver Injury (DILI):	0.748
AMES Toxicity:	0.436
Rat Oral Acute Toxicity:	0.221
Maximum Recommended Daily Dose:	0.074
Skin Sensitization:	0.312
Carcinogencity:	0.058
Eye Corrosion:	0.004
Eye Irritation:	0.261
Respiratory Toxicity:	0.049

Download Data

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

Natural Product: NPC289201

Natural Product ID:	NPC289201
*Common Name:**	6-Hydroxy-1,7-Diphenyl-4-En-3-Heptanone
IUPAC Name:	(E)-6-hydroxy-1,7-diphenylhept-4-en-3-one
Synonyms:
Standard InCHIKey:	TYZZLIGGENRWEF-BUHFOSPRSA-N
Standard InCHI:	InChI=1S/C19H20O2/c20-18(12-11-16-7-3-1-4-8-16)13-14-19(21)15-17-9-5-2-6-10-17/h1-10,13-14,19,21H,11-12,15H2/b14-13+
SMILES:	O=C(/C=C/C(Cc1ccccc1)O)CCc1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL240908
PubChem CID:	24755150
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.	rhizome	n.a.	PMID[18484537]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	root	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
IC50	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	1300.0	nM	PMID[452071]

☑ 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 NPC289201 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	193
0.1-0.2	956
0.2-0.3	2933
0.3-0.4	9001
0.4-0.5	12905
0.5-0.6	12631
0.6-0.7	3503
0.7-0.8	533
0.8-0.85	34
0.85-0.9	5
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.914	High Similarity	NPC206764
0.898	High Similarity	NPC249067
0.8854	High Similarity	NPC317280
0.8854	High Similarity	NPC329387
0.8817	High Similarity	NPC187725
0.8817	High Similarity	NPC141607
0.8571	High Similarity	NPC123476
0.8529	High Similarity	NPC211439
0.8491	Intermediate Similarity	NPC285350
0.8444	Intermediate Similarity	NPC475199
0.8444	Intermediate Similarity	NPC283012
0.8431	Intermediate Similarity	NPC69332
0.8431	Intermediate Similarity	NPC95178
0.8431	Intermediate Similarity	NPC29989
0.8387	Intermediate Similarity	NPC194326
0.837	Intermediate Similarity	NPC99482
0.8298	Intermediate Similarity	NPC477693
0.8298	Intermediate Similarity	NPC477704
0.8286	Intermediate Similarity	NPC252544
0.8286	Intermediate Similarity	NPC321252
0.8252	Intermediate Similarity	NPC70843
0.8247	Intermediate Similarity	NPC34243
0.8241	Intermediate Similarity	NPC23402
0.8211	Intermediate Similarity	NPC231591
0.8208	Intermediate Similarity	NPC158282
0.8208	Intermediate Similarity	NPC177576
0.819	Intermediate Similarity	NPC88141
0.8182	Intermediate Similarity	NPC249435
0.8173	Intermediate Similarity	NPC20485
0.8111	Intermediate Similarity	NPC151405
0.8111	Intermediate Similarity	NPC139901
0.81	Intermediate Similarity	NPC175852
0.81	Intermediate Similarity	NPC210529
0.81	Intermediate Similarity	NPC160548
0.8095	Intermediate Similarity	NPC475282
0.8058	Intermediate Similarity	NPC261573
0.8058	Intermediate Similarity	NPC120693
0.8058	Intermediate Similarity	NPC8931
0.8056	Intermediate Similarity	NPC196673
0.8043	Intermediate Similarity	NPC121478
0.8043	Intermediate Similarity	NPC73637
0.8041	Intermediate Similarity	NPC317645
0.8037	Intermediate Similarity	NPC471188
0.8022	Intermediate Similarity	NPC184030
0.8022	Intermediate Similarity	NPC164449
0.8021	Intermediate Similarity	NPC9822
0.8	Intermediate Similarity	NPC270654
0.8	Intermediate Similarity	NPC141523
0.7981	Intermediate Similarity	NPC321670
0.7961	Intermediate Similarity	NPC255676
0.7961	Intermediate Similarity	NPC329556
0.7959	Intermediate Similarity	NPC77273
0.7944	Intermediate Similarity	NPC476003
0.7944	Intermediate Similarity	NPC116842
0.7938	Intermediate Similarity	NPC213156
0.7938	Intermediate Similarity	NPC240108
0.7935	Intermediate Similarity	NPC117180
0.7925	Intermediate Similarity	NPC317305
0.7905	Intermediate Similarity	NPC188677
0.79	Intermediate Similarity	NPC12695
0.7872	Intermediate Similarity	NPC304538
0.7864	Intermediate Similarity	NPC25458
0.7857	Intermediate Similarity	NPC110704
0.7849	Intermediate Similarity	NPC329319
0.7849	Intermediate Similarity	NPC87299
0.7849	Intermediate Similarity	NPC103326
0.7849	Intermediate Similarity	NPC99394
0.7843	Intermediate Similarity	NPC474308
0.7838	Intermediate Similarity	NPC19290
0.783	Intermediate Similarity	NPC156648
0.7826	Intermediate Similarity	NPC86900
0.7822	Intermediate Similarity	NPC103048
0.781	Intermediate Similarity	NPC471186
0.781	Intermediate Similarity	NPC105899
0.7807	Intermediate Similarity	NPC472981
0.7798	Intermediate Similarity	NPC206414
0.7798	Intermediate Similarity	NPC242957
0.7798	Intermediate Similarity	NPC306977
0.7798	Intermediate Similarity	NPC287055
0.7788	Intermediate Similarity	NPC160382
0.7788	Intermediate Similarity	NPC68269
0.7778	Intermediate Similarity	NPC21162
0.7767	Intermediate Similarity	NPC158623
0.7767	Intermediate Similarity	NPC42211
0.7766	Intermediate Similarity	NPC44830
0.7766	Intermediate Similarity	NPC285773
0.7759	Intermediate Similarity	NPC285394
0.7757	Intermediate Similarity	NPC17525
0.7757	Intermediate Similarity	NPC281604
0.7755	Intermediate Similarity	NPC62765
0.7748	Intermediate Similarity	NPC322197
0.7745	Intermediate Similarity	NPC229242
0.7745	Intermediate Similarity	NPC179411
0.7745	Intermediate Similarity	NPC476120
0.7745	Intermediate Similarity	NPC201967
0.7717	Intermediate Similarity	NPC272260
0.7706	Intermediate Similarity	NPC212718
0.7706	Intermediate Similarity	NPC114682
0.7706	Intermediate Similarity	NPC234376
0.77	Intermediate Similarity	NPC261181
0.7692	Intermediate Similarity	NPC9796
0.7692	Intermediate Similarity	NPC179726
0.7679	Intermediate Similarity	NPC299252
0.7679	Intermediate Similarity	NPC61062
0.7679	Intermediate Similarity	NPC277394
0.7677	Intermediate Similarity	NPC476484
0.767	Intermediate Similarity	NPC118343
0.767	Intermediate Similarity	NPC51333
0.767	Intermediate Similarity	NPC78119
0.767	Intermediate Similarity	NPC216468
0.767	Intermediate Similarity	NPC217621
0.767	Intermediate Similarity	NPC132078
0.767	Intermediate Similarity	NPC130193
0.7664	Intermediate Similarity	NPC470007
0.7647	Intermediate Similarity	NPC278228
0.7647	Intermediate Similarity	NPC253423
0.7647	Intermediate Similarity	NPC156021
0.7642	Intermediate Similarity	NPC269457
0.7642	Intermediate Similarity	NPC134120
0.7642	Intermediate Similarity	NPC474307
0.7636	Intermediate Similarity	NPC272524
0.7636	Intermediate Similarity	NPC265002
0.7634	Intermediate Similarity	NPC71664
0.7634	Intermediate Similarity	NPC127343
0.7632	Intermediate Similarity	NPC182240
0.7629	Intermediate Similarity	NPC69057
0.7619	Intermediate Similarity	NPC301943
0.7619	Intermediate Similarity	NPC135784
0.7619	Intermediate Similarity	NPC474365
0.7615	Intermediate Similarity	NPC265513
0.7615	Intermediate Similarity	NPC474057
0.7604	Intermediate Similarity	NPC95965
0.7596	Intermediate Similarity	NPC294741
0.7596	Intermediate Similarity	NPC469481
0.7596	Intermediate Similarity	NPC213730
0.7593	Intermediate Similarity	NPC40178
0.7593	Intermediate Similarity	NPC318327
0.7589	Intermediate Similarity	NPC471616
0.7579	Intermediate Similarity	NPC273758
0.7573	Intermediate Similarity	NPC260000
0.7573	Intermediate Similarity	NPC145052
0.757	Intermediate Similarity	NPC475905
0.757	Intermediate Similarity	NPC193640
0.757	Intermediate Similarity	NPC477251
0.757	Intermediate Similarity	NPC51174
0.757	Intermediate Similarity	NPC136962
0.757	Intermediate Similarity	NPC25385
0.7568	Intermediate Similarity	NPC87069
0.7568	Intermediate Similarity	NPC474363
0.7565	Intermediate Similarity	NPC473136
0.7565	Intermediate Similarity	NPC265454
0.7565	Intermediate Similarity	NPC34634
0.7565	Intermediate Similarity	NPC470585
0.7556	Intermediate Similarity	NPC108218
0.7553	Intermediate Similarity	NPC12936
0.7553	Intermediate Similarity	NPC273033
0.7549	Intermediate Similarity	NPC61944
0.7547	Intermediate Similarity	NPC280616
0.7547	Intermediate Similarity	NPC171831
0.7547	Intermediate Similarity	NPC242913
0.7545	Intermediate Similarity	NPC477250
0.7545	Intermediate Similarity	NPC471189
0.7545	Intermediate Similarity	NPC66208
0.7545	Intermediate Similarity	NPC268388
0.7544	Intermediate Similarity	NPC318173
0.7527	Intermediate Similarity	NPC469894
0.7524	Intermediate Similarity	NPC244427
0.7524	Intermediate Similarity	NPC222390
0.7524	Intermediate Similarity	NPC304873
0.7524	Intermediate Similarity	NPC7686
0.7524	Intermediate Similarity	NPC40258
0.7524	Intermediate Similarity	NPC91461
0.7524	Intermediate Similarity	NPC284477
0.7523	Intermediate Similarity	NPC95172
0.7522	Intermediate Similarity	NPC128249
0.75	Intermediate Similarity	NPC54647
0.75	Intermediate Similarity	NPC66655
0.75	Intermediate Similarity	NPC280869
0.75	Intermediate Similarity	NPC226699
0.75	Intermediate Similarity	NPC47536
0.75	Intermediate Similarity	NPC34715
0.75	Intermediate Similarity	NPC93181
0.75	Intermediate Similarity	NPC119631
0.75	Intermediate Similarity	NPC476042
0.7479	Intermediate Similarity	NPC79608
0.7478	Intermediate Similarity	NPC473767
0.7478	Intermediate Similarity	NPC472708
0.7477	Intermediate Similarity	NPC128368
0.7477	Intermediate Similarity	NPC286222
0.7477	Intermediate Similarity	NPC470253
0.7476	Intermediate Similarity	NPC240042
0.7475	Intermediate Similarity	NPC1793
0.7475	Intermediate Similarity	NPC199567
0.7456	Intermediate Similarity	NPC471553
0.7455	Intermediate Similarity	NPC183700
0.7455	Intermediate Similarity	NPC133308
0.7455	Intermediate Similarity	NPC222905
0.7453	Intermediate Similarity	NPC91820
0.7453	Intermediate Similarity	NPC274443
0.7453	Intermediate Similarity	NPC247976

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 NPC289201 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	186
0.1-0.2	813
0.2-0.3	1175
0.3-0.4	2794
0.4-0.5	2492
0.5-0.6	1275
0.6-0.7	357
0.7-0.8	56
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.898	High Similarity	NPD1237	Approved
0.82	Intermediate Similarity	NPD2066	Phase 3
0.8137	Intermediate Similarity	NPD6647	Phase 2
0.81	Intermediate Similarity	NPD9495	Approved
0.7961	Intermediate Similarity	NPD1929	Approved
0.7961	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD1930	Approved
0.7879	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD5048	Discontinued
0.7766	Intermediate Similarity	NPD9491	Approved
0.7759	Intermediate Similarity	NPD5157	Phase 1
0.7759	Intermediate Similarity	NPD5159	Phase 2
0.7759	Intermediate Similarity	NPD5158	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD9258	Approved
0.7755	Intermediate Similarity	NPD9256	Approved
0.7714	Intermediate Similarity	NPD5909	Discontinued
0.77	Intermediate Similarity	NPD1202	Approved
0.7692	Intermediate Similarity	NPD1932	Approved
0.7677	Intermediate Similarity	NPD1239	Approved
0.767	Intermediate Similarity	NPD1238	Approved
0.7658	Intermediate Similarity	NPD2629	Approved
0.7619	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD226	Approved
0.7553	Intermediate Similarity	NPD942	Approved
0.7549	Intermediate Similarity	NPD1989	Approved
0.75	Intermediate Similarity	NPD5951	Approved
0.75	Intermediate Similarity	NPD9294	Approved
0.7475	Intermediate Similarity	NPD800	Approved
0.7451	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD1693	Approved
0.7449	Intermediate Similarity	NPD4793	Discontinued
0.7447	Intermediate Similarity	NPD1507	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD1090	Approved
0.74	Intermediate Similarity	NPD1086	Approved
0.74	Intermediate Similarity	NPD1089	Approved
0.7379	Intermediate Similarity	NPD5206	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD9259	Approved
0.7347	Intermediate Similarity	NPD9257	Approved
0.734	Intermediate Similarity	NPD9490	Approved
0.7333	Intermediate Similarity	NPD7798	Approved
0.7308	Intermediate Similarity	NPD1565	Approved
0.7308	Intermediate Similarity	NPD1564	Approved
0.7308	Intermediate Similarity	NPD1566	Phase 3
0.73	Intermediate Similarity	NPD5346	Phase 2
0.73	Intermediate Similarity	NPD5347	Phase 2
0.7297	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD2934	Approved
0.7282	Intermediate Similarity	NPD2933	Approved
0.7273	Intermediate Similarity	NPD2329	Discontinued
0.7273	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD1088	Approved
0.7234	Intermediate Similarity	NPD225	Approved
0.7234	Intermediate Similarity	NPD227	Approved
0.7227	Intermediate Similarity	NPD4878	Approved
0.7216	Intermediate Similarity	NPD3971	Phase 1
0.7212	Intermediate Similarity	NPD2859	Approved
0.7212	Intermediate Similarity	NPD2860	Approved
0.7207	Intermediate Similarity	NPD2067	Discontinued
0.7119	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD2182	Approved
0.71	Intermediate Similarity	NPD1087	Approved
0.7097	Intermediate Similarity	NPD9716	Approved
0.7097	Intermediate Similarity	NPD7008	Discontinued
0.7059	Intermediate Similarity	NPD4136	Approved
0.7059	Intermediate Similarity	NPD4135	Approved
0.7059	Intermediate Similarity	NPD4106	Approved
0.7059	Intermediate Similarity	NPD3672	Approved
0.7059	Intermediate Similarity	NPD3673	Approved
0.7027	Intermediate Similarity	NPD4095	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD1563	Approved
0.7018	Intermediate Similarity	NPD5277	Phase 2
0.7009	Intermediate Similarity	NPD3020	Approved
0.6992	Remote Similarity	NPD4980	Approved
0.699	Remote Similarity	NPD7609	Phase 3
0.6975	Remote Similarity	NPD5306	Approved
0.6975	Remote Similarity	NPD5305	Approved
0.6972	Remote Similarity	NPD5765	Approved
0.696	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1241	Discontinued
0.6953	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD1894	Discontinued
0.6931	Remote Similarity	NPD650	Approved
0.6923	Remote Similarity	NPD1508	Approved
0.6923	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7631	Approved
0.6917	Remote Similarity	NPD4879	Approved
0.6916	Remote Similarity	NPD5926	Approved
0.6909	Remote Similarity	NPD164	Approved
0.6897	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD4105	Approved
0.6891	Remote Similarity	NPD4102	Approved
0.6881	Remote Similarity	NPD4719	Phase 2
0.6875	Remote Similarity	NPD9264	Approved
0.6875	Remote Similarity	NPD9267	Approved
0.6875	Remote Similarity	NPD9263	Approved
0.6875	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.687	Remote Similarity	NPD7094	Approved
0.687	Remote Similarity	NPD6858	Approved
0.686	Remote Similarity	NPD4807	Approved
0.686	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.686	Remote Similarity	NPD1201	Approved
0.686	Remote Similarity	NPD6287	Discontinued
0.686	Remote Similarity	NPD4806	Approved
0.6842	Remote Similarity	NPD4025	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD3019	Approved
0.6833	Remote Similarity	NPD2932	Approved
0.6833	Remote Similarity	NPD2345	Approved
0.6822	Remote Similarity	NPD3495	Discontinued
0.6814	Remote Similarity	NPD9266	Approved
0.6814	Remote Similarity	NPD74	Approved
0.681	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6010	Discontinued
0.6807	Remote Similarity	NPD9545	Approved
0.6803	Remote Similarity	NPD3972	Approved
0.68	Remote Similarity	NPD5204	Approved
0.6796	Remote Similarity	NPD689	Discontinued
0.6792	Remote Similarity	NPD9260	Approved
0.6789	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6685	Approved
0.6783	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD9508	Approved
0.678	Remote Similarity	NPD9493	Approved
0.6774	Remote Similarity	NPD2159	Approved
0.6774	Remote Similarity	NPD1470	Approved
0.6774	Remote Similarity	NPD2625	Approved
0.6774	Remote Similarity	NPD2160	Approved
0.6774	Remote Similarity	NPD2797	Approved
0.6774	Remote Similarity	NPD2626	Approved
0.6774	Remote Similarity	NPD2628	Approved
0.6774	Remote Similarity	NPD2627	Approved
0.6765	Remote Similarity	NPD1282	Approved
0.6759	Remote Similarity	NPD9611	Approved
0.6759	Remote Similarity	NPD9609	Approved
0.6759	Remote Similarity	NPD9612	Approved
0.6754	Remote Similarity	NPD1317	Discontinued
0.6752	Remote Similarity	NPD1246	Approved
0.6746	Remote Similarity	NPD4617	Approved
0.6746	Remote Similarity	NPD4620	Approved
0.6746	Remote Similarity	NPD5201	Approved
0.6746	Remote Similarity	NPD5203	Approved
0.6733	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD1843	Approved
0.6727	Remote Similarity	NPD855	Approved
0.6727	Remote Similarity	NPD854	Approved
0.6723	Remote Similarity	NPD2347	Approved
0.6723	Remote Similarity	NPD7610	Discontinued
0.672	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.672	Remote Similarity	NPD6085	Phase 2
0.672	Remote Similarity	NPD2798	Approved
0.6719	Remote Similarity	NPD7714	Approved
0.6719	Remote Similarity	NPD7715	Approved
0.6698	Remote Similarity	NPD1066	Discontinued
0.6697	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD3317	Approved
0.6694	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD6039	Approved
0.6667	Remote Similarity	NPD2650	Approved
0.6667	Remote Similarity	NPD4452	Approved
0.6667	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4658	Approved
0.6667	Remote Similarity	NPD4445	Approved
0.6667	Remote Similarity	NPD2652	Approved
0.6667	Remote Similarity	NPD7009	Phase 2
0.6667	Remote Similarity	NPD4453	Approved
0.6667	Remote Similarity	NPD4656	Approved
0.6641	Remote Similarity	NPD3268	Approved
0.664	Remote Similarity	NPD1164	Approved
0.6639	Remote Similarity	NPD4576	Approved
0.6639	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD4574	Approved
0.6637	Remote Similarity	NPD467	Phase 1
0.6636	Remote Similarity	NPD2555	Approved
0.6636	Remote Similarity	NPD2553	Approved
0.6636	Remote Similarity	NPD2549	Approved
0.6636	Remote Similarity	NPD2550	Approved
0.6636	Remote Similarity	NPD2552	Approved
0.6636	Remote Similarity	NPD2558	Approved
0.6617	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD4628	Phase 3
0.6589	Remote Similarity	NPD7713	Phase 3
0.6585	Remote Similarity	NPD4215	Approved
0.6585	Remote Similarity	NPD2609	Approved
0.6585	Remote Similarity	NPD4217	Approved
0.6585	Remote Similarity	NPD3131	Approved
0.6585	Remote Similarity	NPD2608	Approved
0.6585	Remote Similarity	NPD2611	Approved
0.6585	Remote Similarity	NPD2612	Approved
0.6585	Remote Similarity	NPD4216	Approved
0.6585	Remote Similarity	NPD4218	Approved
0.6585	Remote Similarity	NPD3132	Approved
0.6585	Remote Similarity	NPD2610	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