NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	354.22
Volume:	397.167
LogP:	4.029
LogD:	2.49
LogS:	-3.604
# Rotatable Bonds:	11
TPSA:	51.21
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.399
Synthetic Accessibility Score:	2.437
Fsp3:	0.522
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.937
MDCK Permeability:	1.7394759197486565e-05
Pgp-inhibitor:	0.942
Pgp-substrate:	0.351
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.894
30% Bioavailability (F30%):	0.974

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.199
Plasma Protein Binding (PPB):	93.64905548095703%
Volume Distribution (VD):	0.893
Pgp-substrate:	0.6939586997032166%

ADMET: Metabolism

CYP1A2-inhibitor:	0.571
CYP1A2-substrate:	0.893
CYP2C19-inhibitor:	0.802
CYP2C19-substrate:	0.074
CYP2C9-inhibitor:	0.908
CYP2C9-substrate:	0.983
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.285
CYP3A4-inhibitor:	0.806
CYP3A4-substrate:	0.287

ADMET: Excretion

Clearance (CL):	3.131
Half-life (T1/2):	0.56

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.593
Drug-inuced Liver Injury (DILI):	0.945
AMES Toxicity:	0.041
Rat Oral Acute Toxicity:	0.995
Maximum Recommended Daily Dose:	0.019
Skin Sensitization:	0.776
Carcinogencity:	0.071
Eye Corrosion:	0.052
Eye Irritation:	0.47
Respiratory Toxicity:	0.09

Download Data

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

Natural Product: NPC477704

Natural Product ID:	NPC477704
*Common Name:**	Trineurone A
IUPAC Name:	2-[(E)-1-hydroxy-11-phenylundec-10-enylidene]cyclohexane-1,3-dione
Synonyms:
Standard InCHIKey:	DDZXBJXXZZXIRJ-MDWZMJQESA-N
Standard InCHI:	InChI=1S/C23H30O3/c24-20(23-21(25)17-12-18-22(23)26)16-11-6-4-2-1-3-5-8-13-19-14-9-7-10-15-19/h7-10,13-15,24H,1-6,11-12,16-18H2/b13-8+
SMILES:	C1CC(=O)C(=C(CCCCCCCC/C=C/C2=CC=CC=C2)O)C(=O)C1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3289508
PubChem CID:	90681780
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000037] Styrenes

*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
NPO33674	Peperomia trineura	Species	Piperaceae	Eukaryota	aerial parts	Encantado, Rio Grande do Sul, Brazil	2006-DEC	PMID[24905499]

☑ 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
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT487	Organism	Cladosporium cladosporioides	Cladosporium cladosporioides	Activity	=	5	ug	PMID[24905499]
NPT488	Organism	Cladosporium sphaerospermum	Cladosporium sphaerospermum	Activity	=	25	ug	PMID[24905499]

☑ 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 NPC477704 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	191
0.1-0.2	1071
0.2-0.3	3287
0.3-0.4	11710
0.4-0.5	15598
0.5-0.6	8950
0.6-0.7	1613
0.7-0.8	252
0.8-0.85	20
0.85-0.9	3
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477693
0.8913	High Similarity	NPC54647
0.8778	High Similarity	NPC34243
0.8506	High Similarity	NPC123476
0.8488	Intermediate Similarity	NPC44830
0.8353	Intermediate Similarity	NPC127343
0.8352	Intermediate Similarity	NPC187725
0.8352	Intermediate Similarity	NPC141607
0.8315	Intermediate Similarity	NPC194326
0.8298	Intermediate Similarity	NPC289201
0.8298	Intermediate Similarity	NPC156021
0.8298	Intermediate Similarity	NPC240042
0.8295	Intermediate Similarity	NPC95965
0.8235	Intermediate Similarity	NPC139901
0.8235	Intermediate Similarity	NPC151405
0.8235	Intermediate Similarity	NPC272260
0.8211	Intermediate Similarity	NPC317280
0.8211	Intermediate Similarity	NPC329387
0.8211	Intermediate Similarity	NPC476120
0.8152	Intermediate Similarity	NPC476484
0.8144	Intermediate Similarity	NPC244427
0.8144	Intermediate Similarity	NPC222390
0.8125	Intermediate Similarity	NPC474308
0.8105	Intermediate Similarity	NPC278228
0.8105	Intermediate Similarity	NPC103048
0.8085	Intermediate Similarity	NPC206764
0.8068	Intermediate Similarity	NPC285773
0.8061	Intermediate Similarity	NPC274443
0.8061	Intermediate Similarity	NPC247976
0.8021	Intermediate Similarity	NPC145052
0.8021	Intermediate Similarity	NPC179411
0.802	Intermediate Similarity	NPC475282
0.8	Intermediate Similarity	NPC179726
0.8	Intermediate Similarity	NPC9796
0.8	Intermediate Similarity	NPC12695
0.798	Intermediate Similarity	NPC329282
0.7961	Intermediate Similarity	NPC218855
0.7957	Intermediate Similarity	NPC110704
0.7935	Intermediate Similarity	NPC231591
0.7931	Intermediate Similarity	NPC477703
0.7931	Intermediate Similarity	NPC164086
0.79	Intermediate Similarity	NPC172483
0.7885	Intermediate Similarity	NPC471481
0.7865	Intermediate Similarity	NPC273758
0.7835	Intermediate Similarity	NPC271475
0.7831	Intermediate Similarity	NPC74458
0.7822	Intermediate Similarity	NPC70843
0.7822	Intermediate Similarity	NPC29989
0.7822	Intermediate Similarity	NPC100767
0.7822	Intermediate Similarity	NPC95178
0.7822	Intermediate Similarity	NPC69332
0.7816	Intermediate Similarity	NPC300205
0.781	Intermediate Similarity	NPC130591
0.781	Intermediate Similarity	NPC234637
0.781	Intermediate Similarity	NPC294458
0.7791	Intermediate Similarity	NPC245966
0.7788	Intermediate Similarity	NPC292834
0.7767	Intermediate Similarity	NPC88141
0.7745	Intermediate Similarity	NPC470007
0.7738	Intermediate Similarity	NPC285679
0.7732	Intermediate Similarity	NPC477767
0.7727	Intermediate Similarity	NPC17408
0.7727	Intermediate Similarity	NPC285716
0.7727	Intermediate Similarity	NPC71664
0.7727	Intermediate Similarity	NPC95868
0.7723	Intermediate Similarity	NPC134120
0.7717	Intermediate Similarity	NPC322387
0.7717	Intermediate Similarity	NPC69057
0.7714	Intermediate Similarity	NPC477475
0.7714	Intermediate Similarity	NPC477476
0.7701	Intermediate Similarity	NPC36342
0.7701	Intermediate Similarity	NPC285470
0.7701	Intermediate Similarity	NPC2785
0.77	Intermediate Similarity	NPC329556
0.7677	Intermediate Similarity	NPC112552
0.7677	Intermediate Similarity	NPC158623
0.7667	Intermediate Similarity	NPC215008
0.7664	Intermediate Similarity	NPC471616
0.766	Intermediate Similarity	NPC86670
0.766	Intermediate Similarity	NPC110420
0.766	Intermediate Similarity	NPC70940
0.766	Intermediate Similarity	NPC67585
0.766	Intermediate Similarity	NPC303967
0.766	Intermediate Similarity	NPC274455
0.7647	Intermediate Similarity	NPC85560
0.7647	Intermediate Similarity	NPC244933
0.7647	Intermediate Similarity	NPC188677
0.764	Intermediate Similarity	NPC273033
0.764	Intermediate Similarity	NPC12936
0.7634	Intermediate Similarity	NPC329064
0.7624	Intermediate Similarity	NPC8931
0.7624	Intermediate Similarity	NPC261573
0.7624	Intermediate Similarity	NPC120693
0.76	Intermediate Similarity	NPC320891
0.7579	Intermediate Similarity	NPC317645
0.7579	Intermediate Similarity	NPC284475
0.7579	Intermediate Similarity	NPC86987
0.7576	Intermediate Similarity	NPC476042
0.7573	Intermediate Similarity	NPC20485
0.7556	Intermediate Similarity	NPC73637
0.7556	Intermediate Similarity	NPC121478
0.7553	Intermediate Similarity	NPC9822
0.7547	Intermediate Similarity	NPC143768
0.7528	Intermediate Similarity	NPC190567
0.7528	Intermediate Similarity	NPC184030
0.7528	Intermediate Similarity	NPC164449
0.7527	Intermediate Similarity	NPC43945
0.7525	Intermediate Similarity	NPC471317
0.7524	Intermediate Similarity	NPC222905
0.7524	Intermediate Similarity	NPC21162
0.7524	Intermediate Similarity	NPC116842
0.7524	Intermediate Similarity	NPC265513
0.75	Intermediate Similarity	NPC94487
0.75	Intermediate Similarity	NPC1682
0.75	Intermediate Similarity	NPC137847
0.75	Intermediate Similarity	NPC76455
0.75	Intermediate Similarity	NPC264728
0.75	Intermediate Similarity	NPC103488
0.75	Intermediate Similarity	NPC155232
0.75	Intermediate Similarity	NPC225079
0.75	Intermediate Similarity	NPC188844
0.75	Intermediate Similarity	NPC153885
0.7476	Intermediate Similarity	NPC25385
0.7476	Intermediate Similarity	NPC193640
0.7476	Intermediate Similarity	NPC475905
0.7475	Intermediate Similarity	NPC260000
0.7474	Intermediate Similarity	NPC84288
0.7473	Intermediate Similarity	NPC288903
0.7473	Intermediate Similarity	NPC477770
0.7453	Intermediate Similarity	NPC186128
0.7453	Intermediate Similarity	NPC474689
0.7451	Intermediate Similarity	NPC249067
0.7447	Intermediate Similarity	NPC157778
0.7444	Intermediate Similarity	NPC145053
0.7444	Intermediate Similarity	NPC73978
0.7431	Intermediate Similarity	NPC108532
0.7429	Intermediate Similarity	NPC95172
0.7426	Intermediate Similarity	NPC25458
0.7426	Intermediate Similarity	NPC475978
0.7426	Intermediate Similarity	NPC474820
0.7423	Intermediate Similarity	NPC238219
0.7412	Intermediate Similarity	NPC208302
0.7404	Intermediate Similarity	NPC141523
0.7404	Intermediate Similarity	NPC156648
0.7404	Intermediate Similarity	NPC226699
0.74	Intermediate Similarity	NPC280869
0.7396	Intermediate Similarity	NPC133461
0.7386	Intermediate Similarity	NPC329318
0.7383	Intermediate Similarity	NPC93287
0.7383	Intermediate Similarity	NPC470253
0.7381	Intermediate Similarity	NPC98880
0.7379	Intermediate Similarity	NPC474307
0.7379	Intermediate Similarity	NPC471186
0.7374	Intermediate Similarity	NPC472788
0.7364	Intermediate Similarity	NPC471553
0.7363	Intermediate Similarity	NPC475199
0.7363	Intermediate Similarity	NPC283012
0.7358	Intermediate Similarity	NPC474057
0.7356	Intermediate Similarity	NPC189371
0.7353	Intermediate Similarity	NPC202613
0.7353	Intermediate Similarity	NPC68269
0.7347	Intermediate Similarity	NPC260233
0.7347	Intermediate Similarity	NPC172925
0.7339	Intermediate Similarity	NPC322197
0.7333	Intermediate Similarity	NPC40178
0.7333	Intermediate Similarity	NPC17525
0.7327	Intermediate Similarity	NPC136810
0.7327	Intermediate Similarity	NPC133809
0.7327	Intermediate Similarity	NPC128248
0.7326	Intermediate Similarity	NPC271437
0.7321	Intermediate Similarity	NPC474223
0.7321	Intermediate Similarity	NPC475827
0.732	Intermediate Similarity	NPC77273
0.732	Intermediate Similarity	NPC323164
0.732	Intermediate Similarity	NPC59677
0.7315	Intermediate Similarity	NPC471721
0.7312	Intermediate Similarity	NPC294134
0.7312	Intermediate Similarity	NPC99482
0.7308	Intermediate Similarity	NPC51174
0.7308	Intermediate Similarity	NPC6984
0.73	Intermediate Similarity	NPC229242
0.73	Intermediate Similarity	NPC120393
0.7297	Intermediate Similarity	NPC318173
0.7294	Intermediate Similarity	NPC95289
0.7292	Intermediate Similarity	NPC62765
0.7292	Intermediate Similarity	NPC173413
0.7273	Intermediate Similarity	NPC469843
0.7273	Intermediate Similarity	NPC469893
0.7262	Intermediate Similarity	NPC311343
0.7255	Intermediate Similarity	NPC284477
0.7248	Intermediate Similarity	NPC93181
0.7248	Intermediate Similarity	NPC215419
0.7248	Intermediate Similarity	NPC285350
0.7241	Intermediate Similarity	NPC208075
0.7241	Intermediate Similarity	NPC108218
0.7238	Intermediate Similarity	NPC211439
0.7238	Intermediate Similarity	NPC34715
0.7238	Intermediate Similarity	NPC470391
0.7238	Intermediate Similarity	NPC47536
0.7232	Intermediate Similarity	NPC204784

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 NPC477704 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	881
0.2-0.3	1382
0.3-0.4	3108
0.4-0.5	2378
0.5-0.6	1011
0.6-0.7	161
0.7-0.8	40
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8778	High Similarity	NPD5122	Clinical (unspecified phase)
0.8256	Intermediate Similarity	NPD226	Approved
0.8125	Intermediate Similarity	NPD2066	Phase 3
0.8111	Intermediate Similarity	NPD4793	Discontinued
0.8068	Intermediate Similarity	NPD9491	Approved
0.7935	Intermediate Similarity	NPD5347	Phase 2
0.7935	Intermediate Similarity	NPD5346	Phase 2
0.7907	Intermediate Similarity	NPD227	Approved
0.7907	Intermediate Similarity	NPD225	Approved
0.7778	Intermediate Similarity	NPD1932	Approved
0.7742	Intermediate Similarity	NPD800	Approved
0.7727	Intermediate Similarity	NPD1507	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD1693	Approved
0.77	Intermediate Similarity	NPD1929	Approved
0.77	Intermediate Similarity	NPD1930	Approved
0.77	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD1086	Approved
0.766	Intermediate Similarity	NPD1089	Approved
0.766	Intermediate Similarity	NPD1090	Approved
0.764	Intermediate Similarity	NPD942	Approved
0.7629	Intermediate Similarity	NPD5206	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD5909	Discontinued
0.7614	Intermediate Similarity	NPD9490	Approved
0.7579	Intermediate Similarity	NPD7609	Phase 3
0.7579	Intermediate Similarity	NPD1239	Approved
0.7527	Intermediate Similarity	NPD650	Approved
0.7524	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1088	Approved
0.75	Intermediate Similarity	NPD7631	Approved
0.7451	Intermediate Similarity	NPD1237	Approved
0.7353	Intermediate Similarity	NPD6647	Phase 2
0.7347	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD1087	Approved
0.7333	Intermediate Similarity	NPD2329	Discontinued
0.7333	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD3672	Approved
0.7292	Intermediate Similarity	NPD9258	Approved
0.7292	Intermediate Similarity	NPD9256	Approved
0.7292	Intermediate Similarity	NPD3673	Approved
0.7228	Intermediate Similarity	NPD3097	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD3495	Discontinued
0.72	Intermediate Similarity	NPD1564	Approved
0.72	Intermediate Similarity	NPD1565	Approved
0.72	Intermediate Similarity	NPD1566	Phase 3
0.7143	Intermediate Similarity	NPD1508	Approved
0.7129	Intermediate Similarity	NPD9495	Approved
0.7105	Intermediate Similarity	NPD4879	Approved
0.7103	Intermediate Similarity	NPD1317	Discontinued
0.71	Intermediate Similarity	NPD1989	Approved
0.7097	Intermediate Similarity	NPD3971	Phase 1
0.7071	Intermediate Similarity	NPD1202	Approved
0.7059	Intermediate Similarity	NPD7798	Approved
0.7053	Intermediate Similarity	NPD9259	Approved
0.7053	Intermediate Similarity	NPD9257	Approved
0.7048	Intermediate Similarity	NPD5048	Discontinued
0.703	Intermediate Similarity	NPD9566	Approved
0.6991	Remote Similarity	NPD7009	Phase 2
0.6983	Remote Similarity	NPD4878	Approved
0.6979	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD9716	Approved
0.6961	Remote Similarity	NPD253	Approved
0.6931	Remote Similarity	NPD1843	Approved
0.6909	Remote Similarity	NPD6858	Approved
0.6909	Remote Similarity	NPD7094	Approved
0.6903	Remote Similarity	NPD7610	Discontinued
0.69	Remote Similarity	NPD1563	Approved
0.69	Remote Similarity	NPD1066	Discontinued
0.6887	Remote Similarity	NPD1018	Approved
0.6857	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5765	Approved
0.6832	Remote Similarity	NPD2933	Approved
0.6832	Remote Similarity	NPD2934	Approved
0.6827	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD2067	Discontinued
0.6786	Remote Similarity	NPD5951	Approved
0.6783	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD2859	Approved
0.6765	Remote Similarity	NPD2860	Approved
0.6759	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD1238	Approved
0.6727	Remote Similarity	NPD3644	Approved
0.6727	Remote Similarity	NPD3643	Approved
0.6727	Remote Similarity	NPD3642	Approved
0.6724	Remote Similarity	NPD2932	Approved
0.6696	Remote Similarity	NPD6010	Discontinued
0.6696	Remote Similarity	NPD1241	Discontinued
0.6667	Remote Similarity	NPD467	Phase 1
0.6667	Remote Similarity	NPD4094	Approved
0.6667	Remote Similarity	NPD6685	Approved
0.6637	Remote Similarity	NPD2629	Approved
0.6637	Remote Similarity	NPD1246	Approved
0.6637	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5278	Discontinued
0.663	Remote Similarity	NPD9294	Approved
0.6607	Remote Similarity	NPD5277	Phase 2
0.6606	Remote Similarity	NPD9263	Approved
0.6606	Remote Similarity	NPD9267	Approved
0.6606	Remote Similarity	NPD9264	Approved
0.6604	Remote Similarity	NPD2648	Phase 3
0.6604	Remote Similarity	NPD2193	Phase 2
0.6604	Remote Similarity	NPD2171	Approved
0.6581	Remote Similarity	NPD3019	Approved
0.6581	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD2345	Approved
0.6577	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD999	Phase 2
0.6571	Remote Similarity	NPD3020	Approved
0.6566	Remote Similarity	NPD1101	Approved
0.6555	Remote Similarity	NPD3972	Approved
0.6549	Remote Similarity	NPD2652	Approved
0.6549	Remote Similarity	NPD2650	Approved
0.6549	Remote Similarity	NPD3598	Phase 3
0.6545	Remote Similarity	NPD9266	Approved
0.6545	Remote Similarity	NPD2182	Approved
0.6545	Remote Similarity	NPD74	Approved
0.6542	Remote Similarity	NPD3357	Discontinued
0.6538	Remote Similarity	NPD4655	Approved
0.6538	Remote Similarity	NPD4657	Approved
0.6538	Remote Similarity	NPD1099	Approved
0.6538	Remote Similarity	NPD1100	Approved
0.6505	Remote Similarity	NPD9260	Approved
0.65	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5159	Phase 2
0.65	Remote Similarity	NPD5157	Phase 1
0.6486	Remote Similarity	NPD664	Approved
0.6481	Remote Similarity	NPD2577	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD164	Approved
0.6476	Remote Similarity	NPD5926	Approved
0.6471	Remote Similarity	NPD1201	Approved
0.6465	Remote Similarity	NPD1282	Approved
0.6465	Remote Similarity	NPD9538	Approved
0.6449	Remote Similarity	NPD2196	Discontinued
0.6437	Remote Similarity	NPD7331	Phase 2
0.6435	Remote Similarity	NPD3317	Approved
0.6422	Remote Similarity	NPD1040	Phase 2
0.6415	Remote Similarity	NPD1067	Discontinued
0.641	Remote Similarity	NPD9545	Approved
0.641	Remote Similarity	NPD1894	Discontinued
0.6408	Remote Similarity	NPD3719	Approved
0.6408	Remote Similarity	NPD845	Approved
0.6408	Remote Similarity	NPD719	Approved
0.6408	Remote Similarity	NPD3718	Approved
0.6408	Remote Similarity	NPD720	Approved
0.64	Remote Similarity	NPD3268	Approved
0.6393	Remote Similarity	NPD2797	Approved
0.6389	Remote Similarity	NPD9261	Approved
0.6387	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD1875	Phase 1
0.6379	Remote Similarity	NPD9493	Approved
0.6379	Remote Similarity	NPD3797	Approved
0.6379	Remote Similarity	NPD5162	Approved
0.6373	Remote Similarity	NPD1007	Discontinued
0.6372	Remote Similarity	NPD6912	Phase 3
0.6372	Remote Similarity	NPD9508	Approved
0.6364	Remote Similarity	NPD1755	Approved
0.6356	Remote Similarity	NPD4102	Approved
0.6356	Remote Similarity	NPD1245	Approved
0.6356	Remote Similarity	NPD4105	Approved
0.6348	Remote Similarity	NPD1711	Phase 2
0.6346	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD4814	Discontinued
0.6346	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD6049	Phase 2
0.6341	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD2798	Approved
0.6341	Remote Similarity	NPD4980	Approved
0.6339	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD1758	Phase 1
0.6316	Remote Similarity	NPD2607	Approved
0.6311	Remote Similarity	NPD6690	Approved
0.6311	Remote Similarity	NPD752	Approved
0.6303	Remote Similarity	NPD5305	Approved
0.6303	Remote Similarity	NPD5306	Approved
0.6303	Remote Similarity	NPD4733	Approved
0.6296	Remote Similarity	NPD6024	Approved
0.6296	Remote Similarity	NPD6027	Approved
0.6293	Remote Similarity	NPD256	Approved
0.6293	Remote Similarity	NPD255	Approved
0.6286	Remote Similarity	NPD844	Approved
0.6283	Remote Similarity	NPD189	Phase 3
0.6283	Remote Similarity	NPD188	Approved
0.6273	Remote Similarity	NPD2197	Approved
0.6273	Remote Similarity	NPD2192	Approved
0.6271	Remote Similarity	NPD3798	Phase 3
0.6271	Remote Similarity	NPD1759	Phase 1
0.627	Remote Similarity	NPD6766	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD111	Approved
0.626	Remote Similarity	NPD1470	Approved
0.625	Remote Similarity	NPD4136	Approved
0.625	Remote Similarity	NPD4135	Approved
0.625	Remote Similarity	NPD3023	Approved
0.625	Remote Similarity	NPD1409	Phase 3
0.625	Remote Similarity	NPD4106	Approved
0.625	Remote Similarity	NPD3026	Approved
0.6239	Remote Similarity	NPD9568	Approved
0.6238	Remote Similarity	NPD531	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