NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	404.26
Volume:	437.316
LogP:	5.075
LogD:	3.625
LogS:	-5.014
# Rotatable Bonds:	12
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.344
Synthetic Accessibility Score:	3.997
Fsp3:	0.625
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.962
MDCK Permeability:	3.263884718762711e-05
Pgp-inhibitor:	0.02
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.233
30% Bioavailability (F30%):	0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.264
Plasma Protein Binding (PPB):	97.63677215576172%
Volume Distribution (VD):	0.7
Pgp-substrate:	0.4950178265571594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.143
CYP1A2-substrate:	0.759
CYP2C19-inhibitor:	0.267
CYP2C19-substrate:	0.753
CYP2C9-inhibitor:	0.645
CYP2C9-substrate:	0.984
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.15
CYP3A4-inhibitor:	0.411
CYP3A4-substrate:	0.131

ADMET: Excretion

Clearance (CL):	9.939
Half-life (T1/2):	0.575

ADMET: Toxicity

hERG Blockers:	0.114
Human Hepatotoxicity (H-HT):	0.096
Drug-inuced Liver Injury (DILI):	0.32
AMES Toxicity:	0.028
Rat Oral Acute Toxicity:	0.01
Maximum Recommended Daily Dose:	0.051
Skin Sensitization:	0.954
Carcinogencity:	0.155
Eye Corrosion:	0.178
Eye Irritation:	0.77
Respiratory Toxicity:	0.328

Download Data

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

Natural Product: NPC477767

Natural Product ID:	NPC477767
*Common Name:**	2-[(3R,6R)-3-hydroxy-6-methyl-6-[(E)-2-methyl-10-phenyldec-9-enyl]dioxan-3-yl]acetic acid
IUPAC Name:	2-[(3R,6R)-3-hydroxy-6-methyl-6-[(E)-2-methyl-10-phenyldec-9-enyl]dioxan-3-yl]acetic acid
Synonyms:
Standard InCHIKey:	FQNCIZGCBWUVSG-XJCXAQTGSA-N
Standard InCHI:	InChI=1S/C24H36O5/c1-20(18-23(2)16-17-24(27,29-28-23)19-22(25)26)12-8-5-3-4-6-9-13-21-14-10-7-11-15-21/h7,9-11,13-15,20,27H,3-6,8,12,16-19H2,1-2H3,(H,25,26)/b13-9+/t20?,23-,24-/m1/s1
SMILES:	CC(CCCCCC/C=C/C1=CC=CC=C1)C[C@]2(CC[C@@](OO2)(CC(=O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	46883221
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
NPO32577	plakortis sp.	Species	Plakinidae	Eukaryota	n.a.	Caribbean	n.a.	PMID[11720540]
NPO32577	plakortis sp.	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[14738400]
NPO32577	plakortis sp.	Species	Plakinidae	Eukaryota	n.a.	rock wall at 96 m depth, near Blue Hole, Orote Peninsula, Guam	n.a.	PMID[19618913]
NPO32577	plakortis sp.	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20235550]
NPO32577	plakortis sp.	Species	Plakinidae	Eukaryota	n.a.	Okinawan	n.a.	PMID[23186727]
NPO32577	plakortis sp.	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[7760075]
NPO32577	plakortis sp.	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9722495]

☑ 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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	128	ug/ml	PMID[19618913]

☑ 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 NPC477767 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	171
0.1-0.2	754
0.2-0.3	2144
0.3-0.4	7720
0.4-0.5	17182
0.5-0.6	12732
0.6-0.7	1827
0.7-0.8	149
0.8-0.85	7
0.85-0.9	7
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9053	High Similarity	NPC271475
0.8969	High Similarity	NPC474820
0.8969	High Similarity	NPC475978
0.8866	High Similarity	NPC94487
0.8614	High Similarity	NPC474111
0.8614	High Similarity	NPC329705
0.8556	High Similarity	NPC477770
0.8556	High Similarity	NPC44830
0.84	Intermediate Similarity	NPC474112
0.8316	Intermediate Similarity	NPC84288
0.8235	Intermediate Similarity	NPC19136
0.8222	Intermediate Similarity	NPC127343
0.8191	Intermediate Similarity	NPC322387
0.8125	Intermediate Similarity	NPC274455
0.8125	Intermediate Similarity	NPC86670
0.8125	Intermediate Similarity	NPC70940
0.8119	Intermediate Similarity	NPC225079
0.8041	Intermediate Similarity	NPC187725
0.8041	Intermediate Similarity	NPC141607
0.7979	Intermediate Similarity	NPC95965
0.7957	Intermediate Similarity	NPC285773
0.7941	Intermediate Similarity	NPC264728
0.7917	Intermediate Similarity	NPC329064
0.7885	Intermediate Similarity	NPC329282
0.7857	Intermediate Similarity	NPC86987
0.7843	Intermediate Similarity	NPC54647
0.7835	Intermediate Similarity	NPC231591
0.78	Intermediate Similarity	NPC206764
0.7798	Intermediate Similarity	NPC477476
0.7798	Intermediate Similarity	NPC477475
0.7767	Intermediate Similarity	NPC128248
0.7767	Intermediate Similarity	NPC136810
0.7767	Intermediate Similarity	NPC133809
0.7745	Intermediate Similarity	NPC120393
0.7736	Intermediate Similarity	NPC244933
0.7736	Intermediate Similarity	NPC85560
0.7732	Intermediate Similarity	NPC477693
0.7732	Intermediate Similarity	NPC477704
0.7727	Intermediate Similarity	NPC294458
0.7647	Intermediate Similarity	NPC469892
0.7647	Intermediate Similarity	NPC469891
0.7647	Intermediate Similarity	NPC469890
0.7642	Intermediate Similarity	NPC321670
0.7619	Intermediate Similarity	NPC329556
0.7607	Intermediate Similarity	NPC236981
0.7593	Intermediate Similarity	NPC475006
0.7579	Intermediate Similarity	NPC288903
0.7549	Intermediate Similarity	NPC469893
0.75	Intermediate Similarity	NPC317645
0.75	Intermediate Similarity	NPC20485
0.75	Intermediate Similarity	NPC7435
0.7476	Intermediate Similarity	NPC226041
0.7475	Intermediate Similarity	NPC9822
0.7458	Intermediate Similarity	NPC138798
0.7455	Intermediate Similarity	NPC475002
0.7455	Intermediate Similarity	NPC95126
0.7453	Intermediate Similarity	NPC247976
0.7451	Intermediate Similarity	NPC172925
0.7434	Intermediate Similarity	NPC9274
0.7429	Intermediate Similarity	NPC158623
0.7423	Intermediate Similarity	NPC294134
0.7423	Intermediate Similarity	NPC475710
0.7414	Intermediate Similarity	NPC474222
0.7414	Intermediate Similarity	NPC475804
0.7414	Intermediate Similarity	NPC475827
0.7414	Intermediate Similarity	NPC474223
0.7411	Intermediate Similarity	NPC172525
0.7407	Intermediate Similarity	NPC100767
0.7407	Intermediate Similarity	NPC94751
0.7407	Intermediate Similarity	NPC142326
0.7407	Intermediate Similarity	NPC193640
0.7407	Intermediate Similarity	NPC475905
0.7407	Intermediate Similarity	NPC25385
0.7404	Intermediate Similarity	NPC179411
0.7396	Intermediate Similarity	NPC270507
0.7387	Intermediate Similarity	NPC218855
0.7379	Intermediate Similarity	NPC261947
0.7353	Intermediate Similarity	NPC34243
0.734	Intermediate Similarity	NPC272260
0.7339	Intermediate Similarity	NPC21929
0.7333	Intermediate Similarity	NPC221825
0.7333	Intermediate Similarity	NPC476042
0.7327	Intermediate Similarity	NPC110704
0.7321	Intermediate Similarity	NPC471481
0.7315	Intermediate Similarity	NPC474307
0.7312	Intermediate Similarity	NPC9796
0.7308	Intermediate Similarity	NPC240042
0.7304	Intermediate Similarity	NPC471553
0.7292	Intermediate Similarity	NPC323103
0.7292	Intermediate Similarity	NPC121478
0.7292	Intermediate Similarity	NPC103387
0.7292	Intermediate Similarity	NPC73637
0.7283	Intermediate Similarity	NPC189371
0.7265	Intermediate Similarity	NPC478015
0.7265	Intermediate Similarity	NPC478014
0.7265	Intermediate Similarity	NPC478016
0.7263	Intermediate Similarity	NPC477703
0.7257	Intermediate Similarity	NPC130591
0.7257	Intermediate Similarity	NPC234637
0.7255	Intermediate Similarity	NPC323164
0.725	Intermediate Similarity	NPC317163
0.7248	Intermediate Similarity	NPC477251
0.7238	Intermediate Similarity	NPC329387
0.7238	Intermediate Similarity	NPC145052
0.7238	Intermediate Similarity	NPC317280
0.7234	Intermediate Similarity	NPC103488
0.7227	Intermediate Similarity	NPC474254
0.7227	Intermediate Similarity	NPC108286
0.7227	Intermediate Similarity	NPC474159
0.7227	Intermediate Similarity	NPC469927
0.7217	Intermediate Similarity	NPC212891
0.7196	Intermediate Similarity	NPC304873
0.7196	Intermediate Similarity	NPC25458
0.7193	Intermediate Similarity	NPC29607
0.7193	Intermediate Similarity	NPC221870
0.7193	Intermediate Similarity	NPC221275
0.7193	Intermediate Similarity	NPC217111
0.7179	Intermediate Similarity	NPC202015
0.717	Intermediate Similarity	NPC217621
0.7168	Intermediate Similarity	NPC93287
0.7156	Intermediate Similarity	NPC471186
0.7155	Intermediate Similarity	NPC45794
0.7143	Intermediate Similarity	NPC213126
0.7143	Intermediate Similarity	NPC291027
0.7143	Intermediate Similarity	NPC169485
0.7143	Intermediate Similarity	NPC74458
0.7143	Intermediate Similarity	NPC289201
0.7143	Intermediate Similarity	NPC267704
0.7143	Intermediate Similarity	NPC317474
0.7143	Intermediate Similarity	NPC84281
0.7143	Intermediate Similarity	NPC155429
0.7119	Intermediate Similarity	NPC80150
0.7117	Intermediate Similarity	NPC31274
0.7117	Intermediate Similarity	NPC40178
0.7107	Intermediate Similarity	NPC478108
0.7105	Intermediate Similarity	NPC471721
0.71	Intermediate Similarity	NPC194326
0.7094	Intermediate Similarity	NPC310467
0.7091	Intermediate Similarity	NPC37914
0.7083	Intermediate Similarity	NPC285716
0.7083	Intermediate Similarity	NPC184030
0.7083	Intermediate Similarity	NPC17408
0.7083	Intermediate Similarity	NPC121800
0.7083	Intermediate Similarity	NPC164449
0.708	Intermediate Similarity	NPC474689
0.708	Intermediate Similarity	NPC292834
0.7075	Intermediate Similarity	NPC175852
0.7075	Intermediate Similarity	NPC229242
0.7075	Intermediate Similarity	NPC160548
0.7075	Intermediate Similarity	NPC210529
0.7075	Intermediate Similarity	NPC476120
0.7071	Intermediate Similarity	NPC99482
0.7071	Intermediate Similarity	NPC123476
0.7069	Intermediate Similarity	NPC108532
0.7069	Intermediate Similarity	NPC105141
0.7069	Intermediate Similarity	NPC242764
0.7065	Intermediate Similarity	NPC285679
0.7064	Intermediate Similarity	NPC472222
0.7064	Intermediate Similarity	NPC472221
0.7059	Intermediate Similarity	NPC164852
0.7053	Intermediate Similarity	NPC121200
0.7043	Intermediate Similarity	NPC186933
0.7027	Intermediate Similarity	NPC156648
0.7027	Intermediate Similarity	NPC47536
0.7025	Intermediate Similarity	NPC477362
0.7021	Intermediate Similarity	NPC469514
0.7019	Intermediate Similarity	NPC261181
0.7018	Intermediate Similarity	NPC206414
0.7018	Intermediate Similarity	NPC242957
0.7018	Intermediate Similarity	NPC474584
0.7018	Intermediate Similarity	NPC306977
0.7018	Intermediate Similarity	NPC287055
0.7016	Intermediate Similarity	NPC69496
0.7009	Intermediate Similarity	NPC12730
0.7009	Intermediate Similarity	NPC325497
0.7009	Intermediate Similarity	NPC94425
0.7009	Intermediate Similarity	NPC245561
0.7009	Intermediate Similarity	NPC169328
0.7	Intermediate Similarity	NPC105899
0.6983	Remote Similarity	NPC260886
0.6983	Remote Similarity	NPC471616
0.6983	Remote Similarity	NPC210531
0.6981	Remote Similarity	NPC293628
0.6981	Remote Similarity	NPC103048
0.6981	Remote Similarity	NPC278228
0.6981	Remote Similarity	NPC253423
0.6981	Remote Similarity	NPC122493
0.6981	Remote Similarity	NPC324569
0.6981	Remote Similarity	NPC10781
0.6979	Remote Similarity	NPC170484
0.6979	Remote Similarity	NPC151405
0.6979	Remote Similarity	NPC139901
0.6972	Remote Similarity	NPC13426
0.6972	Remote Similarity	NPC471317
0.6972	Remote Similarity	NPC160382
0.6972	Remote Similarity	NPC255676
0.697	Remote Similarity	NPC44546
0.697	Remote Similarity	NPC95429
0.6967	Remote Similarity	NPC244454
0.6964	Remote Similarity	NPC281604

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 NPC477767 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	668
0.2-0.3	1294
0.3-0.4	3075
0.4-0.5	2553
0.5-0.6	1051
0.6-0.7	291
0.7-0.8	53
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
0.8632	High Similarity	NPD5122	Clinical (unspecified phase)
0.8602	High Similarity	NPD5346	Phase 2
0.8602	High Similarity	NPD5347	Phase 2
0.8387	Intermediate Similarity	NPD4793	Discontinued
0.8211	Intermediate Similarity	NPD800	Approved
0.8132	Intermediate Similarity	NPD226	Approved
0.8125	Intermediate Similarity	NPD1089	Approved
0.8125	Intermediate Similarity	NPD1086	Approved
0.8125	Intermediate Similarity	NPD1090	Approved
0.802	Intermediate Similarity	NPD2066	Phase 3
0.798	Intermediate Similarity	NPD1693	Approved
0.7959	Intermediate Similarity	NPD1088	Approved
0.7957	Intermediate Similarity	NPD9491	Approved
0.7812	Intermediate Similarity	NPD1087	Approved
0.781	Intermediate Similarity	NPD5048	Discontinued
0.7802	Intermediate Similarity	NPD227	Approved
0.7802	Intermediate Similarity	NPD225	Approved
0.7788	Intermediate Similarity	NPD5765	Approved
0.7755	Intermediate Similarity	NPD3672	Approved
0.7755	Intermediate Similarity	NPD3673	Approved
0.7736	Intermediate Similarity	NPD6685	Approved
0.7677	Intermediate Similarity	NPD1239	Approved
0.7647	Intermediate Similarity	NPD1565	Approved
0.7647	Intermediate Similarity	NPD1566	Phase 3
0.7647	Intermediate Similarity	NPD1564	Approved
0.7619	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1929	Approved
0.7619	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1930	Approved
0.7568	Intermediate Similarity	NPD2652	Approved
0.7568	Intermediate Similarity	NPD2650	Approved
0.7549	Intermediate Similarity	NPD5206	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD5909	Discontinued
0.7527	Intermediate Similarity	NPD9490	Approved
0.75	Intermediate Similarity	NPD7798	Approved
0.7453	Intermediate Similarity	NPD6647	Phase 2
0.7451	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD1989	Approved
0.7358	Intermediate Similarity	NPD1932	Approved
0.7353	Intermediate Similarity	NPD1563	Approved
0.7333	Intermediate Similarity	NPD3097	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2329	Discontinued
0.7257	Intermediate Similarity	NPD6010	Discontinued
0.7248	Intermediate Similarity	NPD467	Phase 1
0.7238	Intermediate Similarity	NPD253	Approved
0.7232	Intermediate Similarity	NPD6912	Phase 3
0.7207	Intermediate Similarity	NPD1317	Discontinued
0.7143	Intermediate Similarity	NPD4216	Approved
0.7143	Intermediate Similarity	NPD2612	Approved
0.7143	Intermediate Similarity	NPD2611	Approved
0.7143	Intermediate Similarity	NPD2609	Approved
0.7143	Intermediate Similarity	NPD3131	Approved
0.7143	Intermediate Similarity	NPD3643	Approved
0.7143	Intermediate Similarity	NPD3132	Approved
0.7143	Intermediate Similarity	NPD4215	Approved
0.7143	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2610	Approved
0.7143	Intermediate Similarity	NPD4217	Approved
0.7143	Intermediate Similarity	NPD3642	Approved
0.7143	Intermediate Similarity	NPD3644	Approved
0.7143	Intermediate Similarity	NPD4218	Approved
0.7143	Intermediate Similarity	NPD2608	Approved
0.7075	Intermediate Similarity	NPD9495	Approved
0.7063	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD2629	Approved
0.7019	Intermediate Similarity	NPD1202	Approved
0.7019	Intermediate Similarity	NPD1066	Discontinued
0.7016	Intermediate Similarity	NPD2613	Approved
0.6983	Remote Similarity	NPD3317	Approved
0.6981	Remote Similarity	NPD9566	Approved
0.6923	Remote Similarity	NPD7631	Approved
0.6903	Remote Similarity	NPD5278	Discontinued
0.6903	Remote Similarity	NPD2067	Discontinued
0.69	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD9256	Approved
0.6893	Remote Similarity	NPD9258	Approved
0.6891	Remote Similarity	NPD5981	Approved
0.687	Remote Similarity	NPD6858	Approved
0.687	Remote Similarity	NPD7094	Approved
0.6869	Remote Similarity	NPD3971	Phase 1
0.686	Remote Similarity	NPD4807	Approved
0.686	Remote Similarity	NPD4806	Approved
0.685	Remote Similarity	NPD3616	Approved
0.685	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.685	Remote Similarity	NPD3615	Approved
0.685	Remote Similarity	NPD2573	Approved
0.685	Remote Similarity	NPD2566	Approved
0.685	Remote Similarity	NPD3614	Approved
0.685	Remote Similarity	NPD2571	Approved
0.685	Remote Similarity	NPD3088	Approved
0.685	Remote Similarity	NPD4746	Phase 3
0.685	Remote Similarity	NPD3087	Approved
0.685	Remote Similarity	NPD2574	Discontinued
0.685	Remote Similarity	NPD3089	Approved
0.685	Remote Similarity	NPD2570	Approved
0.685	Remote Similarity	NPD3090	Approved
0.685	Remote Similarity	NPD4745	Approved
0.6833	Remote Similarity	NPD5306	Approved
0.6833	Remote Similarity	NPD5305	Approved
0.6827	Remote Similarity	NPD7609	Phase 3
0.681	Remote Similarity	NPD3598	Phase 3
0.6789	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD5951	Approved
0.675	Remote Similarity	NPD4105	Approved
0.675	Remote Similarity	NPD4102	Approved
0.6744	Remote Similarity	NPD4685	Phase 3
0.6744	Remote Similarity	NPD4686	Approved
0.6744	Remote Similarity	NPD4684	Phase 3
0.6735	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD7610	Discontinued
0.6723	Remote Similarity	NPD6065	Approved
0.672	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.672	Remote Similarity	NPD6085	Phase 2
0.6697	Remote Similarity	NPD1067	Discontinued
0.6667	Remote Similarity	NPD2182	Approved
0.6667	Remote Similarity	NPD9257	Approved
0.6667	Remote Similarity	NPD9259	Approved
0.6667	Remote Similarity	NPD942	Approved
0.6639	Remote Similarity	NPD4106	Approved
0.6639	Remote Similarity	NPD4576	Approved
0.6639	Remote Similarity	NPD4136	Approved
0.6639	Remote Similarity	NPD4574	Approved
0.6639	Remote Similarity	NPD4135	Approved
0.6636	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6049	Phase 2
0.661	Remote Similarity	NPD1246	Approved
0.661	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD1752	Approved
0.6609	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD1756	Approved
0.6607	Remote Similarity	NPD1237	Approved
0.6607	Remote Similarity	NPD164	Approved
0.6606	Remote Similarity	NPD5926	Approved
0.6589	Remote Similarity	NPD7961	Discontinued
0.6589	Remote Similarity	NPD7715	Approved
0.6589	Remote Similarity	NPD7714	Approved
0.6587	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD9267	Approved
0.6579	Remote Similarity	NPD9263	Approved
0.6579	Remote Similarity	NPD9264	Approved
0.6562	Remote Similarity	NPD9716	Approved
0.6557	Remote Similarity	NPD4199	Phase 3
0.6557	Remote Similarity	NPD2345	Approved
0.6555	Remote Similarity	NPD1348	Approved
0.6555	Remote Similarity	NPD4198	Discontinued
0.6552	Remote Similarity	NPD189	Phase 3
0.6552	Remote Similarity	NPD2201	Approved
0.6552	Remote Similarity	NPD188	Approved
0.6552	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD5927	Discontinued
0.6549	Remote Similarity	NPD1018	Approved
0.6542	Remote Similarity	NPD3719	Approved
0.6542	Remote Similarity	NPD3718	Approved
0.6538	Remote Similarity	NPD1101	Approved
0.6538	Remote Similarity	NPD531	Approved
0.6532	Remote Similarity	NPD6637	Approved
0.6529	Remote Similarity	NPD3798	Phase 3
0.6529	Remote Similarity	NPD7009	Phase 2
0.6529	Remote Similarity	NPD4479	Discontinued
0.6525	Remote Similarity	NPD1373	Approved
0.6525	Remote Similarity	NPD1374	Approved
0.6525	Remote Similarity	NPD1370	Approved
0.6525	Remote Similarity	NPD1280	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD1371	Approved
0.6522	Remote Similarity	NPD9266	Approved
0.6522	Remote Similarity	NPD74	Approved
0.6522	Remote Similarity	NPD476	Approved
0.6514	Remote Similarity	NPD3495	Discontinued
0.6508	Remote Similarity	NPD2797	Approved
0.65	Remote Similarity	NPD3797	Approved
0.65	Remote Similarity	NPD9493	Approved
0.65	Remote Similarity	NPD5162	Approved
0.6481	Remote Similarity	NPD4814	Discontinued
0.648	Remote Similarity	NPD4677	Discontinued
0.6475	Remote Similarity	NPD6994	Approved
0.6475	Remote Similarity	NPD6993	Approved
0.6466	Remote Similarity	NPD3648	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD5239	Approved
0.6466	Remote Similarity	NPD5235	Approved
0.6466	Remote Similarity	NPD4234	Approved
0.6466	Remote Similarity	NPD4233	Approved
0.6466	Remote Similarity	NPD5240	Approved
0.6466	Remote Similarity	NPD5236	Approved
0.6466	Remote Similarity	NPD5237	Approved
0.6452	Remote Similarity	NPD3603	Phase 3
0.6446	Remote Similarity	NPD2115	Approved
0.6446	Remote Similarity	NPD2117	Pre-registration
0.6446	Remote Similarity	NPD2116	Approved
0.6446	Remote Similarity	NPD1758	Phase 1
0.6442	Remote Similarity	NPD650	Approved
0.6441	Remote Similarity	NPD5277	Phase 2
0.6441	Remote Similarity	NPD2607	Approved
0.6429	Remote Similarity	NPD4818	Approved
0.6429	Remote Similarity	NPD4817	Approved
0.6423	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD2860	Approved
0.6422	Remote Similarity	NPD2859	Approved
0.6417	Remote Similarity	NPD256	Approved
0.6417	Remote Similarity	NPD255	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