NPASS Compound

Structure

CID307682 OpenBabel06191716112D 30 30 0 0 0 0 0 0 0 0999 V2000 13.0000 -3.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 0.8660 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 6.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 11.5000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 24 1 0 0 0 0 5 30 1 0 0 0 0 6 8 1 0 0 0 0 6 20 2 0 0 0 0 7 9 2 0 0 0 0 7 20 1 0 0 0 0 8 22 2 0 0 0 0 9 22 1 0 0 0 0 10 13 1 0 0 0 0 10 20 1 0 0 0 0 11 14 1 0 0 0 0 11 19 2 0 0 0 0 12 15 2 0 0 0 0 12 23 1 0 0 0 0 13 24 1 0 0 0 0 14 29 1 0 0 0 0 15 30 1 0 0 0 0 16 18 2 0 0 0 0 16 21 1 0 0 0 0 17 19 1 0 0 0 0 17 21 1 0 0 0 0 21 25 2 0 0 0 0 22 29 1 0 0 0 0 23 24 1 0 0 0 0 23 26 2 0 0 0 0 27 30 2 0 0 0 0 28 30 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	433.19
Volume:	450.173
LogP:	2.153
LogD:	2.244
LogS:	-4.02
# Rotatable Bonds:	12
TPSA:	80.75
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.499
Synthetic Accessibility Score:	3.026
Fsp3:	0.391
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.125
MDCK Permeability:	1.9697352399816737e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.046
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.366
Plasma Protein Binding (PPB):	90.1283950805664%
Volume Distribution (VD):	0.602
Pgp-substrate:	12.913124084472656%

ADMET: Metabolism

CYP1A2-inhibitor:	0.424
CYP1A2-substrate:	0.915
CYP2C19-inhibitor:	0.677
CYP2C19-substrate:	0.865
CYP2C9-inhibitor:	0.832
CYP2C9-substrate:	0.943
CYP2D6-inhibitor:	0.856
CYP2D6-substrate:	0.831
CYP3A4-inhibitor:	0.314
CYP3A4-substrate:	0.82

ADMET: Excretion

Clearance (CL):	0.421
Half-life (T1/2):	0.857

ADMET: Toxicity

hERG Blockers:	0.15
Human Hepatotoxicity (H-HT):	0.62
Drug-inuced Liver Injury (DILI):	0.121
AMES Toxicity:	0.03
Rat Oral Acute Toxicity:	0.03
Maximum Recommended Daily Dose:	0.633
Skin Sensitization:	0.949
Carcinogencity:	0.455
Eye Corrosion:	0.003
Eye Irritation:	0.086
Respiratory Toxicity:	0.388

Download Data

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

Natural Product: NPC307682

Natural Product ID:	NPC307682
*Common Name:**	Methylgerambullone
IUPAC Name:	(E)-N-[2-[4-[(2E)-3,7-dimethyl-5-oxoocta-2,6-dienoxy]phenyl]ethyl]-N-methyl-3-methylsulfonylprop-2-enamide
Synonyms:	Methylgerambullone
Standard InCHIKey:	XBMHYRIXEUNGGG-XKVHLQQPSA-N
Standard InCHI:	InChI=1S/C23H31NO5S/c1-18(2)16-21(25)17-19(3)11-14-29-22-8-6-20(7-9-22)10-13-24(4)23(26)12-15-30(5,27)28/h6-9,11-12,15-16H,10,13-14,17H2,1-5H3/b15-12+,19-11+
SMILES:	CC(=CC(=O)C/C(=C/COc1ccc(cc1)CCN(C)C(=O)/C=C/S(=O)(=O)C)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL591333
PubChem CID:	45258604
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0000051] Aromatic monoterpenoids

*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
NPO13134	Iris japonica	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12690	Caltha palustris	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13134	Iris japonica	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12690	Caltha palustris	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12690	Caltha palustris	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27835	Salvia lutea	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12690	Caltha palustris	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7071	Beilschmiedia brevipes	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13134	Iris japonica	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3161	Populus cana	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9943	Xanthostemon chrysanthus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	3

Activity Type	# Activity
Tissue	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT548	Tissue	Ileum	Cavia porcellus	Inhibition	=	45.31	%	PMID[474615]
NPT548	Tissue	Ileum	Cavia porcellus	Inhibition	=	69.95	%	PMID[474615]
NPT548	Tissue	Ileum	Cavia porcellus	Inhibition	=	78.66	%	PMID[474615]

☑ 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 NPC307682 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	172
0.1-0.2	2208
0.2-0.3	8095
0.3-0.4	9826
0.4-0.5	7514
0.5-0.6	13436
0.6-0.7	1376
0.7-0.8	69
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8207	Intermediate Similarity	NPC189908
0.8162	Intermediate Similarity	NPC218323
0.8071	Intermediate Similarity	NPC266425
0.8043	Intermediate Similarity	NPC283079
0.7943	Intermediate Similarity	NPC132308
0.7832	Intermediate Similarity	NPC196708
0.7667	Intermediate Similarity	NPC296085
0.755	Intermediate Similarity	NPC71629
0.7448	Intermediate Similarity	NPC169766
0.7432	Intermediate Similarity	NPC231572
0.7415	Intermediate Similarity	NPC106606
0.7415	Intermediate Similarity	NPC99078
0.7365	Intermediate Similarity	NPC220923
0.7365	Intermediate Similarity	NPC252107
0.7365	Intermediate Similarity	NPC470707
0.7347	Intermediate Similarity	NPC73883
0.7347	Intermediate Similarity	NPC205178
0.7347	Intermediate Similarity	NPC136330
0.7347	Intermediate Similarity	NPC255817
0.7347	Intermediate Similarity	NPC251454
0.7347	Intermediate Similarity	NPC277042
0.7347	Intermediate Similarity	NPC230698
0.7347	Intermediate Similarity	NPC96406
0.7347	Intermediate Similarity	NPC196609
0.7328	Intermediate Similarity	NPC151530
0.7328	Intermediate Similarity	NPC157473
0.7297	Intermediate Similarity	NPC145446
0.7297	Intermediate Similarity	NPC137172
0.7279	Intermediate Similarity	NPC167096
0.7279	Intermediate Similarity	NPC45783
0.7279	Intermediate Similarity	NPC159150
0.7279	Intermediate Similarity	NPC328419
0.7279	Intermediate Similarity	NPC193673
0.7279	Intermediate Similarity	NPC103947
0.7279	Intermediate Similarity	NPC94280
0.7266	Intermediate Similarity	NPC263835
0.726	Intermediate Similarity	NPC470392
0.7259	Intermediate Similarity	NPC26524
0.7252	Intermediate Similarity	NPC176971
0.7248	Intermediate Similarity	NPC214036
0.7248	Intermediate Similarity	NPC113236
0.7248	Intermediate Similarity	NPC95366
0.7248	Intermediate Similarity	NPC248505
0.7183	Intermediate Similarity	NPC472888
0.7176	Intermediate Similarity	NPC128730
0.7161	Intermediate Similarity	NPC324081
0.7143	Intermediate Similarity	NPC321133
0.7143	Intermediate Similarity	NPC217574
0.7143	Intermediate Similarity	NPC318862
0.7133	Intermediate Similarity	NPC225745
0.7133	Intermediate Similarity	NPC194359
0.7133	Intermediate Similarity	NPC28641
0.7122	Intermediate Similarity	NPC293424
0.7121	Intermediate Similarity	NPC326447
0.7114	Intermediate Similarity	NPC180647
0.7114	Intermediate Similarity	NPC138365
0.7109	Intermediate Similarity	NPC175298
0.7107	Intermediate Similarity	NPC471649
0.7067	Intermediate Similarity	NPC469808
0.7063	Intermediate Similarity	NPC328267
0.7063	Intermediate Similarity	NPC169742
0.7047	Intermediate Similarity	NPC29650
0.7047	Intermediate Similarity	NPC473360
0.7045	Intermediate Similarity	NPC473855
0.7045	Intermediate Similarity	NPC42383
0.7032	Intermediate Similarity	NPC9373
0.7023	Intermediate Similarity	NPC179686
0.7007	Intermediate Similarity	NPC120251
0.7	Intermediate Similarity	NPC13755
0.6986	Remote Similarity	NPC172403
0.698	Remote Similarity	NPC472882
0.6974	Remote Similarity	NPC472883
0.697	Remote Similarity	NPC469505
0.697	Remote Similarity	NPC283546
0.6966	Remote Similarity	NPC124776
0.6957	Remote Similarity	NPC252004
0.6951	Remote Similarity	NPC469479
0.6951	Remote Similarity	NPC254700
0.6944	Remote Similarity	NPC255253
0.6937	Remote Similarity	NPC270811
0.6937	Remote Similarity	NPC203424
0.6937	Remote Similarity	NPC206372
0.6937	Remote Similarity	NPC471073
0.6933	Remote Similarity	NPC470441
0.6923	Remote Similarity	NPC471647
0.6923	Remote Similarity	NPC471646
0.6923	Remote Similarity	NPC471576
0.6917	Remote Similarity	NPC470393
0.6912	Remote Similarity	NPC183648
0.6894	Remote Similarity	NPC298224
0.6894	Remote Similarity	NPC192596
0.6889	Remote Similarity	NPC97811
0.6875	Remote Similarity	NPC119669
0.6871	Remote Similarity	NPC17374
0.6867	Remote Similarity	NPC471651
0.6863	Remote Similarity	NPC128877
0.6861	Remote Similarity	NPC166837
0.6861	Remote Similarity	NPC23332
0.6859	Remote Similarity	NPC244338
0.6857	Remote Similarity	NPC19290
0.6857	Remote Similarity	NPC470860
0.6857	Remote Similarity	NPC268317
0.6849	Remote Similarity	NPC320242
0.6849	Remote Similarity	NPC110131
0.6848	Remote Similarity	NPC471396
0.6842	Remote Similarity	NPC109637
0.6842	Remote Similarity	NPC108875
0.6842	Remote Similarity	NPC38209
0.6842	Remote Similarity	NPC38079
0.6839	Remote Similarity	NPC138438
0.6839	Remote Similarity	NPC308571
0.6839	Remote Similarity	NPC908
0.6838	Remote Similarity	NPC259554
0.6831	Remote Similarity	NPC98748
0.6831	Remote Similarity	NPC43275
0.6831	Remote Similarity	NPC256369
0.6831	Remote Similarity	NPC264976
0.6818	Remote Similarity	NPC212850
0.6818	Remote Similarity	NPC51633
0.6818	Remote Similarity	NPC189724
0.6818	Remote Similarity	NPC307425
0.6818	Remote Similarity	NPC83289
0.6809	Remote Similarity	NPC185738
0.6809	Remote Similarity	NPC469954
0.68	Remote Similarity	NPC118419
0.68	Remote Similarity	NPC274732
0.68	Remote Similarity	NPC329731
0.6797	Remote Similarity	NPC471316
0.6792	Remote Similarity	NPC214239
0.6791	Remote Similarity	NPC473393
0.679	Remote Similarity	NPC470708
0.6788	Remote Similarity	NPC473809
0.6788	Remote Similarity	NPC231251
0.6788	Remote Similarity	NPC25067
0.6788	Remote Similarity	NPC88868
0.6788	Remote Similarity	NPC472923
0.6786	Remote Similarity	NPC284842
0.6779	Remote Similarity	NPC200555
0.6779	Remote Similarity	NPC196026
0.6776	Remote Similarity	NPC11147
0.6774	Remote Similarity	NPC123761
0.677	Remote Similarity	NPC476579
0.6766	Remote Similarity	NPC186617
0.6765	Remote Similarity	NPC291837
0.6763	Remote Similarity	NPC90903
0.6761	Remote Similarity	NPC152159
0.6761	Remote Similarity	NPC159916
0.6759	Remote Similarity	NPC298486
0.6753	Remote Similarity	NPC160747
0.6752	Remote Similarity	NPC161155
0.6752	Remote Similarity	NPC136951
0.6752	Remote Similarity	NPC97004
0.6748	Remote Similarity	NPC287757
0.6748	Remote Similarity	NPC319320
0.6742	Remote Similarity	NPC107101
0.6739	Remote Similarity	NPC57879
0.6736	Remote Similarity	NPC322569
0.6735	Remote Similarity	NPC470858
0.6733	Remote Similarity	NPC257390
0.6733	Remote Similarity	NPC282230
0.6733	Remote Similarity	NPC183348
0.6726	Remote Similarity	NPC473693
0.6726	Remote Similarity	NPC471568
0.6719	Remote Similarity	NPC473661
0.6718	Remote Similarity	NPC313918
0.6716	Remote Similarity	NPC2518
0.6713	Remote Similarity	NPC43435
0.6713	Remote Similarity	NPC37858
0.6712	Remote Similarity	NPC11799
0.6712	Remote Similarity	NPC141252
0.6712	Remote Similarity	NPC211218
0.6712	Remote Similarity	NPC21238
0.6712	Remote Similarity	NPC217277
0.6709	Remote Similarity	NPC469978
0.6709	Remote Similarity	NPC97282
0.6708	Remote Similarity	NPC39431
0.6707	Remote Similarity	NPC57512
0.6707	Remote Similarity	NPC301163
0.6707	Remote Similarity	NPC473502
0.6705	Remote Similarity	NPC4910
0.6692	Remote Similarity	NPC84325
0.6691	Remote Similarity	NPC186469
0.669	Remote Similarity	NPC268348
0.6689	Remote Similarity	NPC470977
0.6689	Remote Similarity	NPC474476
0.6689	Remote Similarity	NPC15083
0.6689	Remote Similarity	NPC470976
0.6689	Remote Similarity	NPC196979
0.6688	Remote Similarity	NPC81026
0.6688	Remote Similarity	NPC472881
0.6685	Remote Similarity	NPC477526
0.6667	Remote Similarity	NPC89630
0.6667	Remote Similarity	NPC8337
0.6667	Remote Similarity	NPC160120
0.6667	Remote Similarity	NPC123011
0.6667	Remote Similarity	NPC221798
0.6667	Remote Similarity	NPC66246
0.6667	Remote Similarity	NPC170546
0.6667	Remote Similarity	NPC31314
0.6667	Remote Similarity	NPC95977

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 NPC307682 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	126
0.1-0.2	765
0.2-0.3	1047
0.3-0.4	2065
0.4-0.5	2697
0.5-0.6	1810
0.6-0.7	601
0.7-0.8	39
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7943	Intermediate Similarity	NPD3142	Approved
0.7943	Intermediate Similarity	NPD3140	Approved
0.7606	Intermediate Similarity	NPD5746	Approved
0.7534	Intermediate Similarity	NPD743	Approved
0.75	Intermediate Similarity	NPD2245	Discovery
0.75	Intermediate Similarity	NPD5356	Approved
0.75	Intermediate Similarity	NPD5745	Approved
0.75	Intermediate Similarity	NPD5355	Approved
0.7445	Intermediate Similarity	NPD2594	Approved
0.7445	Intermediate Similarity	NPD2595	Approved
0.7391	Intermediate Similarity	NPD5262	Discontinued
0.7391	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD3152	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD5564	Approved
0.7353	Intermediate Similarity	NPD3596	Phase 2
0.7347	Intermediate Similarity	NPD2492	Phase 1
0.7315	Intermediate Similarity	NPD1725	Approved
0.731	Intermediate Similarity	NPD3374	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD7131	Phase 3
0.729	Intermediate Similarity	NPD5586	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD1241	Discontinued
0.7248	Intermediate Similarity	NPD3693	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD2486	Discontinued
0.7241	Intermediate Similarity	NPD5163	Phase 2
0.7229	Intermediate Similarity	NPD4503	Phase 2
0.7214	Intermediate Similarity	NPD3294	Phase 2
0.7197	Intermediate Similarity	NPD5373	Approved
0.7197	Intermediate Similarity	NPD5374	Approved
0.7194	Intermediate Similarity	NPD6382	Discontinued
0.7193	Intermediate Similarity	NPD6089	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1670	Discontinued
0.7161	Intermediate Similarity	NPD2335	Discontinued
0.7152	Intermediate Similarity	NPD5085	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2668	Approved
0.7143	Intermediate Similarity	NPD2667	Approved
0.7133	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD6580	Approved
0.7122	Intermediate Similarity	NPD6581	Approved
0.7121	Intermediate Similarity	NPD3134	Approved
0.7105	Intermediate Similarity	NPD2030	Discontinued
0.7083	Intermediate Similarity	NPD4098	Discontinued
0.7071	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD3627	Approved
0.7068	Intermediate Similarity	NPD1358	Approved
0.7063	Intermediate Similarity	NPD1420	Approved
0.7063	Intermediate Similarity	NPD1421	Approved
0.7063	Intermediate Similarity	NPD2429	Approved
0.7063	Intermediate Similarity	NPD7317	Phase 3
0.7063	Intermediate Similarity	NPD2428	Approved
0.7059	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD3146	Approved
0.7051	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD3451	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD2990	Approved
0.7034	Intermediate Similarity	NPD2987	Approved
0.7034	Intermediate Similarity	NPD7018	Phase 2
0.7032	Intermediate Similarity	NPD160	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD2557	Approved
0.7027	Intermediate Similarity	NPD3058	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD2554	Approved
0.7021	Intermediate Similarity	NPD2556	Approved
0.702	Intermediate Similarity	NPD2164	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD5481	Discontinued
0.7006	Intermediate Similarity	NPD6390	Discontinued
0.7006	Intermediate Similarity	NPD1975	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2653	Approved
0.6987	Remote Similarity	NPD5297	Approved
0.6982	Remote Similarity	NPD5441	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD824	Approved
0.6977	Remote Similarity	NPD4483	Discontinued
0.6975	Remote Similarity	NPD7318	Phase 3
0.6974	Remote Similarity	NPD2240	Approved
0.6974	Remote Similarity	NPD2239	Approved
0.6972	Remote Similarity	NPD3447	Discontinued
0.6962	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7577	Discontinued
0.695	Remote Similarity	NPD3445	Approved
0.695	Remote Similarity	NPD3049	Approved
0.695	Remote Similarity	NPD3443	Approved
0.695	Remote Similarity	NPD3444	Approved
0.6948	Remote Similarity	NPD2654	Approved
0.6944	Remote Similarity	NPD6543	Approved
0.6944	Remote Similarity	NPD6540	Phase 3
0.6944	Remote Similarity	NPD6582	Phase 2
0.6944	Remote Similarity	NPD6542	Approved
0.6944	Remote Similarity	NPD6539	Approved
0.6944	Remote Similarity	NPD6583	Phase 3
0.6939	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD4180	Approved
0.6937	Remote Similarity	NPD4179	Approved
0.6928	Remote Similarity	NPD3656	Approved
0.6928	Remote Similarity	NPD5865	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5295	Discontinued
0.6923	Remote Similarity	NPD6066	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3281	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD4210	Discontinued
0.6914	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD4062	Phase 3
0.6909	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD2904	Discontinued
0.6909	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6890	Discontinued
0.6899	Remote Similarity	NPD2186	Approved
0.6894	Remote Similarity	NPD6385	Approved
0.6894	Remote Similarity	NPD6386	Approved
0.689	Remote Similarity	NPD1307	Phase 2
0.689	Remote Similarity	NPD1309	Phase 2
0.6887	Remote Similarity	NPD3052	Approved
0.6887	Remote Similarity	NPD3054	Approved
0.6886	Remote Similarity	NPD2388	Discontinued
0.6879	Remote Similarity	NPD3124	Discontinued
0.6875	Remote Similarity	NPD746	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD4477	Approved
0.6863	Remote Similarity	NPD4476	Approved
0.6852	Remote Similarity	NPD6844	Discontinued
0.6849	Remote Similarity	NPD1820	Approved
0.6849	Remote Similarity	NPD1818	Approved
0.6849	Remote Similarity	NPD1817	Approved
0.6849	Remote Similarity	NPD1819	Approved
0.6846	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD593	Approved
0.6835	Remote Similarity	NPD595	Approved
0.6828	Remote Similarity	NPD3685	Discontinued
0.6824	Remote Similarity	NPD2614	Approved
0.6821	Remote Similarity	NPD4618	Approved
0.6821	Remote Similarity	NPD4622	Approved
0.6816	Remote Similarity	NPD3659	Discontinued
0.6815	Remote Similarity	NPD6666	Approved
0.6815	Remote Similarity	NPD6667	Approved
0.6812	Remote Similarity	NPD821	Approved
0.6809	Remote Similarity	NPD5536	Phase 2
0.6805	Remote Similarity	NPD3366	Approved
0.6803	Remote Similarity	NPD6584	Phase 3
0.68	Remote Similarity	NPD4475	Approved
0.68	Remote Similarity	NPD4474	Approved
0.6797	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD6380	Phase 1
0.6797	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.679	Remote Similarity	NPD5889	Approved
0.679	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.679	Remote Similarity	NPD5890	Approved
0.679	Remote Similarity	NPD7110	Phase 1
0.6788	Remote Similarity	NPD8031	Discontinued
0.6781	Remote Similarity	NPD6541	Approved
0.6781	Remote Similarity	NPD6538	Approved
0.6779	Remote Similarity	NPD3180	Approved
0.6779	Remote Similarity	NPD3166	Approved
0.6779	Remote Similarity	NPD3164	Approved
0.6779	Remote Similarity	NPD3179	Approved
0.6779	Remote Similarity	NPD3165	Approved
0.6779	Remote Similarity	NPD3167	Approved
0.6774	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.677	Remote Similarity	NPD2052	Approved
0.6768	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD5967	Approved
0.6765	Remote Similarity	NPD2684	Approved
0.6765	Remote Similarity	NPD7177	Discontinued
0.6753	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD6032	Approved
0.6753	Remote Similarity	NPD2531	Phase 2
0.675	Remote Similarity	NPD7427	Discontinued
0.6747	Remote Similarity	NPD8245	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD6862	Phase 2
0.6733	Remote Similarity	NPD7294	Phase 1
0.6733	Remote Similarity	NPD5718	Phase 2
0.6732	Remote Similarity	NPD2200	Suspended
0.6732	Remote Similarity	NPD5688	Approved
0.6732	Remote Similarity	NPD5689	Approved
0.6731	Remote Similarity	NPD6364	Approved
0.6731	Remote Similarity	NPD4162	Approved
0.6731	Remote Similarity	NPD44	Approved
0.673	Remote Similarity	NPD4661	Approved
0.673	Remote Similarity	NPD3536	Discontinued
0.673	Remote Similarity	NPD4662	Approved
0.6728	Remote Similarity	NPD2592	Discontinued
0.6728	Remote Similarity	NPD6876	Approved
0.6728	Remote Similarity	NPD22	Approved
0.6728	Remote Similarity	NPD6875	Approved
0.6728	Remote Similarity	NPD2053	Approved
0.6726	Remote Similarity	NPD7608	Discontinued
0.6723	Remote Similarity	NPD5114	Approved
0.6723	Remote Similarity	NPD5112	Approved
0.6723	Remote Similarity	NPD5113	Approved
0.6712	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD682	Discontinued
0.6711	Remote Similarity	NPD4340	Discontinued
0.6711	Remote Similarity	NPD4207	Discontinued
0.671	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD5535	Approved
0.6691	Remote Similarity	NPD7843	Approved
0.6689	Remote Similarity	NPD7905	Discontinued
0.6689	Remote Similarity	NPD3530	Approved
0.6689	Remote Similarity	NPD3531	Approved
0.6689	Remote Similarity	NPD3532	Approved
0.6689	Remote Similarity	NPD7265	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data