NPASS Compound

Structure

CID67296 OpenBabel06191715402D 30 33 0 0 1 0 0 0 0 0999 V2000 3.4159 3.3156 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7020 1.1858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7059 -0.9404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8626 2.2773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7247 1.4539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7319 0.0259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0850 2.5725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7885 0.7791 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5126 0.0407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7058 1.6472 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9224 1.2791 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0449 2.8529 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6053 0.4611 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8584 0.5129 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1928 0.7738 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8435 1.5128 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0299 1.9998 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8884 1.4869 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1793 0.6100 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.5805 -0.1991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8734 0.4870 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7468 -0.9740 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2087 3.8394 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7019 2.0257 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0449 2.9997 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7618 1.9739 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2497 -0.9422 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7319 -0.0259 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5860 -0.3036 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 2 0 0 0 0 3 9 2 0 0 0 0 4 12 1 0 0 0 0 5 13 1 0 0 0 0 6 22 1 0 0 0 0 7 10 1 0 0 0 0 7 12 1 0 0 0 0 8 2 1 6 0 0 0 8 11 1 0 0 0 0 8 20 1 0 0 0 0 9 13 1 0 0 0 0 10 5 1 1 0 0 0 10 15 1 0 0 0 0 11 4 1 1 0 0 0 11 19 1 0 0 0 0 12 23 1 6 0 0 0 13 28 1 1 0 0 0 14 6 1 6 0 0 0 14 16 1 0 0 0 0 14 29 1 0 0 0 0 15 9 1 1 0 0 0 15 19 1 0 0 0 0 16 17 1 0 0 0 0 16 24 1 1 0 0 0 17 18 1 0 0 0 0 17 25 1 6 0 0 0 18 21 1 0 0 0 0 18 26 1 1 0 0 0 19 30 1 6 0 0 0 20 27 2 0 0 0 0 20 30 1 0 0 0 0 21 28 1 6 0 0 0 21 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	426.19
Volume:	408.749
LogP:	0.107
LogD:	0.122
LogS:	-1.724
# Rotatable Bonds:	3
TPSA:	145.91
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.279
Synthetic Accessibility Score:	5.229
Fsp3:	0.762
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:	-6.156
MDCK Permeability:	0.00013307089102454484
Pgp-inhibitor:	0.001
Pgp-substrate:	0.976
Human Intestinal Absorption (HIA):	0.894
20% Bioavailability (F20%):	0.069
30% Bioavailability (F30%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.164
Plasma Protein Binding (PPB):	49.8572998046875%
Volume Distribution (VD):	0.666
Pgp-substrate:	49.29039001464844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.062
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.385
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.025
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.087
CYP3A4-inhibitor:	0.015
CYP3A4-substrate:	0.096

ADMET: Excretion

Clearance (CL):	1.992
Half-life (T1/2):	0.495

ADMET: Toxicity

hERG Blockers:	0.09
Human Hepatotoxicity (H-HT):	0.784
Drug-inuced Liver Injury (DILI):	0.619
AMES Toxicity:	0.047
Rat Oral Acute Toxicity:	0.55
Maximum Recommended Daily Dose:	0.933
Skin Sensitization:	0.099
Carcinogencity:	0.162
Eye Corrosion:	0.004
Eye Irritation:	0.034
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC67296

Natural Product ID:	NPC67296
*Common Name:**	Ixerin F
IUPAC Name:	(3S,3aS,5R,6aR,8S,9aR,9bS)-5-hydroxy-3-methyl-6,9-dimethylidene-8-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3a,4,5,6a,7,8,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one
Synonyms:
Standard InCHIKey:	GHVUDSYPMZZROW-NOYJVBPASA-N
Standard InCHI:	InChI=1S/C21H30O9/c1-7-10-5-13(28-21-18(26)17(25)16(24)14(6-22)29-21)9(3)15(10)19-11(4-12(7)23)8(2)20(27)30-19/h8,10-19,21-26H,1,3-6H2,2H3/t8-,10-,11-,12+,13-,14+,15-,16+,17-,18+,19-,21+/m0/s1
SMILES:	OC[C@H]1O[C@@H](O[C@H]2C[C@@H]3[C@H](C2=C)[C@H]2OC(=O)[C@H]([C@@H]2C[C@H](C3=C)O)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3622759
PubChem CID:	21636023
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001770] Guaianolides and derivatives

*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
NPO32813	ixeris dentata	Species	Asteraceae	Eukaryota	Roots	n.a.	n.a.	PMID[26341134]
NPO8975	Aconitum nemorum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8975	Aconitum nemorum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8975	Aconitum nemorum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2434	Lipotriche scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4151	Rhamnus wightii	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8975	Aconitum nemorum	Species	Ranunculaceae	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	4

Activity Type	# Activity
NON-MOLECULAR	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	18.6	uM	PMID[494240]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	17.5	uM	PMID[494240]
NPT27	Others	Unspecified		Activity	=	101.7	%	PMID[494240]
NPT27	Others	Unspecified		Activity	=	114.2	%	PMID[494240]

☑ 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 NPC67296 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	233
0.1-0.2	1644
0.2-0.3	5871
0.3-0.4	12668
0.4-0.5	10260
0.5-0.6	7369
0.6-0.7	4121
0.7-0.8	485
0.8-0.85	34
0.85-0.9	0
0.9-0.95	7
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9684	High Similarity	NPC80144
0.9677	High Similarity	NPC236580
0.9677	High Similarity	NPC304445
0.957	High Similarity	NPC474297
0.9368	High Similarity	NPC49833
0.9368	High Similarity	NPC249171
0.9184	High Similarity	NPC473148
0.9062	High Similarity	NPC261372
0.9062	High Similarity	NPC263674
0.9062	High Similarity	NPC58267
0.8854	High Similarity	NPC167893
0.8627	High Similarity	NPC170432
0.8614	High Similarity	NPC475928
0.8544	High Similarity	NPC197813
0.8544	High Similarity	NPC80338
0.8544	High Similarity	NPC148270
0.8515	High Similarity	NPC4899
0.8515	High Similarity	NPC35185
0.8515	High Similarity	NPC474730
0.8515	High Similarity	NPC177013
0.85	High Similarity	NPC473146
0.8485	Intermediate Similarity	NPC471150
0.8447	Intermediate Similarity	NPC127235
0.8431	Intermediate Similarity	NPC37240
0.8421	Intermediate Similarity	NPC207114
0.8421	Intermediate Similarity	NPC217983
0.8416	Intermediate Similarity	NPC287539
0.8416	Intermediate Similarity	NPC3488
0.8384	Intermediate Similarity	NPC161293
0.8333	Intermediate Similarity	NPC106668
0.8302	Intermediate Similarity	NPC193741
0.83	Intermediate Similarity	NPC472290
0.83	Intermediate Similarity	NPC474313
0.8286	Intermediate Similarity	NPC110701
0.828	Intermediate Similarity	NPC128246
0.8265	Intermediate Similarity	NPC475788
0.8252	Intermediate Similarity	NPC27687
0.8247	Intermediate Similarity	NPC19087
0.8218	Intermediate Similarity	NPC472015
0.8211	Intermediate Similarity	NPC187661
0.8163	Intermediate Similarity	NPC475925
0.8163	Intermediate Similarity	NPC235051
0.8163	Intermediate Similarity	NPC184063
0.8148	Intermediate Similarity	NPC475924
0.8148	Intermediate Similarity	NPC475851
0.8144	Intermediate Similarity	NPC38392
0.8137	Intermediate Similarity	NPC186861
0.8137	Intermediate Similarity	NPC471381
0.81	Intermediate Similarity	NPC476053
0.81	Intermediate Similarity	NPC472873
0.8091	Intermediate Similarity	NPC277583
0.8065	Intermediate Similarity	NPC126248
0.8061	Intermediate Similarity	NPC297474
0.8061	Intermediate Similarity	NPC54065
0.8041	Intermediate Similarity	NPC470009
0.8039	Intermediate Similarity	NPC37866
0.802	Intermediate Similarity	NPC142529
0.802	Intermediate Similarity	NPC91771
0.802	Intermediate Similarity	NPC476009
0.802	Intermediate Similarity	NPC54731
0.8	Intermediate Similarity	NPC194859
0.8	Intermediate Similarity	NPC224386
0.798	Intermediate Similarity	NPC63193
0.798	Intermediate Similarity	NPC171360
0.798	Intermediate Similarity	NPC133888
0.798	Intermediate Similarity	NPC35959
0.798	Intermediate Similarity	NPC293001
0.798	Intermediate Similarity	NPC57304
0.798	Intermediate Similarity	NPC29821
0.7959	Intermediate Similarity	NPC92974
0.7959	Intermediate Similarity	NPC155935
0.7959	Intermediate Similarity	NPC215556
0.7938	Intermediate Similarity	NPC118601
0.7938	Intermediate Similarity	NPC186148
0.7938	Intermediate Similarity	NPC190753
0.7925	Intermediate Similarity	NPC54737
0.7921	Intermediate Similarity	NPC93869
0.7921	Intermediate Similarity	NPC163228
0.7921	Intermediate Similarity	NPC6765
0.7895	Intermediate Similarity	NPC111409
0.7879	Intermediate Similarity	NPC474323
0.7879	Intermediate Similarity	NPC35809
0.7879	Intermediate Similarity	NPC216284
0.7879	Intermediate Similarity	NPC206614
0.7879	Intermediate Similarity	NPC246173
0.787	Intermediate Similarity	NPC139838
0.787	Intermediate Similarity	NPC59489
0.7857	Intermediate Similarity	NPC178875
0.7857	Intermediate Similarity	NPC58219
0.7857	Intermediate Similarity	NPC79549
0.7857	Intermediate Similarity	NPC177629
0.7843	Intermediate Similarity	NPC306041
0.7835	Intermediate Similarity	NPC304558
0.7835	Intermediate Similarity	NPC236692
0.7835	Intermediate Similarity	NPC309757
0.7822	Intermediate Similarity	NPC274588
0.78	Intermediate Similarity	NPC472197
0.7789	Intermediate Similarity	NPC246076
0.7778	Intermediate Similarity	NPC475960
0.7767	Intermediate Similarity	NPC311904
0.7767	Intermediate Similarity	NPC181151
0.7766	Intermediate Similarity	NPC51507
0.7757	Intermediate Similarity	NPC223450
0.7757	Intermediate Similarity	NPC243998
0.7755	Intermediate Similarity	NPC475773
0.7745	Intermediate Similarity	NPC36954
0.7745	Intermediate Similarity	NPC475900
0.7739	Intermediate Similarity	NPC470829
0.7739	Intermediate Similarity	NPC473228
0.7727	Intermediate Similarity	NPC471251
0.7723	Intermediate Similarity	NPC200237
0.7723	Intermediate Similarity	NPC475912
0.7723	Intermediate Similarity	NPC258216
0.7714	Intermediate Similarity	NPC216911
0.7714	Intermediate Similarity	NPC171759
0.7714	Intermediate Similarity	NPC150923
0.7692	Intermediate Similarity	NPC45125
0.7677	Intermediate Similarity	NPC471149
0.767	Intermediate Similarity	NPC284063
0.767	Intermediate Similarity	NPC24956
0.767	Intermediate Similarity	NPC18019
0.767	Intermediate Similarity	NPC170527
0.7653	Intermediate Similarity	NPC474762
0.7653	Intermediate Similarity	NPC476015
0.7653	Intermediate Similarity	NPC56593
0.7653	Intermediate Similarity	NPC475019
0.7653	Intermediate Similarity	NPC474949
0.7653	Intermediate Similarity	NPC470657
0.7653	Intermediate Similarity	NPC470242
0.7652	Intermediate Similarity	NPC142882
0.7647	Intermediate Similarity	NPC63897
0.7647	Intermediate Similarity	NPC71589
0.7647	Intermediate Similarity	NPC198853
0.7647	Intermediate Similarity	NPC190294
0.7647	Intermediate Similarity	NPC473331
0.7642	Intermediate Similarity	NPC250545
0.7642	Intermediate Similarity	NPC86077
0.7642	Intermediate Similarity	NPC261117
0.7642	Intermediate Similarity	NPC304163
0.7642	Intermediate Similarity	NPC310804
0.7636	Intermediate Similarity	NPC124053
0.7629	Intermediate Similarity	NPC474780
0.7629	Intermediate Similarity	NPC475963
0.7629	Intermediate Similarity	NPC3464
0.7629	Intermediate Similarity	NPC151176
0.7624	Intermediate Similarity	NPC155215
0.7624	Intermediate Similarity	NPC191339
0.7624	Intermediate Similarity	NPC208886
0.7624	Intermediate Similarity	NPC184463
0.7624	Intermediate Similarity	NPC12172
0.7624	Intermediate Similarity	NPC286341
0.7619	Intermediate Similarity	NPC476211
0.7619	Intermediate Similarity	NPC476320
0.76	Intermediate Similarity	NPC283409
0.76	Intermediate Similarity	NPC12872
0.76	Intermediate Similarity	NPC168679
0.7596	Intermediate Similarity	NPC86843
0.7593	Intermediate Similarity	NPC44004
0.7593	Intermediate Similarity	NPC41681
0.7589	Intermediate Similarity	NPC293658
0.7589	Intermediate Similarity	NPC474410
0.7576	Intermediate Similarity	NPC31349
0.7576	Intermediate Similarity	NPC24728
0.7573	Intermediate Similarity	NPC170120
0.7573	Intermediate Similarity	NPC14961
0.7573	Intermediate Similarity	NPC213698
0.7573	Intermediate Similarity	NPC270013
0.757	Intermediate Similarity	NPC474775
0.757	Intermediate Similarity	NPC329834
0.7551	Intermediate Similarity	NPC300082
0.7551	Intermediate Similarity	NPC329749
0.7551	Intermediate Similarity	NPC284534
0.7551	Intermediate Similarity	NPC204105
0.7549	Intermediate Similarity	NPC153590
0.7549	Intermediate Similarity	NPC320089
0.7549	Intermediate Similarity	NPC81419
0.7549	Intermediate Similarity	NPC473234
0.7549	Intermediate Similarity	NPC60386
0.7549	Intermediate Similarity	NPC212486
0.7549	Intermediate Similarity	NPC473263
0.7549	Intermediate Similarity	NPC476300
0.7549	Intermediate Similarity	NPC308656
0.7549	Intermediate Similarity	NPC473273
0.7549	Intermediate Similarity	NPC179746
0.7547	Intermediate Similarity	NPC476230
0.7547	Intermediate Similarity	NPC27474
0.7547	Intermediate Similarity	NPC28304
0.7547	Intermediate Similarity	NPC298255
0.7545	Intermediate Similarity	NPC471250
0.7545	Intermediate Similarity	NPC118225
0.7525	Intermediate Similarity	NPC216826
0.7525	Intermediate Similarity	NPC65665
0.7525	Intermediate Similarity	NPC120021
0.7525	Intermediate Similarity	NPC470573
0.7525	Intermediate Similarity	NPC231710
0.7525	Intermediate Similarity	NPC270908
0.7524	Intermediate Similarity	NPC187268
0.75	Intermediate Similarity	NPC476315
0.75	Intermediate Similarity	NPC100487
0.75	Intermediate Similarity	NPC474917

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 NPC67296 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	238
0.1-0.2	2306
0.2-0.3	3884
0.3-0.4	1838
0.4-0.5	529
0.5-0.6	270
0.6-0.7	80
0.7-0.8	5
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
0.7364	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6686	Approved
0.7288	Intermediate Similarity	NPD8516	Approved
0.7288	Intermediate Similarity	NPD8513	Phase 3
0.7288	Intermediate Similarity	NPD8517	Approved
0.7288	Intermediate Similarity	NPD8515	Approved
0.7281	Intermediate Similarity	NPD8133	Approved
0.7257	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD7507	Approved
0.7184	Intermediate Similarity	NPD6698	Approved
0.7184	Intermediate Similarity	NPD46	Approved
0.7016	Intermediate Similarity	NPD7319	Approved
0.6952	Remote Similarity	NPD7983	Approved
0.6923	Remote Similarity	NPD1695	Approved
0.6916	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6412	Phase 2
0.687	Remote Similarity	NPD6371	Approved
0.6796	Remote Similarity	NPD4249	Approved
0.6752	Remote Similarity	NPD6053	Discontinued
0.6731	Remote Similarity	NPD4250	Approved
0.6731	Remote Similarity	NPD4251	Approved
0.6727	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD8268	Approved
0.6721	Remote Similarity	NPD8267	Approved
0.6721	Remote Similarity	NPD8266	Approved
0.6721	Remote Similarity	NPD8269	Approved
0.672	Remote Similarity	NPD8074	Phase 3
0.6612	Remote Similarity	NPD7328	Approved
0.6612	Remote Similarity	NPD7327	Approved
0.6585	Remote Similarity	NPD8033	Approved
0.6579	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD6435	Approved
0.6557	Remote Similarity	NPD7516	Approved
0.6545	Remote Similarity	NPD7839	Suspended
0.6538	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD8451	Approved
0.6505	Remote Similarity	NPD5362	Discontinued
0.6504	Remote Similarity	NPD8377	Approved
0.6504	Remote Similarity	NPD8294	Approved
0.6496	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD5786	Approved
0.6475	Remote Similarity	NPD7641	Discontinued
0.6457	Remote Similarity	NPD8293	Discontinued
0.6457	Remote Similarity	NPD8448	Approved
0.6452	Remote Similarity	NPD8444	Approved
0.6452	Remote Similarity	NPD8380	Approved
0.6452	Remote Similarity	NPD8379	Approved
0.6452	Remote Similarity	NPD8296	Approved
0.6452	Remote Similarity	NPD8335	Approved
0.6452	Remote Similarity	NPD8378	Approved
0.6429	Remote Similarity	NPD8340	Approved
0.6429	Remote Similarity	NPD8341	Approved
0.6429	Remote Similarity	NPD8342	Approved
0.6429	Remote Similarity	NPD8299	Approved
0.6422	Remote Similarity	NPD5779	Approved
0.6422	Remote Similarity	NPD5778	Approved
0.641	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD7736	Approved
0.64	Remote Similarity	NPD6370	Approved
0.6393	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD7838	Discovery
0.6381	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD5368	Approved
0.6349	Remote Similarity	NPD7830	Approved
0.6349	Remote Similarity	NPD8328	Phase 3
0.6349	Remote Similarity	NPD7829	Approved
0.6349	Remote Similarity	NPD7642	Approved
0.6346	Remote Similarity	NPD7154	Phase 3
0.632	Remote Similarity	NPD7503	Approved
0.6308	Remote Similarity	NPD8390	Approved
0.6308	Remote Similarity	NPD8391	Approved
0.6308	Remote Similarity	NPD8392	Approved
0.6299	Remote Similarity	NPD7492	Approved
0.6283	Remote Similarity	NPD4225	Approved
0.625	Remote Similarity	NPD4269	Approved
0.625	Remote Similarity	NPD6616	Approved
0.625	Remote Similarity	NPD4270	Approved
0.624	Remote Similarity	NPD6054	Approved
0.624	Remote Similarity	NPD6059	Approved
0.6239	Remote Similarity	NPD5785	Approved
0.6228	Remote Similarity	NPD7639	Approved
0.6228	Remote Similarity	NPD7640	Approved
0.6216	Remote Similarity	NPD5282	Discontinued
0.6214	Remote Similarity	NPD4821	Approved
0.6214	Remote Similarity	NPD4819	Approved
0.6214	Remote Similarity	NPD4822	Approved
0.6214	Remote Similarity	NPD4820	Approved
0.6202	Remote Similarity	NPD7078	Approved
0.619	Remote Similarity	NPD6015	Approved
0.619	Remote Similarity	NPD6016	Approved
0.619	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD4271	Approved
0.6176	Remote Similarity	NPD4802	Phase 2
0.6176	Remote Similarity	NPD4268	Approved
0.6176	Remote Similarity	NPD4238	Approved
0.6154	Remote Similarity	NPD5369	Approved
0.6148	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD6101	Approved
0.6147	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD5988	Approved
0.6142	Remote Similarity	NPD8080	Discontinued
0.614	Remote Similarity	NPD7638	Approved
0.6129	Remote Similarity	NPD6009	Approved
0.6121	Remote Similarity	NPD8085	Approved
0.6121	Remote Similarity	NPD8083	Approved
0.6121	Remote Similarity	NPD8138	Approved
0.6121	Remote Similarity	NPD8084	Approved
0.6121	Remote Similarity	NPD8086	Approved
0.6121	Remote Similarity	NPD8082	Approved
0.6121	Remote Similarity	NPD8139	Approved
0.6111	Remote Similarity	NPD6319	Approved
0.6102	Remote Similarity	NPD6008	Approved
0.6075	Remote Similarity	NPD5363	Approved
0.6068	Remote Similarity	NPD8276	Approved
0.6068	Remote Similarity	NPD8275	Approved
0.6066	Remote Similarity	NPD6882	Approved
0.6058	Remote Similarity	NPD4252	Approved
0.6038	Remote Similarity	NPD3669	Approved
0.6038	Remote Similarity	NPD5331	Approved
0.6038	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD5332	Approved
0.6036	Remote Similarity	NPD6411	Approved
0.6034	Remote Similarity	NPD5344	Discontinued
0.6017	Remote Similarity	NPD8081	Approved
0.6016	Remote Similarity	NPD4632	Approved
0.6	Remote Similarity	NPD1779	Approved
0.6	Remote Similarity	NPD7115	Discovery
0.6	Remote Similarity	NPD4790	Discontinued
0.6	Remote Similarity	NPD8273	Phase 1
0.6	Remote Similarity	NPD1780	Approved
0.5982	Remote Similarity	NPD6399	Phase 3
0.5979	Remote Similarity	NPD898	Approved
0.5979	Remote Similarity	NPD896	Approved
0.5979	Remote Similarity	NPD897	Approved
0.597	Remote Similarity	NPD6845	Suspended
0.5969	Remote Similarity	NPD6067	Discontinued
0.5966	Remote Similarity	NPD8393	Approved
0.595	Remote Similarity	NPD6373	Approved
0.595	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.595	Remote Similarity	NPD6372	Approved
0.5938	Remote Similarity	NPD6921	Approved
0.5935	Remote Similarity	NPD8297	Approved
0.5909	Remote Similarity	NPD8337	Approved
0.5909	Remote Similarity	NPD8336	Approved
0.5902	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5896	Remote Similarity	NPD7260	Phase 2
0.5893	Remote Similarity	NPD8034	Phase 2
0.5893	Remote Similarity	NPD8035	Phase 2
0.5893	Remote Similarity	NPD7637	Suspended
0.5868	Remote Similarity	NPD7320	Approved
0.5865	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD6649	Approved
0.5854	Remote Similarity	NPD6650	Approved
0.5847	Remote Similarity	NPD7632	Discontinued
0.5841	Remote Similarity	NPD8171	Discontinued
0.5833	Remote Similarity	NPD6675	Approved
0.5833	Remote Similarity	NPD5739	Approved
0.5833	Remote Similarity	NPD7128	Approved
0.5833	Remote Similarity	NPD6402	Approved
0.5833	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD7524	Approved
0.5789	Remote Similarity	NPD6033	Approved
0.5785	Remote Similarity	NPD5701	Approved
0.5785	Remote Similarity	NPD5697	Approved
0.5785	Remote Similarity	NPD8307	Discontinued
0.5785	Remote Similarity	NPD8140	Approved
0.5763	Remote Similarity	NPD1700	Approved
0.5738	Remote Similarity	NPD6899	Approved
0.5738	Remote Similarity	NPD6881	Approved
0.5735	Remote Similarity	NPD8338	Approved
0.5725	Remote Similarity	NPD7122	Discontinued
0.5725	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5692	Remote Similarity	NPD5983	Phase 2
0.5691	Remote Similarity	NPD6012	Approved
0.5691	Remote Similarity	NPD8305	Approved
0.5691	Remote Similarity	NPD6013	Approved
0.5691	Remote Similarity	NPD8306	Approved
0.5691	Remote Similarity	NPD6014	Approved
0.569	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5678	Remote Similarity	NPD6648	Approved
0.567	Remote Similarity	NPD7909	Approved
0.566	Remote Similarity	NPD7329	Approved
0.5656	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5645	Remote Similarity	NPD8087	Discontinued
0.5645	Remote Similarity	NPD7290	Approved
0.5645	Remote Similarity	NPD6883	Approved
0.5645	Remote Similarity	NPD6421	Discontinued
0.5645	Remote Similarity	NPD7102	Approved
0.5644	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD6084	Phase 2
0.5641	Remote Similarity	NPD6083	Phase 2
0.5636	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.561	Remote Similarity	NPD6011	Approved
0.5606	Remote Similarity	NPD7604	Phase 2
0.5603	Remote Similarity	NPD5695	Phase 3

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