NPASS Compound

Structure

NPC473148 OpenBabel07101719512D 37 40 0 0 1 0 0 0 0 0999 V2000 -6.6939 2.8647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4260 2.8647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5983 -1.7682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0934 0.6637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9683 3.0036 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0366 -0.1325 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 -1.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5600 2.3647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3036 -0.8126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 -0.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1506 2.4280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3147 -0.6636 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9619 0.8647 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8147 0.2024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1356 1.4281 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.5600 1.3647 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1801 1.1333 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2043 2.7512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6939 0.8647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4260 0.8647 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9095 3.7067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6939 -0.1353 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8279 1.3647 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 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 -2.6045 1.9510 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 9 1 0 0 0 0 3 10 2 0 0 0 0 4 11 2 0 0 0 0 5 12 2 0 0 0 0 6 10 1 0 0 0 0 6 15 1 0 0 0 0 7 14 1 0 0 0 0 8 27 1 0 0 0 0 9 19 1 0 0 0 0 10 13 1 0 0 0 0 11 14 1 0 0 0 0 12 24 1 0 0 0 0 13 7 1 1 0 0 0 13 17 1 0 0 0 0 14 35 1 1 0 0 0 15 18 1 0 0 0 0 15 34 1 1 0 0 0 16 8 1 6 0 0 0 16 20 1 0 0 0 0 16 36 1 0 0 0 0 17 11 1 1 0 0 0 17 23 1 0 0 0 0 18 12 1 1 0 0 0 18 23 1 0 0 0 0 19 25 1 0 0 0 0 19 28 1 0 0 0 0 20 21 1 0 0 0 0 20 29 1 1 0 0 0 21 22 1 0 0 0 0 21 30 1 6 0 0 0 22 26 1 0 0 0 0 22 31 1 1 0 0 0 23 37 1 6 0 0 0 24 32 2 0 0 0 0 24 37 1 0 0 0 0 25 33 2 0 0 0 0 25 34 1 0 0 0 0 26 35 1 6 0 0 0 26 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	524.23
Volume:	507.536
LogP:	-0.367
LogD:	0.594
LogS:	-1.767
# Rotatable Bonds:	7
TPSA:	172.21
# H-Bond Aceptor:	11
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.17
Synthetic Accessibility Score:	5.346
Fsp3:	0.692
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.227
MDCK Permeability:	0.00011494356294861063
Pgp-inhibitor:	0.0
Pgp-substrate:	0.014
Human Intestinal Absorption (HIA):	0.705
20% Bioavailability (F20%):	0.039
30% Bioavailability (F30%):	0.968

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.114
Plasma Protein Binding (PPB):	63.05012512207031%
Volume Distribution (VD):	0.651
Pgp-substrate:	32.79054641723633%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.024
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.188
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.03
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.062
CYP3A4-inhibitor:	0.031
CYP3A4-substrate:	0.218

ADMET: Excretion

Clearance (CL):	2.047
Half-life (T1/2):	0.596

ADMET: Toxicity

hERG Blockers:	0.142
Human Hepatotoxicity (H-HT):	0.948
Drug-inuced Liver Injury (DILI):	0.855
AMES Toxicity:	0.079
Rat Oral Acute Toxicity:	0.441
Maximum Recommended Daily Dose:	0.664
Skin Sensitization:	0.055
Carcinogencity:	0.08
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.955

Download Data

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

Natural Product: NPC473148

Natural Product ID:	NPC473148
*Common Name:**	HLZBRVYCKXUHSB-VUUNWOKMSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HLZBRVYCKXUHSB-VUUNWOKMSA-N
Standard InCHI:	InChI=1S/C26H36O11/c1-9(2)19(28)25(33)34-15-6-10(3)13-7-14(11(4)17(13)23-18(15)12(5)24(32)37-23)35-26-22(31)21(30)20(29)16(8-27)36-26/h9,13-23,26-31H,3-8H2,1-2H3/t13-,14-,15+,16+,17-,18+,19?,20+,21-,22+,23+,26+/m0/s1
SMILES:	CC(C)C(C(=O)OC1CC(=C)C2CC(C(=C)C2C3C1C(=C)C(=O)O3)OC4C(C(C(C(O4)CO)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3622765
PubChem CID:	n.a.
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]

☑ 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	=	21.5	uM	PMID[500197]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	18.2	uM	PMID[500197]
NPT27	Others	Unspecified		Activity	=	105.0	%	PMID[500197]
NPT27	Others	Unspecified		Activity	=	97.5	%	PMID[500197]

☑ 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 NPC473148 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	240
0.1-0.2	1623
0.2-0.3	6028
0.3-0.4	12841
0.4-0.5	9994
0.5-0.6	7274
0.6-0.7	4205
0.7-0.8	428
0.8-0.85	51
0.85-0.9	1
0.9-0.95	7
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9579	High Similarity	NPC249171
0.9579	High Similarity	NPC49833
0.9474	High Similarity	NPC304445
0.9474	High Similarity	NPC236580
0.9286	High Similarity	NPC80144
0.9263	High Similarity	NPC167893
0.9184	High Similarity	NPC67296
0.9167	High Similarity	NPC474297
0.9072	High Similarity	NPC263674
0.9072	High Similarity	NPC58267
0.9072	High Similarity	NPC261372
0.8687	High Similarity	NPC474313
0.8627	High Similarity	NPC475928
0.8462	Intermediate Similarity	NPC170432
0.8438	Intermediate Similarity	NPC217983
0.8438	Intermediate Similarity	NPC207114
0.8416	Intermediate Similarity	NPC472015
0.8381	Intermediate Similarity	NPC80338
0.8381	Intermediate Similarity	NPC148270
0.8381	Intermediate Similarity	NPC197813
0.835	Intermediate Similarity	NPC35185
0.835	Intermediate Similarity	NPC474730
0.835	Intermediate Similarity	NPC4899
0.835	Intermediate Similarity	NPC106668
0.835	Intermediate Similarity	NPC177013
0.8333	Intermediate Similarity	NPC473146
0.8317	Intermediate Similarity	NPC471150
0.83	Intermediate Similarity	NPC472873
0.8283	Intermediate Similarity	NPC475788
0.8269	Intermediate Similarity	NPC37240
0.8269	Intermediate Similarity	NPC27687
0.8265	Intermediate Similarity	NPC54065
0.8265	Intermediate Similarity	NPC297474
0.8265	Intermediate Similarity	NPC19087
0.8229	Intermediate Similarity	NPC187661
0.8218	Intermediate Similarity	NPC476009
0.8182	Intermediate Similarity	NPC57304
0.8182	Intermediate Similarity	NPC293001
0.8182	Intermediate Similarity	NPC29821
0.8182	Intermediate Similarity	NPC171360
0.8182	Intermediate Similarity	NPC35959
0.8182	Intermediate Similarity	NPC184063
0.8182	Intermediate Similarity	NPC133888
0.8182	Intermediate Similarity	NPC63193
0.8163	Intermediate Similarity	NPC38392
0.8163	Intermediate Similarity	NPC215556
0.8163	Intermediate Similarity	NPC155935
0.8148	Intermediate Similarity	NPC193741
0.8131	Intermediate Similarity	NPC110701
0.8119	Intermediate Similarity	NPC475900
0.8119	Intermediate Similarity	NPC163228
0.8113	Intermediate Similarity	NPC44004
0.8113	Intermediate Similarity	NPC127235
0.8081	Intermediate Similarity	NPC474323
0.8081	Intermediate Similarity	NPC35809
0.8081	Intermediate Similarity	NPC216284
0.8081	Intermediate Similarity	NPC206614
0.8077	Intermediate Similarity	NPC287539
0.8077	Intermediate Similarity	NPC3488
0.8061	Intermediate Similarity	NPC79549
0.8061	Intermediate Similarity	NPC470009
0.8058	Intermediate Similarity	NPC37866
0.8041	Intermediate Similarity	NPC304558
0.8039	Intermediate Similarity	NPC161293
0.8039	Intermediate Similarity	NPC54731
0.8039	Intermediate Similarity	NPC306041
0.8037	Intermediate Similarity	NPC26617
0.8021	Intermediate Similarity	NPC224386
0.8021	Intermediate Similarity	NPC194859
0.802	Intermediate Similarity	NPC473331
0.8	Intermediate Similarity	NPC475924
0.8	Intermediate Similarity	NPC475851
0.8	Intermediate Similarity	NPC475925
0.8	Intermediate Similarity	NPC235051
0.8	Intermediate Similarity	NPC246076
0.7981	Intermediate Similarity	NPC186861
0.7981	Intermediate Similarity	NPC471381
0.798	Intermediate Similarity	NPC92974
0.798	Intermediate Similarity	NPC283409
0.7963	Intermediate Similarity	NPC68248
0.7961	Intermediate Similarity	NPC311904
0.7941	Intermediate Similarity	NPC93869
0.7941	Intermediate Similarity	NPC6765
0.7917	Intermediate Similarity	NPC128246
0.7905	Intermediate Similarity	NPC216911
0.7885	Intermediate Similarity	NPC45125
0.7879	Intermediate Similarity	NPC58219
0.7879	Intermediate Similarity	NPC471149
0.7879	Intermediate Similarity	NPC177629
0.7864	Intermediate Similarity	NPC76862
0.7864	Intermediate Similarity	NPC158416
0.7864	Intermediate Similarity	NPC24956
0.7864	Intermediate Similarity	NPC142529
0.7864	Intermediate Similarity	NPC470883
0.7864	Intermediate Similarity	NPC39859
0.7864	Intermediate Similarity	NPC91771
0.7864	Intermediate Similarity	NPC18019
0.7857	Intermediate Similarity	NPC56593
0.7843	Intermediate Similarity	NPC190294
0.7843	Intermediate Similarity	NPC274588
0.7822	Intermediate Similarity	NPC329952
0.7822	Intermediate Similarity	NPC155215
0.781	Intermediate Similarity	NPC476320
0.781	Intermediate Similarity	NPC476211
0.7798	Intermediate Similarity	NPC255082
0.7788	Intermediate Similarity	NPC323421
0.7788	Intermediate Similarity	NPC472290
0.7788	Intermediate Similarity	NPC181151
0.7788	Intermediate Similarity	NPC328562
0.7778	Intermediate Similarity	NPC24728
0.7778	Intermediate Similarity	NPC186148
0.7778	Intermediate Similarity	NPC118601
0.7778	Intermediate Similarity	NPC190753
0.7778	Intermediate Similarity	NPC54737
0.7767	Intermediate Similarity	NPC476053
0.7767	Intermediate Similarity	NPC213698
0.7757	Intermediate Similarity	NPC329834
0.7755	Intermediate Similarity	NPC284534
0.7755	Intermediate Similarity	NPC204105
0.7755	Intermediate Similarity	NPC300082
0.7745	Intermediate Similarity	NPC258216
0.7736	Intermediate Similarity	NPC150923
0.7736	Intermediate Similarity	NPC476230
0.7736	Intermediate Similarity	NPC27474
0.7732	Intermediate Similarity	NPC111409
0.7727	Intermediate Similarity	NPC59489
0.7727	Intermediate Similarity	NPC139838
0.7708	Intermediate Similarity	NPC126248
0.77	Intermediate Similarity	NPC178875
0.7692	Intermediate Similarity	NPC31645
0.7692	Intermediate Similarity	NPC170527
0.7685	Intermediate Similarity	NPC474917
0.7677	Intermediate Similarity	NPC162071
0.7677	Intermediate Similarity	NPC476015
0.7677	Intermediate Similarity	NPC236692
0.7677	Intermediate Similarity	NPC309757
0.7677	Intermediate Similarity	NPC475019
0.7677	Intermediate Similarity	NPC64153
0.7677	Intermediate Similarity	NPC474949
0.7677	Intermediate Similarity	NPC474762
0.7672	Intermediate Similarity	NPC142882
0.767	Intermediate Similarity	NPC127019
0.767	Intermediate Similarity	NPC198853
0.767	Intermediate Similarity	NPC63897
0.7664	Intermediate Similarity	NPC86077
0.7664	Intermediate Similarity	NPC261117
0.7664	Intermediate Similarity	NPC474747
0.7664	Intermediate Similarity	NPC310804
0.7647	Intermediate Similarity	NPC184463
0.7647	Intermediate Similarity	NPC133698
0.7647	Intermediate Similarity	NPC131209
0.7647	Intermediate Similarity	NPC472197
0.7642	Intermediate Similarity	NPC70865
0.7636	Intermediate Similarity	NPC475960
0.7636	Intermediate Similarity	NPC392
0.7636	Intermediate Similarity	NPC177524
0.7636	Intermediate Similarity	NPC219900
0.7632	Intermediate Similarity	NPC277583
0.7624	Intermediate Similarity	NPC173926
0.7624	Intermediate Similarity	NPC474951
0.7624	Intermediate Similarity	NPC472872
0.7619	Intermediate Similarity	NPC474182
0.7619	Intermediate Similarity	NPC161493
0.7619	Intermediate Similarity	NPC476612
0.7619	Intermediate Similarity	NPC476613
0.7607	Intermediate Similarity	NPC470829
0.7607	Intermediate Similarity	NPC473228
0.7596	Intermediate Similarity	NPC52044
0.7596	Intermediate Similarity	NPC170120
0.7596	Intermediate Similarity	NPC36954
0.7596	Intermediate Similarity	NPC67584
0.7593	Intermediate Similarity	NPC329704
0.7593	Intermediate Similarity	NPC475945
0.7593	Intermediate Similarity	NPC475871
0.7576	Intermediate Similarity	NPC329749
0.7573	Intermediate Similarity	NPC200237
0.7573	Intermediate Similarity	NPC60386
0.7573	Intermediate Similarity	NPC472196
0.7573	Intermediate Similarity	NPC476300
0.7573	Intermediate Similarity	NPC473273
0.7573	Intermediate Similarity	NPC320089
0.7573	Intermediate Similarity	NPC473234
0.7573	Intermediate Similarity	NPC238090
0.7573	Intermediate Similarity	NPC473263
0.7573	Intermediate Similarity	NPC472874
0.7573	Intermediate Similarity	NPC472195
0.7573	Intermediate Similarity	NPC308656
0.757	Intermediate Similarity	NPC171759
0.757	Intermediate Similarity	NPC473332
0.757	Intermediate Similarity	NPC476228
0.7551	Intermediate Similarity	NPC245665
0.7547	Intermediate Similarity	NPC187268
0.7524	Intermediate Similarity	NPC213078
0.7523	Intermediate Similarity	NPC472748
0.7523	Intermediate Similarity	NPC86095
0.7521	Intermediate Similarity	NPC317635
0.7521	Intermediate Similarity	NPC329008
0.75	Intermediate Similarity	NPC159698
0.75	Intermediate Similarity	NPC320019
0.75	Intermediate Similarity	NPC304163

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 NPC473148 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	243
0.1-0.2	2257
0.2-0.3	3960
0.3-0.4	1791
0.4-0.5	547
0.5-0.6	285
0.6-0.7	65
0.7-0.8	2
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
0.8037	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD6686	Approved
0.7434	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD6698	Approved
0.7379	Intermediate Similarity	NPD46	Approved
0.7304	Intermediate Similarity	NPD8133	Approved
0.7115	Intermediate Similarity	NPD1695	Approved
0.708	Intermediate Similarity	NPD6412	Phase 2
0.7073	Intermediate Similarity	NPD7507	Approved
0.7043	Intermediate Similarity	NPD6371	Approved
0.6909	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7319	Approved
0.6885	Remote Similarity	NPD8516	Approved
0.6885	Remote Similarity	NPD8513	Phase 3
0.6885	Remote Similarity	NPD8515	Approved
0.6885	Remote Similarity	NPD8517	Approved
0.6789	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD7328	Approved
0.6777	Remote Similarity	NPD7327	Approved
0.6748	Remote Similarity	NPD8033	Approved
0.6729	Remote Similarity	NPD7838	Discovery
0.6721	Remote Similarity	NPD7516	Approved
0.6694	Remote Similarity	NPD6370	Approved
0.6693	Remote Similarity	NPD7736	Approved
0.6667	Remote Similarity	NPD8377	Approved
0.6667	Remote Similarity	NPD8294	Approved
0.6639	Remote Similarity	NPD6053	Discontinued
0.6614	Remote Similarity	NPD8293	Discontinued
0.6613	Remote Similarity	NPD8378	Approved
0.6613	Remote Similarity	NPD8296	Approved
0.6613	Remote Similarity	NPD8380	Approved
0.6613	Remote Similarity	NPD8335	Approved
0.6613	Remote Similarity	NPD8379	Approved
0.6613	Remote Similarity	NPD7503	Approved
0.6609	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD4251	Approved
0.6604	Remote Similarity	NPD4250	Approved
0.6587	Remote Similarity	NPD7492	Approved
0.6557	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD5282	Discontinued
0.6535	Remote Similarity	NPD6616	Approved
0.6532	Remote Similarity	NPD6054	Approved
0.6525	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD7983	Approved
0.6509	Remote Similarity	NPD4249	Approved
0.6508	Remote Similarity	NPD8328	Phase 3
0.6504	Remote Similarity	NPD7641	Discontinued
0.6484	Remote Similarity	NPD7078	Approved
0.648	Remote Similarity	NPD8267	Approved
0.648	Remote Similarity	NPD8268	Approved
0.648	Remote Similarity	NPD8269	Approved
0.648	Remote Similarity	NPD8266	Approved
0.6441	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD5785	Approved
0.6418	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6059	Approved
0.6381	Remote Similarity	NPD5362	Discontinued
0.6378	Remote Similarity	NPD7642	Approved
0.6378	Remote Similarity	NPD7830	Approved
0.6378	Remote Similarity	NPD7829	Approved
0.6364	Remote Similarity	NPD6882	Approved
0.6357	Remote Similarity	NPD8074	Phase 3
0.6349	Remote Similarity	NPD6015	Approved
0.6349	Remote Similarity	NPD6016	Approved
0.6325	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD4225	Approved
0.6316	Remote Similarity	NPD7638	Approved
0.6299	Remote Similarity	NPD8080	Discontinued
0.6299	Remote Similarity	NPD5988	Approved
0.629	Remote Similarity	NPD6009	Approved
0.6286	Remote Similarity	NPD6435	Approved
0.6279	Remote Similarity	NPD8451	Approved
0.627	Remote Similarity	NPD6319	Approved
0.6262	Remote Similarity	NPD5363	Approved
0.6261	Remote Similarity	NPD7639	Approved
0.6261	Remote Similarity	NPD7640	Approved
0.625	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD6845	Suspended
0.6231	Remote Similarity	NPD8448	Approved
0.623	Remote Similarity	NPD8297	Approved
0.6226	Remote Similarity	NPD7154	Phase 3
0.622	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.622	Remote Similarity	NPD8444	Approved
0.6214	Remote Similarity	NPD4802	Phase 2
0.6214	Remote Similarity	NPD4238	Approved
0.6207	Remote Similarity	NPD5344	Discontinued
0.619	Remote Similarity	NPD5369	Approved
0.6179	Remote Similarity	NPD4632	Approved
0.6165	Remote Similarity	NPD7260	Phase 2
0.616	Remote Similarity	NPD7115	Discovery
0.616	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD6650	Approved
0.6148	Remote Similarity	NPD6649	Approved
0.614	Remote Similarity	NPD7839	Suspended
0.6132	Remote Similarity	NPD4270	Approved
0.6132	Remote Similarity	NPD4269	Approved
0.6124	Remote Similarity	NPD6067	Discontinued
0.6116	Remote Similarity	NPD6372	Approved
0.6116	Remote Similarity	NPD6373	Approved
0.6095	Remote Similarity	NPD5368	Approved
0.6095	Remote Similarity	NPD4820	Approved
0.6095	Remote Similarity	NPD4822	Approved
0.6095	Remote Similarity	NPD4819	Approved
0.6095	Remote Similarity	NPD4821	Approved
0.609	Remote Similarity	NPD8391	Approved
0.609	Remote Similarity	NPD8390	Approved
0.609	Remote Similarity	NPD8392	Approved
0.6087	Remote Similarity	NPD6084	Phase 2
0.6087	Remote Similarity	NPD6083	Phase 2
0.6077	Remote Similarity	NPD8341	Approved
0.6077	Remote Similarity	NPD8340	Approved
0.6077	Remote Similarity	NPD8299	Approved
0.6077	Remote Similarity	NPD8342	Approved
0.6061	Remote Similarity	NPD8337	Approved
0.6061	Remote Similarity	NPD8336	Approved
0.6058	Remote Similarity	NPD4268	Approved
0.6058	Remote Similarity	NPD4271	Approved
0.6055	Remote Similarity	NPD5786	Approved
0.6033	Remote Similarity	NPD6881	Approved
0.6033	Remote Similarity	NPD7320	Approved
0.6033	Remote Similarity	NPD6899	Approved
0.6018	Remote Similarity	NPD6399	Phase 3
0.6018	Remote Similarity	NPD5779	Approved
0.6018	Remote Similarity	NPD5778	Approved
0.6	Remote Similarity	NPD6675	Approved
0.6	Remote Similarity	NPD5739	Approved
0.6	Remote Similarity	NPD7128	Approved
0.6	Remote Similarity	NPD6402	Approved
0.5984	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.597	Remote Similarity	NPD5956	Approved
0.5969	Remote Similarity	NPD6921	Approved
0.595	Remote Similarity	NPD5697	Approved
0.5943	Remote Similarity	NPD4252	Approved
0.594	Remote Similarity	NPD6033	Approved
0.5935	Remote Similarity	NPD7290	Approved
0.5935	Remote Similarity	NPD7102	Approved
0.5935	Remote Similarity	NPD6883	Approved
0.5935	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD8035	Phase 2
0.5929	Remote Similarity	NPD8034	Phase 2
0.5926	Remote Similarity	NPD5332	Approved
0.5926	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD3669	Approved
0.5926	Remote Similarity	NPD5331	Approved
0.5913	Remote Similarity	NPD5695	Phase 3
0.5909	Remote Similarity	NPD8273	Phase 1
0.5897	Remote Similarity	NPD5696	Approved
0.5893	Remote Similarity	NPD6101	Approved
0.5893	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD4790	Discontinued
0.5887	Remote Similarity	NPD6617	Approved
0.5887	Remote Similarity	NPD6869	Approved
0.5887	Remote Similarity	NPD8130	Phase 1
0.5887	Remote Similarity	NPD6847	Approved
0.5882	Remote Similarity	NPD7632	Discontinued
0.5882	Remote Similarity	NPD8086	Approved
0.5882	Remote Similarity	NPD8084	Approved
0.5882	Remote Similarity	NPD8138	Approved
0.5882	Remote Similarity	NPD8085	Approved
0.5882	Remote Similarity	NPD8338	Approved
0.5882	Remote Similarity	NPD8083	Approved
0.5882	Remote Similarity	NPD8139	Approved
0.5882	Remote Similarity	NPD8082	Approved
0.5878	Remote Similarity	NPD7604	Phase 2
0.5877	Remote Similarity	NPD8171	Discontinued
0.5872	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5868	Remote Similarity	NPD6008	Approved
0.5862	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD898	Approved
0.5859	Remote Similarity	NPD897	Approved
0.5859	Remote Similarity	NPD896	Approved
0.5854	Remote Similarity	NPD6014	Approved
0.5854	Remote Similarity	NPD6013	Approved
0.5854	Remote Similarity	NPD6012	Approved
0.5847	Remote Similarity	NPD6648	Approved
0.5846	Remote Similarity	NPD5983	Phase 2
0.5833	Remote Similarity	NPD8276	Approved
0.5833	Remote Similarity	NPD8275	Approved
0.582	Remote Similarity	NPD5701	Approved
0.5789	Remote Similarity	NPD6411	Approved
0.5789	Remote Similarity	NPD6336	Discontinued
0.5789	Remote Similarity	NPD7637	Suspended
0.5785	Remote Similarity	NPD8081	Approved
0.578	Remote Similarity	NPD6110	Phase 1
0.5772	Remote Similarity	NPD6011	Approved
0.5755	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD1779	Approved
0.5741	Remote Similarity	NPD1780	Approved
0.5738	Remote Similarity	NPD8393	Approved
0.5714	Remote Similarity	NPD7524	Approved
0.5701	Remote Similarity	NPD7329	Approved
0.5691	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.568	Remote Similarity	NPD4634	Approved
0.5676	Remote Similarity	NPD1694	Approved
0.5676	Remote Similarity	NPD7520	Clinical (unspecified phase)

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