NPASS Compound

Structure

CID297474 OpenBabel06191716102D 22 24 0 0 1 0 0 0 0 0999 V2000 -2.9312 1.5294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2596 -2.4705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6975 -4.3185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9511 -1.1703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0694 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4467 -0.8827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5547 0.6645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5147 0.6645 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3456 -1.5144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6975 -3.3585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1132 -0.0861 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9561 -0.0861 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7237 -1.5144 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1698 -1.0220 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0347 -1.4385 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3773 -0.8827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8996 -1.0220 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5288 -2.8785 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8098 -2.4705 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3132 -1.0964 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0347 -2.3985 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 9 2 0 0 0 0 3 10 1 0 0 0 0 5 6 1 0 0 0 0 5 11 1 0 0 0 0 6 13 1 0 0 0 0 7 8 1 0 0 0 0 8 1 1 6 0 0 0 8 11 1 0 0 0 0 9 16 1 0 0 0 0 10 18 2 0 0 0 0 10 21 1 0 0 0 0 11 17 1 1 0 0 0 12 7 1 6 0 0 0 12 14 1 0 0 0 0 12 22 1 0 0 0 0 13 17 1 1 0 0 0 13 19 1 0 0 0 0 14 9 1 1 0 0 0 14 15 1 0 0 0 0 15 17 1 6 0 0 0 15 21 1 0 0 0 0 16 20 2 0 0 0 0 16 22 1 0 0 0 0 17 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	308.16
Volume:	312.961
LogP:	1.776
LogD:	2.321
LogS:	-3.045
# Rotatable Bonds:	2
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.591
Synthetic Accessibility Score:	4.587
Fsp3:	0.765
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.774
MDCK Permeability:	5.97903854213655e-05
Pgp-inhibitor:	0.159
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.453
20% Bioavailability (F20%):	0.368
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.677
Plasma Protein Binding (PPB):	35.14495086669922%
Volume Distribution (VD):	0.639
Pgp-substrate:	52.745460510253906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.136
CYP1A2-substrate:	0.072
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.491
CYP2C9-inhibitor:	0.03
CYP2C9-substrate:	0.069
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.139
CYP3A4-inhibitor:	0.105
CYP3A4-substrate:	0.266

ADMET: Excretion

Clearance (CL):	11.174
Half-life (T1/2):	0.821

ADMET: Toxicity

hERG Blockers:	0.065
Human Hepatotoxicity (H-HT):	0.337
Drug-inuced Liver Injury (DILI):	0.793
AMES Toxicity:	0.043
Rat Oral Acute Toxicity:	0.914
Maximum Recommended Daily Dose:	0.049
Skin Sensitization:	0.824
Carcinogencity:	0.559
Eye Corrosion:	0.626
Eye Irritation:	0.313
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC297474

Natural Product ID:	NPC297474
*Common Name:**	6Alpha-Acetoxy-4Beta-Hydroxy-1Alpha,10Betah-Pseudoguaia-11(13)-En-12,8Alpha-Olide
IUPAC Name:	[(3aS,5R,5aS,8S,8aS,9S,9aR)-8-hydroxy-5,8a-dimethyl-1-methylidene-2-oxo-4,5,5a,6,7,8,9,9a-octahydro-3aH-azuleno[6,5-b]furan-9-yl] acetate
Synonyms:
Standard InCHIKey:	SIPZPOSXKDFDJR-ASINEMROSA-N
Standard InCHI:	InChI=1S/C17H24O5/c1-8-7-12-14(9(2)16(20)22-12)15(21-10(3)18)17(4)11(8)5-6-13(17)19/h8,11-15,19H,2,5-7H2,1,3-4H3/t8-,11+,12+,13+,14-,15+,17+/m1/s1
SMILES:	CC(=O)O[C@H]1[C@H]2[C@@H](OC(=O)C2=C)C[C@H]([C@H]2[C@@]1(C)[C@@H](O)CC2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1912047
PubChem CID:	14414377
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

*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
NPO22238	Inula falconeri	Species	Asteraceae	Eukaryota	aerial parts	Tibet, China	n.a.	PMID[21924800]
NPO2106	Elephantopus carolinianus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2106	Elephantopus carolinianus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15457	Bunodophoron patagonicum	Species	Sphaerophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4106	Pyrola alpina	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2402	Valeriana chionophila	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22449	Ulnaria acus	Species	Fragilariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5581	Psammaplysilla arabica	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO3738	Achillea stepposa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3551	Thymus collinus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2106	Elephantopus carolinianus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18658	Dolichospermum flos-aquae	Species	Aphanizomenonaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO22238	Inula falconeri	Species	Asteraceae	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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	360.0	nM	PMID[543542]

☑ 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 NPC297474 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	246
0.1-0.2	1745
0.2-0.3	6311
0.3-0.4	15055
0.4-0.5	8267
0.5-0.6	7386
0.6-0.7	3058
0.7-0.8	478
0.8-0.85	64
0.85-0.9	37
0.9-0.95	32
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC54065
0.9882	High Similarity	NPC35959
0.9882	High Similarity	NPC63193
0.9882	High Similarity	NPC29821
0.9882	High Similarity	NPC57304
0.9882	High Similarity	NPC293001
0.9882	High Similarity	NPC171360
0.9882	High Similarity	NPC133888
0.9881	High Similarity	NPC155935
0.9765	High Similarity	NPC35809
0.9529	High Similarity	NPC207114
0.9529	High Similarity	NPC217983
0.9524	High Similarity	NPC56593
0.9438	High Similarity	NPC91771
0.9438	High Similarity	NPC142529
0.9438	High Similarity	NPC24956
0.9438	High Similarity	NPC18019
0.9419	High Similarity	NPC215556
0.9412	High Similarity	NPC24728
0.931	High Similarity	NPC19087
0.931	High Similarity	NPC216284
0.9302	High Similarity	NPC471149
0.9302	High Similarity	NPC79549
0.9294	High Similarity	NPC187661
0.9205	High Similarity	NPC184063
0.9195	High Similarity	NPC38392
0.9195	High Similarity	NPC283409
0.9121	High Similarity	NPC311904
0.9111	High Similarity	NPC472873
0.9101	High Similarity	NPC60386
0.9101	High Similarity	NPC473234
0.9101	High Similarity	NPC200237
0.9101	High Similarity	NPC473263
0.9101	High Similarity	NPC473273
0.9101	High Similarity	NPC308656
0.9059	High Similarity	NPC224386
0.9059	High Similarity	NPC194859
0.9048	High Similarity	NPC246076
0.9032	High Similarity	NPC171759
0.9	High Similarity	NPC473331
0.8989	High Similarity	NPC155215
0.8989	High Similarity	NPC286341
0.8989	High Similarity	NPC191339
0.8989	High Similarity	NPC475925
0.8953	High Similarity	NPC284534
0.8953	High Similarity	NPC300082
0.8953	High Similarity	NPC204105
0.8941	High Similarity	NPC111409
0.8941	High Similarity	NPC128246
0.8913	High Similarity	NPC471150
0.8901	High Similarity	NPC213698
0.8901	High Similarity	NPC163228
0.8901	High Similarity	NPC476053
0.8889	High Similarity	NPC153590
0.8889	High Similarity	NPC258216
0.8851	High Similarity	NPC304558
0.8791	High Similarity	NPC127019
0.8764	High Similarity	NPC12872
0.8764	High Similarity	NPC168679
0.8764	High Similarity	NPC472872
0.875	High Similarity	NPC118601
0.875	High Similarity	NPC201658
0.8721	High Similarity	NPC245665
0.871	High Similarity	NPC161493
0.871	High Similarity	NPC213947
0.871	High Similarity	NPC474313
0.871	High Similarity	NPC108475
0.871	High Similarity	NPC170143
0.8706	High Similarity	NPC126248
0.8696	High Similarity	NPC170120
0.8696	High Similarity	NPC67584
0.8696	High Similarity	NPC52044
0.8652	High Similarity	NPC178875
0.8636	High Similarity	NPC64153
0.8636	High Similarity	NPC236692
0.8636	High Similarity	NPC309757
0.8602	High Similarity	NPC126156
0.8602	High Similarity	NPC213078
0.8587	High Similarity	NPC198853
0.8571	High Similarity	NPC133698
0.8571	High Similarity	NPC131209
0.8526	High Similarity	NPC186861
0.8526	High Similarity	NPC471381
0.8506	High Similarity	NPC54468
0.8438	Intermediate Similarity	NPC150923
0.8427	Intermediate Similarity	NPC238593
0.8427	Intermediate Similarity	NPC67493
0.8427	Intermediate Similarity	NPC470242
0.8421	Intermediate Similarity	NPC49833
0.8421	Intermediate Similarity	NPC249171
0.8421	Intermediate Similarity	NPC45125
0.8387	Intermediate Similarity	NPC470010
0.8387	Intermediate Similarity	NPC262133
0.8387	Intermediate Similarity	NPC323008
0.8387	Intermediate Similarity	NPC477131
0.8387	Intermediate Similarity	NPC470013
0.8372	Intermediate Similarity	NPC156658
0.8372	Intermediate Similarity	NPC258965
0.8333	Intermediate Similarity	NPC270270
0.8316	Intermediate Similarity	NPC304445
0.8316	Intermediate Similarity	NPC181151
0.8316	Intermediate Similarity	NPC236580
0.8315	Intermediate Similarity	NPC235792
0.8298	Intermediate Similarity	NPC304886
0.8283	Intermediate Similarity	NPC44004
0.8283	Intermediate Similarity	NPC54737
0.828	Intermediate Similarity	NPC475788
0.828	Intermediate Similarity	NPC472874
0.8276	Intermediate Similarity	NPC47635
0.8265	Intermediate Similarity	NPC221421
0.8265	Intermediate Similarity	NPC473148
0.8261	Intermediate Similarity	NPC37607
0.8261	Intermediate Similarity	NPC301969
0.8242	Intermediate Similarity	NPC224652
0.8242	Intermediate Similarity	NPC91248
0.8229	Intermediate Similarity	NPC221615
0.8222	Intermediate Similarity	NPC162071
0.8202	Intermediate Similarity	NPC156485
0.8163	Intermediate Similarity	NPC80144
0.8161	Intermediate Similarity	NPC73052
0.8161	Intermediate Similarity	NPC51507
0.8161	Intermediate Similarity	NPC290508
0.8161	Intermediate Similarity	NPC293418
0.8161	Intermediate Similarity	NPC6823
0.8144	Intermediate Similarity	NPC70865
0.8132	Intermediate Similarity	NPC190753
0.8132	Intermediate Similarity	NPC186148
0.8125	Intermediate Similarity	NPC477949
0.8119	Intermediate Similarity	NPC68248
0.8105	Intermediate Similarity	NPC157686
0.8105	Intermediate Similarity	NPC259042
0.8105	Intermediate Similarity	NPC167893
0.8095	Intermediate Similarity	NPC143979
0.8095	Intermediate Similarity	NPC320537
0.8085	Intermediate Similarity	NPC135776
0.8065	Intermediate Similarity	NPC474323
0.8065	Intermediate Similarity	NPC206614
0.8061	Intermediate Similarity	NPC67296
0.8043	Intermediate Similarity	NPC177629
0.8043	Intermediate Similarity	NPC58219
0.8039	Intermediate Similarity	NPC59489
0.8039	Intermediate Similarity	NPC139838
0.8021	Intermediate Similarity	NPC476009
0.8021	Intermediate Similarity	NPC284518
0.8021	Intermediate Similarity	NPC474297
0.8	Intermediate Similarity	NPC471382
0.8	Intermediate Similarity	NPC225474
0.8	Intermediate Similarity	NPC469596
0.8	Intermediate Similarity	NPC471380
0.8	Intermediate Similarity	NPC148000
0.8	Intermediate Similarity	NPC203659
0.798	Intermediate Similarity	NPC86077
0.798	Intermediate Similarity	NPC225353
0.7957	Intermediate Similarity	NPC92974
0.7957	Intermediate Similarity	NPC4986
0.7938	Intermediate Similarity	NPC261372
0.7938	Intermediate Similarity	NPC58267
0.7938	Intermediate Similarity	NPC263674
0.7938	Intermediate Similarity	NPC473963
0.7938	Intermediate Similarity	NPC169205
0.7921	Intermediate Similarity	NPC243998
0.7917	Intermediate Similarity	NPC469873
0.7917	Intermediate Similarity	NPC48803
0.7917	Intermediate Similarity	NPC275960
0.7917	Intermediate Similarity	NPC193645
0.7917	Intermediate Similarity	NPC37408
0.7917	Intermediate Similarity	NPC90121
0.7917	Intermediate Similarity	NPC475900
0.7917	Intermediate Similarity	NPC224689
0.79	Intermediate Similarity	NPC474775
0.79	Intermediate Similarity	NPC110989
0.7879	Intermediate Similarity	NPC477950
0.7872	Intermediate Similarity	NPC469368
0.7857	Intermediate Similarity	NPC141191
0.7849	Intermediate Similarity	NPC202672
0.7843	Intermediate Similarity	NPC26617
0.7841	Intermediate Similarity	NPC19841
0.7835	Intermediate Similarity	NPC473964
0.7835	Intermediate Similarity	NPC185553
0.7835	Intermediate Similarity	NPC93245
0.783	Intermediate Similarity	NPC123117
0.7826	Intermediate Similarity	NPC474949
0.7826	Intermediate Similarity	NPC475019
0.7816	Intermediate Similarity	NPC208223
0.7812	Intermediate Similarity	NPC24861
0.7789	Intermediate Similarity	NPC12172
0.7789	Intermediate Similarity	NPC208886
0.7789	Intermediate Similarity	NPC184463
0.7789	Intermediate Similarity	NPC221282
0.7788	Intermediate Similarity	NPC471884
0.7778	Intermediate Similarity	NPC161060
0.7778	Intermediate Similarity	NPC89555
0.7778	Intermediate Similarity	NPC47024
0.7767	Intermediate Similarity	NPC255082
0.7766	Intermediate Similarity	NPC212664
0.7766	Intermediate Similarity	NPC295312
0.7766	Intermediate Similarity	NPC116620
0.7766	Intermediate Similarity	NPC32922
0.7745	Intermediate Similarity	NPC223450
0.7745	Intermediate Similarity	NPC166115

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 NPC297474 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	300
0.1-0.2	2494
0.2-0.3	3871
0.3-0.4	1714
0.4-0.5	423
0.5-0.6	283
0.6-0.7	55
0.7-0.8	10
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
0.7957	Intermediate Similarity	NPD1695	Approved
0.7917	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6371	Approved
0.75	Intermediate Similarity	NPD5785	Approved
0.7447	Intermediate Similarity	NPD4249	Approved
0.7368	Intermediate Similarity	NPD4250	Approved
0.7368	Intermediate Similarity	NPD4251	Approved
0.7158	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD6053	Discontinued
0.7128	Intermediate Similarity	NPD5362	Discontinued
0.7021	Intermediate Similarity	NPD6435	Approved
0.699	Remote Similarity	NPD7638	Approved
0.6989	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD5363	Approved
0.697	Remote Similarity	NPD6698	Approved
0.697	Remote Similarity	NPD46	Approved
0.6931	Remote Similarity	NPD5282	Discontinued
0.6923	Remote Similarity	NPD7639	Approved
0.6923	Remote Similarity	NPD7640	Approved
0.6915	Remote Similarity	NPD5369	Approved
0.6842	Remote Similarity	NPD4269	Approved
0.6842	Remote Similarity	NPD4270	Approved
0.6809	Remote Similarity	NPD4819	Approved
0.6809	Remote Similarity	NPD5368	Approved
0.6809	Remote Similarity	NPD4820	Approved
0.6809	Remote Similarity	NPD4821	Approved
0.6809	Remote Similarity	NPD4822	Approved
0.6804	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD6686	Approved
0.6774	Remote Similarity	NPD4271	Approved
0.6774	Remote Similarity	NPD4268	Approved
0.6771	Remote Similarity	NPD7154	Phase 3
0.6759	Remote Similarity	NPD6008	Approved
0.6735	Remote Similarity	NPD5786	Approved
0.6667	Remote Similarity	NPD4225	Approved
0.6667	Remote Similarity	NPD6399	Phase 3
0.6634	Remote Similarity	NPD7838	Discovery
0.6632	Remote Similarity	NPD4252	Approved
0.6598	Remote Similarity	NPD5332	Approved
0.6598	Remote Similarity	NPD5331	Approved
0.6596	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6083	Phase 2
0.6571	Remote Similarity	NPD6084	Phase 2
0.6569	Remote Similarity	NPD8035	Phase 2
0.6569	Remote Similarity	NPD8034	Phase 2
0.6562	Remote Similarity	NPD4790	Discontinued
0.6545	Remote Similarity	NPD6412	Phase 2
0.6545	Remote Similarity	NPD5697	Approved
0.6538	Remote Similarity	NPD5695	Phase 3
0.6509	Remote Similarity	NPD5696	Approved
0.6495	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD8133	Approved
0.6486	Remote Similarity	NPD6899	Approved
0.6486	Remote Similarity	NPD6881	Approved
0.6486	Remote Similarity	NPD7320	Approved
0.6481	Remote Similarity	NPD7632	Discontinued
0.6465	Remote Similarity	NPD1694	Approved
0.646	Remote Similarity	NPD6649	Approved
0.646	Remote Similarity	NPD6650	Approved
0.6455	Remote Similarity	NPD6675	Approved
0.6455	Remote Similarity	NPD6402	Approved
0.6455	Remote Similarity	NPD7128	Approved
0.6455	Remote Similarity	NPD5739	Approved
0.6446	Remote Similarity	NPD7507	Approved
0.6436	Remote Similarity	NPD6903	Approved
0.6429	Remote Similarity	NPD6012	Approved
0.6429	Remote Similarity	NPD4788	Approved
0.6429	Remote Similarity	NPD6014	Approved
0.6429	Remote Similarity	NPD6013	Approved
0.6429	Remote Similarity	NPD6372	Approved
0.6429	Remote Similarity	NPD6373	Approved
0.6408	Remote Similarity	NPD7637	Suspended
0.6408	Remote Similarity	NPD7983	Approved
0.64	Remote Similarity	NPD7146	Approved
0.64	Remote Similarity	NPD6409	Approved
0.64	Remote Similarity	NPD7334	Approved
0.64	Remote Similarity	NPD7521	Approved
0.64	Remote Similarity	NPD5330	Approved
0.64	Remote Similarity	NPD6684	Approved
0.6396	Remote Similarity	NPD5701	Approved
0.6372	Remote Similarity	NPD7102	Approved
0.6372	Remote Similarity	NPD7290	Approved
0.6372	Remote Similarity	NPD6883	Approved
0.6364	Remote Similarity	NPD3133	Approved
0.6364	Remote Similarity	NPD7492	Approved
0.6364	Remote Similarity	NPD3665	Phase 1
0.6364	Remote Similarity	NPD3666	Approved
0.6353	Remote Similarity	NPD3198	Approved
0.6348	Remote Similarity	NPD4632	Approved
0.6346	Remote Similarity	NPD5779	Approved
0.6346	Remote Similarity	NPD5778	Approved
0.6339	Remote Similarity	NPD6011	Approved
0.6325	Remote Similarity	NPD7115	Discovery
0.6316	Remote Similarity	NPD8130	Phase 1
0.6316	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6847	Approved
0.6316	Remote Similarity	NPD6869	Approved
0.6316	Remote Similarity	NPD6617	Approved
0.6311	Remote Similarity	NPD6616	Approved
0.6303	Remote Similarity	NPD6054	Approved
0.6303	Remote Similarity	NPD6319	Approved
0.63	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.629	Remote Similarity	NPD7319	Approved
0.6283	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD8297	Approved
0.6261	Remote Similarity	NPD6882	Approved
0.626	Remote Similarity	NPD7078	Approved
0.625	Remote Similarity	NPD6015	Approved
0.625	Remote Similarity	NPD6016	Approved
0.625	Remote Similarity	NPD4802	Phase 2
0.625	Remote Similarity	NPD5281	Approved
0.625	Remote Similarity	NPD5693	Phase 1
0.625	Remote Similarity	NPD6411	Approved
0.625	Remote Similarity	NPD4238	Approved
0.625	Remote Similarity	NPD5284	Approved
0.6228	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD4629	Approved
0.6226	Remote Similarity	NPD5210	Approved
0.6214	Remote Similarity	NPD4753	Phase 2
0.621	Remote Similarity	NPD7736	Approved
0.6204	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.62	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD6370	Approved
0.6198	Remote Similarity	NPD5988	Approved
0.6195	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD6009	Approved
0.6182	Remote Similarity	NPD5211	Phase 2
0.6167	Remote Similarity	NPD6059	Approved
0.6162	Remote Similarity	NPD3667	Approved
0.6162	Remote Similarity	NPD5209	Approved
0.6154	Remote Similarity	NPD5207	Approved
0.6147	Remote Similarity	NPD5285	Approved
0.6147	Remote Similarity	NPD4696	Approved
0.6147	Remote Similarity	NPD5286	Approved
0.6134	Remote Similarity	NPD7327	Approved
0.6134	Remote Similarity	NPD7328	Approved
0.6129	Remote Similarity	NPD8293	Discontinued
0.6116	Remote Similarity	NPD8033	Approved
0.6116	Remote Similarity	NPD5983	Phase 2
0.6116	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD4755	Approved
0.6102	Remote Similarity	NPD6274	Approved
0.61	Remote Similarity	NPD6695	Phase 3
0.6091	Remote Similarity	NPD5344	Discontinued
0.6083	Remote Similarity	NPD7516	Approved
0.6078	Remote Similarity	NPD3618	Phase 1
0.6071	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD5141	Approved
0.6071	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD6101	Approved
0.604	Remote Similarity	NPD4786	Approved
0.6038	Remote Similarity	NPD4202	Approved
0.6036	Remote Similarity	NPD5224	Approved
0.6036	Remote Similarity	NPD5226	Approved
0.6036	Remote Similarity	NPD4633	Approved
0.6036	Remote Similarity	NPD5225	Approved
0.6034	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD8377	Approved
0.6033	Remote Similarity	NPD8294	Approved
0.6016	Remote Similarity	NPD7604	Phase 2
0.6016	Remote Similarity	NPD6845	Suspended
0.6	Remote Similarity	NPD4700	Approved
0.5984	Remote Similarity	NPD8296	Approved
0.5984	Remote Similarity	NPD8380	Approved
0.5984	Remote Similarity	NPD7503	Approved
0.5984	Remote Similarity	NPD8379	Approved
0.5984	Remote Similarity	NPD8378	Approved
0.5984	Remote Similarity	NPD8335	Approved
0.5982	Remote Similarity	NPD5175	Approved
0.5982	Remote Similarity	NPD5174	Approved
0.5981	Remote Similarity	NPD6001	Approved
0.5965	Remote Similarity	NPD6685	Approved
0.5965	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD7902	Approved
0.5962	Remote Similarity	NPD5737	Approved
0.5962	Remote Similarity	NPD6672	Approved
0.595	Remote Similarity	NPD7100	Approved
0.595	Remote Similarity	NPD7101	Approved
0.5948	Remote Similarity	NPD4634	Approved
0.5946	Remote Similarity	NPD5223	Approved
0.5946	Remote Similarity	NPD1700	Approved
0.5938	Remote Similarity	NPD3702	Approved
0.5938	Remote Similarity	NPD7260	Phase 2
0.5922	Remote Similarity	NPD5279	Phase 3
0.592	Remote Similarity	NPD6336	Discontinued
0.5918	Remote Similarity	NPD6697	Approved
0.5918	Remote Similarity	NPD6118	Approved
0.5918	Remote Similarity	NPD6114	Approved
0.5918	Remote Similarity	NPD6115	Approved
0.5917	Remote Similarity	NPD6317	Approved
0.5905	Remote Similarity	NPD6051	Approved
0.5905	Remote Similarity	NPD6080	Approved
0.5905	Remote Similarity	NPD6904	Approved
0.5905	Remote Similarity	NPD6673	Approved
0.5887	Remote Similarity	NPD6067	Discontinued
0.5882	Remote Similarity	NPD5766	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