NPASS Compound

Structure

NPC199099 OpenBabel07101718222D 33 35 0 0 1 0 0 0 0 0999 V2000 -0.6581 -4.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5241 2.0219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5739 -5.0762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5739 1.3879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0739 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0267 -0.4817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9400 0.0219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9400 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3794 -1.0169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5241 -3.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 1.5219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 -4.2102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 -2.4781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6581 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 0.0219 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0739 0.5219 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0739 -2.4781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0739 -1.4781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2079 -0.9781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3902 -4.4781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 2.0219 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0739 -4.2102 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4945 0.9706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5739 1.3879 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9400 -1.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0485 -0.2738 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5241 -2.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 0.5219 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5739 -3.3442 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 1 11 1 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 5 20 1 0 0 0 0 6 29 1 0 0 0 0 7 8 1 0 0 0 0 7 19 1 0 0 0 0 8 21 1 0 0 0 0 9 15 1 0 0 0 0 9 20 1 0 0 0 0 10 14 1 0 0 0 0 10 29 1 0 0 0 0 11 23 2 0 0 0 0 11 30 1 0 0 0 0 12 24 2 0 0 0 0 12 31 1 0 0 0 0 13 25 2 0 0 0 0 13 32 1 0 0 0 0 14 16 2 0 0 0 0 14 17 1 0 0 0 0 15 16 1 0 0 0 0 15 30 1 6 0 0 0 17 26 2 0 0 0 0 17 33 1 0 0 0 0 18 19 1 1 0 0 0 18 22 1 0 0 0 0 18 31 1 0 0 0 0 19 4 1 1 0 0 0 19 27 1 0 0 0 0 20 21 1 6 0 0 0 20 32 1 0 0 0 0 21 22 1 1 0 0 0 21 28 1 0 0 0 0 22 16 1 6 0 0 0 22 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	470.18
Volume:	446.909
LogP:	0.72
LogD:	0.624
LogS:	-3.787
# Rotatable Bonds:	8
TPSA:	154.89
# H-Bond Aceptor:	11
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.415
Synthetic Accessibility Score:	5.392
Fsp3:	0.727
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:	-5.289
MDCK Permeability:	7.663649739697576e-05
Pgp-inhibitor:	0.917
Pgp-substrate:	0.687
Human Intestinal Absorption (HIA):	0.765
20% Bioavailability (F20%):	0.957
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.744
Plasma Protein Binding (PPB):	25.165287017822266%
Volume Distribution (VD):	0.623
Pgp-substrate:	64.45948028564453%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.298
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.315
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.01
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.036
CYP3A4-inhibitor:	0.185
CYP3A4-substrate:	0.704

ADMET: Excretion

Clearance (CL):	2.285
Half-life (T1/2):	0.192

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.182
Drug-inuced Liver Injury (DILI):	0.968
AMES Toxicity:	0.361
Rat Oral Acute Toxicity:	0.826
Maximum Recommended Daily Dose:	0.127
Skin Sensitization:	0.461
Carcinogencity:	0.456
Eye Corrosion:	0.013
Eye Irritation:	0.063
Respiratory Toxicity:	0.924

Download Data

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

Natural Product: NPC199099

Natural Product ID:	NPC199099
*Common Name:**	13-O-Methylvernojalcanolide 8-O-Acetate
IUPAC Name:	[(4S,6R,6aS,9R,10S,10aS)-6,10-diacetyloxy-6a,9-dihydroxy-3-(methoxymethyl)-6,9-dimethyl-2-oxo-5,7,8,10-tetrahydro-4H-benzo[h][1]benzofuran-4-yl] acetate
Synonyms:
Standard InCHIKey:	VQMMSXZZPVPGAY-OUOFEDGXSA-N
Standard InCHI:	InChI=1S/C22H30O11/c1-11(23)30-15-9-20(5,32-13(3)25)21(28)8-7-19(4,27)18(31-12(2)24)22(21)16(15)14(10-29-6)17(26)33-22/h15,18,27-28H,7-10H2,1-6H3/t15-,18-,19+,20+,21-,22-/m0/s1
SMILES:	COCC1=C2[C@@H](OC(=O)C)C[C@@]([C@@]3([C@@]2(OC1=O)[C@@H](OC(=O)C)[C@](C)(O)CC3)O)(C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL401161
PubChem CID:	44445368
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:0002048] Cadinanolides

*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
NPO32710	pseudoelephantopus spicatus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[17970595]

☑ 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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[555327]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[555327]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[555327]

☑ 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 NPC199099 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	226
0.1-0.2	1602
0.2-0.3	4612
0.3-0.4	7026
0.4-0.5	14815
0.5-0.6	8414
0.6-0.7	4995
0.7-0.8	957
0.8-0.85	42
0.85-0.9	6
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.8776	High Similarity	NPC472552
0.8723	High Similarity	NPC110022
0.8687	High Similarity	NPC474822
0.8673	High Similarity	NPC472554
0.8529	High Similarity	NPC181994
0.8431	Intermediate Similarity	NPC122816
0.8384	Intermediate Similarity	NPC38855
0.8384	Intermediate Similarity	NPC188968
0.8381	Intermediate Similarity	NPC42658
0.8351	Intermediate Similarity	NPC111273
0.835	Intermediate Similarity	NPC50124
0.8333	Intermediate Similarity	NPC51719
0.8333	Intermediate Similarity	NPC477090
0.8317	Intermediate Similarity	NPC23584
0.8317	Intermediate Similarity	NPC159533
0.83	Intermediate Similarity	NPC11974
0.8269	Intermediate Similarity	NPC299590
0.8265	Intermediate Similarity	NPC472995
0.8252	Intermediate Similarity	NPC471205
0.8218	Intermediate Similarity	NPC11956
0.82	Intermediate Similarity	NPC79303
0.82	Intermediate Similarity	NPC271295
0.819	Intermediate Similarity	NPC177047
0.8163	Intermediate Similarity	NPC276110
0.8155	Intermediate Similarity	NPC471206
0.8144	Intermediate Similarity	NPC472640
0.8144	Intermediate Similarity	NPC472641
0.8144	Intermediate Similarity	NPC7349
0.8137	Intermediate Similarity	NPC165608
0.8137	Intermediate Similarity	NPC99510
0.8081	Intermediate Similarity	NPC129569
0.8077	Intermediate Similarity	NPC67321
0.8077	Intermediate Similarity	NPC187435
0.8065	Intermediate Similarity	NPC32223
0.8061	Intermediate Similarity	NPC105490
0.8041	Intermediate Similarity	NPC78594
0.8039	Intermediate Similarity	NPC109195
0.8039	Intermediate Similarity	NPC471914
0.8039	Intermediate Similarity	NPC295791
0.8039	Intermediate Similarity	NPC475038
0.802	Intermediate Similarity	NPC16601
0.802	Intermediate Similarity	NPC272223
0.8	Intermediate Similarity	NPC38948
0.8	Intermediate Similarity	NPC472998
0.798	Intermediate Similarity	NPC469583
0.798	Intermediate Similarity	NPC471915
0.7963	Intermediate Similarity	NPC477126
0.7961	Intermediate Similarity	NPC471938
0.7961	Intermediate Similarity	NPC281378
0.7961	Intermediate Similarity	NPC61442
0.7961	Intermediate Similarity	NPC72842
0.7938	Intermediate Similarity	NPC472642
0.7925	Intermediate Similarity	NPC475586
0.7925	Intermediate Similarity	NPC206618
0.7917	Intermediate Similarity	NPC242448
0.7909	Intermediate Similarity	NPC58662
0.7905	Intermediate Similarity	NPC473586
0.79	Intermediate Similarity	NPC472997
0.79	Intermediate Similarity	NPC472996
0.79	Intermediate Similarity	NPC475380
0.79	Intermediate Similarity	NPC209297
0.7885	Intermediate Similarity	NPC161775
0.7885	Intermediate Similarity	NPC283850
0.7885	Intermediate Similarity	NPC471937
0.7885	Intermediate Similarity	NPC146731
0.7879	Intermediate Similarity	NPC105375
0.7879	Intermediate Similarity	NPC140277
0.7879	Intermediate Similarity	NPC182826
0.787	Intermediate Similarity	NPC269530
0.7864	Intermediate Similarity	NPC470972
0.7864	Intermediate Similarity	NPC165578
0.7864	Intermediate Similarity	NPC121423
0.7864	Intermediate Similarity	NPC476081
0.7857	Intermediate Similarity	NPC251226
0.7857	Intermediate Similarity	NPC472004
0.7843	Intermediate Similarity	NPC274643
0.7838	Intermediate Similarity	NPC240509
0.783	Intermediate Similarity	NPC475263
0.783	Intermediate Similarity	NPC469916
0.783	Intermediate Similarity	NPC472439
0.783	Intermediate Similarity	NPC306265
0.7822	Intermediate Similarity	NPC120446
0.7822	Intermediate Similarity	NPC473244
0.7822	Intermediate Similarity	NPC311241
0.7822	Intermediate Similarity	NPC100912
0.7822	Intermediate Similarity	NPC475446
0.7822	Intermediate Similarity	NPC254121
0.7818	Intermediate Similarity	NPC470075
0.7818	Intermediate Similarity	NPC471816
0.7812	Intermediate Similarity	NPC473891
0.781	Intermediate Similarity	NPC470980
0.781	Intermediate Similarity	NPC81630
0.7788	Intermediate Similarity	NPC4021
0.7788	Intermediate Similarity	NPC159456
0.7788	Intermediate Similarity	NPC474124
0.7788	Intermediate Similarity	NPC120009
0.7778	Intermediate Similarity	NPC53555
0.7778	Intermediate Similarity	NPC471483
0.7778	Intermediate Similarity	NPC469656
0.7778	Intermediate Similarity	NPC474846
0.7778	Intermediate Similarity	NPC469655
0.7767	Intermediate Similarity	NPC475617
0.7748	Intermediate Similarity	NPC55296
0.7745	Intermediate Similarity	NPC278673
0.7745	Intermediate Similarity	NPC124512
0.7745	Intermediate Similarity	NPC278386
0.7745	Intermediate Similarity	NPC159763
0.7745	Intermediate Similarity	NPC72647
0.7745	Intermediate Similarity	NPC107806
0.7736	Intermediate Similarity	NPC216636
0.7736	Intermediate Similarity	NPC319438
0.7723	Intermediate Similarity	NPC165632
0.7723	Intermediate Similarity	NPC284194
0.7723	Intermediate Similarity	NPC471765
0.7723	Intermediate Similarity	NPC475304
0.7723	Intermediate Similarity	NPC211810
0.7723	Intermediate Similarity	NPC221801
0.7723	Intermediate Similarity	NPC194132
0.7714	Intermediate Similarity	NPC65523
0.7714	Intermediate Similarity	NPC473543
0.7714	Intermediate Similarity	NPC296950
0.7706	Intermediate Similarity	NPC472002
0.7699	Intermediate Similarity	NPC154491
0.7699	Intermediate Similarity	NPC268530
0.7692	Intermediate Similarity	NPC165250
0.7692	Intermediate Similarity	NPC472815
0.7692	Intermediate Similarity	NPC476471
0.7692	Intermediate Similarity	NPC162973
0.7692	Intermediate Similarity	NPC475344
0.7679	Intermediate Similarity	NPC251310
0.7677	Intermediate Similarity	NPC122057
0.767	Intermediate Similarity	NPC475877
0.767	Intermediate Similarity	NPC324841
0.7664	Intermediate Similarity	NPC94377
0.7664	Intermediate Similarity	NPC151393
0.7664	Intermediate Similarity	NPC88701
0.7653	Intermediate Similarity	NPC82876
0.7652	Intermediate Similarity	NPC469352
0.7652	Intermediate Similarity	NPC67251
0.7647	Intermediate Similarity	NPC73911
0.7647	Intermediate Similarity	NPC51499
0.7647	Intermediate Similarity	NPC218064
0.7647	Intermediate Similarity	NPC205143
0.7642	Intermediate Similarity	NPC88349
0.7642	Intermediate Similarity	NPC111952
0.7636	Intermediate Similarity	NPC33360
0.7636	Intermediate Similarity	NPC264153
0.7636	Intermediate Similarity	NPC7921
0.7636	Intermediate Similarity	NPC478212
0.7636	Intermediate Similarity	NPC208998
0.7627	Intermediate Similarity	NPC231529
0.7624	Intermediate Similarity	NPC37603
0.7624	Intermediate Similarity	NPC471786
0.7624	Intermediate Similarity	NPC86893
0.7624	Intermediate Similarity	NPC292178
0.7619	Intermediate Similarity	NPC120321
0.7619	Intermediate Similarity	NPC472821
0.7619	Intermediate Similarity	NPC473523
0.7619	Intermediate Similarity	NPC474575
0.7619	Intermediate Similarity	NPC45897
0.7615	Intermediate Similarity	NPC470076
0.7611	Intermediate Similarity	NPC473636
0.7611	Intermediate Similarity	NPC230513
0.7611	Intermediate Similarity	NPC473839
0.7611	Intermediate Similarity	NPC77689
0.7611	Intermediate Similarity	NPC211093
0.7604	Intermediate Similarity	NPC253604
0.7596	Intermediate Similarity	NPC198992
0.7593	Intermediate Similarity	NPC322912
0.7593	Intermediate Similarity	NPC31522
0.7593	Intermediate Similarity	NPC257853
0.7593	Intermediate Similarity	NPC42662
0.7589	Intermediate Similarity	NPC469684
0.7589	Intermediate Similarity	NPC176513
0.7589	Intermediate Similarity	NPC122033
0.7589	Intermediate Similarity	NPC478204
0.7589	Intermediate Similarity	NPC13713
0.7589	Intermediate Similarity	NPC470854
0.7589	Intermediate Similarity	NPC470775
0.7589	Intermediate Similarity	NPC53396
0.7589	Intermediate Similarity	NPC474483
0.7589	Intermediate Similarity	NPC134430
0.7589	Intermediate Similarity	NPC98249
0.7589	Intermediate Similarity	NPC474654
0.7589	Intermediate Similarity	NPC475809
0.7589	Intermediate Similarity	NPC287343
0.7589	Intermediate Similarity	NPC97908
0.7586	Intermediate Similarity	NPC24651
0.7586	Intermediate Similarity	NPC469790
0.7576	Intermediate Similarity	NPC78973
0.7573	Intermediate Similarity	NPC222303
0.7573	Intermediate Similarity	NPC275086
0.7573	Intermediate Similarity	NPC325229
0.7573	Intermediate Similarity	NPC475068
0.757	Intermediate Similarity	NPC180744
0.757	Intermediate Similarity	NPC143609
0.757	Intermediate Similarity	NPC112780
0.7568	Intermediate Similarity	NPC73314
0.7565	Intermediate Similarity	NPC312833
0.7549	Intermediate Similarity	NPC473153

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 NPC199099 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	196
0.1-0.2	1905
0.2-0.3	3749
0.3-0.4	2143
0.4-0.5	770
0.5-0.6	294
0.6-0.7	79
0.7-0.8	14
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
0.8269	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.819	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7767	Intermediate Similarity	NPD5344	Discontinued
0.7745	Intermediate Similarity	NPD4225	Approved
0.7611	Intermediate Similarity	NPD7516	Approved
0.7522	Intermediate Similarity	NPD7328	Approved
0.7522	Intermediate Similarity	NPD7327	Approved
0.75	Intermediate Similarity	NPD6648	Approved
0.7238	Intermediate Similarity	NPD7638	Approved
0.719	Intermediate Similarity	NPD7319	Approved
0.7182	Intermediate Similarity	NPD6686	Approved
0.7182	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD8296	Approved
0.7179	Intermediate Similarity	NPD8380	Approved
0.7179	Intermediate Similarity	NPD8335	Approved
0.7179	Intermediate Similarity	NPD8379	Approved
0.7179	Intermediate Similarity	NPD8378	Approved
0.7179	Intermediate Similarity	NPD8033	Approved
0.717	Intermediate Similarity	NPD7640	Approved
0.717	Intermediate Similarity	NPD7639	Approved
0.7094	Intermediate Similarity	NPD8294	Approved
0.7094	Intermediate Similarity	NPD8377	Approved
0.7037	Intermediate Similarity	NPD7632	Discontinued
0.6983	Remote Similarity	NPD7115	Discovery
0.6942	Remote Similarity	NPD7507	Approved
0.6893	Remote Similarity	NPD6698	Approved
0.6893	Remote Similarity	NPD7838	Discovery
0.6893	Remote Similarity	NPD46	Approved
0.6807	Remote Similarity	NPD6319	Approved
0.6786	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.675	Remote Similarity	NPD7503	Approved
0.6667	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD6921	Approved
0.6555	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD7637	Suspended
0.6486	Remote Similarity	NPD4159	Approved
0.6475	Remote Similarity	NPD8516	Approved
0.6475	Remote Similarity	NPD8513	Phase 3
0.6475	Remote Similarity	NPD8517	Approved
0.6475	Remote Similarity	NPD8515	Approved
0.6466	Remote Similarity	NPD6371	Approved
0.6455	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD7524	Approved
0.6441	Remote Similarity	NPD4632	Approved
0.6441	Remote Similarity	NPD8133	Approved
0.6436	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD3168	Discontinued
0.6371	Remote Similarity	NPD8328	Phase 3
0.6356	Remote Similarity	NPD8297	Approved
0.6356	Remote Similarity	NPD6053	Discontinued
0.6355	Remote Similarity	NPD7983	Approved
0.632	Remote Similarity	NPD7492	Approved
0.6296	Remote Similarity	NPD5779	Approved
0.6296	Remote Similarity	NPD5778	Approved
0.627	Remote Similarity	NPD6616	Approved
0.6261	Remote Similarity	NPD6008	Approved
0.6261	Remote Similarity	NPD5739	Approved
0.6261	Remote Similarity	NPD6402	Approved
0.6261	Remote Similarity	NPD7128	Approved
0.6261	Remote Similarity	NPD6675	Approved
0.626	Remote Similarity	NPD6054	Approved
0.626	Remote Similarity	NPD6059	Approved
0.6239	Remote Similarity	NPD6373	Approved
0.6239	Remote Similarity	NPD6372	Approved
0.6239	Remote Similarity	NPD7748	Approved
0.622	Remote Similarity	NPD8074	Phase 3
0.622	Remote Similarity	NPD7078	Approved
0.622	Remote Similarity	NPD8293	Discontinued
0.6216	Remote Similarity	NPD7902	Approved
0.621	Remote Similarity	NPD6016	Approved
0.621	Remote Similarity	NPD6015	Approved
0.6207	Remote Similarity	NPD5697	Approved
0.6207	Remote Similarity	NPD5701	Approved
0.6207	Remote Similarity	NPD6412	Phase 2
0.6186	Remote Similarity	NPD4634	Approved
0.6172	Remote Similarity	NPD7736	Approved
0.616	Remote Similarity	NPD5988	Approved
0.616	Remote Similarity	NPD6370	Approved
0.6154	Remote Similarity	NPD6881	Approved
0.6154	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7320	Approved
0.6154	Remote Similarity	NPD6899	Approved
0.6148	Remote Similarity	NPD6009	Approved
0.6147	Remote Similarity	NPD6399	Phase 3
0.6146	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.614	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD6650	Approved
0.6134	Remote Similarity	NPD6649	Approved
0.6102	Remote Similarity	NPD6012	Approved
0.6102	Remote Similarity	NPD6013	Approved
0.6102	Remote Similarity	NPD6014	Approved
0.6095	Remote Similarity	NPD1694	Approved
0.6083	Remote Similarity	NPD6882	Approved
0.608	Remote Similarity	NPD5983	Phase 2
0.6058	Remote Similarity	NPD6695	Phase 3
0.6055	Remote Similarity	NPD7515	Phase 2
0.605	Remote Similarity	NPD6883	Approved
0.605	Remote Similarity	NPD7290	Approved
0.605	Remote Similarity	NPD7102	Approved
0.6022	Remote Similarity	NPD371	Approved
0.6019	Remote Similarity	NPD6051	Approved
0.6017	Remote Similarity	NPD6011	Approved
0.6	Remote Similarity	NPD6617	Approved
0.6	Remote Similarity	NPD6869	Approved
0.6	Remote Similarity	NPD8130	Phase 1
0.6	Remote Similarity	NPD6847	Approved
0.5984	Remote Similarity	NPD7604	Phase 2
0.5957	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD7900	Approved
0.5946	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD5282	Discontinued
0.5929	Remote Similarity	NPD6084	Phase 2
0.5929	Remote Similarity	NPD4755	Approved
0.5929	Remote Similarity	NPD6083	Phase 2
0.5922	Remote Similarity	NPD7525	Registered
0.5913	Remote Similarity	NPD1700	Approved
0.5909	Remote Similarity	NPD8035	Phase 2
0.5909	Remote Similarity	NPD8034	Phase 2
0.5905	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD3669	Approved
0.5893	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD5695	Phase 3
0.5891	Remote Similarity	NPD6336	Discontinued
0.5888	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD3618	Phase 1
0.5887	Remote Similarity	NPD7625	Phase 1
0.5877	Remote Similarity	NPD5696	Approved
0.5872	Remote Similarity	NPD6101	Approved
0.5872	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5868	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD5211	Phase 2
0.5856	Remote Similarity	NPD4202	Approved
0.5847	Remote Similarity	NPD5357	Phase 1
0.5833	Remote Similarity	NPD7750	Discontinued
0.5826	Remote Similarity	NPD5286	Approved
0.5826	Remote Similarity	NPD4696	Approved
0.5826	Remote Similarity	NPD5285	Approved
0.5826	Remote Similarity	NPD4700	Approved
0.5806	Remote Similarity	NPD6274	Approved
0.5802	Remote Similarity	NPD6033	Approved
0.5794	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD7260	Phase 2
0.5781	Remote Similarity	NPD8080	Discontinued
0.5769	Remote Similarity	NPD6930	Phase 2
0.5769	Remote Similarity	NPD6931	Approved
0.5766	Remote Similarity	NPD6411	Approved
0.5766	Remote Similarity	NPD5693	Phase 1
0.5763	Remote Similarity	NPD5141	Approved
0.576	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5746	Remote Similarity	NPD6845	Suspended
0.5741	Remote Similarity	NPD4249	Approved
0.5741	Remote Similarity	NPD7521	Approved
0.5741	Remote Similarity	NPD5330	Approved
0.5741	Remote Similarity	NPD7334	Approved
0.5741	Remote Similarity	NPD6409	Approved
0.5741	Remote Similarity	NPD7146	Approved
0.5741	Remote Similarity	NPD6684	Approved
0.5727	Remote Similarity	NPD5328	Approved
0.5727	Remote Similarity	NPD1695	Approved
0.5726	Remote Similarity	NPD5226	Approved
0.5726	Remote Similarity	NPD5224	Approved
0.5726	Remote Similarity	NPD5225	Approved
0.5726	Remote Similarity	NPD4633	Approved
0.5714	Remote Similarity	NPD4767	Approved
0.5714	Remote Similarity	NPD4768	Approved
0.5693	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD3573	Approved
0.5688	Remote Similarity	NPD4250	Approved
0.5688	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD4251	Approved
0.5678	Remote Similarity	NPD5174	Approved
0.5678	Remote Similarity	NPD5175	Approved
0.5676	Remote Similarity	NPD5785	Approved
0.5673	Remote Similarity	NPD6929	Approved
0.5673	Remote Similarity	NPD7645	Phase 2
0.5669	Remote Similarity	NPD7100	Approved
0.5669	Remote Similarity	NPD7101	Approved
0.566	Remote Similarity	NPD3667	Approved
0.5648	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5648	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD5223	Approved
0.5636	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD6903	Approved
0.5636	Remote Similarity	NPD5737	Approved
0.5636	Remote Similarity	NPD6672	Approved
0.5635	Remote Similarity	NPD6317	Approved
0.5625	Remote Similarity	NPD7087	Discontinued
0.5625	Remote Similarity	NPD6079	Approved
0.562	Remote Similarity	NPD4729	Approved
0.562	Remote Similarity	NPD4730	Approved
0.5619	Remote Similarity	NPD4820	Approved
0.5619	Remote Similarity	NPD4821	Approved
0.5619	Remote Similarity	NPD7332	Phase 2
0.5619	Remote Similarity	NPD4819	Approved
0.5619	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD7514	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