NPASS Compound

Structure

NPC469986 OpenBabel07101718322D 35 38 0 0 1 0 0 0 0 0999 V2000 2.8998 2.3308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8779 -1.4601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2944 4.1149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8262 -0.7564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3391 1.1302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4225 2.6741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0751 2.1536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4509 2.6021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5924 2.0892 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3307 2.0217 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4958 -0.3975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8521 0.2568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6182 0.3693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9487 2.0217 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8781 -1.4750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1678 3.6279 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8208 -0.6519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1397 2.6095 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0215 1.4400 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4808 0.6024 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3243 2.1151 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6397 1.0707 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.6289 0.3507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3392 1.1153 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6074 1.0893 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6397 1.0707 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6373 -0.9104 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3911 -2.3485 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0262 4.1408 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4085 -1.4609 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4874 -0.1622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3652 -0.6166 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 -3.1827 2.6280 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2275 0.2617 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 2 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 6 7 1 0 0 0 0 7 19 1 0 0 0 0 8 9 1 0 0 0 0 8 21 1 0 0 0 0 10 18 1 0 0 0 0 11 20 1 0 0 0 0 11 27 2 0 0 0 0 12 24 1 0 0 0 0 12 32 1 0 0 0 0 13 25 1 0 0 0 0 13 33 1 0 0 0 0 14 18 1 0 0 0 0 14 22 1 0 0 0 0 15 28 2 0 0 0 0 15 32 1 0 0 0 0 16 29 2 0 0 0 0 16 34 1 0 0 0 0 17 30 2 0 0 0 0 17 35 1 0 0 0 0 18 6 1 1 0 0 0 19 25 1 6 0 0 0 19 26 1 0 0 0 0 20 24 1 6 0 0 0 20 25 1 0 0 0 0 21 24 1 1 0 0 0 21 34 1 0 0 0 0 22 26 1 0 0 0 0 22 35 1 0 0 0 0 23 26 1 0 0 0 0 23 31 2 0 0 0 0 23 33 1 0 0 0 0 24 5 1 1 0 0 0 25 9 1 6 0 0 0 26 10 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	490.22
Volume:	487.32
LogP:	1.804
LogD:	1.104
LogS:	-4.061
# Rotatable Bonds:	8
TPSA:	122.27
# H-Bond Aceptor:	9
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.248
Synthetic Accessibility Score:	6.536
Fsp3:	0.731
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.247
MDCK Permeability:	8.086864545475692e-05
Pgp-inhibitor:	0.985
Pgp-substrate:	0.039
Human Intestinal Absorption (HIA):	0.029
20% Bioavailability (F20%):	0.924
30% Bioavailability (F30%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.963
Plasma Protein Binding (PPB):	56.63215637207031%
Volume Distribution (VD):	1.764
Pgp-substrate:	48.22511291503906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.05
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.086
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.02
CYP2D6-inhibitor:	0.029
CYP2D6-substrate:	0.081
CYP3A4-inhibitor:	0.747
CYP3A4-substrate:	0.284

ADMET: Excretion

Clearance (CL):	2.878
Half-life (T1/2):	0.154

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.527
Drug-inuced Liver Injury (DILI):	0.745
AMES Toxicity:	0.683
Rat Oral Acute Toxicity:	0.545
Maximum Recommended Daily Dose:	0.935
Skin Sensitization:	0.34
Carcinogencity:	0.708
Eye Corrosion:	0.088
Eye Irritation:	0.732
Respiratory Toxicity:	0.667

Download Data

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

Natural Product: NPC469986

Natural Product ID:	NPC469986
*Common Name:**	Maoesin F
IUPAC Name:	n.a.
Synonyms:	Maoesin F
Standard InCHIKey:	MSMFJFBUEIHNHZ-KBMFATIWSA-N
Standard InCHI:	InChI=1S/C26H34O9/c1-14-18-6-7-19-25(13-33-23(31)26(19,10-18)22(14)35-17(4)30)9-8-21(34-16(3)29)24(5,20(25)11-27)12-32-15(2)28/h11,18-22H,1,6-10,12-13H2,2-5H3/t18-,19+,20-,21+,22?,24+,25-,26+/m1/s1
SMILES:	O=C[C@@H]1[C@](C)(COC(=O)C)[C@H](CC[C@@]21COC(=O)[C@]13[C@H]2CC[C@H](C1)C(=C)C3OC(=O)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1641895
PubChem CID:	53323114
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene 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
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17020288]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[20949916]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[20949916]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22624550]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	10000.0	nM	PMID[567265]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10000.0	nM	PMID[567265]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	>	10000.0	nM	PMID[567265]

☑ 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 NPC469986 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	266
0.1-0.2	1915
0.2-0.3	6047
0.3-0.4	12475
0.4-0.5	8808
0.5-0.6	6341
0.6-0.7	5401
0.7-0.8	1313
0.8-0.85	117
0.85-0.9	11
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8854	High Similarity	NPC96839
0.88	High Similarity	NPC295366
0.8558	High Similarity	NPC471251
0.8529	High Similarity	NPC471246
0.85	High Similarity	NPC170615
0.8462	Intermediate Similarity	NPC124053
0.8431	Intermediate Similarity	NPC28791
0.8416	Intermediate Similarity	NPC96217
0.84	Intermediate Similarity	NPC39683
0.8365	Intermediate Similarity	NPC471250
0.835	Intermediate Similarity	NPC86852
0.835	Intermediate Similarity	NPC251824
0.8333	Intermediate Similarity	NPC470230
0.8316	Intermediate Similarity	NPC471043
0.83	Intermediate Similarity	NPC287676
0.8265	Intermediate Similarity	NPC217329
0.8261	Intermediate Similarity	NPC170862
0.8252	Intermediate Similarity	NPC37600
0.8218	Intermediate Similarity	NPC253886
0.8218	Intermediate Similarity	NPC236585
0.8218	Intermediate Similarity	NPC148279
0.8218	Intermediate Similarity	NPC289148
0.8218	Intermediate Similarity	NPC163963
0.8218	Intermediate Similarity	NPC52899
0.8218	Intermediate Similarity	NPC121218
0.8208	Intermediate Similarity	NPC94650
0.82	Intermediate Similarity	NPC78427
0.82	Intermediate Similarity	NPC474793
0.82	Intermediate Similarity	NPC16911
0.8163	Intermediate Similarity	NPC100257
0.8163	Intermediate Similarity	NPC224410
0.8155	Intermediate Similarity	NPC47281
0.8137	Intermediate Similarity	NPC275990
0.8137	Intermediate Similarity	NPC76866
0.8137	Intermediate Similarity	NPC304832
0.8137	Intermediate Similarity	NPC148628
0.8137	Intermediate Similarity	NPC88203
0.8137	Intermediate Similarity	NPC246736
0.8137	Intermediate Similarity	NPC286519
0.8137	Intermediate Similarity	NPC214946
0.8131	Intermediate Similarity	NPC40608
0.8119	Intermediate Similarity	NPC108371
0.8113	Intermediate Similarity	NPC255655
0.8105	Intermediate Similarity	NPC175293
0.81	Intermediate Similarity	NPC469810
0.8081	Intermediate Similarity	NPC470229
0.8077	Intermediate Similarity	NPC285927
0.8077	Intermediate Similarity	NPC50535
0.8073	Intermediate Similarity	NPC72772
0.8073	Intermediate Similarity	NPC469794
0.8061	Intermediate Similarity	NPC199543
0.8058	Intermediate Similarity	NPC469985
0.8058	Intermediate Similarity	NPC87927
0.8041	Intermediate Similarity	NPC475776
0.8039	Intermediate Similarity	NPC46848
0.8039	Intermediate Similarity	NPC295276
0.8039	Intermediate Similarity	NPC75941
0.8037	Intermediate Similarity	NPC470311
0.802	Intermediate Similarity	NPC471038
0.802	Intermediate Similarity	NPC472028
0.802	Intermediate Similarity	NPC26270
0.8	Intermediate Similarity	NPC234564
0.8	Intermediate Similarity	NPC472505
0.8	Intermediate Similarity	NPC329910
0.8	Intermediate Similarity	NPC284732
0.8	Intermediate Similarity	NPC78966
0.7981	Intermediate Similarity	NPC474558
0.7981	Intermediate Similarity	NPC98603
0.7981	Intermediate Similarity	NPC202793
0.798	Intermediate Similarity	NPC475118
0.798	Intermediate Similarity	NPC474841
0.798	Intermediate Similarity	NPC47853
0.798	Intermediate Similarity	NPC473434
0.798	Intermediate Similarity	NPC471446
0.7959	Intermediate Similarity	NPC130840
0.7944	Intermediate Similarity	NPC130302
0.7944	Intermediate Similarity	NPC98633
0.7941	Intermediate Similarity	NPC180733
0.7941	Intermediate Similarity	NPC94906
0.7941	Intermediate Similarity	NPC41971
0.7941	Intermediate Similarity	NPC37047
0.7928	Intermediate Similarity	NPC471249
0.7925	Intermediate Similarity	NPC37628
0.7921	Intermediate Similarity	NPC253586
0.7905	Intermediate Similarity	NPC200957
0.7905	Intermediate Similarity	NPC138908
0.79	Intermediate Similarity	NPC210214
0.79	Intermediate Similarity	NPC470232
0.79	Intermediate Similarity	NPC205173
0.7885	Intermediate Similarity	NPC139347
0.7885	Intermediate Similarity	NPC216114
0.7885	Intermediate Similarity	NPC122811
0.787	Intermediate Similarity	NPC270586
0.787	Intermediate Similarity	NPC56025
0.7864	Intermediate Similarity	NPC111292
0.785	Intermediate Similarity	NPC474243
0.785	Intermediate Similarity	NPC274827
0.785	Intermediate Similarity	NPC131903
0.7843	Intermediate Similarity	NPC476807
0.7843	Intermediate Similarity	NPC28864
0.7843	Intermediate Similarity	NPC162459
0.7843	Intermediate Similarity	NPC38471
0.7843	Intermediate Similarity	NPC176845
0.7843	Intermediate Similarity	NPC476806
0.7843	Intermediate Similarity	NPC98837
0.7843	Intermediate Similarity	NPC38296
0.7843	Intermediate Similarity	NPC20479
0.783	Intermediate Similarity	NPC166993
0.783	Intermediate Similarity	NPC176949
0.783	Intermediate Similarity	NPC201908
0.7822	Intermediate Similarity	NPC13949
0.7822	Intermediate Similarity	NPC29410
0.7822	Intermediate Similarity	NPC200054
0.7822	Intermediate Similarity	NPC118159
0.7812	Intermediate Similarity	NPC471042
0.781	Intermediate Similarity	NPC84928
0.78	Intermediate Similarity	NPC470385
0.78	Intermediate Similarity	NPC470386
0.78	Intermediate Similarity	NPC3359
0.7798	Intermediate Similarity	NPC476964
0.7798	Intermediate Similarity	NPC474927
0.7788	Intermediate Similarity	NPC475803
0.7788	Intermediate Similarity	NPC124544
0.7788	Intermediate Similarity	NPC309388
0.7788	Intermediate Similarity	NPC164551
0.7778	Intermediate Similarity	NPC474786
0.7778	Intermediate Similarity	NPC320383
0.7778	Intermediate Similarity	NPC137104
0.7778	Intermediate Similarity	NPC476934
0.7778	Intermediate Similarity	NPC471901
0.7767	Intermediate Similarity	NPC293866
0.7767	Intermediate Similarity	NPC267921
0.7757	Intermediate Similarity	NPC231278
0.7757	Intermediate Similarity	NPC273155
0.7757	Intermediate Similarity	NPC112895
0.7757	Intermediate Similarity	NPC218123
0.7757	Intermediate Similarity	NPC232133
0.7755	Intermediate Similarity	NPC474679
0.7748	Intermediate Similarity	NPC196931
0.7745	Intermediate Similarity	NPC474921
0.7745	Intermediate Similarity	NPC274793
0.7739	Intermediate Similarity	NPC55602
0.7736	Intermediate Similarity	NPC476762
0.7736	Intermediate Similarity	NPC476761
0.7736	Intermediate Similarity	NPC476760
0.7736	Intermediate Similarity	NPC4115
0.7732	Intermediate Similarity	NPC134197
0.7727	Intermediate Similarity	NPC52634
0.7727	Intermediate Similarity	NPC285086
0.7727	Intermediate Similarity	NPC471252
0.7723	Intermediate Similarity	NPC263135
0.7723	Intermediate Similarity	NPC288906
0.7723	Intermediate Similarity	NPC98639
0.7723	Intermediate Similarity	NPC157686
0.7723	Intermediate Similarity	NPC259042
0.7714	Intermediate Similarity	NPC277074
0.7714	Intermediate Similarity	NPC470310
0.7714	Intermediate Similarity	NPC266
0.7714	Intermediate Similarity	NPC209298
0.7708	Intermediate Similarity	NPC474971
0.7708	Intermediate Similarity	NPC98270
0.7706	Intermediate Similarity	NPC329953
0.7706	Intermediate Similarity	NPC470281
0.7706	Intermediate Similarity	NPC213320
0.77	Intermediate Similarity	NPC473690
0.77	Intermediate Similarity	NPC471902
0.77	Intermediate Similarity	NPC294263
0.77	Intermediate Similarity	NPC287118
0.7692	Intermediate Similarity	NPC242666
0.7692	Intermediate Similarity	NPC14634
0.7692	Intermediate Similarity	NPC471790
0.7692	Intermediate Similarity	NPC252614
0.7685	Intermediate Similarity	NPC469983
0.7685	Intermediate Similarity	NPC102741
0.7684	Intermediate Similarity	NPC471037
0.7677	Intermediate Similarity	NPC123252
0.7677	Intermediate Similarity	NPC194485
0.7677	Intermediate Similarity	NPC161638
0.7677	Intermediate Similarity	NPC219937
0.7677	Intermediate Similarity	NPC53890
0.7677	Intermediate Similarity	NPC169933
0.767	Intermediate Similarity	NPC271387
0.767	Intermediate Similarity	NPC153792
0.767	Intermediate Similarity	NPC89099
0.7664	Intermediate Similarity	NPC96333
0.7664	Intermediate Similarity	NPC470952
0.7664	Intermediate Similarity	NPC88833
0.766	Intermediate Similarity	NPC475951
0.7653	Intermediate Similarity	NPC160304
0.7653	Intermediate Similarity	NPC80335
0.7647	Intermediate Similarity	NPC135548
0.7647	Intermediate Similarity	NPC470387
0.7647	Intermediate Similarity	NPC473964
0.7647	Intermediate Similarity	NPC317573
0.7647	Intermediate Similarity	NPC264979
0.7642	Intermediate Similarity	NPC470297
0.7642	Intermediate Similarity	NPC476763
0.7642	Intermediate Similarity	NPC244247
0.7642	Intermediate Similarity	NPC476764
0.7642	Intermediate Similarity	NPC96268

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 NPC469986 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	235
0.1-0.2	2310
0.2-0.3	3952
0.3-0.4	1795
0.4-0.5	426
0.5-0.6	221
0.6-0.7	180
0.7-0.8	31
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
0.7563	Intermediate Similarity	NPD7319	Approved
0.75	Intermediate Similarity	NPD7638	Approved
0.7458	Intermediate Similarity	NPD7507	Approved
0.7431	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD7640	Approved
0.7429	Intermediate Similarity	NPD7639	Approved
0.7426	Intermediate Similarity	NPD8034	Phase 2
0.7426	Intermediate Similarity	NPD8035	Phase 2
0.7411	Intermediate Similarity	NPD8133	Approved
0.7407	Intermediate Similarity	NPD6008	Approved
0.7207	Intermediate Similarity	NPD6372	Approved
0.7207	Intermediate Similarity	NPD6373	Approved
0.7172	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD6409	Approved
0.71	Intermediate Similarity	NPD7334	Approved
0.71	Intermediate Similarity	NPD7146	Approved
0.71	Intermediate Similarity	NPD6684	Approved
0.71	Intermediate Similarity	NPD7521	Approved
0.71	Intermediate Similarity	NPD5330	Approved
0.7091	Intermediate Similarity	NPD7128	Approved
0.7091	Intermediate Similarity	NPD6675	Approved
0.7091	Intermediate Similarity	NPD6402	Approved
0.7091	Intermediate Similarity	NPD5739	Approved
0.708	Intermediate Similarity	NPD6649	Approved
0.708	Intermediate Similarity	NPD6650	Approved
0.7048	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD6319	Approved
0.7027	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6399	Phase 3
0.6972	Remote Similarity	NPD7632	Discontinued
0.6964	Remote Similarity	NPD7320	Approved
0.6964	Remote Similarity	NPD6881	Approved
0.6964	Remote Similarity	NPD6899	Approved
0.6961	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD6903	Approved
0.6923	Remote Similarity	NPD5693	Phase 1
0.6923	Remote Similarity	NPD7115	Discovery
0.6893	Remote Similarity	NPD6051	Approved
0.6875	Remote Similarity	NPD5697	Approved
0.6875	Remote Similarity	NPD5701	Approved
0.687	Remote Similarity	NPD6882	Approved
0.687	Remote Similarity	NPD8297	Approved
0.6842	Remote Similarity	NPD7290	Approved
0.6842	Remote Similarity	NPD7102	Approved
0.6842	Remote Similarity	NPD6883	Approved
0.6842	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6921	Approved
0.6814	Remote Similarity	NPD6686	Approved
0.6804	Remote Similarity	NPD6697	Approved
0.6804	Remote Similarity	NPD6118	Approved
0.6804	Remote Similarity	NPD6115	Approved
0.6804	Remote Similarity	NPD6114	Approved
0.6803	Remote Similarity	NPD7492	Approved
0.6796	Remote Similarity	NPD5737	Approved
0.6796	Remote Similarity	NPD6672	Approved
0.6792	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD7900	Approved
0.6783	Remote Similarity	NPD8130	Phase 1
0.6783	Remote Similarity	NPD6869	Approved
0.6783	Remote Similarity	NPD6847	Approved
0.6783	Remote Similarity	NPD6617	Approved
0.6765	Remote Similarity	NPD6098	Approved
0.6759	Remote Similarity	NPD6083	Phase 2
0.6759	Remote Similarity	NPD6084	Phase 2
0.6754	Remote Similarity	NPD6014	Approved
0.6754	Remote Similarity	NPD6013	Approved
0.6754	Remote Similarity	NPD6012	Approved
0.675	Remote Similarity	NPD6054	Approved
0.675	Remote Similarity	NPD6059	Approved
0.6748	Remote Similarity	NPD6616	Approved
0.6731	Remote Similarity	NPD6673	Approved
0.6731	Remote Similarity	NPD6080	Approved
0.6731	Remote Similarity	NPD6904	Approved
0.6723	Remote Similarity	NPD7327	Approved
0.6723	Remote Similarity	NPD7328	Approved
0.6702	Remote Similarity	NPD5777	Approved
0.67	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD4225	Approved
0.6697	Remote Similarity	NPD5696	Approved
0.6694	Remote Similarity	NPD7078	Approved
0.6694	Remote Similarity	NPD8293	Discontinued
0.6667	Remote Similarity	NPD7516	Approved
0.6667	Remote Similarity	NPD4632	Approved
0.6667	Remote Similarity	NPD3702	Approved
0.6667	Remote Similarity	NPD4697	Phase 3
0.6667	Remote Similarity	NPD6011	Approved
0.664	Remote Similarity	NPD7736	Approved
0.6639	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD6370	Approved
0.6638	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6001	Approved
0.6636	Remote Similarity	NPD7748	Approved
0.6612	Remote Similarity	NPD8377	Approved
0.6612	Remote Similarity	NPD8294	Approved
0.6609	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD4755	Approved
0.6606	Remote Similarity	NPD7902	Approved
0.6604	Remote Similarity	NPD6411	Approved
0.6598	Remote Similarity	NPD6117	Approved
0.6585	Remote Similarity	NPD8328	Phase 3
0.6581	Remote Similarity	NPD6053	Discontinued
0.6579	Remote Similarity	NPD6412	Phase 2
0.6574	Remote Similarity	NPD5695	Phase 3
0.6571	Remote Similarity	NPD5328	Approved
0.6557	Remote Similarity	NPD8335	Approved
0.6557	Remote Similarity	NPD8379	Approved
0.6557	Remote Similarity	NPD8033	Approved
0.6557	Remote Similarity	NPD6016	Approved
0.6557	Remote Similarity	NPD8296	Approved
0.6557	Remote Similarity	NPD8378	Approved
0.6557	Remote Similarity	NPD6015	Approved
0.6557	Remote Similarity	NPD8380	Approved
0.6552	Remote Similarity	NPD4634	Approved
0.6538	Remote Similarity	NPD3573	Approved
0.6531	Remote Similarity	NPD6116	Phase 1
0.6518	Remote Similarity	NPD5211	Phase 2
0.6505	Remote Similarity	NPD1694	Approved
0.6504	Remote Similarity	NPD5988	Approved
0.65	Remote Similarity	NPD6009	Approved
0.6486	Remote Similarity	NPD4696	Approved
0.6486	Remote Similarity	NPD5285	Approved
0.6486	Remote Similarity	NPD4700	Approved
0.6486	Remote Similarity	NPD5286	Approved
0.6476	Remote Similarity	NPD5208	Approved
0.6471	Remote Similarity	NPD4788	Approved
0.6452	Remote Similarity	NPD7604	Phase 2
0.6449	Remote Similarity	NPD6050	Approved
0.6449	Remote Similarity	NPD7515	Phase 2
0.6449	Remote Similarity	NPD7637	Suspended
0.6449	Remote Similarity	NPD6079	Approved
0.6442	Remote Similarity	NPD3618	Phase 1
0.6423	Remote Similarity	NPD5983	Phase 2
0.6423	Remote Similarity	NPD7503	Approved
0.6417	Remote Similarity	NPD6274	Approved
0.6415	Remote Similarity	NPD6101	Approved
0.6415	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD4786	Approved
0.6404	Remote Similarity	NPD5141	Approved
0.6393	Remote Similarity	NPD7100	Approved
0.6393	Remote Similarity	NPD7101	Approved
0.6392	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD4202	Approved
0.6389	Remote Similarity	NPD5779	Approved
0.6389	Remote Similarity	NPD5778	Approved
0.6372	Remote Similarity	NPD4633	Approved
0.6372	Remote Similarity	NPD5225	Approved
0.6372	Remote Similarity	NPD5224	Approved
0.6372	Remote Similarity	NPD5226	Approved
0.6355	Remote Similarity	NPD5692	Phase 3
0.6355	Remote Similarity	NPD5207	Approved
0.6349	Remote Similarity	NPD6336	Discontinued
0.6348	Remote Similarity	NPD4767	Approved
0.6348	Remote Similarity	NPD4768	Approved
0.6316	Remote Similarity	NPD5174	Approved
0.6316	Remote Similarity	NPD5175	Approved
0.6311	Remote Similarity	NPD6335	Approved
0.6296	Remote Similarity	NPD5694	Approved
0.629	Remote Similarity	NPD6909	Approved
0.629	Remote Similarity	NPD6908	Approved
0.629	Remote Similarity	NPD8516	Approved
0.629	Remote Similarity	NPD8513	Phase 3
0.629	Remote Similarity	NPD8517	Approved
0.629	Remote Similarity	NPD8515	Approved
0.6286	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD1700	Approved
0.6283	Remote Similarity	NPD5223	Approved
0.6271	Remote Similarity	NPD6371	Approved
0.6262	Remote Similarity	NPD4753	Phase 2
0.6261	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3665	Phase 1
0.625	Remote Similarity	NPD6033	Approved
0.625	Remote Similarity	NPD3133	Approved
0.625	Remote Similarity	NPD3668	Phase 3
0.625	Remote Similarity	NPD3666	Approved
0.6239	Remote Similarity	NPD4729	Approved
0.6239	Remote Similarity	NPD4730	Approved
0.623	Remote Similarity	NPD6317	Approved
0.6216	Remote Similarity	NPD5221	Approved
0.6216	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD5222	Approved
0.6214	Remote Similarity	NPD3667	Approved
0.6204	Remote Similarity	NPD5785	Approved
0.6179	Remote Similarity	NPD6313	Approved
0.6179	Remote Similarity	NPD6314	Approved
0.6174	Remote Similarity	NPD6052	Approved
0.6174	Remote Similarity	NPD4754	Approved
0.6162	Remote Similarity	NPD3703	Phase 2
0.6161	Remote Similarity	NPD5173	Approved
0.616	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD6868	Approved
0.6147	Remote Similarity	NPD5284	Approved
0.6147	Remote Similarity	NPD5281	Approved
0.6134	Remote Similarity	NPD5247	Approved
0.6134	Remote Similarity	NPD5249	Phase 3
0.6134	Remote Similarity	NPD5248	Approved
0.6134	Remote Similarity	NPD5250	Approved
0.6134	Remote Similarity	NPD5251	Approved
0.6126	Remote Similarity	NPD5210	Approved

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