NPASS Compound

Structure

NPC26046 OpenBabel07101718232D 27 30 0 0 1 0 0 0 0 0999 V2000 2.1766 1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2457 2.7508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3481 -1.8543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3111 -1.8399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1866 0.9809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6161 -1.0312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4021 0.0359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7964 0.3737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0104 -0.6934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6884 1.0429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2607 0.9159 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3297 2.4532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2092 1.5442 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2114 -0.6755 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5953 0.3557 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4125 -0.6575 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4815 1.4820 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9631 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2976 0.9159 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8171 -1.0132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2010 0.0180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6140 3.0976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5476 2.4458 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2536 -1.1265 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5292 -0.7791 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1295 1.5112 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 2 0 0 0 0 2 12 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 6 9 1 0 0 0 0 6 14 1 0 0 0 0 7 8 1 0 0 0 0 7 16 1 0 0 0 0 8 21 1 0 0 0 0 10 13 1 0 0 0 0 10 15 1 0 0 0 0 11 18 1 0 0 0 0 12 23 2 0 0 0 0 12 27 1 0 0 0 0 13 17 1 0 0 0 0 13 24 1 6 0 0 0 14 20 1 0 0 0 0 14 21 1 6 0 0 0 15 21 1 6 0 0 0 15 22 1 0 0 0 0 16 20 1 0 0 0 0 16 25 1 1 0 0 0 17 11 1 1 0 0 0 17 19 1 0 0 0 0 18 22 1 1 0 0 0 18 26 1 0 0 0 0 19 22 1 6 0 0 0 19 27 1 0 0 0 0 21 5 1 6 0 0 0 22 9 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	378.24
Volume:	393.521
LogP:	1.839
LogD:	2.06
LogS:	-3.4
# Rotatable Bonds:	2
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.482
Synthetic Accessibility Score:	6.005
Fsp3:	0.864
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.843
MDCK Permeability:	8.18537810118869e-05
Pgp-inhibitor:	0.039
Pgp-substrate:	0.993
Human Intestinal Absorption (HIA):	0.119
20% Bioavailability (F20%):	0.562
30% Bioavailability (F30%):	0.822

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.306
Plasma Protein Binding (PPB):	38.21123504638672%
Volume Distribution (VD):	0.814
Pgp-substrate:	59.763465881347656%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.061
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.445
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.055
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.124
CYP3A4-inhibitor:	0.101
CYP3A4-substrate:	0.167

ADMET: Excretion

Clearance (CL):	4.192
Half-life (T1/2):	0.664

ADMET: Toxicity

hERG Blockers:	0.067
Human Hepatotoxicity (H-HT):	0.425
Drug-inuced Liver Injury (DILI):	0.044
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.977
Maximum Recommended Daily Dose:	0.995
Skin Sensitization:	0.623
Carcinogencity:	0.118
Eye Corrosion:	0.841
Eye Irritation:	0.371
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC26046

Natural Product ID:	NPC26046
*Common Name:**	QGGYIHJDPBNGNQ-WINDMQPFSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QGGYIHJDPBNGNQ-WINDMQPFSA-N
Standard InCHI:	InChI=1S/C22H34O5/c1-11-17-13(24)10-15-21(5)8-7-16(25)20(3,4)14(21)6-9-22(15,18(11)26)19(17)27-12(2)23/h13-19,24-26H,1,6-10H2,2-5H3/t13-,14+,15-,16-,17+,18+,19+,21+,22+/m0/s1
SMILES:	C=C1[C@@H]2[C@H](C[C@H]3[C@]4(C)CC[C@@H](C(C)(C)[C@H]4CC[C@@]3([C@@H]1O)[C@@H]2OC(=O)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL550506
PubChem CID:	44179096
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane diterpenoids

*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
NPO24459	Isodon pharicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19425589]
NPO24459	Isodon pharicus	Species	Lamiaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[29286250]
NPO24459	Isodon pharicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24459	Isodon pharicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24459	Isodon pharicus	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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2678	Cell Line	NB-4	Homo sapiens	IC50	>	10000.0	nM	PMID[534018]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[534018]
NPT519	Cell Line	SH-SY5Y	Homo sapiens	IC50	>	10000.0	nM	PMID[534018]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	>	10000.0	nM	PMID[534018]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[534018]

☑ 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 NPC26046 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	201
0.1-0.2	1755
0.2-0.3	5535
0.3-0.4	13962
0.4-0.5	8448
0.5-0.6	5040
0.6-0.7	5643
0.7-0.8	1892
0.8-0.85	173
0.85-0.9	29
0.9-0.95	8
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9767	High Similarity	NPC53890
0.9767	High Similarity	NPC219937
0.9767	High Similarity	NPC123252
0.9767	High Similarity	NPC194485
0.9659	High Similarity	NPC3359
0.9535	High Similarity	NPC160304
0.9432	High Similarity	NPC130840
0.9333	High Similarity	NPC241047
0.9231	High Similarity	NPC111834
0.9231	High Similarity	NPC306797
0.9231	High Similarity	NPC169270
0.9231	High Similarity	NPC292718
0.907	High Similarity	NPC256567
0.907	High Similarity	NPC299963
0.8947	High Similarity	NPC31085
0.8925	High Similarity	NPC274793
0.8889	High Similarity	NPC10274
0.8866	High Similarity	NPC37600
0.8854	High Similarity	NPC471467
0.8842	High Similarity	NPC121218
0.8842	High Similarity	NPC144486
0.8842	High Similarity	NPC253886
0.8837	High Similarity	NPC472504
0.8791	High Similarity	NPC219516
0.875	High Similarity	NPC177701
0.8721	High Similarity	NPC157655
0.8646	High Similarity	NPC49532
0.8632	High Similarity	NPC469725
0.8617	High Similarity	NPC304899
0.8617	High Similarity	NPC253115
0.8605	High Similarity	NPC47149
0.8586	High Similarity	NPC470169
0.8586	High Similarity	NPC475781
0.8586	High Similarity	NPC470170
0.8571	High Similarity	NPC47281
0.8557	High Similarity	NPC170615
0.8539	High Similarity	NPC164424
0.8523	High Similarity	NPC232023
0.8511	High Similarity	NPC30477
0.8488	Intermediate Similarity	NPC24504
0.8488	Intermediate Similarity	NPC5604
0.8488	Intermediate Similarity	NPC476316
0.8485	Intermediate Similarity	NPC119855
0.8485	Intermediate Similarity	NPC220217
0.8485	Intermediate Similarity	NPC50535
0.8454	Intermediate Similarity	NPC295276
0.8444	Intermediate Similarity	NPC168231
0.8421	Intermediate Similarity	NPC299654
0.84	Intermediate Similarity	NPC470166
0.8391	Intermediate Similarity	NPC78545
0.8391	Intermediate Similarity	NPC71535
0.8372	Intermediate Similarity	NPC472499
0.8372	Intermediate Similarity	NPC475
0.8372	Intermediate Similarity	NPC472502
0.8372	Intermediate Similarity	NPC472500
0.8351	Intermediate Similarity	NPC471247
0.8351	Intermediate Similarity	NPC208358
0.8351	Intermediate Similarity	NPC108371
0.8333	Intermediate Similarity	NPC475033
0.8333	Intermediate Similarity	NPC475032
0.8316	Intermediate Similarity	NPC473348
0.83	Intermediate Similarity	NPC295366
0.83	Intermediate Similarity	NPC28791
0.8283	Intermediate Similarity	NPC97487
0.8283	Intermediate Similarity	NPC469985
0.8283	Intermediate Similarity	NPC196471
0.8283	Intermediate Similarity	NPC10232
0.8283	Intermediate Similarity	NPC189588
0.8283	Intermediate Similarity	NPC187302
0.8265	Intermediate Similarity	NPC155974
0.8256	Intermediate Similarity	NPC260301
0.8256	Intermediate Similarity	NPC307336
0.8256	Intermediate Similarity	NPC138502
0.8252	Intermediate Similarity	NPC94650
0.8247	Intermediate Similarity	NPC38296
0.8247	Intermediate Similarity	NPC162459
0.8247	Intermediate Similarity	NPC16911
0.8247	Intermediate Similarity	NPC38471
0.8247	Intermediate Similarity	NPC78427
0.8247	Intermediate Similarity	NPC28864
0.8247	Intermediate Similarity	NPC98837
0.8247	Intermediate Similarity	NPC20479
0.8242	Intermediate Similarity	NPC121981
0.8229	Intermediate Similarity	NPC471903
0.8229	Intermediate Similarity	NPC54248
0.8229	Intermediate Similarity	NPC276103
0.8222	Intermediate Similarity	NPC86238
0.8222	Intermediate Similarity	NPC255882
0.8218	Intermediate Similarity	NPC251824
0.8218	Intermediate Similarity	NPC86852
0.8211	Intermediate Similarity	NPC280804
0.8211	Intermediate Similarity	NPC39453
0.8211	Intermediate Similarity	NPC474922
0.8182	Intermediate Similarity	NPC286519
0.8182	Intermediate Similarity	NPC214946
0.8182	Intermediate Similarity	NPC76866
0.8182	Intermediate Similarity	NPC304832
0.8182	Intermediate Similarity	NPC88203
0.8182	Intermediate Similarity	NPC206735
0.8182	Intermediate Similarity	NPC148628
0.8182	Intermediate Similarity	NPC474714
0.8182	Intermediate Similarity	NPC246736
0.8172	Intermediate Similarity	NPC194642
0.8172	Intermediate Similarity	NPC473647
0.8163	Intermediate Similarity	NPC287676
0.8163	Intermediate Similarity	NPC293866
0.8163	Intermediate Similarity	NPC37047
0.8163	Intermediate Similarity	NPC41971
0.8163	Intermediate Similarity	NPC180733
0.8161	Intermediate Similarity	NPC477819
0.8161	Intermediate Similarity	NPC472501
0.8161	Intermediate Similarity	NPC477817
0.8152	Intermediate Similarity	NPC44538
0.8144	Intermediate Similarity	NPC253586
0.814	Intermediate Similarity	NPC38141
0.8132	Intermediate Similarity	NPC266651
0.8125	Intermediate Similarity	NPC205173
0.8119	Intermediate Similarity	NPC165405
0.8111	Intermediate Similarity	NPC5280
0.8111	Intermediate Similarity	NPC473742
0.8105	Intermediate Similarity	NPC296620
0.8105	Intermediate Similarity	NPC473678
0.81	Intermediate Similarity	NPC87927
0.81	Intermediate Similarity	NPC160583
0.8081	Intermediate Similarity	NPC52899
0.8081	Intermediate Similarity	NPC39683
0.8081	Intermediate Similarity	NPC289148
0.8081	Intermediate Similarity	NPC75941
0.8081	Intermediate Similarity	NPC268829
0.8081	Intermediate Similarity	NPC295110
0.8081	Intermediate Similarity	NPC25177
0.8081	Intermediate Similarity	NPC475617
0.8081	Intermediate Similarity	NPC470168
0.8081	Intermediate Similarity	NPC222875
0.8081	Intermediate Similarity	NPC163963
0.8081	Intermediate Similarity	NPC46848
0.8081	Intermediate Similarity	NPC247701
0.8068	Intermediate Similarity	NPC476176
0.8061	Intermediate Similarity	NPC119036
0.8061	Intermediate Similarity	NPC275086
0.8061	Intermediate Similarity	NPC300179
0.8061	Intermediate Similarity	NPC102426
0.8061	Intermediate Similarity	NPC89099
0.8061	Intermediate Similarity	NPC325229
0.8058	Intermediate Similarity	NPC473570
0.8043	Intermediate Similarity	NPC201273
0.8043	Intermediate Similarity	NPC475684
0.8043	Intermediate Similarity	NPC474970
0.8041	Intermediate Similarity	NPC29410
0.8041	Intermediate Similarity	NPC200054
0.8022	Intermediate Similarity	NPC102048
0.8022	Intermediate Similarity	NPC263974
0.8021	Intermediate Similarity	NPC47853
0.802	Intermediate Similarity	NPC152966
0.802	Intermediate Similarity	NPC473543
0.8	Intermediate Similarity	NPC475344
0.8	Intermediate Similarity	NPC275990
0.8	Intermediate Similarity	NPC476471
0.8	Intermediate Similarity	NPC234335
0.8	Intermediate Similarity	NPC198054
0.8	Intermediate Similarity	NPC44537
0.798	Intermediate Similarity	NPC94906
0.798	Intermediate Similarity	NPC251680
0.798	Intermediate Similarity	NPC91497
0.7979	Intermediate Similarity	NPC291875
0.7978	Intermediate Similarity	NPC475679
0.7961	Intermediate Similarity	NPC112895
0.7961	Intermediate Similarity	NPC472218
0.7961	Intermediate Similarity	NPC218123
0.7961	Intermediate Similarity	NPC473517
0.7961	Intermediate Similarity	NPC472219
0.7961	Intermediate Similarity	NPC472217
0.7961	Intermediate Similarity	NPC231278
0.7959	Intermediate Similarity	NPC10864
0.7959	Intermediate Similarity	NPC51499
0.7959	Intermediate Similarity	NPC97867
0.7955	Intermediate Similarity	NPC471045
0.7955	Intermediate Similarity	NPC31828
0.7955	Intermediate Similarity	NPC301707
0.7941	Intermediate Similarity	NPC278628
0.7941	Intermediate Similarity	NPC285927
0.7941	Intermediate Similarity	NPC231530
0.7938	Intermediate Similarity	NPC157686
0.7938	Intermediate Similarity	NPC276110
0.7938	Intermediate Similarity	NPC210214
0.7938	Intermediate Similarity	NPC259042
0.7938	Intermediate Similarity	NPC98639
0.7921	Intermediate Similarity	NPC475623
0.7921	Intermediate Similarity	NPC474124
0.7921	Intermediate Similarity	NPC472821
0.7921	Intermediate Similarity	NPC473694
0.7921	Intermediate Similarity	NPC475334
0.7921	Intermediate Similarity	NPC222153
0.7921	Intermediate Similarity	NPC473523
0.7912	Intermediate Similarity	NPC216420
0.7912	Intermediate Similarity	NPC211135
0.7912	Intermediate Similarity	NPC110778
0.7912	Intermediate Similarity	NPC471037
0.7912	Intermediate Similarity	NPC85095
0.7907	Intermediate Similarity	NPC308440

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 NPC26046 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	174
0.1-0.2	2063
0.2-0.3	4084
0.3-0.4	1954
0.4-0.5	422
0.5-0.6	199
0.6-0.7	214
0.7-0.8	38
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.798	Intermediate Similarity	NPD7639	Approved
0.798	Intermediate Similarity	NPD7640	Approved
0.7879	Intermediate Similarity	NPD7638	Approved
0.7629	Intermediate Similarity	NPD8034	Phase 2
0.7629	Intermediate Similarity	NPD8035	Phase 2
0.7553	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD7328	Approved
0.7477	Intermediate Similarity	NPD7327	Approved
0.7476	Intermediate Similarity	NPD7632	Discontinued
0.7447	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD8033	Approved
0.7411	Intermediate Similarity	NPD7516	Approved
0.7391	Intermediate Similarity	NPD7525	Registered
0.734	Intermediate Similarity	NPD6695	Phase 3
0.7281	Intermediate Similarity	NPD8296	Approved
0.7281	Intermediate Similarity	NPD8380	Approved
0.7281	Intermediate Similarity	NPD8379	Approved
0.7281	Intermediate Similarity	NPD8378	Approved
0.7281	Intermediate Similarity	NPD8335	Approved
0.7273	Intermediate Similarity	NPD8133	Approved
0.7273	Intermediate Similarity	NPD7637	Suspended
0.7264	Intermediate Similarity	NPD7128	Approved
0.7264	Intermediate Similarity	NPD6675	Approved
0.7264	Intermediate Similarity	NPD6402	Approved
0.7264	Intermediate Similarity	NPD5739	Approved
0.72	Intermediate Similarity	NPD6399	Phase 3
0.7193	Intermediate Similarity	NPD8377	Approved
0.7193	Intermediate Similarity	NPD8294	Approved
0.7174	Intermediate Similarity	NPD6118	Approved
0.7174	Intermediate Similarity	NPD6115	Approved
0.7174	Intermediate Similarity	NPD6114	Approved
0.7174	Intermediate Similarity	NPD6697	Approved
0.713	Intermediate Similarity	NPD7320	Approved
0.713	Intermediate Similarity	NPD6881	Approved
0.713	Intermediate Similarity	NPD6899	Approved
0.7097	Intermediate Similarity	NPD6929	Approved
0.7065	Intermediate Similarity	NPD6116	Phase 1
0.7064	Intermediate Similarity	NPD6373	Approved
0.7064	Intermediate Similarity	NPD6372	Approved
0.7041	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7524	Approved
0.7041	Intermediate Similarity	NPD7750	Discontinued
0.7037	Intermediate Similarity	NPD5697	Approved
0.7037	Intermediate Similarity	NPD5701	Approved
0.7021	Intermediate Similarity	NPD6931	Approved
0.7021	Intermediate Similarity	NPD6928	Phase 2
0.7021	Intermediate Similarity	NPD6930	Phase 2
0.7	Intermediate Similarity	NPD7102	Approved
0.7	Intermediate Similarity	NPD7290	Approved
0.7	Intermediate Similarity	NPD6883	Approved
0.6957	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6117	Approved
0.6944	Remote Similarity	NPD6008	Approved
0.6937	Remote Similarity	NPD6617	Approved
0.6937	Remote Similarity	NPD6869	Approved
0.6937	Remote Similarity	NPD6649	Approved
0.6937	Remote Similarity	NPD6847	Approved
0.6937	Remote Similarity	NPD6650	Approved
0.6937	Remote Similarity	NPD8130	Phase 1
0.6923	Remote Similarity	NPD6083	Phase 2
0.6923	Remote Similarity	NPD6084	Phase 2
0.6915	Remote Similarity	NPD7645	Phase 2
0.6909	Remote Similarity	NPD6012	Approved
0.6909	Remote Similarity	NPD6013	Approved
0.6909	Remote Similarity	NPD6014	Approved
0.69	Remote Similarity	NPD6051	Approved
0.6891	Remote Similarity	NPD7507	Approved
0.6882	Remote Similarity	NPD5776	Phase 2
0.6882	Remote Similarity	NPD6925	Approved
0.6875	Remote Similarity	NPD8297	Approved
0.6875	Remote Similarity	NPD6882	Approved
0.686	Remote Similarity	NPD7319	Approved
0.6857	Remote Similarity	NPD4225	Approved
0.6848	Remote Similarity	NPD7339	Approved
0.6848	Remote Similarity	NPD6942	Approved
0.6838	Remote Similarity	NPD7503	Approved
0.6822	Remote Similarity	NPD5211	Phase 2
0.6818	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6011	Approved
0.6814	Remote Similarity	NPD4632	Approved
0.6809	Remote Similarity	NPD7145	Approved
0.6804	Remote Similarity	NPD4788	Approved
0.6796	Remote Similarity	NPD7748	Approved
0.6786	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7087	Discontinued
0.6765	Remote Similarity	NPD7515	Phase 2
0.6762	Remote Similarity	NPD7902	Approved
0.6762	Remote Similarity	NPD4755	Approved
0.6757	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6319	Approved
0.6739	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD4786	Approved
0.6729	Remote Similarity	NPD5344	Discontinued
0.6727	Remote Similarity	NPD6412	Phase 2
0.6726	Remote Similarity	NPD6053	Discontinued
0.67	Remote Similarity	NPD4250	Approved
0.67	Remote Similarity	NPD4251	Approved
0.6699	Remote Similarity	NPD4202	Approved
0.6697	Remote Similarity	NPD5141	Approved
0.6667	Remote Similarity	NPD7492	Approved
0.6667	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6893	Approved
0.6667	Remote Similarity	NPD7514	Phase 3
0.6667	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD7736	Approved
0.6638	Remote Similarity	NPD7115	Discovery
0.6638	Remote Similarity	NPD6009	Approved
0.6636	Remote Similarity	NPD4696	Approved
0.6636	Remote Similarity	NPD5285	Approved
0.6636	Remote Similarity	NPD5286	Approved
0.6636	Remote Similarity	NPD4700	Approved
0.6634	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD6616	Approved
0.661	Remote Similarity	NPD6059	Approved
0.661	Remote Similarity	NPD6054	Approved
0.66	Remote Similarity	NPD7334	Approved
0.66	Remote Similarity	NPD7521	Approved
0.66	Remote Similarity	NPD6409	Approved
0.66	Remote Similarity	NPD6684	Approved
0.66	Remote Similarity	NPD7146	Approved
0.66	Remote Similarity	NPD4249	Approved
0.66	Remote Similarity	NPD5330	Approved
0.6598	Remote Similarity	NPD6902	Approved
0.6583	Remote Similarity	NPD7604	Phase 2
0.6571	Remote Similarity	NPD5695	Phase 3
0.6569	Remote Similarity	NPD5328	Approved
0.6557	Remote Similarity	NPD7078	Approved
0.6557	Remote Similarity	NPD8293	Discontinued
0.6555	Remote Similarity	NPD5983	Phase 2
0.6552	Remote Similarity	NPD6274	Approved
0.6549	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD5696	Approved
0.6538	Remote Similarity	NPD8171	Discontinued
0.6531	Remote Similarity	NPD3667	Approved
0.6526	Remote Similarity	NPD6932	Approved
0.6525	Remote Similarity	NPD7101	Approved
0.6525	Remote Similarity	NPD7100	Approved
0.6518	Remote Similarity	NPD6686	Approved
0.6514	Remote Similarity	NPD5224	Approved
0.6514	Remote Similarity	NPD5225	Approved
0.6514	Remote Similarity	NPD5226	Approved
0.6514	Remote Similarity	NPD4633	Approved
0.65	Remote Similarity	NPD6370	Approved
0.6495	Remote Similarity	NPD4820	Approved
0.6495	Remote Similarity	NPD4819	Approved
0.6495	Remote Similarity	NPD4821	Approved
0.6495	Remote Similarity	NPD4748	Discontinued
0.6495	Remote Similarity	NPD7332	Phase 2
0.6495	Remote Similarity	NPD4822	Approved
0.6481	Remote Similarity	NPD6648	Approved
0.6476	Remote Similarity	NPD7900	Approved
0.6476	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD6336	Discontinued
0.6471	Remote Similarity	NPD6903	Approved
0.646	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD4268	Approved
0.6458	Remote Similarity	NPD4271	Approved
0.6455	Remote Similarity	NPD5175	Approved
0.6455	Remote Similarity	NPD5174	Approved
0.6442	Remote Similarity	NPD6079	Approved
0.6441	Remote Similarity	NPD6335	Approved
0.6436	Remote Similarity	NPD3618	Phase 1
0.6429	Remote Similarity	NPD6898	Phase 1
0.6422	Remote Similarity	NPD5223	Approved
0.6417	Remote Similarity	NPD6015	Approved
0.6417	Remote Similarity	NPD6016	Approved
0.6417	Remote Similarity	NPD6909	Approved
0.6417	Remote Similarity	NPD6908	Approved
0.6415	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD4787	Phase 1
0.6408	Remote Similarity	NPD4753	Phase 2
0.6404	Remote Similarity	NPD4634	Approved
0.64	Remote Similarity	NPD3666	Approved
0.64	Remote Similarity	NPD3665	Phase 1
0.64	Remote Similarity	NPD3133	Approved
0.6392	Remote Similarity	NPD6683	Phase 2
0.6383	Remote Similarity	NPD6926	Approved
0.6383	Remote Similarity	NPD6924	Approved
0.6383	Remote Similarity	NPD4785	Approved
0.6383	Remote Similarity	NPD4784	Approved
0.6381	Remote Similarity	NPD5778	Approved
0.6381	Remote Similarity	NPD5779	Approved
0.6364	Remote Similarity	NPD5988	Approved
0.6356	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD6317	Approved
0.6344	Remote Similarity	NPD4243	Approved
0.6344	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD5777	Approved
0.6339	Remote Similarity	NPD4768	Approved
0.6339	Remote Similarity	NPD4767	Approved
0.6316	Remote Similarity	NPD3702	Approved
0.6316	Remote Similarity	NPD3703	Phase 2
0.6311	Remote Similarity	NPD5737	Approved
0.6311	Remote Similarity	NPD6672	Approved
0.6306	Remote Similarity	NPD4754	Approved
0.6303	Remote Similarity	NPD6314	Approved
0.6303	Remote Similarity	NPD6313	Approved
0.63	Remote Similarity	NPD5362	Discontinued
0.6286	Remote Similarity	NPD6411	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