NPASS Compound

Structure

NPC160304 OpenBabel07101718232D 27 30 0 0 1 0 0 0 0 0999 V2000 -1.4576 2.1380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8709 -0.6519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2424 1.5801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3709 0.2141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2472 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2472 2.1603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6236 1.8002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6236 -0.3600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2650 1.0088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9195 -0.3930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8709 1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0646 1.2185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3709 0.2141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5775 0.3600 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5630 1.1691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2472 0.7201 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8709 1.8002 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.7201 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0896 0.9960 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6236 1.0801 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8709 1.0801 0.0000 C 0 0 2 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 4.8709 1.0801 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3405 2.1440 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7369 2.3002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6634 1.6539 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3709 0.2141 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 2 0 0 0 0 2 13 1 0 0 0 0 5 8 1 0 0 0 0 5 16 1 0 0 0 0 6 7 1 0 0 0 0 6 17 1 0 0 0 0 7 20 1 0 0 0 0 9 15 1 0 0 0 0 10 14 1 0 0 0 0 10 22 1 0 0 0 0 11 21 1 0 0 0 0 11 27 1 0 0 0 0 12 14 1 0 0 0 0 12 19 1 0 0 0 0 13 23 2 0 0 0 0 13 27 1 0 0 0 0 14 9 1 1 0 0 0 15 18 1 0 0 0 0 15 24 1 6 0 0 0 16 20 1 1 0 0 0 16 21 1 0 0 0 0 17 21 1 1 0 0 0 17 25 1 0 0 0 0 18 20 1 1 0 0 0 18 22 1 0 0 0 0 19 22 1 1 0 0 0 19 26 1 0 0 0 0 20 3 1 1 0 0 0 21 4 1 6 0 0 0 22 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	378.24
Volume:	393.521
LogP:	1.915
LogD:	2.04
LogS:	-3.625
# Rotatable Bonds:	3
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.507
Synthetic Accessibility Score:	6.01
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:	-4.881
MDCK Permeability:	1.4577176443708595e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.018
30% Bioavailability (F30%):	0.597

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.76
Plasma Protein Binding (PPB):	35.96051025390625%
Volume Distribution (VD):	0.999
Pgp-substrate:	62.5216064453125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.107
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.605
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.052
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.109
CYP3A4-inhibitor:	0.682
CYP3A4-substrate:	0.16

ADMET: Excretion

Clearance (CL):	3.021
Half-life (T1/2):	0.541

ADMET: Toxicity

hERG Blockers:	0.561
Human Hepatotoxicity (H-HT):	0.262
Drug-inuced Liver Injury (DILI):	0.074
AMES Toxicity:	0.451
Rat Oral Acute Toxicity:	0.982
Maximum Recommended Daily Dose:	0.997
Skin Sensitization:	0.766
Carcinogencity:	0.374
Eye Corrosion:	0.094
Eye Irritation:	0.49
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC160304

Natural Product ID:	NPC160304
*Common Name:**	Excisusin C
IUPAC Name:	n.a.
Synonyms:	Excisusin C
Standard InCHIKey:	CHKPKMQLJUVPLP-DOJKHQBHSA-N
Standard InCHI:	InChI=1S/C22H34O5/c1-12-14-9-15(24)18-20(3)7-6-17(25)21(4,11-27-13(2)23)16(20)5-8-22(18,10-14)19(12)26/h14-19,24-26H,1,5-11H2,2-4H3/t14-,15+,16+,17-,18+,19-,20-,21+,22-/m1/s1
SMILES:	CC(=O)OC[C@]1(C)[C@H](O)CC[C@@]2([C@@H]1CC[C@]13[C@H]2[C@@H](O)C[C@H](C1)C(=C)[C@H]3O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL390108
PubChem CID:	16215670
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
NPO26913	Isodon excisus	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[10896056]
NPO26913	Isodon excisus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374970]
NPO26913	Isodon excisus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17338565]
NPO26913	Isodon excisus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21273070]
NPO26913	Isodon excisus	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[22066578]
NPO26913	Isodon excisus	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	10000.0	nM	PMID[515675]

☑ 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 NPC160304 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	185
0.1-0.2	1661
0.2-0.3	5630
0.3-0.4	15030
0.4-0.5	7444
0.5-0.6	4830
0.6-0.7	5401
0.7-0.8	2261
0.8-0.85	192
0.85-0.9	44
0.9-0.95	10
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9762	High Similarity	NPC219937
0.9762	High Similarity	NPC194485
0.9762	High Similarity	NPC123252
0.9762	High Similarity	NPC53890
0.9535	High Similarity	NPC26046
0.9419	High Similarity	NPC130840
0.9318	High Similarity	NPC241047
0.9277	High Similarity	NPC299963
0.9213	High Similarity	NPC111834
0.9213	High Similarity	NPC306797
0.9213	High Similarity	NPC169270
0.9213	High Similarity	NPC292718
0.9205	High Similarity	NPC3359
0.9036	High Similarity	NPC472504
0.8941	High Similarity	NPC164424
0.8902	High Similarity	NPC24504
0.8902	High Similarity	NPC476316
0.8901	High Similarity	NPC274793
0.8864	High Similarity	NPC10274
0.8837	High Similarity	NPC168231
0.8824	High Similarity	NPC256567
0.8817	High Similarity	NPC253886
0.8817	High Similarity	NPC121218
0.8804	High Similarity	NPC469725
0.8795	High Similarity	NPC47149
0.878	High Similarity	NPC472499
0.878	High Similarity	NPC472500
0.878	High Similarity	NPC472502
0.878	High Similarity	NPC475
0.8764	High Similarity	NPC219516
0.8723	High Similarity	NPC31085
0.869	High Similarity	NPC157655
0.8659	High Similarity	NPC260301
0.8659	High Similarity	NPC307336
0.8659	High Similarity	NPC138502
0.8632	High Similarity	NPC471467
0.8617	High Similarity	NPC144486
0.8617	High Similarity	NPC49532
0.8587	High Similarity	NPC253115
0.8587	High Similarity	NPC304899
0.8571	High Similarity	NPC71535
0.8571	High Similarity	NPC206735
0.8571	High Similarity	NPC78545
0.8554	High Similarity	NPC477819
0.8554	High Similarity	NPC472501
0.8554	High Similarity	NPC477817
0.8542	High Similarity	NPC47281
0.8537	High Similarity	NPC38141
0.8526	High Similarity	NPC170615
0.8526	High Similarity	NPC177701
0.8511	High Similarity	NPC108371
0.8488	Intermediate Similarity	NPC5280
0.8488	Intermediate Similarity	NPC232023
0.8478	Intermediate Similarity	NPC205173
0.8454	Intermediate Similarity	NPC50535
0.8454	Intermediate Similarity	NPC37600
0.8452	Intermediate Similarity	NPC5604
0.8438	Intermediate Similarity	NPC469985
0.8421	Intermediate Similarity	NPC295276
0.8391	Intermediate Similarity	NPC263974
0.8391	Intermediate Similarity	NPC255882
0.8387	Intermediate Similarity	NPC299654
0.8367	Intermediate Similarity	NPC470170
0.8367	Intermediate Similarity	NPC470169
0.8333	Intermediate Similarity	NPC301707
0.8333	Intermediate Similarity	NPC471045
0.8333	Intermediate Similarity	NPC473647
0.8316	Intermediate Similarity	NPC208358
0.8298	Intermediate Similarity	NPC475033
0.8298	Intermediate Similarity	NPC253586
0.8298	Intermediate Similarity	NPC475032
0.8293	Intermediate Similarity	NPC308440
0.8293	Intermediate Similarity	NPC472503
0.828	Intermediate Similarity	NPC98639
0.828	Intermediate Similarity	NPC30477
0.8276	Intermediate Similarity	NPC473742
0.8276	Intermediate Similarity	NPC110778
0.8276	Intermediate Similarity	NPC471037
0.8265	Intermediate Similarity	NPC220217
0.8265	Intermediate Similarity	NPC28791
0.8265	Intermediate Similarity	NPC295366
0.8265	Intermediate Similarity	NPC119855
0.8261	Intermediate Similarity	NPC296620
0.8247	Intermediate Similarity	NPC97487
0.8247	Intermediate Similarity	NPC160583
0.8247	Intermediate Similarity	NPC196471
0.8247	Intermediate Similarity	NPC10232
0.8247	Intermediate Similarity	NPC189588
0.8247	Intermediate Similarity	NPC187302
0.8242	Intermediate Similarity	NPC100313
0.8235	Intermediate Similarity	NPC476176
0.8229	Intermediate Similarity	NPC295110
0.8229	Intermediate Similarity	NPC155974
0.8229	Intermediate Similarity	NPC268829
0.8229	Intermediate Similarity	NPC25177
0.8229	Intermediate Similarity	NPC222875
0.8229	Intermediate Similarity	NPC39683
0.8229	Intermediate Similarity	NPC75941
0.8229	Intermediate Similarity	NPC247701
0.8222	Intermediate Similarity	NPC16377
0.8211	Intermediate Similarity	NPC16911
0.8211	Intermediate Similarity	NPC38471
0.8211	Intermediate Similarity	NPC162459
0.8211	Intermediate Similarity	NPC98837
0.8211	Intermediate Similarity	NPC20479
0.8211	Intermediate Similarity	NPC78427
0.8211	Intermediate Similarity	NPC28864
0.8211	Intermediate Similarity	NPC38296
0.8202	Intermediate Similarity	NPC474970
0.8202	Intermediate Similarity	NPC139724
0.8202	Intermediate Similarity	NPC121981
0.8202	Intermediate Similarity	NPC472505
0.8202	Intermediate Similarity	NPC201273
0.8193	Intermediate Similarity	NPC185536
0.8191	Intermediate Similarity	NPC471903
0.8191	Intermediate Similarity	NPC29410
0.8191	Intermediate Similarity	NPC234564
0.8191	Intermediate Similarity	NPC276103
0.8191	Intermediate Similarity	NPC54248
0.8191	Intermediate Similarity	NPC200054
0.8182	Intermediate Similarity	NPC475781
0.8182	Intermediate Similarity	NPC470166
0.8182	Intermediate Similarity	NPC102048
0.8182	Intermediate Similarity	NPC86238
0.8182	Intermediate Similarity	NPC86852
0.8182	Intermediate Similarity	NPC251824
0.8172	Intermediate Similarity	NPC47853
0.8172	Intermediate Similarity	NPC280804
0.8172	Intermediate Similarity	NPC277399
0.8172	Intermediate Similarity	NPC474922
0.8171	Intermediate Similarity	NPC472506
0.8161	Intermediate Similarity	NPC170985
0.8152	Intermediate Similarity	NPC198054
0.814	Intermediate Similarity	NPC475679
0.814	Intermediate Similarity	NPC304194
0.8132	Intermediate Similarity	NPC194642
0.8132	Intermediate Similarity	NPC16265
0.8125	Intermediate Similarity	NPC251680
0.8125	Intermediate Similarity	NPC293866
0.8125	Intermediate Similarity	NPC41971
0.8125	Intermediate Similarity	NPC471247
0.8125	Intermediate Similarity	NPC37047
0.8125	Intermediate Similarity	NPC287676
0.8125	Intermediate Similarity	NPC180733
0.8118	Intermediate Similarity	NPC31828
0.8111	Intermediate Similarity	NPC134197
0.8111	Intermediate Similarity	NPC269360
0.8111	Intermediate Similarity	NPC264005
0.8111	Intermediate Similarity	NPC33768
0.8105	Intermediate Similarity	NPC10864
0.809	Intermediate Similarity	NPC266651
0.8085	Intermediate Similarity	NPC279974
0.8085	Intermediate Similarity	NPC473348
0.8085	Intermediate Similarity	NPC210214
0.8081	Intermediate Similarity	NPC285927
0.8081	Intermediate Similarity	NPC165405
0.8072	Intermediate Similarity	NPC476736
0.8068	Intermediate Similarity	NPC85095
0.8068	Intermediate Similarity	NPC477818
0.8068	Intermediate Similarity	NPC211135
0.8068	Intermediate Similarity	NPC193870
0.8068	Intermediate Similarity	NPC141941
0.8068	Intermediate Similarity	NPC216420
0.8065	Intermediate Similarity	NPC294263
0.8065	Intermediate Similarity	NPC473690
0.8065	Intermediate Similarity	NPC287118
0.8065	Intermediate Similarity	NPC473678
0.8065	Intermediate Similarity	NPC471902
0.8065	Intermediate Similarity	NPC291373
0.8061	Intermediate Similarity	NPC87927
0.8061	Intermediate Similarity	NPC472821
0.8061	Intermediate Similarity	NPC473523
0.8049	Intermediate Similarity	NPC164045
0.8041	Intermediate Similarity	NPC46848
0.8041	Intermediate Similarity	NPC289148
0.8041	Intermediate Similarity	NPC475617
0.8041	Intermediate Similarity	NPC52899
0.8041	Intermediate Similarity	NPC163963
0.8023	Intermediate Similarity	NPC305835
0.8023	Intermediate Similarity	NPC475727
0.8023	Intermediate Similarity	NPC47808
0.8023	Intermediate Similarity	NPC80297
0.8023	Intermediate Similarity	NPC472742
0.8023	Intermediate Similarity	NPC116119
0.8022	Intermediate Similarity	NPC4309
0.8021	Intermediate Similarity	NPC325229
0.8021	Intermediate Similarity	NPC119036
0.8021	Intermediate Similarity	NPC471038
0.8021	Intermediate Similarity	NPC275086
0.8021	Intermediate Similarity	NPC474793
0.8021	Intermediate Similarity	NPC300179
0.8021	Intermediate Similarity	NPC102426
0.8021	Intermediate Similarity	NPC89099
0.802	Intermediate Similarity	NPC473570
0.8	Intermediate Similarity	NPC475684
0.8	Intermediate Similarity	NPC2783
0.8	Intermediate Similarity	NPC471246
0.8	Intermediate Similarity	NPC329910
0.8	Intermediate Similarity	NPC6605
0.8	Intermediate Similarity	NPC286153

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 NPC160304 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	160
0.1-0.2	2008
0.2-0.3	4116
0.3-0.4	1995
0.4-0.5	414
0.5-0.6	191
0.6-0.7	196
0.7-0.8	67
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8125	Intermediate Similarity	NPD7639	Approved
0.8125	Intermediate Similarity	NPD7640	Approved
0.8021	Intermediate Similarity	NPD7638	Approved
0.7957	Intermediate Similarity	NPD8035	Phase 2
0.7957	Intermediate Similarity	NPD8034	Phase 2
0.7889	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD7525	Registered
0.76	Intermediate Similarity	NPD7632	Discontinued
0.7549	Intermediate Similarity	NPD5739	Approved
0.7549	Intermediate Similarity	NPD6675	Approved
0.7549	Intermediate Similarity	NPD6402	Approved
0.7549	Intermediate Similarity	NPD7128	Approved
0.75	Intermediate Similarity	NPD6114	Approved
0.75	Intermediate Similarity	NPD6118	Approved
0.75	Intermediate Similarity	NPD6697	Approved
0.75	Intermediate Similarity	NPD6115	Approved
0.7431	Intermediate Similarity	NPD7327	Approved
0.7431	Intermediate Similarity	NPD7328	Approved
0.7404	Intermediate Similarity	NPD6899	Approved
0.7404	Intermediate Similarity	NPD7320	Approved
0.7404	Intermediate Similarity	NPD6881	Approved
0.7391	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD6116	Phase 1
0.7383	Intermediate Similarity	NPD8133	Approved
0.7364	Intermediate Similarity	NPD7516	Approved
0.7333	Intermediate Similarity	NPD6373	Approved
0.7333	Intermediate Similarity	NPD6372	Approved
0.732	Intermediate Similarity	NPD6399	Phase 3
0.7308	Intermediate Similarity	NPD5701	Approved
0.7308	Intermediate Similarity	NPD5697	Approved
0.7297	Intermediate Similarity	NPD8294	Approved
0.7297	Intermediate Similarity	NPD8377	Approved
0.7283	Intermediate Similarity	NPD6695	Phase 3
0.7273	Intermediate Similarity	NPD6117	Approved
0.7264	Intermediate Similarity	NPD6883	Approved
0.7264	Intermediate Similarity	NPD7290	Approved
0.7264	Intermediate Similarity	NPD7102	Approved
0.7232	Intermediate Similarity	NPD8378	Approved
0.7232	Intermediate Similarity	NPD8379	Approved
0.7232	Intermediate Similarity	NPD8380	Approved
0.7232	Intermediate Similarity	NPD8335	Approved
0.7232	Intermediate Similarity	NPD8033	Approved
0.7232	Intermediate Similarity	NPD8296	Approved
0.7222	Intermediate Similarity	NPD7645	Phase 2
0.7216	Intermediate Similarity	NPD7637	Suspended
0.72	Intermediate Similarity	NPD6083	Phase 2
0.72	Intermediate Similarity	NPD6084	Phase 2
0.7196	Intermediate Similarity	NPD6869	Approved
0.7196	Intermediate Similarity	NPD6617	Approved
0.7196	Intermediate Similarity	NPD6649	Approved
0.7196	Intermediate Similarity	NPD8130	Phase 1
0.7196	Intermediate Similarity	NPD6847	Approved
0.7196	Intermediate Similarity	NPD6650	Approved
0.7188	Intermediate Similarity	NPD6051	Approved
0.717	Intermediate Similarity	NPD6013	Approved
0.717	Intermediate Similarity	NPD6014	Approved
0.717	Intermediate Similarity	NPD6012	Approved
0.7158	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6928	Phase 2
0.713	Intermediate Similarity	NPD8297	Approved
0.713	Intermediate Similarity	NPD6882	Approved
0.7097	Intermediate Similarity	NPD4788	Approved
0.7087	Intermediate Similarity	NPD5211	Phase 2
0.7079	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD6011	Approved
0.7071	Intermediate Similarity	NPD7748	Approved
0.7045	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7515	Phase 2
0.7037	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD6929	Approved
0.703	Intermediate Similarity	NPD7902	Approved
0.703	Intermediate Similarity	NPD4755	Approved
0.6983	Remote Similarity	NPD7507	Approved
0.6979	Remote Similarity	NPD7750	Discontinued
0.6979	Remote Similarity	NPD7524	Approved
0.6977	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4202	Approved
0.6966	Remote Similarity	NPD7339	Approved
0.6966	Remote Similarity	NPD6942	Approved
0.6961	Remote Similarity	NPD4225	Approved
0.6957	Remote Similarity	NPD6930	Phase 2
0.6957	Remote Similarity	NPD6931	Approved
0.6952	Remote Similarity	NPD5141	Approved
0.693	Remote Similarity	NPD7503	Approved
0.6909	Remote Similarity	NPD4632	Approved
0.6907	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD4696	Approved
0.6893	Remote Similarity	NPD5286	Approved
0.6893	Remote Similarity	NPD5285	Approved
0.6893	Remote Similarity	NPD4700	Approved
0.6887	Remote Similarity	NPD6008	Approved
0.6875	Remote Similarity	NPD6684	Approved
0.6875	Remote Similarity	NPD7334	Approved
0.6875	Remote Similarity	NPD6409	Approved
0.6875	Remote Similarity	NPD7146	Approved
0.6875	Remote Similarity	NPD5330	Approved
0.6875	Remote Similarity	NPD7521	Approved
0.6842	Remote Similarity	NPD4786	Approved
0.6842	Remote Similarity	NPD6319	Approved
0.6837	Remote Similarity	NPD5328	Approved
0.6832	Remote Similarity	NPD5695	Phase 3
0.6822	Remote Similarity	NPD6412	Phase 2
0.6813	Remote Similarity	NPD5776	Phase 2
0.6813	Remote Similarity	NPD6925	Approved
0.6807	Remote Similarity	NPD7319	Approved
0.6796	Remote Similarity	NPD5696	Approved
0.6786	Remote Similarity	NPD6274	Approved
0.6762	Remote Similarity	NPD4633	Approved
0.6762	Remote Similarity	NPD5225	Approved
0.6762	Remote Similarity	NPD5224	Approved
0.6762	Remote Similarity	NPD5226	Approved
0.6759	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD7100	Approved
0.6754	Remote Similarity	NPD7101	Approved
0.6752	Remote Similarity	NPD7492	Approved
0.6739	Remote Similarity	NPD7145	Approved
0.6735	Remote Similarity	NPD6903	Approved
0.6733	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD7900	Approved
0.6726	Remote Similarity	NPD6009	Approved
0.6726	Remote Similarity	NPD7115	Discovery
0.6723	Remote Similarity	NPD7736	Approved
0.6705	Remote Similarity	NPD4787	Phase 1
0.6701	Remote Similarity	NPD3618	Phase 1
0.67	Remote Similarity	NPD6079	Approved
0.67	Remote Similarity	NPD7087	Discontinued
0.6698	Remote Similarity	NPD5175	Approved
0.6698	Remote Similarity	NPD5174	Approved
0.6697	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6059	Approved
0.6696	Remote Similarity	NPD6054	Approved
0.6695	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD4753	Phase 2
0.6667	Remote Similarity	NPD3133	Approved
0.6667	Remote Similarity	NPD7604	Phase 2
0.6667	Remote Similarity	NPD5223	Approved
0.6667	Remote Similarity	NPD6335	Approved
0.6667	Remote Similarity	NPD3666	Approved
0.6667	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3665	Phase 1
0.6639	Remote Similarity	NPD8293	Discontinued
0.6639	Remote Similarity	NPD7078	Approved
0.6638	Remote Similarity	NPD5983	Phase 2
0.6638	Remote Similarity	NPD6908	Approved
0.6638	Remote Similarity	NPD6909	Approved
0.6636	Remote Similarity	NPD4634	Approved
0.6634	Remote Similarity	NPD8171	Discontinued
0.6632	Remote Similarity	NPD3667	Approved
0.6629	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD4243	Approved
0.6629	Remote Similarity	NPD5777	Approved
0.6629	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6686	Approved
0.6598	Remote Similarity	NPD6893	Approved
0.6596	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD4748	Discontinued
0.6596	Remote Similarity	NPD7514	Phase 3
0.6593	Remote Similarity	NPD3702	Approved
0.6593	Remote Similarity	NPD3703	Phase 2
0.6581	Remote Similarity	NPD6370	Approved
0.6579	Remote Similarity	NPD6317	Approved
0.6574	Remote Similarity	NPD4767	Approved
0.6574	Remote Similarity	NPD4768	Approved
0.6566	Remote Similarity	NPD6672	Approved
0.6566	Remote Similarity	NPD5737	Approved
0.6555	Remote Similarity	NPD6336	Discontinued
0.6545	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD4754	Approved
0.6531	Remote Similarity	NPD6098	Approved
0.6526	Remote Similarity	NPD6902	Approved
0.6522	Remote Similarity	NPD6314	Approved
0.6522	Remote Similarity	NPD6313	Approved
0.6518	Remote Similarity	NPD6053	Discontinued
0.6517	Remote Similarity	NPD4244	Approved
0.6517	Remote Similarity	NPD4245	Approved
0.6509	Remote Similarity	NPD5344	Discontinued
0.65	Remote Similarity	NPD6080	Approved
0.65	Remote Similarity	NPD6673	Approved
0.65	Remote Similarity	NPD6904	Approved
0.6496	Remote Similarity	NPD6015	Approved
0.6496	Remote Similarity	NPD6016	Approved
0.6489	Remote Similarity	NPD4195	Approved
0.6486	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD6924	Approved
0.6484	Remote Similarity	NPD4784	Approved
0.6484	Remote Similarity	NPD6926	Approved
0.6484	Remote Similarity	NPD4785	Approved
0.6471	Remote Similarity	NPD5779	Approved
0.6471	Remote Similarity	NPD5778	Approved
0.6465	Remote Similarity	NPD4250	Approved
0.6465	Remote Similarity	NPD4251	Approved
0.6455	Remote Similarity	NPD4730	Approved
0.6455	Remote Similarity	NPD5128	Approved
0.6455	Remote Similarity	NPD4729	Approved
0.6452	Remote Similarity	NPD6932	Approved
0.6442	Remote Similarity	NPD4697	Phase 3
0.6442	Remote Similarity	NPD5222	Approved
0.6442	Remote Similarity	NPD5221	Approved
0.6442	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD5988	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