NPASS Compound

Structure

NPC23298 OpenBabel07101719252D 29 32 0 0 0 0 0 0 0 0999 V2000 -5.1962 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 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 11 1 0 0 0 0 3 23 1 0 0 0 0 4 23 1 0 0 0 0 5 6 1 0 0 0 0 5 11 2 0 0 0 0 6 12 1 0 0 0 0 7 8 2 0 0 0 0 7 14 1 0 0 0 0 8 15 1 0 0 0 0 9 10 2 0 0 0 0 9 13 1 0 0 0 0 10 23 1 0 0 0 0 12 14 2 0 0 0 0 12 16 1 0 0 0 0 13 18 2 0 0 0 0 13 21 1 0 0 0 0 14 24 1 0 0 0 0 15 16 2 0 0 0 0 15 28 1 0 0 0 0 16 19 1 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 17 22 2 0 0 0 0 18 25 1 0 0 0 0 19 26 2 0 0 0 0 20 21 2 0 0 0 0 20 22 1 0 0 0 0 20 27 1 0 0 0 0 21 29 1 0 0 0 0 22 28 1 0 0 0 0 23 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	394.14
Volume:	401.152
LogP:	5.931
LogD:	3.233
LogS:	-2.794
# Rotatable Bonds:	2
TPSA:	100.13
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.329
Synthetic Accessibility Score:	3.37
Fsp3:	0.261
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.825
MDCK Permeability:	1.5367882951977663e-05
Pgp-inhibitor:	0.842
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.4
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	90.4339828491211%
Volume Distribution (VD):	0.585
Pgp-substrate:	10.870343208312988%

ADMET: Metabolism

CYP1A2-inhibitor:	0.564
CYP1A2-substrate:	0.221
CYP2C19-inhibitor:	0.626
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.864
CYP2C9-substrate:	0.913
CYP2D6-inhibitor:	0.442
CYP2D6-substrate:	0.194
CYP3A4-inhibitor:	0.169
CYP3A4-substrate:	0.101

ADMET: Excretion

Clearance (CL):	1.567
Half-life (T1/2):	0.289

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.925
Drug-inuced Liver Injury (DILI):	0.975
AMES Toxicity:	0.475
Rat Oral Acute Toxicity:	0.872
Maximum Recommended Daily Dose:	0.449
Skin Sensitization:	0.802
Carcinogencity:	0.856
Eye Corrosion:	0.003
Eye Irritation:	0.246
Respiratory Toxicity:	0.254

Download Data

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

Natural Product: NPC23298

Natural Product ID:	NPC23298
*Common Name:**	Termicalcicolanone A
IUPAC Name:	5,8,12-trihydroxy-2,2-dimethyl-7-(3-methylbut-2-enyl)pyrano[3,2-b]xanthen-6-one
Synonyms:
Standard InCHIKey:	LIBMYNVOSDZKIY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C23H22O6/c1-11(2)5-6-12-14(24)7-8-15-16(12)19(26)17-18(25)13-9-10-23(3,4)29-21(13)20(27)22(17)28-15/h5,7-10,24-25,27H,6H2,1-4H3
SMILES:	CC(=CCc1c(ccc2c1c(=O)c1c(c3C=CC(C)(C)Oc3c(c1o2)O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL224141
PubChem CID:	16216540
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones [CHEMONTID:0003519] 8-prenylated xanthones

*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
NPO33413	terminalia calcicola	Species	Combretaceae	Eukaryota	n.a.	Madagascar rain forest	n.a.	PMID[17323994]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	40600.0	nM	PMID[520378]

☑ 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 NPC23298 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	481
0.1-0.2	1972
0.2-0.3	4625
0.3-0.4	11034
0.4-0.5	6643
0.5-0.6	3749
0.6-0.7	5163
0.7-0.8	5031
0.8-0.85	2202
0.85-0.9	1121
0.9-0.95	599
0.95-1	77

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC189473
0.9935	High Similarity	NPC239752
0.9935	High Similarity	NPC275780
0.9935	High Similarity	NPC472450
0.9872	High Similarity	NPC39091
0.9872	High Similarity	NPC37870
0.9872	High Similarity	NPC472449
0.9806	High Similarity	NPC229632
0.9806	High Similarity	NPC329760
0.9806	High Similarity	NPC25152
0.9805	High Similarity	NPC139036
0.9805	High Similarity	NPC204290
0.9805	High Similarity	NPC471973
0.9744	High Similarity	NPC236521
0.9744	High Similarity	NPC248638
0.9744	High Similarity	NPC152659
0.9744	High Similarity	NPC207690
0.9742	High Similarity	NPC61010
0.9742	High Similarity	NPC29876
0.9742	High Similarity	NPC167678
0.974	High Similarity	NPC100123
0.974	High Similarity	NPC474290
0.9679	High Similarity	NPC472448
0.9679	High Similarity	NPC83922
0.9677	High Similarity	NPC14353
0.9677	High Similarity	NPC228785
0.9677	High Similarity	NPC320359
0.9677	High Similarity	NPC56085
0.9677	High Similarity	NPC200746
0.9675	High Similarity	NPC136674
0.9618	High Similarity	NPC186686
0.9618	High Similarity	NPC220313
0.9618	High Similarity	NPC146134
0.9618	High Similarity	NPC303460
0.9618	High Similarity	NPC306321
0.9615	High Similarity	NPC278052
0.9615	High Similarity	NPC259456
0.9615	High Similarity	NPC40491
0.9613	High Similarity	NPC476242
0.961	High Similarity	NPC142339
0.961	High Similarity	NPC274730
0.961	High Similarity	NPC68093
0.961	High Similarity	NPC191146
0.956	High Similarity	NPC477154
0.956	High Similarity	NPC117854
0.956	High Similarity	NPC6588
0.9554	High Similarity	NPC474150
0.9554	High Similarity	NPC474162
0.9551	High Similarity	NPC476980
0.9551	High Similarity	NPC45146
0.9551	High Similarity	NPC235018
0.9551	High Similarity	NPC80375
0.9548	High Similarity	NPC236796
0.9548	High Similarity	NPC241904
0.9548	High Similarity	NPC300727
0.9548	High Similarity	NPC474681
0.9548	High Similarity	NPC165977
0.9548	High Similarity	NPC218313
0.9548	High Similarity	NPC78225
0.9548	High Similarity	NPC217677
0.95	High Similarity	NPC476637
0.9497	High Similarity	NPC170245
0.9497	High Similarity	NPC43319
0.9494	High Similarity	NPC270837
0.9494	High Similarity	NPC236132
0.9494	High Similarity	NPC7483
0.949	High Similarity	NPC32694
0.949	High Similarity	NPC234644
0.949	High Similarity	NPC474187
0.9487	High Similarity	NPC235448
0.9487	High Similarity	NPC204879
0.9484	High Similarity	NPC5322
0.9484	High Similarity	NPC471985
0.9484	High Similarity	NPC276444
0.9484	High Similarity	NPC138243
0.9484	High Similarity	NPC6633
0.9484	High Similarity	NPC133970
0.9481	High Similarity	NPC89474
0.9481	High Similarity	NPC280530
0.9481	High Similarity	NPC95842
0.9481	High Similarity	NPC178964
0.9441	High Similarity	NPC101107
0.9437	High Similarity	NPC218226
0.9437	High Similarity	NPC126204
0.9434	High Similarity	NPC326520
0.9434	High Similarity	NPC293319
0.9434	High Similarity	NPC156432
0.943	High Similarity	NPC52204
0.943	High Similarity	NPC294965
0.943	High Similarity	NPC261470
0.9427	High Similarity	NPC118256
0.9427	High Similarity	NPC119209
0.9427	High Similarity	NPC475886
0.9427	High Similarity	NPC474960
0.9427	High Similarity	NPC188433
0.9427	High Similarity	NPC192686
0.9427	High Similarity	NPC474287
0.9427	High Similarity	NPC36217
0.9427	High Similarity	NPC119224
0.9423	High Similarity	NPC476981
0.9423	High Similarity	NPC218871
0.9423	High Similarity	NPC36852
0.9423	High Similarity	NPC476630
0.9423	High Similarity	NPC262286
0.9419	High Similarity	NPC472280
0.9419	High Similarity	NPC200246
0.9379	High Similarity	NPC475805
0.9375	High Similarity	NPC120593
0.9371	High Similarity	NPC41301
0.9371	High Similarity	NPC475985
0.9367	High Similarity	NPC474351
0.9367	High Similarity	NPC278427
0.9367	High Similarity	NPC475883
0.9367	High Similarity	NPC57715
0.9367	High Similarity	NPC474186
0.9367	High Similarity	NPC66288
0.9367	High Similarity	NPC474038
0.9367	High Similarity	NPC266314
0.9367	High Similarity	NPC258331
0.9363	High Similarity	NPC280680
0.9363	High Similarity	NPC95936
0.9363	High Similarity	NPC250214
0.9363	High Similarity	NPC185258
0.9363	High Similarity	NPC172770
0.9359	High Similarity	NPC472907
0.9359	High Similarity	NPC470600
0.9359	High Similarity	NPC472455
0.9355	High Similarity	NPC33051
0.9355	High Similarity	NPC227337
0.9355	High Similarity	NPC70433
0.9355	High Similarity	NPC183878
0.9355	High Similarity	NPC49402
0.9355	High Similarity	NPC231018
0.9355	High Similarity	NPC472905
0.9355	High Similarity	NPC176775
0.9355	High Similarity	NPC69394
0.9355	High Similarity	NPC47781
0.9355	High Similarity	NPC273462
0.9355	High Similarity	NPC160951
0.9355	High Similarity	NPC22519
0.9355	High Similarity	NPC255350
0.9355	High Similarity	NPC170492
0.9355	High Similarity	NPC145379
0.9355	High Similarity	NPC274327
0.9351	High Similarity	NPC202157
0.9325	High Similarity	NPC310794
0.9321	High Similarity	NPC472276
0.9317	High Similarity	NPC476306
0.9313	High Similarity	NPC50960
0.9313	High Similarity	NPC224280
0.9313	High Similarity	NPC62261
0.9313	High Similarity	NPC303174
0.9308	High Similarity	NPC470694
0.9308	High Similarity	NPC201800
0.9308	High Similarity	NPC472402
0.9308	High Similarity	NPC78332
0.9308	High Similarity	NPC206605
0.9304	High Similarity	NPC246478
0.9304	High Similarity	NPC476280
0.9304	High Similarity	NPC475784
0.9299	High Similarity	NPC79053
0.9299	High Similarity	NPC469584
0.9299	High Similarity	NPC223787
0.9299	High Similarity	NPC475267
0.9299	High Similarity	NPC48208
0.9299	High Similarity	NPC474836
0.9299	High Similarity	NPC472910
0.9299	High Similarity	NPC52889
0.9299	High Similarity	NPC472911
0.9299	High Similarity	NPC245758
0.9299	High Similarity	NPC96167
0.9299	High Similarity	NPC284820
0.9299	High Similarity	NPC27337
0.9299	High Similarity	NPC472913
0.9299	High Similarity	NPC473272
0.9299	High Similarity	NPC187745
0.9299	High Similarity	NPC162869
0.9299	High Similarity	NPC222814
0.9299	High Similarity	NPC273843
0.9299	High Similarity	NPC161960
0.9299	High Similarity	NPC474208
0.9299	High Similarity	NPC304008
0.9299	High Similarity	NPC472914
0.9299	High Similarity	NPC472963
0.9299	High Similarity	NPC156057
0.9295	High Similarity	NPC57674
0.9295	High Similarity	NPC230149
0.9295	High Similarity	NPC113906
0.9295	High Similarity	NPC227325
0.9295	High Similarity	NPC256612
0.9295	High Similarity	NPC168247
0.9295	High Similarity	NPC166054
0.9295	High Similarity	NPC196439
0.9295	High Similarity	NPC128863
0.9295	High Similarity	NPC4455
0.9295	High Similarity	NPC50715
0.9295	High Similarity	NPC234255
0.9295	High Similarity	NPC20830
0.9295	High Similarity	NPC183597
0.9295	High Similarity	NPC163780

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 NPC23298 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	425
0.1-0.2	1024
0.2-0.3	1805
0.3-0.4	2701
0.4-0.5	1747
0.5-0.6	916
0.6-0.7	354
0.7-0.8	131
0.8-0.85	30
0.85-0.9	12
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9355	High Similarity	NPD2801	Approved
0.9108	High Similarity	NPD2393	Clinical (unspecified phase)
0.9045	High Similarity	NPD1934	Approved
0.8896	High Similarity	NPD1511	Approved
0.8827	High Similarity	NPD5494	Approved
0.8782	High Similarity	NPD1512	Approved
0.8727	High Similarity	NPD6166	Phase 2
0.8727	High Similarity	NPD6168	Clinical (unspecified phase)
0.8727	High Similarity	NPD6167	Clinical (unspecified phase)
0.8642	High Similarity	NPD3882	Suspended
0.8606	High Similarity	NPD6232	Discontinued
0.8599	High Similarity	NPD4378	Clinical (unspecified phase)
0.8588	High Similarity	NPD4338	Clinical (unspecified phase)
0.8571	High Similarity	NPD5844	Phase 1
0.8571	High Similarity	NPD7054	Approved
0.8563	High Similarity	NPD7473	Discontinued
0.8562	High Similarity	NPD4380	Phase 2
0.8521	High Similarity	NPD7074	Phase 3
0.8521	High Similarity	NPD7472	Approved
0.8519	High Similarity	NPD1465	Phase 2
0.8512	High Similarity	NPD3818	Discontinued
0.8481	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD3817	Phase 2
0.8415	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8405	Intermediate Similarity	NPD7819	Suspended
0.8363	Intermediate Similarity	NPD6797	Phase 2
0.8323	Intermediate Similarity	NPD6959	Discontinued
0.8314	Intermediate Similarity	NPD7251	Discontinued
0.8266	Intermediate Similarity	NPD7808	Phase 3
0.8253	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD7075	Discontinued
0.8242	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD3749	Approved
0.814	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD3750	Approved
0.8107	Intermediate Similarity	NPD1247	Approved
0.8101	Intermediate Similarity	NPD1549	Phase 2
0.8061	Intermediate Similarity	NPD7411	Suspended
0.8025	Intermediate Similarity	NPD1510	Phase 2
0.8024	Intermediate Similarity	NPD5402	Approved
0.8012	Intermediate Similarity	NPD6801	Discontinued
0.8	Intermediate Similarity	NPD943	Approved
0.7989	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD2796	Approved
0.7943	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD2800	Approved
0.7914	Intermediate Similarity	NPD2533	Approved
0.7914	Intermediate Similarity	NPD2534	Approved
0.7914	Intermediate Similarity	NPD2532	Approved
0.7901	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD1240	Approved
0.7862	Intermediate Similarity	NPD2935	Discontinued
0.7861	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD6799	Approved
0.7831	Intermediate Similarity	NPD3226	Approved
0.7812	Intermediate Similarity	NPD2346	Discontinued
0.7803	Intermediate Similarity	NPD3926	Phase 2
0.7799	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD3748	Approved
0.7799	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD6559	Discontinued
0.7796	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD1607	Approved
0.7784	Intermediate Similarity	NPD6599	Discontinued
0.7778	Intermediate Similarity	NPD919	Approved
0.7771	Intermediate Similarity	NPD3751	Discontinued
0.7765	Intermediate Similarity	NPD7768	Phase 2
0.775	Intermediate Similarity	NPD6099	Approved
0.775	Intermediate Similarity	NPD6100	Approved
0.7746	Intermediate Similarity	NPD3787	Discontinued
0.7744	Intermediate Similarity	NPD7390	Discontinued
0.7722	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD6234	Discontinued
0.7658	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD1613	Approved
0.761	Intermediate Similarity	NPD447	Suspended
0.7606	Intermediate Similarity	NPD6777	Approved
0.7606	Intermediate Similarity	NPD6778	Approved
0.7606	Intermediate Similarity	NPD6779	Approved
0.7606	Intermediate Similarity	NPD6781	Approved
0.7606	Intermediate Similarity	NPD6776	Approved
0.7606	Intermediate Similarity	NPD6782	Approved
0.7606	Intermediate Similarity	NPD6780	Approved
0.7605	Intermediate Similarity	NPD5403	Approved
0.7586	Intermediate Similarity	NPD7199	Phase 2
0.758	Intermediate Similarity	NPD4625	Phase 3
0.7578	Intermediate Similarity	NPD2799	Discontinued
0.7571	Intermediate Similarity	NPD7228	Approved
0.7532	Intermediate Similarity	NPD2313	Discontinued
0.7514	Intermediate Similarity	NPD8313	Approved
0.7514	Intermediate Similarity	NPD8312	Approved
0.75	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD920	Approved
0.75	Intermediate Similarity	NPD230	Phase 1
0.75	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1243	Approved
0.7487	Intermediate Similarity	NPD7435	Discontinued
0.7486	Intermediate Similarity	NPD8150	Discontinued
0.7485	Intermediate Similarity	NPD37	Approved
0.7485	Intermediate Similarity	NPD2344	Approved
0.7485	Intermediate Similarity	NPD5401	Approved
0.7485	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD3027	Phase 3
0.7459	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD4967	Phase 2
0.7457	Intermediate Similarity	NPD4966	Approved
0.7457	Intermediate Similarity	NPD4965	Approved
0.7456	Intermediate Similarity	NPD1653	Approved
0.7455	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD5710	Approved
0.7443	Intermediate Similarity	NPD5711	Approved
0.7421	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD7685	Pre-registration
0.7398	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD7783	Phase 2
0.7396	Intermediate Similarity	NPD7698	Approved
0.7396	Intermediate Similarity	NPD7696	Phase 3
0.7396	Intermediate Similarity	NPD7697	Approved
0.7381	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7870	Phase 2
0.7358	Intermediate Similarity	NPD7871	Phase 2
0.7349	Intermediate Similarity	NPD4628	Phase 3
0.7348	Intermediate Similarity	NPD5953	Discontinued
0.7346	Intermediate Similarity	NPD6651	Approved
0.7344	Intermediate Similarity	NPD6823	Phase 2
0.734	Intermediate Similarity	NPD6534	Approved
0.734	Intermediate Similarity	NPD4363	Phase 3
0.734	Intermediate Similarity	NPD4360	Phase 2
0.734	Intermediate Similarity	NPD6535	Approved
0.7333	Intermediate Similarity	NPD7286	Phase 2
0.7333	Intermediate Similarity	NPD7701	Phase 2
0.7321	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD1551	Phase 2
0.7312	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD2309	Approved
0.7305	Intermediate Similarity	NPD6190	Approved
0.7297	Intermediate Similarity	NPD8434	Phase 2
0.7296	Intermediate Similarity	NPD8151	Discontinued
0.7296	Intermediate Similarity	NPD4908	Phase 1
0.7284	Intermediate Similarity	NPD1933	Approved
0.7262	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD7874	Approved
0.7259	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD7229	Phase 3
0.7246	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD9494	Approved
0.7225	Intermediate Similarity	NPD7700	Phase 2
0.7225	Intermediate Similarity	NPD7699	Phase 2
0.7222	Intermediate Similarity	NPD7801	Approved
0.7219	Intermediate Similarity	NPD4287	Approved
0.7215	Intermediate Similarity	NPD1470	Approved
0.7212	Intermediate Similarity	NPD5408	Approved
0.7212	Intermediate Similarity	NPD5404	Approved
0.7212	Intermediate Similarity	NPD5405	Approved
0.7212	Intermediate Similarity	NPD5406	Approved
0.7209	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD3268	Approved
0.72	Intermediate Similarity	NPD4288	Approved
0.7197	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD7584	Approved
0.7184	Intermediate Similarity	NPD6844	Discontinued
0.7179	Intermediate Similarity	NPD1201	Approved
0.7174	Intermediate Similarity	NPD7549	Discontinued
0.7173	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD2798	Approved
0.716	Intermediate Similarity	NPD3300	Phase 2
0.712	Intermediate Similarity	NPD7240	Approved
0.7117	Intermediate Similarity	NPD4060	Phase 1
0.7113	Intermediate Similarity	NPD2493	Approved
0.7113	Intermediate Similarity	NPD2494	Approved
0.7111	Intermediate Similarity	NPD5242	Approved
0.7107	Intermediate Similarity	NPD1203	Approved
0.7107	Intermediate Similarity	NPD2797	Approved
0.7099	Intermediate Similarity	NPD3764	Approved
0.7089	Intermediate Similarity	NPD4749	Approved
0.7076	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7907	Approved
0.7073	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD5124	Phase 1
0.7072	Intermediate Similarity	NPD2403	Approved
0.707	Intermediate Similarity	NPD1610	Phase 2
0.7066	Intermediate Similarity	NPD1471	Phase 3
0.7059	Intermediate Similarity	NPD4111	Phase 1
0.7059	Intermediate Similarity	NPD4665	Approved
0.7048	Intermediate Similarity	NPD4308	Phase 3
0.7048	Intermediate Similarity	NPD7033	Discontinued
0.7031	Intermediate Similarity	NPD4361	Phase 2
0.7031	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD3452	Approved
0.7026	Intermediate Similarity	NPD3450	Approved
0.7025	Intermediate Similarity	NPD9269	Phase 2
0.7025	Intermediate Similarity	NPD1608	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