NPASS Compound

Structure

CID175192 OpenBabel06191715552D 21 23 0 0 1 0 0 0 0 0999 V2000 3.4641 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 1.5000 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 -2.5981 1.5000 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 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 1 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 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 -1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 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 -1.7321 3.0000 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 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 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 3 6 2 0 0 0 0 3 7 1 0 0 0 0 4 6 1 0 0 0 0 4 10 2 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 7 11 2 0 0 0 0 7 16 1 0 0 0 0 8 12 1 0 0 0 0 8 17 1 6 0 0 0 9 14 1 0 0 0 0 9 18 1 1 0 0 0 10 11 1 0 0 0 0 10 21 1 0 0 0 0 11 13 1 0 0 0 0 12 13 1 0 0 0 0 12 15 1 6 0 0 0 13 19 2 0 0 0 0 14 15 1 1 0 0 0 14 20 1 0 0 0 0 15 2 1 1 0 0 0 15 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	294.11
Volume:	284.522
LogP:	1.244
LogD:	1.242
LogS:	-3.113
# Rotatable Bonds:	0
TPSA:	107.22
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.542
Synthetic Accessibility Score:	4.257
Fsp3:	0.533
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:	-5.185
MDCK Permeability:	1.1255539902776945e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.931
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.575

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.323
Plasma Protein Binding (PPB):	77.73312377929688%
Volume Distribution (VD):	0.788
Pgp-substrate:	18.840747833251953%

ADMET: Metabolism

CYP1A2-inhibitor:	0.172
CYP1A2-substrate:	0.469
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.524
CYP2C9-inhibitor:	0.014
CYP2C9-substrate:	0.243
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.171
CYP3A4-inhibitor:	0.244
CYP3A4-substrate:	0.204

ADMET: Excretion

Clearance (CL):	13.382
Half-life (T1/2):	0.264

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.273
Drug-inuced Liver Injury (DILI):	0.529
AMES Toxicity:	0.073
Rat Oral Acute Toxicity:	0.062
Maximum Recommended Daily Dose:	0.09
Skin Sensitization:	0.431
Carcinogencity:	0.312
Eye Corrosion:	0.004
Eye Irritation:	0.028
Respiratory Toxicity:	0.935

Download Data

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

Natural Product: NPC175192

Natural Product ID:	NPC175192
*Common Name:**	Monodictysin A
IUPAC Name:	(1S,3S,4S,4aS,9aS)-1,3,4,8-tetrahydroxy-4a,6-dimethyl-2,3,4,9a-tetrahydro-1H-xanthen-9-one
Synonyms:
Standard InCHIKey:	UMAJXYGKDGKWLP-AOZIVVCUSA-N
Standard InCHI:	InChI=1S/C15H18O6/c1-6-3-7(16)11-10(4-6)21-15(2)12(13(11)19)8(17)5-9(18)14(15)20/h3-4,8-9,12,14,16-18,20H,5H2,1-2H3/t8-,9-,12+,14-,15-/m0/s1
SMILES:	Cc1cc(O)c2c(c1)O[C@]1([C@@H](C2=O)[C@@H](O)C[C@@H]([C@@H]1O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL373944
PubChem CID:	16114918
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

*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
NPO5623	Monodictys putredinis	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[17291041]
NPO5623	Monodictys putredinis	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[18939864]
NPO5623	Monodictys putredinis	Species	n.a.	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
Others	4

Activity Type	# Activity
Individual Protein	4
Others	1
Protein Family	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	IC50	>	400000.0	nM	PMID[554175]
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	Inhibition	<	50.0	%	PMID[554175]
NPT441	Individual Protein	Cytochrome P450 19A1	Homo sapiens	Inhibition	=	32.0	%	PMID[554175]
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	Activity	=	191.1	uM	PMID[554175]
NPT2	Others	Unspecified		IC50	>	50000.0	nM	PMID[554175]
NPT4880	Protein Family	Cytochrome P450 1A	Homo sapiens	Inhibition	=	40.0	%	PMID[554175]

☑ 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 NPC175192 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	390
0.1-0.2	1419
0.2-0.3	3204
0.3-0.4	7416
0.4-0.5	10641
0.5-0.6	4465
0.6-0.7	4806
0.7-0.8	6568
0.8-0.85	3044
0.85-0.9	707
0.9-0.95	31
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9667	High Similarity	NPC164427
0.9597	High Similarity	NPC253904
0.9597	High Similarity	NPC321363
0.953	High Similarity	NPC207346
0.953	High Similarity	NPC46564
0.9342	High Similarity	NPC326910
0.9329	High Similarity	NPC191634
0.9216	High Similarity	NPC68727
0.9211	High Similarity	NPC167903
0.9211	High Similarity	NPC51824
0.9211	High Similarity	NPC470337
0.9211	High Similarity	NPC268992
0.9211	High Similarity	NPC113608
0.9211	High Similarity	NPC470338
0.9161	High Similarity	NPC329091
0.9161	High Similarity	NPC470339
0.9119	High Similarity	NPC225419
0.9114	High Similarity	NPC25361
0.9108	High Similarity	NPC473961
0.9103	High Similarity	NPC472055
0.9103	High Similarity	NPC470810
0.9097	High Similarity	NPC469584
0.9085	High Similarity	NPC470340
0.9085	High Similarity	NPC474843
0.9085	High Similarity	NPC180944
0.9079	High Similarity	NPC202595
0.9051	High Similarity	NPC197168
0.9051	High Similarity	NPC475985
0.9038	High Similarity	NPC476242
0.9038	High Similarity	NPC85121
0.9032	High Similarity	NPC24640
0.9026	High Similarity	NPC301233
0.902	High Similarity	NPC470675
0.902	High Similarity	NPC473131
0.9007	High Similarity	NPC47388
0.9007	High Similarity	NPC470670
0.9007	High Similarity	NPC473133
0.9007	High Similarity	NPC21835
0.9007	High Similarity	NPC85773
0.9	High Similarity	NPC6588
0.9	High Similarity	NPC477154
0.9	High Similarity	NPC474024
0.9	High Similarity	NPC117854
0.8987	High Similarity	NPC215612
0.8987	High Similarity	NPC472964
0.8981	High Similarity	NPC472902
0.8981	High Similarity	NPC155302
0.8981	High Similarity	NPC470183
0.8981	High Similarity	NPC471976
0.8981	High Similarity	NPC161947
0.8974	High Similarity	NPC475267
0.8974	High Similarity	NPC477833
0.8974	High Similarity	NPC472910
0.8974	High Similarity	NPC300727
0.8974	High Similarity	NPC181960
0.8974	High Similarity	NPC48208
0.8974	High Similarity	NPC129684
0.8974	High Similarity	NPC472913
0.8974	High Similarity	NPC241904
0.8974	High Similarity	NPC162869
0.8974	High Similarity	NPC222814
0.8974	High Similarity	NPC472914
0.8974	High Similarity	NPC156057
0.8974	High Similarity	NPC474208
0.8974	High Similarity	NPC472911
0.8974	High Similarity	NPC96167
0.8974	High Similarity	NPC245758
0.8974	High Similarity	NPC299520
0.8974	High Similarity	NPC474836
0.8968	High Similarity	NPC67396
0.8968	High Similarity	NPC37392
0.8968	High Similarity	NPC255807
0.8968	High Similarity	NPC31018
0.8968	High Similarity	NPC472909
0.8961	High Similarity	NPC87708
0.8954	High Similarity	NPC225854
0.8954	High Similarity	NPC338131
0.8947	High Similarity	NPC218569
0.8938	High Similarity	NPC43319
0.8938	High Similarity	NPC170245
0.8933	High Similarity	NPC95751
0.8931	High Similarity	NPC236132
0.8931	High Similarity	NPC7483
0.8924	High Similarity	NPC87431
0.8924	High Similarity	NPC61010
0.8924	High Similarity	NPC474186
0.8924	High Similarity	NPC3629
0.8917	High Similarity	NPC186113
0.8917	High Similarity	NPC473990
0.8917	High Similarity	NPC152904
0.891	High Similarity	NPC235165
0.891	High Similarity	NPC274730
0.891	High Similarity	NPC201837
0.891	High Similarity	NPC255106
0.8903	High Similarity	NPC89474
0.8903	High Similarity	NPC18727
0.8903	High Similarity	NPC74924
0.8903	High Similarity	NPC469405
0.8903	High Similarity	NPC135522
0.8896	High Similarity	NPC263384
0.8896	High Similarity	NPC471676
0.8896	High Similarity	NPC204515
0.8896	High Similarity	NPC244577
0.8896	High Similarity	NPC72958
0.8896	High Similarity	NPC474021
0.8896	High Similarity	NPC472420
0.8896	High Similarity	NPC202157
0.8896	High Similarity	NPC472422
0.8896	High Similarity	NPC471229
0.8896	High Similarity	NPC471677
0.8896	High Similarity	NPC232645
0.8896	High Similarity	NPC474023
0.8889	High Similarity	NPC307052
0.8889	High Similarity	NPC237440
0.8889	High Similarity	NPC241874
0.8889	High Similarity	NPC277032
0.8889	High Similarity	NPC139966
0.8889	High Similarity	NPC270160
0.8882	High Similarity	NPC91902
0.8882	High Similarity	NPC218226
0.8882	High Similarity	NPC71055
0.8875	High Similarity	NPC224280
0.8875	High Similarity	NPC326520
0.8875	High Similarity	NPC234052
0.8875	High Similarity	NPC472049
0.8874	High Similarity	NPC311144
0.8868	High Similarity	NPC472402
0.8868	High Similarity	NPC474162
0.8868	High Similarity	NPC211107
0.8868	High Similarity	NPC474150
0.8867	High Similarity	NPC73028
0.8861	High Similarity	NPC472630
0.8861	High Similarity	NPC263449
0.8861	High Similarity	NPC321399
0.8861	High Similarity	NPC119224
0.8861	High Similarity	NPC14353
0.8861	High Similarity	NPC475886
0.8861	High Similarity	NPC56085
0.8861	High Similarity	NPC200746
0.8861	High Similarity	NPC475784
0.8861	High Similarity	NPC474287
0.8861	High Similarity	NPC36217
0.8861	High Similarity	NPC174953
0.8861	High Similarity	NPC472631
0.8861	High Similarity	NPC228785
0.8859	High Similarity	NPC182421
0.8854	High Similarity	NPC217677
0.8854	High Similarity	NPC472598
0.8854	High Similarity	NPC99597
0.8854	High Similarity	NPC210084
0.8854	High Similarity	NPC165977
0.8854	High Similarity	NPC470402
0.8854	High Similarity	NPC179732
0.8854	High Similarity	NPC223787
0.8854	High Similarity	NPC27337
0.8854	High Similarity	NPC474055
0.8846	High Similarity	NPC45849
0.8846	High Similarity	NPC200761
0.8846	High Similarity	NPC321779
0.8846	High Similarity	NPC477503
0.8846	High Similarity	NPC470327
0.8839	High Similarity	NPC302950
0.8839	High Similarity	NPC106976
0.8839	High Similarity	NPC36835
0.8839	High Similarity	NPC61506
0.8839	High Similarity	NPC9743
0.8839	High Similarity	NPC260491
0.8839	High Similarity	NPC472912
0.8839	High Similarity	NPC180234
0.8839	High Similarity	NPC199100
0.8839	High Similarity	NPC120537
0.8839	High Similarity	NPC210597
0.8839	High Similarity	NPC217149
0.8839	High Similarity	NPC240476
0.8839	High Similarity	NPC216035
0.8839	High Similarity	NPC219582
0.8839	High Similarity	NPC475790
0.8839	High Similarity	NPC260979
0.8839	High Similarity	NPC19721
0.8839	High Similarity	NPC246162
0.8839	High Similarity	NPC101996
0.8839	High Similarity	NPC236637
0.8834	High Similarity	NPC472620
0.8831	High Similarity	NPC267117
0.8831	High Similarity	NPC179183
0.8831	High Similarity	NPC62042
0.8831	High Similarity	NPC151473
0.8824	High Similarity	NPC10097
0.8824	High Similarity	NPC321011
0.8824	High Similarity	NPC294852
0.8824	High Similarity	NPC188679
0.882	High Similarity	NPC469394
0.882	High Similarity	NPC120593
0.882	High Similarity	NPC37870
0.882	High Similarity	NPC178851
0.882	High Similarity	NPC272502
0.882	High Similarity	NPC178173
0.8816	High Similarity	NPC469758
0.8816	High Similarity	NPC290133
0.8816	High Similarity	NPC24136

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 NPC175192 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	338
0.1-0.2	867
0.2-0.3	1768
0.3-0.4	2578
0.4-0.5	1917
0.5-0.6	1035
0.6-0.7	452
0.7-0.8	153
0.8-0.85	40
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8839	High Similarity	NPD1934	Approved
0.8782	High Similarity	NPD2393	Clinical (unspecified phase)
0.8662	High Similarity	NPD2801	Approved
0.8533	High Similarity	NPD1552	Clinical (unspecified phase)
0.8533	High Similarity	NPD1550	Clinical (unspecified phase)
0.8528	High Similarity	NPD6168	Clinical (unspecified phase)
0.8528	High Similarity	NPD6166	Phase 2
0.8528	High Similarity	NPD6167	Clinical (unspecified phase)
0.8477	Intermediate Similarity	NPD1549	Phase 2
0.8471	Intermediate Similarity	NPD4380	Phase 2
0.8457	Intermediate Similarity	NPD6959	Discontinued
0.8442	Intermediate Similarity	NPD1511	Approved
0.8395	Intermediate Similarity	NPD5494	Approved
0.8385	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD6099	Approved
0.8344	Intermediate Similarity	NPD6100	Approved
0.8333	Intermediate Similarity	NPD1512	Approved
0.8323	Intermediate Similarity	NPD7074	Phase 3
0.8323	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD3882	Suspended
0.8313	Intermediate Similarity	NPD3818	Discontinued
0.8272	Intermediate Similarity	NPD7075	Discontinued
0.8269	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD7054	Approved
0.8263	Intermediate Similarity	NPD5844	Phase 1
0.8261	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD7473	Discontinued
0.8235	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD7472	Approved
0.8199	Intermediate Similarity	NPD7819	Suspended
0.8199	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD6232	Discontinued
0.8176	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8166	Intermediate Similarity	NPD6797	Phase 2
0.8158	Intermediate Similarity	NPD1510	Phase 2
0.8153	Intermediate Similarity	NPD2532	Approved
0.8153	Intermediate Similarity	NPD2533	Approved
0.8153	Intermediate Similarity	NPD2534	Approved
0.8148	Intermediate Similarity	NPD5402	Approved
0.8148	Intermediate Similarity	NPD3817	Phase 2
0.8146	Intermediate Similarity	NPD1607	Approved
0.8125	Intermediate Similarity	NPD6599	Discontinued
0.8118	Intermediate Similarity	NPD7251	Discontinued
0.8118	Intermediate Similarity	NPD6559	Discontinued
0.8105	Intermediate Similarity	NPD2796	Approved
0.807	Intermediate Similarity	NPD7808	Phase 3
0.8047	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD6801	Discontinued
0.8013	Intermediate Similarity	NPD1240	Approved
0.8011	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD3751	Discontinued
0.7975	Intermediate Similarity	NPD1465	Phase 2
0.7975	Intermediate Similarity	NPD6799	Approved
0.7964	Intermediate Similarity	NPD3787	Discontinued
0.7953	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD4628	Phase 3
0.7871	Intermediate Similarity	NPD1551	Phase 2
0.7853	Intermediate Similarity	NPD7411	Suspended
0.7834	Intermediate Similarity	NPD2800	Approved
0.7831	Intermediate Similarity	NPD3749	Approved
0.7826	Intermediate Similarity	NPD5403	Approved
0.7816	Intermediate Similarity	NPD8312	Approved
0.7816	Intermediate Similarity	NPD8313	Approved
0.7806	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD8150	Discontinued
0.7784	Intermediate Similarity	NPD8434	Phase 2
0.7778	Intermediate Similarity	NPD1613	Approved
0.7778	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD3226	Approved
0.7707	Intermediate Similarity	NPD2346	Discontinued
0.7705	Intermediate Similarity	NPD6778	Approved
0.7705	Intermediate Similarity	NPD6777	Approved
0.7705	Intermediate Similarity	NPD6781	Approved
0.7705	Intermediate Similarity	NPD6782	Approved
0.7705	Intermediate Similarity	NPD6776	Approved
0.7705	Intermediate Similarity	NPD6779	Approved
0.7705	Intermediate Similarity	NPD6780	Approved
0.7702	Intermediate Similarity	NPD5401	Approved
0.7702	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD3750	Approved
0.7662	Intermediate Similarity	NPD943	Approved
0.7661	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD4749	Approved
0.7647	Intermediate Similarity	NPD5710	Approved
0.7647	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD5711	Approved
0.7613	Intermediate Similarity	NPD230	Phase 1
0.759	Intermediate Similarity	NPD37	Approved
0.7588	Intermediate Similarity	NPD1247	Approved
0.7581	Intermediate Similarity	NPD7435	Discontinued
0.7574	Intermediate Similarity	NPD6234	Discontinued
0.7566	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD7768	Phase 2
0.756	Intermediate Similarity	NPD4967	Phase 2
0.756	Intermediate Similarity	NPD4965	Approved
0.756	Intermediate Similarity	NPD4966	Approved
0.7532	Intermediate Similarity	NPD2935	Discontinued
0.7531	Intermediate Similarity	NPD7390	Discontinued
0.7528	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD447	Suspended
0.75	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3926	Phase 2
0.7487	Intermediate Similarity	NPD7698	Approved
0.7487	Intermediate Similarity	NPD7697	Approved
0.7487	Intermediate Similarity	NPD7696	Phase 3
0.7485	Intermediate Similarity	NPD7199	Phase 2
0.7474	Intermediate Similarity	NPD8151	Discontinued
0.7471	Intermediate Similarity	NPD7228	Approved
0.7468	Intermediate Similarity	NPD4625	Phase 3
0.7468	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD6651	Approved
0.7447	Intermediate Similarity	NPD7870	Phase 2
0.7447	Intermediate Similarity	NPD7871	Phase 2
0.744	Intermediate Similarity	NPD5760	Phase 2
0.744	Intermediate Similarity	NPD5761	Phase 2
0.7433	Intermediate Similarity	NPD6823	Phase 2
0.7432	Intermediate Similarity	NPD6534	Approved
0.7432	Intermediate Similarity	NPD6535	Approved
0.7421	Intermediate Similarity	NPD7701	Phase 2
0.7419	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD4908	Phase 1
0.74	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD1610	Phase 2
0.7396	Intermediate Similarity	NPD7801	Approved
0.7396	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7783	Phase 2
0.7394	Intermediate Similarity	NPD920	Approved
0.7391	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD2344	Approved
0.7368	Intermediate Similarity	NPD919	Approved
0.7358	Intermediate Similarity	NPD7033	Discontinued
0.7358	Intermediate Similarity	NPD3748	Approved
0.7358	Intermediate Similarity	NPD2799	Discontinued
0.7356	Intermediate Similarity	NPD2403	Approved
0.7355	Intermediate Similarity	NPD3027	Phase 3
0.7349	Intermediate Similarity	NPD1653	Approved
0.7344	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD7874	Approved
0.7337	Intermediate Similarity	NPD4363	Phase 3
0.7337	Intermediate Similarity	NPD4360	Phase 2
0.7326	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD7699	Phase 2
0.7312	Intermediate Similarity	NPD7700	Phase 2
0.7308	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD6190	Approved
0.7299	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD1243	Approved
0.7278	Intermediate Similarity	NPD6844	Discontinued
0.7273	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD5953	Discontinued
0.7237	Intermediate Similarity	NPD1608	Approved
0.7232	Intermediate Similarity	NPD7286	Phase 2
0.7226	Intermediate Similarity	NPD2861	Phase 2
0.7222	Intermediate Similarity	NPD2424	Discontinued
0.7208	Intermediate Similarity	NPD1470	Approved
0.7208	Intermediate Similarity	NPD1203	Approved
0.7207	Intermediate Similarity	NPD7685	Pre-registration
0.7197	Intermediate Similarity	NPD2313	Discontinued
0.7197	Intermediate Similarity	NPD3268	Approved
0.7197	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD411	Approved
0.7195	Intermediate Similarity	NPD2309	Approved
0.7186	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD1652	Phase 2
0.7173	Intermediate Similarity	NPD8319	Approved
0.7173	Intermediate Similarity	NPD8320	Phase 1
0.7171	Intermediate Similarity	NPD1201	Approved
0.717	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD5124	Phase 1
0.7161	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD2798	Approved
0.7152	Intermediate Similarity	NPD3300	Phase 2
0.7152	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7229	Phase 3
0.7143	Intermediate Similarity	NPD4308	Phase 3
0.7124	Intermediate Similarity	NPD9717	Approved
0.7118	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD9494	Approved
0.7111	Intermediate Similarity	NPD7240	Approved
0.7101	Intermediate Similarity	NPD7458	Discontinued
0.7098	Intermediate Similarity	NPD7584	Approved
0.7097	Intermediate Similarity	NPD2797	Approved
0.7097	Intermediate Similarity	NPD6212	Phase 3
0.7097	Intermediate Similarity	NPD6213	Phase 3
0.7097	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD5353	Approved
0.7074	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6674	Discontinued
0.707	Intermediate Similarity	NPD6832	Phase 2
0.7069	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6355	Discontinued

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