NPASS Compound

Structure

NPC471973 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 6.9282 -5.0000 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 -1.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -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 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 6.0622 -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 6.0622 -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 -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 2.5981 -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 5.1962 0.0000 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 4.3301 -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 0.0000 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 5.1962 1.0000 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 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 13 1 0 0 0 0 8 23 1 0 0 0 0 9 12 2 0 0 0 0 9 14 1 0 0 0 0 10 15 2 0 0 0 0 10 16 1 0 0 0 0 12 17 1 0 0 0 0 13 15 1 0 0 0 0 13 19 2 0 0 0 0 14 20 2 0 0 0 0 14 24 1 0 0 0 0 15 29 1 0 0 0 0 16 18 2 0 0 0 0 16 28 1 0 0 0 0 17 21 1 0 0 0 0 17 22 2 0 0 0 0 18 19 1 0 0 0 0 18 21 1 0 0 0 0 19 25 1 0 0 0 0 20 22 1 0 0 0 0 20 26 1 0 0 0 0 21 27 2 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:	5.708
LogD:	3.246
LogS:	-2.855
# 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:	3.413
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:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.845
MDCK Permeability:	1.4961427041271236e-05
Pgp-inhibitor:	0.737
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.354
20% Bioavailability (F20%):	0.019
30% Bioavailability (F30%):	0.055

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	90.6191177368164%
Volume Distribution (VD):	0.646
Pgp-substrate:	10.645292282104492%

ADMET: Metabolism

CYP1A2-inhibitor:	0.642
CYP1A2-substrate:	0.259
CYP2C19-inhibitor:	0.543
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.833
CYP2C9-substrate:	0.789
CYP2D6-inhibitor:	0.683
CYP2D6-substrate:	0.189
CYP3A4-inhibitor:	0.212
CYP3A4-substrate:	0.09

ADMET: Excretion

Clearance (CL):	2.8
Half-life (T1/2):	0.427

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.935
Drug-inuced Liver Injury (DILI):	0.979
AMES Toxicity:	0.432
Rat Oral Acute Toxicity:	0.339
Maximum Recommended Daily Dose:	0.779
Skin Sensitization:	0.861
Carcinogencity:	0.783
Eye Corrosion:	0.003
Eye Irritation:	0.523
Respiratory Toxicity:	0.469

Download Data

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

Natural Product: NPC471973

Natural Product ID:	NPC471973
*Common Name:**	NLPCIKWXJPLCOY-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NLPCIKWXJPLCOY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C23H22O6/c1-11(2)5-6-12-9-14(24)20(26)22-17(12)21(27)18-16(28-22)10-15-13(19(18)25)7-8-23(3,4)29-15/h5,7-10,24-26H,6H2,1-4H3
SMILES:	CC(=CCC1=CC(=C(C2=C1C(=O)C3=C(C4=C(C=C3O2)OC(C=C4)(C)C)O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3314600
PubChem CID:	n.a.
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
NPO32711	garcinia esculenta	Species	Clusiaceae	Eukaryota	twigs	n.a.	n.a.	PMID[24960143]

☑ 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	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	10000.0	nM	PMID[530418]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[530418]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	10000.0	nM	PMID[530418]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	50000.0	nM	PMID[530418]
NPT27	Others	Unspecified		IC50	>	10000.0	nM	PMID[530418]

☑ 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 NPC471973 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	458
0.1-0.2	1913
0.2-0.3	4449
0.3-0.4	11188
0.4-0.5	6665
0.5-0.6	3672
0.6-0.7	5117
0.7-0.8	4998
0.8-0.85	2553
0.85-0.9	1175
0.9-0.95	452
0.95-1	57

Similarity Score	Similarity Level	Natural Product ID
0.9868	High Similarity	NPC136674
0.9805	High Similarity	NPC189473
0.9805	High Similarity	NPC23298
0.9742	High Similarity	NPC275780
0.9742	High Similarity	NPC472450
0.9742	High Similarity	NPC239752
0.9737	High Similarity	NPC474681
0.9737	High Similarity	NPC218313
0.9679	High Similarity	NPC37870
0.9679	High Similarity	NPC472449
0.9679	High Similarity	NPC39091
0.9677	High Similarity	NPC186686
0.9675	High Similarity	NPC234644
0.9673	High Similarity	NPC235448
0.9673	High Similarity	NPC204879
0.9671	High Similarity	NPC5322
0.9671	High Similarity	NPC6633
0.9671	High Similarity	NPC133970
0.9613	High Similarity	NPC229632
0.9613	High Similarity	NPC329760
0.9613	High Similarity	NPC25152
0.9613	High Similarity	NPC474150
0.9613	High Similarity	NPC474162
0.961	High Similarity	NPC474960
0.961	High Similarity	NPC204290
0.961	High Similarity	NPC139036
0.961	High Similarity	NPC188433
0.9605	High Similarity	NPC200246
0.9605	High Similarity	NPC472280
0.9554	High Similarity	NPC43319
0.9551	High Similarity	NPC236521
0.9551	High Similarity	NPC207690
0.9551	High Similarity	NPC152659
0.9551	High Similarity	NPC248638
0.9548	High Similarity	NPC29876
0.9548	High Similarity	NPC167678
0.9548	High Similarity	NPC57715
0.9548	High Similarity	NPC61010
0.9545	High Similarity	NPC100123
0.9545	High Similarity	NPC474290
0.9542	High Similarity	NPC472455
0.9542	High Similarity	NPC471985
0.9542	High Similarity	NPC470600
0.9542	High Similarity	NPC472907
0.9539	High Similarity	NPC472905
0.9539	High Similarity	NPC33051
0.9539	High Similarity	NPC49402
0.9539	High Similarity	NPC273462
0.9539	High Similarity	NPC70433
0.9539	High Similarity	NPC227337
0.9494	High Similarity	NPC218226
0.949	High Similarity	NPC293319
0.949	High Similarity	NPC303174
0.9487	High Similarity	NPC83922
0.9487	High Similarity	NPC472448
0.9484	High Similarity	NPC36217
0.9484	High Similarity	NPC56085
0.9484	High Similarity	NPC14353
0.9484	High Similarity	NPC118256
0.9484	High Similarity	NPC228785
0.9484	High Similarity	NPC320359
0.9484	High Similarity	NPC200746
0.9484	High Similarity	NPC192686
0.9484	High Similarity	NPC119209
0.9481	High Similarity	NPC187745
0.9481	High Similarity	NPC52889
0.9481	High Similarity	NPC472963
0.9481	High Similarity	NPC161960
0.9481	High Similarity	NPC304008
0.9477	High Similarity	NPC117992
0.9477	High Similarity	NPC230149
0.9477	High Similarity	NPC234255
0.9477	High Similarity	NPC57674
0.9477	High Similarity	NPC256925
0.9477	High Similarity	NPC152951
0.9477	High Similarity	NPC168247
0.9474	High Similarity	NPC237994
0.947	High Similarity	NPC151473
0.9427	High Similarity	NPC220313
0.9427	High Similarity	NPC146134
0.9427	High Similarity	NPC306321
0.9427	High Similarity	NPC303460
0.9423	High Similarity	NPC40491
0.9423	High Similarity	NPC474038
0.9423	High Similarity	NPC472906
0.9423	High Similarity	NPC259456
0.9423	High Similarity	NPC278052
0.9419	High Similarity	NPC184755
0.9419	High Similarity	NPC476242
0.9419	High Similarity	NPC74178
0.9419	High Similarity	NPC280680
0.9416	High Similarity	NPC274730
0.9416	High Similarity	NPC191146
0.9416	High Similarity	NPC68093
0.9416	High Similarity	NPC142339
0.9416	High Similarity	NPC115853
0.9412	High Similarity	NPC170492
0.9408	High Similarity	NPC154345
0.9371	High Similarity	NPC477154
0.9371	High Similarity	NPC117854
0.9371	High Similarity	NPC476306
0.9371	High Similarity	NPC6588
0.9367	High Similarity	NPC62261
0.9363	High Similarity	NPC201800
0.9363	High Similarity	NPC78332
0.9363	High Similarity	NPC206605
0.9359	High Similarity	NPC476980
0.9359	High Similarity	NPC80375
0.9359	High Similarity	NPC476280
0.9359	High Similarity	NPC475784
0.9359	High Similarity	NPC235018
0.9359	High Similarity	NPC45146
0.9355	High Similarity	NPC273843
0.9355	High Similarity	NPC473272
0.9355	High Similarity	NPC236796
0.9355	High Similarity	NPC300727
0.9355	High Similarity	NPC165977
0.9355	High Similarity	NPC180011
0.9355	High Similarity	NPC241904
0.9355	High Similarity	NPC27337
0.9355	High Similarity	NPC219867
0.9355	High Similarity	NPC284820
0.9355	High Similarity	NPC78225
0.9355	High Similarity	NPC217677
0.9346	High Similarity	NPC471982
0.9342	High Similarity	NPC3825
0.9342	High Similarity	NPC88804
0.9313	High Similarity	NPC476637
0.9313	High Similarity	NPC288813
0.9308	High Similarity	NPC272502
0.9308	High Similarity	NPC170245
0.9304	High Similarity	NPC472625
0.9304	High Similarity	NPC270837
0.9304	High Similarity	NPC7483
0.9304	High Similarity	NPC236132
0.9304	High Similarity	NPC12461
0.9299	High Similarity	NPC32694
0.9299	High Similarity	NPC26326
0.9299	High Similarity	NPC471210
0.9299	High Similarity	NPC474187
0.9299	High Similarity	NPC472632
0.9299	High Similarity	NPC134783
0.9295	High Similarity	NPC46736
0.9295	High Similarity	NPC197856
0.9295	High Similarity	NPC210459
0.929	High Similarity	NPC138243
0.929	High Similarity	NPC278778
0.929	High Similarity	NPC13779
0.929	High Similarity	NPC170026
0.929	High Similarity	NPC24640
0.929	High Similarity	NPC475799
0.929	High Similarity	NPC291878
0.929	High Similarity	NPC276444
0.929	High Similarity	NPC282307
0.929	High Similarity	NPC35038
0.929	High Similarity	NPC195796
0.9286	High Similarity	NPC280530
0.9286	High Similarity	NPC178964
0.9286	High Similarity	NPC89474
0.9286	High Similarity	NPC95842
0.9276	High Similarity	NPC65775
0.9276	High Similarity	NPC10027
0.9255	High Similarity	NPC101107
0.925	High Similarity	NPC126204
0.925	High Similarity	NPC474024
0.9245	High Similarity	NPC156432
0.9245	High Similarity	NPC326520
0.9241	High Similarity	NPC474033
0.9241	High Similarity	NPC294965
0.9241	High Similarity	NPC472964
0.9241	High Similarity	NPC52204
0.9241	High Similarity	NPC474034
0.9241	High Similarity	NPC261470
0.9236	High Similarity	NPC474287
0.9236	High Similarity	NPC472624
0.9236	High Similarity	NPC472902
0.9236	High Similarity	NPC299436
0.9236	High Similarity	NPC119224
0.9236	High Similarity	NPC475886
0.9236	High Similarity	NPC174953
0.9236	High Similarity	NPC321399
0.9236	High Similarity	NPC297212
0.9231	High Similarity	NPC237418
0.9231	High Similarity	NPC262286
0.9231	High Similarity	NPC476981
0.9231	High Similarity	NPC36852
0.9231	High Similarity	NPC218871
0.9231	High Similarity	NPC471209
0.9231	High Similarity	NPC472598
0.9231	High Similarity	NPC299520
0.9231	High Similarity	NPC129684
0.9231	High Similarity	NPC291508
0.9231	High Similarity	NPC474055
0.9231	High Similarity	NPC476630
0.9226	High Similarity	NPC470327
0.9226	High Similarity	NPC477503
0.9226	High Similarity	NPC67396
0.9226	High Similarity	NPC45849
0.9226	High Similarity	NPC200761
0.9221	High Similarity	NPC63187

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 NPC471973 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	410
0.1-0.2	1019
0.2-0.3	1725
0.3-0.4	2714
0.4-0.5	1762
0.5-0.6	947
0.6-0.7	392
0.7-0.8	132
0.8-0.85	33
0.85-0.9	12
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9161	High Similarity	NPD2393	Clinical (unspecified phase)
0.9161	High Similarity	NPD2801	Approved
0.9097	High Similarity	NPD1934	Approved
0.8947	High Similarity	NPD1511	Approved
0.8831	High Similarity	NPD1512	Approved
0.8805	High Similarity	NPD3882	Suspended
0.8773	High Similarity	NPD6167	Clinical (unspecified phase)
0.8773	High Similarity	NPD6168	Clinical (unspecified phase)
0.8773	High Similarity	NPD6166	Phase 2
0.865	High Similarity	NPD6232	Discontinued
0.8645	High Similarity	NPD4378	Clinical (unspecified phase)
0.8645	High Similarity	NPD7410	Clinical (unspecified phase)
0.8642	High Similarity	NPD5494	Approved
0.8614	High Similarity	NPD7054	Approved
0.8608	High Similarity	NPD4380	Phase 2
0.8606	High Similarity	NPD7473	Discontinued
0.8563	High Similarity	NPD7472	Approved
0.8563	High Similarity	NPD7074	Phase 3
0.8562	High Similarity	NPD1465	Phase 2
0.8562	High Similarity	NPD7819	Suspended
0.8554	High Similarity	NPD3818	Discontinued
0.8509	High Similarity	NPD3817	Phase 2
0.8457	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8412	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8405	Intermediate Similarity	NPD7075	Discontinued
0.8402	Intermediate Similarity	NPD6797	Phase 2
0.8395	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8393	Intermediate Similarity	NPD5844	Phase 1
0.8364	Intermediate Similarity	NPD6959	Discontinued
0.8353	Intermediate Similarity	NPD7251	Discontinued
0.8333	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8312	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8312	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8304	Intermediate Similarity	NPD7808	Phase 3
0.8293	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD3749	Approved
0.8269	Intermediate Similarity	NPD3750	Approved
0.8258	Intermediate Similarity	NPD1549	Phase 2
0.821	Intermediate Similarity	NPD7411	Suspended
0.8182	Intermediate Similarity	NPD1510	Phase 2
0.8176	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD6801	Discontinued
0.8158	Intermediate Similarity	NPD943	Approved
0.8141	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD2796	Approved
0.8039	Intermediate Similarity	NPD1240	Approved
0.8	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6799	Approved
0.7977	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD2800	Approved
0.795	Intermediate Similarity	NPD2532	Approved
0.795	Intermediate Similarity	NPD2534	Approved
0.795	Intermediate Similarity	NPD2533	Approved
0.7949	Intermediate Similarity	NPD3748	Approved
0.7949	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD3926	Phase 2
0.7935	Intermediate Similarity	NPD1607	Approved
0.7929	Intermediate Similarity	NPD1247	Approved
0.7927	Intermediate Similarity	NPD6599	Discontinued
0.7923	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD919	Approved
0.7904	Intermediate Similarity	NPD7768	Phase 2
0.7898	Intermediate Similarity	NPD6100	Approved
0.7898	Intermediate Similarity	NPD6099	Approved
0.7895	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD3226	Approved
0.7848	Intermediate Similarity	NPD2346	Discontinued
0.7844	Intermediate Similarity	NPD5402	Approved
0.7834	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD6559	Discontinued
0.7821	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7390	Discontinued
0.7744	Intermediate Similarity	NPD5403	Approved
0.7735	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD4625	Phase 3
0.7722	Intermediate Similarity	NPD2799	Discontinued
0.7719	Intermediate Similarity	NPD7199	Phase 2
0.7706	Intermediate Similarity	NPD6234	Discontinued
0.7701	Intermediate Similarity	NPD3751	Discontinued
0.7692	Intermediate Similarity	NPD1613	Approved
0.7692	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD3787	Discontinued
0.7673	Intermediate Similarity	NPD2935	Discontinued
0.7654	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD447	Suspended
0.764	Intermediate Similarity	NPD1243	Approved
0.764	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD2344	Approved
0.7622	Intermediate Similarity	NPD5401	Approved
0.76	Intermediate Similarity	NPD7228	Approved
0.7593	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD2313	Discontinued
0.7564	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD8313	Approved
0.7542	Intermediate Similarity	NPD8312	Approved
0.7532	Intermediate Similarity	NPD230	Phase 1
0.753	Intermediate Similarity	NPD920	Approved
0.7515	Intermediate Similarity	NPD37	Approved
0.7515	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3027	Phase 3
0.7485	Intermediate Similarity	NPD4965	Approved
0.7485	Intermediate Similarity	NPD4966	Approved
0.7485	Intermediate Similarity	NPD4967	Phase 2
0.7485	Intermediate Similarity	NPD4628	Phase 3
0.7484	Intermediate Similarity	NPD6651	Approved
0.7472	Intermediate Similarity	NPD5953	Discontinued
0.7471	Intermediate Similarity	NPD5710	Approved
0.7471	Intermediate Similarity	NPD5711	Approved
0.7455	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD1551	Phase 2
0.7452	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD6778	Approved
0.7447	Intermediate Similarity	NPD6780	Approved
0.7447	Intermediate Similarity	NPD6776	Approved
0.7447	Intermediate Similarity	NPD6782	Approved
0.7447	Intermediate Similarity	NPD6781	Approved
0.7447	Intermediate Similarity	NPD6777	Approved
0.7447	Intermediate Similarity	NPD6779	Approved
0.7439	Intermediate Similarity	NPD2309	Approved
0.7436	Intermediate Similarity	NPD4908	Phase 1
0.743	Intermediate Similarity	NPD7685	Pre-registration
0.7421	Intermediate Similarity	NPD1933	Approved
0.7418	Intermediate Similarity	NPD8150	Discontinued
0.741	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD9494	Approved
0.7366	Intermediate Similarity	NPD4360	Phase 2
0.7366	Intermediate Similarity	NPD4363	Phase 3
0.736	Intermediate Similarity	NPD7286	Phase 2
0.7355	Intermediate Similarity	NPD1470	Approved
0.7346	Intermediate Similarity	NPD5404	Approved
0.7346	Intermediate Similarity	NPD5405	Approved
0.7346	Intermediate Similarity	NPD5406	Approved
0.7346	Intermediate Similarity	NPD5408	Approved
0.7342	Intermediate Similarity	NPD3268	Approved
0.7338	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD4287	Approved
0.733	Intermediate Similarity	NPD7435	Discontinued
0.7326	Intermediate Similarity	NPD4288	Approved
0.732	Intermediate Similarity	NPD8151	Discontinued
0.732	Intermediate Similarity	NPD1201	Approved
0.7308	Intermediate Similarity	NPD2798	Approved
0.7287	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1653	Approved
0.7273	Intermediate Similarity	NPD7229	Phase 3
0.725	Intermediate Similarity	NPD4060	Phase 1
0.7245	Intermediate Similarity	NPD7783	Phase 2
0.7245	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD2797	Approved
0.7244	Intermediate Similarity	NPD1203	Approved
0.724	Intermediate Similarity	NPD7697	Approved
0.724	Intermediate Similarity	NPD7696	Phase 3
0.724	Intermediate Similarity	NPD7698	Approved
0.7233	Intermediate Similarity	NPD3764	Approved
0.7229	Intermediate Similarity	NPD6190	Approved
0.7228	Intermediate Similarity	NPD8434	Phase 2
0.7226	Intermediate Similarity	NPD4749	Approved
0.7216	Intermediate Similarity	NPD7584	Approved
0.7208	Intermediate Similarity	NPD1610	Phase 2
0.7205	Intermediate Similarity	NPD5124	Phase 1
0.7205	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7870	Phase 2
0.7202	Intermediate Similarity	NPD7871	Phase 2
0.7202	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD1471	Phase 3
0.7188	Intermediate Similarity	NPD6823	Phase 2
0.7181	Intermediate Similarity	NPD6534	Approved
0.7181	Intermediate Similarity	NPD6535	Approved
0.7179	Intermediate Similarity	NPD7701	Phase 2
0.7178	Intermediate Similarity	NPD4308	Phase 3
0.7178	Intermediate Similarity	NPD7033	Discontinued
0.7161	Intermediate Similarity	NPD1608	Approved
0.7143	Intermediate Similarity	NPD7240	Approved
0.7143	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4361	Phase 2
0.7135	Intermediate Similarity	NPD7458	Discontinued
0.7135	Intermediate Similarity	NPD2494	Approved
0.7135	Intermediate Similarity	NPD2493	Approved
0.7135	Intermediate Similarity	NPD5242	Approved
0.7107	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD7874	Approved
0.7097	Intermediate Similarity	NPD422	Phase 1
0.7097	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD2403	Approved
0.7083	Intermediate Similarity	NPD3300	Phase 2
0.7071	Intermediate Similarity	NPD7801	Approved
0.707	Intermediate Similarity	NPD3225	Approved
0.7068	Intermediate Similarity	NPD7699	Phase 2
0.7068	Intermediate Similarity	NPD7700	Phase 2
0.7066	Intermediate Similarity	NPD7003	Approved
0.7059	Intermediate Similarity	NPD1548	Phase 1
0.7052	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD9717	Approved
0.7051	Intermediate Similarity	NPD9269	Phase 2

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