NPASS Compound

Structure

NPC95936 OpenBabel07101718292D 26 28 0 0 1 0 0 0 0 0999 V2000 -5.1962 3.0000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 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 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 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 -3.4641 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 -5.1962 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 -2.5981 1.5000 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 0.5000 0.0000 C 0 0 2 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 -1.7321 2.0000 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 -1.7321 -0.0000 0.0000 C 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 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 -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 12 1 0 0 0 0 2 12 1 0 0 0 0 3 25 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 2 0 0 0 0 7 13 2 0 0 0 0 8 13 1 0 0 0 0 9 10 1 0 0 0 0 9 12 2 0 0 0 0 10 14 1 0 0 0 0 11 15 1 0 0 0 0 11 16 1 0 0 0 0 14 18 2 0 0 0 0 14 19 1 0 0 0 0 15 17 1 0 0 0 0 15 22 2 0 0 0 0 16 13 1 6 0 0 0 16 26 1 0 0 0 0 17 18 1 0 0 0 0 17 20 2 0 0 0 0 18 23 1 0 0 0 0 19 21 2 0 0 0 0 19 24 1 0 0 0 0 20 21 1 0 0 0 0 20 26 1 0 0 0 0 21 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	354.15
Volume:	368.962
LogP:	4.872
LogD:	3.088
LogS:	-4.176
# Rotatable Bonds:	4
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.8
Synthetic Accessibility Score:	3.195
Fsp3:	0.286
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.862
MDCK Permeability:	1.555037852085661e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.072
Plasma Protein Binding (PPB):	98.27670288085938%
Volume Distribution (VD):	0.575
Pgp-substrate:	4.937316417694092%

ADMET: Metabolism

CYP1A2-inhibitor:	0.359
CYP1A2-substrate:	0.614
CYP2C19-inhibitor:	0.942
CYP2C19-substrate:	0.562
CYP2C9-inhibitor:	0.927
CYP2C9-substrate:	0.936
CYP2D6-inhibitor:	0.473
CYP2D6-substrate:	0.367
CYP3A4-inhibitor:	0.42
CYP3A4-substrate:	0.229

ADMET: Excretion

Clearance (CL):	7.286
Half-life (T1/2):	0.164

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.781
Drug-inuced Liver Injury (DILI):	0.864
AMES Toxicity:	0.036
Rat Oral Acute Toxicity:	0.878
Maximum Recommended Daily Dose:	0.439
Skin Sensitization:	0.882
Carcinogencity:	0.153
Eye Corrosion:	0.003
Eye Irritation:	0.431
Respiratory Toxicity:	0.679

Download Data

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

Natural Product: NPC95936

Natural Product ID:	NPC95936
*Common Name:**	Microfolione
IUPAC Name:	(2R)-5,7-dihydroxy-8-methoxy-6-(3-methylbut-2-enyl)-2-phenyl-2,3-dihydrochromen-4-one
Synonyms:	Microfolione
Standard InCHIKey:	IMGRRXXTMXIKTA-MRXNPFEDSA-N
Standard InCHI:	InChI=1S/C21H22O5/c1-12(2)9-10-14-18(23)17-15(22)11-16(13-7-5-4-6-8-13)26-20(17)21(25-3)19(14)24/h4-9,16,23-24H,10-11H2,1-3H3/t16-/m1/s1
SMILES:	COc1c2O[C@H](CC(=O)c2c(c(c1O)CC=C(C)C)O)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL498989
PubChem CID:	637437
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003646] 6-prenylated flavans [CHEMONTID:0003507] 6-prenylated flavanones

*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
NPO32494	cedrelopsis microfoliata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350164]

☑ 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
Others	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	Activity	=	20.0	%	PMID[501664]
NPT248	Individual Protein	Estrogen receptor beta	Homo sapiens	Activity	=	20.0	%	PMID[501664]

☑ 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 NPC95936 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	415
0.1-0.2	1571
0.2-0.3	4153
0.3-0.4	9820
0.4-0.5	8369
0.5-0.6	3418
0.6-0.7	4838
0.7-0.8	5408
0.8-0.85	2525
0.85-0.9	1598
0.9-0.95	491
0.95-1	91

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC250214
0.9801	High Similarity	NPC78225
0.9801	High Similarity	NPC162869
0.9801	High Similarity	NPC156057
0.9801	High Similarity	NPC474836
0.9801	High Similarity	NPC223787
0.9801	High Similarity	NPC474208
0.9801	High Similarity	NPC475267
0.9801	High Similarity	NPC48208
0.9739	High Similarity	NPC266314
0.9735	High Similarity	NPC255106
0.9735	High Similarity	NPC191146
0.9735	High Similarity	NPC35038
0.9735	High Similarity	NPC195796
0.9735	High Similarity	NPC68093
0.9735	High Similarity	NPC235165
0.9735	High Similarity	NPC278778
0.9735	High Similarity	NPC291878
0.9671	High Similarity	NPC472910
0.9671	High Similarity	NPC472911
0.9671	High Similarity	NPC27337
0.9671	High Similarity	NPC245758
0.9671	High Similarity	NPC472598
0.9671	High Similarity	NPC222814
0.9671	High Similarity	NPC99597
0.9671	High Similarity	NPC210084
0.9671	High Similarity	NPC36852
0.9671	High Similarity	NPC472914
0.9671	High Similarity	NPC291508
0.9671	High Similarity	NPC262286
0.9671	High Similarity	NPC96167
0.9671	High Similarity	NPC474055
0.9671	High Similarity	NPC472913
0.9669	High Similarity	NPC45849
0.9669	High Similarity	NPC200761
0.9669	High Similarity	NPC37392
0.9669	High Similarity	NPC470327
0.9669	High Similarity	NPC477503
0.9605	High Similarity	NPC209614
0.9605	High Similarity	NPC470328
0.9605	High Similarity	NPC138243
0.9605	High Similarity	NPC472916
0.9605	High Similarity	NPC472626
0.9603	High Similarity	NPC192083
0.9603	High Similarity	NPC18727
0.9603	High Similarity	NPC213896
0.9551	High Similarity	NPC326520
0.9548	High Similarity	NPC472448
0.9548	High Similarity	NPC83922
0.9548	High Similarity	NPC81679
0.9545	High Similarity	NPC14353
0.9545	High Similarity	NPC263449
0.9545	High Similarity	NPC118256
0.9545	High Similarity	NPC56085
0.9545	High Similarity	NPC204290
0.9545	High Similarity	NPC472624
0.9545	High Similarity	NPC282009
0.9545	High Similarity	NPC476980
0.9545	High Similarity	NPC36217
0.9545	High Similarity	NPC228785
0.9545	High Similarity	NPC192686
0.9545	High Similarity	NPC287328
0.9545	High Similarity	NPC119209
0.9542	High Similarity	NPC470402
0.9542	High Similarity	NPC469584
0.9539	High Similarity	NPC321779
0.9539	High Similarity	NPC168247
0.9539	High Similarity	NPC472909
0.9539	High Similarity	NPC2928
0.9539	High Similarity	NPC113906
0.9539	High Similarity	NPC117992
0.9539	High Similarity	NPC57674
0.9539	High Similarity	NPC152951
0.9539	High Similarity	NPC213622
0.9539	High Similarity	NPC226025
0.9539	High Similarity	NPC230149
0.9536	High Similarity	NPC180234
0.9536	High Similarity	NPC106976
0.9536	High Similarity	NPC120537
0.9536	High Similarity	NPC219582
0.9536	High Similarity	NPC302950
0.9536	High Similarity	NPC236637
0.9536	High Similarity	NPC199100
0.949	High Similarity	NPC170245
0.9487	High Similarity	NPC7483
0.9487	High Similarity	NPC41301
0.9487	High Similarity	NPC124038
0.9487	High Similarity	NPC220313
0.9484	High Similarity	NPC134783
0.9484	High Similarity	NPC61010
0.9484	High Similarity	NPC472634
0.9484	High Similarity	NPC471499
0.9484	High Similarity	NPC167678
0.9484	High Similarity	NPC471210
0.9484	High Similarity	NPC26326
0.9484	High Similarity	NPC308992
0.9484	High Similarity	NPC29876
0.9484	High Similarity	NPC474038
0.9484	High Similarity	NPC474186
0.9484	High Similarity	NPC472632
0.9484	High Similarity	NPC258331
0.9484	High Similarity	NPC474187
0.9484	High Similarity	NPC40491
0.9484	High Similarity	NPC278052
0.9481	High Similarity	NPC100123
0.9481	High Similarity	NPC152904
0.9481	High Similarity	NPC22192
0.9474	High Similarity	NPC227337
0.9474	High Similarity	NPC74924
0.9474	High Similarity	NPC176775
0.9474	High Similarity	NPC145379
0.9474	High Similarity	NPC69394
0.9474	High Similarity	NPC255350
0.9474	High Similarity	NPC472915
0.9474	High Similarity	NPC183878
0.9474	High Similarity	NPC231018
0.9474	High Similarity	NPC273462
0.9474	High Similarity	NPC298692
0.9474	High Similarity	NPC167091
0.9474	High Similarity	NPC206238
0.9474	High Similarity	NPC70433
0.9474	High Similarity	NPC47781
0.9474	High Similarity	NPC49402
0.9474	High Similarity	NPC22519
0.9474	High Similarity	NPC88645
0.9474	High Similarity	NPC33051
0.9474	High Similarity	NPC274327
0.9474	High Similarity	NPC160951
0.9474	High Similarity	NPC271779
0.9474	High Similarity	NPC292214
0.947	High Similarity	NPC117579
0.947	High Similarity	NPC204515
0.943	High Similarity	NPC117854
0.943	High Similarity	NPC6588
0.943	High Similarity	NPC477154
0.9427	High Similarity	NPC300053
0.9427	High Similarity	NPC470457
0.9427	High Similarity	NPC62261
0.9427	High Similarity	NPC472277
0.9427	High Similarity	NPC224280
0.9427	High Similarity	NPC108433
0.9427	High Similarity	NPC239752
0.9427	High Similarity	NPC275780
0.9427	High Similarity	NPC472450
0.9423	High Similarity	NPC220912
0.9423	High Similarity	NPC474033
0.9423	High Similarity	NPC476247
0.9423	High Similarity	NPC474034
0.9423	High Similarity	NPC472635
0.9423	High Similarity	NPC201800
0.9423	High Similarity	NPC474162
0.9423	High Similarity	NPC261470
0.9423	High Similarity	NPC474150
0.9419	High Similarity	NPC472631
0.9419	High Similarity	NPC475784
0.9419	High Similarity	NPC474287
0.9419	High Similarity	NPC472630
0.9419	High Similarity	NPC470326
0.9419	High Similarity	NPC475886
0.9419	High Similarity	NPC246478
0.9419	High Similarity	NPC320359
0.9419	High Similarity	NPC174953
0.9416	High Similarity	NPC471479
0.9416	High Similarity	NPC181960
0.9416	High Similarity	NPC217677
0.9416	High Similarity	NPC471515
0.9416	High Similarity	NPC129684
0.9416	High Similarity	NPC473272
0.9416	High Similarity	NPC241904
0.9416	High Similarity	NPC471209
0.9416	High Similarity	NPC284820
0.9416	High Similarity	NPC299520
0.9416	High Similarity	NPC476981
0.9416	High Similarity	NPC300727
0.9416	High Similarity	NPC165977
0.9412	High Similarity	NPC163780
0.9412	High Similarity	NPC196439
0.9412	High Similarity	NPC227325
0.9412	High Similarity	NPC256612
0.9412	High Similarity	NPC167815
0.9412	High Similarity	NPC50715
0.9412	High Similarity	NPC201136
0.9412	High Similarity	NPC134287
0.9412	High Similarity	NPC130589
0.9412	High Similarity	NPC146165
0.9412	High Similarity	NPC4455
0.9412	High Similarity	NPC256925
0.9412	High Similarity	NPC92659
0.9412	High Similarity	NPC20830
0.9412	High Similarity	NPC2476
0.9412	High Similarity	NPC138360
0.9412	High Similarity	NPC183597
0.9412	High Similarity	NPC280339
0.9412	High Similarity	NPC128863
0.9412	High Similarity	NPC39184
0.9408	High Similarity	NPC39007
0.9408	High Similarity	NPC71334
0.9408	High Similarity	NPC198826
0.9408	High Similarity	NPC188203
0.9408	High Similarity	NPC131624

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 NPC95936 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	364
0.1-0.2	936
0.2-0.3	1775
0.3-0.4	2665
0.4-0.5	1774
0.5-0.6	976
0.6-0.7	471
0.7-0.8	134
0.8-0.85	33
0.85-0.9	14
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9603	High Similarity	NPD2393	Clinical (unspecified phase)
0.9536	High Similarity	NPD1934	Approved
0.9474	High Similarity	NPD2801	Approved
0.9062	High Similarity	NPD6166	Phase 2
0.9062	High Similarity	NPD6168	Clinical (unspecified phase)
0.9062	High Similarity	NPD6167	Clinical (unspecified phase)
0.9051	High Similarity	NPD5494	Approved
0.8981	High Similarity	NPD3882	Suspended
0.8882	High Similarity	NPD1511	Approved
0.8841	High Similarity	NPD7074	Phase 3
0.8834	High Similarity	NPD3818	Discontinued
0.8795	High Similarity	NPD4338	Clinical (unspecified phase)
0.8782	High Similarity	NPD4380	Phase 2
0.878	High Similarity	NPD7054	Approved
0.8766	High Similarity	NPD1512	Approved
0.8742	High Similarity	NPD4868	Clinical (unspecified phase)
0.8727	High Similarity	NPD7472	Approved
0.8701	High Similarity	NPD4378	Clinical (unspecified phase)
0.8688	High Similarity	NPD7075	Discontinued
0.8679	High Similarity	NPD3817	Phase 2
0.8616	High Similarity	NPD7096	Clinical (unspecified phase)
0.8609	High Similarity	NPD1550	Clinical (unspecified phase)
0.8609	High Similarity	NPD1552	Clinical (unspecified phase)
0.8563	High Similarity	NPD6797	Phase 2
0.8554	High Similarity	NPD5844	Phase 1
0.8553	High Similarity	NPD1549	Phase 2
0.8512	High Similarity	NPD7251	Discontinued
0.8476	Intermediate Similarity	NPD6232	Discontinued
0.8462	Intermediate Similarity	NPD7808	Phase 3
0.8457	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8447	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8434	Intermediate Similarity	NPD7473	Discontinued
0.8385	Intermediate Similarity	NPD7819	Suspended
0.8344	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD6801	Discontinued
0.8303	Intermediate Similarity	NPD1247	Approved
0.8303	Intermediate Similarity	NPD6959	Discontinued
0.8301	Intermediate Similarity	NPD2796	Approved
0.8261	Intermediate Similarity	NPD7411	Suspended
0.8235	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD1510	Phase 2
0.8221	Intermediate Similarity	NPD5402	Approved
0.8187	Intermediate Similarity	NPD6559	Discontinued
0.8165	Intermediate Similarity	NPD6799	Approved
0.816	Intermediate Similarity	NPD1465	Phase 2
0.8092	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD943	Approved
0.8092	Intermediate Similarity	NPD1240	Approved
0.8092	Intermediate Similarity	NPD1613	Approved
0.8065	Intermediate Similarity	NPD2935	Discontinued
0.8025	Intermediate Similarity	NPD2800	Approved
0.8	Intermediate Similarity	NPD2533	Approved
0.8	Intermediate Similarity	NPD2532	Approved
0.8	Intermediate Similarity	NPD2534	Approved
0.7987	Intermediate Similarity	NPD1607	Approved
0.7975	Intermediate Similarity	NPD6599	Discontinued
0.7966	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD919	Approved
0.7947	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD3027	Phase 3
0.7882	Intermediate Similarity	NPD3926	Phase 2
0.7881	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD7768	Phase 2
0.7806	Intermediate Similarity	NPD230	Phase 1
0.7799	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD5403	Approved
0.7778	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7772	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD6234	Discontinued
0.7744	Intermediate Similarity	NPD1653	Approved
0.7736	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD447	Suspended
0.7692	Intermediate Similarity	NPD3749	Approved
0.7683	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD920	Approved
0.7673	Intermediate Similarity	NPD2346	Discontinued
0.7669	Intermediate Similarity	NPD5401	Approved
0.7644	Intermediate Similarity	NPD3751	Discontinued
0.7643	Intermediate Similarity	NPD6651	Approved
0.764	Intermediate Similarity	NPD4628	Phase 3
0.764	Intermediate Similarity	NPD3750	Approved
0.7616	Intermediate Similarity	NPD3787	Discontinued
0.7614	Intermediate Similarity	NPD5953	Discontinued
0.7613	Intermediate Similarity	NPD2313	Discontinued
0.7613	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD1551	Phase 2
0.76	Intermediate Similarity	NPD7286	Phase 2
0.7593	Intermediate Similarity	NPD6190	Approved
0.759	Intermediate Similarity	NPD3226	Approved
0.7561	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD37	Approved
0.7558	Intermediate Similarity	NPD7199	Phase 2
0.7547	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD2799	Discontinued
0.7547	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD7228	Approved
0.7532	Intermediate Similarity	NPD9494	Approved
0.7529	Intermediate Similarity	NPD4967	Phase 2
0.7529	Intermediate Similarity	NPD4966	Approved
0.7529	Intermediate Similarity	NPD4965	Approved
0.7528	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD5711	Approved
0.7514	Intermediate Similarity	NPD5710	Approved
0.75	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6100	Approved
0.75	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6099	Approved
0.7487	Intermediate Similarity	NPD6777	Approved
0.7487	Intermediate Similarity	NPD6779	Approved
0.7487	Intermediate Similarity	NPD6782	Approved
0.7487	Intermediate Similarity	NPD6778	Approved
0.7487	Intermediate Similarity	NPD6780	Approved
0.7487	Intermediate Similarity	NPD6776	Approved
0.7487	Intermediate Similarity	NPD6781	Approved
0.7486	Intermediate Similarity	NPD8313	Approved
0.7486	Intermediate Similarity	NPD8312	Approved
0.7471	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD1243	Approved
0.7468	Intermediate Similarity	NPD1933	Approved
0.7455	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD2344	Approved
0.7439	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD4360	Phase 2
0.7405	Intermediate Similarity	NPD4363	Phase 3
0.7396	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7390	Discontinued
0.7386	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7685	Pre-registration
0.7372	Intermediate Similarity	NPD4908	Phase 1
0.7368	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7435	Discontinued
0.7363	Intermediate Similarity	NPD8150	Discontinued
0.7363	Intermediate Similarity	NPD8434	Phase 2
0.7353	Intermediate Similarity	NPD6844	Discontinued
0.7329	Intermediate Similarity	NPD3748	Approved
0.7326	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD6535	Approved
0.7312	Intermediate Similarity	NPD6534	Approved
0.7308	Intermediate Similarity	NPD2861	Phase 2
0.7301	Intermediate Similarity	NPD2424	Discontinued
0.7282	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD7783	Phase 2
0.7277	Intermediate Similarity	NPD7696	Phase 3
0.7277	Intermediate Similarity	NPD7698	Approved
0.7277	Intermediate Similarity	NPD7697	Approved
0.7273	Intermediate Similarity	NPD5242	Approved
0.7273	Intermediate Similarity	NPD2309	Approved
0.7268	Intermediate Similarity	NPD8151	Discontinued
0.7267	Intermediate Similarity	NPD5353	Approved
0.7255	Intermediate Similarity	NPD1610	Phase 2
0.7254	Intermediate Similarity	NPD7584	Approved
0.725	Intermediate Similarity	NPD5124	Phase 1
0.725	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD7870	Phase 2
0.724	Intermediate Similarity	NPD7871	Phase 2
0.7233	Intermediate Similarity	NPD6233	Phase 2
0.7225	Intermediate Similarity	NPD6823	Phase 2
0.7222	Intermediate Similarity	NPD7033	Discontinued
0.7216	Intermediate Similarity	NPD7229	Phase 3
0.7216	Intermediate Similarity	NPD7701	Phase 2
0.7215	Intermediate Similarity	NPD4625	Phase 3
0.7196	Intermediate Similarity	NPD7700	Phase 2
0.7196	Intermediate Similarity	NPD7699	Phase 2
0.7179	Intermediate Similarity	NPD1203	Approved
0.7176	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6798	Discontinued
0.7152	Intermediate Similarity	NPD6832	Phase 2
0.7143	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7874	Approved
0.711	Intermediate Similarity	NPD8455	Phase 2
0.7107	Intermediate Similarity	NPD7801	Approved
0.7105	Intermediate Similarity	NPD1548	Phase 1
0.7097	Intermediate Similarity	NPD9269	Phase 2
0.7093	Intermediate Similarity	NPD6385	Approved
0.7093	Intermediate Similarity	NPD6386	Approved
0.709	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD4361	Phase 2
0.7088	Intermediate Similarity	NPD7240	Approved
0.7081	Intermediate Similarity	NPD4060	Phase 1
0.7076	Intermediate Similarity	NPD7458	Discontinued
0.7074	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD6212	Phase 3
0.7074	Intermediate Similarity	NPD6213	Phase 3
0.7063	Intermediate Similarity	NPD3268	Approved
0.7049	Intermediate Similarity	NPD7549	Discontinued
0.7048	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6674	Discontinued
0.7048	Intermediate Similarity	NPD1652	Phase 2
0.7039	Intermediate Similarity	NPD2403	Approved
0.7037	Intermediate Similarity	NPD6355	Discontinued
0.7033	Intermediate Similarity	NPD3823	Discontinued
0.703	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD2899	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