NPASS Compound

Structure

CID36217 OpenBabel06191715362D 32 34 0 0 1 0 0 0 0 0999 V2000 -2.5981 3.5000 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 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 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 2.5981 -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 -1.0000 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 -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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 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 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 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 -0.0000 2.0000 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 -0.8660 0.5000 0.0000 C 0 0 1 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 -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 3.4641 -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 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 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 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 15 1 0 0 0 0 5 31 1 0 0 0 0 6 8 1 0 0 0 0 6 14 2 0 0 0 0 7 9 1 0 0 0 0 7 15 2 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 10 11 2 0 0 0 0 10 16 1 0 0 0 0 11 22 1 0 0 0 0 12 19 2 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 13 23 1 0 0 0 0 16 17 2 0 0 0 0 17 25 1 0 0 0 0 18 19 1 0 0 0 0 18 26 2 0 0 0 0 19 27 1 0 0 0 0 20 24 2 0 0 0 0 20 28 1 0 0 0 0 21 24 1 0 0 0 0 21 29 2 0 0 0 0 22 25 2 0 0 0 0 22 31 1 0 0 0 0 23 16 1 6 0 0 0 23 32 1 0 0 0 0 24 26 1 0 0 0 0 25 30 1 0 0 0 0 26 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	438.2
Volume:	461.596
LogP:	6.737
LogD:	3.872
LogS:	-2.957
# Rotatable Bonds:	6
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.513
Synthetic Accessibility Score:	3.617
Fsp3:	0.346
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:	-4.814
MDCK Permeability:	1.3804125956085045e-05
Pgp-inhibitor:	0.818
Pgp-substrate:	0.884
Human Intestinal Absorption (HIA):	0.025
20% Bioavailability (F20%):	0.854
30% Bioavailability (F30%):	0.293

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	87.68221282958984%
Volume Distribution (VD):	0.968
Pgp-substrate:	13.5090913772583%

ADMET: Metabolism

CYP1A2-inhibitor:	0.298
CYP1A2-substrate:	0.827
CYP2C19-inhibitor:	0.952
CYP2C19-substrate:	0.144
CYP2C9-inhibitor:	0.909
CYP2C9-substrate:	0.956
CYP2D6-inhibitor:	0.765
CYP2D6-substrate:	0.543
CYP3A4-inhibitor:	0.375
CYP3A4-substrate:	0.203

ADMET: Excretion

Clearance (CL):	16.559
Half-life (T1/2):	0.198

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.906
Drug-inuced Liver Injury (DILI):	0.773
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.816
Maximum Recommended Daily Dose:	0.448
Skin Sensitization:	0.933
Carcinogencity:	0.121
Eye Corrosion:	0.003
Eye Irritation:	0.562
Respiratory Toxicity:	0.943

Download Data

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

Natural Product: NPC36217

Natural Product ID:	NPC36217
*Common Name:**	5,7,3'-Trihydroxy-4'-Methoxy-8,2'-Di(3-Methyl-2-Butenyl)-(2S)-Flavanone
IUPAC Name:	(2S)-5,7-dihydroxy-2-[3-hydroxy-4-methoxy-2-(3-methylbut-2-enyl)phenyl]-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
Synonyms:
Standard InCHIKey:	LGSFAJAWSUQNON-QHCPKHFHSA-N
Standard InCHI:	InChI=1S/C26H30O6/c1-14(2)6-8-17-16(10-11-22(31-5)25(17)30)23-13-21(29)24-20(28)12-19(27)18(26(24)32-23)9-7-15(3)4/h6-7,10-12,23,27-28,30H,8-9,13H2,1-5H3/t23-/m0/s1
SMILES:	CC(=CCc1c(ccc(c1O)OC)[C@@H]1CC(=O)c2c(cc(c(CC=C(C)C)c2O1)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL470666
PubChem CID:	3012486
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003645] 2'-prenylated flavans [CHEMONTID:0003588] 2'-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
NPO32946	dendrolobium tanceolatum	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[15217275]
NPO22556	Dendrolobium lanceolatum	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[15217275]
NPO22556	Dendrolobium lanceolatum	Species	Fabaceae	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
MIC	1

Activity Type	# Activity
Cell Line	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	=	8.1	ug.mL-1	PMID[466427]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	3.3	ug.mL-1	PMID[466427]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	12.5	ug.mL-1	PMID[466427]

☑ 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 NPC36217 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	418
0.1-0.2	1560
0.2-0.3	3787
0.3-0.4	9467
0.4-0.5	8857
0.5-0.6	3137
0.6-0.7	4625
0.7-0.8	5502
0.8-0.85	2926
0.85-0.9	1889
0.9-0.95	453
0.95-1	76

Similarity Score	Similarity Level	Natural Product ID
0.9869	High Similarity	NPC201800
0.9805	High Similarity	NPC186686
0.9803	High Similarity	NPC210459
0.9801	High Similarity	NPC195796
0.9801	High Similarity	NPC35038
0.9801	High Similarity	NPC278778
0.9801	High Similarity	NPC291878
0.9742	High Similarity	NPC293319
0.9739	High Similarity	NPC299436
0.9739	High Similarity	NPC321399
0.9737	High Similarity	NPC472598
0.9737	High Similarity	NPC27337
0.9737	High Similarity	NPC291508
0.9737	High Similarity	NPC474055
0.9735	High Similarity	NPC67396
0.9735	High Similarity	NPC477503
0.9735	High Similarity	NPC45849
0.9735	High Similarity	NPC200761
0.9735	High Similarity	NPC470327
0.9679	High Similarity	NPC43319
0.9673	High Similarity	NPC85121
0.9671	High Similarity	NPC24640
0.9671	High Similarity	NPC470328
0.9671	High Similarity	NPC209614
0.9671	High Similarity	NPC472626
0.9669	High Similarity	NPC192083
0.9669	High Similarity	NPC18727
0.9669	High Similarity	NPC213896
0.9618	High Similarity	NPC218226
0.9615	High Similarity	NPC326520
0.9615	High Similarity	NPC475888
0.9613	High Similarity	NPC211107
0.9613	High Similarity	NPC472964
0.961	High Similarity	NPC282009
0.961	High Similarity	NPC56085
0.961	High Similarity	NPC472624
0.961	High Similarity	NPC472902
0.961	High Similarity	NPC119209
0.961	High Similarity	NPC228785
0.961	High Similarity	NPC287328
0.961	High Similarity	NPC192686
0.961	High Similarity	NPC14353
0.961	High Similarity	NPC118256
0.9608	High Similarity	NPC136674
0.9608	High Similarity	NPC223787
0.9605	High Similarity	NPC321779
0.9605	High Similarity	NPC226025
0.9603	High Similarity	NPC302950
0.9603	High Similarity	NPC106976
0.9603	High Similarity	NPC219582
0.9603	High Similarity	NPC236637
0.9554	High Similarity	NPC170245
0.9551	High Similarity	NPC220313
0.9551	High Similarity	NPC7483
0.9551	High Similarity	NPC474240
0.9548	High Similarity	NPC474186
0.9548	High Similarity	NPC472634
0.9548	High Similarity	NPC471499
0.9548	High Similarity	NPC40491
0.9548	High Similarity	NPC26326
0.9548	High Similarity	NPC61010
0.9548	High Similarity	NPC472632
0.9548	High Similarity	NPC278052
0.9548	High Similarity	NPC471210
0.9548	High Similarity	NPC474187
0.9548	High Similarity	NPC474038
0.9545	High Similarity	NPC250214
0.9545	High Similarity	NPC235448
0.9545	High Similarity	NPC95936
0.9545	High Similarity	NPC22192
0.9545	High Similarity	NPC100123
0.9539	High Similarity	NPC74924
0.9539	High Similarity	NPC298692
0.9494	High Similarity	NPC477154
0.9494	High Similarity	NPC474024
0.9494	High Similarity	NPC6588
0.9494	High Similarity	NPC117854
0.949	High Similarity	NPC239752
0.949	High Similarity	NPC472450
0.949	High Similarity	NPC472277
0.949	High Similarity	NPC62261
0.949	High Similarity	NPC275780
0.9487	High Similarity	NPC474034
0.9487	High Similarity	NPC474150
0.9487	High Similarity	NPC474162
0.9487	High Similarity	NPC472635
0.9487	High Similarity	NPC474033
0.9487	High Similarity	NPC476247
0.9484	High Similarity	NPC472630
0.9484	High Similarity	NPC470326
0.9484	High Similarity	NPC174953
0.9484	High Similarity	NPC474960
0.9484	High Similarity	NPC471973
0.9484	High Similarity	NPC475784
0.9484	High Similarity	NPC475886
0.9484	High Similarity	NPC320359
0.9484	High Similarity	NPC472631
0.9484	High Similarity	NPC474287
0.9481	High Similarity	NPC162869
0.9481	High Similarity	NPC78225
0.9481	High Similarity	NPC284820
0.9481	High Similarity	NPC156057
0.9481	High Similarity	NPC471479
0.9481	High Similarity	NPC217677
0.9481	High Similarity	NPC300727
0.9481	High Similarity	NPC474208
0.9481	High Similarity	NPC471515
0.9481	High Similarity	NPC475267
0.9481	High Similarity	NPC474836
0.9481	High Similarity	NPC472963
0.9481	High Similarity	NPC165977
0.9481	High Similarity	NPC241904
0.9481	High Similarity	NPC471209
0.9481	High Similarity	NPC129684
0.9481	High Similarity	NPC299520
0.9481	High Similarity	NPC48208
0.9481	High Similarity	NPC473272
0.9477	High Similarity	NPC117992
0.9477	High Similarity	NPC230149
0.9477	High Similarity	NPC168247
0.9477	High Similarity	NPC57674
0.9477	High Similarity	NPC152951
0.9474	High Similarity	NPC471982
0.9474	High Similarity	NPC260979
0.9474	High Similarity	NPC472912
0.947	High Similarity	NPC338131
0.9437	High Similarity	NPC4200
0.943	High Similarity	NPC477517
0.943	High Similarity	NPC272502
0.943	High Similarity	NPC39091
0.9427	High Similarity	NPC152659
0.9427	High Similarity	NPC205265
0.9427	High Similarity	NPC124038
0.9427	High Similarity	NPC472281
0.9427	High Similarity	NPC18100
0.9427	High Similarity	NPC23298
0.9427	High Similarity	NPC236132
0.9427	High Similarity	NPC248638
0.9427	High Similarity	NPC472625
0.9427	High Similarity	NPC197168
0.9427	High Similarity	NPC236521
0.9427	High Similarity	NPC475985
0.9427	High Similarity	NPC189473
0.9423	High Similarity	NPC474351
0.9423	High Similarity	NPC471211
0.9423	High Similarity	NPC134783
0.9423	High Similarity	NPC475883
0.9423	High Similarity	NPC474239
0.9423	High Similarity	NPC32694
0.9423	High Similarity	NPC471212
0.9423	High Similarity	NPC266314
0.9423	High Similarity	NPC142252
0.9419	High Similarity	NPC117418
0.9419	High Similarity	NPC473990
0.9419	High Similarity	NPC476242
0.9419	High Similarity	NPC53545
0.9419	High Similarity	NPC329091
0.9416	High Similarity	NPC274730
0.9416	High Similarity	NPC471500
0.9416	High Similarity	NPC326037
0.9416	High Similarity	NPC320825
0.9416	High Similarity	NPC13858
0.9416	High Similarity	NPC191146
0.9416	High Similarity	NPC68093
0.9416	High Similarity	NPC235165
0.9416	High Similarity	NPC255106
0.9416	High Similarity	NPC142339
0.9416	High Similarity	NPC472907
0.9416	High Similarity	NPC227062
0.9412	High Similarity	NPC227337
0.9412	High Similarity	NPC273462
0.9412	High Similarity	NPC49402
0.9412	High Similarity	NPC70433
0.9412	High Similarity	NPC33051
0.9412	High Similarity	NPC469550
0.9412	High Similarity	NPC472905
0.9371	High Similarity	NPC150131
0.9367	High Similarity	NPC303174
0.9367	High Similarity	NPC473286
0.9367	High Similarity	NPC300053
0.9367	High Similarity	NPC108433
0.9367	High Similarity	NPC25361
0.9363	High Similarity	NPC229632
0.9363	High Similarity	NPC25152
0.9359	High Similarity	NPC328102
0.9359	High Similarity	NPC476283
0.9359	High Similarity	NPC235018
0.9359	High Similarity	NPC45146
0.9359	High Similarity	NPC470183
0.9355	High Similarity	NPC472910
0.9355	High Similarity	NPC52530
0.9355	High Similarity	NPC36852
0.9355	High Similarity	NPC236796
0.9355	High Similarity	NPC52889
0.9355	High Similarity	NPC96167
0.9355	High Similarity	NPC472914
0.9355	High Similarity	NPC245758
0.9355	High Similarity	NPC67876
0.9355	High Similarity	NPC99597
0.9355	High Similarity	NPC210084

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 NPC36217 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	368
0.1-0.2	935
0.2-0.3	1689
0.3-0.4	2609
0.4-0.5	1802
0.5-0.6	1005
0.6-0.7	520
0.7-0.8	163
0.8-0.85	33
0.85-0.9	20
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9669	High Similarity	NPD2393	Clinical (unspecified phase)
0.9603	High Similarity	NPD1934	Approved
0.9161	High Similarity	NPD2801	Approved
0.9125	High Similarity	NPD6166	Phase 2
0.9125	High Similarity	NPD6167	Clinical (unspecified phase)
0.9125	High Similarity	NPD6168	Clinical (unspecified phase)
0.8947	High Similarity	NPD1511	Approved
0.8924	High Similarity	NPD3882	Suspended
0.8902	High Similarity	NPD7074	Phase 3
0.8875	High Similarity	NPD5494	Approved
0.8846	High Similarity	NPD4380	Phase 2
0.8841	High Similarity	NPD7054	Approved
0.8831	High Similarity	NPD1512	Approved
0.8797	High Similarity	NPD7819	Suspended
0.8788	High Similarity	NPD7472	Approved
0.878	High Similarity	NPD3818	Discontinued
0.8766	High Similarity	NPD4378	Clinical (unspecified phase)
0.8765	High Similarity	NPD6232	Discontinued
0.875	High Similarity	NPD7075	Discontinued
0.8742	High Similarity	NPD3817	Phase 2
0.8727	High Similarity	NPD5844	Phase 1
0.872	High Similarity	NPD7473	Discontinued
0.8704	High Similarity	NPD6959	Discontinued
0.8688	High Similarity	NPD4868	Clinical (unspecified phase)
0.8679	High Similarity	NPD7096	Clinical (unspecified phase)
0.8675	High Similarity	NPD1552	Clinical (unspecified phase)
0.8675	High Similarity	NPD1550	Clinical (unspecified phase)
0.8625	High Similarity	NPD8443	Clinical (unspecified phase)
0.8623	High Similarity	NPD6797	Phase 2
0.8618	High Similarity	NPD1549	Phase 2
0.8571	High Similarity	NPD7251	Discontinued
0.8521	High Similarity	NPD7808	Phase 3
0.8521	High Similarity	NPD4338	Clinical (unspecified phase)
0.8519	High Similarity	NPD4381	Clinical (unspecified phase)
0.8447	Intermediate Similarity	NPD1465	Phase 2
0.8393	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD6801	Discontinued
0.8366	Intermediate Similarity	NPD2796	Approved
0.8323	Intermediate Similarity	NPD7411	Suspended
0.8301	Intermediate Similarity	NPD1510	Phase 2
0.8291	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8246	Intermediate Similarity	NPD6559	Discontinued
0.8228	Intermediate Similarity	NPD6799	Approved
0.8187	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD2534	Approved
0.8176	Intermediate Similarity	NPD2533	Approved
0.8176	Intermediate Similarity	NPD2532	Approved
0.8158	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD1240	Approved
0.8158	Intermediate Similarity	NPD1613	Approved
0.8148	Intermediate Similarity	NPD6599	Discontinued
0.8141	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD1607	Approved
0.8039	Intermediate Similarity	NPD943	Approved
0.8038	Intermediate Similarity	NPD3750	Approved
0.8036	Intermediate Similarity	NPD1247	Approved
0.8024	Intermediate Similarity	NPD6234	Discontinued
0.8024	Intermediate Similarity	NPD919	Approved
0.8023	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8022	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7768	Phase 2
0.7975	Intermediate Similarity	NPD2800	Approved
0.7964	Intermediate Similarity	NPD3749	Approved
0.7961	Intermediate Similarity	NPD3027	Phase 3
0.7952	Intermediate Similarity	NPD5402	Approved
0.7947	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD3926	Phase 2
0.7929	Intermediate Similarity	NPD7199	Phase 2
0.7898	Intermediate Similarity	NPD2935	Discontinued
0.7866	Intermediate Similarity	NPD3226	Approved
0.7862	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD5403	Approved
0.7848	Intermediate Similarity	NPD2346	Discontinued
0.7836	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7833	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD37	Approved
0.7812	Intermediate Similarity	NPD4628	Phase 3
0.7803	Intermediate Similarity	NPD7228	Approved
0.7803	Intermediate Similarity	NPD3751	Discontinued
0.7798	Intermediate Similarity	NPD4965	Approved
0.7798	Intermediate Similarity	NPD4966	Approved
0.7798	Intermediate Similarity	NPD4967	Phase 2
0.7785	Intermediate Similarity	NPD6099	Approved
0.7785	Intermediate Similarity	NPD6100	Approved
0.7778	Intermediate Similarity	NPD7390	Discontinued
0.7778	Intermediate Similarity	NPD3787	Discontinued
0.7756	Intermediate Similarity	NPD230	Phase 1
0.7753	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD8313	Approved
0.774	Intermediate Similarity	NPD8312	Approved
0.773	Intermediate Similarity	NPD5401	Approved
0.7722	Intermediate Similarity	NPD3748	Approved
0.7684	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD5711	Approved
0.7674	Intermediate Similarity	NPD5710	Approved
0.7673	Intermediate Similarity	NPD1551	Phase 2
0.7643	Intermediate Similarity	NPD447	Suspended
0.7636	Intermediate Similarity	NPD920	Approved
0.7622	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD4625	Phase 3
0.761	Intermediate Similarity	NPD2799	Discontinued
0.7595	Intermediate Similarity	NPD6651	Approved
0.759	Intermediate Similarity	NPD1653	Approved
0.7571	Intermediate Similarity	NPD5953	Discontinued
0.7561	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD7286	Phase 2
0.7554	Intermediate Similarity	NPD4360	Phase 2
0.7554	Intermediate Similarity	NPD4363	Phase 3
0.7548	Intermediate Similarity	NPD4908	Phase 1
0.7545	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD6782	Approved
0.754	Intermediate Similarity	NPD6777	Approved
0.754	Intermediate Similarity	NPD6780	Approved
0.754	Intermediate Similarity	NPD6776	Approved
0.754	Intermediate Similarity	NPD6779	Approved
0.754	Intermediate Similarity	NPD6781	Approved
0.754	Intermediate Similarity	NPD6778	Approved
0.7532	Intermediate Similarity	NPD1933	Approved
0.7531	Intermediate Similarity	NPD1243	Approved
0.7516	Intermediate Similarity	NPD2344	Approved
0.7515	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD8150	Discontinued
0.75	Intermediate Similarity	NPD8151	Discontinued
0.75	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD9494	Approved
0.7471	Intermediate Similarity	NPD7229	Phase 3
0.7468	Intermediate Similarity	NPD4060	Phase 1
0.7452	Intermediate Similarity	NPD2313	Discontinued
0.7451	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD6190	Approved
0.7434	Intermediate Similarity	NPD1610	Phase 2
0.7434	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD7685	Pre-registration
0.7423	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7435	Discontinued
0.7418	Intermediate Similarity	NPD8434	Phase 2
0.741	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2309	Approved
0.7333	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7240	Approved
0.7333	Intermediate Similarity	NPD7783	Phase 2
0.733	Intermediate Similarity	NPD7697	Approved
0.733	Intermediate Similarity	NPD5242	Approved
0.733	Intermediate Similarity	NPD7696	Phase 3
0.733	Intermediate Similarity	NPD7698	Approved
0.732	Intermediate Similarity	NPD1201	Approved
0.7317	Intermediate Similarity	NPD6674	Discontinued
0.7306	Intermediate Similarity	NPD7584	Approved
0.7292	Intermediate Similarity	NPD7870	Phase 2
0.7292	Intermediate Similarity	NPD7871	Phase 2
0.7284	Intermediate Similarity	NPD7033	Discontinued
0.7277	Intermediate Similarity	NPD6823	Phase 2
0.7273	Intermediate Similarity	NPD6535	Approved
0.7273	Intermediate Similarity	NPD6534	Approved
0.7268	Intermediate Similarity	NPD7701	Phase 2
0.7267	Intermediate Similarity	NPD8455	Phase 2
0.7261	Intermediate Similarity	NPD2861	Phase 2
0.7256	Intermediate Similarity	NPD2424	Discontinued
0.7244	Intermediate Similarity	NPD1470	Approved
0.7244	Intermediate Similarity	NPD1203	Approved
0.7239	Intermediate Similarity	NPD5404	Approved
0.7239	Intermediate Similarity	NPD5405	Approved
0.7239	Intermediate Similarity	NPD5406	Approved
0.7239	Intermediate Similarity	NPD5408	Approved
0.7235	Intermediate Similarity	NPD7458	Discontinued
0.7234	Intermediate Similarity	NPD4361	Phase 2
0.7234	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD3268	Approved
0.7233	Intermediate Similarity	NPD6798	Discontinued
0.7225	Intermediate Similarity	NPD2494	Approved
0.7225	Intermediate Similarity	NPD5353	Approved
0.7225	Intermediate Similarity	NPD2493	Approved
0.7216	Intermediate Similarity	NPD8127	Discontinued
0.7215	Intermediate Similarity	NPD6832	Phase 2
0.7205	Intermediate Similarity	NPD5124	Phase 1
0.7205	Intermediate Similarity	NPD6355	Discontinued
0.7205	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD2798	Approved
0.7194	Intermediate Similarity	NPD7874	Approved
0.7194	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1548	Phase 1
0.7161	Intermediate Similarity	NPD1608	Approved
0.716	Intermediate Similarity	NPD6273	Approved
0.7158	Intermediate Similarity	NPD7699	Phase 2
0.7158	Intermediate Similarity	NPD7700	Phase 2
0.7157	Intermediate Similarity	NPD7801	Approved
0.7135	Intermediate Similarity	NPD3450	Approved
0.7135	Intermediate Similarity	NPD3452	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