NPASS Compound

Structure

NPC62261 OpenBabel07101718312D 25 28 0 0 1 0 0 0 0 0999 V2000 4.3301 -0.5000 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 -1.7321 -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 -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 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 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 -0.0000 1.0000 0.0000 C 0 0 2 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 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 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 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 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 23 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 9 1 0 0 0 0 5 10 2 0 0 0 0 6 11 2 0 0 0 0 6 12 1 0 0 0 0 7 13 1 0 0 0 0 7 24 1 0 0 0 0 8 11 1 0 0 0 0 8 15 2 0 0 0 0 9 16 2 0 0 0 0 9 18 1 0 0 0 0 10 16 1 0 0 0 0 10 19 1 0 0 0 0 11 23 1 0 0 0 0 12 14 2 0 0 0 0 12 25 1 0 0 0 0 13 18 1 1 0 0 0 13 25 1 0 0 0 0 14 15 1 0 0 0 0 14 17 1 0 0 0 0 15 20 1 0 0 0 0 16 24 1 0 0 0 0 17 18 1 0 0 0 0 17 21 2 0 0 0 0 18 22 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	344.09
Volume:	328.735
LogP:	2.808
LogD:	2.323
LogS:	-3.712
# Rotatable Bonds:	1
TPSA:	105.45
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.722
Synthetic Accessibility Score:	3.728
Fsp3:	0.278
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.266
MDCK Permeability:	9.35483149078209e-06
Pgp-inhibitor:	0.012
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.051
Plasma Protein Binding (PPB):	96.8261489868164%
Volume Distribution (VD):	0.724
Pgp-substrate:	5.184964179992676%

ADMET: Metabolism

CYP1A2-inhibitor:	0.815
CYP1A2-substrate:	0.836
CYP2C19-inhibitor:	0.597
CYP2C19-substrate:	0.651
CYP2C9-inhibitor:	0.642
CYP2C9-substrate:	0.527
CYP2D6-inhibitor:	0.417
CYP2D6-substrate:	0.301
CYP3A4-inhibitor:	0.553
CYP3A4-substrate:	0.623

ADMET: Excretion

Clearance (CL):	8.273
Half-life (T1/2):	0.389

ADMET: Toxicity

hERG Blockers:	0.052
Human Hepatotoxicity (H-HT):	0.383
Drug-inuced Liver Injury (DILI):	0.493
AMES Toxicity:	0.182
Rat Oral Acute Toxicity:	0.417
Maximum Recommended Daily Dose:	0.128
Skin Sensitization:	0.91
Carcinogencity:	0.613
Eye Corrosion:	0.003
Eye Irritation:	0.722
Respiratory Toxicity:	0.029

Download Data

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

Natural Product: NPC62261

Natural Product ID:	NPC62261
*Common Name:**	Boeravinone C
IUPAC Name:	(6aR,12aS)-4,11,12a-trihydroxy-9-methoxy-10-methyl-6,6a-dihydrochromeno[3,4-b]chromen-12-one
Synonyms:	Boeravinone C
Standard InCHIKey:	ZVSXALWTWGTZSP-ACJLOTCBSA-N
Standard InCHI:	InChI=1S/C18H16O7/c1-8-11(23-2)6-12-14(15(8)20)17(21)18(22)9-4-3-5-10(19)16(9)24-7-13(18)25-12/h3-6,13,19-20,22H,7H2,1-2H3/t13-,18+/m1/s1
SMILES:	COc1cc2O[C@@H]3COc4c([C@]3(C(=O)c2c(c1C)O)O)cccc4O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL426722
PubChem CID:	13940642
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0001607] Rotenoids [CHEMONTID:0003528] Rotenones

*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
NPO33416	boerhaavia diffusa	Species	n.a.	n.a.	roots	n.a.	n.a.	PMID[16792408]
NPO33416	boerhaavia diffusa	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[23914900]

☑ 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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1422	Individual Protein	ATP-binding cassette sub-family G member 2	Homo sapiens	Activity	=	31.0	%	PMID[482624]

☑ 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 NPC62261 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	422
0.1-0.2	1754
0.2-0.3	4285
0.3-0.4	10279
0.4-0.5	7589
0.5-0.6	3544
0.6-0.7	4825
0.7-0.8	5388
0.8-0.85	2668
0.85-0.9	1554
0.9-0.95	355
0.95-1	34

Similarity Score	Similarity Level	Natural Product ID
0.9806	High Similarity	NPC173137
0.9745	High Similarity	NPC224280
0.9684	High Similarity	NPC471213
0.9682	High Similarity	NPC472625
0.9679	High Similarity	NPC472632
0.9679	High Similarity	NPC134783
0.9679	High Similarity	NPC471210
0.962	High Similarity	NPC234052
0.962	High Similarity	NPC293319
0.9618	High Similarity	NPC474033
0.9618	High Similarity	NPC474034
0.9618	High Similarity	NPC474150
0.9618	High Similarity	NPC474162
0.9615	High Similarity	NPC287328
0.9615	High Similarity	NPC282009
0.9615	High Similarity	NPC119209
0.9615	High Similarity	NPC118256
0.9615	High Similarity	NPC192686
0.9615	High Similarity	NPC174953
0.9613	High Similarity	NPC27337
0.9613	High Similarity	NPC471209
0.9568	High Similarity	NPC108202
0.9563	High Similarity	NPC152477
0.9563	High Similarity	NPC177480
0.956	High Similarity	NPC477517
0.9557	High Similarity	NPC41301
0.9557	High Similarity	NPC186686
0.9554	High Similarity	NPC474038
0.9554	High Similarity	NPC471212
0.9554	High Similarity	NPC471499
0.9554	High Similarity	NPC471211
0.9551	High Similarity	NPC55738
0.9551	High Similarity	NPC22192
0.9551	High Similarity	NPC473990
0.9548	High Similarity	NPC291878
0.9548	High Similarity	NPC278778
0.9548	High Similarity	NPC195796
0.9548	High Similarity	NPC35038
0.95	High Similarity	NPC117854
0.95	High Similarity	NPC477154
0.95	High Similarity	NPC8965
0.95	High Similarity	NPC6588
0.949	High Similarity	NPC470326
0.949	High Similarity	NPC472624
0.949	High Similarity	NPC36217
0.949	High Similarity	NPC475784
0.949	High Similarity	NPC470183
0.9487	High Similarity	NPC472598
0.9487	High Similarity	NPC284820
0.9487	High Similarity	NPC471479
0.9487	High Similarity	NPC474055
0.9487	High Similarity	NPC471515
0.9487	High Similarity	NPC291508
0.9487	High Similarity	NPC67876
0.9487	High Similarity	NPC473272
0.9484	High Similarity	NPC477503
0.9484	High Similarity	NPC470327
0.9484	High Similarity	NPC45849
0.9484	High Similarity	NPC200761
0.9444	High Similarity	NPC121333
0.9441	High Similarity	NPC165456
0.9441	High Similarity	NPC242395
0.9441	High Similarity	NPC288813
0.9441	High Similarity	NPC326877
0.9437	High Similarity	NPC43319
0.9437	High Similarity	NPC120593
0.9434	High Similarity	NPC248638
0.9434	High Similarity	NPC236521
0.9434	High Similarity	NPC124038
0.9434	High Similarity	NPC152659
0.943	High Similarity	NPC289771
0.943	High Similarity	NPC472634
0.943	High Similarity	NPC26326
0.9427	High Similarity	NPC250214
0.9427	High Similarity	NPC152904
0.9427	High Similarity	NPC95936
0.9427	High Similarity	NPC204879
0.9423	High Similarity	NPC472626
0.9423	High Similarity	NPC470328
0.9423	High Similarity	NPC209614
0.9423	High Similarity	NPC13858
0.9423	High Similarity	NPC471500
0.9423	High Similarity	NPC474638
0.9423	High Similarity	NPC326037
0.9423	High Similarity	NPC320825
0.9423	High Similarity	NPC470600
0.9419	High Similarity	NPC192083
0.9419	High Similarity	NPC74924
0.9419	High Similarity	NPC18727
0.9419	High Similarity	NPC213896
0.9383	High Similarity	NPC102277
0.9383	High Similarity	NPC279209
0.9383	High Similarity	NPC74559
0.9379	High Similarity	NPC474024
0.9379	High Similarity	NPC150131
0.9379	High Similarity	NPC218226
0.9375	High Similarity	NPC58223
0.9375	High Similarity	NPC7688
0.9375	High Similarity	NPC7154
0.9375	High Similarity	NPC36916
0.9375	High Similarity	NPC36
0.9375	High Similarity	NPC300053
0.9375	High Similarity	NPC472450
0.9375	High Similarity	NPC239752
0.9375	High Similarity	NPC108433
0.9375	High Similarity	NPC472277
0.9375	High Similarity	NPC475888
0.9375	High Similarity	NPC72787
0.9375	High Similarity	NPC125039
0.9375	High Similarity	NPC275780
0.9371	High Similarity	NPC472448
0.9371	High Similarity	NPC472635
0.9371	High Similarity	NPC476247
0.9371	High Similarity	NPC83922
0.9371	High Similarity	NPC25152
0.9371	High Similarity	NPC211107
0.9371	High Similarity	NPC201800
0.9371	High Similarity	NPC78332
0.9367	High Similarity	NPC472630
0.9367	High Similarity	NPC263449
0.9367	High Similarity	NPC471973
0.9367	High Similarity	NPC204290
0.9367	High Similarity	NPC472631
0.9363	High Similarity	NPC52889
0.9363	High Similarity	NPC129684
0.9363	High Similarity	NPC162869
0.9363	High Similarity	NPC156057
0.9363	High Similarity	NPC48208
0.9363	High Similarity	NPC136674
0.9363	High Similarity	NPC78225
0.9363	High Similarity	NPC474681
0.9363	High Similarity	NPC474208
0.9363	High Similarity	NPC218313
0.9363	High Similarity	NPC52530
0.9363	High Similarity	NPC299520
0.9363	High Similarity	NPC223787
0.9363	High Similarity	NPC474836
0.9363	High Similarity	NPC475267
0.9359	High Similarity	NPC226025
0.9359	High Similarity	NPC117992
0.9359	High Similarity	NPC168247
0.9359	High Similarity	NPC321779
0.9359	High Similarity	NPC152951
0.9359	High Similarity	NPC57674
0.9359	High Similarity	NPC230149
0.9359	High Similarity	NPC256925
0.9359	High Similarity	NPC476169
0.9355	High Similarity	NPC210597
0.9355	High Similarity	NPC219582
0.9355	High Similarity	NPC236637
0.9355	High Similarity	NPC106976
0.9355	High Similarity	NPC302950
0.9325	High Similarity	NPC186847
0.9325	High Similarity	NPC257667
0.9325	High Similarity	NPC472454
0.9317	High Similarity	NPC235610
0.9317	High Similarity	NPC170245
0.9317	High Similarity	NPC39091
0.9317	High Similarity	NPC472449
0.9317	High Similarity	NPC173292
0.9313	High Similarity	NPC273959
0.9313	High Similarity	NPC205265
0.9313	High Similarity	NPC472281
0.9313	High Similarity	NPC474240
0.9313	High Similarity	NPC189473
0.9313	High Similarity	NPC18100
0.9313	High Similarity	NPC23298
0.9308	High Similarity	NPC61010
0.9308	High Similarity	NPC142252
0.9308	High Similarity	NPC57715
0.9308	High Similarity	NPC29876
0.9308	High Similarity	NPC234644
0.9308	High Similarity	NPC167678
0.9308	High Similarity	NPC266314
0.9308	High Similarity	NPC308992
0.9304	High Similarity	NPC184755
0.9304	High Similarity	NPC210459
0.9304	High Similarity	NPC117418
0.9304	High Similarity	NPC53545
0.9304	High Similarity	NPC74178
0.9299	High Similarity	NPC471985
0.9299	High Similarity	NPC6633
0.9299	High Similarity	NPC472455
0.9299	High Similarity	NPC303255
0.9299	High Similarity	NPC191146
0.9299	High Similarity	NPC255106
0.9299	High Similarity	NPC146636
0.9299	High Similarity	NPC235165
0.9299	High Similarity	NPC68093
0.9299	High Similarity	NPC250922
0.9299	High Similarity	NPC24640
0.9299	High Similarity	NPC133970
0.9299	High Similarity	NPC5322
0.9295	High Similarity	NPC227337
0.9295	High Similarity	NPC203080
0.9295	High Similarity	NPC209760
0.9295	High Similarity	NPC141212
0.9295	High Similarity	NPC49402
0.9295	High Similarity	NPC273462
0.9295	High Similarity	NPC70433

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 NPC62261 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	396
0.1-0.2	948
0.2-0.3	1819
0.3-0.4	2614
0.4-0.5	1774
0.5-0.6	977
0.6-0.7	432
0.7-0.8	142
0.8-0.85	31
0.85-0.9	11
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9419	High Similarity	NPD2393	Clinical (unspecified phase)
0.9375	High Similarity	NPD6168	Clinical (unspecified phase)
0.9375	High Similarity	NPD6167	Clinical (unspecified phase)
0.9375	High Similarity	NPD6166	Phase 2
0.9355	High Similarity	NPD1934	Approved
0.9057	High Similarity	NPD3882	Suspended
0.9051	High Similarity	NPD2801	Approved
0.9006	High Similarity	NPD5494	Approved
0.8916	High Similarity	NPD7074	Phase 3
0.8862	High Similarity	NPD6797	Phase 2
0.8855	High Similarity	NPD7054	Approved
0.8846	High Similarity	NPD1512	Approved
0.881	High Similarity	NPD7251	Discontinued
0.8802	High Similarity	NPD7472	Approved
0.8782	High Similarity	NPD4378	Clinical (unspecified phase)
0.8765	High Similarity	NPD7075	Discontinued
0.8758	High Similarity	NPD3817	Phase 2
0.8757	High Similarity	NPD7808	Phase 3
0.8757	High Similarity	NPD4338	Clinical (unspecified phase)
0.8742	High Similarity	NPD4380	Phase 2
0.8718	High Similarity	NPD1511	Approved
0.8704	High Similarity	NPD4868	Clinical (unspecified phase)
0.8696	High Similarity	NPD7096	Clinical (unspecified phase)
0.8683	High Similarity	NPD3818	Discontinued
0.8631	High Similarity	NPD7804	Clinical (unspecified phase)
0.8529	High Similarity	NPD7993	Clinical (unspecified phase)
0.8528	High Similarity	NPD8443	Clinical (unspecified phase)
0.8494	Intermediate Similarity	NPD6959	Discontinued
0.8452	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8443	Intermediate Similarity	NPD6232	Discontinued
0.8424	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8412	Intermediate Similarity	NPD5844	Phase 1
0.8405	Intermediate Similarity	NPD6801	Discontinued
0.8402	Intermediate Similarity	NPD7473	Discontinued
0.8397	Intermediate Similarity	NPD1549	Phase 2
0.8354	Intermediate Similarity	NPD7819	Suspended
0.8354	Intermediate Similarity	NPD1465	Phase 2
0.8313	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD6799	Approved
0.8232	Intermediate Similarity	NPD7411	Suspended
0.8193	Intermediate Similarity	NPD5402	Approved
0.8171	Intermediate Similarity	NPD6599	Discontinued
0.8166	Intermediate Similarity	NPD1247	Approved
0.8153	Intermediate Similarity	NPD2796	Approved
0.8089	Intermediate Similarity	NPD1510	Phase 2
0.807	Intermediate Similarity	NPD3926	Phase 2
0.8057	Intermediate Similarity	NPD6559	Discontinued
0.8047	Intermediate Similarity	NPD919	Approved
0.8023	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD5403	Approved
0.7978	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD1240	Approved
0.7949	Intermediate Similarity	NPD943	Approved
0.7949	Intermediate Similarity	NPD1613	Approved
0.7949	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD3751	Discontinued
0.7929	Intermediate Similarity	NPD7768	Phase 2
0.7907	Intermediate Similarity	NPD3787	Discontinued
0.7888	Intermediate Similarity	NPD2800	Approved
0.7882	Intermediate Similarity	NPD3749	Approved
0.7866	Intermediate Similarity	NPD2532	Approved
0.7866	Intermediate Similarity	NPD2534	Approved
0.7866	Intermediate Similarity	NPD5401	Approved
0.7866	Intermediate Similarity	NPD2533	Approved
0.7848	Intermediate Similarity	NPD1607	Approved
0.7845	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD3027	Phase 3
0.7754	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD6234	Discontinued
0.773	Intermediate Similarity	NPD3750	Approved
0.7727	Intermediate Similarity	NPD7228	Approved
0.7716	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD2935	Discontinued
0.7683	Intermediate Similarity	NPD6190	Approved
0.7673	Intermediate Similarity	NPD230	Phase 1
0.7669	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD8312	Approved
0.7667	Intermediate Similarity	NPD8313	Approved
0.766	Intermediate Similarity	NPD6782	Approved
0.766	Intermediate Similarity	NPD6781	Approved
0.766	Intermediate Similarity	NPD6778	Approved
0.766	Intermediate Similarity	NPD6777	Approved
0.766	Intermediate Similarity	NPD6780	Approved
0.766	Intermediate Similarity	NPD6779	Approved
0.766	Intermediate Similarity	NPD6776	Approved
0.7657	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7637	Intermediate Similarity	NPD8150	Discontinued
0.7622	Intermediate Similarity	NPD4628	Phase 3
0.7595	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD6100	Approved
0.7593	Intermediate Similarity	NPD6099	Approved
0.7574	Intermediate Similarity	NPD3226	Approved
0.7562	Intermediate Similarity	NPD447	Suspended
0.756	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD920	Approved
0.7556	Intermediate Similarity	NPD7685	Pre-registration
0.7546	Intermediate Similarity	NPD2346	Discontinued
0.7544	Intermediate Similarity	NPD37	Approved
0.7543	Intermediate Similarity	NPD7199	Phase 2
0.7541	Intermediate Similarity	NPD8434	Phase 2
0.7539	Intermediate Similarity	NPD7696	Phase 3
0.7539	Intermediate Similarity	NPD7697	Approved
0.7539	Intermediate Similarity	NPD7435	Discontinued
0.7539	Intermediate Similarity	NPD7698	Approved
0.7531	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD2799	Discontinued
0.7514	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD4966	Approved
0.7514	Intermediate Similarity	NPD4967	Phase 2
0.7514	Intermediate Similarity	NPD4965	Approved
0.75	Intermediate Similarity	NPD5953	Discontinued
0.75	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD4363	Phase 3
0.7487	Intermediate Similarity	NPD4360	Phase 2
0.7486	Intermediate Similarity	NPD7286	Phase 2
0.7485	Intermediate Similarity	NPD1551	Phase 2
0.7485	Intermediate Similarity	NPD7390	Discontinued
0.7484	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD7701	Phase 2
0.7468	Intermediate Similarity	NPD4908	Phase 1
0.744	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD2344	Approved
0.7436	Intermediate Similarity	NPD8151	Discontinued
0.7423	Intermediate Similarity	NPD3748	Approved
0.7412	Intermediate Similarity	NPD1653	Approved
0.741	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD7871	Phase 2
0.7409	Intermediate Similarity	NPD7870	Phase 2
0.7407	Intermediate Similarity	NPD6651	Approved
0.7405	Intermediate Similarity	NPD9494	Approved
0.7401	Intermediate Similarity	NPD5710	Approved
0.7401	Intermediate Similarity	NPD5711	Approved
0.7394	Intermediate Similarity	NPD6535	Approved
0.7394	Intermediate Similarity	NPD6534	Approved
0.7381	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD2313	Discontinued
0.7368	Intermediate Similarity	NPD7699	Phase 2
0.7368	Intermediate Similarity	NPD7700	Phase 2
0.736	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD7783	Phase 2
0.7349	Intermediate Similarity	NPD1243	Approved
0.7346	Intermediate Similarity	NPD1933	Approved
0.7344	Intermediate Similarity	NPD2493	Approved
0.7344	Intermediate Similarity	NPD2494	Approved
0.7337	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7584	Approved
0.7321	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD2403	Approved
0.7312	Intermediate Similarity	NPD4625	Phase 3
0.731	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7874	Approved
0.7305	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD8455	Phase 2
0.7289	Intermediate Similarity	NPD2424	Discontinued
0.7284	Intermediate Similarity	NPD4060	Phase 1
0.7283	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7801	Approved
0.7268	Intermediate Similarity	NPD7240	Approved
0.7267	Intermediate Similarity	NPD6798	Discontinued
0.7267	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD5242	Approved
0.7262	Intermediate Similarity	NPD2309	Approved
0.7261	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD3452	Approved
0.7254	Intermediate Similarity	NPD3450	Approved
0.7244	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1610	Phase 2
0.7239	Intermediate Similarity	NPD6355	Discontinued
0.7239	Intermediate Similarity	NPD5124	Phase 1
0.7239	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD8320	Phase 1
0.7231	Intermediate Similarity	NPD4583	Approved
0.7231	Intermediate Similarity	NPD4582	Approved
0.7231	Intermediate Similarity	NPD8319	Approved
0.7216	Intermediate Similarity	NPD6823	Phase 2
0.7212	Intermediate Similarity	NPD7033	Discontinued
0.7207	Intermediate Similarity	NPD7229	Phase 3
0.7206	Intermediate Similarity	NPD7907	Approved
0.7192	Intermediate Similarity	NPD4111	Phase 1
0.7192	Intermediate Similarity	NPD4665	Approved
0.7179	Intermediate Similarity	NPD4002	Approved
0.7179	Intermediate Similarity	NPD4004	Approved
0.7168	Intermediate Similarity	NPD7458	Discontinued
0.7159	Intermediate Similarity	NPD5353	Approved
0.7143	Intermediate Similarity	NPD6844	Discontinued
0.7135	Intermediate Similarity	NPD2973	Approved
0.7135	Intermediate Similarity	NPD2975	Approved
0.7135	Intermediate Similarity	NPD2974	Approved
0.7126	Intermediate Similarity	NPD7266	Discontinued
0.7117	Intermediate Similarity	NPD6233	Phase 2
0.7083	Intermediate Similarity	NPD4361	Phase 2
0.7083	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD2861	Phase 2
0.7063	Intermediate Similarity	NPD1203	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