NPASS Compound

Structure

NPC136641 OpenBabel07101718332D 25 28 0 0 1 0 0 0 0 0999 V2000 -3.8480 -0.9695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 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 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2007 -0.4343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0827 -3.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8698 -1.1774 0.0000 C 0 0 1 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 -1.5827 -2.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2226 -0.6422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 -1.5933 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 -2.5608 -2.1285 0.0000 C 0 0 2 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 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 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 -0.5534 0.1009 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2300 -2.8716 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1045 -2.9945 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 2 20 1 0 0 0 0 3 20 1 0 0 0 0 4 5 2 0 0 0 0 4 11 1 0 0 0 0 5 13 1 0 0 0 0 6 7 2 0 0 0 0 6 11 1 0 0 0 0 7 20 1 0 0 0 0 8 10 1 0 0 0 0 8 14 1 0 0 0 0 9 12 2 0 0 0 0 9 24 1 0 0 0 0 10 1 1 1 0 0 0 10 17 1 0 0 0 0 11 18 2 0 0 0 0 12 15 1 0 0 0 0 12 17 1 0 0 0 0 13 16 2 0 0 0 0 13 21 1 0 0 0 0 14 15 1 0 0 0 0 14 22 2 0 0 0 0 15 19 2 0 0 0 0 16 18 1 0 0 0 0 16 19 1 0 0 0 0 17 23 1 6 0 0 0 18 25 1 0 0 0 0 19 24 1 0 0 0 0 20 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	340.13
Volume:	345.746
LogP:	3.615
LogD:	3.49
LogS:	-4.045
# Rotatable Bonds:	1
TPSA:	79.9
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.817
Synthetic Accessibility Score:	4.14
Fsp3:	0.35
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.776
MDCK Permeability:	2.0826939362450503e-05
Pgp-inhibitor:	0.016
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.147
Plasma Protein Binding (PPB):	97.10620880126953%
Volume Distribution (VD):	0.589
Pgp-substrate:	3.249230146408081%

ADMET: Metabolism

CYP1A2-inhibitor:	0.722
CYP1A2-substrate:	0.469
CYP2C19-inhibitor:	0.419
CYP2C19-substrate:	0.139
CYP2C9-inhibitor:	0.728
CYP2C9-substrate:	0.816
CYP2D6-inhibitor:	0.846
CYP2D6-substrate:	0.328
CYP3A4-inhibitor:	0.705
CYP3A4-substrate:	0.193

ADMET: Excretion

Clearance (CL):	2.989
Half-life (T1/2):	0.131

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.779
Drug-inuced Liver Injury (DILI):	0.885
AMES Toxicity:	0.091
Rat Oral Acute Toxicity:	0.944
Maximum Recommended Daily Dose:	0.584
Skin Sensitization:	0.133
Carcinogencity:	0.891
Eye Corrosion:	0.003
Eye Irritation:	0.027
Respiratory Toxicity:	0.937

Download Data

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

Natural Product: NPC136641

Natural Product ID:	NPC136641
*Common Name:**	Massarinin B
IUPAC Name:	(6S,7R)-7-hydroxy-3-(7-hydroxy-2,2-dimethylchromen-8-yl)-6-methyl-6,7-dihydro-5H-2-benzofuran-4-one
Synonyms:
Standard InCHIKey:	SRUGXOLNOMJETJ-DYZYQPBXSA-N
Standard InCHI:	InChI=1S/C20H20O5/c1-10-8-14(22)15-12(17(10)23)9-24-19(15)16-13(21)5-4-11-6-7-20(2,3)25-18(11)16/h4-7,9-10,17,21,23H,8H2,1-3H3/t10-,17+/m0/s1
SMILES:	C[C@H]1CC(=O)c2c(coc2c2c(ccc3C=CC(C)(C)Oc23)O)[C@@H]1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL510291
PubChem CID:	10382606
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0003522] 2,2-dimethyl-1-benzopyrans

*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
NPO32853	massarina tunicata	Species	Massarinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10096869]
NPO32853	massarina tunicata	Species	Massarinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12542349]

☑ 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
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	23.0	mm	PMID[502815]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	12.0	mm	PMID[502815]

☑ 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 NPC136641 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	389
0.1-0.2	1582
0.2-0.3	3313
0.3-0.4	8517
0.4-0.5	10409
0.5-0.6	4056
0.6-0.7	5461
0.7-0.8	5880
0.8-0.85	2319
0.85-0.9	749
0.9-0.95	21
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9427	High Similarity	NPC476350
0.9427	High Similarity	NPC476349
0.9419	High Similarity	NPC158261
0.9419	High Similarity	NPC42458
0.9363	High Similarity	NPC296957
0.9363	High Similarity	NPC260902
0.9299	High Similarity	NPC247677
0.9299	High Similarity	NPC160015
0.9119	High Similarity	NPC268360
0.9119	High Similarity	NPC65504
0.9108	High Similarity	NPC67654
0.9074	High Similarity	NPC100849
0.9068	High Similarity	NPC472346
0.9062	High Similarity	NPC40583
0.9051	High Similarity	NPC472462
0.9051	High Similarity	NPC122365
0.9051	High Similarity	NPC213608
0.9051	High Similarity	NPC1477
0.9045	High Similarity	NPC156244
0.9038	High Similarity	NPC317492
0.9	High Similarity	NPC269495
0.9	High Similarity	NPC212967
0.9	High Similarity	NPC44199
0.9	High Similarity	NPC96342
0.9	High Similarity	NPC164110
0.9	High Similarity	NPC246647
0.8994	High Similarity	NPC99199
0.8994	High Similarity	NPC148938
0.8987	High Similarity	NPC5871
0.8981	High Similarity	NPC476185
0.8981	High Similarity	NPC29777
0.8981	High Similarity	NPC471115
0.8981	High Similarity	NPC321896
0.8974	High Similarity	NPC168085
0.8951	High Similarity	NPC74854
0.8951	High Similarity	NPC30655
0.8951	High Similarity	NPC45124
0.8944	High Similarity	NPC472877
0.8938	High Similarity	NPC180924
0.8931	High Similarity	NPC210942
0.8931	High Similarity	NPC235333
0.8931	High Similarity	NPC72370
0.8931	High Similarity	NPC169990
0.8924	High Similarity	NPC170169
0.8924	High Similarity	NPC471675
0.8917	High Similarity	NPC5173
0.8917	High Similarity	NPC226644
0.8917	High Similarity	NPC37226
0.8917	High Similarity	NPC221868
0.8917	High Similarity	NPC37208
0.8917	High Similarity	NPC39929
0.8917	High Similarity	NPC296030
0.891	High Similarity	NPC308200
0.8909	High Similarity	NPC476459
0.8903	High Similarity	NPC224714
0.8896	High Similarity	NPC193998
0.8889	High Similarity	NPC115432
0.8889	High Similarity	NPC260296
0.8889	High Similarity	NPC49009
0.8889	High Similarity	NPC470810
0.8875	High Similarity	NPC297531
0.8875	High Similarity	NPC198490
0.8875	High Similarity	NPC213936
0.8868	High Similarity	NPC263676
0.8868	High Similarity	NPC87708
0.8868	High Similarity	NPC327269
0.8868	High Similarity	NPC285623
0.8868	High Similarity	NPC207624
0.8868	High Similarity	NPC31627
0.8868	High Similarity	NPC476238
0.8862	High Similarity	NPC472584
0.8861	High Similarity	NPC61258
0.8861	High Similarity	NPC472633
0.8861	High Similarity	NPC78335
0.8861	High Similarity	NPC37348
0.8861	High Similarity	NPC230713
0.8854	High Similarity	NPC145467
0.8854	High Similarity	NPC135325
0.8854	High Similarity	NPC272194
0.8854	High Similarity	NPC39195
0.8848	High Similarity	NPC53640
0.8846	High Similarity	NPC73320
0.8846	High Similarity	NPC472629
0.8841	High Similarity	NPC155640
0.8841	High Similarity	NPC38591
0.8834	High Similarity	NPC14822
0.8827	High Similarity	NPC244750
0.8827	High Similarity	NPC226287
0.882	High Similarity	NPC474386
0.882	High Similarity	NPC164427
0.8812	High Similarity	NPC329844
0.8812	High Similarity	NPC183874
0.8812	High Similarity	NPC193200
0.8805	High Similarity	NPC23668
0.8805	High Similarity	NPC474744
0.8805	High Similarity	NPC115324
0.8805	High Similarity	NPC470675
0.8805	High Similarity	NPC232645
0.8805	High Similarity	NPC472636
0.8805	High Similarity	NPC149526
0.8805	High Similarity	NPC193976
0.8805	High Similarity	NPC290671
0.8805	High Similarity	NPC474772
0.8805	High Similarity	NPC473131
0.8805	High Similarity	NPC116604
0.8805	High Similarity	NPC72958
0.8805	High Similarity	NPC474417
0.8805	High Similarity	NPC58668
0.8805	High Similarity	NPC106372
0.8805	High Similarity	NPC472423
0.8802	High Similarity	NPC120220
0.8802	High Similarity	NPC131866
0.8797	High Similarity	NPC473016
0.8797	High Similarity	NPC100985
0.8797	High Similarity	NPC65589
0.8797	High Similarity	NPC470461
0.8797	High Similarity	NPC471114
0.8797	High Similarity	NPC97028
0.8797	High Similarity	NPC65775
0.8797	High Similarity	NPC97029
0.8797	High Similarity	NPC178202
0.8797	High Similarity	NPC158338
0.8797	High Similarity	NPC10027
0.8797	High Similarity	NPC288036
0.879	High Similarity	NPC130581
0.879	High Similarity	NPC473077
0.879	High Similarity	NPC12148
0.879	High Similarity	NPC296998
0.8788	High Similarity	NPC474591
0.8782	High Similarity	NPC271288
0.8782	High Similarity	NPC470890
0.8782	High Similarity	NPC124780
0.8782	High Similarity	NPC234629
0.8782	High Similarity	NPC131568
0.8782	High Similarity	NPC311144
0.8782	High Similarity	NPC311741
0.8782	High Similarity	NPC131579
0.8782	High Similarity	NPC87486
0.878	High Similarity	NPC472402
0.878	High Similarity	NPC219861
0.8773	High Similarity	NPC95472
0.8773	High Similarity	NPC239270
0.8773	High Similarity	NPC169
0.8773	High Similarity	NPC303210
0.8773	High Similarity	NPC304839
0.8773	High Similarity	NPC220582
0.8765	High Similarity	NPC282390
0.8765	High Similarity	NPC270044
0.8765	High Similarity	NPC281137
0.8765	High Similarity	NPC196448
0.8758	High Similarity	NPC474542
0.875	High Similarity	NPC130015
0.875	High Similarity	NPC154683
0.875	High Similarity	NPC40356
0.875	High Similarity	NPC142308
0.875	High Similarity	NPC38361
0.875	High Similarity	NPC474843
0.875	High Similarity	NPC473996
0.875	High Similarity	NPC253872
0.8743	High Similarity	NPC53252
0.8742	High Similarity	NPC202595
0.8742	High Similarity	NPC135303
0.8742	High Similarity	NPC148423
0.8742	High Similarity	NPC167576
0.8742	High Similarity	NPC474735
0.8742	High Similarity	NPC472421
0.8742	High Similarity	NPC472406
0.8735	High Similarity	NPC323137
0.8734	High Similarity	NPC6511
0.8734	High Similarity	NPC470460
0.8734	High Similarity	NPC7025
0.8734	High Similarity	NPC27221
0.8734	High Similarity	NPC266572
0.8734	High Similarity	NPC256672
0.8727	High Similarity	NPC472581
0.8727	High Similarity	NPC109180
0.8727	High Similarity	NPC159508
0.8726	High Similarity	NPC475052
0.8726	High Similarity	NPC187282
0.8726	High Similarity	NPC67805
0.8726	High Similarity	NPC124729
0.8726	High Similarity	NPC470647
0.8726	High Similarity	NPC142405
0.8726	High Similarity	NPC24136
0.8726	High Similarity	NPC301276
0.8726	High Similarity	NPC54577
0.8726	High Similarity	NPC476088
0.8726	High Similarity	NPC88964
0.8726	High Similarity	NPC83357
0.8726	High Similarity	NPC51641
0.8726	High Similarity	NPC214774
0.8726	High Similarity	NPC210826
0.8726	High Similarity	NPC300267
0.8726	High Similarity	NPC195621
0.8726	High Similarity	NPC299011
0.8726	High Similarity	NPC176229
0.8726	High Similarity	NPC477955
0.8726	High Similarity	NPC267375
0.8726	High Similarity	NPC111786
0.8726	High Similarity	NPC312973

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 NPC136641 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	342
0.1-0.2	941
0.2-0.3	1656
0.3-0.4	2610
0.4-0.5	2002
0.5-0.6	1050
0.6-0.7	368
0.7-0.8	153
0.8-0.85	26
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8662	High Similarity	NPD4378	Clinical (unspecified phase)
0.848	Intermediate Similarity	NPD6559	Discontinued
0.8466	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD920	Approved
0.8415	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8395	Intermediate Similarity	NPD4380	Phase 2
0.8383	Intermediate Similarity	NPD6959	Discontinued
0.8333	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD3749	Approved
0.8313	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD1549	Phase 2
0.8269	Intermediate Similarity	NPD2796	Approved
0.8242	Intermediate Similarity	NPD7819	Suspended
0.8228	Intermediate Similarity	NPD2800	Approved
0.8217	Intermediate Similarity	NPD2344	Approved
0.8214	Intermediate Similarity	NPD5494	Approved
0.8205	Intermediate Similarity	NPD1510	Phase 2
0.8199	Intermediate Similarity	NPD2533	Approved
0.8199	Intermediate Similarity	NPD2532	Approved
0.8199	Intermediate Similarity	NPD2534	Approved
0.8187	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD7473	Discontinued
0.8182	Intermediate Similarity	NPD1934	Approved
0.814	Intermediate Similarity	NPD3818	Discontinued
0.8133	Intermediate Similarity	NPD2801	Approved
0.8118	Intermediate Similarity	NPD6232	Discontinued
0.8095	Intermediate Similarity	NPD7075	Discontinued
0.8095	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD6801	Discontinued
0.8059	Intermediate Similarity	NPD1247	Approved
0.8036	Intermediate Similarity	NPD3882	Suspended
0.8034	Intermediate Similarity	NPD8434	Phase 2
0.8025	Intermediate Similarity	NPD1511	Approved
0.8024	Intermediate Similarity	NPD5761	Phase 2
0.8024	Intermediate Similarity	NPD5760	Phase 2
0.8024	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7411	Suspended
0.8012	Intermediate Similarity	NPD2309	Approved
0.8011	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1243	Approved
0.7989	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD1607	Approved
0.7949	Intermediate Similarity	NPD1240	Approved
0.7941	Intermediate Similarity	NPD919	Approved
0.7937	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD7768	Phase 2
0.7927	Intermediate Similarity	NPD1512	Approved
0.7919	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD6166	Phase 2
0.7886	Intermediate Similarity	NPD5844	Phase 1
0.7875	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD3926	Phase 2
0.784	Intermediate Similarity	NPD3750	Approved
0.7812	Intermediate Similarity	NPD1551	Phase 2
0.7784	Intermediate Similarity	NPD3226	Approved
0.7784	Intermediate Similarity	NPD7054	Approved
0.7765	Intermediate Similarity	NPD3817	Phase 2
0.775	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD7074	Phase 3
0.774	Intermediate Similarity	NPD7472	Approved
0.7738	Intermediate Similarity	NPD6599	Discontinued
0.7702	Intermediate Similarity	NPD6099	Approved
0.7702	Intermediate Similarity	NPD6100	Approved
0.7697	Intermediate Similarity	NPD6797	Phase 2
0.7697	Intermediate Similarity	NPD6799	Approved
0.7669	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD5402	Approved
0.7654	Intermediate Similarity	NPD1471	Phase 3
0.7654	Intermediate Similarity	NPD7251	Discontinued
0.764	Intermediate Similarity	NPD2799	Discontinued
0.7627	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD6651	Approved
0.7622	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD7808	Phase 3
0.7611	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD5710	Approved
0.76	Intermediate Similarity	NPD5711	Approved
0.76	Intermediate Similarity	NPD7229	Phase 3
0.7598	Intermediate Similarity	NPD5953	Discontinued
0.7593	Intermediate Similarity	NPD2935	Discontinued
0.759	Intermediate Similarity	NPD7390	Discontinued
0.7581	Intermediate Similarity	NPD4360	Phase 2
0.7581	Intermediate Similarity	NPD4363	Phase 3
0.7568	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD5403	Approved
0.7546	Intermediate Similarity	NPD2346	Discontinued
0.7545	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD4361	Phase 2
0.754	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD3748	Approved
0.7531	Intermediate Similarity	NPD7033	Discontinued
0.7515	Intermediate Similarity	NPD4628	Phase 3
0.7486	Intermediate Similarity	NPD7286	Phase 2
0.7484	Intermediate Similarity	NPD2313	Discontinued
0.7484	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD2296	Approved
0.7442	Intermediate Similarity	NPD37	Approved
0.744	Intermediate Similarity	NPD5401	Approved
0.743	Intermediate Similarity	NPD3751	Discontinued
0.7429	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD4625	Phase 3
0.7414	Intermediate Similarity	NPD4967	Phase 2
0.7414	Intermediate Similarity	NPD4966	Approved
0.7414	Intermediate Similarity	NPD4965	Approved
0.741	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD8313	Approved
0.7377	Intermediate Similarity	NPD8312	Approved
0.7366	Intermediate Similarity	NPD4287	Approved
0.7358	Intermediate Similarity	NPD4908	Phase 1
0.7346	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD5124	Phase 1
0.7341	Intermediate Similarity	NPD6280	Approved
0.7341	Intermediate Similarity	NPD6279	Approved
0.733	Intermediate Similarity	NPD6234	Discontinued
0.7308	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD3787	Discontinued
0.7303	Intermediate Similarity	NPD6808	Phase 2
0.7299	Intermediate Similarity	NPD1465	Phase 2
0.7292	Intermediate Similarity	NPD6776	Approved
0.7292	Intermediate Similarity	NPD6781	Approved
0.7292	Intermediate Similarity	NPD6777	Approved
0.7292	Intermediate Similarity	NPD6782	Approved
0.7292	Intermediate Similarity	NPD6778	Approved
0.7292	Intermediate Similarity	NPD6779	Approved
0.7292	Intermediate Similarity	NPD6780	Approved
0.7283	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD3268	Approved
0.7247	Intermediate Similarity	NPD7199	Phase 2
0.7244	Intermediate Similarity	NPD1610	Phase 2
0.7235	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD2798	Approved
0.7204	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6273	Approved
0.7181	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7697	Approved
0.7179	Intermediate Similarity	NPD7435	Discontinued
0.7179	Intermediate Similarity	NPD7698	Approved
0.7179	Intermediate Similarity	NPD7696	Phase 3
0.7178	Intermediate Similarity	NPD943	Approved
0.7174	Intermediate Similarity	NPD6765	Approved
0.7174	Intermediate Similarity	NPD6764	Approved
0.7172	Intermediate Similarity	NPD8151	Discontinued
0.717	Intermediate Similarity	NPD1470	Approved
0.717	Intermediate Similarity	NPD2797	Approved
0.7166	Intermediate Similarity	NPD8150	Discontinued
0.716	Intermediate Similarity	NPD3764	Approved
0.716	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD1729	Discontinued
0.7143	Intermediate Similarity	NPD7870	Phase 2
0.7143	Intermediate Similarity	NPD7871	Phase 2
0.7143	Intermediate Similarity	NPD7228	Approved
0.7135	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD2403	Approved
0.7126	Intermediate Similarity	NPD6002	Phase 3
0.7126	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6004	Phase 3
0.7126	Intermediate Similarity	NPD6005	Phase 3
0.7126	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD4308	Phase 3
0.7101	Intermediate Similarity	NPD7003	Approved
0.71	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7783	Phase 2
0.7097	Intermediate Similarity	NPD1548	Phase 1
0.7083	Intermediate Similarity	NPD2424	Discontinued
0.7081	Intermediate Similarity	NPD2861	Phase 2
0.7073	Intermediate Similarity	NPD1613	Approved
0.7073	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD7584	Approved
0.7069	Intermediate Similarity	NPD7458	Discontinued
0.7066	Intermediate Similarity	NPD5406	Approved
0.7066	Intermediate Similarity	NPD5404	Approved
0.7066	Intermediate Similarity	NPD5405	Approved
0.7066	Intermediate Similarity	NPD5408	Approved
0.7063	Intermediate Similarity	NPD1203	Approved
0.7062	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6844	Discontinued
0.7044	Intermediate Similarity	NPD4749	Approved
0.7041	Intermediate Similarity	NPD2654	Approved
0.7037	Intermediate Similarity	NPD6832	Phase 2
0.7035	Intermediate Similarity	NPD7701	Phase 2
0.7031	Intermediate Similarity	NPD6534	Approved
0.7031	Intermediate Similarity	NPD6535	Approved
0.7025	Intermediate Similarity	NPD1201	Approved
0.7021	Intermediate Similarity	NPD6784	Approved
0.7021	Intermediate Similarity	NPD6785	Approved
0.7015	Intermediate Similarity	NPD7801	Approved
0.701	Intermediate Similarity	NPD8404	Phase 2
0.7	Intermediate Similarity	NPD1876	Approved
0.6989	Remote Similarity	NPD3658	Clinical (unspecified phase)

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