NPASS Compound

Structure

NPC470461 OpenBabel07101718312D 28 30 0 0 1 0 0 0 0 0999 V2000 0.0000 -3.0000 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 1.7321 -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 2.5981 0.5000 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 3 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 -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 3.4641 -1.0000 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 0.5000 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 -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 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 0.0000 -1.0000 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 4.3301 -1.5000 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 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 27 1 0 0 0 0 3 4 1 0 0 0 0 3 11 1 0 0 0 0 4 12 1 0 0 0 0 5 6 1 0 0 0 0 5 13 2 0 0 0 0 6 15 2 0 0 0 0 7 12 2 0 0 0 0 7 13 1 0 0 0 0 8 14 2 0 0 0 0 8 16 1 0 0 0 0 9 14 1 0 0 0 0 9 17 2 0 0 0 0 10 11 1 0 0 0 0 10 22 1 0 0 0 0 12 15 1 0 0 0 0 13 20 1 0 0 0 0 14 23 1 0 0 0 0 15 24 1 0 0 0 0 16 18 2 0 0 0 0 16 25 1 0 0 0 0 17 18 1 0 0 0 0 17 28 1 0 0 0 0 18 19 1 0 0 0 0 19 21 1 0 0 0 0 19 26 2 0 0 0 0 20 21 2 0 0 0 0 20 28 1 0 0 0 0 21 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	386.14
Volume:	386.543
LogP:	3.409
LogD:	2.806
LogS:	-3.767
# Rotatable Bonds:	6
TPSA:	120.36
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.513
Synthetic Accessibility Score:	3.152
Fsp3:	0.286
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:	-4.899
MDCK Permeability:	8.703700586920604e-06
Pgp-inhibitor:	0.006
Pgp-substrate:	0.298
Human Intestinal Absorption (HIA):	0.029
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.616

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	97.53008270263672%
Volume Distribution (VD):	0.53
Pgp-substrate:	2.5317130088806152%

ADMET: Metabolism

CYP1A2-inhibitor:	0.953
CYP1A2-substrate:	0.718
CYP2C19-inhibitor:	0.497
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.751
CYP2C9-substrate:	0.882
CYP2D6-inhibitor:	0.822
CYP2D6-substrate:	0.616
CYP3A4-inhibitor:	0.475
CYP3A4-substrate:	0.109

ADMET: Excretion

Clearance (CL):	6.989
Half-life (T1/2):	0.867

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.088
Drug-inuced Liver Injury (DILI):	0.961
AMES Toxicity:	0.574
Rat Oral Acute Toxicity:	0.116
Maximum Recommended Daily Dose:	0.507
Skin Sensitization:	0.812
Carcinogencity:	0.035
Eye Corrosion:	0.003
Eye Irritation:	0.814
Respiratory Toxicity:	0.077

Download Data

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

Natural Product: NPC470461

Natural Product ID:	NPC470461
*Common Name:**	Dodoviscin I
IUPAC Name:	5,7-dihydroxy-2-[4-hydroxy-3-(4-hydroxy-3-methylbutyl)phenyl]-3-methoxychromen-4-one
Synonyms:	dodoviscin I
Standard InCHIKey:	LMOYOATYLHNKNP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H22O7/c1-11(10-22)3-4-12-7-13(5-6-15(12)24)20-21(27-2)19(26)18-16(25)8-14(23)9-17(18)28-20/h5-9,11,22-25H,3-4,10H2,1-2H3
SMILES:	OCC(CCc1cc(ccc1O)c1oc2cc(O)cc(c2c(=O)c1OC)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2037154
PubChem CID:	57408289
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0003502] 3'-prenylated flavones

*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
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19719093]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22512738]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	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
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	189.6	%	PMID[547077]

☑ 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 NPC470461 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	412
0.1-0.2	1660
0.2-0.3	4106
0.3-0.4	10103
0.4-0.5	8190
0.5-0.6	3855
0.6-0.7	5491
0.7-0.8	4340
0.8-0.85	2248
0.85-0.9	1848
0.9-0.95	420
0.95-1	24

Similarity Score	Similarity Level	Natural Product ID
0.993	High Similarity	NPC470460
0.9789	High Similarity	NPC178343
0.9789	High Similarity	NPC470458
0.9789	High Similarity	NPC306488
0.9789	High Similarity	NPC5820
0.9718	High Similarity	NPC216538
0.9718	High Similarity	NPC273538
0.9718	High Similarity	NPC326500
0.9655	High Similarity	NPC61258
0.965	High Similarity	NPC124729
0.9648	High Similarity	NPC158874
0.9648	High Similarity	NPC9117
0.9648	High Similarity	NPC24821
0.9648	High Similarity	NPC190637
0.9648	High Similarity	NPC212932
0.9648	High Similarity	NPC293053
0.958	High Similarity	NPC224714
0.9577	High Similarity	NPC473042
0.9577	High Similarity	NPC200694
0.9524	High Similarity	NPC217149
0.9524	High Similarity	NPC216035
0.9517	High Similarity	NPC296869
0.9517	High Similarity	NPC244407
0.9514	High Similarity	NPC472629
0.9507	High Similarity	NPC282300
0.9507	High Similarity	NPC262094
0.9507	High Similarity	NPC90582
0.9459	High Similarity	NPC236756
0.9459	High Similarity	NPC193200
0.9459	High Similarity	NPC311579
0.9456	High Similarity	NPC254412
0.9456	High Similarity	NPC262038
0.9456	High Similarity	NPC262039
0.9456	High Similarity	NPC278476
0.9456	High Similarity	NPC319910
0.9452	High Similarity	NPC5173
0.9448	High Similarity	NPC308200
0.9448	High Similarity	NPC14001
0.9448	High Similarity	NPC166757
0.9444	High Similarity	NPC470890
0.9444	High Similarity	NPC87486
0.9444	High Similarity	NPC271288
0.9444	High Similarity	NPC124780
0.9437	High Similarity	NPC59951
0.9437	High Similarity	NPC103342
0.9437	High Similarity	NPC159275
0.9437	High Similarity	NPC146679
0.9437	High Similarity	NPC103904
0.9437	High Similarity	NPC241100
0.9437	High Similarity	NPC230285
0.9437	High Similarity	NPC184536
0.9396	High Similarity	NPC217706
0.9396	High Similarity	NPC207809
0.9396	High Similarity	NPC304745
0.9396	High Similarity	NPC259710
0.9396	High Similarity	NPC111341
0.9396	High Similarity	NPC304207
0.9396	High Similarity	NPC48579
0.9392	High Similarity	NPC35567
0.9392	High Similarity	NPC138288
0.9392	High Similarity	NPC171651
0.9392	High Similarity	NPC243171
0.9388	High Similarity	NPC37348
0.9388	High Similarity	NPC105136
0.9388	High Similarity	NPC29777
0.9388	High Similarity	NPC471115
0.9388	High Similarity	NPC474735
0.9384	High Similarity	NPC39195
0.9384	High Similarity	NPC145467
0.9384	High Similarity	NPC6511
0.9384	High Similarity	NPC168085
0.9379	High Similarity	NPC220418
0.9379	High Similarity	NPC474161
0.9379	High Similarity	NPC476088
0.9375	High Similarity	NPC85162
0.9375	High Similarity	NPC476178
0.9375	High Similarity	NPC278249
0.9375	High Similarity	NPC475705
0.9375	High Similarity	NPC107177
0.9375	High Similarity	NPC51887
0.9375	High Similarity	NPC81697
0.9375	High Similarity	NPC301751
0.9375	High Similarity	NPC117836
0.9375	High Similarity	NPC125894
0.9375	High Similarity	NPC223812
0.9375	High Similarity	NPC77794
0.9375	High Similarity	NPC245482
0.9371	High Similarity	NPC469404
0.9371	High Similarity	NPC110969
0.9371	High Similarity	NPC136840
0.9366	High Similarity	NPC241838
0.9366	High Similarity	NPC78913
0.9366	High Similarity	NPC217186
0.9366	High Similarity	NPC96565
0.9366	High Similarity	NPC301217
0.9366	High Similarity	NPC220062
0.9366	High Similarity	NPC216978
0.9366	High Similarity	NPC303633
0.9366	High Similarity	NPC152042
0.9366	High Similarity	NPC143799
0.9366	High Similarity	NPC53181
0.9366	High Similarity	NPC18260
0.9366	High Similarity	NPC55018
0.9333	High Similarity	NPC10754
0.9333	High Similarity	NPC20530
0.9333	High Similarity	NPC215917
0.9329	High Similarity	NPC293286
0.9329	High Similarity	NPC180301
0.9329	High Similarity	NPC268193
0.9329	High Similarity	NPC248793
0.932	High Similarity	NPC317492
0.932	High Similarity	NPC471114
0.932	High Similarity	NPC269420
0.9315	High Similarity	NPC104406
0.9315	High Similarity	NPC296998
0.9315	High Similarity	NPC79469
0.9315	High Similarity	NPC473077
0.9315	High Similarity	NPC24673
0.9315	High Similarity	NPC97716
0.9315	High Similarity	NPC201731
0.9315	High Similarity	NPC237635
0.931	High Similarity	NPC131568
0.931	High Similarity	NPC234629
0.931	High Similarity	NPC473013
0.931	High Similarity	NPC473015
0.931	High Similarity	NPC131579
0.931	High Similarity	NPC319752
0.931	High Similarity	NPC311741
0.931	High Similarity	NPC235217
0.931	High Similarity	NPC473014
0.931	High Similarity	NPC311144
0.9306	High Similarity	NPC78
0.9306	High Similarity	NPC66515
0.9306	High Similarity	NPC32739
0.9306	High Similarity	NPC324436
0.9306	High Similarity	NPC177354
0.9306	High Similarity	NPC328164
0.9306	High Similarity	NPC306829
0.9306	High Similarity	NPC166482
0.9306	High Similarity	NPC125855
0.9306	High Similarity	NPC194432
0.9306	High Similarity	NPC226636
0.9306	High Similarity	NPC296917
0.9306	High Similarity	NPC166934
0.9306	High Similarity	NPC148757
0.9306	High Similarity	NPC324134
0.9306	High Similarity	NPC228504
0.9306	High Similarity	NPC10937
0.9306	High Similarity	NPC220998
0.9306	High Similarity	NPC76372
0.9306	High Similarity	NPC182852
0.9306	High Similarity	NPC40833
0.9306	High Similarity	NPC162476
0.9306	High Similarity	NPC107572
0.9306	High Similarity	NPC227579
0.9306	High Similarity	NPC37496
0.9306	High Similarity	NPC64915
0.9306	High Similarity	NPC11561
0.9306	High Similarity	NPC265040
0.9306	High Similarity	NPC76338
0.9306	High Similarity	NPC167624
0.9306	High Similarity	NPC223500
0.9306	High Similarity	NPC1089
0.9306	High Similarity	NPC161506
0.9306	High Similarity	NPC148545
0.9301	High Similarity	NPC204985
0.9301	High Similarity	NPC270883
0.9301	High Similarity	NPC213659
0.9301	High Similarity	NPC269652
0.9301	High Similarity	NPC76445
0.9301	High Similarity	NPC172986
0.9301	High Similarity	NPC284550
0.9301	High Similarity	NPC281207
0.9301	High Similarity	NPC261227
0.9301	High Similarity	NPC48624
0.9301	High Similarity	NPC129853
0.9301	High Similarity	NPC172250
0.9301	High Similarity	NPC259166
0.9301	High Similarity	NPC144118
0.9301	High Similarity	NPC80962
0.9301	High Similarity	NPC150522
0.9301	High Similarity	NPC326109
0.9301	High Similarity	NPC219917
0.9301	High Similarity	NPC215311
0.9296	High Similarity	NPC276905
0.9296	High Similarity	NPC201395
0.9272	High Similarity	NPC281137
0.9272	High Similarity	NPC282390
0.9267	High Similarity	NPC476169
0.9267	High Similarity	NPC133392
0.9262	High Similarity	NPC210597
0.9262	High Similarity	NPC161881
0.9262	High Similarity	NPC56232
0.9262	High Similarity	NPC10807
0.9262	High Similarity	NPC150123
0.9262	High Similarity	NPC244583
0.9257	High Similarity	NPC321896
0.9257	High Similarity	NPC476185
0.9257	High Similarity	NPC472633
0.9252	High Similarity	NPC266572

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 NPC470461 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	374
0.1-0.2	933
0.2-0.3	1687
0.3-0.4	2643
0.4-0.5	1902
0.5-0.6	1050
0.6-0.7	380
0.7-0.8	117
0.8-0.85	40
0.85-0.9	21
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9718	High Similarity	NPD4378	Clinical (unspecified phase)
0.902	High Similarity	NPD7075	Discontinued
0.9007	High Similarity	NPD6801	Discontinued
0.9	High Similarity	NPD4380	Phase 2
0.8958	High Similarity	NPD1552	Clinical (unspecified phase)
0.8958	High Similarity	NPD1550	Clinical (unspecified phase)
0.8951	High Similarity	NPD1510	Phase 2
0.8947	High Similarity	NPD2393	Clinical (unspecified phase)
0.8947	High Similarity	NPD7096	Clinical (unspecified phase)
0.8919	High Similarity	NPD7410	Clinical (unspecified phase)
0.8897	High Similarity	NPD1549	Phase 2
0.8889	High Similarity	NPD2796	Approved
0.8889	High Similarity	NPD8443	Clinical (unspecified phase)
0.8868	High Similarity	NPD7804	Clinical (unspecified phase)
0.8733	High Similarity	NPD1512	Approved
0.8725	High Similarity	NPD6799	Approved
0.8693	High Similarity	NPD7411	Suspended
0.8671	High Similarity	NPD1240	Approved
0.8654	High Similarity	NPD4381	Clinical (unspecified phase)
0.8645	High Similarity	NPD3817	Phase 2
0.8636	High Similarity	NPD1934	Approved
0.86	High Similarity	NPD1511	Approved
0.859	High Similarity	NPD3882	Suspended
0.8581	High Similarity	NPD2801	Approved
0.8581	High Similarity	NPD7819	Suspended
0.8562	High Similarity	NPD6166	Phase 2
0.8562	High Similarity	NPD6168	Clinical (unspecified phase)
0.8562	High Similarity	NPD6167	Clinical (unspecified phase)
0.8552	High Similarity	NPD1607	Approved
0.8506	High Similarity	NPD6599	Discontinued
0.8431	Intermediate Similarity	NPD5403	Approved
0.8415	Intermediate Similarity	NPD6797	Phase 2
0.8375	Intermediate Similarity	NPD6959	Discontinued
0.8364	Intermediate Similarity	NPD7251	Discontinued
0.8354	Intermediate Similarity	NPD7768	Phase 2
0.8333	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD2800	Approved
0.8333	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD7808	Phase 3
0.8301	Intermediate Similarity	NPD5401	Approved
0.8291	Intermediate Similarity	NPD5402	Approved
0.8278	Intermediate Similarity	NPD3750	Approved
0.8267	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD3818	Discontinued
0.8204	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD5494	Approved
0.8194	Intermediate Similarity	NPD920	Approved
0.8182	Intermediate Similarity	NPD7054	Approved
0.8176	Intermediate Similarity	NPD6651	Approved
0.8151	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD2935	Discontinued
0.8133	Intermediate Similarity	NPD7074	Phase 3
0.8133	Intermediate Similarity	NPD7472	Approved
0.8133	Intermediate Similarity	NPD1551	Phase 2
0.8092	Intermediate Similarity	NPD1243	Approved
0.8067	Intermediate Similarity	NPD2799	Discontinued
0.8065	Intermediate Similarity	NPD2532	Approved
0.8065	Intermediate Similarity	NPD2534	Approved
0.8065	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD2533	Approved
0.8061	Intermediate Similarity	NPD7473	Discontinued
0.8052	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD1247	Approved
0.8036	Intermediate Similarity	NPD6559	Discontinued
0.8027	Intermediate Similarity	NPD2313	Discontinued
0.8027	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD919	Approved
0.7988	Intermediate Similarity	NPD6232	Discontinued
0.7976	Intermediate Similarity	NPD5953	Discontinued
0.7964	Intermediate Similarity	NPD7286	Phase 2
0.7963	Intermediate Similarity	NPD3749	Approved
0.7947	Intermediate Similarity	NPD3748	Approved
0.7943	Intermediate Similarity	NPD4360	Phase 2
0.7943	Intermediate Similarity	NPD4363	Phase 3
0.7901	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD4908	Phase 1
0.7857	Intermediate Similarity	NPD5844	Phase 1
0.7853	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD2344	Approved
0.7829	Intermediate Similarity	NPD7033	Discontinued
0.7806	Intermediate Similarity	NPD4628	Phase 3
0.7797	Intermediate Similarity	NPD4361	Phase 2
0.7797	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD3268	Approved
0.7778	Intermediate Similarity	NPD1610	Phase 2
0.7778	Intermediate Similarity	NPD6100	Approved
0.7778	Intermediate Similarity	NPD6099	Approved
0.7765	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD2798	Approved
0.775	Intermediate Similarity	NPD3226	Approved
0.7748	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD5124	Phase 1
0.7746	Intermediate Similarity	NPD1548	Phase 1
0.7712	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD1203	Approved
0.7687	Intermediate Similarity	NPD2797	Approved
0.7658	Intermediate Similarity	NPD7390	Discontinued
0.7655	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD6832	Phase 2
0.7643	Intermediate Similarity	NPD2309	Approved
0.7627	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD3926	Phase 2
0.7613	Intermediate Similarity	NPD2346	Discontinued
0.758	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD943	Approved
0.755	Intermediate Similarity	NPD6798	Discontinued
0.7534	Intermediate Similarity	NPD422	Phase 1
0.7516	Intermediate Similarity	NPD6355	Discontinued
0.75	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD3751	Discontinued
0.7484	Intermediate Similarity	NPD4308	Phase 3
0.7483	Intermediate Similarity	NPD9717	Approved
0.7471	Intermediate Similarity	NPD2403	Approved
0.7456	Intermediate Similarity	NPD7229	Phase 3
0.7456	Intermediate Similarity	NPD5710	Approved
0.7456	Intermediate Similarity	NPD3787	Discontinued
0.7456	Intermediate Similarity	NPD5711	Approved
0.7451	Intermediate Similarity	NPD4060	Phase 1
0.7451	Intermediate Similarity	NPD1613	Approved
0.7451	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD3267	Approved
0.745	Intermediate Similarity	NPD3266	Approved
0.7423	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD7458	Discontinued
0.7412	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD2654	Approved
0.7403	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD8434	Phase 2
0.7399	Intermediate Similarity	NPD1729	Discontinued
0.7389	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD1471	Phase 3
0.7386	Intermediate Similarity	NPD6233	Phase 2
0.7383	Intermediate Similarity	NPD3225	Approved
0.738	Intermediate Similarity	NPD7584	Approved
0.7368	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4625	Phase 3
0.7365	Intermediate Similarity	NPD1608	Approved
0.7349	Intermediate Similarity	NPD1465	Phase 2
0.733	Intermediate Similarity	NPD8313	Approved
0.733	Intermediate Similarity	NPD8312	Approved
0.732	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD4288	Approved
0.7303	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7199	Phase 2
0.729	Intermediate Similarity	NPD230	Phase 1
0.7289	Intermediate Similarity	NPD6844	Discontinued
0.7278	Intermediate Similarity	NPD6004	Phase 3
0.7278	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6002	Phase 3
0.7278	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6005	Phase 3
0.7261	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD9545	Approved
0.7255	Intermediate Similarity	NPD3027	Phase 3
0.725	Intermediate Similarity	NPD7003	Approved
0.7248	Intermediate Similarity	NPD3972	Approved
0.7246	Intermediate Similarity	NPD5760	Phase 2
0.7246	Intermediate Similarity	NPD5761	Phase 2
0.7243	Intermediate Similarity	NPD6776	Approved
0.7243	Intermediate Similarity	NPD6782	Approved
0.7243	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD6780	Approved
0.7243	Intermediate Similarity	NPD6778	Approved
0.7243	Intermediate Similarity	NPD6777	Approved
0.7243	Intermediate Similarity	NPD6781	Approved
0.7243	Intermediate Similarity	NPD6779	Approved
0.7239	Intermediate Similarity	NPD5049	Phase 3
0.7237	Intermediate Similarity	NPD2861	Phase 2
0.7237	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD2424	Discontinued
0.7229	Intermediate Similarity	NPD5890	Approved
0.7229	Intermediate Similarity	NPD5889	Approved
0.7226	Intermediate Similarity	NPD4307	Phase 2
0.7219	Intermediate Similarity	NPD7435	Discontinued
0.7208	Intermediate Similarity	NPD1296	Phase 2
0.7207	Intermediate Similarity	NPD8150	Discontinued
0.7205	Intermediate Similarity	NPD3887	Approved
0.7205	Intermediate Similarity	NPD2354	Approved
0.7205	Intermediate Similarity	NPD6190	Approved
0.72	Intermediate Similarity	NPD4749	Approved
0.7188	Intermediate Similarity	NPD1652	Phase 2
0.7186	Intermediate Similarity	NPD37	Approved
0.7181	Intermediate Similarity	NPD1201	Approved
0.7179	Intermediate Similarity	NPD447	Suspended
0.7179	Intermediate Similarity	NPD1933	Approved
0.7171	Intermediate Similarity	NPD1019	Discontinued
0.7162	Intermediate Similarity	NPD17	Approved
0.716	Intermediate Similarity	NPD4965	Approved
0.716	Intermediate Similarity	NPD4966	Approved
0.716	Intermediate Similarity	NPD4967	Phase 2
0.7153	Intermediate Similarity	NPD1241	Discontinued
0.7143	Intermediate Similarity	NPD8455	Phase 2
0.7134	Intermediate Similarity	NPD6273	Approved
0.7128	Intermediate Similarity	NPD7696	Phase 3
0.7128	Intermediate Similarity	NPD7697	Approved
0.7128	Intermediate Similarity	NPD7698	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