NPASS Compound

Structure

CID301123 OpenBabel06191716112D 23 25 0 0 0 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -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 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 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 -0.0000 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 -3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 22 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 6 9 2 0 0 0 0 7 9 1 0 0 0 0 8 10 2 0 0 0 0 8 11 1 0 0 0 0 9 15 1 0 0 0 0 10 12 1 0 0 0 0 10 18 1 0 0 0 0 11 16 2 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 17 2 0 0 0 0 13 14 1 0 0 0 0 13 19 2 0 0 0 0 14 15 2 0 0 0 0 14 20 1 0 0 0 0 15 23 1 0 0 0 0 16 17 1 0 0 0 0 16 22 1 0 0 0 0 17 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.08
Volume:	308.569
LogP:	3.214
LogD:	2.593
LogS:	-3.765
# Rotatable Bonds:	3
TPSA:	89.13
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.772
Synthetic Accessibility Score:	2.297
Fsp3:	0.118
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:	-4.898
MDCK Permeability:	2.1105848645674996e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	92.30754852294922%
Volume Distribution (VD):	0.746
Pgp-substrate:	9.308594703674316%

ADMET: Metabolism

CYP1A2-inhibitor:	0.889
CYP1A2-substrate:	0.925
CYP2C19-inhibitor:	0.338
CYP2C19-substrate:	0.083
CYP2C9-inhibitor:	0.817
CYP2C9-substrate:	0.78
CYP2D6-inhibitor:	0.467
CYP2D6-substrate:	0.249
CYP3A4-inhibitor:	0.444
CYP3A4-substrate:	0.157

ADMET: Excretion

Clearance (CL):	3.36
Half-life (T1/2):	0.746

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.131
Drug-inuced Liver Injury (DILI):	0.985
AMES Toxicity:	0.659
Rat Oral Acute Toxicity:	0.217
Maximum Recommended Daily Dose:	0.033
Skin Sensitization:	0.515
Carcinogencity:	0.148
Eye Corrosion:	0.004
Eye Irritation:	0.633
Respiratory Toxicity:	0.18

Download Data

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

Natural Product: NPC301123

Natural Product ID:	NPC301123
*Common Name:**	Gnaphaliin B
IUPAC Name:	3,5-dihydroxy-7,8-dimethoxy-2-phenylchromen-4-one
Synonyms:	Gnaphaliin B
Standard InCHIKey:	CILMBWBPHLLNEH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H14O6/c1-21-11-8-10(18)12-13(19)14(20)15(9-6-4-3-5-7-9)23-17(12)16(11)22-2/h3-8,18,20H,1-2H3
SMILES:	COc1cc(c2c(=O)c(c(c3ccccc3)oc2c1OC)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL549907
PubChem CID:	5491798
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0001136] Flavonols

*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
NPO23659	Rostellularia procumbens	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO23659	Rostellularia procumbens	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO23659	Rostellularia procumbens	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20174	Limonium aureum	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12600	Trametes cinnabarina	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23285	Neocallitropsis pancheri	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24948	Stevia lemmoni	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24695	Campanula kolenatiana	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8973	Orthosiphon grandiflorus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22332	Primula imperialis	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23659	Rostellularia procumbens	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO19577	Streptomyces albosporeus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO23127	Mussaenda shikokiana	Species	Rubiaceae	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
EC50	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	63.05	ug.mL-1	PMID[468347]

☑ 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 NPC301123 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	480
0.1-0.2	2045
0.2-0.3	5283
0.3-0.4	11455
0.4-0.5	5595
0.5-0.6	4083
0.6-0.7	5142
0.7-0.8	4776
0.8-0.85	1856
0.85-0.9	1104
0.9-0.95	612
0.95-1	266

Similarity Score	Similarity Level	Natural Product ID
0.9932	High Similarity	NPC86485
0.9864	High Similarity	NPC44079
0.9864	High Similarity	NPC32557
0.9864	High Similarity	NPC201451
0.9864	High Similarity	NPC26227
0.9864	High Similarity	NPC189960
0.9862	High Similarity	NPC306821
0.9797	High Similarity	NPC266960
0.9797	High Similarity	NPC43243
0.9797	High Similarity	NPC49824
0.9797	High Similarity	NPC98661
0.9797	High Similarity	NPC247017
0.9797	High Similarity	NPC178854
0.9797	High Similarity	NPC245546
0.9795	High Similarity	NPC226973
0.9795	High Similarity	NPC208043
0.9793	High Similarity	NPC159103
0.9732	High Similarity	NPC93376
0.9732	High Similarity	NPC287979
0.9732	High Similarity	NPC305663
0.9732	High Similarity	NPC75215
0.9732	High Similarity	NPC203891
0.9732	High Similarity	NPC227192
0.9732	High Similarity	NPC176665
0.9732	High Similarity	NPC224137
0.9732	High Similarity	NPC163524
0.9732	High Similarity	NPC101830
0.9732	High Similarity	NPC189179
0.9732	High Similarity	NPC110070
0.9728	High Similarity	NPC239128
0.9728	High Similarity	NPC187498
0.9728	High Similarity	NPC275722
0.9728	High Similarity	NPC222830
0.9728	High Similarity	NPC57030
0.9728	High Similarity	NPC71334
0.9728	High Similarity	NPC83508
0.9728	High Similarity	NPC301323
0.9728	High Similarity	NPC188203
0.9728	High Similarity	NPC293183
0.9728	High Similarity	NPC156222
0.9728	High Similarity	NPC100887
0.9728	High Similarity	NPC256283
0.9728	High Similarity	NPC198826
0.9728	High Similarity	NPC120163
0.9728	High Similarity	NPC212678
0.9728	High Similarity	NPC275836
0.9728	High Similarity	NPC131624
0.9728	High Similarity	NPC25270
0.9728	High Similarity	NPC241498
0.9728	High Similarity	NPC162313
0.9728	High Similarity	NPC134677
0.9726	High Similarity	NPC50728
0.9726	High Similarity	NPC166753
0.9667	High Similarity	NPC143828
0.9667	High Similarity	NPC25495
0.9667	High Similarity	NPC4481
0.9667	High Similarity	NPC152166
0.9667	High Similarity	NPC204854
0.9667	High Similarity	NPC22472
0.9667	High Similarity	NPC19687
0.9667	High Similarity	NPC191459
0.9667	High Similarity	NPC7846
0.9667	High Similarity	NPC18607
0.9667	High Similarity	NPC300943
0.9667	High Similarity	NPC105242
0.9667	High Similarity	NPC176300
0.9667	High Similarity	NPC253634
0.9667	High Similarity	NPC288669
0.9667	High Similarity	NPC18772
0.9667	High Similarity	NPC115798
0.9667	High Similarity	NPC9609
0.9667	High Similarity	NPC261004
0.9667	High Similarity	NPC130894
0.9664	High Similarity	NPC474520
0.9664	High Similarity	NPC292107
0.9662	High Similarity	NPC69394
0.9662	High Similarity	NPC183878
0.9662	High Similarity	NPC246204
0.9662	High Similarity	NPC22519
0.9662	High Similarity	NPC160951
0.9662	High Similarity	NPC145379
0.9662	High Similarity	NPC176775
0.9662	High Similarity	NPC274327
0.9662	High Similarity	NPC47781
0.9662	High Similarity	NPC231018
0.9662	High Similarity	NPC255350
0.966	High Similarity	NPC200740
0.966	High Similarity	NPC54394
0.966	High Similarity	NPC225731
0.966	High Similarity	NPC308451
0.966	High Similarity	NPC117579
0.966	High Similarity	NPC236769
0.966	High Similarity	NPC252933
0.966	High Similarity	NPC125062
0.9658	High Similarity	NPC328119
0.9655	High Similarity	NPC12200
0.96	High Similarity	NPC78302
0.96	High Similarity	NPC472438
0.96	High Similarity	NPC7973
0.96	High Similarity	NPC29841
0.96	High Similarity	NPC235215
0.9597	High Similarity	NPC20830
0.9597	High Similarity	NPC183597
0.9597	High Similarity	NPC50715
0.9597	High Similarity	NPC227325
0.9597	High Similarity	NPC163780
0.9597	High Similarity	NPC214138
0.9597	High Similarity	NPC196439
0.9597	High Similarity	NPC201136
0.9597	High Similarity	NPC128863
0.9597	High Similarity	NPC213622
0.9597	High Similarity	NPC146165
0.9597	High Similarity	NPC167815
0.9597	High Similarity	NPC92659
0.9597	High Similarity	NPC4455
0.9597	High Similarity	NPC256612
0.9597	High Similarity	NPC2476
0.9597	High Similarity	NPC138360
0.9597	High Similarity	NPC280339
0.9595	High Similarity	NPC55205
0.9595	High Similarity	NPC27208
0.9595	High Similarity	NPC142540
0.9595	High Similarity	NPC82325
0.9595	High Similarity	NPC279989
0.9592	High Similarity	NPC219330
0.9592	High Similarity	NPC184136
0.9589	High Similarity	NPC195202
0.9589	High Similarity	NPC261548
0.9536	High Similarity	NPC193842
0.9536	High Similarity	NPC152904
0.9533	High Similarity	NPC100916
0.9533	High Similarity	NPC55619
0.9533	High Similarity	NPC200388
0.9533	High Similarity	NPC268161
0.9533	High Similarity	NPC265511
0.953	High Similarity	NPC280937
0.953	High Similarity	NPC236223
0.953	High Similarity	NPC276409
0.953	High Similarity	NPC179126
0.953	High Similarity	NPC270620
0.953	High Similarity	NPC75279
0.953	High Similarity	NPC472915
0.953	High Similarity	NPC250822
0.953	High Similarity	NPC78326
0.9527	High Similarity	NPC133953
0.9527	High Similarity	NPC28274
0.9527	High Similarity	NPC149614
0.9527	High Similarity	NPC76376
0.9527	High Similarity	NPC50403
0.9524	High Similarity	NPC296197
0.9524	High Similarity	NPC259713
0.9524	High Similarity	NPC270465
0.9524	High Similarity	NPC69752
0.9524	High Similarity	NPC223579
0.9524	High Similarity	NPC17286
0.9524	High Similarity	NPC183950
0.9524	High Similarity	NPC52005
0.9524	High Similarity	NPC137062
0.9524	High Similarity	NPC87125
0.9524	High Similarity	NPC195351
0.9524	High Similarity	NPC287101
0.9524	High Similarity	NPC216318
0.9521	High Similarity	NPC62536
0.9521	High Similarity	NPC33265
0.9474	High Similarity	NPC263449
0.9474	High Similarity	NPC246478
0.947	High Similarity	NPC476981
0.947	High Similarity	NPC470402
0.9467	High Similarity	NPC472909
0.9467	High Similarity	NPC37392
0.9467	High Similarity	NPC208197
0.9467	High Similarity	NPC2928
0.9463	High Similarity	NPC199100
0.9463	High Similarity	NPC60972
0.9463	High Similarity	NPC39732
0.9463	High Similarity	NPC180234
0.9463	High Similarity	NPC123886
0.9463	High Similarity	NPC120537
0.9459	High Similarity	NPC179183
0.9459	High Similarity	NPC45873
0.9459	High Similarity	NPC149127
0.9459	High Similarity	NPC77858
0.9459	High Similarity	NPC201547
0.9459	High Similarity	NPC156953
0.9459	High Similarity	NPC188871
0.9459	High Similarity	NPC259058
0.9459	High Similarity	NPC286342
0.9456	High Similarity	NPC120464
0.9452	High Similarity	NPC110639
0.9452	High Similarity	NPC14958
0.9452	High Similarity	NPC40818
0.9452	High Similarity	NPC106461
0.9452	High Similarity	NPC215932
0.9412	High Similarity	NPC308992
0.9408	High Similarity	NPC195832
0.9404	High Similarity	NPC235165
0.9404	High Similarity	NPC303255
0.9404	High Similarity	NPC255106
0.9404	High Similarity	NPC472916
0.94	High Similarity	NPC292214

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 NPC301123 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	450
0.1-0.2	1006
0.2-0.3	1906
0.3-0.4	2679
0.4-0.5	1673
0.5-0.6	954
0.6-0.7	332
0.7-0.8	96
0.8-0.85	34
0.85-0.9	11
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9662	High Similarity	NPD2801	Approved
0.932	High Similarity	NPD1512	Approved
0.9205	High Similarity	NPD1934	Approved
0.9184	High Similarity	NPD1511	Approved
0.915	High Similarity	NPD3882	Suspended
0.9085	High Similarity	NPD3817	Phase 2
0.8993	High Similarity	NPD4378	Clinical (unspecified phase)
0.8896	High Similarity	NPD2393	Clinical (unspecified phase)
0.8868	High Similarity	NPD6168	Clinical (unspecified phase)
0.8868	High Similarity	NPD6167	Clinical (unspecified phase)
0.8868	High Similarity	NPD6166	Phase 2
0.8834	High Similarity	NPD4338	Clinical (unspecified phase)
0.8642	High Similarity	NPD3818	Discontinued
0.8616	High Similarity	NPD5494	Approved
0.8606	High Similarity	NPD7808	Phase 3
0.8598	High Similarity	NPD6797	Phase 2
0.8589	High Similarity	NPD7054	Approved
0.8562	High Similarity	NPD1247	Approved
0.8545	High Similarity	NPD7251	Discontinued
0.8537	High Similarity	NPD7472	Approved
0.8523	High Similarity	NPD1552	Clinical (unspecified phase)
0.8523	High Similarity	NPD1550	Clinical (unspecified phase)
0.8514	High Similarity	NPD1510	Phase 2
0.8481	Intermediate Similarity	NPD5402	Approved
0.8467	Intermediate Similarity	NPD1549	Phase 2
0.8431	Intermediate Similarity	NPD6799	Approved
0.8424	Intermediate Similarity	NPD7074	Phase 3
0.8395	Intermediate Similarity	NPD6232	Discontinued
0.8375	Intermediate Similarity	NPD7075	Discontinued
0.8367	Intermediate Similarity	NPD1240	Approved
0.8354	Intermediate Similarity	NPD7473	Discontinued
0.8344	Intermediate Similarity	NPD4380	Phase 2
0.8333	Intermediate Similarity	NPD2796	Approved
0.8313	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD1607	Approved
0.8239	Intermediate Similarity	NPD6801	Discontinued
0.8232	Intermediate Similarity	NPD3926	Phase 2
0.8224	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.821	Intermediate Similarity	NPD919	Approved
0.8144	Intermediate Similarity	NPD5844	Phase 1
0.8144	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD943	Approved
0.8113	Intermediate Similarity	NPD6599	Discontinued
0.8075	Intermediate Similarity	NPD7819	Suspended
0.8075	Intermediate Similarity	NPD1465	Phase 2
0.8067	Intermediate Similarity	NPD447	Suspended
0.8047	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD5403	Approved
0.8025	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD5401	Approved
0.8	Intermediate Similarity	NPD3750	Approved
0.7974	Intermediate Similarity	NPD2935	Discontinued
0.795	Intermediate Similarity	NPD7411	Suspended
0.7935	Intermediate Similarity	NPD2800	Approved
0.7908	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD6959	Discontinued
0.7857	Intermediate Similarity	NPD1551	Phase 2
0.7852	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD230	Phase 1
0.7818	Intermediate Similarity	NPD3749	Approved
0.7812	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD3751	Discontinued
0.7763	Intermediate Similarity	NPD1613	Approved
0.7763	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD1933	Approved
0.7702	Intermediate Similarity	NPD920	Approved
0.7692	Intermediate Similarity	NPD2344	Approved
0.7688	Intermediate Similarity	NPD2534	Approved
0.7688	Intermediate Similarity	NPD2532	Approved
0.7688	Intermediate Similarity	NPD2533	Approved
0.7688	Intermediate Similarity	NPD6559	Discontinued
0.7677	Intermediate Similarity	NPD3748	Approved
0.7651	Intermediate Similarity	NPD7768	Phase 2
0.7647	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD3787	Discontinued
0.7632	Intermediate Similarity	NPD2313	Discontinued
0.7625	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD6190	Approved
0.7607	Intermediate Similarity	NPD3226	Approved
0.7595	Intermediate Similarity	NPD1243	Approved
0.7595	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD3027	Phase 3
0.7564	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD9494	Approved
0.7546	Intermediate Similarity	NPD1653	Approved
0.7533	Intermediate Similarity	NPD1203	Approved
0.7516	Intermediate Similarity	NPD6099	Approved
0.7516	Intermediate Similarity	NPD6100	Approved
0.75	Intermediate Similarity	NPD2309	Approved
0.75	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7199	Phase 2
0.7468	Intermediate Similarity	NPD2346	Discontinued
0.7466	Intermediate Similarity	NPD1548	Phase 1
0.7453	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD2799	Discontinued
0.7443	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD4628	Phase 3
0.7436	Intermediate Similarity	NPD6651	Approved
0.7429	Intermediate Similarity	NPD5953	Discontinued
0.7416	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD7286	Phase 2
0.74	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD422	Phase 1
0.7372	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD6844	Discontinued
0.7365	Intermediate Similarity	NPD37	Approved
0.7355	Intermediate Similarity	NPD6233	Phase 2
0.7353	Intermediate Similarity	NPD6234	Discontinued
0.7341	Intermediate Similarity	NPD2403	Approved
0.7337	Intermediate Similarity	NPD4965	Approved
0.7337	Intermediate Similarity	NPD4967	Phase 2
0.7337	Intermediate Similarity	NPD4966	Approved
0.7333	Intermediate Similarity	NPD9717	Approved
0.7301	Intermediate Similarity	NPD7390	Discontinued
0.729	Intermediate Similarity	NPD3268	Approved
0.7283	Intermediate Similarity	NPD5242	Approved
0.7278	Intermediate Similarity	NPD8434	Phase 2
0.7273	Intermediate Similarity	NPD6832	Phase 2
0.7273	Intermediate Similarity	NPD4908	Phase 1
0.7267	Intermediate Similarity	NPD1610	Phase 2
0.7267	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD2798	Approved
0.7243	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD3225	Approved
0.7233	Intermediate Similarity	NPD7033	Discontinued
0.7233	Intermediate Similarity	NPD4308	Phase 3
0.7222	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1608	Approved
0.7219	Intermediate Similarity	NPD6780	Approved
0.7219	Intermediate Similarity	NPD6776	Approved
0.7219	Intermediate Similarity	NPD6781	Approved
0.7219	Intermediate Similarity	NPD6778	Approved
0.7219	Intermediate Similarity	NPD6779	Approved
0.7219	Intermediate Similarity	NPD9269	Phase 2
0.7219	Intermediate Similarity	NPD6777	Approved
0.7219	Intermediate Similarity	NPD6782	Approved
0.7208	Intermediate Similarity	NPD3018	Phase 2
0.7202	Intermediate Similarity	NPD6385	Approved
0.7202	Intermediate Similarity	NPD6386	Approved
0.7195	Intermediate Similarity	NPD4357	Discontinued
0.7191	Intermediate Similarity	NPD7685	Pre-registration
0.719	Intermediate Similarity	NPD2797	Approved
0.7181	Intermediate Similarity	NPD9268	Approved
0.7179	Intermediate Similarity	NPD6798	Discontinued
0.7179	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD411	Approved
0.7176	Intermediate Similarity	NPD5353	Approved
0.7162	Intermediate Similarity	NPD5536	Phase 2
0.716	Intermediate Similarity	NPD2654	Approved
0.7143	Intermediate Similarity	NPD1471	Phase 3
0.7143	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD4360	Phase 2
0.7135	Intermediate Similarity	NPD4363	Phase 3
0.7126	Intermediate Similarity	NPD5710	Approved
0.7126	Intermediate Similarity	NPD5711	Approved
0.7108	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD7696	Phase 3
0.7105	Intermediate Similarity	NPD7698	Approved
0.7105	Intermediate Similarity	NPD7435	Discontinued
0.7105	Intermediate Similarity	NPD1481	Phase 2
0.7105	Intermediate Similarity	NPD7697	Approved
0.7097	Intermediate Similarity	NPD2861	Phase 2
0.7088	Intermediate Similarity	NPD8150	Discontinued
0.7078	Intermediate Similarity	NPD3266	Approved
0.7078	Intermediate Similarity	NPD1470	Approved
0.7078	Intermediate Similarity	NPD3267	Approved
0.7076	Intermediate Similarity	NPD4288	Approved
0.7073	Intermediate Similarity	NPD2354	Approved
0.7068	Intermediate Similarity	NPD7870	Phase 2
0.7068	Intermediate Similarity	NPD7871	Phase 2
0.7062	Intermediate Similarity	NPD7228	Approved
0.7059	Intermediate Similarity	NPD2982	Phase 2
0.7059	Intermediate Similarity	NPD2983	Phase 2
0.7056	Intermediate Similarity	NPD7549	Discontinued
0.7048	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6355	Discontinued
0.7039	Intermediate Similarity	NPD1535	Discovery
0.7039	Intermediate Similarity	NPD1201	Approved
0.7029	Intermediate Similarity	NPD7229	Phase 3
0.702	Intermediate Similarity	NPD17	Approved
0.7017	Intermediate Similarity	NPD8313	Approved
0.7017	Intermediate Similarity	NPD8312	Approved
0.7006	Intermediate Similarity	NPD4625	Phase 3
0.7005	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD4361	Phase 2
0.7	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD9545	Approved
0.6993	Remote Similarity	NPD2981	Phase 2
0.6981	Remote Similarity	NPD4060	Phase 1
0.6981	Remote Similarity	NPD4307	Phase 2

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