NPASS Compound

Structure

NPC473042 OpenBabel07101718192D 22 24 0 0 0 0 0 0 0 0999 V2000 3.4641 -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 -1.7321 1.0000 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 -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 -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 -3.4641 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 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 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -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 -4.3301 1.5000 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 -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 7 1 0 0 0 0 2 4 1 0 0 0 0 2 8 2 0 0 0 0 3 5 2 0 0 0 0 3 8 1 0 0 0 0 4 9 2 0 0 0 0 5 9 1 0 0 0 0 6 10 2 0 0 0 0 6 11 1 0 0 0 0 7 10 1 0 0 0 0 7 13 2 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 10 18 1 0 0 0 0 11 12 2 0 0 0 0 11 22 1 0 0 0 0 12 13 1 0 0 0 0 12 14 1 0 0 0 0 13 19 1 0 0 0 0 14 15 1 0 0 0 0 14 20 2 0 0 0 0 15 16 2 0 0 0 0 15 21 1 0 0 0 0 16 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	300.06
Volume:	291.273
LogP:	2.995
LogD:	1.881
LogS:	-3.45
# Rotatable Bonds:	1
TPSA:	111.13
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.549
Synthetic Accessibility Score:	2.504
Fsp3:	0.062
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:	-5.002
MDCK Permeability:	9.322215191787109e-06
Pgp-inhibitor:	0.005
Pgp-substrate:	0.02
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.043
30% Bioavailability (F30%):	0.923

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	98.69255828857422%
Volume Distribution (VD):	0.415
Pgp-substrate:	3.9408087730407715%

ADMET: Metabolism

CYP1A2-inhibitor:	0.94
CYP1A2-substrate:	0.161
CYP2C19-inhibitor:	0.174
CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.664
CYP2C9-substrate:	0.688
CYP2D6-inhibitor:	0.601
CYP2D6-substrate:	0.207
CYP3A4-inhibitor:	0.33
CYP3A4-substrate:	0.09

ADMET: Excretion

Clearance (CL):	5.593
Half-life (T1/2):	0.902

ADMET: Toxicity

hERG Blockers:	0.071
Human Hepatotoxicity (H-HT):	0.078
Drug-inuced Liver Injury (DILI):	0.979
AMES Toxicity:	0.692
Rat Oral Acute Toxicity:	0.152
Maximum Recommended Daily Dose:	0.163
Skin Sensitization:	0.875
Carcinogencity:	0.116
Eye Corrosion:	0.005
Eye Irritation:	0.926
Respiratory Toxicity:	0.076

Download Data

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

Natural Product: NPC473042

Natural Product ID:	NPC473042
*Common Name:**	6-Methykaempferol
IUPAC Name:	3,5,7-trihydroxy-2-(4-hydroxyphenyl)-6-methylchromen-4-one
Synonyms:
Standard InCHIKey:	NHMKZNNXBMLIHF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H12O6/c1-7-10(18)6-11-12(13(7)19)14(20)15(21)16(22-11)8-2-4-9(17)5-3-8/h2-6,17-19,21H,1H3
SMILES:	Oc1ccc(cc1)c1oc2cc(O)c(c(c2c(=O)c1O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3604313
PubChem CID:	44259048
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
NPO5755.1	Bauhinia glauca	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[26096681]

☑ 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
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.	Inhibition	=	25.99	%	PMID[549881]

☑ 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 NPC473042 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	508
0.1-0.2	2126
0.2-0.3	5243
0.3-0.4	11552
0.4-0.5	5562
0.5-0.6	4290
0.6-0.7	5402
0.7-0.8	4079
0.8-0.85	2133
0.85-0.9	1299
0.9-0.95	442
0.95-1	61

Similarity Score	Similarity Level	Natural Product ID
0.9927	High Similarity	NPC293053
0.9927	High Similarity	NPC190637
0.9927	High Similarity	NPC24821
0.9927	High Similarity	NPC212932
0.9927	High Similarity	NPC9117
0.9855	High Similarity	NPC216538
0.9855	High Similarity	NPC273538
0.9855	High Similarity	NPC326500
0.9854	High Similarity	NPC200694
0.9784	High Similarity	NPC178343
0.9784	High Similarity	NPC306488
0.9784	High Similarity	NPC5820
0.9784	High Similarity	NPC124729
0.9714	High Similarity	NPC166757
0.9714	High Similarity	NPC14001
0.9706	High Similarity	NPC201395
0.9645	High Similarity	NPC244407
0.9645	High Similarity	NPC296869
0.9643	High Similarity	NPC220418
0.964	High Similarity	NPC158874
0.9635	High Similarity	NPC18260
0.9635	High Similarity	NPC152042
0.9635	High Similarity	NPC78913
0.9635	High Similarity	NPC220062
0.9635	High Similarity	NPC55018
0.9635	High Similarity	NPC241838
0.9635	High Similarity	NPC303633
0.9635	High Similarity	NPC143799
0.9635	High Similarity	NPC301217
0.9635	High Similarity	NPC96565
0.9635	High Similarity	NPC216978
0.9577	High Similarity	NPC269420
0.9577	High Similarity	NPC470461
0.9565	High Similarity	NPC281207
0.9565	High Similarity	NPC269652
0.9565	High Similarity	NPC261227
0.9565	High Similarity	NPC241100
0.9565	High Similarity	NPC103342
0.9565	High Similarity	NPC270883
0.9565	High Similarity	NPC103904
0.9565	High Similarity	NPC146679
0.9565	High Similarity	NPC172986
0.9565	High Similarity	NPC230285
0.9565	High Similarity	NPC184536
0.9565	High Similarity	NPC59951
0.9565	High Similarity	NPC159275
0.9559	High Similarity	NPC281917
0.9559	High Similarity	NPC216361
0.9559	High Similarity	NPC187432
0.9559	High Similarity	NPC116775
0.9559	High Similarity	NPC256042
0.951	High Similarity	NPC61258
0.9507	High Similarity	NPC470460
0.9504	High Similarity	NPC470458
0.95	High Similarity	NPC11700
0.95	High Similarity	NPC219915
0.9496	High Similarity	NPC90582
0.9496	High Similarity	NPC110969
0.9496	High Similarity	NPC205006
0.9496	High Similarity	NPC262094
0.9496	High Similarity	NPC156590
0.9496	High Similarity	NPC136840
0.9496	High Similarity	NPC64908
0.9496	High Similarity	NPC147688
0.9496	High Similarity	NPC118840
0.9496	High Similarity	NPC282300
0.9493	High Similarity	NPC217186
0.9493	High Similarity	NPC53181
0.9489	High Similarity	NPC299379
0.9489	High Similarity	NPC228661
0.9433	High Similarity	NPC224714
0.9433	High Similarity	NPC234629
0.9433	High Similarity	NPC311741
0.9429	High Similarity	NPC217083
0.9429	High Similarity	NPC293852
0.9429	High Similarity	NPC226636
0.9429	High Similarity	NPC299080
0.9429	High Similarity	NPC11561
0.9429	High Similarity	NPC78803
0.9429	High Similarity	NPC59739
0.9429	High Similarity	NPC214236
0.9429	High Similarity	NPC62840
0.9429	High Similarity	NPC144499
0.9424	High Similarity	NPC235239
0.9424	High Similarity	NPC305355
0.9424	High Similarity	NPC475680
0.9424	High Similarity	NPC150522
0.9424	High Similarity	NPC69769
0.942	High Similarity	NPC276905
0.9416	High Similarity	NPC13408
0.9416	High Similarity	NPC29353
0.9416	High Similarity	NPC124784
0.9416	High Similarity	NPC231772
0.9416	High Similarity	NPC473887
0.9416	High Similarity	NPC127447
0.9416	High Similarity	NPC194281
0.9416	High Similarity	NPC234133
0.9416	High Similarity	NPC47815
0.9412	High Similarity	NPC248872
0.9379	High Similarity	NPC63187
0.9379	High Similarity	NPC37684
0.9379	High Similarity	NPC45934
0.9379	High Similarity	NPC142527
0.9379	High Similarity	NPC157784
0.9371	High Similarity	NPC168085
0.9366	High Similarity	NPC472629
0.9366	High Similarity	NPC154217
0.9362	High Similarity	NPC38219
0.9362	High Similarity	NPC106985
0.9362	High Similarity	NPC18585
0.9362	High Similarity	NPC166138
0.9362	High Similarity	NPC470216
0.9357	High Similarity	NPC14871
0.9357	High Similarity	NPC4743
0.9357	High Similarity	NPC469404
0.9357	High Similarity	NPC213322
0.9357	High Similarity	NPC103362
0.9357	High Similarity	NPC3188
0.9357	High Similarity	NPC324386
0.9357	High Similarity	NPC312391
0.9353	High Similarity	NPC295384
0.9348	High Similarity	NPC266597
0.9348	High Similarity	NPC250266
0.9338	High Similarity	NPC93756
0.9338	High Similarity	NPC78540
0.9338	High Similarity	NPC50898
0.9338	High Similarity	NPC108113
0.9338	High Similarity	NPC213216
0.9338	High Similarity	NPC274121
0.9315	High Similarity	NPC236756
0.9315	High Similarity	NPC311579
0.9315	High Similarity	NPC193200
0.931	High Similarity	NPC319910
0.931	High Similarity	NPC254412
0.931	High Similarity	NPC59162
0.931	High Similarity	NPC262039
0.931	High Similarity	NPC278476
0.931	High Similarity	NPC304295
0.931	High Similarity	NPC262038
0.931	High Similarity	NPC205046
0.9306	High Similarity	NPC5173
0.9306	High Similarity	NPC317492
0.9301	High Similarity	NPC24673
0.9301	High Similarity	NPC97716
0.9301	High Similarity	NPC201731
0.9301	High Similarity	NPC237635
0.9301	High Similarity	NPC296998
0.9301	High Similarity	NPC104406
0.9301	High Similarity	NPC308200
0.9301	High Similarity	NPC79469
0.9301	High Similarity	NPC473077
0.9296	High Similarity	NPC470890
0.9296	High Similarity	NPC1886
0.9296	High Similarity	NPC319752
0.9296	High Similarity	NPC87486
0.9296	High Similarity	NPC124780
0.9296	High Similarity	NPC271288
0.9296	High Similarity	NPC196137
0.9291	High Similarity	NPC10937
0.9291	High Similarity	NPC64915
0.9291	High Similarity	NPC324436
0.9291	High Similarity	NPC227579
0.9291	High Similarity	NPC223500
0.9291	High Similarity	NPC328164
0.9291	High Similarity	NPC40833
0.9291	High Similarity	NPC37496
0.9291	High Similarity	NPC265040
0.9291	High Similarity	NPC76338
0.9291	High Similarity	NPC1089
0.9291	High Similarity	NPC177354
0.9291	High Similarity	NPC296917
0.9291	High Similarity	NPC161506
0.9291	High Similarity	NPC32739
0.9291	High Similarity	NPC36181
0.9291	High Similarity	NPC78
0.9291	High Similarity	NPC66515
0.9291	High Similarity	NPC306829
0.9291	High Similarity	NPC194432
0.9291	High Similarity	NPC324134
0.9291	High Similarity	NPC166482
0.9291	High Similarity	NPC167624
0.9291	High Similarity	NPC220998
0.9291	High Similarity	NPC125855
0.9291	High Similarity	NPC182852
0.9291	High Similarity	NPC107572
0.9291	High Similarity	NPC162476
0.9291	High Similarity	NPC228504
0.9291	High Similarity	NPC148757
0.9291	High Similarity	NPC76372
0.9291	High Similarity	NPC166934
0.9291	High Similarity	NPC204469
0.9286	High Similarity	NPC172250
0.9286	High Similarity	NPC219917
0.9286	High Similarity	NPC204985
0.9286	High Similarity	NPC259166
0.9286	High Similarity	NPC48624
0.9286	High Similarity	NPC101366
0.9286	High Similarity	NPC213659
0.9286	High Similarity	NPC215311
0.9286	High Similarity	NPC144118

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 NPC473042 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	464
0.1-0.2	1014
0.2-0.3	1801
0.3-0.4	2733
0.4-0.5	1710
0.5-0.6	969
0.6-0.7	308
0.7-0.8	90
0.8-0.85	43
0.85-0.9	12
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9855	High Similarity	NPD4378	Clinical (unspecified phase)
0.9161	High Similarity	NPD7410	Clinical (unspecified phase)
0.9097	High Similarity	NPD1512	Approved
0.9071	High Similarity	NPD1550	Clinical (unspecified phase)
0.9071	High Similarity	NPD1552	Clinical (unspecified phase)
0.9065	High Similarity	NPD1510	Phase 2
0.9007	High Similarity	NPD1549	Phase 2
0.8958	High Similarity	NPD1511	Approved
0.8926	High Similarity	NPD2393	Clinical (unspecified phase)
0.8913	High Similarity	NPD1240	Approved
0.8874	High Similarity	NPD7075	Discontinued
0.8865	High Similarity	NPD2796	Approved
0.8851	High Similarity	NPD4380	Phase 2
0.88	High Similarity	NPD7096	Clinical (unspecified phase)
0.8786	High Similarity	NPD1607	Approved
0.8742	High Similarity	NPD8443	Clinical (unspecified phase)
0.8733	High Similarity	NPD6801	Discontinued
0.8733	High Similarity	NPD1934	Approved
0.8681	High Similarity	NPD2800	Approved
0.8675	High Similarity	NPD2801	Approved
0.8667	High Similarity	NPD7411	Suspended
0.8621	High Similarity	NPD3750	Approved
0.8608	High Similarity	NPD7804	Clinical (unspecified phase)
0.8571	High Similarity	NPD6799	Approved
0.8553	High Similarity	NPD7819	Suspended
0.8506	High Similarity	NPD4381	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD3817	Phase 2
0.8442	Intermediate Similarity	NPD3882	Suspended
0.8425	Intermediate Similarity	NPD1243	Approved
0.8418	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8418	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8418	Intermediate Similarity	NPD6166	Phase 2
0.8369	Intermediate Similarity	NPD2313	Discontinued
0.8356	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8355	Intermediate Similarity	NPD6599	Discontinued
0.8344	Intermediate Similarity	NPD6959	Discontinued
0.8323	Intermediate Similarity	NPD7768	Phase 2
0.8302	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8299	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8278	Intermediate Similarity	NPD920	Approved
0.8276	Intermediate Similarity	NPD3748	Approved
0.8269	Intermediate Similarity	NPD3749	Approved
0.8219	Intermediate Similarity	NPD2935	Discontinued
0.8219	Intermediate Similarity	NPD1551	Phase 2
0.8163	Intermediate Similarity	NPD2344	Approved
0.816	Intermediate Similarity	NPD6797	Phase 2
0.8158	Intermediate Similarity	NPD5403	Approved
0.8151	Intermediate Similarity	NPD2799	Discontinued
0.8146	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD5401	Approved
0.8138	Intermediate Similarity	NPD6651	Approved
0.8133	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8112	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD7251	Discontinued
0.8086	Intermediate Similarity	NPD3818	Discontinued
0.8063	Intermediate Similarity	NPD6232	Discontinued
0.8061	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD7808	Phase 3
0.8052	Intermediate Similarity	NPD3226	Approved
0.805	Intermediate Similarity	NPD5494	Approved
0.8037	Intermediate Similarity	NPD7054	Approved
0.8027	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD2532	Approved
0.8026	Intermediate Similarity	NPD2534	Approved
0.8026	Intermediate Similarity	NPD2533	Approved
0.8025	Intermediate Similarity	NPD7473	Discontinued
0.8025	Intermediate Similarity	NPD5402	Approved
0.8014	Intermediate Similarity	NPD1203	Approved
0.8	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1247	Approved
0.7988	Intermediate Similarity	NPD7472	Approved
0.7988	Intermediate Similarity	NPD7074	Phase 3
0.7987	Intermediate Similarity	NPD919	Approved
0.7952	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD2309	Approved
0.7939	Intermediate Similarity	NPD5953	Discontinued
0.7927	Intermediate Similarity	NPD7286	Phase 2
0.7919	Intermediate Similarity	NPD2346	Discontinued
0.7892	Intermediate Similarity	NPD6559	Discontinued
0.7877	Intermediate Similarity	NPD943	Approved
0.7862	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD3268	Approved
0.7862	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD422	Phase 1
0.7852	Intermediate Similarity	NPD6099	Approved
0.7852	Intermediate Similarity	NPD6100	Approved
0.7843	Intermediate Similarity	NPD7390	Discontinued
0.7832	Intermediate Similarity	NPD2798	Approved
0.7826	Intermediate Similarity	NPD1548	Phase 1
0.7801	Intermediate Similarity	NPD9717	Approved
0.7785	Intermediate Similarity	NPD4308	Phase 3
0.7762	Intermediate Similarity	NPD2797	Approved
0.773	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD1610	Phase 2
0.7724	Intermediate Similarity	NPD4908	Phase 1
0.7711	Intermediate Similarity	NPD5844	Phase 1
0.7701	Intermediate Similarity	NPD4360	Phase 2
0.7701	Intermediate Similarity	NPD4363	Phase 3
0.7692	Intermediate Similarity	NPD3225	Approved
0.7683	Intermediate Similarity	NPD3926	Phase 2
0.7667	Intermediate Similarity	NPD7033	Discontinued
0.7647	Intermediate Similarity	NPD4628	Phase 3
0.7647	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD3267	Approved
0.7639	Intermediate Similarity	NPD3266	Approved
0.7625	Intermediate Similarity	NPD1465	Phase 2
0.7619	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD6832	Phase 2
0.7578	Intermediate Similarity	NPD4288	Approved
0.7566	Intermediate Similarity	NPD1471	Phase 3
0.7557	Intermediate Similarity	NPD4361	Phase 2
0.7557	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD1608	Approved
0.7551	Intermediate Similarity	NPD4625	Phase 3
0.755	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD4307	Phase 2
0.75	Intermediate Similarity	NPD1296	Phase 2
0.75	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1201	Approved
0.7468	Intermediate Similarity	NPD2654	Approved
0.7467	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD447	Suspended
0.7467	Intermediate Similarity	NPD5124	Phase 1
0.741	Intermediate Similarity	NPD5711	Approved
0.741	Intermediate Similarity	NPD5710	Approved
0.74	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD1613	Approved
0.7397	Intermediate Similarity	NPD1470	Approved
0.7397	Intermediate Similarity	NPD1164	Approved
0.7386	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD411	Approved
0.7383	Intermediate Similarity	NPD6798	Discontinued
0.7383	Intermediate Similarity	NPD3764	Approved
0.7372	Intermediate Similarity	NPD2354	Approved
0.7362	Intermediate Similarity	NPD2296	Approved
0.7358	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD1729	Discontinued
0.7351	Intermediate Similarity	NPD230	Phase 1
0.7351	Intermediate Similarity	NPD1933	Approved
0.7343	Intermediate Similarity	NPD17	Approved
0.7338	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD3751	Discontinued
0.7324	Intermediate Similarity	NPD9545	Approved
0.7321	Intermediate Similarity	NPD2403	Approved
0.731	Intermediate Similarity	NPD3972	Approved
0.731	Intermediate Similarity	NPD1481	Phase 2
0.7305	Intermediate Similarity	NPD9493	Approved
0.7305	Intermediate Similarity	NPD7229	Phase 3
0.7296	Intermediate Similarity	NPD5049	Phase 3
0.7273	Intermediate Similarity	NPD5406	Approved
0.7273	Intermediate Similarity	NPD5404	Approved
0.7273	Intermediate Similarity	NPD4287	Approved
0.7273	Intermediate Similarity	NPD5405	Approved
0.7273	Intermediate Similarity	NPD5408	Approved
0.7267	Intermediate Similarity	NPD7458	Discontinued
0.726	Intermediate Similarity	NPD4749	Approved
0.7243	Intermediate Similarity	NPD7584	Approved
0.7241	Intermediate Similarity	NPD1535	Discovery
0.7237	Intermediate Similarity	NPD6355	Discontinued
0.7233	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD1019	Discontinued
0.7226	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD2353	Approved
0.7222	Intermediate Similarity	NPD6585	Discontinued
0.7219	Intermediate Similarity	NPD6233	Phase 2
0.7219	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD1241	Discontinued
0.7202	Intermediate Similarity	NPD3787	Discontinued
0.7198	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD7003	Approved
0.7178	Intermediate Similarity	NPD5889	Approved
0.7178	Intermediate Similarity	NPD5890	Approved
0.7171	Intermediate Similarity	NPD4060	Phase 1
0.717	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD8434	Phase 2
0.7134	Intermediate Similarity	NPD6844	Discontinued
0.7133	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD6776	Approved
0.7104	Intermediate Similarity	NPD6782	Approved
0.7104	Intermediate Similarity	NPD6779	Approved
0.7104	Intermediate Similarity	NPD6780	Approved
0.7104	Intermediate Similarity	NPD6781	Approved
0.7104	Intermediate Similarity	NPD6777	Approved
0.7104	Intermediate Similarity	NPD6778	Approved
0.7095	Intermediate Similarity	NPD1876	Approved
0.7086	Intermediate Similarity	NPD8312	Approved
0.7086	Intermediate Similarity	NPD3027	Phase 3
0.7086	Intermediate Similarity	NPD8313	Approved
0.707	Intermediate Similarity	NPD2424	Discontinued
0.7069	Intermediate Similarity	NPD6104	Discontinued
0.7067	Intermediate Similarity	NPD2861	Phase 2
0.7051	Intermediate Similarity	NPD4476	Approved
0.7051	Intermediate Similarity	NPD4477	Approved
0.7044	Intermediate Similarity	NPD3887	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