NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	272.1
Volume:	284.885
LogP:	3.447
LogD:	2.966
LogS:	-3.694
# Rotatable Bonds:	4
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.839
Synthetic Accessibility Score:	2.47
Fsp3:	0.188
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.669
MDCK Permeability:	1.4478345292445738e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.019
30% Bioavailability (F30%):	0.107

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.141
Plasma Protein Binding (PPB):	98.32783508300781%
Volume Distribution (VD):	0.54
Pgp-substrate:	0.9019492268562317%

ADMET: Metabolism

CYP1A2-inhibitor:	0.936
CYP1A2-substrate:	0.932
CYP2C19-inhibitor:	0.945
CYP2C19-substrate:	0.133
CYP2C9-inhibitor:	0.881
CYP2C9-substrate:	0.96
CYP2D6-inhibitor:	0.869
CYP2D6-substrate:	0.893
CYP3A4-inhibitor:	0.894
CYP3A4-substrate:	0.356

ADMET: Excretion

Clearance (CL):	6.566
Half-life (T1/2):	0.562

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.08
Drug-inuced Liver Injury (DILI):	0.657
AMES Toxicity:	0.61
Rat Oral Acute Toxicity:	0.203
Maximum Recommended Daily Dose:	0.07
Skin Sensitization:	0.515
Carcinogencity:	0.262
Eye Corrosion:	0.004
Eye Irritation:	0.807
Respiratory Toxicity:	0.259

Download Data

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

Natural Product: NPC213603

Natural Product ID:	NPC213603
*Common Name:**	Angolensin
IUPAC Name:	1-(2,4-dihydroxyphenyl)-2-(4-methoxyphenyl)propan-1-one
Synonyms:
Standard InCHIKey:	CCOJFDRSZSSKOG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H16O4/c1-10(11-3-6-13(20-2)7-4-11)16(19)14-8-5-12(17)9-15(14)18/h3-10,17-18H,1-2H3
SMILES:	CC(c1ccc(cc1)OC)C(=O)c1ccc(cc1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1373918
PubChem CID:	3584988
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002612] Alpha-methyldeoxybenzoin flavonoids

*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
NPO7255	Pterocarpus indicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7255	Pterocarpus indicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7255	Pterocarpus indicus	Species	Fabaceae	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
IC50	2
Potency	11

Activity Type	# Activity
Individual Protein	11
PROTEIN COMPLEX	2
Protein-Protein Interaction	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	35481.3	nM	PMID[523696]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	35481.3	nM	PMID[523696]
NPT583	Individual Protein	Inositol monophosphatase 1	Rattus norvegicus	Potency	=	3981.1	nM	PMID[523696]
NPT442	Individual Protein	Ferritin light chain	Equus caballus	Potency	=	28183.8	nM	PMID[523696]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	19952.6	nM	PMID[523696]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	3981.1	nM	PMID[523696]
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	56234.1	nM	PMID[523696]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	23109.3	nM	PMID[523696]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	25929.0	nM	PMID[523696]
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	25118.9	nM	PMID[523696]
NPT22906	PROTEIN COMPLEX	Urease subunit alpha/Urease subunit beta	Helicobacter pylori (strain ATCC 700392 / 26695) (Campylobacterpylori)	IC50	=	1050000.0	nM	PMID[523697]
NPT99	Individual Protein	Peroxisome proliferator-activated receptor gamma	Homo sapiens	IC50	=	26000.0	nM	PMID[523698]

☑ 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 NPC213603 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	342
0.1-0.2	1565
0.2-0.3	3830
0.3-0.4	9865
0.4-0.5	8381
0.5-0.6	3613
0.6-0.7	5976
0.7-0.8	5765
0.8-0.85	2034
0.85-0.9	1031
0.9-0.95	243
0.95-1	52

Similarity Score	Similarity Level	Natural Product ID
0.9699	High Similarity	NPC472368
0.9695	High Similarity	NPC286336
0.9627	High Similarity	NPC109232
0.9627	High Similarity	NPC477956
0.9624	High Similarity	NPC153979
0.9621	High Similarity	NPC131039
0.9618	High Similarity	NPC312318
0.9618	High Similarity	NPC159623
0.9618	High Similarity	NPC144051
0.9618	High Similarity	NPC263670
0.9618	High Similarity	NPC472365
0.9618	High Similarity	NPC28753
0.9618	High Similarity	NPC18877
0.9618	High Similarity	NPC175098
0.9618	High Similarity	NPC337373
0.9618	High Similarity	NPC82225
0.9618	High Similarity	NPC204960
0.9618	High Similarity	NPC188646
0.9618	High Similarity	NPC242294
0.9618	High Similarity	NPC139813
0.9618	High Similarity	NPC192304
0.9618	High Similarity	NPC294593
0.9618	High Similarity	NPC56031
0.9618	High Similarity	NPC20560
0.9615	High Similarity	NPC262359
0.9556	High Similarity	NPC265178
0.9556	High Similarity	NPC11056
0.9552	High Similarity	NPC21350
0.9549	High Similarity	NPC66349
0.9549	High Similarity	NPC472364
0.9549	High Similarity	NPC249606
0.9549	High Similarity	NPC12165
0.9549	High Similarity	NPC150399
0.9549	High Similarity	NPC41461
0.9549	High Similarity	NPC25287
0.9549	High Similarity	NPC472367
0.9549	High Similarity	NPC477242
0.9549	High Similarity	NPC1486
0.9549	High Similarity	NPC98115
0.9549	High Similarity	NPC477243
0.9549	High Similarity	NPC473391
0.9549	High Similarity	NPC186838
0.9549	High Similarity	NPC476333
0.9549	High Similarity	NPC24394
0.9549	High Similarity	NPC168105
0.9549	High Similarity	NPC274109
0.9549	High Similarity	NPC477244
0.9542	High Similarity	NPC129132
0.9542	High Similarity	NPC205468
0.9542	High Similarity	NPC87231
0.9542	High Similarity	NPC212631
0.9542	High Similarity	NPC257756
0.9485	High Similarity	NPC232021
0.9485	High Similarity	NPC126534
0.9485	High Similarity	NPC40118
0.9485	High Similarity	NPC49108
0.9481	High Similarity	NPC472366
0.9478	High Similarity	NPC303644
0.9478	High Similarity	NPC209560
0.9478	High Similarity	NPC294409
0.9478	High Similarity	NPC162680
0.9478	High Similarity	NPC181124
0.9478	High Similarity	NPC7013
0.9478	High Similarity	NPC472419
0.9478	High Similarity	NPC317119
0.9478	High Similarity	NPC116632
0.9474	High Similarity	NPC156092
0.9474	High Similarity	NPC13575
0.9466	High Similarity	NPC475008
0.9466	High Similarity	NPC128348
0.9466	High Similarity	NPC308037
0.9466	High Similarity	NPC309717
0.9466	High Similarity	NPC189106
0.9466	High Similarity	NPC66384
0.9466	High Similarity	NPC64359
0.9466	High Similarity	NPC313618
0.9466	High Similarity	NPC186097
0.9466	High Similarity	NPC475009
0.9466	High Similarity	NPC112192
0.9466	High Similarity	NPC164236
0.9416	High Similarity	NPC297600
0.9416	High Similarity	NPC202981
0.9412	High Similarity	NPC144118
0.9412	High Similarity	NPC80962
0.9412	High Similarity	NPC215311
0.9412	High Similarity	NPC213659
0.9412	High Similarity	NPC48624
0.9412	High Similarity	NPC326109
0.9412	High Similarity	NPC259166
0.9412	High Similarity	NPC219917
0.9412	High Similarity	NPC172250
0.9412	High Similarity	NPC204985
0.9407	High Similarity	NPC309154
0.9407	High Similarity	NPC12175
0.9407	High Similarity	NPC124269
0.9407	High Similarity	NPC55162
0.9407	High Similarity	NPC90665
0.9407	High Similarity	NPC279668
0.9407	High Similarity	NPC278323
0.9398	High Similarity	NPC103842
0.9353	High Similarity	NPC477955
0.9353	High Similarity	NPC299011
0.9353	High Similarity	NPC25844
0.9343	High Similarity	NPC268204
0.9343	High Similarity	NPC321980
0.9343	High Similarity	NPC52789
0.9343	High Similarity	NPC470089
0.9343	High Similarity	NPC26051
0.9343	High Similarity	NPC469404
0.9343	High Similarity	NPC55832
0.9343	High Similarity	NPC470087
0.9338	High Similarity	NPC283429
0.9338	High Similarity	NPC470211
0.9338	High Similarity	NPC295384
0.9333	High Similarity	NPC23870
0.9333	High Similarity	NPC188879
0.9328	High Similarity	NPC234560
0.9328	High Similarity	NPC39426
0.9323	High Similarity	NPC27643
0.9313	High Similarity	NPC247779
0.9281	High Similarity	NPC311144
0.9281	High Similarity	NPC271288
0.9281	High Similarity	NPC476055
0.9281	High Similarity	NPC184649
0.9281	High Similarity	NPC303185
0.9281	High Similarity	NPC328623
0.9275	High Similarity	NPC148545
0.927	High Similarity	NPC101366
0.927	High Similarity	NPC253822
0.927	High Similarity	NPC284550
0.927	High Similarity	NPC129853
0.927	High Similarity	NPC76445
0.9265	High Similarity	NPC471620
0.9265	High Similarity	NPC251681
0.9265	High Similarity	NPC243528
0.9259	High Similarity	NPC240593
0.9259	High Similarity	NPC87545
0.9259	High Similarity	NPC235428
0.9237	High Similarity	NPC211120
0.9237	High Similarity	NPC212379
0.9237	High Similarity	NPC69235
0.922	High Similarity	NPC39195
0.922	High Similarity	NPC152233
0.9209	High Similarity	NPC166138
0.9209	High Similarity	NPC117836
0.9209	High Similarity	NPC301751
0.9209	High Similarity	NPC18585
0.9209	High Similarity	NPC51887
0.9209	High Similarity	NPC113770
0.9209	High Similarity	NPC245482
0.9209	High Similarity	NPC106985
0.9209	High Similarity	NPC476178
0.9209	High Similarity	NPC475705
0.9203	High Similarity	NPC250755
0.9203	High Similarity	NPC282300
0.9203	High Similarity	NPC110969
0.9197	High Similarity	NPC261234
0.9197	High Similarity	NPC316480
0.9191	High Similarity	NPC250266
0.9191	High Similarity	NPC266597
0.9191	High Similarity	NPC255801
0.9191	High Similarity	NPC228661
0.9191	High Similarity	NPC322301
0.9191	High Similarity	NPC212767
0.9179	High Similarity	NPC223354
0.9173	High Similarity	NPC27490
0.916	High Similarity	NPC186098
0.916	High Similarity	NPC80694
0.9149	High Similarity	NPC308200
0.9149	High Similarity	NPC261271
0.9149	High Similarity	NPC475348
0.9143	High Similarity	NPC473015
0.9143	High Similarity	NPC230943
0.9143	High Similarity	NPC234629
0.9143	High Similarity	NPC473013
0.9143	High Similarity	NPC311741
0.9137	High Similarity	NPC11561
0.9137	High Similarity	NPC226636
0.9137	High Similarity	NPC144499
0.9137	High Similarity	NPC119663
0.9137	High Similarity	NPC471417
0.913	High Similarity	NPC159275
0.913	High Similarity	NPC110228
0.913	High Similarity	NPC241100
0.913	High Similarity	NPC261227
0.913	High Similarity	NPC235239
0.913	High Similarity	NPC69769
0.913	High Similarity	NPC172986
0.913	High Similarity	NPC6407
0.913	High Similarity	NPC188243
0.913	High Similarity	NPC270883
0.9124	High Similarity	NPC280284
0.9124	High Similarity	NPC188947
0.9124	High Similarity	NPC99333
0.9124	High Similarity	NPC118813
0.9118	High Similarity	NPC47815
0.9118	High Similarity	NPC13408
0.9118	High Similarity	NPC29353
0.9118	High Similarity	NPC124784
0.9118	High Similarity	NPC193792

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 NPC213603 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	320
0.1-0.2	966
0.2-0.3	1427
0.3-0.4	2522
0.4-0.5	2004
0.5-0.6	1243
0.6-0.7	461
0.7-0.8	147
0.8-0.85	45
0.85-0.9	10
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9466	High Similarity	NPD1240	Approved
0.9328	High Similarity	NPD1510	Phase 2
0.9323	High Similarity	NPD1607	Approved
0.9007	High Similarity	NPD4378	Clinical (unspecified phase)
0.8986	High Similarity	NPD1549	Phase 2
0.8913	High Similarity	NPD1550	Clinical (unspecified phase)
0.8913	High Similarity	NPD1552	Clinical (unspecified phase)
0.8841	High Similarity	NPD2796	Approved
0.8741	High Similarity	NPD7410	Clinical (unspecified phase)
0.8716	High Similarity	NPD8443	Clinical (unspecified phase)
0.8714	High Similarity	NPD970	Clinical (unspecified phase)
0.8699	High Similarity	NPD4380	Phase 2
0.8571	High Similarity	NPD2935	Discontinued
0.8542	High Similarity	NPD6799	Approved
0.8523	High Similarity	NPD7819	Suspended
0.8523	High Similarity	NPD2393	Clinical (unspecified phase)
0.8514	High Similarity	NPD7411	Suspended
0.8489	Intermediate Similarity	NPD6651	Approved
0.8477	Intermediate Similarity	NPD7075	Discontinued
0.8462	Intermediate Similarity	NPD3750	Approved
0.8456	Intermediate Similarity	NPD1934	Approved
0.8446	Intermediate Similarity	NPD6599	Discontinued
0.8444	Intermediate Similarity	NPD2798	Approved
0.8414	Intermediate Similarity	NPD1511	Approved
0.8411	Intermediate Similarity	NPD3882	Suspended
0.84	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD2801	Approved
0.838	Intermediate Similarity	NPD2344	Approved
0.8369	Intermediate Similarity	NPD2799	Discontinued
0.8355	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8345	Intermediate Similarity	NPD943	Approved
0.8333	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.831	Intermediate Similarity	NPD1551	Phase 2
0.8299	Intermediate Similarity	NPD1512	Approved
0.8289	Intermediate Similarity	NPD7768	Phase 2
0.8269	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8264	Intermediate Similarity	NPD2800	Approved
0.8239	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD3749	Approved
0.8217	Intermediate Similarity	NPD7473	Discontinued
0.8212	Intermediate Similarity	NPD6801	Discontinued
0.8201	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8151	Intermediate Similarity	NPD2309	Approved
0.8148	Intermediate Similarity	NPD3972	Approved
0.8141	Intermediate Similarity	NPD6232	Discontinued
0.8138	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8112	Intermediate Similarity	NPD3748	Approved
0.8108	Intermediate Similarity	NPD2533	Approved
0.8108	Intermediate Similarity	NPD2532	Approved
0.8108	Intermediate Similarity	NPD2534	Approved
0.8102	Intermediate Similarity	NPD1203	Approved
0.8077	Intermediate Similarity	NPD6959	Discontinued
0.8038	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD6166	Phase 2
0.8038	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD1243	Approved
0.8013	Intermediate Similarity	NPD5494	Approved
0.7987	Intermediate Similarity	NPD3817	Phase 2
0.7959	Intermediate Similarity	NPD4628	Phase 3
0.7943	Intermediate Similarity	NPD3268	Approved
0.7937	Intermediate Similarity	NPD3818	Discontinued
0.7931	Intermediate Similarity	NPD6100	Approved
0.7931	Intermediate Similarity	NPD6099	Approved
0.7929	Intermediate Similarity	NPD6832	Phase 2
0.7929	Intermediate Similarity	NPD4908	Phase 1
0.7919	Intermediate Similarity	NPD7390	Discontinued
0.7914	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD5953	Discontinued
0.7899	Intermediate Similarity	NPD1876	Approved
0.7895	Intermediate Similarity	NPD9493	Approved
0.7891	Intermediate Similarity	NPD2654	Approved
0.7888	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7883	Intermediate Similarity	NPD9717	Approved
0.7881	Intermediate Similarity	NPD920	Approved
0.7881	Intermediate Similarity	NPD5403	Approved
0.7852	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD2797	Approved
0.784	Intermediate Similarity	NPD7074	Phase 3
0.7821	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD2313	Discontinued
0.781	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD1610	Phase 2
0.7778	Intermediate Similarity	NPD7054	Approved
0.7778	Intermediate Similarity	NPD7286	Phase 2
0.7778	Intermediate Similarity	NPD7458	Discontinued
0.7763	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD3926	Phase 2
0.7748	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD5401	Approved
0.774	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD7472	Approved
0.7718	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD7003	Approved
0.7714	Intermediate Similarity	NPD1470	Approved
0.7714	Intermediate Similarity	NPD1164	Approved
0.7683	Intermediate Similarity	NPD6797	Phase 2
0.7681	Intermediate Similarity	NPD1201	Approved
0.7662	Intermediate Similarity	NPD3226	Approved
0.7647	Intermediate Similarity	NPD9545	Approved
0.7643	Intermediate Similarity	NPD5402	Approved
0.7636	Intermediate Similarity	NPD7251	Discontinued
0.7636	Intermediate Similarity	NPD6559	Discontinued
0.7635	Intermediate Similarity	NPD2346	Discontinued
0.7626	Intermediate Similarity	NPD1608	Approved
0.7619	Intermediate Similarity	NPD4308	Phase 3
0.759	Intermediate Similarity	NPD7808	Phase 3
0.7589	Intermediate Similarity	NPD3266	Approved
0.7589	Intermediate Similarity	NPD3267	Approved
0.7569	Intermediate Similarity	NPD3764	Approved
0.7568	Intermediate Similarity	NPD5404	Approved
0.7568	Intermediate Similarity	NPD5408	Approved
0.7568	Intermediate Similarity	NPD5406	Approved
0.7568	Intermediate Similarity	NPD5405	Approved
0.7561	Intermediate Similarity	NPD5844	Phase 1
0.7554	Intermediate Similarity	NPD422	Phase 1
0.7534	Intermediate Similarity	NPD230	Phase 1
0.7534	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD2296	Approved
0.7518	Intermediate Similarity	NPD1548	Phase 1
0.75	Intermediate Similarity	NPD919	Approved
0.75	Intermediate Similarity	NPD7033	Discontinued
0.7485	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD5711	Approved
0.7469	Intermediate Similarity	NPD5710	Approved
0.7468	Intermediate Similarity	NPD1465	Phase 2
0.7464	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD4360	Phase 2
0.7457	Intermediate Similarity	NPD4363	Phase 3
0.7448	Intermediate Similarity	NPD411	Approved
0.7447	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD4288	Approved
0.7415	Intermediate Similarity	NPD1933	Approved
0.7415	Intermediate Similarity	NPD6355	Discontinued
0.7415	Intermediate Similarity	NPD447	Suspended
0.7414	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD4361	Phase 2
0.741	Intermediate Similarity	NPD17	Approved
0.7407	Intermediate Similarity	NPD1241	Discontinued
0.7407	Intermediate Similarity	NPD1247	Approved
0.7403	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD1471	Phase 3
0.74	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1283	Approved
0.7379	Intermediate Similarity	NPD3027	Phase 3
0.7372	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD9494	Approved
0.7347	Intermediate Similarity	NPD4307	Phase 2
0.7338	Intermediate Similarity	NPD1651	Approved
0.7338	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD4749	Approved
0.7324	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD1729	Discontinued
0.7296	Intermediate Similarity	NPD6279	Approved
0.7296	Intermediate Similarity	NPD6280	Approved
0.7293	Intermediate Similarity	NPD9266	Approved
0.7293	Intermediate Similarity	NPD74	Approved
0.7292	Intermediate Similarity	NPD1019	Discontinued
0.7273	Intermediate Similarity	NPD3225	Approved
0.7273	Intermediate Similarity	NPD2403	Approved
0.726	Intermediate Similarity	NPD4625	Phase 3
0.7247	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD3847	Discontinued
0.7233	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD940	Approved
0.7231	Intermediate Similarity	NPD846	Approved
0.7225	Intermediate Similarity	NPD4287	Approved
0.7219	Intermediate Similarity	NPD6104	Discontinued
0.7218	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD9264	Approved
0.7218	Intermediate Similarity	NPD9267	Approved
0.7218	Intermediate Similarity	NPD9263	Approved
0.7211	Intermediate Similarity	NPD6798	Discontinued
0.7211	Intermediate Similarity	NPD1296	Phase 2
0.7208	Intermediate Similarity	NPD2354	Approved
0.7195	Intermediate Similarity	NPD7199	Phase 2
0.7194	Intermediate Similarity	NPD5536	Phase 2
0.7192	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7577	Discontinued
0.7188	Intermediate Similarity	NPD37	Approved
0.7183	Intermediate Similarity	NPD1281	Approved
0.7181	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD5124	Phase 1
0.7179	Intermediate Similarity	NPD4662	Approved
0.7179	Intermediate Similarity	NPD4661	Approved
0.7175	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD4626	Approved
0.7152	Intermediate Similarity	NPD7229	Phase 3
0.7152	Intermediate Similarity	NPD6808	Phase 2
0.7134	Intermediate Similarity	NPD6273	Approved
0.7133	Intermediate Similarity	NPD9269	Phase 2
0.7133	Intermediate Similarity	NPD1481	Phase 2
0.7123	Intermediate Similarity	NPD2861	Phase 2
0.7123	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD4060	Phase 1

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