NPASS Compound

Structure

NPC472368 OpenBabel07101718322D 24 25 0 0 0 0 0 0 0 0999 V2000 1.7321 -1.0000 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 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 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 1.7321 0.0000 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 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 3.4641 -1.0000 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 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 14 2 0 0 0 0 8 16 2 0 0 0 0 9 10 2 0 0 0 0 9 14 1 0 0 0 0 10 17 1 0 0 0 0 11 15 2 0 0 0 0 11 18 1 0 0 0 0 12 15 1 0 0 0 0 12 19 2 0 0 0 0 13 16 1 0 0 0 0 14 16 1 0 0 0 0 15 23 1 0 0 0 0 17 20 1 0 0 0 0 17 21 2 0 0 0 0 18 20 2 0 0 0 0 18 22 1 0 0 0 0 19 20 1 0 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	326.15
Volume:	351.432
LogP:	4.378
LogD:	3.971
LogS:	-5.99
# Rotatable Bonds:	6
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.63
Synthetic Accessibility Score:	2.297
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.919
MDCK Permeability:	1.4127782378636766e-05
Pgp-inhibitor:	0.083
Pgp-substrate:	0.678
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.449

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.101
Plasma Protein Binding (PPB):	100.26956939697266%
Volume Distribution (VD):	0.544
Pgp-substrate:	0.9693933725357056%

ADMET: Metabolism

CYP1A2-inhibitor:	0.966
CYP1A2-substrate:	0.952
CYP2C19-inhibitor:	0.967
CYP2C19-substrate:	0.461
CYP2C9-inhibitor:	0.903
CYP2C9-substrate:	0.969
CYP2D6-inhibitor:	0.932
CYP2D6-substrate:	0.917
CYP3A4-inhibitor:	0.897
CYP3A4-substrate:	0.445

ADMET: Excretion

Clearance (CL):	5.992
Half-life (T1/2):	0.212

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.04
Drug-inuced Liver Injury (DILI):	0.801
AMES Toxicity:	0.311
Rat Oral Acute Toxicity:	0.091
Maximum Recommended Daily Dose:	0.607
Skin Sensitization:	0.564
Carcinogencity:	0.58
Eye Corrosion:	0.019
Eye Irritation:	0.978
Respiratory Toxicity:	0.78

Download Data

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

Natural Product: NPC472368

Natural Product ID:	NPC472368
*Common Name:**	IOUMYYINEDYFTK-MDZDMXLPSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	IOUMYYINEDYFTK-MDZDMXLPSA-N
Standard InCHI:	InChI=1S/C20H22O4/c1-13(2)16-8-6-5-7-14(16)9-10-17(21)20-18(22)11-15(23-3)12-19(20)24-4/h5-13,22H,1-4H3/b10-9+
SMILES:	CC(C)C1=CC=CC=C1C=CC(=O)C2=C(C=C(C=C2OC)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3393850
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003472] 2'-Hydroxychalcones

*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
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11830162]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12809361]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	root	n.a.	n.a.	PMID[25597012]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26193	Piper methysticum	Species	Piperaceae	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	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.	IC50	=	2700.0	nM	PMID[516879]

☑ 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 NPC472368 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	358
0.1-0.2	1495
0.2-0.3	3659
0.3-0.4	9759
0.4-0.5	8743
0.5-0.6	3516
0.6-0.7	6008
0.7-0.8	5904
0.8-0.85	1969
0.85-0.9	965
0.9-0.95	272
0.95-1	49

Similarity Score	Similarity Level	Natural Product ID
0.9848	High Similarity	NPC472367
0.9848	High Similarity	NPC476333
0.9776	High Similarity	NPC472366
0.9699	High Similarity	NPC213603
0.9697	High Similarity	NPC286336
0.9632	High Similarity	NPC49108
0.9627	High Similarity	NPC153979
0.9621	High Similarity	NPC188646
0.9621	High Similarity	NPC204960
0.9621	High Similarity	NPC242294
0.9621	High Similarity	NPC56031
0.9621	High Similarity	NPC472365
0.9621	High Similarity	NPC139813
0.9621	High Similarity	NPC294593
0.9621	High Similarity	NPC18877
0.9621	High Similarity	NPC192304
0.9621	High Similarity	NPC312318
0.9621	High Similarity	NPC159623
0.9621	High Similarity	NPC263670
0.9621	High Similarity	NPC20560
0.9621	High Similarity	NPC144051
0.9621	High Similarity	NPC28753
0.9621	High Similarity	NPC175098
0.9621	High Similarity	NPC337373
0.9621	High Similarity	NPC82225
0.9552	High Similarity	NPC98115
0.9552	High Similarity	NPC477242
0.9552	High Similarity	NPC477243
0.9552	High Similarity	NPC186838
0.9552	High Similarity	NPC168105
0.9552	High Similarity	NPC274109
0.9552	High Similarity	NPC66349
0.9552	High Similarity	NPC477244
0.9552	High Similarity	NPC1486
0.9552	High Similarity	NPC249606
0.9552	High Similarity	NPC12165
0.9552	High Similarity	NPC150399
0.9552	High Similarity	NPC41461
0.9552	High Similarity	NPC25287
0.9545	High Similarity	NPC129132
0.9545	High Similarity	NPC205468
0.9545	High Similarity	NPC87231
0.9545	High Similarity	NPC212631
0.9545	High Similarity	NPC257756
0.9489	High Similarity	NPC126534
0.9489	High Similarity	NPC232021
0.9489	High Similarity	NPC40118
0.9485	High Similarity	NPC477956
0.9481	High Similarity	NPC317119
0.9481	High Similarity	NPC472419
0.9478	High Similarity	NPC156092
0.9478	High Similarity	NPC13575
0.9478	High Similarity	NPC131039
0.947	High Similarity	NPC186097
0.947	High Similarity	NPC128348
0.947	High Similarity	NPC475009
0.947	High Similarity	NPC112192
0.947	High Similarity	NPC262359
0.947	High Similarity	NPC475008
0.947	High Similarity	NPC189106
0.947	High Similarity	NPC66384
0.947	High Similarity	NPC164236
0.947	High Similarity	NPC64359
0.947	High Similarity	NPC308037
0.947	High Similarity	NPC313618
0.947	High Similarity	NPC309717
0.9416	High Similarity	NPC265178
0.9416	High Similarity	NPC11056
0.9412	High Similarity	NPC21350
0.9412	High Similarity	NPC124269
0.9407	High Similarity	NPC24394
0.9407	High Similarity	NPC473391
0.9407	High Similarity	NPC472364
0.9403	High Similarity	NPC103842
0.9348	High Similarity	NPC250755
0.9343	High Similarity	NPC470211
0.9343	High Similarity	NPC109232
0.9338	High Similarity	NPC294409
0.9338	High Similarity	NPC162680
0.9338	High Similarity	NPC7013
0.9338	High Similarity	NPC303644
0.9338	High Similarity	NPC181124
0.9338	High Similarity	NPC116632
0.9338	High Similarity	NPC188879
0.9338	High Similarity	NPC209560
0.9328	High Similarity	NPC27643
0.9318	High Similarity	NPC247779
0.9281	High Similarity	NPC202981
0.9281	High Similarity	NPC297600
0.9275	High Similarity	NPC215311
0.9275	High Similarity	NPC129853
0.9275	High Similarity	NPC172250
0.9275	High Similarity	NPC48624
0.9275	High Similarity	NPC259166
0.9275	High Similarity	NPC219917
0.9275	High Similarity	NPC213659
0.9275	High Similarity	NPC144118
0.9275	High Similarity	NPC204985
0.9275	High Similarity	NPC284550
0.9275	High Similarity	NPC326109
0.9275	High Similarity	NPC76445
0.9275	High Similarity	NPC80962
0.927	High Similarity	NPC279668
0.927	High Similarity	NPC309154
0.927	High Similarity	NPC471620
0.927	High Similarity	NPC278323
0.927	High Similarity	NPC243528
0.927	High Similarity	NPC12175
0.927	High Similarity	NPC90665
0.927	High Similarity	NPC55162
0.927	High Similarity	NPC251681
0.9265	High Similarity	NPC240593
0.9242	High Similarity	NPC69235
0.9242	High Similarity	NPC212379
0.9242	High Similarity	NPC211120
0.922	High Similarity	NPC477955
0.922	High Similarity	NPC25844
0.922	High Similarity	NPC299011
0.9209	High Similarity	NPC110969
0.9209	High Similarity	NPC321980
0.9209	High Similarity	NPC26051
0.9209	High Similarity	NPC470089
0.9209	High Similarity	NPC52789
0.9209	High Similarity	NPC282300
0.9209	High Similarity	NPC470087
0.9209	High Similarity	NPC268204
0.9209	High Similarity	NPC469404
0.9209	High Similarity	NPC55832
0.9203	High Similarity	NPC295384
0.9203	High Similarity	NPC261234
0.9203	High Similarity	NPC283429
0.9197	High Similarity	NPC250266
0.9197	High Similarity	NPC266597
0.9197	High Similarity	NPC23870
0.9191	High Similarity	NPC234560
0.9191	High Similarity	NPC39426
0.9167	High Similarity	NPC186098
0.9167	High Similarity	NPC80694
0.9161	High Similarity	NPC329933
0.9149	High Similarity	NPC473015
0.9149	High Similarity	NPC328623
0.9149	High Similarity	NPC311144
0.9149	High Similarity	NPC271288
0.9149	High Similarity	NPC476055
0.9149	High Similarity	NPC303185
0.9149	High Similarity	NPC473013
0.9149	High Similarity	NPC184649
0.9143	High Similarity	NPC310340
0.9143	High Similarity	NPC11561
0.9143	High Similarity	NPC226636
0.9143	High Similarity	NPC84266
0.9137	High Similarity	NPC101366
0.9137	High Similarity	NPC6407
0.9137	High Similarity	NPC270883
0.9137	High Similarity	NPC241100
0.9137	High Similarity	NPC69769
0.9137	High Similarity	NPC188243
0.9137	High Similarity	NPC172986
0.9137	High Similarity	NPC261227
0.9137	High Similarity	NPC253822
0.9137	High Similarity	NPC159275
0.9137	High Similarity	NPC110228
0.913	High Similarity	NPC188947
0.913	High Similarity	NPC280284
0.913	High Similarity	NPC118813
0.913	High Similarity	NPC99333
0.9124	High Similarity	NPC87545
0.9124	High Similarity	NPC235428
0.9124	High Similarity	NPC473887
0.9124	High Similarity	NPC194281
0.9124	High Similarity	NPC187826
0.9124	High Similarity	NPC234133
0.9124	High Similarity	NPC231772
0.9124	High Similarity	NPC127447
0.9124	High Similarity	NPC13408
0.9124	High Similarity	NPC29353
0.9124	High Similarity	NPC47815
0.9124	High Similarity	NPC124784
0.9118	High Similarity	NPC164136
0.9118	High Similarity	NPC144027
0.9118	High Similarity	NPC236974
0.9111	High Similarity	NPC15834
0.9111	High Similarity	NPC215875
0.9104	High Similarity	NPC324482
0.9097	High Similarity	NPC85131
0.9091	High Similarity	NPC128428
0.9091	High Similarity	NPC305518
0.9091	High Similarity	NPC39195
0.9091	High Similarity	NPC172329
0.9091	High Similarity	NPC2569
0.9091	High Similarity	NPC152233
0.9085	High Similarity	NPC225173
0.9085	High Similarity	NPC163846
0.9078	High Similarity	NPC106985
0.9078	High Similarity	NPC257097
0.9078	High Similarity	NPC150408
0.9078	High Similarity	NPC149026
0.9078	High Similarity	NPC117836
0.9078	High Similarity	NPC223812
0.9078	High Similarity	NPC143896

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 NPC472368 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	325
0.1-0.2	946
0.2-0.3	1421
0.3-0.4	2545
0.4-0.5	2021
0.5-0.6	1219
0.6-0.7	468
0.7-0.8	156
0.8-0.85	37
0.85-0.9	9
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.947	High Similarity	NPD1240	Approved
0.9328	High Similarity	NPD1607	Approved
0.9191	High Similarity	NPD1510	Phase 2
0.8993	High Similarity	NPD1549	Phase 2
0.8921	High Similarity	NPD1550	Clinical (unspecified phase)
0.8921	High Similarity	NPD1552	Clinical (unspecified phase)
0.8881	High Similarity	NPD4378	Clinical (unspecified phase)
0.8857	High Similarity	NPD970	Clinical (unspecified phase)
0.875	High Similarity	NPD7410	Clinical (unspecified phase)
0.8714	High Similarity	NPD2796	Approved
0.8658	High Similarity	NPD7819	Suspended
0.8601	High Similarity	NPD3750	Approved
0.86	High Similarity	NPD8443	Clinical (unspecified phase)
0.8581	High Similarity	NPD4380	Phase 2
0.8552	High Similarity	NPD6799	Approved
0.8523	High Similarity	NPD7411	Suspended
0.85	High Similarity	NPD6651	Approved
0.8456	Intermediate Similarity	NPD6599	Discontinued
0.8411	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8366	Intermediate Similarity	NPD3749	Approved
0.8366	Intermediate Similarity	NPD7075	Discontinued
0.8344	Intermediate Similarity	NPD1934	Approved
0.8344	Intermediate Similarity	NPD7473	Discontinued
0.8322	Intermediate Similarity	NPD2935	Discontinued
0.8301	Intermediate Similarity	NPD3882	Suspended
0.8299	Intermediate Similarity	NPD1511	Approved
0.8289	Intermediate Similarity	NPD2801	Approved
0.8289	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD6232	Discontinued
0.8252	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8252	Intermediate Similarity	NPD3748	Approved
0.8247	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD2532	Approved
0.8243	Intermediate Similarity	NPD2534	Approved
0.8243	Intermediate Similarity	NPD2533	Approved
0.8224	Intermediate Similarity	NPD6801	Discontinued
0.8219	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD6959	Discontinued
0.8194	Intermediate Similarity	NPD1551	Phase 2
0.8188	Intermediate Similarity	NPD2798	Approved
0.8188	Intermediate Similarity	NPD1512	Approved
0.8182	Intermediate Similarity	NPD7768	Phase 2
0.8165	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8151	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8151	Intermediate Similarity	NPD2800	Approved
0.8138	Intermediate Similarity	NPD2344	Approved
0.8125	Intermediate Similarity	NPD2799	Discontinued
0.8099	Intermediate Similarity	NPD943	Approved
0.8029	Intermediate Similarity	NPD3972	Approved
0.7986	Intermediate Similarity	NPD1203	Approved
0.7945	Intermediate Similarity	NPD6099	Approved
0.7945	Intermediate Similarity	NPD6100	Approved
0.7937	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD6166	Phase 2
0.7937	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD7390	Discontinued
0.7919	Intermediate Similarity	NPD2309	Approved
0.7914	Intermediate Similarity	NPD1876	Approved
0.7911	Intermediate Similarity	NPD5494	Approved
0.7905	Intermediate Similarity	NPD1243	Approved
0.7905	Intermediate Similarity	NPD2654	Approved
0.7895	Intermediate Similarity	NPD5403	Approved
0.7885	Intermediate Similarity	NPD3817	Phase 2
0.7852	Intermediate Similarity	NPD4628	Phase 3
0.784	Intermediate Similarity	NPD3818	Discontinued
0.7832	Intermediate Similarity	NPD3268	Approved
0.7818	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD6832	Phase 2
0.7817	Intermediate Similarity	NPD4908	Phase 1
0.7805	Intermediate Similarity	NPD5953	Discontinued
0.7792	Intermediate Similarity	NPD3226	Approved
0.7791	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD7286	Phase 2
0.7778	Intermediate Similarity	NPD9493	Approved
0.7778	Intermediate Similarity	NPD920	Approved
0.777	Intermediate Similarity	NPD9717	Approved
0.7763	Intermediate Similarity	NPD5401	Approved
0.7755	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD7074	Phase 3
0.7733	Intermediate Similarity	NPD7003	Approved
0.773	Intermediate Similarity	NPD2797	Approved
0.773	Intermediate Similarity	NPD1470	Approved
0.7722	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD3764	Approved
0.7708	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD1201	Approved
0.7698	Intermediate Similarity	NPD1610	Phase 2
0.7698	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD7054	Approved
0.7683	Intermediate Similarity	NPD5844	Phase 1
0.7664	Intermediate Similarity	NPD9545	Approved
0.7662	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD3926	Phase 2
0.7651	Intermediate Similarity	NPD2346	Discontinued
0.7647	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD7472	Approved
0.7616	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD1465	Phase 2
0.7593	Intermediate Similarity	NPD5710	Approved
0.7593	Intermediate Similarity	NPD5711	Approved
0.759	Intermediate Similarity	NPD6797	Phase 2
0.7586	Intermediate Similarity	NPD2313	Discontinued
0.7584	Intermediate Similarity	NPD5404	Approved
0.7584	Intermediate Similarity	NPD5406	Approved
0.7584	Intermediate Similarity	NPD5405	Approved
0.7584	Intermediate Similarity	NPD5408	Approved
0.7571	Intermediate Similarity	NPD422	Phase 1
0.7564	Intermediate Similarity	NPD7458	Discontinued
0.7547	Intermediate Similarity	NPD5402	Approved
0.7547	Intermediate Similarity	NPD4288	Approved
0.7545	Intermediate Similarity	NPD7251	Discontinued
0.7545	Intermediate Similarity	NPD6559	Discontinued
0.7536	Intermediate Similarity	NPD1548	Phase 1
0.7518	Intermediate Similarity	NPD1608	Approved
0.7517	Intermediate Similarity	NPD7033	Discontinued
0.75	Intermediate Similarity	NPD7808	Phase 3
0.7483	Intermediate Similarity	NPD3266	Approved
0.7483	Intermediate Similarity	NPD1164	Approved
0.7483	Intermediate Similarity	NPD3267	Approved
0.7432	Intermediate Similarity	NPD230	Phase 1
0.7417	Intermediate Similarity	NPD1471	Phase 3
0.7413	Intermediate Similarity	NPD1283	Approved
0.7407	Intermediate Similarity	NPD919	Approved
0.74	Intermediate Similarity	NPD4308	Phase 3
0.7397	Intermediate Similarity	NPD4625	Phase 3
0.7396	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD4363	Phase 3
0.7371	Intermediate Similarity	NPD4360	Phase 2
0.7357	Intermediate Similarity	NPD1651	Approved
0.7357	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD4287	Approved
0.733	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD4361	Phase 2
0.7329	Intermediate Similarity	NPD2296	Approved
0.7321	Intermediate Similarity	NPD1729	Discontinued
0.7317	Intermediate Similarity	NPD7199	Phase 2
0.7317	Intermediate Similarity	NPD1247	Approved
0.7315	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD1933	Approved
0.7312	Intermediate Similarity	NPD37	Approved
0.7308	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD17	Approved
0.7299	Intermediate Similarity	NPD1241	Discontinued
0.7292	Intermediate Similarity	NPD3225	Approved
0.7279	Intermediate Similarity	NPD3027	Phase 3
0.7278	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7229	Phase 3
0.7263	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD6104	Discontinued
0.723	Intermediate Similarity	NPD411	Approved
0.723	Intermediate Similarity	NPD1296	Phase 2
0.7229	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4749	Approved
0.7222	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD1281	Approved
0.7202	Intermediate Similarity	NPD3751	Discontinued
0.72	Intermediate Similarity	NPD5124	Phase 1
0.72	Intermediate Similarity	NPD6355	Discontinued
0.72	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD447	Suspended
0.7195	Intermediate Similarity	NPD6234	Discontinued
0.7192	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD1019	Discontinued
0.7191	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD2403	Approved
0.7185	Intermediate Similarity	NPD9266	Approved
0.7185	Intermediate Similarity	NPD74	Approved
0.7183	Intermediate Similarity	NPD4626	Approved
0.7178	Intermediate Similarity	NPD4967	Phase 2
0.7178	Intermediate Similarity	NPD4966	Approved
0.7178	Intermediate Similarity	NPD4965	Approved
0.7152	Intermediate Similarity	NPD6273	Approved
0.7151	Intermediate Similarity	NPD8312	Approved
0.7151	Intermediate Similarity	NPD8313	Approved
0.7143	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9494	Approved
0.7135	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD4060	Phase 1
0.7133	Intermediate Similarity	NPD4307	Phase 2
0.7133	Intermediate Similarity	NPD3847	Discontinued
0.7124	Intermediate Similarity	NPD4477	Approved
0.7124	Intermediate Similarity	NPD4476	Approved
0.7121	Intermediate Similarity	NPD940	Approved
0.7121	Intermediate Similarity	NPD846	Approved
0.7115	Intermediate Similarity	NPD2354	Approved
0.7114	Intermediate Similarity	NPD6798	Discontinued
0.7111	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD9267	Approved
0.7111	Intermediate Similarity	NPD9264	Approved
0.7111	Intermediate Similarity	NPD9263	Approved
0.7099	Intermediate Similarity	NPD6280	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