NPASS Compound

Structure

CID62258 OpenBabel06191715402D 22 23 0 0 1 0 0 0 0 0999 V2000 9.5263 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -2.0000 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 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 2.5981 -1.5000 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 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 -2.0000 0.0000 C 0 0 1 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 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 6 1 0 0 0 0 3 7 2 0 0 0 0 4 5 1 0 0 0 0 4 8 2 0 0 0 0 5 9 1 0 0 0 0 6 15 2 0 0 0 0 7 15 1 0 0 0 0 8 15 1 0 0 0 0 9 17 1 0 0 0 0 10 12 1 0 0 0 0 10 16 1 0 0 0 0 11 13 2 0 0 0 0 11 16 1 0 0 0 0 12 17 1 0 0 0 0 13 18 1 0 0 0 0 14 16 2 0 0 0 0 14 19 1 0 0 0 0 17 20 1 6 0 0 0 18 19 2 0 0 0 0 18 21 1 0 0 0 0 19 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	298.16
Volume:	327.983
LogP:	3.06
LogD:	3.346
LogS:	-3.483
# Rotatable Bonds:	7
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.68
Synthetic Accessibility Score:	2.651
Fsp3:	0.263
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.874
MDCK Permeability:	1.4316003216663375e-05
Pgp-inhibitor:	0.014
Pgp-substrate:	0.177
Human Intestinal Absorption (HIA):	0.045
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.069
Plasma Protein Binding (PPB):	97.6709213256836%
Volume Distribution (VD):	0.578
Pgp-substrate:	2.0369515419006348%

ADMET: Metabolism

CYP1A2-inhibitor:	0.93
CYP1A2-substrate:	0.265
CYP2C19-inhibitor:	0.866
CYP2C19-substrate:	0.103
CYP2C9-inhibitor:	0.693
CYP2C9-substrate:	0.941
CYP2D6-inhibitor:	0.888
CYP2D6-substrate:	0.892
CYP3A4-inhibitor:	0.426
CYP3A4-substrate:	0.262

ADMET: Excretion

Clearance (CL):	14.016
Half-life (T1/2):	0.898

ADMET: Toxicity

hERG Blockers:	0.126
Human Hepatotoxicity (H-HT):	0.056
Drug-inuced Liver Injury (DILI):	0.019
AMES Toxicity:	0.276
Rat Oral Acute Toxicity:	0.039
Maximum Recommended Daily Dose:	0.876
Skin Sensitization:	0.958
Carcinogencity:	0.508
Eye Corrosion:	0.148
Eye Irritation:	0.98
Respiratory Toxicity:	0.559

Download Data

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

Natural Product: NPC62258

Natural Product ID:	NPC62258
*Common Name:**	(S,E)-4-(3-Hydroxy-7-Phenylhept-6-Enyl)Benzene-1,2-Diol
IUPAC Name:	4-[(E,3S)-3-hydroxy-7-phenylhept-6-enyl]benzene-1,2-diol
Synonyms:
Standard InCHIKey:	OELWYQGRQUQQPD-AUNFYEFLSA-N
Standard InCHI:	InChI=1S/C19H22O3/c20-17(9-5-4-8-15-6-2-1-3-7-15)12-10-16-11-13-18(21)19(22)14-16/h1-4,6-8,11,13-14,17,20-22H,5,9-10,12H2/b8-4+/t17-/m0/s1
SMILES:	O[C@H](CCc1ccc(c(c1)O)O)CC/C=C/c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL459648
PubChem CID:	44560893
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids

*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
NPO22901	Curcuma comosa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/np100392m]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	DOI[10.1021/np100392m]
NPO22901	Curcuma comosa	Species	Zingiberaceae	Eukaryota	rhizomes	Kampaengsaen district, Nakhon Pathom province, Thailand	n.a.	PMID[18554915]
NPO22901	Curcuma comosa	Species	Zingiberaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[20196571]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[20879743]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21807513]
NPO22901	Curcuma comosa	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[23910596]
NPO22901	Curcuma comosa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8176399]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22901	Curcuma comosa	Species	Zingiberaceae	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
Others	2

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	45.98	%	PMID[533354]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	51.5	%	PMID[533354]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	3860.0	nM	PMID[533355]

☑ 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 NPC62258 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	303
0.1-0.2	1502
0.2-0.3	4857
0.3-0.4	13550
0.4-0.5	5651
0.5-0.6	8547
0.6-0.7	5795
0.7-0.8	2116
0.8-0.85	282
0.85-0.9	68
0.9-0.95	15
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC55617
0.9902	High Similarity	NPC147634
0.9902	High Similarity	NPC79793
0.9902	High Similarity	NPC174096
0.9902	High Similarity	NPC226401
0.9902	High Similarity	NPC120982
0.9806	High Similarity	NPC187583
0.9806	High Similarity	NPC179002
0.9806	High Similarity	NPC257430
0.9528	High Similarity	NPC120280
0.9314	High Similarity	NPC471511
0.9307	High Similarity	NPC110764
0.9238	High Similarity	NPC228343
0.9238	High Similarity	NPC254833
0.9223	High Similarity	NPC239291
0.9208	High Similarity	NPC294741
0.9126	High Similarity	NPC12278
0.9109	High Similarity	NPC131587
0.9109	High Similarity	NPC51333
0.9109	High Similarity	NPC132078
0.9109	High Similarity	NPC216468
0.9109	High Similarity	NPC78119
0.9099	High Similarity	NPC109371
0.9099	High Similarity	NPC470214
0.9099	High Similarity	NPC470215
0.9091	High Similarity	NPC145023
0.9091	High Similarity	NPC610
0.9091	High Similarity	NPC200988
0.9091	High Similarity	NPC175799
0.9074	High Similarity	NPC471485
0.9029	High Similarity	NPC196479
0.902	High Similarity	NPC213730
0.902	High Similarity	NPC223393
0.9018	High Similarity	NPC34634
0.9018	High Similarity	NPC265454
0.901	High Similarity	NPC109955
0.9009	High Similarity	NPC86198
0.8952	High Similarity	NPC477814
0.8938	High Similarity	NPC207613
0.8932	High Similarity	NPC91461
0.8932	High Similarity	NPC40258
0.8932	High Similarity	NPC7686
0.8929	High Similarity	NPC70084
0.8889	High Similarity	NPC297657
0.886	High Similarity	NPC113865
0.886	High Similarity	NPC312675
0.886	High Similarity	NPC262156
0.886	High Similarity	NPC470212
0.886	High Similarity	NPC473853
0.886	High Similarity	NPC184651
0.886	High Similarity	NPC290451
0.886	High Similarity	NPC324571
0.886	High Similarity	NPC343720
0.886	High Similarity	NPC54872
0.886	High Similarity	NPC127389
0.8812	High Similarity	NPC274678
0.8796	High Similarity	NPC44732
0.8785	High Similarity	NPC233835
0.8783	High Similarity	NPC86900
0.8772	High Similarity	NPC98305
0.8762	High Similarity	NPC323810
0.8762	High Similarity	NPC120719
0.875	High Similarity	NPC164386
0.8716	High Similarity	NPC308689
0.8716	High Similarity	NPC268032
0.8713	High Similarity	NPC76938
0.8713	High Similarity	NPC151715
0.8707	High Similarity	NPC473451
0.8707	High Similarity	NPC471693
0.8679	High Similarity	NPC233396
0.8679	High Similarity	NPC154899
0.8673	High Similarity	NPC470626
0.8641	High Similarity	NPC474073
0.8627	High Similarity	NPC107522
0.8627	High Similarity	NPC26244
0.8627	High Similarity	NPC32714
0.8621	High Similarity	NPC85488
0.8611	High Similarity	NPC262365
0.8609	High Similarity	NPC470848
0.8609	High Similarity	NPC470849
0.8598	High Similarity	NPC135464
0.8598	High Similarity	NPC92623
0.8596	High Similarity	NPC281298
0.8596	High Similarity	NPC24474
0.8596	High Similarity	NPC310338
0.8596	High Similarity	NPC141791
0.8596	High Similarity	NPC263386
0.8596	High Similarity	NPC311595
0.8584	High Similarity	NPC293619
0.8571	High Similarity	NPC101025
0.8571	High Similarity	NPC471578
0.8559	High Similarity	NPC148627
0.8547	High Similarity	NPC280704
0.8544	High Similarity	NPC216520
0.8544	High Similarity	NPC132271
0.8544	High Similarity	NPC473388
0.8544	High Similarity	NPC292730
0.8544	High Similarity	NPC82664
0.8522	High Similarity	NPC95614
0.8522	High Similarity	NPC56214
0.8522	High Similarity	NPC232316
0.8522	High Similarity	NPC242885
0.8522	High Similarity	NPC472071
0.8522	High Similarity	NPC117780
0.8522	High Similarity	NPC227217
0.8522	High Similarity	NPC165133
0.8519	High Similarity	NPC176527
0.8515	High Similarity	NPC45040
0.8509	High Similarity	NPC474214
0.8509	High Similarity	NPC144343
0.8496	Intermediate Similarity	NPC299252
0.8496	Intermediate Similarity	NPC277394
0.8496	Intermediate Similarity	NPC61062
0.8491	Intermediate Similarity	NPC477801
0.8491	Intermediate Similarity	NPC477802
0.8487	Intermediate Similarity	NPC94179
0.8482	Intermediate Similarity	NPC473137
0.8482	Intermediate Similarity	NPC12656
0.8475	Intermediate Similarity	NPC257682
0.8475	Intermediate Similarity	NPC146355
0.8475	Intermediate Similarity	NPC131747
0.8468	Intermediate Similarity	NPC51698
0.8462	Intermediate Similarity	NPC321402
0.8462	Intermediate Similarity	NPC471794
0.8448	Intermediate Similarity	NPC470414
0.844	Intermediate Similarity	NPC58427
0.844	Intermediate Similarity	NPC114392
0.844	Intermediate Similarity	NPC34864
0.844	Intermediate Similarity	NPC105727
0.8435	Intermediate Similarity	NPC474320
0.8431	Intermediate Similarity	NPC138117
0.8431	Intermediate Similarity	NPC325292
0.8426	Intermediate Similarity	NPC19149
0.8421	Intermediate Similarity	NPC277588
0.8421	Intermediate Similarity	NPC86947
0.8417	Intermediate Similarity	NPC79715
0.8417	Intermediate Similarity	NPC165045
0.8417	Intermediate Similarity	NPC231607
0.8417	Intermediate Similarity	NPC118533
0.8417	Intermediate Similarity	NPC264900
0.8417	Intermediate Similarity	NPC108659
0.8416	Intermediate Similarity	NPC192
0.8416	Intermediate Similarity	NPC300017
0.8403	Intermediate Similarity	NPC194519
0.839	Intermediate Similarity	NPC31344
0.839	Intermediate Similarity	NPC317769
0.8381	Intermediate Similarity	NPC92730
0.8376	Intermediate Similarity	NPC160380
0.8376	Intermediate Similarity	NPC38996
0.8376	Intermediate Similarity	NPC147654
0.8376	Intermediate Similarity	NPC472271
0.8362	Intermediate Similarity	NPC475245
0.8362	Intermediate Similarity	NPC223451
0.835	Intermediate Similarity	NPC128062
0.8348	Intermediate Similarity	NPC309434
0.8348	Intermediate Similarity	NPC275519
0.8348	Intermediate Similarity	NPC474040
0.8347	Intermediate Similarity	NPC252307
0.8347	Intermediate Similarity	NPC245826
0.8347	Intermediate Similarity	NPC186843
0.8347	Intermediate Similarity	NPC98631
0.8347	Intermediate Similarity	NPC474178
0.8347	Intermediate Similarity	NPC206615
0.8347	Intermediate Similarity	NPC470213
0.8333	Intermediate Similarity	NPC178284
0.8333	Intermediate Similarity	NPC191037
0.8333	Intermediate Similarity	NPC58607
0.8319	Intermediate Similarity	NPC48990
0.8319	Intermediate Similarity	NPC114901
0.8319	Intermediate Similarity	NPC293701
0.8318	Intermediate Similarity	NPC168829
0.8304	Intermediate Similarity	NPC471179
0.8304	Intermediate Similarity	NPC228425
0.8291	Intermediate Similarity	NPC24125
0.8288	Intermediate Similarity	NPC252544
0.8288	Intermediate Similarity	NPC321252
0.8288	Intermediate Similarity	NPC475018
0.8288	Intermediate Similarity	NPC63345
0.8286	Intermediate Similarity	NPC32674
0.8286	Intermediate Similarity	NPC225464
0.8279	Intermediate Similarity	NPC212015
0.8279	Intermediate Similarity	NPC476968
0.8279	Intermediate Similarity	NPC170844
0.8279	Intermediate Similarity	NPC475875
0.8279	Intermediate Similarity	NPC184092
0.8276	Intermediate Similarity	NPC217174
0.8276	Intermediate Similarity	NPC191866
0.8276	Intermediate Similarity	NPC268572
0.8273	Intermediate Similarity	NPC11554
0.8273	Intermediate Similarity	NPC75440
0.8269	Intermediate Similarity	NPC313650
0.8264	Intermediate Similarity	NPC118787
0.8264	Intermediate Similarity	NPC41706
0.8264	Intermediate Similarity	NPC319625
0.8264	Intermediate Similarity	NPC183181
0.8264	Intermediate Similarity	NPC111247
0.8264	Intermediate Similarity	NPC292056
0.8264	Intermediate Similarity	NPC163332
0.8264	Intermediate Similarity	NPC147821
0.8264	Intermediate Similarity	NPC5428

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 NPC62258 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	299
0.1-0.2	930
0.2-0.3	1472
0.3-0.4	2878
0.4-0.5	1894
0.5-0.6	1100
0.6-0.7	471
0.7-0.8	95
0.8-0.85	7
0.85-0.9	2
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9238	High Similarity	NPD3022	Approved
0.9238	High Similarity	NPD3021	Approved
0.8627	High Similarity	NPD2859	Approved
0.8627	High Similarity	NPD2860	Approved
0.8558	High Similarity	NPD3020	Approved
0.8529	High Similarity	NPD2934	Approved
0.8529	High Similarity	NPD2933	Approved
0.8279	Intermediate Similarity	NPD3027	Phase 3
0.8214	Intermediate Similarity	NPD228	Approved
0.8067	Intermediate Similarity	NPD3092	Approved
0.8051	Intermediate Similarity	NPD9381	Approved
0.8051	Intermediate Similarity	NPD9384	Approved
0.8034	Intermediate Similarity	NPD3091	Approved
0.8	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7982	Intermediate Similarity	NPD9377	Approved
0.7982	Intermediate Similarity	NPD9379	Approved
0.7963	Intermediate Similarity	NPD1242	Phase 1
0.7937	Intermediate Similarity	NPD3061	Approved
0.7937	Intermediate Similarity	NPD3062	Approved
0.7937	Intermediate Similarity	NPD3059	Approved
0.7925	Intermediate Similarity	NPD844	Approved
0.7913	Intermediate Similarity	NPD5283	Phase 1
0.7869	Intermediate Similarity	NPD5310	Approved
0.7869	Intermediate Similarity	NPD5311	Approved
0.7812	Intermediate Similarity	NPD5314	Approved
0.7805	Intermediate Similarity	NPD3055	Approved
0.7805	Intermediate Similarity	NPD3053	Approved
0.7805	Intermediate Similarity	NPD3094	Phase 2
0.7795	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7795	Intermediate Similarity	NPD1613	Approved
0.7795	Intermediate Similarity	NPD3620	Phase 2
0.7795	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7787	Intermediate Similarity	NPD9622	Approved
0.7787	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7685	Intermediate Similarity	NPD288	Approved
0.7652	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD111	Approved
0.7638	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD2684	Approved
0.7603	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD3095	Discontinued
0.76	Intermediate Similarity	NPD9621	Approved
0.76	Intermediate Similarity	NPD9619	Approved
0.76	Intermediate Similarity	NPD9620	Approved
0.7576	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD7266	Discontinued
0.7568	Intermediate Similarity	NPD940	Approved
0.7568	Intermediate Similarity	NPD846	Approved
0.7561	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD2342	Discontinued
0.7538	Intermediate Similarity	NPD823	Approved
0.7538	Intermediate Similarity	NPD817	Approved
0.7521	Intermediate Similarity	NPD1357	Approved
0.7521	Intermediate Similarity	NPD7635	Approved
0.75	Intermediate Similarity	NPD597	Approved
0.75	Intermediate Similarity	NPD598	Approved
0.75	Intermediate Similarity	NPD601	Approved
0.748	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD3028	Approved
0.7458	Intermediate Similarity	NPD2234	Approved
0.7458	Intermediate Similarity	NPD2229	Approved
0.7458	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD2228	Approved
0.7442	Intermediate Similarity	NPD1132	Approved
0.7442	Intermediate Similarity	NPD1130	Approved
0.7442	Intermediate Similarity	NPD1136	Approved
0.7431	Intermediate Similarity	NPD1809	Phase 2
0.7414	Intermediate Similarity	NPD1792	Phase 2
0.7414	Intermediate Similarity	NPD4750	Phase 3
0.7414	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD845	Approved
0.7402	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD2861	Phase 2
0.7377	Intermediate Similarity	NPD4093	Discontinued
0.7373	Intermediate Similarity	NPD7843	Approved
0.736	Intermediate Similarity	NPD4659	Approved
0.736	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7157	Approved
0.7323	Intermediate Similarity	NPD6584	Phase 3
0.7317	Intermediate Similarity	NPD5846	Approved
0.7317	Intermediate Similarity	NPD2932	Approved
0.7317	Intermediate Similarity	NPD4059	Approved
0.7317	Intermediate Similarity	NPD6516	Phase 2
0.7317	Intermediate Similarity	NPD2286	Discontinued
0.7317	Intermediate Similarity	NPD3019	Approved
0.7304	Intermediate Similarity	NPD1445	Approved
0.7304	Intermediate Similarity	NPD968	Approved
0.7304	Intermediate Similarity	NPD1444	Approved
0.728	Intermediate Similarity	NPD2561	Approved
0.728	Intermediate Similarity	NPD2562	Approved
0.7266	Intermediate Similarity	NPD5736	Approved
0.7252	Intermediate Similarity	NPD943	Approved
0.7252	Intermediate Similarity	NPD826	Approved
0.7252	Intermediate Similarity	NPD825	Approved
0.7252	Intermediate Similarity	NPD4060	Phase 1
0.725	Intermediate Similarity	NPD9618	Approved
0.725	Intermediate Similarity	NPD9614	Approved
0.7244	Intermediate Similarity	NPD4103	Phase 2
0.7244	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD6190	Approved
0.7213	Intermediate Similarity	NPD5536	Phase 2
0.7206	Intermediate Similarity	NPD3060	Approved
0.7193	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD6671	Approved
0.7188	Intermediate Similarity	NPD258	Approved
0.7188	Intermediate Similarity	NPD257	Approved
0.7176	Intermediate Similarity	NPD2674	Phase 3
0.7167	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD9634	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD8166	Discontinued
0.7143	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2235	Phase 2
0.7143	Intermediate Similarity	NPD2231	Phase 2
0.7121	Intermediate Similarity	NPD1558	Phase 1
0.7119	Intermediate Similarity	NPD5451	Approved
0.7109	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD290	Approved
0.7087	Intermediate Similarity	NPD6583	Phase 3
0.7087	Intermediate Similarity	NPD6582	Phase 2
0.7073	Intermediate Similarity	NPD856	Approved
0.7073	Intermediate Similarity	NPD9616	Approved
0.7073	Intermediate Similarity	NPD16	Approved
0.7073	Intermediate Similarity	NPD9613	Approved
0.7073	Intermediate Similarity	NPD9615	Approved
0.7071	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD3645	Discontinued
0.7068	Intermediate Similarity	NPD5735	Approved
0.7063	Intermediate Similarity	NPD1610	Phase 2
0.7045	Intermediate Similarity	NPD6407	Approved
0.7045	Intermediate Similarity	NPD6663	Approved
0.7045	Intermediate Similarity	NPD6405	Approved
0.704	Intermediate Similarity	NPD1751	Approved
0.704	Intermediate Similarity	NPD4589	Approved
0.703	Intermediate Similarity	NPD9294	Approved
0.7016	Intermediate Similarity	NPD5304	Approved
0.7016	Intermediate Similarity	NPD316	Approved
0.7016	Intermediate Similarity	NPD1548	Phase 1
0.7016	Intermediate Similarity	NPD5303	Approved
0.7015	Intermediate Similarity	NPD2568	Approved
0.7	Intermediate Similarity	NPD9494	Approved
0.7	Intermediate Similarity	NPD9569	Approved
0.6985	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD9570	Approved
0.6984	Remote Similarity	NPD3421	Phase 3
0.6983	Remote Similarity	NPD9608	Approved
0.6983	Remote Similarity	NPD9610	Approved
0.6978	Remote Similarity	NPD5241	Discontinued
0.697	Remote Similarity	NPD3144	Approved
0.697	Remote Similarity	NPD3145	Approved
0.6967	Remote Similarity	NPD2629	Approved
0.6957	Remote Similarity	NPD4162	Approved
0.6957	Remote Similarity	NPD5177	Phase 3
0.6953	Remote Similarity	NPD2982	Phase 2
0.6953	Remote Similarity	NPD2983	Phase 2
0.6947	Remote Similarity	NPD4908	Phase 1
0.6947	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD9094	Approved
0.694	Remote Similarity	NPD555	Phase 2
0.6935	Remote Similarity	NPD318	Approved
0.6935	Remote Similarity	NPD317	Approved
0.6929	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD3845	Phase 1
0.6917	Remote Similarity	NPD259	Phase 1
0.6912	Remote Similarity	NPD7743	Approved
0.6912	Remote Similarity	NPD7742	Approved
0.6906	Remote Similarity	NPD6331	Phase 2
0.6905	Remote Similarity	NPD4626	Approved
0.6905	Remote Similarity	NPD2667	Approved
0.6905	Remote Similarity	NPD2668	Approved
0.6897	Remote Similarity	NPD9500	Approved
0.6894	Remote Similarity	NPD7095	Approved
0.688	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD2421	Approved
0.6879	Remote Similarity	NPD2420	Approved
0.6875	Remote Similarity	NPD2233	Approved
0.6875	Remote Similarity	NPD2981	Phase 2
0.6875	Remote Similarity	NPD2232	Approved
0.6875	Remote Similarity	NPD9296	Approved
0.6875	Remote Similarity	NPD2230	Approved
0.6875	Remote Similarity	NPD3455	Phase 2
0.687	Remote Similarity	NPD3018	Phase 2
0.6866	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD2238	Phase 2
0.6866	Remote Similarity	NPD4140	Approved
0.685	Remote Similarity	NPD3847	Discontinued
0.6842	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5109	Approved
0.6842	Remote Similarity	NPD5111	Phase 2
0.6842	Remote Similarity	NPD6798	Discontinued
0.6842	Remote Similarity	NPD9495	Approved
0.6842	Remote Similarity	NPD5110	Phase 2
0.6838	Remote Similarity	NPD4538	Approved
0.6838	Remote Similarity	NPD1237	Approved
0.6838	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD4536	Approved
0.6835	Remote Similarity	NPD4236	Phase 3
0.6835	Remote Similarity	NPD4237	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