NPASS Compound

Structure

NPC257430 OpenBabel07101719522D 24 25 0 0 1 0 0 0 0 0999 V2000 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 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 3.4641 -0.0000 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 6.0622 -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 -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 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 2 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 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 O 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 6 1 0 0 0 0 1 13 2 0 0 0 0 2 7 2 0 0 0 0 2 13 1 0 0 0 0 3 8 1 0 0 0 0 3 13 1 0 0 0 0 4 9 1 0 0 0 0 4 14 1 0 0 0 0 5 10 2 0 0 0 0 5 14 1 0 0 0 0 6 15 2 0 0 0 0 7 15 1 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 14 2 0 0 0 0 11 19 1 0 0 0 0 12 16 1 0 0 0 0 12 17 1 0 0 0 0 15 20 1 0 0 0 0 16 21 1 6 0 0 0 17 22 1 6 0 0 0 18 19 2 0 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.16
Volume:	348.2
LogP:	2.308
LogD:	2.465
LogS:	-2.68
# Rotatable Bonds:	8
TPSA:	101.15
# H-Bond Aceptor:	5
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.478
Synthetic Accessibility Score:	2.96
Fsp3:	0.368
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.333
MDCK Permeability:	5.986211363051552e-06
Pgp-inhibitor:	0.006
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.618
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.037
Plasma Protein Binding (PPB):	93.38895416259766%
Volume Distribution (VD):	0.965
Pgp-substrate:	11.02187442779541%

ADMET: Metabolism

CYP1A2-inhibitor:	0.602
CYP1A2-substrate:	0.118
CYP2C19-inhibitor:	0.706
CYP2C19-substrate:	0.077
CYP2C9-inhibitor:	0.696
CYP2C9-substrate:	0.927
CYP2D6-inhibitor:	0.773
CYP2D6-substrate:	0.86
CYP3A4-inhibitor:	0.295
CYP3A4-substrate:	0.29

ADMET: Excretion

Clearance (CL):	17.339
Half-life (T1/2):	0.934

ADMET: Toxicity

hERG Blockers:	0.094
Human Hepatotoxicity (H-HT):	0.191
Drug-inuced Liver Injury (DILI):	0.012
AMES Toxicity:	0.348
Rat Oral Acute Toxicity:	0.075
Maximum Recommended Daily Dose:	0.971
Skin Sensitization:	0.963
Carcinogencity:	0.307
Eye Corrosion:	0.094
Eye Irritation:	0.962
Respiratory Toxicity:	0.498

Download Data

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

Natural Product: NPC257430

Natural Product ID:	NPC257430
*Common Name:**	4-[(3R,5S)-3,5-Dihydroxy-7-(4-Hydroxyphenyl)Heptyl]Benzene-1,2-Diol
IUPAC Name:	4-[(3R,5S)-3,5-dihydroxy-7-(4-hydroxyphenyl)heptyl]benzene-1,2-diol
Synonyms:
Standard InCHIKey:	XLTITIJKWVRJMS-DLBZAZTESA-N
Standard InCHI:	InChI=1S/C19H24O5/c20-15-6-1-13(2-7-15)3-8-16(21)12-17(22)9-4-14-5-10-18(23)19(24)11-14/h1-2,5-7,10-11,16-17,20-24H,3-4,8-9,12H2/t16-,17+/m0/s1
SMILES:	c1cc(ccc1CC[C@@H](C[C@@H](CCc1ccc(c(c1)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1824567
PubChem CID:	53387510
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]
NPO22901	Curcuma comosa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22741	Curcuma kwangsiensis	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	7

Activity Type	# Activity
Cell Line	1
Individual Protein	1
NON-MOLECULAR	4
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	3130.0	nM	PMID[450108]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	<	17.0	%	PMID[450109]
NPT27	Others	Unspecified		Activity	=	71.6	%	PMID[450109]
NPT27	Others	Unspecified		Activity	>	91.9	%	PMID[450109]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	-23.7	%	PMID[450109]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	-10.9	%	PMID[450109]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	-3.7	%	PMID[450109]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	-0.7	%	PMID[450109]

☑ 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 NPC257430 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	313
0.1-0.2	1388
0.2-0.3	4622
0.3-0.4	13313
0.4-0.5	5888
0.5-0.6	8045
0.6-0.7	6370
0.7-0.8	2357
0.8-0.85	300
0.85-0.9	75
0.9-0.95	15
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC179002
1.0	High Similarity	NPC187583
0.9903	High Similarity	NPC147634
0.9903	High Similarity	NPC79793
0.9903	High Similarity	NPC174096
0.9903	High Similarity	NPC226401
0.9903	High Similarity	NPC120982
0.9806	High Similarity	NPC62258
0.9806	High Similarity	NPC55617
0.9533	High Similarity	NPC120280
0.932	High Similarity	NPC471511
0.9279	High Similarity	NPC470214
0.9279	High Similarity	NPC109371
0.9279	High Similarity	NPC470215
0.9245	High Similarity	NPC254833
0.9245	High Similarity	NPC228343
0.9189	High Similarity	NPC86198
0.9126	High Similarity	NPC40258
0.9126	High Similarity	NPC91461
0.9126	High Similarity	NPC7686
0.9126	High Similarity	NPC110764
0.9107	High Similarity	NPC70084
0.9099	High Similarity	NPC610
0.9099	High Similarity	NPC200988
0.9099	High Similarity	NPC145023
0.9099	High Similarity	NPC175799
0.9083	High Similarity	NPC471485
0.9048	High Similarity	NPC239291
0.9035	High Similarity	NPC54872
0.9035	High Similarity	NPC470212
0.9035	High Similarity	NPC324571
0.9035	High Similarity	NPC473853
0.9035	High Similarity	NPC262156
0.9035	High Similarity	NPC312675
0.9035	High Similarity	NPC343720
0.9035	High Similarity	NPC113865
0.9035	High Similarity	NPC184651
0.9029	High Similarity	NPC294741
0.9029	High Similarity	NPC213730
0.9029	High Similarity	NPC223393
0.9027	High Similarity	NPC265454
0.9027	High Similarity	NPC34634
0.8952	High Similarity	NPC12278
0.8947	High Similarity	NPC207613
0.8932	High Similarity	NPC78119
0.8932	High Similarity	NPC216468
0.8932	High Similarity	NPC132078
0.8932	High Similarity	NPC51333
0.8932	High Similarity	NPC131587
0.8899	High Similarity	NPC268032
0.8899	High Similarity	NPC297657
0.8879	High Similarity	NPC473451
0.8857	High Similarity	NPC196479
0.8835	High Similarity	NPC109955
0.8807	High Similarity	NPC44732
0.8793	High Similarity	NPC86900
0.8785	High Similarity	NPC477814
0.8783	High Similarity	NPC98305
0.8774	High Similarity	NPC323810
0.8772	High Similarity	NPC24474
0.8772	High Similarity	NPC311595
0.8727	High Similarity	NPC308689
0.8718	High Similarity	NPC280704
0.8718	High Similarity	NPC471693
0.8707	High Similarity	NPC290451
0.8707	High Similarity	NPC127389
0.8696	High Similarity	NPC472071
0.8692	High Similarity	NPC154899
0.8692	High Similarity	NPC233396
0.8684	High Similarity	NPC474214
0.8684	High Similarity	NPC144343
0.8684	High Similarity	NPC470626
0.8661	High Similarity	NPC473137
0.8655	High Similarity	NPC94179
0.8644	High Similarity	NPC257682
0.8644	High Similarity	NPC146355
0.8644	High Similarity	NPC131747
0.8641	High Similarity	NPC274678
0.8632	High Similarity	NPC85488
0.8624	High Similarity	NPC233835
0.8624	High Similarity	NPC34864
0.8624	High Similarity	NPC58427
0.8624	High Similarity	NPC105727
0.8624	High Similarity	NPC114392
0.8621	High Similarity	NPC470848
0.8621	High Similarity	NPC470849
0.8611	High Similarity	NPC92623
0.8611	High Similarity	NPC135464
0.8609	High Similarity	NPC474320
0.8609	High Similarity	NPC263386
0.8609	High Similarity	NPC141791
0.8598	High Similarity	NPC120719
0.8596	High Similarity	NPC293619
0.8596	High Similarity	NPC277588
0.8596	High Similarity	NPC164386
0.8583	High Similarity	NPC165045
0.8583	High Similarity	NPC231607
0.8583	High Similarity	NPC264900
0.8583	High Similarity	NPC118533
0.8583	High Similarity	NPC79715
0.8583	High Similarity	NPC108659
0.8571	High Similarity	NPC148627
0.8544	High Similarity	NPC76938
0.8544	High Similarity	NPC151715
0.8534	High Similarity	NPC117780
0.8534	High Similarity	NPC223451
0.8534	High Similarity	NPC165133
0.8534	High Similarity	NPC227217
0.8534	High Similarity	NPC232316
0.8534	High Similarity	NPC95614
0.8534	High Similarity	NPC56214
0.8534	High Similarity	NPC242885
0.8532	High Similarity	NPC176527
0.8512	High Similarity	NPC470213
0.8512	High Similarity	NPC252307
0.8512	High Similarity	NPC98631
0.8512	High Similarity	NPC245826
0.8512	High Similarity	NPC186843
0.8512	High Similarity	NPC474178
0.8512	High Similarity	NPC206615
0.8509	High Similarity	NPC299252
0.8509	High Similarity	NPC61062
0.8509	High Similarity	NPC277394
0.8505	High Similarity	NPC477802
0.8505	High Similarity	NPC477801
0.8496	Intermediate Similarity	NPC12656
0.8487	Intermediate Similarity	NPC293701
0.8487	Intermediate Similarity	NPC48990
0.8487	Intermediate Similarity	NPC114901
0.8482	Intermediate Similarity	NPC51698
0.8476	Intermediate Similarity	NPC474073
0.8468	Intermediate Similarity	NPC63345
0.8468	Intermediate Similarity	NPC475018
0.8462	Intermediate Similarity	NPC107522
0.8462	Intermediate Similarity	NPC24125
0.8462	Intermediate Similarity	NPC26244
0.8462	Intermediate Similarity	NPC470414
0.8462	Intermediate Similarity	NPC32714
0.8455	Intermediate Similarity	NPC262365
0.8448	Intermediate Similarity	NPC310338
0.8448	Intermediate Similarity	NPC217174
0.8448	Intermediate Similarity	NPC281298
0.8448	Intermediate Similarity	NPC191866
0.8443	Intermediate Similarity	NPC184092
0.8443	Intermediate Similarity	NPC170844
0.8443	Intermediate Similarity	NPC212015
0.8443	Intermediate Similarity	NPC475875
0.8443	Intermediate Similarity	NPC476968
0.843	Intermediate Similarity	NPC163332
0.843	Intermediate Similarity	NPC111247
0.843	Intermediate Similarity	NPC118787
0.843	Intermediate Similarity	NPC292056
0.843	Intermediate Similarity	NPC147821
0.843	Intermediate Similarity	NPC41706
0.843	Intermediate Similarity	NPC183181
0.843	Intermediate Similarity	NPC319625
0.843	Intermediate Similarity	NPC5428
0.8421	Intermediate Similarity	NPC474486
0.8421	Intermediate Similarity	NPC472893
0.8417	Intermediate Similarity	NPC194519
0.8411	Intermediate Similarity	NPC471578
0.8411	Intermediate Similarity	NPC101025
0.8403	Intermediate Similarity	NPC317769
0.8403	Intermediate Similarity	NPC136319
0.8403	Intermediate Similarity	NPC31344
0.839	Intermediate Similarity	NPC472271
0.839	Intermediate Similarity	NPC476343
0.839	Intermediate Similarity	NPC266045
0.839	Intermediate Similarity	NPC147654
0.839	Intermediate Similarity	NPC38996
0.839	Intermediate Similarity	NPC237667
0.839	Intermediate Similarity	NPC160380
0.8381	Intermediate Similarity	NPC473388
0.8381	Intermediate Similarity	NPC132271
0.8381	Intermediate Similarity	NPC216520
0.8381	Intermediate Similarity	NPC292730
0.8381	Intermediate Similarity	NPC82664
0.8376	Intermediate Similarity	NPC475245
0.8374	Intermediate Similarity	NPC174495
0.8374	Intermediate Similarity	NPC257582
0.8374	Intermediate Similarity	NPC92164
0.8374	Intermediate Similarity	NPC77040
0.8374	Intermediate Similarity	NPC145305
0.8374	Intermediate Similarity	NPC187998
0.8374	Intermediate Similarity	NPC64201
0.8374	Intermediate Similarity	NPC153739
0.8374	Intermediate Similarity	NPC241522
0.8374	Intermediate Similarity	NPC242807
0.8374	Intermediate Similarity	NPC42300
0.8362	Intermediate Similarity	NPC309434
0.8362	Intermediate Similarity	NPC474040
0.8362	Intermediate Similarity	NPC275519
0.8361	Intermediate Similarity	NPC148982
0.8361	Intermediate Similarity	NPC72529
0.835	Intermediate Similarity	NPC45040
0.8348	Intermediate Similarity	NPC301651
0.8348	Intermediate Similarity	NPC473556
0.8347	Intermediate Similarity	NPC58607
0.8347	Intermediate Similarity	NPC191037
0.8347	Intermediate Similarity	NPC178284

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 NPC257430 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	282
0.1-0.2	871
0.2-0.3	1561
0.3-0.4	2863
0.4-0.5	1877
0.5-0.6	1112
0.6-0.7	482
0.7-0.8	91
0.8-0.85	9
0.85-0.9	0
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9245	High Similarity	NPD3021	Approved
0.9245	High Similarity	NPD3022	Approved
0.8462	Intermediate Similarity	NPD2860	Approved
0.8462	Intermediate Similarity	NPD2859	Approved
0.8443	Intermediate Similarity	NPD3027	Phase 3
0.8396	Intermediate Similarity	NPD3020	Approved
0.8365	Intermediate Similarity	NPD2933	Approved
0.8365	Intermediate Similarity	NPD2934	Approved
0.807	Intermediate Similarity	NPD228	Approved
0.7982	Intermediate Similarity	NPD1242	Phase 1
0.7967	Intermediate Similarity	NPD3094	Phase 2
0.7953	Intermediate Similarity	NPD3061	Approved
0.7953	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD3059	Approved
0.7953	Intermediate Similarity	NPD3062	Approved
0.7953	Intermediate Similarity	NPD1613	Approved
0.7934	Intermediate Similarity	NPD3092	Approved
0.7931	Intermediate Similarity	NPD5283	Phase 1
0.7917	Intermediate Similarity	NPD9384	Approved
0.7917	Intermediate Similarity	NPD9381	Approved
0.7899	Intermediate Similarity	NPD3091	Approved
0.785	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7845	Intermediate Similarity	NPD9377	Approved
0.7845	Intermediate Similarity	NPD9379	Approved
0.7829	Intermediate Similarity	NPD5314	Approved
0.7805	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD844	Approved
0.7742	Intermediate Similarity	NPD5311	Approved
0.7742	Intermediate Similarity	NPD5310	Approved
0.7727	Intermediate Similarity	NPD7266	Discontinued
0.768	Intermediate Similarity	NPD3055	Approved
0.768	Intermediate Similarity	NPD3053	Approved
0.7674	Intermediate Similarity	NPD3620	Phase 2
0.7674	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7672	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD9622	Approved
0.7638	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7623	Intermediate Similarity	NPD3095	Discontinued
0.7589	Intermediate Similarity	NPD846	Approved
0.7589	Intermediate Similarity	NPD940	Approved
0.7559	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD288	Approved
0.7519	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3028	Approved
0.75	Intermediate Similarity	NPD2684	Approved
0.75	Intermediate Similarity	NPD111	Approved
0.75	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD9621	Approved
0.748	Intermediate Similarity	NPD9619	Approved
0.748	Intermediate Similarity	NPD9620	Approved
0.748	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7479	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD4750	Phase 3
0.7424	Intermediate Similarity	NPD817	Approved
0.7424	Intermediate Similarity	NPD823	Approved
0.7414	Intermediate Similarity	NPD2342	Discontinued
0.7405	Intermediate Similarity	NPD943	Approved
0.7398	Intermediate Similarity	NPD1357	Approved
0.7395	Intermediate Similarity	NPD7635	Approved
0.7395	Intermediate Similarity	NPD7843	Approved
0.7385	Intermediate Similarity	NPD601	Approved
0.7385	Intermediate Similarity	NPD597	Approved
0.7385	Intermediate Similarity	NPD598	Approved
0.7381	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD6190	Approved
0.736	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD7157	Approved
0.7333	Intermediate Similarity	NPD2228	Approved
0.7333	Intermediate Similarity	NPD2229	Approved
0.7333	Intermediate Similarity	NPD2234	Approved
0.7328	Intermediate Similarity	NPD1136	Approved
0.7328	Intermediate Similarity	NPD1132	Approved
0.7328	Intermediate Similarity	NPD1130	Approved
0.7297	Intermediate Similarity	NPD1809	Phase 2
0.7288	Intermediate Similarity	NPD1792	Phase 2
0.7288	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD2861	Phase 2
0.7273	Intermediate Similarity	NPD825	Approved
0.7273	Intermediate Similarity	NPD845	Approved
0.7273	Intermediate Similarity	NPD826	Approved
0.7273	Intermediate Similarity	NPD4060	Phase 1
0.7258	Intermediate Similarity	NPD4093	Discontinued
0.7244	Intermediate Similarity	NPD4659	Approved
0.7236	Intermediate Similarity	NPD5536	Phase 2
0.7226	Intermediate Similarity	NPD3060	Approved
0.7209	Intermediate Similarity	NPD258	Approved
0.7209	Intermediate Similarity	NPD6584	Phase 3
0.7209	Intermediate Similarity	NPD257	Approved
0.72	Intermediate Similarity	NPD5846	Approved
0.72	Intermediate Similarity	NPD4059	Approved
0.72	Intermediate Similarity	NPD3019	Approved
0.72	Intermediate Similarity	NPD6516	Phase 2
0.72	Intermediate Similarity	NPD2932	Approved
0.72	Intermediate Similarity	NPD2286	Discontinued
0.7197	Intermediate Similarity	NPD6405	Approved
0.7197	Intermediate Similarity	NPD6407	Approved
0.719	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD9634	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD968	Approved
0.7179	Intermediate Similarity	NPD1444	Approved
0.7179	Intermediate Similarity	NPD1445	Approved
0.7174	Intermediate Similarity	NPD8166	Discontinued
0.7167	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD2561	Approved
0.7165	Intermediate Similarity	NPD2562	Approved
0.7164	Intermediate Similarity	NPD2568	Approved
0.7154	Intermediate Similarity	NPD5736	Approved
0.7132	Intermediate Similarity	NPD9570	Approved
0.7132	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD4103	Phase 2
0.7132	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD9618	Approved
0.7131	Intermediate Similarity	NPD9614	Approved
0.7119	Intermediate Similarity	NPD290	Approved
0.7109	Intermediate Similarity	NPD2983	Phase 2
0.7109	Intermediate Similarity	NPD2982	Phase 2
0.7099	Intermediate Similarity	NPD4908	Phase 1
0.7087	Intermediate Similarity	NPD1610	Phase 2
0.7073	Intermediate Similarity	NPD6671	Approved
0.7069	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD2674	Phase 3
0.704	Intermediate Similarity	NPD1548	Phase 1
0.7031	Intermediate Similarity	NPD2231	Phase 2
0.7031	Intermediate Similarity	NPD2235	Phase 2
0.7031	Intermediate Similarity	NPD2981	Phase 2
0.7023	Intermediate Similarity	NPD3018	Phase 2
0.7023	Intermediate Similarity	NPD9569	Approved
0.7015	Intermediate Similarity	NPD1558	Phase 1
0.7007	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5451	Approved
0.6992	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD4538	Approved
0.6985	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD4536	Approved
0.6978	Remote Similarity	NPD5177	Phase 3
0.6978	Remote Similarity	NPD4162	Approved
0.6978	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6582	Phase 2
0.6977	Remote Similarity	NPD6583	Phase 3
0.6972	Remote Similarity	NPD3645	Discontinued
0.6972	Remote Similarity	NPD9094	Approved
0.6972	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD555	Phase 2
0.6963	Remote Similarity	NPD5735	Approved
0.696	Remote Similarity	NPD16	Approved
0.696	Remote Similarity	NPD9616	Approved
0.696	Remote Similarity	NPD856	Approved
0.696	Remote Similarity	NPD9615	Approved
0.696	Remote Similarity	NPD9613	Approved
0.694	Remote Similarity	NPD259	Phase 1
0.694	Remote Similarity	NPD6663	Approved
0.6939	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD5588	Approved
0.6934	Remote Similarity	NPD5960	Phase 3
0.6929	Remote Similarity	NPD1751	Approved
0.6929	Remote Similarity	NPD4589	Approved
0.6917	Remote Similarity	NPD7095	Approved
0.6905	Remote Similarity	NPD5303	Approved
0.6905	Remote Similarity	NPD316	Approved
0.6905	Remote Similarity	NPD5304	Approved
0.6899	Remote Similarity	NPD9269	Phase 2
0.6897	Remote Similarity	NPD3455	Phase 2
0.6894	Remote Similarity	NPD9494	Approved
0.6893	Remote Similarity	NPD9294	Approved
0.6889	Remote Similarity	NPD2238	Phase 2
0.6879	Remote Similarity	NPD5241	Discontinued
0.6875	Remote Similarity	NPD3847	Discontinued
0.6875	Remote Similarity	NPD3421	Phase 3
0.6871	Remote Similarity	NPD1934	Approved
0.6866	Remote Similarity	NPD6798	Discontinued
0.6866	Remote Similarity	NPD5109	Approved
0.6866	Remote Similarity	NPD5111	Phase 2
0.6866	Remote Similarity	NPD5110	Phase 2
0.6866	Remote Similarity	NPD3145	Approved
0.6866	Remote Similarity	NPD3144	Approved
0.6864	Remote Similarity	NPD9608	Approved
0.6864	Remote Similarity	NPD9610	Approved
0.6857	Remote Similarity	NPD4236	Phase 3
0.6857	Remote Similarity	NPD4237	Approved
0.6855	Remote Similarity	NPD2629	Approved
0.6853	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD230	Phase 1
0.6838	Remote Similarity	NPD275	Approved
0.6838	Remote Similarity	NPD6355	Discontinued
0.6838	Remote Similarity	NPD274	Approved
0.6838	Remote Similarity	NPD291	Approved
0.6831	Remote Similarity	NPD3845	Phase 1
0.6831	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD5535	Approved
0.6825	Remote Similarity	NPD318	Approved
0.6825	Remote Similarity	NPD317	Approved
0.6824	Remote Similarity	NPD2978	Approved
0.6824	Remote Similarity	NPD2977	Approved
0.6822	Remote Similarity	NPD1091	Approved
0.6822	Remote Similarity	NPD3705	Approved
0.6815	Remote Similarity	NPD6233	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data