NPASS Compound

Structure

NPC86198 OpenBabel07101719252D 30 31 0 0 1 0 0 0 0 0999 V2000 0.0000 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 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 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 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 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -5.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 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 -0.8660 -7.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 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 -1.7321 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 16 1 0 0 0 0 3 8 1 0 0 0 0 3 17 2 0 0 0 0 4 9 2 0 0 0 0 4 17 1 0 0 0 0 5 10 1 0 0 0 0 5 17 1 0 0 0 0 6 11 1 0 0 0 0 6 18 1 0 0 0 0 7 12 2 0 0 0 0 7 18 1 0 0 0 0 8 19 2 0 0 0 0 9 19 1 0 0 0 0 12 22 1 0 0 0 0 13 18 2 0 0 0 0 13 23 1 0 0 0 0 14 20 1 0 0 0 0 14 21 1 0 0 0 0 15 24 2 0 0 0 0 15 29 1 0 0 0 0 16 25 2 0 0 0 0 16 30 1 0 0 0 0 19 26 1 0 0 0 0 20 10 1 6 0 0 0 20 29 1 0 0 0 0 21 11 1 1 0 0 0 21 30 1 0 0 0 0 22 23 2 0 0 0 0 22 27 1 0 0 0 0 23 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.18
Volume:	429.691
LogP:	3.007
LogD:	3.023
LogS:	-3.117
# Rotatable Bonds:	12
TPSA:	113.29
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.4
Synthetic Accessibility Score:	3.26
Fsp3:	0.391
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.859
MDCK Permeability:	2.777387089736294e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.023
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.979
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.018
Plasma Protein Binding (PPB):	96.07878875732422%
Volume Distribution (VD):	0.803
Pgp-substrate:	4.9703264236450195%

ADMET: Metabolism

CYP1A2-inhibitor:	0.373
CYP1A2-substrate:	0.058
CYP2C19-inhibitor:	0.64
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.663
CYP2C9-substrate:	0.97
CYP2D6-inhibitor:	0.922
CYP2D6-substrate:	0.857
CYP3A4-inhibitor:	0.529
CYP3A4-substrate:	0.23

ADMET: Excretion

Clearance (CL):	4.497
Half-life (T1/2):	0.952

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.795
Drug-inuced Liver Injury (DILI):	0.783
AMES Toxicity:	0.181
Rat Oral Acute Toxicity:	0.01
Maximum Recommended Daily Dose:	0.984
Skin Sensitization:	0.951
Carcinogencity:	0.458
Eye Corrosion:	0.028
Eye Irritation:	0.749
Respiratory Toxicity:	0.053

Download Data

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

Natural Product: NPC86198

Natural Product ID:	NPC86198
*Common Name:**	(3R,5R)-3,5-Diacetoxy-1-(3,4-Dihydroxyphenyl)-7-(4-Hydroxyphenyl)Heptane
IUPAC Name:	[(3R,5R)-5-acetyloxy-7-(3,4-dihydroxyphenyl)-1-(4-hydroxyphenyl)heptan-3-yl] acetate
Synonyms:
Standard InCHIKey:	PBCHINDGXDDCEA-NHCUHLMSSA-N
Standard InCHI:	InChI=1S/C23H28O7/c1-15(24)29-20(10-5-17-3-8-19(26)9-4-17)14-21(30-16(2)25)11-6-18-7-12-22(27)23(28)13-18/h3-4,7-9,12-13,20-21,26-28H,5-6,10-11,14H2,1-2H3/t20-,21-/m1/s1
SMILES:	CC(=O)O[C@@H](C[C@H](OC(=O)C)CCc1ccc(c(c1)O)O)CCc1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1824575
PubChem CID:	54577121
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	2
Others	8

Activity Type	# Activity
Cell Line	1
Individual Protein	1
NON-MOLECULAR	6
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	=	10670.0	nM	PMID[465621]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	<	17.0	%	PMID[465622]
NPT27	Others	Unspecified		Activity	=	92.3	%	PMID[465622]
NPT27	Others	Unspecified		Activity	=	95.2	%	PMID[465622]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[465622]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	27.3	%	PMID[465622]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	7.3	%	PMID[465622]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	8.1	%	PMID[465622]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	6.3	%	PMID[465622]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	3.6	%	PMID[465622]

☑ 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 NPC86198 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	220
0.1-0.2	1075
0.2-0.3	3181
0.3-0.4	9350
0.4-0.5	10268
0.5-0.6	6122
0.6-0.7	8840
0.7-0.8	3250
0.8-0.85	321
0.85-0.9	51
0.9-0.95	10
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.991	High Similarity	NPC70084
0.991	High Similarity	NPC470214
0.991	High Similarity	NPC470215
0.991	High Similarity	NPC109371
0.9909	High Similarity	NPC175799
0.9909	High Similarity	NPC145023
0.9909	High Similarity	NPC200988
0.9909	High Similarity	NPC610
0.9391	High Similarity	NPC470849
0.9391	High Similarity	NPC470848
0.9217	High Similarity	NPC263386
0.9217	High Similarity	NPC141791
0.9189	High Similarity	NPC187583
0.9189	High Similarity	NPC257430
0.9189	High Similarity	NPC179002
0.913	High Similarity	NPC309434
0.9099	High Similarity	NPC174096
0.9099	High Similarity	NPC226401
0.9099	High Similarity	NPC63345
0.9099	High Similarity	NPC79793
0.9099	High Similarity	NPC147634
0.9099	High Similarity	NPC120982
0.9027	High Similarity	NPC264558
0.9009	High Similarity	NPC62258
0.9009	High Similarity	NPC55617
0.8983	High Similarity	NPC472271
0.8983	High Similarity	NPC147654
0.8966	High Similarity	NPC203124
0.8966	High Similarity	NPC275519
0.8957	High Similarity	NPC281277
0.8898	High Similarity	NPC98305
0.887	High Similarity	NPC233669
0.8839	High Similarity	NPC254833
0.8839	High Similarity	NPC228343
0.8783	High Similarity	NPC120280
0.8783	High Similarity	NPC33749
0.8783	High Similarity	NPC328593
0.8783	High Similarity	NPC261453
0.877	High Similarity	NPC120225
0.877	High Similarity	NPC213552
0.876	High Similarity	NPC85565
0.8727	High Similarity	NPC471511
0.8707	High Similarity	NPC474967
0.8696	High Similarity	NPC95381
0.8696	High Similarity	NPC148969
0.8689	High Similarity	NPC289459
0.8684	High Similarity	NPC297657
0.8667	High Similarity	NPC312675
0.8667	High Similarity	NPC473853
0.8667	High Similarity	NPC470212
0.8667	High Similarity	NPC324571
0.8667	High Similarity	NPC54872
0.8667	High Similarity	NPC113865
0.8667	High Similarity	NPC262156
0.8667	High Similarity	NPC343720
0.8667	High Similarity	NPC184651
0.8661	High Similarity	NPC67247
0.8655	High Similarity	NPC34634
0.8655	High Similarity	NPC265454
0.8607	High Similarity	NPC288945
0.8607	High Similarity	NPC246704
0.8583	High Similarity	NPC207613
0.856	High Similarity	NPC83062
0.8559	High Similarity	NPC65791
0.8559	High Similarity	NPC278652
0.8527	High Similarity	NPC471988
0.8525	High Similarity	NPC473451
0.8522	High Similarity	NPC226250
0.8516	High Similarity	NPC135127
0.8516	High Similarity	NPC106406
0.8512	High Similarity	NPC322332
0.8487	Intermediate Similarity	NPC470626
0.8482	Intermediate Similarity	NPC239291
0.8468	Intermediate Similarity	NPC94179
0.8468	Intermediate Similarity	NPC118584
0.8468	Intermediate Similarity	NPC196479
0.8462	Intermediate Similarity	NPC217472
0.8462	Intermediate Similarity	NPC281780
0.8455	Intermediate Similarity	NPC146886
0.8455	Intermediate Similarity	NPC60517
0.8455	Intermediate Similarity	NPC223393
0.8455	Intermediate Similarity	NPC146355
0.8455	Intermediate Similarity	NPC20443
0.8455	Intermediate Similarity	NPC131747
0.8455	Intermediate Similarity	NPC257682
0.8448	Intermediate Similarity	NPC131530
0.8443	Intermediate Similarity	NPC86900
0.8438	Intermediate Similarity	NPC155209
0.8438	Intermediate Similarity	NPC168799
0.8435	Intermediate Similarity	NPC183700
0.8435	Intermediate Similarity	NPC222084
0.8425	Intermediate Similarity	NPC198388
0.8417	Intermediate Similarity	NPC24474
0.8417	Intermediate Similarity	NPC311595
0.8417	Intermediate Similarity	NPC241634
0.8413	Intermediate Similarity	NPC241354
0.8413	Intermediate Similarity	NPC30174
0.8407	Intermediate Similarity	NPC1075
0.8407	Intermediate Similarity	NPC1786
0.8407	Intermediate Similarity	NPC294902
0.8407	Intermediate Similarity	NPC92623
0.8407	Intermediate Similarity	NPC135464
0.8407	Intermediate Similarity	NPC477814
0.8403	Intermediate Similarity	NPC293619
0.84	Intermediate Similarity	NPC79715
0.84	Intermediate Similarity	NPC264900
0.84	Intermediate Similarity	NPC108659
0.84	Intermediate Similarity	NPC231607
0.8387	Intermediate Similarity	NPC67951
0.8387	Intermediate Similarity	NPC280767
0.8385	Intermediate Similarity	NPC154485
0.8385	Intermediate Similarity	NPC471872
0.8378	Intermediate Similarity	NPC40258
0.8378	Intermediate Similarity	NPC110764
0.8378	Intermediate Similarity	NPC7686
0.8378	Intermediate Similarity	NPC91461
0.8376	Intermediate Similarity	NPC471485
0.8374	Intermediate Similarity	NPC471693
0.8374	Intermediate Similarity	NPC317769
0.8374	Intermediate Similarity	NPC31344
0.8374	Intermediate Similarity	NPC280704
0.8374	Intermediate Similarity	NPC306100
0.8372	Intermediate Similarity	NPC68779
0.8372	Intermediate Similarity	NPC4982
0.8372	Intermediate Similarity	NPC5310
0.8372	Intermediate Similarity	NPC886
0.8372	Intermediate Similarity	NPC34293
0.8372	Intermediate Similarity	NPC300776
0.8372	Intermediate Similarity	NPC287597
0.8372	Intermediate Similarity	NPC176814
0.8362	Intermediate Similarity	NPC268032
0.8361	Intermediate Similarity	NPC127389
0.8361	Intermediate Similarity	NPC290451
0.8359	Intermediate Similarity	NPC18074
0.8359	Intermediate Similarity	NPC25581
0.8359	Intermediate Similarity	NPC5419
0.8359	Intermediate Similarity	NPC61
0.8347	Intermediate Similarity	NPC165133
0.8347	Intermediate Similarity	NPC232316
0.8347	Intermediate Similarity	NPC242885
0.8347	Intermediate Similarity	NPC56214
0.8347	Intermediate Similarity	NPC227217
0.8347	Intermediate Similarity	NPC117780
0.8347	Intermediate Similarity	NPC95614
0.8346	Intermediate Similarity	NPC217052
0.8346	Intermediate Similarity	NPC329344
0.8346	Intermediate Similarity	NPC237506
0.8346	Intermediate Similarity	NPC32626
0.8333	Intermediate Similarity	NPC474214
0.8333	Intermediate Similarity	NPC474178
0.8333	Intermediate Similarity	NPC252307
0.8333	Intermediate Similarity	NPC245826
0.8333	Intermediate Similarity	NPC63126
0.8333	Intermediate Similarity	NPC144343
0.8333	Intermediate Similarity	NPC478215
0.8333	Intermediate Similarity	NPC206205
0.8333	Intermediate Similarity	NPC110313
0.8321	Intermediate Similarity	NPC308976
0.8321	Intermediate Similarity	NPC67349
0.8321	Intermediate Similarity	NPC126206
0.8321	Intermediate Similarity	NPC279676
0.8319	Intermediate Similarity	NPC277394
0.8319	Intermediate Similarity	NPC61062
0.8319	Intermediate Similarity	NPC233396
0.8319	Intermediate Similarity	NPC123559
0.8319	Intermediate Similarity	NPC299252
0.8319	Intermediate Similarity	NPC154899
0.8308	Intermediate Similarity	NPC113295
0.8308	Intermediate Similarity	NPC123988
0.8306	Intermediate Similarity	NPC293701
0.8306	Intermediate Similarity	NPC469568
0.8306	Intermediate Similarity	NPC114901
0.8306	Intermediate Similarity	NPC48990
0.8293	Intermediate Similarity	NPC85488
0.8291	Intermediate Similarity	NPC51698
0.8288	Intermediate Similarity	NPC213730
0.8288	Intermediate Similarity	NPC294741
0.8281	Intermediate Similarity	NPC318799
0.8279	Intermediate Similarity	NPC470414
0.8279	Intermediate Similarity	NPC204466
0.8273	Intermediate Similarity	NPC109955
0.8271	Intermediate Similarity	NPC100675
0.8268	Intermediate Similarity	NPC475875
0.8268	Intermediate Similarity	NPC184092
0.8264	Intermediate Similarity	NPC160235
0.8264	Intermediate Similarity	NPC310338
0.8264	Intermediate Similarity	NPC281298
0.8264	Intermediate Similarity	NPC474320
0.8258	Intermediate Similarity	NPC68092
0.8258	Intermediate Similarity	NPC197316
0.8258	Intermediate Similarity	NPC476383
0.8258	Intermediate Similarity	NPC81515
0.8258	Intermediate Similarity	NPC64141
0.8258	Intermediate Similarity	NPC472350
0.8258	Intermediate Similarity	NPC89105
0.8254	Intermediate Similarity	NPC319625
0.8254	Intermediate Similarity	NPC118787
0.8254	Intermediate Similarity	NPC165045
0.8254	Intermediate Similarity	NPC183181
0.8254	Intermediate Similarity	NPC147821

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 NPC86198 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	189
0.1-0.2	776
0.2-0.3	1505
0.3-0.4	2624
0.4-0.5	2095
0.5-0.6	1132
0.6-0.7	723
0.7-0.8	104
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8839	High Similarity	NPD3021	Approved
0.8839	High Similarity	NPD3022	Approved
0.8258	Intermediate Similarity	NPD7266	Discontinued
0.8125	Intermediate Similarity	NPD3027	Phase 3
0.8091	Intermediate Similarity	NPD2860	Approved
0.8091	Intermediate Similarity	NPD2859	Approved
0.8036	Intermediate Similarity	NPD3020	Approved
0.8	Intermediate Similarity	NPD2933	Approved
0.8	Intermediate Similarity	NPD2934	Approved
0.7939	Intermediate Similarity	NPD825	Approved
0.7939	Intermediate Similarity	NPD4060	Phase 1
0.7939	Intermediate Similarity	NPD826	Approved
0.7937	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7899	Intermediate Similarity	NPD228	Approved
0.7829	Intermediate Similarity	NPD5736	Approved
0.781	Intermediate Similarity	NPD8166	Discontinued
0.7769	Intermediate Similarity	NPD5283	Phase 1
0.7754	Intermediate Similarity	NPD6190	Approved
0.7669	Intermediate Similarity	NPD1613	Approved
0.7669	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD258	Approved
0.7615	Intermediate Similarity	NPD257	Approved
0.7612	Intermediate Similarity	NPD555	Phase 2
0.7594	Intermediate Similarity	NPD6663	Approved
0.7576	Intermediate Similarity	NPD7095	Approved
0.7541	Intermediate Similarity	NPD5535	Approved
0.7538	Intermediate Similarity	NPD3094	Phase 2
0.7522	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD6798	Discontinued
0.75	Intermediate Similarity	NPD3455	Phase 2
0.75	Intermediate Similarity	NPD3092	Approved
0.75	Intermediate Similarity	NPD1242	Phase 1
0.75	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD6355	Discontinued
0.7481	Intermediate Similarity	NPD230	Phase 1
0.7463	Intermediate Similarity	NPD259	Phase 1
0.7463	Intermediate Similarity	NPD6233	Phase 2
0.746	Intermediate Similarity	NPD3091	Approved
0.7456	Intermediate Similarity	NPD844	Approved
0.7429	Intermediate Similarity	NPD4110	Phase 3
0.7429	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD3847	Discontinued
0.7419	Intermediate Similarity	NPD2629	Approved
0.7407	Intermediate Similarity	NPD3061	Approved
0.7407	Intermediate Similarity	NPD3620	Phase 2
0.7407	Intermediate Similarity	NPD3062	Approved
0.7407	Intermediate Similarity	NPD3059	Approved
0.7407	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD3053	Approved
0.7405	Intermediate Similarity	NPD3055	Approved
0.7398	Intermediate Similarity	NPD9377	Approved
0.7398	Intermediate Similarity	NPD9379	Approved
0.7381	Intermediate Similarity	NPD5536	Phase 2
0.7355	Intermediate Similarity	NPD2684	Approved
0.7344	Intermediate Similarity	NPD9384	Approved
0.7344	Intermediate Similarity	NPD4626	Approved
0.7344	Intermediate Similarity	NPD9381	Approved
0.7338	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4062	Phase 3
0.7328	Intermediate Similarity	NPD5310	Approved
0.7328	Intermediate Similarity	NPD5311	Approved
0.7299	Intermediate Similarity	NPD5314	Approved
0.7293	Intermediate Similarity	NPD9569	Approved
0.7288	Intermediate Similarity	NPD940	Approved
0.7288	Intermediate Similarity	NPD846	Approved
0.7287	Intermediate Similarity	NPD3496	Discontinued
0.7279	Intermediate Similarity	NPD4140	Approved
0.7279	Intermediate Similarity	NPD943	Approved
0.7273	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1358	Approved
0.7266	Intermediate Similarity	NPD9570	Approved
0.7266	Intermediate Similarity	NPD5691	Approved
0.7266	Intermediate Similarity	NPD1357	Approved
0.7266	Intermediate Similarity	NPD2935	Discontinued
0.7258	Intermediate Similarity	NPD7843	Approved
0.7252	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD9622	Approved
0.7241	Intermediate Similarity	NPD288	Approved
0.7236	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD275	Approved
0.7226	Intermediate Similarity	NPD274	Approved
0.7222	Intermediate Similarity	NPD7157	Approved
0.7222	Intermediate Similarity	NPD4198	Discontinued
0.7219	Intermediate Similarity	NPD6234	Discontinued
0.7218	Intermediate Similarity	NPD6584	Phase 3
0.7209	Intermediate Similarity	NPD3019	Approved
0.7209	Intermediate Similarity	NPD2932	Approved
0.7209	Intermediate Similarity	NPD3095	Discontinued
0.7203	Intermediate Similarity	NPD3028	Approved
0.7203	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1283	Approved
0.719	Intermediate Similarity	NPD3134	Approved
0.7188	Intermediate Similarity	NPD1894	Discontinued
0.7183	Intermediate Similarity	NPD4628	Phase 3
0.7182	Intermediate Similarity	NPD111	Approved
0.7181	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD9269	Phase 2
0.7174	Intermediate Similarity	NPD6653	Approved
0.7164	Intermediate Similarity	NPD2861	Phase 2
0.7154	Intermediate Similarity	NPD4750	Phase 3
0.7143	Intermediate Similarity	NPD2438	Suspended
0.7143	Intermediate Similarity	NPD6032	Approved
0.7132	Intermediate Similarity	NPD5585	Approved
0.7132	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD7635	Approved
0.7114	Intermediate Similarity	NPD1934	Approved
0.7111	Intermediate Similarity	NPD4908	Phase 1
0.7099	Intermediate Similarity	NPD1535	Discovery
0.7092	Intermediate Similarity	NPD5763	Approved
0.7092	Intermediate Similarity	NPD5762	Approved
0.709	Intermediate Similarity	NPD9620	Approved
0.709	Intermediate Similarity	NPD9621	Approved
0.709	Intermediate Similarity	NPD9619	Approved
0.7087	Intermediate Similarity	NPD6671	Approved
0.7077	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD1653	Approved
0.7063	Intermediate Similarity	NPD2229	Approved
0.7063	Intermediate Similarity	NPD2228	Approved
0.7063	Intermediate Similarity	NPD2234	Approved
0.7059	Intermediate Similarity	NPD9536	Phase 1
0.7059	Intermediate Similarity	NPD9537	Phase 1
0.7054	Intermediate Similarity	NPD9545	Approved
0.7049	Intermediate Similarity	NPD968	Approved
0.7045	Intermediate Similarity	NPD1608	Approved
0.7045	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD1481	Phase 2
0.7042	Intermediate Similarity	NPD4534	Discontinued
0.7037	Intermediate Similarity	NPD9494	Approved
0.7029	Intermediate Similarity	NPD2979	Phase 3
0.7029	Intermediate Similarity	NPD1558	Phase 1
0.7016	Intermediate Similarity	NPD1792	Phase 2
0.7015	Intermediate Similarity	NPD2797	Approved
0.7009	Intermediate Similarity	NPD1809	Phase 2
0.7007	Intermediate Similarity	NPD3764	Approved
0.7007	Intermediate Similarity	NPD601	Approved
0.7007	Intermediate Similarity	NPD598	Approved
0.7007	Intermediate Similarity	NPD597	Approved
0.7007	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7097	Phase 1
0.7	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD37	Approved
0.7	Intermediate Similarity	NPD4093	Discontinued
0.6993	Remote Similarity	NPD3060	Approved
0.6992	Remote Similarity	NPD6582	Phase 2
0.6992	Remote Similarity	NPD2342	Discontinued
0.6992	Remote Similarity	NPD2982	Phase 2
0.6992	Remote Similarity	NPD290	Approved
0.6992	Remote Similarity	NPD6583	Phase 3
0.6992	Remote Similarity	NPD2983	Phase 2
0.6983	Remote Similarity	NPD845	Approved
0.6978	Remote Similarity	NPD4340	Discontinued
0.6974	Remote Similarity	NPD4965	Approved
0.6974	Remote Similarity	NPD4967	Phase 2
0.6974	Remote Similarity	NPD4966	Approved
0.697	Remote Similarity	NPD422	Phase 1
0.697	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1610	Phase 2
0.697	Remote Similarity	NPD1281	Approved
0.697	Remote Similarity	NPD3705	Approved
0.6967	Remote Similarity	NPD5048	Discontinued
0.6957	Remote Similarity	NPD1132	Approved
0.6957	Remote Similarity	NPD6405	Approved
0.6957	Remote Similarity	NPD2674	Phase 3
0.6957	Remote Similarity	NPD6407	Approved
0.6957	Remote Similarity	NPD1136	Approved
0.6957	Remote Similarity	NPD1130	Approved
0.6953	Remote Similarity	NPD256	Approved
0.6953	Remote Similarity	NPD255	Approved
0.695	Remote Similarity	NPD7033	Discontinued
0.6947	Remote Similarity	NPD1778	Approved
0.6947	Remote Similarity	NPD5846	Approved
0.6947	Remote Similarity	NPD4059	Approved
0.6947	Remote Similarity	NPD6516	Phase 2
0.694	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD5163	Phase 2
0.6929	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD817	Approved
0.6929	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD823	Approved
0.6923	Remote Similarity	NPD5958	Discontinued
0.6923	Remote Similarity	NPD1548	Phase 1
0.6917	Remote Similarity	NPD2981	Phase 2
0.6912	Remote Similarity	NPD3018	Phase 2
0.6911	Remote Similarity	NPD1445	Approved
0.6911	Remote Similarity	NPD1444	Approved
0.6906	Remote Similarity	NPD6346	Approved
0.6905	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD7228	Approved
0.6891	Remote Similarity	NPD9495	Approved
0.6889	Remote Similarity	NPD1164	Approved
0.6889	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD3268	Approved
0.688	Remote Similarity	NPD5451	Approved
0.6879	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4536	Approved
0.6879	Remote Similarity	NPD4538	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