NPASS Compound

Structure

CID279209 OpenBabel06191716082D 35 39 0 0 1 0 0 0 0 0999 V2000 -3.0878 1.7891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -2.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5491 -1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 -2.7770 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8793 -1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 -4.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -4.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -3.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 0.9230 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 33 1 0 0 0 0 2 3 2 0 0 0 0 2 10 1 0 0 0 0 3 15 1 0 0 0 0 4 11 2 0 0 0 0 4 13 1 0 0 0 0 5 11 1 0 0 0 0 5 17 2 0 0 0 0 6 10 2 0 0 0 0 6 18 1 0 0 0 0 7 12 2 0 0 0 0 7 16 1 0 0 0 0 8 12 1 0 0 0 0 8 19 2 0 0 0 0 9 26 1 0 0 0 0 12 27 1 0 0 0 0 13 14 1 0 0 0 0 13 25 2 0 0 0 0 14 9 1 1 0 0 0 14 23 1 0 0 0 0 15 18 2 0 0 0 0 15 28 1 0 0 0 0 16 20 2 0 0 0 0 16 29 1 0 0 0 0 17 25 1 0 0 0 0 17 30 1 0 0 0 0 18 33 1 0 0 0 0 19 20 1 0 0 0 0 19 34 1 0 0 0 0 20 21 1 0 0 0 0 21 22 1 0 0 0 0 21 31 2 0 0 0 0 22 24 1 0 0 0 0 22 32 1 6 0 0 0 23 10 1 6 0 0 0 23 35 1 0 0 0 0 24 11 1 1 0 0 0 24 34 1 0 0 0 0 25 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	482.12
Volume:	459.711
LogP:	1.896
LogD:	2.23
LogS:	-4.919
# Rotatable Bonds:	4
TPSA:	166.14
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.325
Synthetic Accessibility Score:	4.199
Fsp3:	0.24
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.291
MDCK Permeability:	5.6396625041088555e-06
Pgp-inhibitor:	0.048
Pgp-substrate:	0.036
Human Intestinal Absorption (HIA):	0.167
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.03
Plasma Protein Binding (PPB):	93.77666473388672%
Volume Distribution (VD):	0.633
Pgp-substrate:	9.719922065734863%

ADMET: Metabolism

CYP1A2-inhibitor:	0.052
CYP1A2-substrate:	0.156
CYP2C19-inhibitor:	0.04
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.576
CYP2C9-substrate:	0.779
CYP2D6-inhibitor:	0.097
CYP2D6-substrate:	0.225
CYP3A4-inhibitor:	0.642
CYP3A4-substrate:	0.256

ADMET: Excretion

Clearance (CL):	7.02
Half-life (T1/2):	0.451

ADMET: Toxicity

hERG Blockers:	0.064
Human Hepatotoxicity (H-HT):	0.303
Drug-inuced Liver Injury (DILI):	0.932
AMES Toxicity:	0.159
Rat Oral Acute Toxicity:	0.494
Maximum Recommended Daily Dose:	0.884
Skin Sensitization:	0.783
Carcinogencity:	0.141
Eye Corrosion:	0.003
Eye Irritation:	0.368
Respiratory Toxicity:	0.044

Download Data

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

Natural Product: NPC279209

Natural Product ID:	NPC279209
*Common Name:**	Silychristin
IUPAC Name:	(2R,3R)-3,5,7-trihydroxy-2-[(2R,3S)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-5-yl]-2,3-dihydrochromen-4-one
Synonyms:	(+)-Silychristin; Silychristin
Standard InCHIKey:	BMLIIPOXVWESJG-LMBCONBSSA-N
Standard InCHI:	InChI=1S/C25H22O10/c1-33-18-6-10(2-3-15(18)28)23-14(9-26)13-4-11(5-17(30)25(13)35-23)24-22(32)21(31)20-16(29)7-12(27)8-19(20)34-24/h2-8,14,22-24,26-30,32H,9H2,1H3/t14-,22+,23+,24-/m1/s1
SMILES:	COc1cc(ccc1O)[C@H]1[C@H](CO)c2cc(cc(c2O1)O)[C@@H]1[C@H](C(=O)c2c(cc(cc2O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL130493
PubChem CID:	441764
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO21361	Anastatica hierochuntica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12643908]
NPO5645	Silybum marianum	Species	Asteraceae	Eukaryota	n.a.	whole plant	n.a.	PMID[16394559]
NPO21361	Anastatica hierochuntica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20189399]
NPO5645	Silybum marianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24456525]
NPO5645	Silybum marianum	Species	Asteraceae	Eukaryota	Seeds	n.a.	n.a.	PMID[24597776]
NPO5645	Silybum marianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5645	Silybum marianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5645	Silybum marianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5645	Silybum marianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21361	Anastatica hierochuntica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5645	Silybum marianum	Species	Asteraceae	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	9
Ki	4
Others	9

Activity Type	# Activity
Individual Protein	14
Others	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	KA	=	3.548	10'6L/mol	PMID[520985]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	KSV	=	0.1924	10'4L/mol	PMID[520985]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Kis	=	37.3	uM	PMID[520985]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Ki	=	15200.0	nM	PMID[520985]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Ki	=	15400.0	nM	PMID[520985]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	=	28800.0	nM	PMID[520985]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Ki	=	2100.0	nM	PMID[520985]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	=	3200.0	nM	PMID[520985]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Kis	=	2.9	uM	PMID[520985]
NPT1568	Individual Protein	Trypsin I	Bos taurus	IC50	=	144400	nM	PMID[9406602]
NPT622	Individual Protein	Solute carrier organic anion transporter family member 2B1	Homo sapiens	IC50	=	3600	nM	PMID[23401473]
NPT2	Others	Unspecified		Inhibition	=	4.1	%	PMID[520984]
NPT2	Others	Unspecified		Inhibition	=	1.3	%	PMID[520984]
NPT2	Others	Unspecified		Inhibition	=	3.8	%	PMID[520984]
NPT2	Others	Unspecified		Inhibition	=	17.4	%	PMID[520984]
NPT27	Others	Unspecified		Inhibition	<	8.8	%	PMID[520984]
NPT2	Others	Unspecified		IC50	>	50000.0	nM	PMID[520986]
NPT2	Others	Unspecified		IC50	=	144400	nM	PMID[7673925]
NPT2	Others	Unspecified		IC50	>	130000	nM	PMID[23673225]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	IC50	=	9000	nM	PMID[23401473]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	IC50	=	36400	nM	PMID[23401473]

☑ 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 NPC279209 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	428
0.1-0.2	1654
0.2-0.3	3610
0.3-0.4	9461
0.4-0.5	8962
0.5-0.6	3619
0.6-0.7	4823
0.7-0.8	5513
0.8-0.85	2744
0.85-0.9	1607
0.9-0.95	257
0.95-1	19

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC102277
0.956	High Similarity	NPC471499
0.956	High Similarity	NPC142252
0.9503	High Similarity	NPC58223
0.9503	High Similarity	NPC36916
0.9503	High Similarity	NPC72787
0.9503	High Similarity	NPC7688
0.9503	High Similarity	NPC125039
0.9503	High Similarity	NPC7154
0.9503	High Similarity	NPC36
0.95	High Similarity	NPC476247
0.95	High Similarity	NPC472635
0.9497	High Similarity	NPC282009
0.9497	High Similarity	NPC470326
0.9497	High Similarity	NPC287328
0.9451	High Similarity	NPC472454
0.9451	High Similarity	NPC257667
0.9451	High Similarity	NPC186847
0.9444	High Similarity	NPC471213
0.9441	High Similarity	NPC472625
0.9437	High Similarity	NPC26326
0.9437	High Similarity	NPC158188
0.9437	High Similarity	NPC289771
0.9434	High Similarity	NPC22192
0.9401	High Similarity	NPC244903
0.9387	High Similarity	NPC260266
0.9387	High Similarity	NPC150131
0.9383	High Similarity	NPC62261
0.9375	High Similarity	NPC472624
0.9371	High Similarity	NPC474055
0.9371	High Similarity	NPC472598
0.9333	High Similarity	NPC121333
0.9329	High Similarity	NPC475212
0.9329	High Similarity	NPC165456
0.9329	High Similarity	NPC107627
0.9321	High Similarity	NPC124038
0.9317	High Similarity	NPC474038
0.9317	High Similarity	NPC66618
0.9317	High Similarity	NPC472634
0.9317	High Similarity	NPC113163
0.9317	High Similarity	NPC165970
0.9317	High Similarity	NPC84324
0.9317	High Similarity	NPC288131
0.9317	High Similarity	NPC472632
0.9317	High Similarity	NPC305987
0.9313	High Similarity	NPC284127
0.9313	High Similarity	NPC53545
0.9313	High Similarity	NPC172202
0.9313	High Similarity	NPC476410
0.9313	High Similarity	NPC117418
0.9308	High Similarity	NPC320825
0.9308	High Similarity	NPC195796
0.9308	High Similarity	NPC278778
0.9308	High Similarity	NPC35038
0.9308	High Similarity	NPC250922
0.9308	High Similarity	NPC13858
0.9308	High Similarity	NPC326037
0.9308	High Similarity	NPC291878
0.9268	High Similarity	NPC295082
0.9264	High Similarity	NPC472277
0.9264	High Similarity	NPC475888
0.9259	High Similarity	NPC474150
0.9259	High Similarity	NPC474034
0.9259	High Similarity	NPC474162
0.9259	High Similarity	NPC211107
0.9259	High Similarity	NPC474033
0.9255	High Similarity	NPC475784
0.9255	High Similarity	NPC192686
0.9255	High Similarity	NPC472631
0.9255	High Similarity	NPC472962
0.9255	High Similarity	NPC36217
0.9255	High Similarity	NPC118256
0.9255	High Similarity	NPC472630
0.9255	High Similarity	NPC470183
0.9255	High Similarity	NPC174953
0.9255	High Similarity	NPC472961
0.9255	High Similarity	NPC101731
0.9255	High Similarity	NPC119209
0.925	High Similarity	NPC471479
0.925	High Similarity	NPC52530
0.925	High Similarity	NPC27337
0.925	High Similarity	NPC291508
0.925	High Similarity	NPC63454
0.925	High Similarity	NPC471515
0.925	High Similarity	NPC183851
0.9245	High Similarity	NPC321779
0.9245	High Similarity	NPC477503
0.9245	High Similarity	NPC45849
0.9245	High Similarity	NPC200761
0.9245	High Similarity	NPC470327
0.9217	High Similarity	NPC4200
0.9212	High Similarity	NPC152477
0.9212	High Similarity	NPC242395
0.9212	High Similarity	NPC188079
0.9212	High Similarity	NPC288813
0.9207	High Similarity	NPC320741
0.9207	High Similarity	NPC235610
0.9207	High Similarity	NPC171985
0.9207	High Similarity	NPC224851
0.9207	High Similarity	NPC128293
0.9207	High Similarity	NPC119589
0.9207	High Similarity	NPC43065
0.9202	High Similarity	NPC18100
0.9202	High Similarity	NPC474240
0.9202	High Similarity	NPC186686
0.9202	High Similarity	NPC205265
0.9202	High Similarity	NPC472281
0.9202	High Similarity	NPC476295
0.9202	High Similarity	NPC41301
0.9202	High Similarity	NPC273959
0.9198	High Similarity	NPC187354
0.9198	High Similarity	NPC471211
0.9198	High Similarity	NPC173137
0.9198	High Similarity	NPC471212
0.9198	High Similarity	NPC471210
0.9198	High Similarity	NPC266314
0.9193	High Similarity	NPC473990
0.9187	High Similarity	NPC472626
0.9187	High Similarity	NPC78492
0.9187	High Similarity	NPC209614
0.9187	High Similarity	NPC471500
0.9187	High Similarity	NPC470328
0.9187	High Similarity	NPC208152
0.9182	High Similarity	NPC244250
0.9182	High Similarity	NPC20907
0.9182	High Similarity	NPC18727
0.9182	High Similarity	NPC192083
0.9182	High Similarity	NPC213896
0.9157	High Similarity	NPC131866
0.9152	High Similarity	NPC470456
0.9152	High Similarity	NPC243877
0.9152	High Similarity	NPC474024
0.9152	High Similarity	NPC14662
0.9146	High Similarity	NPC470457
0.9146	High Similarity	NPC326520
0.9146	High Similarity	NPC471788
0.9146	High Similarity	NPC477840
0.9146	High Similarity	NPC300053
0.9146	High Similarity	NPC293319
0.9146	High Similarity	NPC108433
0.9146	High Similarity	NPC224280
0.9141	High Similarity	NPC201800
0.9141	High Similarity	NPC477841
0.9141	High Similarity	NPC219927
0.9136	High Similarity	NPC321399
0.9136	High Similarity	NPC328102
0.9136	High Similarity	NPC476283
0.9136	High Similarity	NPC263449
0.913	High Similarity	NPC129684
0.913	High Similarity	NPC473272
0.913	High Similarity	NPC223787
0.913	High Similarity	NPC471209
0.913	High Similarity	NPC67876
0.913	High Similarity	NPC299520
0.913	High Similarity	NPC284820
0.9125	High Similarity	NPC304745
0.9125	High Similarity	NPC226025
0.9125	High Similarity	NPC111341
0.9119	High Similarity	NPC216035
0.9119	High Similarity	NPC260979
0.9119	High Similarity	NPC219582
0.9119	High Similarity	NPC61506
0.9119	High Similarity	NPC236637
0.9119	High Similarity	NPC217149
0.9119	High Similarity	NPC302950
0.9119	High Similarity	NPC260491
0.9119	High Similarity	NPC9743
0.9119	High Similarity	NPC246162
0.9119	High Similarity	NPC106976
0.9119	High Similarity	NPC472912
0.9119	High Similarity	NPC36835
0.9119	High Similarity	NPC240476
0.9119	High Similarity	NPC19721
0.9107	High Similarity	NPC108202
0.9096	High Similarity	NPC300307
0.9096	High Similarity	NPC177480
0.9096	High Similarity	NPC326877
0.9091	High Similarity	NPC173292
0.9091	High Similarity	NPC13481
0.9091	High Similarity	NPC207575
0.9091	High Similarity	NPC43319
0.9091	High Similarity	NPC477517
0.9091	High Similarity	NPC470462
0.9091	High Similarity	NPC170245
0.9085	High Similarity	NPC470459
0.9085	High Similarity	NPC472582
0.9085	High Similarity	NPC63438
0.908	High Similarity	NPC301256
0.908	High Similarity	NPC112418
0.908	High Similarity	NPC134783
0.908	High Similarity	NPC312273
0.908	High Similarity	NPC308992
0.908	High Similarity	NPC474239
0.9074	High Similarity	NPC123544
0.9074	High Similarity	NPC55738
0.9074	High Similarity	NPC250214
0.9074	High Similarity	NPC210459
0.9074	High Similarity	NPC95936
0.9068	High Similarity	NPC20530
0.9068	High Similarity	NPC215917

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 NPC279209 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	380
0.1-0.2	917
0.2-0.3	1743
0.3-0.4	2653
0.4-0.5	1823
0.5-0.6	983
0.6-0.7	466
0.7-0.8	131
0.8-0.85	31
0.85-0.9	18
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9503	High Similarity	NPD6168	Clinical (unspecified phase)
0.9503	High Similarity	NPD6167	Clinical (unspecified phase)
0.9503	High Similarity	NPD6166	Phase 2
0.9182	High Similarity	NPD2393	Clinical (unspecified phase)
0.9119	High Similarity	NPD1934	Approved
0.8951	High Similarity	NPD3882	Suspended
0.8902	High Similarity	NPD5494	Approved
0.8817	High Similarity	NPD7074	Phase 3
0.881	High Similarity	NPD3818	Discontinued
0.8773	High Similarity	NPD8443	Clinical (unspecified phase)
0.8765	High Similarity	NPD6797	Phase 2
0.8758	High Similarity	NPD4380	Phase 2
0.8757	High Similarity	NPD7054	Approved
0.872	High Similarity	NPD4868	Clinical (unspecified phase)
0.8713	High Similarity	NPD7251	Discontinued
0.8712	High Similarity	NPD2801	Approved
0.8706	High Similarity	NPD7472	Approved
0.8667	High Similarity	NPD7075	Discontinued
0.8663	High Similarity	NPD7808	Phase 3
0.8663	High Similarity	NPD4338	Clinical (unspecified phase)
0.8659	High Similarity	NPD3817	Phase 2
0.8625	High Similarity	NPD1512	Approved
0.8562	High Similarity	NPD4378	Clinical (unspecified phase)
0.8547	High Similarity	NPD7993	Clinical (unspecified phase)
0.8538	High Similarity	NPD5844	Phase 1
0.8538	High Similarity	NPD7804	Clinical (unspecified phase)
0.8529	High Similarity	NPD7473	Discontinued
0.8512	High Similarity	NPD6959	Discontinued
0.85	High Similarity	NPD1511	Approved
0.8485	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD6232	Discontinued
0.8443	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8424	Intermediate Similarity	NPD6801	Discontinued
0.8391	Intermediate Similarity	NPD6559	Discontinued
0.8364	Intermediate Similarity	NPD7411	Suspended
0.8333	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD7819	Suspended
0.8239	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8198	Intermediate Similarity	NPD3926	Phase 2
0.8187	Intermediate Similarity	NPD1549	Phase 2
0.815	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD5402	Approved
0.8101	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8081	Intermediate Similarity	NPD7199	Phase 2
0.8081	Intermediate Similarity	NPD1247	Approved
0.807	Intermediate Similarity	NPD919	Approved
0.8049	Intermediate Similarity	NPD6799	Approved
0.8047	Intermediate Similarity	NPD1465	Phase 2
0.8012	Intermediate Similarity	NPD5403	Approved
0.7976	Intermediate Similarity	NPD6599	Discontinued
0.7965	Intermediate Similarity	NPD6234	Discontinued
0.7955	Intermediate Similarity	NPD7228	Approved
0.7953	Intermediate Similarity	NPD7768	Phase 2
0.795	Intermediate Similarity	NPD2796	Approved
0.7907	Intermediate Similarity	NPD3749	Approved
0.7904	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD5401	Approved
0.7888	Intermediate Similarity	NPD1510	Phase 2
0.7882	Intermediate Similarity	NPD37	Approved
0.788	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7869	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD1613	Approved
0.7862	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD4966	Approved
0.7849	Intermediate Similarity	NPD4965	Approved
0.7849	Intermediate Similarity	NPD4967	Phase 2
0.7805	Intermediate Similarity	NPD2800	Approved
0.779	Intermediate Similarity	NPD8313	Approved
0.779	Intermediate Similarity	NPD8312	Approved
0.7784	Intermediate Similarity	NPD2532	Approved
0.7784	Intermediate Similarity	NPD2534	Approved
0.7784	Intermediate Similarity	NPD2533	Approved
0.7753	Intermediate Similarity	NPD3751	Discontinued
0.775	Intermediate Similarity	NPD1240	Approved
0.7736	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7735	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD3787	Discontinued
0.7713	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD3027	Phase 3
0.7663	Intermediate Similarity	NPD8434	Phase 2
0.7663	Intermediate Similarity	NPD8150	Discontinued
0.7654	Intermediate Similarity	NPD1607	Approved
0.764	Intermediate Similarity	NPD943	Approved
0.7636	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD7390	Discontinued
0.7619	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD4908	Phase 1
0.761	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD6190	Approved
0.7592	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7592	Intermediate Similarity	NPD6781	Approved
0.7592	Intermediate Similarity	NPD6776	Approved
0.7592	Intermediate Similarity	NPD6777	Approved
0.7592	Intermediate Similarity	NPD6778	Approved
0.7592	Intermediate Similarity	NPD6779	Approved
0.7592	Intermediate Similarity	NPD6780	Approved
0.7592	Intermediate Similarity	NPD6782	Approved
0.7582	Intermediate Similarity	NPD7685	Pre-registration
0.7574	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD4628	Phase 3
0.7545	Intermediate Similarity	NPD3750	Approved
0.7515	Intermediate Similarity	NPD2935	Discontinued
0.7513	Intermediate Similarity	NPD4363	Phase 3
0.7513	Intermediate Similarity	NPD4360	Phase 2
0.75	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3226	Approved
0.7486	Intermediate Similarity	NPD7240	Approved
0.7485	Intermediate Similarity	NPD920	Approved
0.7474	Intermediate Similarity	NPD7435	Discontinued
0.747	Intermediate Similarity	NPD2344	Approved
0.7462	Intermediate Similarity	NPD8151	Discontinued
0.7455	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD1653	Approved
0.7439	Intermediate Similarity	NPD6651	Approved
0.7436	Intermediate Similarity	NPD7871	Phase 2
0.7436	Intermediate Similarity	NPD7870	Phase 2
0.743	Intermediate Similarity	NPD7229	Phase 3
0.7429	Intermediate Similarity	NPD8455	Phase 2
0.741	Intermediate Similarity	NPD6099	Approved
0.741	Intermediate Similarity	NPD6100	Approved
0.7385	Intermediate Similarity	NPD7698	Approved
0.7385	Intermediate Similarity	NPD7696	Phase 3
0.7385	Intermediate Similarity	NPD7697	Approved
0.7381	Intermediate Similarity	NPD1243	Approved
0.7378	Intermediate Similarity	NPD230	Phase 1
0.7374	Intermediate Similarity	NPD8127	Discontinued
0.7368	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD2799	Discontinued
0.7337	Intermediate Similarity	NPD5953	Discontinued
0.7333	Intermediate Similarity	NPD5710	Approved
0.7333	Intermediate Similarity	NPD5711	Approved
0.733	Intermediate Similarity	NPD6534	Approved
0.733	Intermediate Similarity	NPD6535	Approved
0.7323	Intermediate Similarity	NPD7701	Phase 2
0.7305	Intermediate Similarity	NPD1551	Phase 2
0.7301	Intermediate Similarity	NPD6798	Discontinued
0.7301	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD7801	Approved
0.73	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD7783	Phase 2
0.7294	Intermediate Similarity	NPD2309	Approved
0.7292	Intermediate Similarity	NPD4361	Phase 2
0.7292	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD2494	Approved
0.7282	Intermediate Similarity	NPD2493	Approved
0.7273	Intermediate Similarity	NPD6355	Discontinued
0.7273	Intermediate Similarity	NPD7584	Approved
0.7273	Intermediate Similarity	NPD447	Suspended
0.7263	Intermediate Similarity	NPD2490	Approved
0.7263	Intermediate Similarity	NPD2488	Approved
0.7262	Intermediate Similarity	NPD2346	Discontinued
0.7259	Intermediate Similarity	NPD4582	Approved
0.7259	Intermediate Similarity	NPD4583	Approved
0.7253	Intermediate Similarity	NPD2403	Approved
0.725	Intermediate Similarity	NPD7874	Approved
0.725	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD3748	Approved
0.7235	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD7286	Phase 2
0.722	Intermediate Similarity	NPD4111	Phase 1
0.722	Intermediate Similarity	NPD4665	Approved
0.7216	Intermediate Similarity	NPD7700	Phase 2
0.7216	Intermediate Similarity	NPD7699	Phase 2
0.7212	Intermediate Similarity	NPD4060	Phase 1
0.7208	Intermediate Similarity	NPD4004	Approved
0.7208	Intermediate Similarity	NPD7680	Approved
0.7208	Intermediate Similarity	NPD4002	Approved
0.72	Intermediate Similarity	NPD7458	Discontinued
0.7194	Intermediate Similarity	NPD3450	Approved
0.7194	Intermediate Similarity	NPD3452	Approved
0.7179	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6674	Discontinued
0.7172	Intermediate Similarity	NPD8320	Phase 1
0.7172	Intermediate Similarity	NPD8319	Approved
0.717	Intermediate Similarity	NPD1610	Phase 2
0.7169	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD1933	Approved
0.7169	Intermediate Similarity	NPD5124	Phase 1
0.7157	Intermediate Similarity	NPD6823	Phase 2
0.7152	Intermediate Similarity	NPD6233	Phase 2
0.715	Intermediate Similarity	NPD7907	Approved
0.7143	Intermediate Similarity	NPD7033	Discontinued
0.7135	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD5761	Phase 2
0.7135	Intermediate Similarity	NPD5760	Phase 2
0.7126	Intermediate Similarity	NPD6273	Approved
0.7119	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD2424	Discontinued
0.7117	Intermediate Similarity	NPD9494	Approved
0.7117	Intermediate Similarity	NPD2861	Phase 2
0.7091	Intermediate Similarity	NPD2313	Discontinued
0.7081	Intermediate Similarity	NPD2163	Approved
0.7081	Intermediate Similarity	NPD4379	Clinical (unspecified phase)

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