NPASS Compound

Structure

CID185258 OpenBabel06191715562D 29 31 0 0 0 0 0 0 0 0999 V2000 5.1962 -2.0000 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 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9641 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -2.8660 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 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 3.4641 0.0000 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 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 2 11 1 0 0 0 0 3 11 1 0 0 0 0 4 23 1 0 0 0 0 5 23 1 0 0 0 0 6 23 1 0 0 0 0 7 8 1 0 0 0 0 7 11 2 0 0 0 0 8 12 1 0 0 0 0 9 13 1 0 0 0 0 9 14 2 0 0 0 0 10 15 2 0 0 0 0 10 16 1 0 0 0 0 12 20 2 0 0 0 0 12 22 1 0 0 0 0 13 16 2 0 0 0 0 13 19 1 0 0 0 0 14 15 1 0 0 0 0 14 24 1 0 0 0 0 15 25 1 0 0 0 0 16 29 1 0 0 0 0 17 19 1 0 0 0 0 17 21 1 0 0 0 0 17 22 2 0 0 0 0 18 20 1 0 0 0 0 18 21 2 0 0 0 0 18 23 1 0 0 0 0 19 26 2 0 0 0 0 20 27 1 0 0 0 0 21 28 1 0 0 0 0 22 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	396.16
Volume:	409.708
LogP:	5.492
LogD:	2.669
LogS:	-3.192
# Rotatable Bonds:	4
TPSA:	111.13
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.288
Synthetic Accessibility Score:	3.313
Fsp3:	0.261
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:	-4.915
MDCK Permeability:	1.3465275515045505e-05
Pgp-inhibitor:	0.855
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.194
20% Bioavailability (F20%):	0.925
30% Bioavailability (F30%):	0.305

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	92.5689697265625%
Volume Distribution (VD):	0.891
Pgp-substrate:	12.614272117614746%

ADMET: Metabolism

CYP1A2-inhibitor:	0.737
CYP1A2-substrate:	0.22
CYP2C19-inhibitor:	0.365
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.757
CYP2C9-substrate:	0.695
CYP2D6-inhibitor:	0.428
CYP2D6-substrate:	0.193
CYP3A4-inhibitor:	0.15
CYP3A4-substrate:	0.087

ADMET: Excretion

Clearance (CL):	1.536
Half-life (T1/2):	0.583

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.285
Drug-inuced Liver Injury (DILI):	0.867
AMES Toxicity:	0.492
Rat Oral Acute Toxicity:	0.21
Maximum Recommended Daily Dose:	0.547
Skin Sensitization:	0.933
Carcinogencity:	0.261
Eye Corrosion:	0.003
Eye Irritation:	0.891
Respiratory Toxicity:	0.278

Download Data

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

Natural Product: NPC185258

Natural Product ID:	NPC185258
*Common Name:**	Macluraxanthone B
IUPAC Name:	1,3,6,7-tetrahydroxy-2-(2-methylbut-3-en-2-yl)-4-(3-methylbut-2-enyl)xanthen-9-one
Synonyms:
Standard InCHIKey:	QFYDCUMYVXSZFJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C23H24O6/c1-6-23(4,5)18-20(27)12(8-7-11(2)3)22-17(21(18)28)19(26)13-9-14(24)15(25)10-16(13)29-22/h6-7,9-10,24-25,27-28H,1,8H2,2-5H3
SMILES:	C=CC(c1c(O)c(CC=C(C)C)c2c(c1O)c(=O)c1c(o2)cc(c(c1)O)O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL370126
PubChem CID:	5353737
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones [CHEMONTID:0003518] 4-prenylated xanthones

*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
NPO27239	Maclura tinctoria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11087602]
NPO27239	Maclura tinctoria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12932124]
NPO27239	Maclura tinctoria	Species	Moraceae	Eukaryota	n.a.	stem	n.a.	PMID[12932124]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[15787460]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15787460]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16203143]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16919944]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	root bark	n.a.	n.a.	PMID[17608532]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17950599]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	fruits	n.a.	n.a.	PMID[19113968]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	Roots	n.a.	n.a.	PMID[19191562]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[19280148]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19285413]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19660948]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[21319773]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	Roots	n.a.	n.a.	PMID[25322455]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	root barks	purchased from the local herbal market, Chungbuk, Korea	2012-JUL	PMID[26227773]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27239	Maclura tinctoria	Species	Moraceae	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
EC50	1
IC50	11
LD50	5

Activity Type	# Activity
Cell Line	8
Individual Protein	2
NON-MOLECULAR	1
Organism	1
Others	4
Tissue	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	LD50	=	28.0	uM	PMID[558825]
NPT116	Cell Line	HL-60	Homo sapiens	LD50	=	29.5	uM	PMID[558825]
NPT146	Cell Line	SK-OV-3	Homo sapiens	LD50	=	23.1	uM	PMID[558825]
NPT196	Cell Line	AGS	Homo sapiens	LD50	=	15.2	uM	PMID[558825]
NPT81	Cell Line	A549	Homo sapiens	LD50	=	25.8	uM	PMID[558825]
NPT1214	Individual Protein	Acyl coenzyme A:cholesterol acyltransferase 1	Homo sapiens	IC50	=	96000.0	nM	PMID[558826]
NPT2584	Individual Protein	Acyl coenzyme A:cholesterol acyltransferase 2	Homo sapiens	IC50	=	112000.0	nM	PMID[558826]
NPT315	Cell Line	CEM-SS	Homo sapiens	IC50	=	2.2	ug.mL-1	PMID[558828]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	2880.0	nM	PMID[558829]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	4240.0	nM	PMID[558829]
NPT1	Others	Radical scavenging activity		IC50	=	15400.0	nM	PMID[558825]
NPT1	Others	Radical scavenging activity		IC50	=	47800.0	nM	PMID[558825]
NPT1	Others	Radical scavenging activity		IC50	=	74100.0	nM	PMID[558825]
NPT614	Tissue	Plasma	Rattus norvegicus	IC50	=	4500.0	nM	PMID[558826]
NPT2	Others	Unspecified		IC50	=	38200.0	nM	PMID[558827]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	1.0	ug.mL-1	PMID[558828]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	13300.0	nM	PMID[558830]

☑ 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 NPC185258 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	451
0.1-0.2	1825
0.2-0.3	4231
0.3-0.4	10683
0.4-0.5	7480
0.5-0.6	3630
0.6-0.7	5230
0.7-0.8	5015
0.8-0.85	2332
0.85-0.9	1208
0.9-0.95	565
0.95-1	47

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC172770
0.9933	High Similarity	NPC79053
0.9868	High Similarity	NPC472275
0.9803	High Similarity	NPC235018
0.9803	High Similarity	NPC45146
0.9739	High Similarity	NPC32694
0.9675	High Similarity	NPC470694
0.9673	High Similarity	NPC80375
0.9671	High Similarity	NPC161960
0.9671	High Similarity	NPC187745
0.9671	High Similarity	NPC304008
0.9669	High Similarity	NPC113906
0.9613	High Similarity	NPC220313
0.9613	High Similarity	NPC472278
0.9613	High Similarity	NPC473313
0.9613	High Similarity	NPC329669
0.9613	High Similarity	NPC303460
0.9613	High Similarity	NPC306321
0.9605	High Similarity	NPC191146
0.9605	High Similarity	NPC115853
0.9605	High Similarity	NPC68093
0.9605	High Similarity	NPC138243
0.9605	High Similarity	NPC142339
0.9548	High Similarity	NPC329760
0.9542	High Similarity	NPC262286
0.9542	High Similarity	NPC180011
0.9542	High Similarity	NPC36852
0.9542	High Similarity	NPC219867
0.9542	High Similarity	NPC236796
0.9542	High Similarity	NPC78225
0.9484	High Similarity	NPC167678
0.9484	High Similarity	NPC29876
0.9484	High Similarity	NPC234644
0.9481	High Similarity	NPC100123
0.9481	High Similarity	NPC235448
0.9477	High Similarity	NPC3980
0.9474	High Similarity	NPC227337
0.9474	High Similarity	NPC33051
0.9474	High Similarity	NPC89474
0.9474	High Similarity	NPC273462
0.9474	High Similarity	NPC70433
0.9474	High Similarity	NPC49402
0.9427	High Similarity	NPC473286
0.9427	High Similarity	NPC472277
0.9423	High Similarity	NPC83922
0.9423	High Similarity	NPC472448
0.9419	High Similarity	NPC188433
0.9419	High Similarity	NPC228785
0.9419	High Similarity	NPC119224
0.9419	High Similarity	NPC14353
0.9419	High Similarity	NPC56085
0.9419	High Similarity	NPC476980
0.9419	High Similarity	NPC320359
0.9419	High Similarity	NPC204290
0.9412	High Similarity	NPC117992
0.9412	High Similarity	NPC230149
0.9412	High Similarity	NPC168247
0.9412	High Similarity	NPC57674
0.9412	High Similarity	NPC152951
0.9408	High Similarity	NPC249570
0.9404	High Similarity	NPC88804
0.9404	High Similarity	NPC3825
0.9404	High Similarity	NPC62042
0.94	High Similarity	NPC37135
0.94	High Similarity	NPC186397
0.94	High Similarity	NPC276930
0.94	High Similarity	NPC194856
0.9367	High Similarity	NPC277480
0.9363	High Similarity	NPC187491
0.9363	High Similarity	NPC18100
0.9363	High Similarity	NPC189473
0.9363	High Similarity	NPC207690
0.9363	High Similarity	NPC205265
0.9363	High Similarity	NPC23298
0.9363	High Similarity	NPC319200
0.9363	High Similarity	NPC472281
0.9359	High Similarity	NPC266314
0.9359	High Similarity	NPC40491
0.9359	High Similarity	NPC278052
0.9359	High Similarity	NPC258331
0.9359	High Similarity	NPC259456
0.9359	High Similarity	NPC61010
0.9359	High Similarity	NPC57715
0.9355	High Similarity	NPC46736
0.9355	High Similarity	NPC197856
0.9355	High Similarity	NPC250214
0.9355	High Similarity	NPC95936
0.9351	High Similarity	NPC472916
0.9351	High Similarity	NPC274730
0.9351	High Similarity	NPC276444
0.9346	High Similarity	NPC476631
0.9346	High Similarity	NPC292214
0.9346	High Similarity	NPC88645
0.9346	High Similarity	NPC206238
0.9346	High Similarity	NPC271779
0.9346	High Similarity	NPC167091
0.9346	High Similarity	NPC213896
0.9346	High Similarity	NPC192083
0.9342	High Similarity	NPC154345
0.9342	High Similarity	NPC202157
0.9342	High Similarity	NPC251110
0.9338	High Similarity	NPC266499
0.9338	High Similarity	NPC223988
0.9333	High Similarity	NPC207729
0.9313	High Similarity	NPC472276
0.9304	High Similarity	NPC37183
0.9304	High Similarity	NPC239752
0.9304	High Similarity	NPC472450
0.9304	High Similarity	NPC275780
0.9299	High Similarity	NPC25152
0.9299	High Similarity	NPC206605
0.9295	High Similarity	NPC476283
0.9295	High Similarity	NPC476280
0.9295	High Similarity	NPC297212
0.929	High Similarity	NPC136674
0.929	High Similarity	NPC476981
0.929	High Similarity	NPC99597
0.929	High Similarity	NPC210084
0.929	High Similarity	NPC472911
0.929	High Similarity	NPC222814
0.929	High Similarity	NPC165977
0.929	High Similarity	NPC291508
0.929	High Similarity	NPC469584
0.929	High Similarity	NPC472913
0.929	High Similarity	NPC472914
0.929	High Similarity	NPC474208
0.929	High Similarity	NPC299520
0.929	High Similarity	NPC474836
0.929	High Similarity	NPC129684
0.929	High Similarity	NPC241904
0.929	High Similarity	NPC96167
0.929	High Similarity	NPC475267
0.929	High Similarity	NPC245758
0.929	High Similarity	NPC162869
0.929	High Similarity	NPC181960
0.929	High Similarity	NPC156057
0.929	High Similarity	NPC476630
0.929	High Similarity	NPC218313
0.929	High Similarity	NPC474681
0.929	High Similarity	NPC217677
0.929	High Similarity	NPC223787
0.929	High Similarity	NPC300727
0.929	High Similarity	NPC48208
0.929	High Similarity	NPC472910
0.929	High Similarity	NPC218871
0.9286	High Similarity	NPC472280
0.9286	High Similarity	NPC321779
0.9286	High Similarity	NPC256612
0.9286	High Similarity	NPC256925
0.9286	High Similarity	NPC2928
0.9286	High Similarity	NPC20830
0.9281	High Similarity	NPC161277
0.9281	High Similarity	NPC157784
0.9281	High Similarity	NPC39007
0.9281	High Similarity	NPC106976
0.9281	High Similarity	NPC37684
0.9281	High Similarity	NPC199100
0.9281	High Similarity	NPC180234
0.9281	High Similarity	NPC120537
0.9281	High Similarity	NPC101996
0.9281	High Similarity	NPC63187
0.9276	High Similarity	NPC61620
0.9276	High Similarity	NPC227122
0.9276	High Similarity	NPC184136
0.9276	High Similarity	NPC248102
0.9272	High Similarity	NPC118726
0.9272	High Similarity	NPC12367
0.925	High Similarity	NPC288813
0.9245	High Similarity	NPC37870
0.9245	High Similarity	NPC39091
0.9245	High Similarity	NPC472449
0.9241	High Similarity	NPC7483
0.9241	High Similarity	NPC236132
0.9241	High Similarity	NPC248638
0.9241	High Similarity	NPC152659
0.9241	High Similarity	NPC12461
0.9241	High Similarity	NPC236521
0.9241	High Similarity	NPC41301
0.9236	High Similarity	NPC474187
0.9231	High Similarity	NPC204879
0.9231	High Similarity	NPC210459
0.9231	High Similarity	NPC329091
0.9231	High Similarity	NPC476242
0.9226	High Similarity	NPC255106
0.9226	High Similarity	NPC291878
0.9226	High Similarity	NPC235165
0.9226	High Similarity	NPC133970
0.9226	High Similarity	NPC195796
0.9226	High Similarity	NPC6633
0.9226	High Similarity	NPC470600
0.9226	High Similarity	NPC472455
0.9226	High Similarity	NPC5322
0.9226	High Similarity	NPC278778
0.9226	High Similarity	NPC35038
0.9221	High Similarity	NPC183878
0.9221	High Similarity	NPC74924
0.9221	High Similarity	NPC255350
0.9221	High Similarity	NPC22519
0.9221	High Similarity	NPC176775
0.9221	High Similarity	NPC69394

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 NPC185258 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	406
0.1-0.2	997
0.2-0.3	1686
0.3-0.4	2735
0.4-0.5	1812
0.5-0.6	984
0.6-0.7	364
0.7-0.8	112
0.8-0.85	42
0.85-0.9	8
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9346	High Similarity	NPD2393	Clinical (unspecified phase)
0.9221	High Similarity	NPD2801	Approved
0.9032	High Similarity	NPD1934	Approved
0.9007	High Similarity	NPD1511	Approved
0.8889	High Similarity	NPD1512	Approved
0.8812	High Similarity	NPD5494	Approved
0.8742	High Similarity	NPD3882	Suspended
0.8701	High Similarity	NPD4378	Clinical (unspecified phase)
0.8598	High Similarity	NPD6166	Phase 2
0.8598	High Similarity	NPD6168	Clinical (unspecified phase)
0.8598	High Similarity	NPD6167	Clinical (unspecified phase)
0.8544	High Similarity	NPD4380	Phase 2
0.8509	High Similarity	NPD4868	Clinical (unspecified phase)
0.85	High Similarity	NPD7819	Suspended
0.8494	Intermediate Similarity	NPD3818	Discontinued
0.8462	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8457	Intermediate Similarity	NPD7075	Discontinued
0.8431	Intermediate Similarity	NPD1549	Phase 2
0.8393	Intermediate Similarity	NPD7074	Phase 3
0.8385	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8377	Intermediate Similarity	NPD2800	Approved
0.8366	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8366	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD6232	Discontinued
0.8353	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD943	Approved
0.8333	Intermediate Similarity	NPD3817	Phase 2
0.8333	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD5844	Phase 1
0.8333	Intermediate Similarity	NPD7054	Approved
0.8323	Intermediate Similarity	NPD7473	Discontinued
0.8284	Intermediate Similarity	NPD7472	Approved
0.8272	Intermediate Similarity	NPD1465	Phase 2
0.8261	Intermediate Similarity	NPD7411	Suspended
0.8235	Intermediate Similarity	NPD1510	Phase 2
0.8235	Intermediate Similarity	NPD6797	Phase 2
0.8232	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD1240	Approved
0.8199	Intermediate Similarity	NPD6599	Discontinued
0.8193	Intermediate Similarity	NPD6959	Discontinued
0.8187	Intermediate Similarity	NPD7251	Discontinued
0.8182	Intermediate Similarity	NPD2796	Approved
0.8182	Intermediate Similarity	NPD2935	Discontinued
0.8105	Intermediate Similarity	NPD1607	Approved
0.8098	Intermediate Similarity	NPD6801	Discontinued
0.8084	Intermediate Similarity	NPD1247	Approved
0.805	Intermediate Similarity	NPD6799	Approved
0.8047	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8035	Intermediate Similarity	NPD7808	Phase 3
0.8023	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD3749	Approved
0.8012	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5402	Approved
0.7977	Intermediate Similarity	NPD6559	Discontinued
0.7975	Intermediate Similarity	NPD3750	Approved
0.7952	Intermediate Similarity	NPD7768	Phase 2
0.7949	Intermediate Similarity	NPD6100	Approved
0.7949	Intermediate Similarity	NPD6099	Approved
0.7947	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD3226	Approved
0.7898	Intermediate Similarity	NPD2346	Discontinued
0.7888	Intermediate Similarity	NPD2532	Approved
0.7888	Intermediate Similarity	NPD2534	Approved
0.7888	Intermediate Similarity	NPD2533	Approved
0.7885	Intermediate Similarity	NPD2799	Discontinued
0.7885	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD3926	Phase 2
0.7881	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD230	Phase 1
0.7799	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD2344	Approved
0.7765	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD6651	Approved
0.7751	Intermediate Similarity	NPD919	Approved
0.775	Intermediate Similarity	NPD4628	Phase 3
0.7742	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD1613	Approved
0.7727	Intermediate Similarity	NPD2313	Discontinued
0.7692	Intermediate Similarity	NPD447	Suspended
0.7688	Intermediate Similarity	NPD1243	Approved
0.7683	Intermediate Similarity	NPD920	Approved
0.768	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD3748	Approved
0.7614	Intermediate Similarity	NPD5953	Discontinued
0.761	Intermediate Similarity	NPD1551	Phase 2
0.7607	Intermediate Similarity	NPD7390	Discontinued
0.76	Intermediate Similarity	NPD7286	Phase 2
0.7593	Intermediate Similarity	NPD2309	Approved
0.7576	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD5403	Approved
0.7561	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD3751	Discontinued
0.7528	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD8434	Phase 2
0.7455	Intermediate Similarity	NPD5401	Approved
0.7442	Intermediate Similarity	NPD6234	Discontinued
0.7439	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD4625	Phase 3
0.7436	Intermediate Similarity	NPD3027	Phase 3
0.7425	Intermediate Similarity	NPD1653	Approved
0.7423	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD5711	Approved
0.7414	Intermediate Similarity	NPD5710	Approved
0.7414	Intermediate Similarity	NPD3787	Discontinued
0.7403	Intermediate Similarity	NPD1203	Approved
0.7394	Intermediate Similarity	NPD6776	Approved
0.7394	Intermediate Similarity	NPD6779	Approved
0.7394	Intermediate Similarity	NPD6780	Approved
0.7394	Intermediate Similarity	NPD6777	Approved
0.7394	Intermediate Similarity	NPD6781	Approved
0.7394	Intermediate Similarity	NPD6778	Approved
0.7394	Intermediate Similarity	NPD6782	Approved
0.7389	Intermediate Similarity	NPD8313	Approved
0.7389	Intermediate Similarity	NPD8312	Approved
0.7378	Intermediate Similarity	NPD6190	Approved
0.7372	Intermediate Similarity	NPD4908	Phase 1
0.7358	Intermediate Similarity	NPD1933	Approved
0.7356	Intermediate Similarity	NPD7199	Phase 2
0.7355	Intermediate Similarity	NPD2798	Approved
0.7349	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD9269	Phase 2
0.7312	Intermediate Similarity	NPD4360	Phase 2
0.7312	Intermediate Similarity	NPD4363	Phase 3
0.7308	Intermediate Similarity	NPD9494	Approved
0.729	Intermediate Similarity	NPD1470	Approved
0.7289	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD3268	Approved
0.7278	Intermediate Similarity	NPD7458	Discontinued
0.7277	Intermediate Similarity	NPD7435	Discontinued
0.7273	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD8150	Discontinued
0.7255	Intermediate Similarity	NPD1610	Phase 2
0.7255	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD6844	Discontinued
0.7251	Intermediate Similarity	NPD37	Approved
0.7247	Intermediate Similarity	NPD7228	Approved
0.7225	Intermediate Similarity	NPD4966	Approved
0.7225	Intermediate Similarity	NPD4965	Approved
0.7225	Intermediate Similarity	NPD4967	Phase 2
0.7216	Intermediate Similarity	NPD7229	Phase 3
0.7208	Intermediate Similarity	NPD3972	Approved
0.7208	Intermediate Similarity	NPD9717	Approved
0.7208	Intermediate Similarity	NPD1608	Approved
0.7197	Intermediate Similarity	NPD2861	Phase 2
0.7193	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7697	Approved
0.7188	Intermediate Similarity	NPD7698	Approved
0.7188	Intermediate Similarity	NPD7696	Phase 3
0.7182	Intermediate Similarity	NPD7685	Pre-registration
0.7179	Intermediate Similarity	NPD2797	Approved
0.7179	Intermediate Similarity	NPD8151	Discontinued
0.7178	Intermediate Similarity	NPD5408	Approved
0.7178	Intermediate Similarity	NPD5406	Approved
0.7178	Intermediate Similarity	NPD5404	Approved
0.7178	Intermediate Similarity	NPD5405	Approved
0.7176	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD5242	Approved
0.717	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD4749	Approved
0.7152	Intermediate Similarity	NPD6832	Phase 2
0.715	Intermediate Similarity	NPD7871	Phase 2
0.715	Intermediate Similarity	NPD7870	Phase 2
0.7143	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1201	Approved
0.7135	Intermediate Similarity	NPD6823	Phase 2
0.7134	Intermediate Similarity	NPD1471	Phase 3
0.7128	Intermediate Similarity	NPD6535	Approved
0.7128	Intermediate Similarity	NPD7701	Phase 2
0.7128	Intermediate Similarity	NPD6534	Approved
0.7117	Intermediate Similarity	NPD4308	Phase 3
0.711	Intermediate Similarity	NPD5761	Phase 2
0.711	Intermediate Similarity	NPD5760	Phase 2
0.7108	Intermediate Similarity	NPD7003	Approved
0.7108	Intermediate Similarity	NPD8166	Discontinued
0.7107	Intermediate Similarity	NPD7783	Phase 2
0.7107	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4287	Approved
0.709	Intermediate Similarity	NPD4361	Phase 2
0.709	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD7584	Approved
0.7069	Intermediate Similarity	NPD4288	Approved
0.7069	Intermediate Similarity	NPD2296	Approved
0.7063	Intermediate Similarity	NPD411	Approved
0.7063	Intermediate Similarity	NPD3764	Approved
0.7059	Intermediate Similarity	NPD9268	Approved
0.7056	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7874	Approved
0.7039	Intermediate Similarity	NPD2403	Approved
0.7032	Intermediate Similarity	NPD422	Phase 1
0.703	Intermediate Similarity	NPD2343	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