NPASS Compound

Structure

NPC329669 OpenBabel07101719252D 29 32 0 0 1 0 0 0 0 0999 V2000 -1.7321 3.0000 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 5.1369 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3412 -2.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2923 -2.4781 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 -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 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 -1.0000 0.0000 C 0 0 3 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 0.8660 -0.5000 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 -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 0.0000 -2.0000 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.8090 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 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 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 10 1 0 0 0 0 2 10 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 7 1 0 0 0 0 6 10 2 0 0 0 0 7 12 1 0 0 0 0 8 13 1 0 0 0 0 8 14 2 0 0 0 0 9 15 2 0 0 0 0 9 16 1 0 0 0 0 11 23 1 0 0 0 0 11 28 1 0 0 0 0 12 19 2 0 0 0 0 12 22 1 0 0 0 0 13 20 1 0 0 0 0 13 22 2 0 0 0 0 14 19 1 0 0 0 0 14 24 1 0 0 0 0 15 17 1 0 0 0 0 15 29 1 0 0 0 0 16 18 2 0 0 0 0 16 28 1 0 0 0 0 17 20 1 0 0 0 0 17 21 2 0 0 0 0 18 21 1 0 0 0 0 18 23 1 0 0 0 0 19 25 1 0 0 0 0 20 26 2 0 0 0 0 21 27 1 0 0 0 0 22 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	396.16
Volume:	403.788
LogP:	5.45
LogD:	2.739
LogS:	-3.377
# Rotatable Bonds:	2
TPSA:	100.13
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.332
Synthetic Accessibility Score:	3.783
Fsp3:	0.348
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:	-4.885
MDCK Permeability:	1.3607611435872968e-05
Pgp-inhibitor:	0.334
Pgp-substrate:	0.063
Human Intestinal Absorption (HIA):	0.074
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.022

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	88.45500946044922%
Volume Distribution (VD):	0.916
Pgp-substrate:	12.383706092834473%

ADMET: Metabolism

CYP1A2-inhibitor:	0.461
CYP1A2-substrate:	0.557
CYP2C19-inhibitor:	0.409
CYP2C19-substrate:	0.091
CYP2C9-inhibitor:	0.783
CYP2C9-substrate:	0.733
CYP2D6-inhibitor:	0.213
CYP2D6-substrate:	0.216
CYP3A4-inhibitor:	0.125
CYP3A4-substrate:	0.172

ADMET: Excretion

Clearance (CL):	3.462
Half-life (T1/2):	0.356

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.887
Drug-inuced Liver Injury (DILI):	0.947
AMES Toxicity:	0.4
Rat Oral Acute Toxicity:	0.492
Maximum Recommended Daily Dose:	0.733
Skin Sensitization:	0.89
Carcinogencity:	0.372
Eye Corrosion:	0.003
Eye Irritation:	0.822
Respiratory Toxicity:	0.506

Download Data

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

Natural Product: NPC329669

Natural Product ID:	NPC329669
*Common Name:**	Cudraxanthone M
IUPAC Name:	4,7,8-trihydroxy-2,3,3-trimethyl-9-(3-methylbut-2-enyl)-2H-furo[3,2-b]xanthen-5-one
Synonyms:	Cudraxanthone M
Standard InCHIKey:	ZYJVDWWKUSJAQY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C23H24O6/c1-10(2)6-7-12-19(25)14(24)8-13-20(26)17-15(29-22(12)13)9-16-18(21(17)27)23(4,5)11(3)28-16/h6,8-9,11,24-25,27H,7H2,1-5H3
SMILES:	CC1C(C2=C(O1)C=C3C(=C2O)C(=O)C4=CC(=C(C(=C4O3)CC=C(C)C)O)O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL371024
PubChem CID:	11689770
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
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]

☑ 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	2
LD50	5

Activity Type	# Activity
Cell Line	5
Individual Protein	5
NON-MOLECULAR	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	=	12.1	uM	PMID[521705]
NPT116	Cell Line	HL-60	Homo sapiens	LD50	=	8.2	uM	PMID[521705]
NPT146	Cell Line	SK-OV-3	Homo sapiens	LD50	=	14.6	uM	PMID[521705]
NPT196	Cell Line	AGS	Homo sapiens	LD50	=	4.1	uM	PMID[521705]
NPT81	Cell Line	A549	Homo sapiens	LD50	=	11.8	uM	PMID[521705]
NPT1214	Individual Protein	Acyl coenzyme A:cholesterol acyltransferase 1	Homo sapiens	IC50	=	56800.0	nM	PMID[521706]
NPT2584	Individual Protein	Acyl coenzyme A:cholesterol acyltransferase 2	Homo sapiens	IC50	=	23200.0	nM	PMID[521706]
NPT344	Individual Protein	Sialidase	Clostridium perfringens	Ki	=	98.0	nM	PMID[521708]
NPT344	Individual Protein	Sialidase	Clostridium perfringens	Ki	=	510.1	nM	PMID[521708]
NPT344	Individual Protein	Sialidase	Clostridium perfringens	IC50	=	186.0	nM	PMID[521708]
NPT1	Others	Radical scavenging activity		IC50	=	10400.0	nM	PMID[521705]
NPT1	Others	Radical scavenging activity		IC50	=	26000.0	nM	PMID[521705]
NPT1	Others	Radical scavenging activity		IC50	=	42600.0	nM	PMID[521705]
NPT614	Tissue	Plasma	Rattus norvegicus	IC50	=	2200.0	nM	PMID[521706]
NPT2	Others	Unspecified		IC50	>	100000.0	nM	PMID[521707]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	10400.0	nM	PMID[521709]

☑ 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 NPC329669 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	435
0.1-0.2	1653
0.2-0.3	3694
0.3-0.4	9241
0.4-0.5	9395
0.5-0.6	3689
0.6-0.7	5113
0.7-0.8	5114
0.8-0.85	2513
0.85-0.9	1386
0.9-0.95	437
0.95-1	27

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473313
1.0	High Similarity	NPC472278
0.9808	High Similarity	NPC473286
0.9744	High Similarity	NPC18100
0.9682	High Similarity	NPC472277
0.9618	High Similarity	NPC472281
0.9618	High Similarity	NPC205265
0.9615	High Similarity	NPC472275
0.9613	High Similarity	NPC172770
0.9613	High Similarity	NPC185258
0.9563	High Similarity	NPC472276
0.9557	High Similarity	NPC326520
0.9557	High Similarity	NPC37183
0.9554	High Similarity	NPC81679
0.9551	High Similarity	NPC476283
0.9548	High Similarity	NPC79053
0.9548	High Similarity	NPC196448
0.9545	High Similarity	NPC113906
0.95	High Similarity	NPC288813
0.9497	High Similarity	NPC170245
0.9497	High Similarity	NPC277480
0.949	High Similarity	NPC187354
0.949	High Similarity	NPC32694
0.943	High Similarity	NPC470694
0.9427	High Similarity	NPC235018
0.9427	High Similarity	NPC45146
0.9423	High Similarity	NPC223787
0.9423	High Similarity	NPC36852
0.9423	High Similarity	NPC262286
0.9416	High Similarity	NPC106976
0.9371	High Similarity	NPC273959
0.9371	High Similarity	NPC124038
0.9371	High Similarity	NPC220313
0.9371	High Similarity	NPC475985
0.9363	High Similarity	NPC95936
0.9363	High Similarity	NPC250214
0.9363	High Similarity	NPC329091
0.9359	High Similarity	NPC138243
0.9359	High Similarity	NPC142339
0.9355	High Similarity	NPC74924
0.9355	High Similarity	NPC192083
0.9355	High Similarity	NPC298692
0.9355	High Similarity	NPC213896
0.9313	High Similarity	NPC300053
0.9313	High Similarity	NPC108433
0.9308	High Similarity	NPC220912
0.9304	High Similarity	NPC472624
0.9304	High Similarity	NPC328102
0.9304	High Similarity	NPC80375
0.9304	High Similarity	NPC14353
0.9304	High Similarity	NPC56085
0.9304	High Similarity	NPC228785
0.9299	High Similarity	NPC99597
0.9299	High Similarity	NPC469584
0.9299	High Similarity	NPC475267
0.9299	High Similarity	NPC474208
0.9299	High Similarity	NPC48208
0.9299	High Similarity	NPC291508
0.9299	High Similarity	NPC474836
0.9299	High Similarity	NPC236796
0.9299	High Similarity	NPC156057
0.9299	High Similarity	NPC304008
0.9299	High Similarity	NPC78225
0.9299	High Similarity	NPC187745
0.9299	High Similarity	NPC162869
0.9299	High Similarity	NPC180011
0.9299	High Similarity	NPC219867
0.9299	High Similarity	NPC161960
0.9299	High Similarity	NPC210084
0.9295	High Similarity	NPC45849
0.9295	High Similarity	NPC321779
0.9295	High Similarity	NPC470327
0.9295	High Similarity	NPC200761
0.9295	High Similarity	NPC477503
0.9259	High Similarity	NPC152477
0.9255	High Similarity	NPC173292
0.9255	High Similarity	NPC235610
0.9255	High Similarity	NPC128293
0.925	High Similarity	NPC306321
0.925	High Similarity	NPC7483
0.925	High Similarity	NPC303460
0.925	High Similarity	NPC41301
0.9245	High Similarity	NPC474186
0.9245	High Similarity	NPC278052
0.9245	High Similarity	NPC134783
0.9245	High Similarity	NPC228383
0.9245	High Similarity	NPC266314
0.9245	High Similarity	NPC61010
0.9245	High Similarity	NPC40491
0.9241	High Similarity	NPC469658
0.9241	High Similarity	NPC85121
0.9241	High Similarity	NPC210459
0.9241	High Similarity	NPC100123
0.9236	High Similarity	NPC472916
0.9236	High Similarity	NPC235165
0.9236	High Similarity	NPC470328
0.9236	High Similarity	NPC278778
0.9236	High Similarity	NPC35038
0.9236	High Similarity	NPC191146
0.9236	High Similarity	NPC68093
0.9236	High Similarity	NPC255106
0.9236	High Similarity	NPC291878
0.9236	High Similarity	NPC472626
0.9236	High Similarity	NPC115853
0.9236	High Similarity	NPC195796
0.9236	High Similarity	NPC209614
0.9231	High Similarity	NPC89474
0.9226	High Similarity	NPC204515
0.9207	High Similarity	NPC310794
0.9198	High Similarity	NPC50394
0.9198	High Similarity	NPC117854
0.9198	High Similarity	NPC477154
0.9198	High Similarity	NPC6588
0.9198	High Similarity	NPC247973
0.9187	High Similarity	NPC83922
0.9187	High Similarity	NPC329760
0.9187	High Similarity	NPC472448
0.9187	High Similarity	NPC472635
0.9182	High Similarity	NPC320359
0.9182	High Similarity	NPC321399
0.9182	High Similarity	NPC475886
0.9182	High Similarity	NPC36217
0.9182	High Similarity	NPC119224
0.9182	High Similarity	NPC474287
0.9182	High Similarity	NPC476980
0.9177	High Similarity	NPC165977
0.9177	High Similarity	NPC474055
0.9177	High Similarity	NPC129684
0.9177	High Similarity	NPC241904
0.9177	High Similarity	NPC472911
0.9177	High Similarity	NPC27337
0.9177	High Similarity	NPC245758
0.9177	High Similarity	NPC222814
0.9177	High Similarity	NPC472910
0.9177	High Similarity	NPC217677
0.9177	High Similarity	NPC300727
0.9177	High Similarity	NPC299520
0.9177	High Similarity	NPC472914
0.9177	High Similarity	NPC471209
0.9177	High Similarity	NPC181960
0.9177	High Similarity	NPC96167
0.9177	High Similarity	NPC472598
0.9177	High Similarity	NPC472913
0.9172	High Similarity	NPC57674
0.9172	High Similarity	NPC67396
0.9172	High Similarity	NPC37392
0.9172	High Similarity	NPC134287
0.9172	High Similarity	NPC2928
0.9172	High Similarity	NPC168247
0.9172	High Similarity	NPC117992
0.9172	High Similarity	NPC230149
0.9172	High Similarity	NPC152951
0.9172	High Similarity	NPC130589
0.9167	High Similarity	NPC101996
0.9167	High Similarity	NPC249570
0.9161	High Similarity	NPC62042
0.9156	High Similarity	NPC194856
0.9146	High Similarity	NPC28589
0.9146	High Similarity	NPC248593
0.9146	High Similarity	NPC307286
0.9146	High Similarity	NPC121333
0.9141	High Similarity	NPC242395
0.9141	High Similarity	NPC165456
0.9136	High Similarity	NPC472452
0.9136	High Similarity	NPC119589
0.913	High Similarity	NPC197168
0.913	High Similarity	NPC236521
0.913	High Similarity	NPC248638
0.913	High Similarity	NPC476295
0.913	High Similarity	NPC319200
0.913	High Similarity	NPC152659
0.913	High Similarity	NPC236132
0.913	High Similarity	NPC187491
0.9125	High Similarity	NPC474187
0.9125	High Similarity	NPC475883
0.9125	High Similarity	NPC258331
0.9125	High Similarity	NPC57715
0.9125	High Similarity	NPC474351
0.9125	High Similarity	NPC29876
0.9125	High Similarity	NPC308992
0.9125	High Similarity	NPC234644
0.9125	High Similarity	NPC167678
0.9119	High Similarity	NPC476242
0.9119	High Similarity	NPC22192
0.9119	High Similarity	NPC235448
0.9114	High Similarity	NPC24640
0.9114	High Similarity	NPC274730
0.9114	High Similarity	NPC3980
0.9108	High Similarity	NPC271779
0.9108	High Similarity	NPC167091
0.9108	High Similarity	NPC273462
0.9108	High Similarity	NPC227337
0.9108	High Similarity	NPC70433
0.9108	High Similarity	NPC88645
0.9108	High Similarity	NPC49402
0.9108	High Similarity	NPC476631
0.9108	High Similarity	NPC280937
0.9108	High Similarity	NPC292214
0.9108	High Similarity	NPC472915
0.9108	High Similarity	NPC33051

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 NPC329669 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	374
0.1-0.2	943
0.2-0.3	1792
0.3-0.4	2629
0.4-0.5	1903
0.5-0.6	952
0.6-0.7	387
0.7-0.8	116
0.8-0.85	41
0.85-0.9	11
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9355	High Similarity	NPD2393	Clinical (unspecified phase)
0.9062	High Similarity	NPD5494	Approved
0.9045	High Similarity	NPD1934	Approved
0.8987	High Similarity	NPD2801	Approved
0.8875	High Similarity	NPD3882	Suspended
0.8735	High Similarity	NPD3818	Discontinued
0.8654	High Similarity	NPD1511	Approved
0.8642	High Similarity	NPD4868	Clinical (unspecified phase)
0.8614	High Similarity	NPD6166	Phase 2
0.8614	High Similarity	NPD6168	Clinical (unspecified phase)
0.8614	High Similarity	NPD6167	Clinical (unspecified phase)
0.8562	High Similarity	NPD4380	Phase 2
0.8544	High Similarity	NPD1512	Approved
0.8481	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8476	Intermediate Similarity	NPD7075	Discontinued
0.8452	Intermediate Similarity	NPD1549	Phase 2
0.8412	Intermediate Similarity	NPD7074	Phase 3
0.8405	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8405	Intermediate Similarity	NPD7819	Suspended
0.8397	Intermediate Similarity	NPD2800	Approved
0.8387	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8372	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8353	Intermediate Similarity	NPD7054	Approved
0.8353	Intermediate Similarity	NPD5844	Phase 1
0.8323	Intermediate Similarity	NPD6959	Discontinued
0.8304	Intermediate Similarity	NPD7472	Approved
0.8256	Intermediate Similarity	NPD6797	Phase 2
0.8253	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD3817	Phase 2
0.8214	Intermediate Similarity	NPD1247	Approved
0.8208	Intermediate Similarity	NPD7251	Discontinued
0.8208	Intermediate Similarity	NPD6559	Discontinued
0.8205	Intermediate Similarity	NPD2796	Approved
0.8171	Intermediate Similarity	NPD7411	Suspended
0.8166	Intermediate Similarity	NPD6232	Discontinued
0.815	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD1510	Phase 2
0.8137	Intermediate Similarity	NPD2534	Approved
0.8137	Intermediate Similarity	NPD2533	Approved
0.8137	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD2532	Approved
0.8129	Intermediate Similarity	NPD7473	Discontinued
0.8121	Intermediate Similarity	NPD6801	Discontinued
0.811	Intermediate Similarity	NPD6599	Discontinued
0.8072	Intermediate Similarity	NPD1465	Phase 2
0.8057	Intermediate Similarity	NPD7808	Phase 3
0.8035	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD5402	Approved
0.8	Intermediate Similarity	NPD943	Approved
0.8	Intermediate Similarity	NPD1240	Approved
0.7975	Intermediate Similarity	NPD2935	Discontinued
0.7965	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD6799	Approved
0.7929	Intermediate Similarity	NPD3749	Approved
0.7907	Intermediate Similarity	NPD3926	Phase 2
0.7898	Intermediate Similarity	NPD1607	Approved
0.7882	Intermediate Similarity	NPD919	Approved
0.787	Intermediate Similarity	NPD7768	Phase 2
0.7834	Intermediate Similarity	NPD230	Phase 1
0.7818	Intermediate Similarity	NPD920	Approved
0.779	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4628	Phase 3
0.7778	Intermediate Similarity	NPD6234	Discontinued
0.7771	Intermediate Similarity	NPD1613	Approved
0.7771	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD6099	Approved
0.775	Intermediate Similarity	NPD6100	Approved
0.7722	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD1243	Approved
0.7705	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD2344	Approved
0.7697	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD8434	Phase 2
0.7677	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD6651	Approved
0.7669	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD3750	Approved
0.7654	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD5711	Approved
0.7644	Intermediate Similarity	NPD5710	Approved
0.7628	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD3226	Approved
0.7606	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD5403	Approved
0.7593	Intermediate Similarity	NPD2346	Discontinued
0.7588	Intermediate Similarity	NPD37	Approved
0.7578	Intermediate Similarity	NPD2799	Discontinued
0.7578	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD7228	Approved
0.7571	Intermediate Similarity	NPD3751	Discontinued
0.7558	Intermediate Similarity	NPD4967	Phase 2
0.7558	Intermediate Similarity	NPD4965	Approved
0.7558	Intermediate Similarity	NPD4966	Approved
0.7542	Intermediate Similarity	NPD5953	Discontinued
0.7531	Intermediate Similarity	NPD1551	Phase 2
0.7528	Intermediate Similarity	NPD7286	Phase 2
0.7515	Intermediate Similarity	NPD2309	Approved
0.7486	Intermediate Similarity	NPD7199	Phase 2
0.7485	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD5401	Approved
0.7468	Intermediate Similarity	NPD3027	Phase 3
0.7456	Intermediate Similarity	NPD1653	Approved
0.7443	Intermediate Similarity	NPD3787	Discontinued
0.7425	Intermediate Similarity	NPD7390	Discontinued
0.7421	Intermediate Similarity	NPD6781	Approved
0.7421	Intermediate Similarity	NPD2313	Discontinued
0.7421	Intermediate Similarity	NPD6777	Approved
0.7421	Intermediate Similarity	NPD6782	Approved
0.7421	Intermediate Similarity	NPD6776	Approved
0.7421	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD6780	Approved
0.7421	Intermediate Similarity	NPD6778	Approved
0.7421	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD6779	Approved
0.7418	Intermediate Similarity	NPD8313	Approved
0.7418	Intermediate Similarity	NPD8312	Approved
0.741	Intermediate Similarity	NPD6190	Approved
0.7401	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD447	Suspended
0.7381	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD3748	Approved
0.7349	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD7229	Phase 3
0.7342	Intermediate Similarity	NPD2861	Phase 2
0.7341	Intermediate Similarity	NPD5760	Phase 2
0.7341	Intermediate Similarity	NPD5761	Phase 2
0.734	Intermediate Similarity	NPD4363	Phase 3
0.734	Intermediate Similarity	NPD4360	Phase 2
0.7321	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7685	Pre-registration
0.7306	Intermediate Similarity	NPD7435	Discontinued
0.7297	Intermediate Similarity	NPD8150	Discontinued
0.7296	Intermediate Similarity	NPD8151	Discontinued
0.7296	Intermediate Similarity	NPD4908	Phase 1
0.729	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD6844	Discontinued
0.7233	Intermediate Similarity	NPD9494	Approved
0.7225	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7698	Approved
0.7216	Intermediate Similarity	NPD7696	Phase 3
0.7216	Intermediate Similarity	NPD7697	Approved
0.7213	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD4361	Phase 2
0.7211	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7458	Discontinued
0.7205	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1610	Phase 2
0.7179	Intermediate Similarity	NPD7871	Phase 2
0.7179	Intermediate Similarity	NPD7870	Phase 2
0.7178	Intermediate Similarity	NPD1933	Approved
0.7173	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD2403	Approved
0.7165	Intermediate Similarity	NPD6823	Phase 2
0.7158	Intermediate Similarity	NPD6535	Approved
0.7158	Intermediate Similarity	NPD6534	Approved
0.7157	Intermediate Similarity	NPD7907	Approved
0.7157	Intermediate Similarity	NPD7701	Phase 2
0.7152	Intermediate Similarity	NPD7033	Discontinued
0.7143	Intermediate Similarity	NPD4625	Phase 3
0.7143	Intermediate Similarity	NPD4111	Phase 1
0.7143	Intermediate Similarity	NPD4665	Approved
0.7136	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD7783	Phase 2
0.7135	Intermediate Similarity	NPD6273	Approved
0.7134	Intermediate Similarity	NPD9269	Phase 2
0.7126	Intermediate Similarity	NPD2424	Discontinued
0.712	Intermediate Similarity	NPD7240	Approved
0.7113	Intermediate Similarity	NPD2493	Approved
0.7113	Intermediate Similarity	NPD2494	Approved
0.7111	Intermediate Similarity	NPD5242	Approved
0.7107	Intermediate Similarity	NPD7584	Approved
0.7107	Intermediate Similarity	NPD1203	Approved
0.7104	Intermediate Similarity	NPD1729	Discontinued
0.7102	Intermediate Similarity	NPD5353	Approved
0.7099	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD8127	Discontinued
0.7089	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD7874	Approved
0.7085	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2654	Approved
0.7081	Intermediate Similarity	NPD6832	Phase 2
0.7079	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD1471	Phase 3
0.7063	Intermediate Similarity	NPD2798	Approved
0.705	Intermediate Similarity	NPD7801	Approved
0.7047	Intermediate Similarity	NPD7699	Phase 2
0.7047	Intermediate Similarity	NPD7700	Phase 2
0.7041	Intermediate Similarity	NPD8166	Discontinued
0.7037	Intermediate Similarity	NPD4287	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