NPASS Compound

Structure

CID235448 OpenBabel06191716032D 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 3.4641 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 5.0000 0.0000 C 0 0 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 2.5981 3.5000 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 2.5981 1.5000 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 2.5981 4.5000 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 -2.5981 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 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 -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 1.7321 -0.0000 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 -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 -0.0000 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 -1.0000 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 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 12 2 0 0 0 0 9 14 1 0 0 0 0 10 13 2 0 0 0 0 10 15 1 0 0 0 0 12 16 1 0 0 0 0 13 18 1 0 0 0 0 13 24 1 0 0 0 0 14 19 2 0 0 0 0 14 25 1 0 0 0 0 15 17 2 0 0 0 0 15 29 1 0 0 0 0 16 20 1 0 0 0 0 16 22 2 0 0 0 0 17 20 1 0 0 0 0 17 21 1 0 0 0 0 18 21 2 0 0 0 0 18 23 1 0 0 0 0 19 22 1 0 0 0 0 19 26 1 0 0 0 0 20 27 2 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:	5.502
LogD:	2.757
LogS:	-3.31
# 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:	3.492
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:	-4.89
MDCK Permeability:	1.2857883120886981e-05
Pgp-inhibitor:	0.9
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.265
20% Bioavailability (F20%):	0.918
30% Bioavailability (F30%):	0.519

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	92.5338134765625%
Volume Distribution (VD):	0.921
Pgp-substrate:	11.743237495422363%

ADMET: Metabolism

CYP1A2-inhibitor:	0.79
CYP1A2-substrate:	0.222
CYP2C19-inhibitor:	0.473
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.765
CYP2C9-substrate:	0.742
CYP2D6-inhibitor:	0.531
CYP2D6-substrate:	0.181
CYP3A4-inhibitor:	0.162
CYP3A4-substrate:	0.071

ADMET: Excretion

Clearance (CL):	1.266
Half-life (T1/2):	0.6

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.187
Drug-inuced Liver Injury (DILI):	0.944
AMES Toxicity:	0.539
Rat Oral Acute Toxicity:	0.116
Maximum Recommended Daily Dose:	0.408
Skin Sensitization:	0.898
Carcinogencity:	0.237
Eye Corrosion:	0.005
Eye Irritation:	0.907
Respiratory Toxicity:	0.238

Download Data

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

Natural Product: NPC235448

Natural Product ID:	NPC235448
*Common Name:**	Alvaxanthone
IUPAC Name:	1,3,5,6-tetrahydroxy-2-(2-methylbut-3-en-2-yl)-8-(3-methylbut-2-enyl)xanthen-9-one
Synonyms:	Alvaxanthone
Standard InCHIKey:	IXUNODGMZUQIQP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C23H24O6/c1-6-23(4,5)18-13(24)10-15-17(21(18)28)20(27)16-12(8-7-11(2)3)9-14(25)19(26)22(16)29-15/h6-7,9-10,24-26,28H,1,8H2,2-5H3
SMILES:	C=CC(C)(C)c1c(cc2c(c(=O)c3c(CC=C(C)C)cc(c(c3o2)O)O)c1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL478937
PubChem CID:	12305823
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:0003519] 8-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
NPO29752	Cudrania cochinchinensis	n.a.	n.a.	n.a.	roots	n.a.	n.a.	PMID[11170668]
NPO29752	Cudrania cochinchinensis	n.a.	n.a.	n.a.	roots	n.a.	n.a.	PMID[12932139]
NPO25837	Euphorbia micractina	Species	Euphorbiaceae	Eukaryota	Roots	Zhang County, Gansu Province, China	2002-Sep	PMID[19702283]
NPO25837	Euphorbia micractina	Species	Euphorbiaceae	Eukaryota	n.a.	root	n.a.	PMID[21534583]
NPO25837	Euphorbia micractina	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[23691978]
NPO29752	Cudrania cochinchinensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO24502	Rosa roxburghii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23156	Maclura cochinchinensis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24502	Rosa roxburghii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19038	Zanha golungensis	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25806	Streptomyces violaceus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO25837	Euphorbia micractina	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26671	Hapalosiphon welwitschii	Species	Hapalosiphonaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO26101	Andropogon zizanioides	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23156	Maclura cochinchinensis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28994	Acacia horrida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24502	Rosa roxburghii	Species	Rosaceae	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
Others	3

Activity Type	# Activity
Cell Line	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT924	Cell Line	HSC-2	Homo sapiens	CC50	=	22000.0	nM	PMID[571546]
NPT924	Cell Line	HSC-2	Homo sapiens	Ratio	=	1.1	n.a.	PMID[571546]
NPT27	Others	Unspecified		CC50	=	25000.0	nM	PMID[571546]

☑ 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 NPC235448 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	458
0.1-0.2	1881
0.2-0.3	4271
0.3-0.4	10734
0.4-0.5	7325
0.5-0.6	3635
0.6-0.7	5201
0.7-0.8	5218
0.8-0.85	2479
0.85-0.9	1021
0.9-0.95	436
0.95-1	38

Similarity Score	Similarity Level	Natural Product ID
0.9801	High Similarity	NPC136674
0.9801	High Similarity	NPC161960
0.9801	High Similarity	NPC304008
0.9801	High Similarity	NPC187745
0.974	High Similarity	NPC220313
0.9735	High Similarity	NPC115853
0.9673	High Similarity	NPC235018
0.9673	High Similarity	NPC45146
0.9673	High Similarity	NPC471973
0.9671	High Similarity	NPC219867
0.9671	High Similarity	NPC180011
0.961	High Similarity	NPC32694
0.961	High Similarity	NPC234644
0.9608	High Similarity	NPC100123
0.9603	High Similarity	NPC49402
0.9603	High Similarity	NPC227337
0.9603	High Similarity	NPC273462
0.9603	High Similarity	NPC70433
0.9603	High Similarity	NPC33051
0.9545	High Similarity	NPC14353
0.9545	High Similarity	NPC188433
0.9545	High Similarity	NPC80375
0.9545	High Similarity	NPC56085
0.9545	High Similarity	NPC320359
0.9545	High Similarity	NPC36217
0.9545	High Similarity	NPC228785
0.9539	High Similarity	NPC168247
0.9539	High Similarity	NPC117992
0.9539	High Similarity	NPC57674
0.9539	High Similarity	NPC152951
0.9539	High Similarity	NPC230149
0.9533	High Similarity	NPC151473
0.9487	High Similarity	NPC189473
0.9487	High Similarity	NPC319200
0.9487	High Similarity	NPC187491
0.9487	High Similarity	NPC23298
0.9484	High Similarity	NPC61010
0.9484	High Similarity	NPC472906
0.9484	High Similarity	NPC57715
0.9484	High Similarity	NPC40491
0.9484	High Similarity	NPC278052
0.9481	High Similarity	NPC172770
0.9481	High Similarity	NPC185258
0.9477	High Similarity	NPC191146
0.9477	High Similarity	NPC142339
0.9477	High Similarity	NPC274730
0.9477	High Similarity	NPC68093
0.9477	High Similarity	NPC472907
0.9474	High Similarity	NPC472905
0.9427	High Similarity	NPC472277
0.9427	High Similarity	NPC239752
0.9427	High Similarity	NPC472450
0.9427	High Similarity	NPC275780
0.9423	High Similarity	NPC25152
0.9423	High Similarity	NPC470694
0.9423	High Similarity	NPC201800
0.9416	High Similarity	NPC78225
0.9416	High Similarity	NPC217677
0.9416	High Similarity	NPC79053
0.9416	High Similarity	NPC472963
0.9416	High Similarity	NPC236796
0.9416	High Similarity	NPC241904
0.9416	High Similarity	NPC165977
0.9416	High Similarity	NPC218313
0.9416	High Similarity	NPC300727
0.9416	High Similarity	NPC474681
0.9416	High Similarity	NPC111969
0.9412	High Similarity	NPC472280
0.9412	High Similarity	NPC256925
0.9367	High Similarity	NPC472449
0.9367	High Similarity	NPC37870
0.9367	High Similarity	NPC39091
0.9363	High Similarity	NPC18100
0.9363	High Similarity	NPC7483
0.9363	High Similarity	NPC236132
0.9363	High Similarity	NPC186686
0.9363	High Similarity	NPC236521
0.9363	High Similarity	NPC152659
0.9363	High Similarity	NPC205265
0.9363	High Similarity	NPC472281
0.9363	High Similarity	NPC303460
0.9363	High Similarity	NPC248638
0.9363	High Similarity	NPC306321
0.9359	High Similarity	NPC474187
0.9359	High Similarity	NPC472275
0.9355	High Similarity	NPC204879
0.9355	High Similarity	NPC46736
0.9355	High Similarity	NPC197856
0.9355	High Similarity	NPC476242
0.9355	High Similarity	NPC210459
0.9351	High Similarity	NPC278778
0.9351	High Similarity	NPC133970
0.9351	High Similarity	NPC6633
0.9351	High Similarity	NPC5322
0.9351	High Similarity	NPC291878
0.9351	High Similarity	NPC138243
0.9351	High Similarity	NPC195796
0.9351	High Similarity	NPC470600
0.9351	High Similarity	NPC35038
0.9351	High Similarity	NPC3980
0.9351	High Similarity	NPC472455
0.9346	High Similarity	NPC89474
0.9308	High Similarity	NPC476306
0.9304	High Similarity	NPC473286
0.9304	High Similarity	NPC293319
0.9304	High Similarity	NPC326520
0.9299	High Similarity	NPC474162
0.9299	High Similarity	NPC78332
0.9299	High Similarity	NPC206605
0.9299	High Similarity	NPC229632
0.9299	High Similarity	NPC329760
0.9299	High Similarity	NPC474150
0.9295	High Similarity	NPC204290
0.9295	High Similarity	NPC474960
0.9295	High Similarity	NPC139036
0.9295	High Similarity	NPC475886
0.9295	High Similarity	NPC474287
0.9295	High Similarity	NPC200746
0.9295	High Similarity	NPC299436
0.9295	High Similarity	NPC476280
0.9295	High Similarity	NPC119224
0.9295	High Similarity	NPC321399
0.9295	High Similarity	NPC297212
0.929	High Similarity	NPC27337
0.929	High Similarity	NPC36852
0.929	High Similarity	NPC291508
0.929	High Similarity	NPC472598
0.929	High Similarity	NPC474055
0.929	High Similarity	NPC299520
0.929	High Similarity	NPC129684
0.929	High Similarity	NPC262286
0.929	High Similarity	NPC273843
0.9286	High Similarity	NPC200246
0.9286	High Similarity	NPC477503
0.9286	High Similarity	NPC67396
0.9286	High Similarity	NPC234255
0.9286	High Similarity	NPC45849
0.9286	High Similarity	NPC200761
0.9286	High Similarity	NPC470327
0.9281	High Similarity	NPC260979
0.9281	High Similarity	NPC257648
0.9281	High Similarity	NPC471982
0.9281	High Similarity	NPC472912
0.9281	High Similarity	NPC237994
0.9281	High Similarity	NPC477231
0.9276	High Similarity	NPC3825
0.9276	High Similarity	NPC29231
0.9276	High Similarity	NPC88804
0.9272	High Similarity	NPC196277
0.9272	High Similarity	NPC43669
0.9272	High Similarity	NPC272721
0.925	High Similarity	NPC288813
0.9245	High Similarity	NPC43319
0.9245	High Similarity	NPC170245
0.9241	High Similarity	NPC270837
0.9241	High Similarity	NPC207690
0.9241	High Similarity	NPC12461
0.9241	High Similarity	NPC146134
0.9236	High Similarity	NPC266314
0.9236	High Similarity	NPC475883
0.9236	High Similarity	NPC167678
0.9236	High Similarity	NPC474351
0.9236	High Similarity	NPC29876
0.9236	High Similarity	NPC474186
0.9231	High Similarity	NPC85121
0.9231	High Similarity	NPC250214
0.9231	High Similarity	NPC95936
0.9231	High Similarity	NPC474290
0.9226	High Similarity	NPC472626
0.9226	High Similarity	NPC470328
0.9226	High Similarity	NPC13779
0.9226	High Similarity	NPC24640
0.9226	High Similarity	NPC209614
0.9226	High Similarity	NPC475799
0.9226	High Similarity	NPC471985
0.9221	High Similarity	NPC18727
0.9221	High Similarity	NPC213896
0.9221	High Similarity	NPC469550
0.9221	High Similarity	NPC192083
0.9216	High Similarity	NPC202157
0.9216	High Similarity	NPC154345
0.9216	High Similarity	NPC31363
0.9205	High Similarity	NPC77378
0.9187	High Similarity	NPC218226
0.9187	High Similarity	NPC477154
0.9187	High Similarity	NPC6588
0.9187	High Similarity	NPC117854
0.9182	High Similarity	NPC303174
0.9182	High Similarity	NPC62261
0.9182	High Similarity	NPC475888
0.9177	High Similarity	NPC211107
0.9177	High Similarity	NPC83922
0.9177	High Similarity	NPC472448
0.9177	High Similarity	NPC294965
0.9177	High Similarity	NPC472964
0.9172	High Similarity	NPC118256
0.9172	High Similarity	NPC472902
0.9172	High Similarity	NPC282009
0.9172	High Similarity	NPC476980
0.9172	High Similarity	NPC472624

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 NPC235448 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	410
0.1-0.2	1011
0.2-0.3	1708
0.3-0.4	2745
0.4-0.5	1758
0.5-0.6	951
0.6-0.7	398
0.7-0.8	124
0.8-0.85	29
0.85-0.9	12
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9221	High Similarity	NPD2393	Clinical (unspecified phase)
0.9156	High Similarity	NPD1934	Approved
0.9097	High Similarity	NPD2801	Approved
0.8882	High Similarity	NPD1511	Approved
0.8861	High Similarity	NPD3882	Suspended
0.8766	High Similarity	NPD1512	Approved
0.8712	High Similarity	NPD6168	Clinical (unspecified phase)
0.8712	High Similarity	NPD6167	Clinical (unspecified phase)
0.8712	High Similarity	NPD6166	Phase 2
0.8704	High Similarity	NPD6232	Discontinued
0.8659	High Similarity	NPD7473	Discontinued
0.8616	High Similarity	NPD7819	Suspended
0.8581	High Similarity	NPD4378	Clinical (unspecified phase)
0.858	High Similarity	NPD5494	Approved
0.8503	High Similarity	NPD7074	Phase 3
0.85	High Similarity	NPD1465	Phase 2
0.8494	Intermediate Similarity	NPD3818	Discontinued
0.8457	Intermediate Similarity	NPD7075	Discontinued
0.8447	Intermediate Similarity	NPD3817	Phase 2
0.8443	Intermediate Similarity	NPD7054	Approved
0.8428	Intermediate Similarity	NPD4380	Phase 2
0.8395	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8393	Intermediate Similarity	NPD7472	Approved
0.8385	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8366	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8366	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD5844	Phase 1
0.8312	Intermediate Similarity	NPD1549	Phase 2
0.8303	Intermediate Similarity	NPD6959	Discontinued
0.8258	Intermediate Similarity	NPD2800	Approved
0.8246	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD6797	Phase 2
0.8212	Intermediate Similarity	NPD943	Approved
0.8199	Intermediate Similarity	NPD6599	Discontinued
0.8187	Intermediate Similarity	NPD7251	Discontinued
0.8148	Intermediate Similarity	NPD7411	Suspended
0.814	Intermediate Similarity	NPD7808	Phase 3
0.8121	Intermediate Similarity	NPD3749	Approved
0.8121	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8117	Intermediate Similarity	NPD1510	Phase 2
0.8098	Intermediate Similarity	NPD6801	Discontinued
0.8092	Intermediate Similarity	NPD1240	Approved
0.8089	Intermediate Similarity	NPD3750	Approved
0.8077	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD6099	Approved
0.8065	Intermediate Similarity	NPD2796	Approved
0.8065	Intermediate Similarity	NPD6100	Approved
0.805	Intermediate Similarity	NPD6799	Approved
0.8012	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2533	Approved
0.8	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2534	Approved
0.8	Intermediate Similarity	NPD2532	Approved
0.7988	Intermediate Similarity	NPD3926	Phase 2
0.7987	Intermediate Similarity	NPD1607	Approved
0.7967	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD3226	Approved
0.7898	Intermediate Similarity	NPD2346	Discontinued
0.7885	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD6559	Discontinued
0.787	Intermediate Similarity	NPD1247	Approved
0.7857	Intermediate Similarity	NPD919	Approved
0.7844	Intermediate Similarity	NPD7768	Phase 2
0.7771	Intermediate Similarity	NPD2799	Discontinued
0.7771	Intermediate Similarity	NPD3748	Approved
0.7765	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD7199	Phase 2
0.7756	Intermediate Similarity	NPD6651	Approved
0.7751	Intermediate Similarity	NPD6234	Discontinued
0.775	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD4628	Phase 3
0.7742	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD1613	Approved
0.7722	Intermediate Similarity	NPD2935	Discontinued
0.7716	Intermediate Similarity	NPD7390	Discontinued
0.7692	Intermediate Similarity	NPD447	Suspended
0.7688	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD5402	Approved
0.7674	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD2344	Approved
0.7662	Intermediate Similarity	NPD4625	Phase 3
0.7582	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD230	Phase 1
0.7578	Intermediate Similarity	NPD1243	Approved
0.7576	Intermediate Similarity	NPD5403	Approved
0.756	Intermediate Similarity	NPD37	Approved
0.7548	Intermediate Similarity	NPD3027	Phase 3
0.7543	Intermediate Similarity	NPD3751	Discontinued
0.7543	Intermediate Similarity	NPD7228	Approved
0.7529	Intermediate Similarity	NPD4967	Phase 2
0.7529	Intermediate Similarity	NPD4966	Approved
0.7529	Intermediate Similarity	NPD4965	Approved
0.7528	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD5711	Approved
0.7514	Intermediate Similarity	NPD5710	Approved
0.7514	Intermediate Similarity	NPD3787	Discontinued
0.7514	Intermediate Similarity	NPD5953	Discontinued
0.75	Intermediate Similarity	NPD1551	Phase 2
0.75	Intermediate Similarity	NPD2313	Discontinued
0.75	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD8313	Approved
0.7486	Intermediate Similarity	NPD8312	Approved
0.7485	Intermediate Similarity	NPD2309	Approved
0.747	Intermediate Similarity	NPD920	Approved
0.7468	Intermediate Similarity	NPD1933	Approved
0.7455	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD5401	Approved
0.7419	Intermediate Similarity	NPD9494	Approved
0.7403	Intermediate Similarity	NPD1470	Approved
0.7401	Intermediate Similarity	NPD7286	Phase 2
0.7386	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD4908	Phase 1
0.7368	Intermediate Similarity	NPD1201	Approved
0.7363	Intermediate Similarity	NPD8434	Phase 2
0.7349	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD7229	Phase 3
0.7302	Intermediate Similarity	NPD6779	Approved
0.7302	Intermediate Similarity	NPD6776	Approved
0.7302	Intermediate Similarity	NPD6778	Approved
0.7302	Intermediate Similarity	NPD6777	Approved
0.7302	Intermediate Similarity	NPD6780	Approved
0.7302	Intermediate Similarity	NPD6782	Approved
0.7302	Intermediate Similarity	NPD6781	Approved
0.7296	Intermediate Similarity	NPD4060	Phase 1
0.729	Intermediate Similarity	NPD1203	Approved
0.7284	Intermediate Similarity	NPD5408	Approved
0.7284	Intermediate Similarity	NPD5404	Approved
0.7284	Intermediate Similarity	NPD5405	Approved
0.7284	Intermediate Similarity	NPD5406	Approved
0.7278	Intermediate Similarity	NPD3268	Approved
0.7278	Intermediate Similarity	NPD7458	Discontinued
0.7278	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD8151	Discontinued
0.7268	Intermediate Similarity	NPD8150	Discontinued
0.7255	Intermediate Similarity	NPD1610	Phase 2
0.7244	Intermediate Similarity	NPD2798	Approved
0.7239	Intermediate Similarity	NPD1471	Phase 3
0.7219	Intermediate Similarity	NPD4360	Phase 2
0.7219	Intermediate Similarity	NPD4363	Phase 3
0.7219	Intermediate Similarity	NPD1653	Approved
0.7212	Intermediate Similarity	NPD7003	Approved
0.7208	Intermediate Similarity	NPD1608	Approved
0.7189	Intermediate Similarity	NPD4287	Approved
0.7188	Intermediate Similarity	NPD7435	Discontinued
0.7182	Intermediate Similarity	NPD7685	Pre-registration
0.7179	Intermediate Similarity	NPD2797	Approved
0.7175	Intermediate Similarity	NPD5242	Approved
0.7173	Intermediate Similarity	NPD2494	Approved
0.7173	Intermediate Similarity	NPD2493	Approved
0.717	Intermediate Similarity	NPD3764	Approved
0.717	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD6190	Approved
0.7168	Intermediate Similarity	NPD4288	Approved
0.7161	Intermediate Similarity	NPD4749	Approved
0.7143	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD8166	Discontinued
0.7107	Intermediate Similarity	NPD7783	Phase 2
0.7107	Intermediate Similarity	NPD7095	Approved
0.7107	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6273	Approved
0.7098	Intermediate Similarity	NPD7698	Approved
0.7098	Intermediate Similarity	NPD7697	Approved
0.7098	Intermediate Similarity	NPD7696	Phase 3
0.7097	Intermediate Similarity	NPD9717	Approved
0.7097	Intermediate Similarity	NPD9269	Phase 2
0.7097	Intermediate Similarity	NPD3972	Approved
0.7093	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD4361	Phase 2
0.709	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD7240	Approved
0.7083	Intermediate Similarity	NPD3450	Approved
0.7083	Intermediate Similarity	NPD3452	Approved
0.7065	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD4583	Approved
0.7062	Intermediate Similarity	NPD7871	Phase 2
0.7062	Intermediate Similarity	NPD7870	Phase 2
0.7062	Intermediate Similarity	NPD4582	Approved
0.7062	Intermediate Similarity	NPD8127	Discontinued
0.7059	Intermediate Similarity	NPD2490	Approved
0.7059	Intermediate Similarity	NPD2488	Approved
0.7048	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD6823	Phase 2
0.7044	Intermediate Similarity	NPD6832	Phase 2
0.7044	Intermediate Similarity	NPD7907	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