NPASS Compound

Structure

NPC79053 OpenBabel07101719512D 24 26 0 0 0 0 0 0 0 0999 V2000 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 1.8660 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 -2.0000 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 -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 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 -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 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 0.8660 -0.5000 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 -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 1.7321 -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 0.0000 -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 4 2 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 4 18 1 0 0 0 0 5 8 1 0 0 0 0 5 9 2 0 0 0 0 6 11 2 0 0 0 0 6 12 1 0 0 0 0 7 10 2 0 0 0 0 7 13 1 0 0 0 0 8 13 2 0 0 0 0 8 16 1 0 0 0 0 9 10 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 14 1 0 0 0 0 11 21 1 0 0 0 0 12 15 2 0 0 0 0 12 22 1 0 0 0 0 13 24 1 0 0 0 0 14 16 1 0 0 0 0 14 17 2 0 0 0 0 15 17 1 0 0 0 0 15 18 1 0 0 0 0 16 23 2 0 0 0 0 17 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.09
Volume:	325.865
LogP:	3.734
LogD:	2.738
LogS:	-3.824
# Rotatable Bonds:	2
TPSA:	111.13
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.326
Synthetic Accessibility Score:	3.05
Fsp3:	0.167
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.97
MDCK Permeability:	1.2739380508719478e-05
Pgp-inhibitor:	0.031
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.029
20% Bioavailability (F20%):	0.467
30% Bioavailability (F30%):	0.643

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	94.24653625488281%
Volume Distribution (VD):	0.819
Pgp-substrate:	11.708484649658203%

ADMET: Metabolism

CYP1A2-inhibitor:	0.953
CYP1A2-substrate:	0.482
CYP2C19-inhibitor:	0.116
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.656
CYP2C9-substrate:	0.82
CYP2D6-inhibitor:	0.315
CYP2D6-substrate:	0.225
CYP3A4-inhibitor:	0.19
CYP3A4-substrate:	0.107

ADMET: Excretion

Clearance (CL):	1.662
Half-life (T1/2):	0.843

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.085
Drug-inuced Liver Injury (DILI):	0.954
AMES Toxicity:	0.741
Rat Oral Acute Toxicity:	0.121
Maximum Recommended Daily Dose:	0.876
Skin Sensitization:	0.931
Carcinogencity:	0.115
Eye Corrosion:	0.024
Eye Irritation:	0.932
Respiratory Toxicity:	0.191

Download Data

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

Natural Product: NPC79053

Natural Product ID:	NPC79053
*Common Name:**	Cudratricusxanthone L
IUPAC Name:	1,3,6,7-tetrahydroxy-4-(2-methylbut-3-en-2-yl)xanthen-9-one
Synonyms:	cudratricusxanthone L
Standard InCHIKey:	FJCLLPPQHWALHG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H16O6/c1-4-18(2,3)15-12(22)6-11(21)14-16(23)8-5-9(19)10(20)7-13(8)24-17(14)15/h4-7,19-22H,1H2,2-3H3
SMILES:	C=CC(C)(C)c1c(cc(c2c(=O)c3cc(c(cc3oc12)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL228337
PubChem CID:	16757392
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

*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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT892	Individual Protein	Monoamine oxidase A	Mus musculus	IC50	>	150000.0	nM	PMID[499337]

☑ 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 NPC79053 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	448
0.1-0.2	2038
0.2-0.3	4553
0.3-0.4	11368
0.4-0.5	6505
0.5-0.6	3806
0.6-0.7	5269
0.7-0.8	4904
0.8-0.85	2156
0.85-0.9	1075
0.9-0.95	543
0.95-1	32

Similarity Score	Similarity Level	Natural Product ID
0.9933	High Similarity	NPC172770
0.9933	High Similarity	NPC185258
0.9803	High Similarity	NPC472275
0.9737	High Similarity	NPC235018
0.9737	High Similarity	NPC80375
0.9737	High Similarity	NPC45146
0.9675	High Similarity	NPC306321
0.9675	High Similarity	NPC303460
0.9673	High Similarity	NPC32694
0.9669	High Similarity	NPC115853
0.961	High Similarity	NPC470694
0.9605	High Similarity	NPC304008
0.9605	High Similarity	NPC219867
0.9605	High Similarity	NPC180011
0.9605	High Similarity	NPC161960
0.9605	High Similarity	NPC187745
0.9603	High Similarity	NPC113906
0.9548	High Similarity	NPC329669
0.9548	High Similarity	NPC473313
0.9548	High Similarity	NPC472278
0.9548	High Similarity	NPC220313
0.9539	High Similarity	NPC68093
0.9539	High Similarity	NPC191146
0.9539	High Similarity	NPC142339
0.9539	High Similarity	NPC138243
0.9484	High Similarity	NPC329760
0.9481	High Similarity	NPC188433
0.9477	High Similarity	NPC36852
0.9477	High Similarity	NPC78225
0.9477	High Similarity	NPC262286
0.9477	High Similarity	NPC236796
0.9423	High Similarity	NPC205265
0.9423	High Similarity	NPC472281
0.9419	High Similarity	NPC234644
0.9419	High Similarity	NPC57715
0.9419	High Similarity	NPC167678
0.9419	High Similarity	NPC29876
0.9416	High Similarity	NPC100123
0.9416	High Similarity	NPC235448
0.9412	High Similarity	NPC3980
0.9408	High Similarity	NPC49402
0.9408	High Similarity	NPC70433
0.9408	High Similarity	NPC33051
0.9408	High Similarity	NPC89474
0.9408	High Similarity	NPC227337
0.9408	High Similarity	NPC273462
0.9396	High Similarity	NPC207729
0.9371	High Similarity	NPC472276
0.9363	High Similarity	NPC473286
0.9363	High Similarity	NPC472277
0.9359	High Similarity	NPC472448
0.9359	High Similarity	NPC83922
0.9355	High Similarity	NPC476980
0.9355	High Similarity	NPC204290
0.9355	High Similarity	NPC228785
0.9355	High Similarity	NPC14353
0.9355	High Similarity	NPC119224
0.9355	High Similarity	NPC56085
0.9355	High Similarity	NPC320359
0.9346	High Similarity	NPC57674
0.9346	High Similarity	NPC230149
0.9346	High Similarity	NPC256925
0.9346	High Similarity	NPC117992
0.9346	High Similarity	NPC168247
0.9346	High Similarity	NPC152951
0.9342	High Similarity	NPC161277
0.9342	High Similarity	NPC249570
0.9342	High Similarity	NPC39007
0.9338	High Similarity	NPC248102
0.9338	High Similarity	NPC62042
0.9338	High Similarity	NPC3825
0.9338	High Similarity	NPC88804
0.9333	High Similarity	NPC276930
0.9333	High Similarity	NPC37135
0.9333	High Similarity	NPC186397
0.9333	High Similarity	NPC194856
0.9304	High Similarity	NPC277480
0.9299	High Similarity	NPC207690
0.9299	High Similarity	NPC18100
0.9299	High Similarity	NPC319200
0.9299	High Similarity	NPC189473
0.9299	High Similarity	NPC23298
0.9299	High Similarity	NPC187491
0.9295	High Similarity	NPC258331
0.9295	High Similarity	NPC61010
0.9295	High Similarity	NPC40491
0.9295	High Similarity	NPC259456
0.9295	High Similarity	NPC278052
0.9295	High Similarity	NPC266314
0.929	High Similarity	NPC197856
0.929	High Similarity	NPC250214
0.929	High Similarity	NPC95936
0.929	High Similarity	NPC46736
0.9286	High Similarity	NPC274730
0.9286	High Similarity	NPC470600
0.9286	High Similarity	NPC276444
0.9286	High Similarity	NPC472916
0.9281	High Similarity	NPC88645
0.9281	High Similarity	NPC206238
0.9281	High Similarity	NPC213896
0.9281	High Similarity	NPC167091
0.9281	High Similarity	NPC271779
0.9281	High Similarity	NPC192083
0.9281	High Similarity	NPC292214
0.9281	High Similarity	NPC476631
0.9276	High Similarity	NPC251110
0.9276	High Similarity	NPC202157
0.9276	High Similarity	NPC154345
0.9276	High Similarity	NPC171010
0.9272	High Similarity	NPC266499
0.9272	High Similarity	NPC223988
0.9241	High Similarity	NPC239752
0.9241	High Similarity	NPC275780
0.9241	High Similarity	NPC37183
0.9241	High Similarity	NPC472450
0.9236	High Similarity	NPC220912
0.9236	High Similarity	NPC25152
0.9236	High Similarity	NPC261470
0.9236	High Similarity	NPC206605
0.9231	High Similarity	NPC476283
0.9231	High Similarity	NPC476280
0.9231	High Similarity	NPC297212
0.9226	High Similarity	NPC472911
0.9226	High Similarity	NPC156057
0.9226	High Similarity	NPC474208
0.9226	High Similarity	NPC291508
0.9226	High Similarity	NPC241904
0.9226	High Similarity	NPC162869
0.9226	High Similarity	NPC476630
0.9226	High Similarity	NPC96167
0.9226	High Similarity	NPC474681
0.9226	High Similarity	NPC99597
0.9226	High Similarity	NPC469584
0.9226	High Similarity	NPC165977
0.9226	High Similarity	NPC217677
0.9226	High Similarity	NPC472914
0.9226	High Similarity	NPC472913
0.9226	High Similarity	NPC218313
0.9226	High Similarity	NPC136674
0.9226	High Similarity	NPC210084
0.9226	High Similarity	NPC475267
0.9226	High Similarity	NPC222814
0.9226	High Similarity	NPC476981
0.9226	High Similarity	NPC300727
0.9226	High Similarity	NPC223787
0.9226	High Similarity	NPC474836
0.9226	High Similarity	NPC218871
0.9226	High Similarity	NPC472910
0.9226	High Similarity	NPC245758
0.9226	High Similarity	NPC129684
0.9226	High Similarity	NPC48208
0.9226	High Similarity	NPC299520
0.9226	High Similarity	NPC181960
0.9221	High Similarity	NPC472280
0.9221	High Similarity	NPC321779
0.9221	High Similarity	NPC2928
0.9221	High Similarity	NPC256612
0.9221	High Similarity	NPC200246
0.9221	High Similarity	NPC20830
0.9216	High Similarity	NPC101996
0.9216	High Similarity	NPC180234
0.9216	High Similarity	NPC63187
0.9216	High Similarity	NPC120537
0.9216	High Similarity	NPC157784
0.9216	High Similarity	NPC106976
0.9216	High Similarity	NPC37684
0.9216	High Similarity	NPC199100
0.9211	High Similarity	NPC61620
0.9211	High Similarity	NPC184136
0.9211	High Similarity	NPC227122
0.9205	High Similarity	NPC118726
0.9205	High Similarity	NPC12367
0.9187	High Similarity	NPC288813
0.9182	High Similarity	NPC37870
0.9182	High Similarity	NPC472449
0.9182	High Similarity	NPC39091
0.9177	High Similarity	NPC152659
0.9177	High Similarity	NPC236521
0.9177	High Similarity	NPC41301
0.9177	High Similarity	NPC248638
0.9177	High Similarity	NPC7483
0.9177	High Similarity	NPC236132
0.9177	High Similarity	NPC12461
0.9177	High Similarity	NPC146134
0.9172	High Similarity	NPC228383
0.9172	High Similarity	NPC474187
0.9167	High Similarity	NPC204879
0.9167	High Similarity	NPC210459
0.9167	High Similarity	NPC476242
0.9167	High Similarity	NPC329091
0.9161	High Similarity	NPC195796
0.9161	High Similarity	NPC255106
0.9161	High Similarity	NPC278778
0.9161	High Similarity	NPC6633
0.9161	High Similarity	NPC133970
0.9161	High Similarity	NPC291878
0.9161	High Similarity	NPC235165
0.9161	High Similarity	NPC472455
0.9161	High Similarity	NPC5322
0.9161	High Similarity	NPC35038

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 NPC79053 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	426
0.1-0.2	1020
0.2-0.3	1804
0.3-0.4	2760
0.4-0.5	1710
0.5-0.6	950
0.6-0.7	324
0.7-0.8	110
0.8-0.85	36
0.85-0.9	6
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9281	High Similarity	NPD2393	Clinical (unspecified phase)
0.9156	High Similarity	NPD2801	Approved
0.8968	High Similarity	NPD1934	Approved
0.894	High Similarity	NPD1511	Approved
0.8824	High Similarity	NPD1512	Approved
0.875	High Similarity	NPD5494	Approved
0.8679	High Similarity	NPD3882	Suspended
0.8636	High Similarity	NPD4378	Clinical (unspecified phase)
0.8537	High Similarity	NPD6166	Phase 2
0.8537	High Similarity	NPD6168	Clinical (unspecified phase)
0.8537	High Similarity	NPD6167	Clinical (unspecified phase)
0.8481	Intermediate Similarity	NPD4380	Phase 2
0.8447	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD7819	Suspended
0.8434	Intermediate Similarity	NPD3818	Discontinued
0.8431	Intermediate Similarity	NPD2800	Approved
0.8397	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8395	Intermediate Similarity	NPD7075	Discontinued
0.8366	Intermediate Similarity	NPD1549	Phase 2
0.8333	Intermediate Similarity	NPD7074	Phase 3
0.8323	Intermediate Similarity	NPD1465	Phase 2
0.8323	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD6232	Discontinued
0.8301	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8301	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8294	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8274	Intermediate Similarity	NPD5844	Phase 1
0.8274	Intermediate Similarity	NPD7054	Approved
0.8272	Intermediate Similarity	NPD3817	Phase 2
0.8272	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD943	Approved
0.8263	Intermediate Similarity	NPD7473	Discontinued
0.8242	Intermediate Similarity	NPD6959	Discontinued
0.8225	Intermediate Similarity	NPD7472	Approved
0.8199	Intermediate Similarity	NPD7411	Suspended
0.8176	Intermediate Similarity	NPD6797	Phase 2
0.8171	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.817	Intermediate Similarity	NPD1510	Phase 2
0.8148	Intermediate Similarity	NPD6801	Discontinued
0.8146	Intermediate Similarity	NPD1240	Approved
0.8137	Intermediate Similarity	NPD6599	Discontinued
0.8129	Intermediate Similarity	NPD7251	Discontinued
0.8117	Intermediate Similarity	NPD2796	Approved
0.8117	Intermediate Similarity	NPD2935	Discontinued
0.8039	Intermediate Similarity	NPD1607	Approved
0.8024	Intermediate Similarity	NPD1247	Approved
0.7988	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD6799	Approved
0.7977	Intermediate Similarity	NPD7808	Phase 3
0.7965	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD3749	Approved
0.7939	Intermediate Similarity	NPD5402	Approved
0.7919	Intermediate Similarity	NPD6559	Discontinued
0.7911	Intermediate Similarity	NPD3750	Approved
0.7892	Intermediate Similarity	NPD7768	Phase 2
0.7885	Intermediate Similarity	NPD6100	Approved
0.7885	Intermediate Similarity	NPD6099	Approved
0.7881	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD3226	Approved
0.7834	Intermediate Similarity	NPD2346	Discontinued
0.7826	Intermediate Similarity	NPD2533	Approved
0.7826	Intermediate Similarity	NPD2532	Approved
0.7826	Intermediate Similarity	NPD2534	Approved
0.7824	Intermediate Similarity	NPD3926	Phase 2
0.7821	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD2799	Discontinued
0.7821	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD6651	Approved
0.7799	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD230	Phase 1
0.7736	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD920	Approved
0.7722	Intermediate Similarity	NPD2344	Approved
0.7709	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD919	Approved
0.7688	Intermediate Similarity	NPD4628	Phase 3
0.7677	Intermediate Similarity	NPD1613	Approved
0.7677	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD2313	Discontinued
0.7644	Intermediate Similarity	NPD7286	Phase 2
0.7628	Intermediate Similarity	NPD447	Suspended
0.7625	Intermediate Similarity	NPD1243	Approved
0.7624	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD3748	Approved
0.7557	Intermediate Similarity	NPD5953	Discontinued
0.7547	Intermediate Similarity	NPD1551	Phase 2
0.7546	Intermediate Similarity	NPD7390	Discontinued
0.7531	Intermediate Similarity	NPD2309	Approved
0.7515	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD5403	Approved
0.75	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD3751	Discontinued
0.7472	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD8434	Phase 2
0.7394	Intermediate Similarity	NPD5401	Approved
0.7384	Intermediate Similarity	NPD6234	Discontinued
0.7378	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD4625	Phase 3
0.7372	Intermediate Similarity	NPD3027	Phase 3
0.7365	Intermediate Similarity	NPD1653	Approved
0.7362	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD5711	Approved
0.7356	Intermediate Similarity	NPD3787	Discontinued
0.7356	Intermediate Similarity	NPD5710	Approved
0.734	Intermediate Similarity	NPD6776	Approved
0.734	Intermediate Similarity	NPD6779	Approved
0.734	Intermediate Similarity	NPD6780	Approved
0.734	Intermediate Similarity	NPD6781	Approved
0.734	Intermediate Similarity	NPD6778	Approved
0.734	Intermediate Similarity	NPD6782	Approved
0.734	Intermediate Similarity	NPD6777	Approved
0.7338	Intermediate Similarity	NPD1203	Approved
0.7333	Intermediate Similarity	NPD8313	Approved
0.7333	Intermediate Similarity	NPD8312	Approved
0.7317	Intermediate Similarity	NPD6190	Approved
0.7308	Intermediate Similarity	NPD4908	Phase 1
0.7299	Intermediate Similarity	NPD7199	Phase 2
0.7296	Intermediate Similarity	NPD1933	Approved
0.729	Intermediate Similarity	NPD2798	Approved
0.7289	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD4360	Phase 2
0.7258	Intermediate Similarity	NPD4363	Phase 3
0.7255	Intermediate Similarity	NPD9269	Phase 2
0.7244	Intermediate Similarity	NPD9494	Approved
0.7229	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1470	Approved
0.7225	Intermediate Similarity	NPD7435	Discontinued
0.7219	Intermediate Similarity	NPD7458	Discontinued
0.7216	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD3268	Approved
0.7213	Intermediate Similarity	NPD8150	Discontinued
0.7208	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6844	Discontinued
0.7193	Intermediate Similarity	NPD37	Approved
0.7191	Intermediate Similarity	NPD7228	Approved
0.719	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD1610	Phase 2
0.7168	Intermediate Similarity	NPD4967	Phase 2
0.7168	Intermediate Similarity	NPD4965	Approved
0.7168	Intermediate Similarity	NPD4966	Approved
0.7159	Intermediate Similarity	NPD7229	Phase 3
0.7143	Intermediate Similarity	NPD1608	Approved
0.7143	Intermediate Similarity	NPD3972	Approved
0.7143	Intermediate Similarity	NPD9717	Approved
0.7135	Intermediate Similarity	NPD7698	Approved
0.7135	Intermediate Similarity	NPD7696	Phase 3
0.7135	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7697	Approved
0.7134	Intermediate Similarity	NPD2861	Phase 2
0.7128	Intermediate Similarity	NPD8151	Discontinued
0.7127	Intermediate Similarity	NPD7685	Pre-registration
0.7119	Intermediate Similarity	NPD5242	Approved
0.7118	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD5404	Approved
0.7117	Intermediate Similarity	NPD5406	Approved
0.7117	Intermediate Similarity	NPD5405	Approved
0.7117	Intermediate Similarity	NPD5408	Approved
0.7115	Intermediate Similarity	NPD2797	Approved
0.7107	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD7871	Phase 2
0.7098	Intermediate Similarity	NPD7870	Phase 2
0.7097	Intermediate Similarity	NPD4749	Approved
0.709	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6832	Phase 2
0.7083	Intermediate Similarity	NPD6823	Phase 2
0.7081	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD2403	Approved
0.7078	Intermediate Similarity	NPD1201	Approved
0.7077	Intermediate Similarity	NPD7701	Phase 2
0.7074	Intermediate Similarity	NPD6534	Approved
0.7074	Intermediate Similarity	NPD6535	Approved
0.7073	Intermediate Similarity	NPD1471	Phase 3
0.7056	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7783	Phase 2
0.7055	Intermediate Similarity	NPD4308	Phase 3
0.7052	Intermediate Similarity	NPD5761	Phase 2
0.7052	Intermediate Similarity	NPD5760	Phase 2
0.7048	Intermediate Similarity	NPD7003	Approved
0.7048	Intermediate Similarity	NPD8166	Discontinued
0.7043	Intermediate Similarity	NPD4287	Approved
0.7037	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4361	Phase 2
0.7033	Intermediate Similarity	NPD6104	Discontinued
0.7026	Intermediate Similarity	NPD7584	Approved
0.7017	Intermediate Similarity	NPD1729	Discontinued
0.7011	Intermediate Similarity	NPD4288	Approved
0.7011	Intermediate Similarity	NPD2296	Approved
0.7005	Intermediate Similarity	NPD7874	Approved
0.7005	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD411	Approved
0.7	Intermediate Similarity	NPD3764	Approved
0.6993	Remote Similarity	NPD9268	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