NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	228.04
Volume:	224.441
LogP:	2.599
LogD:	2.508
LogS:	-3.462
# Rotatable Bonds:	0
TPSA:	70.67
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.579
Synthetic Accessibility Score:	2.086
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.738
MDCK Permeability:	1.1159031600982416e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.919
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.809
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.03
Plasma Protein Binding (PPB):	92.59375762939453%
Volume Distribution (VD):	0.661
Pgp-substrate:	12.106879234313965%

ADMET: Metabolism

CYP1A2-inhibitor:	0.981
CYP1A2-substrate:	0.253
CYP2C19-inhibitor:	0.453
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.317
CYP2C9-substrate:	0.95
CYP2D6-inhibitor:	0.801
CYP2D6-substrate:	0.89
CYP3A4-inhibitor:	0.855
CYP3A4-substrate:	0.174

ADMET: Excretion

Clearance (CL):	7.488
Half-life (T1/2):	0.827

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.149
Drug-inuced Liver Injury (DILI):	0.914
AMES Toxicity:	0.662
Rat Oral Acute Toxicity:	0.175
Maximum Recommended Daily Dose:	0.855
Skin Sensitization:	0.937
Carcinogencity:	0.744
Eye Corrosion:	0.082
Eye Irritation:	0.98
Respiratory Toxicity:	0.189

Download Data

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

Natural Product: NPC159855

Natural Product ID:	NPC159855
*Common Name:**	2,6-Dihydroxyxanthone
IUPAC Name:	2,6-dihydroxyxanthen-9-one
Synonyms:
Standard InCHIKey:	UHFHFHSHVGUMIQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H8O4/c14-7-2-4-11-10(5-7)13(16)9-3-1-8(15)6-12(9)17-11/h1-6,14-15H
SMILES:	Oc1ccc2c(c1)c(=O)c1c(o2)cc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3357570
PubChem CID:	14408256
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.	n.a.	n.a.	PMID[15787460]
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[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	6

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	32400.0	nM	PMID[491703]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	92400.0	nM	PMID[491703]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	52200.0	nM	PMID[491703]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	88900.0	nM	PMID[491703]
NPT2641	Cell Line	COLO 320	Homo sapiens	IC50	=	31500.0	nM	PMID[491703]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	30000.0	nM	PMID[491702]

☑ 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 NPC159855 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	545
0.1-0.2	2216
0.2-0.3	5669
0.3-0.4	12146
0.4-0.5	4644
0.5-0.6	4464
0.6-0.7	5352
0.7-0.8	4279
0.8-0.85	1981
0.85-0.9	1139
0.9-0.95	245
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC169479
0.9706	High Similarity	NPC18457
0.9645	High Similarity	NPC186397
0.9645	High Similarity	NPC37135
0.9577	High Similarity	NPC266499
0.9577	High Similarity	NPC223988
0.9565	High Similarity	NPC145673
0.951	High Similarity	NPC101957
0.951	High Similarity	NPC120105
0.9507	High Similarity	NPC194856
0.9507	High Similarity	NPC276930
0.9485	High Similarity	NPC9985
0.9485	High Similarity	NPC239495
0.9444	High Similarity	NPC251110
0.9444	High Similarity	NPC149614
0.9437	High Similarity	NPC207729
0.9424	High Similarity	NPC182421
0.9375	High Similarity	NPC61620
0.9375	High Similarity	NPC248102
0.9375	High Similarity	NPC179183
0.9375	High Similarity	NPC227122
0.9375	High Similarity	NPC62042
0.9371	High Similarity	NPC12367
0.9371	High Similarity	NPC118726
0.9315	High Similarity	NPC271779
0.9315	High Similarity	NPC167091
0.9315	High Similarity	NPC206238
0.9315	High Similarity	NPC88645
0.9315	High Similarity	NPC292214
0.931	High Similarity	NPC204515
0.931	High Similarity	NPC117579
0.9301	High Similarity	NPC130230
0.9301	High Similarity	NPC275772
0.9301	High Similarity	NPC239312
0.9296	High Similarity	NPC155144
0.9296	High Similarity	NPC184649
0.9296	High Similarity	NPC303185
0.9291	High Similarity	NPC73028
0.9286	High Similarity	NPC275734
0.9281	High Similarity	NPC329225
0.9281	High Similarity	NPC472460
0.9281	High Similarity	NPC147686
0.927	High Similarity	NPC172262
0.9247	High Similarity	NPC39007
0.9247	High Similarity	NPC161277
0.9247	High Similarity	NPC474843
0.9247	High Similarity	NPC101996
0.9247	High Similarity	NPC199100
0.9247	High Similarity	NPC180234
0.9247	High Similarity	NPC120537
0.9241	High Similarity	NPC45873
0.9241	High Similarity	NPC470107
0.9236	High Similarity	NPC196277
0.9236	High Similarity	NPC43669
0.9236	High Similarity	NPC272721
0.9231	High Similarity	NPC299011
0.9231	High Similarity	NPC196114
0.9225	High Similarity	NPC113770
0.9214	High Similarity	NPC316480
0.9214	High Similarity	NPC261234
0.9209	High Similarity	NPC13768
0.9209	High Similarity	NPC32441
0.9209	High Similarity	NPC107586
0.9209	High Similarity	NPC287246
0.9209	High Similarity	NPC212767
0.9209	High Similarity	NPC275055
0.9209	High Similarity	NPC290291
0.9209	High Similarity	NPC299379
0.9209	High Similarity	NPC84585
0.9209	High Similarity	NPC296490
0.9209	High Similarity	NPC228661
0.9209	High Similarity	NPC12296
0.9209	High Similarity	NPC476480
0.9209	High Similarity	NPC243083
0.9209	High Similarity	NPC79943
0.9209	High Similarity	NPC295261
0.9197	High Similarity	NPC213216
0.9197	High Similarity	NPC78540
0.9197	High Similarity	NPC57601
0.9197	High Similarity	NPC50898
0.9197	High Similarity	NPC274121
0.9184	High Similarity	NPC178964
0.9184	High Similarity	NPC95842
0.9184	High Similarity	NPC472915
0.9184	High Similarity	NPC280530
0.9178	High Similarity	NPC171010
0.9178	High Similarity	NPC202157
0.9172	High Similarity	NPC183959
0.9172	High Similarity	NPC195351
0.9172	High Similarity	NPC216318
0.9172	High Similarity	NPC1612
0.9172	High Similarity	NPC296197
0.9172	High Similarity	NPC17286
0.9172	High Similarity	NPC259713
0.9167	High Similarity	NPC77378
0.9167	High Similarity	NPC46941
0.9161	High Similarity	NPC70136
0.9161	High Similarity	NPC469764
0.9161	High Similarity	NPC311144
0.9155	High Similarity	NPC310340
0.9155	High Similarity	NPC202981
0.9155	High Similarity	NPC144499
0.9149	High Similarity	NPC69769
0.9143	High Similarity	NPC188947
0.9143	High Similarity	NPC99333
0.9143	High Similarity	NPC118813
0.9143	High Similarity	NPC280284
0.9137	High Similarity	NPC216361
0.9137	High Similarity	NPC281917
0.9137	High Similarity	NPC256042
0.9137	High Similarity	NPC187432
0.9137	High Similarity	NPC193792
0.9137	High Similarity	NPC116775
0.9137	High Similarity	NPC87545
0.9137	High Similarity	NPC235428
0.9128	High Similarity	NPC181960
0.9128	High Similarity	NPC99597
0.9128	High Similarity	NPC210084
0.9122	High Similarity	NPC37392
0.9122	High Similarity	NPC2928
0.9122	High Similarity	NPC113906
0.9122	High Similarity	NPC472909
0.9118	High Similarity	NPC141549
0.911	High Similarity	NPC29231
0.911	High Similarity	NPC184136
0.911	High Similarity	NPC77858
0.911	High Similarity	NPC37348
0.911	High Similarity	NPC306821
0.9103	High Similarity	NPC294852
0.9103	High Similarity	NPC321011
0.9103	High Similarity	NPC218490
0.9103	High Similarity	NPC218569
0.9103	High Similarity	NPC188679
0.9103	High Similarity	NPC39195
0.9097	High Similarity	NPC469758
0.9097	High Similarity	NPC187282
0.9097	High Similarity	NPC290133
0.9097	High Similarity	NPC24136
0.9097	High Similarity	NPC231013
0.9091	High Similarity	NPC18585
0.9091	High Similarity	NPC106985
0.9091	High Similarity	NPC166138
0.9091	High Similarity	NPC279121
0.9085	High Similarity	NPC3188
0.9078	High Similarity	NPC265871
0.9078	High Similarity	NPC225153
0.9078	High Similarity	NPC329203
0.9078	High Similarity	NPC274784
0.9078	High Similarity	NPC20709
0.9078	High Similarity	NPC222342
0.9078	High Similarity	NPC150648
0.9078	High Similarity	NPC310135
0.9071	High Similarity	NPC250266
0.9071	High Similarity	NPC266597
0.9067	High Similarity	NPC185258
0.9067	High Similarity	NPC172770
0.9065	High Similarity	NPC234560
0.9065	High Similarity	NPC39426
0.906	High Similarity	NPC472916
0.906	High Similarity	NPC235165
0.906	High Similarity	NPC201837
0.906	High Similarity	NPC255106
0.906	High Similarity	NPC191146
0.906	High Similarity	NPC138243
0.906	High Similarity	NPC68093
0.9054	High Similarity	NPC280937
0.9054	High Similarity	NPC89474
0.9051	High Similarity	NPC113006
0.9048	High Similarity	NPC226973
0.9048	High Similarity	NPC308451
0.9048	High Similarity	NPC208043
0.9048	High Similarity	NPC225731
0.9044	High Similarity	NPC278787
0.9041	High Similarity	NPC294502
0.9041	High Similarity	NPC200221
0.9041	High Similarity	NPC65775
0.9041	High Similarity	NPC105512
0.9041	High Similarity	NPC10027
0.9034	High Similarity	NPC21835
0.9034	High Similarity	NPC308200
0.9034	High Similarity	NPC17816
0.9034	High Similarity	NPC51443
0.9034	High Similarity	NPC74881
0.9034	High Similarity	NPC168803
0.9034	High Similarity	NPC95864
0.9028	High Similarity	NPC311741
0.9028	High Similarity	NPC131766
0.9028	High Similarity	NPC234629
0.9028	High Similarity	NPC98926
0.9021	High Similarity	NPC1534
0.9021	High Similarity	NPC175013
0.9021	High Similarity	NPC473042
0.9014	High Similarity	NPC270883
0.9014	High Similarity	NPC110228
0.9014	High Similarity	NPC284550
0.9014	High Similarity	NPC281207
0.9014	High Similarity	NPC261227
0.9014	High Similarity	NPC76445
0.9014	High Similarity	NPC188243
0.9014	High Similarity	NPC129853

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 NPC159855 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	515
0.1-0.2	1003
0.2-0.3	1743
0.3-0.4	2731
0.4-0.5	1711
0.5-0.6	1003
0.6-0.7	281
0.7-0.8	106
0.8-0.85	42
0.85-0.9	10
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9281	High Similarity	NPD1549	Phase 2
0.9209	High Similarity	NPD1550	Clinical (unspecified phase)
0.9209	High Similarity	NPD1552	Clinical (unspecified phase)
0.9091	High Similarity	NPD1511	Approved
0.9065	High Similarity	NPD1510	Phase 2
0.8966	High Similarity	NPD1512	Approved
0.8926	High Similarity	NPD2801	Approved
0.8913	High Similarity	NPD1240	Approved
0.8897	High Similarity	NPD4378	Clinical (unspecified phase)
0.8859	High Similarity	NPD1934	Approved
0.88	High Similarity	NPD2393	Clinical (unspecified phase)
0.8786	High Similarity	NPD1607	Approved
0.8639	High Similarity	NPD7410	Clinical (unspecified phase)
0.8601	High Similarity	NPD2796	Approved
0.86	High Similarity	NPD4380	Phase 2
0.8553	High Similarity	NPD7819	Suspended
0.8506	High Similarity	NPD3749	Approved
0.8506	High Similarity	NPD4381	Clinical (unspecified phase)
0.8493	Intermediate Similarity	NPD3750	Approved
0.8442	Intermediate Similarity	NPD3882	Suspended
0.8421	Intermediate Similarity	NPD7411	Suspended
0.8397	Intermediate Similarity	NPD5494	Approved
0.8387	Intermediate Similarity	NPD7075	Discontinued
0.838	Intermediate Similarity	NPD943	Approved
0.8377	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8356	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8345	Intermediate Similarity	NPD1551	Phase 2
0.8345	Intermediate Similarity	NPD2935	Discontinued
0.8323	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD3818	Discontinued
0.8312	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD6166	Phase 2
0.8302	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8299	Intermediate Similarity	NPD2800	Approved
0.8258	Intermediate Similarity	NPD5402	Approved
0.8228	Intermediate Similarity	NPD6959	Discontinued
0.82	Intermediate Similarity	NPD6799	Approved
0.8194	Intermediate Similarity	NPD1465	Phase 2
0.8171	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD2344	Approved
0.8151	Intermediate Similarity	NPD3748	Approved
0.8151	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8143	Intermediate Similarity	NPD1203	Approved
0.8141	Intermediate Similarity	NPD3817	Phase 2
0.8112	Intermediate Similarity	NPD2313	Discontinued
0.8098	Intermediate Similarity	NPD7074	Phase 3
0.8075	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD1243	Approved
0.8052	Intermediate Similarity	NPD3226	Approved
0.8041	Intermediate Similarity	NPD2346	Discontinued
0.8039	Intermediate Similarity	NPD920	Approved
0.8037	Intermediate Similarity	NPD7054	Approved
0.8026	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD6801	Discontinued
0.8	Intermediate Similarity	NPD6599	Discontinued
0.8	Intermediate Similarity	NPD1247	Approved
0.7988	Intermediate Similarity	NPD7472	Approved
0.7986	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD7768	Phase 2
0.7973	Intermediate Similarity	NPD6100	Approved
0.7973	Intermediate Similarity	NPD6099	Approved
0.7972	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD6232	Discontinued
0.7947	Intermediate Similarity	NPD2309	Approved
0.7939	Intermediate Similarity	NPD6797	Phase 2
0.7933	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD5844	Phase 1
0.7927	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD7473	Discontinued
0.7908	Intermediate Similarity	NPD2532	Approved
0.7908	Intermediate Similarity	NPD2534	Approved
0.7908	Intermediate Similarity	NPD2533	Approved
0.7905	Intermediate Similarity	NPD2799	Discontinued
0.7902	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD7251	Discontinued
0.7892	Intermediate Similarity	NPD6559	Discontinued
0.7881	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD1610	Phase 2
0.7844	Intermediate Similarity	NPD7808	Phase 3
0.7831	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD447	Suspended
0.7806	Intermediate Similarity	NPD5403	Approved
0.7801	Intermediate Similarity	NPD9717	Approved
0.7792	Intermediate Similarity	NPD5401	Approved
0.7785	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7762	Intermediate Similarity	NPD1470	Approved
0.7755	Intermediate Similarity	NPD1613	Approved
0.7755	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD5953	Discontinued
0.7711	Intermediate Similarity	NPD7286	Phase 2
0.7703	Intermediate Similarity	NPD230	Phase 1
0.7698	Intermediate Similarity	NPD1548	Phase 1
0.7683	Intermediate Similarity	NPD3926	Phase 2
0.7676	Intermediate Similarity	NPD1608	Approved
0.7654	Intermediate Similarity	NPD919	Approved
0.7651	Intermediate Similarity	NPD3751	Discontinued
0.7651	Intermediate Similarity	NPD6651	Approved
0.7619	Intermediate Similarity	NPD411	Approved
0.7613	Intermediate Similarity	NPD7390	Discontinued
0.7606	Intermediate Similarity	NPD422	Phase 1
0.7606	Intermediate Similarity	NPD1201	Approved
0.7603	Intermediate Similarity	NPD4908	Phase 1
0.7586	Intermediate Similarity	NPD2798	Approved
0.7584	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD6844	Discontinued
0.7552	Intermediate Similarity	NPD1481	Phase 2
0.755	Intermediate Similarity	NPD4308	Phase 3
0.7534	Intermediate Similarity	NPD2861	Phase 2
0.7532	Intermediate Similarity	NPD4628	Phase 3
0.7529	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3764	Approved
0.75	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3268	Approved
0.7486	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1535	Discovery
0.7483	Intermediate Similarity	NPD6832	Phase 2
0.7471	Intermediate Similarity	NPD4287	Approved
0.7469	Intermediate Similarity	NPD4288	Approved
0.7468	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD17	Approved
0.7452	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD1471	Phase 3
0.7448	Intermediate Similarity	NPD3225	Approved
0.7432	Intermediate Similarity	NPD4625	Phase 3
0.741	Intermediate Similarity	NPD5710	Approved
0.741	Intermediate Similarity	NPD3787	Discontinued
0.741	Intermediate Similarity	NPD5711	Approved
0.7397	Intermediate Similarity	NPD2797	Approved
0.7383	Intermediate Similarity	NPD1296	Phase 2
0.7379	Intermediate Similarity	NPD4749	Approved
0.7362	Intermediate Similarity	NPD2296	Approved
0.7351	Intermediate Similarity	NPD1933	Approved
0.7324	Intermediate Similarity	NPD9545	Approved
0.732	Intermediate Similarity	NPD7033	Discontinued
0.7312	Intermediate Similarity	NPD1653	Approved
0.731	Intermediate Similarity	NPD9269	Phase 2
0.7305	Intermediate Similarity	NPD9493	Approved
0.7305	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD4363	Phase 3
0.7303	Intermediate Similarity	NPD4360	Phase 2
0.7293	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD4307	Phase 2
0.7284	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD8313	Approved
0.7283	Intermediate Similarity	NPD8312	Approved
0.7279	Intermediate Similarity	NPD3267	Approved
0.7279	Intermediate Similarity	NPD3266	Approved
0.7279	Intermediate Similarity	NPD1164	Approved
0.7273	Intermediate Similarity	NPD5408	Approved
0.7273	Intermediate Similarity	NPD5404	Approved
0.7273	Intermediate Similarity	NPD5405	Approved
0.7273	Intermediate Similarity	NPD9268	Approved
0.7273	Intermediate Similarity	NPD5406	Approved
0.7267	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD2654	Approved
0.7234	Intermediate Similarity	NPD6671	Approved
0.723	Intermediate Similarity	NPD1019	Discontinued
0.7214	Intermediate Similarity	NPD1241	Discontinued
0.7202	Intermediate Similarity	NPD7229	Phase 3
0.7198	Intermediate Similarity	NPD6778	Approved
0.7198	Intermediate Similarity	NPD6779	Approved
0.7198	Intermediate Similarity	NPD6777	Approved
0.7198	Intermediate Similarity	NPD6782	Approved
0.7198	Intermediate Similarity	NPD6780	Approved
0.7198	Intermediate Similarity	NPD6781	Approved
0.7198	Intermediate Similarity	NPD6776	Approved
0.7192	Intermediate Similarity	NPD3972	Approved
0.7181	Intermediate Similarity	NPD9494	Approved
0.7175	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6190	Approved
0.7151	Intermediate Similarity	NPD1729	Discontinued
0.7115	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD3027	Phase 3
0.7081	Intermediate Similarity	NPD7696	Phase 3
0.7081	Intermediate Similarity	NPD7698	Approved
0.7081	Intermediate Similarity	NPD7435	Discontinued
0.7081	Intermediate Similarity	NPD7697	Approved
0.7072	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD4361	Phase 2
0.7069	Intermediate Similarity	NPD6104	Discontinued
0.7066	Intermediate Similarity	NPD6971	Discontinued
0.7062	Intermediate Similarity	NPD8434	Phase 2
0.7044	Intermediate Similarity	NPD2354	Approved
0.7043	Intermediate Similarity	NPD7871	Phase 2
0.7043	Intermediate Similarity	NPD7870	Phase 2
0.7041	Intermediate Similarity	NPD7199	Phase 2
0.7039	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD2403	Approved
0.7013	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD5124	Phase 1
0.7011	Intermediate Similarity	NPD1252	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6233	Phase 2

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