NPASS Compound

Structure

CID318173 OpenBabel06191716142D 22 24 0 0 1 0 0 0 0 0999 V2000 1.7321 -4.0000 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 2.5981 -1.5000 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 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 10 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 9 1 0 0 0 0 5 12 2 0 0 0 0 6 7 2 0 0 0 0 6 11 1 0 0 0 0 7 13 1 0 0 0 0 8 10 1 0 0 0 0 8 19 1 0 0 0 0 9 11 2 0 0 0 0 10 14 1 0 0 0 0 11 12 1 0 0 0 0 12 15 1 0 0 0 0 13 15 2 0 0 0 0 13 16 1 0 0 0 0 14 16 1 0 0 0 0 14 17 2 0 0 0 0 15 18 1 0 0 0 0 16 20 2 0 0 0 0 17 18 1 0 0 0 0 17 21 1 0 0 0 0 18 22 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	296.1
Volume:	308.284
LogP:	3.708
LogD:	2.154
LogS:	-3.492
# Rotatable Bonds:	2
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.291
Synthetic Accessibility Score:	3.282
Fsp3:	0.167
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.999
MDCK Permeability:	1.7347687389701605e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.08
20% Bioavailability (F20%):	0.072
30% Bioavailability (F30%):	0.952

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	96.98912048339844%
Volume Distribution (VD):	0.508
Pgp-substrate:	2.185199499130249%

ADMET: Metabolism

CYP1A2-inhibitor:	0.919
CYP1A2-substrate:	0.901
CYP2C19-inhibitor:	0.059
CYP2C19-substrate:	0.174
CYP2C9-inhibitor:	0.481
CYP2C9-substrate:	0.651
CYP2D6-inhibitor:	0.57
CYP2D6-substrate:	0.264
CYP3A4-inhibitor:	0.141
CYP3A4-substrate:	0.139

ADMET: Excretion

Clearance (CL):	5.77
Half-life (T1/2):	0.608

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.037
Drug-inuced Liver Injury (DILI):	0.957
AMES Toxicity:	0.772
Rat Oral Acute Toxicity:	0.121
Maximum Recommended Daily Dose:	0.832
Skin Sensitization:	0.951
Carcinogencity:	0.706
Eye Corrosion:	0.004
Eye Irritation:	0.925
Respiratory Toxicity:	0.866

Download Data

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

Natural Product: NPC318173

Natural Product ID:	NPC318173
*Common Name:**	Danshenxinkun A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MHCXKYJBQMJPRJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H16O4/c1-9-4-3-5-12-11(9)6-7-13-15(12)18(22)17(21)14(16(13)20)10(2)8-19/h3-7,10,19,21H,8H2,1-2H3
SMILES:	OCC(C1=C(O)C(=O)c2c(C1=O)ccc1c2cccc1C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL390741
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[11374966]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16038550]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17583950]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18855446]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20455578]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21775156]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23286284]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24108414]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27569393]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29185738]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30351923]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[3655791]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	roots	n.a.	n.a.	PMID[9834151]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	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
IC50	5

Activity Type	# Activity
Cell Line	1
Individual Protein	1
NON-MOLECULAR	1
PROTEIN FAMILY	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT196	Cell Line	AGS	Homo sapiens	IC50	>	50000.0	nM	PMID[514912]
NPT21802	PROTEIN FAMILY	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	IC50	>	20000.0	nM	PMID[514912]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[514912]
NPT68	Individual Protein	Aldose reductase	Rattus norvegicus	IC50	=	870.96	nM	PMID[514913]

☑ 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 NPC318173 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	224
0.1-0.2	1124
0.2-0.3	2572
0.3-0.4	7778
0.4-0.5	13717
0.5-0.6	11871
0.6-0.7	4748
0.7-0.8	600
0.8-0.85	42
0.85-0.9	14
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9554	High Similarity	NPC222968
0.9554	High Similarity	NPC80605
0.9554	High Similarity	NPC323440
0.9316	High Similarity	NPC318067
0.9189	High Similarity	NPC292834
0.9107	High Similarity	NPC143768
0.8992	High Similarity	NPC328107
0.885	High Similarity	NPC186128
0.8818	High Similarity	NPC172483
0.8818	High Similarity	NPC134120
0.8772	High Similarity	NPC470253
0.8761	High Similarity	NPC265513
0.8739	High Similarity	NPC100767
0.8696	High Similarity	NPC326664
0.8636	High Similarity	NPC274443
0.8632	High Similarity	NPC469843
0.8571	High Similarity	NPC476645
0.8548	High Similarity	NPC478162
0.8548	High Similarity	NPC478165
0.8545	High Similarity	NPC222390
0.8545	High Similarity	NPC244427
0.8534	High Similarity	NPC67377
0.8534	High Similarity	NPC196673
0.8496	Intermediate Similarity	NPC203732
0.8468	Intermediate Similarity	NPC247976
0.8462	Intermediate Similarity	NPC215419
0.8417	Intermediate Similarity	NPC202015
0.8319	Intermediate Similarity	NPC471186
0.8306	Intermediate Similarity	NPC295664
0.8279	Intermediate Similarity	NPC144547
0.8279	Intermediate Similarity	NPC472981
0.8276	Intermediate Similarity	NPC474057
0.8273	Intermediate Similarity	NPC49994
0.8264	Intermediate Similarity	NPC204784
0.8246	Intermediate Similarity	NPC83409
0.8246	Intermediate Similarity	NPC185763
0.823	Intermediate Similarity	NPC329282
0.822	Intermediate Similarity	NPC471721
0.8205	Intermediate Similarity	NPC471189
0.8205	Intermediate Similarity	NPC218855
0.8197	Intermediate Similarity	NPC988
0.8197	Intermediate Similarity	NPC289432
0.8197	Intermediate Similarity	NPC105709
0.8182	Intermediate Similarity	NPC156021
0.8145	Intermediate Similarity	NPC65627
0.8142	Intermediate Similarity	NPC329556
0.8136	Intermediate Similarity	NPC93287
0.812	Intermediate Similarity	NPC137315
0.811	Intermediate Similarity	NPC51448
0.811	Intermediate Similarity	NPC115797
0.8092	Intermediate Similarity	NPC23894
0.8067	Intermediate Similarity	NPC241851
0.8067	Intermediate Similarity	NPC130591
0.8067	Intermediate Similarity	NPC234637
0.8062	Intermediate Similarity	NPC27659
0.8051	Intermediate Similarity	NPC66208
0.8049	Intermediate Similarity	NPC232958
0.803	Intermediate Similarity	NPC309056
0.8017	Intermediate Similarity	NPC112903
0.8017	Intermediate Similarity	NPC158157
0.8	Intermediate Similarity	NPC228936
0.8	Intermediate Similarity	NPC470764
0.7983	Intermediate Similarity	NPC471481
0.7965	Intermediate Similarity	NPC112552
0.7955	Intermediate Similarity	NPC474659
0.7953	Intermediate Similarity	NPC236405
0.7949	Intermediate Similarity	NPC192577
0.7946	Intermediate Similarity	NPC134882
0.7937	Intermediate Similarity	NPC85511
0.7937	Intermediate Similarity	NPC51079
0.7934	Intermediate Similarity	NPC135730
0.7931	Intermediate Similarity	NPC142326
0.7931	Intermediate Similarity	NPC94751
0.792	Intermediate Similarity	NPC167323
0.792	Intermediate Similarity	NPC269923
0.7909	Intermediate Similarity	NPC34243
0.7909	Intermediate Similarity	NPC238219
0.7907	Intermediate Similarity	NPC96024
0.7903	Intermediate Similarity	NPC77000
0.7903	Intermediate Similarity	NPC238861
0.7899	Intermediate Similarity	NPC471188
0.7899	Intermediate Similarity	NPC280789
0.7891	Intermediate Similarity	NPC81135
0.7874	Intermediate Similarity	NPC164014
0.7857	Intermediate Similarity	NPC265220
0.7857	Intermediate Similarity	NPC239185
0.7851	Intermediate Similarity	NPC93181
0.7851	Intermediate Similarity	NPC474095
0.7851	Intermediate Similarity	NPC217111
0.784	Intermediate Similarity	NPC476234
0.7838	Intermediate Similarity	NPC260233
0.7833	Intermediate Similarity	NPC13784
0.7818	Intermediate Similarity	NPC153885
0.7818	Intermediate Similarity	NPC155232
0.7812	Intermediate Similarity	NPC328997
0.7812	Intermediate Similarity	NPC294050
0.7807	Intermediate Similarity	NPC109514
0.7807	Intermediate Similarity	NPC476993
0.7805	Intermediate Similarity	NPC61651
0.7805	Intermediate Similarity	NPC471553
0.7803	Intermediate Similarity	NPC58685
0.7797	Intermediate Similarity	NPC318327
0.7797	Intermediate Similarity	NPC470252
0.7788	Intermediate Similarity	NPC145052
0.7788	Intermediate Similarity	NPC75724
0.7786	Intermediate Similarity	NPC136588
0.7786	Intermediate Similarity	NPC199253
0.7786	Intermediate Similarity	NPC31799
0.7786	Intermediate Similarity	NPC55949
0.7778	Intermediate Similarity	NPC37914
0.7778	Intermediate Similarity	NPC475957
0.7769	Intermediate Similarity	NPC48248
0.776	Intermediate Similarity	NPC472679
0.776	Intermediate Similarity	NPC472680
0.7759	Intermediate Similarity	NPC249067
0.7752	Intermediate Similarity	NPC15837
0.7752	Intermediate Similarity	NPC474106
0.7748	Intermediate Similarity	NPC289883
0.7744	Intermediate Similarity	NPC310662
0.7744	Intermediate Similarity	NPC78307
0.7727	Intermediate Similarity	NPC93015
0.7727	Intermediate Similarity	NPC133461
0.7719	Intermediate Similarity	NPC476042
0.7714	Intermediate Similarity	NPC478160
0.7712	Intermediate Similarity	NPC211439
0.7712	Intermediate Similarity	NPC470391
0.771	Intermediate Similarity	NPC34414
0.771	Intermediate Similarity	NPC471832
0.771	Intermediate Similarity	NPC146647
0.771	Intermediate Similarity	NPC171460
0.7705	Intermediate Similarity	NPC186933
0.7699	Intermediate Similarity	NPC103048
0.7698	Intermediate Similarity	NPC478164
0.7692	Intermediate Similarity	NPC316553
0.7687	Intermediate Similarity	NPC212207
0.7687	Intermediate Similarity	NPC50924
0.7687	Intermediate Similarity	NPC202225
0.7669	Intermediate Similarity	NPC70622
0.7667	Intermediate Similarity	NPC291799
0.7664	Intermediate Similarity	NPC470407
0.7658	Intermediate Similarity	NPC1682
0.7658	Intermediate Similarity	NPC188844
0.7656	Intermediate Similarity	NPC325740
0.7656	Intermediate Similarity	NPC472681
0.7647	Intermediate Similarity	NPC264022
0.7642	Intermediate Similarity	NPC62138
0.7636	Intermediate Similarity	NPC173413
0.7636	Intermediate Similarity	NPC277277
0.7632	Intermediate Similarity	NPC329387
0.7632	Intermediate Similarity	NPC317280
0.763	Intermediate Similarity	NPC283088
0.7619	Intermediate Similarity	NPC133302
0.7615	Intermediate Similarity	NPC146239
0.7612	Intermediate Similarity	NPC225051
0.7612	Intermediate Similarity	NPC52407
0.7612	Intermediate Similarity	NPC115458
0.7611	Intermediate Similarity	NPC219573
0.7611	Intermediate Similarity	NPC12695
0.7611	Intermediate Similarity	NPC185208
0.7597	Intermediate Similarity	NPC142956
0.7597	Intermediate Similarity	NPC199273
0.7594	Intermediate Similarity	NPC244699
0.7594	Intermediate Similarity	NPC471851
0.7586	Intermediate Similarity	NPC320891
0.7581	Intermediate Similarity	NPC212891
0.7578	Intermediate Similarity	NPC91478
0.7576	Intermediate Similarity	NPC276238
0.7576	Intermediate Similarity	NPC262819
0.7576	Intermediate Similarity	NPC49272
0.7574	Intermediate Similarity	NPC475549
0.7568	Intermediate Similarity	NPC284475
0.7563	Intermediate Similarity	NPC470007
0.7561	Intermediate Similarity	NPC274839
0.7561	Intermediate Similarity	NPC474408
0.7557	Intermediate Similarity	NPC72667
0.7545	Intermediate Similarity	NPC418308
0.7544	Intermediate Similarity	NPC289201
0.7542	Intermediate Similarity	NPC105899
0.754	Intermediate Similarity	NPC472708
0.7538	Intermediate Similarity	NPC123506
0.7537	Intermediate Similarity	NPC144257
0.7522	Intermediate Similarity	NPC172925
0.7522	Intermediate Similarity	NPC472880
0.7521	Intermediate Similarity	NPC133308
0.7519	Intermediate Similarity	NPC198305
0.7519	Intermediate Similarity	NPC140118
0.7519	Intermediate Similarity	NPC12881
0.7518	Intermediate Similarity	NPC305060
0.7518	Intermediate Similarity	NPC79627
0.7518	Intermediate Similarity	NPC29932
0.75	Intermediate Similarity	NPC120545
0.75	Intermediate Similarity	NPC9274
0.75	Intermediate Similarity	NPC59677
0.75	Intermediate Similarity	NPC323420
0.75	Intermediate Similarity	NPC18785
0.75	Intermediate Similarity	NPC136810
0.75	Intermediate Similarity	NPC248068
0.75	Intermediate Similarity	NPC128248
0.75	Intermediate Similarity	NPC475282
0.75	Intermediate Similarity	NPC260886

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 NPC318173 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	203
0.1-0.2	889
0.2-0.3	1227
0.3-0.4	2752
0.4-0.5	2531
0.5-0.6	1263
0.6-0.7	243
0.7-0.8	38
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8596	High Similarity	NPD4141	Clinical (unspecified phase)
0.8142	Intermediate Similarity	NPD1929	Approved
0.8142	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.8142	Intermediate Similarity	NPD1930	Approved
0.813	Intermediate Similarity	NPD4879	Approved
0.8053	Intermediate Similarity	NPD1932	Approved
0.7949	Intermediate Similarity	NPD2329	Discontinued
0.7903	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7876	Intermediate Similarity	NPD2066	Phase 3
0.7857	Intermediate Similarity	NPD3495	Discontinued
0.7851	Intermediate Similarity	NPD5951	Approved
0.7759	Intermediate Similarity	NPD1237	Approved
0.7658	Intermediate Similarity	NPD7631	Approved
0.7619	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD4878	Approved
0.7568	Intermediate Similarity	NPD7609	Phase 3
0.7522	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD7961	Discontinued
0.746	Intermediate Similarity	NPD7009	Phase 2
0.7444	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD7008	Discontinued
0.7434	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7610	Discontinued
0.7364	Intermediate Similarity	NPD650	Approved
0.7355	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD1989	Approved
0.7295	Intermediate Similarity	NPD1317	Discontinued
0.7287	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1470	Approved
0.7257	Intermediate Similarity	NPD1239	Approved
0.7241	Intermediate Similarity	NPD1566	Phase 3
0.7241	Intermediate Similarity	NPD1564	Approved
0.7241	Intermediate Similarity	NPD1565	Approved
0.7227	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD1693	Approved
0.7168	Intermediate Similarity	NPD1090	Approved
0.7168	Intermediate Similarity	NPD1089	Approved
0.7168	Intermediate Similarity	NPD1086	Approved
0.7087	Intermediate Similarity	NPD3317	Approved
0.7083	Intermediate Similarity	NPD7236	Approved
0.708	Intermediate Similarity	NPD800	Approved
0.7077	Intermediate Similarity	NPD2345	Approved
0.7073	Intermediate Similarity	NPD2182	Approved
0.7071	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD1088	Approved
0.7043	Intermediate Similarity	NPD1508	Approved
0.7008	Intermediate Similarity	NPD2629	Approved
0.6984	Remote Similarity	NPD6858	Approved
0.6984	Remote Similarity	NPD7094	Approved
0.6983	Remote Similarity	NPD1563	Approved
0.6972	Remote Similarity	NPD2346	Discontinued
0.697	Remote Similarity	NPD1201	Approved
0.6963	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.696	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7239	Suspended
0.6947	Remote Similarity	NPD2932	Approved
0.6944	Remote Similarity	NPD7003	Approved
0.6929	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD8165	Discontinued
0.6903	Remote Similarity	NPD1087	Approved
0.6901	Remote Similarity	NPD5404	Approved
0.6901	Remote Similarity	NPD5405	Approved
0.6901	Remote Similarity	NPD5406	Approved
0.6901	Remote Similarity	NPD5408	Approved
0.6899	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD5909	Discontinued
0.6885	Remote Similarity	NPD164	Approved
0.6871	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD5157	Phase 1
0.6866	Remote Similarity	NPD5159	Phase 2
0.6864	Remote Similarity	NPD1843	Approved
0.6853	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5618	Discontinued
0.6818	Remote Similarity	NPD942	Approved
0.6818	Remote Similarity	NPD3019	Approved
0.6815	Remote Similarity	NPD1876	Approved
0.6815	Remote Similarity	NPD1283	Approved
0.6803	Remote Similarity	NPD6647	Phase 2
0.68	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD3972	Approved
0.6763	Remote Similarity	NPD5422	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD1651	Approved
0.6735	Remote Similarity	NPD3300	Phase 2
0.6716	Remote Similarity	NPD6287	Discontinued
0.6715	Remote Similarity	NPD2798	Approved
0.6713	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD2799	Discontinued
0.6695	Remote Similarity	NPD1202	Approved
0.6689	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD3226	Approved
0.6689	Remote Similarity	NPD7390	Discontinued
0.6689	Remote Similarity	NPD7458	Discontinued
0.6643	Remote Similarity	NPD2313	Discontinued
0.6643	Remote Similarity	NPD3764	Approved
0.6642	Remote Similarity	NPD3023	Approved
0.6642	Remote Similarity	NPD3026	Approved
0.6639	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD1471	Phase 3
0.6618	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD3025	Approved
0.6617	Remote Similarity	NPD3024	Approved
0.6617	Remote Similarity	NPD1245	Approved
0.6614	Remote Similarity	NPD2067	Discontinued
0.6612	Remote Similarity	NPD9495	Approved
0.66	Remote Similarity	NPD6273	Approved
0.6599	Remote Similarity	NPD4628	Phase 3
0.6594	Remote Similarity	NPD4980	Approved
0.6593	Remote Similarity	NPD1281	Approved
0.6591	Remote Similarity	NPD6065	Approved
0.6589	Remote Similarity	NPD7635	Approved
0.6571	Remote Similarity	NPD6966	Discovery
0.6567	Remote Similarity	NPD5836	Discontinued
0.6565	Remote Similarity	NPD4198	Discontinued
0.656	Remote Similarity	NPD5048	Discontinued
0.6557	Remote Similarity	NPD1238	Approved
0.6549	Remote Similarity	NPD2979	Phase 3
0.6549	Remote Similarity	NPD9491	Approved
0.6547	Remote Similarity	NPD7084	Phase 3
0.6541	Remote Similarity	NPD4479	Discontinued
0.6538	Remote Similarity	NPD6010	Discontinued
0.6538	Remote Similarity	NPD7057	Phase 3
0.6538	Remote Similarity	NPD7058	Phase 2
0.6531	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD1164	Approved
0.6507	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD5347	Phase 2
0.6496	Remote Similarity	NPD5346	Phase 2
0.6493	Remote Similarity	NPD5981	Approved
0.6489	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD1246	Approved
0.6486	Remote Similarity	NPD8166	Discontinued
0.6479	Remote Similarity	NPD7715	Approved
0.6479	Remote Similarity	NPD7714	Approved
0.6458	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD2342	Discontinued
0.6444	Remote Similarity	NPD5126	Approved
0.6444	Remote Similarity	NPD5125	Phase 3
0.6444	Remote Similarity	NPD5306	Approved
0.6444	Remote Similarity	NPD4199	Phase 3
0.6444	Remote Similarity	NPD5305	Approved
0.6441	Remote Similarity	NPD3673	Approved
0.6441	Remote Similarity	NPD9258	Approved
0.6441	Remote Similarity	NPD3672	Approved
0.6441	Remote Similarity	NPD9256	Approved
0.6434	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4695	Discontinued
0.6429	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD8150	Discontinued
0.6424	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD7798	Approved
0.642	Remote Similarity	NPD7473	Discontinued
0.641	Remote Similarity	NPD7819	Suspended
0.64	Remote Similarity	NPD5765	Approved
0.6397	Remote Similarity	NPD4135	Approved
0.6397	Remote Similarity	NPD4136	Approved
0.6397	Remote Similarity	NPD4106	Approved
0.6395	Remote Similarity	NPD2344	Approved
0.6391	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD6685	Approved
0.6372	Remote Similarity	NPD226	Approved
0.637	Remote Similarity	NPD7305	Phase 1
0.6364	Remote Similarity	NPD6049	Phase 2
0.6364	Remote Similarity	NPD7713	Phase 3
0.6364	Remote Similarity	NPD6663	Approved
0.6364	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD6085	Phase 2
0.6357	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.635	Remote Similarity	NPD4807	Approved
0.635	Remote Similarity	NPD4806	Approved
0.6335	Remote Similarity	NPD6232	Discontinued
0.6331	Remote Similarity	NPD1574	Approved
0.6327	Remote Similarity	NPD2531	Phase 2
0.6327	Remote Similarity	NPD2935	Discontinued
0.6327	Remote Similarity	NPD2438	Suspended
0.6325	Remote Similarity	NPD4793	Discontinued
0.6324	Remote Similarity	NPD3095	Discontinued
0.632	Remote Similarity	NPD2648	Phase 3
0.632	Remote Similarity	NPD2193	Phase 2
0.6312	Remote Similarity	NPD5736	Approved
0.6306	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD3880	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD3091	Approved
0.6294	Remote Similarity	NPD3268	Approved
0.6294	Remote Similarity	NPD6766	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD2846	Clinical (unspecified phase)
0.629	Remote Similarity	NPD3020	Approved
0.6288	Remote Similarity	NPD2650	Approved
0.6288	Remote Similarity	NPD2652	Approved
0.6286	Remote Similarity	NPD1593	Approved
0.628	Remote Similarity	NPD7799	Discontinued
0.627	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD4576	Approved
0.6269	Remote Similarity	NPD4574	Approved
0.6267	Remote Similarity	NPD3750	Approved
0.6259	Remote Similarity	NPD4308	Phase 3
0.6259	Remote Similarity	NPD1510	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