NPASS Compound

Structure

CID278652 OpenBabel06191716082D 23 24 0 0 0 0 0 0 0 0999 V2000 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 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 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 -4.3301 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 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 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 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 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 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 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 -5.1962 3.0000 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 -3.4641 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 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 5 2 0 0 0 0 1 10 1 0 0 0 0 2 6 2 0 0 0 0 2 10 1 0 0 0 0 3 7 2 0 0 0 0 3 11 1 0 0 0 0 4 8 2 0 0 0 0 4 11 1 0 0 0 0 5 12 1 0 0 0 0 6 13 1 0 0 0 0 7 14 1 0 0 0 0 8 16 1 0 0 0 0 9 10 2 0 0 0 0 9 15 1 0 0 0 0 11 12 2 0 0 0 0 12 17 1 0 0 0 0 13 15 2 0 0 0 0 13 18 1 0 0 0 0 14 17 2 0 0 0 0 14 19 1 0 0 0 0 15 20 1 0 0 0 0 16 21 2 0 0 0 0 16 22 1 0 0 0 0 17 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.08
Volume:	314.489
LogP:	2.848
LogD:	2.429
LogS:	-2.769
# Rotatable Bonds:	4
TPSA:	118.22
# H-Bond Aceptor:	6
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.336
Synthetic Accessibility Score:	2.621
Fsp3:	0.0
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:	-5.582
MDCK Permeability:	1.1859233381983358e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.021
30% Bioavailability (F30%):	0.145

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	99.77111053466797%
Volume Distribution (VD):	0.327
Pgp-substrate:	0.9856764078140259%

ADMET: Metabolism

CYP1A2-inhibitor:	0.12
CYP1A2-substrate:	0.086
CYP2C19-inhibitor:	0.035
CYP2C19-substrate:	0.043
CYP2C9-inhibitor:	0.491
CYP2C9-substrate:	0.228
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.217
CYP3A4-inhibitor:	0.039
CYP3A4-substrate:	0.04

ADMET: Excretion

Clearance (CL):	10.857
Half-life (T1/2):	0.937

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.55
Drug-inuced Liver Injury (DILI):	0.863
AMES Toxicity:	0.618
Rat Oral Acute Toxicity:	0.626
Maximum Recommended Daily Dose:	0.273
Skin Sensitization:	0.968
Carcinogencity:	0.301
Eye Corrosion:	0.008
Eye Irritation:	0.924
Respiratory Toxicity:	0.371

Download Data

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

Natural Product: NPC278652

Natural Product ID:	NPC278652
*Common Name:**	Salvianolic Acid F
IUPAC Name:	(E)-3-[2-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]-3,4-dihydroxyphenyl]prop-2-enoic acid
Synonyms:	Salvianolic Acid F
Standard InCHIKey:	PULWRMOKQNWQBD-LZSLGQGWSA-N
Standard InCHI:	InChI=1S/C17H14O6/c18-13-6-2-10(9-15(13)20)1-5-12-11(4-8-16(21)22)3-7-14(19)17(12)23/h1-9,18-20,23H,(H,21,22)/b5-1+,8-4+
SMILES:	OC(=O)/C=C/c1ccc(c(c1/C=C/c1ccc(c(c1)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464884
PubChem CID:	10903113
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes

*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]
NPO24054	Tournefortia sarmentosa	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12027757]
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]
NPO24054	Tournefortia sarmentosa	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24054	Tournefortia sarmentosa	Species	Heliotropiaceae	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]
NPO24054	Tournefortia sarmentosa	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
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	1
Others	1

Activity Type	# Activity
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	5440.0	nM	PMID[495410]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	0.8	n.a.	PMID[495410]

☑ 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 NPC278652 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	305
0.1-0.2	1669
0.2-0.3	4320
0.3-0.4	12896
0.4-0.5	5818
0.5-0.6	7156
0.6-0.7	8137
0.7-0.8	2243
0.8-0.85	124
0.85-0.9	25
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9099	High Similarity	NPC297657
0.9	High Similarity	NPC233835
0.8991	High Similarity	NPC1786
0.8991	High Similarity	NPC294902
0.8991	High Similarity	NPC1075
0.8966	High Similarity	NPC141791
0.8966	High Similarity	NPC263386
0.8879	High Similarity	NPC275519
0.8814	High Similarity	NPC470848
0.8814	High Similarity	NPC470849
0.8739	High Similarity	NPC147654
0.8707	High Similarity	NPC299252
0.8707	High Similarity	NPC61062
0.8707	High Similarity	NPC277394
0.8684	High Similarity	NPC51698
0.8636	High Similarity	NPC471511
0.8632	High Similarity	NPC610
0.8632	High Similarity	NPC175799
0.8632	High Similarity	NPC145023
0.8632	High Similarity	NPC200988
0.8596	High Similarity	NPC226250
0.8584	High Similarity	NPC254833
0.8584	High Similarity	NPC228343
0.8559	High Similarity	NPC203124
0.8559	High Similarity	NPC239291
0.8559	High Similarity	NPC86198
0.8559	High Similarity	NPC309434
0.8532	High Similarity	NPC223393
0.8522	High Similarity	NPC131530
0.8509	High Similarity	NPC222084
0.8487	Intermediate Similarity	NPC109371
0.8487	Intermediate Similarity	NPC217174
0.8487	Intermediate Similarity	NPC470214
0.8487	Intermediate Similarity	NPC470215
0.8487	Intermediate Similarity	NPC70084
0.8468	Intermediate Similarity	NPC79672
0.8468	Intermediate Similarity	NPC52087
0.8448	Intermediate Similarity	NPC95381
0.8448	Intermediate Similarity	NPC471485
0.8443	Intermediate Similarity	NPC212541
0.84	Intermediate Similarity	NPC478215
0.839	Intermediate Similarity	NPC281277
0.8387	Intermediate Similarity	NPC213552
0.8387	Intermediate Similarity	NPC120225
0.8376	Intermediate Similarity	NPC33749
0.8376	Intermediate Similarity	NPC328593
0.8376	Intermediate Similarity	NPC261453
0.8376	Intermediate Similarity	NPC217472
0.8374	Intermediate Similarity	NPC288945
0.8372	Intermediate Similarity	NPC72918
0.8349	Intermediate Similarity	NPC109955
0.8348	Intermediate Similarity	NPC147634
0.8348	Intermediate Similarity	NPC79793
0.8348	Intermediate Similarity	NPC226401
0.8348	Intermediate Similarity	NPC120982
0.8348	Intermediate Similarity	NPC174096
0.8319	Intermediate Similarity	NPC19149
0.8306	Intermediate Similarity	NPC289459
0.8305	Intermediate Similarity	NPC474967
0.8305	Intermediate Similarity	NPC233669
0.8304	Intermediate Similarity	NPC93831
0.8293	Intermediate Similarity	NPC285345
0.8291	Intermediate Similarity	NPC148969
0.8291	Intermediate Similarity	NPC264558
0.8279	Intermediate Similarity	NPC472271
0.8279	Intermediate Similarity	NPC237667
0.8279	Intermediate Similarity	NPC198336
0.8276	Intermediate Similarity	NPC179002
0.8276	Intermediate Similarity	NPC187583
0.8276	Intermediate Similarity	NPC257430
0.8264	Intermediate Similarity	NPC472071
0.8261	Intermediate Similarity	NPC62258
0.8261	Intermediate Similarity	NPC55617
0.8226	Intermediate Similarity	NPC246704
0.822	Intermediate Similarity	NPC120280
0.8214	Intermediate Similarity	NPC196479
0.8214	Intermediate Similarity	NPC470202
0.8211	Intermediate Similarity	NPC86900
0.8211	Intermediate Similarity	NPC283514
0.8205	Intermediate Similarity	NPC471179
0.8197	Intermediate Similarity	NPC236520
0.8197	Intermediate Similarity	NPC294361
0.8195	Intermediate Similarity	NPC38473
0.819	Intermediate Similarity	NPC183700
0.8189	Intermediate Similarity	NPC30174
0.8189	Intermediate Similarity	NPC83062
0.8182	Intermediate Similarity	NPC32674
0.8182	Intermediate Similarity	NPC156313
0.8182	Intermediate Similarity	NPC176893
0.8167	Intermediate Similarity	NPC16030
0.8167	Intermediate Similarity	NPC65791
0.8165	Intermediate Similarity	NPC246679
0.8165	Intermediate Similarity	NPC257182
0.816	Intermediate Similarity	NPC67951
0.816	Intermediate Similarity	NPC197832
0.8158	Intermediate Similarity	NPC477814
0.8151	Intermediate Similarity	NPC4665
0.8151	Intermediate Similarity	NPC472893
0.8145	Intermediate Similarity	NPC306100
0.8145	Intermediate Similarity	NPC53567
0.8142	Intermediate Similarity	NPC120719
0.813	Intermediate Similarity	NPC39029
0.8125	Intermediate Similarity	NPC110764
0.812	Intermediate Similarity	NPC228609
0.812	Intermediate Similarity	NPC268032
0.8115	Intermediate Similarity	NPC475245
0.811	Intermediate Similarity	NPC234175
0.8108	Intermediate Similarity	NPC130193
0.8106	Intermediate Similarity	NPC62907
0.8103	Intermediate Similarity	NPC79543
0.8099	Intermediate Similarity	NPC107588
0.8099	Intermediate Similarity	NPC137537
0.8099	Intermediate Similarity	NPC144343
0.8099	Intermediate Similarity	NPC164706
0.8099	Intermediate Similarity	NPC70744
0.8099	Intermediate Similarity	NPC272471
0.8095	Intermediate Similarity	NPC118584
0.808	Intermediate Similarity	NPC85565
0.808	Intermediate Similarity	NPC60517
0.808	Intermediate Similarity	NPC146886
0.808	Intermediate Similarity	NPC20443
0.8077	Intermediate Similarity	NPC294226
0.8077	Intermediate Similarity	NPC471749
0.8074	Intermediate Similarity	NPC6568
0.8073	Intermediate Similarity	NPC32977
0.8073	Intermediate Similarity	NPC81010
0.807	Intermediate Similarity	NPC303141
0.807	Intermediate Similarity	NPC243677
0.8062	Intermediate Similarity	NPC198388
0.8062	Intermediate Similarity	NPC318799
0.8053	Intermediate Similarity	NPC168393
0.8053	Intermediate Similarity	NPC233827
0.8053	Intermediate Similarity	NPC135784
0.8051	Intermediate Similarity	NPC228988
0.8049	Intermediate Similarity	NPC109083
0.8049	Intermediate Similarity	NPC269843
0.8049	Intermediate Similarity	NPC224814
0.8049	Intermediate Similarity	NPC14007
0.8049	Intermediate Similarity	NPC60962
0.8049	Intermediate Similarity	NPC189844
0.8047	Intermediate Similarity	NPC470747
0.8033	Intermediate Similarity	NPC241634
0.803	Intermediate Similarity	NPC476699
0.803	Intermediate Similarity	NPC223836
0.8018	Intermediate Similarity	NPC201967
0.8017	Intermediate Similarity	NPC470039
0.8017	Intermediate Similarity	NPC114392
0.8017	Intermediate Similarity	NPC277588
0.8017	Intermediate Similarity	NPC206341
0.8017	Intermediate Similarity	NPC58427
0.8017	Intermediate Similarity	NPC105727
0.8017	Intermediate Similarity	NPC34864
0.8015	Intermediate Similarity	NPC473054
0.8	Intermediate Similarity	NPC25581
0.8	Intermediate Similarity	NPC5419
0.8	Intermediate Similarity	NPC18074
0.8	Intermediate Similarity	NPC61
0.8	Intermediate Similarity	NPC107522
0.8	Intermediate Similarity	NPC274678
0.7985	Intermediate Similarity	NPC134969
0.7984	Intermediate Similarity	NPC117609
0.7983	Intermediate Similarity	NPC317869
0.7982	Intermediate Similarity	NPC12278
0.797	Intermediate Similarity	NPC290030
0.7969	Intermediate Similarity	NPC110313
0.7969	Intermediate Similarity	NPC95537
0.7967	Intermediate Similarity	NPC2058
0.7967	Intermediate Similarity	NPC265454
0.7967	Intermediate Similarity	NPC34634
0.7967	Intermediate Similarity	NPC202474
0.7966	Intermediate Similarity	NPC95716
0.7955	Intermediate Similarity	NPC43353
0.7951	Intermediate Similarity	NPC63126
0.7949	Intermediate Similarity	NPC202647
0.7946	Intermediate Similarity	NPC131587
0.7939	Intermediate Similarity	NPC155209
0.7939	Intermediate Similarity	NPC168799
0.7937	Intermediate Similarity	NPC471927
0.7937	Intermediate Similarity	NPC469568
0.7937	Intermediate Similarity	NPC224342
0.7931	Intermediate Similarity	NPC260952
0.7931	Intermediate Similarity	NPC176527
0.7926	Intermediate Similarity	NPC290664
0.7923	Intermediate Similarity	NPC243305
0.792	Intermediate Similarity	NPC244351
0.7917	Intermediate Similarity	NPC197513
0.791	Intermediate Similarity	NPC182249
0.791	Intermediate Similarity	NPC76032
0.791	Intermediate Similarity	NPC132723
0.7909	Intermediate Similarity	NPC128062
0.7909	Intermediate Similarity	NPC245187
0.7907	Intermediate Similarity	NPC94810
0.7907	Intermediate Similarity	NPC208536
0.7903	Intermediate Similarity	NPC204466
0.7903	Intermediate Similarity	NPC241001
0.7903	Intermediate Similarity	NPC307253
0.7903	Intermediate Similarity	NPC470414
0.7903	Intermediate Similarity	NPC98305
0.7903	Intermediate Similarity	NPC24125
0.7899	Intermediate Similarity	NPC46940

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 NPC278652 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	270
0.1-0.2	1009
0.2-0.3	1395
0.3-0.4	2944
0.4-0.5	1837
0.5-0.6	1168
0.6-0.7	448
0.7-0.8	77
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8584	High Similarity	NPD3021	Approved
0.8584	High Similarity	NPD3022	Approved
0.7857	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7788	Intermediate Similarity	NPD3020	Approved
0.7748	Intermediate Similarity	NPD2933	Approved
0.7748	Intermediate Similarity	NPD2934	Approved
0.7727	Intermediate Similarity	NPD943	Approved
0.7727	Intermediate Similarity	NPD4060	Phase 1
0.768	Intermediate Similarity	NPD4626	Approved
0.7679	Intermediate Similarity	NPD2860	Approved
0.7679	Intermediate Similarity	NPD2859	Approved
0.7647	Intermediate Similarity	NPD7266	Discontinued
0.7627	Intermediate Similarity	NPD2342	Discontinued
0.7609	Intermediate Similarity	NPD8166	Discontinued
0.7521	Intermediate Similarity	NPD228	Approved
0.75	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD9269	Phase 2
0.75	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD1164	Approved
0.7462	Intermediate Similarity	NPD1470	Approved
0.7459	Intermediate Similarity	NPD9379	Approved
0.7459	Intermediate Similarity	NPD7635	Approved
0.7459	Intermediate Similarity	NPD9377	Approved
0.7456	Intermediate Similarity	NPD288	Approved
0.7445	Intermediate Similarity	NPD5404	Approved
0.7445	Intermediate Similarity	NPD5408	Approved
0.7445	Intermediate Similarity	NPD5405	Approved
0.7445	Intermediate Similarity	NPD5406	Approved
0.7444	Intermediate Similarity	NPD3764	Approved
0.7422	Intermediate Similarity	NPD1201	Approved
0.7414	Intermediate Similarity	NPD1242	Phase 1
0.7414	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD258	Approved
0.7405	Intermediate Similarity	NPD257	Approved
0.7368	Intermediate Similarity	NPD844	Approved
0.7348	Intermediate Similarity	NPD9569	Approved
0.7323	Intermediate Similarity	NPD5691	Approved
0.7313	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD6190	Approved
0.7302	Intermediate Similarity	NPD5536	Phase 2
0.7295	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD3019	Approved
0.7266	Intermediate Similarity	NPD2932	Approved
0.7258	Intermediate Similarity	NPD5283	Phase 1
0.7252	Intermediate Similarity	NPD5310	Approved
0.7252	Intermediate Similarity	NPD5311	Approved
0.7218	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD5736	Approved
0.7197	Intermediate Similarity	NPD3055	Approved
0.7197	Intermediate Similarity	NPD3053	Approved
0.7194	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD2935	Discontinued
0.719	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD9268	Approved
0.7154	Intermediate Similarity	NPD3092	Approved
0.7153	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD230	Phase 1
0.7143	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD2286	Discontinued
0.7132	Intermediate Similarity	NPD259	Phase 1
0.7131	Intermediate Similarity	NPD74	Approved
0.7131	Intermediate Similarity	NPD9266	Approved
0.7121	Intermediate Similarity	NPD1283	Approved
0.7113	Intermediate Similarity	NPD3750	Approved
0.7111	Intermediate Similarity	NPD9537	Phase 1
0.7111	Intermediate Similarity	NPD9536	Phase 1
0.7111	Intermediate Similarity	NPD7095	Approved
0.7111	Intermediate Similarity	NPD3027	Phase 3
0.7109	Intermediate Similarity	NPD3091	Approved
0.7099	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD111	Approved
0.708	Intermediate Similarity	NPD825	Approved
0.708	Intermediate Similarity	NPD1613	Approved
0.708	Intermediate Similarity	NPD826	Approved
0.708	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD3496	Discontinued
0.7075	Intermediate Similarity	NPD3455	Phase 2
0.7073	Intermediate Similarity	NPD4750	Phase 3
0.7069	Intermediate Similarity	NPD1809	Phase 2
0.7068	Intermediate Similarity	NPD3094	Phase 2
0.7059	Intermediate Similarity	NPD846	Approved
0.7059	Intermediate Similarity	NPD940	Approved
0.7054	Intermediate Similarity	NPD4093	Discontinued
0.7049	Intermediate Similarity	NPD9263	Approved
0.7049	Intermediate Similarity	NPD9264	Approved
0.7049	Intermediate Similarity	NPD9267	Approved
0.7043	Intermediate Similarity	NPD845	Approved
0.7029	Intermediate Similarity	NPD274	Approved
0.7029	Intermediate Similarity	NPD555	Phase 2
0.7029	Intermediate Similarity	NPD275	Approved
0.7023	Intermediate Similarity	NPD422	Phase 1
0.7023	Intermediate Similarity	NPD1611	Approved
0.7008	Intermediate Similarity	NPD709	Approved
0.7007	Intermediate Similarity	NPD6663	Approved
0.7	Intermediate Similarity	NPD9381	Approved
0.7	Intermediate Similarity	NPD4059	Approved
0.7	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD9384	Approved
0.7	Intermediate Similarity	NPD1465	Phase 2
0.6977	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD3028	Approved
0.6966	Remote Similarity	NPD1511	Approved
0.6963	Remote Similarity	NPD9494	Approved
0.6957	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD3061	Approved
0.6957	Remote Similarity	NPD3059	Approved
0.6957	Remote Similarity	NPD3620	Phase 2
0.6957	Remote Similarity	NPD3062	Approved
0.6953	Remote Similarity	NPD9493	Approved
0.694	Remote Similarity	NPD1203	Approved
0.694	Remote Similarity	NPD2797	Approved
0.694	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD1792	Phase 2
0.6929	Remote Similarity	NPD497	Approved
0.6911	Remote Similarity	NPD1358	Approved
0.6908	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD447	Suspended
0.6906	Remote Similarity	NPD6355	Discontinued
0.6905	Remote Similarity	NPD5535	Approved
0.6901	Remote Similarity	NPD2346	Discontinued
0.6894	Remote Similarity	NPD1535	Discovery
0.6894	Remote Similarity	NPD1281	Approved
0.6892	Remote Similarity	NPD1653	Approved
0.6885	Remote Similarity	NPD9697	Approved
0.6879	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD2799	Discontinued
0.6875	Remote Similarity	NPD7003	Approved
0.6871	Remote Similarity	NPD1512	Approved
0.687	Remote Similarity	NPD3095	Discontinued
0.6866	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD3225	Approved
0.6857	Remote Similarity	NPD5314	Approved
0.6853	Remote Similarity	NPD970	Clinical (unspecified phase)
0.685	Remote Similarity	NPD2229	Approved
0.685	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.685	Remote Similarity	NPD2234	Approved
0.685	Remote Similarity	NPD2228	Approved
0.685	Remote Similarity	NPD498	Approved
0.685	Remote Similarity	NPD495	Approved
0.685	Remote Similarity	NPD496	Approved
0.6849	Remote Similarity	NPD2421	Approved
0.6849	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD2420	Approved
0.6846	Remote Similarity	NPD9545	Approved
0.6842	Remote Similarity	NPD1481	Phase 2
0.6831	Remote Similarity	NPD9570	Approved
0.6829	Remote Similarity	NPD3134	Approved
0.6822	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD3026	Approved
0.6818	Remote Similarity	NPD3847	Discontinued
0.6818	Remote Similarity	NPD3023	Approved
0.6812	Remote Similarity	NPD6798	Discontinued
0.6812	Remote Similarity	NPD3268	Approved
0.6797	Remote Similarity	NPD5951	Approved
0.6797	Remote Similarity	NPD9281	Approved
0.6795	Remote Similarity	NPD6232	Discontinued
0.6794	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD3024	Approved
0.6794	Remote Similarity	NPD3025	Approved
0.6791	Remote Similarity	NPD9622	Approved
0.6783	Remote Similarity	NPD5762	Approved
0.6783	Remote Similarity	NPD5763	Approved
0.6781	Remote Similarity	NPD3300	Phase 2
0.6761	Remote Similarity	NPD3748	Approved
0.6759	Remote Similarity	NPD4628	Phase 3
0.6757	Remote Similarity	NPD3971	Phase 1
0.6744	Remote Similarity	NPD6671	Approved
0.6744	Remote Similarity	NPD256	Approved
0.6744	Remote Similarity	NPD255	Approved
0.6742	Remote Similarity	NPD4589	Approved
0.6742	Remote Similarity	NPD1751	Approved
0.6721	Remote Similarity	NPD9261	Approved
0.6718	Remote Similarity	NPD1759	Phase 1
0.6718	Remote Similarity	NPD5303	Approved
0.6718	Remote Similarity	NPD5304	Approved
0.6718	Remote Similarity	NPD1894	Discontinued
0.6716	Remote Similarity	NPD1608	Approved
0.6715	Remote Similarity	NPD2861	Phase 2
0.6714	Remote Similarity	NPD6346	Approved
0.6714	Remote Similarity	NPD4140	Approved
0.6714	Remote Similarity	NPD1558	Phase 1
0.6711	Remote Similarity	NPD1934	Approved
0.671	Remote Similarity	NPD6234	Discontinued
0.6694	Remote Similarity	NPD1444	Approved
0.6694	Remote Similarity	NPD1445	Approved
0.6693	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD9568	Approved
0.6691	Remote Similarity	NPD2313	Discontinued
0.6689	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD3882	Suspended
0.6667	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7473	Discontinued
0.6667	Remote Similarity	NPD2801	Approved
0.6667	Remote Similarity	NPD3845	Phase 1
0.6667	Remote Similarity	NPD1651	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