NPASS Compound

Structure

NPC232228 OpenBabel07101719142D 32 34 0 0 1 0 0 0 0 0999 V2000 8.6603 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -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 6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 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 7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -2.0000 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 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 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 2.5981 -0.5000 0.0000 O 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 13 2 0 0 0 0 4 14 2 0 0 0 0 5 7 2 0 0 0 0 5 12 1 0 0 0 0 6 8 2 0 0 0 0 6 13 1 0 0 0 0 7 16 1 0 0 0 0 8 18 1 0 0 0 0 9 12 2 0 0 0 0 9 15 1 0 0 0 0 10 23 1 0 0 0 0 11 12 1 0 0 0 0 11 30 1 0 0 0 0 13 14 1 0 0 0 0 14 24 1 0 0 0 0 15 16 2 0 0 0 0 15 25 1 0 0 0 0 16 31 1 0 0 0 0 17 10 1 6 0 0 0 17 19 1 0 0 0 0 17 32 1 0 0 0 0 18 26 2 0 0 0 0 18 30 1 0 0 0 0 19 20 1 0 0 0 0 19 27 1 1 0 0 0 20 21 1 0 0 0 0 20 28 1 6 0 0 0 21 22 1 0 0 0 0 21 29 1 1 0 0 0 22 31 1 6 0 0 0 22 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	448.14
Volume:	430.209
LogP:	1.428
LogD:	1.358
LogS:	-2.508
# Rotatable Bonds:	8
TPSA:	166.14
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.251
Synthetic Accessibility Score:	3.751
Fsp3:	0.318
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.296
MDCK Permeability:	1.0913578989857342e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.039
Human Intestinal Absorption (HIA):	0.384
20% Bioavailability (F20%):	0.293
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.192
Plasma Protein Binding (PPB):	96.87184143066406%
Volume Distribution (VD):	0.399
Pgp-substrate:	3.0140671730041504%

ADMET: Metabolism

CYP1A2-inhibitor:	0.242
CYP1A2-substrate:	0.042
CYP2C19-inhibitor:	0.052
CYP2C19-substrate:	0.105
CYP2C9-inhibitor:	0.127
CYP2C9-substrate:	0.699
CYP2D6-inhibitor:	0.502
CYP2D6-substrate:	0.312
CYP3A4-inhibitor:	0.041
CYP3A4-substrate:	0.107

ADMET: Excretion

Clearance (CL):	5.992
Half-life (T1/2):	0.924

ADMET: Toxicity

hERG Blockers:	0.11
Human Hepatotoxicity (H-HT):	0.036
Drug-inuced Liver Injury (DILI):	0.041
AMES Toxicity:	0.437
Rat Oral Acute Toxicity:	0.141
Maximum Recommended Daily Dose:	0.004
Skin Sensitization:	0.945
Carcinogencity:	0.168
Eye Corrosion:	0.003
Eye Irritation:	0.104
Respiratory Toxicity:	0.019

Download Data

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

Natural Product: NPC232228

Natural Product ID:	NPC232228
*Common Name:**	Salviifoside B
IUPAC Name:	[3-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl (E)-3-(2-hydroxyphenyl)prop-2-enoate
Synonyms:	Salviifoside B
Standard InCHIKey:	GRIARFWENNSKKF-CKNMYDPISA-N
Standard InCHI:	InChI=1S/C22H24O10/c23-10-17-19(27)20(28)21(29)22(32-17)31-16-7-5-12(9-15(16)25)11-30-18(26)8-6-13-3-1-2-4-14(13)24/h1-9,17,19-25,27-29H,10-11H2/b8-6+/t17-,19-,20+,21-,22-/m1/s1
SMILES:	c1ccc(c(c1)/C=C/C(=O)OCc1ccc(c(c1)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL551124
PubChem CID:	45271726
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic glycosides

*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
NPO672	Alangium salviifolium	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1171883]
NPO672	Alangium salviifolium	Species	Cornaceae	Eukaryota	leaves	n.a.	n.a.	PMID[19500975]
NPO672	Alangium salviifolium	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31513408]
NPO672	Alangium salviifolium	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO672	Alangium salviifolium	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	43.2	ng/ml	PMID[466012]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	24.4	ng/ml	PMID[466012]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	11.2	ng/ml	PMID[466012]

☑ 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 NPC232228 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	347
0.1-0.2	1583
0.2-0.3	4181
0.3-0.4	9426
0.4-0.5	8633
0.5-0.6	4469
0.6-0.7	7536
0.7-0.8	5250
0.8-0.85	915
0.85-0.9	299
0.9-0.95	50
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9855	High Similarity	NPC199928
0.9854	High Similarity	NPC292443
0.9781	High Similarity	NPC478239
0.9779	High Similarity	NPC186406
0.9708	High Similarity	NPC157816
0.9565	High Similarity	NPC140502
0.9562	High Similarity	NPC202700
0.95	High Similarity	NPC476864
0.95	High Similarity	NPC476868
0.95	High Similarity	NPC476869
0.95	High Similarity	NPC476866
0.9489	High Similarity	NPC100389
0.9485	High Similarity	NPC186418
0.9433	High Similarity	NPC476865
0.9429	High Similarity	NPC476867
0.9424	High Similarity	NPC145319
0.9371	High Similarity	NPC106138
0.9366	High Similarity	NPC41844
0.9362	High Similarity	NPC252292
0.9362	High Similarity	NPC100998
0.9362	High Similarity	NPC476382
0.9362	High Similarity	NPC34927
0.9362	High Similarity	NPC34587
0.9343	High Similarity	NPC471665
0.9343	High Similarity	NPC166180
0.9343	High Similarity	NPC471664
0.9343	High Similarity	NPC37468
0.9343	High Similarity	NPC157554
0.9301	High Similarity	NPC93924
0.9301	High Similarity	NPC478237
0.9291	High Similarity	NPC110063
0.9275	High Similarity	NPC126206
0.9247	High Similarity	NPC150442
0.9241	High Similarity	NPC213197
0.9236	High Similarity	NPC206264
0.9236	High Similarity	NPC313334
0.9236	High Similarity	NPC212670
0.9231	High Similarity	NPC232992
0.9225	High Similarity	NPC262182
0.9225	High Similarity	NPC216819
0.9225	High Similarity	NPC83743
0.9225	High Similarity	NPC287615
0.9209	High Similarity	NPC226005
0.9197	High Similarity	NPC886
0.9197	High Similarity	NPC34293
0.9197	High Similarity	NPC287597
0.9178	High Similarity	NPC53587
0.9178	High Similarity	NPC169404
0.9178	High Similarity	NPC176186
0.9172	High Similarity	NPC476871
0.9149	High Similarity	NPC475084
0.9137	High Similarity	NPC138738
0.9137	High Similarity	NPC470413
0.9137	High Similarity	NPC78363
0.913	High Similarity	NPC476870
0.9103	High Similarity	NPC471062
0.9103	High Similarity	NPC470933
0.9103	High Similarity	NPC306890
0.9103	High Similarity	NPC111785
0.9103	High Similarity	NPC259347
0.9103	High Similarity	NPC473427
0.9103	High Similarity	NPC476398
0.9103	High Similarity	NPC476386
0.9103	High Similarity	NPC94871
0.9097	High Similarity	NPC52740
0.9085	High Similarity	NPC252169
0.9067	High Similarity	NPC478269
0.906	High Similarity	NPC228357
0.9058	High Similarity	NPC87696
0.9058	High Similarity	NPC135127
0.9054	High Similarity	NPC191046
0.9054	High Similarity	NPC194095
0.9054	High Similarity	NPC327032
0.9048	High Similarity	NPC215060
0.9048	High Similarity	NPC476352
0.9041	High Similarity	NPC470927
0.9041	High Similarity	NPC257970
0.9041	High Similarity	NPC470934
0.9041	High Similarity	NPC188393
0.9034	High Similarity	NPC476348
0.9034	High Similarity	NPC201148
0.9034	High Similarity	NPC210611
0.9034	High Similarity	NPC192763
0.9034	High Similarity	NPC215095
0.9034	High Similarity	NPC261122
0.9034	High Similarity	NPC187398
0.9034	High Similarity	NPC199311
0.9034	High Similarity	NPC28651
0.9034	High Similarity	NPC96294
0.9034	High Similarity	NPC3460
0.9034	High Similarity	NPC300262
0.9034	High Similarity	NPC80732
0.9007	High Similarity	NPC106944
0.9	High Similarity	NPC65530
0.9	High Similarity	NPC260425
0.9	High Similarity	NPC59324
0.8993	High Similarity	NPC214729
0.8993	High Similarity	NPC55040
0.8978	High Similarity	NPC166168
0.8973	High Similarity	NPC478242
0.8973	High Similarity	NPC283839
0.8973	High Similarity	NPC90896
0.8971	High Similarity	NPC477294
0.8971	High Similarity	NPC477293
0.8971	High Similarity	NPC229784
0.8966	High Similarity	NPC476347
0.8958	High Similarity	NPC475096
0.8958	High Similarity	NPC138915
0.8947	High Similarity	NPC478267
0.8944	High Similarity	NPC476385
0.8944	High Similarity	NPC469661
0.8944	High Similarity	NPC134405
0.8936	High Similarity	NPC321184
0.8936	High Similarity	NPC476383
0.8936	High Similarity	NPC81515
0.8936	High Similarity	NPC212770
0.8936	High Similarity	NPC68092
0.8936	High Similarity	NPC321638
0.8936	High Similarity	NPC89105
0.8936	High Similarity	NPC472350
0.8936	High Similarity	NPC328273
0.8936	High Similarity	NPC171134
0.8936	High Similarity	NPC197316
0.8936	High Similarity	NPC205195
0.8936	High Similarity	NPC64141
0.8936	High Similarity	NPC98777
0.8933	High Similarity	NPC471405
0.8933	High Similarity	NPC11411
0.8929	High Similarity	NPC242028
0.8929	High Similarity	NPC177035
0.8929	High Similarity	NPC52277
0.8929	High Similarity	NPC199459
0.8929	High Similarity	NPC203230
0.8921	High Similarity	NPC187194
0.8921	High Similarity	NPC476411
0.8919	High Similarity	NPC36130
0.8919	High Similarity	NPC134905
0.8919	High Similarity	NPC478268
0.8913	High Similarity	NPC473285
0.8912	High Similarity	NPC205727
0.8912	High Similarity	NPC294522
0.8912	High Similarity	NPC114740
0.8912	High Similarity	NPC120426
0.8912	High Similarity	NPC21184
0.8897	High Similarity	NPC125755
0.8897	High Similarity	NPC40222
0.8897	High Similarity	NPC99515
0.8897	High Similarity	NPC268515
0.8897	High Similarity	NPC232880
0.8897	High Similarity	NPC190714
0.8897	High Similarity	NPC146540
0.8889	High Similarity	NPC76176
0.8889	High Similarity	NPC168579
0.8889	High Similarity	NPC469313
0.8889	High Similarity	NPC138227
0.8889	High Similarity	NPC297342
0.8881	High Similarity	NPC265648
0.8881	High Similarity	NPC222433
0.8881	High Similarity	NPC469559
0.8881	High Similarity	NPC189115
0.8874	High Similarity	NPC133984
0.8867	High Similarity	NPC10205
0.8865	High Similarity	NPC124149
0.8859	High Similarity	NPC157898
0.8851	High Similarity	NPC125823
0.8851	High Similarity	NPC143480
0.8851	High Similarity	NPC7145
0.8851	High Similarity	NPC85192
0.8844	High Similarity	NPC30688
0.8844	High Similarity	NPC176903
0.8841	High Similarity	NPC9912
0.8841	High Similarity	NPC248307
0.8841	High Similarity	NPC219677
0.8841	High Similarity	NPC65942
0.8836	High Similarity	NPC31325
0.8836	High Similarity	NPC227902
0.8836	High Similarity	NPC114505
0.8836	High Similarity	NPC275284
0.8836	High Similarity	NPC15956
0.8836	High Similarity	NPC213074
0.8836	High Similarity	NPC193473
0.8836	High Similarity	NPC224674
0.8832	High Similarity	NPC307110
0.8832	High Similarity	NPC166040
0.8832	High Similarity	NPC248355
0.8828	High Similarity	NPC163898
0.8828	High Similarity	NPC277867
0.8828	High Similarity	NPC473909
0.8828	High Similarity	NPC143120
0.8828	High Similarity	NPC274960
0.8828	High Similarity	NPC161700
0.8824	High Similarity	NPC476873
0.8819	High Similarity	NPC470950
0.8819	High Similarity	NPC185307
0.8819	High Similarity	NPC46092
0.8819	High Similarity	NPC37793
0.8816	High Similarity	NPC160780
0.8816	High Similarity	NPC289811
0.8811	High Similarity	NPC47471
0.8811	High Similarity	NPC476377

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 NPC232228 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	288
0.1-0.2	861
0.2-0.3	1856
0.3-0.4	2764
0.4-0.5	1742
0.5-0.6	962
0.6-0.7	575
0.7-0.8	93
0.8-0.85	8
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9236	High Similarity	NPD1653	Approved
0.8936	High Similarity	NPD7266	Discontinued
0.838	Intermediate Similarity	NPD1613	Approved
0.838	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD3818	Discontinued
0.8282	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD7054	Approved
0.8248	Intermediate Similarity	NPD1091	Approved
0.821	Intermediate Similarity	NPD7074	Phase 3
0.821	Intermediate Similarity	NPD7472	Approved
0.8205	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8099	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD6797	Phase 2
0.8042	Intermediate Similarity	NPD3027	Phase 3
0.8038	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8028	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7685	Pre-registration
0.8	Intermediate Similarity	NPD7251	Discontinued
0.7952	Intermediate Similarity	NPD7808	Phase 3
0.7947	Intermediate Similarity	NPD6190	Approved
0.7933	Intermediate Similarity	NPD6674	Discontinued
0.7898	Intermediate Similarity	NPD1934	Approved
0.7875	Intermediate Similarity	NPD6234	Discontinued
0.7872	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD7228	Approved
0.7848	Intermediate Similarity	NPD8455	Phase 2
0.7843	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD37	Approved
0.7784	Intermediate Similarity	NPD6559	Discontinued
0.7778	Intermediate Similarity	NPD7199	Phase 2
0.775	Intermediate Similarity	NPD4966	Approved
0.775	Intermediate Similarity	NPD4967	Phase 2
0.775	Intermediate Similarity	NPD4965	Approved
0.7744	Intermediate Similarity	NPD6166	Phase 2
0.7744	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD3817	Phase 2
0.7655	Intermediate Similarity	NPD2861	Phase 2
0.7635	Intermediate Similarity	NPD4060	Phase 1
0.7625	Intermediate Similarity	NPD2801	Approved
0.7625	Intermediate Similarity	NPD1465	Phase 2
0.7605	Intermediate Similarity	NPD5844	Phase 1
0.7602	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD8312	Approved
0.7588	Intermediate Similarity	NPD8313	Approved
0.7584	Intermediate Similarity	NPD1933	Approved
0.7582	Intermediate Similarity	NPD1652	Phase 2
0.7576	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD4628	Phase 3
0.7531	Intermediate Similarity	NPD3882	Suspended
0.7518	Intermediate Similarity	NPD1357	Approved
0.75	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1511	Approved
0.7485	Intermediate Similarity	NPD7075	Discontinued
0.7483	Intermediate Similarity	NPD3705	Approved
0.7469	Intermediate Similarity	NPD5402	Approved
0.7468	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD4340	Discontinued
0.7438	Intermediate Similarity	NPD4380	Phase 2
0.7413	Intermediate Similarity	NPD3496	Discontinued
0.7405	Intermediate Similarity	NPD1512	Approved
0.7383	Intermediate Similarity	NPD6798	Discontinued
0.7376	Intermediate Similarity	NPD5536	Phase 2
0.7371	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7240	Approved
0.7368	Intermediate Similarity	NPD7097	Phase 1
0.7365	Intermediate Similarity	NPD4908	Phase 1
0.7361	Intermediate Similarity	NPD422	Phase 1
0.7361	Intermediate Similarity	NPD1610	Phase 2
0.7358	Intermediate Similarity	NPD5403	Approved
0.7355	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD5124	Phase 1
0.7351	Intermediate Similarity	NPD447	Suspended
0.7349	Intermediate Similarity	NPD8127	Discontinued
0.7337	Intermediate Similarity	NPD3751	Discontinued
0.7333	Intermediate Similarity	NPD6233	Phase 2
0.7329	Intermediate Similarity	NPD3225	Approved
0.7325	Intermediate Similarity	NPD5058	Phase 3
0.7324	Intermediate Similarity	NPD1548	Phase 1
0.7319	Intermediate Similarity	NPD228	Approved
0.7301	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD3018	Phase 2
0.7267	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6801	Discontinued
0.7237	Intermediate Similarity	NPD230	Phase 1
0.7237	Intermediate Similarity	NPD6355	Discontinued
0.7233	Intermediate Similarity	NPD5401	Approved
0.7233	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD5762	Approved
0.7226	Intermediate Similarity	NPD5763	Approved
0.7225	Intermediate Similarity	NPD7549	Discontinued
0.7216	Intermediate Similarity	NPD6841	Approved
0.7216	Intermediate Similarity	NPD6842	Approved
0.7216	Intermediate Similarity	NPD6843	Phase 3
0.7208	Intermediate Similarity	NPD7033	Discontinued
0.7205	Intermediate Similarity	NPD3687	Approved
0.7205	Intermediate Similarity	NPD3686	Approved
0.7202	Intermediate Similarity	NPD3787	Discontinued
0.7202	Intermediate Similarity	NPD6232	Discontinued
0.72	Intermediate Similarity	NPD7095	Approved
0.7197	Intermediate Similarity	NPD3750	Approved
0.7195	Intermediate Similarity	NPD2978	Approved
0.7195	Intermediate Similarity	NPD2977	Approved
0.7195	Intermediate Similarity	NPD7819	Suspended
0.7191	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1549	Phase 2
0.7171	Intermediate Similarity	NPD1558	Phase 1
0.717	Intermediate Similarity	NPD6799	Approved
0.7161	Intermediate Similarity	NPD2935	Discontinued
0.7161	Intermediate Similarity	NPD1551	Phase 2
0.7153	Intermediate Similarity	NPD1358	Approved
0.7153	Intermediate Similarity	NPD290	Approved
0.7143	Intermediate Similarity	NPD2983	Phase 2
0.7143	Intermediate Similarity	NPD4536	Approved
0.7143	Intermediate Similarity	NPD2982	Phase 2
0.7143	Intermediate Similarity	NPD4538	Approved
0.7143	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD1778	Approved
0.7097	Intermediate Similarity	NPD5960	Phase 3
0.7097	Intermediate Similarity	NPD5588	Approved
0.7092	Intermediate Similarity	NPD5283	Phase 1
0.7089	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD4110	Phase 3
0.7089	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5494	Approved
0.7081	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6653	Approved
0.7076	Intermediate Similarity	NPD7473	Discontinued
0.7075	Intermediate Similarity	NPD2981	Phase 2
0.7073	Intermediate Similarity	NPD7411	Suspended
0.707	Intermediate Similarity	NPD2424	Discontinued
0.7069	Intermediate Similarity	NPD7039	Approved
0.7069	Intermediate Similarity	NPD7038	Approved
0.7067	Intermediate Similarity	NPD9494	Approved
0.7059	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3620	Phase 2
0.7055	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD6032	Approved
0.7049	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD1203	Approved
0.7047	Intermediate Similarity	NPD2797	Approved
0.7021	Intermediate Similarity	NPD7843	Approved
0.7021	Intermediate Similarity	NPD5535	Approved
0.6993	Remote Similarity	NPD6671	Approved
0.6993	Remote Similarity	NPD4062	Phase 3
0.6993	Remote Similarity	NPD7157	Approved
0.6989	Remote Similarity	NPD7680	Approved
0.6986	Remote Similarity	NPD4626	Approved
0.6981	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.698	Remote Similarity	NPD8651	Approved
0.6978	Remote Similarity	NPD2684	Approved
0.6975	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD4625	Phase 3
0.6964	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4357	Discontinued
0.6957	Remote Similarity	NPD968	Approved
0.6957	Remote Similarity	NPD3134	Approved
0.6951	Remote Similarity	NPD7458	Discontinued
0.6948	Remote Similarity	NPD4140	Approved
0.6937	Remote Similarity	NPD2677	Approved
0.6928	Remote Similarity	NPD3268	Approved
0.6928	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD5585	Approved
0.6918	Remote Similarity	NPD5691	Approved
0.6918	Remote Similarity	NPD5177	Phase 3
0.6918	Remote Similarity	NPD3060	Approved
0.6914	Remote Similarity	NPD4123	Phase 3
0.6914	Remote Similarity	NPD3536	Discontinued
0.6914	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD4749	Approved
0.6909	Remote Similarity	NPD6599	Discontinued
0.6908	Remote Similarity	NPD6832	Phase 2
0.6905	Remote Similarity	NPD7768	Phase 2
0.6903	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD1375	Discontinued
0.6892	Remote Similarity	NPD1535	Discovery
0.6884	Remote Similarity	NPD9697	Approved
0.6882	Remote Similarity	NPD4666	Phase 3
0.6879	Remote Similarity	NPD3748	Approved
0.6879	Remote Similarity	NPD1510	Phase 2
0.6875	Remote Similarity	NPD8166	Discontinued
0.6871	Remote Similarity	NPD6516	Phase 2
0.6871	Remote Similarity	NPD5846	Approved
0.6867	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6386	Approved
0.6867	Remote Similarity	NPD6385	Approved
0.6859	Remote Similarity	NPD2492	Phase 1
0.6854	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD1774	Approved
0.6849	Remote Similarity	NPD1894	Discontinued
0.6848	Remote Similarity	NPD3111	Phase 1

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