NPASS Compound

Structure

NPC475695 OpenBabel07101718182D 23 23 0 0 1 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 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 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 5.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 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 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 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 0.0000 C 0 0 3 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 6.0622 -1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.5622 -2.3660 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 4.3301 -1.5000 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 7.7942 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 8 1 0 0 0 0 2 4 2 0 0 0 0 2 8 1 0 0 0 0 3 9 1 0 0 0 0 4 11 1 0 0 0 0 5 8 2 0 0 0 0 5 10 1 0 0 0 0 6 14 1 0 0 0 0 6 15 1 0 0 0 0 7 14 1 0 0 0 0 7 23 1 0 0 0 0 9 10 2 0 0 0 0 9 16 1 0 0 0 0 10 17 1 0 0 0 0 11 18 2 0 0 0 0 11 23 1 0 0 0 0 12 13 1 0 0 0 0 12 14 1 0 0 0 0 12 19 1 0 0 0 0 13 20 2 0 0 0 0 13 21 1 0 0 0 0 14 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.08
Volume:	305.437
LogP:	-0.166
LogD:	-0.157
LogS:	-1.217
# Rotatable Bonds:	8
TPSA:	164.75
# H-Bond Aceptor:	9
# H-Bond Donor:	6
# Rings:	1
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.147
Synthetic Accessibility Score:	3.429
Fsp3:	0.286
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.113
MDCK Permeability:	0.00022804886975791305
Pgp-inhibitor:	0.001
Pgp-substrate:	0.948
Human Intestinal Absorption (HIA):	0.402
20% Bioavailability (F20%):	0.869
30% Bioavailability (F30%):	0.969

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.622
Plasma Protein Binding (PPB):	70.4219741821289%
Volume Distribution (VD):	0.56
Pgp-substrate:	42.60910415649414%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.066
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.022
CYP2C9-substrate:	0.454
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.145
CYP3A4-inhibitor:	0.072
CYP3A4-substrate:	0.042

ADMET: Excretion

Clearance (CL):	2.053
Half-life (T1/2):	0.942

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.088
Drug-inuced Liver Injury (DILI):	0.774
AMES Toxicity:	0.237
Rat Oral Acute Toxicity:	0.033
Maximum Recommended Daily Dose:	0.376
Skin Sensitization:	0.4
Carcinogencity:	0.28
Eye Corrosion:	0.003
Eye Irritation:	0.028
Respiratory Toxicity:	0.205

Download Data

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

Natural Product: NPC475695

Natural Product ID:	NPC475695
*Common Name:**	4-(3-(3,4-Dihydroxyphenyl)Acryloyloxy)-2,3-Dihydroxy-3-(Hydroxymethyl)Butanoic Acid
IUPAC Name:	3-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxymethyl]-2,3,4-trihydroxybutanoic acid
Synonyms:
Standard InCHIKey:	BMVREUNZOSAHNV-DUXPYHPUSA-N
Standard InCHI:	InChI=1S/C14H16O9/c15-6-14(22,12(19)13(20)21)7-23-11(18)4-2-8-1-3-9(16)10(17)5-8/h1-5,12,15-17,19,22H,6-7H2,(H,20,21)/b4-2+
SMILES:	C1=CC(=C(C=C1C=CC(=O)OCC(CO)(C(C(=O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL511877
PubChem CID:	11012871
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0000059] Coumaric acids and derivatives

*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
NPO12110	Bauhinia tarapotensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473417]
NPO12110	Bauhinia tarapotensis	Species	Fabaceae	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
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	0.484	n.a.	PMID[475037]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	25.2	n.a.	PMID[475037]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	20.5	n.a.	PMID[475037]

☑ 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 NPC475695 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	301
0.1-0.2	1225
0.2-0.3	4142
0.3-0.4	9352
0.4-0.5	9228
0.5-0.6	6056
0.6-0.7	10276
0.7-0.8	1915
0.8-0.85	142
0.85-0.9	48
0.9-0.95	7
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9669	High Similarity	NPC168653
0.9669	High Similarity	NPC251407
0.9587	High Similarity	NPC132921
0.936	High Similarity	NPC329344
0.936	High Similarity	NPC32626
0.936	High Similarity	NPC237506
0.936	High Similarity	NPC217052
0.935	High Similarity	NPC147192
0.9219	High Similarity	NPC474895
0.9008	High Similarity	NPC279676
0.9008	High Similarity	NPC67349
0.8908	High Similarity	NPC217472
0.8872	High Similarity	NPC179505
0.8872	High Similarity	NPC156709
0.8833	High Similarity	NPC233669
0.88	High Similarity	NPC474275
0.88	High Similarity	NPC224208
0.8797	High Similarity	NPC37250
0.8797	High Similarity	NPC278068
0.8797	High Similarity	NPC219428
0.8797	High Similarity	NPC152942
0.8797	High Similarity	NPC142703
0.8797	High Similarity	NPC302857
0.8788	High Similarity	NPC470572
0.876	High Similarity	NPC281277
0.875	High Similarity	NPC328593
0.875	High Similarity	NPC33749
0.875	High Similarity	NPC261453
0.8731	High Similarity	NPC476820
0.8731	High Similarity	NPC26241
0.8731	High Similarity	NPC274891
0.8731	High Similarity	NPC303683
0.8731	High Similarity	NPC205751
0.8731	High Similarity	NPC295492
0.8731	High Similarity	NPC476819
0.8731	High Similarity	NPC474875
0.8689	High Similarity	NPC65791
0.8678	High Similarity	NPC474967
0.8672	High Similarity	NPC476873
0.8667	High Similarity	NPC95381
0.8657	High Similarity	NPC220942
0.8618	High Similarity	NPC309434
0.8605	High Similarity	NPC232880
0.8603	High Similarity	NPC224389
0.8603	High Similarity	NPC477335
0.8603	High Similarity	NPC13818
0.8603	High Similarity	NPC297517
0.8603	High Similarity	NPC206095
0.8603	High Similarity	NPC35702
0.8603	High Similarity	NPC471027
0.8594	High Similarity	NPC118584
0.8551	High Similarity	NPC53884
0.8551	High Similarity	NPC258671
0.855	High Similarity	NPC108553
0.8548	High Similarity	NPC241634
0.854	High Similarity	NPC258469
0.854	High Similarity	NPC319628
0.854	High Similarity	NPC43158
0.854	High Similarity	NPC277315
0.854	High Similarity	NPC37331
0.854	High Similarity	NPC303090
0.854	High Similarity	NPC192831
0.854	High Similarity	NPC284948
0.854	High Similarity	NPC472016
0.854	High Similarity	NPC220664
0.8538	High Similarity	NPC477294
0.8538	High Similarity	NPC477293
0.8538	High Similarity	NPC229784
0.8516	High Similarity	NPC67951
0.8504	High Similarity	NPC285345
0.85	High Similarity	NPC192568
0.85	High Similarity	NPC226250
0.85	High Similarity	NPC471076
0.8496	Intermediate Similarity	NPC106406
0.8496	Intermediate Similarity	NPC68517
0.8485	Intermediate Similarity	NPC61
0.8485	Intermediate Similarity	NPC18074
0.8485	Intermediate Similarity	NPC25581
0.8485	Intermediate Similarity	NPC473924
0.8485	Intermediate Similarity	NPC5419
0.8478	Intermediate Similarity	NPC304956
0.8468	Intermediate Similarity	NPC203124
0.8433	Intermediate Similarity	NPC182217
0.8433	Intermediate Similarity	NPC70680
0.8433	Intermediate Similarity	NPC233350
0.8429	Intermediate Similarity	NPC283081
0.8429	Intermediate Similarity	NPC299090
0.8429	Intermediate Similarity	NPC229264
0.8429	Intermediate Similarity	NPC322660
0.8429	Intermediate Similarity	NPC221383
0.8429	Intermediate Similarity	NPC143892
0.8421	Intermediate Similarity	NPC254398
0.8421	Intermediate Similarity	NPC168799
0.8421	Intermediate Similarity	NPC155209
0.8413	Intermediate Similarity	NPC204466
0.8413	Intermediate Similarity	NPC470848
0.8413	Intermediate Similarity	NPC470849
0.8409	Intermediate Similarity	NPC219677
0.8409	Intermediate Similarity	NPC198388
0.84	Intermediate Similarity	NPC141791
0.84	Intermediate Similarity	NPC263386
0.8359	Intermediate Similarity	NPC306100
0.8357	Intermediate Similarity	NPC98356
0.8346	Intermediate Similarity	NPC473285
0.8346	Intermediate Similarity	NPC70752
0.8345	Intermediate Similarity	NPC50221
0.8345	Intermediate Similarity	NPC114242
0.8333	Intermediate Similarity	NPC202474
0.832	Intermediate Similarity	NPC275519
0.8286	Intermediate Similarity	NPC477333
0.8284	Intermediate Similarity	NPC475468
0.8279	Intermediate Similarity	NPC131530
0.8248	Intermediate Similarity	NPC283560
0.8248	Intermediate Similarity	NPC24295
0.8235	Intermediate Similarity	NPC1786
0.8235	Intermediate Similarity	NPC294902
0.8235	Intermediate Similarity	NPC1075
0.8231	Intermediate Similarity	NPC197832
0.8222	Intermediate Similarity	NPC135127
0.8222	Intermediate Similarity	NPC471110
0.8222	Intermediate Similarity	NPC886
0.8222	Intermediate Similarity	NPC34293
0.8222	Intermediate Similarity	NPC287597
0.8222	Intermediate Similarity	NPC471883
0.8214	Intermediate Similarity	NPC474692
0.8203	Intermediate Similarity	NPC147654
0.8201	Intermediate Similarity	NPC477277
0.8201	Intermediate Similarity	NPC477278
0.8188	Intermediate Similarity	NPC105525
0.8188	Intermediate Similarity	NPC225036
0.8188	Intermediate Similarity	NPC471875
0.8188	Intermediate Similarity	NPC75763
0.8188	Intermediate Similarity	NPC12218
0.8182	Intermediate Similarity	NPC42464
0.8182	Intermediate Similarity	NPC110313
0.8175	Intermediate Similarity	NPC70744
0.8175	Intermediate Similarity	NPC63126
0.8175	Intermediate Similarity	NPC272471
0.8175	Intermediate Similarity	NPC137537
0.8175	Intermediate Similarity	NPC164706
0.8175	Intermediate Similarity	NPC104514
0.8175	Intermediate Similarity	NPC107588
0.8162	Intermediate Similarity	NPC470990
0.8162	Intermediate Similarity	NPC476870
0.8154	Intermediate Similarity	NPC60517
0.8154	Intermediate Similarity	NPC146886
0.8154	Intermediate Similarity	NPC20443
0.8154	Intermediate Similarity	NPC246704
0.8148	Intermediate Similarity	NPC471749
0.8148	Intermediate Similarity	NPC289572
0.8148	Intermediate Similarity	NPC157478
0.8148	Intermediate Similarity	NPC200422
0.8148	Intermediate Similarity	NPC295406
0.8138	Intermediate Similarity	NPC95498
0.8138	Intermediate Similarity	NPC246566
0.8134	Intermediate Similarity	NPC318799
0.8134	Intermediate Similarity	NPC281798
0.8129	Intermediate Similarity	NPC477279
0.8125	Intermediate Similarity	NPC32197
0.8125	Intermediate Similarity	NPC476872
0.8125	Intermediate Similarity	NPC306343
0.812	Intermediate Similarity	NPC226855
0.812	Intermediate Similarity	NPC48315
0.812	Intermediate Similarity	NPC477300
0.8116	Intermediate Similarity	NPC328273
0.8116	Intermediate Similarity	NPC239943
0.8116	Intermediate Similarity	NPC321184
0.8116	Intermediate Similarity	NPC171134
0.8116	Intermediate Similarity	NPC321638
0.8112	Intermediate Similarity	NPC43123
0.811	Intermediate Similarity	NPC70084
0.811	Intermediate Similarity	NPC470214
0.811	Intermediate Similarity	NPC470215
0.811	Intermediate Similarity	NPC109371
0.8102	Intermediate Similarity	NPC186418
0.8102	Intermediate Similarity	NPC157554
0.8099	Intermediate Similarity	NPC473867
0.8092	Intermediate Similarity	NPC289459
0.8062	Intermediate Similarity	NPC11724
0.8058	Intermediate Similarity	NPC289690
0.8058	Intermediate Similarity	NPC147379
0.8058	Intermediate Similarity	NPC288452
0.8047	Intermediate Similarity	NPC2058
0.8045	Intermediate Similarity	NPC109275
0.8043	Intermediate Similarity	NPC78363
0.8043	Intermediate Similarity	NPC476376
0.8043	Intermediate Similarity	NPC260425
0.8031	Intermediate Similarity	NPC86198
0.803	Intermediate Similarity	NPC120225
0.803	Intermediate Similarity	NPC213552
0.8029	Intermediate Similarity	NPC29317
0.8029	Intermediate Similarity	NPC229638
0.8029	Intermediate Similarity	NPC267539
0.8029	Intermediate Similarity	NPC71108
0.8029	Intermediate Similarity	NPC204257
0.8029	Intermediate Similarity	NPC176102
0.8029	Intermediate Similarity	NPC254832
0.8029	Intermediate Similarity	NPC311742
0.8015	Intermediate Similarity	NPC288945
0.8015	Intermediate Similarity	NPC469568

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 NPC475695 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	242
0.1-0.2	782
0.2-0.3	1937
0.3-0.4	2848
0.4-0.5	1789
0.5-0.6	1119
0.6-0.7	401
0.7-0.8	31
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.854	High Similarity	NPD6190	Approved
0.7986	Intermediate Similarity	NPD7266	Discontinued
0.7883	Intermediate Similarity	NPD230	Phase 1
0.7803	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD9494	Approved
0.75	Intermediate Similarity	NPD447	Suspended
0.7463	Intermediate Similarity	NPD9269	Phase 2
0.745	Intermediate Similarity	NPD1653	Approved
0.744	Intermediate Similarity	NPD1358	Approved
0.7344	Intermediate Similarity	NPD228	Approved
0.7329	Intermediate Similarity	NPD8166	Discontinued
0.7292	Intermediate Similarity	NPD9570	Approved
0.7273	Intermediate Similarity	NPD5536	Phase 2
0.7226	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD9545	Approved
0.7214	Intermediate Similarity	NPD3027	Phase 3
0.7197	Intermediate Similarity	NPD9493	Approved
0.7183	Intermediate Similarity	NPD826	Approved
0.7183	Intermediate Similarity	NPD825	Approved
0.7171	Intermediate Similarity	NPD3455	Phase 2
0.7164	Intermediate Similarity	NPD9268	Approved
0.7164	Intermediate Similarity	NPD1357	Approved
0.7134	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD3882	Suspended
0.7113	Intermediate Similarity	NPD6233	Phase 2
0.7092	Intermediate Similarity	NPD7095	Approved
0.7087	Intermediate Similarity	NPD3134	Approved
0.7083	Intermediate Similarity	NPD6653	Approved
0.7077	Intermediate Similarity	NPD969	Suspended
0.7063	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD4060	Phase 1
0.7063	Intermediate Similarity	NPD943	Approved
0.7063	Intermediate Similarity	NPD1613	Approved
0.7055	Intermediate Similarity	NPD2935	Discontinued
0.7054	Intermediate Similarity	NPD3021	Approved
0.7054	Intermediate Similarity	NPD3022	Approved
0.7051	Intermediate Similarity	NPD5402	Approved
0.7051	Intermediate Similarity	NPD3817	Phase 2
0.7037	Intermediate Similarity	NPD3818	Discontinued
0.7019	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6166	Phase 2
0.7014	Intermediate Similarity	NPD555	Phase 2
0.7012	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5647	Approved
0.6974	Remote Similarity	NPD1512	Approved
0.697	Remote Similarity	NPD7685	Pre-registration
0.6934	Remote Similarity	NPD3496	Discontinued
0.6923	Remote Similarity	NPD1934	Approved
0.6923	Remote Similarity	NPD6798	Discontinued
0.6909	Remote Similarity	NPD6797	Phase 2
0.6905	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6355	Discontinued
0.6879	Remote Similarity	NPD2801	Approved
0.6879	Remote Similarity	NPD257	Approved
0.6879	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD258	Approved
0.6875	Remote Similarity	NPD4062	Phase 3
0.6875	Remote Similarity	NPD259	Phase 1
0.6867	Remote Similarity	NPD4628	Phase 3
0.6867	Remote Similarity	NPD7251	Discontinued
0.6861	Remote Similarity	NPD9381	Approved
0.6861	Remote Similarity	NPD9384	Approved
0.6855	Remote Similarity	NPD7075	Discontinued
0.6846	Remote Similarity	NPD2424	Discontinued
0.6846	Remote Similarity	NPD74	Approved
0.6846	Remote Similarity	NPD9266	Approved
0.6842	Remote Similarity	NPD1511	Approved
0.6835	Remote Similarity	NPD9717	Approved
0.6831	Remote Similarity	NPD9569	Approved
0.6818	Remote Similarity	NPD5403	Approved
0.6813	Remote Similarity	NPD6234	Discontinued
0.6809	Remote Similarity	NPD1203	Approved
0.6806	Remote Similarity	NPD3764	Approved
0.6803	Remote Similarity	NPD7097	Phase 1
0.68	Remote Similarity	NPD9495	Approved
0.6795	Remote Similarity	NPD4380	Phase 2
0.6794	Remote Similarity	NPD2067	Discontinued
0.6791	Remote Similarity	NPD2629	Approved
0.6791	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD7054	Approved
0.6783	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD9264	Approved
0.6769	Remote Similarity	NPD9267	Approved
0.6769	Remote Similarity	NPD290	Approved
0.6769	Remote Similarity	NPD9263	Approved
0.6767	Remote Similarity	NPD7843	Approved
0.6755	Remote Similarity	NPD4110	Phase 3
0.6755	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD7472	Approved
0.6747	Remote Similarity	NPD7074	Phase 3
0.6742	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD4198	Discontinued
0.6741	Remote Similarity	NPD7157	Approved
0.6739	Remote Similarity	NPD4626	Approved
0.6739	Remote Similarity	NPD1778	Approved
0.6732	Remote Similarity	NPD6799	Approved
0.6732	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD7808	Phase 3
0.6718	Remote Similarity	NPD2684	Approved
0.6713	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD5736	Approved
0.6712	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD37	Approved
0.6709	Remote Similarity	NPD6801	Discontinued
0.6691	Remote Similarity	NPD694	Clinical (unspecified phase)
0.669	Remote Similarity	NPD411	Approved
0.669	Remote Similarity	NPD987	Approved
0.6688	Remote Similarity	NPD5401	Approved
0.6687	Remote Similarity	NPD4965	Approved
0.6687	Remote Similarity	NPD6232	Discontinued
0.6687	Remote Similarity	NPD4966	Approved
0.6687	Remote Similarity	NPD4967	Phase 2
0.6667	Remote Similarity	NPD5691	Approved
0.6667	Remote Similarity	NPD3687	Approved
0.6667	Remote Similarity	NPD4340	Discontinued
0.6667	Remote Similarity	NPD3686	Approved
0.6667	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8150	Discontinued
0.6667	Remote Similarity	NPD9622	Approved
0.6667	Remote Similarity	NPD1465	Phase 2
0.6646	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD1091	Approved
0.6643	Remote Similarity	NPD1535	Discovery
0.6642	Remote Similarity	NPD9379	Approved
0.6642	Remote Similarity	NPD9377	Approved
0.6641	Remote Similarity	NPD291	Approved
0.6627	Remote Similarity	NPD7228	Approved
0.6627	Remote Similarity	NPD3751	Discontinued
0.6626	Remote Similarity	NPD8127	Discontinued
0.6623	Remote Similarity	NPD4357	Discontinued
0.6623	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD9536	Phase 1
0.6621	Remote Similarity	NPD9537	Phase 1
0.66	Remote Similarity	NPD1551	Phase 2
0.66	Remote Similarity	NPD6032	Approved
0.6599	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD3620	Phase 2
0.6596	Remote Similarity	NPD1481	Phase 2
0.6593	Remote Similarity	NPD5283	Phase 1
0.659	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD1652	Phase 2
0.6575	Remote Similarity	NPD1048	Approved
0.6573	Remote Similarity	NPD1164	Approved
0.6569	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD7473	Discontinued
0.6562	Remote Similarity	NPD1242	Phase 1
0.6556	Remote Similarity	NPD5763	Approved
0.6556	Remote Similarity	NPD5762	Approved
0.6554	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD274	Approved
0.6554	Remote Similarity	NPD1933	Approved
0.6554	Remote Similarity	NPD275	Approved
0.6552	Remote Similarity	NPD6832	Phase 2
0.6547	Remote Similarity	NPD5585	Approved
0.6544	Remote Similarity	NPD9281	Approved
0.6536	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD2799	Discontinued
0.6533	Remote Similarity	NPD7033	Discontinued
0.6531	Remote Similarity	NPD6663	Approved
0.6531	Remote Similarity	NPD520	Approved
0.6528	Remote Similarity	NPD9619	Approved
0.6528	Remote Similarity	NPD1019	Discontinued
0.6528	Remote Similarity	NPD9620	Approved
0.6528	Remote Similarity	NPD9621	Approved
0.6525	Remote Similarity	NPD3705	Approved
0.6525	Remote Similarity	NPD422	Phase 1
0.6519	Remote Similarity	NPD824	Approved
0.6514	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD5958	Discontinued
0.6513	Remote Similarity	NPD4534	Discontinued
0.65	Remote Similarity	NPD111	Approved
0.649	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.649	Remote Similarity	NPD2438	Suspended
0.6488	Remote Similarity	NPD5844	Phase 1
0.6486	Remote Similarity	NPD3062	Approved
0.6486	Remote Similarity	NPD3061	Approved
0.6486	Remote Similarity	NPD3059	Approved
0.6485	Remote Similarity	NPD3787	Discontinued
0.6478	Remote Similarity	NPD6599	Discontinued
0.6475	Remote Similarity	NPD1894	Discontinued
0.6474	Remote Similarity	NPD2534	Approved
0.6474	Remote Similarity	NPD2533	Approved
0.6474	Remote Similarity	NPD2532	Approved
0.6474	Remote Similarity	NPD8434	Phase 2
0.6471	Remote Similarity	NPD6559	Discontinued
0.6471	Remote Similarity	NPD1241	Discontinued
0.6463	Remote Similarity	NPD3144	Approved
0.6463	Remote Similarity	NPD598	Approved
0.6463	Remote Similarity	NPD597	Approved
0.6463	Remote Similarity	NPD601	Approved
0.6463	Remote Similarity	NPD2313	Discontinued
0.6463	Remote Similarity	NPD3145	Approved
0.6462	Remote Similarity	NPD6647	Phase 2
0.6462	Remote Similarity	NPD9261	Approved
0.646	Remote Similarity	NPD7972	Discontinued
0.6458	Remote Similarity	NPD6362	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