NPASS Compound

Structure

NPC24295 OpenBabel07101719252D 35 37 0 0 1 0 0 0 0 0999 V2000 -1.7321 -2.0000 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 4.7321 -2.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7321 -0.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2321 -1.5981 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 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7321 -2.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7321 -0.7321 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 2.7321 -0.7321 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 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2321 -1.5981 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 6.2321 -1.5981 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 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2321 0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2321 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 2 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 7.2321 -1.5981 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 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2321 0.1340 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 1.7321 2.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2321 1.8660 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 2.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 1 15 2 0 0 0 0 2 8 2 0 0 0 0 2 15 1 0 0 0 0 3 9 1 0 0 0 0 3 16 2 0 0 0 0 4 10 2 0 0 0 0 4 16 1 0 0 0 0 5 11 2 0 0 0 0 5 15 1 0 0 0 0 6 12 2 0 0 0 0 6 16 1 0 0 0 0 7 17 2 0 0 0 0 8 17 1 0 0 0 0 9 18 2 0 0 0 0 10 18 1 0 0 0 0 11 21 1 0 0 0 0 12 22 1 0 0 0 0 13 19 1 0 0 0 0 13 25 1 0 0 0 0 14 20 1 0 0 0 0 14 25 1 0 0 0 0 17 26 1 0 0 0 0 18 27 1 0 0 0 0 19 23 1 0 0 0 0 19 28 1 6 0 0 0 20 23 1 0 0 0 0 20 34 1 1 0 0 0 21 29 2 0 0 0 0 21 34 1 0 0 0 0 22 30 2 0 0 0 0 22 35 1 0 0 0 0 23 31 1 6 0 0 0 24 32 2 0 0 0 0 24 33 1 0 0 0 0 25 24 1 1 0 0 0 25 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	484.14
Volume:	474.188
LogP:	2.382
LogD:	0.909
LogS:	-2.365
# Rotatable Bonds:	9
TPSA:	170.82
# H-Bond Aceptor:	10
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.287
Synthetic Accessibility Score:	3.964
Fsp3:	0.24
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.191
MDCK Permeability:	1.7266167560592294e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.872
Human Intestinal Absorption (HIA):	0.452
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.07
Plasma Protein Binding (PPB):	97.3759994506836%
Volume Distribution (VD):	0.249
Pgp-substrate:	1.3234089612960815%

ADMET: Metabolism

CYP1A2-inhibitor:	0.114
CYP1A2-substrate:	0.02
CYP2C19-inhibitor:	0.177
CYP2C19-substrate:	0.053
CYP2C9-inhibitor:	0.636
CYP2C9-substrate:	0.961
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.158
CYP3A4-inhibitor:	0.527
CYP3A4-substrate:	0.088

ADMET: Excretion

Clearance (CL):	2.285
Half-life (T1/2):	0.931

ADMET: Toxicity

hERG Blockers:	0.122
Human Hepatotoxicity (H-HT):	0.155
Drug-inuced Liver Injury (DILI):	0.102
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.261
Maximum Recommended Daily Dose:	0.358
Skin Sensitization:	0.903
Carcinogencity:	0.2
Eye Corrosion:	0.003
Eye Irritation:	0.021
Respiratory Toxicity:	0.051

Download Data

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

Natural Product: NPC24295

Natural Product ID:	NPC24295
*Common Name:**	1,5-Di-O-Cis-P-Coumaroylquinic Acid
IUPAC Name:	(1S,3R,4R,5R)-3,4-dihydroxy-1,5-bis[[(Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy]cyclohexane-1-carboxylic acid
Synonyms:
Standard InCHIKey:	OVQYRMPAHZWNGN-BRKZRULUSA-N
Standard InCHI:	InChI=1S/C25H24O10/c26-17-7-1-15(2-8-17)5-11-21(29)34-20-14-25(24(32)33,13-19(28)23(20)31)35-22(30)12-6-16-3-9-18(27)10-4-16/h1-12,19-20,23,26-28,31H,13-14H2,(H,32,33)/b11-5-,12-6-/t19-,20-,23-,25+/m1/s1
SMILES:	c1cc(ccc1/C=CC(=O)O[C@@H]1C[C@@](C[C@H]([C@H]1O)O)(C(=O)O)OC(=O)/C=Cc1ccc(cc1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2349425
PubChem CID:	71718401
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001292] Cyclic alcohols and derivatives [CHEMONTID:0002509] Cyclitols and derivatives [CHEMONTID:0002512] Quinic 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
NPO33307	pimpinella brachycarpa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23462643]

☑ 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
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT34	Cell Line	BV-2	Mus musculus	Activity	=	96.0	%	PMID[473146]
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	52790.0	nM	PMID[473146]

☑ 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 NPC24295 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	316
0.1-0.2	1215
0.2-0.3	3013
0.3-0.4	6865
0.4-0.5	10259
0.5-0.6	6296
0.6-0.7	9192
0.7-0.8	5264
0.8-0.85	186
0.85-0.9	40
0.9-0.95	24
0.95-1	27

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC283560
0.9704	High Similarity	NPC37331
0.9704	High Similarity	NPC284948
0.9704	High Similarity	NPC220664
0.9704	High Similarity	NPC319628
0.9704	High Similarity	NPC303090
0.9695	High Similarity	NPC68517
0.963	High Similarity	NPC224389
0.963	High Similarity	NPC206095
0.963	High Similarity	NPC471027
0.963	High Similarity	NPC35702
0.963	High Similarity	NPC297517
0.963	High Similarity	NPC477335
0.963	High Similarity	NPC13818
0.9621	High Similarity	NPC182217
0.9621	High Similarity	NPC233350
0.9621	High Similarity	NPC70680
0.9559	High Similarity	NPC277315
0.9559	High Similarity	NPC472016
0.9559	High Similarity	NPC192831
0.9559	High Similarity	NPC43158
0.9559	High Similarity	NPC258469
0.9407	High Similarity	NPC37250
0.9407	High Similarity	NPC142703
0.9407	High Similarity	NPC302857
0.9407	High Similarity	NPC152942
0.9407	High Similarity	NPC219428
0.9407	High Similarity	NPC278068
0.9357	High Similarity	NPC192568
0.9357	High Similarity	NPC471076
0.9338	High Similarity	NPC476819
0.9338	High Similarity	NPC474875
0.9338	High Similarity	NPC295492
0.9338	High Similarity	NPC476820
0.9338	High Similarity	NPC205751
0.9338	High Similarity	NPC303683
0.9338	High Similarity	NPC274891
0.9338	High Similarity	NPC26241
0.9281	High Similarity	NPC477333
0.9155	High Similarity	NPC42464
0.9149	High Similarity	NPC322660
0.9091	High Similarity	NPC306343
0.9085	High Similarity	NPC43123
0.9028	High Similarity	NPC477334
0.8966	High Similarity	NPC163883
0.8966	High Similarity	NPC93498
0.8944	High Similarity	NPC98356
0.8904	High Similarity	NPC146277
0.8904	High Similarity	NPC19380
0.8851	High Similarity	NPC470896
0.8851	High Similarity	NPC473275
0.8824	High Similarity	NPC61
0.8824	High Similarity	NPC18074
0.8824	High Similarity	NPC25581
0.8824	High Similarity	NPC5419
0.8803	High Similarity	NPC50221
0.8803	High Similarity	NPC114242
0.8786	High Similarity	NPC156709
0.8786	High Similarity	NPC179505
0.8784	High Similarity	NPC145425
0.8767	High Similarity	NPC252979
0.8759	High Similarity	NPC155209
0.8759	High Similarity	NPC168799
0.875	High Similarity	NPC229264
0.875	High Similarity	NPC198388
0.875	High Similarity	NPC108553
0.8671	High Similarity	NPC226738
0.8671	High Similarity	NPC190587
0.8671	High Similarity	NPC22176
0.8671	High Similarity	NPC121573
0.8643	High Similarity	NPC279676
0.8643	High Similarity	NPC67349
0.86	High Similarity	NPC134925
0.8592	High Similarity	NPC38473
0.8562	High Similarity	NPC142528
0.8561	High Similarity	NPC474895
0.8531	High Similarity	NPC477278
0.8531	High Similarity	NPC477277
0.8523	High Similarity	NPC44730
0.8489	Intermediate Similarity	NPC477281
0.8489	Intermediate Similarity	NPC19719
0.8489	Intermediate Similarity	NPC477280
0.8462	Intermediate Similarity	NPC477279
0.8435	Intermediate Similarity	NPC120621
0.8435	Intermediate Similarity	NPC248257
0.8429	Intermediate Similarity	NPC106406
0.8417	Intermediate Similarity	NPC323379
0.8417	Intermediate Similarity	NPC327204
0.8414	Intermediate Similarity	NPC160378
0.8411	Intermediate Similarity	NPC203757
0.8406	Intermediate Similarity	NPC237506
0.8406	Intermediate Similarity	NPC217052
0.8406	Intermediate Similarity	NPC32626
0.8406	Intermediate Similarity	NPC329344
0.8392	Intermediate Similarity	NPC289690
0.8392	Intermediate Similarity	NPC105525
0.8392	Intermediate Similarity	NPC225036
0.8392	Intermediate Similarity	NPC75763
0.8392	Intermediate Similarity	NPC12218
0.8392	Intermediate Similarity	NPC288452
0.8389	Intermediate Similarity	NPC140151
0.8387	Intermediate Similarity	NPC227297
0.8378	Intermediate Similarity	NPC92117
0.8378	Intermediate Similarity	NPC75945
0.8367	Intermediate Similarity	NPC299090
0.8367	Intermediate Similarity	NPC283081
0.8367	Intermediate Similarity	NPC143892
0.8367	Intermediate Similarity	NPC221383
0.8357	Intermediate Similarity	NPC471749
0.8345	Intermediate Similarity	NPC318799
0.8345	Intermediate Similarity	NPC478250
0.8333	Intermediate Similarity	NPC246566
0.8333	Intermediate Similarity	NPC95498
0.8322	Intermediate Similarity	NPC239943
0.8322	Intermediate Similarity	NPC259576
0.8322	Intermediate Similarity	NPC32197
0.8322	Intermediate Similarity	NPC221091
0.8311	Intermediate Similarity	NPC472969
0.831	Intermediate Similarity	NPC471345
0.8299	Intermediate Similarity	NPC473867
0.8288	Intermediate Similarity	NPC474692
0.8288	Intermediate Similarity	NPC304956
0.828	Intermediate Similarity	NPC471823
0.8278	Intermediate Similarity	NPC3746
0.8278	Intermediate Similarity	NPC44260
0.8278	Intermediate Similarity	NPC205037
0.8278	Intermediate Similarity	NPC61152
0.8278	Intermediate Similarity	NPC16024
0.8267	Intermediate Similarity	NPC300329
0.8255	Intermediate Similarity	NPC476394
0.8255	Intermediate Similarity	NPC98809
0.8252	Intermediate Similarity	NPC302583
0.8252	Intermediate Similarity	NPC100558
0.8252	Intermediate Similarity	NPC84789
0.8252	Intermediate Similarity	NPC310252
0.8248	Intermediate Similarity	NPC475695
0.8231	Intermediate Similarity	NPC53884
0.8231	Intermediate Similarity	NPC258671
0.8228	Intermediate Similarity	NPC128403
0.8212	Intermediate Similarity	NPC106818
0.8212	Intermediate Similarity	NPC75695
0.8207	Intermediate Similarity	NPC9218
0.8201	Intermediate Similarity	NPC94810
0.82	Intermediate Similarity	NPC473091
0.8188	Intermediate Similarity	NPC288416
0.8188	Intermediate Similarity	NPC81835
0.8188	Intermediate Similarity	NPC98009
0.8182	Intermediate Similarity	NPC40920
0.8182	Intermediate Similarity	NPC223335
0.8175	Intermediate Similarity	NPC83218
0.8175	Intermediate Similarity	NPC126991
0.8169	Intermediate Similarity	NPC34293
0.8169	Intermediate Similarity	NPC886
0.8169	Intermediate Similarity	NPC248150
0.8169	Intermediate Similarity	NPC287597
0.8163	Intermediate Similarity	NPC229036
0.8163	Intermediate Similarity	NPC473090
0.8163	Intermediate Similarity	NPC470130
0.8162	Intermediate Similarity	NPC14141
0.8158	Intermediate Similarity	NPC475216
0.8158	Intermediate Similarity	NPC266084
0.8158	Intermediate Similarity	NPC475595
0.8158	Intermediate Similarity	NPC87403
0.8158	Intermediate Similarity	NPC475162
0.8158	Intermediate Similarity	NPC475145
0.8158	Intermediate Similarity	NPC83663
0.8158	Intermediate Similarity	NPC473544
0.8153	Intermediate Similarity	NPC161151
0.8146	Intermediate Similarity	NPC243891
0.8146	Intermediate Similarity	NPC119252
0.8133	Intermediate Similarity	NPC473719
0.8129	Intermediate Similarity	NPC79332
0.8129	Intermediate Similarity	NPC471750
0.8129	Intermediate Similarity	NPC287872
0.8129	Intermediate Similarity	NPC74319
0.8129	Intermediate Similarity	NPC469654
0.8117	Intermediate Similarity	NPC239019
0.8117	Intermediate Similarity	NPC247629
0.8116	Intermediate Similarity	NPC168653
0.8116	Intermediate Similarity	NPC471157
0.8116	Intermediate Similarity	NPC251407
0.8112	Intermediate Similarity	NPC123988
0.8112	Intermediate Similarity	NPC18646
0.8108	Intermediate Similarity	NPC475528
0.8108	Intermediate Similarity	NPC108455
0.8105	Intermediate Similarity	NPC194095
0.8105	Intermediate Similarity	NPC191046
0.8105	Intermediate Similarity	NPC125487
0.8105	Intermediate Similarity	NPC477299
0.8105	Intermediate Similarity	NPC327032
0.8105	Intermediate Similarity	NPC281703
0.8102	Intermediate Similarity	NPC85565
0.8099	Intermediate Similarity	NPC114116
0.8092	Intermediate Similarity	NPC476434
0.8092	Intermediate Similarity	NPC36130
0.8092	Intermediate Similarity	NPC267091
0.8092	Intermediate Similarity	NPC205918
0.8092	Intermediate Similarity	NPC134905
0.8089	Intermediate Similarity	NPC144557
0.8089	Intermediate Similarity	NPC4013

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 NPC24295 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	262
0.1-0.2	757
0.2-0.3	1623
0.3-0.4	2708
0.4-0.5	2099
0.5-0.6	1125
0.6-0.7	497
0.7-0.8	78
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9704	High Similarity	NPD6190	Approved
0.8	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD230	Phase 1
0.7958	Intermediate Similarity	NPD6233	Phase 2
0.7945	Intermediate Similarity	NPD7266	Discontinued
0.7834	Intermediate Similarity	NPD7075	Discontinued
0.7821	Intermediate Similarity	NPD5402	Approved
0.7785	Intermediate Similarity	NPD4628	Phase 3
0.7762	Intermediate Similarity	NPD3764	Approved
0.7758	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7721	Intermediate Similarity	NPD9545	Approved
0.7707	Intermediate Similarity	NPD3817	Phase 2
0.7692	Intermediate Similarity	NPD6801	Discontinued
0.7677	Intermediate Similarity	NPD4380	Phase 2
0.7669	Intermediate Similarity	NPD3751	Discontinued
0.7643	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD6798	Discontinued
0.7632	Intermediate Similarity	NPD6799	Approved
0.7597	Intermediate Similarity	NPD5403	Approved
0.7547	Intermediate Similarity	NPD3882	Suspended
0.7546	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD6166	Phase 2
0.7531	Intermediate Similarity	NPD3787	Discontinued
0.7516	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7685	Pre-registration
0.7471	Intermediate Similarity	NPD8150	Discontinued
0.7468	Intermediate Similarity	NPD5401	Approved
0.7455	Intermediate Similarity	NPD3818	Discontinued
0.7447	Intermediate Similarity	NPD9269	Phase 2
0.7425	Intermediate Similarity	NPD6797	Phase 2
0.7421	Intermediate Similarity	NPD2801	Approved
0.741	Intermediate Similarity	NPD5844	Phase 1
0.7397	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7251	Discontinued
0.7368	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD8434	Phase 2
0.7365	Intermediate Similarity	NPD6355	Discontinued
0.7358	Intermediate Similarity	NPD1934	Approved
0.7358	Intermediate Similarity	NPD37	Approved
0.7347	Intermediate Similarity	NPD4062	Phase 3
0.7346	Intermediate Similarity	NPD6234	Discontinued
0.7342	Intermediate Similarity	NPD6599	Discontinued
0.7337	Intermediate Similarity	NPD7808	Phase 3
0.7329	Intermediate Similarity	NPD7095	Approved
0.7329	Intermediate Similarity	NPD4965	Approved
0.7329	Intermediate Similarity	NPD4967	Phase 2
0.7329	Intermediate Similarity	NPD4966	Approved
0.7325	Intermediate Similarity	NPD1653	Approved
0.732	Intermediate Similarity	NPD8166	Discontinued
0.7317	Intermediate Similarity	NPD6232	Discontinued
0.7312	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1512	Approved
0.7305	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD9268	Approved
0.7273	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD4340	Discontinued
0.7244	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7033	Discontinued
0.7219	Intermediate Similarity	NPD1510	Phase 2
0.7211	Intermediate Similarity	NPD3027	Phase 3
0.7205	Intermediate Similarity	NPD1465	Phase 2
0.7202	Intermediate Similarity	NPD7054	Approved
0.719	Intermediate Similarity	NPD1549	Phase 2
0.7188	Intermediate Similarity	NPD7411	Suspended
0.7186	Intermediate Similarity	NPD7473	Discontinued
0.7181	Intermediate Similarity	NPD943	Approved
0.7179	Intermediate Similarity	NPD1511	Approved
0.7171	Intermediate Similarity	NPD2935	Discontinued
0.7164	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7472	Approved
0.716	Intermediate Similarity	NPD7074	Phase 3
0.7153	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7199	Phase 2
0.7143	Intermediate Similarity	NPD7228	Approved
0.7134	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7819	Suspended
0.7099	Intermediate Similarity	NPD8455	Phase 2
0.7097	Intermediate Similarity	NPD3750	Approved
0.7088	Intermediate Similarity	NPD7435	Discontinued
0.7075	Intermediate Similarity	NPD9494	Approved
0.7067	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD4060	Phase 1
0.7067	Intermediate Similarity	NPD1613	Approved
0.7063	Intermediate Similarity	NPD3455	Phase 2
0.7059	Intermediate Similarity	NPD1551	Phase 2
0.7051	Intermediate Similarity	NPD2354	Approved
0.7051	Intermediate Similarity	NPD3887	Approved
0.705	Intermediate Similarity	NPD2629	Approved
0.7025	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD6534	Approved
0.7022	Intermediate Similarity	NPD6535	Approved
0.7014	Intermediate Similarity	NPD1535	Discovery
0.7	Intermediate Similarity	NPD4198	Discontinued
0.6993	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD3225	Approved
0.6977	Remote Similarity	NPD6559	Discontinued
0.6975	Remote Similarity	NPD6385	Approved
0.6975	Remote Similarity	NPD6386	Approved
0.697	Remote Similarity	NPD3749	Approved
0.6968	Remote Similarity	NPD4534	Discontinued
0.6968	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD5958	Discontinued
0.6966	Remote Similarity	NPD1481	Phase 2
0.6966	Remote Similarity	NPD1608	Approved
0.6957	Remote Similarity	NPD8320	Phase 1
0.6957	Remote Similarity	NPD8319	Approved
0.6954	Remote Similarity	NPD1240	Approved
0.6951	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD2796	Approved
0.6946	Remote Similarity	NPD8127	Discontinued
0.6934	Remote Similarity	NPD2067	Discontinued
0.6928	Remote Similarity	NPD7097	Phase 1
0.6923	Remote Similarity	NPD6779	Approved
0.6923	Remote Similarity	NPD6777	Approved
0.6923	Remote Similarity	NPD6776	Approved
0.6923	Remote Similarity	NPD6781	Approved
0.6923	Remote Similarity	NPD6778	Approved
0.6923	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6782	Approved
0.6923	Remote Similarity	NPD6780	Approved
0.6909	Remote Similarity	NPD7768	Phase 2
0.6906	Remote Similarity	NPD7699	Phase 2
0.6906	Remote Similarity	NPD7700	Phase 2
0.6899	Remote Similarity	NPD7236	Approved
0.6897	Remote Similarity	NPD8312	Approved
0.6897	Remote Similarity	NPD8313	Approved
0.6887	Remote Similarity	NPD6663	Approved
0.6886	Remote Similarity	NPD5494	Approved
0.6879	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD8368	Discontinued
0.6879	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD1607	Approved
0.6862	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD7874	Approved
0.6853	Remote Similarity	NPD1894	Discontinued
0.6852	Remote Similarity	NPD3226	Approved
0.6852	Remote Similarity	NPD7458	Discontinued
0.6851	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD5353	Approved
0.6846	Remote Similarity	NPD5736	Approved
0.6839	Remote Similarity	NPD5405	Approved
0.6839	Remote Similarity	NPD5404	Approved
0.6839	Remote Similarity	NPD5406	Approved
0.6839	Remote Similarity	NPD5408	Approved
0.6831	Remote Similarity	NPD9493	Approved
0.6824	Remote Similarity	NPD2797	Approved
0.6824	Remote Similarity	NPD1203	Approved
0.6821	Remote Similarity	NPD3268	Approved
0.6815	Remote Similarity	NPD1652	Phase 2
0.6813	Remote Similarity	NPD2533	Approved
0.6813	Remote Similarity	NPD2532	Approved
0.6813	Remote Similarity	NPD2534	Approved
0.6809	Remote Similarity	NPD690	Clinical (unspecified phase)
0.68	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD8361	Approved
0.6798	Remote Similarity	NPD8435	Approved
0.6798	Remote Similarity	NPD8360	Approved
0.6797	Remote Similarity	NPD447	Suspended
0.6795	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD2353	Approved
0.6792	Remote Similarity	NPD7440	Discontinued
0.679	Remote Similarity	NPD7239	Suspended
0.6788	Remote Similarity	NPD1358	Approved
0.6783	Remote Similarity	NPD5536	Phase 2
0.6782	Remote Similarity	NPD7038	Approved
0.6782	Remote Similarity	NPD7039	Approved
0.6782	Remote Similarity	NPD7240	Approved
0.6779	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD3748	Approved
0.6772	Remote Similarity	NPD3400	Discontinued
0.677	Remote Similarity	NPD6273	Approved
0.677	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5048	Discontinued
0.6765	Remote Similarity	NPD5242	Approved
0.6761	Remote Similarity	NPD8407	Phase 2
0.6759	Remote Similarity	NPD17	Approved
0.6753	Remote Similarity	NPD6653	Approved
0.6748	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD6959	Discontinued
0.6733	Remote Similarity	NPD2861	Phase 2
0.6733	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD9570	Approved
0.6731	Remote Similarity	NPD2438	Suspended
0.6731	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD919	Approved
0.672	Remote Similarity	NPD7697	Approved
0.672	Remote Similarity	NPD7696	Phase 3
0.672	Remote Similarity	NPD7698	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