NPASS Compound

Structure

NPC145425 OpenBabel07101719132D 38 40 0 0 1 0 0 0 0 0999 V2000 -2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 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 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 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 5.1962 -0.0000 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 0.8660 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 -1.7321 -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 -0.0000 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 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 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 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 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 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 -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 6.9282 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 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 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 6.0000 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 -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 -2.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 5.0000 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 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 35 1 0 0 0 0 2 36 1 0 0 0 0 3 5 2 0 0 0 0 3 12 1 0 0 0 0 4 6 2 0 0 0 0 4 12 1 0 0 0 0 5 14 1 0 0 0 0 6 20 1 0 0 0 0 7 12 2 0 0 0 0 7 15 1 0 0 0 0 8 13 2 0 0 0 0 8 17 1 0 0 0 0 9 13 1 0 0 0 0 9 18 2 0 0 0 0 10 16 1 0 0 0 0 10 25 1 0 0 0 0 11 19 1 0 0 0 0 11 25 1 0 0 0 0 13 23 1 0 0 0 0 14 15 2 0 0 0 0 14 26 1 0 0 0 0 15 27 1 0 0 0 0 16 22 1 0 0 0 0 16 28 1 1 0 0 0 17 21 2 0 0 0 0 17 35 1 0 0 0 0 18 21 1 0 0 0 0 18 36 1 0 0 0 0 19 22 1 0 0 0 0 19 37 1 6 0 0 0 20 29 2 0 0 0 0 20 38 1 0 0 0 0 21 30 1 0 0 0 0 22 38 1 6 0 0 0 23 31 2 0 0 0 0 23 37 1 0 0 0 0 24 25 1 0 0 0 0 24 32 2 0 0 0 0 24 33 1 0 0 0 0 25 34 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	534.14
Volume:	503.195
LogP:	1.717
LogD:	0.673
LogS:	-3.145
# Rotatable Bonds:	10
TPSA:	209.51
# H-Bond Aceptor:	13
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.158
Synthetic Accessibility Score:	4.035
Fsp3:	0.32
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.115
MDCK Permeability:	3.020160693267826e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.95
Human Intestinal Absorption (HIA):	0.869
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.413
Plasma Protein Binding (PPB):	93.18720245361328%
Volume Distribution (VD):	0.566
Pgp-substrate:	11.826961517333984%

ADMET: Metabolism

CYP1A2-inhibitor:	0.072
CYP1A2-substrate:	0.081
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.282
CYP2C9-substrate:	0.265
CYP2D6-inhibitor:	0.021
CYP2D6-substrate:	0.15
CYP3A4-inhibitor:	0.079
CYP3A4-substrate:	0.052

ADMET: Excretion

Clearance (CL):	9.145
Half-life (T1/2):	0.96

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.254
Drug-inuced Liver Injury (DILI):	0.444
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.898
Skin Sensitization:	0.266
Carcinogencity:	0.098
Eye Corrosion:	0.003
Eye Irritation:	0.075
Respiratory Toxicity:	0.291

Download Data

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

Natural Product: NPC145425

Natural Product ID:	NPC145425
*Common Name:**	4-O-Caffeoyl-3-O-Syringoyl Quinic Acid
IUPAC Name:	(1S,3S,4R,5S)-4-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,3-dihydroxy-5-(4-hydroxy-3,5-dimethoxybenzoyl)oxycyclohexane-1-carboxylic acid
Synonyms:
Standard InCHIKey:	PYGQEDZSTFIHHP-FXSUHYAKSA-N
Standard InCHI:	InChI=1S/C25H26O13/c1-35-17-8-13(9-18(36-2)21(17)30)23(31)37-19-11-25(34,24(32)33)10-16(28)22(19)38-20(29)6-4-12-3-5-14(26)15(27)7-12/h3-9,16,19,22,26-28,30,34H,10-11H2,1-2H3,(H,32,33)/b6-4+/t16-,19-,22+,25-/m0/s1
SMILES:	COc1cc(cc(c1O)OC)C(=O)O[C@H]1C[C@@](O)(C[C@@H]([C@H]1OC(=O)/C=C/c1ccc(c(c1)O)O)O)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1088452
PubChem CID:	46185596
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
NPO32755	erycibe hainanesis	Species	Convolvulaceae	Eukaryota	roots and stems	Hainan Province, China	2008-Mar	PMID[20092289]

☑ 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	2

Activity Type	# Activity
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT27	Others	Unspecified		Survival	=	61.0	%	PMID[540255]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	42.2	%	PMID[540255]

☑ 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 NPC145425 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	348
0.1-0.2	1467
0.2-0.3	3748
0.3-0.4	8403
0.4-0.5	9607
0.5-0.6	4178
0.6-0.7	5274
0.7-0.8	7314
0.8-0.85	1987
0.85-0.9	300
0.9-0.95	63
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9796	High Similarity	NPC93498
0.9796	High Similarity	NPC163883
0.973	High Similarity	NPC19380
0.973	High Similarity	NPC146277
0.966	High Similarity	NPC306343
0.9592	High Similarity	NPC42464
0.9524	High Similarity	NPC43123
0.94	High Similarity	NPC75695
0.9388	High Similarity	NPC98356
0.9267	High Similarity	NPC473091
0.9252	High Similarity	NPC114242
0.9252	High Similarity	NPC50221
0.9221	High Similarity	NPC472860
0.9205	High Similarity	NPC252979
0.9184	High Similarity	NPC277315
0.9184	High Similarity	NPC43158
0.9184	High Similarity	NPC258469
0.9184	High Similarity	NPC192831
0.9184	High Similarity	NPC472016
0.9167	High Similarity	NPC472859
0.9167	High Similarity	NPC25389
0.9167	High Similarity	NPC311803
0.9161	High Similarity	NPC160780
0.9161	High Similarity	NPC289811
0.9156	High Similarity	NPC473275
0.9156	High Similarity	NPC470896
0.9133	High Similarity	NPC472969
0.9122	High Similarity	NPC226738
0.9122	High Similarity	NPC190587
0.9122	High Similarity	NPC22176
0.9122	High Similarity	NPC121573
0.9116	High Similarity	NPC297517
0.9116	High Similarity	NPC206095
0.9116	High Similarity	NPC13818
0.9116	High Similarity	NPC224389
0.9116	High Similarity	NPC477335
0.9116	High Similarity	NPC35702
0.9116	High Similarity	NPC471027
0.9108	High Similarity	NPC285108
0.9108	High Similarity	NPC33298
0.9103	High Similarity	NPC166277
0.9103	High Similarity	NPC203020
0.9103	High Similarity	NPC119125
0.9103	High Similarity	NPC476373
0.9103	High Similarity	NPC239966
0.9103	High Similarity	NPC53889
0.9097	High Similarity	NPC1913
0.9073	High Similarity	NPC476394
0.9073	High Similarity	NPC98809
0.9054	High Similarity	NPC220664
0.9054	High Similarity	NPC37331
0.9054	High Similarity	NPC319628
0.9054	High Similarity	NPC284948
0.9054	High Similarity	NPC303090
0.9038	High Similarity	NPC74319
0.9038	High Similarity	NPC287872
0.9038	High Similarity	NPC87317
0.902	High Similarity	NPC246566
0.902	High Similarity	NPC95498
0.9007	High Similarity	NPC192568
0.9007	High Similarity	NPC471076
0.9007	High Similarity	NPC142528
0.8994	High Similarity	NPC142614
0.8987	High Similarity	NPC476372
0.8987	High Similarity	NPC476371
0.8987	High Similarity	NPC4013
0.8987	High Similarity	NPC90905
0.8981	High Similarity	NPC24164
0.8981	High Similarity	NPC289346
0.8981	High Similarity	NPC24627
0.898	High Similarity	NPC295492
0.898	High Similarity	NPC474875
0.898	High Similarity	NPC205751
0.898	High Similarity	NPC476820
0.898	High Similarity	NPC476819
0.898	High Similarity	NPC26241
0.898	High Similarity	NPC274891
0.898	High Similarity	NPC303683
0.8974	High Similarity	NPC114179
0.8974	High Similarity	NPC156818
0.8974	High Similarity	NPC289322
0.8974	High Similarity	NPC160512
0.8974	High Similarity	NPC38779
0.8974	High Similarity	NPC68324
0.8954	High Similarity	NPC243891
0.8938	High Similarity	NPC471823
0.8912	High Similarity	NPC152942
0.8912	High Similarity	NPC302857
0.8912	High Similarity	NPC37250
0.8912	High Similarity	NPC219428
0.8912	High Similarity	NPC142703
0.8912	High Similarity	NPC278068
0.891	High Similarity	NPC300845
0.891	High Similarity	NPC88803
0.891	High Similarity	NPC104983
0.891	High Similarity	NPC250436
0.891	High Similarity	NPC134925
0.891	High Similarity	NPC291948
0.8903	High Similarity	NPC327032
0.8903	High Similarity	NPC194095
0.8903	High Similarity	NPC191046
0.8896	High Similarity	NPC476434
0.8896	High Similarity	NPC267091
0.8896	High Similarity	NPC476374
0.8882	High Similarity	NPC294972
0.8882	High Similarity	NPC248257
0.8882	High Similarity	NPC120621
0.8875	High Similarity	NPC471788
0.8867	High Similarity	NPC473090
0.8867	High Similarity	NPC134975
0.8854	High Similarity	NPC226759
0.8854	High Similarity	NPC133984
0.8851	High Similarity	NPC225036
0.8851	High Similarity	NPC12218
0.8851	High Similarity	NPC75763
0.8851	High Similarity	NPC105525
0.8846	High Similarity	NPC203757
0.8844	High Similarity	NPC125417
0.8844	High Similarity	NPC95679
0.8844	High Similarity	NPC25305
0.8844	High Similarity	NPC112068
0.8844	High Similarity	NPC110899
0.8839	High Similarity	NPC310661
0.8839	High Similarity	NPC105827
0.8839	High Similarity	NPC44730
0.8834	High Similarity	NPC102851
0.8834	High Similarity	NPC476370
0.8834	High Similarity	NPC5786
0.8831	High Similarity	NPC140151
0.8827	High Similarity	NPC197708
0.8827	High Similarity	NPC280493
0.8827	High Similarity	NPC658
0.8824	High Similarity	NPC92117
0.8824	High Similarity	NPC107636
0.8824	High Similarity	NPC75945
0.8816	High Similarity	NPC165389
0.8816	High Similarity	NPC322660
0.8808	High Similarity	NPC477333
0.8805	High Similarity	NPC308992
0.8805	High Similarity	NPC112418
0.8792	High Similarity	NPC326065
0.879	High Similarity	NPC471405
0.879	High Similarity	NPC318432
0.8784	High Similarity	NPC24295
0.8784	High Similarity	NPC283560
0.8784	High Similarity	NPC239943
0.8782	High Similarity	NPC469888
0.8782	High Similarity	NPC197188
0.8782	High Similarity	NPC238672
0.8782	High Similarity	NPC43872
0.8782	High Similarity	NPC287504
0.8782	High Similarity	NPC291510
0.8782	High Similarity	NPC25127
0.8782	High Similarity	NPC144801
0.8782	High Similarity	NPC116850
0.8774	High Similarity	NPC36130
0.8774	High Similarity	NPC134905
0.8765	High Similarity	NPC283041
0.8765	High Similarity	NPC116745
0.8765	High Similarity	NPC295082
0.8758	High Similarity	NPC191930
0.875	High Similarity	NPC471745
0.875	High Similarity	NPC9370
0.875	High Similarity	NPC287495
0.875	High Similarity	NPC42797
0.875	High Similarity	NPC41009
0.8742	High Similarity	NPC471744
0.8742	High Similarity	NPC263449
0.8734	High Similarity	NPC224137
0.8734	High Similarity	NPC75215
0.8734	High Similarity	NPC67876
0.8734	High Similarity	NPC222689
0.8734	High Similarity	NPC93376
0.8734	High Similarity	NPC52530
0.8734	High Similarity	NPC35598
0.8734	High Similarity	NPC227192
0.8734	High Similarity	NPC189179
0.8734	High Similarity	NPC470402
0.8727	High Similarity	NPC84482
0.8727	High Similarity	NPC169645
0.8727	High Similarity	NPC477848
0.8726	High Similarity	NPC10205
0.8725	High Similarity	NPC288452
0.8725	High Similarity	NPC289690
0.8718	High Similarity	NPC61152
0.8718	High Similarity	NPC3746
0.8718	High Similarity	NPC44260
0.8718	High Similarity	NPC474656
0.8718	High Similarity	NPC16024
0.8718	High Similarity	NPC205037
0.8718	High Similarity	NPC289968
0.8712	High Similarity	NPC95421
0.8712	High Similarity	NPC198125
0.8707	High Similarity	NPC233350
0.8707	High Similarity	NPC18646
0.8707	High Similarity	NPC70680
0.8707	High Similarity	NPC182217
0.8704	High Similarity	NPC20237
0.8701	High Similarity	NPC474903
0.8696	High Similarity	NPC249181

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 NPC145425 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	293
0.1-0.2	865
0.2-0.3	1803
0.3-0.4	2611
0.4-0.5	1913
0.5-0.6	1032
0.6-0.7	475
0.7-0.8	126
0.8-0.85	27
0.85-0.9	4
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9054	High Similarity	NPD6190	Approved
0.891	High Similarity	NPD4868	Clinical (unspecified phase)
0.8642	High Similarity	NPD6166	Phase 2
0.8642	High Similarity	NPD6168	Clinical (unspecified phase)
0.8642	High Similarity	NPD6167	Clinical (unspecified phase)
0.8614	High Similarity	NPD4338	Clinical (unspecified phase)
0.8608	High Similarity	NPD3817	Phase 2
0.8606	High Similarity	NPD7993	Clinical (unspecified phase)
0.8571	High Similarity	NPD230	Phase 1
0.8553	High Similarity	NPD3882	Suspended
0.8544	High Similarity	NPD2801	Approved
0.8481	Intermediate Similarity	NPD1934	Approved
0.8424	Intermediate Similarity	NPD3818	Discontinued
0.8373	Intermediate Similarity	NPD5844	Phase 1
0.8313	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD6232	Discontinued
0.828	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8274	Intermediate Similarity	NPD6797	Phase 2
0.8272	Intermediate Similarity	NPD7075	Discontinued
0.8263	Intermediate Similarity	NPD7054	Approved
0.8261	Intermediate Similarity	NPD5402	Approved
0.8246	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8225	Intermediate Similarity	NPD7685	Pre-registration
0.8225	Intermediate Similarity	NPD7251	Discontinued
0.8217	Intermediate Similarity	NPD1512	Approved
0.8214	Intermediate Similarity	NPD7074	Phase 3
0.8214	Intermediate Similarity	NPD7472	Approved
0.8199	Intermediate Similarity	NPD1465	Phase 2
0.8176	Intermediate Similarity	NPD7808	Phase 3
0.8144	Intermediate Similarity	NPD7473	Discontinued
0.8137	Intermediate Similarity	NPD6801	Discontinued
0.8125	Intermediate Similarity	NPD4380	Phase 2
0.811	Intermediate Similarity	NPD6234	Discontinued
0.8089	Intermediate Similarity	NPD6799	Approved
0.8089	Intermediate Similarity	NPD1511	Approved
0.8086	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD3027	Phase 3
0.8025	Intermediate Similarity	NPD37	Approved
0.8013	Intermediate Similarity	NPD4628	Phase 3
0.8	Intermediate Similarity	NPD1653	Approved
0.7988	Intermediate Similarity	NPD4967	Phase 2
0.7988	Intermediate Similarity	NPD4966	Approved
0.7988	Intermediate Similarity	NPD4965	Approved
0.7975	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD5403	Approved
0.7919	Intermediate Similarity	NPD9494	Approved
0.7882	Intermediate Similarity	NPD7228	Approved
0.7844	Intermediate Similarity	NPD5494	Approved
0.7823	Intermediate Similarity	NPD9269	Phase 2
0.7818	Intermediate Similarity	NPD5353	Approved
0.7812	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD5401	Approved
0.7811	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7809	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD7199	Phase 2
0.7791	Intermediate Similarity	NPD6599	Discontinued
0.7758	Intermediate Similarity	NPD7819	Suspended
0.7744	Intermediate Similarity	NPD7411	Suspended
0.7733	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD6233	Phase 2
0.7707	Intermediate Similarity	NPD7266	Discontinued
0.7706	Intermediate Similarity	NPD5242	Approved
0.7697	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1510	Phase 2
0.7674	Intermediate Similarity	NPD3751	Discontinued
0.7662	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD1613	Approved
0.7658	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD1549	Phase 2
0.7651	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD2935	Discontinued
0.7636	Intermediate Similarity	NPD6386	Approved
0.7636	Intermediate Similarity	NPD6385	Approved
0.7613	Intermediate Similarity	NPD447	Suspended
0.761	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD6559	Discontinued
0.7595	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD8434	Phase 2
0.7574	Intermediate Similarity	NPD919	Approved
0.7562	Intermediate Similarity	NPD3750	Approved
0.7551	Intermediate Similarity	NPD9268	Approved
0.7548	Intermediate Similarity	NPD1240	Approved
0.7548	Intermediate Similarity	NPD943	Approved
0.7544	Intermediate Similarity	NPD3787	Discontinued
0.7532	Intermediate Similarity	NPD1551	Phase 2
0.7532	Intermediate Similarity	NPD2796	Approved
0.75	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3926	Phase 2
0.7486	Intermediate Similarity	NPD8150	Discontinued
0.7485	Intermediate Similarity	NPD1247	Approved
0.7485	Intermediate Similarity	NPD2532	Approved
0.7485	Intermediate Similarity	NPD2533	Approved
0.7485	Intermediate Similarity	NPD2534	Approved
0.7483	Intermediate Similarity	NPD9545	Approved
0.7457	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD7768	Phase 2
0.7453	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD1607	Approved
0.7419	Intermediate Similarity	NPD3764	Approved
0.7419	Intermediate Similarity	NPD6798	Discontinued
0.7412	Intermediate Similarity	NPD3749	Approved
0.7403	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD7039	Approved
0.7401	Intermediate Similarity	NPD7038	Approved
0.7401	Intermediate Similarity	NPD7240	Approved
0.7394	Intermediate Similarity	NPD7435	Discontinued
0.7384	Intermediate Similarity	NPD6959	Discontinued
0.7358	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD6776	Approved
0.7326	Intermediate Similarity	NPD6777	Approved
0.7326	Intermediate Similarity	NPD6780	Approved
0.7326	Intermediate Similarity	NPD6781	Approved
0.7326	Intermediate Similarity	NPD6778	Approved
0.7326	Intermediate Similarity	NPD6779	Approved
0.7326	Intermediate Similarity	NPD6782	Approved
0.7317	Intermediate Similarity	NPD4357	Discontinued
0.7305	Intermediate Similarity	NPD3455	Phase 2
0.7283	Intermediate Similarity	NPD8127	Discontinued
0.7278	Intermediate Similarity	NPD1933	Approved
0.7273	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD3748	Approved
0.7244	Intermediate Similarity	NPD7095	Approved
0.7239	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD3226	Approved
0.7195	Intermediate Similarity	NPD2354	Approved
0.7195	Intermediate Similarity	NPD3887	Approved
0.719	Intermediate Similarity	NPD2983	Phase 2
0.719	Intermediate Similarity	NPD2982	Phase 2
0.7182	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD5536	Phase 2
0.717	Intermediate Similarity	NPD6355	Discontinued
0.7165	Intermediate Similarity	NPD7874	Approved
0.7165	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD4062	Phase 3
0.7151	Intermediate Similarity	NPD5953	Discontinued
0.7143	Intermediate Similarity	NPD7033	Discontinued
0.7134	Intermediate Similarity	NPD8166	Discontinued
0.7127	Intermediate Similarity	NPD8313	Approved
0.7127	Intermediate Similarity	NPD8312	Approved
0.7126	Intermediate Similarity	NPD6273	Approved
0.7124	Intermediate Similarity	NPD2981	Phase 2
0.7124	Intermediate Similarity	NPD1608	Approved
0.712	Intermediate Similarity	NPD7697	Approved
0.712	Intermediate Similarity	NPD7698	Approved
0.712	Intermediate Similarity	NPD7696	Phase 3
0.7115	Intermediate Similarity	NPD3018	Phase 2
0.7113	Intermediate Similarity	NPD8151	Discontinued
0.711	Intermediate Similarity	NPD6971	Discontinued
0.7101	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7458	Discontinued
0.7097	Intermediate Similarity	NPD1203	Approved
0.709	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7871	Phase 2
0.7083	Intermediate Similarity	NPD7870	Phase 2
0.7083	Intermediate Similarity	NPD920	Approved
0.7073	Intermediate Similarity	NPD1652	Phase 2
0.7072	Intermediate Similarity	NPD7549	Discontinued
0.707	Intermediate Similarity	NPD6832	Phase 2
0.7066	Intermediate Similarity	NPD3146	Approved
0.7066	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD7701	Phase 2
0.7059	Intermediate Similarity	NPD6534	Approved
0.7059	Intermediate Similarity	NPD6535	Approved
0.7045	Intermediate Similarity	NPD7229	Phase 3
0.7039	Intermediate Similarity	NPD7286	Phase 2
0.7037	Intermediate Similarity	NPD4308	Phase 3
0.7035	Intermediate Similarity	NPD8455	Phase 2
0.7031	Intermediate Similarity	NPD7680	Approved
0.703	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD4110	Phase 3
0.7018	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4060	Phase 1
0.6994	Remote Similarity	NPD6100	Approved
0.6994	Remote Similarity	NPD6099	Approved
0.6964	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD4908	Phase 1
0.6957	Remote Similarity	NPD4340	Discontinued
0.6957	Remote Similarity	NPD5124	Phase 1
0.6957	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7783	Phase 2
0.6954	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7801	Approved
0.6951	Remote Similarity	NPD2353	Approved
0.6951	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD5711	Approved
0.6949	Remote Similarity	NPD5710	Approved
0.6948	Remote Similarity	NPD422	Phase 1
0.6947	Remote Similarity	NPD7700	Phase 2
0.6947	Remote Similarity	NPD7699	Phase 2
0.6946	Remote Similarity	NPD7440	Discontinued
0.6933	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD2799	Discontinued

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