NPASS Compound

Structure

NPC44730 OpenBabel07101718322D 41 44 0 0 1 0 0 0 0 0999 V2000 2.1431 6.7411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0286 3.4694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0468 3.6636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7864 3.4005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1808 2.1636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1877 2.3824 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9128 4.1636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3797 4.3141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1808 1.1636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5999 1.5734 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9128 2.1636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3688 4.1050 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1814 0.6333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4487 -0.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0468 2.6636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7810 3.2960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7788 3.6636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9675 5.1231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7788 2.6636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9620 5.0186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4244 -0.0446 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5827 -0.3364 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3147 0.6636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0067 0.6599 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0458 -0.6572 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6691 -0.7431 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6537 1.8541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.6449 4.1636 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5608 6.0366 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6449 2.1636 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4487 1.1636 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0012 0.5554 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5842 -1.4999 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5863 2.2151 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5498 5.8276 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1251 2.4813 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3147 -0.3364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4189 -0.1491 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4781 0.6581 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 36 1 0 0 0 0 2 37 1 0 0 0 0 3 7 2 0 0 0 0 3 15 1 0 0 0 0 4 8 2 0 0 0 0 4 16 1 0 0 0 0 5 9 2 0 0 0 0 5 15 1 0 0 0 0 6 10 2 0 0 0 0 6 16 1 0 0 0 0 7 17 1 0 0 0 0 8 18 1 0 0 0 0 9 23 1 0 0 0 0 10 24 1 0 0 0 0 11 15 2 0 0 0 0 11 19 1 0 0 0 0 12 16 2 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 13 28 1 0 0 0 0 14 38 1 0 0 0 0 17 19 2 0 0 0 0 17 29 1 0 0 0 0 18 20 2 0 0 0 0 18 30 1 0 0 0 0 19 31 1 0 0 0 0 20 36 1 0 0 0 0 21 25 1 0 0 0 0 21 39 1 1 0 0 0 22 14 1 1 0 0 0 22 26 1 0 0 0 0 22 40 1 0 0 0 0 23 32 2 0 0 0 0 23 38 1 0 0 0 0 24 33 2 0 0 0 0 24 39 1 0 0 0 0 25 26 1 0 0 0 0 25 34 1 1 0 0 0 26 41 1 6 0 0 0 27 35 2 0 0 0 0 27 37 1 0 0 0 0 28 27 1 6 0 0 0 28 40 1 0 0 0 0 28 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	572.15
Volume:	543.89
LogP:	2.751
LogD:	1.7
LogS:	-3.607
# Rotatable Bonds:	12
TPSA:	187.51
# H-Bond Aceptor:	13
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.146
Synthetic Accessibility Score:	5.204
Fsp3:	0.321
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:	-5.789
MDCK Permeability:	4.2710827983682975e-05
Pgp-inhibitor:	0.133
Pgp-substrate:	0.46
Human Intestinal Absorption (HIA):	0.899
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.161
Plasma Protein Binding (PPB):	98.8984375%
Volume Distribution (VD):	0.385
Pgp-substrate:	1.951517105102539%

ADMET: Metabolism

CYP1A2-inhibitor:	0.401
CYP1A2-substrate:	0.685
CYP2C19-inhibitor:	0.412
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.885
CYP2C9-substrate:	0.662
CYP2D6-inhibitor:	0.281
CYP2D6-substrate:	0.487
CYP3A4-inhibitor:	0.769
CYP3A4-substrate:	0.296

ADMET: Excretion

Clearance (CL):	11.147
Half-life (T1/2):	0.948

ADMET: Toxicity

hERG Blockers:	0.205
Human Hepatotoxicity (H-HT):	0.344
Drug-inuced Liver Injury (DILI):	0.918
AMES Toxicity:	0.322
Rat Oral Acute Toxicity:	0.194
Maximum Recommended Daily Dose:	0.911
Skin Sensitization:	0.959
Carcinogencity:	0.291
Eye Corrosion:	0.003
Eye Irritation:	0.041
Respiratory Toxicity:	0.192

Download Data

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

Natural Product: NPC44730

Natural Product ID:	NPC44730
*Common Name:**	Rel-(1S,2R,3R,5S,7R)-Methyl 7-Caffeoyloxymethyl-2-Hydroxy-3-Feruloyloxy-6,8-Dioxabicyclo[3.2.1]Octane-5-Carboxylate
IUPAC Name:	methyl (1S,2R,3R,5S,7R)-7-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxymethyl]-2-hydroxy-3-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy-6,8-dioxabicyclo[3.2.1]octane-5-carboxylate
Synonyms:
Standard InCHIKey:	YEMWKQFIGUCZFS-PBYGLRBLSA-N
Standard InCHI:	InChI=1S/C28H28O13/c1-36-20-12-16(4-8-18(20)30)6-10-24(33)39-21-13-28(27(35)37-2)40-22(26(41-28)25(21)34)14-38-23(32)9-5-15-3-7-17(29)19(31)11-15/h3-12,21-22,25-26,29-31,34H,13-14H2,1-2H3/b9-5+,10-6+/t21-,22-,25-,26-,28+/m1/s1
SMILES:	COc1cc(/C=C/C(=O)O[C@@H]2C[C@@]3(O[C@@H]([C@H]([C@@H]2O)O3)COC(=O)/C=C/c2ccc(c(c2)O)O)C(=O)OC)ccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1077097
PubChem CID:	46184565
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
NPO12088	Conyza canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20121251]
NPO12088	Conyza canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22612410]
NPO12088	Conyza canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12088	Conyza canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12088	Conyza canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12088	Conyza canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	2
Others	3

Activity Type	# Activity
Others	5

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	IC50	=	94650.0	nM	PMID[472663]
NPT2	Others	Unspecified	Inhibition	=	11.0	%	PMID[472663]
NPT2	Others	Unspecified	Inhibition	=	10.8	%	PMID[472663]
NPT2	Others	Unspecified	IC50	=	59810.0	nM	PMID[472663]
NPT2	Others	Unspecified	Inhibition	=	48.1	%	PMID[472663]

☑ 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 NPC44730 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	324
0.1-0.2	1280
0.2-0.3	2989
0.3-0.4	6756
0.4-0.5	10472
0.5-0.6	6174
0.6-0.7	7642
0.7-0.8	6286
0.8-0.85	625
0.85-0.9	136
0.9-0.95	11
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9342	High Similarity	NPC226759
0.9211	High Similarity	NPC38699
0.915	High Similarity	NPC471405
0.9145	High Similarity	NPC327032
0.9145	High Similarity	NPC191046
0.9145	High Similarity	NPC194095
0.9122	High Similarity	NPC98356
0.9103	High Similarity	NPC289690
0.9103	High Similarity	NPC288452
0.9097	High Similarity	NPC44507
0.9091	High Similarity	NPC40920
0.9091	High Similarity	NPC472860
0.9091	High Similarity	NPC223335
0.9085	High Similarity	NPC10205
0.9067	High Similarity	NPC478242
0.9067	High Similarity	NPC476394
0.9067	High Similarity	NPC98809
0.9032	High Similarity	NPC469654
0.9026	High Similarity	NPC473275
0.9026	High Similarity	NPC163635
0.9026	High Similarity	NPC470896
0.9013	High Similarity	NPC36130
0.9013	High Similarity	NPC93498
0.9013	High Similarity	NPC163883
0.9013	High Similarity	NPC134905
0.9	High Similarity	NPC472969
0.898	High Similarity	NPC140502
0.8974	High Similarity	NPC203020
0.8974	High Similarity	NPC239966
0.8968	High Similarity	NPC133984
0.8954	High Similarity	NPC299706
0.8954	High Similarity	NPC146277
0.8954	High Similarity	NPC157898
0.8954	High Similarity	NPC19380
0.8954	High Similarity	NPC61604
0.8954	High Similarity	NPC115466
0.8954	High Similarity	NPC245615
0.8954	High Similarity	NPC137813
0.8947	High Similarity	NPC243891
0.8947	High Similarity	NPC300329
0.8933	High Similarity	NPC143892
0.8933	High Similarity	NPC221383
0.8933	High Similarity	NPC283081
0.8933	High Similarity	NPC299090
0.891	High Similarity	NPC160780
0.891	High Similarity	NPC289811
0.8889	High Similarity	NPC267091
0.8882	High Similarity	NPC221091
0.8882	High Similarity	NPC259576
0.8874	High Similarity	NPC192568
0.8874	High Similarity	NPC471076
0.8874	High Similarity	NPC98009
0.8859	High Similarity	NPC160378
0.8859	High Similarity	NPC110063
0.8846	High Similarity	NPC1913
0.8846	High Similarity	NPC286919
0.8846	High Similarity	NPC475663
0.8839	High Similarity	NPC145425
0.8816	High Similarity	NPC111785
0.8805	High Similarity	NPC223006
0.8805	High Similarity	NPC272750
0.8805	High Similarity	NPC227297
0.8805	High Similarity	NPC173729
0.8805	High Similarity	NPC134047
0.88	High Similarity	NPC476382
0.88	High Similarity	NPC34927
0.88	High Similarity	NPC53884
0.88	High Similarity	NPC262182
0.88	High Similarity	NPC287615
0.88	High Similarity	NPC100998
0.88	High Similarity	NPC258671
0.88	High Similarity	NPC216819
0.88	High Similarity	NPC34587
0.88	High Similarity	NPC252292
0.88	High Similarity	NPC83743
0.8797	High Similarity	NPC311803
0.8797	High Similarity	NPC472859
0.8797	High Similarity	NPC25389
0.8792	High Similarity	NPC303090
0.8792	High Similarity	NPC319628
0.8792	High Similarity	NPC472016
0.8792	High Similarity	NPC43158
0.8792	High Similarity	NPC284948
0.8792	High Similarity	NPC220664
0.8792	High Similarity	NPC258469
0.8792	High Similarity	NPC37331
0.8792	High Similarity	NPC192831
0.8792	High Similarity	NPC277315
0.8792	High Similarity	NPC478239
0.879	High Similarity	NPC179914
0.879	High Similarity	NPC469384
0.8784	High Similarity	NPC100675
0.8782	High Similarity	NPC478055
0.8776	High Similarity	NPC284409
0.8776	High Similarity	NPC226005
0.8774	High Similarity	NPC477299
0.8766	High Similarity	NPC95498
0.8766	High Similarity	NPC75695
0.8766	High Similarity	NPC246566
0.8766	High Similarity	NPC476434
0.8766	High Similarity	NPC203664
0.8765	High Similarity	NPC72249
0.8759	High Similarity	NPC135127
0.8758	High Similarity	NPC188393
0.8758	High Similarity	NPC470934
0.8758	High Similarity	NPC229882
0.8758	High Similarity	NPC205054
0.8758	High Similarity	NPC158635
0.8742	High Similarity	NPC473867
0.8742	High Similarity	NPC285108
0.8742	High Similarity	NPC33298
0.8742	High Similarity	NPC144557
0.8734	High Similarity	NPC119125
0.8734	High Similarity	NPC166277
0.8733	High Similarity	NPC473090
0.8733	High Similarity	NPC304956
0.8725	High Similarity	NPC52664
0.8725	High Similarity	NPC35702
0.8725	High Similarity	NPC471027
0.8725	High Similarity	NPC31751
0.8725	High Similarity	NPC157816
0.8725	High Similarity	NPC206095
0.8725	High Similarity	NPC253722
0.8725	High Similarity	NPC477335
0.8725	High Similarity	NPC224389
0.8725	High Similarity	NPC297517
0.8725	High Similarity	NPC253481
0.8725	High Similarity	NPC13818
0.8718	High Similarity	NPC131532
0.8716	High Similarity	NPC295492
0.8716	High Similarity	NPC26241
0.8716	High Similarity	NPC303683
0.8716	High Similarity	NPC274891
0.8716	High Similarity	NPC476819
0.8716	High Similarity	NPC205751
0.8716	High Similarity	NPC476820
0.8716	High Similarity	NPC474875
0.8707	High Similarity	NPC126206
0.8701	High Similarity	NPC140151
0.8701	High Similarity	NPC32079
0.869	High Similarity	NPC155209
0.869	High Similarity	NPC168799
0.8684	High Similarity	NPC232992
0.8671	High Similarity	NPC74319
0.8671	High Similarity	NPC76211
0.8671	High Similarity	NPC287872
0.8662	High Similarity	NPC228357
0.8659	High Similarity	NPC316539
0.8659	High Similarity	NPC4390
0.8658	High Similarity	NPC186406
0.8649	High Similarity	NPC152942
0.8649	High Similarity	NPC219428
0.8649	High Similarity	NPC302857
0.8649	High Similarity	NPC142703
0.8649	High Similarity	NPC37250
0.8649	High Similarity	NPC278068
0.8645	High Similarity	NPC289438
0.8645	High Similarity	NPC478268
0.8642	High Similarity	NPC128403
0.8642	High Similarity	NPC149244
0.8642	High Similarity	NPC48640
0.8642	High Similarity	NPC116745
0.8639	High Similarity	NPC471664
0.8639	High Similarity	NPC471665
0.8639	High Similarity	NPC157554
0.8639	High Similarity	NPC90431
0.8636	High Similarity	NPC473091
0.8634	High Similarity	NPC475738
0.8634	High Similarity	NPC180586
0.8627	High Similarity	NPC201148
0.8627	High Similarity	NPC80732
0.8627	High Similarity	NPC192763
0.8627	High Similarity	NPC199311
0.8627	High Similarity	NPC28651
0.8627	High Similarity	NPC300262
0.8627	High Similarity	NPC261122
0.8627	High Similarity	NPC215095
0.8627	High Similarity	NPC210611
0.8627	High Similarity	NPC3460
0.8625	High Similarity	NPC476011
0.8625	High Similarity	NPC246024
0.8621	High Similarity	NPC25581
0.8621	High Similarity	NPC61
0.8621	High Similarity	NPC18074
0.8621	High Similarity	NPC5419
0.8618	High Similarity	NPC287495
0.8618	High Similarity	NPC199928
0.8618	High Similarity	NPC9370
0.8616	High Similarity	NPC289346
0.8609	High Similarity	NPC232228
0.86	High Similarity	NPC67467
0.8598	High Similarity	NPC153755
0.8598	High Similarity	NPC190003
0.8598	High Similarity	NPC175107
0.8591	High Similarity	NPC322021
0.8591	High Similarity	NPC147379
0.859	High Similarity	NPC105827
0.859	High Similarity	NPC310661
0.8589	High Similarity	NPC21956
0.8581	High Similarity	NPC310252

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 NPC44730 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	266
0.1-0.2	758
0.2-0.3	1692
0.3-0.4	2583
0.4-0.5	2151
0.5-0.6	1107
0.6-0.7	488
0.7-0.8	95
0.8-0.85	8
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8792	High Similarity	NPD6190	Approved
0.8563	High Similarity	NPD8055	Clinical (unspecified phase)
0.8553	High Similarity	NPD6143	Clinical (unspecified phase)
0.8494	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8434	Intermediate Similarity	NPD7685	Pre-registration
0.8415	Intermediate Similarity	NPD3818	Discontinued
0.84	Intermediate Similarity	NPD7266	Discontinued
0.8323	Intermediate Similarity	NPD6234	Discontinued
0.8313	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD3882	Suspended
0.8263	Intermediate Similarity	NPD6797	Phase 2
0.8239	Intermediate Similarity	NPD37	Approved
0.8214	Intermediate Similarity	NPD7251	Discontinued
0.8199	Intermediate Similarity	NPD4965	Approved
0.8199	Intermediate Similarity	NPD4966	Approved
0.8199	Intermediate Similarity	NPD4967	Phase 2
0.8193	Intermediate Similarity	NPD7228	Approved
0.8166	Intermediate Similarity	NPD7808	Phase 3
0.8153	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD7054	Approved
0.8137	Intermediate Similarity	NPD3817	Phase 2
0.8121	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD7074	Phase 3
0.8095	Intermediate Similarity	NPD7472	Approved
0.8072	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD6166	Phase 2
0.8047	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD1934	Approved
0.8	Intermediate Similarity	NPD7199	Phase 2
0.7987	Intermediate Similarity	NPD1653	Approved
0.7927	Intermediate Similarity	NPD7075	Discontinued
0.7885	Intermediate Similarity	NPD4628	Phase 3
0.7853	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD2801	Approved
0.7829	Intermediate Similarity	NPD230	Phase 1
0.7818	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD6233	Phase 2
0.78	Intermediate Similarity	NPD3027	Phase 3
0.7765	Intermediate Similarity	NPD3751	Discontinued
0.7755	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD1465	Phase 2
0.7744	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD5844	Phase 1
0.7719	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD5402	Approved
0.7697	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD6559	Discontinued
0.7688	Intermediate Similarity	NPD7240	Approved
0.7684	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD6801	Discontinued
0.7669	Intermediate Similarity	NPD4380	Phase 2
0.7667	Intermediate Similarity	NPD9494	Approved
0.764	Intermediate Similarity	NPD1512	Approved
0.7633	Intermediate Similarity	NPD6232	Discontinued
0.7633	Intermediate Similarity	NPD3787	Discontinued
0.7632	Intermediate Similarity	NPD6798	Discontinued
0.7625	Intermediate Similarity	NPD6799	Approved
0.7597	Intermediate Similarity	NPD6355	Discontinued
0.7532	Intermediate Similarity	NPD1613	Approved
0.7532	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1511	Approved
0.7515	Intermediate Similarity	NPD6385	Approved
0.7515	Intermediate Similarity	NPD6386	Approved
0.7515	Intermediate Similarity	NPD5494	Approved
0.75	Intermediate Similarity	NPD7473	Discontinued
0.7485	Intermediate Similarity	NPD5403	Approved
0.7471	Intermediate Similarity	NPD8127	Discontinued
0.7468	Intermediate Similarity	NPD4062	Phase 3
0.7425	Intermediate Similarity	NPD8455	Phase 2
0.7419	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD3705	Approved
0.7375	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD8434	Phase 2
0.7372	Intermediate Similarity	NPD1933	Approved
0.7362	Intermediate Similarity	NPD5401	Approved
0.7362	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD919	Approved
0.7351	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD6599	Discontinued
0.7342	Intermediate Similarity	NPD7033	Discontinued
0.7338	Intermediate Similarity	NPD7095	Approved
0.7329	Intermediate Similarity	NPD4110	Phase 3
0.7329	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7819	Suspended
0.7308	Intermediate Similarity	NPD4060	Phase 1
0.7303	Intermediate Similarity	NPD8313	Approved
0.7303	Intermediate Similarity	NPD8312	Approved
0.7297	Intermediate Similarity	NPD1357	Approved
0.7296	Intermediate Similarity	NPD2935	Discontinued
0.729	Intermediate Similarity	NPD3764	Approved
0.7287	Intermediate Similarity	NPD7680	Approved
0.7287	Intermediate Similarity	NPD7435	Discontinued
0.7279	Intermediate Similarity	NPD5536	Phase 2
0.7278	Intermediate Similarity	NPD5353	Approved
0.7273	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD4340	Discontinued
0.7261	Intermediate Similarity	NPD447	Suspended
0.7256	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD3146	Approved
0.723	Intermediate Similarity	NPD9545	Approved
0.7222	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD8166	Discontinued
0.7219	Intermediate Similarity	NPD1608	Approved
0.7208	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD1549	Phase 2
0.7202	Intermediate Similarity	NPD7411	Suspended
0.7191	Intermediate Similarity	NPD7039	Approved
0.7191	Intermediate Similarity	NPD7038	Approved
0.7186	Intermediate Similarity	NPD3455	Phase 2
0.7186	Intermediate Similarity	NPD7458	Discontinued
0.7184	Intermediate Similarity	NPD3926	Phase 2
0.7184	Intermediate Similarity	NPD5242	Approved
0.717	Intermediate Similarity	NPD7097	Phase 1
0.7168	Intermediate Similarity	NPD1247	Approved
0.7152	Intermediate Similarity	NPD2534	Approved
0.7152	Intermediate Similarity	NPD2532	Approved
0.7152	Intermediate Similarity	NPD2533	Approved
0.7143	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7028	Phase 2
0.7143	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD5058	Phase 3
0.7128	Intermediate Similarity	NPD6778	Approved
0.7128	Intermediate Similarity	NPD6777	Approved
0.7128	Intermediate Similarity	NPD6780	Approved
0.7128	Intermediate Similarity	NPD6776	Approved
0.7128	Intermediate Similarity	NPD6782	Approved
0.7128	Intermediate Similarity	NPD6781	Approved
0.7128	Intermediate Similarity	NPD6779	Approved
0.7125	Intermediate Similarity	NPD1510	Phase 2
0.7118	Intermediate Similarity	NPD2978	Approved
0.7118	Intermediate Similarity	NPD2977	Approved
0.7107	Intermediate Similarity	NPD6653	Approved
0.7105	Intermediate Similarity	NPD9269	Phase 2
0.7103	Intermediate Similarity	NPD228	Approved
0.7099	Intermediate Similarity	NPD5958	Discontinued
0.7099	Intermediate Similarity	NPD4534	Discontinued
0.7099	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD4357	Discontinued
0.7088	Intermediate Similarity	NPD8150	Discontinued
0.7073	Intermediate Similarity	NPD2354	Approved
0.7073	Intermediate Similarity	NPD3887	Approved
0.7062	Intermediate Similarity	NPD2163	Approved
0.7062	Intermediate Similarity	NPD7874	Approved
0.7062	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6674	Discontinued
0.7039	Intermediate Similarity	NPD1091	Approved
0.7037	Intermediate Similarity	NPD5763	Approved
0.7037	Intermediate Similarity	NPD5762	Approved
0.702	Intermediate Similarity	NPD17	Approved
0.7012	Intermediate Similarity	NPD3750	Approved
0.7012	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6273	Approved
0.7	Intermediate Similarity	NPD2493	Approved
0.7	Intermediate Similarity	NPD2494	Approved
0.6994	Remote Similarity	NPD3749	Approved
0.6987	Remote Similarity	NPD2861	Phase 2
0.6982	Remote Similarity	NPD3226	Approved
0.6981	Remote Similarity	NPD1240	Approved
0.6981	Remote Similarity	NPD943	Approved
0.6981	Remote Similarity	NPD3620	Phase 2
0.6981	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.698	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD2438	Suspended
0.6975	Remote Similarity	NPD2796	Approved
0.6968	Remote Similarity	NPD2797	Approved
0.6962	Remote Similarity	NPD3268	Approved
0.6951	Remote Similarity	NPD1652	Phase 2
0.6949	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7296	Approved
0.6933	Remote Similarity	NPD6004	Phase 3
0.6933	Remote Similarity	NPD6002	Phase 3
0.6933	Remote Similarity	NPD6005	Phase 3
0.6933	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD7229	Phase 3
0.6928	Remote Similarity	NPD1535	Discovery
0.6927	Remote Similarity	NPD7698	Approved
0.6927	Remote Similarity	NPD7696	Phase 3
0.6927	Remote Similarity	NPD7697	Approved
0.6923	Remote Similarity	NPD5647	Approved
0.6923	Remote Similarity	NPD3687	Approved
0.6923	Remote Similarity	NPD8151	Discontinued
0.6923	Remote Similarity	NPD3686	Approved
0.6911	Remote Similarity	NPD3450	Approved
0.6911	Remote Similarity	NPD3452	Approved
0.6903	Remote Similarity	NPD3225	Approved
0.6901	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD1607	Approved
0.6892	Remote Similarity	NPD5283	Phase 1
0.6891	Remote Similarity	NPD4582	Approved
0.6891	Remote Similarity	NPD7870	Phase 2
0.6891	Remote Similarity	NPD8320	Phase 1
0.6891	Remote Similarity	NPD4583	Approved
0.6891	Remote Similarity	NPD8319	Approved
0.6891	Remote Similarity	NPD7871	Phase 2

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