NPASS Compound

Structure

NPC469654 OpenBabel07101718192D 43 45 0 0 1 0 0 0 0 0999 V2000 -3.3888 -2.9348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.0136 1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6465 -0.2270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1139 -1.0742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5416 0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2360 0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1574 -1.0742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6248 -1.9214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6944 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2360 1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3888 -0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1139 0.6202 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8472 1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3888 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6248 -0.2270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6465 -1.9214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6944 -0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5416 -1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8472 0.4891 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0832 1.9565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6944 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6944 -0.9783 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8472 -1.4674 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.4720 1.9565 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -9.3192 1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9783 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.1357 2.3146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6248 1.4674 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 1.9565 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1574 -2.7686 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0832 2.9348 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5416 0.4891 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5416 -1.4674 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8472 -2.4457 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4720 2.9348 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3192 0.4891 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6248 3.1618 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1574 2.3146 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5416 -2.4457 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.1664 1.9565 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8472 -1.4674 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 -6.7776 0.9783 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 39 1 0 0 0 0 2 40 1 0 0 0 0 3 7 1 0 0 0 0 3 15 2 0 0 0 0 4 8 2 0 0 0 0 4 15 1 0 0 0 0 5 9 2 0 0 0 0 5 14 1 0 0 0 0 6 10 2 0 0 0 0 6 14 1 0 0 0 0 7 16 2 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 10 20 1 0 0 0 0 11 14 2 0 0 0 0 11 18 1 0 0 0 0 12 15 1 0 0 0 0 12 28 1 0 0 0 0 13 29 1 0 0 0 0 16 30 1 0 0 0 0 17 18 2 0 0 0 0 17 41 1 0 0 0 0 18 39 1 0 0 0 0 19 13 1 6 0 0 0 19 21 1 0 0 0 0 19 42 1 0 0 0 0 20 31 2 0 0 0 0 20 43 1 0 0 0 0 21 22 1 0 0 0 0 21 32 1 1 0 0 0 22 23 1 0 0 0 0 22 33 1 6 0 0 0 23 26 1 0 0 0 0 23 34 1 1 0 0 0 24 25 1 0 0 0 0 24 28 1 0 0 0 0 24 35 1 0 0 0 0 25 36 2 0 0 0 0 25 40 1 0 0 0 0 26 41 1 6 0 0 0 26 42 1 0 0 0 0 27 28 1 0 0 0 0 27 37 2 0 0 0 0 27 38 1 0 0 0 0 28 43 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	608.17
Volume:	572.663
LogP:	0.136
LogD:	-0.146
LogS:	-2.735
# Rotatable Bonds:	14
TPSA:	238.97
# H-Bond Aceptor:	15
# H-Bond Donor:	7
# Rings:	3
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.11
Synthetic Accessibility Score:	4.493
Fsp3:	0.393
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.218
MDCK Permeability:	6.0733284044545144e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.965
Human Intestinal Absorption (HIA):	0.845
20% Bioavailability (F20%):	0.755
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.13
Plasma Protein Binding (PPB):	64.78661346435547%
Volume Distribution (VD):	0.296
Pgp-substrate:	19.498456954956055%

ADMET: Metabolism

CYP1A2-inhibitor:	0.064
CYP1A2-substrate:	0.063
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.728
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.15
CYP3A4-inhibitor:	0.086
CYP3A4-substrate:	0.029

ADMET: Excretion

Clearance (CL):	1.963
Half-life (T1/2):	0.928

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.134
Drug-inuced Liver Injury (DILI):	0.85
AMES Toxicity:	0.052
Rat Oral Acute Toxicity:	0.019
Maximum Recommended Daily Dose:	0.003
Skin Sensitization:	0.086
Carcinogencity:	0.018
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.012

Download Data

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

Natural Product: NPC469654

Natural Product ID:	NPC469654
*Common Name:**	Shomaside D
IUPAC Name:	3-hydroxy-2-[(4-hydroxyphenyl)methyl]-4-methoxy-2-[(E)-3-[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoyl]oxy-4-oxobutanoic acid
Synonyms:	Shomaside D
Standard InCHIKey:	SWZFUPSKOHNPFU-JUHWEFMQSA-N
Standard InCHI:	InChI=1S/C28H32O15/c1-39-18-11-14(5-9-17(18)41-26-23(34)22(33)21(32)19(13-29)42-26)6-10-20(31)43-28(27(37)38,24(35)25(36)40-2)12-15-3-7-16(30)8-4-15/h3-11,19,21-24,26,29-30,32-35H,12-13H2,1-2H3,(H,37,38)/b10-6+/t19-,21-,22+,23-,24?,26-,28?/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2ccc(cc2OC)/C=C/C(=O)OC(C(C(=O)OC)O)(C(=O)O)Cc2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1096592
PubChem CID:	46209908
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic glycosides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO32999	cimicifuga heracleifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20192237]
NPO30530	Cimicifuga dahurica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20192237]
NPO30530	Cimicifuga dahurica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30530	Cimicifuga dahurica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	>	658000.0	nM	PMID[557197]

☑ 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 NPC469654 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	349
0.1-0.2	1374
0.2-0.3	3180
0.3-0.4	7025
0.4-0.5	10063
0.5-0.6	5873
0.6-0.7	6708
0.7-0.8	6855
0.8-0.85	1105
0.85-0.9	157
0.9-0.95	4
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9933	High Similarity	NPC40920
0.9933	High Similarity	NPC223335
0.9803	High Similarity	NPC44507
0.9226	High Similarity	NPC163635
0.9161	High Similarity	NPC38699
0.9145	High Similarity	NPC478242
0.9139	High Similarity	NPC283081
0.9139	High Similarity	NPC221383
0.9139	High Similarity	NPC299090
0.9139	High Similarity	NPC143892
0.9067	High Similarity	NPC304956
0.9038	High Similarity	NPC131532
0.9038	High Similarity	NPC10205
0.9032	High Similarity	NPC44730
0.9032	High Similarity	NPC115466
0.9032	High Similarity	NPC245615
0.9032	High Similarity	NPC61604
0.9032	High Similarity	NPC299706
0.9026	High Similarity	NPC300329
0.902	High Similarity	NPC111785
0.9007	High Similarity	NPC53884
0.9007	High Similarity	NPC258671
0.8981	High Similarity	NPC478055
0.8981	High Similarity	NPC471405
0.8974	High Similarity	NPC191046
0.8974	High Similarity	NPC327032
0.8974	High Similarity	NPC194095
0.8968	High Similarity	NPC36130
0.8968	High Similarity	NPC134905
0.8968	High Similarity	NPC95498
0.8968	High Similarity	NPC246566
0.8961	High Similarity	NPC259576
0.8961	High Similarity	NPC158635
0.8961	High Similarity	NPC221091
0.8961	High Similarity	NPC229882
0.8951	High Similarity	NPC128403
0.8924	High Similarity	NPC226759
0.891	High Similarity	NPC137813
0.8882	High Similarity	NPC227297
0.8874	High Similarity	NPC478239
0.8854	High Similarity	NPC477299
0.8854	High Similarity	NPC160882
0.8831	High Similarity	NPC116229
0.8812	High Similarity	NPC239966
0.8812	High Similarity	NPC203020
0.8808	High Similarity	NPC140502
0.8808	High Similarity	NPC157816
0.8805	High Similarity	NPC133984
0.8797	High Similarity	NPC186316
0.8795	High Similarity	NPC473630
0.879	High Similarity	NPC157898
0.8774	High Similarity	NPC106138
0.8758	High Similarity	NPC34587
0.8758	High Similarity	NPC100998
0.8758	High Similarity	NPC476382
0.8758	High Similarity	NPC34927
0.8758	High Similarity	NPC71780
0.8758	High Similarity	NPC252292
0.875	High Similarity	NPC160780
0.875	High Similarity	NPC469384
0.875	High Similarity	NPC289811
0.8743	High Similarity	NPC472380
0.8743	High Similarity	NPC472384
0.8743	High Similarity	NPC472382
0.8742	High Similarity	NPC186406
0.8742	High Similarity	NPC228357
0.8735	High Similarity	NPC4390
0.872	High Similarity	NPC116745
0.8704	High Similarity	NPC61594
0.8704	High Similarity	NPC56735
0.8704	High Similarity	NPC148273
0.8701	High Similarity	NPC476865
0.8701	High Similarity	NPC199928
0.8693	High Similarity	NPC110063
0.8693	High Similarity	NPC232228
0.8693	High Similarity	NPC160378
0.8688	High Similarity	NPC472860
0.8688	High Similarity	NPC475663
0.8688	High Similarity	NPC1913
0.8688	High Similarity	NPC286919
0.8683	High Similarity	NPC264735
0.8675	High Similarity	NPC153755
0.8675	High Similarity	NPC175107
0.8675	High Similarity	NPC288452
0.8675	High Similarity	NPC179505
0.8675	High Similarity	NPC156709
0.8675	High Similarity	NPC289690
0.8675	High Similarity	NPC190003
0.8671	High Similarity	NPC87403
0.8654	High Similarity	NPC98809
0.8654	High Similarity	NPC476394
0.865	High Similarity	NPC147596
0.8645	High Similarity	NPC232992
0.8642	High Similarity	NPC472859
0.8642	High Similarity	NPC25389
0.8642	High Similarity	NPC311803
0.8636	High Similarity	NPC476868
0.8636	High Similarity	NPC476866
0.8636	High Similarity	NPC476864
0.8636	High Similarity	NPC476869
0.8634	High Similarity	NPC231475
0.8634	High Similarity	NPC57072
0.8631	High Similarity	NPC268533
0.8631	High Similarity	NPC472385
0.8631	High Similarity	NPC198324
0.8625	High Similarity	NPC470896
0.8625	High Similarity	NPC473275
0.8614	High Similarity	NPC235260
0.8614	High Similarity	NPC20505
0.8614	High Similarity	NPC206123
0.8614	High Similarity	NPC155763
0.8614	High Similarity	NPC244776
0.8614	High Similarity	NPC212748
0.8614	High Similarity	NPC72249
0.8614	High Similarity	NPC116864
0.8609	High Similarity	NPC100389
0.8608	High Similarity	NPC106818
0.8606	High Similarity	NPC298847
0.8605	High Similarity	NPC475360
0.86	High Similarity	NPC37468
0.8599	High Similarity	NPC470934
0.8599	High Similarity	NPC471214
0.8599	High Similarity	NPC188393
0.8599	High Similarity	NPC205054
0.8599	High Similarity	NPC32197
0.8598	High Similarity	NPC88243
0.8598	High Similarity	NPC165720
0.859	High Similarity	NPC1580
0.859	High Similarity	NPC192568
0.859	High Similarity	NPC473138
0.859	High Similarity	NPC472969
0.859	High Similarity	NPC28776
0.859	High Similarity	NPC471076
0.8589	High Similarity	NPC33298
0.8589	High Similarity	NPC22324
0.8589	High Similarity	NPC285108
0.8581	High Similarity	NPC98356
0.858	High Similarity	NPC119125
0.858	High Similarity	NPC173837
0.858	High Similarity	NPC139571
0.858	High Similarity	NPC166277
0.858	High Similarity	NPC477895
0.858	High Similarity	NPC217520
0.858	High Similarity	NPC35167
0.8571	High Similarity	NPC49344
0.8571	High Similarity	NPC101191
0.8571	High Similarity	NPC476867
0.8571	High Similarity	NPC292443
0.8571	High Similarity	NPC115760
0.8571	High Similarity	NPC237435
0.8571	High Similarity	NPC477848
0.8571	High Similarity	NPC43211
0.8571	High Similarity	NPC210094
0.8571	High Similarity	NPC135277
0.8563	High Similarity	NPC472386
0.8555	High Similarity	NPC205721
0.8554	High Similarity	NPC270578
0.8554	High Similarity	NPC52382
0.8554	High Similarity	NPC229687
0.8554	High Similarity	NPC138927
0.8554	High Similarity	NPC120099
0.8554	High Similarity	NPC223747
0.8554	High Similarity	NPC225434
0.8554	High Similarity	NPC219904
0.8554	High Similarity	NPC203050
0.8553	High Similarity	NPC202700
0.8553	High Similarity	NPC19380
0.8553	High Similarity	NPC146277
0.8543	High Similarity	NPC67349
0.8543	High Similarity	NPC279676
0.8543	High Similarity	NPC470413
0.8543	High Similarity	NPC126206
0.8543	High Similarity	NPC138738
0.8538	High Similarity	NPC470445
0.8538	High Similarity	NPC36138
0.8538	High Similarity	NPC470447
0.8538	High Similarity	NPC470449
0.8538	High Similarity	NPC470446
0.8537	High Similarity	NPC88043
0.8537	High Similarity	NPC223006
0.8537	High Similarity	NPC134047
0.8537	High Similarity	NPC272750
0.8537	High Similarity	NPC173729
0.8535	High Similarity	NPC306890
0.8535	High Similarity	NPC259347
0.8535	High Similarity	NPC94871
0.8535	High Similarity	NPC476398
0.8535	High Similarity	NPC470933
0.8535	High Similarity	NPC471062
0.8535	High Similarity	NPC476386
0.8535	High Similarity	NPC473427
0.8528	High Similarity	NPC217950
0.8526	High Similarity	NPC229264
0.8521	High Similarity	NPC89127
0.8521	High Similarity	NPC233994
0.8521	High Similarity	NPC471669
0.8521	High Similarity	NPC144097
0.8521	High Similarity	NPC61904
0.8521	High Similarity	NPC211532
0.8519	High Similarity	NPC179914

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 NPC469654 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	298
0.1-0.2	843
0.2-0.3	1739
0.3-0.4	2580
0.4-0.5	1951
0.5-0.6	1050
0.6-0.7	539
0.7-0.8	136
0.8-0.85	14
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD4338	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD7808	Phase 3
0.8402	Intermediate Similarity	NPD7251	Discontinued
0.8393	Intermediate Similarity	NPD7074	Phase 3
0.8383	Intermediate Similarity	NPD3818	Discontinued
0.8366	Intermediate Similarity	NPD7266	Discontinued
0.8343	Intermediate Similarity	NPD6797	Phase 2
0.8333	Intermediate Similarity	NPD7054	Approved
0.8284	Intermediate Similarity	NPD7472	Approved
0.8269	Intermediate Similarity	NPD6190	Approved
0.8187	Intermediate Similarity	NPD7685	Pre-registration
0.8121	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD7075	Discontinued
0.8118	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD3817	Phase 2
0.8103	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD1653	Approved
0.8061	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD7228	Approved
0.805	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD6166	Phase 2
0.7988	Intermediate Similarity	NPD1934	Approved
0.7988	Intermediate Similarity	NPD37	Approved
0.7977	Intermediate Similarity	NPD6559	Discontinued
0.7964	Intermediate Similarity	NPD6234	Discontinued
0.7953	Intermediate Similarity	NPD3751	Discontinued
0.7952	Intermediate Similarity	NPD4967	Phase 2
0.7952	Intermediate Similarity	NPD4966	Approved
0.7952	Intermediate Similarity	NPD4965	Approved
0.7952	Intermediate Similarity	NPD3882	Suspended
0.7939	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD5402	Approved
0.7886	Intermediate Similarity	NPD8312	Approved
0.7886	Intermediate Similarity	NPD8313	Approved
0.7882	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD8455	Phase 2
0.7831	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD6233	Phase 2
0.7771	Intermediate Similarity	NPD6801	Discontinued
0.7765	Intermediate Similarity	NPD7199	Phase 2
0.775	Intermediate Similarity	NPD4628	Phase 3
0.7727	Intermediate Similarity	NPD6798	Discontinued
0.7725	Intermediate Similarity	NPD2801	Approved
0.7719	Intermediate Similarity	NPD3787	Discontinued
0.7692	Intermediate Similarity	NPD6355	Discontinued
0.7683	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD5403	Approved
0.767	Intermediate Similarity	NPD7240	Approved
0.7667	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD7095	Approved
0.7647	Intermediate Similarity	NPD7435	Discontinued
0.7616	Intermediate Similarity	NPD6232	Discontinued
0.7607	Intermediate Similarity	NPD6799	Approved
0.76	Intermediate Similarity	NPD5844	Phase 1
0.7595	Intermediate Similarity	NPD7097	Phase 1
0.7586	Intermediate Similarity	NPD7473	Discontinued
0.758	Intermediate Similarity	NPD1933	Approved
0.7561	Intermediate Similarity	NPD5401	Approved
0.7558	Intermediate Similarity	NPD8127	Discontinued
0.7556	Intermediate Similarity	NPD8434	Phase 2
0.7548	Intermediate Similarity	NPD3027	Phase 3
0.7545	Intermediate Similarity	NPD4380	Phase 2
0.7516	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1613	Approved
0.7515	Intermediate Similarity	NPD1512	Approved
0.7515	Intermediate Similarity	NPD7819	Suspended
0.7515	Intermediate Similarity	NPD1465	Phase 2
0.7469	Intermediate Similarity	NPD6674	Discontinued
0.7468	Intermediate Similarity	NPD447	Suspended
0.7452	Intermediate Similarity	NPD4062	Phase 3
0.744	Intermediate Similarity	NPD6599	Discontinued
0.7438	Intermediate Similarity	NPD7033	Discontinued
0.7409	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD7874	Approved
0.7405	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD4060	Phase 1
0.7399	Intermediate Similarity	NPD5494	Approved
0.7394	Intermediate Similarity	NPD6777	Approved
0.7394	Intermediate Similarity	NPD6776	Approved
0.7394	Intermediate Similarity	NPD6779	Approved
0.7394	Intermediate Similarity	NPD6780	Approved
0.7394	Intermediate Similarity	NPD1511	Approved
0.7394	Intermediate Similarity	NPD6781	Approved
0.7394	Intermediate Similarity	NPD6778	Approved
0.7394	Intermediate Similarity	NPD6782	Approved
0.7391	Intermediate Similarity	NPD2935	Discontinued
0.7386	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD4110	Phase 3
0.7317	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD1549	Phase 2
0.7294	Intermediate Similarity	NPD7411	Suspended
0.7278	Intermediate Similarity	NPD3226	Approved
0.7278	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD7697	Approved
0.7277	Intermediate Similarity	NPD7696	Phase 3
0.7277	Intermediate Similarity	NPD7698	Approved
0.7261	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD1091	Approved
0.725	Intermediate Similarity	NPD230	Phase 1
0.725	Intermediate Similarity	NPD4340	Discontinued
0.7249	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD919	Approved
0.724	Intermediate Similarity	NPD8320	Phase 1
0.724	Intermediate Similarity	NPD7870	Phase 2
0.724	Intermediate Similarity	NPD7871	Phase 2
0.724	Intermediate Similarity	NPD8319	Approved
0.7239	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7768	Phase 2
0.7216	Intermediate Similarity	NPD7701	Phase 2
0.7204	Intermediate Similarity	NPD7296	Approved
0.7197	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD4534	Discontinued
0.7194	Intermediate Similarity	NPD7783	Phase 2
0.7194	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6386	Approved
0.7193	Intermediate Similarity	NPD6385	Approved
0.7188	Intermediate Similarity	NPD7680	Approved
0.7182	Intermediate Similarity	NPD7038	Approved
0.7182	Intermediate Similarity	NPD7039	Approved
0.7179	Intermediate Similarity	NPD8151	Discontinued
0.7175	Intermediate Similarity	NPD3926	Phase 2
0.7174	Intermediate Similarity	NPD8150	Discontinued
0.7168	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6832	Phase 2
0.7143	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6823	Phase 2
0.7134	Intermediate Similarity	NPD5763	Approved
0.7134	Intermediate Similarity	NPD2346	Discontinued
0.7134	Intermediate Similarity	NPD5762	Approved
0.7128	Intermediate Similarity	NPD6535	Approved
0.7128	Intermediate Similarity	NPD6534	Approved
0.7126	Intermediate Similarity	NPD5058	Phase 3
0.7117	Intermediate Similarity	NPD2799	Discontinued
0.7108	Intermediate Similarity	NPD8166	Discontinued
0.7108	Intermediate Similarity	NPD3750	Approved
0.7107	Intermediate Similarity	NPD7801	Approved
0.7105	Intermediate Similarity	NPD7700	Phase 2
0.7105	Intermediate Similarity	NPD7699	Phase 2
0.7099	Intermediate Similarity	NPD6653	Approved
0.7097	Intermediate Similarity	NPD1608	Approved
0.7093	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD5958	Discontinued
0.7089	Intermediate Similarity	NPD9494	Approved
0.7076	Intermediate Similarity	NPD7458	Discontinued
0.7073	Intermediate Similarity	NPD1551	Phase 2
0.7073	Intermediate Similarity	NPD2796	Approved
0.707	Intermediate Similarity	NPD2797	Approved
0.7066	Intermediate Similarity	NPD2354	Approved
0.7066	Intermediate Similarity	NPD3887	Approved
0.7063	Intermediate Similarity	NPD3764	Approved
0.7063	Intermediate Similarity	NPD2313	Discontinued
0.7062	Intermediate Similarity	NPD1247	Approved
0.7044	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD3146	Approved
0.7041	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5536	Phase 2
0.7039	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7028	Phase 2
0.7032	Intermediate Similarity	NPD3705	Approved
0.7025	Intermediate Similarity	NPD5647	Approved
0.7012	Intermediate Similarity	NPD1510	Phase 2
0.7	Intermediate Similarity	NPD6273	Approved
0.699	Remote Similarity	NPD7584	Approved
0.6989	Remote Similarity	NPD3749	Approved
0.6988	Remote Similarity	NPD2424	Discontinued
0.6981	Remote Similarity	NPD2861	Phase 2
0.6977	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD5353	Approved
0.697	Remote Similarity	NPD6032	Approved
0.6966	Remote Similarity	NPD6959	Discontinued
0.6963	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD1203	Approved
0.6957	Remote Similarity	NPD3268	Approved
0.6954	Remote Similarity	NPD7585	Approved
0.6948	Remote Similarity	NPD1357	Approved
0.6946	Remote Similarity	NPD1652	Phase 2
0.6933	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD5124	Phase 1
0.6923	Remote Similarity	NPD1535	Discovery
0.6919	Remote Similarity	NPD3686	Approved
0.6919	Remote Similarity	NPD3687	Approved
0.6914	Remote Similarity	NPD7972	Discontinued
0.6909	Remote Similarity	NPD4308	Phase 3
0.6904	Remote Similarity	NPD7583	Approved
0.6903	Remote Similarity	NPD17	Approved
0.6901	Remote Similarity	NPD5049	Phase 3
0.6901	Remote Similarity	NPD7314	Clinical (unspecified phase)

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