NPASS Compound

Structure

NPC476376 OpenBabel07101718192D 46 49 0 0 1 0 0 0 0 0999 V2000 -8.6603 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 6.0000 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 -5.1962 5.0000 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 -6.9282 -0.0000 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 -8.6603 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.7942 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 2 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 -9.5263 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.6603 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.5263 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 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 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 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 7.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 6.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 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 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 4 2 0 0 0 0 2 11 1 0 0 0 0 3 5 2 0 0 0 0 3 11 1 0 0 0 0 4 12 1 0 0 0 0 5 17 1 0 0 0 0 6 11 2 0 0 0 0 6 13 1 0 0 0 0 7 29 1 0 0 0 0 8 41 1 0 0 0 0 9 42 1 0 0 0 0 10 1 1 6 0 0 0 10 18 1 0 0 0 0 10 43 1 0 0 0 0 12 13 2 0 0 0 0 12 30 1 0 0 0 0 13 31 1 0 0 0 0 14 7 1 1 0 0 0 14 19 1 0 0 0 0 14 45 1 0 0 0 0 15 8 1 1 0 0 0 15 20 1 0 0 0 0 15 43 1 0 0 0 0 16 9 1 1 0 0 0 16 25 1 0 0 0 0 16 44 1 0 0 0 0 17 32 2 0 0 0 0 17 46 1 0 0 0 0 18 21 1 0 0 0 0 18 33 1 1 0 0 0 19 22 1 0 0 0 0 19 34 1 6 0 0 0 20 21 1 0 0 0 0 20 35 1 6 0 0 0 21 36 1 6 0 0 0 22 23 1 0 0 0 0 22 37 1 1 0 0 0 23 28 1 0 0 0 0 23 38 1 6 0 0 0 24 26 1 0 0 0 0 24 27 1 0 0 0 0 24 39 1 6 0 0 0 25 26 1 0 0 0 0 25 46 1 6 0 0 0 26 41 1 1 0 0 0 27 40 1 1 0 0 0 27 44 1 0 0 0 0 28 42 1 1 0 0 0 28 45 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	664.22
Volume:	603.66
LogP:	-1.394
LogD:	-1.411
LogS:	-1.525
# Rotatable Bonds:	11
TPSA:	294.98
# H-Bond Aceptor:	18
# H-Bond Donor:	11
# Rings:	4
# Heavy Atoms:	18

MedChem Properties

QED Drug-Likeness Score:	0.063
Synthetic Accessibility Score:	5.212
Fsp3:	0.679
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.652
MDCK Permeability:	0.0001466914254706353
Pgp-inhibitor:	0.001
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.995
20% Bioavailability (F20%):	0.974
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.214
Plasma Protein Binding (PPB):	60.75952911376953%
Volume Distribution (VD):	0.312
Pgp-substrate:	35.71146011352539%

ADMET: Metabolism

CYP1A2-inhibitor:	0.027
CYP1A2-substrate:	0.005
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.038
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.092
CYP3A4-inhibitor:	0.02
CYP3A4-substrate:	0.002

ADMET: Excretion

Clearance (CL):	0.793
Half-life (T1/2):	0.739

ADMET: Toxicity

hERG Blockers:	0.334
Human Hepatotoxicity (H-HT):	0.504
Drug-inuced Liver Injury (DILI):	0.396
AMES Toxicity:	0.391
Rat Oral Acute Toxicity:	0.176
Maximum Recommended Daily Dose:	0.002
Skin Sensitization:	0.954
Carcinogencity:	0.031
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.05

Download Data

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

Natural Product: NPC476376

Natural Product ID:	NPC476376
*Common Name:**	Kankanose
IUPAC Name:	[(2R,3R,4R,5R,6R)-5,6-dihydroxy-2-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-4-[[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]methoxy]oxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Synonyms:	Kankanose
Standard InCHIKey:	KNOFCZGZWCPZEU-QTPUSYSKSA-N
Standard InCHI:	InChI=1S/C28H40O18/c1-10-18(33)21(36)20(35)15(43-10)8-41-26-24(39)27(40)44-16(9-42-28-23(38)22(37)19(34)14(7-29)45-28)25(26)46-17(32)5-3-11-2-4-12(30)13(31)6-11/h2-6,10,14-16,18-31,33-40H,7-9H2,1H3/b5-3+/t10-,14+,15-,16+,18-,19+,20-,21+,22-,23+,24+,25+,26+,27+,28+/m0/s1
SMILES:	CC1C(C(C(C(O1)COC2C(C(OC(C2OC(=O)C=CC3=CC(=C(C=C3)O)O)COC4C(C(C(C(O4)CO)O)O)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL590293
PubChem CID:	46228757
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
NPO6964	Cistanche tubulosa	Species	Orobanchaceae	Eukaryota	fresh stems	n.a.	n.a.	PMID[20159656]
NPO6964	Cistanche tubulosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6964	Cistanche tubulosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6964	Cistanche tubulosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6964	Cistanche tubulosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
Others	8

Activity Type	# Activity
Cell Line	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	-4.9	%	PMID[522503]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	-1.3	%	PMID[522503]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	-7.9	%	PMID[522503]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	-2.8	%	PMID[522503]
NPT1460	Cell Line	L929	Mus musculus	Inhibition	=	-1.1	%	PMID[522503]
NPT1460	Cell Line	L929	Mus musculus	Inhibition	=	2.2	%	PMID[522503]
NPT1460	Cell Line	L929	Mus musculus	Inhibition	=	1.3	%	PMID[522503]
NPT1460	Cell Line	L929	Mus musculus	Inhibition	=	0.8	%	PMID[522503]

☑ 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 NPC476376 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	310
0.1-0.2	1339
0.2-0.3	3294
0.3-0.4	7721
0.4-0.5	9672
0.5-0.6	9178
0.6-0.7	8069
0.7-0.8	2698
0.8-0.85	243
0.85-0.9	97
0.9-0.95	54
0.95-1	22

Similarity Score	Similarity Level	Natural Product ID
0.963	High Similarity	NPC476380
0.963	High Similarity	NPC269141
0.963	High Similarity	NPC205864
0.963	High Similarity	NPC76406
0.963	High Similarity	NPC119537
0.963	High Similarity	NPC175214
0.963	High Similarity	NPC476384
0.963	High Similarity	NPC476397
0.963	High Similarity	NPC476381
0.963	High Similarity	NPC247032
0.963	High Similarity	NPC112
0.963	High Similarity	NPC264632
0.963	High Similarity	NPC96795
0.963	High Similarity	NPC298257
0.963	High Similarity	NPC476378
0.963	High Similarity	NPC476375
0.9627	High Similarity	NPC476377
0.9627	High Similarity	NPC134405
0.9627	High Similarity	NPC476385
0.9627	High Similarity	NPC47471
0.9624	High Similarity	NPC68092
0.9624	High Similarity	NPC472350
0.9624	High Similarity	NPC81515
0.9624	High Similarity	NPC89105
0.9624	High Similarity	NPC64141
0.9624	High Similarity	NPC476383
0.9624	High Similarity	NPC205195
0.9624	High Similarity	NPC197316
0.9615	High Similarity	NPC473285
0.9559	High Similarity	NPC64195
0.9556	High Similarity	NPC222433
0.9556	High Similarity	NPC265648
0.9552	High Similarity	NPC473799
0.9552	High Similarity	NPC475530
0.9549	High Similarity	NPC260425
0.947	High Similarity	NPC471883
0.942	High Similarity	NPC229505
0.9416	High Similarity	NPC300894
0.9416	High Similarity	NPC141455
0.9416	High Similarity	NPC296954
0.9416	High Similarity	NPC196063
0.9403	High Similarity	NPC78363
0.9385	High Similarity	NPC477293
0.9385	High Similarity	NPC229784
0.9385	High Similarity	NPC477294
0.9343	High Similarity	NPC105005
0.9323	High Similarity	NPC287597
0.9323	High Similarity	NPC886
0.9323	High Similarity	NPC34293
0.9308	High Similarity	NPC232880
0.9254	High Similarity	NPC476870
0.9248	High Similarity	NPC254398
0.9242	High Similarity	NPC219677
0.9231	High Similarity	NPC476873
0.922	High Similarity	NPC476398
0.922	High Similarity	NPC94871
0.922	High Similarity	NPC471062
0.922	High Similarity	NPC306890
0.922	High Similarity	NPC476386
0.922	High Similarity	NPC473427
0.922	High Similarity	NPC470933
0.922	High Similarity	NPC259347
0.9214	High Similarity	NPC232992
0.9209	High Similarity	NPC34587
0.9209	High Similarity	NPC100998
0.9209	High Similarity	NPC476382
0.9209	High Similarity	NPC252292
0.9209	High Similarity	NPC34927
0.9191	High Similarity	NPC171134
0.9191	High Similarity	NPC321184
0.9191	High Similarity	NPC328273
0.9191	High Similarity	NPC321638
0.9173	High Similarity	NPC473924
0.9155	High Similarity	NPC257970
0.9155	High Similarity	NPC470927
0.9143	High Similarity	NPC476865
0.9137	High Similarity	NPC476867
0.9111	High Similarity	NPC263829
0.9098	High Similarity	NPC138777
0.9098	High Similarity	NPC225384
0.9098	High Similarity	NPC46137
0.9098	High Similarity	NPC235294
0.9098	High Similarity	NPC246869
0.9084	High Similarity	NPC106677
0.9071	High Similarity	NPC476869
0.9071	High Similarity	NPC476866
0.9071	High Similarity	NPC476864
0.9071	High Similarity	NPC476868
0.9065	High Similarity	NPC40305
0.9044	High Similarity	NPC157554
0.9021	High Similarity	NPC188393
0.9021	High Similarity	NPC470934
0.9014	High Similarity	NPC23677
0.9008	High Similarity	NPC471157
0.8993	High Similarity	NPC140502
0.8993	High Similarity	NPC296643
0.8986	High Similarity	NPC202700
0.8939	High Similarity	NPC471882
0.8939	High Similarity	NPC173150
0.8939	High Similarity	NPC156692
0.8939	High Similarity	NPC35288
0.8939	High Similarity	NPC471881
0.8939	High Similarity	NPC45224
0.8936	High Similarity	NPC262182
0.8936	High Similarity	NPC287615
0.8936	High Similarity	NPC216819
0.8936	High Similarity	NPC83743
0.8931	High Similarity	NPC126991
0.8931	High Similarity	NPC83218
0.8929	High Similarity	NPC478239
0.8921	High Similarity	NPC186406
0.8913	High Similarity	NPC100389
0.8913	High Similarity	NPC220942
0.8913	High Similarity	NPC226005
0.8905	High Similarity	NPC470572
0.8897	High Similarity	NPC106818
0.8889	High Similarity	NPC254275
0.8889	High Similarity	NPC69367
0.8881	High Similarity	NPC80732
0.8881	High Similarity	NPC201148
0.8881	High Similarity	NPC3460
0.8881	High Similarity	NPC192763
0.8881	High Similarity	NPC215095
0.8881	High Similarity	NPC261122
0.8881	High Similarity	NPC28651
0.8881	High Similarity	NPC199311
0.8881	High Similarity	NPC210611
0.8881	High Similarity	NPC300262
0.8865	High Similarity	NPC110063
0.8864	High Similarity	NPC61181
0.8857	High Similarity	NPC157816
0.8846	High Similarity	NPC52097
0.8836	High Similarity	NPC87403
0.8806	High Similarity	NPC184092
0.8797	High Similarity	NPC103533
0.8797	High Similarity	NPC288416
0.8769	High Similarity	NPC11724
0.8768	High Similarity	NPC186418
0.8768	High Similarity	NPC37468
0.8759	High Similarity	NPC35731
0.8759	High Similarity	NPC476871
0.8741	High Similarity	NPC199928
0.8732	High Similarity	NPC297342
0.8732	High Similarity	NPC292443
0.8732	High Similarity	NPC232228
0.8731	High Similarity	NPC225307
0.8722	High Similarity	NPC252114
0.8707	High Similarity	NPC471874
0.8705	High Similarity	NPC101686
0.8705	High Similarity	NPC469364
0.8705	High Similarity	NPC65262
0.8699	High Similarity	NPC85192
0.8699	High Similarity	NPC125823
0.8699	High Similarity	NPC143480
0.8699	High Similarity	NPC7145
0.8692	High Similarity	NPC476872
0.869	High Similarity	NPC478242
0.869	High Similarity	NPC90896
0.869	High Similarity	NPC106138
0.869	High Similarity	NPC283839
0.8686	High Similarity	NPC28637
0.8676	High Similarity	NPC478255
0.8657	High Similarity	NPC264900
0.8657	High Similarity	NPC108659
0.8657	High Similarity	NPC79715
0.8657	High Similarity	NPC231607
0.8639	High Similarity	NPC289967
0.8639	High Similarity	NPC478268
0.8639	High Similarity	NPC472611
0.8639	High Similarity	NPC472612
0.8626	High Similarity	NPC266045
0.8626	High Similarity	NPC55608
0.8621	High Similarity	NPC473138
0.8621	High Similarity	NPC28776
0.8582	High Similarity	NPC94179
0.8571	High Similarity	NPC478249
0.8571	High Similarity	NPC269914
0.8571	High Similarity	NPC304152
0.8561	High Similarity	NPC123988
0.8552	High Similarity	NPC18789
0.854	High Similarity	NPC248307
0.854	High Similarity	NPC65942
0.8531	High Similarity	NPC113680
0.8531	High Similarity	NPC204644
0.8531	High Similarity	NPC278961
0.8529	High Similarity	NPC253595
0.8529	High Similarity	NPC307110
0.8507	High Similarity	NPC90318
0.8503	High Similarity	NPC12006
0.85	High Similarity	NPC177035
0.85	High Similarity	NPC471872
0.85	High Similarity	NPC199459
0.85	High Similarity	NPC154485
0.85	High Similarity	NPC52277
0.8497	Intermediate Similarity	NPC246024
0.8493	Intermediate Similarity	NPC478237
0.8489	Intermediate Similarity	NPC135127
0.8489	Intermediate Similarity	NPC169398
0.8483	Intermediate Similarity	NPC473867
0.8462	Intermediate Similarity	NPC473873

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 NPC476376 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	786
0.2-0.3	1769
0.3-0.4	3017
0.4-0.5	1882
0.5-0.6	1106
0.6-0.7	299
0.7-0.8	27
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9624	High Similarity	NPD7266	Discontinued
0.8311	Intermediate Similarity	NPD1653	Approved
0.8027	Intermediate Similarity	NPD6190	Approved
0.7744	Intermediate Similarity	NPD7685	Pre-registration
0.773	Intermediate Similarity	NPD7074	Phase 3
0.773	Intermediate Similarity	NPD7472	Approved
0.7669	Intermediate Similarity	NPD7054	Approved
0.7636	Intermediate Similarity	NPD7251	Discontinued
0.7607	Intermediate Similarity	NPD7228	Approved
0.7576	Intermediate Similarity	NPD6797	Phase 2
0.7534	Intermediate Similarity	NPD230	Phase 1
0.75	Intermediate Similarity	NPD3027	Phase 3
0.7485	Intermediate Similarity	NPD7808	Phase 3
0.7429	Intermediate Similarity	NPD1091	Approved
0.7381	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD8166	Discontinued
0.7358	Intermediate Similarity	NPD8455	Phase 2
0.7347	Intermediate Similarity	NPD1613	Approved
0.7347	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD6674	Discontinued
0.7289	Intermediate Similarity	NPD3818	Discontinued
0.7284	Intermediate Similarity	NPD6234	Discontinued
0.7251	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7240	Approved
0.7214	Intermediate Similarity	NPD1357	Approved
0.7188	Intermediate Similarity	NPD37	Approved
0.7183	Intermediate Similarity	NPD3705	Approved
0.716	Intermediate Similarity	NPD4966	Approved
0.716	Intermediate Similarity	NPD4965	Approved
0.716	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD4967	Phase 2
0.7135	Intermediate Similarity	NPD8312	Approved
0.7135	Intermediate Similarity	NPD8313	Approved
0.7075	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD6166	Phase 2
0.7066	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD9545	Approved
0.7018	Intermediate Similarity	NPD6559	Discontinued
0.7007	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD969	Suspended
0.7007	Intermediate Similarity	NPD228	Approved
0.6985	Remote Similarity	NPD3022	Approved
0.6985	Remote Similarity	NPD3021	Approved
0.6981	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD1934	Approved
0.6974	Remote Similarity	NPD7097	Phase 1
0.6974	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD1652	Phase 2
0.6963	Remote Similarity	NPD1358	Approved
0.6933	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4628	Phase 3
0.6897	Remote Similarity	NPD9269	Phase 2
0.6894	Remote Similarity	NPD3455	Phase 2
0.6886	Remote Similarity	NPD7199	Phase 2
0.6886	Remote Similarity	NPD8127	Discontinued
0.6854	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD4380	Phase 2
0.6842	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5844	Phase 1
0.6842	Remote Similarity	NPD5124	Phase 1
0.6839	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD5536	Phase 2
0.6829	Remote Similarity	NPD1465	Phase 2
0.6813	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD7075	Discontinued
0.6806	Remote Similarity	NPD5125	Phase 3
0.6806	Remote Similarity	NPD5126	Approved
0.6797	Remote Similarity	NPD6653	Approved
0.6788	Remote Similarity	NPD3817	Phase 2
0.6779	Remote Similarity	NPD9494	Approved
0.6776	Remote Similarity	NPD4060	Phase 1
0.6765	Remote Similarity	NPD3134	Approved
0.6759	Remote Similarity	NPD3496	Discontinued
0.6757	Remote Similarity	NPD7680	Approved
0.6732	Remote Similarity	NPD4340	Discontinued
0.673	Remote Similarity	NPD5058	Phase 3
0.6728	Remote Similarity	NPD3687	Approved
0.6728	Remote Similarity	NPD3686	Approved
0.6727	Remote Similarity	NPD2977	Approved
0.6727	Remote Similarity	NPD2978	Approved
0.6727	Remote Similarity	NPD2801	Approved
0.6714	Remote Similarity	NPD7843	Approved
0.6712	Remote Similarity	NPD422	Phase 1
0.6711	Remote Similarity	NPD6233	Phase 2
0.6706	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.669	Remote Similarity	NPD9381	Approved
0.669	Remote Similarity	NPD7157	Approved
0.669	Remote Similarity	NPD9384	Approved
0.6689	Remote Similarity	NPD7095	Approved
0.6687	Remote Similarity	NPD5402	Approved
0.6685	Remote Similarity	NPD6843	Phase 3
0.6685	Remote Similarity	NPD6842	Approved
0.6685	Remote Similarity	NPD6841	Approved
0.6667	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5736	Approved
0.6667	Remote Similarity	NPD826	Approved
0.6667	Remote Similarity	NPD3620	Phase 2
0.6667	Remote Similarity	NPD825	Approved
0.6667	Remote Similarity	NPD2861	Phase 2
0.6667	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9570	Approved
0.6647	Remote Similarity	NPD3882	Suspended
0.6646	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD3764	Approved
0.6644	Remote Similarity	NPD3094	Phase 2
0.6631	Remote Similarity	NPD8319	Approved
0.6631	Remote Similarity	NPD8320	Phase 1
0.6627	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD5763	Approved
0.6624	Remote Similarity	NPD5762	Approved
0.6623	Remote Similarity	NPD1933	Approved
0.6623	Remote Similarity	NPD4908	Phase 1
0.6623	Remote Similarity	NPD447	Suspended
0.6622	Remote Similarity	NPD2982	Phase 2
0.6622	Remote Similarity	NPD2983	Phase 2
0.6622	Remote Similarity	NPD9622	Approved
0.6621	Remote Similarity	NPD9268	Approved
0.6605	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.659	Remote Similarity	NPD3751	Discontinued
0.6587	Remote Similarity	NPD5353	Approved
0.6585	Remote Similarity	NPD7458	Discontinued
0.6584	Remote Similarity	NPD1511	Approved
0.6581	Remote Similarity	NPD5314	Approved
0.6579	Remote Similarity	NPD8151	Discontinued
0.6575	Remote Similarity	NPD4626	Approved
0.6571	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD5403	Approved
0.6561	Remote Similarity	NPD2935	Discontinued
0.6558	Remote Similarity	NPD3061	Approved
0.6558	Remote Similarity	NPD3059	Approved
0.6558	Remote Similarity	NPD3062	Approved
0.6556	Remote Similarity	NPD3018	Phase 2
0.6554	Remote Similarity	NPD2981	Phase 2
0.655	Remote Similarity	NPD6232	Discontinued
0.6549	Remote Similarity	NPD5283	Phase 1
0.6547	Remote Similarity	NPD2684	Approved
0.6541	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD4536	Approved
0.6538	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD4538	Approved
0.6536	Remote Similarity	NPD6798	Discontinued
0.6536	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD8150	Discontinued
0.6532	Remote Similarity	NPD7473	Discontinued
0.6527	Remote Similarity	NPD7819	Suspended
0.6517	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD6355	Discontinued
0.6516	Remote Similarity	NPD555	Phase 2
0.6507	Remote Similarity	NPD5691	Approved
0.6506	Remote Similarity	NPD6386	Approved
0.6506	Remote Similarity	NPD6385	Approved
0.6503	Remote Similarity	NPD1512	Approved
0.65	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4110	Phase 3
0.6497	Remote Similarity	NPD7549	Discontinued
0.6494	Remote Similarity	NPD6663	Approved
0.649	Remote Similarity	NPD9620	Approved
0.649	Remote Similarity	NPD9621	Approved
0.649	Remote Similarity	NPD9619	Approved
0.6489	Remote Similarity	NPD7435	Discontinued
0.6486	Remote Similarity	NPD7699	Phase 2
0.6486	Remote Similarity	NPD3092	Approved
0.6486	Remote Similarity	NPD7700	Phase 2
0.6481	Remote Similarity	NPD4357	Discontinued
0.6478	Remote Similarity	NPD2424	Discontinued
0.6475	Remote Similarity	NPD290	Approved
0.6474	Remote Similarity	NPD2492	Phase 1
0.6467	Remote Similarity	NPD6801	Discontinued
0.6467	Remote Similarity	NPD8651	Approved
0.6467	Remote Similarity	NPD3225	Approved
0.6463	Remote Similarity	NPD1778	Approved
0.6463	Remote Similarity	NPD2122	Discontinued
0.6458	Remote Similarity	NPD6671	Approved
0.6457	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD3787	Discontinued
0.6452	Remote Similarity	NPD4140	Approved
0.6452	Remote Similarity	NPD1558	Phase 1
0.6452	Remote Similarity	NPD943	Approved
0.6446	Remote Similarity	NPD7028	Phase 2
0.6442	Remote Similarity	NPD5401	Approved
0.6442	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD7038	Approved
0.6441	Remote Similarity	NPD7039	Approved
0.6438	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD4236	Phase 3
0.6438	Remote Similarity	NPD3060	Approved
0.6438	Remote Similarity	NPD4237	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