NPASS Compound

Structure

CID321184 OpenBabel06191716152D 42 45 0 0 1 0 0 0 0 0999 V2000 -3.4166 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5506 2.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3776 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2437 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2826 1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4166 3.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3776 -1.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3776 1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6845 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8185 1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1097 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 4.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0646 -2.6037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6691 -0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5506 1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2437 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2826 2.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2437 -1.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1097 -1.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 3.0933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3776 2.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 1.5933 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6456 2.5933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7796 1.0933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8090 -1.4013 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9135 1.5933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9135 -0.4067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1691 -1.6092 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6456 4.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8736 -3.1915 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1486 3.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2437 -2.9067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9757 -1.9067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2437 3.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5116 1.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5522 -2.0704 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9781 -2.1970 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0475 1.0933 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 0.9135 2.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5116 3.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 0.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 1 15 2 0 0 0 0 2 6 2 0 0 0 0 2 15 1 0 0 0 0 3 7 2 0 0 0 0 3 16 1 0 0 0 0 4 8 2 0 0 0 0 4 16 1 0 0 0 0 5 17 2 0 0 0 0 6 17 1 0 0 0 0 7 18 1 0 0 0 0 8 21 1 0 0 0 0 9 10 1 0 0 0 0 9 15 1 0 0 0 0 10 38 1 0 0 0 0 11 16 2 0 0 0 0 11 19 1 0 0 0 0 12 29 1 0 0 0 0 13 28 1 0 0 0 0 13 30 1 0 0 0 0 14 28 1 0 0 0 0 14 39 1 0 0 0 0 17 31 1 0 0 0 0 18 19 2 0 0 0 0 18 32 1 0 0 0 0 19 33 1 0 0 0 0 20 12 1 6 0 0 0 20 23 1 0 0 0 0 20 40 1 0 0 0 0 21 34 2 0 0 0 0 21 41 1 0 0 0 0 22 23 1 0 0 0 0 22 24 1 0 0 0 0 22 35 1 6 0 0 0 23 41 1 1 0 0 0 24 26 1 0 0 0 0 24 42 1 1 0 0 0 25 27 1 0 0 0 0 25 28 1 6 0 0 0 25 36 1 0 0 0 0 26 38 1 6 0 0 0 26 40 1 0 0 0 0 27 39 1 0 0 0 0 27 42 1 1 0 0 0 28 37 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	594.19
Volume:	560.59
LogP:	0.744
LogD:	0.194
LogS:	-2.443
# Rotatable Bonds:	12
TPSA:	225.06
# H-Bond Aceptor:	14
# H-Bond Donor:	8
# Rings:	4
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.088
Synthetic Accessibility Score:	4.654
Fsp3:	0.464
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.481
MDCK Permeability:	9.303288607043214e-06
Pgp-inhibitor:	0.006
Pgp-substrate:	0.986
Human Intestinal Absorption (HIA):	0.983
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.113
Plasma Protein Binding (PPB):	92.59561157226562%
Volume Distribution (VD):	0.266
Pgp-substrate:	8.893165588378906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.04
CYP1A2-substrate:	0.019
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.022
CYP2C9-substrate:	0.166
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.152
CYP3A4-inhibitor:	0.114
CYP3A4-substrate:	0.112

ADMET: Excretion

Clearance (CL):	1.878
Half-life (T1/2):	0.892

ADMET: Toxicity

hERG Blockers:	0.288
Human Hepatotoxicity (H-HT):	0.145
Drug-inuced Liver Injury (DILI):	0.04
AMES Toxicity:	0.24
Rat Oral Acute Toxicity:	0.092
Maximum Recommended Daily Dose:	0.004
Skin Sensitization:	0.957
Carcinogencity:	0.066
Eye Corrosion:	0.003
Eye Irritation:	0.022
Respiratory Toxicity:	0.016

Download Data

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

Natural Product: NPC321184

Natural Product ID:	NPC321184
*Common Name:**	Beta-(4-Hydroxyphenyl)Ethyl-4-O-E-Caffeoyl-O-[Beta-D-Apiofuranosyl-(1->2)]-Beta-D-Glucopyranoside
IUPAC Name:	[(2R,3S,4S,5R,6R)-5-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4-hydroxy-2-(hydroxymethyl)-6-[2-(4-hydroxyphenyl)ethoxy]oxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Synonyms:
Standard InCHIKey:	TXTPNFUSMTWSFE-JCJVHILYSA-N
Standard InCHI:	InChI=1S/C28H34O14/c29-12-20-23(41-21(34)8-4-16-3-7-18(32)19(33)11-16)22(35)24(42-27-25(36)28(37,13-30)14-39-27)26(40-20)38-10-9-15-1-5-17(31)6-2-15/h1-8,11,20,22-27,29-33,35-37H,9-10,12-14H2/b8-4+/t20-,22+,23-,24-,25+,26-,27+,28-/m1/s1
SMILES:	OC[C@H]1O[C@@H](OCCc2ccc(cc2)O)[C@@H]([C@H]([C@@H]1OC(=O)/C=C/c1ccc(c(c1)O)O)O)O[C@@H]1OC[C@]([C@H]1O)(O)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1689257
PubChem CID:	51042201
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
NPO19548	Lepisorus contortus	Species	Polypodiaceae	Eukaryota	whole plant	Gongshan County, Yunnan, China	n.a.	PMID[21261296]
NPO19548	Lepisorus contortus	Species	Polypodiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21261296]
NPO19548	Lepisorus contortus	Species	Polypodiaceae	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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT441	Individual Protein	Cytochrome P450 19A1	Homo sapiens	IC50	=	30700.0	nM	PMID[470280]

☑ 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 NPC321184 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	307
0.1-0.2	1258
0.2-0.3	2987
0.3-0.4	7397
0.4-0.5	10478
0.5-0.6	8060
0.6-0.7	8854
0.7-0.8	2837
0.8-0.85	315
0.85-0.9	157
0.9-0.95	43
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC321638
1.0	High Similarity	NPC328273
1.0	High Similarity	NPC171134
0.9704	High Similarity	NPC105005
0.9704	High Similarity	NPC40305
0.9695	High Similarity	NPC287597
0.9695	High Similarity	NPC886
0.9695	High Similarity	NPC34293
0.9632	High Similarity	NPC196063
0.9632	High Similarity	NPC296954
0.9632	High Similarity	NPC300894
0.9632	High Similarity	NPC141455
0.9624	High Similarity	NPC260425
0.9552	High Similarity	NPC476383
0.9552	High Similarity	NPC197316
0.9552	High Similarity	NPC205195
0.9552	High Similarity	NPC81515
0.9552	High Similarity	NPC89105
0.9552	High Similarity	NPC472350
0.9552	High Similarity	NPC68092
0.9552	High Similarity	NPC64141
0.9542	High Similarity	NPC473924
0.9493	High Similarity	NPC229505
0.9478	High Similarity	NPC78363
0.947	High Similarity	NPC254398
0.9466	High Similarity	NPC478255
0.9466	High Similarity	NPC219677
0.9412	High Similarity	NPC476385
0.9412	High Similarity	NPC134405
0.9412	High Similarity	NPC476377
0.9412	High Similarity	NPC47471
0.9398	High Similarity	NPC471883
0.9348	High Similarity	NPC110063
0.9343	High Similarity	NPC222433
0.9343	High Similarity	NPC265648
0.9338	High Similarity	NPC473799
0.9338	High Similarity	NPC475530
0.9328	High Similarity	NPC476870
0.9313	High Similarity	NPC477294
0.9313	High Similarity	NPC477293
0.9313	High Similarity	NPC229784
0.9275	High Similarity	NPC264632
0.9275	High Similarity	NPC476380
0.9275	High Similarity	NPC205864
0.9275	High Similarity	NPC476375
0.9275	High Similarity	NPC119537
0.9275	High Similarity	NPC112
0.9275	High Similarity	NPC76406
0.9275	High Similarity	NPC476384
0.9275	High Similarity	NPC298257
0.9275	High Similarity	NPC96795
0.9275	High Similarity	NPC476378
0.9275	High Similarity	NPC247032
0.9275	High Similarity	NPC175214
0.9275	High Similarity	NPC476381
0.9275	High Similarity	NPC269141
0.9275	High Similarity	NPC476397
0.9248	High Similarity	NPC473285
0.9237	High Similarity	NPC232880
0.9237	High Similarity	NPC225307
0.9225	High Similarity	NPC470934
0.9225	High Similarity	NPC188393
0.9209	High Similarity	NPC64195
0.9203	High Similarity	NPC140502
0.9191	High Similarity	NPC476376
0.916	High Similarity	NPC476873
0.916	High Similarity	NPC288416
0.9143	High Similarity	NPC287615
0.9143	High Similarity	NPC262182
0.9143	High Similarity	NPC100998
0.9143	High Similarity	NPC476382
0.9143	High Similarity	NPC34587
0.9143	High Similarity	NPC252292
0.9143	High Similarity	NPC83743
0.9143	High Similarity	NPC216819
0.9143	High Similarity	NPC34927
0.913	High Similarity	NPC186406
0.9118	High Similarity	NPC470572
0.903	High Similarity	NPC46137
0.903	High Similarity	NPC235294
0.9015	High Similarity	NPC264900
0.9015	High Similarity	NPC231607
0.9015	High Similarity	NPC79715
0.9015	High Similarity	NPC108659
0.9014	High Similarity	NPC232992
0.9008	High Similarity	NPC126991
0.9008	High Similarity	NPC83218
0.9008	High Similarity	NPC90318
0.9	High Similarity	NPC478239
0.8986	High Similarity	NPC220942
0.8986	High Similarity	NPC226005
0.8966	High Similarity	NPC478268
0.8963	High Similarity	NPC254275
0.8951	High Similarity	NPC199311
0.8951	High Similarity	NPC192763
0.8951	High Similarity	NPC3460
0.8951	High Similarity	NPC215095
0.8951	High Similarity	NPC261122
0.8951	High Similarity	NPC210611
0.8951	High Similarity	NPC300262
0.8951	High Similarity	NPC201148
0.8951	High Similarity	NPC80732
0.8951	High Similarity	NPC28651
0.8939	High Similarity	NPC94179
0.8939	High Similarity	NPC471157
0.8936	High Similarity	NPC292443
0.8936	High Similarity	NPC476867
0.8936	High Similarity	NPC232228
0.8929	High Similarity	NPC296643
0.8929	High Similarity	NPC157816
0.8905	High Similarity	NPC123988
0.8897	High Similarity	NPC28637
0.8889	High Similarity	NPC94871
0.8889	High Similarity	NPC306890
0.8889	High Similarity	NPC476398
0.8889	High Similarity	NPC283839
0.8889	High Similarity	NPC90896
0.8889	High Similarity	NPC478242
0.8889	High Similarity	NPC476386
0.8889	High Similarity	NPC106138
0.8889	High Similarity	NPC473427
0.8889	High Similarity	NPC138777
0.8889	High Similarity	NPC471062
0.8889	High Similarity	NPC225384
0.8889	High Similarity	NPC470933
0.8889	High Similarity	NPC259347
0.8889	High Similarity	NPC246869
0.8881	High Similarity	NPC184092
0.8873	High Similarity	NPC476869
0.8873	High Similarity	NPC476868
0.8873	High Similarity	NPC476866
0.8873	High Similarity	NPC476864
0.8872	High Similarity	NPC173150
0.8872	High Similarity	NPC471881
0.8872	High Similarity	NPC106677
0.8872	High Similarity	NPC471882
0.8872	High Similarity	NPC156692
0.8872	High Similarity	NPC45224
0.8872	High Similarity	NPC35288
0.8841	High Similarity	NPC154485
0.8841	High Similarity	NPC157554
0.8841	High Similarity	NPC471872
0.8836	High Similarity	NPC106818
0.8828	High Similarity	NPC257970
0.8828	High Similarity	NPC470927
0.8819	High Similarity	NPC473138
0.8819	High Similarity	NPC28776
0.8811	High Similarity	NPC199928
0.8811	High Similarity	NPC473867
0.8811	High Similarity	NPC476865
0.8806	High Similarity	NPC148982
0.8803	High Similarity	NPC297342
0.8797	High Similarity	NPC252114
0.8797	High Similarity	NPC61181
0.8792	High Similarity	NPC226759
0.8786	High Similarity	NPC202700
0.8779	High Similarity	NPC52097
0.8777	High Similarity	NPC84789
0.8777	High Similarity	NPC310252
0.8777	High Similarity	NPC100558
0.8777	High Similarity	NPC302583
0.8776	High Similarity	NPC87403
0.8768	High Similarity	NPC263829
0.8767	High Similarity	NPC143480
0.8767	High Similarity	NPC7145
0.8767	High Similarity	NPC85192
0.8767	High Similarity	NPC125823
0.875	High Similarity	NPC18789
0.8732	High Similarity	NPC46092
0.8732	High Similarity	NPC478250
0.8731	High Similarity	NPC103533
0.8725	High Similarity	NPC11411
0.8723	High Similarity	NPC472711
0.8714	High Similarity	NPC100389
0.8712	High Similarity	NPC178449
0.8712	High Similarity	NPC470907
0.8712	High Similarity	NPC232454
0.8707	High Similarity	NPC472612
0.8707	High Similarity	NPC472611
0.8707	High Similarity	NPC289967
0.8705	High Similarity	NPC199459
0.8705	High Similarity	NPC177035
0.8705	High Similarity	NPC471664
0.8705	High Similarity	NPC52277
0.8705	High Similarity	NPC186418
0.8705	High Similarity	NPC471665
0.8702	High Similarity	NPC147654
0.8702	High Similarity	NPC266045
0.8702	High Similarity	NPC11724
0.8696	High Similarity	NPC135127
0.8696	High Similarity	NPC470881
0.8671	High Similarity	NPC84181
0.8671	High Similarity	NPC283995
0.8671	High Similarity	NPC129417
0.8671	High Similarity	NPC470235
0.8649	High Similarity	NPC471874
0.8643	High Similarity	NPC470413
0.8643	High Similarity	NPC126206
0.8643	High Similarity	NPC138738
0.8639	High Similarity	NPC269914

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 NPC321184 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	240
0.1-0.2	740
0.2-0.3	1591
0.3-0.4	2936
0.4-0.5	2095
0.5-0.6	1169
0.6-0.7	344
0.7-0.8	33
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
0.9552	High Similarity	NPD7266	Discontinued
0.8345	Intermediate Similarity	NPD6190	Approved
0.8255	Intermediate Similarity	NPD1653	Approved
0.7914	Intermediate Similarity	NPD7685	Pre-registration
0.7778	Intermediate Similarity	NPD7228	Approved
0.7778	Intermediate Similarity	NPD3818	Discontinued
0.7748	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD3027	Phase 3
0.7673	Intermediate Similarity	NPD6234	Discontinued
0.7655	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD1613	Approved
0.7622	Intermediate Similarity	NPD7054	Approved
0.7619	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD37	Approved
0.7576	Intermediate Similarity	NPD7472	Approved
0.7576	Intermediate Similarity	NPD7074	Phase 3
0.7547	Intermediate Similarity	NPD4965	Approved
0.7547	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD4966	Approved
0.7547	Intermediate Similarity	NPD4967	Phase 2
0.7545	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7251	Discontinued
0.7425	Intermediate Similarity	NPD6797	Phase 2
0.7394	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD6559	Discontinued
0.7379	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD1091	Approved
0.7376	Intermediate Similarity	NPD3705	Approved
0.7372	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD230	Phase 1
0.7337	Intermediate Similarity	NPD7808	Phase 3
0.732	Intermediate Similarity	NPD8166	Discontinued
0.7312	Intermediate Similarity	NPD8455	Phase 2
0.731	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD1357	Approved
0.7279	Intermediate Similarity	NPD3764	Approved
0.7278	Intermediate Similarity	NPD7240	Approved
0.7267	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD7199	Phase 2
0.7255	Intermediate Similarity	NPD6674	Discontinued
0.7234	Intermediate Similarity	NPD5125	Phase 3
0.7234	Intermediate Similarity	NPD5126	Approved
0.7226	Intermediate Similarity	NPD5058	Phase 3
0.7206	Intermediate Similarity	NPD969	Suspended
0.7185	Intermediate Similarity	NPD3021	Approved
0.7185	Intermediate Similarity	NPD3022	Approved
0.7143	Intermediate Similarity	NPD1934	Approved
0.7124	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD2977	Approved
0.7099	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD2978	Approved
0.7097	Intermediate Similarity	NPD4628	Phase 3
0.7093	Intermediate Similarity	NPD8312	Approved
0.7093	Intermediate Similarity	NPD8313	Approved
0.7075	Intermediate Similarity	NPD2861	Phase 2
0.7066	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD3455	Phase 2
0.7039	Intermediate Similarity	NPD7097	Phase 1
0.7024	Intermediate Similarity	NPD6166	Phase 2
0.7024	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD4340	Discontinued
0.7019	Intermediate Similarity	NPD4380	Phase 2
0.7012	Intermediate Similarity	NPD3882	Suspended
0.7006	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.698	Remote Similarity	NPD7095	Approved
0.697	Remote Similarity	NPD7075	Discontinued
0.6961	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD228	Approved
0.6954	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD4060	Phase 1
0.6951	Remote Similarity	NPD3817	Phase 2
0.6946	Remote Similarity	NPD8127	Discontinued
0.6923	Remote Similarity	NPD1652	Phase 2
0.6902	Remote Similarity	NPD7680	Approved
0.6901	Remote Similarity	NPD5536	Phase 2
0.6901	Remote Similarity	NPD5844	Phase 1
0.689	Remote Similarity	NPD2801	Approved
0.689	Remote Similarity	NPD1465	Phase 2
0.6887	Remote Similarity	NPD6233	Phase 2
0.6883	Remote Similarity	NPD5588	Approved
0.6863	Remote Similarity	NPD5314	Approved
0.6863	Remote Similarity	NPD6653	Approved
0.6857	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD1511	Approved
0.6853	Remote Similarity	NPD9545	Approved
0.6849	Remote Similarity	NPD9269	Phase 2
0.6848	Remote Similarity	NPD5402	Approved
0.6846	Remote Similarity	NPD5736	Approved
0.6842	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3059	Approved
0.6842	Remote Similarity	NPD3062	Approved
0.6842	Remote Similarity	NPD3061	Approved
0.6842	Remote Similarity	NPD3751	Discontinued
0.6842	Remote Similarity	NPD3620	Phase 2
0.6824	Remote Similarity	NPD3094	Phase 2
0.6797	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD6355	Discontinued
0.6797	Remote Similarity	NPD5124	Phase 1
0.6795	Remote Similarity	NPD5762	Approved
0.6795	Remote Similarity	NPD5763	Approved
0.6788	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD1358	Approved
0.6774	Remote Similarity	NPD7033	Discontinued
0.677	Remote Similarity	NPD1512	Approved
0.677	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD9384	Approved
0.6759	Remote Similarity	NPD9381	Approved
0.6738	Remote Similarity	NPD5283	Phase 1
0.6732	Remote Similarity	NPD943	Approved
0.6731	Remote Similarity	NPD9570	Approved
0.6731	Remote Similarity	NPD2935	Discontinued
0.6728	Remote Similarity	NPD5403	Approved
0.6712	Remote Similarity	NPD3496	Discontinued
0.6711	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD6798	Discontinued
0.671	Remote Similarity	NPD4536	Approved
0.671	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.671	Remote Similarity	NPD4538	Approved
0.6709	Remote Similarity	NPD4237	Approved
0.6709	Remote Similarity	NPD4236	Phase 3
0.6709	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD7028	Phase 2
0.6706	Remote Similarity	NPD3787	Discontinued
0.6706	Remote Similarity	NPD6232	Discontinued
0.6689	Remote Similarity	NPD4908	Phase 1
0.6689	Remote Similarity	NPD2983	Phase 2
0.6689	Remote Similarity	NPD2982	Phase 2
0.6688	Remote Similarity	NPD1933	Approved
0.6687	Remote Similarity	NPD3687	Approved
0.6687	Remote Similarity	NPD7819	Suspended
0.6687	Remote Similarity	NPD3686	Approved
0.6687	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7473	Discontinued
0.6685	Remote Similarity	NPD8150	Discontinued
0.6667	Remote Similarity	NPD6663	Approved
0.6667	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1610	Phase 2
0.6667	Remote Similarity	NPD7843	Approved
0.6667	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4110	Phase 3
0.6667	Remote Similarity	NPD6385	Approved
0.6667	Remote Similarity	NPD3092	Approved
0.6667	Remote Similarity	NPD422	Phase 1
0.6667	Remote Similarity	NPD5960	Phase 3
0.6667	Remote Similarity	NPD6386	Approved
0.6648	Remote Similarity	NPD6843	Phase 3
0.6648	Remote Similarity	NPD6842	Approved
0.6648	Remote Similarity	NPD6841	Approved
0.6648	Remote Similarity	NPD7549	Discontinued
0.6646	Remote Similarity	NPD2424	Discontinued
0.6646	Remote Similarity	NPD4357	Discontinued
0.6646	Remote Similarity	NPD7458	Discontinued
0.6645	Remote Similarity	NPD2492	Phase 1
0.6645	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD7157	Approved
0.6631	Remote Similarity	NPD7435	Discontinued
0.6627	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD6801	Discontinued
0.6623	Remote Similarity	NPD4140	Approved
0.6623	Remote Similarity	NPD826	Approved
0.6623	Remote Similarity	NPD3018	Phase 2
0.6623	Remote Similarity	NPD9494	Approved
0.6623	Remote Similarity	NPD825	Approved
0.6623	Remote Similarity	NPD1558	Phase 1
0.6622	Remote Similarity	NPD2981	Phase 2
0.6621	Remote Similarity	NPD1548	Phase 1
0.6605	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD5401	Approved
0.6604	Remote Similarity	NPD3060	Approved
0.6604	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD8320	Phase 1
0.6596	Remote Similarity	NPD8319	Approved
0.6594	Remote Similarity	NPD3134	Approved
0.6593	Remote Similarity	NPD1242	Phase 1
0.6592	Remote Similarity	NPD8434	Phase 2
0.6591	Remote Similarity	NPD2934	Approved
0.6591	Remote Similarity	NPD2933	Approved
0.6591	Remote Similarity	NPD7039	Approved
0.6591	Remote Similarity	NPD7038	Approved
0.6588	Remote Similarity	NPD5494	Approved
0.6584	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD1375	Discontinued
0.6577	Remote Similarity	NPD9622	Approved
0.6575	Remote Similarity	NPD9268	Approved
0.6562	Remote Similarity	NPD3750	Approved
0.6562	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD7999	Approved
0.6561	Remote Similarity	NPD4108	Discontinued
0.6558	Remote Similarity	NPD4062	Phase 3
0.6557	Remote Similarity	NPD6534	Approved
0.6557	Remote Similarity	NPD6535	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