NPASS Compound

Structure

NPC471066 OpenBabel07101719152D 43 46 0 0 1 0 0 0 0 0999 V2000 -6.0622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -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 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -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 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1753 1.7319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -6.5000 0.0000 C 0 0 0 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 -1.7321 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1808 1.8364 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6808 2.7024 0.0000 C 0 0 2 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 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7026 2.4945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 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 5.7631 2.5409 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 -0.8660 -7.5000 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 4.0875 3.6160 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 1.9595 3.1637 0.0000 O 0 0 0 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 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5116 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 1 7 1 0 0 0 0 1 16 2 0 0 0 0 2 8 2 0 0 0 0 2 16 1 0 0 0 0 3 9 1 0 0 0 0 3 17 2 0 0 0 0 4 10 2 0 0 0 0 4 17 1 0 0 0 0 5 11 1 0 0 0 0 5 16 1 0 0 0 0 6 12 1 0 0 0 0 6 17 1 0 0 0 0 7 18 2 0 0 0 0 8 18 1 0 0 0 0 9 19 2 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 13 20 1 0 0 0 0 13 21 1 0 0 0 0 14 31 1 0 0 0 0 15 40 1 0 0 0 0 18 32 1 0 0 0 0 19 33 1 0 0 0 0 20 34 2 0 0 0 0 21 12 1 1 0 0 0 21 41 1 0 0 0 0 22 14 1 1 0 0 0 22 24 1 0 0 0 0 22 42 1 0 0 0 0 23 15 1 1 0 0 0 23 25 1 0 0 0 0 23 43 1 0 0 0 0 24 27 1 0 0 0 0 24 35 1 6 0 0 0 25 26 1 0 0 0 0 25 36 1 6 0 0 0 26 28 1 0 0 0 0 26 37 1 1 0 0 0 27 29 1 0 0 0 0 27 38 1 6 0 0 0 28 30 1 0 0 0 0 28 39 1 6 0 0 0 29 40 1 1 0 0 0 29 42 1 0 0 0 0 30 41 1 1 0 0 0 30 43 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	608.25
Volume:	589.028
LogP:	-0.211
LogD:	-0.29
LogS:	-2.454
# Rotatable Bonds:	14
TPSA:	215.83
# H-Bond Aceptor:	13
# H-Bond Donor:	8
# Rings:	4
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.133
Synthetic Accessibility Score:	4.584
Fsp3:	0.567
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:	-6.286
MDCK Permeability:	8.918986168282572e-06
Pgp-inhibitor:	0.01
Pgp-substrate:	0.986
Human Intestinal Absorption (HIA):	0.996
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.17
Plasma Protein Binding (PPB):	67.83076477050781%
Volume Distribution (VD):	0.177
Pgp-substrate:	13.17568588256836%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.017
CYP2C19-inhibitor:	0.039
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.018
CYP2C9-substrate:	0.56
CYP2D6-inhibitor:	0.021
CYP2D6-substrate:	0.223
CYP3A4-inhibitor:	0.009
CYP3A4-substrate:	0.051

ADMET: Excretion

Clearance (CL):	1.354
Half-life (T1/2):	0.876

ADMET: Toxicity

hERG Blockers:	0.462
Human Hepatotoxicity (H-HT):	0.161
Drug-inuced Liver Injury (DILI):	0.019
AMES Toxicity:	0.289
Rat Oral Acute Toxicity:	0.265
Maximum Recommended Daily Dose:	0.041
Skin Sensitization:	0.908
Carcinogencity:	0.256
Eye Corrosion:	0.003
Eye Irritation:	0.063
Respiratory Toxicity:	0.03

Download Data

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

Natural Product: NPC471066

Natural Product ID:	NPC471066
*Common Name:**	(5S)-5-Hydroxy-1,7-Bis-(4-Hydroxyphenyl)-3-Heptanone-5-O-Beta-D-Apiofuranosyl-(1->6)-Beta-D-Glucopyranoside
IUPAC Name:	(5S)-5-[(2R,3R,4S,5S,6R)-6-[[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-1,7-bis(4-hydroxyphenyl)heptan-3-one
Synonyms:
Standard InCHIKey:	UGYZLORFQGTFRN-SHYGZIMPSA-N
Standard InCHI:	InChI=1S/C30H40O13/c31-14-22-24(35)27(38)29(42-22)40-15-23-25(36)26(37)28(39)30(43-23)41-21(12-6-17-3-9-19(33)10-4-17)13-20(34)11-5-16-1-7-18(32)8-2-16/h1-4,7-10,21-33,35-39H,5-6,11-15H2/t21-,22+,23+,24+,25+,26-,27+,28+,29+,30+/m0/s1
SMILES:	C1=CC(=CC=C1CCC(CC(=O)CCC2=CC=C(C=C2)O)OC3C(C(C(C(O3)COC4C(C(C(O4)CO)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2346810
PubChem CID:	71720155
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids [CHEMONTID:0000356] Curcuminoids

*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
NPO32876	alnus hirsuta f. sibirica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23465614]

☑ 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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	24.8	%	PMID[490551]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	34.6	%	PMID[490551]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	88.4	%	PMID[490551]

☑ 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 NPC471066 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	291
0.1-0.2	1003
0.2-0.3	2482
0.3-0.4	5950
0.4-0.5	11899
0.5-0.6	7854
0.6-0.7	10933
0.7-0.8	2141
0.8-0.85	110
0.85-0.9	21
0.9-0.95	10
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471095
0.9921	High Similarity	NPC164172
0.984	High Similarity	NPC470122
0.984	High Similarity	NPC17968
0.984	High Similarity	NPC469705
0.968	High Similarity	NPC158673
0.9615	High Similarity	NPC469696
0.9453	High Similarity	NPC476407
0.92	High Similarity	NPC471067
0.9167	High Similarity	NPC180171
0.9167	High Similarity	NPC103398
0.9167	High Similarity	NPC158325
0.9127	High Similarity	NPC178449
0.9127	High Similarity	NPC470907
0.9127	High Similarity	NPC232454
0.904	High Similarity	NPC469703
0.904	High Similarity	NPC201402
0.904	High Similarity	NPC160854
0.904	High Similarity	NPC469704
0.8968	High Similarity	NPC469686
0.8905	High Similarity	NPC148080
0.8905	High Similarity	NPC469623
0.8855	High Similarity	NPC469549
0.8846	High Similarity	NPC469687
0.881	High Similarity	NPC469702
0.881	High Similarity	NPC282409
0.8741	High Similarity	NPC123988
0.874	High Similarity	NPC476448
0.874	High Similarity	NPC476445
0.874	High Similarity	NPC469548
0.8722	High Similarity	NPC478255
0.8705	High Similarity	NPC478250
0.8676	High Similarity	NPC471345
0.8636	High Similarity	NPC225307
0.8613	High Similarity	NPC310252
0.8613	High Similarity	NPC100558
0.8613	High Similarity	NPC302583
0.8613	High Similarity	NPC84789
0.8582	High Similarity	NPC281798
0.8561	High Similarity	NPC264900
0.8561	High Similarity	NPC288416
0.8561	High Similarity	NPC231607
0.8561	High Similarity	NPC108659
0.8561	High Similarity	NPC79715
0.855	High Similarity	NPC123704
0.8531	High Similarity	NPC473138
0.8531	High Similarity	NPC28776
0.8531	High Similarity	NPC120728
0.8527	High Similarity	NPC55608
0.8521	High Similarity	NPC212808
0.8492	Intermediate Similarity	NPC148055
0.8485	Intermediate Similarity	NPC94179
0.848	Intermediate Similarity	NPC157338
0.8462	Intermediate Similarity	NPC469927
0.8444	Intermediate Similarity	NPC235294
0.8444	Intermediate Similarity	NPC46137
0.8433	Intermediate Similarity	NPC184092
0.8414	Intermediate Similarity	NPC35097
0.8403	Intermediate Similarity	NPC116229
0.8397	Intermediate Similarity	NPC236981
0.8394	Intermediate Similarity	NPC169398
0.838	Intermediate Similarity	NPC194938
0.838	Intermediate Similarity	NPC296659
0.838	Intermediate Similarity	NPC202391
0.8333	Intermediate Similarity	NPC470330
0.8322	Intermediate Similarity	NPC475528
0.8321	Intermediate Similarity	NPC28637
0.8309	Intermediate Similarity	NPC246869
0.8309	Intermediate Similarity	NPC138777
0.8309	Intermediate Similarity	NPC225384
0.8286	Intermediate Similarity	NPC171134
0.8286	Intermediate Similarity	NPC324262
0.8286	Intermediate Similarity	NPC62800
0.8286	Intermediate Similarity	NPC321638
0.8286	Intermediate Similarity	NPC328273
0.8286	Intermediate Similarity	NPC321184
0.8284	Intermediate Similarity	NPC471881
0.8284	Intermediate Similarity	NPC471882
0.8284	Intermediate Similarity	NPC156692
0.8284	Intermediate Similarity	NPC45224
0.8284	Intermediate Similarity	NPC173150
0.8284	Intermediate Similarity	NPC35288
0.8271	Intermediate Similarity	NPC90318
0.8271	Intermediate Similarity	NPC83218
0.8271	Intermediate Similarity	NPC126991
0.8264	Intermediate Similarity	NPC143246
0.8264	Intermediate Similarity	NPC119773
0.8264	Intermediate Similarity	NPC474268
0.8264	Intermediate Similarity	NPC475539
0.8264	Intermediate Similarity	NPC473147
0.8248	Intermediate Similarity	NPC254275
0.8243	Intermediate Similarity	NPC245615
0.8243	Intermediate Similarity	NPC257847
0.8243	Intermediate Similarity	NPC61604
0.8243	Intermediate Similarity	NPC259182
0.8243	Intermediate Similarity	NPC121001
0.8243	Intermediate Similarity	NPC299706
0.8243	Intermediate Similarity	NPC115466
0.8243	Intermediate Similarity	NPC87403
0.824	Intermediate Similarity	NPC177576
0.8222	Intermediate Similarity	NPC148982
0.8219	Intermediate Similarity	NPC287294
0.8214	Intermediate Similarity	NPC101686
0.8214	Intermediate Similarity	NPC469364
0.8214	Intermediate Similarity	NPC65262
0.8209	Intermediate Similarity	NPC471157
0.8209	Intermediate Similarity	NPC252114
0.8209	Intermediate Similarity	NPC61181
0.8203	Intermediate Similarity	NPC473556
0.8203	Intermediate Similarity	NPC301651
0.8203	Intermediate Similarity	NPC175771
0.8201	Intermediate Similarity	NPC263829
0.82	Intermediate Similarity	NPC265480
0.82	Intermediate Similarity	NPC478055
0.82	Intermediate Similarity	NPC149368
0.8189	Intermediate Similarity	NPC313193
0.8188	Intermediate Similarity	NPC160882
0.8188	Intermediate Similarity	NPC106625
0.8182	Intermediate Similarity	NPC52097
0.8176	Intermediate Similarity	NPC106818
0.8163	Intermediate Similarity	NPC12006
0.8163	Intermediate Similarity	NPC158635
0.8163	Intermediate Similarity	NPC229882
0.816	Intermediate Similarity	NPC252544
0.816	Intermediate Similarity	NPC321252
0.8158	Intermediate Similarity	NPC130489
0.8158	Intermediate Similarity	NPC200708
0.8158	Intermediate Similarity	NPC208676
0.8156	Intermediate Similarity	NPC220942
0.8151	Intermediate Similarity	NPC472339
0.8148	Intermediate Similarity	NPC106677
0.8148	Intermediate Similarity	NPC103533
0.8146	Intermediate Similarity	NPC122809
0.8143	Intermediate Similarity	NPC470572
0.8143	Intermediate Similarity	NPC472132
0.8138	Intermediate Similarity	NPC291153
0.8133	Intermediate Similarity	NPC99233
0.8133	Intermediate Similarity	NPC97052
0.8133	Intermediate Similarity	NPC169248
0.8133	Intermediate Similarity	NPC39351
0.8133	Intermediate Similarity	NPC26195
0.8133	Intermediate Similarity	NPC72649
0.8133	Intermediate Similarity	NPC131532
0.8133	Intermediate Similarity	NPC38699
0.8129	Intermediate Similarity	NPC886
0.8129	Intermediate Similarity	NPC287597
0.8129	Intermediate Similarity	NPC34293
0.8125	Intermediate Similarity	NPC63304
0.8121	Intermediate Similarity	NPC259767
0.8121	Intermediate Similarity	NPC88484
0.8108	Intermediate Similarity	NPC474620
0.8106	Intermediate Similarity	NPC11724
0.8106	Intermediate Similarity	NPC266045
0.8095	Intermediate Similarity	NPC96599
0.8085	Intermediate Similarity	NPC260425
0.8079	Intermediate Similarity	NPC206378
0.8079	Intermediate Similarity	NPC163635
0.8079	Intermediate Similarity	NPC170475
0.8079	Intermediate Similarity	NPC127406
0.8067	Intermediate Similarity	NPC83283
0.8067	Intermediate Similarity	NPC143851
0.8067	Intermediate Similarity	NPC476194
0.8067	Intermediate Similarity	NPC29763
0.8067	Intermediate Similarity	NPC39360
0.8067	Intermediate Similarity	NPC210003
0.8058	Intermediate Similarity	NPC114116
0.8056	Intermediate Similarity	NPC40305
0.8056	Intermediate Similarity	NPC105005
0.8047	Intermediate Similarity	NPC285350
0.8042	Intermediate Similarity	NPC472711
0.8041	Intermediate Similarity	NPC240592
0.8041	Intermediate Similarity	NPC117346
0.8039	Intermediate Similarity	NPC271270
0.8039	Intermediate Similarity	NPC142860
0.8039	Intermediate Similarity	NPC97285
0.8039	Intermediate Similarity	NPC246469
0.803	Intermediate Similarity	NPC476872
0.8029	Intermediate Similarity	NPC11025
0.8029	Intermediate Similarity	NPC214246
0.8029	Intermediate Similarity	NPC253595
0.8028	Intermediate Similarity	NPC68092
0.8028	Intermediate Similarity	NPC197316
0.8028	Intermediate Similarity	NPC81515
0.8028	Intermediate Similarity	NPC64141
0.8028	Intermediate Similarity	NPC220936
0.8028	Intermediate Similarity	NPC476383
0.8028	Intermediate Similarity	NPC89105
0.8028	Intermediate Similarity	NPC31745
0.8028	Intermediate Similarity	NPC205195
0.8028	Intermediate Similarity	NPC472350
0.8026	Intermediate Similarity	NPC288084
0.8026	Intermediate Similarity	NPC23817
0.8026	Intermediate Similarity	NPC177742
0.8026	Intermediate Similarity	NPC197896
0.8026	Intermediate Similarity	NPC156457
0.8026	Intermediate Similarity	NPC161749
0.8026	Intermediate Similarity	NPC6985
0.8026	Intermediate Similarity	NPC43638
0.8026	Intermediate Similarity	NPC313163
0.8026	Intermediate Similarity	NPC258035

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 NPC471066 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	238
0.1-0.2	672
0.2-0.3	1353
0.3-0.4	2763
0.4-0.5	2445
0.5-0.6	1243
0.6-0.7	402
0.7-0.8	34
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8028	Intermediate Similarity	NPD7266	Discontinued
0.8026	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD3818	Discontinued
0.7712	Intermediate Similarity	NPD8455	Phase 2
0.7688	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD6559	Discontinued
0.764	Intermediate Similarity	NPD7074	Phase 3
0.7632	Intermediate Similarity	NPD4380	Phase 2
0.7578	Intermediate Similarity	NPD7054	Approved
0.7531	Intermediate Similarity	NPD7472	Approved
0.7516	Intermediate Similarity	NPD7228	Approved
0.745	Intermediate Similarity	NPD6190	Approved
0.7448	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD1091	Approved
0.7439	Intermediate Similarity	NPD7251	Discontinued
0.7419	Intermediate Similarity	NPD37	Approved
0.7405	Intermediate Similarity	NPD6234	Discontinued
0.7394	Intermediate Similarity	NPD7808	Phase 3
0.7389	Intermediate Similarity	NPD4966	Approved
0.7389	Intermediate Similarity	NPD4965	Approved
0.7389	Intermediate Similarity	NPD4967	Phase 2
0.7378	Intermediate Similarity	NPD6797	Phase 2
0.7351	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD7075	Discontinued
0.7299	Intermediate Similarity	NPD5125	Phase 3
0.7299	Intermediate Similarity	NPD5126	Approved
0.7297	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6233	Phase 2
0.7289	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD7033	Discontinued
0.7248	Intermediate Similarity	NPD1549	Phase 2
0.7246	Intermediate Similarity	NPD8312	Approved
0.7246	Intermediate Similarity	NPD8313	Approved
0.7222	Intermediate Similarity	NPD6798	Discontinued
0.7222	Intermediate Similarity	NPD3764	Approved
0.7197	Intermediate Similarity	NPD1934	Approved
0.7192	Intermediate Similarity	NPD6355	Discontinued
0.7171	Intermediate Similarity	NPD5058	Phase 3
0.7152	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD4628	Phase 3
0.7152	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3400	Discontinued
0.7126	Intermediate Similarity	NPD7685	Pre-registration
0.7126	Intermediate Similarity	NPD7240	Approved
0.7123	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7199	Phase 2
0.7097	Intermediate Similarity	NPD5403	Approved
0.7095	Intermediate Similarity	NPD7097	Phase 1
0.7089	Intermediate Similarity	NPD6801	Discontinued
0.7078	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD5048	Discontinued
0.7073	Intermediate Similarity	NPD6166	Phase 2
0.7073	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD3787	Discontinued
0.7055	Intermediate Similarity	NPD6663	Approved
0.7052	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD1510	Phase 2
0.7034	Intermediate Similarity	NPD3027	Phase 3
0.7014	Intermediate Similarity	NPD5736	Approved
0.7007	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1613	Approved
0.7	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD2859	Approved
0.6984	Remote Similarity	NPD2860	Approved
0.6968	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD5401	Approved
0.6957	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5647	Approved
0.6943	Remote Similarity	NPD1653	Approved
0.6939	Remote Similarity	NPD4062	Phase 3
0.6933	Remote Similarity	NPD5588	Approved
0.6929	Remote Similarity	NPD2932	Approved
0.6929	Remote Similarity	NPD3019	Approved
0.6918	Remote Similarity	NPD7411	Suspended
0.6909	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD9545	Approved
0.6905	Remote Similarity	NPD2934	Approved
0.6905	Remote Similarity	NPD2933	Approved
0.6903	Remote Similarity	NPD6799	Approved
0.6897	Remote Similarity	NPD2861	Phase 2
0.6894	Remote Similarity	NPD5402	Approved
0.6892	Remote Similarity	NPD943	Approved
0.6892	Remote Similarity	NPD1240	Approved
0.6886	Remote Similarity	NPD3751	Discontinued
0.6875	Remote Similarity	NPD3094	Phase 2
0.6863	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD2629	Approved
0.6859	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD3882	Suspended
0.6838	Remote Similarity	NPD7843	Approved
0.6832	Remote Similarity	NPD7819	Suspended
0.6832	Remote Similarity	NPD2801	Approved
0.6831	Remote Similarity	NPD1201	Approved
0.6831	Remote Similarity	NPD1535	Discovery
0.6822	Remote Similarity	NPD3020	Approved
0.6818	Remote Similarity	NPD8166	Discontinued
0.6818	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.68	Remote Similarity	NPD1607	Approved
0.6795	Remote Similarity	NPD1511	Approved
0.6792	Remote Similarity	NPD7458	Discontinued
0.679	Remote Similarity	NPD3817	Phase 2
0.6786	Remote Similarity	NPD1894	Discontinued
0.6783	Remote Similarity	NPD1481	Phase 2
0.678	Remote Similarity	NPD6534	Approved
0.678	Remote Similarity	NPD6535	Approved
0.6776	Remote Similarity	NPD9570	Approved
0.6776	Remote Similarity	NPD2796	Approved
0.6776	Remote Similarity	NPD2935	Discontinued
0.6765	Remote Similarity	NPD969	Suspended
0.676	Remote Similarity	NPD7700	Phase 2
0.676	Remote Similarity	NPD7699	Phase 2
0.6759	Remote Similarity	NPD1470	Approved
0.6755	Remote Similarity	NPD4538	Approved
0.6755	Remote Similarity	NPD4536	Approved
0.6755	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD6674	Discontinued
0.6752	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6599	Discontinued
0.6743	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD3021	Approved
0.6741	Remote Similarity	NPD3022	Approved
0.6735	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD4908	Phase 1
0.6732	Remote Similarity	NPD6005	Phase 3
0.6732	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD6004	Phase 3
0.6732	Remote Similarity	NPD6002	Phase 3
0.6722	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD3092	Approved
0.6713	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD1610	Phase 2
0.6713	Remote Similarity	NPD3705	Approved
0.6712	Remote Similarity	NPD2798	Approved
0.6711	Remote Similarity	NPD5960	Phase 3
0.671	Remote Similarity	NPD2575	Approved
0.671	Remote Similarity	NPD3750	Approved
0.6709	Remote Similarity	NPD1512	Approved
0.6703	Remote Similarity	NPD6823	Phase 2
0.6691	Remote Similarity	NPD7157	Approved
0.6689	Remote Similarity	NPD6653	Approved
0.6689	Remote Similarity	NPD7095	Approved
0.6689	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD5958	Discontinued
0.6688	Remote Similarity	NPD2424	Discontinued
0.6685	Remote Similarity	NPD6781	Approved
0.6685	Remote Similarity	NPD6777	Approved
0.6685	Remote Similarity	NPD6778	Approved
0.6685	Remote Similarity	NPD6780	Approved
0.6685	Remote Similarity	NPD6779	Approved
0.6685	Remote Similarity	NPD6782	Approved
0.6685	Remote Similarity	NPD6776	Approved
0.6667	Remote Similarity	NPD7680	Approved
0.6667	Remote Similarity	NPD5408	Approved
0.6667	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7435	Discontinued
0.6667	Remote Similarity	NPD1548	Phase 1
0.6667	Remote Similarity	NPD5404	Approved
0.6667	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5405	Approved
0.6667	Remote Similarity	NPD2684	Approved
0.6667	Remote Similarity	NPD5406	Approved
0.6649	Remote Similarity	NPD7584	Approved
0.6646	Remote Similarity	NPD7768	Phase 2
0.6646	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD2797	Approved
0.6644	Remote Similarity	NPD3268	Approved
0.6644	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD1164	Approved
0.6643	Remote Similarity	NPD3847	Discontinued
0.663	Remote Similarity	NPD8319	Approved
0.663	Remote Similarity	NPD8320	Phase 1
0.6629	Remote Similarity	NPD6212	Phase 3
0.6629	Remote Similarity	NPD6213	Phase 3
0.6629	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD8434	Phase 2
0.6629	Remote Similarity	NPD8150	Discontinued
0.6627	Remote Similarity	NPD7473	Discontinued
0.6627	Remote Similarity	NPD5494	Approved
0.6623	Remote Similarity	NPD4340	Discontinued
0.6623	Remote Similarity	NPD230	Phase 1
0.6623	Remote Similarity	NPD1933	Approved
0.6622	Remote Similarity	NPD6832	Phase 2
0.6621	Remote Similarity	NPD4659	Approved
0.6621	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.662	Remote Similarity	NPD1357	Approved
0.6617	Remote Similarity	NPD1237	Approved
0.6615	Remote Similarity	NPD9495	Approved
0.6609	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD3749	Approved
0.66	Remote Similarity	NPD6407	Approved
0.66	Remote Similarity	NPD6405	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