NPASS Compound

Structure

NPC473576 OpenBabel07101718292D 41 46 0 0 1 0 0 0 0 0999 V2000 4.1497 -7.1875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6395 -7.6667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2888 -2.5242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7679 -3.3542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3091 -2.2674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7883 -1.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8299 -4.3125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6599 -3.8333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9796 -7.6667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3198 -1.9167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4898 -1.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8299 -3.3542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4898 -4.3125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8299 -0.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3198 -4.7917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9796 -2.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8096 -4.3125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8299 -0.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8096 -7.1875 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.3198 -2.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1497 -3.3542 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.9167 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6599 -1.9167 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9796 -4.7917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8096 -6.2292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1497 -6.2292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8096 -3.3542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8299 -1.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4898 -3.3542 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6599 -2.8750 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8299 -1.4375 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1497 -4.3125 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8299 -0.4792 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.6395 -5.7500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9796 -6.7083 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3198 -6.7083 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7883 -0.4792 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 4.9796 -5.7500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 21 1 0 0 0 0 3 29 1 0 0 0 0 4 29 1 0 0 0 0 5 30 1 0 0 0 0 6 30 1 0 0 0 0 7 31 1 0 0 0 0 9 21 1 0 0 0 0 10 11 1 0 0 0 0 10 22 2 0 0 0 0 11 25 1 0 0 0 0 12 13 1 0 0 0 0 12 24 1 0 0 0 0 13 32 1 0 0 0 0 14 16 1 0 0 0 0 14 31 1 0 0 0 0 15 17 1 0 0 0 0 16 34 1 0 0 0 0 18 23 1 0 0 0 0 18 29 1 0 0 0 0 19 26 1 0 0 0 0 19 29 1 0 0 0 0 20 33 1 0 0 0 0 20 40 1 0 0 0 0 21 27 1 0 0 0 0 22 23 1 0 0 0 0 22 31 1 0 0 0 0 23 34 1 6 0 0 0 24 30 1 0 0 0 0 24 33 1 1 0 0 0 25 32 1 1 0 0 0 25 33 1 0 0 0 0 26 34 1 1 0 0 0 26 41 1 0 0 0 0 27 36 2 0 0 0 0 27 41 1 0 0 0 0 28 37 2 0 0 0 0 28 38 1 0 0 0 0 30 35 1 0 0 0 0 31 32 1 1 0 0 0 32 8 1 1 0 0 0 33 15 1 6 0 0 0 34 28 1 1 0 0 0 35 17 1 6 0 0 0 35 39 1 0 0 0 0 35 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	570.39
Volume:	607.409
LogP:	6.569
LogD:	4.695
LogS:	-5.286
# Rotatable Bonds:	5
TPSA:	93.06
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	7
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.276
Synthetic Accessibility Score:	6.475
Fsp3:	0.886
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:	-5.412
MDCK Permeability:	1.8699236534303054e-05
Pgp-inhibitor:	0.246
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	0.09
30% Bioavailability (F30%):	0.263

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.808
Plasma Protein Binding (PPB):	90.56620788574219%
Volume Distribution (VD):	0.969
Pgp-substrate:	5.894953727722168%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.68
CYP2C19-inhibitor:	0.041
CYP2C19-substrate:	0.777
CYP2C9-inhibitor:	0.242
CYP2C9-substrate:	0.053
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.075
CYP3A4-inhibitor:	0.719
CYP3A4-substrate:	0.452

ADMET: Excretion

Clearance (CL):	10.778
Half-life (T1/2):	0.023

ADMET: Toxicity

hERG Blockers:	0.071
Human Hepatotoxicity (H-HT):	0.395
Drug-inuced Liver Injury (DILI):	0.026
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.53
Maximum Recommended Daily Dose:	0.921
Skin Sensitization:	0.08
Carcinogencity:	0.58
Eye Corrosion:	0.007
Eye Irritation:	0.016
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC473576

Natural Product ID:	NPC473576
*Common Name:**	WVLBJJGQOYFFGO-WABPBFBFSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WVLBJJGQOYFFGO-WABPBFBFSA-N
Standard InCHI:	InChI=1S/C35H54O6/c1-9-21(2)27(36)41-26-19-29(3,4)18-23-22-10-11-25-32(8,31(22,7)14-16-34(23,26)28(37)38)13-12-24-30(5,6)35(39)17-15-33(24,25)20-40-35/h10,21,23-26,39H,9,11-20H2,1-8H3,(H,37,38)/t21?,23-,24-,25-,26+,31+,32+,33+,34-,35-/m0/s1
SMILES:	CCC(C)C(=O)OC1CC(CC2C1(CCC3(C2=CCC4C3(CCC5C46CCC(C5(C)C)(OC6)O)C)C)C(=O)O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL446232
PubChem CID:	21592384
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO6442	Lippia turbinata	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170663]
NPO6442	Lippia turbinata	Species	Verbenaceae	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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	128000.0	nM	PMID[543777]

☑ 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 NPC473576 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	237
0.1-0.2	1572
0.2-0.3	5037
0.3-0.4	11818
0.4-0.5	11088
0.5-0.6	5562
0.6-0.7	4666
0.7-0.8	1923
0.8-0.85	366
0.85-0.9	403
0.9-0.95	23
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475156
0.9457	High Similarity	NPC474963
0.9388	High Similarity	NPC475570
0.9293	High Similarity	NPC473483
0.9247	High Similarity	NPC23621
0.9247	High Similarity	NPC184006
0.9247	High Similarity	NPC78580
0.9158	High Similarity	NPC158347
0.9149	High Similarity	NPC195715
0.9149	High Similarity	NPC23241
0.8958	High Similarity	NPC476879
0.8958	High Similarity	NPC476878
0.8958	High Similarity	NPC26413
0.8947	High Similarity	NPC474727
0.8936	High Similarity	NPC86368
0.8932	High Similarity	NPC80843
0.8932	High Similarity	NPC1046
0.8925	High Similarity	NPC113989
0.8925	High Similarity	NPC120840
0.8846	High Similarity	NPC238935
0.8846	High Similarity	NPC475208
0.8835	High Similarity	NPC31839
0.883	High Similarity	NPC470590
0.883	High Similarity	NPC288833
0.883	High Similarity	NPC77099
0.883	High Similarity	NPC282616
0.883	High Similarity	NPC285184
0.883	High Similarity	NPC60755
0.883	High Similarity	NPC228784
0.883	High Similarity	NPC966
0.883	High Similarity	NPC155120
0.883	High Similarity	NPC324341
0.8817	High Similarity	NPC30522
0.8762	High Similarity	NPC164389
0.8762	High Similarity	NPC475486
0.875	High Similarity	NPC48249
0.8738	High Similarity	NPC270667
0.8738	High Similarity	NPC136877
0.8738	High Similarity	NPC56713
0.8738	High Similarity	NPC29069
0.8738	High Similarity	NPC474589
0.8738	High Similarity	NPC164194
0.8738	High Similarity	NPC90856
0.8738	High Similarity	NPC242611
0.8738	High Similarity	NPC269095
0.8738	High Similarity	NPC127056
0.8738	High Similarity	NPC78046
0.8738	High Similarity	NPC59804
0.8738	High Similarity	NPC475296
0.8738	High Similarity	NPC174679
0.8738	High Similarity	NPC279554
0.8723	High Similarity	NPC86372
0.8723	High Similarity	NPC474728
0.8723	High Similarity	NPC172361
0.8713	High Similarity	NPC475611
0.8679	High Similarity	NPC37134
0.8679	High Similarity	NPC288205
0.8679	High Similarity	NPC26626
0.8679	High Similarity	NPC44170
0.8679	High Similarity	NPC51465
0.8679	High Similarity	NPC75287
0.8679	High Similarity	NPC291903
0.8679	High Similarity	NPC476992
0.8679	High Similarity	NPC305267
0.8673	High Similarity	NPC58942
0.8673	High Similarity	NPC164349
0.8673	High Similarity	NPC260149
0.866	High Similarity	NPC98874
0.8654	High Similarity	NPC211798
0.8654	High Similarity	NPC235841
0.8654	High Similarity	NPC164419
0.8654	High Similarity	NPC473481
0.8654	High Similarity	NPC297208
0.8654	High Similarity	NPC108748
0.8654	High Similarity	NPC30397
0.8654	High Similarity	NPC179434
0.8646	High Similarity	NPC222047
0.8646	High Similarity	NPC74751
0.8646	High Similarity	NPC296164
0.8646	High Similarity	NPC159365
0.8641	High Similarity	NPC204407
0.8641	High Similarity	NPC306746
0.8641	High Similarity	NPC167383
0.8641	High Similarity	NPC137917
0.8641	High Similarity	NPC237503
0.8641	High Similarity	NPC57362
0.8632	High Similarity	NPC6255
0.8632	High Similarity	NPC471588
0.8632	High Similarity	NPC475708
0.8627	High Similarity	NPC473538
0.8627	High Similarity	NPC283849
0.8617	High Similarity	NPC293048
0.8617	High Similarity	NPC234346
0.8617	High Similarity	NPC270768
0.8617	High Similarity	NPC61543
0.8617	High Similarity	NPC59263
0.8617	High Similarity	NPC130520
0.8617	High Similarity	NPC121798
0.8617	High Similarity	NPC263393
0.8617	High Similarity	NPC225585
0.8617	High Similarity	NPC127689
0.8602	High Similarity	NPC46912
0.8602	High Similarity	NPC162107
0.8598	High Similarity	NPC473824
0.8598	High Similarity	NPC220160
0.8598	High Similarity	NPC309223
0.8598	High Similarity	NPC300419
0.8598	High Similarity	NPC191827
0.8598	High Similarity	NPC323359
0.8598	High Similarity	NPC104137
0.8598	High Similarity	NPC102505
0.8598	High Similarity	NPC123522
0.8598	High Similarity	NPC69811
0.8598	High Similarity	NPC475514
0.8598	High Similarity	NPC33012
0.8598	High Similarity	NPC286457
0.8598	High Similarity	NPC473452
0.8598	High Similarity	NPC470876
0.8598	High Similarity	NPC8524
0.8598	High Similarity	NPC475119
0.8598	High Similarity	NPC475209
0.8598	High Similarity	NPC85154
0.8585	High Similarity	NPC110861
0.8571	High Similarity	NPC139894
0.8571	High Similarity	NPC104400
0.8571	High Similarity	NPC324875
0.8571	High Similarity	NPC475516
0.8571	High Similarity	NPC104071
0.8571	High Similarity	NPC473383
0.8571	High Similarity	NPC256798
0.8571	High Similarity	NPC276093
0.8571	High Similarity	NPC292677
0.8571	High Similarity	NPC473373
0.8571	High Similarity	NPC471383
0.8571	High Similarity	NPC128925
0.8571	High Similarity	NPC101744
0.8571	High Similarity	NPC475504
0.8571	High Similarity	NPC100383
0.8571	High Similarity	NPC102439
0.8571	High Similarity	NPC79718
0.8571	High Similarity	NPC139044
0.8571	High Similarity	NPC109079
0.8571	High Similarity	NPC10320
0.8571	High Similarity	NPC469946
0.8571	High Similarity	NPC257468
0.8558	High Similarity	NPC476880
0.8558	High Similarity	NPC7870
0.8558	High Similarity	NPC199457
0.8558	High Similarity	NPC75747
0.8558	High Similarity	NPC476886
0.8558	High Similarity	NPC476883
0.8558	High Similarity	NPC110139
0.8558	High Similarity	NPC476885
0.8558	High Similarity	NPC68419
0.8558	High Similarity	NPC274507
0.8558	High Similarity	NPC220984
0.8558	High Similarity	NPC476882
0.8558	High Similarity	NPC476884
0.8558	High Similarity	NPC102914
0.8558	High Similarity	NPC108709
0.8558	High Similarity	NPC476887
0.8558	High Similarity	NPC476881
0.8557	High Similarity	NPC148523
0.8544	High Similarity	NPC476123
0.8544	High Similarity	NPC284807
0.8544	High Similarity	NPC177246
0.8544	High Similarity	NPC28198
0.8542	High Similarity	NPC298554
0.8526	High Similarity	NPC470589
0.8526	High Similarity	NPC126369
0.8526	High Similarity	NPC130278
0.8526	High Similarity	NPC111110
0.8519	High Similarity	NPC473459
0.8519	High Similarity	NPC105800
0.8519	High Similarity	NPC232237
0.8519	High Similarity	NPC237191
0.8511	High Similarity	NPC52169
0.8511	High Similarity	NPC40552
0.8511	High Similarity	NPC182797
0.8511	High Similarity	NPC246708
0.8505	High Similarity	NPC268954
0.85	High Similarity	NPC476888
0.85	High Similarity	NPC93744
0.8495	Intermediate Similarity	NPC91525
0.8495	Intermediate Similarity	NPC325594
0.8495	Intermediate Similarity	NPC10005
0.8495	Intermediate Similarity	NPC329943
0.8495	Intermediate Similarity	NPC9892
0.8491	Intermediate Similarity	NPC114304
0.8491	Intermediate Similarity	NPC150400
0.8491	Intermediate Similarity	NPC258885
0.8491	Intermediate Similarity	NPC204458
0.8491	Intermediate Similarity	NPC96641
0.8491	Intermediate Similarity	NPC124296
0.8491	Intermediate Similarity	NPC174720
0.8491	Intermediate Similarity	NPC241909
0.8491	Intermediate Similarity	NPC189884
0.8491	Intermediate Similarity	NPC295823
0.8491	Intermediate Similarity	NPC473826
0.8491	Intermediate Similarity	NPC155410

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 NPC473576 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	211
0.1-0.2	1848
0.2-0.3	3887
0.3-0.4	2132
0.4-0.5	634
0.5-0.6	250
0.6-0.7	157
0.7-0.8	24
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8646	High Similarity	NPD7748	Approved
0.8384	Intermediate Similarity	NPD7902	Approved
0.8247	Intermediate Similarity	NPD7515	Phase 2
0.8142	Intermediate Similarity	NPD8328	Phase 3
0.8091	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.8081	Intermediate Similarity	NPD7900	Approved
0.8081	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7944	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.77	Intermediate Similarity	NPD8035	Phase 2
0.77	Intermediate Similarity	NPD6411	Approved
0.77	Intermediate Similarity	NPD8034	Phase 2
0.7624	Intermediate Similarity	NPD6399	Phase 3
0.7596	Intermediate Similarity	NPD7638	Approved
0.7553	Intermediate Similarity	NPD7645	Phase 2
0.7524	Intermediate Similarity	NPD7640	Approved
0.7524	Intermediate Similarity	NPD7639	Approved
0.75	Intermediate Similarity	NPD6101	Approved
0.75	Intermediate Similarity	NPD8133	Approved
0.75	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD6412	Phase 2
0.7417	Intermediate Similarity	NPD7736	Approved
0.74	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD7128	Approved
0.7339	Intermediate Similarity	NPD5739	Approved
0.7339	Intermediate Similarity	NPD6675	Approved
0.7339	Intermediate Similarity	NPD6402	Approved
0.73	Intermediate Similarity	NPD3573	Approved
0.7282	Intermediate Similarity	NPD5778	Approved
0.7282	Intermediate Similarity	NPD5779	Approved
0.7257	Intermediate Similarity	NPD6882	Approved
0.7213	Intermediate Similarity	NPD7319	Approved
0.7207	Intermediate Similarity	NPD6881	Approved
0.7207	Intermediate Similarity	NPD6899	Approved
0.7207	Intermediate Similarity	NPD6686	Approved
0.7207	Intermediate Similarity	NPD7320	Approved
0.72	Intermediate Similarity	NPD6684	Approved
0.72	Intermediate Similarity	NPD7334	Approved
0.72	Intermediate Similarity	NPD7146	Approved
0.72	Intermediate Similarity	NPD7521	Approved
0.72	Intermediate Similarity	NPD6409	Approved
0.72	Intermediate Similarity	NPD3618	Phase 1
0.72	Intermediate Similarity	NPD5330	Approved
0.719	Intermediate Similarity	NPD8293	Discontinued
0.7172	Intermediate Similarity	NPD4786	Approved
0.717	Intermediate Similarity	NPD6083	Phase 2
0.717	Intermediate Similarity	NPD6084	Phase 2
0.7168	Intermediate Similarity	NPD8130	Phase 1
0.7167	Intermediate Similarity	NPD7492	Approved
0.7157	Intermediate Similarity	NPD5328	Approved
0.7157	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD7115	Discovery
0.7143	Intermediate Similarity	NPD6373	Approved
0.7143	Intermediate Similarity	NPD6372	Approved
0.7143	Intermediate Similarity	NPD3667	Approved
0.7119	Intermediate Similarity	NPD8294	Approved
0.7119	Intermediate Similarity	NPD6059	Approved
0.7119	Intermediate Similarity	NPD6054	Approved
0.7119	Intermediate Similarity	NPD8377	Approved
0.7117	Intermediate Similarity	NPD5701	Approved
0.7117	Intermediate Similarity	NPD5697	Approved
0.7107	Intermediate Similarity	NPD6616	Approved
0.7107	Intermediate Similarity	NPD7507	Approved
0.7105	Intermediate Similarity	NPD8297	Approved
0.708	Intermediate Similarity	NPD7102	Approved
0.708	Intermediate Similarity	NPD7290	Approved
0.708	Intermediate Similarity	NPD6883	Approved
0.7059	Intermediate Similarity	NPD8513	Phase 3
0.7059	Intermediate Similarity	NPD8516	Approved
0.7059	Intermediate Similarity	NPD8378	Approved
0.7059	Intermediate Similarity	NPD8517	Approved
0.7059	Intermediate Similarity	NPD8335	Approved
0.7059	Intermediate Similarity	NPD8380	Approved
0.7059	Intermediate Similarity	NPD8515	Approved
0.7059	Intermediate Similarity	NPD8033	Approved
0.7059	Intermediate Similarity	NPD8379	Approved
0.7059	Intermediate Similarity	NPD6672	Approved
0.7059	Intermediate Similarity	NPD8296	Approved
0.7059	Intermediate Similarity	NPD6903	Approved
0.7059	Intermediate Similarity	NPD5737	Approved
0.7054	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD7078	Approved
0.7019	Intermediate Similarity	NPD6079	Approved
0.7018	Intermediate Similarity	NPD6847	Approved
0.7018	Intermediate Similarity	NPD6649	Approved
0.7018	Intermediate Similarity	NPD6617	Approved
0.7018	Intermediate Similarity	NPD6650	Approved
0.7018	Intermediate Similarity	NPD6869	Approved
0.7	Intermediate Similarity	NPD6370	Approved
0.6991	Remote Similarity	NPD6013	Approved
0.6991	Remote Similarity	NPD6014	Approved
0.6991	Remote Similarity	NPD6012	Approved
0.6981	Remote Similarity	NPD5695	Phase 3
0.6975	Remote Similarity	NPD6319	Approved
0.6944	Remote Similarity	NPD5696	Approved
0.6944	Remote Similarity	NPD4225	Approved
0.6917	Remote Similarity	NPD6016	Approved
0.6917	Remote Similarity	NPD6015	Approved
0.6909	Remote Similarity	NPD7632	Discontinued
0.6907	Remote Similarity	NPD6115	Approved
0.6907	Remote Similarity	NPD6114	Approved
0.6907	Remote Similarity	NPD6697	Approved
0.6907	Remote Similarity	NPD6118	Approved
0.6903	Remote Similarity	NPD6011	Approved
0.6875	Remote Similarity	NPD6008	Approved
0.687	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD6009	Approved
0.6863	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.686	Remote Similarity	NPD5988	Approved
0.6857	Remote Similarity	NPD7637	Suspended
0.6852	Remote Similarity	NPD4755	Approved
0.6842	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD3666	Approved
0.6832	Remote Similarity	NPD3668	Phase 3
0.6832	Remote Similarity	NPD3133	Approved
0.6832	Remote Similarity	NPD3665	Phase 1
0.6822	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD7327	Approved
0.6807	Remote Similarity	NPD7328	Approved
0.6792	Remote Similarity	NPD4202	Approved
0.6783	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD4634	Approved
0.6768	Remote Similarity	NPD7525	Registered
0.6759	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5221	Approved
0.6759	Remote Similarity	NPD7732	Phase 3
0.6759	Remote Similarity	NPD7839	Suspended
0.6759	Remote Similarity	NPD7614	Phase 1
0.6759	Remote Similarity	NPD5222	Approved
0.6759	Remote Similarity	NPD4697	Phase 3
0.6752	Remote Similarity	NPD4632	Approved
0.675	Remote Similarity	NPD7516	Approved
0.6727	Remote Similarity	NPD4700	Approved
0.6727	Remote Similarity	NPD4696	Approved
0.6727	Remote Similarity	NPD5286	Approved
0.6727	Remote Similarity	NPD5285	Approved
0.6701	Remote Similarity	NPD6117	Approved
0.6699	Remote Similarity	NPD6098	Approved
0.6697	Remote Similarity	NPD5173	Approved
0.6667	Remote Similarity	NPD4753	Phase 2
0.6667	Remote Similarity	NPD6904	Approved
0.6667	Remote Similarity	NPD6080	Approved
0.6667	Remote Similarity	NPD6673	Approved
0.6639	Remote Similarity	NPD6868	Approved
0.6639	Remote Similarity	NPD7503	Approved
0.6639	Remote Similarity	NPD6274	Approved
0.6634	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD6116	Phase 1
0.6612	Remote Similarity	NPD7100	Approved
0.6612	Remote Similarity	NPD7101	Approved
0.6607	Remote Similarity	NPD5225	Approved
0.6607	Remote Similarity	NPD5224	Approved
0.6607	Remote Similarity	NPD5211	Phase 2
0.6607	Remote Similarity	NPD5226	Approved
0.6607	Remote Similarity	NPD4633	Approved
0.66	Remote Similarity	NPD4695	Discontinued
0.6587	Remote Similarity	NPD6033	Approved
0.6581	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD5174	Approved
0.6549	Remote Similarity	NPD5175	Approved
0.6532	Remote Similarity	NPD6067	Discontinued
0.6532	Remote Similarity	NPD7604	Phase 2
0.6529	Remote Similarity	NPD6335	Approved
0.6522	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD5223	Approved
0.6508	Remote Similarity	NPD8074	Phase 3
0.6504	Remote Similarity	NPD6908	Approved
0.6504	Remote Similarity	NPD6909	Approved
0.6504	Remote Similarity	NPD5983	Phase 2
0.6495	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD5141	Approved
0.6491	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4221	Approved
0.6471	Remote Similarity	NPD4223	Phase 3
0.6446	Remote Similarity	NPD6317	Approved
0.6442	Remote Similarity	NPD1694	Approved
0.6442	Remote Similarity	NPD5329	Approved
0.6435	Remote Similarity	NPD4768	Approved
0.6435	Remote Similarity	NPD4767	Approved
0.6429	Remote Similarity	NPD6942	Approved
0.6429	Remote Similarity	NPD7339	Approved
0.6429	Remote Similarity	NPD6336	Discontinued
0.6422	Remote Similarity	NPD6001	Approved
0.6422	Remote Similarity	NPD5282	Discontinued
0.6415	Remote Similarity	NPD5208	Approved
0.6404	Remote Similarity	NPD4754	Approved
0.6393	Remote Similarity	NPD6313	Approved
0.6393	Remote Similarity	NPD6314	Approved
0.6389	Remote Similarity	NPD5284	Approved
0.6389	Remote Similarity	NPD5693	Phase 1
0.6389	Remote Similarity	NPD5281	Approved
0.6389	Remote Similarity	NPD7983	Approved
0.6389	Remote Similarity	NPD6050	Approved
0.6381	Remote Similarity	NPD5279	Phase 3
0.6371	Remote Similarity	NPD6921	Approved
0.6364	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5210	Approved
0.6364	Remote Similarity	NPD4629	Approved
0.6355	Remote Similarity	NPD6051	Approved
0.6346	Remote Similarity	NPD4197	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