NPASS Compound

Structure

CID178853 OpenBabel06191715552D 35 40 0 0 1 0 0 0 0 0999 V2000 2.4271 2.7634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 2.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0880 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8966 1.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3200 -1.4430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3200 -3.1750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2219 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3559 -2.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7045 2.5823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1045 1.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9540 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8200 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2219 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -1.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9540 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7226 1.1810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6180 2.1756 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0880 -2.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3559 -1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2219 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4899 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3559 0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0880 -1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4899 0.1910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8200 -2.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3559 1.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1266 1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8200 -2.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3200 -3.1750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9135 0.5933 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 2 18 1 0 0 0 0 4 26 1 0 0 0 0 5 32 1 0 0 0 0 6 33 1 0 0 0 0 7 8 1 0 0 0 0 7 19 1 0 0 0 0 9 10 1 0 0 0 0 9 17 1 0 0 0 0 11 12 1 0 0 0 0 11 25 1 0 0 0 0 12 27 1 0 0 0 0 13 21 1 0 0 0 0 13 23 1 0 0 0 0 14 22 1 0 0 0 0 14 24 1 0 0 0 0 15 19 1 0 0 0 0 15 27 1 0 0 0 0 16 17 1 0 0 0 0 16 34 1 0 0 0 0 17 1 1 1 0 0 0 18 28 1 6 0 0 0 18 29 1 0 0 0 0 19 25 1 6 0 0 0 20 8 1 6 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 21 25 1 1 0 0 0 22 26 1 1 0 0 0 23 26 1 0 0 0 0 23 30 2 0 0 0 0 24 29 1 1 0 0 0 24 35 1 0 0 0 0 25 3 1 1 0 0 0 26 29 1 6 0 0 0 27 32 1 0 0 0 0 27 33 1 0 0 0 0 28 10 1 1 0 0 0 28 34 1 0 0 0 0 28 35 1 0 0 0 0 29 31 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	490.33
Volume:	508.906
LogP:	4.291
LogD:	3.852
LogS:	-4.391
# Rotatable Bonds:	2
TPSA:	74.22
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.565
Synthetic Accessibility Score:	5.817
Fsp3:	0.966
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.776
MDCK Permeability:	2.305058114870917e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.084
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.824
30% Bioavailability (F30%):	0.279

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.621
Plasma Protein Binding (PPB):	83.0335922241211%
Volume Distribution (VD):	1.092
Pgp-substrate:	2.6957201957702637%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.976
CYP2C19-inhibitor:	0.088
CYP2C19-substrate:	0.895
CYP2C9-inhibitor:	0.094
CYP2C9-substrate:	0.013
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.184
CYP3A4-inhibitor:	0.87
CYP3A4-substrate:	0.621

ADMET: Excretion

Clearance (CL):	11.355
Half-life (T1/2):	0.222

ADMET: Toxicity

hERG Blockers:	0.638
Human Hepatotoxicity (H-HT):	0.493
Drug-inuced Liver Injury (DILI):	0.286
AMES Toxicity:	0.096
Rat Oral Acute Toxicity:	0.673
Maximum Recommended Daily Dose:	0.522
Skin Sensitization:	0.953
Carcinogencity:	0.815
Eye Corrosion:	0.081
Eye Irritation:	0.097
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC178853

Natural Product ID:	NPC178853
*Common Name:**	Asparacosin B
IUPAC Name:	n.a.
Synonyms:	Asparacosin B
Standard InCHIKey:	FJZMHTUXQXEAPK-RSLKRIGASA-N
Standard InCHI:	InChI=1S/C29H46O6/c1-17-9-10-28(34-16-17)18(2)29(31)24(35-28)14-22-20-8-7-19-15-27(32-5,33-6)12-11-25(19,3)21(20)13-23(30)26(22,29)4/h17-22,24,31H,7-16H2,1-6H3/t17-,18-,19-,20-,21+,22+,24+,25+,26-,28-,29-/m1/s1
SMILES:	C[C@@H]1CC[C@@]2([C@@H](C)[C@]3([C@H](C[C@H]4[C@@H]5CC[C@@H]6CC(CC[C@]6(C)[C@H]5CC(=O)[C@]34C)(OC)OC)O2)O)OC1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL473454
PubChem CID:	21575013
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
NPO11694	Asparagus cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14987058]
NPO11694	Asparagus cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11694	Asparagus cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11694	Asparagus cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11694	Asparagus cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11694	Asparagus cochinchinensis	Species	Asparagaceae	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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[523241]
NPT1851	Cell Line	Col2	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[523241]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[523241]
NPT1034	Cell Line	Lu1	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[523241]
NPT737	Cell Line	HUVEC	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[523241]

☑ 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 NPC178853 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	484
0.1-0.2	3801
0.2-0.3	9086
0.3-0.4	13516
0.4-0.5	6468
0.5-0.6	4811
0.6-0.7	3353
0.7-0.8	1044
0.8-0.85	106
0.85-0.9	26
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9043	High Similarity	NPC161035
0.8932	High Similarity	NPC473062
0.8812	High Similarity	NPC215408
0.88	High Similarity	NPC107385
0.8763	High Similarity	NPC476728
0.8713	High Similarity	NPC470167
0.87	High Similarity	NPC470172
0.866	High Similarity	NPC305808
0.8641	High Similarity	NPC202898
0.8641	High Similarity	NPC92890
0.8641	High Similarity	NPC475319
0.8614	High Similarity	NPC471253
0.8614	High Similarity	NPC473406
0.8598	High Similarity	NPC475490
0.8571	High Similarity	NPC116683
0.8558	High Similarity	NPC233433
0.8558	High Similarity	NPC473817
0.8558	High Similarity	NPC220836
0.8558	High Similarity	NPC94086
0.8558	High Similarity	NPC273002
0.8558	High Similarity	NPC92297
0.8529	High Similarity	NPC100078
0.8515	High Similarity	NPC213528
0.8515	High Similarity	NPC244969
0.8505	High Similarity	NPC79193
0.85	High Similarity	NPC20028
0.8485	Intermediate Similarity	NPC471241
0.8447	Intermediate Similarity	NPC166079
0.8431	Intermediate Similarity	NPC34562
0.8416	Intermediate Similarity	NPC477172
0.8396	Intermediate Similarity	NPC469824
0.8349	Intermediate Similarity	NPC179429
0.8333	Intermediate Similarity	NPC61688
0.8333	Intermediate Similarity	NPC310031
0.8333	Intermediate Similarity	NPC471254
0.8333	Intermediate Similarity	NPC80191
0.8317	Intermediate Similarity	NPC41843
0.83	Intermediate Similarity	NPC472273
0.8283	Intermediate Similarity	NPC215570
0.8269	Intermediate Similarity	NPC306776
0.8265	Intermediate Similarity	NPC476189
0.8241	Intermediate Similarity	NPC97002
0.8211	Intermediate Similarity	NPC80700
0.82	Intermediate Similarity	NPC156377
0.82	Intermediate Similarity	NPC193785
0.8182	Intermediate Similarity	NPC470424
0.8182	Intermediate Similarity	NPC206878
0.8173	Intermediate Similarity	NPC88469
0.8172	Intermediate Similarity	NPC24556
0.8155	Intermediate Similarity	NPC80640
0.8148	Intermediate Similarity	NPC477489
0.8148	Intermediate Similarity	NPC477492
0.8144	Intermediate Similarity	NPC228059
0.8137	Intermediate Similarity	NPC80417
0.8113	Intermediate Similarity	NPC469826
0.8085	Intermediate Similarity	NPC268578
0.8085	Intermediate Similarity	NPC292458
0.8085	Intermediate Similarity	NPC217559
0.8073	Intermediate Similarity	NPC102619
0.8039	Intermediate Similarity	NPC253995
0.8037	Intermediate Similarity	NPC227879
0.8037	Intermediate Similarity	NPC208333
0.8037	Intermediate Similarity	NPC87393
0.8021	Intermediate Similarity	NPC474448
0.802	Intermediate Similarity	NPC475785
0.8019	Intermediate Similarity	NPC203974
0.8	Intermediate Similarity	NPC470423
0.8	Intermediate Similarity	NPC227260
0.8	Intermediate Similarity	NPC267637
0.7982	Intermediate Similarity	NPC471245
0.798	Intermediate Similarity	NPC59006
0.7979	Intermediate Similarity	NPC317066
0.7963	Intermediate Similarity	NPC470622
0.7963	Intermediate Similarity	NPC66513
0.7963	Intermediate Similarity	NPC106760
0.7959	Intermediate Similarity	NPC200580
0.7944	Intermediate Similarity	NPC55973
0.7938	Intermediate Similarity	NPC263802
0.7938	Intermediate Similarity	NPC161928
0.7938	Intermediate Similarity	NPC210658
0.7925	Intermediate Similarity	NPC273189
0.7925	Intermediate Similarity	NPC184805
0.7921	Intermediate Similarity	NPC473067
0.7921	Intermediate Similarity	NPC17336
0.7921	Intermediate Similarity	NPC473065
0.7921	Intermediate Similarity	NPC474399
0.7921	Intermediate Similarity	NPC473064
0.7917	Intermediate Similarity	NPC232044
0.7917	Intermediate Similarity	NPC273290
0.7909	Intermediate Similarity	NPC178981
0.7909	Intermediate Similarity	NPC471248
0.79	Intermediate Similarity	NPC182740
0.79	Intermediate Similarity	NPC256104
0.79	Intermediate Similarity	NPC472237
0.79	Intermediate Similarity	NPC211845
0.79	Intermediate Similarity	NPC311246
0.79	Intermediate Similarity	NPC472238
0.79	Intermediate Similarity	NPC122083
0.79	Intermediate Similarity	NPC167644
0.789	Intermediate Similarity	NPC272242
0.789	Intermediate Similarity	NPC122339
0.7879	Intermediate Similarity	NPC77756
0.7879	Intermediate Similarity	NPC473542
0.787	Intermediate Similarity	NPC228190
0.787	Intermediate Similarity	NPC236753
0.787	Intermediate Similarity	NPC469825
0.7864	Intermediate Similarity	NPC472144
0.7857	Intermediate Similarity	NPC477614
0.7857	Intermediate Similarity	NPC128475
0.7857	Intermediate Similarity	NPC226491
0.785	Intermediate Similarity	NPC67745
0.785	Intermediate Similarity	NPC471461
0.785	Intermediate Similarity	NPC471430
0.7849	Intermediate Similarity	NPC245029
0.7849	Intermediate Similarity	NPC31302
0.7843	Intermediate Similarity	NPC475765
0.7838	Intermediate Similarity	NPC470115
0.7838	Intermediate Similarity	NPC470116
0.7835	Intermediate Similarity	NPC476726
0.7835	Intermediate Similarity	NPC476727
0.7835	Intermediate Similarity	NPC472272
0.783	Intermediate Similarity	NPC469827
0.7822	Intermediate Similarity	NPC30687
0.7822	Intermediate Similarity	NPC309127
0.7822	Intermediate Similarity	NPC477224
0.7822	Intermediate Similarity	NPC45959
0.7822	Intermediate Similarity	NPC175
0.7822	Intermediate Similarity	NPC252253
0.7822	Intermediate Similarity	NPC247877
0.7822	Intermediate Similarity	NPC3538
0.7822	Intermediate Similarity	NPC113500
0.7822	Intermediate Similarity	NPC477495
0.7818	Intermediate Similarity	NPC471244
0.7818	Intermediate Similarity	NPC473303
0.7812	Intermediate Similarity	NPC50438
0.781	Intermediate Similarity	NPC114700
0.781	Intermediate Similarity	NPC134967
0.781	Intermediate Similarity	NPC470029
0.781	Intermediate Similarity	NPC310138
0.7807	Intermediate Similarity	NPC108072
0.78	Intermediate Similarity	NPC149966
0.78	Intermediate Similarity	NPC5632
0.78	Intermediate Similarity	NPC36372
0.78	Intermediate Similarity	NPC475878
0.7798	Intermediate Similarity	NPC473324
0.7798	Intermediate Similarity	NPC471093
0.7789	Intermediate Similarity	NPC296734
0.7789	Intermediate Similarity	NPC477936
0.7789	Intermediate Similarity	NPC470611
0.7788	Intermediate Similarity	NPC470030
0.7778	Intermediate Similarity	NPC224414
0.7778	Intermediate Similarity	NPC102725
0.7778	Intermediate Similarity	NPC189663
0.7778	Intermediate Similarity	NPC67653
0.7778	Intermediate Similarity	NPC472079
0.7778	Intermediate Similarity	NPC63841
0.7778	Intermediate Similarity	NPC82955
0.7778	Intermediate Similarity	NPC89860
0.7778	Intermediate Similarity	NPC471459
0.7767	Intermediate Similarity	NPC472145
0.7767	Intermediate Similarity	NPC470028
0.7767	Intermediate Similarity	NPC274200
0.7767	Intermediate Similarity	NPC233649
0.7766	Intermediate Similarity	NPC470609
0.7766	Intermediate Similarity	NPC248944
0.7766	Intermediate Similarity	NPC7479
0.7766	Intermediate Similarity	NPC257296
0.7757	Intermediate Similarity	NPC4115
0.7757	Intermediate Similarity	NPC307660
0.7757	Intermediate Similarity	NPC130511
0.7748	Intermediate Similarity	NPC471252
0.7745	Intermediate Similarity	NPC287354
0.7745	Intermediate Similarity	NPC62407
0.7732	Intermediate Similarity	NPC290612
0.7727	Intermediate Similarity	NPC29505
0.7727	Intermediate Similarity	NPC63244
0.7723	Intermediate Similarity	NPC277774
0.7723	Intermediate Similarity	NPC149400
0.7723	Intermediate Similarity	NPC472231
0.7723	Intermediate Similarity	NPC325828
0.7723	Intermediate Similarity	NPC88962
0.7723	Intermediate Similarity	NPC177834
0.7723	Intermediate Similarity	NPC477547
0.7723	Intermediate Similarity	NPC48339
0.7723	Intermediate Similarity	NPC141769
0.7723	Intermediate Similarity	NPC477451
0.7723	Intermediate Similarity	NPC144790
0.7723	Intermediate Similarity	NPC474379
0.7723	Intermediate Similarity	NPC472232
0.7723	Intermediate Similarity	NPC249204
0.7723	Intermediate Similarity	NPC234352
0.7723	Intermediate Similarity	NPC297348
0.7723	Intermediate Similarity	NPC250393
0.7714	Intermediate Similarity	NPC472081
0.7714	Intermediate Similarity	NPC298266
0.7714	Intermediate Similarity	NPC259654
0.7714	Intermediate Similarity	NPC475574
0.7714	Intermediate Similarity	NPC476512
0.7714	Intermediate Similarity	NPC108227
0.7708	Intermediate Similarity	NPC472744

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 NPC178853 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	515
0.1-0.2	3854
0.2-0.3	3239
0.3-0.4	888
0.4-0.5	307
0.5-0.6	226
0.6-0.7	103
0.7-0.8	17
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8713	High Similarity	NPD8170	Clinical (unspecified phase)
0.7766	Intermediate Similarity	NPD6928	Phase 2
0.7723	Intermediate Similarity	NPD8171	Discontinued
0.7652	Intermediate Similarity	NPD6054	Approved
0.7652	Intermediate Similarity	NPD6059	Approved
0.7521	Intermediate Similarity	NPD6370	Approved
0.75	Intermediate Similarity	NPD7736	Approved
0.7436	Intermediate Similarity	NPD6016	Approved
0.7436	Intermediate Similarity	NPD6015	Approved
0.7395	Intermediate Similarity	NPD7492	Approved
0.7383	Intermediate Similarity	NPD1700	Approved
0.7373	Intermediate Similarity	NPD5988	Approved
0.7333	Intermediate Similarity	NPD6616	Approved
0.7295	Intermediate Similarity	NPD7319	Approved
0.7273	Intermediate Similarity	NPD8293	Discontinued
0.7273	Intermediate Similarity	NPD7078	Approved
0.7207	Intermediate Similarity	NPD6412	Phase 2
0.719	Intermediate Similarity	NPD7507	Approved
0.713	Intermediate Similarity	NPD8133	Approved
0.7073	Intermediate Similarity	NPD6033	Approved
0.7053	Intermediate Similarity	NPD3703	Phase 2
0.7053	Intermediate Similarity	NPD3702	Approved
0.7027	Intermediate Similarity	NPD4056	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD4057	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD6114	Approved
0.701	Intermediate Similarity	NPD6115	Approved
0.701	Intermediate Similarity	NPD6118	Approved
0.701	Intermediate Similarity	NPD6697	Approved
0.6991	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD6319	Approved
0.6915	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD6116	Phase 1
0.6864	Remote Similarity	NPD6940	Discontinued
0.6809	Remote Similarity	NPD4245	Approved
0.6809	Remote Similarity	NPD4244	Approved
0.6804	Remote Similarity	NPD6117	Approved
0.6783	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5360	Phase 3
0.6774	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD7991	Discontinued
0.6748	Remote Similarity	NPD8328	Phase 3
0.6737	Remote Similarity	NPD5777	Approved
0.6724	Remote Similarity	NPD4634	Approved
0.6702	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD3698	Phase 2
0.6702	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6008	Approved
0.6667	Remote Similarity	NPD4238	Approved
0.6667	Remote Similarity	NPD4802	Phase 2
0.6667	Remote Similarity	NPD6009	Approved
0.6636	Remote Similarity	NPD8034	Phase 2
0.6636	Remote Similarity	NPD8035	Phase 2
0.6612	Remote Similarity	NPD7328	Approved
0.6612	Remote Similarity	NPD7327	Approved
0.661	Remote Similarity	NPD6882	Approved
0.6557	Remote Similarity	NPD7516	Approved
0.6555	Remote Similarity	NPD4632	Approved
0.6552	Remote Similarity	NPD7320	Approved
0.6526	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6402	Approved
0.6522	Remote Similarity	NPD5739	Approved
0.6522	Remote Similarity	NPD7128	Approved
0.6522	Remote Similarity	NPD6675	Approved
0.6504	Remote Similarity	NPD8377	Approved
0.6504	Remote Similarity	NPD8294	Approved
0.6496	Remote Similarity	NPD6373	Approved
0.6496	Remote Similarity	NPD6372	Approved
0.648	Remote Similarity	NPD6067	Discontinued
0.6471	Remote Similarity	NPD1779	Approved
0.6471	Remote Similarity	NPD8297	Approved
0.6471	Remote Similarity	NPD1780	Approved
0.6458	Remote Similarity	NPD4789	Approved
0.6452	Remote Similarity	NPD8033	Approved
0.6452	Remote Similarity	NPD8380	Approved
0.6452	Remote Similarity	NPD8296	Approved
0.6452	Remote Similarity	NPD8379	Approved
0.6452	Remote Similarity	NPD8335	Approved
0.6452	Remote Similarity	NPD8378	Approved
0.6434	Remote Similarity	NPD5956	Approved
0.641	Remote Similarity	NPD6881	Approved
0.641	Remote Similarity	NPD6899	Approved
0.6392	Remote Similarity	NPD6081	Approved
0.6392	Remote Similarity	NPD4758	Discontinued
0.6387	Remote Similarity	NPD6650	Approved
0.6387	Remote Similarity	NPD6649	Approved
0.6346	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD3669	Approved
0.6339	Remote Similarity	NPD4755	Approved
0.6337	Remote Similarity	NPD5364	Discontinued
0.6325	Remote Similarity	NPD5701	Approved
0.6325	Remote Similarity	NPD5697	Approved
0.632	Remote Similarity	NPD6921	Approved
0.6303	Remote Similarity	NPD7102	Approved
0.6303	Remote Similarity	NPD6883	Approved
0.6303	Remote Similarity	NPD7290	Approved
0.6277	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD6399	Phase 3
0.626	Remote Similarity	NPD7115	Discovery
0.625	Remote Similarity	NPD8130	Phase 1
0.625	Remote Similarity	NPD6617	Approved
0.625	Remote Similarity	NPD6847	Approved
0.625	Remote Similarity	NPD6869	Approved
0.6228	Remote Similarity	NPD5286	Approved
0.6228	Remote Similarity	NPD4700	Approved
0.6228	Remote Similarity	NPD5285	Approved
0.6228	Remote Similarity	NPD4696	Approved
0.6226	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.622	Remote Similarity	NPD7604	Phase 2
0.6218	Remote Similarity	NPD6013	Approved
0.6218	Remote Similarity	NPD6014	Approved
0.6218	Remote Similarity	NPD6012	Approved
0.6211	Remote Similarity	NPD4224	Phase 2
0.619	Remote Similarity	NPD4788	Approved
0.619	Remote Similarity	NPD5983	Phase 2
0.6176	Remote Similarity	NPD3671	Phase 1
0.6134	Remote Similarity	NPD6011	Approved
0.6134	Remote Similarity	NPD6686	Approved
0.6124	Remote Similarity	NPD6336	Discontinued
0.6122	Remote Similarity	NPD4787	Phase 1
0.6121	Remote Similarity	NPD8085	Approved
0.6121	Remote Similarity	NPD8083	Approved
0.6121	Remote Similarity	NPD8084	Approved
0.6121	Remote Similarity	NPD8139	Approved
0.6121	Remote Similarity	NPD5224	Approved
0.6121	Remote Similarity	NPD5211	Phase 2
0.6121	Remote Similarity	NPD8138	Approved
0.6121	Remote Similarity	NPD4633	Approved
0.6121	Remote Similarity	NPD5226	Approved
0.6121	Remote Similarity	NPD5225	Approved
0.6121	Remote Similarity	NPD8086	Approved
0.6121	Remote Similarity	NPD8082	Approved
0.6116	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD8275	Approved
0.6068	Remote Similarity	NPD5174	Approved
0.6068	Remote Similarity	NPD8276	Approved
0.6068	Remote Similarity	NPD5175	Approved
0.6063	Remote Similarity	NPD7503	Approved
0.6063	Remote Similarity	NPD8513	Phase 3
0.6063	Remote Similarity	NPD8517	Approved
0.6063	Remote Similarity	NPD8515	Approved
0.6063	Remote Similarity	NPD8516	Approved
0.6053	Remote Similarity	NPD6083	Phase 2
0.6053	Remote Similarity	NPD6084	Phase 2
0.6034	Remote Similarity	NPD5223	Approved
0.6018	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD8081	Approved
0.6017	Remote Similarity	NPD5141	Approved
0.6	Remote Similarity	NPD5696	Approved
0.6	Remote Similarity	NPD7638	Approved
0.6	Remote Similarity	NPD5328	Approved
0.5982	Remote Similarity	NPD4202	Approved
0.5966	Remote Similarity	NPD4768	Approved
0.5966	Remote Similarity	NPD8393	Approved
0.5966	Remote Similarity	NPD4767	Approved
0.5966	Remote Similarity	NPD6920	Discontinued
0.595	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD7639	Approved
0.5948	Remote Similarity	NPD7640	Approved
0.5941	Remote Similarity	NPD1810	Approved
0.5941	Remote Similarity	NPD1811	Approved
0.5938	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD4754	Approved
0.592	Remote Similarity	NPD6274	Approved
0.5913	Remote Similarity	NPD7902	Approved
0.5909	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5906	Remote Similarity	NPD7100	Approved
0.5906	Remote Similarity	NPD7101	Approved
0.5902	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD6079	Approved
0.5877	Remote Similarity	NPD5695	Phase 3
0.5872	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5868	Remote Similarity	NPD5128	Approved
0.5868	Remote Similarity	NPD8174	Phase 2
0.5868	Remote Similarity	NPD4729	Approved
0.5868	Remote Similarity	NPD4730	Approved
0.5856	Remote Similarity	NPD4753	Phase 2
0.5847	Remote Similarity	NPD7632	Discontinued
0.5833	Remote Similarity	NPD4786	Approved
0.5827	Remote Similarity	NPD6335	Approved
0.5826	Remote Similarity	NPD4697	Phase 3
0.5814	Remote Similarity	NPD6908	Approved
0.5814	Remote Similarity	NPD6909	Approved
0.5812	Remote Similarity	NPD8418	Phase 2
0.5806	Remote Similarity	NPD6053	Discontinued
0.58	Remote Similarity	NPD2687	Approved
0.58	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.58	Remote Similarity	NPD2686	Approved
0.58	Remote Similarity	NPD2254	Approved
0.5789	Remote Similarity	NPD7748	Approved
0.5789	Remote Similarity	NPD5282	Discontinued
0.5781	Remote Similarity	NPD4522	Approved
0.5772	Remote Similarity	NPD5251	Approved
0.5772	Remote Similarity	NPD5249	Phase 3
0.5772	Remote Similarity	NPD5248	Approved
0.5772	Remote Similarity	NPD5247	Approved
0.5772	Remote Similarity	NPD5250	Approved
0.5766	Remote Similarity	NPD6903	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