NPASS Compound

Structure

CID144068 OpenBabel06191715502D 48 54 0 0 1 0 0 0 0 0999 V2000 3.1042 2.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4570 3.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8301 -0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 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 -0.0000 -1.0000 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 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5370 0.7609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1261 2.7601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8171 0.1910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.7942 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0622 -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 -4.3301 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0622 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 1 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 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.5263 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 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 -8.6603 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0125 0.1064 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 34 1 0 0 0 0 5 34 1 0 0 0 0 7 36 1 0 0 0 0 9 10 1 0 0 0 0 9 20 2 0 0 0 0 10 37 1 0 0 0 0 11 12 1 0 0 0 0 11 36 1 0 0 0 0 13 21 1 0 0 0 0 14 22 1 0 0 0 0 14 26 1 0 0 0 0 15 24 1 0 0 0 0 15 35 1 0 0 0 0 16 39 1 0 0 0 0 17 38 1 0 0 0 0 17 45 1 0 0 0 0 18 21 1 0 0 0 0 19 40 2 0 0 0 0 19 46 1 0 0 0 0 20 27 1 0 0 0 0 20 35 1 0 0 0 0 21 38 1 6 0 0 0 22 27 1 0 0 0 0 22 41 1 6 0 0 0 23 13 1 6 0 0 0 23 31 1 0 0 0 0 23 45 1 0 0 0 0 24 32 1 0 0 0 0 24 46 1 1 0 0 0 25 16 1 6 0 0 0 25 28 1 0 0 0 0 25 47 1 0 0 0 0 26 34 1 0 0 0 0 26 35 1 6 0 0 0 27 36 1 1 0 0 0 28 29 1 0 0 0 0 28 42 1 1 0 0 0 29 30 1 0 0 0 0 29 43 1 6 0 0 0 30 33 1 0 0 0 0 30 44 1 1 0 0 0 31 37 1 6 0 0 0 31 38 1 0 0 0 0 32 34 1 0 0 0 0 32 48 1 6 0 0 0 33 47 1 0 0 0 0 33 48 1 6 0 0 0 35 6 1 6 0 0 0 36 37 1 1 0 0 0 37 8 1 6 0 0 0 38 12 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	676.42
Volume:	688.538
LogP:	4.296
LogD:	4.087
LogS:	-4.466
# Rotatable Bonds:	6
TPSA:	155.14
# H-Bond Aceptor:	10
# H-Bond Donor:	5
# Rings:	7
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.166
Synthetic Accessibility Score:	6.636
Fsp3:	0.921
Lipinski Rule-of-5:	Accepted
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:	-5.366
MDCK Permeability:	2.448947270750068e-05
Pgp-inhibitor:	0.971
Pgp-substrate:	0.171
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.03
30% Bioavailability (F30%):	0.893

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	81.4669418334961%
Volume Distribution (VD):	0.775
Pgp-substrate:	9.40298843383789%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.132
CYP2C19-inhibitor:	0.004
CYP2C19-substrate:	0.686
CYP2C9-inhibitor:	0.016
CYP2C9-substrate:	0.01
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.055
CYP3A4-inhibitor:	0.438
CYP3A4-substrate:	0.432

ADMET: Excretion

Clearance (CL):	1.22
Half-life (T1/2):	0.402

ADMET: Toxicity

hERG Blockers:	0.452
Human Hepatotoxicity (H-HT):	0.227
Drug-inuced Liver Injury (DILI):	0.576
AMES Toxicity:	0.062
Rat Oral Acute Toxicity:	0.422
Maximum Recommended Daily Dose:	0.411
Skin Sensitization:	0.459
Carcinogencity:	0.11
Eye Corrosion:	0.004
Eye Irritation:	0.012
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC144068

Natural Product ID:	NPC144068
*Common Name:**	Rubianoside I
IUPAC Name:	n.a.
Synonyms:	Rubianoside I
Standard InCHIKey:	NCVHJBCXBZFWRS-BGKZYWRXSA-N
Standard InCHI:	InChI=1S/C38H60O10/c1-18(2)21-13-23-31-37(8)10-9-20-27(36(37,7)11-12-38(21,31)17-45-23)22(41)14-26-34(4,5)32(24(46-19(3)40)15-35(20,26)6)48-33-30(44)29(43)28(42)25(16-39)47-33/h9,18,21-33,39,41-44H,10-17H2,1-8H3/t21-,22-,23-,24+,25+,26-,27-,28+,29-,30+,31+,32-,33-,35+,36-,37+,38+/m0/s1
SMILES:	CC(C)[C@@H]1C[C@H]2[C@@H]3[C@@]4(C)CC=C5[C@@H]([C@H](C[C@H]6C(C)(C)[C@H]([C@@H](C[C@]56C)OC(=O)C)O[C@H]5[C@@H]([C@H]([C@@H]([C@@H](CO)O5)O)O)O)O)[C@]4(C)CC[C@@]13CO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL445475
PubChem CID:	21629628
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
NPO16607	Rubia yunnanensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350148]
NPO16607	Rubia yunnanensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12762798]
NPO16607	Rubia yunnanensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21044847]
NPO16607	Rubia yunnanensis	Species	Rubiaceae	Eukaryota	n.a.	root	n.a.	PMID[21973054]
NPO16607	Rubia yunnanensis	Species	Rubiaceae	Eukaryota	roots	n.a.	n.a.	PMID[21973054]
NPO16607	Rubia yunnanensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16607	Rubia yunnanensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16607	Rubia yunnanensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
Others	5

Activity Type	# Activity
Others	5

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	Inhibition	=	1.5	%	PMID[528430]
NPT2	Others	Unspecified	Inhibition	=	-8.0	%	PMID[528430]
NPT2	Others	Unspecified	Inhibition	=	-0.3	%	PMID[528430]
NPT2	Others	Unspecified	Inhibition	=	5.1	%	PMID[528430]
NPT2	Others	Unspecified	Inhibition	=	-3.2	%	PMID[528430]

☑ 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 NPC144068 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	251
0.1-0.2	1819
0.2-0.3	5896
0.3-0.4	13363
0.4-0.5	8731
0.5-0.6	5757
0.6-0.7	3752
0.7-0.8	2050
0.8-0.85	681
0.85-0.9	297
0.9-0.95	99
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9619	High Similarity	NPC114188
0.9333	High Similarity	NPC295980
0.9266	High Similarity	NPC63609
0.9245	High Similarity	NPC43976
0.9245	High Similarity	NPC51925
0.9245	High Similarity	NPC154085
0.9245	High Similarity	NPC125361
0.9245	High Similarity	NPC296761
0.9238	High Similarity	NPC234160
0.9182	High Similarity	NPC477807
0.9174	High Similarity	NPC477808
0.9151	High Similarity	NPC476541
0.9151	High Similarity	NPC38217
0.9151	High Similarity	NPC472988
0.9151	High Similarity	NPC476538
0.9151	High Similarity	NPC476540
0.9151	High Similarity	NPC476539
0.9143	High Similarity	NPC242748
0.9143	High Similarity	NPC181845
0.9143	High Similarity	NPC473199
0.9099	High Similarity	NPC160888
0.9099	High Similarity	NPC475403
0.9091	High Similarity	NPC477031
0.9091	High Similarity	NPC212660
0.9074	High Similarity	NPC197231
0.9074	High Similarity	NPC470748
0.9074	High Similarity	NPC65167
0.9074	High Similarity	NPC476547
0.9065	High Similarity	NPC475670
0.9065	High Similarity	NPC477027
0.9065	High Similarity	NPC477026
0.9065	High Similarity	NPC306131
0.9065	High Similarity	NPC70204
0.9057	High Similarity	NPC14704
0.9057	High Similarity	NPC230507
0.9057	High Similarity	NPC113044
0.9057	High Similarity	NPC161676
0.9057	High Similarity	NPC283829
0.9057	High Similarity	NPC470432
0.9057	High Similarity	NPC226642
0.9057	High Similarity	NPC305423
0.9057	High Similarity	NPC473469
0.9048	High Similarity	NPC475365
0.9048	High Similarity	NPC31430
0.9048	High Similarity	NPC85593
0.9018	High Similarity	NPC473633
0.9018	High Similarity	NPC229962
0.9018	High Similarity	NPC476085
0.9018	High Similarity	NPC195560
0.8991	High Similarity	NPC244431
0.8991	High Similarity	NPC210569
0.8991	High Similarity	NPC32361
0.8991	High Similarity	NPC263359
0.8991	High Similarity	NPC31896
0.8991	High Similarity	NPC19888
0.8972	High Similarity	NPC7213
0.8972	High Similarity	NPC98696
0.8962	High Similarity	NPC473923
0.8962	High Similarity	NPC473476
0.8962	High Similarity	NPC26798
0.8952	High Similarity	NPC213190
0.8952	High Similarity	NPC16573
0.8942	High Similarity	NPC155974
0.8938	High Similarity	NPC198325
0.8938	High Similarity	NPC50689
0.8938	High Similarity	NPC233391
0.8938	High Similarity	NPC473566
0.8938	High Similarity	NPC207243
0.8938	High Similarity	NPC475358
0.8929	High Similarity	NPC475357
0.8909	High Similarity	NPC476693
0.8909	High Similarity	NPC79900
0.8899	High Similarity	NPC285410
0.8899	High Similarity	NPC250481
0.8899	High Similarity	NPC263827
0.8899	High Similarity	NPC475247
0.8899	High Similarity	NPC294129
0.8899	High Similarity	NPC13190
0.8889	High Similarity	NPC150372
0.8889	High Similarity	NPC6806
0.8889	High Similarity	NPC249265
0.8889	High Similarity	NPC171073
0.8889	High Similarity	NPC309278
0.8889	High Similarity	NPC40440
0.8889	High Similarity	NPC477809
0.8889	High Similarity	NPC73243
0.8889	High Similarity	NPC475550
0.8889	High Similarity	NPC218571
0.8889	High Similarity	NPC22779
0.8889	High Similarity	NPC84956
0.8889	High Similarity	NPC244086
0.8889	High Similarity	NPC470433
0.8889	High Similarity	NPC475333
0.8889	High Similarity	NPC232054
0.8889	High Similarity	NPC300557
0.8889	High Similarity	NPC42482
0.8889	High Similarity	NPC102016
0.8889	High Similarity	NPC224098
0.8889	High Similarity	NPC95051
0.8889	High Similarity	NPC248746
0.8889	High Similarity	NPC208383
0.8889	High Similarity	NPC194207
0.8889	High Similarity	NPC46190
0.8889	High Similarity	NPC476835
0.887	High Similarity	NPC256983
0.8868	High Similarity	NPC470064
0.8868	High Similarity	NPC470062
0.8868	High Similarity	NPC470059
0.8868	High Similarity	NPC165033
0.8868	High Similarity	NPC470061
0.8868	High Similarity	NPC470058
0.8868	High Similarity	NPC470885
0.8868	High Similarity	NPC187400
0.8868	High Similarity	NPC273879
0.8868	High Similarity	NPC470060
0.8868	High Similarity	NPC221562
0.8868	High Similarity	NPC470043
0.8868	High Similarity	NPC470057
0.8868	High Similarity	NPC312774
0.8868	High Similarity	NPC173583
0.886	High Similarity	NPC231518
0.886	High Similarity	NPC475219
0.8857	High Similarity	NPC312553
0.8857	High Similarity	NPC288694
0.8857	High Similarity	NPC159036
0.8857	High Similarity	NPC136816
0.8857	High Similarity	NPC154452
0.885	High Similarity	NPC32177
0.885	High Similarity	NPC5883
0.885	High Similarity	NPC236973
0.885	High Similarity	NPC55532
0.885	High Similarity	NPC44899
0.885	High Similarity	NPC30483
0.885	High Similarity	NPC470897
0.885	High Similarity	NPC29639
0.885	High Similarity	NPC304260
0.885	High Similarity	NPC292467
0.885	High Similarity	NPC329905
0.885	High Similarity	NPC469756
0.8846	High Similarity	NPC473200
0.8846	High Similarity	NPC208358
0.8846	High Similarity	NPC282669
0.8846	High Similarity	NPC7341
0.8839	High Similarity	NPC93883
0.8839	High Similarity	NPC152615
0.8839	High Similarity	NPC203862
0.8829	High Similarity	NPC167183
0.8829	High Similarity	NPC32707
0.8829	High Similarity	NPC477810
0.8818	High Similarity	NPC112274
0.8807	High Similarity	NPC224314
0.8807	High Similarity	NPC141433
0.8807	High Similarity	NPC23808
0.8807	High Similarity	NPC269297
0.8807	High Similarity	NPC247037
0.8807	High Similarity	NPC87998
0.8807	High Similarity	NPC477811
0.8807	High Similarity	NPC222202
0.8796	High Similarity	NPC220427
0.8785	High Similarity	NPC474569
0.8785	High Similarity	NPC470056
0.8785	High Similarity	NPC470055
0.8783	High Similarity	NPC193893
0.8783	High Similarity	NPC43842
0.8774	High Similarity	NPC31907
0.8774	High Similarity	NPC155010
0.8774	High Similarity	NPC472252
0.8774	High Similarity	NPC16520
0.8774	High Similarity	NPC8039
0.8774	High Similarity	NPC120123
0.8774	High Similarity	NPC473020
0.8774	High Similarity	NPC131479
0.8774	High Similarity	NPC473198
0.8774	High Similarity	NPC475701
0.8774	High Similarity	NPC157659
0.8774	High Similarity	NPC245280
0.8774	High Similarity	NPC189852
0.8774	High Similarity	NPC286969
0.8774	High Similarity	NPC211879
0.8774	High Similarity	NPC114874
0.8772	High Similarity	NPC475556
0.8772	High Similarity	NPC107607
0.8772	High Similarity	NPC72260
0.8772	High Similarity	NPC471406
0.8772	High Similarity	NPC475136
0.8772	High Similarity	NPC475629
0.8772	High Similarity	NPC474466
0.8762	High Similarity	NPC21064
0.8762	High Similarity	NPC129372
0.8762	High Similarity	NPC88000
0.8762	High Similarity	NPC472023
0.8762	High Similarity	NPC160734
0.8762	High Similarity	NPC47566
0.8762	High Similarity	NPC309425
0.8762	High Similarity	NPC121072
0.8762	High Similarity	NPC4831
0.8761	High Similarity	NPC472080
0.8761	High Similarity	NPC218093
0.875	High Similarity	NPC310341
0.875	High Similarity	NPC193382

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 NPC144068 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	216
0.1-0.2	2048
0.2-0.3	4246
0.3-0.4	1763
0.4-0.5	432
0.5-0.6	268
0.6-0.7	131
0.7-0.8	33
0.8-0.85	3
0.85-0.9	10
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.886	High Similarity	NPD8033	Approved
0.8772	High Similarity	NPD8377	Approved
0.8772	High Similarity	NPD8294	Approved
0.8696	High Similarity	NPD8380	Approved
0.8696	High Similarity	NPD8379	Approved
0.8696	High Similarity	NPD8378	Approved
0.8696	High Similarity	NPD8296	Approved
0.8696	High Similarity	NPD8335	Approved
0.8684	High Similarity	NPD7516	Approved
0.8596	High Similarity	NPD7328	Approved
0.8596	High Similarity	NPD7327	Approved
0.822	Intermediate Similarity	NPD7503	Approved
0.8099	Intermediate Similarity	NPD7507	Approved
0.8053	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD6412	Phase 2
0.7967	Intermediate Similarity	NPD7736	Approved
0.7931	Intermediate Similarity	NPD8133	Approved
0.7925	Intermediate Similarity	NPD8171	Discontinued
0.7903	Intermediate Similarity	NPD7319	Approved
0.7742	Intermediate Similarity	NPD8293	Discontinued
0.7731	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD8328	Phase 3
0.7561	Intermediate Similarity	NPD6370	Approved
0.7544	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD8449	Approved
0.744	Intermediate Similarity	NPD7492	Approved
0.7398	Intermediate Similarity	NPD6054	Approved
0.7398	Intermediate Similarity	NPD6059	Approved
0.7385	Intermediate Similarity	NPD8450	Suspended
0.7381	Intermediate Similarity	NPD6616	Approved
0.735	Intermediate Similarity	NPD6686	Approved
0.7323	Intermediate Similarity	NPD7078	Approved
0.7257	Intermediate Similarity	NPD7638	Approved
0.725	Intermediate Similarity	NPD6882	Approved
0.725	Intermediate Similarity	NPD8297	Approved
0.7222	Intermediate Similarity	NPD6067	Discontinued
0.72	Intermediate Similarity	NPD6016	Approved
0.72	Intermediate Similarity	NPD6015	Approved
0.7193	Intermediate Similarity	NPD7639	Approved
0.7193	Intermediate Similarity	NPD7640	Approved
0.7154	Intermediate Similarity	NPD6009	Approved
0.7143	Intermediate Similarity	NPD5988	Approved
0.7122	Intermediate Similarity	NPD7625	Phase 1
0.712	Intermediate Similarity	NPD6319	Approved
0.7115	Intermediate Similarity	NPD6928	Phase 2
0.7063	Intermediate Similarity	NPD8513	Phase 3
0.7063	Intermediate Similarity	NPD8516	Approved
0.7063	Intermediate Similarity	NPD8515	Approved
0.7063	Intermediate Similarity	NPD8517	Approved
0.7059	Intermediate Similarity	NPD7320	Approved
0.7049	Intermediate Similarity	NPD4632	Approved
0.7034	Intermediate Similarity	NPD5739	Approved
0.7034	Intermediate Similarity	NPD6402	Approved
0.7034	Intermediate Similarity	NPD6008	Approved
0.7034	Intermediate Similarity	NPD7128	Approved
0.7034	Intermediate Similarity	NPD6675	Approved
0.7	Intermediate Similarity	NPD6372	Approved
0.7	Intermediate Similarity	NPD6373	Approved
0.6964	Remote Similarity	NPD6399	Phase 3
0.6952	Remote Similarity	NPD7525	Registered
0.6917	Remote Similarity	NPD6899	Approved
0.6917	Remote Similarity	NPD6881	Approved
0.6903	Remote Similarity	NPD7748	Approved
0.6885	Remote Similarity	NPD8130	Phase 1
0.6885	Remote Similarity	NPD6649	Approved
0.6885	Remote Similarity	NPD6650	Approved
0.6875	Remote Similarity	NPD8035	Phase 2
0.6875	Remote Similarity	NPD8034	Phase 2
0.687	Remote Similarity	NPD6033	Approved
0.687	Remote Similarity	NPD7902	Approved
0.6857	Remote Similarity	NPD7645	Phase 2
0.6833	Remote Similarity	NPD5701	Approved
0.6833	Remote Similarity	NPD5697	Approved
0.6818	Remote Similarity	NPD7524	Approved
0.6803	Remote Similarity	NPD7102	Approved
0.6803	Remote Similarity	NPD6883	Approved
0.6803	Remote Similarity	NPD7290	Approved
0.6748	Remote Similarity	NPD6847	Approved
0.6748	Remote Similarity	NPD6617	Approved
0.6748	Remote Similarity	NPD6869	Approved
0.6746	Remote Similarity	NPD7115	Discovery
0.6731	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD7515	Phase 2
0.6724	Remote Similarity	NPD6084	Phase 2
0.6724	Remote Similarity	NPD6083	Phase 2
0.6721	Remote Similarity	NPD6014	Approved
0.6721	Remote Similarity	NPD6012	Approved
0.6721	Remote Similarity	NPD6013	Approved
0.6692	Remote Similarity	NPD7604	Phase 2
0.6667	Remote Similarity	NPD4225	Approved
0.6667	Remote Similarity	NPD5983	Phase 2
0.6639	Remote Similarity	NPD7632	Discontinued
0.6639	Remote Similarity	NPD6011	Approved
0.6636	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD7339	Approved
0.6635	Remote Similarity	NPD6942	Approved
0.6613	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD7900	Approved
0.6607	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD6336	Discontinued
0.6585	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD4755	Approved
0.6552	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD6051	Approved
0.6545	Remote Similarity	NPD4786	Approved
0.6545	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD4634	Approved
0.6522	Remote Similarity	NPD4202	Approved
0.6518	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5285	Approved
0.6471	Remote Similarity	NPD5286	Approved
0.6471	Remote Similarity	NPD4700	Approved
0.6471	Remote Similarity	NPD4696	Approved
0.646	Remote Similarity	NPD6903	Approved
0.6455	Remote Similarity	NPD6695	Phase 3
0.6435	Remote Similarity	NPD7637	Suspended
0.6429	Remote Similarity	NPD6053	Discontinued
0.6429	Remote Similarity	NPD7521	Approved
0.6429	Remote Similarity	NPD6684	Approved
0.6429	Remote Similarity	NPD7334	Approved
0.6429	Remote Similarity	NPD6409	Approved
0.6429	Remote Similarity	NPD7146	Approved
0.6429	Remote Similarity	NPD5330	Approved
0.6417	Remote Similarity	NPD5344	Discontinued
0.641	Remote Similarity	NPD5695	Phase 3
0.641	Remote Similarity	NPD7991	Discontinued
0.6406	Remote Similarity	NPD6274	Approved
0.6404	Remote Similarity	NPD5328	Approved
0.64	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD5956	Approved
0.6387	Remote Similarity	NPD5696	Approved
0.6385	Remote Similarity	NPD7100	Approved
0.6385	Remote Similarity	NPD7101	Approved
0.6372	Remote Similarity	NPD7750	Discontinued
0.6371	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3667	Approved
0.6364	Remote Similarity	NPD4633	Approved
0.6364	Remote Similarity	NPD5211	Phase 2
0.6364	Remote Similarity	NPD5225	Approved
0.6364	Remote Similarity	NPD5224	Approved
0.6364	Remote Similarity	NPD5226	Approved
0.6341	Remote Similarity	NPD4768	Approved
0.6341	Remote Similarity	NPD4767	Approved
0.6311	Remote Similarity	NPD5174	Approved
0.6311	Remote Similarity	NPD5175	Approved
0.6308	Remote Similarity	NPD6335	Approved
0.6304	Remote Similarity	NPD8338	Approved
0.6296	Remote Similarity	NPD8074	Phase 3
0.6293	Remote Similarity	NPD6079	Approved
0.6288	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD6908	Approved
0.6288	Remote Similarity	NPD6909	Approved
0.6283	Remote Similarity	NPD3618	Phase 1
0.6281	Remote Similarity	NPD5223	Approved
0.6281	Remote Similarity	NPD4159	Approved
0.6279	Remote Similarity	NPD6940	Discontinued
0.6262	Remote Similarity	NPD6933	Approved
0.6261	Remote Similarity	NPD4753	Phase 2
0.626	Remote Similarity	NPD5141	Approved
0.625	Remote Similarity	NPD3665	Phase 1
0.625	Remote Similarity	NPD8337	Approved
0.625	Remote Similarity	NPD8336	Approved
0.625	Remote Similarity	NPD3133	Approved
0.625	Remote Similarity	NPD3666	Approved
0.624	Remote Similarity	NPD4730	Approved
0.624	Remote Similarity	NPD4729	Approved
0.6239	Remote Similarity	NPD6929	Approved
0.6231	Remote Similarity	NPD6317	Approved
0.6228	Remote Similarity	NPD4250	Approved
0.6228	Remote Similarity	NPD4251	Approved
0.6226	Remote Similarity	NPD4784	Approved
0.6226	Remote Similarity	NPD4785	Approved
0.6211	Remote Similarity	NPD7799	Discontinued
0.619	Remote Similarity	NPD4243	Approved
0.6186	Remote Similarity	NPD6001	Approved
0.6183	Remote Similarity	NPD6314	Approved
0.6183	Remote Similarity	NPD6313	Approved
0.6182	Remote Similarity	NPD6930	Phase 2
0.6182	Remote Similarity	NPD6931	Approved
0.6182	Remote Similarity	NPD4748	Discontinued
0.6179	Remote Similarity	NPD4754	Approved
0.6174	Remote Similarity	NPD6672	Approved
0.6174	Remote Similarity	NPD5737	Approved
0.616	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.616	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6411	Approved
0.6147	Remote Similarity	NPD6697	Approved
0.6147	Remote Similarity	NPD6115	Approved
0.6147	Remote Similarity	NPD6118	Approved
0.6147	Remote Similarity	NPD6114	Approved
0.6142	Remote Similarity	NPD5251	Approved
0.6142	Remote Similarity	NPD5247	Approved
0.6142	Remote Similarity	NPD5249	Phase 3
0.6142	Remote Similarity	NPD5248	Approved
0.6142	Remote Similarity	NPD5250	Approved
0.614	Remote Similarity	NPD4249	Approved
0.614	Remote Similarity	NPD6098	Approved
0.6121	Remote Similarity	NPD6673	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