NPASS Compound

Structure

NPC470274 OpenBabel07101718192D 47 52 0 0 1 0 0 0 0 0999 V2000 -4.1161 -6.3564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8363 -2.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7213 1.4612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1913 -2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1913 0.4135 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 7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 0.5000 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 -3.4980 -4.4543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4762 -4.6622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1890 -3.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 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 -4.1369 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -0.1910 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 -1.7321 -2.0000 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 5.1962 -0.0000 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 -5.7633 -5.8212 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 -4.7852 -5.6132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8581 -2.7601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7431 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 1 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 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3364 2.5827 0.0000 C 0 0 0 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 -2.5981 -0.5000 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 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.0724 -6.7722 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 0.8364 3.4487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 2.4781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 3 27 2 0 0 0 0 4 37 1 0 0 0 0 6 46 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 13 1 0 0 0 0 9 14 2 0 0 0 0 10 11 1 0 0 0 0 10 12 1 0 0 0 0 11 25 2 0 0 0 0 12 26 1 0 0 0 0 13 28 2 0 0 0 0 14 28 1 0 0 0 0 15 17 1 0 0 0 0 15 29 1 0 0 0 0 16 18 1 0 0 0 0 16 33 1 0 0 0 0 17 38 1 0 0 0 0 19 20 1 0 0 0 0 19 37 1 0 0 0 0 20 39 1 0 0 0 0 21 28 1 0 0 0 0 22 32 1 0 0 0 0 23 25 1 0 0 0 0 23 42 2 0 0 0 0 24 39 1 0 0 0 0 24 40 1 0 0 0 0 26 2 1 1 0 0 0 26 29 1 0 0 0 0 27 34 1 0 0 0 0 27 35 1 0 0 0 0 29 37 1 1 0 0 0 30 21 1 6 0 0 0 30 36 1 0 0 0 0 30 41 1 0 0 0 0 31 22 1 1 0 0 0 31 34 1 0 0 0 0 31 47 1 0 0 0 0 32 38 1 6 0 0 0 32 39 1 0 0 0 0 33 41 2 3 0 0 0 33 43 1 0 0 0 0 34 40 1 1 0 0 0 35 44 2 0 0 0 0 35 47 1 0 0 0 0 36 45 2 0 0 0 0 36 46 1 0 0 0 0 37 38 1 1 0 0 0 38 5 1 6 0 0 0 39 40 1 6 0 0 0 40 18 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	643.39
Volume:	689.067
LogP:	5.629
LogD:	4.773
LogS:	-4.82
# Rotatable Bonds:	14
TPSA:	98.77
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.151
Synthetic Accessibility Score:	5.662
Fsp3:	0.65
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	3
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.173
MDCK Permeability:	4.483311568037607e-05
Pgp-inhibitor:	0.683
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.029
30% Bioavailability (F30%):	0.775

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.025
Plasma Protein Binding (PPB):	98.13750457763672%
Volume Distribution (VD):	0.429
Pgp-substrate:	2.18698787689209%

ADMET: Metabolism

CYP1A2-inhibitor:	0.025
CYP1A2-substrate:	0.534
CYP2C19-inhibitor:	0.758
CYP2C19-substrate:	0.721
CYP2C9-inhibitor:	0.861
CYP2C9-substrate:	0.112
CYP2D6-inhibitor:	0.581
CYP2D6-substrate:	0.285
CYP3A4-inhibitor:	0.976
CYP3A4-substrate:	0.772

ADMET: Excretion

Clearance (CL):	4.18
Half-life (T1/2):	0.25

ADMET: Toxicity

hERG Blockers:	0.873
Human Hepatotoxicity (H-HT):	0.404
Drug-inuced Liver Injury (DILI):	0.241
AMES Toxicity:	0.031
Rat Oral Acute Toxicity:	0.601
Maximum Recommended Daily Dose:	0.895
Skin Sensitization:	0.954
Carcinogencity:	0.177
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.933

Download Data

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

Natural Product: NPC470274

Natural Product ID:	NPC470274
*Common Name:**	SHEQTFKRFVRGDB-LTUKQXDOSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	SHEQTFKRFVRGDB-LTUKQXDOSA-N
Standard InCHI:	InChI=1S/C40H53NO6/c1-25(23-42)11-10-12-26(2)29-15-17-38(5)32-22-31-34(27(3)35(44)47-31)40(24-39(32,40)20-19-37(29,38)4)18-16-33(43)41-30(36(45)46-6)21-28-13-8-7-9-14-28/h7-9,11,13-14,23,26,29-32,34H,3,10,12,15-22,24H2,1-2,4-6H3,(H,41,43)/b25-11+/t26-,29-,30+,31-,32+,34-,37-,38+,39+,40-/m1/s1
SMILES:	CC(CCC=C(C)C=O)C1CCC2(C1(CCC34C2CC5C(C3(C4)CCC(=O)NC(CC6=CC=CC=C6)C(=O)OC)C(=C)C(=O)O5)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1939894
PubChem CID:	57396440
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
NPO33315	gardenia spp.	Species	Rubiaceae	Eukaryota	n.a.	Thai	n.a.	PMID[22142538]

☑ 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	1

Activity Type	# Activity
Tissue	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT177	Tissue	Aorta	Rattus norvegicus	Inhibition	=	10.0	%	PMID[508304]

☑ 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 NPC470274 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	186
0.1-0.2	857
0.2-0.3	1928
0.3-0.4	4900
0.4-0.5	22345
0.5-0.6	10822
0.6-0.7	1601
0.7-0.8	57
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7937	Intermediate Similarity	NPC476750
0.7823	Intermediate Similarity	NPC246913
0.7823	Intermediate Similarity	NPC470278
0.7771	Intermediate Similarity	NPC472761
0.777	Intermediate Similarity	NPC470276
0.7692	Intermediate Similarity	NPC160493
0.76	Intermediate Similarity	NPC90693
0.76	Intermediate Similarity	NPC64897
0.759	Intermediate Similarity	NPC476749
0.7582	Intermediate Similarity	NPC239770
0.7571	Intermediate Similarity	NPC470275
0.7552	Intermediate Similarity	NPC190663
0.755	Intermediate Similarity	NPC203486
0.7548	Intermediate Similarity	NPC473922
0.7535	Intermediate Similarity	NPC310467
0.7517	Intermediate Similarity	NPC475138
0.7516	Intermediate Similarity	NPC262324
0.75	Intermediate Similarity	NPC262216
0.7465	Intermediate Similarity	NPC169328
0.7419	Intermediate Similarity	NPC79921
0.7403	Intermediate Similarity	NPC243893
0.7391	Intermediate Similarity	NPC275839
0.7386	Intermediate Similarity	NPC208725
0.7378	Intermediate Similarity	NPC235460
0.7362	Intermediate Similarity	NPC93343
0.7353	Intermediate Similarity	NPC120667
0.7353	Intermediate Similarity	NPC278272
0.7347	Intermediate Similarity	NPC12881
0.7347	Intermediate Similarity	NPC140118
0.7342	Intermediate Similarity	NPC470273
0.7333	Intermediate Similarity	NPC73644
0.732	Intermediate Similarity	NPC329913
0.731	Intermediate Similarity	NPC80150
0.7308	Intermediate Similarity	NPC261709
0.7308	Intermediate Similarity	NPC111586
0.7308	Intermediate Similarity	NPC108852
0.7308	Intermediate Similarity	NPC473440
0.7299	Intermediate Similarity	NPC475649
0.7296	Intermediate Similarity	NPC173934
0.7273	Intermediate Similarity	NPC471864
0.7267	Intermediate Similarity	NPC472413
0.7267	Intermediate Similarity	NPC116057
0.725	Intermediate Similarity	NPC94602
0.7241	Intermediate Similarity	NPC475345
0.7233	Intermediate Similarity	NPC31171
0.7233	Intermediate Similarity	NPC237240
0.7233	Intermediate Similarity	NPC475578
0.7225	Intermediate Similarity	NPC476113
0.7222	Intermediate Similarity	NPC475561
0.7222	Intermediate Similarity	NPC152812
0.7222	Intermediate Similarity	NPC475417
0.7209	Intermediate Similarity	NPC475427
0.7208	Intermediate Similarity	NPC126516
0.7208	Intermediate Similarity	NPC4242
0.7208	Intermediate Similarity	NPC48929
0.7208	Intermediate Similarity	NPC471911
0.7205	Intermediate Similarity	NPC201692
0.72	Intermediate Similarity	NPC171007
0.72	Intermediate Similarity	NPC190849
0.72	Intermediate Similarity	NPC473220
0.72	Intermediate Similarity	NPC470753
0.72	Intermediate Similarity	NPC169913
0.7197	Intermediate Similarity	NPC234548
0.7197	Intermediate Similarity	NPC248287
0.7197	Intermediate Similarity	NPC161069
0.7188	Intermediate Similarity	NPC473541
0.7181	Intermediate Similarity	NPC47667
0.7181	Intermediate Similarity	NPC4974
0.7179	Intermediate Similarity	NPC475373
0.7179	Intermediate Similarity	NPC153007
0.7172	Intermediate Similarity	NPC237420
0.7171	Intermediate Similarity	NPC183722
0.7152	Intermediate Similarity	NPC217801
0.7152	Intermediate Similarity	NPC475128
0.7143	Intermediate Similarity	NPC472656
0.7133	Intermediate Similarity	NPC275576
0.7133	Intermediate Similarity	NPC470765
0.7124	Intermediate Similarity	NPC42423
0.7124	Intermediate Similarity	NPC72915
0.7107	Intermediate Similarity	NPC63737
0.7105	Intermediate Similarity	NPC225103
0.7101	Intermediate Similarity	NPC71205
0.7091	Intermediate Similarity	NPC114808
0.7091	Intermediate Similarity	NPC472657
0.7091	Intermediate Similarity	NPC472658
0.7075	Intermediate Similarity	NPC45777
0.7075	Intermediate Similarity	NPC477061
0.7059	Intermediate Similarity	NPC473443
0.7059	Intermediate Similarity	NPC472388
0.7037	Intermediate Similarity	NPC476757
0.702	Intermediate Similarity	NPC473082
0.7019	Intermediate Similarity	NPC135121
0.7019	Intermediate Similarity	NPC138775
0.7019	Intermediate Similarity	NPC260194
0.7017	Intermediate Similarity	NPC471754
0.7017	Intermediate Similarity	NPC206211
0.7017	Intermediate Similarity	NPC275170
0.7017	Intermediate Similarity	NPC471629
0.7017	Intermediate Similarity	NPC324251
0.7017	Intermediate Similarity	NPC306001
0.7017	Intermediate Similarity	NPC317882
0.7017	Intermediate Similarity	NPC473400
0.7012	Intermediate Similarity	NPC93666
0.7	Intermediate Similarity	NPC140021
0.6993	Remote Similarity	NPC273814
0.6982	Remote Similarity	NPC67080
0.6975	Remote Similarity	NPC471162
0.6974	Remote Similarity	NPC210950
0.6974	Remote Similarity	NPC473423
0.6974	Remote Similarity	NPC199738
0.6968	Remote Similarity	NPC80599
0.6968	Remote Similarity	NPC475493
0.6968	Remote Similarity	NPC209851
0.6959	Remote Similarity	NPC478015
0.6959	Remote Similarity	NPC478014
0.6959	Remote Similarity	NPC478016
0.6957	Remote Similarity	NPC477468
0.6957	Remote Similarity	NPC131966
0.6957	Remote Similarity	NPC191387
0.6954	Remote Similarity	NPC472414
0.6948	Remote Similarity	NPC147561
0.6943	Remote Similarity	NPC478140
0.6943	Remote Similarity	NPC194970
0.6937	Remote Similarity	NPC16912
0.6937	Remote Similarity	NPC471862
0.6933	Remote Similarity	NPC35996
0.6928	Remote Similarity	NPC195224
0.6923	Remote Similarity	NPC473300
0.6923	Remote Similarity	NPC453583
0.6923	Remote Similarity	NPC475336
0.6923	Remote Similarity	NPC132847
0.6914	Remote Similarity	NPC328824
0.6914	Remote Similarity	NPC471912
0.6914	Remote Similarity	NPC80895
0.6909	Remote Similarity	NPC125033
0.6908	Remote Similarity	NPC470816
0.6908	Remote Similarity	NPC470818
0.6908	Remote Similarity	NPC477366
0.6906	Remote Similarity	NPC327699
0.6903	Remote Similarity	NPC246079
0.6903	Remote Similarity	NPC472418
0.6899	Remote Similarity	NPC173569
0.6899	Remote Similarity	NPC477874
0.6894	Remote Similarity	NPC477217
0.6894	Remote Similarity	NPC475135
0.6894	Remote Similarity	NPC201244
0.6894	Remote Similarity	NPC5620
0.689	Remote Similarity	NPC66894
0.689	Remote Similarity	NPC8102
0.6887	Remote Similarity	NPC477362
0.6887	Remote Similarity	NPC473938
0.6887	Remote Similarity	NPC469742
0.6886	Remote Similarity	NPC261659
0.6885	Remote Similarity	NPC67246
0.6885	Remote Similarity	NPC33372
0.6875	Remote Similarity	NPC90614
0.6875	Remote Similarity	NPC97667
0.6875	Remote Similarity	NPC100913
0.6875	Remote Similarity	NPC171207
0.6875	Remote Similarity	NPC275592
0.6871	Remote Similarity	NPC301946
0.6871	Remote Similarity	NPC277053
0.6871	Remote Similarity	NPC84129
0.6867	Remote Similarity	NPC253591
0.6863	Remote Similarity	NPC477357
0.6863	Remote Similarity	NPC477365
0.6859	Remote Similarity	NPC244866
0.6855	Remote Similarity	NPC249817
0.6846	Remote Similarity	NPC476183
0.6842	Remote Similarity	NPC293164
0.6842	Remote Similarity	NPC473083
0.6842	Remote Similarity	NPC471394
0.6839	Remote Similarity	NPC49272
0.6836	Remote Similarity	NPC203005
0.6835	Remote Similarity	NPC11266
0.6835	Remote Similarity	NPC176883
0.6835	Remote Similarity	NPC477896
0.6835	Remote Similarity	NPC477893
0.6832	Remote Similarity	NPC291599
0.6832	Remote Similarity	NPC476978
0.6832	Remote Similarity	NPC27377
0.6832	Remote Similarity	NPC97947
0.6832	Remote Similarity	NPC118080
0.6832	Remote Similarity	NPC472576
0.6832	Remote Similarity	NPC87448
0.6832	Remote Similarity	NPC41481
0.6832	Remote Similarity	NPC224491
0.6829	Remote Similarity	NPC56731
0.6829	Remote Similarity	NPC473602
0.6823	Remote Similarity	NPC470280
0.6821	Remote Similarity	NPC472415
0.6821	Remote Similarity	NPC12016
0.6818	Remote Similarity	NPC211713
0.6818	Remote Similarity	NPC71271
0.6818	Remote Similarity	NPC296712
0.6818	Remote Similarity	NPC88378
0.6818	Remote Similarity	NPC230331
0.6818	Remote Similarity	NPC477370
0.6813	Remote Similarity	NPC22676
0.6813	Remote Similarity	NPC475482

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 NPC470274 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	138
0.1-0.2	450
0.2-0.3	902
0.3-0.4	2117
0.4-0.5	3728
0.5-0.6	1656
0.6-0.7	159
0.7-0.8	0
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
0.7338	Intermediate Similarity	NPD3643	Approved
0.7338	Intermediate Similarity	NPD3644	Approved
0.7338	Intermediate Similarity	NPD3642	Approved
0.7294	Intermediate Similarity	NPD7997	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5981	Approved
0.7233	Intermediate Similarity	NPD7274	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD5618	Discontinued
0.7172	Intermediate Similarity	NPD4479	Discontinued
0.7162	Intermediate Similarity	NPD5108	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4738	Phase 2
0.7039	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD7961	Discontinued
0.6875	Remote Similarity	NPD6858	Approved
0.6875	Remote Similarity	NPD7094	Approved
0.6875	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD7236	Approved
0.6842	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD8407	Phase 2
0.6826	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD6852	Discontinued
0.678	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD8435	Approved
0.6776	Remote Similarity	NPD8361	Approved
0.6776	Remote Similarity	NPD8360	Approved
0.6772	Remote Similarity	NPD8643	Discontinued
0.6766	Remote Similarity	NPD7239	Suspended
0.6757	Remote Similarity	NPD6065	Approved
0.6738	Remote Similarity	NPD8485	Approved
0.6735	Remote Similarity	NPD1348	Approved
0.6728	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD2218	Phase 2
0.6711	Remote Similarity	NPD2217	Approved
0.671	Remote Similarity	NPD7084	Phase 3
0.6709	Remote Similarity	NPD8416	Discontinued
0.6709	Remote Similarity	NPD8265	Approved
0.6707	Remote Similarity	NPD8323	Discontinued
0.6686	Remote Similarity	NPD7315	Approved
0.6667	Remote Similarity	NPD4766	Approved
0.6667	Remote Similarity	NPD4209	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8368	Discontinued
0.6647	Remote Similarity	NPD6390	Discontinued
0.6646	Remote Similarity	NPD7715	Approved
0.6646	Remote Similarity	NPD7714	Approved
0.6646	Remote Similarity	NPD6663	Approved
0.6632	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD2584	Suspended
0.6579	Remote Similarity	NPD2956	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD4685	Phase 3
0.6562	Remote Similarity	NPD4684	Phase 3
0.6562	Remote Similarity	NPD4686	Approved
0.6541	Remote Similarity	NPD3616	Approved
0.6541	Remote Similarity	NPD2573	Approved
0.6541	Remote Similarity	NPD3088	Approved
0.6541	Remote Similarity	NPD3615	Approved
0.6541	Remote Similarity	NPD3089	Approved
0.6541	Remote Similarity	NPD3087	Approved
0.6541	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD2566	Approved
0.6541	Remote Similarity	NPD2570	Approved
0.6541	Remote Similarity	NPD4746	Phase 3
0.6541	Remote Similarity	NPD3614	Approved
0.6541	Remote Similarity	NPD3090	Approved
0.6541	Remote Similarity	NPD2571	Approved
0.6541	Remote Similarity	NPD4745	Approved
0.6541	Remote Similarity	NPD2574	Discontinued
0.6538	Remote Similarity	NPD7962	Phase 2
0.6536	Remote Similarity	NPD4215	Approved
0.6536	Remote Similarity	NPD4217	Approved
0.6536	Remote Similarity	NPD4216	Approved
0.6536	Remote Similarity	NPD2610	Approved
0.6536	Remote Similarity	NPD3132	Approved
0.6536	Remote Similarity	NPD4218	Approved
0.6536	Remote Similarity	NPD2611	Approved
0.6536	Remote Similarity	NPD2608	Approved
0.6536	Remote Similarity	NPD3131	Approved
0.6536	Remote Similarity	NPD2609	Approved
0.6536	Remote Similarity	NPD2612	Approved
0.6533	Remote Similarity	NPD7610	Discontinued
0.6522	Remote Similarity	NPD8172	Phase 2
0.6522	Remote Similarity	NPD8173	Phase 2
0.6519	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6623	Phase 3
0.6497	Remote Similarity	NPD5736	Approved
0.6486	Remote Similarity	NPD2652	Approved
0.6486	Remote Similarity	NPD2650	Approved
0.6477	Remote Similarity	NPD6746	Phase 2
0.6467	Remote Similarity	NPD4576	Approved
0.6467	Remote Similarity	NPD4574	Approved
0.6463	Remote Similarity	NPD7720	Phase 2
0.6461	Remote Similarity	NPD7687	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD2613	Approved
0.6446	Remote Similarity	NPD8166	Discontinued
0.6444	Remote Similarity	NPD7799	Discontinued
0.6442	Remote Similarity	NPD6864	Phase 2
0.6442	Remote Similarity	NPD6865	Phase 2
0.6441	Remote Similarity	NPD8127	Discontinued
0.6438	Remote Similarity	NPD7713	Phase 3
0.6438	Remote Similarity	NPD8118	Discontinued
0.6429	Remote Similarity	NPD6287	Discontinued
0.6429	Remote Similarity	NPD4480	Approved
0.6429	Remote Similarity	NPD8165	Discontinued
0.6424	Remote Similarity	NPD7522	Discontinued
0.642	Remote Similarity	NPD2157	Approved
0.6419	Remote Similarity	NPD2607	Approved
0.6416	Remote Similarity	NPD7011	Discontinued
0.641	Remote Similarity	NPD2198	Approved
0.641	Remote Similarity	NPD2199	Approved
0.6406	Remote Similarity	NPD7565	Approved
0.6392	Remote Similarity	NPD3662	Phase 3
0.6392	Remote Similarity	NPD3663	Approved
0.6392	Remote Similarity	NPD3664	Approved
0.6392	Remote Similarity	NPD3661	Approved
0.6386	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD8404	Phase 2
0.6379	Remote Similarity	NPD7972	Discontinued
0.6375	Remote Similarity	NPD4621	Approved
0.6375	Remote Similarity	NPD4619	Approved
0.6369	Remote Similarity	NPD6302	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD4230	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD6273	Approved
0.6352	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.635	Remote Similarity	NPD8462	Phase 1
0.6347	Remote Similarity	NPD3400	Discontinued
0.6347	Remote Similarity	NPD7487	Discontinued
0.6347	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD5706	Approved
0.6345	Remote Similarity	NPD5705	Approved
0.6345	Remote Similarity	NPD5704	Approved
0.634	Remote Similarity	NPD4504	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD3455	Phase 2
0.6327	Remote Similarity	NPD4233	Approved
0.6327	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD4234	Approved
0.6323	Remote Similarity	NPD4806	Approved
0.6323	Remote Similarity	NPD4807	Approved
0.6316	Remote Similarity	NPD7606	Phase 3
0.6312	Remote Similarity	NPD7008	Discontinued
0.6312	Remote Similarity	NPD3136	Phase 2
0.6312	Remote Similarity	NPD6039	Approved
0.631	Remote Similarity	NPD7602	Clinical (unspecified phase)
0.631	Remote Similarity	NPD7683	Discontinued
0.631	Remote Similarity	NPD7740	Clinical (unspecified phase)
0.6307	Remote Similarity	NPD7057	Phase 3
0.6307	Remote Similarity	NPD7058	Phase 2
0.6296	Remote Similarity	NPD6309	Approved
0.6296	Remote Similarity	NPD6346	Approved
0.6296	Remote Similarity	NPD3373	Approved
0.6296	Remote Similarity	NPD6310	Approved
0.6296	Remote Similarity	NPD6311	Approved
0.6294	Remote Similarity	NPD8161	Suspended
0.6289	Remote Similarity	NPD5204	Approved
0.6289	Remote Similarity	NPD7828	Discontinued
0.6287	Remote Similarity	NPD7179	Phase 2
0.6286	Remote Similarity	NPD4335	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD7599	Phase 2
0.6284	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD6637	Approved
0.6282	Remote Similarity	NPD3880	Clinical (unspecified phase)
0.628	Remote Similarity	NPD2569	Approved
0.628	Remote Similarity	NPD2567	Approved
0.6276	Remote Similarity	NPD7497	Discontinued
0.6275	Remote Similarity	NPD2617	Discontinued
0.6275	Remote Similarity	NPD7741	Discontinued
0.6265	Remote Similarity	NPD2174	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD3881	Discontinued
0.6257	Remote Similarity	NPD7613	Discontinued
0.625	Remote Similarity	NPD5203	Approved
0.625	Remote Similarity	NPD5201	Approved
0.625	Remote Similarity	NPD4874	Phase 2
0.625	Remote Similarity	NPD4617	Approved
0.625	Remote Similarity	NPD4620	Approved
0.625	Remote Similarity	NPD6647	Phase 2
0.6242	Remote Similarity	NPD6025	Phase 1
0.6235	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD8032	Phase 2
0.6235	Remote Similarity	NPD7478	Approved
0.6229	Remote Similarity	NPD8019	Approved
0.6226	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6225	Remote Similarity	NPD5951	Approved
0.6225	Remote Similarity	NPD2629	Approved
0.6224	Remote Similarity	NPD4760	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD7795	Phase 2
0.6222	Remote Similarity	NPD7608	Discontinued
0.622	Remote Similarity	NPD6073	Approved
0.622	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.622	Remote Similarity	NPD5725	Approved
0.6213	Remote Similarity	NPD7295	Approved
0.6207	Remote Similarity	NPD8417	Discontinued
0.6207	Remote Similarity	NPD5909	Discontinued
0.6207	Remote Similarity	NPD6502	Phase 2

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