NPASS Compound

Structure

NPC474583 OpenBabel07101719522D 35 39 0 0 1 0 0 0 0 0999 V2000 -0.3364 3.3147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8364 2.4487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3612 -1.2330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0817 4.4714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1638 0.7804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4837 1.9714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3497 -0.5286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2157 -0.0286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4152 -1.6113 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4097 -1.5068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6176 1.4714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2157 2.9714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7516 0.9714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3497 2.4714 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 -1.7213 0.4612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8364 2.4487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0303 -0.4898 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.9478 3.9714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4837 -0.0286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0085 -0.6977 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6176 -0.5286 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4837 0.9714 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.2157 0.9714 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.0817 2.4714 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7431 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0817 1.4714 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7516 -0.0286 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.3497 1.4714 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -8.9478 2.9714 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -9.8138 4.4714 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9478 0.9714 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 4 20 1 0 0 0 0 7 8 1 0 0 0 0 7 22 2 0 0 0 0 8 26 1 0 0 0 0 9 10 1 0 0 0 0 9 23 1 0 0 0 0 10 24 1 0 0 0 0 11 14 1 0 0 0 0 11 25 1 0 0 0 0 12 15 1 0 0 0 0 12 27 1 0 0 0 0 13 16 1 0 0 0 0 13 21 1 0 0 0 0 14 30 1 0 0 0 0 15 31 1 0 0 0 0 16 32 1 0 0 0 0 17 19 1 0 0 0 0 17 28 1 0 0 0 0 18 21 2 0 0 0 0 19 3 1 1 0 0 0 19 23 1 0 0 0 0 20 33 2 3 0 0 0 20 34 1 0 0 0 0 21 28 1 0 0 0 0 22 24 1 0 0 0 0 22 25 1 0 0 0 0 23 30 1 1 0 0 0 24 30 1 1 0 0 0 25 31 1 1 0 0 0 26 29 1 0 0 0 0 26 31 1 1 0 0 0 27 29 1 0 0 0 0 27 33 1 1 0 0 0 28 32 2 0 0 0 0 29 35 1 1 0 0 0 30 5 1 1 0 0 0 31 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	480.37
Volume:	530.978
LogP:	5.061
LogD:	5.286
LogS:	-5.438
# Rotatable Bonds:	5
TPSA:	61.69
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.467
Synthetic Accessibility Score:	5.145
Fsp3:	0.806
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.787
MDCK Permeability:	2.4106833734549582e-05
Pgp-inhibitor:	0.935
Pgp-substrate:	0.715
Human Intestinal Absorption (HIA):	0.044
20% Bioavailability (F20%):	0.99
30% Bioavailability (F30%):	0.972

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	93.35977172851562%
Volume Distribution (VD):	1.064
Pgp-substrate:	1.423807978630066%

ADMET: Metabolism

CYP1A2-inhibitor:	0.049
CYP1A2-substrate:	0.26
CYP2C19-inhibitor:	0.081
CYP2C19-substrate:	0.836
CYP2C9-inhibitor:	0.245
CYP2C9-substrate:	0.07
CYP2D6-inhibitor:	0.276
CYP2D6-substrate:	0.81
CYP3A4-inhibitor:	0.788
CYP3A4-substrate:	0.676

ADMET: Excretion

Clearance (CL):	2.733
Half-life (T1/2):	0.207

ADMET: Toxicity

hERG Blockers:	0.307
Human Hepatotoxicity (H-HT):	0.652
Drug-inuced Liver Injury (DILI):	0.095
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.115
Maximum Recommended Daily Dose:	0.357
Skin Sensitization:	0.457
Carcinogencity:	0.006
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.954

Download Data

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

Natural Product: NPC474583

Natural Product ID:	NPC474583
*Common Name:**	Lokysterolamine B
IUPAC Name:	N-[(3S,4R,5R,9R,10R,13R,14R,17R)-4-hydroxy-10,13-dimethyl-17-[(2R)-1-(4-propan-2-ylidene-2,3-dihydropyrrol-5-yl)propan-2-yl]-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]acetamide
Synonyms:
Standard InCHIKey:	QUNQBOZYERAKAG-QFGHJUQXSA-N
Standard InCHI:	InChI=1S/C31H48N2O2/c1-18(2)21-13-16-32-28(21)17-19(3)23-9-10-24-22-7-8-26-29(35)27(33-20(4)34)12-15-31(26,6)25(22)11-14-30(23,24)5/h7,19,23-27,29,35H,8-17H2,1-6H3,(H,33,34)/t19-,23-,24+,25+,26+,27+,29-,30-,31-/m1/s1
SMILES:	CC(CC1=NCCC1=C(C)C)C2CCC3C2(CCC4C3=CCC5C4(CCC(C5O)NC(=O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL474921
PubChem CID:	21123588
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
NPO32780	corticium sp.	Species	Corticiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12193035]
NPO32780	corticium sp.	Species	Corticiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17391049]
NPO32780	corticium sp.	Species	Corticiaceae	Eukaryota	n.a.	New Britain, Papua New Guinea	n.a.	PMID[24195491]
NPO32780	corticium sp.	Species	Corticiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7964780]

☑ 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	4
Others	4

Activity Type	# Activity
Cell Line	4
Organism	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	1.0	ug.mL-1	PMID[548192]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	0.5	ug.mL-1	PMID[548192]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	1.0	ug.mL-1	PMID[548192]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	>	2.0	ug.mL-1	PMID[548192]
NPT2	Others	Unspecified		Activity	=	0.48	n.a.	PMID[548192]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	8.0	mm	PMID[548192]
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	0.0	mm	PMID[548192]
NPT2	Others	Unspecified		Activity	>	12.5	n.a.	PMID[548192]

☑ 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 NPC474583 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	95
0.1-0.2	845
0.2-0.3	11433
0.3-0.4	15877
0.4-0.5	8691
0.5-0.6	4831
0.6-0.7	859
0.7-0.8	56
0.8-0.85	6
0.85-0.9	1
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9495	High Similarity	NPC25340
0.9223	High Similarity	NPC56796
0.8713	High Similarity	NPC471083
0.8462	Intermediate Similarity	NPC55462
0.8317	Intermediate Similarity	NPC240650
0.8218	Intermediate Similarity	NPC476903
0.82	Intermediate Similarity	NPC280710
0.82	Intermediate Similarity	NPC243985
0.8173	Intermediate Similarity	NPC50815
0.8148	Intermediate Similarity	NPC472359
0.8037	Intermediate Similarity	NPC169375
0.8	Intermediate Similarity	NPC247060
0.7925	Intermediate Similarity	NPC293299
0.7925	Intermediate Similarity	NPC45365
0.781	Intermediate Similarity	NPC275686
0.7757	Intermediate Similarity	NPC241879
0.77	Intermediate Similarity	NPC34754
0.7679	Intermediate Similarity	NPC469968
0.7679	Intermediate Similarity	NPC80834
0.7636	Intermediate Similarity	NPC159367
0.7593	Intermediate Similarity	NPC90538
0.7523	Intermediate Similarity	NPC119329
0.75	Intermediate Similarity	NPC328052
0.7458	Intermediate Similarity	NPC242692
0.7455	Intermediate Similarity	NPC36497
0.7358	Intermediate Similarity	NPC289140
0.7333	Intermediate Similarity	NPC473314
0.7297	Intermediate Similarity	NPC258130
0.729	Intermediate Similarity	NPC140300
0.7281	Intermediate Similarity	NPC66862
0.7264	Intermediate Similarity	NPC272732
0.7264	Intermediate Similarity	NPC311164
0.725	Intermediate Similarity	NPC472458
0.7232	Intermediate Similarity	NPC46981
0.7228	Intermediate Similarity	NPC75810
0.7222	Intermediate Similarity	NPC140685
0.7222	Intermediate Similarity	NPC91604
0.7193	Intermediate Similarity	NPC472313
0.7193	Intermediate Similarity	NPC72753
0.7188	Intermediate Similarity	NPC189883
0.7179	Intermediate Similarity	NPC165396
0.7143	Intermediate Similarity	NPC1319
0.713	Intermediate Similarity	NPC167419
0.713	Intermediate Similarity	NPC474459
0.713	Intermediate Similarity	NPC474164
0.7113	Intermediate Similarity	NPC214570
0.7083	Intermediate Similarity	NPC257347
0.7083	Intermediate Similarity	NPC471723
0.7083	Intermediate Similarity	NPC141071
0.7073	Intermediate Similarity	NPC237286
0.7071	Intermediate Similarity	NPC236112
0.7069	Intermediate Similarity	NPC474452
0.7059	Intermediate Similarity	NPC152684
0.7041	Intermediate Similarity	NPC138621
0.7041	Intermediate Similarity	NPC275910
0.7041	Intermediate Similarity	NPC285761
0.7041	Intermediate Similarity	NPC167037
0.7041	Intermediate Similarity	NPC244385
0.7041	Intermediate Similarity	NPC6978
0.703	Intermediate Similarity	NPC246956
0.7027	Intermediate Similarity	NPC176012
0.701	Intermediate Similarity	NPC107059
0.701	Intermediate Similarity	NPC300324
0.701	Intermediate Similarity	NPC237460
0.701	Intermediate Similarity	NPC46160
0.701	Intermediate Similarity	NPC134330
0.701	Intermediate Similarity	NPC73875
0.701	Intermediate Similarity	NPC321381
0.701	Intermediate Similarity	NPC202642
0.701	Intermediate Similarity	NPC129165
0.701	Intermediate Similarity	NPC321016
0.701	Intermediate Similarity	NPC240604
0.7	Intermediate Similarity	NPC135799
0.7	Intermediate Similarity	NPC192456
0.7	Intermediate Similarity	NPC474531
0.6991	Remote Similarity	NPC86906
0.699	Remote Similarity	NPC166458
0.6972	Remote Similarity	NPC4834
0.697	Remote Similarity	NPC30986
0.697	Remote Similarity	NPC209430
0.697	Remote Similarity	NPC80530
0.697	Remote Similarity	NPC273410
0.6964	Remote Similarity	NPC98765
0.6949	Remote Similarity	NPC470540
0.6939	Remote Similarity	NPC155986
0.6939	Remote Similarity	NPC318495
0.6939	Remote Similarity	NPC198968
0.6937	Remote Similarity	NPC118275
0.6931	Remote Similarity	NPC224072
0.6931	Remote Similarity	NPC283277
0.6931	Remote Similarity	NPC30166
0.6931	Remote Similarity	NPC39966
0.6931	Remote Similarity	NPC470049
0.6907	Remote Similarity	NPC28657
0.6907	Remote Similarity	NPC121744
0.6907	Remote Similarity	NPC22105
0.6907	Remote Similarity	NPC230301
0.6907	Remote Similarity	NPC285893
0.6907	Remote Similarity	NPC304309
0.6907	Remote Similarity	NPC288035
0.6907	Remote Similarity	NPC118508
0.6907	Remote Similarity	NPC134847
0.6907	Remote Similarity	NPC322353
0.6907	Remote Similarity	NPC162742
0.6907	Remote Similarity	NPC136188
0.6903	Remote Similarity	NPC212874
0.69	Remote Similarity	NPC13554
0.69	Remote Similarity	NPC236237
0.69	Remote Similarity	NPC102253
0.69	Remote Similarity	NPC322313
0.6875	Remote Similarity	NPC474140
0.6869	Remote Similarity	NPC87604
0.6869	Remote Similarity	NPC473943
0.6869	Remote Similarity	NPC85346
0.6869	Remote Similarity	NPC477514
0.6869	Remote Similarity	NPC477522
0.6869	Remote Similarity	NPC65897
0.6869	Remote Similarity	NPC186191
0.6869	Remote Similarity	NPC302041
0.6869	Remote Similarity	NPC205455
0.6869	Remote Similarity	NPC474216
0.6864	Remote Similarity	NPC478137
0.6857	Remote Similarity	NPC324405
0.6837	Remote Similarity	NPC470362
0.6837	Remote Similarity	NPC247325
0.6837	Remote Similarity	NPC244488
0.6837	Remote Similarity	NPC113733
0.6832	Remote Similarity	NPC470383
0.68	Remote Similarity	NPC328714
0.68	Remote Similarity	NPC47982
0.68	Remote Similarity	NPC84694
0.68	Remote Similarity	NPC28862
0.68	Remote Similarity	NPC109546
0.68	Remote Similarity	NPC81306
0.68	Remote Similarity	NPC143182
0.6796	Remote Similarity	NPC478102
0.6796	Remote Similarity	NPC470077
0.6796	Remote Similarity	NPC124172
0.6796	Remote Similarity	NPC209802
0.6768	Remote Similarity	NPC34019
0.6765	Remote Similarity	NPC218616
0.6765	Remote Similarity	NPC202389
0.6765	Remote Similarity	NPC201852
0.6765	Remote Similarity	NPC248886
0.6765	Remote Similarity	NPC296701
0.6765	Remote Similarity	NPC101462
0.6765	Remote Similarity	NPC87489
0.6765	Remote Similarity	NPC20853
0.6765	Remote Similarity	NPC49964
0.6759	Remote Similarity	NPC93027
0.6754	Remote Similarity	NPC475239
0.6733	Remote Similarity	NPC26117
0.6733	Remote Similarity	NPC234193
0.6733	Remote Similarity	NPC241290
0.6733	Remote Similarity	NPC164840
0.6733	Remote Similarity	NPC209944
0.6731	Remote Similarity	NPC318390
0.6731	Remote Similarity	NPC24733
0.6729	Remote Similarity	NPC84171
0.6726	Remote Similarity	NPC152718
0.6701	Remote Similarity	NPC182717
0.6701	Remote Similarity	NPC201373
0.67	Remote Similarity	NPC76931
0.67	Remote Similarity	NPC18603
0.67	Remote Similarity	NPC318136
0.67	Remote Similarity	NPC312328
0.67	Remote Similarity	NPC307965
0.6699	Remote Similarity	NPC477818
0.6699	Remote Similarity	NPC317458
0.6699	Remote Similarity	NPC207013
0.6699	Remote Similarity	NPC113978
0.6699	Remote Similarity	NPC110778
0.6696	Remote Similarity	NPC477292
0.6695	Remote Similarity	NPC79238
0.6694	Remote Similarity	NPC469943
0.6667	Remote Similarity	NPC24277
0.6667	Remote Similarity	NPC253645
0.6667	Remote Similarity	NPC474970
0.6667	Remote Similarity	NPC264245
0.6667	Remote Similarity	NPC474759
0.6667	Remote Similarity	NPC47761
0.6667	Remote Similarity	NPC257962
0.6667	Remote Similarity	NPC132847
0.6667	Remote Similarity	NPC6707
0.6667	Remote Similarity	NPC147835
0.6667	Remote Similarity	NPC94462
0.6667	Remote Similarity	NPC474683
0.6667	Remote Similarity	NPC85001
0.6667	Remote Similarity	NPC7505
0.6667	Remote Similarity	NPC23852
0.6667	Remote Similarity	NPC474731
0.6667	Remote Similarity	NPC125399
0.6667	Remote Similarity	NPC474563
0.6667	Remote Similarity	NPC82986
0.6667	Remote Similarity	NPC6391
0.6667	Remote Similarity	NPC474752
0.6667	Remote Similarity	NPC209620
0.6667	Remote Similarity	NPC96319
0.6667	Remote Similarity	NPC261266
0.6667	Remote Similarity	NPC95920

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 NPC474583 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	95
0.1-0.2	426
0.2-0.3	3263
0.3-0.4	4127
0.4-0.5	888
0.5-0.6	277
0.6-0.7	71
0.7-0.8	3
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
0.767	Intermediate Similarity	NPD5771	Approved
0.7019	Intermediate Similarity	NPD4722	Approved
0.7019	Intermediate Similarity	NPD4723	Approved
0.6907	Remote Similarity	NPD7339	Approved
0.6907	Remote Similarity	NPD6942	Approved
0.69	Remote Similarity	NPD7525	Registered
0.6667	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD8418	Phase 2
0.6545	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD6939	Phase 2
0.6495	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD5328	Approved
0.6476	Remote Similarity	NPD4786	Approved
0.6471	Remote Similarity	NPD6420	Discontinued
0.6471	Remote Similarity	NPD7645	Phase 2
0.6465	Remote Similarity	NPD6924	Approved
0.6465	Remote Similarity	NPD6926	Approved
0.6429	Remote Similarity	NPD4243	Approved
0.6396	Remote Similarity	NPD5707	Approved
0.6364	Remote Similarity	NPD6079	Approved
0.6355	Remote Similarity	NPD3618	Phase 1
0.6337	Remote Similarity	NPD6933	Approved
0.6306	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.63	Remote Similarity	NPD4784	Approved
0.63	Remote Similarity	NPD4785	Approved
0.6289	Remote Similarity	NPD6705	Phase 1
0.6286	Remote Similarity	NPD3667	Approved
0.6273	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD6404	Discontinued
0.6224	Remote Similarity	NPD6922	Approved
0.6224	Remote Similarity	NPD6923	Approved
0.6179	Remote Similarity	NPD8298	Phase 2
0.6176	Remote Similarity	NPD1346	Approved
0.6168	Remote Similarity	NPD3133	Approved
0.6168	Remote Similarity	NPD3666	Approved
0.6168	Remote Similarity	NPD3665	Phase 1
0.6162	Remote Similarity	NPD7143	Approved
0.6162	Remote Similarity	NPD7144	Approved
0.6161	Remote Similarity	NPD4202	Approved
0.6154	Remote Similarity	NPD6929	Approved
0.6147	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6131	Remote Similarity	NPD6334	Approved
0.6131	Remote Similarity	NPD6333	Approved
0.6126	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD6700	Approved
0.61	Remote Similarity	NPD7151	Approved
0.61	Remote Similarity	NPD7152	Approved
0.61	Remote Similarity	NPD7150	Approved
0.6098	Remote Similarity	NPD7335	Phase 2
0.6098	Remote Similarity	NPD7336	Phase 2
0.6098	Remote Similarity	NPD7337	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD7509	Discontinued
0.6095	Remote Similarity	NPD6931	Approved
0.6095	Remote Similarity	NPD4748	Discontinued
0.6095	Remote Similarity	NPD6930	Phase 2
0.609	Remote Similarity	NPD6914	Discontinued
0.6087	Remote Similarity	NPD7919	Phase 3
0.6087	Remote Similarity	NPD7920	Phase 3
0.608	Remote Similarity	NPD7755	Approved
0.608	Remote Similarity	NPD7754	Approved
0.6078	Remote Similarity	NPD5275	Approved
0.6078	Remote Similarity	NPD4190	Phase 3
0.6063	Remote Similarity	NPD7522	Discontinued
0.6034	Remote Similarity	NPD8088	Phase 1
0.6033	Remote Similarity	NPD8174	Phase 2
0.6	Remote Similarity	NPD6640	Phase 3
0.6	Remote Similarity	NPD4195	Approved
0.6	Remote Similarity	NPD5357	Phase 1
0.6	Remote Similarity	NPD5222	Approved
0.6	Remote Similarity	NPD4697	Phase 3
0.6	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5221	Approved
0.5969	Remote Similarity	NPD6909	Approved
0.5969	Remote Similarity	NPD6908	Approved
0.5963	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD5776	Phase 2
0.5962	Remote Similarity	NPD6925	Approved
0.5962	Remote Similarity	NPD6932	Approved
0.5948	Remote Similarity	NPD4755	Approved
0.5948	Remote Similarity	NPD5173	Approved
0.5929	Remote Similarity	NPD6703	Approved
0.5929	Remote Similarity	NPD6702	Approved
0.5926	Remote Similarity	NPD6695	Phase 3
0.5909	Remote Similarity	NPD5279	Phase 3
0.5905	Remote Similarity	NPD7145	Approved
0.5893	Remote Similarity	NPD4753	Phase 2
0.5877	Remote Similarity	NPD6399	Phase 3
0.5872	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5868	Remote Similarity	NPD7333	Discontinued
0.5849	Remote Similarity	NPD6683	Phase 2
0.5847	Remote Similarity	NPD5286	Approved
0.5847	Remote Similarity	NPD4700	Approved
0.5847	Remote Similarity	NPD4696	Approved
0.5847	Remote Similarity	NPD5285	Approved
0.5833	Remote Similarity	NPD4223	Phase 3
0.5833	Remote Similarity	NPD4221	Approved
0.5818	Remote Similarity	NPD5329	Approved
0.5818	Remote Similarity	NPD6893	Approved
0.5798	Remote Similarity	NPD5223	Approved
0.5794	Remote Similarity	NPD7514	Phase 3
0.5789	Remote Similarity	NPD7515	Phase 2
0.5772	Remote Similarity	NPD7320	Approved
0.5763	Remote Similarity	NPD7638	Approved
0.5763	Remote Similarity	NPD5290	Discontinued
0.5755	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.575	Remote Similarity	NPD5224	Approved
0.575	Remote Similarity	NPD5211	Phase 2
0.575	Remote Similarity	NPD5225	Approved
0.575	Remote Similarity	NPD5226	Approved
0.575	Remote Similarity	NPD4633	Approved
0.5741	Remote Similarity	NPD6902	Approved
0.5738	Remote Similarity	NPD6675	Approved
0.5738	Remote Similarity	NPD6920	Discontinued
0.5738	Remote Similarity	NPD7128	Approved
0.5738	Remote Similarity	NPD6402	Approved
0.5738	Remote Similarity	NPD5739	Approved
0.5727	Remote Similarity	NPD3668	Phase 3
0.5727	Remote Similarity	NPD4197	Approved
0.5726	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7750	Discontinued
0.5714	Remote Similarity	NPD7524	Approved
0.5714	Remote Similarity	NPD7640	Approved
0.5714	Remote Similarity	NPD7639	Approved
0.5702	Remote Similarity	NPD5174	Approved
0.5702	Remote Similarity	NPD5175	Approved
0.5702	Remote Similarity	NPD4754	Approved
0.5691	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.5685	Remote Similarity	NPD7625	Phase 1
0.5678	Remote Similarity	NPD6084	Phase 2
0.5678	Remote Similarity	NPD6083	Phase 2
0.5667	Remote Similarity	NPD4159	Approved
0.5664	Remote Similarity	NPD6903	Approved
0.5656	Remote Similarity	NPD5141	Approved
0.5652	Remote Similarity	NPD8449	Approved
0.5648	Remote Similarity	NPD7332	Phase 2
0.5645	Remote Similarity	NPD6899	Approved
0.5645	Remote Similarity	NPD6881	Approved
0.5645	Remote Similarity	NPD6415	Discontinued
0.5641	Remote Similarity	NPD5210	Approved
0.5641	Remote Similarity	NPD4629	Approved
0.5636	Remote Similarity	NPD4788	Approved
0.5631	Remote Similarity	NPD3187	Discontinued
0.5625	Remote Similarity	NPD7521	Approved
0.5625	Remote Similarity	NPD4138	Approved
0.5625	Remote Similarity	NPD7146	Approved
0.5625	Remote Similarity	NPD7334	Approved
0.5625	Remote Similarity	NPD5330	Approved
0.5625	Remote Similarity	NPD4688	Approved
0.5625	Remote Similarity	NPD6409	Approved
0.5625	Remote Similarity	NPD4689	Approved
0.5625	Remote Similarity	NPD6684	Approved
0.5625	Remote Similarity	NPD4690	Approved
0.5625	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD4693	Phase 3
0.5625	Remote Similarity	NPD5205	Approved
0.5619	Remote Similarity	NPD8264	Approved
0.5614	Remote Similarity	NPD6051	Approved
0.5612	Remote Similarity	NPD8450	Suspended
0.561	Remote Similarity	NPD4768	Approved
0.561	Remote Similarity	NPD4767	Approved
0.56	Remote Similarity	NPD6373	Approved
0.56	Remote Similarity	NPD6372	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