NPASS Compound

Structure

NPC471201 OpenBabel07101718182D 42 43 0 0 1 0 0 0 0 0999 V2000 2.1582 1.8182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8854 13.9807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4731 13.1717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2921 14.8942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2083 6.0724 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6150 6.9859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7961 5.2634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0664 12.2581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0272 7.7949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7043 15.7033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3893 4.3498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6542 11.4491 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4340 8.7085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1110 16.6168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9771 3.5408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2475 10.5356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8462 9.5175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5233 17.4258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 -0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 1.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3776 0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 1.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 -0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9245 18.4439 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5704 2.6272 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.6456 0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2529 10.4310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3776 1.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9300 18.3394 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9135 0.4067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1691 1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5759 2.5227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6691 0.7431 0.0000 C 0 0 0 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 3.3313 19.3574 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6651 11.2401 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2437 1.9067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3422 19.1484 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0119 3.3317 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5522 2.0704 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6637 0.6386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 3 1 0 0 0 0 2 4 1 0 0 0 0 3 8 1 0 0 0 0 4 10 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 9 1 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 9 13 1 0 0 0 0 10 14 1 0 0 0 0 11 15 1 0 0 0 0 12 16 1 0 0 0 0 13 17 1 0 0 0 0 14 18 1 0 0 0 0 15 25 1 0 0 0 0 16 27 1 0 0 0 0 17 27 1 0 0 0 0 18 29 1 0 0 0 0 19 21 1 0 0 0 0 19 26 2 0 0 0 0 20 22 2 0 0 0 0 20 26 1 0 0 0 0 21 28 2 0 0 0 0 22 28 1 0 0 0 0 23 26 1 0 0 0 0 24 29 1 0 0 0 0 24 36 1 0 0 0 0 25 32 1 0 0 0 0 27 37 2 0 0 0 0 28 38 1 0 0 0 0 29 39 1 1 0 0 0 30 23 1 1 0 0 0 30 33 1 0 0 0 0 30 35 1 0 0 0 0 31 32 1 0 0 0 0 31 33 2 0 0 0 0 31 34 1 0 0 0 0 32 40 2 0 0 0 0 33 41 1 0 0 0 0 34 35 2 0 0 0 0 34 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	587.38
Volume:	633.58
LogP:	6.883
LogD:	4.144
LogS:	-3.687
# Rotatable Bonds:	24
TPSA:	151.08
# H-Bond Aceptor:	8
# H-Bond Donor:	6
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.057
Synthetic Accessibility Score:	3.822
Fsp3:	0.647
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.679
MDCK Permeability:	2.235976717201993e-05
Pgp-inhibitor:	0.449
Pgp-substrate:	0.683
Human Intestinal Absorption (HIA):	0.266
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	100.87435150146484%
Volume Distribution (VD):	0.381
Pgp-substrate:	0.2816275358200073%

ADMET: Metabolism

CYP1A2-inhibitor:	0.195
CYP1A2-substrate:	0.306
CYP2C19-inhibitor:	0.694
CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.485
CYP2C9-substrate:	0.983
CYP2D6-inhibitor:	0.95
CYP2D6-substrate:	0.304
CYP3A4-inhibitor:	0.504
CYP3A4-substrate:	0.221

ADMET: Excretion

Clearance (CL):	5.582
Half-life (T1/2):	0.795

ADMET: Toxicity

hERG Blockers:	0.061
Human Hepatotoxicity (H-HT):	0.295
Drug-inuced Liver Injury (DILI):	0.736
AMES Toxicity:	0.037
Rat Oral Acute Toxicity:	0.307
Maximum Recommended Daily Dose:	0.298
Skin Sensitization:	0.816
Carcinogencity:	0.046
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.757

Download Data

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

Natural Product: NPC471201

Natural Product ID:	NPC471201
*Common Name:**	Virgineone Aglycone
IUPAC Name:	(21R)-21,22-dihydroxy-1-[(2S)-3-hydroxy-2-[(4-hydroxyphenyl)methyl]-5-oxo-1,2-dihydropyrrol-4-yl]-2-methyldocosane-1,11-dione
Synonyms:
Standard InCHIKey:	PTFXIKSSFZFPSE-NSAALAIOSA-N
Standard InCHI:	InChI=1S/C34H53NO7/c1-25(32(40)31-33(41)30(35-34(31)42)23-26-19-21-28(38)22-20-26)15-11-7-5-6-9-13-17-27(37)16-12-8-3-2-4-10-14-18-29(39)24-36/h19-22,25,29-30,36,38-39,41H,2-18,23-24H2,1H3,(H,35,42)/t25?,29-,30+/m1/s1
SMILES:	OC[C@@H](CCCCCCCCCC(=O)CCCCCCCCC(C(=O)C1=C(O)[C@@H](N=C1O)Cc1ccc(cc1)O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2386696
PubChem CID:	73354958
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0004646] 1-hydroxy-2-unsubstituted benzenoids

*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
NPO32505	Clonostachys sp.	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[23806109]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
MIC	11

Activity Type	# Activity
Organism	11

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	5.5	ug.mL-1	PMID[538942]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	2.8	ug.mL-1	PMID[538942]
NPT21	Organism	Aspergillus niger	Aspergillus niger	MIC	>	88.0	ug.mL-1	PMID[538942]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	>	88.0	ug.mL-1	PMID[538942]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	88.0	ug.mL-1	PMID[538942]

☑ 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 NPC471201 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	146
0.1-0.2	762
0.2-0.3	3166
0.3-0.4	10726
0.4-0.5	8833
0.5-0.6	14903
0.6-0.7	3920
0.7-0.8	224
0.8-0.85	6
0.85-0.9	4
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9398	High Similarity	NPC322526
0.9323	High Similarity	NPC473055
0.9323	High Similarity	NPC473052
0.9313	High Similarity	NPC328070
0.8836	High Similarity	NPC476194
0.8309	Intermediate Similarity	NPC296712
0.8271	Intermediate Similarity	NPC474862
0.8116	Intermediate Similarity	NPC478147
0.8028	Intermediate Similarity	NPC6570
0.8	Intermediate Similarity	NPC45191
0.7974	Intermediate Similarity	NPC471203
0.7931	Intermediate Similarity	NPC91953
0.7926	Intermediate Similarity	NPC473051
0.7926	Intermediate Similarity	NPC473050
0.791	Intermediate Similarity	NPC319950
0.7879	Intermediate Similarity	NPC317254
0.7862	Intermediate Similarity	NPC197921
0.7842	Intermediate Similarity	NPC476353
0.7817	Intermediate Similarity	NPC244866
0.7808	Intermediate Similarity	NPC251439
0.7769	Intermediate Similarity	NPC474149
0.7762	Intermediate Similarity	NPC169766
0.7752	Intermediate Similarity	NPC317305
0.7737	Intermediate Similarity	NPC142577
0.7721	Intermediate Similarity	NPC190663
0.7692	Intermediate Similarity	NPC258056
0.7687	Intermediate Similarity	NPC469360
0.7669	Intermediate Similarity	NPC285350
0.766	Intermediate Similarity	NPC116057
0.7647	Intermediate Similarity	NPC283760
0.7622	Intermediate Similarity	NPC326966
0.7619	Intermediate Similarity	NPC150712
0.7612	Intermediate Similarity	NPC23402
0.7609	Intermediate Similarity	NPC27581
0.7609	Intermediate Similarity	NPC160493
0.7606	Intermediate Similarity	NPC325651
0.7586	Intermediate Similarity	NPC473360
0.7576	Intermediate Similarity	NPC177576
0.7547	Intermediate Similarity	NPC71205
0.7538	Intermediate Similarity	NPC142297
0.7537	Intermediate Similarity	NPC118202
0.7535	Intermediate Similarity	NPC472413
0.7534	Intermediate Similarity	NPC6913
0.7534	Intermediate Similarity	NPC64205
0.7534	Intermediate Similarity	NPC208725
0.75	Intermediate Similarity	NPC132771
0.75	Intermediate Similarity	NPC252544
0.75	Intermediate Similarity	NPC321252
0.7483	Intermediate Similarity	NPC16188
0.7482	Intermediate Similarity	NPC268348
0.7481	Intermediate Similarity	NPC188010
0.7462	Intermediate Similarity	NPC231705
0.7451	Intermediate Similarity	NPC473491
0.7448	Intermediate Similarity	NPC470392
0.7438	Intermediate Similarity	NPC15506
0.7429	Intermediate Similarity	NPC86900
0.7429	Intermediate Similarity	NPC469927
0.7419	Intermediate Similarity	NPC39431
0.7417	Intermediate Similarity	NPC473804
0.7389	Intermediate Similarity	NPC56635
0.7375	Intermediate Similarity	NPC63931
0.7372	Intermediate Similarity	NPC476268
0.7372	Intermediate Similarity	NPC38458
0.7372	Intermediate Similarity	NPC311737
0.7368	Intermediate Similarity	NPC119569
0.7358	Intermediate Similarity	NPC156348
0.7355	Intermediate Similarity	NPC262166
0.7343	Intermediate Similarity	NPC305717
0.7338	Intermediate Similarity	NPC478016
0.7338	Intermediate Similarity	NPC34634
0.7338	Intermediate Similarity	NPC80150
0.7338	Intermediate Similarity	NPC478015
0.7338	Intermediate Similarity	NPC265454
0.7338	Intermediate Similarity	NPC478014
0.7333	Intermediate Similarity	NPC168861
0.7319	Intermediate Similarity	NPC249435
0.731	Intermediate Similarity	NPC120251
0.7303	Intermediate Similarity	NPC81026
0.7299	Intermediate Similarity	NPC82963
0.7299	Intermediate Similarity	NPC106551
0.7299	Intermediate Similarity	NPC281686
0.7299	Intermediate Similarity	NPC188867
0.729	Intermediate Similarity	NPC233702
0.7286	Intermediate Similarity	NPC98305
0.7284	Intermediate Similarity	NPC209463
0.7279	Intermediate Similarity	NPC477680
0.7278	Intermediate Similarity	NPC212699
0.7278	Intermediate Similarity	NPC207675
0.7273	Intermediate Similarity	NPC476444
0.7273	Intermediate Similarity	NPC26108
0.7261	Intermediate Similarity	NPC123011
0.7261	Intermediate Similarity	NPC256689
0.7261	Intermediate Similarity	NPC244509
0.7256	Intermediate Similarity	NPC328494
0.7254	Intermediate Similarity	NPC307020
0.7244	Intermediate Similarity	NPC202198
0.7237	Intermediate Similarity	NPC266741
0.7231	Intermediate Similarity	NPC178902
0.723	Intermediate Similarity	NPC113325
0.723	Intermediate Similarity	NPC279045
0.7218	Intermediate Similarity	NPC24101
0.7218	Intermediate Similarity	NPC153690
0.7218	Intermediate Similarity	NPC96224
0.7203	Intermediate Similarity	NPC171372
0.7203	Intermediate Similarity	NPC472414
0.7197	Intermediate Similarity	NPC70843
0.7195	Intermediate Similarity	NPC314693
0.7195	Intermediate Similarity	NPC196091
0.7192	Intermediate Similarity	NPC183722
0.7192	Intermediate Similarity	NPC474546
0.7185	Intermediate Similarity	NPC114682
0.7183	Intermediate Similarity	NPC472415
0.7169	Intermediate Similarity	NPC136797
0.7164	Intermediate Similarity	NPC88141
0.7164	Intermediate Similarity	NPC326187
0.7162	Intermediate Similarity	NPC228511
0.7153	Intermediate Similarity	NPC29477
0.7152	Intermediate Similarity	NPC89831
0.7152	Intermediate Similarity	NPC476989
0.7143	Intermediate Similarity	NPC182240
0.7143	Intermediate Similarity	NPC275538
0.7143	Intermediate Similarity	NPC239697
0.7143	Intermediate Similarity	NPC268572
0.7134	Intermediate Similarity	NPC280022
0.7134	Intermediate Similarity	NPC101207
0.7133	Intermediate Similarity	NPC236795
0.7133	Intermediate Similarity	NPC236981
0.7133	Intermediate Similarity	NPC313694
0.7133	Intermediate Similarity	NPC242159
0.7125	Intermediate Similarity	NPC244336
0.7123	Intermediate Similarity	NPC469930
0.7123	Intermediate Similarity	NPC278308
0.7115	Intermediate Similarity	NPC324081
0.7108	Intermediate Similarity	NPC12890
0.7105	Intermediate Similarity	NPC33011
0.7099	Intermediate Similarity	NPC67080
0.7097	Intermediate Similarity	NPC313414
0.7095	Intermediate Similarity	NPC88667
0.709	Intermediate Similarity	NPC31274
0.7089	Intermediate Similarity	NPC68967
0.7086	Intermediate Similarity	NPC471316
0.7083	Intermediate Similarity	NPC95733
0.7083	Intermediate Similarity	NPC231767
0.7083	Intermediate Similarity	NPC62101
0.708	Intermediate Similarity	NPC309808
0.7071	Intermediate Similarity	NPC104514
0.7071	Intermediate Similarity	NPC122009
0.7071	Intermediate Similarity	NPC5932
0.7071	Intermediate Similarity	NPC310467
0.707	Intermediate Similarity	NPC153644
0.7068	Intermediate Similarity	NPC95178
0.7068	Intermediate Similarity	NPC69332
0.7068	Intermediate Similarity	NPC29989
0.7068	Intermediate Similarity	NPC188677
0.7067	Intermediate Similarity	NPC109580
0.7066	Intermediate Similarity	NPC95412
0.7055	Intermediate Similarity	NPC12022
0.7055	Intermediate Similarity	NPC71271
0.7055	Intermediate Similarity	NPC145888
0.7055	Intermediate Similarity	NPC161593
0.7055	Intermediate Similarity	NPC293641
0.7055	Intermediate Similarity	NPC20404
0.7055	Intermediate Similarity	NPC20287
0.7055	Intermediate Similarity	NPC477839
0.7055	Intermediate Similarity	NPC16031
0.7054	Intermediate Similarity	NPC260000
0.7051	Intermediate Similarity	NPC146097
0.7051	Intermediate Similarity	NPC227905
0.7051	Intermediate Similarity	NPC339338
0.705	Intermediate Similarity	NPC28951
0.705	Intermediate Similarity	NPC325646
0.7045	Intermediate Similarity	NPC8931
0.7045	Intermediate Similarity	NPC261573
0.7045	Intermediate Similarity	NPC120693
0.7042	Intermediate Similarity	NPC86966
0.7042	Intermediate Similarity	NPC56634
0.7037	Intermediate Similarity	NPC95172
0.7037	Intermediate Similarity	NPC290566
0.7037	Intermediate Similarity	NPC145638
0.7034	Intermediate Similarity	NPC127975
0.7029	Intermediate Similarity	NPC142599
0.7027	Intermediate Similarity	NPC257390
0.7027	Intermediate Similarity	NPC473724
0.7027	Intermediate Similarity	NPC42423
0.7025	Intermediate Similarity	NPC56685
0.7025	Intermediate Similarity	NPC261934
0.7025	Intermediate Similarity	NPC5194
0.7021	Intermediate Similarity	NPC43275
0.7021	Intermediate Similarity	NPC473767
0.7018	Intermediate Similarity	NPC469973
0.7015	Intermediate Similarity	NPC228737
0.7014	Intermediate Similarity	NPC14141
0.7007	Intermediate Similarity	NPC17693
0.7007	Intermediate Similarity	NPC48525
0.7006	Intermediate Similarity	NPC137627
0.7006	Intermediate Similarity	NPC476743
0.7	Intermediate Similarity	NPC169328
0.7	Intermediate Similarity	NPC280869
0.7	Intermediate Similarity	NPC283468
0.6992	Remote Similarity	NPC211551

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 NPC471201 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	116
0.1-0.2	449
0.2-0.3	927
0.3-0.4	1911
0.4-0.5	2883
0.5-0.6	2241
0.6-0.7	590
0.7-0.8	33
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
0.7929	Intermediate Similarity	NPD3136	Phase 2
0.7808	Intermediate Similarity	NPD7978	Discontinued
0.7692	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD3400	Discontinued
0.7445	Intermediate Similarity	NPD1759	Phase 1
0.7405	Intermediate Similarity	NPD7972	Discontinued
0.7383	Intermediate Similarity	NPD7450	Phase 2
0.7372	Intermediate Similarity	NPD1758	Phase 1
0.7299	Intermediate Similarity	NPD9568	Approved
0.7278	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD9570	Approved
0.7254	Intermediate Similarity	NPD4659	Approved
0.7226	Intermediate Similarity	NPD256	Approved
0.7226	Intermediate Similarity	NPD255	Approved
0.7179	Intermediate Similarity	NPD6390	Discontinued
0.7171	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD6682	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD317	Approved
0.7122	Intermediate Similarity	NPD318	Approved
0.7114	Intermediate Similarity	NPD555	Phase 2
0.7103	Intermediate Similarity	NPD7451	Discontinued
0.7101	Intermediate Similarity	NPD3823	Discontinued
0.7095	Intermediate Similarity	NPD259	Phase 1
0.7086	Intermediate Similarity	NPD6866	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6867	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD2561	Approved
0.7063	Intermediate Similarity	NPD2562	Approved
0.7055	Intermediate Similarity	NPD9569	Approved
0.705	Intermediate Similarity	NPD3123	Discovery
0.7047	Intermediate Similarity	NPD825	Approved
0.7047	Intermediate Similarity	NPD826	Approved
0.7037	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD4103	Phase 2
0.7034	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7523	Phase 3
0.7025	Intermediate Similarity	NPD7131	Phase 3
0.702	Intermediate Similarity	NPD3554	Approved
0.702	Intermediate Similarity	NPD3553	Approved
0.702	Intermediate Similarity	NPD3552	Approved
0.702	Intermediate Similarity	NPD3555	Approved
0.7019	Intermediate Similarity	NPD7495	Discontinued
0.7018	Intermediate Similarity	NPD5028	Approved
0.7018	Intermediate Similarity	NPD4954	Approved
0.7018	Intermediate Similarity	NPD36	Approved
0.7018	Intermediate Similarity	NPD5026	Approved
0.7018	Intermediate Similarity	NPD4955	Approved
0.7018	Intermediate Similarity	NPD5034	Approved
0.7	Intermediate Similarity	NPD856	Approved
0.7	Intermediate Similarity	NPD16	Approved
0.6986	Remote Similarity	NPD257	Approved
0.6986	Remote Similarity	NPD258	Approved
0.6972	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6325	Discontinued
0.6959	Remote Similarity	NPD5030	Phase 2
0.6959	Remote Similarity	NPD4738	Phase 2
0.6957	Remote Similarity	NPD2228	Approved
0.6957	Remote Similarity	NPD2234	Approved
0.6957	Remote Similarity	NPD2229	Approved
0.6944	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD3455	Phase 2
0.6917	Remote Similarity	NPD9610	Approved
0.6917	Remote Similarity	NPD9608	Approved
0.6914	Remote Similarity	NPD8019	Approved
0.6906	Remote Similarity	NPD9618	Approved
0.6906	Remote Similarity	NPD9614	Approved
0.6897	Remote Similarity	NPD5157	Phase 1
0.6897	Remote Similarity	NPD9622	Approved
0.6897	Remote Similarity	NPD5159	Phase 2
0.6897	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD5035	Approved
0.6857	Remote Similarity	NPD5038	Approved
0.6857	Remote Similarity	NPD5037	Approved
0.6846	Remote Similarity	NPD9537	Phase 1
0.6846	Remote Similarity	NPD9536	Phase 1
0.6831	Remote Similarity	NPD2218	Phase 2
0.6831	Remote Similarity	NPD2217	Approved
0.6818	Remote Similarity	NPD2239	Approved
0.6818	Remote Similarity	NPD2240	Approved
0.6818	Remote Similarity	NPD2161	Phase 2
0.6806	Remote Similarity	NPD3421	Phase 3
0.6803	Remote Similarity	NPD1135	Approved
0.6803	Remote Similarity	NPD1131	Approved
0.6803	Remote Similarity	NPD1129	Approved
0.6803	Remote Similarity	NPD1134	Approved
0.6803	Remote Similarity	NPD1133	Approved
0.68	Remote Similarity	NPD601	Approved
0.68	Remote Similarity	NPD597	Approved
0.68	Remote Similarity	NPD5036	Approved
0.68	Remote Similarity	NPD598	Approved
0.679	Remote Similarity	NPD6502	Phase 2
0.6786	Remote Similarity	NPD7315	Approved
0.6781	Remote Similarity	NPD3685	Discontinued
0.6781	Remote Similarity	NPD1755	Approved
0.6759	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD1132	Approved
0.6755	Remote Similarity	NPD2674	Phase 3
0.6755	Remote Similarity	NPD1136	Approved
0.6755	Remote Similarity	NPD1130	Approved
0.6744	Remote Similarity	NPD7695	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD9381	Approved
0.6736	Remote Similarity	NPD9384	Approved
0.6735	Remote Similarity	NPD196	Phase 1
0.6732	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD7318	Phase 3
0.6713	Remote Similarity	NPD5303	Approved
0.6713	Remote Similarity	NPD5304	Approved
0.6712	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD6346	Approved
0.671	Remote Similarity	NPD5712	Approved
0.6704	Remote Similarity	NPD3819	Phase 2
0.6704	Remote Similarity	NPD5968	Phase 3
0.6691	Remote Similarity	NPD1444	Approved
0.6691	Remote Similarity	NPD1445	Approved
0.6689	Remote Similarity	NPD3145	Approved
0.6689	Remote Similarity	NPD2627	Approved
0.6689	Remote Similarity	NPD2625	Approved
0.6689	Remote Similarity	NPD3144	Approved
0.6689	Remote Similarity	NPD2626	Approved
0.6689	Remote Similarity	NPD2159	Approved
0.6689	Remote Similarity	NPD2628	Approved
0.6689	Remote Similarity	NPD2160	Approved
0.6688	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD6836	Approved
0.6667	Remote Similarity	NPD3300	Phase 2
0.6667	Remote Similarity	NPD5031	Approved
0.6667	Remote Similarity	NPD5029	Approved
0.6667	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD274	Approved
0.6667	Remote Similarity	NPD275	Approved
0.6667	Remote Similarity	NPD4207	Discontinued
0.6667	Remote Similarity	NPD5027	Approved
0.6647	Remote Similarity	NPD5137	Approved
0.6647	Remote Similarity	NPD5557	Phase 1
0.6646	Remote Similarity	NPD7526	Approved
0.6646	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD52	Approved
0.6646	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD7066	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6676	Phase 2
0.6645	Remote Similarity	NPD7477	Discontinued
0.6645	Remote Similarity	NPD6405	Approved
0.6645	Remote Similarity	NPD6407	Approved
0.6644	Remote Similarity	NPD9621	Approved
0.6644	Remote Similarity	NPD9620	Approved
0.6644	Remote Similarity	NPD9619	Approved
0.6643	Remote Similarity	NPD9616	Approved
0.6643	Remote Similarity	NPD9613	Approved
0.6643	Remote Similarity	NPD9615	Approved
0.6642	Remote Similarity	NPD855	Approved
0.6642	Remote Similarity	NPD854	Approved
0.6629	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD3909	Discontinued
0.6627	Remote Similarity	NPD3286	Discontinued
0.6623	Remote Similarity	NPD823	Approved
0.6623	Remote Similarity	NPD8172	Phase 2
0.6623	Remote Similarity	NPD5314	Approved
0.6623	Remote Similarity	NPD8173	Phase 2
0.6623	Remote Similarity	NPD2568	Approved
0.6623	Remote Similarity	NPD817	Approved
0.6621	Remote Similarity	NPD3019	Approved
0.6621	Remote Similarity	NPD2932	Approved
0.6619	Remote Similarity	NPD3644	Approved
0.6619	Remote Similarity	NPD3642	Approved
0.6619	Remote Similarity	NPD3643	Approved
0.661	Remote Similarity	NPD3154	Approved
0.661	Remote Similarity	NPD3153	Approved
0.6609	Remote Similarity	NPD7959	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD8303	Discontinued
0.6606	Remote Similarity	NPD7317	Phase 3
0.6606	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD8131	Suspended
0.6604	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD3061	Approved
0.6601	Remote Similarity	NPD3059	Approved
0.6601	Remote Similarity	NPD3062	Approved
0.66	Remote Similarity	NPD4208	Discontinued
0.6597	Remote Similarity	NPD316	Approved
0.6588	Remote Similarity	NPD7608	Discontinued
0.6584	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD4662	Approved
0.6584	Remote Similarity	NPD4661	Approved
0.6584	Remote Similarity	NPD3536	Discontinued
0.6577	Remote Similarity	NPD3053	Approved
0.6577	Remote Similarity	NPD3055	Approved
0.6575	Remote Similarity	NPD3143	Discontinued
0.6571	Remote Similarity	NPD8014	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD6809	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD4093	Discontinued
0.6547	Remote Similarity	NPD1792	Phase 2
0.6545	Remote Similarity	NPD6677	Suspended
0.6545	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD9609	Approved
0.6541	Remote Similarity	NPD8166	Discontinued
0.6541	Remote Similarity	NPD9611	Approved
0.6541	Remote Similarity	NPD9612	Approved
0.6541	Remote Similarity	NPD2575	Approved
0.6536	Remote Similarity	NPD1423	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