NPASS Compound

Structure

CID328287 OpenBabel06191716202D 42 48 0 0 1 0 0 0 0 0999 V2000 3.2270 0.0146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6166 -0.9263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3448 5.9694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4170 0.4767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2991 3.1619 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3164 4.1011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7970 1.3969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8249 4.1733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4493 6.0331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6118 0.0063 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.0096 1.8571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8208 3.2457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8017 0.4684 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4772 2.7072 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5116 4.5856 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6366 4.6419 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6226 2.7773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8113 1.3887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6724 3.1917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4383 4.1735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4379 3.2309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0458 3.2216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0143 2.7856 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6178 1.8488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8505 2.7371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2445 2.7597 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6897 4.1309 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2565 4.6319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0630 4.1607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8065 0.4601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7909 3.2560 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 0.0048 -0.9326 0.0000 N 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 -6.4601 1.7748 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4230 1.3783 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8334 1.8046 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2417 1.8266 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6118 -0.0103 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5287 5.5180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6434 5.5743 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2510 5.5647 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8849 4.6154 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 10 1 0 0 0 0 3 39 1 0 0 0 0 4 10 1 0 0 0 0 5 6 2 0 0 0 0 5 14 1 0 0 0 0 6 15 1 0 0 0 0 7 11 1 0 0 0 0 7 13 2 0 0 0 0 8 12 1 0 0 0 0 9 40 1 0 0 0 0 9 41 1 0 0 0 0 10 13 1 0 0 0 0 11 18 1 0 0 0 0 11 23 2 0 0 0 0 12 17 2 0 0 0 0 12 23 1 0 0 0 0 13 33 1 0 0 0 0 14 19 1 0 0 0 0 14 34 1 1 0 0 0 15 27 1 0 0 0 0 15 39 1 1 0 0 0 16 8 1 6 0 0 0 16 20 1 0 0 0 0 16 40 1 0 0 0 0 17 21 1 0 0 0 0 17 24 1 0 0 0 0 18 24 2 0 0 0 0 18 30 1 0 0 0 0 19 25 1 1 0 0 0 19 27 1 0 0 0 0 20 21 2 0 0 0 0 20 28 1 0 0 0 0 21 26 1 0 0 0 0 22 25 1 0 0 0 0 22 26 2 0 0 0 0 22 29 1 0 0 0 0 23 31 1 0 0 0 0 24 35 1 0 0 0 0 25 36 2 0 0 0 0 26 37 1 0 0 0 0 27 42 1 1 0 0 0 28 29 2 0 0 0 0 28 41 1 0 0 0 0 29 42 1 0 0 0 0 30 33 1 0 0 0 0 30 38 2 0 0 0 0 32 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	596.16
Volume:	557.493
LogP:	5.579
LogD:	2.883
LogS:	-5.015
# Rotatable Bonds:	3
TPSA:	165.86
# H-Bond Aceptor:	11
# H-Bond Donor:	6
# Rings:	7
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.102
Synthetic Accessibility Score:	5.437
Fsp3:	0.367
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:	-5.479
MDCK Permeability:	4.76102559332503e-06
Pgp-inhibitor:	0.424
Pgp-substrate:	0.086
Human Intestinal Absorption (HIA):	0.132
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.019

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	93.39974212646484%
Volume Distribution (VD):	1.212
Pgp-substrate:	4.018619060516357%

ADMET: Metabolism

CYP1A2-inhibitor:	0.157
CYP1A2-substrate:	0.495
CYP2C19-inhibitor:	0.054
CYP2C19-substrate:	0.246
CYP2C9-inhibitor:	0.792
CYP2C9-substrate:	0.812
CYP2D6-inhibitor:	0.334
CYP2D6-substrate:	0.119
CYP3A4-inhibitor:	0.114
CYP3A4-substrate:	0.065

ADMET: Excretion

Clearance (CL):	2.792
Half-life (T1/2):	0.069

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.098
Drug-inuced Liver Injury (DILI):	0.959
AMES Toxicity:	0.693
Rat Oral Acute Toxicity:	0.057
Maximum Recommended Daily Dose:	0.976
Skin Sensitization:	0.163
Carcinogencity:	0.728
Eye Corrosion:	0.003
Eye Irritation:	0.084
Respiratory Toxicity:	0.239

Download Data

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

Natural Product: NPC328287

Natural Product ID:	NPC328287
*Common Name:**	LGOPVBMUGSRUOT-NLGWJYKOSA-N
IUPAC Name:	n.a.
Synonyms:	SCH-54445
Standard InCHIKey:	LGOPVBMUGSRUOT-NLGWJYKOSA-N
Standard InCHI:	InChI=1S/C30H29ClN2O9/c1-4-10(2)13-7-11-18(30(38)33(13)32)24(35)17-12(23(11)31)8-16-20-21(17)26(37)22-25(36)19-14(34)5-6-15(39-3)27(19)42-29(22)28(20)41-9-40-16/h5-7,10,14-16,19,27,34-35,37H,4,8-9,32H2,1-3H3/t10?,14-,15+,16+,19+,27+/m0/s1
SMILES:	CCC(C)C1=CC2=C(C(=C3C(=C2Cl)CC4C5=C3C(=C6C(=O)C7C(C=CC(C7OC6=C5OCO4)OC)O)O)O)C(=O)N1N
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL449377
PubChem CID:	10054253
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones

*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
NPO30192	Actinoplanes	Genus	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9170295]

☑ 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
LD50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	LD50	=	1.0	mg.kg-1	PMID[493330]

☑ 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 NPC328287 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	567
0.1-0.2	2598
0.2-0.3	9862
0.3-0.4	8651
0.4-0.5	9442
0.5-0.6	10547
0.6-0.7	986
0.7-0.8	42
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7404	Intermediate Similarity	NPC315914
0.722	Intermediate Similarity	NPC198163
0.7208	Intermediate Similarity	NPC185031
0.7208	Intermediate Similarity	NPC316292
0.7202	Intermediate Similarity	NPC49690
0.7195	Intermediate Similarity	NPC321046
0.7156	Intermediate Similarity	NPC154720
0.7143	Intermediate Similarity	NPC245059
0.7143	Intermediate Similarity	NPC212290
0.7143	Intermediate Similarity	NPC193676
0.7143	Intermediate Similarity	NPC84494
0.713	Intermediate Similarity	NPC475246
0.7116	Intermediate Similarity	NPC213052
0.711	Intermediate Similarity	NPC470453
0.711	Intermediate Similarity	NPC164047
0.711	Intermediate Similarity	NPC470448
0.711	Intermediate Similarity	NPC470452
0.7104	Intermediate Similarity	NPC473618
0.7103	Intermediate Similarity	NPC241874
0.7103	Intermediate Similarity	NPC474004
0.7094	Intermediate Similarity	NPC316368
0.7094	Intermediate Similarity	NPC284236
0.7083	Intermediate Similarity	NPC199533
0.7083	Intermediate Similarity	NPC470454
0.7083	Intermediate Similarity	NPC146803
0.7083	Intermediate Similarity	NPC3718
0.7082	Intermediate Similarity	NPC478048
0.7078	Intermediate Similarity	NPC476203
0.7075	Intermediate Similarity	NPC25361
0.707	Intermediate Similarity	NPC223375
0.707	Intermediate Similarity	NPC267254
0.707	Intermediate Similarity	NPC475825
0.707	Intermediate Similarity	NPC256760
0.7064	Intermediate Similarity	NPC277710
0.7064	Intermediate Similarity	NPC299149
0.7064	Intermediate Similarity	NPC153578
0.7064	Intermediate Similarity	NPC114257
0.7059	Intermediate Similarity	NPC105591
0.7059	Intermediate Similarity	NPC179947
0.7056	Intermediate Similarity	NPC472381
0.7056	Intermediate Similarity	NPC259905
0.7056	Intermediate Similarity	NPC472383
0.7054	Intermediate Similarity	NPC314020
0.7054	Intermediate Similarity	NPC214901
0.7051	Intermediate Similarity	NPC478047
0.7051	Intermediate Similarity	NPC180210
0.7051	Intermediate Similarity	NPC478046
0.7051	Intermediate Similarity	NPC321226
0.7051	Intermediate Similarity	NPC314914
0.7051	Intermediate Similarity	NPC328856
0.7051	Intermediate Similarity	NPC46958
0.7045	Intermediate Similarity	NPC148710
0.7043	Intermediate Similarity	NPC153365
0.7042	Intermediate Similarity	NPC120593
0.7042	Intermediate Similarity	NPC178173
0.7037	Intermediate Similarity	NPC199357
0.7037	Intermediate Similarity	NPC239549
0.7037	Intermediate Similarity	NPC208668
0.7037	Intermediate Similarity	NPC204693
0.7037	Intermediate Similarity	NPC51774
0.7037	Intermediate Similarity	NPC236191
0.7034	Intermediate Similarity	NPC170101
0.7032	Intermediate Similarity	NPC475161
0.7032	Intermediate Similarity	NPC477860
0.7028	Intermediate Similarity	NPC197168
0.7023	Intermediate Similarity	NPC183357
0.7023	Intermediate Similarity	NPC22195
0.7023	Intermediate Similarity	NPC78734
0.7023	Intermediate Similarity	NPC150767
0.7023	Intermediate Similarity	NPC105511
0.7023	Intermediate Similarity	NPC44558
0.7023	Intermediate Similarity	NPC21190
0.7021	Intermediate Similarity	NPC82056
0.7018	Intermediate Similarity	NPC168584
0.7018	Intermediate Similarity	NPC472387
0.7014	Intermediate Similarity	NPC87583
0.7012	Intermediate Similarity	NPC316461
0.7009	Intermediate Similarity	NPC38964
0.7009	Intermediate Similarity	NPC220369
0.7009	Intermediate Similarity	NPC93099
0.7005	Intermediate Similarity	NPC63105
0.7005	Intermediate Similarity	NPC472607
0.7005	Intermediate Similarity	NPC102028
0.7	Intermediate Similarity	NPC186113
0.7	Intermediate Similarity	NPC132111
0.7	Intermediate Similarity	NPC473883
0.7	Intermediate Similarity	NPC257728
0.6996	Remote Similarity	NPC264938
0.6991	Remote Similarity	NPC259152
0.6991	Remote Similarity	NPC3583
0.6991	Remote Similarity	NPC205076
0.6991	Remote Similarity	NPC271385
0.6991	Remote Similarity	NPC475155
0.6991	Remote Similarity	NPC111536
0.6991	Remote Similarity	NPC301683
0.6991	Remote Similarity	NPC76128
0.6991	Remote Similarity	NPC260263
0.6991	Remote Similarity	NPC307518
0.6991	Remote Similarity	NPC48773
0.6991	Remote Similarity	NPC156977
0.6991	Remote Similarity	NPC472386
0.6991	Remote Similarity	NPC5029
0.6991	Remote Similarity	NPC30432
0.6991	Remote Similarity	NPC474857
0.6986	Remote Similarity	NPC324742
0.6986	Remote Similarity	NPC244903
0.6982	Remote Similarity	NPC174486
0.6981	Remote Similarity	NPC56735
0.6981	Remote Similarity	NPC473961
0.6981	Remote Similarity	NPC61594
0.6978	Remote Similarity	NPC315351
0.6978	Remote Similarity	NPC316412
0.6977	Remote Similarity	NPC469931
0.6977	Remote Similarity	NPC170675
0.6977	Remote Similarity	NPC45638
0.6977	Remote Similarity	NPC201292
0.6977	Remote Similarity	NPC226294
0.6977	Remote Similarity	NPC58053
0.6977	Remote Similarity	NPC246274
0.6977	Remote Similarity	NPC471457
0.6977	Remote Similarity	NPC93337
0.6977	Remote Similarity	NPC188079
0.6977	Remote Similarity	NPC105025
0.6977	Remote Similarity	NPC210042
0.6977	Remote Similarity	NPC475942
0.6977	Remote Similarity	NPC95855
0.6977	Remote Similarity	NPC112755
0.6977	Remote Similarity	NPC186807
0.6972	Remote Similarity	NPC169733
0.6964	Remote Similarity	NPC48474
0.6964	Remote Similarity	NPC264302
0.6963	Remote Similarity	NPC178851
0.6963	Remote Similarity	NPC272502
0.6957	Remote Similarity	NPC257266
0.6948	Remote Similarity	NPC127415
0.6948	Remote Similarity	NPC147596
0.6947	Remote Similarity	NPC313453
0.6944	Remote Similarity	NPC51326
0.6944	Remote Similarity	NPC293004
0.6944	Remote Similarity	NPC103307
0.6944	Remote Similarity	NPC471416
0.6944	Remote Similarity	NPC224462
0.6944	Remote Similarity	NPC231194
0.6944	Remote Similarity	NPC298778
0.6944	Remote Similarity	NPC474434
0.6944	Remote Similarity	NPC34287
0.6944	Remote Similarity	NPC218488
0.6941	Remote Similarity	NPC476619
0.6941	Remote Similarity	NPC476618
0.6941	Remote Similarity	NPC476623
0.6941	Remote Similarity	NPC476621
0.6941	Remote Similarity	NPC476620
0.6941	Remote Similarity	NPC476622
0.6941	Remote Similarity	NPC67302
0.6937	Remote Similarity	NPC191606
0.6937	Remote Similarity	NPC241847
0.6934	Remote Similarity	NPC66288
0.693	Remote Similarity	NPC146792
0.693	Remote Similarity	NPC225419
0.693	Remote Similarity	NPC135345
0.693	Remote Similarity	NPC6588
0.693	Remote Similarity	NPC477154
0.693	Remote Similarity	NPC45618
0.693	Remote Similarity	NPC117854
0.693	Remote Similarity	NPC474024
0.693	Remote Similarity	NPC477502
0.693	Remote Similarity	NPC58716
0.6927	Remote Similarity	NPC142996
0.6927	Remote Similarity	NPC294629
0.6927	Remote Similarity	NPC108202
0.6927	Remote Similarity	NPC68381
0.6927	Remote Similarity	NPC474345
0.6923	Remote Similarity	NPC315253
0.6916	Remote Similarity	NPC261012
0.6916	Remote Similarity	NPC313274
0.6916	Remote Similarity	NPC314738
0.6916	Remote Similarity	NPC109403
0.6912	Remote Similarity	NPC476405
0.6912	Remote Similarity	NPC254540
0.6912	Remote Similarity	NPC315619
0.6912	Remote Similarity	NPC117260
0.6912	Remote Similarity	NPC172807
0.6912	Remote Similarity	NPC4200
0.6912	Remote Similarity	NPC188618
0.6912	Remote Similarity	NPC211594
0.6909	Remote Similarity	NPC473682
0.6909	Remote Similarity	NPC126784
0.6909	Remote Similarity	NPC110941
0.6909	Remote Similarity	NPC241423
0.6909	Remote Similarity	NPC473571
0.6909	Remote Similarity	NPC470444
0.6909	Remote Similarity	NPC470443
0.6905	Remote Similarity	NPC314743
0.6903	Remote Similarity	NPC83019
0.6901	Remote Similarity	NPC229632
0.6898	Remote Similarity	NPC229687
0.6898	Remote Similarity	NPC209296
0.6898	Remote Similarity	NPC177480
0.6898	Remote Similarity	NPC183036
0.6898	Remote Similarity	NPC471287

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 NPC328287 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	345
0.1-0.2	673
0.2-0.3	1224
0.3-0.4	2331
0.4-0.5	2813
0.5-0.6	1549
0.6-0.7	209
0.7-0.8	6
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
0.7333	Intermediate Similarity	NPD7584	Approved
0.7042	Intermediate Similarity	NPD7654	Discontinued
0.7004	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7585	Approved
0.6996	Remote Similarity	NPD4363	Phase 3
0.6996	Remote Similarity	NPD4360	Phase 2
0.6983	Remote Similarity	NPD7783	Phase 2
0.6983	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7583	Approved
0.693	Remote Similarity	NPD6823	Phase 2
0.6929	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD8059	Phase 3
0.6926	Remote Similarity	NPD7701	Phase 2
0.6916	Remote Similarity	NPD6776	Approved
0.6916	Remote Similarity	NPD6782	Approved
0.6916	Remote Similarity	NPD6780	Approved
0.6916	Remote Similarity	NPD6777	Approved
0.6916	Remote Similarity	NPD6781	Approved
0.6916	Remote Similarity	NPD6779	Approved
0.6916	Remote Similarity	NPD6778	Approved
0.69	Remote Similarity	NPD7696	Phase 3
0.69	Remote Similarity	NPD7698	Approved
0.69	Remote Similarity	NPD7697	Approved
0.6898	Remote Similarity	NPD7054	Approved
0.6866	Remote Similarity	NPD7074	Phase 3
0.6866	Remote Similarity	NPD7472	Approved
0.6862	Remote Similarity	NPD8366	Approved
0.6842	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD7801	Approved
0.682	Remote Similarity	NPD5844	Phase 1
0.6818	Remote Similarity	NPD8491	Approved
0.6814	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD4361	Phase 2
0.6797	Remote Similarity	NPD7870	Phase 2
0.6797	Remote Similarity	NPD7871	Phase 2
0.6773	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6773	Remote Similarity	NPD7808	Phase 3
0.677	Remote Similarity	NPD6534	Approved
0.677	Remote Similarity	NPD6535	Approved
0.6758	Remote Similarity	NPD6797	Phase 2
0.6754	Remote Similarity	NPD7700	Phase 2
0.6754	Remote Similarity	NPD7699	Phase 2
0.6752	Remote Similarity	NPD8151	Discontinued
0.6741	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD7473	Discontinued
0.6727	Remote Similarity	NPD7251	Discontinued
0.6726	Remote Similarity	NPD6212	Phase 3
0.6726	Remote Similarity	NPD6213	Phase 3
0.6726	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.671	Remote Similarity	NPD5006	Approved
0.671	Remote Similarity	NPD5005	Approved
0.6698	Remote Similarity	NPD6959	Discontinued
0.6697	Remote Similarity	NPD3818	Discontinued
0.6682	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD6166	Phase 2
0.6682	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD7435	Discontinued
0.6667	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6232	Discontinued
0.6667	Remote Similarity	NPD8312	Approved
0.6667	Remote Similarity	NPD8313	Approved
0.6653	Remote Similarity	NPD7874	Approved
0.6653	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD6559	Discontinued
0.6651	Remote Similarity	NPD5494	Approved
0.664	Remote Similarity	NPD8067	Phase 3
0.6608	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD8319	Approved
0.6581	Remote Similarity	NPD8320	Phase 1
0.658	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6576	Remote Similarity	NPD8367	Approved
0.6558	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6553	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD8461	Discontinued
0.6552	Remote Similarity	NPD4914	Approved
0.6545	Remote Similarity	NPD7228	Approved
0.6538	Remote Similarity	NPD8492	Approved
0.6537	Remote Similarity	NPD4420	Approved
0.6495	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD2801	Approved
0.6463	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD8469	Approved
0.6449	Remote Similarity	NPD1934	Approved
0.6449	Remote Similarity	NPD37	Approved
0.6435	Remote Similarity	NPD4966	Approved
0.6435	Remote Similarity	NPD4967	Phase 2
0.6435	Remote Similarity	NPD4965	Approved
0.6432	Remote Similarity	NPD8150	Discontinued
0.6426	Remote Similarity	NPD4387	Approved
0.6426	Remote Similarity	NPD4386	Approved
0.6423	Remote Similarity	NPD6997	Phase 2
0.64	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD8153	Approved
0.6385	Remote Similarity	NPD8152	Approved
0.6376	Remote Similarity	NPD6234	Discontinued
0.6355	Remote Similarity	NPD4380	Phase 2
0.6348	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD7549	Discontinued
0.6324	Remote Similarity	NPD7942	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD7922	Phase 1
0.6323	Remote Similarity	NPD7177	Discontinued
0.6323	Remote Similarity	NPD3751	Discontinued
0.632	Remote Similarity	NPD3819	Phase 2
0.6314	Remote Similarity	NPD7048	Phase 3
0.6313	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6309	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD8285	Discontinued
0.6298	Remote Similarity	NPD5544	Approved
0.629	Remote Similarity	NPD5710	Approved
0.629	Remote Similarity	NPD5711	Approved
0.6284	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD7240	Approved
0.6282	Remote Similarity	NPD4915	Approved
0.6282	Remote Similarity	NPD4388	Approved
0.6272	Remote Similarity	NPD8054	Approved
0.6272	Remote Similarity	NPD8053	Approved
0.627	Remote Similarity	NPD7930	Approved
0.6267	Remote Similarity	NPD7819	Suspended
0.6261	Remote Similarity	NPD7291	Discontinued
0.6261	Remote Similarity	NPD5242	Approved
0.6255	Remote Similarity	NPD4974	Approved
0.6255	Remote Similarity	NPD7827	Phase 1
0.6255	Remote Similarity	NPD4975	Approved
0.625	Remote Similarity	NPD7907	Approved
0.6239	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD3817	Phase 2
0.6239	Remote Similarity	NPD5402	Approved
0.6235	Remote Similarity	NPD4665	Approved
0.6235	Remote Similarity	NPD4111	Phase 1
0.6234	Remote Similarity	NPD5910	Clinical (unspecified phase)
0.6221	Remote Similarity	NPD6844	Discontinued
0.6216	Remote Similarity	NPD3787	Discontinued
0.6211	Remote Similarity	NPD7038	Approved
0.6211	Remote Similarity	NPD7039	Approved
0.6203	Remote Similarity	NPD5457	Discontinued
0.6197	Remote Similarity	NPD2533	Approved
0.6197	Remote Similarity	NPD2534	Approved
0.6197	Remote Similarity	NPD2532	Approved
0.6196	Remote Similarity	NPD6723	Discontinued
0.6196	Remote Similarity	NPD6625	Approved
0.6193	Remote Similarity	NPD1465	Phase 2
0.619	Remote Similarity	NPD7693	Approved
0.619	Remote Similarity	NPD6674	Discontinued
0.6182	Remote Similarity	NPD7075	Discontinued
0.6179	Remote Similarity	NPD7047	Phase 3
0.6174	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6171	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6171	Remote Similarity	NPD7199	Phase 2
0.6169	Remote Similarity	NPD2899	Discontinued
0.6164	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.616	Remote Similarity	NPD6874	Approved
0.615	Remote Similarity	NPD6020	Phase 2
0.615	Remote Similarity	NPD8156	Discontinued
0.6147	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD8398	Clinical (unspecified phase)
0.6144	Remote Similarity	NPD5543	Approved
0.6144	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD3882	Suspended
0.6125	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD4846	Phase 2
0.6123	Remote Similarity	NPD5441	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.612	Remote Similarity	NPD7805	Phase 3
0.6114	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD8099	Discontinued
0.6106	Remote Similarity	NPD8252	Approved
0.6106	Remote Similarity	NPD8251	Approved
0.6101	Remote Similarity	NPD7411	Suspended
0.6094	Remote Similarity	NPD8361	Approved
0.6094	Remote Similarity	NPD8360	Approved
0.6093	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD7162	Approved
0.6092	Remote Similarity	NPD7810	Phase 3
0.6092	Remote Similarity	NPD7811	Phase 3
0.6089	Remote Similarity	NPD2403	Approved
0.6089	Remote Similarity	NPD8404	Phase 2
0.6087	Remote Similarity	NPD7224	Discontinued
0.6087	Remote Similarity	NPD7223	Discontinued
0.6079	Remote Similarity	NPD4873	Discontinued
0.6075	Remote Similarity	NPD1511	Approved
0.6073	Remote Similarity	NPD6801	Discontinued
0.6068	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD7768	Phase 2
0.6062	Remote Similarity	NPD3446	Phase 1
0.6045	Remote Similarity	NPD8455	Phase 2
0.6045	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6043	Remote Similarity	NPD3936	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD3450	Approved
0.6042	Remote Similarity	NPD3452	Approved
0.6042	Remote Similarity	NPD2494	Approved
0.6042	Remote Similarity	NPD2493	Approved
0.6037	Remote Similarity	NPD1653	Approved
0.6033	Remote Similarity	NPD4582	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