NPASS Compound

Structure

CID191395 OpenBabel06191715572D 23 25 0 0 0 0 0 0 0 0999 V2000 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 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 3.0000 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 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 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 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 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 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 4 1 0 0 0 0 3 5 2 0 0 0 0 3 6 1 0 0 0 0 4 10 1 0 0 0 0 5 12 1 0 0 0 0 6 13 2 0 0 0 0 7 10 2 0 0 0 0 7 14 1 0 0 0 0 8 11 1 0 0 0 0 8 15 2 0 0 0 0 9 11 2 0 0 0 0 9 16 1 0 0 0 0 10 17 1 0 0 0 0 11 19 1 0 0 0 0 12 17 2 0 0 0 0 12 18 1 0 0 0 0 13 18 1 0 0 0 0 13 20 1 0 0 0 0 14 18 2 0 0 0 0 14 21 1 0 0 0 0 15 17 1 0 0 0 0 15 23 1 0 0 0 0 16 22 2 0 0 0 0 16 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	312.1
Volume:	317.074
LogP:	4.183
LogD:	2.483
LogS:	-4.095
# Rotatable Bonds:	3
TPSA:	90.9
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.688
Synthetic Accessibility Score:	2.95
Fsp3:	0.167
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.846
MDCK Permeability:	1.2571543265949003e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.816
Human Intestinal Absorption (HIA):	0.062
20% Bioavailability (F20%):	0.995
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	99.27005004882812%
Volume Distribution (VD):	0.447
Pgp-substrate:	1.3822295665740967%

ADMET: Metabolism

CYP1A2-inhibitor:	0.977
CYP1A2-substrate:	0.63
CYP2C19-inhibitor:	0.125
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.629
CYP2C9-substrate:	0.861
CYP2D6-inhibitor:	0.719
CYP2D6-substrate:	0.526
CYP3A4-inhibitor:	0.384
CYP3A4-substrate:	0.086

ADMET: Excretion

Clearance (CL):	4.28
Half-life (T1/2):	0.568

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.106
Drug-inuced Liver Injury (DILI):	0.879
AMES Toxicity:	0.512
Rat Oral Acute Toxicity:	0.071
Maximum Recommended Daily Dose:	0.265
Skin Sensitization:	0.713
Carcinogencity:	0.365
Eye Corrosion:	0.012
Eye Irritation:	0.938
Respiratory Toxicity:	0.628

Download Data

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

Natural Product: NPC191395

Natural Product ID:	NPC191395
*Common Name:**	Phaeochromycins A
IUPAC Name:	6-(4,5-dihydroxy-2-propylnaphthalen-1-yl)-4-hydroxypyran-2-one
Synonyms:
Standard InCHIKey:	XGGZRXUATHGLQU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H16O5/c1-2-4-10-7-14(21)18-12(5-3-6-13(18)20)17(10)15-8-11(19)9-16(22)23-15/h3,5-9,19-21H,2,4H2,1H3
SMILES:	CCCc1cc(c2c(cccc2O)c1c1cc(cc(=O)o1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL487190
PubChem CID:	54694607
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0002441] Naphthols and derivatives

*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
NPO14727.1	Streptomyces phaeochromogenes ll-p018	Subspecies	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[16124774]

☑ 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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1441	Individual Protein	MAP kinase-activated protein kinase 2	Homo sapiens	IC50	=	39000.0	nM	PMID[487085]

☑ 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 NPC191395 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	415
0.1-0.2	1913
0.2-0.3	4241
0.3-0.4	10414
0.4-0.5	7671
0.5-0.6	4012
0.6-0.7	5844
0.7-0.8	5275
0.8-0.85	2326
0.85-0.9	497
0.9-0.95	86
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9449	High Similarity	NPC315769
0.938	High Similarity	NPC185777
0.8978	High Similarity	NPC36732
0.8777	High Similarity	NPC86069
0.8712	High Similarity	NPC32463
0.8657	High Similarity	NPC472524
0.8623	High Similarity	NPC472523
0.8615	High Similarity	NPC105031
0.8603	High Similarity	NPC115861
0.8593	High Similarity	NPC131950
0.8561	High Similarity	NPC215300
0.855	High Similarity	NPC170485
0.8507	High Similarity	NPC160623
0.8507	High Similarity	NPC282508
0.8496	Intermediate Similarity	NPC16577
0.8489	Intermediate Similarity	NPC168471
0.8485	Intermediate Similarity	NPC53781
0.8485	Intermediate Similarity	NPC473221
0.8485	Intermediate Similarity	NPC46978
0.8462	Intermediate Similarity	NPC142863
0.8421	Intermediate Similarity	NPC38017
0.8409	Intermediate Similarity	NPC82299
0.8397	Intermediate Similarity	NPC228503
0.8397	Intermediate Similarity	NPC138248
0.8394	Intermediate Similarity	NPC37410
0.8392	Intermediate Similarity	NPC163846
0.8392	Intermediate Similarity	NPC225173
0.838	Intermediate Similarity	NPC260152
0.837	Intermediate Similarity	NPC8899
0.8367	Intermediate Similarity	NPC477691
0.8346	Intermediate Similarity	NPC243688
0.8333	Intermediate Similarity	NPC133463
0.8333	Intermediate Similarity	NPC206525
0.8333	Intermediate Similarity	NPC472648
0.8333	Intermediate Similarity	NPC191462
0.8333	Intermediate Similarity	NPC105718
0.8333	Intermediate Similarity	NPC170328
0.8333	Intermediate Similarity	NPC168259
0.8333	Intermediate Similarity	NPC278955
0.8333	Intermediate Similarity	NPC125801
0.8333	Intermediate Similarity	NPC472647
0.8333	Intermediate Similarity	NPC113495
0.8333	Intermediate Similarity	NPC472649
0.8309	Intermediate Similarity	NPC469611
0.8308	Intermediate Similarity	NPC476633
0.8299	Intermediate Similarity	NPC477690
0.8299	Intermediate Similarity	NPC175978
0.8299	Intermediate Similarity	NPC217447
0.8296	Intermediate Similarity	NPC254000
0.8288	Intermediate Similarity	NPC205766
0.8281	Intermediate Similarity	NPC63010
0.8276	Intermediate Similarity	NPC105415
0.8276	Intermediate Similarity	NPC37139
0.8273	Intermediate Similarity	NPC474886
0.8273	Intermediate Similarity	NPC56329
0.8273	Intermediate Similarity	NPC472646
0.8273	Intermediate Similarity	NPC35550
0.8273	Intermediate Similarity	NPC71465
0.8273	Intermediate Similarity	NPC266006
0.8273	Intermediate Similarity	NPC242715
0.8261	Intermediate Similarity	NPC258780
0.8254	Intermediate Similarity	NPC249270
0.8254	Intermediate Similarity	NPC107240
0.8252	Intermediate Similarity	NPC151607
0.8252	Intermediate Similarity	NPC475719
0.8252	Intermediate Similarity	NPC101255
0.8252	Intermediate Similarity	NPC43716
0.8252	Intermediate Similarity	NPC42540
0.8248	Intermediate Similarity	NPC469610
0.824	Intermediate Similarity	NPC46940
0.8231	Intermediate Similarity	NPC102639
0.8219	Intermediate Similarity	NPC118000
0.8219	Intermediate Similarity	NPC97028
0.8219	Intermediate Similarity	NPC158338
0.8219	Intermediate Similarity	NPC100985
0.8219	Intermediate Similarity	NPC65589
0.8219	Intermediate Similarity	NPC233267
0.8219	Intermediate Similarity	NPC288036
0.8219	Intermediate Similarity	NPC205501
0.8219	Intermediate Similarity	NPC162976
0.8219	Intermediate Similarity	NPC291049
0.8219	Intermediate Similarity	NPC97029
0.8214	Intermediate Similarity	NPC132804
0.8214	Intermediate Similarity	NPC275061
0.8214	Intermediate Similarity	NPC220344
0.8214	Intermediate Similarity	NPC243996
0.8209	Intermediate Similarity	NPC257947
0.8209	Intermediate Similarity	NPC66331
0.8203	Intermediate Similarity	NPC470760
0.8201	Intermediate Similarity	NPC118919
0.8201	Intermediate Similarity	NPC30632
0.8201	Intermediate Similarity	NPC50455
0.8195	Intermediate Similarity	NPC93219
0.8195	Intermediate Similarity	NPC244495
0.8195	Intermediate Similarity	NPC293801
0.8195	Intermediate Similarity	NPC232387
0.8194	Intermediate Similarity	NPC471608
0.8188	Intermediate Similarity	NPC473107
0.8182	Intermediate Similarity	NPC471731
0.8182	Intermediate Similarity	NPC159721
0.8175	Intermediate Similarity	NPC165612
0.8175	Intermediate Similarity	NPC19157
0.8175	Intermediate Similarity	NPC117846
0.8169	Intermediate Similarity	NPC93640
0.8169	Intermediate Similarity	NPC20631
0.8163	Intermediate Similarity	NPC158866
0.816	Intermediate Similarity	NPC95716
0.816	Intermediate Similarity	NPC151537
0.8156	Intermediate Similarity	NPC273623
0.8156	Intermediate Similarity	NPC12668
0.8156	Intermediate Similarity	NPC308768
0.8154	Intermediate Similarity	NPC282255
0.8154	Intermediate Similarity	NPC103916
0.8151	Intermediate Similarity	NPC7025
0.8151	Intermediate Similarity	NPC256672
0.8151	Intermediate Similarity	NPC27221
0.8148	Intermediate Similarity	NPC185066
0.8148	Intermediate Similarity	NPC219923
0.8146	Intermediate Similarity	NPC474373
0.8143	Intermediate Similarity	NPC266453
0.8143	Intermediate Similarity	NPC131198
0.8143	Intermediate Similarity	NPC230919
0.8143	Intermediate Similarity	NPC200935
0.8143	Intermediate Similarity	NPC22902
0.8134	Intermediate Similarity	NPC101894
0.8129	Intermediate Similarity	NPC69029
0.8129	Intermediate Similarity	NPC10314
0.8129	Intermediate Similarity	NPC200557
0.8129	Intermediate Similarity	NPC241241
0.8129	Intermediate Similarity	NPC108198
0.8129	Intermediate Similarity	NPC294884
0.8129	Intermediate Similarity	NPC158142
0.8125	Intermediate Similarity	NPC71739
0.8125	Intermediate Similarity	NPC125617
0.8125	Intermediate Similarity	NPC115808
0.8125	Intermediate Similarity	NPC471305
0.8121	Intermediate Similarity	NPC329844
0.8121	Intermediate Similarity	NPC169990
0.8121	Intermediate Similarity	NPC210942
0.812	Intermediate Similarity	NPC265413
0.812	Intermediate Similarity	NPC140521
0.812	Intermediate Similarity	NPC270030
0.812	Intermediate Similarity	NPC224342
0.812	Intermediate Similarity	NPC10154
0.8116	Intermediate Similarity	NPC31849
0.8112	Intermediate Similarity	NPC250755
0.8112	Intermediate Similarity	NPC471733
0.8108	Intermediate Similarity	NPC133856
0.8108	Intermediate Similarity	NPC258249
0.8106	Intermediate Similarity	NPC325301
0.8106	Intermediate Similarity	NPC74137
0.8102	Intermediate Similarity	NPC37009
0.8102	Intermediate Similarity	NPC15543
0.8102	Intermediate Similarity	NPC66430
0.8099	Intermediate Similarity	NPC310370
0.8099	Intermediate Similarity	NPC265075
0.8099	Intermediate Similarity	NPC71046
0.8099	Intermediate Similarity	NPC183642
0.8099	Intermediate Similarity	NPC170812
0.8099	Intermediate Similarity	NPC138149
0.8099	Intermediate Similarity	NPC470986
0.8095	Intermediate Similarity	NPC329933
0.8095	Intermediate Similarity	NPC43525
0.8095	Intermediate Similarity	NPC247219
0.8092	Intermediate Similarity	NPC100108
0.8092	Intermediate Similarity	NPC277798
0.8092	Intermediate Similarity	NPC129176
0.8088	Intermediate Similarity	NPC222108
0.8088	Intermediate Similarity	NPC96719
0.8088	Intermediate Similarity	NPC471519
0.8088	Intermediate Similarity	NPC471518
0.8085	Intermediate Similarity	NPC218131
0.8085	Intermediate Similarity	NPC105847
0.8085	Intermediate Similarity	NPC243759
0.8082	Intermediate Similarity	NPC34802
0.8082	Intermediate Similarity	NPC123202
0.8082	Intermediate Similarity	NPC7943
0.8082	Intermediate Similarity	NPC22005
0.8079	Intermediate Similarity	NPC263483
0.8079	Intermediate Similarity	NPC143328
0.8077	Intermediate Similarity	NPC184302
0.8071	Intermediate Similarity	NPC202846
0.8071	Intermediate Similarity	NPC143139
0.8071	Intermediate Similarity	NPC205442
0.8071	Intermediate Similarity	NPC158481
0.8067	Intermediate Similarity	NPC66029
0.806	Intermediate Similarity	NPC476653
0.806	Intermediate Similarity	NPC124030
0.806	Intermediate Similarity	NPC249836
0.8058	Intermediate Similarity	NPC125649
0.8058	Intermediate Similarity	NPC175943
0.8056	Intermediate Similarity	NPC471824
0.8056	Intermediate Similarity	NPC84266
0.8054	Intermediate Similarity	NPC223720
0.8054	Intermediate Similarity	NPC273483
0.8047	Intermediate Similarity	NPC84999
0.8047	Intermediate Similarity	NPC246760
0.8045	Intermediate Similarity	NPC315807
0.8043	Intermediate Similarity	NPC476389
0.8043	Intermediate Similarity	NPC194277

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 NPC191395 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	399
0.1-0.2	1001
0.2-0.3	1577
0.3-0.4	2621
0.4-0.5	1907
0.5-0.6	1091
0.6-0.7	362
0.7-0.8	129
0.8-0.85	48
0.85-0.9	14
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8496	Intermediate Similarity	NPD4625	Phase 3
0.8438	Intermediate Similarity	NPD4626	Approved
0.8217	Intermediate Similarity	NPD5691	Approved
0.8043	Intermediate Similarity	NPD4060	Phase 1
0.8042	Intermediate Similarity	NPD3750	Approved
0.803	Intermediate Similarity	NPD422	Phase 1
0.8014	Intermediate Similarity	NPD5405	Approved
0.8014	Intermediate Similarity	NPD5404	Approved
0.8014	Intermediate Similarity	NPD5408	Approved
0.8014	Intermediate Similarity	NPD5406	Approved
0.7917	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7899	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD1611	Approved
0.7871	Intermediate Similarity	NPD6232	Discontinued
0.7852	Intermediate Similarity	NPD1283	Approved
0.7794	Intermediate Similarity	NPD2797	Approved
0.7778	Intermediate Similarity	NPD4749	Approved
0.7778	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD3764	Approved
0.7763	Intermediate Similarity	NPD7819	Suspended
0.7762	Intermediate Similarity	NPD2935	Discontinued
0.7754	Intermediate Similarity	NPD4908	Phase 1
0.773	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD5124	Phase 1
0.7722	Intermediate Similarity	NPD7473	Discontinued
0.7703	Intermediate Similarity	NPD2533	Approved
0.7703	Intermediate Similarity	NPD2534	Approved
0.7703	Intermediate Similarity	NPD2532	Approved
0.7698	Intermediate Similarity	NPD2342	Discontinued
0.7692	Intermediate Similarity	NPD3748	Approved
0.7674	Intermediate Similarity	NPD7635	Approved
0.7671	Intermediate Similarity	NPD7003	Approved
0.7643	Intermediate Similarity	NPD3268	Approved
0.763	Intermediate Similarity	NPD1281	Approved
0.763	Intermediate Similarity	NPD1610	Phase 2
0.7625	Intermediate Similarity	NPD5844	Phase 1
0.7616	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD3226	Approved
0.7603	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD1548	Phase 1
0.7591	Intermediate Similarity	NPD3225	Approved
0.7586	Intermediate Similarity	NPD2346	Discontinued
0.7584	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD4750	Phase 3
0.7569	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD7768	Phase 2
0.7537	Intermediate Similarity	NPD1651	Approved
0.7535	Intermediate Similarity	NPD2979	Phase 3
0.7518	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD6100	Approved
0.7517	Intermediate Similarity	NPD6099	Approved
0.7517	Intermediate Similarity	NPD7390	Discontinued
0.75	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD6959	Discontinued
0.7467	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD6696	Suspended
0.7448	Intermediate Similarity	NPD4308	Phase 3
0.7431	Intermediate Similarity	NPD4097	Suspended
0.7429	Intermediate Similarity	NPD2861	Phase 2
0.7429	Intermediate Similarity	NPD5736	Approved
0.7429	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD4140	Approved
0.7405	Intermediate Similarity	NPD5535	Approved
0.7397	Intermediate Similarity	NPD2438	Suspended
0.7372	Intermediate Similarity	NPD1201	Approved
0.7355	Intermediate Similarity	NPD37	Approved
0.7351	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD5762	Approved
0.7347	Intermediate Similarity	NPD5763	Approved
0.7347	Intermediate Similarity	NPD7266	Discontinued
0.7342	Intermediate Similarity	NPD6234	Discontinued
0.7329	Intermediate Similarity	NPD1510	Phase 2
0.7329	Intermediate Similarity	NPD2799	Discontinued
0.7325	Intermediate Similarity	NPD4966	Approved
0.7325	Intermediate Similarity	NPD4965	Approved
0.7325	Intermediate Similarity	NPD4967	Phase 2
0.7324	Intermediate Similarity	NPD3027	Phase 3
0.7324	Intermediate Similarity	NPD7095	Approved
0.7319	Intermediate Similarity	NPD1608	Approved
0.7315	Intermediate Similarity	NPD4628	Phase 3
0.7312	Intermediate Similarity	NPD7229	Phase 3
0.731	Intermediate Similarity	NPD1607	Approved
0.7308	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD940	Approved
0.7302	Intermediate Similarity	NPD846	Approved
0.7299	Intermediate Similarity	NPD3496	Discontinued
0.7292	Intermediate Similarity	NPD1613	Approved
0.7292	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD7411	Suspended
0.7286	Intermediate Similarity	NPD3266	Approved
0.7286	Intermediate Similarity	NPD1470	Approved
0.7286	Intermediate Similarity	NPD1164	Approved
0.7286	Intermediate Similarity	NPD3267	Approved
0.728	Intermediate Similarity	NPD3020	Approved
0.7279	Intermediate Similarity	NPD1551	Phase 2
0.7279	Intermediate Similarity	NPD2531	Phase 2
0.7278	Intermediate Similarity	NPD7075	Discontinued
0.7278	Intermediate Similarity	NPD3749	Approved
0.7233	Intermediate Similarity	NPD5709	Phase 3
0.7226	Intermediate Similarity	NPD2286	Discontinued
0.7226	Intermediate Similarity	NPD3019	Approved
0.7226	Intermediate Similarity	NPD2932	Approved
0.7226	Intermediate Similarity	NPD1778	Approved
0.7226	Intermediate Similarity	NPD4380	Phase 2
0.7222	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1242	Phase 1
0.7222	Intermediate Similarity	NPD6663	Approved
0.7211	Intermediate Similarity	NPD7033	Discontinued
0.72	Intermediate Similarity	NPD8166	Discontinued
0.7197	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1465	Phase 2
0.7192	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4666	Phase 3
0.7177	Intermediate Similarity	NPD2860	Approved
0.7177	Intermediate Similarity	NPD844	Approved
0.7177	Intermediate Similarity	NPD2859	Approved
0.7176	Intermediate Similarity	NPD3022	Approved
0.7176	Intermediate Similarity	NPD3021	Approved
0.7172	Intermediate Similarity	NPD4307	Phase 2
0.7172	Intermediate Similarity	NPD1240	Approved
0.7171	Intermediate Similarity	NPD1511	Approved
0.7171	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD6559	Discontinued
0.7162	Intermediate Similarity	NPD4477	Approved
0.7162	Intermediate Similarity	NPD4476	Approved
0.7153	Intermediate Similarity	NPD2313	Discontinued
0.7152	Intermediate Similarity	NPD4288	Approved
0.7152	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7177	Discontinued
0.7134	Intermediate Similarity	NPD6801	Discontinued
0.7133	Intermediate Similarity	NPD1652	Phase 2
0.7133	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD4340	Discontinued
0.712	Intermediate Similarity	NPD288	Approved
0.7115	Intermediate Similarity	NPD6599	Discontinued
0.7114	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD709	Approved
0.7111	Intermediate Similarity	NPD6671	Approved
0.7107	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6666	Approved
0.7105	Intermediate Similarity	NPD6667	Approved
0.7103	Intermediate Similarity	NPD8032	Phase 2
0.7101	Intermediate Similarity	NPD5126	Approved
0.7101	Intermediate Similarity	NPD5125	Phase 3
0.7101	Intermediate Similarity	NPD17	Approved
0.7099	Intermediate Similarity	NPD5710	Approved
0.7099	Intermediate Similarity	NPD5711	Approved
0.7097	Intermediate Similarity	NPD2933	Approved
0.7097	Intermediate Similarity	NPD2934	Approved
0.7097	Intermediate Similarity	NPD1653	Approved
0.7095	Intermediate Similarity	NPD4108	Discontinued
0.709	Intermediate Similarity	NPD1398	Phase 1
0.7089	Intermediate Similarity	NPD2801	Approved
0.7081	Intermediate Similarity	NPD6746	Phase 2
0.708	Intermediate Similarity	NPD9545	Approved
0.708	Intermediate Similarity	NPD3091	Approved
0.7078	Intermediate Similarity	NPD6273	Approved
0.7078	Intermediate Similarity	NPD1512	Approved
0.707	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD1549	Phase 2
0.7059	Intermediate Similarity	NPD7340	Approved
0.7051	Intermediate Similarity	NPD7458	Discontinued
0.705	Intermediate Similarity	NPD3847	Discontinued
0.7047	Intermediate Similarity	NPD2796	Approved
0.7044	Intermediate Similarity	NPD3817	Phase 2
0.7042	Intermediate Similarity	NPD1203	Approved
0.7042	Intermediate Similarity	NPD3094	Phase 2
0.7037	Intermediate Similarity	NPD497	Approved
0.7037	Intermediate Similarity	NPD7199	Phase 2
0.7034	Intermediate Similarity	NPD6798	Discontinued
0.7034	Intermediate Similarity	NPD1296	Phase 2
0.7034	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7228	Approved
0.7025	Intermediate Similarity	NPD1934	Approved
0.7021	Intermediate Similarity	NPD1669	Approved
0.7021	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD6674	Discontinued
0.702	Intermediate Similarity	NPD1243	Approved
0.7013	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD230	Phase 1
0.7007	Intermediate Similarity	NPD7644	Approved
0.7007	Intermediate Similarity	NPD6355	Discontinued
0.7	Intermediate Similarity	NPD3092	Approved
0.7	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD4624	Approved
0.6993	Remote Similarity	NPD2798	Approved
0.698	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD4059	Approved
0.6977	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD8651	Approved
0.6968	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD498	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