NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	194.06
Volume:	189.018
LogP:	1.177
LogD:	0.818
LogS:	-1.797
# Rotatable Bonds:	0
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.528
Synthetic Accessibility Score:	3.139
Fsp3:	0.3
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.016
MDCK Permeability:	6.314351139735663e-06
Pgp-inhibitor:	0.003
Pgp-substrate:	0.053
Human Intestinal Absorption (HIA):	0.507
20% Bioavailability (F20%):	0.988
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.259
Plasma Protein Binding (PPB):	53.95885467529297%
Volume Distribution (VD):	0.828
Pgp-substrate:	47.835994720458984%

ADMET: Metabolism

CYP1A2-inhibitor:	0.477
CYP1A2-substrate:	0.32
CYP2C19-inhibitor:	0.053
CYP2C19-substrate:	0.087
CYP2C9-inhibitor:	0.062
CYP2C9-substrate:	0.687
CYP2D6-inhibitor:	0.057
CYP2D6-substrate:	0.288
CYP3A4-inhibitor:	0.065
CYP3A4-substrate:	0.166

ADMET: Excretion

Clearance (CL):	16.456
Half-life (T1/2):	0.773

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.098
Drug-inuced Liver Injury (DILI):	0.317
AMES Toxicity:	0.329
Rat Oral Acute Toxicity:	0.585
Maximum Recommended Daily Dose:	0.244
Skin Sensitization:	0.894
Carcinogencity:	0.426
Eye Corrosion:	0.03
Eye Irritation:	0.948
Respiratory Toxicity:	0.711

Download Data

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

Natural Product: NPC147757

Natural Product ID:	NPC147757
*Common Name:**	6-Hydroxy-Isosclerone
IUPAC Name:	(4S)-4,6,8-trihydroxy-3,4-dihydro-2H-naphthalen-1-one
Synonyms:	6-Hydroxy-Isosclerone
Standard InCHIKey:	YIIXGDYMMKWBPB-ZETCQYMHSA-N
Standard InCHI:	InChI=1S/C10H10O4/c11-5-3-6-7(12)1-2-8(13)10(6)9(14)4-5/h3-4,7,11-12,14H,1-2H2/t7-/m0/s1
SMILES:	Oc1cc2[C@@H](O)CCC(=O)c2c(c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL510767
PubChem CID:	44585560
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000048] Tetralins

*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
NPO25302	Viola philippica	Species	Violaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14519932]
NPO32546	ymf 1.01029	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[18479163]
NPO28287	Magnaporthe oryzae	Species	Magnaporthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26258762]
NPO25302	Viola philippica	Species	Violaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25302	Viola philippica	Species	Violaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28287	Magnaporthe oryzae	Species	Magnaporthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3641	Polyporus tuberaster	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16391	Protea neriifolia	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO318	Glycosmis trichanthera	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4567	Senecio chrysocoma	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6773	Bryoria implexa	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25302	Viola philippica	Species	Violaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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	1
Others	4

Activity Type	# Activity
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT593	Organism	Bursaphelenchus xylophilus	Bursaphelenchus xylophilus	Activity	=	51.2	%	PMID[450415]
NPT593	Organism	Bursaphelenchus xylophilus	Bursaphelenchus xylophilus	Activity	=	23.7	%	PMID[450415]
NPT593	Organism	Bursaphelenchus xylophilus	Bursaphelenchus xylophilus	Activity	=	57.3	%	PMID[450415]
NPT593	Organism	Bursaphelenchus xylophilus	Bursaphelenchus xylophilus	Activity	=	46.7	%	PMID[450415]
NPT115	Organism	Mycobacterium tuberculosis H37Ra	Mycobacterium tuberculosis H37Ra	MIC	=	12.5	ug.mL-1	PMID[450416]

☑ 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 NPC147757 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	354
0.1-0.2	1421
0.2-0.3	3831
0.3-0.4	10118
0.4-0.5	9130
0.5-0.6	4731
0.6-0.7	6789
0.7-0.8	5400
0.8-0.85	705
0.85-0.9	196
0.9-0.95	20
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.984	High Similarity	NPC478190
0.9225	High Similarity	NPC17843
0.9213	High Similarity	NPC247250
0.9213	High Similarity	NPC767
0.9173	High Similarity	NPC190457
0.9127	High Similarity	NPC10926
0.9111	High Similarity	NPC474961
0.9111	High Similarity	NPC137649
0.9062	High Similarity	NPC179898
0.9055	High Similarity	NPC8745
0.9048	High Similarity	NPC13238
0.9037	High Similarity	NPC204045
0.9037	High Similarity	NPC305845
0.8992	High Similarity	NPC120488
0.8992	High Similarity	NPC92624
0.8992	High Similarity	NPC102829
0.8978	High Similarity	NPC244691
0.8978	High Similarity	NPC471906
0.8976	High Similarity	NPC201728
0.8976	High Similarity	NPC477454
0.8976	High Similarity	NPC262671
0.8971	High Similarity	NPC135524
0.8952	High Similarity	NPC473662
0.8952	High Similarity	NPC216297
0.8952	High Similarity	NPC7151
0.8939	High Similarity	NPC44437
0.8939	High Similarity	NPC282780
0.8939	High Similarity	NPC166480
0.8923	High Similarity	NPC259942
0.8915	High Similarity	NPC41263
0.8906	High Similarity	NPC473691
0.8889	High Similarity	NPC268052
0.8881	High Similarity	NPC170742
0.8864	High Similarity	NPC40524
0.8864	High Similarity	NPC213485
0.8864	High Similarity	NPC267205
0.8864	High Similarity	NPC139074
0.8815	High Similarity	NPC175552
0.8815	High Similarity	NPC475974
0.881	High Similarity	NPC224273
0.881	High Similarity	NPC143427
0.881	High Similarity	NPC242895
0.881	High Similarity	NPC73532
0.881	High Similarity	NPC267552
0.881	High Similarity	NPC19174
0.881	High Similarity	NPC45438
0.881	High Similarity	NPC115159
0.8806	High Similarity	NPC235115
0.8806	High Similarity	NPC254847
0.8797	High Similarity	NPC474519
0.879	High Similarity	NPC40649
0.879	High Similarity	NPC209486
0.8779	High Similarity	NPC62219
0.8759	High Similarity	NPC244923
0.875	High Similarity	NPC32360
0.875	High Similarity	NPC143438
0.875	High Similarity	NPC474655
0.8741	High Similarity	NPC53414
0.8741	High Similarity	NPC471905
0.8741	High Similarity	NPC474849
0.8741	High Similarity	NPC178467
0.8741	High Similarity	NPC65837
0.8741	High Similarity	NPC53206
0.8741	High Similarity	NPC474771
0.8741	High Similarity	NPC149372
0.874	High Similarity	NPC133909
0.874	High Similarity	NPC32032
0.8731	High Similarity	NPC130899
0.8731	High Similarity	NPC283590
0.8731	High Similarity	NPC70859
0.8731	High Similarity	NPC61153
0.873	High Similarity	NPC146642
0.873	High Similarity	NPC297186
0.8722	High Similarity	NPC314048
0.8722	High Similarity	NPC153783
0.8712	High Similarity	NPC469526
0.8712	High Similarity	NPC475042
0.8712	High Similarity	NPC219892
0.8712	High Similarity	NPC189823
0.8712	High Similarity	NPC34070
0.8705	High Similarity	NPC48762
0.8696	High Similarity	NPC73061
0.8686	High Similarity	NPC156872
0.8686	High Similarity	NPC155205
0.8676	High Similarity	NPC33144
0.8676	High Similarity	NPC94248
0.8676	High Similarity	NPC478200
0.8676	High Similarity	NPC212693
0.8676	High Similarity	NPC472403
0.8676	High Similarity	NPC472602
0.8676	High Similarity	NPC9121
0.8676	High Similarity	NPC191835
0.8676	High Similarity	NPC177307
0.8667	High Similarity	NPC191976
0.8661	High Similarity	NPC156139
0.8657	High Similarity	NPC474394
0.8651	High Similarity	NPC294037
0.8647	High Similarity	NPC135801
0.8643	High Similarity	NPC34482
0.8636	High Similarity	NPC26697
0.8636	High Similarity	NPC247477
0.8636	High Similarity	NPC233056
0.8636	High Similarity	NPC17840
0.8623	High Similarity	NPC187843
0.8623	High Similarity	NPC110810
0.8623	High Similarity	NPC158634
0.8623	High Similarity	NPC290550
0.8613	High Similarity	NPC242994
0.8613	High Similarity	NPC247409
0.8613	High Similarity	NPC105456
0.8613	High Similarity	NPC92655
0.8613	High Similarity	NPC138099
0.8613	High Similarity	NPC139634
0.8605	High Similarity	NPC74507
0.8605	High Similarity	NPC152525
0.8605	High Similarity	NPC68756
0.8605	High Similarity	NPC234890
0.8603	High Similarity	NPC70380
0.8603	High Similarity	NPC71256
0.8603	High Similarity	NPC290030
0.8593	High Similarity	NPC278375
0.8593	High Similarity	NPC129752
0.8592	High Similarity	NPC153417
0.8583	High Similarity	NPC248363
0.8583	High Similarity	NPC149246
0.8582	High Similarity	NPC52407
0.8582	High Similarity	NPC470570
0.8582	High Similarity	NPC48036
0.8571	High Similarity	NPC21599
0.8571	High Similarity	NPC158222
0.8571	High Similarity	NPC193703
0.8571	High Similarity	NPC161617
0.8561	High Similarity	NPC49108
0.856	High Similarity	NPC230349
0.8551	High Similarity	NPC181560
0.8551	High Similarity	NPC169452
0.8551	High Similarity	NPC158472
0.8551	High Similarity	NPC203063
0.8551	High Similarity	NPC183345
0.8531	High Similarity	NPC477221
0.8529	High Similarity	NPC223836
0.8529	High Similarity	NPC118919
0.8529	High Similarity	NPC315275
0.8521	High Similarity	NPC290194
0.8519	High Similarity	NPC175943
0.8516	High Similarity	NPC196976
0.8516	High Similarity	NPC198336
0.8516	High Similarity	NPC215392
0.8511	High Similarity	NPC257558
0.8511	High Similarity	NPC83272
0.8507	High Similarity	NPC175738
0.8507	High Similarity	NPC70622
0.8504	High Similarity	NPC159525
0.85	High Similarity	NPC354984
0.85	High Similarity	NPC469542
0.85	High Similarity	NPC478202
0.85	High Similarity	NPC472006
0.85	High Similarity	NPC51106
0.85	High Similarity	NPC238629
0.8489	Intermediate Similarity	NPC472603
0.8489	Intermediate Similarity	NPC246638
0.8489	Intermediate Similarity	NPC313123
0.8489	Intermediate Similarity	NPC90411
0.8489	Intermediate Similarity	NPC472904
0.8489	Intermediate Similarity	NPC472605
0.8489	Intermediate Similarity	NPC472604
0.8489	Intermediate Similarity	NPC53649
0.8489	Intermediate Similarity	NPC472035
0.8489	Intermediate Similarity	NPC478217
0.8489	Intermediate Similarity	NPC182421
0.8489	Intermediate Similarity	NPC478201
0.8485	Intermediate Similarity	NPC95537
0.8483	Intermediate Similarity	NPC470337
0.8483	Intermediate Similarity	NPC470340
0.8483	Intermediate Similarity	NPC268992
0.8483	Intermediate Similarity	NPC470338
0.8483	Intermediate Similarity	NPC51824
0.8483	Intermediate Similarity	NPC474843
0.8483	Intermediate Similarity	NPC113608
0.8478	Intermediate Similarity	NPC472903
0.8478	Intermediate Similarity	NPC88269
0.8478	Intermediate Similarity	NPC275356
0.8478	Intermediate Similarity	NPC52358
0.8478	Intermediate Similarity	NPC162939
0.8478	Intermediate Similarity	NPC471819
0.8473	Intermediate Similarity	NPC267846
0.8472	Intermediate Similarity	NPC147735
0.8472	Intermediate Similarity	NPC202595
0.8467	Intermediate Similarity	NPC135837
0.8467	Intermediate Similarity	NPC193792
0.8467	Intermediate Similarity	NPC301915
0.8467	Intermediate Similarity	NPC261292
0.8456	Intermediate Similarity	NPC182496
0.8456	Intermediate Similarity	NPC161632
0.8456	Intermediate Similarity	NPC290803
0.8456	Intermediate Similarity	NPC180905
0.8451	Intermediate Similarity	NPC107625
0.845	Intermediate Similarity	NPC91105
0.845	Intermediate Similarity	NPC283514
0.8444	Intermediate Similarity	NPC37299

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 NPC147757 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	316
0.1-0.2	919
0.2-0.3	1779
0.3-0.4	2848
0.4-0.5	1851
0.5-0.6	1002
0.6-0.7	340
0.7-0.8	86
0.8-0.85	8
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8806	High Similarity	NPD1509	Clinical (unspecified phase)
0.8667	High Similarity	NPD651	Clinical (unspecified phase)
0.8647	High Similarity	NPD943	Approved
0.8345	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.831	Intermediate Similarity	NPD7390	Discontinued
0.8261	Intermediate Similarity	NPD1510	Phase 2
0.8258	Intermediate Similarity	NPD1470	Approved
0.8231	Intermediate Similarity	NPD1201	Approved
0.8189	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8143	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8143	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8102	Intermediate Similarity	NPD1240	Approved
0.8085	Intermediate Similarity	NPD1549	Phase 2
0.7986	Intermediate Similarity	NPD1607	Approved
0.7931	Intermediate Similarity	NPD1511	Approved
0.7895	Intermediate Similarity	NPD9269	Phase 2
0.7877	Intermediate Similarity	NPD2532	Approved
0.7877	Intermediate Similarity	NPD2534	Approved
0.7877	Intermediate Similarity	NPD2533	Approved
0.7867	Intermediate Similarity	NPD1934	Approved
0.7863	Intermediate Similarity	NPD9268	Approved
0.7852	Intermediate Similarity	NPD4380	Phase 2
0.7823	Intermediate Similarity	NPD1512	Approved
0.7815	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD230	Phase 1
0.7755	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD6959	Discontinued
0.7697	Intermediate Similarity	NPD7819	Suspended
0.7697	Intermediate Similarity	NPD2801	Approved
0.7692	Intermediate Similarity	NPD5408	Approved
0.7692	Intermediate Similarity	NPD5405	Approved
0.7692	Intermediate Similarity	NPD5404	Approved
0.7692	Intermediate Similarity	NPD5406	Approved
0.7603	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD3882	Suspended
0.7591	Intermediate Similarity	NPD1164	Approved
0.758	Intermediate Similarity	NPD6232	Discontinued
0.7569	Intermediate Similarity	NPD2796	Approved
0.7548	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD7473	Discontinued
0.7534	Intermediate Similarity	NPD2800	Approved
0.7532	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3818	Discontinued
0.7484	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6166	Phase 2
0.7483	Intermediate Similarity	NPD3750	Approved
0.7448	Intermediate Similarity	NPD2935	Discontinued
0.7448	Intermediate Similarity	NPD1551	Phase 2
0.7436	Intermediate Similarity	NPD3749	Approved
0.7422	Intermediate Similarity	NPD74	Approved
0.7422	Intermediate Similarity	NPD9266	Approved
0.7372	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD9493	Approved
0.7346	Intermediate Similarity	NPD7054	Approved
0.7344	Intermediate Similarity	NPD9267	Approved
0.7344	Intermediate Similarity	NPD9263	Approved
0.7344	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD9264	Approved
0.7333	Intermediate Similarity	NPD6799	Approved
0.7325	Intermediate Similarity	NPD7075	Discontinued
0.7308	Intermediate Similarity	NPD3817	Phase 2
0.7308	Intermediate Similarity	NPD5402	Approved
0.7301	Intermediate Similarity	NPD7074	Phase 3
0.7301	Intermediate Similarity	NPD7472	Approved
0.7285	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD1242	Phase 1
0.7273	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD3300	Phase 2
0.7259	Intermediate Similarity	NPD9545	Approved
0.7256	Intermediate Similarity	NPD6797	Phase 2
0.725	Intermediate Similarity	NPD5711	Approved
0.725	Intermediate Similarity	NPD5710	Approved
0.7244	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1465	Phase 2
0.7241	Intermediate Similarity	NPD6651	Approved
0.7233	Intermediate Similarity	NPD5494	Approved
0.7226	Intermediate Similarity	NPD7411	Suspended
0.7212	Intermediate Similarity	NPD7251	Discontinued
0.7206	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD3764	Approved
0.7179	Intermediate Similarity	NPD6801	Discontinued
0.7169	Intermediate Similarity	NPD7808	Phase 3
0.7162	Intermediate Similarity	NPD2344	Approved
0.7161	Intermediate Similarity	NPD6599	Discontinued
0.7143	Intermediate Similarity	NPD3748	Approved
0.7134	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD5844	Phase 1
0.7099	Intermediate Similarity	NPD4750	Phase 3
0.7097	Intermediate Similarity	NPD3226	Approved
0.7095	Intermediate Similarity	NPD6100	Approved
0.7095	Intermediate Similarity	NPD6099	Approved
0.7092	Intermediate Similarity	NPD1203	Approved
0.709	Intermediate Similarity	NPD9281	Approved
0.7087	Intermediate Similarity	NPD940	Approved
0.7087	Intermediate Similarity	NPD846	Approved
0.7086	Intermediate Similarity	NPD6190	Approved
0.7083	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD920	Approved
0.7078	Intermediate Similarity	NPD5403	Approved
0.7073	Intermediate Similarity	NPD3751	Discontinued
0.7059	Intermediate Similarity	NPD5401	Approved
0.7059	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD2346	Discontinued
0.7044	Intermediate Similarity	NPD7768	Phase 2
0.7031	Intermediate Similarity	NPD9261	Approved
0.7029	Intermediate Similarity	NPD2932	Approved
0.7029	Intermediate Similarity	NPD3019	Approved
0.7027	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6559	Discontinued
0.6977	Remote Similarity	NPD1237	Approved
0.6974	Remote Similarity	NPD2309	Approved
0.6962	Remote Similarity	NPD37	Approved
0.6954	Remote Similarity	NPD2654	Approved
0.6954	Remote Similarity	NPD1243	Approved
0.6939	Remote Similarity	NPD447	Suspended
0.6936	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD3787	Discontinued
0.6929	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD520	Approved
0.6913	Remote Similarity	NPD2799	Discontinued
0.6908	Remote Similarity	NPD3400	Discontinued
0.6908	Remote Similarity	NPD4628	Phase 3
0.6901	Remote Similarity	NPD8150	Discontinued
0.6879	Remote Similarity	NPD9717	Approved
0.6875	Remote Similarity	NPD9494	Approved
0.6871	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD1613	Approved
0.6871	Remote Similarity	NPD1247	Approved
0.6864	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD2313	Discontinued
0.6845	Remote Similarity	NPD5953	Discontinued
0.6842	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD4965	Approved
0.6832	Remote Similarity	NPD4966	Approved
0.6832	Remote Similarity	NPD4967	Phase 2
0.6826	Remote Similarity	NPD7286	Phase 2
0.6824	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD1610	Phase 2
0.6806	Remote Similarity	NPD2798	Approved
0.6788	Remote Similarity	NPD3926	Phase 2
0.6781	Remote Similarity	NPD3027	Phase 3
0.6772	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD36	Approved
0.6765	Remote Similarity	NPD4955	Approved
0.6765	Remote Similarity	NPD5028	Approved
0.6765	Remote Similarity	NPD4954	Approved
0.6765	Remote Similarity	NPD5026	Approved
0.6765	Remote Similarity	NPD5034	Approved
0.6763	Remote Similarity	NPD1548	Phase 1
0.6761	Remote Similarity	NPD6534	Approved
0.6761	Remote Similarity	NPD6535	Approved
0.6755	Remote Similarity	NPD9570	Approved
0.6748	Remote Similarity	NPD6234	Discontinued
0.6748	Remote Similarity	NPD919	Approved
0.6736	Remote Similarity	NPD3094	Phase 2
0.6735	Remote Similarity	NPD411	Approved
0.6731	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6020	Phase 2
0.6725	Remote Similarity	NPD8312	Approved
0.6725	Remote Similarity	NPD8313	Approved
0.6725	Remote Similarity	NPD5035	Approved
0.6712	Remote Similarity	NPD6832	Phase 2
0.6711	Remote Similarity	NPD1471	Phase 3
0.6706	Remote Similarity	NPD5030	Phase 2
0.6705	Remote Similarity	NPD5037	Approved
0.6705	Remote Similarity	NPD5038	Approved
0.669	Remote Similarity	NPD422	Phase 1
0.6689	Remote Similarity	NPD6663	Approved
0.6688	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6777	Approved
0.6667	Remote Similarity	NPD4363	Phase 3
0.6667	Remote Similarity	NPD6780	Approved
0.6667	Remote Similarity	NPD1283	Approved
0.6667	Remote Similarity	NPD6776	Approved
0.6667	Remote Similarity	NPD1876	Approved
0.6667	Remote Similarity	NPD6779	Approved
0.6667	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6782	Approved
0.6667	Remote Similarity	NPD6778	Approved
0.6667	Remote Similarity	NPD6781	Approved
0.6667	Remote Similarity	NPD4360	Phase 2
0.6649	Remote Similarity	NPD8151	Discontinued
0.6648	Remote Similarity	NPD7699	Phase 2
0.6648	Remote Similarity	NPD7700	Phase 2
0.6647	Remote Similarity	NPD5036	Approved
0.6646	Remote Similarity	NPD6844	Discontinued
0.6646	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD5736	Approved
0.6643	Remote Similarity	NPD3091	Approved
0.6643	Remote Similarity	NPD1608	Approved
0.6643	Remote Similarity	NPD3972	Approved
0.663	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD7229	Phase 3

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