NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	178.06
Volume:	180.228
LogP:	0.854
LogD:	0.955
LogS:	-2.263
# Rotatable Bonds:	0
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.631
Synthetic Accessibility Score:	2.914
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:	-4.576
MDCK Permeability:	1.3875666809326503e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.142
Human Intestinal Absorption (HIA):	0.147
20% Bioavailability (F20%):	0.945
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.436
Plasma Protein Binding (PPB):	32.45834732055664%
Volume Distribution (VD):	0.823
Pgp-substrate:	64.78082275390625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.211
CYP1A2-substrate:	0.502
CYP2C19-inhibitor:	0.094
CYP2C19-substrate:	0.286
CYP2C9-inhibitor:	0.044
CYP2C9-substrate:	0.818
CYP2D6-inhibitor:	0.053
CYP2D6-substrate:	0.617
CYP3A4-inhibitor:	0.011
CYP3A4-substrate:	0.264

ADMET: Excretion

Clearance (CL):	8.312
Half-life (T1/2):	0.744

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.132
Drug-inuced Liver Injury (DILI):	0.145
AMES Toxicity:	0.477
Rat Oral Acute Toxicity:	0.366
Maximum Recommended Daily Dose:	0.29
Skin Sensitization:	0.435
Carcinogencity:	0.392
Eye Corrosion:	0.008
Eye Irritation:	0.797
Respiratory Toxicity:	0.263

Download Data

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

Natural Product: NPC216297

Natural Product ID:	NPC216297
*Common Name:**	(-)-Isosclerone
IUPAC Name:	(4R)-4,8-dihydroxy-3,4-dihydro-2H-naphthalen-1-one
Synonyms:	(-)-Isosclerone
Standard InCHIKey:	ZXYYTDCENDYKBR-SSDOTTSWSA-N
Standard InCHI:	InChI=1S/C10H10O3/c11-7-4-5-9(13)10-6(7)2-1-3-8(10)12/h1-3,7,11-12H,4-5H2/t7-/m1/s1
SMILES:	c1cc2[C@@H](CCC(=O)c2c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL482610
PubChem CID:	44576009
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
NPO26892	Juglans mandshurica	Species	Juglandaceae	Eukaryota	roots	n.a.	n.a.	PMID[12444709]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	leaf	n.a.	PMID[14727919]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	root	n.a.	PMID[14727919]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	xylem	n.a.	PMID[14727919]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	bark	n.a.	PMID[14727919]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	pericarp	n.a.	PMID[18496782]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25466114]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[28737396]
NPO26892	Juglans mandshurica	Species	Juglandaceae	Eukaryota	Roots	n.a.	n.a.	PMID[9599266]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	leaf	n.a.	Database[Article]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Embryo	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Stem Bark	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Testa	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26892.1	Juglans mandshurica var. sieboldiana	Varieties	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26892.1	Juglans mandshurica var. sieboldiana	Varieties	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20411	Engelhardia roxburghiana	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26892	Juglans mandshurica	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26892.1	Juglans mandshurica var. sieboldiana	Varieties	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20411	Engelhardia roxburghiana	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26892	Juglans mandshurica	Species	Juglandaceae	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
Others	12

Activity Type	# Activity
Organism	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2231	Organism	Cornus florida	Cornus florida	Activity	=	12.0	mm2	PMID[525056]
NPT2231	Organism	Cornus florida	Cornus florida	Activity	=	5.0	mm2	PMID[525056]
NPT2231	Organism	Cornus florida	Cornus florida	Activity	=	13.0	mm2	PMID[525056]
NPT2232	Organism	Senna obtusifolia	Senna obtusifolia	Activity	=	2.0	mm2	PMID[525056]
NPT2233	Organism	Sida spinosa	Sida spinosa	Activity	=	18.0	mm2	PMID[525056]
NPT2234	Organism	Convolvulaceae	Convolvulaceae	Activity	=	4.0	mm2	PMID[525056]
NPT2235	Organism	Datura stramonium	Datura stramonium	Activity	=	6.0	mm2	PMID[525056]
NPT2236	Organism	Sorghum halepense	Sorghum halepense	Activity	=	13.0	mm2	PMID[525056]
NPT2237	Organism	Sorghum	Sorghum	Activity	=	7.0	mm2	PMID[525056]
NPT125	Organism	Chenopodium album	Chenopodium album	Activity	=	5.0	mm2	PMID[525056]
NPT2238	Organism	Nasturtium officinale	Nasturtium officinale	Activity	=	14.0	mm2	PMID[525056]
NPT2239	Organism	Ambrosia artemisiifolia	Ambrosia artemisiifolia	Activity	=	12.0	mm2	PMID[525056]

☑ 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 NPC216297 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	287
0.1-0.2	1404
0.2-0.3	3574
0.3-0.4	10334
0.4-0.5	9116
0.5-0.6	6003
0.6-0.7	9179
0.7-0.8	2496
0.8-0.85	209
0.85-0.9	76
0.9-0.95	14
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC7151
1.0	High Similarity	NPC473662
0.9573	High Similarity	NPC74507
0.9573	High Similarity	NPC234890
0.9407	High Similarity	NPC68756
0.9407	High Similarity	NPC152525
0.9256	High Similarity	NPC247250
0.9256	High Similarity	NPC767
0.9174	High Similarity	NPC470841
0.913	High Similarity	NPC108288
0.8983	High Similarity	NPC285829
0.8983	High Similarity	NPC206778
0.8974	High Similarity	NPC41567
0.8966	High Similarity	NPC477453
0.896	High Similarity	NPC17843
0.8952	High Similarity	NPC136588
0.8952	High Similarity	NPC147757
0.8952	High Similarity	NPC199253
0.8917	High Similarity	NPC300274
0.8917	High Similarity	NPC217756
0.8898	High Similarity	NPC232178
0.8879	High Similarity	NPC240163
0.8843	High Similarity	NPC375356
0.881	High Similarity	NPC242358
0.881	High Similarity	NPC478190
0.881	High Similarity	NPC246693
0.881	High Similarity	NPC70622
0.881	High Similarity	NPC110609
0.878	High Similarity	NPC51037
0.878	High Similarity	NPC96915
0.877	High Similarity	NPC310540
0.876	High Similarity	NPC307174
0.874	High Similarity	NPC314048
0.874	High Similarity	NPC52407
0.8729	High Similarity	NPC125252
0.8729	High Similarity	NPC269414
0.8718	High Similarity	NPC161304
0.8699	High Similarity	NPC103540
0.8699	High Similarity	NPC240744
0.8699	High Similarity	NPC167055
0.8678	High Similarity	NPC198336
0.8673	High Similarity	NPC211439
0.8661	High Similarity	NPC477406
0.8651	High Similarity	NPC31799
0.864	High Similarity	NPC237225
0.8632	High Similarity	NPC163154
0.8629	High Similarity	NPC136342
0.8629	High Similarity	NPC3224
0.8629	High Similarity	NPC227741
0.8629	High Similarity	NPC295202
0.8629	High Similarity	NPC49647
0.8629	High Similarity	NPC306765
0.8618	High Similarity	NPC173978
0.8618	High Similarity	NPC142956
0.8615	High Similarity	NPC305060
0.8607	High Similarity	NPC244351
0.8607	High Similarity	NPC283514
0.8596	High Similarity	NPC224584
0.8583	High Similarity	NPC184579
0.8583	High Similarity	NPC233165
0.856	High Similarity	NPC471530
0.8548	High Similarity	NPC131799
0.8509	High Similarity	NPC141523
0.8509	High Similarity	NPC34715
0.8504	High Similarity	NPC475741
0.8492	Intermediate Similarity	NPC165257
0.8492	Intermediate Similarity	NPC48248
0.8492	Intermediate Similarity	NPC282923
0.848	Intermediate Similarity	NPC1991
0.848	Intermediate Similarity	NPC231774
0.848	Intermediate Similarity	NPC160499
0.8443	Intermediate Similarity	NPC159760
0.8443	Intermediate Similarity	NPC179092
0.8443	Intermediate Similarity	NPC301987
0.8443	Intermediate Similarity	NPC292665
0.8443	Intermediate Similarity	NPC35856
0.8443	Intermediate Similarity	NPC115188
0.8443	Intermediate Similarity	NPC178395
0.8443	Intermediate Similarity	NPC244994
0.8443	Intermediate Similarity	NPC222876
0.8443	Intermediate Similarity	NPC26433
0.8443	Intermediate Similarity	NPC272454
0.8438	Intermediate Similarity	NPC205992
0.8438	Intermediate Similarity	NPC7012
0.8438	Intermediate Similarity	NPC85342
0.8425	Intermediate Similarity	NPC99731
0.8425	Intermediate Similarity	NPC474546
0.8425	Intermediate Similarity	NPC146647
0.8425	Intermediate Similarity	NPC34414
0.8409	Intermediate Similarity	NPC173980
0.8376	Intermediate Similarity	NPC114682
0.8359	Intermediate Similarity	NPC31539
0.8359	Intermediate Similarity	NPC198305
0.8359	Intermediate Similarity	NPC55949
0.8348	Intermediate Similarity	NPC303264
0.8347	Intermediate Similarity	NPC249435
0.8347	Intermediate Similarity	NPC184527
0.8346	Intermediate Similarity	NPC95537
0.8346	Intermediate Similarity	NPC114620
0.8346	Intermediate Similarity	NPC103337
0.8333	Intermediate Similarity	NPC472047
0.832	Intermediate Similarity	NPC265910
0.832	Intermediate Similarity	NPC91475
0.832	Intermediate Similarity	NPC236189
0.8306	Intermediate Similarity	NPC46634
0.8305	Intermediate Similarity	NPC231717
0.8296	Intermediate Similarity	NPC137649
0.8295	Intermediate Similarity	NPC244699
0.8295	Intermediate Similarity	NPC470831
0.8295	Intermediate Similarity	NPC214702
0.8295	Intermediate Similarity	NPC93015
0.8293	Intermediate Similarity	NPC190971
0.8281	Intermediate Similarity	NPC92624
0.8281	Intermediate Similarity	NPC278928
0.8279	Intermediate Similarity	NPC182240
0.8279	Intermediate Similarity	NPC473767
0.8271	Intermediate Similarity	NPC126739
0.8271	Intermediate Similarity	NPC197666
0.8268	Intermediate Similarity	NPC473787
0.8264	Intermediate Similarity	NPC28169
0.8258	Intermediate Similarity	NPC315275
0.8254	Intermediate Similarity	NPC472592
0.8254	Intermediate Similarity	NPC287473
0.8244	Intermediate Similarity	NPC474097
0.8244	Intermediate Similarity	NPC288089
0.824	Intermediate Similarity	NPC477153
0.824	Intermediate Similarity	NPC275145
0.8226	Intermediate Similarity	NPC120545
0.8217	Intermediate Similarity	NPC117609
0.8217	Intermediate Similarity	NPC259942
0.8209	Intermediate Similarity	NPC29771
0.8209	Intermediate Similarity	NPC190457
0.8209	Intermediate Similarity	NPC111422
0.8209	Intermediate Similarity	NPC299405
0.8209	Intermediate Similarity	NPC477408
0.8209	Intermediate Similarity	NPC476477
0.8209	Intermediate Similarity	NPC256463
0.8209	Intermediate Similarity	NPC216312
0.8209	Intermediate Similarity	NPC471602
0.8209	Intermediate Similarity	NPC306835
0.8189	Intermediate Similarity	NPC71610
0.8189	Intermediate Similarity	NPC8745
0.8182	Intermediate Similarity	NPC281513
0.8182	Intermediate Similarity	NPC312800
0.8182	Intermediate Similarity	NPC142027
0.8182	Intermediate Similarity	NPC22222
0.8182	Intermediate Similarity	NPC161632
0.8182	Intermediate Similarity	NPC27407
0.8175	Intermediate Similarity	NPC117794
0.8175	Intermediate Similarity	NPC4012
0.8175	Intermediate Similarity	NPC13238
0.8174	Intermediate Similarity	NPC163734
0.8168	Intermediate Similarity	NPC43627
0.8168	Intermediate Similarity	NPC53896
0.8168	Intermediate Similarity	NPC115458
0.8168	Intermediate Similarity	NPC225051
0.8168	Intermediate Similarity	NPC294226
0.8168	Intermediate Similarity	NPC171968
0.8167	Intermediate Similarity	NPC285350
0.8167	Intermediate Similarity	NPC118288
0.8167	Intermediate Similarity	NPC276111
0.8162	Intermediate Similarity	NPC474961
0.8162	Intermediate Similarity	NPC474300
0.8162	Intermediate Similarity	NPC85310
0.8162	Intermediate Similarity	NPC469520
0.816	Intermediate Similarity	NPC91478
0.8154	Intermediate Similarity	NPC41847
0.8154	Intermediate Similarity	NPC205360
0.8154	Intermediate Similarity	NPC72669
0.8154	Intermediate Similarity	NPC474517
0.8154	Intermediate Similarity	NPC471851
0.8148	Intermediate Similarity	NPC241349
0.8148	Intermediate Similarity	NPC220496
0.8148	Intermediate Similarity	NPC32749
0.8148	Intermediate Similarity	NPC183345
0.8148	Intermediate Similarity	NPC147542
0.8148	Intermediate Similarity	NPC42262
0.8148	Intermediate Similarity	NPC37992
0.8148	Intermediate Similarity	NPC327916
0.8145	Intermediate Similarity	NPC472046
0.814	Intermediate Similarity	NPC120488
0.814	Intermediate Similarity	NPC102829
0.8136	Intermediate Similarity	NPC252544
0.8136	Intermediate Similarity	NPC321252
0.8134	Intermediate Similarity	NPC206207
0.8134	Intermediate Similarity	NPC61590
0.813	Intermediate Similarity	NPC195262
0.813	Intermediate Similarity	NPC188814
0.8125	Intermediate Similarity	NPC181715
0.812	Intermediate Similarity	NPC155211
0.812	Intermediate Similarity	NPC474813
0.812	Intermediate Similarity	NPC272268
0.812	Intermediate Similarity	NPC141934
0.8115	Intermediate Similarity	NPC160199
0.811	Intermediate Similarity	NPC10926
0.811	Intermediate Similarity	NPC477454
0.8106	Intermediate Similarity	NPC282780
0.8106	Intermediate Similarity	NPC50924
0.8106	Intermediate Similarity	NPC166480
0.8106	Intermediate Similarity	NPC44437

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 NPC216297 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	279
0.1-0.2	930
0.2-0.3	1431
0.3-0.4	2698
0.4-0.5	2099
0.5-0.6	1173
0.6-0.7	482
0.7-0.8	55
0.8-0.85	0
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.913	High Similarity	NPD405	Clinical (unspecified phase)
0.8833	High Similarity	NPD1201	Approved
0.8699	High Similarity	NPD1470	Approved
0.7966	Intermediate Similarity	NPD74	Approved
0.7966	Intermediate Similarity	NPD9266	Approved
0.7886	Intermediate Similarity	NPD9493	Approved
0.7881	Intermediate Similarity	NPD9264	Approved
0.7881	Intermediate Similarity	NPD9263	Approved
0.7881	Intermediate Similarity	NPD9267	Approved
0.7852	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD1164	Approved
0.782	Intermediate Similarity	NPD943	Approved
0.7778	Intermediate Similarity	NPD1237	Approved
0.7656	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD2346	Discontinued
0.7589	Intermediate Similarity	NPD3300	Phase 2
0.7542	Intermediate Similarity	NPD9261	Approved
0.7536	Intermediate Similarity	NPD5408	Approved
0.7536	Intermediate Similarity	NPD5404	Approved
0.7536	Intermediate Similarity	NPD2935	Discontinued
0.7536	Intermediate Similarity	NPD5405	Approved
0.7536	Intermediate Similarity	NPD5406	Approved
0.75	Intermediate Similarity	NPD2798	Approved
0.75	Intermediate Similarity	NPD2932	Approved
0.75	Intermediate Similarity	NPD3019	Approved
0.7483	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD1510	Phase 2
0.744	Intermediate Similarity	NPD9281	Approved
0.7429	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD1240	Approved
0.7424	Intermediate Similarity	NPD1203	Approved
0.7413	Intermediate Similarity	NPD7390	Discontinued
0.7407	Intermediate Similarity	NPD2313	Discontinued
0.7373	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD2344	Approved
0.7324	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD1607	Approved
0.7305	Intermediate Similarity	NPD1549	Phase 2
0.7295	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD3226	Approved
0.7279	Intermediate Similarity	NPD3764	Approved
0.7265	Intermediate Similarity	NPD288	Approved
0.7246	Intermediate Similarity	NPD447	Suspended
0.7226	Intermediate Similarity	NPD520	Approved
0.7214	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD2799	Discontinued
0.7209	Intermediate Similarity	NPD9545	Approved
0.7197	Intermediate Similarity	NPD9717	Approved
0.7179	Intermediate Similarity	NPD844	Approved
0.7172	Intermediate Similarity	NPD1511	Approved
0.7163	Intermediate Similarity	NPD1551	Phase 2
0.7154	Intermediate Similarity	NPD2342	Discontinued
0.7153	Intermediate Similarity	NPD2309	Approved
0.7143	Intermediate Similarity	NPD7635	Approved
0.7133	Intermediate Similarity	NPD1934	Approved
0.7133	Intermediate Similarity	NPD6844	Discontinued
0.7122	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD4380	Phase 2
0.7101	Intermediate Similarity	NPD6663	Approved
0.709	Intermediate Similarity	NPD1283	Approved
0.709	Intermediate Similarity	NPD1876	Approved
0.7086	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD3091	Approved
0.7075	Intermediate Similarity	NPD1512	Approved
0.7059	Intermediate Similarity	NPD9495	Approved
0.7059	Intermediate Similarity	NPD9494	Approved
0.7059	Intermediate Similarity	NPD5736	Approved
0.7047	Intermediate Similarity	NPD2649	Approved
0.7047	Intermediate Similarity	NPD2651	Approved
0.7047	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5402	Approved
0.7029	Intermediate Similarity	NPD411	Approved
0.7023	Intermediate Similarity	NPD1651	Approved
0.7015	Intermediate Similarity	NPD1755	Approved
0.7007	Intermediate Similarity	NPD2532	Approved
0.7007	Intermediate Similarity	NPD2533	Approved
0.7007	Intermediate Similarity	NPD2534	Approved
0.7007	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD6832	Phase 2
0.7	Intermediate Similarity	NPD3020	Approved
0.6993	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD2801	Approved
0.6974	Remote Similarity	NPD7819	Suspended
0.6966	Remote Similarity	NPD3750	Approved
0.6953	Remote Similarity	NPD1241	Discontinued
0.6949	Remote Similarity	NPD2934	Approved
0.6949	Remote Similarity	NPD2933	Approved
0.694	Remote Similarity	NPD9269	Phase 2
0.6923	Remote Similarity	NPD6959	Discontinued
0.6923	Remote Similarity	NPD2796	Approved
0.6917	Remote Similarity	NPD3026	Approved
0.6917	Remote Similarity	NPD3023	Approved
0.6914	Remote Similarity	NPD5028	Approved
0.6914	Remote Similarity	NPD4954	Approved
0.6914	Remote Similarity	NPD5034	Approved
0.6914	Remote Similarity	NPD5026	Approved
0.6914	Remote Similarity	NPD4955	Approved
0.6914	Remote Similarity	NPD36	Approved
0.6911	Remote Similarity	NPD164	Approved
0.6899	Remote Similarity	NPD5951	Approved
0.6897	Remote Similarity	NPD9258	Approved
0.6897	Remote Similarity	NPD9256	Approved
0.6894	Remote Similarity	NPD9268	Approved
0.6894	Remote Similarity	NPD3024	Approved
0.6894	Remote Similarity	NPD3025	Approved
0.6891	Remote Similarity	NPD2859	Approved
0.6891	Remote Similarity	NPD2860	Approved
0.6883	Remote Similarity	NPD3882	Suspended
0.6879	Remote Similarity	NPD230	Phase 1
0.6879	Remote Similarity	NPD6232	Discontinued
0.6875	Remote Similarity	NPD1471	Phase 3
0.6871	Remote Similarity	NPD8313	Approved
0.6871	Remote Similarity	NPD8312	Approved
0.6866	Remote Similarity	NPD3092	Approved
0.6866	Remote Similarity	NPD1281	Approved
0.6864	Remote Similarity	NPD845	Approved
0.6861	Remote Similarity	NPD1019	Discontinued
0.6855	Remote Similarity	NPD7473	Discontinued
0.6852	Remote Similarity	NPD5030	Phase 2
0.685	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.685	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD7003	Approved
0.6849	Remote Similarity	NPD3400	Discontinued
0.6846	Remote Similarity	NPD6273	Approved
0.6842	Remote Similarity	NPD4626	Approved
0.6839	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD1929	Approved
0.6829	Remote Similarity	NPD1930	Approved
0.6825	Remote Similarity	NPD2182	Approved
0.6818	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD4878	Approved
0.6815	Remote Similarity	NPD1608	Approved
0.6815	Remote Similarity	NPD3972	Approved
0.6813	Remote Similarity	NPD3818	Discontinued
0.6807	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD1242	Phase 1
0.68	Remote Similarity	NPD5403	Approved
0.6797	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD6166	Phase 2
0.6792	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD2797	Approved
0.6788	Remote Similarity	NPD3094	Phase 2
0.6779	Remote Similarity	NPD5401	Approved
0.6779	Remote Similarity	NPD4661	Approved
0.6779	Remote Similarity	NPD4662	Approved
0.6772	Remote Similarity	NPD3021	Approved
0.6772	Remote Similarity	NPD3022	Approved
0.6772	Remote Similarity	NPD1792	Phase 2
0.6772	Remote Similarity	NPD4750	Phase 3
0.6769	Remote Similarity	NPD9618	Approved
0.6769	Remote Similarity	NPD2629	Approved
0.6769	Remote Similarity	NPD9614	Approved
0.6748	Remote Similarity	NPD1932	Approved
0.6747	Remote Similarity	NPD5037	Approved
0.6747	Remote Similarity	NPD8150	Discontinued
0.6747	Remote Similarity	NPD5038	Approved
0.6739	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD8166	Discontinued
0.6735	Remote Similarity	NPD4628	Phase 3
0.6731	Remote Similarity	NPD3749	Approved
0.6723	Remote Similarity	NPD1202	Approved
0.6721	Remote Similarity	NPD1238	Approved
0.6716	Remote Similarity	NPD3095	Discontinued
0.6716	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD1759	Phase 1
0.6691	Remote Similarity	NPD1481	Phase 2
0.669	Remote Similarity	NPD9570	Approved
0.6689	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD6190	Approved
0.6687	Remote Similarity	NPD5036	Approved
0.6667	Remote Similarity	NPD7054	Approved
0.6667	Remote Similarity	NPD3496	Discontinued
0.6667	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD968	Approved
0.6667	Remote Similarity	NPD3268	Approved
0.6667	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2800	Approved
0.6642	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD5157	Phase 1
0.6642	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD5691	Approved
0.6642	Remote Similarity	NPD5159	Phase 2
0.6641	Remote Similarity	NPD497	Approved
0.6626	Remote Similarity	NPD7074	Phase 3
0.6626	Remote Similarity	NPD7472	Approved
0.6624	Remote Similarity	NPD7075	Discontinued
0.6622	Remote Similarity	NPD1196	Approved
0.6621	Remote Similarity	NPD3748	Approved
0.6621	Remote Similarity	NPD4308	Phase 3
0.6619	Remote Similarity	NPD5647	Approved
0.6618	Remote Similarity	NPD5350	Clinical (unspecified phase)

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