NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	206.09
Volume:	214.82
LogP:	2.274
LogD:	2.36
LogS:	-3.683
# Rotatable Bonds:	2
TPSA:	35.53
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.744
Synthetic Accessibility Score:	1.882
Fsp3:	0.417
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.609
MDCK Permeability:	2.730091910052579e-05
Pgp-inhibitor:	0.013
Pgp-substrate:	0.014
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.992
Plasma Protein Binding (PPB):	67.17548370361328%
Volume Distribution (VD):	0.715
Pgp-substrate:	18.441802978515625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.956
CYP1A2-substrate:	0.941
CYP2C19-inhibitor:	0.654
CYP2C19-substrate:	0.836
CYP2C9-inhibitor:	0.17
CYP2C9-substrate:	0.84
CYP2D6-inhibitor:	0.163
CYP2D6-substrate:	0.898
CYP3A4-inhibitor:	0.067
CYP3A4-substrate:	0.308

ADMET: Excretion

Clearance (CL):	9.066
Half-life (T1/2):	0.765

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.203
Drug-inuced Liver Injury (DILI):	0.624
AMES Toxicity:	0.132
Rat Oral Acute Toxicity:	0.081
Maximum Recommended Daily Dose:	0.359
Skin Sensitization:	0.397
Carcinogencity:	0.195
Eye Corrosion:	0.026
Eye Irritation:	0.543
Respiratory Toxicity:	0.678

Download Data

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

Natural Product: NPC30216

Natural Product ID:	NPC30216
*Common Name:**	6,7-Dimethoxy-3,4-Dihydro-2H-Naphthalen-1-One
IUPAC Name:	6,7-dimethoxy-3,4-dihydro-2H-naphthalen-1-one
Synonyms:
Standard InCHIKey:	YNNJHKOXXBIJKK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H14O3/c1-14-11-6-8-4-3-5-10(13)9(8)7-12(11)15-2/h6-7H,3-5H2,1-2H3
SMILES:	COc1cc2CCCC(=O)c2cc1OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1889024
PubChem CID:	266816
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
NPO10597	Fructus syzygii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO10597	Fructus syzygii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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
Potency	8

Activity Type	# Activity
Individual Protein	7
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	100000.0	nM	PMID[505372]
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	17782.8	nM	PMID[505372]
NPT1474	Individual Protein	ATP-dependent Clp protease proteolytic subunit	Bacillus subtilis (strain 168)	Potency	n.a.	28183.8	nM	PMID[505372]
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	14125.4	nM	PMID[505372]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	16360.1	nM	PMID[505372]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	14581.0	nM	PMID[505372]
NPT7	Individual Protein	Thioredoxin reductase 1, cytoplasmic	Rattus norvegicus	Potency	n.a.	70794.6	nM	PMID[505372]
NPT2	Others	Unspecified		Potency	n.a.	125.9	nM	PMID[505372]

☑ 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 NPC30216 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	394
0.1-0.2	1818
0.2-0.3	5089
0.3-0.4	12017
0.4-0.5	5364
0.5-0.6	4654
0.6-0.7	9625
0.7-0.8	3505
0.8-0.85	177
0.85-0.9	42
0.9-0.95	8
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9492	High Similarity	NPC225245
0.9256	High Similarity	NPC474691
0.9141	High Similarity	NPC88065
0.9141	High Similarity	NPC89504
0.9141	High Similarity	NPC95485
0.9008	High Similarity	NPC295317
0.896	High Similarity	NPC286683
0.896	High Similarity	NPC32163
0.896	High Similarity	NPC16651
0.8931	High Similarity	NPC470962
0.888	High Similarity	NPC177925
0.8864	High Similarity	NPC223336
0.876	High Similarity	NPC153453
0.875	High Similarity	NPC66905
0.873	High Similarity	NPC154275
0.873	High Similarity	NPC474737
0.8667	High Similarity	NPC137920
0.8667	High Similarity	NPC192597
0.8667	High Similarity	NPC86455
0.8667	High Similarity	NPC229218
0.8667	High Similarity	NPC125134
0.8667	High Similarity	NPC141817
0.8667	High Similarity	NPC176030
0.8667	High Similarity	NPC169214
0.8651	High Similarity	NPC473626
0.8644	High Similarity	NPC23332
0.8615	High Similarity	NPC50763
0.8593	High Similarity	NPC84273
0.8559	High Similarity	NPC183648
0.8525	High Similarity	NPC469954
0.8516	High Similarity	NPC203719
0.8516	High Similarity	NPC117237
0.8507	High Similarity	NPC46947
0.8478	Intermediate Similarity	NPC160777
0.8478	Intermediate Similarity	NPC73416
0.8462	Intermediate Similarity	NPC285776
0.8462	Intermediate Similarity	NPC299010
0.845	Intermediate Similarity	NPC304747
0.8438	Intermediate Similarity	NPC179777
0.8421	Intermediate Similarity	NPC208760
0.8421	Intermediate Similarity	NPC139519
0.8413	Intermediate Similarity	NPC114298
0.8406	Intermediate Similarity	NPC308006
0.8406	Intermediate Similarity	NPC309169
0.8406	Intermediate Similarity	NPC196941
0.8406	Intermediate Similarity	NPC229787
0.8406	Intermediate Similarity	NPC472836
0.8397	Intermediate Similarity	NPC239134
0.8397	Intermediate Similarity	NPC164295
0.8382	Intermediate Similarity	NPC28398
0.8374	Intermediate Similarity	NPC185738
0.8372	Intermediate Similarity	NPC5018
0.8372	Intermediate Similarity	NPC123228
0.8372	Intermediate Similarity	NPC276466
0.8372	Intermediate Similarity	NPC123722
0.8372	Intermediate Similarity	NPC151167
0.837	Intermediate Similarity	NPC44573
0.8359	Intermediate Similarity	NPC120066
0.8346	Intermediate Similarity	NPC242372
0.8346	Intermediate Similarity	NPC311339
0.8346	Intermediate Similarity	NPC182646
0.8346	Intermediate Similarity	NPC4181
0.8346	Intermediate Similarity	NPC164778
0.8346	Intermediate Similarity	NPC144662
0.8346	Intermediate Similarity	NPC257976
0.8333	Intermediate Similarity	NPC239608
0.8333	Intermediate Similarity	NPC50954
0.8333	Intermediate Similarity	NPC46880
0.8333	Intermediate Similarity	NPC111888
0.8333	Intermediate Similarity	NPC183103
0.8333	Intermediate Similarity	NPC46161
0.8321	Intermediate Similarity	NPC298268
0.8295	Intermediate Similarity	NPC90128
0.8295	Intermediate Similarity	NPC84076
0.8295	Intermediate Similarity	NPC303680
0.8293	Intermediate Similarity	NPC268317
0.8284	Intermediate Similarity	NPC143649
0.8281	Intermediate Similarity	NPC273686
0.8281	Intermediate Similarity	NPC312404
0.8271	Intermediate Similarity	NPC283823
0.8271	Intermediate Similarity	NPC288743
0.8271	Intermediate Similarity	NPC159418
0.8261	Intermediate Similarity	NPC28326
0.8261	Intermediate Similarity	NPC11314
0.8261	Intermediate Similarity	NPC312256
0.8258	Intermediate Similarity	NPC279596
0.8244	Intermediate Similarity	NPC304622
0.824	Intermediate Similarity	NPC299406
0.8235	Intermediate Similarity	NPC325625
0.8227	Intermediate Similarity	NPC52692
0.8227	Intermediate Similarity	NPC474999
0.8222	Intermediate Similarity	NPC77955
0.8222	Intermediate Similarity	NPC471182
0.8214	Intermediate Similarity	NPC30890
0.8214	Intermediate Similarity	NPC225351
0.8209	Intermediate Similarity	NPC155098
0.8188	Intermediate Similarity	NPC58229
0.8188	Intermediate Similarity	NPC110419
0.8182	Intermediate Similarity	NPC57879
0.8182	Intermediate Similarity	NPC54626
0.8175	Intermediate Similarity	NPC4796
0.8169	Intermediate Similarity	NPC476058
0.8169	Intermediate Similarity	NPC472839
0.816	Intermediate Similarity	NPC166591
0.816	Intermediate Similarity	NPC205502
0.8143	Intermediate Similarity	NPC207732
0.8143	Intermediate Similarity	NPC142165
0.8143	Intermediate Similarity	NPC275278
0.8134	Intermediate Similarity	NPC327410
0.8129	Intermediate Similarity	NPC185607
0.8125	Intermediate Similarity	NPC473201
0.8125	Intermediate Similarity	NPC272566
0.8125	Intermediate Similarity	NPC474414
0.8125	Intermediate Similarity	NPC144283
0.8125	Intermediate Similarity	NPC118427
0.8125	Intermediate Similarity	NPC78505
0.8125	Intermediate Similarity	NPC302783
0.8125	Intermediate Similarity	NPC220577
0.8116	Intermediate Similarity	NPC326065
0.8116	Intermediate Similarity	NPC908
0.8116	Intermediate Similarity	NPC138438
0.8112	Intermediate Similarity	NPC237441
0.8112	Intermediate Similarity	NPC300983
0.8112	Intermediate Similarity	NPC37220
0.811	Intermediate Similarity	NPC471877
0.8106	Intermediate Similarity	NPC150809
0.8102	Intermediate Similarity	NPC233780
0.8102	Intermediate Similarity	NPC284409
0.8099	Intermediate Similarity	NPC179309
0.8099	Intermediate Similarity	NPC58373
0.8092	Intermediate Similarity	NPC428300
0.8092	Intermediate Similarity	NPC223807
0.8092	Intermediate Similarity	NPC45537
0.8092	Intermediate Similarity	NPC470841
0.8088	Intermediate Similarity	NPC324929
0.8088	Intermediate Similarity	NPC471670
0.8088	Intermediate Similarity	NPC160425
0.8085	Intermediate Similarity	NPC213482
0.8085	Intermediate Similarity	NPC224687
0.8085	Intermediate Similarity	NPC136278
0.8085	Intermediate Similarity	NPC474446
0.808	Intermediate Similarity	NPC150919
0.808	Intermediate Similarity	NPC280001
0.8077	Intermediate Similarity	NPC53305
0.8077	Intermediate Similarity	NPC257589
0.8074	Intermediate Similarity	NPC237330
0.8071	Intermediate Similarity	NPC119663
0.8071	Intermediate Similarity	NPC476054
0.8071	Intermediate Similarity	NPC254659
0.8071	Intermediate Similarity	NPC473090
0.8069	Intermediate Similarity	NPC312338
0.8069	Intermediate Similarity	NPC164912
0.8069	Intermediate Similarity	NPC149889
0.8065	Intermediate Similarity	NPC220540
0.806	Intermediate Similarity	NPC239302
0.8056	Intermediate Similarity	NPC58310
0.8056	Intermediate Similarity	NPC58661
0.8056	Intermediate Similarity	NPC295977
0.8051	Intermediate Similarity	NPC292792
0.8051	Intermediate Similarity	NPC38209
0.8047	Intermediate Similarity	NPC201777
0.8045	Intermediate Similarity	NPC172673
0.8042	Intermediate Similarity	NPC475848
0.8042	Intermediate Similarity	NPC474306
0.8042	Intermediate Similarity	NPC474903
0.8029	Intermediate Similarity	NPC474274
0.8029	Intermediate Similarity	NPC186647
0.8029	Intermediate Similarity	NPC110899
0.8029	Intermediate Similarity	NPC95679
0.8029	Intermediate Similarity	NPC125417
0.8029	Intermediate Similarity	NPC112068
0.8029	Intermediate Similarity	NPC25305
0.8029	Intermediate Similarity	NPC157944
0.8028	Intermediate Similarity	NPC24257
0.8028	Intermediate Similarity	NPC195919
0.8028	Intermediate Similarity	NPC231013
0.8028	Intermediate Similarity	NPC216314
0.8028	Intermediate Similarity	NPC153620
0.8028	Intermediate Similarity	NPC165389
0.8028	Intermediate Similarity	NPC120924
0.8016	Intermediate Similarity	NPC171023
0.8015	Intermediate Similarity	NPC474264
0.8015	Intermediate Similarity	NPC92207
0.8015	Intermediate Similarity	NPC204592
0.8015	Intermediate Similarity	NPC38101
0.8015	Intermediate Similarity	NPC127937
0.8015	Intermediate Similarity	NPC22644
0.8015	Intermediate Similarity	NPC274613
0.8015	Intermediate Similarity	NPC276014
0.8014	Intermediate Similarity	NPC327052
0.8014	Intermediate Similarity	NPC113089
0.8014	Intermediate Similarity	NPC91694
0.8014	Intermediate Similarity	NPC300603
0.8014	Intermediate Similarity	NPC27106
0.8014	Intermediate Similarity	NPC293201
0.8014	Intermediate Similarity	NPC182842
0.8	Intermediate Similarity	NPC118332
0.8	Intermediate Similarity	NPC470406
0.8	Intermediate Similarity	NPC316062
0.8	Intermediate Similarity	NPC472838

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 NPC30216 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	382
0.1-0.2	1034
0.2-0.3	1552
0.3-0.4	2714
0.4-0.5	1798
0.5-0.6	1085
0.6-0.7	478
0.7-0.8	101
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8516	High Similarity	NPD9494	Approved
0.8374	Intermediate Similarity	NPD5536	Phase 2
0.8281	Intermediate Similarity	NPD1876	Approved
0.8268	Intermediate Similarity	NPD3972	Approved
0.8095	Intermediate Similarity	NPD1651	Approved
0.8049	Intermediate Similarity	NPD1241	Discontinued
0.7959	Intermediate Similarity	NPD5978	Approved
0.7959	Intermediate Similarity	NPD5977	Approved
0.7923	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD1281	Approved
0.7903	Intermediate Similarity	NPD5283	Phase 1
0.7847	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD1283	Approved
0.7635	Intermediate Similarity	NPD6386	Approved
0.7635	Intermediate Similarity	NPD6385	Approved
0.7615	Intermediate Similarity	NPD17	Approved
0.7609	Intermediate Similarity	NPD447	Suspended
0.76	Intermediate Similarity	NPD228	Approved
0.76	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD1471	Phase 3
0.755	Intermediate Similarity	NPD3882	Suspended
0.7536	Intermediate Similarity	NPD1240	Approved
0.7535	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD2801	Approved
0.7517	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD5494	Approved
0.75	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD230	Phase 1
0.7482	Intermediate Similarity	NPD1933	Approved
0.7481	Intermediate Similarity	NPD2798	Approved
0.7467	Intermediate Similarity	NPD1934	Approved
0.7465	Intermediate Similarity	NPD2344	Approved
0.7444	Intermediate Similarity	NPD1608	Approved
0.7431	Intermediate Similarity	NPD4628	Phase 3
0.7429	Intermediate Similarity	NPD1607	Approved
0.7419	Intermediate Similarity	NPD6232	Discontinued
0.7417	Intermediate Similarity	NPD1465	Phase 2
0.741	Intermediate Similarity	NPD3142	Approved
0.741	Intermediate Similarity	NPD3140	Approved
0.74	Intermediate Similarity	NPD6873	Phase 2
0.7397	Intermediate Similarity	NPD1511	Approved
0.7394	Intermediate Similarity	NPD2796	Approved
0.7389	Intermediate Similarity	NPD7473	Discontinued
0.7372	Intermediate Similarity	NPD3926	Phase 2
0.7368	Intermediate Similarity	NPD3705	Approved
0.7368	Intermediate Similarity	NPD3817	Phase 2
0.7343	Intermediate Similarity	NPD2353	Approved
0.7343	Intermediate Similarity	NPD2346	Discontinued
0.7343	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6876	Approved
0.7333	Intermediate Similarity	NPD6875	Approved
0.7328	Intermediate Similarity	NPD9545	Approved
0.7324	Intermediate Similarity	NPD1510	Phase 2
0.7324	Intermediate Similarity	NPD3748	Approved
0.7324	Intermediate Similarity	NPD2799	Discontinued
0.7308	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1512	Approved
0.7286	Intermediate Similarity	NPD943	Approved
0.7286	Intermediate Similarity	NPD2979	Phase 3
0.7285	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD7110	Phase 1
0.728	Intermediate Similarity	NPD1358	Approved
0.7273	Intermediate Similarity	NPD2438	Suspended
0.7273	Intermediate Similarity	NPD2935	Discontinued
0.7273	Intermediate Similarity	NPD5691	Approved
0.7267	Intermediate Similarity	NPD2649	Approved
0.7267	Intermediate Similarity	NPD824	Approved
0.7267	Intermediate Similarity	NPD2651	Approved
0.7261	Intermediate Similarity	NPD5242	Approved
0.726	Intermediate Similarity	NPD2309	Approved
0.726	Intermediate Similarity	NPD3887	Approved
0.7255	Intermediate Similarity	NPD5353	Approved
0.7244	Intermediate Similarity	NPD1247	Approved
0.7226	Intermediate Similarity	NPD919	Approved
0.7219	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7028	Phase 2
0.7218	Intermediate Similarity	NPD4626	Approved
0.7214	Intermediate Similarity	NPD8032	Phase 2
0.7208	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD7003	Approved
0.7192	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD4110	Phase 3
0.719	Intermediate Similarity	NPD7819	Suspended
0.719	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5844	Phase 1
0.7181	Intermediate Similarity	NPD6273	Approved
0.7177	Intermediate Similarity	NPD164	Approved
0.7162	Intermediate Similarity	NPD6799	Approved
0.7152	Intermediate Similarity	NPD7458	Discontinued
0.7143	Intermediate Similarity	NPD5111	Phase 2
0.7143	Intermediate Similarity	NPD5110	Phase 2
0.7143	Intermediate Similarity	NPD2354	Approved
0.7143	Intermediate Similarity	NPD9268	Approved
0.7143	Intermediate Similarity	NPD5109	Approved
0.7143	Intermediate Similarity	NPD3764	Approved
0.7133	Intermediate Similarity	NPD3639	Approved
0.7133	Intermediate Similarity	NPD3641	Approved
0.7133	Intermediate Similarity	NPD3640	Phase 3
0.7123	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD6832	Phase 2
0.7113	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD3750	Approved
0.7063	Intermediate Similarity	NPD3134	Approved
0.7059	Intermediate Similarity	NPD9269	Phase 2
0.7055	Intermediate Similarity	NPD1549	Phase 2
0.7042	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD3620	Phase 2
0.7039	Intermediate Similarity	NPD3226	Approved
0.7034	Intermediate Similarity	NPD2531	Phase 2
0.7029	Intermediate Similarity	NPD3266	Approved
0.7029	Intermediate Similarity	NPD3267	Approved
0.7029	Intermediate Similarity	NPD1470	Approved
0.7021	Intermediate Similarity	NPD2313	Discontinued
0.7019	Intermediate Similarity	NPD3818	Discontinued
0.7015	Intermediate Similarity	NPD5585	Approved
0.7013	Intermediate Similarity	NPD37	Approved
0.7007	Intermediate Similarity	NPD1243	Approved
0.7	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6166	Phase 2
0.7	Intermediate Similarity	NPD3146	Approved
0.7	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6599	Discontinued
0.6993	Remote Similarity	NPD3657	Discovery
0.6986	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD1201	Approved
0.6977	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD8166	Discontinued
0.6953	Remote Similarity	NPD2182	Approved
0.695	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.694	Remote Similarity	NPD1894	Discontinued
0.6934	Remote Similarity	NPD9717	Approved
0.6934	Remote Similarity	NPD2981	Phase 2
0.6923	Remote Similarity	NPD4307	Phase 2
0.6917	Remote Similarity	NPD9493	Approved
0.6906	Remote Similarity	NPD1203	Approved
0.6903	Remote Similarity	NPD6280	Approved
0.6903	Remote Similarity	NPD6279	Approved
0.6889	Remote Similarity	NPD3024	Approved
0.6889	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD1357	Approved
0.6889	Remote Similarity	NPD3025	Approved
0.6887	Remote Similarity	NPD2532	Approved
0.6887	Remote Similarity	NPD2534	Approved
0.6887	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD2533	Approved
0.6884	Remote Similarity	NPD2982	Phase 2
0.6884	Remote Similarity	NPD2983	Phase 2
0.6883	Remote Similarity	NPD4380	Phase 2
0.6879	Remote Similarity	NPD4967	Phase 2
0.6879	Remote Similarity	NPD4966	Approved
0.6879	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4965	Approved
0.6875	Remote Similarity	NPD6355	Discontinued
0.6875	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD7054	Approved
0.6864	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD1019	Discontinued
0.6855	Remote Similarity	NPD1238	Approved
0.6848	Remote Similarity	NPD7685	Pre-registration
0.6842	Remote Similarity	NPD709	Approved
0.6838	Remote Similarity	NPD3019	Approved
0.6838	Remote Similarity	NPD2932	Approved
0.6831	Remote Similarity	NPD7095	Approved
0.6831	Remote Similarity	NPD3027	Phase 3
0.6829	Remote Similarity	NPD7472	Approved
0.6829	Remote Similarity	NPD7074	Phase 3
0.6822	Remote Similarity	NPD2684	Approved
0.6821	Remote Similarity	NPD4357	Discontinued
0.6818	Remote Similarity	NPD3455	Phase 2
0.6813	Remote Similarity	NPD7199	Phase 2
0.6813	Remote Similarity	NPD8127	Discontinued
0.6813	Remote Similarity	NPD2821	Approved
0.6812	Remote Similarity	NPD1481	Phase 2
0.6809	Remote Similarity	NPD3018	Phase 2
0.6806	Remote Similarity	NPD4060	Phase 1
0.6803	Remote Similarity	NPD6099	Approved
0.6803	Remote Similarity	NPD4476	Approved
0.6803	Remote Similarity	NPD4477	Approved
0.6803	Remote Similarity	NPD6100	Approved
0.68	Remote Similarity	NPD6190	Approved
0.6797	Remote Similarity	NPD920	Approved
0.6797	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD6234	Discontinued
0.6788	Remote Similarity	NPD3023	Approved
0.6788	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD3847	Discontinued
0.6788	Remote Similarity	NPD3026	Approved
0.6786	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD2797	Approved
0.6783	Remote Similarity	NPD6798	Discontinued
0.6783	Remote Similarity	NPD3268	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