NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	188.08
Volume:	203.394
LogP:	3.371
LogD:	3.402
LogS:	-3.453
# Rotatable Bonds:	1
TPSA:	29.46
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.745
Synthetic Accessibility Score:	1.883
Fsp3:	0.167
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.564
MDCK Permeability:	2.0434195903362706e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.714
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.395
30% Bioavailability (F30%):	0.388

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.444
Plasma Protein Binding (PPB):	95.6363296508789%
Volume Distribution (VD):	0.684
Pgp-substrate:	3.3993687629699707%

ADMET: Metabolism

CYP1A2-inhibitor:	0.987
CYP1A2-substrate:	0.948
CYP2C19-inhibitor:	0.811
CYP2C19-substrate:	0.571
CYP2C9-inhibitor:	0.555
CYP2C9-substrate:	0.912
CYP2D6-inhibitor:	0.821
CYP2D6-substrate:	0.912
CYP3A4-inhibitor:	0.522
CYP3A4-substrate:	0.354

ADMET: Excretion

Clearance (CL):	11.945
Half-life (T1/2):	0.737

ADMET: Toxicity

hERG Blockers:	0.051
Human Hepatotoxicity (H-HT):	0.05
Drug-inuced Liver Injury (DILI):	0.289
AMES Toxicity:	0.68
Rat Oral Acute Toxicity:	0.112
Maximum Recommended Daily Dose:	0.452
Skin Sensitization:	0.93
Carcinogencity:	0.704
Eye Corrosion:	0.67
Eye Irritation:	0.99
Respiratory Toxicity:	0.789

Download Data

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

Natural Product: NPC63010

Natural Product ID:	NPC63010
*Common Name:**	8-Methoxy-3-Methylnaphthalen-1-Ol
IUPAC Name:	8-methoxy-3-methylnaphthalen-1-ol
Synonyms:
Standard InCHIKey:	IJJNDUUHBYEDNU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H12O2/c1-8-6-9-4-3-5-11(14-2)12(9)10(13)7-8/h3-7,13H,1-2H3
SMILES:	Cc1cc2cccc(c2c(c1)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2071228
PubChem CID:	11355930
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
NPO32707	burman diospyros burmanica	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[22858297]

☑ 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	2
Others	1

Activity Type	# Activity
Cell Line	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100000.0	nM	PMID[520171]
NPT841	Organism	Leishmania major	Leishmania major	IC50	=	50000.0	nM	PMID[520171]
NPT2	Others	Unspecified		Ratio IC50	>	2.0	n.a.	PMID[520171]

☑ 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 NPC63010 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	432
0.1-0.2	2111
0.2-0.3	5418
0.3-0.4	12955
0.4-0.5	4358
0.5-0.6	6056
0.6-0.7	8369
0.7-0.8	2662
0.8-0.85	249
0.85-0.9	74
0.9-0.95	10
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9735	High Similarity	NPC100108
0.9735	High Similarity	NPC277798
0.9167	High Similarity	NPC53781
0.916	High Similarity	NPC105031
0.9091	High Similarity	NPC215300
0.9091	High Similarity	NPC38017
0.9091	High Similarity	NPC23012
0.9076	High Similarity	NPC138248
0.9076	High Similarity	NPC228503
0.906	High Similarity	NPC129176
0.9043	High Similarity	NPC221549
0.9043	High Similarity	NPC244816
0.9043	High Similarity	NPC50521
0.9	High Similarity	NPC278955
0.9	High Similarity	NPC105718
0.8974	High Similarity	NPC103916
0.8966	High Similarity	NPC190514
0.8926	High Similarity	NPC170485
0.8889	High Similarity	NPC184302
0.887	High Similarity	NPC167934
0.887	High Similarity	NPC808
0.887	High Similarity	NPC283169
0.8862	High Similarity	NPC16577
0.886	High Similarity	NPC141003
0.886	High Similarity	NPC35344
0.8852	High Similarity	NPC473221
0.8793	High Similarity	NPC150624
0.8783	High Similarity	NPC249270
0.8783	High Similarity	NPC470837
0.877	High Similarity	NPC82299
0.876	High Similarity	NPC61685
0.8739	High Similarity	NPC102639
0.8727	High Similarity	NPC238696
0.872	High Similarity	NPC282508
0.8718	High Similarity	NPC33270
0.8718	High Similarity	NPC69261
0.8718	High Similarity	NPC195466
0.8689	High Similarity	NPC4286
0.8689	High Similarity	NPC76119
0.8689	High Similarity	NPC293801
0.8667	High Similarity	NPC476633
0.8661	High Similarity	NPC274876
0.8636	High Similarity	NPC168393
0.8621	High Similarity	NPC276737
0.8621	High Similarity	NPC22610
0.8595	High Similarity	NPC18128
0.8595	High Similarity	NPC77789
0.8594	High Similarity	NPC37410
0.8584	High Similarity	NPC75440
0.8571	High Similarity	NPC160623
0.8559	High Similarity	NPC25648
0.8547	High Similarity	NPC53906
0.8537	High Similarity	NPC113495
0.8527	High Similarity	NPC472648
0.8527	High Similarity	NPC472649
0.8527	High Similarity	NPC191462
0.8527	High Similarity	NPC115861
0.8527	High Similarity	NPC133463
0.8527	High Similarity	NPC472647
0.8527	High Similarity	NPC206525
0.8527	High Similarity	NPC170328
0.8525	High Similarity	NPC261992
0.8509	High Similarity	NPC58865
0.8492	Intermediate Similarity	NPC254000
0.8487	Intermediate Similarity	NPC131118
0.8475	Intermediate Similarity	NPC203113
0.8475	Intermediate Similarity	NPC141090
0.8462	Intermediate Similarity	NPC56329
0.8462	Intermediate Similarity	NPC151656
0.8462	Intermediate Similarity	NPC266453
0.8462	Intermediate Similarity	NPC230919
0.8462	Intermediate Similarity	NPC71465
0.8462	Intermediate Similarity	NPC266006
0.8462	Intermediate Similarity	NPC242715
0.8462	Intermediate Similarity	NPC472646
0.8462	Intermediate Similarity	NPC200935
0.845	Intermediate Similarity	NPC258780
0.8448	Intermediate Similarity	NPC46940
0.8448	Intermediate Similarity	NPC98372
0.8443	Intermediate Similarity	NPC152946
0.8443	Intermediate Similarity	NPC57199
0.8443	Intermediate Similarity	NPC188997
0.8435	Intermediate Similarity	NPC94045
0.8435	Intermediate Similarity	NPC303521
0.843	Intermediate Similarity	NPC212559
0.843	Intermediate Similarity	NPC45663
0.8425	Intermediate Similarity	NPC15543
0.8413	Intermediate Similarity	NPC222108
0.8413	Intermediate Similarity	NPC96719
0.8407	Intermediate Similarity	NPC67250
0.8403	Intermediate Similarity	NPC127894
0.8403	Intermediate Similarity	NPC15860
0.8403	Intermediate Similarity	NPC474933
0.8403	Intermediate Similarity	NPC219070
0.8403	Intermediate Similarity	NPC470759
0.84	Intermediate Similarity	NPC46978
0.8397	Intermediate Similarity	NPC105847
0.8397	Intermediate Similarity	NPC275061
0.8397	Intermediate Similarity	NPC220344
0.8397	Intermediate Similarity	NPC243996
0.8397	Intermediate Similarity	NPC243759
0.8397	Intermediate Similarity	NPC132804
0.8397	Intermediate Similarity	NPC218131
0.8393	Intermediate Similarity	NPC474603
0.8393	Intermediate Similarity	NPC12987
0.8393	Intermediate Similarity	NPC241224
0.839	Intermediate Similarity	NPC232165
0.8385	Intermediate Similarity	NPC30632
0.8372	Intermediate Similarity	NPC160697
0.8362	Intermediate Similarity	NPC275627
0.8362	Intermediate Similarity	NPC296920
0.8362	Intermediate Similarity	NPC151537
0.8362	Intermediate Similarity	NPC95716
0.8362	Intermediate Similarity	NPC470723
0.8362	Intermediate Similarity	NPC90520
0.8361	Intermediate Similarity	NPC48623
0.8361	Intermediate Similarity	NPC168707
0.8348	Intermediate Similarity	NPC314187
0.8346	Intermediate Similarity	NPC315769
0.8333	Intermediate Similarity	NPC233320
0.8333	Intermediate Similarity	NPC308768
0.8333	Intermediate Similarity	NPC12668
0.8333	Intermediate Similarity	NPC273623
0.8321	Intermediate Similarity	NPC22902
0.832	Intermediate Similarity	NPC223953
0.8319	Intermediate Similarity	NPC312105
0.8319	Intermediate Similarity	NPC229147
0.8319	Intermediate Similarity	NPC114064
0.8319	Intermediate Similarity	NPC117115
0.8319	Intermediate Similarity	NPC85292
0.8319	Intermediate Similarity	NPC54507
0.8308	Intermediate Similarity	NPC108198
0.8308	Intermediate Similarity	NPC69029
0.8308	Intermediate Similarity	NPC294884
0.8308	Intermediate Similarity	NPC200557
0.8308	Intermediate Similarity	NPC158142
0.8308	Intermediate Similarity	NPC10314
0.8308	Intermediate Similarity	NPC241241
0.8306	Intermediate Similarity	NPC111088
0.8305	Intermediate Similarity	NPC107240
0.8304	Intermediate Similarity	NPC12870
0.8304	Intermediate Similarity	NPC24327
0.8295	Intermediate Similarity	NPC469610
0.8293	Intermediate Similarity	NPC30462
0.8291	Intermediate Similarity	NPC228452
0.8291	Intermediate Similarity	NPC280606
0.8291	Intermediate Similarity	NPC302371
0.8281	Intermediate Similarity	NPC191395
0.8281	Intermediate Similarity	NPC8899
0.8279	Intermediate Similarity	NPC218753
0.8279	Intermediate Similarity	NPC131868
0.8276	Intermediate Similarity	NPC168657
0.8276	Intermediate Similarity	NPC224870
0.8276	Intermediate Similarity	NPC132720
0.8273	Intermediate Similarity	NPC156313
0.8268	Intermediate Similarity	NPC471518
0.8268	Intermediate Similarity	NPC471519
0.8264	Intermediate Similarity	NPC151197
0.8261	Intermediate Similarity	NPC241549
0.8261	Intermediate Similarity	NPC201959
0.8261	Intermediate Similarity	NPC174981
0.8254	Intermediate Similarity	NPC236760
0.8254	Intermediate Similarity	NPC266555
0.8246	Intermediate Similarity	NPC113457
0.8244	Intermediate Similarity	NPC202846
0.8244	Intermediate Similarity	NPC143139
0.8244	Intermediate Similarity	NPC205442
0.8235	Intermediate Similarity	NPC185541
0.8235	Intermediate Similarity	NPC84999
0.8235	Intermediate Similarity	NPC464
0.8235	Intermediate Similarity	NPC246760
0.8235	Intermediate Similarity	NPC301321
0.8231	Intermediate Similarity	NPC473107
0.8231	Intermediate Similarity	NPC125649
0.823	Intermediate Similarity	NPC272029
0.8226	Intermediate Similarity	NPC121115
0.8226	Intermediate Similarity	NPC84086
0.822	Intermediate Similarity	NPC117846
0.822	Intermediate Similarity	NPC715
0.8217	Intermediate Similarity	NPC218884
0.8217	Intermediate Similarity	NPC228843
0.8217	Intermediate Similarity	NPC469611
0.8214	Intermediate Similarity	NPC300166
0.8211	Intermediate Similarity	NPC251259
0.8209	Intermediate Similarity	NPC183709
0.8209	Intermediate Similarity	NPC175838
0.8205	Intermediate Similarity	NPC224527
0.8203	Intermediate Similarity	NPC126836
0.819	Intermediate Similarity	NPC202647
0.819	Intermediate Similarity	NPC33728
0.819	Intermediate Similarity	NPC19808
0.8189	Intermediate Similarity	NPC154866
0.8182	Intermediate Similarity	NPC329980
0.8182	Intermediate Similarity	NPC139047
0.8175	Intermediate Similarity	NPC470724
0.8174	Intermediate Similarity	NPC151477
0.8168	Intermediate Similarity	NPC313081
0.8167	Intermediate Similarity	NPC261973
0.816	Intermediate Similarity	NPC5796
0.816	Intermediate Similarity	NPC206487

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 NPC63010 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	400
0.1-0.2	1060
0.2-0.3	1347
0.3-0.4	2818
0.4-0.5	1713
0.5-0.6	1129
0.6-0.7	557
0.7-0.8	115
0.8-0.85	9
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8862	High Similarity	NPD4625	Phase 3
0.8525	High Similarity	NPD3600	Clinical (unspecified phase)
0.8347	Intermediate Similarity	NPD4626	Approved
0.8333	Intermediate Similarity	NPD2342	Discontinued
0.8306	Intermediate Similarity	NPD1283	Approved
0.8291	Intermediate Similarity	NPD7635	Approved
0.8264	Intermediate Similarity	NPD1651	Approved
0.8235	Intermediate Similarity	NPD709	Approved
0.8211	Intermediate Similarity	NPD1611	Approved
0.8175	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD4097	Suspended
0.808	Intermediate Similarity	NPD4749	Approved
0.8067	Intermediate Similarity	NPD1398	Phase 1
0.8065	Intermediate Similarity	NPD1610	Phase 2
0.8065	Intermediate Similarity	NPD1281	Approved
0.8018	Intermediate Similarity	NPD288	Approved
0.7967	Intermediate Similarity	NPD5691	Approved
0.7939	Intermediate Similarity	NPD4060	Phase 1
0.7937	Intermediate Similarity	NPD1669	Approved
0.7934	Intermediate Similarity	NPD6671	Approved
0.7928	Intermediate Similarity	NPD844	Approved
0.7923	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7923	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD1548	Phase 1
0.7881	Intermediate Similarity	NPD4750	Phase 3
0.7874	Intermediate Similarity	NPD6696	Suspended
0.7869	Intermediate Similarity	NPD7340	Approved
0.7778	Intermediate Similarity	NPD968	Approved
0.7769	Intermediate Similarity	NPD4908	Phase 1
0.775	Intermediate Similarity	NPD228	Approved
0.7717	Intermediate Similarity	NPD2232	Approved
0.7717	Intermediate Similarity	NPD2230	Approved
0.7717	Intermediate Similarity	NPD2233	Approved
0.7705	Intermediate Similarity	NPD497	Approved
0.7652	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7623	Intermediate Similarity	NPD496	Approved
0.7623	Intermediate Similarity	NPD495	Approved
0.7623	Intermediate Similarity	NPD498	Approved
0.7623	Intermediate Similarity	NPD5283	Phase 1
0.7615	Intermediate Similarity	NPD4624	Approved
0.7609	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD845	Approved
0.7576	Intermediate Similarity	NPD3027	Phase 3
0.7565	Intermediate Similarity	NPD3020	Approved
0.7563	Intermediate Similarity	NPD290	Approved
0.7557	Intermediate Similarity	NPD2861	Phase 2
0.7557	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7537	Intermediate Similarity	NPD1613	Approved
0.7537	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD6099	Approved
0.7518	Intermediate Similarity	NPD2935	Discontinued
0.7518	Intermediate Similarity	NPD6100	Approved
0.75	Intermediate Similarity	NPD1242	Phase 1
0.748	Intermediate Similarity	NPD2286	Discontinued
0.7456	Intermediate Similarity	NPD2860	Approved
0.7456	Intermediate Similarity	NPD2859	Approved
0.7436	Intermediate Similarity	NPD940	Approved
0.7436	Intermediate Similarity	NPD846	Approved
0.7429	Intermediate Similarity	NPD7003	Approved
0.7426	Intermediate Similarity	NPD1607	Approved
0.7407	Intermediate Similarity	NPD2979	Phase 3
0.7407	Intermediate Similarity	NPD3620	Phase 2
0.7407	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD2797	Approved
0.7402	Intermediate Similarity	NPD3445	Approved
0.7402	Intermediate Similarity	NPD3444	Approved
0.7402	Intermediate Similarity	NPD3443	Approved
0.7398	Intermediate Similarity	NPD1138	Approved
0.7394	Intermediate Similarity	NPD7041	Phase 2
0.7394	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD5327	Phase 3
0.7379	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD2933	Approved
0.7368	Intermediate Similarity	NPD2934	Approved
0.7364	Intermediate Similarity	NPD422	Phase 1
0.736	Intermediate Similarity	NPD6387	Discontinued
0.7348	Intermediate Similarity	NPD6584	Phase 3
0.7344	Intermediate Similarity	NPD1778	Approved
0.7338	Intermediate Similarity	NPD2346	Discontinued
0.7323	Intermediate Similarity	NPD3091	Approved
0.7319	Intermediate Similarity	NPD4108	Discontinued
0.7317	Intermediate Similarity	NPD1139	Approved
0.7317	Intermediate Similarity	NPD1137	Approved
0.7308	Intermediate Similarity	NPD1608	Approved
0.7304	Intermediate Similarity	NPD1809	Phase 2
0.7302	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD3021	Approved
0.7295	Intermediate Similarity	NPD3022	Approved
0.7295	Intermediate Similarity	NPD5451	Approved
0.7293	Intermediate Similarity	NPD1712	Approved
0.7292	Intermediate Similarity	NPD6090	Discontinued
0.7279	Intermediate Similarity	NPD4140	Approved
0.7279	Intermediate Similarity	NPD2238	Phase 2
0.7279	Intermediate Similarity	NPD1240	Approved
0.7266	Intermediate Similarity	NPD2438	Suspended
0.7259	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD1201	Approved
0.7227	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD5735	Approved
0.7217	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD5762	Approved
0.7214	Intermediate Similarity	NPD5763	Approved
0.7213	Intermediate Similarity	NPD2684	Approved
0.7209	Intermediate Similarity	NPD2668	Approved
0.7209	Intermediate Similarity	NPD2667	Approved
0.719	Intermediate Similarity	NPD6232	Discontinued
0.7185	Intermediate Similarity	NPD1024	Discontinued
0.7183	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD3892	Phase 2
0.7176	Intermediate Similarity	NPD1840	Phase 2
0.7174	Intermediate Similarity	NPD2157	Approved
0.7174	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD6353	Approved
0.7164	Intermediate Similarity	NPD3018	Phase 2
0.7163	Intermediate Similarity	NPD7037	Approved
0.7163	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD1792	Phase 2
0.7154	Intermediate Similarity	NPD3496	Discontinued
0.7143	Intermediate Similarity	NPD4476	Approved
0.7143	Intermediate Similarity	NPD2531	Phase 2
0.7143	Intermediate Similarity	NPD4477	Approved
0.7132	Intermediate Similarity	NPD3268	Approved
0.7121	Intermediate Similarity	NPD6582	Phase 2
0.7121	Intermediate Similarity	NPD6583	Phase 3
0.7121	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD600	Approved
0.7111	Intermediate Similarity	NPD596	Approved
0.7109	Intermediate Similarity	NPD7644	Approved
0.7103	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD3092	Approved
0.709	Intermediate Similarity	NPD3690	Phase 2
0.709	Intermediate Similarity	NPD3691	Phase 2
0.7087	Intermediate Similarity	NPD2557	Approved
0.7087	Intermediate Similarity	NPD7157	Approved
0.708	Intermediate Similarity	NPD9295	Approved
0.7077	Intermediate Similarity	NPD17	Approved
0.7077	Intermediate Similarity	NPD2932	Approved
0.7077	Intermediate Similarity	NPD4059	Approved
0.7077	Intermediate Similarity	NPD3019	Approved
0.7071	Intermediate Similarity	NPD1510	Phase 2
0.7071	Intermediate Similarity	NPD4308	Phase 3
0.7071	Intermediate Similarity	NPD2154	Approved
0.7071	Intermediate Similarity	NPD2155	Approved
0.7071	Intermediate Similarity	NPD2156	Approved
0.7071	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD5929	Approved
0.7063	Intermediate Similarity	NPD3750	Approved
0.7051	Intermediate Similarity	NPD7473	Discontinued
0.7045	Intermediate Similarity	NPD2231	Phase 2
0.7045	Intermediate Similarity	NPD2235	Phase 2
0.7034	Intermediate Similarity	NPD6087	Phase 1
0.7027	Intermediate Similarity	NPD3226	Approved
0.7023	Intermediate Similarity	NPD3847	Discontinued
0.7021	Intermediate Similarity	NPD1551	Phase 2
0.7015	Intermediate Similarity	NPD1470	Approved
0.7015	Intermediate Similarity	NPD3094	Phase 2
0.7015	Intermediate Similarity	NPD1203	Approved
0.7013	Intermediate Similarity	NPD6959	Discontinued
0.7007	Intermediate Similarity	NPD1039	Discontinued
0.7007	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5585	Approved
0.7	Intermediate Similarity	NPD4093	Discontinued
0.6993	Remote Similarity	NPD6674	Discontinued
0.6993	Remote Similarity	NPD5177	Phase 3
0.6992	Remote Similarity	NPD2982	Phase 2
0.6992	Remote Similarity	NPD2983	Phase 2
0.6986	Remote Similarity	NPD2532	Approved
0.6986	Remote Similarity	NPD2534	Approved
0.6986	Remote Similarity	NPD2533	Approved
0.6986	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD821	Approved
0.6984	Remote Similarity	NPD5535	Approved
0.6984	Remote Similarity	NPD7843	Approved
0.697	Remote Similarity	NPD1091	Approved
0.6963	Remote Similarity	NPD2798	Approved
0.6957	Remote Similarity	NPD839	Approved
0.6957	Remote Similarity	NPD4475	Approved
0.6957	Remote Similarity	NPD840	Approved
0.6957	Remote Similarity	NPD4474	Approved
0.6954	Remote Similarity	NPD7819	Suspended
0.6947	Remote Similarity	NPD1751	Approved
0.6947	Remote Similarity	NPD3095	Discontinued
0.694	Remote Similarity	NPD8651	Approved
0.694	Remote Similarity	NPD1876	Approved
0.694	Remote Similarity	NPD3225	Approved
0.6939	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD4319	Phase 2
0.6934	Remote Similarity	NPD7095	Approved
0.6929	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1182	Approved
0.6917	Remote Similarity	NPD2981	Phase 2
0.6917	Remote Similarity	NPD3972	Approved
0.6912	Remote Similarity	NPD5736	Approved
0.6911	Remote Similarity	NPD1444	Approved
0.6911	Remote Similarity	NPD1445	Approved
0.6901	Remote Similarity	NPD5404	Approved
0.6901	Remote Similarity	NPD5405	Approved
0.6901	Remote Similarity	NPD5406	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