NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	160.05
Volume:	168.802
LogP:	2.406
LogD:	2.549
LogS:	-2.357
# Rotatable Bonds:	0
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.62
Synthetic Accessibility Score:	1.79
Fsp3:	0.0
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:	-4.582
MDCK Permeability:	1.6563839380978607e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.051
20% Bioavailability (F20%):	0.971
30% Bioavailability (F30%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.08
Plasma Protein Binding (PPB):	91.91324615478516%
Volume Distribution (VD):	0.766
Pgp-substrate:	6.160491943359375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.985
CYP1A2-substrate:	0.428
CYP2C19-inhibitor:	0.354
CYP2C19-substrate:	0.079
CYP2C9-inhibitor:	0.278
CYP2C9-substrate:	0.904
CYP2D6-inhibitor:	0.783
CYP2D6-substrate:	0.855
CYP3A4-inhibitor:	0.397
CYP3A4-substrate:	0.153

ADMET: Excretion

Clearance (CL):	15.364
Half-life (T1/2):	0.886

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.038
Drug-inuced Liver Injury (DILI):	0.257
AMES Toxicity:	0.714
Rat Oral Acute Toxicity:	0.646
Maximum Recommended Daily Dose:	0.789
Skin Sensitization:	0.948
Carcinogencity:	0.611
Eye Corrosion:	0.587
Eye Irritation:	0.991
Respiratory Toxicity:	0.827

Download Data

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

Natural Product: NPC202647

Natural Product ID:	NPC202647
*Common Name:**	1,3-Naphthalenediol
IUPAC Name:	naphthalene-1,3-diol
Synonyms:	NSC-115890
Standard InCHIKey:	XOOMNEFVDUTJPP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H8O2/c11-8-5-7-3-1-2-4-9(7)10(12)6-8/h1-6,11-12H
SMILES:	Oc1cc2ccccc2c(c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL381547
PubChem CID:	8601
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
NPO31136	Cassia tora	Species	Fabaceae	Eukaryota	seeds	n.a.	n.a.	PMID[26483136]
NPO31136	Cassia tora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31136	Cassia tora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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
ED50	2
IC50	1

Activity Type	# Activity
Cell Line	2
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1855	Cell Line	HFL1	Homo sapiens	ED50	=	100.0	uM	PMID[515214]
NPT550	Cell Line	T-24	Homo sapiens	ED50	=	70.0	uM	PMID[515214]
NPT366	Individual Protein	Quinone reductase 2	Homo sapiens	IC50	=	3300.0	nM	PMID[515215]

☑ 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 NPC202647 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	567
0.1-0.2	2292
0.2-0.3	7386
0.3-0.4	12045
0.4-0.5	4607
0.5-0.6	7252
0.6-0.7	6584
0.7-0.8	1709
0.8-0.85	174
0.85-0.9	61
0.9-0.95	19
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9412	High Similarity	NPC292452
0.9406	High Similarity	NPC168393
0.9346	High Similarity	NPC107240
0.932	High Similarity	NPC248904
0.9314	High Similarity	NPC30506
0.9314	High Similarity	NPC102216
0.9266	High Similarity	NPC470760
0.9208	High Similarity	NPC275053
0.9208	High Similarity	NPC161571
0.9208	High Similarity	NPC248573
0.9174	High Similarity	NPC115808
0.9135	High Similarity	NPC67250
0.9126	High Similarity	NPC119860
0.9118	High Similarity	NPC100340
0.9118	High Similarity	NPC143659
0.9065	High Similarity	NPC476632
0.9065	High Similarity	NPC165770
0.9065	High Similarity	NPC225679
0.9065	High Similarity	NPC4493
0.9038	High Similarity	NPC474839
0.901	High Similarity	NPC291789
0.901	High Similarity	NPC32674
0.901	High Similarity	NPC156313
0.8981	High Similarity	NPC43525
0.8981	High Similarity	NPC166995
0.8972	High Similarity	NPC224870
0.8962	High Similarity	NPC174981
0.8942	High Similarity	NPC241891
0.8929	High Similarity	NPC217174
0.8922	High Similarity	NPC80027
0.8909	High Similarity	NPC472893
0.8899	High Similarity	NPC117846
0.8889	High Similarity	NPC224527
0.8879	High Similarity	NPC19808
0.8879	High Similarity	NPC33728
0.8857	High Similarity	NPC134829
0.885	High Similarity	NPC472071
0.8846	High Similarity	NPC233827
0.8818	High Similarity	NPC249270
0.8807	High Similarity	NPC473521
0.8785	High Similarity	NPC63698
0.8785	High Similarity	NPC95344
0.8785	High Similarity	NPC61885
0.8785	High Similarity	NPC233835
0.8774	High Similarity	NPC118286
0.8774	High Similarity	NPC109691
0.8774	High Similarity	NPC470700
0.8774	High Similarity	NPC39097
0.8774	High Similarity	NPC39664
0.8774	High Similarity	NPC302681
0.8772	High Similarity	NPC102639
0.8739	High Similarity	NPC246760
0.8739	High Similarity	NPC84999
0.8727	High Similarity	NPC263753
0.8716	High Similarity	NPC268032
0.8716	High Similarity	NPC151537
0.8696	High Similarity	NPC39029
0.8696	High Similarity	NPC237667
0.8692	High Similarity	NPC176527
0.8692	High Similarity	NPC54844
0.8679	High Similarity	NPC471350
0.8679	High Similarity	NPC246056
0.8661	High Similarity	NPC261973
0.8654	High Similarity	NPC10588
0.8654	High Similarity	NPC166761
0.8632	High Similarity	NPC138248
0.8632	High Similarity	NPC228503
0.8627	High Similarity	NPC274678
0.8624	High Similarity	NPC475018
0.8621	High Similarity	NPC120172
0.8611	High Similarity	NPC58427
0.8611	High Similarity	NPC105727
0.8611	High Similarity	NPC34864
0.8611	High Similarity	NPC114392
0.8598	High Similarity	NPC54765
0.8585	High Similarity	NPC327811
0.8585	High Similarity	NPC244513
0.8585	High Similarity	NPC227458
0.8585	High Similarity	NPC254965
0.8585	High Similarity	NPC218879
0.8584	High Similarity	NPC221549
0.8584	High Similarity	NPC195466
0.8584	High Similarity	NPC244816
0.8584	High Similarity	NPC50521
0.8571	High Similarity	NPC284011
0.8571	High Similarity	NPC72947
0.8559	High Similarity	NPC23804
0.8559	High Similarity	NPC261343
0.8559	High Similarity	NPC278955
0.8559	High Similarity	NPC105718
0.8547	High Similarity	NPC53567
0.8545	High Similarity	NPC95716
0.8532	High Similarity	NPC186385
0.8532	High Similarity	NPC58865
0.8532	High Similarity	NPC314187
0.8532	High Similarity	NPC299568
0.8529	High Similarity	NPC128062
0.8529	High Similarity	NPC245187
0.8522	High Similarity	NPC69006
0.8519	High Similarity	NPC232523
0.8519	High Similarity	NPC204901
0.8519	High Similarity	NPC158253
0.8509	High Similarity	NPC144343
0.8505	High Similarity	NPC37802
0.8496	Intermediate Similarity	NPC203113
0.8491	Intermediate Similarity	NPC168303
0.8491	Intermediate Similarity	NPC242342
0.8491	Intermediate Similarity	NPC302219
0.8491	Intermediate Similarity	NPC313030
0.8491	Intermediate Similarity	NPC106396
0.8491	Intermediate Similarity	NPC71002
0.8491	Intermediate Similarity	NPC146798
0.8491	Intermediate Similarity	NPC85479
0.8491	Intermediate Similarity	NPC53051
0.8491	Intermediate Similarity	NPC222522
0.8491	Intermediate Similarity	NPC94351
0.8491	Intermediate Similarity	NPC249828
0.8491	Intermediate Similarity	NPC24404
0.8491	Intermediate Similarity	NPC168829
0.8487	Intermediate Similarity	NPC170485
0.8475	Intermediate Similarity	NPC97578
0.8475	Intermediate Similarity	NPC224342
0.8468	Intermediate Similarity	NPC46940
0.8431	Intermediate Similarity	NPC295295
0.8431	Intermediate Similarity	NPC271440
0.8426	Intermediate Similarity	NPC99836
0.8426	Intermediate Similarity	NPC12640
0.8426	Intermediate Similarity	NPC201662
0.8421	Intermediate Similarity	NPC277588
0.8417	Intermediate Similarity	NPC53781
0.8417	Intermediate Similarity	NPC473221
0.8411	Intermediate Similarity	NPC238696
0.8411	Intermediate Similarity	NPC288411
0.8407	Intermediate Similarity	NPC167934
0.8407	Intermediate Similarity	NPC808
0.8403	Intermediate Similarity	NPC105031
0.8403	Intermediate Similarity	NPC113495
0.8396	Intermediate Similarity	NPC12221
0.8396	Intermediate Similarity	NPC166313
0.8396	Intermediate Similarity	NPC192032
0.8396	Intermediate Similarity	NPC147310
0.8396	Intermediate Similarity	NPC24407
0.8396	Intermediate Similarity	NPC11280
0.8396	Intermediate Similarity	NPC294186
0.8396	Intermediate Similarity	NPC137415
0.8378	Intermediate Similarity	NPC296920
0.8378	Intermediate Similarity	NPC90520
0.8365	Intermediate Similarity	NPC202986
0.8362	Intermediate Similarity	NPC223451
0.8348	Intermediate Similarity	NPC206
0.8347	Intermediate Similarity	NPC215300
0.8347	Intermediate Similarity	NPC38017
0.8333	Intermediate Similarity	NPC141090
0.8333	Intermediate Similarity	NPC9292
0.8333	Intermediate Similarity	NPC150624
0.8333	Intermediate Similarity	NPC138942
0.8333	Intermediate Similarity	NPC82299
0.8333	Intermediate Similarity	NPC145659
0.8333	Intermediate Similarity	NPC45040
0.8305	Intermediate Similarity	NPC74137
0.8304	Intermediate Similarity	NPC280606
0.8291	Intermediate Similarity	NPC24125
0.8276	Intermediate Similarity	NPC176893
0.8276	Intermediate Similarity	NPC191866
0.8273	Intermediate Similarity	NPC11554
0.8261	Intermediate Similarity	NPC474933
0.8261	Intermediate Similarity	NPC69261
0.8261	Intermediate Similarity	NPC33270
0.8246	Intermediate Similarity	NPC185541
0.8246	Intermediate Similarity	NPC464
0.823	Intermediate Similarity	NPC319803
0.823	Intermediate Similarity	NPC322239
0.823	Intermediate Similarity	NPC471485
0.823	Intermediate Similarity	NPC715
0.822	Intermediate Similarity	NPC476633
0.8208	Intermediate Similarity	NPC92730
0.8205	Intermediate Similarity	NPC3239
0.8205	Intermediate Similarity	NPC282255
0.8197	Intermediate Similarity	NPC148366
0.8197	Intermediate Similarity	NPC311293
0.819	Intermediate Similarity	NPC132271
0.819	Intermediate Similarity	NPC48781
0.819	Intermediate Similarity	NPC292730
0.819	Intermediate Similarity	NPC63010
0.819	Intermediate Similarity	NPC82664
0.819	Intermediate Similarity	NPC9592
0.819	Intermediate Similarity	NPC216520
0.819	Intermediate Similarity	NPC190514
0.8182	Intermediate Similarity	NPC305603
0.8182	Intermediate Similarity	NPC151477
0.8182	Intermediate Similarity	NPC223953
0.8182	Intermediate Similarity	NPC61033
0.8174	Intermediate Similarity	NPC85292
0.8174	Intermediate Similarity	NPC54507
0.8174	Intermediate Similarity	NPC229147
0.8173	Intermediate Similarity	NPC76938
0.8173	Intermediate Similarity	NPC151715
0.8165	Intermediate Similarity	NPC239291
0.8158	Intermediate Similarity	NPC473137
0.8158	Intermediate Similarity	NPC180508

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 NPC202647 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	503
0.1-0.2	1025
0.2-0.3	1590
0.3-0.4	3024
0.4-0.5	1605
0.5-0.6	1001
0.6-0.7	343
0.7-0.8	49
0.8-0.85	8
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9208	High Similarity	NPD1242	Phase 1
0.875	High Similarity	NPD940	Approved
0.875	High Similarity	NPD846	Approved
0.8532	High Similarity	NPD4750	Phase 3
0.8208	Intermediate Similarity	NPD3020	Approved
0.8182	Intermediate Similarity	NPD2342	Discontinued
0.8173	Intermediate Similarity	NPD2933	Approved
0.8173	Intermediate Similarity	NPD2934	Approved
0.8095	Intermediate Similarity	NPD2860	Approved
0.8095	Intermediate Similarity	NPD2859	Approved
0.8067	Intermediate Similarity	NPD1610	Phase 2
0.8034	Intermediate Similarity	NPD1548	Phase 1
0.8019	Intermediate Similarity	NPD288	Approved
0.7984	Intermediate Similarity	NPD4625	Phase 3
0.7982	Intermediate Similarity	NPD7635	Approved
0.7963	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD844	Approved
0.7876	Intermediate Similarity	NPD3021	Approved
0.7876	Intermediate Similarity	NPD3022	Approved
0.783	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD111	Approved
0.7623	Intermediate Similarity	NPD1201	Approved
0.7619	Intermediate Similarity	NPD4908	Phase 1
0.7603	Intermediate Similarity	NPD2286	Discontinued
0.7593	Intermediate Similarity	NPD1809	Phase 2
0.757	Intermediate Similarity	NPD845	Approved
0.7557	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD9089	Approved
0.7519	Intermediate Similarity	NPD1613	Approved
0.7519	Intermediate Similarity	NPD943	Approved
0.7519	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4749	Approved
0.748	Intermediate Similarity	NPD422	Phase 1
0.7479	Intermediate Similarity	NPD709	Approved
0.7438	Intermediate Similarity	NPD3091	Approved
0.7426	Intermediate Similarity	NPD9093	Approved
0.7422	Intermediate Similarity	NPD3027	Phase 3
0.7414	Intermediate Similarity	NPD1792	Phase 2
0.7395	Intermediate Similarity	NPD497	Approved
0.7395	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD1470	Approved
0.7377	Intermediate Similarity	NPD4093	Discontinued
0.7339	Intermediate Similarity	NPD3092	Approved
0.7323	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD2932	Approved
0.7317	Intermediate Similarity	NPD3019	Approved
0.7317	Intermediate Similarity	NPD4059	Approved
0.7311	Intermediate Similarity	NPD495	Approved
0.7311	Intermediate Similarity	NPD496	Approved
0.7311	Intermediate Similarity	NPD498	Approved
0.7297	Intermediate Similarity	NPD9273	Approved
0.7295	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD2861	Phase 2
0.7246	Intermediate Similarity	NPD7390	Discontinued
0.7244	Intermediate Similarity	NPD1164	Approved
0.7244	Intermediate Similarity	NPD3094	Phase 2
0.7239	Intermediate Similarity	NPD5404	Approved
0.7239	Intermediate Similarity	NPD5408	Approved
0.7239	Intermediate Similarity	NPD5405	Approved
0.7239	Intermediate Similarity	NPD5406	Approved
0.7177	Intermediate Similarity	NPD1751	Approved
0.7168	Intermediate Similarity	NPD3028	Approved
0.7167	Intermediate Similarity	NPD2229	Approved
0.7167	Intermediate Similarity	NPD2234	Approved
0.7167	Intermediate Similarity	NPD2228	Approved
0.7155	Intermediate Similarity	NPD1444	Approved
0.7155	Intermediate Similarity	NPD1445	Approved
0.7153	Intermediate Similarity	NPD3750	Approved
0.7143	Intermediate Similarity	NPD228	Approved
0.7143	Intermediate Similarity	NPD2568	Approved
0.7132	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD3018	Phase 2
0.7121	Intermediate Similarity	NPD1240	Approved
0.7119	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD9094	Approved
0.7099	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD9379	Approved
0.7083	Intermediate Similarity	NPD9377	Approved
0.7059	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD6671	Approved
0.704	Intermediate Similarity	NPD3095	Discontinued
0.704	Intermediate Similarity	NPD4626	Approved
0.704	Intermediate Similarity	NPD4589	Approved
0.7037	Intermediate Similarity	NPD1510	Phase 2
0.7031	Intermediate Similarity	NPD1283	Approved
0.7016	Intermediate Similarity	NPD5304	Approved
0.7016	Intermediate Similarity	NPD5303	Approved
0.7015	Intermediate Similarity	NPD1607	Approved
0.7009	Intermediate Similarity	NPD968	Approved
0.6992	Remote Similarity	NPD4060	Phase 1
0.6992	Remote Similarity	NPD1555	Discontinued
0.6992	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD6099	Approved
0.6985	Remote Similarity	NPD6100	Approved
0.6983	Remote Similarity	NPD9608	Approved
0.6983	Remote Similarity	NPD9610	Approved
0.697	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.696	Remote Similarity	NPD1651	Approved
0.6953	Remote Similarity	NPD2982	Phase 2
0.6953	Remote Similarity	NPD1669	Approved
0.6953	Remote Similarity	NPD2983	Phase 2
0.6934	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD6405	Approved
0.6917	Remote Similarity	NPD6407	Approved
0.6906	Remote Similarity	NPD3892	Phase 2
0.6905	Remote Similarity	NPD9381	Approved
0.6905	Remote Similarity	NPD9384	Approved
0.6905	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD4097	Suspended
0.6885	Remote Similarity	NPD5283	Phase 1
0.6879	Remote Similarity	NPD1511	Approved
0.6875	Remote Similarity	NPD2981	Phase 2
0.6875	Remote Similarity	NPD9269	Phase 2
0.687	Remote Similarity	NPD5736	Approved
0.6866	Remote Similarity	NPD2238	Phase 2
0.686	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3764	Approved
0.6825	Remote Similarity	NPD9268	Approved
0.6812	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD1281	Approved
0.6797	Remote Similarity	NPD1611	Approved
0.6794	Remote Similarity	NPD599	Approved
0.6794	Remote Similarity	NPD858	Approved
0.6794	Remote Similarity	NPD602	Approved
0.6794	Remote Similarity	NPD2195	Approved
0.6794	Remote Similarity	NPD859	Approved
0.6794	Remote Similarity	NPD2194	Approved
0.6788	Remote Similarity	NPD3748	Approved
0.6788	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD1512	Approved
0.6769	Remote Similarity	NPD5311	Approved
0.6769	Remote Similarity	NPD6696	Suspended
0.6769	Remote Similarity	NPD5310	Approved
0.6767	Remote Similarity	NPD5156	Approved
0.6767	Remote Similarity	NPD5155	Approved
0.6763	Remote Similarity	NPD1549	Phase 2
0.6752	Remote Similarity	NPD9500	Approved
0.6752	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.675	Remote Similarity	NPD9266	Approved
0.675	Remote Similarity	NPD74	Approved
0.6748	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD2233	Approved
0.6744	Remote Similarity	NPD1608	Approved
0.6744	Remote Similarity	NPD1840	Phase 2
0.6744	Remote Similarity	NPD2561	Approved
0.6744	Remote Similarity	NPD2232	Approved
0.6744	Remote Similarity	NPD2230	Approved
0.6744	Remote Similarity	NPD2562	Approved
0.6742	Remote Similarity	NPD3635	Approved
0.6742	Remote Similarity	NPD3637	Approved
0.6742	Remote Similarity	NPD3636	Approved
0.6739	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD9087	Approved
0.6719	Remote Similarity	NPD1980	Approved
0.6719	Remote Similarity	NPD3026	Approved
0.6719	Remote Similarity	NPD1983	Approved
0.6719	Remote Similarity	NPD3023	Approved
0.6719	Remote Similarity	NPD1981	Approved
0.6718	Remote Similarity	NPD3053	Approved
0.6718	Remote Similarity	NPD1133	Approved
0.6718	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD1129	Approved
0.6718	Remote Similarity	NPD1135	Approved
0.6718	Remote Similarity	NPD1134	Approved
0.6718	Remote Similarity	NPD4103	Phase 2
0.6718	Remote Similarity	NPD3055	Approved
0.6718	Remote Similarity	NPD1131	Approved
0.6714	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD9614	Approved
0.6694	Remote Similarity	NPD9618	Approved
0.6694	Remote Similarity	NPD1793	Approved
0.6694	Remote Similarity	NPD1791	Approved
0.6693	Remote Similarity	NPD3025	Approved
0.6693	Remote Similarity	NPD3024	Approved
0.6693	Remote Similarity	NPD5691	Approved
0.6692	Remote Similarity	NPD3594	Approved
0.6692	Remote Similarity	NPD4659	Approved
0.6692	Remote Similarity	NPD9622	Approved
0.6692	Remote Similarity	NPD2605	Approved
0.6692	Remote Similarity	NPD2606	Approved
0.6692	Remote Similarity	NPD3595	Approved
0.6691	Remote Similarity	NPD4726	Approved
0.6691	Remote Similarity	NPD4725	Approved
0.6691	Remote Similarity	NPD4721	Approved
0.6667	Remote Similarity	NPD4624	Approved
0.6667	Remote Similarity	NPD9267	Approved
0.6667	Remote Similarity	NPD6663	Approved
0.6667	Remote Similarity	NPD9264	Approved
0.6667	Remote Similarity	NPD290	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