NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	194.09
Volume:	200.161
LogP:	0.679
LogD:	0.912
LogS:	-1.898
# Rotatable Bonds:	1
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.713
Synthetic Accessibility Score:	3.134
Fsp3:	0.455
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:	-4.743
MDCK Permeability:	1.4822299817751627e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.713
Human Intestinal Absorption (HIA):	0.041
20% Bioavailability (F20%):	0.053
30% Bioavailability (F30%):	0.858

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.199
Plasma Protein Binding (PPB):	16.172395706176758%
Volume Distribution (VD):	2.901
Pgp-substrate:	68.30645751953125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.058
CYP1A2-substrate:	0.928
CYP2C19-inhibitor:	0.034
CYP2C19-substrate:	0.89
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.861
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.863
CYP3A4-inhibitor:	0.006
CYP3A4-substrate:	0.567

ADMET: Excretion

Clearance (CL):	6.458
Half-life (T1/2):	0.716

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.104
Drug-inuced Liver Injury (DILI):	0.038
AMES Toxicity:	0.14
Rat Oral Acute Toxicity:	0.085
Maximum Recommended Daily Dose:	0.851
Skin Sensitization:	0.258
Carcinogencity:	0.069
Eye Corrosion:	0.004
Eye Irritation:	0.274
Respiratory Toxicity:	0.196

Download Data

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

Natural Product: NPC470837

Natural Product ID:	NPC470837
*Common Name:**	Nodulisporol
IUPAC Name:	5-methoxy-1,2,3,4-tetrahydronaphthalene-1,4-diol
Synonyms:	nodulisporol
Standard InCHIKey:	AHHAFDIASKKVSM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H14O3/c1-14-10-4-2-3-7-8(12)5-6-9(13)11(7)10/h2-4,8-9,12-13H,5-6H2,1H3
SMILES:	COc1cccc2c1C(O)CCC2O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL226191
PubChem CID:	44423670
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
NPO33177	nodulisporium sp.	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12270179]
NPO33177	nodulisporium sp.	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12542359]
NPO33177	nodulisporium sp.	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17363259]
NPO33177	nodulisporium sp.	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25978520]

☑ 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	6

Activity Type	# Activity
Individual Protein	3
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2216	Individual Protein	DNA polymerase beta	Rattus norvegicus	IC50	>	1000000.0	nM	PMID[532809]
NPT4232	Individual Protein	DNA polymerase delta subunit 1	Homo sapiens	IC50	>	1000000.0	nM	PMID[532809]
NPT3732	Individual Protein	DNA polymerase lambda	Homo sapiens	IC50	=	168000.0	nM	PMID[532809]
NPT2	Others	Unspecified		IC50	>	1000000.0	nM	PMID[532809]

☑ 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 NPC470837 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	289
0.1-0.2	1502
0.2-0.3	4508
0.3-0.4	12756
0.4-0.5	5710
0.5-0.6	6444
0.6-0.7	8585
0.7-0.8	2694
0.8-0.85	178
0.85-0.9	27
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9252	High Similarity	NPC241549
0.8947	High Similarity	NPC283616
0.8947	High Similarity	NPC329980
0.8879	High Similarity	NPC100108
0.8879	High Similarity	NPC277798
0.885	High Similarity	NPC301321
0.8807	High Similarity	NPC233320
0.8783	High Similarity	NPC63010
0.8704	High Similarity	NPC130817
0.8667	High Similarity	NPC76119
0.8667	High Similarity	NPC4286
0.8661	High Similarity	NPC275627
0.8624	High Similarity	NPC471350
0.8571	High Similarity	NPC188997
0.8559	High Similarity	NPC102639
0.8559	High Similarity	NPC129176
0.8559	High Similarity	NPC169450
0.8534	High Similarity	NPC221549
0.8534	High Similarity	NPC244816
0.8534	High Similarity	NPC50521
0.8522	High Similarity	NPC808
0.85	High Similarity	NPC261992
0.8448	Intermediate Similarity	NPC290470
0.8448	Intermediate Similarity	NPC154256
0.8448	Intermediate Similarity	NPC150624
0.8421	Intermediate Similarity	NPC228452
0.8421	Intermediate Similarity	NPC98372
0.8417	Intermediate Similarity	NPC18128
0.8417	Intermediate Similarity	NPC152946
0.8417	Intermediate Similarity	NPC77789
0.8403	Intermediate Similarity	NPC473875
0.8393	Intermediate Similarity	NPC75440
0.8378	Intermediate Similarity	NPC67250
0.8376	Intermediate Similarity	NPC33270
0.8376	Intermediate Similarity	NPC69261
0.8374	Intermediate Similarity	NPC470841
0.8364	Intermediate Similarity	NPC12987
0.8364	Intermediate Similarity	NPC474603
0.8364	Intermediate Similarity	NPC241224
0.8362	Intermediate Similarity	NPC167934
0.8362	Intermediate Similarity	NPC283169
0.8362	Intermediate Similarity	NPC232165
0.8361	Intermediate Similarity	NPC278955
0.8361	Intermediate Similarity	NPC105718
0.8347	Intermediate Similarity	NPC248786
0.8333	Intermediate Similarity	NPC100870
0.832	Intermediate Similarity	NPC470727
0.8319	Intermediate Similarity	NPC232295
0.8319	Intermediate Similarity	NPC474272
0.8305	Intermediate Similarity	NPC190514
0.8304	Intermediate Similarity	NPC194034
0.8293	Intermediate Similarity	NPC470724
0.8291	Intermediate Similarity	NPC203113
0.8279	Intermediate Similarity	NPC228503
0.8279	Intermediate Similarity	NPC138248
0.8276	Intermediate Similarity	NPC276737
0.8276	Intermediate Similarity	NPC22610
0.8273	Intermediate Similarity	NPC233827
0.8273	Intermediate Similarity	NPC168393
0.8268	Intermediate Similarity	NPC138940
0.8264	Intermediate Similarity	NPC57199
0.8261	Intermediate Similarity	NPC474920
0.8261	Intermediate Similarity	NPC302371
0.8254	Intermediate Similarity	NPC284232
0.825	Intermediate Similarity	NPC96423
0.8246	Intermediate Similarity	NPC94045
0.8241	Intermediate Similarity	NPC88420
0.824	Intermediate Similarity	NPC472797
0.8235	Intermediate Similarity	NPC184302
0.8235	Intermediate Similarity	NPC32152
0.8226	Intermediate Similarity	NPC473221
0.822	Intermediate Similarity	NPC195466
0.8214	Intermediate Similarity	NPC30416
0.8211	Intermediate Similarity	NPC476254
0.8211	Intermediate Similarity	NPC470726
0.8211	Intermediate Similarity	NPC131397
0.8211	Intermediate Similarity	NPC293801
0.8211	Intermediate Similarity	NPC113495
0.8211	Intermediate Similarity	NPC105031
0.8205	Intermediate Similarity	NPC53906
0.819	Intermediate Similarity	NPC141003
0.819	Intermediate Similarity	NPC35344
0.8174	Intermediate Similarity	NPC90520
0.8174	Intermediate Similarity	NPC195873
0.8174	Intermediate Similarity	NPC296920
0.8167	Intermediate Similarity	NPC474131
0.816	Intermediate Similarity	NPC38017
0.816	Intermediate Similarity	NPC23012
0.8151	Intermediate Similarity	NPC474214
0.8145	Intermediate Similarity	NPC82299
0.8145	Intermediate Similarity	NPC170485
0.8142	Intermediate Similarity	NPC66834
0.8142	Intermediate Similarity	NPC251306
0.8136	Intermediate Similarity	NPC141090
0.8131	Intermediate Similarity	NPC245187
0.813	Intermediate Similarity	NPC61685
0.8115	Intermediate Similarity	NPC120638
0.8115	Intermediate Similarity	NPC46586
0.8115	Intermediate Similarity	NPC204535
0.8115	Intermediate Similarity	NPC74137
0.8115	Intermediate Similarity	NPC217756
0.8108	Intermediate Similarity	NPC24327
0.8108	Intermediate Similarity	NPC305205
0.8108	Intermediate Similarity	NPC12870
0.8103	Intermediate Similarity	NPC280606
0.8099	Intermediate Similarity	NPC475529
0.8099	Intermediate Similarity	NPC45663
0.8091	Intermediate Similarity	NPC130103
0.8091	Intermediate Similarity	NPC174911
0.8087	Intermediate Similarity	NPC137685
0.8087	Intermediate Similarity	NPC168657
0.8087	Intermediate Similarity	NPC132720
0.8087	Intermediate Similarity	NPC303521
0.8083	Intermediate Similarity	NPC474320
0.8083	Intermediate Similarity	NPC20230
0.8083	Intermediate Similarity	NPC121866
0.8083	Intermediate Similarity	NPC51341
0.8083	Intermediate Similarity	NPC135961
0.8083	Intermediate Similarity	NPC38181
0.8083	Intermediate Similarity	NPC471449
0.808	Intermediate Similarity	NPC53781
0.808	Intermediate Similarity	NPC242032
0.808	Intermediate Similarity	NPC469386
0.8077	Intermediate Similarity	NPC92932
0.8073	Intermediate Similarity	NPC474073
0.8073	Intermediate Similarity	NPC156313
0.807	Intermediate Similarity	NPC201959
0.8067	Intermediate Similarity	NPC127894
0.8067	Intermediate Similarity	NPC474933
0.8067	Intermediate Similarity	NPC470759
0.8067	Intermediate Similarity	NPC15860
0.8067	Intermediate Similarity	NPC219070
0.8065	Intermediate Similarity	NPC81641
0.8053	Intermediate Similarity	NPC113457
0.8053	Intermediate Similarity	NPC164576
0.8051	Intermediate Similarity	NPC464
0.8051	Intermediate Similarity	NPC473718
0.8051	Intermediate Similarity	NPC185541
0.8049	Intermediate Similarity	NPC474130
0.8049	Intermediate Similarity	NPC474160
0.8049	Intermediate Similarity	NPC280704
0.8047	Intermediate Similarity	NPC85595
0.8036	Intermediate Similarity	NPC475225
0.8036	Intermediate Similarity	NPC38079
0.8036	Intermediate Similarity	NPC108875
0.8036	Intermediate Similarity	NPC475580
0.8033	Intermediate Similarity	NPC168707
0.8033	Intermediate Similarity	NPC470212
0.8033	Intermediate Similarity	NPC48623
0.8033	Intermediate Similarity	NPC113865
0.8033	Intermediate Similarity	NPC473853
0.8033	Intermediate Similarity	NPC184651
0.8033	Intermediate Similarity	NPC212965
0.8033	Intermediate Similarity	NPC54872
0.8033	Intermediate Similarity	NPC476633
0.8033	Intermediate Similarity	NPC312675
0.8033	Intermediate Similarity	NPC324571
0.8033	Intermediate Similarity	NPC343720
0.8033	Intermediate Similarity	NPC285289
0.8033	Intermediate Similarity	NPC262156
0.8031	Intermediate Similarity	NPC196193
0.8018	Intermediate Similarity	NPC300166
0.8018	Intermediate Similarity	NPC12221
0.8017	Intermediate Similarity	NPC135467
0.8017	Intermediate Similarity	NPC35071
0.8017	Intermediate Similarity	NPC177475
0.8017	Intermediate Similarity	NPC103916
0.8017	Intermediate Similarity	NPC148615
0.8017	Intermediate Similarity	NPC260832
0.8016	Intermediate Similarity	NPC215300
0.8016	Intermediate Similarity	NPC38604
0.8016	Intermediate Similarity	NPC211179
0.8	Intermediate Similarity	NPC51087
0.8	Intermediate Similarity	NPC474040
0.8	Intermediate Similarity	NPC161856
0.7984	Intermediate Similarity	NPC248557
0.7983	Intermediate Similarity	NPC54507
0.7983	Intermediate Similarity	NPC114064
0.7983	Intermediate Similarity	NPC229147
0.7983	Intermediate Similarity	NPC85292
0.7983	Intermediate Similarity	NPC69539
0.7982	Intermediate Similarity	NPC320439
0.7982	Intermediate Similarity	NPC227894
0.7969	Intermediate Similarity	NPC153019
0.7967	Intermediate Similarity	NPC270326
0.7967	Intermediate Similarity	NPC474864
0.7967	Intermediate Similarity	NPC85488
0.7966	Intermediate Similarity	NPC180508
0.7966	Intermediate Similarity	NPC228287
0.7965	Intermediate Similarity	NPC154899
0.7965	Intermediate Similarity	NPC233396
0.7965	Intermediate Similarity	NPC470393
0.7955	Intermediate Similarity	NPC472151
0.7953	Intermediate Similarity	NPC471518
0.7953	Intermediate Similarity	NPC97326
0.7953	Intermediate Similarity	NPC158477
0.7953	Intermediate Similarity	NPC472796
0.7953	Intermediate Similarity	NPC190144
0.7953	Intermediate Similarity	NPC469951
0.7953	Intermediate Similarity	NPC471519

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 NPC470837 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	290
0.1-0.2	962
0.2-0.3	1607
0.3-0.4	2680
0.4-0.5	1738
0.5-0.6	1112
0.6-0.7	632
0.7-0.8	124
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8304	Intermediate Similarity	NPD290	Approved
0.8214	Intermediate Similarity	NPD968	Approved
0.8205	Intermediate Similarity	NPD6671	Approved
0.8205	Intermediate Similarity	NPD709	Approved
0.8049	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.8016	Intermediate Similarity	NPD600	Approved
0.8016	Intermediate Similarity	NPD596	Approved
0.8	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7967	Intermediate Similarity	NPD2232	Approved
0.7967	Intermediate Similarity	NPD2230	Approved
0.7967	Intermediate Similarity	NPD2233	Approved
0.7937	Intermediate Similarity	NPD2861	Phase 2
0.7928	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD2238	Phase 2
0.7886	Intermediate Similarity	NPD1610	Phase 2
0.7869	Intermediate Similarity	NPD4626	Approved
0.7863	Intermediate Similarity	NPD228	Approved
0.7851	Intermediate Similarity	NPD1548	Phase 1
0.7829	Intermediate Similarity	NPD839	Approved
0.7829	Intermediate Similarity	NPD840	Approved
0.7823	Intermediate Similarity	NPD2231	Phase 2
0.7823	Intermediate Similarity	NPD2235	Phase 2
0.7812	Intermediate Similarity	NPD3027	Phase 3
0.7812	Intermediate Similarity	NPD4625	Phase 3
0.7805	Intermediate Similarity	NPD3496	Discontinued
0.7769	Intermediate Similarity	NPD1613	Approved
0.7769	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD1091	Approved
0.7742	Intermediate Similarity	NPD1611	Approved
0.7731	Intermediate Similarity	NPD1398	Phase 1
0.7658	Intermediate Similarity	NPD288	Approved
0.7652	Intermediate Similarity	NPD4097	Suspended
0.7647	Intermediate Similarity	NPD7635	Approved
0.7642	Intermediate Similarity	NPD5691	Approved
0.7634	Intermediate Similarity	NPD4060	Phase 1
0.7619	Intermediate Similarity	NPD4749	Approved
0.7615	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD2684	Approved
0.7597	Intermediate Similarity	NPD4908	Phase 1
0.7583	Intermediate Similarity	NPD5283	Phase 1
0.7574	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD844	Approved
0.7559	Intermediate Similarity	NPD1283	Approved
0.7559	Intermediate Similarity	NPD6696	Suspended
0.7541	Intermediate Similarity	NPD7340	Approved
0.754	Intermediate Similarity	NPD1840	Phase 2
0.7519	Intermediate Similarity	NPD1712	Approved
0.75	Intermediate Similarity	NPD4140	Approved
0.75	Intermediate Similarity	NPD1357	Approved
0.75	Intermediate Similarity	NPD3443	Approved
0.75	Intermediate Similarity	NPD3444	Approved
0.75	Intermediate Similarity	NPD3445	Approved
0.75	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3620	Phase 2
0.75	Intermediate Similarity	NPD1651	Approved
0.75	Intermediate Similarity	NPD9295	Approved
0.7481	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD5327	Phase 3
0.748	Intermediate Similarity	NPD1669	Approved
0.7462	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD7157	Approved
0.7445	Intermediate Similarity	NPD5177	Phase 3
0.7444	Intermediate Similarity	NPD5735	Approved
0.7442	Intermediate Similarity	NPD4624	Approved
0.744	Intermediate Similarity	NPD1778	Approved
0.7426	Intermediate Similarity	NPD5762	Approved
0.7426	Intermediate Similarity	NPD5763	Approved
0.7419	Intermediate Similarity	NPD3091	Approved
0.7407	Intermediate Similarity	NPD2154	Approved
0.7407	Intermediate Similarity	NPD2156	Approved
0.7407	Intermediate Similarity	NPD2155	Approved
0.7405	Intermediate Similarity	NPD1024	Discontinued
0.7395	Intermediate Similarity	NPD4750	Phase 3
0.7385	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD2342	Discontinued
0.7368	Intermediate Similarity	NPD3020	Approved
0.7364	Intermediate Similarity	NPD2797	Approved
0.736	Intermediate Similarity	NPD5585	Approved
0.7355	Intermediate Similarity	NPD821	Approved
0.7355	Intermediate Similarity	NPD7843	Approved
0.7353	Intermediate Similarity	NPD2935	Discontinued
0.7338	Intermediate Similarity	NPD2677	Approved
0.7323	Intermediate Similarity	NPD422	Phase 1
0.7323	Intermediate Similarity	NPD1281	Approved
0.7321	Intermediate Similarity	NPD2934	Approved
0.7321	Intermediate Similarity	NPD2933	Approved
0.7308	Intermediate Similarity	NPD558	Phase 2
0.7308	Intermediate Similarity	NPD6584	Phase 3
0.7304	Intermediate Similarity	NPD1242	Phase 1
0.7302	Intermediate Similarity	NPD2667	Approved
0.7302	Intermediate Similarity	NPD2668	Approved
0.728	Intermediate Similarity	NPD1182	Approved
0.7266	Intermediate Similarity	NPD3892	Phase 2
0.7266	Intermediate Similarity	NPD1608	Approved
0.7259	Intermediate Similarity	NPD6353	Approved
0.7259	Intermediate Similarity	NPD6653	Approved
0.7257	Intermediate Similarity	NPD2859	Approved
0.7257	Intermediate Similarity	NPD2860	Approved
0.725	Intermediate Similarity	NPD5451	Approved
0.7241	Intermediate Similarity	NPD940	Approved
0.7241	Intermediate Similarity	NPD846	Approved
0.7236	Intermediate Similarity	NPD497	Approved
0.7234	Intermediate Similarity	NPD7041	Phase 2
0.7234	Intermediate Similarity	NPD6087	Phase 1
0.7234	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD845	Approved
0.7231	Intermediate Similarity	NPD3094	Phase 2
0.7213	Intermediate Similarity	NPD1138	Approved
0.7188	Intermediate Similarity	NPD3092	Approved
0.7188	Intermediate Similarity	NPD3705	Approved
0.7177	Intermediate Similarity	NPD2557	Approved
0.7176	Intermediate Similarity	NPD3691	Phase 2
0.7176	Intermediate Similarity	NPD3690	Phase 2
0.7168	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD3095	Discontinued
0.7154	Intermediate Similarity	NPD498	Approved
0.7154	Intermediate Similarity	NPD496	Approved
0.7154	Intermediate Similarity	NPD495	Approved
0.7132	Intermediate Similarity	NPD2157	Approved
0.7131	Intermediate Similarity	NPD1137	Approved
0.7131	Intermediate Similarity	NPD1139	Approved
0.7122	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD3018	Phase 2
0.7107	Intermediate Similarity	NPD3022	Approved
0.7107	Intermediate Similarity	NPD1792	Phase 2
0.7107	Intermediate Similarity	NPD3021	Approved
0.7103	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6100	Approved
0.7101	Intermediate Similarity	NPD6032	Approved
0.7101	Intermediate Similarity	NPD6099	Approved
0.7097	Intermediate Similarity	NPD9614	Approved
0.7097	Intermediate Similarity	NPD9618	Approved
0.7094	Intermediate Similarity	NPD291	Approved
0.7092	Intermediate Similarity	NPD5241	Discontinued
0.7092	Intermediate Similarity	NPD3692	Discontinued
0.709	Intermediate Similarity	NPD3268	Approved
0.709	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD1336	Approved
0.7077	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD6583	Phase 3
0.7077	Intermediate Similarity	NPD4359	Approved
0.7077	Intermediate Similarity	NPD6582	Phase 2
0.7071	Intermediate Similarity	NPD6674	Discontinued
0.7063	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD9697	Approved
0.7059	Intermediate Similarity	NPD6355	Discontinued
0.7054	Intermediate Similarity	NPD9365	Approved
0.7054	Intermediate Similarity	NPD1535	Discovery
0.704	Intermediate Similarity	NPD6387	Discontinued
0.7037	Intermediate Similarity	NPD6233	Phase 2
0.7037	Intermediate Similarity	NPD4474	Approved
0.7037	Intermediate Similarity	NPD4475	Approved
0.7031	Intermediate Similarity	NPD17	Approved
0.7031	Intermediate Similarity	NPD2554	Approved
0.7031	Intermediate Similarity	NPD6516	Phase 2
0.7031	Intermediate Similarity	NPD2556	Approved
0.7031	Intermediate Similarity	NPD5846	Approved
0.7029	Intermediate Similarity	NPD7033	Discontinued
0.7029	Intermediate Similarity	NPD1753	Discontinued
0.7029	Intermediate Similarity	NPD4108	Discontinued
0.7023	Intermediate Similarity	NPD8651	Approved
0.7023	Intermediate Similarity	NPD3225	Approved
0.7016	Intermediate Similarity	NPD1241	Discontinued
0.7014	Intermediate Similarity	NPD6090	Discontinued
0.7008	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD1894	Discontinued
0.7	Intermediate Similarity	NPD9717	Approved
0.7	Intermediate Similarity	NPD2424	Discontinued
0.7	Intermediate Similarity	NPD3134	Approved
0.7	Intermediate Similarity	NPD1481	Phase 2
0.6992	Remote Similarity	NPD2237	Approved
0.6985	Remote Similarity	NPD1240	Approved
0.6985	Remote Similarity	NPD2979	Phase 3
0.6985	Remote Similarity	NPD3597	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD9493	Approved
0.6978	Remote Similarity	NPD4477	Approved
0.6978	Remote Similarity	NPD4476	Approved
0.6977	Remote Similarity	NPD3847	Discontinued
0.6972	Remote Similarity	NPD111	Approved
0.697	Remote Similarity	NPD6362	Approved
0.697	Remote Similarity	NPD1203	Approved
0.697	Remote Similarity	NPD1794	Approved
0.6963	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD1048	Approved
0.6963	Remote Similarity	NPD1039	Discontinued
0.6963	Remote Similarity	NPD6798	Discontinued
0.6959	Remote Similarity	NPD37	Approved
0.6957	Remote Similarity	NPD1809	Phase 2
0.6957	Remote Similarity	NPD4538	Approved
0.6957	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4536	Approved
0.6953	Remote Similarity	NPD3049	Approved
0.6947	Remote Similarity	NPD2983	Phase 2
0.6947	Remote Similarity	NPD2982	Phase 2
0.6947	Remote Similarity	NPD3685	Discontinued
0.6942	Remote Similarity	NPD1358	Approved
0.6935	Remote Similarity	NPD5535	Approved
0.6934	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD447	Suspended

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