NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	268.15
Volume:	295.977
LogP:	4.412
LogD:	4.074
LogS:	-3.51
# Rotatable Bonds:	1
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.819
Synthetic Accessibility Score:	3.256
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.744
MDCK Permeability:	1.5013937627372798e-05
Pgp-inhibitor:	0.075
Pgp-substrate:	0.977
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.064
30% Bioavailability (F30%):	0.043

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.14
Plasma Protein Binding (PPB):	97.55731964111328%
Volume Distribution (VD):	1.959
Pgp-substrate:	1.648015022277832%

ADMET: Metabolism

CYP1A2-inhibitor:	0.882
CYP1A2-substrate:	0.917
CYP2C19-inhibitor:	0.956
CYP2C19-substrate:	0.546
CYP2C9-inhibitor:	0.861
CYP2C9-substrate:	0.975
CYP2D6-inhibitor:	0.919
CYP2D6-substrate:	0.909
CYP3A4-inhibitor:	0.704
CYP3A4-substrate:	0.649

ADMET: Excretion

Clearance (CL):	18.019
Half-life (T1/2):	0.452

ADMET: Toxicity

hERG Blockers:	0.05
Human Hepatotoxicity (H-HT):	0.133
Drug-inuced Liver Injury (DILI):	0.322
AMES Toxicity:	0.069
Rat Oral Acute Toxicity:	0.245
Maximum Recommended Daily Dose:	0.815
Skin Sensitization:	0.65
Carcinogencity:	0.319
Eye Corrosion:	0.02
Eye Irritation:	0.924
Respiratory Toxicity:	0.639

Download Data

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

Natural Product: NPC11554

Natural Product ID:	NPC11554
*Common Name:**	(8R, 7's, 8's)-4,4'-Bis-(Hydroxy)-6,7'-Cyclolignan
IUPAC Name:	(6R,7S,8S)-8-(4-hydroxyphenyl)-6,7-dimethyl-5,6,7,8-tetrahydronaphthalen-2-ol
Synonyms:
Standard InCHIKey:	SFHVHQMPRGEUDC-SOZUMNATSA-N
Standard InCHI:	InChI=1S/C18H20O2/c1-11-9-14-5-8-16(20)10-17(14)18(12(11)2)13-3-6-15(19)7-4-13/h3-8,10-12,18-20H,9H2,1-2H3/t11-,12+,18+/m1/s1
SMILES:	Oc1ccc(cc1)[C@@H]1[C@@H](C)[C@H](C)Cc2c1cc(O)cc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL259174
PubChem CID:	44450583
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003425] Aryltetralin lignans

*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
NPO2754	Iryanthera lancifolia	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10579855]
NPO2754	Iryanthera lancifolia	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18242997]
NPO2754	Iryanthera lancifolia	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	MED	=	10.0	uM	PMID[468726]
NPT83	Cell Line	MCF7	Homo sapiens	Ratio	=	6.4	n.a.	PMID[468726]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	0.01	%	PMID[468726]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	77.8	%	PMID[468726]

☑ 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 NPC11554 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	284
0.1-0.2	1890
0.2-0.3	4174
0.3-0.4	12135
0.4-0.5	7190
0.5-0.6	9322
0.6-0.7	5646
0.7-0.8	1650
0.8-0.85	294
0.85-0.9	95
0.9-0.95	15
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9519	High Similarity	NPC95716
0.9429	High Similarity	NPC46940
0.934	High Similarity	NPC715
0.9333	High Similarity	NPC322753
0.9252	High Similarity	NPC195922
0.9238	High Similarity	NPC141782
0.9151	High Similarity	NPC260323
0.9151	High Similarity	NPC176279
0.9143	High Similarity	NPC58865
0.9135	High Similarity	NPC151477
0.9074	High Similarity	NPC268160
0.9065	High Similarity	NPC250323
0.9057	High Similarity	NPC13482
0.9038	High Similarity	NPC271274
0.9	High Similarity	NPC216520
0.9	High Similarity	NPC132271
0.9	High Similarity	NPC292730
0.9	High Similarity	NPC473388
0.9	High Similarity	NPC82664
0.8991	High Similarity	NPC147179
0.8991	High Similarity	NPC192948
0.8991	High Similarity	NPC35797
0.8972	High Similarity	NPC151537
0.8972	High Similarity	NPC77772
0.8962	High Similarity	NPC314187
0.8942	High Similarity	NPC117115
0.8919	High Similarity	NPC48342
0.8919	High Similarity	NPC164649
0.8911	High Similarity	NPC32674
0.8909	High Similarity	NPC219112
0.8909	High Similarity	NPC308311
0.8909	High Similarity	NPC308828
0.8909	High Similarity	NPC477137
0.8909	High Similarity	NPC38893
0.8909	High Similarity	NPC471668
0.89	High Similarity	NPC26244
0.89	High Similarity	NPC274678
0.8879	High Similarity	NPC296683
0.8857	High Similarity	NPC21594
0.8839	High Similarity	NPC42657
0.8829	High Similarity	NPC477136
0.8829	High Similarity	NPC304510
0.8829	High Similarity	NPC299180
0.8829	High Similarity	NPC16030
0.8829	High Similarity	NPC172219
0.8824	High Similarity	NPC92730
0.8818	High Similarity	NPC84999
0.8818	High Similarity	NPC246760
0.8807	High Similarity	NPC322239
0.8807	High Similarity	NPC321589
0.88	High Similarity	NPC76938
0.88	High Similarity	NPC151715
0.8796	High Similarity	NPC266937
0.8796	High Similarity	NPC470770
0.8785	High Similarity	NPC228343
0.8785	High Similarity	NPC254833
0.8762	High Similarity	NPC138942
0.8761	High Similarity	NPC103916
0.8761	High Similarity	NPC190501
0.8761	High Similarity	NPC99734
0.8761	High Similarity	NPC318552
0.875	High Similarity	NPC168829
0.875	High Similarity	NPC471671
0.875	High Similarity	NPC469609
0.8739	High Similarity	NPC92
0.8739	High Similarity	NPC469663
0.8739	High Similarity	NPC141001
0.8738	High Similarity	NPC211885
0.8727	High Similarity	NPC471534
0.8727	High Similarity	NPC107240
0.8725	High Similarity	NPC225464
0.8716	High Similarity	NPC62867
0.8716	High Similarity	NPC177962
0.8713	High Similarity	NPC32714
0.8704	High Similarity	NPC132720
0.8684	High Similarity	NPC328504
0.8673	High Similarity	NPC126002
0.8673	High Similarity	NPC469644
0.8673	High Similarity	NPC151197
0.8673	High Similarity	NPC93071
0.8667	High Similarity	NPC238696
0.8667	High Similarity	NPC254965
0.8667	High Similarity	NPC288411
0.8667	High Similarity	NPC327811
0.8667	High Similarity	NPC323810
0.8654	High Similarity	NPC51015
0.8649	High Similarity	NPC469719
0.8636	High Similarity	NPC317869
0.8609	High Similarity	NPC77569
0.8609	High Similarity	NPC142198
0.86	High Similarity	NPC45040
0.86	High Similarity	NPC304541
0.8598	High Similarity	NPC320439
0.8596	High Similarity	NPC135467
0.8596	High Similarity	NPC260832
0.8585	High Similarity	NPC239291
0.8571	High Similarity	NPC474387
0.8571	High Similarity	NPC257540
0.8571	High Similarity	NPC154511
0.8571	High Similarity	NPC261973
0.8571	High Similarity	NPC474358
0.8571	High Similarity	NPC247858
0.8571	High Similarity	NPC137496
0.8559	High Similarity	NPC249270
0.8558	High Similarity	NPC294741
0.8558	High Similarity	NPC72729
0.8545	High Similarity	NPC228425
0.8545	High Similarity	NPC471179
0.8544	High Similarity	NPC79241
0.8544	High Similarity	NPC6597
0.8544	High Similarity	NPC156313
0.8544	High Similarity	NPC77492
0.8534	High Similarity	NPC176208
0.8534	High Similarity	NPC30462
0.8522	High Similarity	NPC32322
0.8522	High Similarity	NPC259703
0.8515	High Similarity	NPC162314
0.8515	High Similarity	NPC94139
0.8515	High Similarity	NPC306884
0.8515	High Similarity	NPC147284
0.8515	High Similarity	NPC3358
0.8515	High Similarity	NPC210497
0.8509	High Similarity	NPC176893
0.8505	High Similarity	NPC54765
0.85	High Similarity	NPC192
0.8476	Intermediate Similarity	NPC12221
0.8475	Intermediate Similarity	NPC29008
0.8475	Intermediate Similarity	NPC228771
0.8475	Intermediate Similarity	NPC266705
0.8468	Intermediate Similarity	NPC117846
0.8462	Intermediate Similarity	NPC78119
0.8462	Intermediate Similarity	NPC216468
0.8462	Intermediate Similarity	NPC132078
0.8462	Intermediate Similarity	NPC51333
0.8455	Intermediate Similarity	NPC476632
0.8455	Intermediate Similarity	NPC165770
0.8455	Intermediate Similarity	NPC4493
0.8455	Intermediate Similarity	NPC225679
0.8455	Intermediate Similarity	NPC224527
0.8448	Intermediate Similarity	NPC475166
0.8448	Intermediate Similarity	NPC162935
0.8448	Intermediate Similarity	NPC249340
0.8448	Intermediate Similarity	NPC253627
0.8447	Intermediate Similarity	NPC312132
0.8447	Intermediate Similarity	NPC202986
0.8447	Intermediate Similarity	NPC259512
0.8431	Intermediate Similarity	NPC316301
0.8431	Intermediate Similarity	NPC245187
0.8431	Intermediate Similarity	NPC128062
0.8431	Intermediate Similarity	NPC27323
0.8421	Intermediate Similarity	NPC154030
0.8421	Intermediate Similarity	NPC206
0.8421	Intermediate Similarity	NPC328694
0.84	Intermediate Similarity	NPC123273
0.84	Intermediate Similarity	NPC177420
0.84	Intermediate Similarity	NPC242240
0.84	Intermediate Similarity	NPC258219
0.84	Intermediate Similarity	NPC280347
0.84	Intermediate Similarity	NPC318325
0.8396	Intermediate Similarity	NPC168393
0.8396	Intermediate Similarity	NPC233827
0.8381	Intermediate Similarity	NPC225506
0.8381	Intermediate Similarity	NPC213730
0.8378	Intermediate Similarity	NPC166995
0.8378	Intermediate Similarity	NPC43525
0.8376	Intermediate Similarity	NPC11250
0.8376	Intermediate Similarity	NPC71094
0.8376	Intermediate Similarity	NPC321402
0.8376	Intermediate Similarity	NPC471794
0.8362	Intermediate Similarity	NPC129176
0.8362	Intermediate Similarity	NPC241001
0.835	Intermediate Similarity	NPC222146
0.835	Intermediate Similarity	NPC8392
0.8349	Intermediate Similarity	NPC75440
0.8349	Intermediate Similarity	NPC233835
0.8349	Intermediate Similarity	NPC95344
0.8349	Intermediate Similarity	NPC201959
0.8349	Intermediate Similarity	NPC262365
0.8348	Intermediate Similarity	NPC31296
0.8348	Intermediate Similarity	NPC258366
0.8348	Intermediate Similarity	NPC473974
0.8348	Intermediate Similarity	NPC79933
0.8333	Intermediate Similarity	NPC55903
0.8333	Intermediate Similarity	NPC477814
0.8333	Intermediate Similarity	NPC470760
0.8319	Intermediate Similarity	NPC9067
0.8318	Intermediate Similarity	NPC30506
0.8318	Intermediate Similarity	NPC241891
0.8318	Intermediate Similarity	NPC475225
0.8318	Intermediate Similarity	NPC272029
0.8318	Intermediate Similarity	NPC471511
0.8318	Intermediate Similarity	NPC475580
0.8317	Intermediate Similarity	NPC55561
0.8305	Intermediate Similarity	NPC471187
0.8305	Intermediate Similarity	NPC198014
0.8304	Intermediate Similarity	NPC263753
0.8302	Intermediate Similarity	NPC40258
0.8302	Intermediate Similarity	NPC7686
0.8302	Intermediate Similarity	NPC252105
0.8302	Intermediate Similarity	NPC91461

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 NPC11554 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	303
0.1-0.2	1072
0.2-0.3	1035
0.3-0.4	2853
0.4-0.5	2008
0.5-0.6	1271
0.6-0.7	474
0.7-0.8	108
0.8-0.85	14
0.85-0.9	11
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.92	High Similarity	NPD3020	Approved
0.8919	High Similarity	NPD3091	Approved
0.89	High Similarity	NPD2859	Approved
0.89	High Similarity	NPD2860	Approved
0.88	High Similarity	NPD2933	Approved
0.88	High Similarity	NPD2934	Approved
0.8785	High Similarity	NPD3021	Approved
0.8785	High Similarity	NPD3022	Approved
0.8774	High Similarity	NPD2342	Discontinued
0.8761	High Similarity	NPD3019	Approved
0.8761	High Similarity	NPD4059	Approved
0.8716	High Similarity	NPD7635	Approved
0.8673	High Similarity	NPD4093	Discontinued
0.8609	High Similarity	NPD3092	Approved
0.8596	High Similarity	NPD2932	Approved
0.8447	Intermediate Similarity	NPD288	Approved
0.8435	Intermediate Similarity	NPD3095	Discontinued
0.8435	Intermediate Similarity	NPD2286	Discontinued
0.8431	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.835	Intermediate Similarity	NPD844	Approved
0.8319	Intermediate Similarity	NPD3094	Phase 2
0.8182	Intermediate Similarity	NPD5736	Approved
0.8155	Intermediate Similarity	NPD845	Approved
0.8151	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.812	Intermediate Similarity	NPD1751	Approved
0.8108	Intermediate Similarity	NPD4750	Phase 3
0.8108	Intermediate Similarity	NPD1792	Phase 2
0.8051	Intermediate Similarity	NPD3023	Approved
0.8051	Intermediate Similarity	NPD3026	Approved
0.8049	Intermediate Similarity	NPD5155	Approved
0.8049	Intermediate Similarity	NPD5156	Approved
0.8037	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD1242	Phase 1
0.8034	Intermediate Similarity	NPD3024	Approved
0.8034	Intermediate Similarity	NPD3025	Approved
0.8017	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1809	Phase 2
0.7982	Intermediate Similarity	NPD2229	Approved
0.7982	Intermediate Similarity	NPD2228	Approved
0.7982	Intermediate Similarity	NPD2234	Approved
0.7967	Intermediate Similarity	NPD2606	Approved
0.7967	Intermediate Similarity	NPD2605	Approved
0.7951	Intermediate Similarity	NPD4624	Approved
0.792	Intermediate Similarity	NPD6663	Approved
0.79	Intermediate Similarity	NPD111	Approved
0.7886	Intermediate Similarity	NPD3637	Approved
0.7886	Intermediate Similarity	NPD3636	Approved
0.7886	Intermediate Similarity	NPD3635	Approved
0.7838	Intermediate Similarity	NPD1445	Approved
0.7838	Intermediate Similarity	NPD1444	Approved
0.7833	Intermediate Similarity	NPD1201	Approved
0.7823	Intermediate Similarity	NPD3595	Approved
0.7823	Intermediate Similarity	NPD3594	Approved
0.7805	Intermediate Similarity	NPD2195	Approved
0.7805	Intermediate Similarity	NPD2194	Approved
0.7798	Intermediate Similarity	NPD846	Approved
0.7798	Intermediate Similarity	NPD940	Approved
0.7778	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD3620	Phase 2
0.7706	Intermediate Similarity	NPD3028	Approved
0.7705	Intermediate Similarity	NPD5327	Phase 3
0.7672	Intermediate Similarity	NPD5283	Phase 1
0.7667	Intermediate Similarity	NPD4626	Approved
0.7647	Intermediate Similarity	NPD5304	Approved
0.7647	Intermediate Similarity	NPD5303	Approved
0.7642	Intermediate Similarity	NPD1283	Approved
0.7619	Intermediate Similarity	NPD4625	Phase 3
0.7615	Intermediate Similarity	NPD7743	Approved
0.7615	Intermediate Similarity	NPD7742	Approved
0.7607	Intermediate Similarity	NPD497	Approved
0.7597	Intermediate Similarity	NPD4097	Suspended
0.7583	Intermediate Similarity	NPD1651	Approved
0.7581	Intermediate Similarity	NPD1470	Approved
0.7578	Intermediate Similarity	NPD4140	Approved
0.7578	Intermediate Similarity	NPD4060	Phase 1
0.7541	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD495	Approved
0.7521	Intermediate Similarity	NPD496	Approved
0.7521	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD498	Approved
0.7521	Intermediate Similarity	NPD4589	Approved
0.7521	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.752	Intermediate Similarity	NPD6584	Phase 3
0.7519	Intermediate Similarity	NPD5735	Approved
0.75	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7478	Intermediate Similarity	NPD5451	Approved
0.7462	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD6353	Approved
0.746	Intermediate Similarity	NPD2861	Phase 2
0.7444	Intermediate Similarity	NPD7037	Approved
0.7422	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD1669	Approved
0.7402	Intermediate Similarity	NPD4908	Phase 1
0.7398	Intermediate Similarity	NPD1281	Approved
0.7395	Intermediate Similarity	NPD6671	Approved
0.7388	Intermediate Similarity	NPD3638	Discontinued
0.7368	Intermediate Similarity	NPD4725	Approved
0.7368	Intermediate Similarity	NPD4726	Approved
0.7368	Intermediate Similarity	NPD4721	Approved
0.735	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD228	Approved
0.7348	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD2232	Approved
0.7339	Intermediate Similarity	NPD2233	Approved
0.7339	Intermediate Similarity	NPD2230	Approved
0.7295	Intermediate Similarity	NPD5691	Approved
0.7293	Intermediate Similarity	NPD5408	Approved
0.7293	Intermediate Similarity	NPD5404	Approved
0.7293	Intermediate Similarity	NPD5406	Approved
0.7293	Intermediate Similarity	NPD5405	Approved
0.7288	Intermediate Similarity	NPD5535	Approved
0.7287	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD4659	Approved
0.728	Intermediate Similarity	NPD6582	Phase 2
0.728	Intermediate Similarity	NPD4749	Approved
0.728	Intermediate Similarity	NPD6583	Phase 3
0.7279	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD1610	Phase 2
0.7257	Intermediate Similarity	NPD9500	Approved
0.725	Intermediate Similarity	NPD709	Approved
0.7236	Intermediate Similarity	NPD2667	Approved
0.7236	Intermediate Similarity	NPD2668	Approved
0.7231	Intermediate Similarity	NPD8032	Phase 2
0.7227	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7095	Approved
0.7206	Intermediate Similarity	NPD8166	Discontinued
0.7193	Intermediate Similarity	NPD9610	Approved
0.7193	Intermediate Similarity	NPD9608	Approved
0.719	Intermediate Similarity	NPD7340	Approved
0.7174	Intermediate Similarity	NPD7041	Phase 2
0.7174	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD2421	Approved
0.7174	Intermediate Similarity	NPD2420	Approved
0.7167	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD1791	Approved
0.7167	Intermediate Similarity	NPD5951	Approved
0.7167	Intermediate Similarity	NPD1793	Approved
0.7165	Intermediate Similarity	NPD3055	Approved
0.7165	Intermediate Similarity	NPD4103	Phase 2
0.7165	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD3053	Approved
0.7154	Intermediate Similarity	NPD3764	Approved
0.7143	Intermediate Similarity	NPD9379	Approved
0.7143	Intermediate Similarity	NPD9377	Approved
0.7143	Intermediate Similarity	NPD7718	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD2684	Approved
0.709	Intermediate Similarity	NPD4108	Discontinued
0.7087	Intermediate Similarity	NPD5310	Approved
0.7087	Intermediate Similarity	NPD5311	Approved
0.7087	Intermediate Similarity	NPD6696	Suspended
0.7083	Intermediate Similarity	NPD1398	Phase 1
0.708	Intermediate Similarity	NPD7003	Approved
0.7077	Intermediate Similarity	NPD3027	Phase 3
0.7073	Intermediate Similarity	NPD7330	Discontinued
0.7069	Intermediate Similarity	NPD968	Approved
0.7059	Intermediate Similarity	NPD4257	Approved
0.7059	Intermediate Similarity	NPD4256	Phase 2
0.705	Intermediate Similarity	NPD7390	Discontinued
0.7049	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6346	Approved
0.7045	Intermediate Similarity	NPD3110	Approved
0.7045	Intermediate Similarity	NPD3109	Approved
0.7045	Intermediate Similarity	NPD2979	Phase 3
0.7025	Intermediate Similarity	NPD475	Phase 2
0.7023	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3645	Discontinued
0.6992	Remote Similarity	NPD3657	Discovery
0.6985	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD1611	Approved
0.6978	Remote Similarity	NPD3845	Phase 1
0.6977	Remote Similarity	NPD7451	Discontinued
0.6967	Remote Similarity	NPD7157	Approved
0.696	Remote Similarity	NPD6516	Phase 2
0.696	Remote Similarity	NPD5846	Approved
0.695	Remote Similarity	NPD3364	Phase 3
0.695	Remote Similarity	NPD6273	Approved
0.6935	Remote Similarity	NPD1548	Phase 1
0.693	Remote Similarity	NPD1616	Discontinued
0.6929	Remote Similarity	NPD1608	Approved
0.6929	Remote Similarity	NPD2561	Approved
0.6929	Remote Similarity	NPD2562	Approved
0.6917	Remote Similarity	NPD2238	Phase 2
0.6912	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD8131	Suspended
0.6905	Remote Similarity	NPD1980	Approved
0.6905	Remote Similarity	NPD1981	Approved
0.6905	Remote Similarity	NPD1983	Approved
0.6905	Remote Similarity	NPD3847	Discontinued
0.6905	Remote Similarity	NPD3421	Phase 3
0.6899	Remote Similarity	NPD2797	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