NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	250.16
Volume:	263.425
LogP:	2.468
LogD:	2.134
LogS:	-3.548
# Rotatable Bonds:	0
TPSA:	49.83
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.53
Synthetic Accessibility Score:	5.069
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.661
MDCK Permeability:	1.757706922944635e-05
Pgp-inhibitor:	0.014
Pgp-substrate:	0.046
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.031
30% Bioavailability (F30%):	0.039

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.917
Plasma Protein Binding (PPB):	70.4128646850586%
Volume Distribution (VD):	1.462
Pgp-substrate:	21.616159439086914%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.788
CYP2C19-inhibitor:	0.057
CYP2C19-substrate:	0.835
CYP2C9-inhibitor:	0.03
CYP2C9-substrate:	0.08
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.106
CYP3A4-inhibitor:	0.255
CYP3A4-substrate:	0.729

ADMET: Excretion

Clearance (CL):	11.211
Half-life (T1/2):	0.437

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.234
Drug-inuced Liver Injury (DILI):	0.728
AMES Toxicity:	0.905
Rat Oral Acute Toxicity:	0.878
Maximum Recommended Daily Dose:	0.375
Skin Sensitization:	0.902
Carcinogencity:	0.963
Eye Corrosion:	0.586
Eye Irritation:	0.457
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC90446

Natural Product ID:	NPC90446
*Common Name:**	Oxycurcumenol Epoxide
IUPAC Name:	(1S,3aS,7S,8aS)-8a-hydroxy-1,3',3',4-tetramethylspiro[2,3,3a,8-tetrahydro-1H-azulene-7,2'-oxirane]-6-one
Synonyms:	Oxycurcumenol Epoxide
Standard InCHIKey:	QKVASKAIMFWWHV-LWWSYDQCSA-N
Standard InCHI:	InChI=1S/C15H22O3/c1-9-7-12(16)15(13(3,4)18-15)8-14(17)10(2)5-6-11(9)14/h7,10-11,17H,5-6,8H2,1-4H3/t10-,11-,14-,15+/m0/s1
SMILES:	CC1=CC(=O)[C@]2(C[C@@]3([C@@H](C)CC[C@@H]13)O)C(C)(C)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2332432
PubChem CID:	10264129
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002874] Guaianes

*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
NPO17780	Curcuma heyneana	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[23387824]
NPO18068	Curcuma phaeocaulis	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[23755850]
NPO18068	Curcuma phaeocaulis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17780	Curcuma heyneana	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18068	Curcuma phaeocaulis	Species	Zingiberaceae	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
IC50	1
Others	1

Activity Type	# Activity
Cell Line	1
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	<	65.0	%	PMID[548337]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	57400.0	nM	PMID[548338]

☑ 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 NPC90446 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	199
0.1-0.2	1652
0.2-0.3	7939
0.3-0.4	16476
0.4-0.5	9052
0.5-0.6	5614
0.6-0.7	1654
0.7-0.8	109
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8148	Intermediate Similarity	NPC77501
0.7901	Intermediate Similarity	NPC300940
0.7765	Intermediate Similarity	NPC66677
0.7765	Intermediate Similarity	NPC84185
0.7765	Intermediate Similarity	NPC471890
0.7674	Intermediate Similarity	NPC30675
0.7674	Intermediate Similarity	NPC164218
0.7629	Intermediate Similarity	NPC477356
0.7619	Intermediate Similarity	NPC115719
0.7619	Intermediate Similarity	NPC141346
0.7619	Intermediate Similarity	NPC142759
0.7619	Intermediate Similarity	NPC25908
0.7619	Intermediate Similarity	NPC473437
0.7619	Intermediate Similarity	NPC124289
0.7604	Intermediate Similarity	NPC477355
0.759	Intermediate Similarity	NPC7382
0.7561	Intermediate Similarity	NPC469737
0.7528	Intermediate Similarity	NPC475796
0.7528	Intermediate Similarity	NPC165287
0.75	Intermediate Similarity	NPC89374
0.75	Intermediate Similarity	NPC87090
0.75	Intermediate Similarity	NPC251435
0.7447	Intermediate Similarity	NPC125180
0.7423	Intermediate Similarity	NPC470541
0.7423	Intermediate Similarity	NPC109556
0.7412	Intermediate Similarity	NPC215481
0.7396	Intermediate Similarity	NPC477354
0.7391	Intermediate Similarity	NPC476706
0.7391	Intermediate Similarity	NPC476707
0.7391	Intermediate Similarity	NPC315911
0.7381	Intermediate Similarity	NPC469691
0.7381	Intermediate Similarity	NPC167049
0.7374	Intermediate Similarity	NPC118405
0.7353	Intermediate Similarity	NPC117604
0.7333	Intermediate Similarity	NPC156485
0.7317	Intermediate Similarity	NPC477449
0.7317	Intermediate Similarity	NPC477448
0.7303	Intermediate Similarity	NPC256750
0.7303	Intermediate Similarity	NPC133844
0.7303	Intermediate Similarity	NPC20262
0.7294	Intermediate Similarity	NPC469678
0.7294	Intermediate Similarity	NPC469669
0.7294	Intermediate Similarity	NPC475771
0.7283	Intermediate Similarity	NPC197333
0.7283	Intermediate Similarity	NPC471739
0.7273	Intermediate Similarity	NPC237190
0.7273	Intermediate Similarity	NPC206079
0.7263	Intermediate Similarity	NPC202824
0.7263	Intermediate Similarity	NPC475488
0.7263	Intermediate Similarity	NPC477361
0.7262	Intermediate Similarity	NPC92909
0.7262	Intermediate Similarity	NPC107783
0.7245	Intermediate Similarity	NPC64742
0.7245	Intermediate Similarity	NPC221615
0.7241	Intermediate Similarity	NPC476627
0.7222	Intermediate Similarity	NPC473629
0.7209	Intermediate Similarity	NPC182848
0.7209	Intermediate Similarity	NPC226242
0.7191	Intermediate Similarity	NPC39411
0.7191	Intermediate Similarity	NPC255580
0.7191	Intermediate Similarity	NPC78677
0.7191	Intermediate Similarity	NPC59994
0.7188	Intermediate Similarity	NPC298919
0.7176	Intermediate Similarity	NPC206875
0.7172	Intermediate Similarity	NPC280963
0.7159	Intermediate Similarity	NPC476624
0.7159	Intermediate Similarity	NPC472013
0.7158	Intermediate Similarity	NPC476705
0.7157	Intermediate Similarity	NPC314244
0.7143	Intermediate Similarity	NPC207689
0.7143	Intermediate Similarity	NPC144258
0.7128	Intermediate Similarity	NPC170775
0.7126	Intermediate Similarity	NPC195785
0.7126	Intermediate Similarity	NPC472014
0.7126	Intermediate Similarity	NPC15975
0.7126	Intermediate Similarity	NPC53581
0.7126	Intermediate Similarity	NPC103987
0.7113	Intermediate Similarity	NPC67584
0.7113	Intermediate Similarity	NPC52044
0.71	Intermediate Similarity	NPC207885
0.71	Intermediate Similarity	NPC112613
0.71	Intermediate Similarity	NPC164598
0.71	Intermediate Similarity	NPC474339
0.71	Intermediate Similarity	NPC477950
0.7097	Intermediate Similarity	NPC237540
0.7097	Intermediate Similarity	NPC471738
0.7079	Intermediate Similarity	NPC233352
0.7079	Intermediate Similarity	NPC824
0.7079	Intermediate Similarity	NPC138492
0.7065	Intermediate Similarity	NPC476628
0.7065	Intermediate Similarity	NPC15838
0.7065	Intermediate Similarity	NPC36350
0.7065	Intermediate Similarity	NPC132629
0.7065	Intermediate Similarity	NPC96621
0.7059	Intermediate Similarity	NPC309190
0.7059	Intermediate Similarity	NPC474741
0.7053	Intermediate Similarity	NPC301969
0.7053	Intermediate Similarity	NPC37607
0.7045	Intermediate Similarity	NPC19443
0.7045	Intermediate Similarity	NPC321180
0.7041	Intermediate Similarity	NPC9812
0.7041	Intermediate Similarity	NPC213078
0.7041	Intermediate Similarity	NPC94337
0.7037	Intermediate Similarity	NPC205618
0.7037	Intermediate Similarity	NPC261782
0.7037	Intermediate Similarity	NPC469326
0.7033	Intermediate Similarity	NPC62214
0.7033	Intermediate Similarity	NPC108045
0.7033	Intermediate Similarity	NPC475622
0.703	Intermediate Similarity	NPC478176
0.7021	Intermediate Similarity	NPC224652
0.7021	Intermediate Similarity	NPC475902
0.701	Intermediate Similarity	NPC124207
0.7	Intermediate Similarity	NPC112167
0.7	Intermediate Similarity	NPC286229
0.7	Intermediate Similarity	NPC474353
0.7	Intermediate Similarity	NPC470241
0.7	Intermediate Similarity	NPC171665
0.699	Remote Similarity	NPC190867
0.6989	Remote Similarity	NPC67493
0.6989	Remote Similarity	NPC476043
0.6979	Remote Similarity	NPC26865
0.6979	Remote Similarity	NPC144629
0.6977	Remote Similarity	NPC469641
0.6977	Remote Similarity	NPC472966
0.6977	Remote Similarity	NPC469643
0.6972	Remote Similarity	NPC475305
0.697	Remote Similarity	NPC161493
0.697	Remote Similarity	NPC471916
0.697	Remote Similarity	NPC477949
0.697	Remote Similarity	NPC470834
0.6966	Remote Similarity	NPC471740
0.6966	Remote Similarity	NPC276647
0.6966	Remote Similarity	NPC301769
0.6966	Remote Similarity	NPC261125
0.6966	Remote Similarity	NPC622
0.6966	Remote Similarity	NPC32758
0.6966	Remote Similarity	NPC181195
0.6961	Remote Similarity	NPC470839
0.6957	Remote Similarity	NPC120726
0.6957	Remote Similarity	NPC472480
0.6957	Remote Similarity	NPC32565
0.6951	Remote Similarity	NPC197089
0.6947	Remote Similarity	NPC41217
0.6947	Remote Similarity	NPC212664
0.6947	Remote Similarity	NPC326627
0.6947	Remote Similarity	NPC310010
0.6941	Remote Similarity	NPC106309
0.6941	Remote Similarity	NPC144627
0.6939	Remote Similarity	NPC469873
0.6939	Remote Similarity	NPC261341
0.6923	Remote Similarity	NPC193347
0.6923	Remote Similarity	NPC89555
0.6915	Remote Similarity	NPC201658
0.6909	Remote Similarity	NPC475401
0.6907	Remote Similarity	NPC233118
0.6907	Remote Similarity	NPC109414
0.6905	Remote Similarity	NPC144647
0.69	Remote Similarity	NPC244411
0.6889	Remote Similarity	NPC45495
0.6882	Remote Similarity	NPC471185
0.6882	Remote Similarity	NPC165162
0.6882	Remote Similarity	NPC78089
0.6882	Remote Similarity	NPC245434
0.6875	Remote Similarity	NPC2946
0.6875	Remote Similarity	NPC477684
0.6875	Remote Similarity	NPC129419
0.6875	Remote Similarity	NPC77337
0.6869	Remote Similarity	NPC272411
0.6867	Remote Similarity	NPC476626
0.6863	Remote Similarity	NPC25639
0.6863	Remote Similarity	NPC474747
0.6854	Remote Similarity	NPC207772
0.6854	Remote Similarity	NPC474056
0.6848	Remote Similarity	NPC245665
0.6847	Remote Similarity	NPC477092
0.6842	Remote Similarity	NPC241507
0.6842	Remote Similarity	NPC53158
0.6842	Remote Similarity	NPC476708
0.6842	Remote Similarity	NPC471941
0.6837	Remote Similarity	NPC127019
0.6837	Remote Similarity	NPC167219
0.6837	Remote Similarity	NPC121825
0.6837	Remote Similarity	NPC477131
0.6835	Remote Similarity	NPC469321
0.6832	Remote Similarity	NPC469872
0.6832	Remote Similarity	NPC469864
0.6827	Remote Similarity	NPC44004
0.6824	Remote Similarity	NPC280256
0.6822	Remote Similarity	NPC475495
0.6818	Remote Similarity	NPC271070
0.6813	Remote Similarity	NPC136150
0.6809	Remote Similarity	NPC261721
0.6809	Remote Similarity	NPC107787
0.6804	Remote Similarity	NPC300312
0.6804	Remote Similarity	NPC133698
0.6804	Remote Similarity	NPC111114
0.6804	Remote Similarity	NPC155215
0.6804	Remote Similarity	NPC20713
0.6804	Remote Similarity	NPC261607

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 NPC90446 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	199
0.1-0.2	2329
0.2-0.3	4267
0.3-0.4	1659
0.4-0.5	414
0.5-0.6	176
0.6-0.7	105
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7188	Intermediate Similarity	NPD5282	Discontinued
0.7143	Intermediate Similarity	NPD4197	Approved
0.7113	Intermediate Similarity	NPD5695	Phase 3
0.7071	Intermediate Similarity	NPD5696	Approved
0.7065	Intermediate Similarity	NPD5329	Approved
0.7	Intermediate Similarity	NPD5369	Approved
0.6989	Remote Similarity	NPD4694	Approved
0.6989	Remote Similarity	NPD5690	Phase 2
0.6989	Remote Similarity	NPD5280	Approved
0.697	Remote Similarity	NPD6084	Phase 2
0.697	Remote Similarity	NPD6083	Phase 2
0.6947	Remote Similarity	NPD4753	Phase 2
0.6923	Remote Similarity	NPD4223	Phase 3
0.6923	Remote Similarity	NPD4221	Approved
0.6809	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD6904	Approved
0.6771	Remote Similarity	NPD6080	Approved
0.6771	Remote Similarity	NPD1695	Approved
0.6771	Remote Similarity	NPD6673	Approved
0.6768	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD5210	Approved
0.6768	Remote Similarity	NPD4629	Approved
0.6762	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD6371	Approved
0.6702	Remote Similarity	NPD5363	Approved
0.6701	Remote Similarity	NPD5692	Phase 3
0.6667	Remote Similarity	NPD7128	Approved
0.6667	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD6675	Approved
0.6667	Remote Similarity	NPD6402	Approved
0.6667	Remote Similarity	NPD4518	Approved
0.6636	Remote Similarity	NPD6373	Approved
0.6636	Remote Similarity	NPD6372	Approved
0.6634	Remote Similarity	NPD4755	Approved
0.6633	Remote Similarity	NPD5284	Approved
0.6633	Remote Similarity	NPD6050	Approved
0.6633	Remote Similarity	NPD5693	Phase 1
0.6633	Remote Similarity	NPD5694	Approved
0.6633	Remote Similarity	NPD5281	Approved
0.6632	Remote Similarity	NPD4693	Phase 3
0.6632	Remote Similarity	NPD5205	Approved
0.6632	Remote Similarity	NPD6098	Approved
0.6632	Remote Similarity	NPD4688	Approved
0.6632	Remote Similarity	NPD4138	Approved
0.6632	Remote Similarity	NPD4690	Approved
0.6632	Remote Similarity	NPD5279	Phase 3
0.6632	Remote Similarity	NPD4689	Approved
0.6604	Remote Similarity	NPD5701	Approved
0.6604	Remote Similarity	NPD5697	Approved
0.6566	Remote Similarity	NPD5133	Approved
0.6559	Remote Similarity	NPD6435	Approved
0.6559	Remote Similarity	NPD4270	Approved
0.6559	Remote Similarity	NPD4269	Approved
0.6548	Remote Similarity	NPD7331	Phase 2
0.6542	Remote Similarity	NPD6899	Approved
0.6542	Remote Similarity	NPD7320	Approved
0.6542	Remote Similarity	NPD6881	Approved
0.6531	Remote Similarity	NPD5785	Approved
0.6522	Remote Similarity	NPD4695	Discontinued
0.6514	Remote Similarity	NPD6649	Approved
0.6514	Remote Similarity	NPD6650	Approved
0.6505	Remote Similarity	NPD5285	Approved
0.6505	Remote Similarity	NPD5286	Approved
0.6505	Remote Similarity	NPD4700	Approved
0.6505	Remote Similarity	NPD4696	Approved
0.6495	Remote Similarity	NPD5737	Approved
0.6495	Remote Similarity	NPD6672	Approved
0.6484	Remote Similarity	NPD3617	Approved
0.6481	Remote Similarity	NPD6013	Approved
0.6481	Remote Similarity	NPD6012	Approved
0.6481	Remote Similarity	NPD6014	Approved
0.6458	Remote Similarity	NPD5786	Approved
0.6429	Remote Similarity	NPD7341	Phase 2
0.6422	Remote Similarity	NPD6883	Approved
0.6422	Remote Similarity	NPD7290	Approved
0.6422	Remote Similarity	NPD7102	Approved
0.6421	Remote Similarity	NPD3133	Approved
0.6421	Remote Similarity	NPD3666	Approved
0.6421	Remote Similarity	NPD3665	Phase 1
0.64	Remote Similarity	NPD6399	Phase 3
0.64	Remote Similarity	NPD4202	Approved
0.6389	Remote Similarity	NPD6011	Approved
0.6381	Remote Similarity	NPD5225	Approved
0.6381	Remote Similarity	NPD4633	Approved
0.6381	Remote Similarity	NPD5226	Approved
0.6381	Remote Similarity	NPD5211	Phase 2
0.6381	Remote Similarity	NPD5224	Approved
0.6364	Remote Similarity	NPD5207	Approved
0.6364	Remote Similarity	NPD6869	Approved
0.6364	Remote Similarity	NPD6847	Approved
0.6364	Remote Similarity	NPD6617	Approved
0.6364	Remote Similarity	NPD8130	Phase 1
0.6364	Remote Similarity	NPD4096	Approved
0.6344	Remote Similarity	NPD4252	Approved
0.6344	Remote Similarity	NPD5368	Approved
0.6337	Remote Similarity	NPD6001	Approved
0.6327	Remote Similarity	NPD5208	Approved
0.6321	Remote Similarity	NPD5175	Approved
0.6321	Remote Similarity	NPD5174	Approved
0.6316	Remote Similarity	NPD5362	Discontinued
0.6311	Remote Similarity	NPD5959	Approved
0.6306	Remote Similarity	NPD8297	Approved
0.6306	Remote Similarity	NPD6882	Approved
0.6289	Remote Similarity	NPD3618	Phase 1
0.6286	Remote Similarity	NPD5223	Approved
0.6275	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD5654	Approved
0.6273	Remote Similarity	NPD4634	Approved
0.6262	Remote Similarity	NPD5141	Approved
0.625	Remote Similarity	NPD4786	Approved
0.6237	Remote Similarity	NPD4195	Approved
0.6228	Remote Similarity	NPD7115	Discovery
0.6226	Remote Similarity	NPD5091	Approved
0.6216	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD4697	Phase 3
0.6211	Remote Similarity	NPD3667	Approved
0.6207	Remote Similarity	NPD6059	Approved
0.6207	Remote Similarity	NPD6054	Approved
0.6207	Remote Similarity	NPD6319	Approved
0.6204	Remote Similarity	NPD6008	Approved
0.6204	Remote Similarity	NPD4767	Approved
0.6204	Remote Similarity	NPD4768	Approved
0.619	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.617	Remote Similarity	NPD4822	Approved
0.617	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.617	Remote Similarity	NPD4819	Approved
0.617	Remote Similarity	NPD4820	Approved
0.617	Remote Similarity	NPD4821	Approved
0.6168	Remote Similarity	NPD4754	Approved
0.6154	Remote Similarity	NPD6016	Approved
0.6154	Remote Similarity	NPD6015	Approved
0.614	Remote Similarity	NPD6274	Approved
0.6122	Remote Similarity	NPD7521	Approved
0.6122	Remote Similarity	NPD5330	Approved
0.6122	Remote Similarity	NPD7334	Approved
0.6122	Remote Similarity	NPD6409	Approved
0.6122	Remote Similarity	NPD6684	Approved
0.6122	Remote Similarity	NPD7146	Approved
0.6105	Remote Similarity	NPD4139	Approved
0.6105	Remote Similarity	NPD4692	Approved
0.6102	Remote Similarity	NPD5988	Approved
0.6102	Remote Similarity	NPD6370	Approved
0.61	Remote Similarity	NPD5328	Approved
0.6091	Remote Similarity	NPD4729	Approved
0.6091	Remote Similarity	NPD4730	Approved
0.6091	Remote Similarity	NPD5128	Approved
0.6058	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD5222	Approved
0.6058	Remote Similarity	NPD5221	Approved
0.604	Remote Similarity	NPD46	Approved
0.604	Remote Similarity	NPD6698	Approved
0.602	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.602	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD6053	Discontinued
0.6	Remote Similarity	NPD7492	Approved
0.6	Remote Similarity	NPD5173	Approved
0.6	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6903	Approved
0.6	Remote Similarity	NPD6614	Approved
0.5983	Remote Similarity	NPD7101	Approved
0.5983	Remote Similarity	NPD7100	Approved
0.5982	Remote Similarity	NPD5249	Phase 3
0.5982	Remote Similarity	NPD5247	Approved
0.5982	Remote Similarity	NPD5248	Approved
0.5982	Remote Similarity	NPD5250	Approved
0.5982	Remote Similarity	NPD5251	Approved
0.598	Remote Similarity	NPD6079	Approved
0.5979	Remote Similarity	NPD7154	Phase 3
0.5979	Remote Similarity	NPD4788	Approved
0.5977	Remote Similarity	NPD3704	Approved
0.5977	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.596	Remote Similarity	NPD4519	Discontinued
0.596	Remote Similarity	NPD4623	Approved
0.5957	Remote Similarity	NPD4271	Approved
0.5957	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD4268	Approved
0.595	Remote Similarity	NPD6616	Approved
0.5948	Remote Similarity	NPD6317	Approved
0.5941	Remote Similarity	NPD6101	Approved
0.5941	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD5217	Approved
0.5929	Remote Similarity	NPD5216	Approved
0.5929	Remote Similarity	NPD5215	Approved
0.5902	Remote Similarity	NPD8293	Discontinued
0.5902	Remote Similarity	NPD7078	Approved
0.5897	Remote Similarity	NPD6313	Approved
0.5897	Remote Similarity	NPD6335	Approved
0.5897	Remote Similarity	NPD6314	Approved
0.5889	Remote Similarity	NPD4747	Approved
0.5882	Remote Similarity	NPD6909	Approved
0.5882	Remote Similarity	NPD6908	Approved
0.5859	Remote Similarity	NPD1696	Phase 3
0.5856	Remote Similarity	NPD6412	Phase 2
0.5854	Remote Similarity	NPD7736	Approved
0.5851	Remote Similarity	NPD4756	Discovery
0.5847	Remote Similarity	NPD4522	Approved
0.5841	Remote Similarity	NPD5169	Approved
0.5841	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD5135	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