NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	334.25
Volume:	361.281
LogP:	3.948
LogD:	3.897
LogS:	-4.798
# Rotatable Bonds:	0
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.671
Synthetic Accessibility Score:	5.494
Fsp3:	0.952
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.875
MDCK Permeability:	2.4749346266617067e-05
Pgp-inhibitor:	0.64
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.724
30% Bioavailability (F30%):	0.955

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.121
Plasma Protein Binding (PPB):	96.31768798828125%
Volume Distribution (VD):	1.093
Pgp-substrate:	2.7532570362091064%

ADMET: Metabolism

CYP1A2-inhibitor:	0.067
CYP1A2-substrate:	0.366
CYP2C19-inhibitor:	0.086
CYP2C19-substrate:	0.901
CYP2C9-inhibitor:	0.216
CYP2C9-substrate:	0.283
CYP2D6-inhibitor:	0.119
CYP2D6-substrate:	0.256
CYP3A4-inhibitor:	0.873
CYP3A4-substrate:	0.39

ADMET: Excretion

Clearance (CL):	5.619
Half-life (T1/2):	0.294

ADMET: Toxicity

hERG Blockers:	0.064
Human Hepatotoxicity (H-HT):	0.141
Drug-inuced Liver Injury (DILI):	0.132
AMES Toxicity:	0.051
Rat Oral Acute Toxicity:	0.043
Maximum Recommended Daily Dose:	0.801
Skin Sensitization:	0.849
Carcinogencity:	0.212
Eye Corrosion:	0.394
Eye Irritation:	0.923
Respiratory Toxicity:	0.904

Download Data

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

Natural Product: NPC478227

Natural Product ID:	NPC478227
*Common Name:**	(1R,2R,5S,6R,8R,11S)-6-hydroxy-5,6,8,12-tetramethyl-14-oxatetracyclo[10.3.3.01,11.02,8]octadecan-13-one
IUPAC Name:	(1R,2R,5S,6R,8R,11S)-6-hydroxy-5,6,8,12-tetramethyl-14-oxatetracyclo[10.3.3.01,11.02,8]octadecan-13-one
Synonyms:
Standard InCHIKey:	VVKQWVWKEMJKNY-XTKBPKJXSA-N
Standard InCHI:	InChI=1S/C21H34O3/c1-14-6-7-15-18(2,12-20(14,4)23)11-8-16-19(3)9-5-10-21(15,16)13-24-17(19)22/h14-16,23H,5-13H2,1-4H3/t14-,15+,16+,18+,19?,20+,21+/m0/s1
SMILES:	C[C@H]1CC[C@@H]2[C@](CC[C@H]3[C@@]24CCCC3(C(=O)OC4)C)(C[C@@]1(C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	162818712
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001244] Delta valerolactones

*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
NPO33694	Ligularia f ischeri	Species	Asteraceae	Eukaryota	leaves and roots	Baoji, Shanxi Province, China	2013-AUG	PMID[28783337]

☑ 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

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

☑ 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 NPC478227 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	387
0.1-0.2	3311
0.2-0.3	13797
0.3-0.4	10653
0.4-0.5	6773
0.5-0.6	5711
0.6-0.7	1798
0.7-0.8	251
0.8-0.85	15
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8551	High Similarity	NPC41542
0.8493	Intermediate Similarity	NPC179858
0.8333	Intermediate Similarity	NPC469940
0.831	Intermediate Similarity	NPC178541
0.8261	Intermediate Similarity	NPC230047
0.8261	Intermediate Similarity	NPC19311
0.8194	Intermediate Similarity	NPC477929
0.8169	Intermediate Similarity	NPC478228
0.8056	Intermediate Similarity	NPC469941
0.8056	Intermediate Similarity	NPC252032
0.8056	Intermediate Similarity	NPC476734
0.8056	Intermediate Similarity	NPC319671
0.8026	Intermediate Similarity	NPC477918
0.8026	Intermediate Similarity	NPC474404
0.8	Intermediate Similarity	NPC469791
0.8	Intermediate Similarity	NPC477934
0.7949	Intermediate Similarity	NPC472853
0.7922	Intermediate Similarity	NPC31031
0.7922	Intermediate Similarity	NPC199965
0.7922	Intermediate Similarity	NPC476732
0.7922	Intermediate Similarity	NPC243594
0.7917	Intermediate Similarity	NPC474954
0.7917	Intermediate Similarity	NPC31187
0.7917	Intermediate Similarity	NPC281203
0.7917	Intermediate Similarity	NPC469724
0.7917	Intermediate Similarity	NPC470956
0.7917	Intermediate Similarity	NPC100917
0.7895	Intermediate Similarity	NPC477933
0.7895	Intermediate Similarity	NPC477932
0.7887	Intermediate Similarity	NPC42060
0.7867	Intermediate Similarity	NPC167702
0.7867	Intermediate Similarity	NPC280026
0.7867	Intermediate Similarity	NPC74639
0.7848	Intermediate Similarity	NPC58631
0.7848	Intermediate Similarity	NPC280781
0.7848	Intermediate Similarity	NPC48756
0.7826	Intermediate Similarity	NPC306750
0.7808	Intermediate Similarity	NPC64466
0.7808	Intermediate Similarity	NPC295788
0.7808	Intermediate Similarity	NPC196197
0.7792	Intermediate Similarity	NPC180199
0.7792	Intermediate Similarity	NPC477919
0.7778	Intermediate Similarity	NPC476928
0.7763	Intermediate Similarity	NPC472311
0.7763	Intermediate Similarity	NPC212733
0.775	Intermediate Similarity	NPC102156
0.775	Intermediate Similarity	NPC61107
0.775	Intermediate Similarity	NPC477936
0.775	Intermediate Similarity	NPC477935
0.775	Intermediate Similarity	NPC148740
0.775	Intermediate Similarity	NPC289486
0.7733	Intermediate Similarity	NPC475230
0.7722	Intermediate Similarity	NPC261616
0.7703	Intermediate Similarity	NPC108131
0.7703	Intermediate Similarity	NPC477850
0.7692	Intermediate Similarity	NPC185465
0.7671	Intermediate Similarity	NPC260319
0.7671	Intermediate Similarity	NPC180777
0.7671	Intermediate Similarity	NPC103647
0.7671	Intermediate Similarity	NPC2568
0.7662	Intermediate Similarity	NPC4209
0.7662	Intermediate Similarity	NPC471046
0.7662	Intermediate Similarity	NPC474020
0.7639	Intermediate Similarity	NPC84562
0.7639	Intermediate Similarity	NPC268736
0.7639	Intermediate Similarity	NPC477931
0.7632	Intermediate Similarity	NPC477930
0.7632	Intermediate Similarity	NPC96759
0.7625	Intermediate Similarity	NPC48673
0.7625	Intermediate Similarity	NPC476071
0.7625	Intermediate Similarity	NPC474870
0.7625	Intermediate Similarity	NPC20096
0.7625	Intermediate Similarity	NPC271572
0.76	Intermediate Similarity	NPC197701
0.76	Intermediate Similarity	NPC472309
0.7595	Intermediate Similarity	NPC320144
0.7595	Intermediate Similarity	NPC80891
0.7595	Intermediate Similarity	NPC201276
0.7568	Intermediate Similarity	NPC474962
0.7564	Intermediate Similarity	NPC317913
0.7564	Intermediate Similarity	NPC112463
0.7564	Intermediate Similarity	NPC143133
0.7564	Intermediate Similarity	NPC298168
0.7564	Intermediate Similarity	NPC307865
0.7564	Intermediate Similarity	NPC207010
0.7561	Intermediate Similarity	NPC237938
0.7561	Intermediate Similarity	NPC477434
0.7561	Intermediate Similarity	NPC219535
0.7534	Intermediate Similarity	NPC474221
0.7534	Intermediate Similarity	NPC130459
0.7534	Intermediate Similarity	NPC478180
0.7534	Intermediate Similarity	NPC472984
0.7531	Intermediate Similarity	NPC474605
0.7531	Intermediate Similarity	NPC164289
0.7531	Intermediate Similarity	NPC242771
0.7531	Intermediate Similarity	NPC476292
0.7531	Intermediate Similarity	NPC311642
0.7531	Intermediate Similarity	NPC100366
0.75	Intermediate Similarity	NPC109510
0.75	Intermediate Similarity	NPC125366
0.75	Intermediate Similarity	NPC81759
0.747	Intermediate Similarity	NPC62572
0.747	Intermediate Similarity	NPC131350
0.747	Intermediate Similarity	NPC477205
0.7468	Intermediate Similarity	NPC472608
0.7468	Intermediate Similarity	NPC26029
0.7468	Intermediate Similarity	NPC80089
0.7468	Intermediate Similarity	NPC329117
0.7468	Intermediate Similarity	NPC224802
0.7468	Intermediate Similarity	NPC34046
0.7468	Intermediate Similarity	NPC171426
0.7468	Intermediate Similarity	NPC324700
0.7467	Intermediate Similarity	NPC91369
0.7465	Intermediate Similarity	NPC235788
0.7439	Intermediate Similarity	NPC259173
0.7439	Intermediate Similarity	NPC472847
0.7439	Intermediate Similarity	NPC471037
0.7436	Intermediate Similarity	NPC104806
0.7436	Intermediate Similarity	NPC476601
0.7432	Intermediate Similarity	NPC473225
0.7412	Intermediate Similarity	NPC255176
0.7407	Intermediate Similarity	NPC327002
0.7407	Intermediate Similarity	NPC77311
0.7407	Intermediate Similarity	NPC12933
0.7403	Intermediate Similarity	NPC472854
0.7403	Intermediate Similarity	NPC55508
0.7381	Intermediate Similarity	NPC120395
0.7381	Intermediate Similarity	NPC83242
0.7381	Intermediate Similarity	NPC248216
0.7381	Intermediate Similarity	NPC92139
0.7375	Intermediate Similarity	NPC245029
0.7375	Intermediate Similarity	NPC73013
0.7375	Intermediate Similarity	NPC31302
0.7375	Intermediate Similarity	NPC472310
0.7368	Intermediate Similarity	NPC72343
0.7368	Intermediate Similarity	NPC156277
0.7368	Intermediate Similarity	NPC290058
0.7368	Intermediate Similarity	NPC151018
0.7368	Intermediate Similarity	NPC320549
0.7368	Intermediate Similarity	NPC58057
0.7349	Intermediate Similarity	NPC319909
0.7349	Intermediate Similarity	NPC156981
0.7349	Intermediate Similarity	NPC473299
0.7349	Intermediate Similarity	NPC471044
0.7349	Intermediate Similarity	NPC473336
0.7342	Intermediate Similarity	NPC66105
0.7333	Intermediate Similarity	NPC131892
0.7333	Intermediate Similarity	NPC324607
0.7333	Intermediate Similarity	NPC213178
0.7333	Intermediate Similarity	NPC327728
0.7333	Intermediate Similarity	NPC321732
0.7333	Intermediate Similarity	NPC6120
0.7317	Intermediate Similarity	NPC30583
0.7308	Intermediate Similarity	NPC125767
0.7308	Intermediate Similarity	NPC27349
0.7308	Intermediate Similarity	NPC24014
0.7308	Intermediate Similarity	NPC21220
0.7294	Intermediate Similarity	NPC239938
0.7294	Intermediate Similarity	NPC470920
0.7286	Intermediate Similarity	NPC469924
0.7284	Intermediate Similarity	NPC476265
0.7284	Intermediate Similarity	NPC274522
0.7284	Intermediate Similarity	NPC1882
0.7284	Intermediate Similarity	NPC477851
0.7273	Intermediate Similarity	NPC177826
0.7273	Intermediate Similarity	NPC36310
0.7273	Intermediate Similarity	NPC474123
0.7273	Intermediate Similarity	NPC477229
0.7273	Intermediate Similarity	NPC68426
0.7273	Intermediate Similarity	NPC282905
0.7273	Intermediate Similarity	NPC232112
0.7273	Intermediate Similarity	NPC248567
0.7273	Intermediate Similarity	NPC310766
0.7262	Intermediate Similarity	NPC477445
0.725	Intermediate Similarity	NPC476810
0.725	Intermediate Similarity	NPC321514
0.7241	Intermediate Similarity	NPC185529
0.7241	Intermediate Similarity	NPC472146
0.7241	Intermediate Similarity	NPC77756
0.7237	Intermediate Similarity	NPC476731
0.7229	Intermediate Similarity	NPC476100
0.7229	Intermediate Similarity	NPC269684
0.7229	Intermediate Similarity	NPC472744
0.7215	Intermediate Similarity	NPC472486
0.7215	Intermediate Similarity	NPC475742
0.7215	Intermediate Similarity	NPC472487
0.7215	Intermediate Similarity	NPC5767
0.7209	Intermediate Similarity	NPC56413
0.7209	Intermediate Similarity	NPC236459
0.7209	Intermediate Similarity	NPC476435
0.7209	Intermediate Similarity	NPC473319
0.7209	Intermediate Similarity	NPC3032
0.7209	Intermediate Similarity	NPC476379
0.7209	Intermediate Similarity	NPC131104
0.72	Intermediate Similarity	NPC290445
0.72	Intermediate Similarity	NPC36616
0.7195	Intermediate Similarity	NPC232625
0.7195	Intermediate Similarity	NPC50658
0.7191	Intermediate Similarity	NPC240617
0.7191	Intermediate Similarity	NPC470424

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 NPC478227 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	459
0.1-0.2	3450
0.2-0.3	3530
0.3-0.4	1070
0.4-0.5	339
0.5-0.6	235
0.6-0.7	42
0.7-0.8	24
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.875	High Similarity	NPD3702	Approved
0.7887	Intermediate Similarity	NPD4224	Phase 2
0.7867	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD5777	Approved
0.7662	Intermediate Similarity	NPD6117	Approved
0.76	Intermediate Similarity	NPD6081	Approved
0.7564	Intermediate Similarity	NPD6116	Phase 1
0.75	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD6115	Approved
0.7468	Intermediate Similarity	NPD6114	Approved
0.7468	Intermediate Similarity	NPD6697	Approved
0.7468	Intermediate Similarity	NPD6118	Approved
0.7467	Intermediate Similarity	NPD4244	Approved
0.7467	Intermediate Similarity	NPD4789	Approved
0.7467	Intermediate Similarity	NPD4245	Approved
0.7432	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD5360	Phase 3
0.7368	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3698	Phase 2
0.7089	Intermediate Similarity	NPD3703	Phase 2
0.6923	Remote Similarity	NPD4758	Discontinued
0.686	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD1780	Approved
0.6786	Remote Similarity	NPD1779	Approved
0.6778	Remote Similarity	NPD8034	Phase 2
0.6778	Remote Similarity	NPD8035	Phase 2
0.6703	Remote Similarity	NPD6399	Phase 3
0.6667	Remote Similarity	NPD3725	Approved
0.6667	Remote Similarity	NPD3726	Approved
0.663	Remote Similarity	NPD7748	Approved
0.6628	Remote Similarity	NPD4788	Approved
0.6628	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD3669	Approved
0.6627	Remote Similarity	NPD5364	Discontinued
0.6627	Remote Similarity	NPD3671	Phase 1
0.6596	Remote Similarity	NPD6083	Phase 2
0.6596	Remote Similarity	NPD6084	Phase 2
0.6591	Remote Similarity	NPD7334	Approved
0.6591	Remote Similarity	NPD6409	Approved
0.6591	Remote Similarity	NPD5330	Approved
0.6591	Remote Similarity	NPD7146	Approved
0.6591	Remote Similarity	NPD7521	Approved
0.6591	Remote Similarity	NPD6684	Approved
0.6575	Remote Similarity	NPD3198	Approved
0.6517	Remote Similarity	NPD3573	Approved
0.6447	Remote Similarity	NPD7909	Approved
0.6444	Remote Similarity	NPD6672	Approved
0.6444	Remote Similarity	NPD6903	Approved
0.6444	Remote Similarity	NPD5737	Approved
0.6444	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD7902	Approved
0.6418	Remote Similarity	NPD2266	Phase 2
0.6413	Remote Similarity	NPD6411	Approved
0.6413	Remote Similarity	NPD7515	Phase 2
0.6404	Remote Similarity	NPD6098	Approved
0.6383	Remote Similarity	NPD5695	Phase 3
0.6364	Remote Similarity	NPD634	Phase 3
0.6364	Remote Similarity	NPD4786	Approved
0.6354	Remote Similarity	NPD5696	Approved
0.6337	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD3667	Approved
0.63	Remote Similarity	NPD5739	Approved
0.63	Remote Similarity	NPD6402	Approved
0.63	Remote Similarity	NPD7128	Approved
0.63	Remote Similarity	NPD6675	Approved
0.6286	Remote Similarity	NPD3186	Phase 1
0.625	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD4238	Approved
0.6235	Remote Similarity	NPD4802	Phase 2
0.6235	Remote Similarity	NPD3617	Approved
0.6196	Remote Similarity	NPD6673	Approved
0.6196	Remote Similarity	NPD6080	Approved
0.6196	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD5328	Approved
0.6196	Remote Similarity	NPD6101	Approved
0.6196	Remote Similarity	NPD6904	Approved
0.618	Remote Similarity	NPD3665	Phase 1
0.618	Remote Similarity	NPD3133	Approved
0.618	Remote Similarity	NPD3666	Approved
0.6176	Remote Similarity	NPD6881	Approved
0.6176	Remote Similarity	NPD7320	Approved
0.6176	Remote Similarity	NPD6899	Approved
0.6173	Remote Similarity	NPD4787	Phase 1
0.6136	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD4223	Phase 3
0.6136	Remote Similarity	NPD4221	Approved
0.6117	Remote Similarity	NPD6372	Approved
0.6117	Remote Similarity	NPD6373	Approved
0.6111	Remote Similarity	NPD5329	Approved
0.6105	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD7900	Approved
0.6092	Remote Similarity	NPD6928	Phase 2
0.6087	Remote Similarity	NPD5208	Approved
0.6078	Remote Similarity	NPD5697	Approved
0.6078	Remote Similarity	NPD5701	Approved
0.6071	Remote Similarity	NPD2257	Approved
0.6064	Remote Similarity	NPD6079	Approved
0.6058	Remote Similarity	NPD7290	Approved
0.6058	Remote Similarity	NPD6883	Approved
0.6058	Remote Similarity	NPD7102	Approved
0.6044	Remote Similarity	NPD3618	Phase 1
0.6042	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.604	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD4692	Approved
0.6023	Remote Similarity	NPD4139	Approved
0.6022	Remote Similarity	NPD4753	Phase 2
0.602	Remote Similarity	NPD7638	Approved
0.6019	Remote Similarity	NPD6011	Approved
0.6	Remote Similarity	NPD6869	Approved
0.6	Remote Similarity	NPD6617	Approved
0.6	Remote Similarity	NPD4197	Approved
0.6	Remote Similarity	NPD8130	Phase 1
0.6	Remote Similarity	NPD6650	Approved
0.6	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6649	Approved
0.6	Remote Similarity	NPD6847	Approved
0.5979	Remote Similarity	NPD7614	Phase 1
0.597	Remote Similarity	NPD2699	Approved
0.5962	Remote Similarity	NPD6013	Approved
0.5962	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD6014	Approved
0.5962	Remote Similarity	NPD6012	Approved
0.596	Remote Similarity	NPD8418	Phase 2
0.596	Remote Similarity	NPD7640	Approved
0.596	Remote Similarity	NPD7639	Approved
0.5952	Remote Similarity	NPD1810	Approved
0.5952	Remote Similarity	NPD1811	Approved
0.5943	Remote Similarity	NPD6882	Approved
0.5943	Remote Similarity	NPD8297	Approved
0.5909	Remote Similarity	NPD4695	Discontinued
0.5909	Remote Similarity	NPD387	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD6050	Approved
0.5895	Remote Similarity	NPD5693	Phase 1
0.5895	Remote Similarity	NPD5284	Approved
0.5895	Remote Similarity	NPD5281	Approved
0.589	Remote Similarity	NPD3730	Approved
0.589	Remote Similarity	NPD3728	Approved
0.5888	Remote Similarity	NPD8133	Approved
0.587	Remote Similarity	NPD4138	Approved
0.587	Remote Similarity	NPD5205	Approved
0.587	Remote Similarity	NPD4688	Approved
0.587	Remote Similarity	NPD4690	Approved
0.587	Remote Similarity	NPD4693	Phase 3
0.587	Remote Similarity	NPD4519	Discontinued
0.587	Remote Similarity	NPD4623	Approved
0.587	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.587	Remote Similarity	NPD4689	Approved
0.5865	Remote Similarity	NPD6686	Approved
0.5842	Remote Similarity	NPD7632	Discontinued
0.5833	Remote Similarity	NPD4202	Approved
0.5825	Remote Similarity	NPD6920	Discontinued
0.5824	Remote Similarity	NPD3668	Phase 3
0.5816	Remote Similarity	NPD7732	Phase 3
0.5816	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.581	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD5692	Phase 3
0.5789	Remote Similarity	NPD5207	Approved
0.5783	Remote Similarity	NPD2687	Approved
0.5783	Remote Similarity	NPD2686	Approved
0.5783	Remote Similarity	NPD2254	Approved
0.5773	Remote Similarity	NPD6001	Approved
0.5769	Remote Similarity	NPD6412	Phase 2
0.5758	Remote Similarity	NPD4755	Approved
0.5758	Remote Similarity	NPD2270	Approved
0.5755	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.575	Remote Similarity	NPD7341	Phase 2
0.5743	Remote Similarity	NPD1700	Approved
0.5732	Remote Similarity	NPD229	Approved
0.5732	Remote Similarity	NPD6705	Phase 1
0.5729	Remote Similarity	NPD5694	Approved
0.5727	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4629	Approved
0.5714	Remote Similarity	NPD5210	Approved
0.5699	Remote Similarity	NPD4694	Approved
0.5699	Remote Similarity	NPD5280	Approved
0.5699	Remote Similarity	NPD5279	Phase 3
0.5699	Remote Similarity	NPD5690	Phase 2
0.5684	Remote Similarity	NPD6051	Approved
0.5676	Remote Similarity	NPD6335	Approved
0.5673	Remote Similarity	NPD6008	Approved
0.567	Remote Similarity	NPD5778	Approved
0.567	Remote Similarity	NPD5779	Approved
0.5664	Remote Similarity	NPD6921	Approved
0.5657	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD4697	Phase 3
0.5657	Remote Similarity	NPD5222	Approved
0.5657	Remote Similarity	NPD5221	Approved
0.5652	Remote Similarity	NPD386	Approved
0.5652	Remote Similarity	NPD388	Approved
0.5644	Remote Similarity	NPD4696	Approved
0.5644	Remote Similarity	NPD4700	Approved
0.5644	Remote Similarity	NPD5286	Approved
0.5644	Remote Similarity	NPD5285	Approved
0.5641	Remote Similarity	NPD9656	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