NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	342.19
Volume:	349.512
LogP:	3.47
LogD:	3.312
LogS:	-3.73
# Rotatable Bonds:	2
TPSA:	61.8
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.862
Synthetic Accessibility Score:	6.114
Fsp3:	0.65
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:	-5.416
MDCK Permeability:	9.31174054130679e-06
Pgp-inhibitor:	0.004
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.098
20% Bioavailability (F20%):	0.837
30% Bioavailability (F30%):	0.274

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.856
Plasma Protein Binding (PPB):	72.59590148925781%
Volume Distribution (VD):	1.674
Pgp-substrate:	25.61530113220215%

ADMET: Metabolism

CYP1A2-inhibitor:	0.785
CYP1A2-substrate:	0.783
CYP2C19-inhibitor:	0.648
CYP2C19-substrate:	0.827
CYP2C9-inhibitor:	0.669
CYP2C9-substrate:	0.596
CYP2D6-inhibitor:	0.61
CYP2D6-substrate:	0.912
CYP3A4-inhibitor:	0.546
CYP3A4-substrate:	0.584

ADMET: Excretion

Clearance (CL):	9.513
Half-life (T1/2):	0.499

ADMET: Toxicity

hERG Blockers:	0.148
Human Hepatotoxicity (H-HT):	0.523
Drug-inuced Liver Injury (DILI):	0.633
AMES Toxicity:	0.176
Rat Oral Acute Toxicity:	0.382
Maximum Recommended Daily Dose:	0.893
Skin Sensitization:	0.25
Carcinogencity:	0.433
Eye Corrosion:	0.003
Eye Irritation:	0.029
Respiratory Toxicity:	0.913

Download Data

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

Natural Product: NPC478075

Natural Product ID:	NPC478075
*Common Name:**	(1'S,2S,5'R,7'R,8'S,9'S)-9'-ethyl-5'-hydroxy-5-methoxyspiro[1H-indole-2,6'-3-azatricyclo[5.3.1.03,8]undecane]-3-one
IUPAC Name:	(1'S,2S,5'R,7'R,8'S,9'S)-9'-ethyl-5'-hydroxy-5-methoxyspiro[1H-indole-2,6'-3-azatricyclo[5.3.1.03,8]undecane]-3-one
Synonyms:
Standard InCHIKey:	DSABJRUCTHPZJA-ADDQASITSA-N
Standard InCHI:	InChI=1S/C20H26N2O3/c1-3-12-6-11-7-15-18(12)22(9-11)10-17(23)20(15)19(24)14-8-13(25-2)4-5-16(14)21-20/h4-5,8,11-12,15,17-18,21,23H,3,6-7,9-10H2,1-2H3/t11-,12-,15+,17+,18-,20-/m0/s1
SMILES:	CC[C@H]1C[C@H]2C[C@@H]3[C@H]1N(C2)C[C@H]([C@]34C(=O)C5=C(N4)C=CC(=C5)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	122179179
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000221] Quinolizidines

*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
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18778099]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18778099]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[24773071]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	stem-bark	Pahang, Malaysia	2003-JUN	PMID[25919190]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26918761]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27077800]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29319316]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30869890]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32356659]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	53200	nM	PMID[25919190]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	25	ug/ml	PMID[25919190]

☑ 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 NPC478075 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	320
0.1-0.2	1584
0.2-0.3	6437
0.3-0.4	11017
0.4-0.5	11983
0.5-0.6	10086
0.6-0.7	1190
0.7-0.8	79
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8019	Intermediate Similarity	NPC122886
0.7897	Intermediate Similarity	NPC21425
0.7822	Intermediate Similarity	NPC138830
0.7778	Intermediate Similarity	NPC478078
0.7778	Intermediate Similarity	NPC472118
0.7742	Intermediate Similarity	NPC93653
0.7638	Intermediate Similarity	NPC5630
0.7638	Intermediate Similarity	NPC474059
0.7633	Intermediate Similarity	NPC195787
0.7633	Intermediate Similarity	NPC246140
0.7617	Intermediate Similarity	NPC288110
0.7608	Intermediate Similarity	NPC477160
0.7574	Intermediate Similarity	NPC230313
0.7559	Intermediate Similarity	NPC234772
0.7549	Intermediate Similarity	NPC100863
0.7545	Intermediate Similarity	NPC301501
0.7525	Intermediate Similarity	NPC473007
0.7513	Intermediate Similarity	NPC314659
0.7476	Intermediate Similarity	NPC329567
0.7476	Intermediate Similarity	NPC330683
0.7462	Intermediate Similarity	NPC197335
0.7429	Intermediate Similarity	NPC198160
0.7416	Intermediate Similarity	NPC87714
0.7406	Intermediate Similarity	NPC471304
0.7406	Intermediate Similarity	NPC25961
0.7406	Intermediate Similarity	NPC269449
0.7399	Intermediate Similarity	NPC139373
0.7393	Intermediate Similarity	NPC478083
0.7391	Intermediate Similarity	NPC67904
0.7389	Intermediate Similarity	NPC473004
0.738	Intermediate Similarity	NPC329932
0.7379	Intermediate Similarity	NPC218733
0.7379	Intermediate Similarity	NPC132874
0.7379	Intermediate Similarity	NPC265642
0.7379	Intermediate Similarity	NPC138615
0.7378	Intermediate Similarity	NPC154922
0.7376	Intermediate Similarity	NPC473008
0.7376	Intermediate Similarity	NPC473458
0.7368	Intermediate Similarity	NPC469451
0.734	Intermediate Similarity	NPC22476
0.7339	Intermediate Similarity	NPC318525
0.7339	Intermediate Similarity	NPC10653
0.7336	Intermediate Similarity	NPC119722
0.7336	Intermediate Similarity	NPC159815
0.7333	Intermediate Similarity	NPC475147
0.7324	Intermediate Similarity	NPC474366
0.7321	Intermediate Similarity	NPC1464
0.7317	Intermediate Similarity	NPC243626
0.7313	Intermediate Similarity	NPC151171
0.7313	Intermediate Similarity	NPC87391
0.7309	Intermediate Similarity	NPC223242
0.7302	Intermediate Similarity	NPC217903
0.7299	Intermediate Similarity	NPC477161
0.7295	Intermediate Similarity	NPC112937
0.7293	Intermediate Similarity	NPC469452
0.7291	Intermediate Similarity	NPC45389
0.7286	Intermediate Similarity	NPC270301
0.7285	Intermediate Similarity	NPC19175
0.7281	Intermediate Similarity	NPC469450
0.7281	Intermediate Similarity	NPC195636
0.7273	Intermediate Similarity	NPC120239
0.7269	Intermediate Similarity	NPC189661
0.7268	Intermediate Similarity	NPC203972
0.7264	Intermediate Similarity	NPC212123
0.7257	Intermediate Similarity	NPC160113
0.7257	Intermediate Similarity	NPC476220
0.7256	Intermediate Similarity	NPC116178
0.7256	Intermediate Similarity	NPC10732
0.7256	Intermediate Similarity	NPC127996
0.7252	Intermediate Similarity	NPC476436
0.7248	Intermediate Similarity	NPC77777
0.7244	Intermediate Similarity	NPC474192
0.7244	Intermediate Similarity	NPC475720
0.7238	Intermediate Similarity	NPC474077
0.7236	Intermediate Similarity	NPC85613
0.7236	Intermediate Similarity	NPC5167
0.7236	Intermediate Similarity	NPC283810
0.7233	Intermediate Similarity	NPC198401
0.7227	Intermediate Similarity	NPC128476
0.7222	Intermediate Similarity	NPC321166
0.7217	Intermediate Similarity	NPC113455
0.7215	Intermediate Similarity	NPC222046
0.7212	Intermediate Similarity	NPC71124
0.7209	Intermediate Similarity	NPC295479
0.7209	Intermediate Similarity	NPC220241
0.7207	Intermediate Similarity	NPC115588
0.7204	Intermediate Similarity	NPC41216
0.7202	Intermediate Similarity	NPC126556
0.7196	Intermediate Similarity	NPC475133
0.7189	Intermediate Similarity	NPC298449
0.7183	Intermediate Similarity	NPC222561
0.7182	Intermediate Similarity	NPC476069
0.7182	Intermediate Similarity	NPC472099
0.7178	Intermediate Similarity	NPC49184
0.7171	Intermediate Similarity	NPC203628
0.7169	Intermediate Similarity	NPC96321
0.7169	Intermediate Similarity	NPC182853
0.7165	Intermediate Similarity	NPC299582
0.7149	Intermediate Similarity	NPC291173
0.7143	Intermediate Similarity	NPC157931
0.7143	Intermediate Similarity	NPC471513
0.7143	Intermediate Similarity	NPC30749
0.7136	Intermediate Similarity	NPC206109
0.7136	Intermediate Similarity	NPC114039
0.713	Intermediate Similarity	NPC476258
0.713	Intermediate Similarity	NPC304837
0.7123	Intermediate Similarity	NPC207971
0.7118	Intermediate Similarity	NPC131977
0.7114	Intermediate Similarity	NPC472163
0.7113	Intermediate Similarity	NPC204867
0.711	Intermediate Similarity	NPC176113
0.7109	Intermediate Similarity	NPC469732
0.7103	Intermediate Similarity	NPC308943
0.7097	Intermediate Similarity	NPC305542
0.7095	Intermediate Similarity	NPC5374
0.7095	Intermediate Similarity	NPC241263
0.7093	Intermediate Similarity	NPC476429
0.7091	Intermediate Similarity	NPC195120
0.7091	Intermediate Similarity	NPC87560
0.7089	Intermediate Similarity	NPC268077
0.7089	Intermediate Similarity	NPC313112
0.7089	Intermediate Similarity	NPC301292
0.7087	Intermediate Similarity	NPC1820
0.7075	Intermediate Similarity	NPC15987
0.7075	Intermediate Similarity	NPC288759
0.7072	Intermediate Similarity	NPC118189
0.707	Intermediate Similarity	NPC100573
0.707	Intermediate Similarity	NPC207873
0.7065	Intermediate Similarity	NPC70092
0.7064	Intermediate Similarity	NPC268223
0.7062	Intermediate Similarity	NPC127178
0.7062	Intermediate Similarity	NPC257763
0.7056	Intermediate Similarity	NPC475816
0.7054	Intermediate Similarity	NPC231924
0.7051	Intermediate Similarity	NPC218303
0.7048	Intermediate Similarity	NPC234933
0.7047	Intermediate Similarity	NPC133817
0.7047	Intermediate Similarity	NPC476443
0.7041	Intermediate Similarity	NPC472115
0.7041	Intermediate Similarity	NPC472114
0.7039	Intermediate Similarity	NPC473569
0.7033	Intermediate Similarity	NPC303214
0.7032	Intermediate Similarity	NPC55470
0.7028	Intermediate Similarity	NPC232600
0.7019	Intermediate Similarity	NPC254957
0.7009	Intermediate Similarity	NPC14339
0.7004	Intermediate Similarity	NPC477397
0.6996	Remote Similarity	NPC329830
0.6996	Remote Similarity	NPC76478
0.6995	Remote Similarity	NPC477159
0.6995	Remote Similarity	NPC473005
0.6991	Remote Similarity	NPC248903
0.699	Remote Similarity	NPC477186
0.699	Remote Similarity	NPC477998
0.6987	Remote Similarity	NPC329631
0.6986	Remote Similarity	NPC473006
0.6981	Remote Similarity	NPC329793
0.6964	Remote Similarity	NPC148124
0.6961	Remote Similarity	NPC97584
0.696	Remote Similarity	NPC311906
0.6951	Remote Similarity	NPC118154
0.6951	Remote Similarity	NPC157983
0.6947	Remote Similarity	NPC26928
0.6947	Remote Similarity	NPC144691
0.6946	Remote Similarity	NPC329982
0.6943	Remote Similarity	NPC49547
0.6942	Remote Similarity	NPC14994
0.6941	Remote Similarity	NPC470481
0.6941	Remote Similarity	NPC472098
0.6941	Remote Similarity	NPC470482
0.6937	Remote Similarity	NPC134702
0.6936	Remote Similarity	NPC208522
0.6934	Remote Similarity	NPC317727
0.6931	Remote Similarity	NPC475094
0.6931	Remote Similarity	NPC218594
0.6931	Remote Similarity	NPC99043
0.6923	Remote Similarity	NPC25401
0.6923	Remote Similarity	NPC469722
0.6923	Remote Similarity	NPC28510
0.6923	Remote Similarity	NPC469928
0.692	Remote Similarity	NPC99724
0.692	Remote Similarity	NPC7560
0.692	Remote Similarity	NPC46259
0.6919	Remote Similarity	NPC472191
0.6917	Remote Similarity	NPC478080
0.6913	Remote Similarity	NPC473105
0.6908	Remote Similarity	NPC284706
0.6904	Remote Similarity	NPC70172
0.6898	Remote Similarity	NPC45190
0.6898	Remote Similarity	NPC472111
0.6897	Remote Similarity	NPC166169
0.6895	Remote Similarity	NPC220337
0.6895	Remote Similarity	NPC82541
0.6893	Remote Similarity	NPC262725
0.6888	Remote Similarity	NPC176983
0.6887	Remote Similarity	NPC17677
0.6883	Remote Similarity	NPC39370
0.6878	Remote Similarity	NPC148391
0.6875	Remote Similarity	NPC22689
0.6875	Remote Similarity	NPC105055

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 NPC478075 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	204
0.1-0.2	600
0.2-0.3	863
0.3-0.4	1623
0.4-0.5	2761
0.5-0.6	2552
0.6-0.7	534
0.7-0.8	13
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
0.7788	Intermediate Similarity	NPD4493	Discontinued
0.7729	Intermediate Similarity	NPD4082	Approved
0.7667	Intermediate Similarity	NPD4492	Approved
0.7667	Intermediate Similarity	NPD4494	Approved
0.7614	Intermediate Similarity	NPD6021	Clinical (unspecified phase)
0.7592	Intermediate Similarity	NPD5183	Approved
0.7592	Intermediate Similarity	NPD5186	Approved
0.7581	Intermediate Similarity	NPD3783	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD5860	Discontinued
0.75	Intermediate Similarity	NPD5433	Clinical (unspecified phase)
0.7489	Intermediate Similarity	NPD7186	Phase 3
0.7488	Intermediate Similarity	NPD3893	Discontinued
0.7476	Intermediate Similarity	NPD2907	Approved
0.7476	Intermediate Similarity	NPD2906	Approved
0.7476	Intermediate Similarity	NPD4022	Approved
0.7476	Intermediate Similarity	NPD3472	Approved
0.7466	Intermediate Similarity	NPD6199	Discontinued
0.7442	Intermediate Similarity	NPD3940	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD4596	Phase 1
0.7416	Intermediate Similarity	NPD4456	Clinical (unspecified phase)
0.7406	Intermediate Similarity	NPD3372	Discontinued
0.7383	Intermediate Similarity	NPD4455	Discontinued
0.7379	Intermediate Similarity	NPD5196	Approved
0.7379	Intermediate Similarity	NPD5197	Approved
0.7379	Intermediate Similarity	NPD5194	Approved
0.7371	Intermediate Similarity	NPD1945	Phase 1
0.7346	Intermediate Similarity	NPD5143	Clinical (unspecified phase)
0.7309	Intermediate Similarity	NPD4981	Phase 2
0.7295	Intermediate Similarity	NPD5071	Phase 2
0.7291	Intermediate Similarity	NPD5896	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD3437	Discontinued
0.726	Intermediate Similarity	NPD6874	Approved
0.7256	Intermediate Similarity	NPD3888	Discontinued
0.7251	Intermediate Similarity	NPD4467	Phase 2
0.7251	Intermediate Similarity	NPD4465	Phase 2
0.7241	Intermediate Similarity	NPD6608	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD6293	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD3153	Approved
0.7228	Intermediate Similarity	NPD3154	Approved
0.7189	Intermediate Similarity	NPD4562	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD5603	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD3912	Discontinued
0.7156	Intermediate Similarity	NPD8149	Discontinued
0.715	Intermediate Similarity	NPD6654	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD3050	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD7560	Approved
0.7122	Intermediate Similarity	NPD4259	Approved
0.7122	Intermediate Similarity	NPD4258	Approved
0.712	Intermediate Similarity	NPD2672	Discontinued
0.7109	Intermediate Similarity	NPD6321	Discontinued
0.7109	Intermediate Similarity	NPD3416	Discontinued
0.7108	Intermediate Similarity	NPD4515	Suspended
0.7101	Intermediate Similarity	NPD5610	Approved
0.7089	Intermediate Similarity	NPD1294	Discontinued
0.7081	Intermediate Similarity	NPD7238	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD7556	Discontinued
0.7059	Intermediate Similarity	NPD5496	Approved
0.7053	Intermediate Similarity	NPD5937	Approved
0.705	Intermediate Similarity	NPD5334	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD7597	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5928	Phase 1
0.7032	Intermediate Similarity	NPD5293	Phase 2
0.703	Intermediate Similarity	NPD7149	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD6533	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD7479	Phase 2
0.7009	Intermediate Similarity	NPD5102	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD2681	Approved
0.7005	Intermediate Similarity	NPD2680	Approved
0.7	Intermediate Similarity	NPD5195	Discontinued
0.6991	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD2899	Discontinued
0.6972	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD4668	Phase 2
0.6963	Remote Similarity	NPD6478	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD4078	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD6242	Discontinued
0.6948	Remote Similarity	NPD6238	Discontinued
0.6948	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD7301	Phase 3
0.6938	Remote Similarity	NPD7262	Phase 1
0.6935	Remote Similarity	NPD5680	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD5609	Approved
0.6934	Remote Similarity	NPD5608	Approved
0.6933	Remote Similarity	NPD7279	Phase 2
0.6933	Remote Similarity	NPD7820	Phase 3
0.6933	Remote Similarity	NPD7278	Phase 2
0.6931	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.693	Remote Similarity	NPD6250	Discontinued
0.6919	Remote Similarity	NPD5515	Phase 2
0.6919	Remote Similarity	NPD4979	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD7627	Approved
0.6916	Remote Similarity	NPD7626	Approved
0.6912	Remote Similarity	NPD4859	Phase 1
0.6907	Remote Similarity	NPD1769	Discontinued
0.6903	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD5416	Discontinued
0.6884	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD7225	Discontinued
0.6861	Remote Similarity	NPD4429	Discontinued
0.6861	Remote Similarity	NPD7293	Approved
0.6856	Remote Similarity	NPD5022	Discontinued
0.6849	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD5025	Approved
0.684	Remote Similarity	NPD7922	Phase 1
0.6834	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD3983	Phase 3
0.6822	Remote Similarity	NPD6805	Discontinued
0.682	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD683	Approved
0.6816	Remote Similarity	NPD5997	Discontinued
0.6802	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD5600	Discontinued
0.6797	Remote Similarity	NPD5151	Clinical (unspecified phase)
0.679	Remote Similarity	NPD8091	Phase 3
0.6784	Remote Similarity	NPD6037	Discontinued
0.6781	Remote Similarity	NPD7853	Phase 2
0.6777	Remote Similarity	NPD4539	Phase 1
0.6774	Remote Similarity	NPD3298	Approved
0.6774	Remote Similarity	NPD6644	Discontinued
0.6769	Remote Similarity	NPD7994	Phase 2
0.6763	Remote Similarity	NPD6618	Phase 2
0.6762	Remote Similarity	NPD5871	Discontinued
0.6759	Remote Similarity	NPD7071	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD7300	Phase 3
0.6758	Remote Similarity	NPD7302	Phase 3
0.6744	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD6790	Phase 1
0.6737	Remote Similarity	NPD6017	Discontinued
0.6736	Remote Similarity	NPD3641	Approved
0.6736	Remote Similarity	NPD3640	Phase 3
0.6736	Remote Similarity	NPD3639	Approved
0.6735	Remote Similarity	NPD7708	Approved
0.6734	Remote Similarity	NPD4796	Discontinued
0.6733	Remote Similarity	NPD2248	Approved
0.6733	Remote Similarity	NPD2246	Approved
0.6732	Remote Similarity	NPD6297	Approved
0.6723	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD1743	Approved
0.6717	Remote Similarity	NPD1742	Approved
0.6717	Remote Similarity	NPD19	Approved
0.6714	Remote Similarity	NPD5582	Discontinued
0.6711	Remote Similarity	NPD7292	Approved
0.6701	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.67	Remote Similarity	NPD3422	Phase 3
0.67	Remote Similarity	NPD3423	Phase 2
0.6699	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD3297	Approved
0.6696	Remote Similarity	NPD3393	Approved
0.6696	Remote Similarity	NPD3899	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD3394	Approved
0.6696	Remote Similarity	NPD3259	Approved
0.6696	Remote Similarity	NPD3389	Approved
0.6695	Remote Similarity	NPD4561	Discontinued
0.6684	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD6851	Approved
0.6683	Remote Similarity	NPD6853	Approved
0.6682	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD4154	Approved
0.6682	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8358	Approved
0.6667	Remote Similarity	NPD8161	Suspended
0.6667	Remote Similarity	NPD8463	Approved
0.6667	Remote Similarity	NPD1802	Approved
0.6667	Remote Similarity	NPD2339	Phase 3
0.6667	Remote Similarity	NPD2649	Approved
0.6667	Remote Similarity	NPD2651	Approved
0.6667	Remote Similarity	NPD1801	Approved
0.6652	Remote Similarity	NPD7031	Phase 1
0.6652	Remote Similarity	NPD4679	Discontinued
0.6651	Remote Similarity	NPD7205	Discontinued
0.6651	Remote Similarity	NPD7569	Approved
0.6651	Remote Similarity	NPD7570	Approved
0.665	Remote Similarity	NPD4330	Approved
0.665	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.665	Remote Similarity	NPD6844	Discontinued
0.665	Remote Similarity	NPD4329	Approved
0.664	Remote Similarity	NPD7925	Phase 2
0.664	Remote Similarity	NPD7924	Phase 2
0.6638	Remote Similarity	NPD7542	Phase 3
0.6638	Remote Similarity	NPD3006	Discontinued
0.6637	Remote Similarity	NPD5632	Approved
0.6636	Remote Similarity	NPD7222	Phase 2
0.6636	Remote Similarity	NPD3964	Approved
0.6634	Remote Similarity	NPD4166	Phase 2
0.6634	Remote Similarity	NPD5670	Approved
0.6627	Remote Similarity	NPD7803	Approved
0.6624	Remote Similarity	NPD4373	Phase 2
0.6624	Remote Similarity	NPD6625	Approved
0.6622	Remote Similarity	NPD7475	Clinical (unspecified phase)

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