NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	374.18
Volume:	367.093
LogP:	1.226
LogD:	1.208
LogS:	-2.542
# Rotatable Bonds:	2
TPSA:	91.26
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.692
Synthetic Accessibility Score:	6.503
Fsp3:	0.65
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:	-5.295
MDCK Permeability:	2.805257827276364e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.912
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.148

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.303
Plasma Protein Binding (PPB):	10.811296463012695%
Volume Distribution (VD):	0.477
Pgp-substrate:	77.14646911621094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.877
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.835
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.083
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.177
CYP3A4-inhibitor:	0.135
CYP3A4-substrate:	0.857

ADMET: Excretion

Clearance (CL):	9.505
Half-life (T1/2):	0.038

ADMET: Toxicity

hERG Blockers:	0.311
Human Hepatotoxicity (H-HT):	0.31
Drug-inuced Liver Injury (DILI):	0.059
AMES Toxicity:	0.893
Rat Oral Acute Toxicity:	0.457
Maximum Recommended Daily Dose:	0.883
Skin Sensitization:	0.519
Carcinogencity:	0.845
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC477159

Natural Product ID:	NPC477159
*Common Name:**	(1S,2S,4S,7S,8S,9S,12S)-7-ethyl-7,12-dihydroxy-1'-methoxyspiro[11-oxa-5-azatricyclo[6.3.1.04,9]dodecane-2,3'-indole]-2'-one
IUPAC Name:	(1S,2S,4S,7S,8S,9S,12S)-7-ethyl-7,12-dihydroxy-1'-methoxyspiro[11-oxa-5-azatricyclo[6.3.1.04,9]dodecane-2,3'-indole]-2'-one
Synonyms:
Standard InCHIKey:	WPBBGAHDYHELMX-AAGOSNAUSA-N
Standard InCHI:	InChI=1S/C20H26N2O5/c1-3-19(25)10-21-13-8-20(17-16(23)15(19)11(13)9-27-17)12-6-4-5-7-14(12)22(26-2)18(20)24/h4-7,11,13,15-17,21,23,25H,3,8-10H2,1-2H3/t11-,13+,15+,16+,17-,19-,20+/m1/s1
SMILES:	CC[C@]1(CN[C@H]2C[C@@]3([C@H]4[C@H]([C@@H]1[C@@H]2CO4)O)C5=CC=CC=C5N(C3=O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	122181714
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0003758] Gelsemium alkaloids

*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
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16643063]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16989532]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24256496]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	leaves and vine stems	Xishuangbanna Tropical Botanical Garden (XTBG), Chinese Academy of Science (CAS), Mengla County, Yunnan Province, China	2009-OCT	PMID[26103517]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26222693]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	25000	nM	PMID[26103517]

☑ 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 NPC477159 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	237
0.1-0.2	1175
0.2-0.3	3670
0.3-0.4	17916
0.4-0.5	15214
0.5-0.6	3936
0.6-0.7	494
0.7-0.8	43
0.8-0.85	6
0.85-0.9	3
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9128	High Similarity	NPC284706
0.9018	High Similarity	NPC176983
0.8788	High Similarity	NPC286871
0.8773	High Similarity	NPC29285
0.8678	High Similarity	NPC245741
0.8475	Intermediate Similarity	NPC282092
0.8457	Intermediate Similarity	NPC477160
0.8276	Intermediate Similarity	NPC13367
0.8162	Intermediate Similarity	NPC475559
0.807	Intermediate Similarity	NPC309531
0.807	Intermediate Similarity	NPC472102
0.807	Intermediate Similarity	NPC143457
0.8054	Intermediate Similarity	NPC230313
0.8023	Intermediate Similarity	NPC129624
0.7968	Intermediate Similarity	NPC302548
0.7931	Intermediate Similarity	NPC472106
0.7816	Intermediate Similarity	NPC472101
0.7816	Intermediate Similarity	NPC472120
0.7766	Intermediate Similarity	NPC243626
0.768	Intermediate Similarity	NPC14339
0.7647	Intermediate Similarity	NPC473008
0.7614	Intermediate Similarity	NPC85651
0.7614	Intermediate Similarity	NPC472117
0.7592	Intermediate Similarity	NPC90967
0.7584	Intermediate Similarity	NPC214960
0.7584	Intermediate Similarity	NPC279527
0.7566	Intermediate Similarity	NPC473004
0.7543	Intermediate Similarity	NPC113946
0.7541	Intermediate Similarity	NPC475094
0.7527	Intermediate Similarity	NPC476441
0.7462	Intermediate Similarity	NPC477161
0.7459	Intermediate Similarity	NPC476428
0.7433	Intermediate Similarity	NPC473007
0.7433	Intermediate Similarity	NPC259626
0.7418	Intermediate Similarity	NPC476425
0.7416	Intermediate Similarity	NPC472121
0.7396	Intermediate Similarity	NPC221687
0.738	Intermediate Similarity	NPC2933
0.7374	Intermediate Similarity	NPC313757
0.7374	Intermediate Similarity	NPC477173
0.7368	Intermediate Similarity	NPC473298
0.7337	Intermediate Similarity	NPC470488
0.7327	Intermediate Similarity	NPC475778
0.7326	Intermediate Similarity	NPC256288
0.7322	Intermediate Similarity	NPC285622
0.7322	Intermediate Similarity	NPC96901
0.731	Intermediate Similarity	NPC472103
0.7308	Intermediate Similarity	NPC472118
0.7297	Intermediate Similarity	NPC476326
0.7296	Intermediate Similarity	NPC475489
0.7277	Intermediate Similarity	NPC22689
0.7277	Intermediate Similarity	NPC105055
0.7268	Intermediate Similarity	NPC473375
0.7268	Intermediate Similarity	NPC97100
0.7259	Intermediate Similarity	NPC471512
0.7249	Intermediate Similarity	NPC52262
0.7238	Intermediate Similarity	NPC471124
0.7236	Intermediate Similarity	NPC477178
0.7236	Intermediate Similarity	NPC254850
0.7236	Intermediate Similarity	NPC477180
0.7236	Intermediate Similarity	NPC470489
0.7236	Intermediate Similarity	NPC477181
0.7228	Intermediate Similarity	NPC214626
0.7228	Intermediate Similarity	NPC251212
0.7228	Intermediate Similarity	NPC234999
0.7228	Intermediate Similarity	NPC139085
0.7219	Intermediate Similarity	NPC11149
0.7216	Intermediate Similarity	NPC34717
0.7214	Intermediate Similarity	NPC471950
0.7214	Intermediate Similarity	NPC471945
0.7211	Intermediate Similarity	NPC473615
0.7204	Intermediate Similarity	NPC260075
0.72	Intermediate Similarity	NPC477174
0.72	Intermediate Similarity	NPC470490
0.7198	Intermediate Similarity	NPC472115
0.7198	Intermediate Similarity	NPC472114
0.7186	Intermediate Similarity	NPC477179
0.7178	Intermediate Similarity	NPC471946
0.7178	Intermediate Similarity	NPC471951
0.7173	Intermediate Similarity	NPC229484
0.7173	Intermediate Similarity	NPC181928
0.7167	Intermediate Similarity	NPC315368
0.7159	Intermediate Similarity	NPC475763
0.715	Intermediate Similarity	NPC25401
0.7135	Intermediate Similarity	NPC292675
0.7129	Intermediate Similarity	NPC475259
0.7129	Intermediate Similarity	NPC470491
0.7126	Intermediate Similarity	NPC264589
0.7111	Intermediate Similarity	NPC471122
0.7074	Intermediate Similarity	NPC218594
0.7074	Intermediate Similarity	NPC99043
0.7059	Intermediate Similarity	NPC191817
0.7059	Intermediate Similarity	NPC475359
0.7043	Intermediate Similarity	NPC177261
0.7035	Intermediate Similarity	NPC214428
0.703	Intermediate Similarity	NPC277350
0.7029	Intermediate Similarity	NPC472100
0.701	Intermediate Similarity	NPC474059
0.7	Intermediate Similarity	NPC475962
0.6995	Remote Similarity	NPC14994
0.6995	Remote Similarity	NPC478075
0.6963	Remote Similarity	NPC159963
0.6961	Remote Similarity	NPC211525
0.6961	Remote Similarity	NPC153694
0.6957	Remote Similarity	NPC473006
0.694	Remote Similarity	NPC282339
0.694	Remote Similarity	NPC99632
0.6935	Remote Similarity	NPC100863
0.6927	Remote Similarity	NPC97584
0.6923	Remote Similarity	NPC97380
0.6923	Remote Similarity	NPC148468
0.6923	Remote Similarity	NPC63210
0.6923	Remote Similarity	NPC243673
0.6923	Remote Similarity	NPC36495
0.6923	Remote Similarity	NPC263709
0.6923	Remote Similarity	NPC310403
0.6919	Remote Similarity	NPC278887
0.6889	Remote Similarity	NPC478076
0.6885	Remote Similarity	NPC68650
0.6885	Remote Similarity	NPC225319
0.6885	Remote Similarity	NPC474058
0.6881	Remote Similarity	NPC474116
0.6879	Remote Similarity	NPC315051
0.6878	Remote Similarity	NPC203202
0.6878	Remote Similarity	NPC264482
0.6872	Remote Similarity	NPC316405
0.6866	Remote Similarity	NPC470497
0.6865	Remote Similarity	NPC470069
0.6865	Remote Similarity	NPC52059
0.6862	Remote Similarity	NPC293255
0.6862	Remote Similarity	NPC21752
0.6862	Remote Similarity	NPC210415
0.6862	Remote Similarity	NPC298851
0.6862	Remote Similarity	NPC276993
0.6862	Remote Similarity	NPC181138
0.6845	Remote Similarity	NPC469915
0.6845	Remote Similarity	NPC469743
0.6842	Remote Similarity	NPC186669
0.6831	Remote Similarity	NPC193410
0.6816	Remote Similarity	NPC107828
0.6816	Remote Similarity	NPC90358
0.6806	Remote Similarity	NPC321211
0.6806	Remote Similarity	NPC6974
0.6798	Remote Similarity	NPC471436
0.6798	Remote Similarity	NPC162730
0.6793	Remote Similarity	NPC248117
0.6792	Remote Similarity	NPC288110
0.6782	Remote Similarity	NPC138830
0.6776	Remote Similarity	NPC61013
0.6769	Remote Similarity	NPC291759
0.6766	Remote Similarity	NPC52557
0.6758	Remote Similarity	NPC161827
0.6758	Remote Similarity	NPC475316
0.6758	Remote Similarity	NPC473486
0.6749	Remote Similarity	NPC136573
0.6749	Remote Similarity	NPC176371
0.6746	Remote Similarity	NPC69496
0.6743	Remote Similarity	NPC470301
0.6723	Remote Similarity	NPC311330
0.6722	Remote Similarity	NPC318086
0.672	Remote Similarity	NPC113056
0.672	Remote Similarity	NPC138293
0.6718	Remote Similarity	NPC322621
0.6718	Remote Similarity	NPC133591
0.6716	Remote Similarity	NPC473005
0.6713	Remote Similarity	NPC122886
0.6712	Remote Similarity	NPC473781
0.6712	Remote Similarity	NPC35390
0.6712	Remote Similarity	NPC470631
0.6704	Remote Similarity	NPC212799
0.6703	Remote Similarity	NPC201424
0.6702	Remote Similarity	NPC224970
0.6702	Remote Similarity	NPC469462
0.6702	Remote Similarity	NPC223595
0.6702	Remote Similarity	NPC167724
0.6701	Remote Similarity	NPC175474
0.67	Remote Similarity	NPC21483
0.67	Remote Similarity	NPC198205
0.67	Remote Similarity	NPC67904
0.6684	Remote Similarity	NPC262725
0.6684	Remote Similarity	NPC38823
0.6684	Remote Similarity	NPC207033
0.6683	Remote Similarity	NPC311054
0.6683	Remote Similarity	NPC55493
0.6683	Remote Similarity	NPC149708
0.6683	Remote Similarity	NPC112752
0.6667	Remote Similarity	NPC10732
0.6667	Remote Similarity	NPC127996
0.6667	Remote Similarity	NPC287358
0.6651	Remote Similarity	NPC234772
0.6651	Remote Similarity	NPC473458
0.665	Remote Similarity	NPC329833
0.665	Remote Similarity	NPC473815
0.665	Remote Similarity	NPC475847
0.665	Remote Similarity	NPC185742
0.665	Remote Similarity	NPC241024
0.6649	Remote Similarity	NPC469726
0.6649	Remote Similarity	NPC470548
0.6649	Remote Similarity	NPC329338
0.6634	Remote Similarity	NPC198390

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 NPC477159 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	154
0.1-0.2	464
0.2-0.3	710
0.3-0.4	1852
0.4-0.5	3715
0.5-0.6	2080
0.6-0.7	174
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
0.7644	Intermediate Similarity	NPD5715	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD7105	Phase 1
0.7143	Intermediate Similarity	NPD5941	Approved
0.7143	Intermediate Similarity	NPD5942	Approved
0.7111	Intermediate Similarity	NPD7599	Phase 2
0.7079	Intermediate Similarity	NPD4121	Phase 3
0.7079	Intermediate Similarity	NPD4120	Approved
0.7039	Intermediate Similarity	NPD5742	Approved
0.7039	Intermediate Similarity	NPD5743	Approved
0.7039	Intermediate Similarity	NPD5741	Approved
0.6954	Remote Similarity	NPD5024	Approved
0.6898	Remote Similarity	NPD3824	Phase 1
0.6885	Remote Similarity	NPD7600	Phase 2
0.6882	Remote Similarity	NPD5184	Approved
0.6882	Remote Similarity	NPD5182	Approved
0.6882	Remote Similarity	NPD5185	Approved
0.6859	Remote Similarity	NPD6879	Phase 2
0.6859	Remote Similarity	NPD6878	Phase 2
0.6854	Remote Similarity	NPD4682	Phase 2
0.6814	Remote Similarity	NPD1294	Discontinued
0.6813	Remote Similarity	NPD1663	Discontinued
0.6746	Remote Similarity	NPD2613	Approved
0.672	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.672	Remote Similarity	NPD3790	Phase 2
0.67	Remote Similarity	NPD6805	Discontinued
0.6667	Remote Similarity	NPD6238	Discontinued
0.6648	Remote Similarity	NPD3625	Discontinued
0.6634	Remote Similarity	NPD5003	Discontinued
0.6628	Remote Similarity	NPD2570	Approved
0.6628	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD3089	Approved
0.6628	Remote Similarity	NPD2571	Approved
0.6628	Remote Similarity	NPD2573	Approved
0.6628	Remote Similarity	NPD2566	Approved
0.6628	Remote Similarity	NPD2574	Discontinued
0.6628	Remote Similarity	NPD3615	Approved
0.6628	Remote Similarity	NPD4746	Phase 3
0.6628	Remote Similarity	NPD4745	Approved
0.6628	Remote Similarity	NPD3088	Approved
0.6628	Remote Similarity	NPD3087	Approved
0.6628	Remote Similarity	NPD3090	Approved
0.6628	Remote Similarity	NPD3616	Approved
0.6628	Remote Similarity	NPD3614	Approved
0.6627	Remote Similarity	NPD4215	Approved
0.6627	Remote Similarity	NPD2609	Approved
0.6627	Remote Similarity	NPD3131	Approved
0.6627	Remote Similarity	NPD2611	Approved
0.6627	Remote Similarity	NPD4216	Approved
0.6627	Remote Similarity	NPD4217	Approved
0.6627	Remote Similarity	NPD3132	Approved
0.6627	Remote Similarity	NPD4218	Approved
0.6627	Remote Similarity	NPD2610	Approved
0.6627	Remote Similarity	NPD2608	Approved
0.6627	Remote Similarity	NPD2612	Approved
0.6618	Remote Similarity	NPD4601	Approved
0.6618	Remote Similarity	NPD4600	Approved
0.6615	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD3437	Discontinued
0.6583	Remote Similarity	NPD4499	Approved
0.658	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD2820	Phase 3
0.6559	Remote Similarity	NPD33	Approved
0.6559	Remote Similarity	NPD4393	Approved
0.6556	Remote Similarity	NPD6609	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD4685	Phase 3
0.6552	Remote Similarity	NPD4686	Approved
0.6552	Remote Similarity	NPD4684	Phase 3
0.6538	Remote Similarity	NPD1405	Approved
0.6536	Remote Similarity	NPD2575	Approved
0.6517	Remote Similarity	NPD2365	Approved
0.6514	Remote Similarity	NPD3912	Discontinued
0.651	Remote Similarity	NPD5997	Discontinued
0.649	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD6295	Approved
0.6477	Remote Similarity	NPD6316	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD6294	Approved
0.6468	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD5947	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD4602	Approved
0.6439	Remote Similarity	NPD5196	Approved
0.6439	Remote Similarity	NPD5197	Approved
0.6439	Remote Similarity	NPD5194	Approved
0.6421	Remote Similarity	NPD7036	Phase 3
0.6421	Remote Similarity	NPD7035	Approved
0.642	Remote Similarity	NPD8173	Phase 2
0.642	Remote Similarity	NPD8172	Phase 2
0.642	Remote Similarity	NPD6073	Approved
0.6418	Remote Similarity	NPD2565	Phase 2
0.6418	Remote Similarity	NPD2564	Approved
0.6412	Remote Similarity	NPD6792	Phase 3
0.6411	Remote Similarity	NPD8114	Approved
0.6411	Remote Similarity	NPD8115	Approved
0.6409	Remote Similarity	NPD7785	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD7295	Approved
0.6408	Remote Similarity	NPD6249	Phase 2
0.6408	Remote Similarity	NPD6248	Phase 2
0.6406	Remote Similarity	NPD5183	Approved
0.6406	Remote Similarity	NPD5186	Approved
0.64	Remote Similarity	NPD6484	Approved
0.64	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6483	Approved
0.6393	Remote Similarity	NPD7528	Approved
0.6392	Remote Similarity	NPD5466	Approved
0.6392	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.639	Remote Similarity	NPD3828	Approved
0.6386	Remote Similarity	NPD8240	Discontinued
0.6386	Remote Similarity	NPD5076	Approved
0.6386	Remote Similarity	NPD5077	Approved
0.6386	Remote Similarity	NPD5042	Phase 1
0.6384	Remote Similarity	NPD6342	Discontinued
0.6382	Remote Similarity	NPD6557	Phase 2
0.6381	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD2869	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD4152	Approved
0.6364	Remote Similarity	NPD6395	Phase 2
0.6364	Remote Similarity	NPD6396	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7252	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5487	Phase 1
0.6359	Remote Similarity	NPD4668	Phase 2
0.6359	Remote Similarity	NPD5748	Phase 2
0.6358	Remote Similarity	NPD2918	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD2919	Clinical (unspecified phase)
0.635	Remote Similarity	NPD3153	Approved
0.635	Remote Similarity	NPD3154	Approved
0.6347	Remote Similarity	NPD7805	Phase 3
0.6346	Remote Similarity	NPD7727	Phase 2
0.634	Remote Similarity	NPD7854	Phase 2
0.6339	Remote Similarity	NPD1801	Approved
0.6339	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD1802	Approved
0.6338	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD5430	Discontinued
0.6331	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD3449	Discontinued
0.6322	Remote Similarity	NPD4738	Phase 2
0.6316	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.631	Remote Similarity	NPD8417	Discontinued
0.6307	Remote Similarity	NPD5296	Approved
0.6303	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD4177	Approved
0.6301	Remote Similarity	NPD4175	Approved
0.63	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD519	Approved
0.6293	Remote Similarity	NPD7256	Discontinued
0.6292	Remote Similarity	NPD6358	Phase 2
0.6292	Remote Similarity	NPD5318	Discontinued
0.629	Remote Similarity	NPD1879	Approved
0.6286	Remote Similarity	NPD7205	Discontinued
0.6286	Remote Similarity	NPD5581	Approved
0.6275	Remote Similarity	NPD7570	Approved
0.6275	Remote Similarity	NPD7569	Approved
0.6268	Remote Similarity	NPD7817	Phase 1
0.6264	Remote Similarity	NPD5263	Approved
0.6264	Remote Similarity	NPD6676	Phase 2
0.6264	Remote Similarity	NPD7487	Discontinued
0.6264	Remote Similarity	NPD5918	Discontinued
0.6263	Remote Similarity	NPD2511	Approved
0.6257	Remote Similarity	NPD5086	Approved
0.6257	Remote Similarity	NPD3648	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD7593	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD5426	Phase 3
0.6244	Remote Similarity	NPD7300	Phase 3
0.6244	Remote Similarity	NPD5498	Phase 2
0.6244	Remote Similarity	NPD7302	Phase 3
0.6243	Remote Similarity	NPD7011	Discontinued
0.6243	Remote Similarity	NPD8630	Approved
0.6243	Remote Similarity	NPD5993	Phase 1
0.6243	Remote Similarity	NPD6768	Approved
0.6238	Remote Similarity	NPD4951	Discontinued
0.6238	Remote Similarity	NPD6891	Phase 2
0.6236	Remote Similarity	NPD5725	Approved
0.6236	Remote Similarity	NPD6102	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD7186	Phase 3
0.6232	Remote Similarity	NPD5195	Discontinued
0.6229	Remote Similarity	NPD4497	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD2638	Clinical (unspecified phase)
0.6225	Remote Similarity	NPD6659	Phase 2
0.6224	Remote Similarity	NPD3423	Phase 2
0.6224	Remote Similarity	NPD3422	Phase 3
0.6221	Remote Similarity	NPD1036	Approved
0.6218	Remote Similarity	NPD5823	Approved
0.6216	Remote Similarity	NPD7820	Phase 3
0.6216	Remote Similarity	NPD4432	Discontinued
0.6214	Remote Similarity	NPD7944	Discontinued
0.6214	Remote Similarity	NPD4427	Phase 2
0.6212	Remote Similarity	NPD7881	Approved
0.6211	Remote Similarity	NPD6723	Discontinued
0.6211	Remote Similarity	NPD4514	Approved
0.6211	Remote Similarity	NPD7114	Clinical (unspecified phase)
0.621	Remote Similarity	NPD7878	Phase 2
0.6209	Remote Similarity	NPD6301	Phase 2
0.6207	Remote Similarity	NPD4334	Discontinued
0.6204	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6201	Remote Similarity	NPD3864	Clinical (unspecified phase)
0.62	Remote Similarity	NPD5596	Phase 2
0.6196	Remote Similarity	NPD3141	Discontinued
0.6195	Remote Similarity	NPD5937	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