NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	370.15
Volume:	361.82
LogP:	1.965
LogD:	1.853
LogS:	-4.459
# Rotatable Bonds:	3
TPSA:	77.43
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.754
Synthetic Accessibility Score:	6.588
Fsp3:	0.55
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.937
MDCK Permeability:	1.4396629012480844e-05
Pgp-inhibitor:	0.855
Pgp-substrate:	0.124
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.018
30% Bioavailability (F30%):	0.903

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.851
Plasma Protein Binding (PPB):	58.094268798828125%
Volume Distribution (VD):	1.44
Pgp-substrate:	41.78623962402344%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.867
CYP2C19-inhibitor:	0.041
CYP2C19-substrate:	0.888
CYP2C9-inhibitor:	0.031
CYP2C9-substrate:	0.083
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.211
CYP3A4-inhibitor:	0.863
CYP3A4-substrate:	0.909

ADMET: Excretion

Clearance (CL):	10.806
Half-life (T1/2):	0.176

ADMET: Toxicity

hERG Blockers:	0.42
Human Hepatotoxicity (H-HT):	0.433
Drug-inuced Liver Injury (DILI):	0.643
AMES Toxicity:	0.929
Rat Oral Acute Toxicity:	0.192
Maximum Recommended Daily Dose:	0.89
Skin Sensitization:	0.856
Carcinogencity:	0.884
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.77

Download Data

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

Natural Product: NPC477161

Natural Product ID:	NPC477161
*Common Name:**	(1R,2S,4S,8R,9S)-1',6'-dimethoxy-2'-oxospiro[11-oxa-5-azatricyclo[6.3.1.04,9]dodec-6-ene-2,3'-indole]-7-carbaldehyde
IUPAC Name:	(1R,2S,4S,8R,9S)-1',6'-dimethoxy-2'-oxospiro[11-oxa-5-azatricyclo[6.3.1.04,9]dodec-6-ene-2,3'-indole]-7-carbaldehyde
Synonyms:
Standard InCHIKey:	HICAXUMNKFUXNW-RSXWSOLBSA-N
Standard InCHI:	InChI=1S/C20H22N2O5/c1-25-12-3-4-15-17(5-12)22(26-2)19(24)20(15)7-16-14-10-27-18(20)6-13(14)11(9-23)8-21-16/h3-5,8-9,13-14,16,18,21H,6-7,10H2,1-2H3/t13-,14-,16-,18+,20-/m0/s1
SMILES:	COC1=CC2=C(C=C1)[C@]3(C[C@H]4[C@H]5CO[C@@H]3C[C@H]5C(=CN4)C=O)C(=O)N2OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	122181683
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	7

Activity Type	# Activity
Cell Line	6
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	8500	nM	PMID[26103517]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	7300	nM	PMID[26103517]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	9300	nM	PMID[26103517]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000	nM	PMID[26103517]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	10000	nM	PMID[26103517]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	25000	nM	PMID[26103517]
NPT2	Others	Unspecified		IC50	>	10000	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 NPC477161 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	371
0.1-0.2	2115
0.2-0.3	9178
0.3-0.4	8638
0.4-0.5	16522
0.5-0.6	5100
0.6-0.7	709
0.7-0.8	54
0.8-0.85	4
0.85-0.9	3
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9239	High Similarity	NPC230313
0.9135	High Similarity	NPC243626
0.8824	High Similarity	NPC473004
0.8817	High Similarity	NPC473008
0.8691	High Similarity	NPC100863
0.8629	High Similarity	NPC477160
0.8602	High Similarity	NPC473007
0.815	Intermediate Similarity	NPC14339
0.8029	Intermediate Similarity	NPC77777
0.801	Intermediate Similarity	NPC473006
0.8	Intermediate Similarity	NPC22476
0.797	Intermediate Similarity	NPC87714
0.7961	Intermediate Similarity	NPC10732
0.795	Intermediate Similarity	NPC67904
0.7838	Intermediate Similarity	NPC286871
0.7838	Intermediate Similarity	NPC176983
0.7833	Intermediate Similarity	NPC41216
0.7783	Intermediate Similarity	NPC473005
0.7766	Intermediate Similarity	NPC473569
0.7707	Intermediate Similarity	NPC475147
0.7677	Intermediate Similarity	NPC474059
0.7644	Intermediate Similarity	NPC475133
0.7639	Intermediate Similarity	NPC122886
0.7622	Intermediate Similarity	NPC29285
0.7619	Intermediate Similarity	NPC159815
0.7598	Intermediate Similarity	NPC138830
0.7559	Intermediate Similarity	NPC126556
0.755	Intermediate Similarity	NPC203628
0.7547	Intermediate Similarity	NPC189661
0.7477	Intermediate Similarity	NPC195636
0.7476	Intermediate Similarity	NPC232600
0.7462	Intermediate Similarity	NPC477159
0.7453	Intermediate Similarity	NPC119722
0.7435	Intermediate Similarity	NPC214960
0.7435	Intermediate Similarity	NPC279527
0.7426	Intermediate Similarity	NPC204970
0.7402	Intermediate Similarity	NPC303214
0.7382	Intermediate Similarity	NPC299582
0.7376	Intermediate Similarity	NPC1820
0.7373	Intermediate Similarity	NPC318525
0.7373	Intermediate Similarity	NPC476069
0.7373	Intermediate Similarity	NPC10653
0.7371	Intermediate Similarity	NPC127996
0.7363	Intermediate Similarity	NPC284706
0.7339	Intermediate Similarity	NPC128476
0.7333	Intermediate Similarity	NPC291173
0.7324	Intermediate Similarity	NPC82541
0.7321	Intermediate Similarity	NPC207971
0.7299	Intermediate Similarity	NPC478075
0.729	Intermediate Similarity	NPC470482
0.729	Intermediate Similarity	NPC470481
0.7286	Intermediate Similarity	NPC268077
0.7277	Intermediate Similarity	NPC269449
0.726	Intermediate Similarity	NPC127178
0.7251	Intermediate Similarity	NPC195787
0.7251	Intermediate Similarity	NPC246140
0.7246	Intermediate Similarity	NPC71124
0.7241	Intermediate Similarity	NPC174629
0.7241	Intermediate Similarity	NPC45389
0.724	Intermediate Similarity	NPC21638
0.724	Intermediate Similarity	NPC19175
0.724	Intermediate Similarity	NPC115588
0.7228	Intermediate Similarity	NPC21425
0.7225	Intermediate Similarity	NPC143457
0.7209	Intermediate Similarity	NPC264176
0.7194	Intermediate Similarity	NPC96901
0.7194	Intermediate Similarity	NPC73280
0.7193	Intermediate Similarity	NPC151171
0.7172	Intermediate Similarity	NPC186669
0.7162	Intermediate Similarity	NPC231924
0.7157	Intermediate Similarity	NPC5630
0.7136	Intermediate Similarity	NPC198160
0.713	Intermediate Similarity	NPC476436
0.7129	Intermediate Similarity	NPC241263
0.7123	Intermediate Similarity	NPC473041
0.7105	Intermediate Similarity	NPC154922
0.7104	Intermediate Similarity	NPC46259
0.71	Intermediate Similarity	NPC469722
0.7098	Intermediate Similarity	NPC470480
0.7093	Intermediate Similarity	NPC473105
0.7071	Intermediate Similarity	NPC13367
0.7053	Intermediate Similarity	NPC254957
0.7051	Intermediate Similarity	NPC116178
0.7048	Intermediate Similarity	NPC5374
0.7032	Intermediate Similarity	NPC152768
0.7032	Intermediate Similarity	NPC148183
0.703	Intermediate Similarity	NPC314659
0.7018	Intermediate Similarity	NPC321166
0.7018	Intermediate Similarity	NPC217903
0.7015	Intermediate Similarity	NPC70092
0.7014	Intermediate Similarity	NPC37957
0.7014	Intermediate Similarity	NPC219397
0.701	Intermediate Similarity	NPC472121
0.7	Intermediate Similarity	NPC305984
0.7	Intermediate Similarity	NPC234933
0.6995	Remote Similarity	NPC245741
0.6991	Remote Similarity	NPC311906
0.698	Remote Similarity	NPC28368
0.698	Remote Similarity	NPC197335
0.6974	Remote Similarity	NPC139373
0.6974	Remote Similarity	NPC476429
0.6968	Remote Similarity	NPC303658
0.696	Remote Similarity	NPC223242
0.6957	Remote Similarity	NPC28510
0.6955	Remote Similarity	NPC234772
0.6953	Remote Similarity	NPC113455
0.6951	Remote Similarity	NPC198503
0.695	Remote Similarity	NPC264482
0.695	Remote Similarity	NPC203202
0.6948	Remote Similarity	NPC1464
0.694	Remote Similarity	NPC475816
0.6937	Remote Similarity	NPC288110
0.6937	Remote Similarity	NPC153923
0.6931	Remote Similarity	NPC242000
0.6931	Remote Similarity	NPC39822
0.6927	Remote Similarity	NPC282092
0.6927	Remote Similarity	NPC87391
0.6926	Remote Similarity	NPC131977
0.6926	Remote Similarity	NPC184680
0.6919	Remote Similarity	NPC112937
0.6916	Remote Similarity	NPC194740
0.6912	Remote Similarity	NPC97584
0.6906	Remote Similarity	NPC472099
0.6898	Remote Similarity	NPC222561
0.6897	Remote Similarity	NPC470784
0.6897	Remote Similarity	NPC470785
0.689	Remote Similarity	NPC471825
0.6881	Remote Similarity	NPC6974
0.6881	Remote Similarity	NPC476651
0.688	Remote Similarity	NPC469451
0.6872	Remote Similarity	NPC473458
0.6869	Remote Similarity	NPC288759
0.6867	Remote Similarity	NPC469450
0.6866	Remote Similarity	NPC205926
0.6864	Remote Similarity	NPC120239
0.6863	Remote Similarity	NPC159963
0.6861	Remote Similarity	NPC222046
0.6856	Remote Similarity	NPC113946
0.685	Remote Similarity	NPC210415
0.685	Remote Similarity	NPC214626
0.685	Remote Similarity	NPC139085
0.685	Remote Similarity	NPC276993
0.685	Remote Similarity	NPC293255
0.685	Remote Similarity	NPC251212
0.685	Remote Similarity	NPC298851
0.685	Remote Similarity	NPC21752
0.685	Remote Similarity	NPC181138
0.6847	Remote Similarity	NPC283810
0.6847	Remote Similarity	NPC313327
0.6845	Remote Similarity	NPC308197
0.6845	Remote Similarity	NPC262725
0.6844	Remote Similarity	NPC148124
0.6842	Remote Similarity	NPC114039
0.6842	Remote Similarity	NPC66777
0.6842	Remote Similarity	NPC471762
0.6842	Remote Similarity	NPC206109
0.684	Remote Similarity	NPC160113
0.684	Remote Similarity	NPC476220
0.6832	Remote Similarity	NPC260075
0.6827	Remote Similarity	NPC22689
0.6827	Remote Similarity	NPC105055
0.6826	Remote Similarity	NPC475720
0.6826	Remote Similarity	NPC474192
0.6824	Remote Similarity	NPC301501
0.6822	Remote Similarity	NPC329932
0.682	Remote Similarity	NPC249583
0.6818	Remote Similarity	NPC308137
0.6818	Remote Similarity	NPC310211
0.6818	Remote Similarity	NPC471652
0.6816	Remote Similarity	NPC96321
0.6812	Remote Similarity	NPC14994
0.6809	Remote Similarity	NPC469452
0.6806	Remote Similarity	NPC313112
0.6806	Remote Similarity	NPC301292
0.6804	Remote Similarity	NPC25961
0.6802	Remote Similarity	NPC470002
0.6802	Remote Similarity	NPC470001
0.68	Remote Similarity	NPC329830
0.68	Remote Similarity	NPC99724
0.6798	Remote Similarity	NPC218594
0.6798	Remote Similarity	NPC478078
0.6798	Remote Similarity	NPC99043
0.6794	Remote Similarity	NPC25401
0.6791	Remote Similarity	NPC15987
0.6791	Remote Similarity	NPC295898
0.6789	Remote Similarity	NPC90185
0.6786	Remote Similarity	NPC309531
0.6786	Remote Similarity	NPC93653
0.6786	Remote Similarity	NPC472102
0.6777	Remote Similarity	NPC198401
0.6769	Remote Similarity	NPC123241
0.6765	Remote Similarity	NPC5167
0.6765	Remote Similarity	NPC85613
0.6761	Remote Similarity	NPC218733
0.6761	Remote Similarity	NPC132874
0.6761	Remote Similarity	NPC265642
0.6761	Remote Similarity	NPC138615
0.6756	Remote Similarity	NPC150239
0.6753	Remote Similarity	NPC161827
0.6751	Remote Similarity	NPC293458

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 NPC477161 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	231
0.1-0.2	641
0.2-0.3	987
0.3-0.4	1722
0.4-0.5	3214
0.5-0.6	2083
0.6-0.7	263
0.7-0.8	9
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
0.7725	Intermediate Similarity	NPD5183	Approved
0.7725	Intermediate Similarity	NPD5186	Approved
0.7554	Intermediate Similarity	NPD814	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD6238	Discontinued
0.7277	Intermediate Similarity	NPD6608	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD6457	Approved
0.7215	Intermediate Similarity	NPD3437	Discontinued
0.7188	Intermediate Similarity	NPD4981	Phase 2
0.7163	Intermediate Similarity	NPD5071	Phase 2
0.715	Intermediate Similarity	NPD1307	Phase 2
0.715	Intermediate Similarity	NPD1309	Phase 2
0.7129	Intermediate Similarity	NPD6021	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD3912	Discontinued
0.7109	Intermediate Similarity	NPD6795	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7255	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD5937	Approved
0.7073	Intermediate Similarity	NPD5896	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD6533	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4084	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD7174	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5334	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD7626	Approved
0.6948	Remote Similarity	NPD7627	Approved
0.6944	Remote Similarity	NPD4859	Phase 1
0.6942	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5496	Approved
0.692	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD6321	Discontinued
0.6884	Remote Similarity	NPD4465	Phase 2
0.6884	Remote Similarity	NPD4467	Phase 2
0.6881	Remote Similarity	NPD7479	Phase 2
0.6881	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD4082	Approved
0.6857	Remote Similarity	NPD7256	Discontinued
0.6849	Remote Similarity	NPD4493	Discontinued
0.6847	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.684	Remote Similarity	NPD4668	Phase 2
0.6832	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4492	Approved
0.6818	Remote Similarity	NPD4494	Approved
0.6808	Remote Similarity	NPD3297	Approved
0.6806	Remote Similarity	NPD1294	Discontinued
0.6798	Remote Similarity	NPD3899	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD3511	Discontinued
0.6782	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6773	Remote Similarity	NPD683	Approved
0.6771	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.677	Remote Similarity	NPD8311	Discontinued
0.6766	Remote Similarity	NPD2248	Approved
0.6766	Remote Similarity	NPD2246	Approved
0.6766	Remote Similarity	NPD6790	Phase 1
0.6759	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5293	Phase 2
0.6756	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD7186	Phase 3
0.6749	Remote Similarity	NPD5313	Approved
0.6749	Remote Similarity	NPD5312	Approved
0.6744	Remote Similarity	NPD7476	Discontinued
0.6743	Remote Similarity	NPD4596	Phase 1
0.6739	Remote Similarity	NPD4952	Phase 3
0.6728	Remote Similarity	NPD3298	Approved
0.6728	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD6644	Discontinued
0.6727	Remote Similarity	NPD3893	Discontinued
0.6714	Remote Similarity	NPD5515	Phase 2
0.6714	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD4154	Approved
0.6712	Remote Similarity	NPD8027	Approved
0.6699	Remote Similarity	NPD7190	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD1945	Phase 1
0.6682	Remote Similarity	NPD7559	Phase 2
0.6681	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3793	Phase 3
0.6667	Remote Similarity	NPD3888	Discontinued
0.6667	Remote Similarity	NPD3964	Approved
0.6652	Remote Similarity	NPD4373	Phase 2
0.6651	Remote Similarity	NPD4539	Phase 1
0.6651	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD4455	Discontinued
0.6636	Remote Similarity	NPD3472	Approved
0.6636	Remote Similarity	NPD4022	Approved
0.6622	Remote Similarity	NPD6719	Approved
0.6622	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD6357	Discontinued
0.6608	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD3592	Approved
0.6606	Remote Similarity	NPD3591	Approved
0.6603	Remote Similarity	NPD3153	Approved
0.6603	Remote Similarity	NPD3154	Approved
0.6602	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD5997	Discontinued
0.6598	Remote Similarity	NPD1670	Discontinued
0.6595	Remote Similarity	NPD6199	Discontinued
0.6594	Remote Similarity	NPD7820	Phase 3
0.6593	Remote Similarity	NPD5632	Approved
0.6588	Remote Similarity	NPD5928	Phase 1
0.6586	Remote Similarity	NPD7803	Approved
0.6585	Remote Similarity	NPD5600	Discontinued
0.6585	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD4166	Phase 2
0.6578	Remote Similarity	NPD6744	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD8149	Discontinued
0.6577	Remote Similarity	NPD3372	Discontinued
0.6577	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD4456	Clinical (unspecified phase)
0.657	Remote Similarity	NPD5637	Discontinued
0.657	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD6720	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD3441	Approved
0.6567	Remote Similarity	NPD3442	Approved
0.6566	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.656	Remote Similarity	NPD7316	Discontinued
0.6557	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD7668	Phase 2
0.6535	Remote Similarity	NPD2247	Approved
0.6535	Remote Similarity	NPD2249	Approved
0.6535	Remote Similarity	NPD6242	Discontinued
0.6526	Remote Similarity	NPD3479	Discontinued
0.6522	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7279	Phase 2
0.6522	Remote Similarity	NPD7278	Phase 2
0.6518	Remote Similarity	NPD7956	Approved
0.6518	Remote Similarity	NPD7955	Approved
0.6515	Remote Similarity	NPD1769	Discontinued
0.6514	Remote Similarity	NPD3416	Discontinued
0.6513	Remote Similarity	NPD7560	Approved
0.6511	Remote Similarity	NPD6723	Discontinued
0.6504	Remote Similarity	NPD5025	Approved
0.6502	Remote Similarity	NPD5860	Discontinued
0.65	Remote Similarity	NPD7891	Discontinued
0.6498	Remote Similarity	NPD4846	Phase 2
0.6498	Remote Similarity	NPD6874	Approved
0.6498	Remote Similarity	NPD5547	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD7528	Approved
0.649	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.649	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD743	Approved
0.6485	Remote Similarity	NPD5823	Approved
0.6482	Remote Similarity	NPD2842	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD1305	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD2216	Approved
0.6471	Remote Similarity	NPD2215	Approved
0.6468	Remote Similarity	NPD4885	Approved
0.6468	Remote Similarity	NPD6519	Phase 2
0.6465	Remote Similarity	NPD7669	Phase 3
0.6458	Remote Similarity	NPD6716	Phase 1
0.6455	Remote Similarity	NPD6478	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD2681	Approved
0.6453	Remote Similarity	NPD6107	Approved
0.6453	Remote Similarity	NPD2680	Approved
0.6448	Remote Similarity	NPD8459	Approved
0.6448	Remote Similarity	NPD8460	Approved
0.6444	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD7225	Discontinued
0.6443	Remote Similarity	NPD1802	Approved
0.6443	Remote Similarity	NPD1801	Approved
0.6442	Remote Similarity	NPD5445	Approved
0.6441	Remote Similarity	NPD6625	Approved
0.6439	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD7805	Phase 3
0.6435	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD4259	Approved
0.6432	Remote Similarity	NPD4258	Approved
0.6426	Remote Similarity	NPD7708	Approved
0.6419	Remote Similarity	NPD3631	Phase 3
0.6415	Remote Similarity	NPD4515	Suspended
0.6413	Remote Similarity	NPD2907	Approved
0.6413	Remote Similarity	NPD5950	Discontinued
0.6413	Remote Similarity	NPD2916	Discontinued
0.6413	Remote Similarity	NPD2906	Approved
0.6406	Remote Similarity	NPD4979	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD5994	Discontinued
0.64	Remote Similarity	NPD7272	Discontinued
0.6398	Remote Similarity	NPD6851	Approved
0.6398	Remote Similarity	NPD6618	Phase 2
0.6398	Remote Similarity	NPD6853	Approved
0.6396	Remote Similarity	NPD3003	Approved
0.6392	Remote Similarity	NPD4041	Approved
0.6388	Remote Similarity	NPD4679	Discontinued
0.6385	Remote Similarity	NPD5188	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD3874	Discontinued
0.6378	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD2822	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD3983	Phase 3
0.6373	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD7178	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD6296	Discontinued
0.6368	Remote Similarity	NPD822	Approved
0.6364	Remote Similarity	NPD6297	Approved
0.6364	Remote Similarity	NPD6879	Phase 2
0.6364	Remote Similarity	NPD6878	Phase 2
0.636	Remote Similarity	NPD5561	Approved
0.636	Remote Similarity	NPD5562	Approved
0.6359	Remote Similarity	NPD6365	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