NPASS Compound

Structure

CID284706 OpenBabel06191716092D 26 30 0 0 1 0 0 0 0 0999 V2000 3.5200 1.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1263 3.8029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6269 0.7482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3689 2.6821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8213 3.4789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9527 1.8096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8576 3.4030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4004 0.4004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6503 -0.6836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9890 1.7337 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9667 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4414 2.5304 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8599 1.3367 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5663 1.3672 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.3672 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5109 1.2895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4004 0.9667 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9667 0.9667 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.9667 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.4855 2.2559 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.9861 2.2952 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9363 2.2603 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1043 0.1943 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2525 2.8444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2332 -0.1346 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 25 1 0 0 0 0 3 14 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 10 2 0 0 0 0 7 13 2 0 0 0 0 9 11 1 0 0 0 0 9 26 1 0 0 0 0 10 13 1 0 0 0 0 10 18 1 0 0 0 0 11 12 1 0 0 0 0 11 19 1 6 0 0 0 12 8 1 6 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 14 22 2 0 0 0 0 15 16 1 0 0 0 0 15 19 1 6 0 0 0 15 23 1 0 0 0 0 16 18 1 1 0 0 0 16 26 1 0 0 0 0 17 18 1 0 0 0 0 17 21 1 0 0 0 0 17 24 2 0 0 0 0 18 8 1 6 0 0 0 19 14 1 1 0 0 0 19 20 1 0 0 0 0 21 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	358.15
Volume:	347.16
LogP:	1.026
LogD:	1.076
LogS:	-3.885
# Rotatable Bonds:	3
TPSA:	88.1
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.808
Synthetic Accessibility Score:	6.44
Fsp3:	0.579
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:	-5.435
MDCK Permeability:	1.126802817452699e-05
Pgp-inhibitor:	0.035
Pgp-substrate:	0.993
Human Intestinal Absorption (HIA):	0.891
20% Bioavailability (F20%):	0.955
30% Bioavailability (F30%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.341
Plasma Protein Binding (PPB):	13.33857536315918%
Volume Distribution (VD):	0.652
Pgp-substrate:	75.3287124633789%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.833
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.923
CYP2C9-inhibitor:	0.013
CYP2C9-substrate:	0.717
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.529
CYP3A4-inhibitor:	0.026
CYP3A4-substrate:	0.912

ADMET: Excretion

Clearance (CL):	7.34
Half-life (T1/2):	0.227

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.326
Drug-inuced Liver Injury (DILI):	0.116
AMES Toxicity:	0.757
Rat Oral Acute Toxicity:	0.051
Maximum Recommended Daily Dose:	0.908
Skin Sensitization:	0.684
Carcinogencity:	0.815
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.455

Download Data

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

Natural Product: NPC284706

Natural Product ID:	NPC284706
*Common Name:**	Gelsemoxonine
IUPAC Name:	n.a.
Synonyms:	Gelsemoxonine
Standard InCHIKey:	KCKQVEIIPULRFW-SAAOQMMJSA-N
Standard InCHI:	InChI=1S/C19H22N2O5/c1-3-14(22)19-11-9-26-16(15(19)23)18(8-12(11)20-19)10-6-4-5-7-13(10)21(25-2)17(18)24/h4-7,11-12,15-16,20,23H,3,8-9H2,1-2H3/t11-,12+,15+,16-,18+,19-/m1/s1
SMILES:	CCC(=O)[C@]12[C@@H]3CO[C@H]([C@@H]1O)[C@]1(C[C@@H]3N2)c2ccccc2N(C1=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL524079
PubChem CID:	44583831
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives

*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
EC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT762	Cell Line	A-431	Homo sapiens	EC50	>	100000.0	nM	PMID[519911]

☑ 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 NPC284706 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	245
0.1-0.2	1280
0.2-0.3	5312
0.3-0.4	21370
0.4-0.5	10855
0.5-0.6	3240
0.6-0.7	361
0.7-0.8	26
0.8-0.85	6
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9128	High Similarity	NPC477159
0.8529	High Similarity	NPC286871
0.8421	Intermediate Similarity	NPC176983
0.8232	Intermediate Similarity	NPC245741
0.8187	Intermediate Similarity	NPC29285
0.8045	Intermediate Similarity	NPC13367
0.8043	Intermediate Similarity	NPC282092
0.7868	Intermediate Similarity	NPC477160
0.7841	Intermediate Similarity	NPC143457
0.776	Intermediate Similarity	NPC475559
0.776	Intermediate Similarity	NPC302548
0.774	Intermediate Similarity	NPC472102
0.774	Intermediate Similarity	NPC309531
0.7609	Intermediate Similarity	NPC129624
0.7565	Intermediate Similarity	NPC243626
0.7565	Intermediate Similarity	NPC230313
0.7487	Intermediate Similarity	NPC14339
0.7473	Intermediate Similarity	NPC279527
0.7473	Intermediate Similarity	NPC214960
0.7433	Intermediate Similarity	NPC475094
0.7394	Intermediate Similarity	NPC11149
0.7363	Intermediate Similarity	NPC477161
0.7333	Intermediate Similarity	NPC113946
0.7322	Intermediate Similarity	NPC472106
0.7312	Intermediate Similarity	NPC285622
0.731	Intermediate Similarity	NPC90967
0.7308	Intermediate Similarity	NPC472120
0.7308	Intermediate Similarity	NPC472121
0.7308	Intermediate Similarity	NPC472101
0.7277	Intermediate Similarity	NPC477173
0.7241	Intermediate Similarity	NPC470488
0.7219	Intermediate Similarity	NPC96901
0.7213	Intermediate Similarity	NPC472117
0.7204	Intermediate Similarity	NPC472118
0.7179	Intermediate Similarity	NPC473298
0.7179	Intermediate Similarity	NPC473008
0.7158	Intermediate Similarity	NPC315368
0.715	Intermediate Similarity	NPC52262
0.7143	Intermediate Similarity	NPC470489
0.7143	Intermediate Similarity	NPC476441
0.7121	Intermediate Similarity	NPC221687
0.7114	Intermediate Similarity	NPC475489
0.7107	Intermediate Similarity	NPC473004
0.7085	Intermediate Similarity	NPC97100
0.7085	Intermediate Similarity	NPC473375
0.7083	Intermediate Similarity	NPC476428
0.7081	Intermediate Similarity	NPC313757
0.7059	Intermediate Similarity	NPC477180
0.7059	Intermediate Similarity	NPC477178
0.7059	Intermediate Similarity	NPC477181
0.7059	Intermediate Similarity	NPC254850
0.7039	Intermediate Similarity	NPC471945
0.7039	Intermediate Similarity	NPC471950
0.7037	Intermediate Similarity	NPC476425
0.7035	Intermediate Similarity	NPC34717
0.7024	Intermediate Similarity	NPC470490
0.7024	Intermediate Similarity	NPC477174
0.701	Intermediate Similarity	NPC477179
0.7006	Intermediate Similarity	NPC472103
0.7005	Intermediate Similarity	NPC472114
0.7005	Intermediate Similarity	NPC471951
0.7005	Intermediate Similarity	NPC22689
0.7005	Intermediate Similarity	NPC472115
0.7005	Intermediate Similarity	NPC105055
0.7005	Intermediate Similarity	NPC471946
0.6995	Remote Similarity	NPC471512
0.699	Remote Similarity	NPC181928
0.6974	Remote Similarity	NPC259626
0.6974	Remote Similarity	NPC473007
0.6971	Remote Similarity	NPC475359
0.6971	Remote Similarity	NPC191817
0.6957	Remote Similarity	NPC475259
0.6957	Remote Similarity	NPC470491
0.6947	Remote Similarity	NPC139085
0.6947	Remote Similarity	NPC251212
0.6947	Remote Similarity	NPC214626
0.6944	Remote Similarity	NPC122886
0.6935	Remote Similarity	NPC85651
0.6931	Remote Similarity	NPC469915
0.6927	Remote Similarity	NPC476326
0.6927	Remote Similarity	NPC260075
0.6923	Remote Similarity	NPC2933
0.6923	Remote Similarity	NPC97584
0.6908	Remote Similarity	NPC478075
0.6905	Remote Similarity	NPC475778
0.6904	Remote Similarity	NPC14994
0.6891	Remote Similarity	NPC218594
0.6891	Remote Similarity	NPC99043
0.6884	Remote Similarity	NPC25401
0.6882	Remote Similarity	NPC474058
0.6872	Remote Similarity	NPC256288
0.6865	Remote Similarity	NPC153694
0.6865	Remote Similarity	NPC211525
0.6862	Remote Similarity	NPC52059
0.6862	Remote Similarity	NPC470069
0.6862	Remote Similarity	NPC471124
0.6847	Remote Similarity	NPC100863
0.6845	Remote Similarity	NPC282339
0.6845	Remote Similarity	NPC99632
0.6842	Remote Similarity	NPC469743
0.6828	Remote Similarity	NPC263709
0.6828	Remote Similarity	NPC148468
0.6828	Remote Similarity	NPC97380
0.6828	Remote Similarity	NPC310403
0.6828	Remote Similarity	NPC243673
0.6828	Remote Similarity	NPC63210
0.681	Remote Similarity	NPC234999
0.6796	Remote Similarity	NPC471436
0.6791	Remote Similarity	NPC225319
0.6791	Remote Similarity	NPC68650
0.6786	Remote Similarity	NPC159963
0.678	Remote Similarity	NPC470497
0.678	Remote Similarity	NPC315051
0.6776	Remote Similarity	NPC475763
0.6768	Remote Similarity	NPC473615
0.6753	Remote Similarity	NPC186669
0.674	Remote Similarity	NPC264589
0.6738	Remote Similarity	NPC471122
0.6738	Remote Similarity	NPC36495
0.6734	Remote Similarity	NPC229484
0.6701	Remote Similarity	NPC203202
0.6701	Remote Similarity	NPC264482
0.67	Remote Similarity	NPC292675
0.67	Remote Similarity	NPC316405
0.6699	Remote Similarity	NPC214428
0.6699	Remote Similarity	NPC277350
0.6684	Remote Similarity	NPC21752
0.6684	Remote Similarity	NPC293255
0.6684	Remote Similarity	NPC276993
0.6684	Remote Similarity	NPC298851
0.6684	Remote Similarity	NPC210415
0.6684	Remote Similarity	NPC181138
0.6684	Remote Similarity	NPC177261
0.6667	Remote Similarity	NPC474059
0.6667	Remote Similarity	NPC161827
0.665	Remote Similarity	NPC475962
0.6649	Remote Similarity	NPC193410
0.6649	Remote Similarity	NPC278887
0.6648	Remote Similarity	NPC470301
0.6635	Remote Similarity	NPC474116
0.6633	Remote Similarity	NPC6974
0.6633	Remote Similarity	NPC321211
0.6632	Remote Similarity	NPC113056
0.6632	Remote Similarity	NPC138293
0.6615	Remote Similarity	NPC224970
0.6615	Remote Similarity	NPC223595
0.6615	Remote Similarity	NPC167724
0.6614	Remote Similarity	NPC248117
0.6614	Remote Similarity	NPC201424
0.6613	Remote Similarity	NPC478076
0.6602	Remote Similarity	NPC149708
0.6596	Remote Similarity	NPC61013
0.6589	Remote Similarity	NPC10732
0.6579	Remote Similarity	NPC293458
0.6573	Remote Similarity	NPC287358
0.657	Remote Similarity	NPC107828
0.657	Remote Similarity	NPC90358
0.6564	Remote Similarity	NPC469726
0.6564	Remote Similarity	NPC329338
0.656	Remote Similarity	NPC288110
0.6558	Remote Similarity	NPC473006
0.6557	Remote Similarity	NPC472100
0.6555	Remote Similarity	NPC162730
0.655	Remote Similarity	NPC322621
0.6538	Remote Similarity	NPC138830
0.6538	Remote Similarity	NPC14812
0.6528	Remote Similarity	NPC470971
0.6522	Remote Similarity	NPC470499
0.6515	Remote Similarity	NPC166169
0.6508	Remote Similarity	NPC123241
0.6507	Remote Similarity	NPC176371
0.6507	Remote Similarity	NPC136573
0.6505	Remote Similarity	NPC314223
0.65	Remote Similarity	NPC302235
0.6492	Remote Similarity	NPC476231
0.6489	Remote Similarity	NPC474877
0.6476	Remote Similarity	NPC1464
0.6459	Remote Similarity	NPC67904
0.6458	Remote Similarity	NPC328270
0.6456	Remote Similarity	NPC198205
0.6456	Remote Similarity	NPC21483
0.6448	Remote Similarity	NPC311330
0.6444	Remote Similarity	NPC477176
0.6444	Remote Similarity	NPC470729
0.6442	Remote Similarity	NPC311054
0.6442	Remote Similarity	NPC112752
0.6442	Remote Similarity	NPC52557
0.6441	Remote Similarity	NPC475271
0.6439	Remote Similarity	NPC55493
0.6438	Remote Similarity	NPC248601
0.6438	Remote Similarity	NPC77777
0.6435	Remote Similarity	NPC127996
0.6435	Remote Similarity	NPC151976
0.6432	Remote Similarity	NPC212799
0.6429	Remote Similarity	NPC473458
0.6422	Remote Similarity	NPC234772
0.6422	Remote Similarity	NPC5630
0.6422	Remote Similarity	NPC204491
0.6422	Remote Similarity	NPC314333
0.6422	Remote Similarity	NPC128582

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 NPC284706 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	158
0.1-0.2	482
0.2-0.3	786
0.3-0.4	2115
0.4-0.5	3775
0.5-0.6	1750
0.6-0.7	84
0.7-0.8	0
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
0.7232	Intermediate Similarity	NPD5941	Approved
0.7232	Intermediate Similarity	NPD5942	Approved
0.7198	Intermediate Similarity	NPD7599	Phase 2
0.7182	Intermediate Similarity	NPD7105	Phase 1
0.7045	Intermediate Similarity	NPD5024	Approved
0.703	Intermediate Similarity	NPD6805	Discontinued
0.6973	Remote Similarity	NPD7600	Phase 2
0.6957	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD1663	Discontinued
0.6719	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD6879	Phase 2
0.6684	Remote Similarity	NPD6878	Phase 2
0.6634	Remote Similarity	NPD5076	Approved
0.6634	Remote Similarity	NPD5077	Approved
0.6613	Remote Similarity	NPD4121	Phase 3
0.6613	Remote Similarity	NPD4120	Approved
0.661	Remote Similarity	NPD6073	Approved
0.6603	Remote Similarity	NPD7205	Discontinued
0.6587	Remote Similarity	NPD6238	Discontinued
0.6578	Remote Similarity	NPD5741	Approved
0.6578	Remote Similarity	NPD5742	Approved
0.6578	Remote Similarity	NPD5743	Approved
0.6576	Remote Similarity	NPD4682	Phase 2
0.6564	Remote Similarity	NPD5466	Approved
0.6546	Remote Similarity	NPD3824	Phase 1
0.6545	Remote Similarity	NPD3790	Phase 2
0.6497	Remote Similarity	NPD5184	Approved
0.6497	Remote Similarity	NPD5185	Approved
0.6497	Remote Similarity	NPD5182	Approved
0.6457	Remote Similarity	NPD5263	Approved
0.6425	Remote Similarity	NPD5725	Approved
0.6422	Remote Similarity	NPD4499	Approved
0.6415	Remote Similarity	NPD4467	Phase 2
0.6415	Remote Similarity	NPD4465	Phase 2
0.6414	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6484	Approved
0.6404	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD5296	Approved
0.6404	Remote Similarity	NPD6483	Approved
0.64	Remote Similarity	NPD4175	Approved
0.64	Remote Similarity	NPD4177	Approved
0.6398	Remote Similarity	NPD7528	Approved
0.6393	Remote Similarity	NPD2820	Phase 3
0.6387	Remote Similarity	NPD33	Approved
0.6387	Remote Similarity	NPD4393	Approved
0.6386	Remote Similarity	NPD6557	Phase 2
0.6378	Remote Similarity	NPD6609	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD4602	Approved
0.6374	Remote Similarity	NPD3625	Discontinued
0.6364	Remote Similarity	NPD2919	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD2613	Approved
0.6364	Remote Similarity	NPD2918	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4668	Phase 2
0.6344	Remote Similarity	NPD1801	Approved
0.6344	Remote Similarity	NPD1802	Approved
0.6339	Remote Similarity	NPD2365	Approved
0.6338	Remote Similarity	NPD1294	Discontinued
0.6323	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD3828	Approved
0.6313	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.631	Remote Similarity	NPD4432	Discontinued
0.6308	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD4601	Approved
0.6303	Remote Similarity	NPD4600	Approved
0.63	Remote Similarity	NPD2869	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD6294	Approved
0.6298	Remote Similarity	NPD6295	Approved
0.6286	Remote Similarity	NPD5196	Approved
0.6286	Remote Similarity	NPD5194	Approved
0.6286	Remote Similarity	NPD5197	Approved
0.628	Remote Similarity	NPD6665	Discontinued
0.6277	Remote Similarity	NPD5748	Phase 2
0.6277	Remote Similarity	NPD1405	Approved
0.6275	Remote Similarity	NPD3154	Approved
0.6275	Remote Similarity	NPD3153	Approved
0.6271	Remote Similarity	NPD4676	Approved
0.6263	Remote Similarity	NPD5997	Discontinued
0.6262	Remote Similarity	NPD8115	Approved
0.6262	Remote Similarity	NPD8114	Approved
0.6257	Remote Similarity	NPD3087	Approved
0.6257	Remote Similarity	NPD4745	Approved
0.6257	Remote Similarity	NPD7634	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD3088	Approved
0.6257	Remote Similarity	NPD3615	Approved
0.6257	Remote Similarity	NPD3089	Approved
0.6257	Remote Similarity	NPD2574	Discontinued
0.6257	Remote Similarity	NPD2573	Approved
0.6257	Remote Similarity	NPD3616	Approved
0.6257	Remote Similarity	NPD2571	Approved
0.6257	Remote Similarity	NPD3090	Approved
0.6257	Remote Similarity	NPD2570	Approved
0.6257	Remote Similarity	NPD3614	Approved
0.6257	Remote Similarity	NPD4746	Phase 3
0.6257	Remote Similarity	NPD2566	Approved
0.6256	Remote Similarity	NPD5430	Discontinued
0.625	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6768	Approved
0.625	Remote Similarity	NPD8630	Approved
0.6243	Remote Similarity	NPD2609	Approved
0.6243	Remote Similarity	NPD2610	Approved
0.6243	Remote Similarity	NPD4215	Approved
0.6243	Remote Similarity	NPD2611	Approved
0.6243	Remote Similarity	NPD8173	Phase 2
0.6243	Remote Similarity	NPD2608	Approved
0.6243	Remote Similarity	NPD3132	Approved
0.6243	Remote Similarity	NPD2612	Approved
0.6243	Remote Similarity	NPD8172	Phase 2
0.6243	Remote Similarity	NPD4216	Approved
0.6243	Remote Similarity	NPD4218	Approved
0.6243	Remote Similarity	NPD4217	Approved
0.6243	Remote Similarity	NPD3131	Approved
0.6238	Remote Similarity	NPD5003	Discontinued
0.6237	Remote Similarity	NPD7785	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD8240	Discontinued
0.6231	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD4981	Phase 2
0.6226	Remote Similarity	NPD6519	Phase 2
0.6224	Remote Similarity	NPD5823	Approved
0.6219	Remote Similarity	NPD3782	Discontinued
0.6209	Remote Similarity	NPD6342	Discontinued
0.6207	Remote Similarity	NPD3072	Approved
0.6207	Remote Similarity	NPD3071	Approved
0.6207	Remote Similarity	NPD3073	Approved
0.6204	Remote Similarity	NPD6518	Discontinued
0.6197	Remote Similarity	NPD7817	Phase 1
0.6196	Remote Similarity	NPD4152	Approved
0.6188	Remote Similarity	NPD4686	Approved
0.6188	Remote Similarity	NPD4685	Phase 3
0.6188	Remote Similarity	NPD4684	Phase 3
0.6181	Remote Similarity	NPD7854	Phase 2
0.618	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD4493	Discontinued
0.6161	Remote Similarity	NPD3437	Discontinued
0.6158	Remote Similarity	NPD4151	Approved
0.6158	Remote Similarity	NPD5993	Phase 1
0.6157	Remote Similarity	NPD7001	Phase 3
0.615	Remote Similarity	NPD7295	Approved
0.615	Remote Similarity	NPD2887	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD4762	Approved
0.6149	Remote Similarity	NPD4761	Approved
0.6146	Remote Similarity	NPD7267	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD4738	Phase 2
0.6138	Remote Similarity	NPD979	Approved
0.6136	Remote Similarity	NPD6792	Phase 3
0.6136	Remote Similarity	NPD7301	Phase 3
0.6133	Remote Similarity	NPD7805	Phase 3
0.6132	Remote Similarity	NPD5856	Discontinued
0.6131	Remote Similarity	NPD5137	Approved
0.613	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD1879	Approved
0.6126	Remote Similarity	NPD3399	Approved
0.6124	Remote Similarity	NPD7569	Approved
0.6124	Remote Similarity	NPD7570	Approved
0.6121	Remote Similarity	NPD7727	Phase 2
0.612	Remote Similarity	NPD5318	Discontinued
0.6117	Remote Similarity	NPD4041	Approved
0.6114	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD519	Approved
0.6111	Remote Similarity	NPD5426	Phase 3
0.6111	Remote Similarity	NPD5581	Approved
0.6111	Remote Similarity	NPD2037	Approved
0.6108	Remote Similarity	NPD3227	Phase 2
0.6108	Remote Similarity	NPD7014	Clinical (unspecified phase)
0.6108	Remote Similarity	NPD4329	Approved
0.6108	Remote Similarity	NPD4330	Approved
0.6106	Remote Similarity	NPD2564	Approved
0.6106	Remote Similarity	NPD4258	Approved
0.6106	Remote Similarity	NPD2565	Phase 2
0.6106	Remote Similarity	NPD4259	Approved
0.6101	Remote Similarity	NPD7302	Phase 3
0.6101	Remote Similarity	NPD7300	Phase 3
0.61	Remote Similarity	NPD7593	Clinical (unspecified phase)
0.6099	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD2096	Phase 2
0.6098	Remote Similarity	NPD2091	Phase 2
0.6096	Remote Similarity	NPD2387	Approved
0.6096	Remote Similarity	NPD2575	Approved
0.6096	Remote Similarity	NPD7186	Phase 3
0.6096	Remote Similarity	NPD5918	Discontinued
0.6091	Remote Similarity	NPD7595	Discontinued
0.6091	Remote Similarity	NPD7470	Discontinued
0.6091	Remote Similarity	NPD7035	Approved
0.6091	Remote Similarity	NPD7036	Phase 3
0.6087	Remote Similarity	NPD6891	Phase 2
0.6085	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6085	Remote Similarity	NPD5195	Discontinued
0.6081	Remote Similarity	NPD4562	Clinical (unspecified phase)
0.608	Remote Similarity	NPD5183	Approved
0.608	Remote Similarity	NPD5186	Approved
0.608	Remote Similarity	NPD2369	Discontinued
0.6079	Remote Similarity	NPD3912	Discontinued
0.6078	Remote Similarity	NPD3470	Approved
0.6078	Remote Similarity	NPD3471	Approved
0.6077	Remote Similarity	NPD5042	Phase 1
0.6077	Remote Similarity	NPD6659	Phase 2
0.6077	Remote Similarity	NPD5747	Discontinued
0.6073	Remote Similarity	NPD5982	Phase 2

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