NPASS Compound

Structure

NPC474270 OpenBabel07101718292D 31 36 0 0 1 0 0 0 0 0999 V2000 3.1800 1.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6954 0.9491 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1024 4.7546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3723 3.1380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5516 4.3944 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6149 2.8419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7687 0.8884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6654 3.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9424 3.9707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2315 2.1916 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5314 3.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2230 3.7619 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5314 4.5944 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2132 3.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8652 0.4597 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5345 1.8452 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5298 2.6749 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7002 1.6726 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3694 1.6879 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0224 4.3627 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6654 2.1235 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0315 3.1714 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4609 2.6435 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8219 4.9634 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4830 1.5285 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4919 4.3162 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6329 1.4025 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3044 2.0425 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 3 21 1 0 0 0 0 4 11 1 0 0 0 0 4 14 2 0 0 0 0 5 13 1 0 0 0 0 6 12 1 0 0 0 0 6 16 1 0 0 0 0 7 20 1 0 0 0 0 8 11 1 0 0 0 0 8 23 2 0 0 0 0 9 21 1 0 0 0 0 9 26 1 0 0 0 0 10 24 2 0 0 0 0 10 27 1 0 0 0 0 11 13 2 0 0 0 0 12 5 1 6 0 0 0 12 21 1 0 0 0 0 13 28 1 0 0 0 0 14 17 1 0 0 0 0 14 28 1 0 0 0 0 15 7 1 6 0 0 0 15 18 1 0 0 0 0 15 29 1 0 0 0 0 16 22 1 1 0 0 0 16 27 1 0 0 0 0 17 20 1 6 0 0 0 17 30 1 0 0 0 0 18 22 1 1 0 0 0 18 31 1 0 0 0 0 19 25 2 0 0 0 0 19 29 1 0 0 0 0 20 2 1 6 0 0 0 20 30 1 0 0 0 0 21 26 1 0 0 0 0 22 19 1 1 0 0 0 22 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	432.14
Volume:	403.659
LogP:	2.672
LogD:	2.038
LogS:	-4.593
# Rotatable Bonds:	4
TPSA:	120.4
# H-Bond Aceptor:	9
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.399
Synthetic Accessibility Score:	6.714
Fsp3:	0.682
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	3
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.113
MDCK Permeability:	4.94454252475407e-05
Pgp-inhibitor:	0.121
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.07
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.323
Plasma Protein Binding (PPB):	75.57035064697266%
Volume Distribution (VD):	2.03
Pgp-substrate:	22.522859573364258%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.772
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.596
CYP2C9-inhibitor:	0.024
CYP2C9-substrate:	0.015
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.186
CYP3A4-inhibitor:	0.217
CYP3A4-substrate:	0.484

ADMET: Excretion

Clearance (CL):	3.15
Half-life (T1/2):	0.248

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.926
Drug-inuced Liver Injury (DILI):	0.96
AMES Toxicity:	0.96
Rat Oral Acute Toxicity:	0.53
Maximum Recommended Daily Dose:	0.93
Skin Sensitization:	0.61
Carcinogencity:	0.864
Eye Corrosion:	0.017
Eye Irritation:	0.027
Respiratory Toxicity:	0.922

Download Data

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

Natural Product: NPC474270

Natural Product ID:	NPC474270
*Common Name:**	IBSBJNRWYFJSMO-QKJAREJLSA-N
IUPAC Name:	n.a.
Synonyms:	15,16-Epoxylophotoxin
Standard InCHIKey:	IBSBJNRWYFJSMO-QKJAREJLSA-N
Standard InCHI:	InChI=1S/C22H24O9/c1-10(24)27-16-6-12(21(3)9-26-21)5-13-11(8-23)4-14(28-13)17-20(2,30-17)7-15-18-22(16,31-18)19(25)29-15/h4,8,12,15-18H,5-7,9H2,1-3H3/t12-,15-,16+,17+,18-,20+,21?,22-/m0/s1
SMILES:	O=Cc1cc2oc1C[C@@H](C[C@@H](OC(=O)C)[C@@]13[C@H]([C@H](C[C@@]4([C@@H]2O4)C)OC3=O)O1)C1(C)OC1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464533
PubChem CID:	44566484
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO32683	lophogorgia peruana	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17190454]

☑ 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
GI50	3
Others	3

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	=	5800.0	nM	PMID[477557]
NPT81	Cell Line	A549	Homo sapiens	GI50	=	6000.0	nM	PMID[477557]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	=	4600.0	nM	PMID[477557]
NPT81	Cell Line	A549	Homo sapiens	TGI	=	9700.0	nM	PMID[477557]
NPT139	Cell Line	HT-29	Homo sapiens	TGI	=	6200.0	nM	PMID[477557]
NPT139	Cell Line	HT-29	Homo sapiens	LC50	=	9200.0	nM	PMID[477557]

☑ 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 NPC474270 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	421
0.1-0.2	1675
0.2-0.3	4449
0.3-0.4	9694
0.4-0.5	10158
0.5-0.6	7013
0.6-0.7	8385
0.7-0.8	861
0.8-0.85	18
0.85-0.9	5
0.9-0.95	7
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475904
0.9929	High Similarity	NPC474255
0.9929	High Similarity	NPC474220
0.9929	High Similarity	NPC471618
0.9787	High Similarity	NPC475864
0.9718	High Similarity	NPC474317
0.9577	High Similarity	NPC195920
0.9441	High Similarity	NPC37488
0.9388	High Similarity	NPC474378
0.9388	High Similarity	NPC474219
0.9225	High Similarity	NPC282973
0.9167	High Similarity	NPC110305
0.9028	High Similarity	NPC248795
0.9021	High Similarity	NPC474615
0.8671	High Similarity	NPC200718
0.8621	High Similarity	NPC286130
0.86	High Similarity	NPC104924
0.8523	High Similarity	NPC22248
0.8523	High Similarity	NPC254198
0.8462	Intermediate Similarity	NPC136340
0.8392	Intermediate Similarity	NPC45947
0.8387	Intermediate Similarity	NPC470380
0.8378	Intermediate Similarity	NPC107571
0.8288	Intermediate Similarity	NPC106247
0.8272	Intermediate Similarity	NPC473753
0.8272	Intermediate Similarity	NPC473766
0.8239	Intermediate Similarity	NPC473368
0.8231	Intermediate Similarity	NPC159786
0.8224	Intermediate Similarity	NPC86935
0.8212	Intermediate Similarity	NPC473152
0.8187	Intermediate Similarity	NPC475381
0.8187	Intermediate Similarity	NPC333139
0.8187	Intermediate Similarity	NPC305016
0.8182	Intermediate Similarity	NPC137570
0.8176	Intermediate Similarity	NPC303217
0.8129	Intermediate Similarity	NPC19747
0.8121	Intermediate Similarity	NPC473268
0.811	Intermediate Similarity	NPC472895
0.8105	Intermediate Similarity	NPC261733
0.8105	Intermediate Similarity	NPC307346
0.8105	Intermediate Similarity	NPC267004
0.8105	Intermediate Similarity	NPC218712
0.8095	Intermediate Similarity	NPC474426
0.8095	Intermediate Similarity	NPC474407
0.8095	Intermediate Similarity	NPC474425
0.8089	Intermediate Similarity	NPC18135
0.8075	Intermediate Similarity	NPC191828
0.8065	Intermediate Similarity	NPC221809
0.8063	Intermediate Similarity	NPC286722
0.8061	Intermediate Similarity	NPC302392
0.8037	Intermediate Similarity	NPC123088
0.8037	Intermediate Similarity	NPC276735
0.8037	Intermediate Similarity	NPC261184
0.8027	Intermediate Similarity	NPC471545
0.8012	Intermediate Similarity	NPC475295
0.8012	Intermediate Similarity	NPC237155
0.8012	Intermediate Similarity	NPC473473
0.8	Intermediate Similarity	NPC126723
0.8	Intermediate Similarity	NPC107646
0.8	Intermediate Similarity	NPC209364
0.8	Intermediate Similarity	NPC263265
0.8	Intermediate Similarity	NPC474542
0.8	Intermediate Similarity	NPC62799
0.8	Intermediate Similarity	NPC60973
0.7987	Intermediate Similarity	NPC84479
0.7975	Intermediate Similarity	NPC14499
0.7975	Intermediate Similarity	NPC469846
0.7975	Intermediate Similarity	NPC476035
0.7975	Intermediate Similarity	NPC285567
0.7975	Intermediate Similarity	NPC475039
0.7963	Intermediate Similarity	NPC25255
0.7939	Intermediate Similarity	NPC279768
0.7939	Intermediate Similarity	NPC476850
0.7939	Intermediate Similarity	NPC476861
0.7939	Intermediate Similarity	NPC270312
0.7931	Intermediate Similarity	NPC184391
0.7929	Intermediate Similarity	NPC472665
0.7927	Intermediate Similarity	NPC56358
0.7922	Intermediate Similarity	NPC80635
0.7914	Intermediate Similarity	NPC470939
0.7914	Intermediate Similarity	NPC193798
0.7905	Intermediate Similarity	NPC45358
0.7888	Intermediate Similarity	NPC278010
0.7888	Intermediate Similarity	NPC104736
0.7888	Intermediate Similarity	NPC295608
0.7888	Intermediate Similarity	NPC250769
0.7879	Intermediate Similarity	NPC121995
0.7875	Intermediate Similarity	NPC114880
0.787	Intermediate Similarity	NPC167340
0.7866	Intermediate Similarity	NPC283209
0.7862	Intermediate Similarity	NPC216810
0.7857	Intermediate Similarity	NPC469848
0.7853	Intermediate Similarity	NPC472653
0.7853	Intermediate Similarity	NPC287559
0.7848	Intermediate Similarity	NPC211625
0.7844	Intermediate Similarity	NPC470995
0.784	Intermediate Similarity	NPC81405
0.784	Intermediate Similarity	NPC187149
0.784	Intermediate Similarity	NPC304692
0.7838	Intermediate Similarity	NPC17681
0.7834	Intermediate Similarity	NPC224418
0.7831	Intermediate Similarity	NPC472651
0.7826	Intermediate Similarity	NPC131725
0.7826	Intermediate Similarity	NPC75310
0.7826	Intermediate Similarity	NPC44675
0.7826	Intermediate Similarity	NPC214541
0.7818	Intermediate Similarity	NPC476860
0.7818	Intermediate Similarity	NPC472664
0.7818	Intermediate Similarity	NPC476858
0.7818	Intermediate Similarity	NPC476856
0.7818	Intermediate Similarity	NPC476857
0.7815	Intermediate Similarity	NPC146872
0.7812	Intermediate Similarity	NPC75906
0.7806	Intermediate Similarity	NPC205071
0.7806	Intermediate Similarity	NPC470741
0.7806	Intermediate Similarity	NPC223415
0.7805	Intermediate Similarity	NPC117986
0.7805	Intermediate Similarity	NPC197596
0.7805	Intermediate Similarity	NPC68848
0.7805	Intermediate Similarity	NPC5079
0.7805	Intermediate Similarity	NPC188649
0.7799	Intermediate Similarity	NPC46551
0.7798	Intermediate Similarity	NPC159232
0.7798	Intermediate Similarity	NPC294512
0.7791	Intermediate Similarity	NPC116639
0.7791	Intermediate Similarity	NPC140952
0.7791	Intermediate Similarity	NPC477403
0.7785	Intermediate Similarity	NPC473428
0.7785	Intermediate Similarity	NPC473344
0.7785	Intermediate Similarity	NPC471544
0.7785	Intermediate Similarity	NPC97740
0.7784	Intermediate Similarity	NPC472652
0.7784	Intermediate Similarity	NPC271235
0.7778	Intermediate Similarity	NPC469485
0.7778	Intermediate Similarity	NPC41880
0.7771	Intermediate Similarity	NPC23387
0.7771	Intermediate Similarity	NPC276676
0.7771	Intermediate Similarity	NPC475779
0.777	Intermediate Similarity	NPC21460
0.7764	Intermediate Similarity	NPC308555
0.7758	Intermediate Similarity	NPC302369
0.7758	Intermediate Similarity	NPC234660
0.7758	Intermediate Similarity	NPC51568
0.7758	Intermediate Similarity	NPC288602
0.7758	Intermediate Similarity	NPC134254
0.7758	Intermediate Similarity	NPC88841
0.7758	Intermediate Similarity	NPC39986
0.7758	Intermediate Similarity	NPC476197
0.7751	Intermediate Similarity	NPC144288
0.775	Intermediate Similarity	NPC240214
0.7744	Intermediate Similarity	NPC335761
0.7738	Intermediate Similarity	NPC88593
0.7736	Intermediate Similarity	NPC329180
0.7733	Intermediate Similarity	NPC470740
0.773	Intermediate Similarity	NPC470625
0.773	Intermediate Similarity	NPC195954
0.773	Intermediate Similarity	NPC261597
0.773	Intermediate Similarity	NPC173544
0.773	Intermediate Similarity	NPC88007
0.773	Intermediate Similarity	NPC1408
0.773	Intermediate Similarity	NPC472283
0.773	Intermediate Similarity	NPC36655
0.773	Intermediate Similarity	NPC246841
0.773	Intermediate Similarity	NPC299038
0.7725	Intermediate Similarity	NPC476853
0.7725	Intermediate Similarity	NPC179015
0.7725	Intermediate Similarity	NPC173149
0.7724	Intermediate Similarity	NPC188377
0.7724	Intermediate Similarity	NPC65735
0.7722	Intermediate Similarity	NPC71821
0.7722	Intermediate Similarity	NPC10088
0.7712	Intermediate Similarity	NPC236532
0.7707	Intermediate Similarity	NPC105381
0.7707	Intermediate Similarity	NPC10302
0.7702	Intermediate Similarity	NPC475777
0.7702	Intermediate Similarity	NPC44577
0.7702	Intermediate Similarity	NPC268905
0.7697	Intermediate Similarity	NPC18986
0.7697	Intermediate Similarity	NPC472668
0.7688	Intermediate Similarity	NPC156189
0.7683	Intermediate Similarity	NPC472779
0.7683	Intermediate Similarity	NPC474932
0.7683	Intermediate Similarity	NPC475967
0.7669	Intermediate Similarity	NPC254163
0.7665	Intermediate Similarity	NPC86800
0.7661	Intermediate Similarity	NPC176413
0.7661	Intermediate Similarity	NPC56953
0.7658	Intermediate Similarity	NPC233763
0.7658	Intermediate Similarity	NPC262198
0.7654	Intermediate Similarity	NPC288534
0.7654	Intermediate Similarity	NPC57998
0.7651	Intermediate Similarity	NPC14822
0.7651	Intermediate Similarity	NPC472669
0.7651	Intermediate Similarity	NPC471168
0.7647	Intermediate Similarity	NPC120220
0.7643	Intermediate Similarity	NPC137295
0.764	Intermediate Similarity	NPC191104
0.7639	Intermediate Similarity	NPC1848
0.7636	Intermediate Similarity	NPC477402
0.7632	Intermediate Similarity	NPC92941

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 NPC474270 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	345
0.1-0.2	1084
0.2-0.3	2264
0.3-0.4	2782
0.4-0.5	1813
0.5-0.6	640
0.6-0.7	214
0.7-0.8	7
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8187	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD8434	Phase 2
0.7453	Intermediate Similarity	NPD920	Approved
0.7425	Intermediate Similarity	NPD919	Approved
0.7375	Intermediate Similarity	NPD6799	Approved
0.7329	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD1471	Phase 3
0.7317	Intermediate Similarity	NPD6599	Discontinued
0.7289	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD7075	Discontinued
0.7251	Intermediate Similarity	NPD3926	Phase 2
0.7235	Intermediate Similarity	NPD1247	Approved
0.7229	Intermediate Similarity	NPD6801	Discontinued
0.7215	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD6764	Approved
0.7159	Intermediate Similarity	NPD6765	Approved
0.7143	Intermediate Similarity	NPD3817	Phase 2
0.7143	Intermediate Similarity	NPD5402	Approved
0.7134	Intermediate Similarity	NPD5403	Approved
0.7125	Intermediate Similarity	NPD1243	Approved
0.7117	Intermediate Similarity	NPD5401	Approved
0.7081	Intermediate Similarity	NPD4628	Phase 3
0.7076	Intermediate Similarity	NPD5494	Approved
0.7044	Intermediate Similarity	NPD2796	Approved
0.7037	Intermediate Similarity	NPD3887	Approved
0.7029	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD6832	Phase 2
0.7	Intermediate Similarity	NPD6784	Approved
0.7	Intermediate Similarity	NPD6785	Approved
0.7	Intermediate Similarity	NPD3882	Suspended
0.7	Intermediate Similarity	NPD2344	Approved
0.6994	Remote Similarity	NPD6808	Phase 2
0.6982	Remote Similarity	NPD5761	Phase 2
0.6982	Remote Similarity	NPD5760	Phase 2
0.6928	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD2403	Approved
0.6882	Remote Similarity	NPD7819	Suspended
0.6875	Remote Similarity	NPD2799	Discontinued
0.6872	Remote Similarity	NPD6559	Discontinued
0.686	Remote Similarity	NPD3749	Approved
0.6845	Remote Similarity	NPD3226	Approved
0.6836	Remote Similarity	NPD3751	Discontinued
0.6835	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD2309	Approved
0.6807	Remote Similarity	NPD2532	Approved
0.6807	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD2534	Approved
0.6807	Remote Similarity	NPD2533	Approved
0.6792	Remote Similarity	NPD6355	Discontinued
0.679	Remote Similarity	NPD2353	Approved
0.679	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD1019	Discontinued
0.6765	Remote Similarity	NPD7411	Suspended
0.6763	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD17	Approved
0.6752	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD3818	Discontinued
0.6728	Remote Similarity	NPD1551	Phase 2
0.6726	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD6279	Approved
0.6725	Remote Similarity	NPD6280	Approved
0.672	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD2313	Discontinued
0.6707	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD2800	Approved
0.6706	Remote Similarity	NPD4380	Phase 2
0.6705	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD3787	Discontinued
0.6704	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6002	Phase 3
0.6687	Remote Similarity	NPD447	Suspended
0.6687	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6005	Phase 3
0.6687	Remote Similarity	NPD6004	Phase 3
0.6684	Remote Similarity	NPD8285	Discontinued
0.6667	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9092	Discovery
0.6667	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5647	Approved
0.6667	Remote Similarity	NPD7033	Discontinued
0.6648	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD1549	Phase 2
0.663	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD6166	Phase 2
0.6629	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD1934	Approved
0.6627	Remote Similarity	NPD2354	Approved
0.6623	Remote Similarity	NPD9717	Approved
0.6623	Remote Similarity	NPD1608	Approved
0.6592	Remote Similarity	NPD7473	Discontinued
0.659	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD2346	Discontinued
0.6585	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD1933	Approved
0.6575	Remote Similarity	NPD2067	Discontinued
0.6567	Remote Similarity	NPD8404	Phase 2
0.6564	Remote Similarity	NPD3748	Approved
0.6562	Remote Similarity	NPD6233	Phase 2
0.6561	Remote Similarity	NPD2798	Approved
0.6538	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6797	Phase 2
0.6538	Remote Similarity	NPD1876	Approved
0.6536	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD8313	Approved
0.6522	Remote Similarity	NPD8312	Approved
0.6517	Remote Similarity	NPD6232	Discontinued
0.6516	Remote Similarity	NPD3972	Approved
0.6509	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD7251	Discontinued
0.6503	Remote Similarity	NPD7685	Pre-registration
0.65	Remote Similarity	NPD6798	Discontinued
0.6497	Remote Similarity	NPD3266	Approved
0.6497	Remote Similarity	NPD3267	Approved
0.6494	Remote Similarity	NPD7972	Discontinued
0.6494	Remote Similarity	NPD2801	Approved
0.648	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD7808	Phase 3
0.6464	Remote Similarity	NPD2163	Approved
0.6463	Remote Similarity	NPD1510	Phase 2
0.6457	Remote Similarity	NPD5353	Approved
0.645	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD5953	Discontinued
0.6444	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6190	Approved
0.6425	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD2935	Discontinued
0.642	Remote Similarity	NPD7768	Phase 2
0.642	Remote Similarity	NPD4967	Phase 2
0.642	Remote Similarity	NPD4307	Phase 2
0.642	Remote Similarity	NPD1240	Approved
0.642	Remote Similarity	NPD4965	Approved
0.642	Remote Similarity	NPD4966	Approved
0.6417	Remote Similarity	NPD8150	Discontinued
0.6412	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD3146	Approved
0.6412	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD2654	Approved
0.6405	Remote Similarity	NPD9545	Approved
0.64	Remote Similarity	NPD1241	Discontinued
0.6398	Remote Similarity	NPD3268	Approved
0.6398	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD3764	Approved
0.6398	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD2182	Approved
0.6393	Remote Similarity	NPD7074	Phase 3
0.6392	Remote Similarity	NPD1203	Approved
0.638	Remote Similarity	NPD230	Phase 1
0.6379	Remote Similarity	NPD6385	Approved
0.6379	Remote Similarity	NPD6386	Approved
0.6378	Remote Similarity	NPD7435	Discontinued
0.6374	Remote Similarity	NPD1512	Approved
0.6374	Remote Similarity	NPD7799	Discontinued
0.6369	Remote Similarity	NPD3750	Approved
0.6369	Remote Similarity	NPD6959	Discontinued
0.6369	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5585	Approved
0.6364	Remote Similarity	NPD2296	Approved
0.6358	Remote Similarity	NPD4062	Phase 3
0.6352	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD6234	Discontinued
0.6347	Remote Similarity	NPD2897	Discontinued
0.6347	Remote Similarity	NPD5958	Discontinued
0.6341	Remote Similarity	NPD1607	Approved
0.6341	Remote Similarity	NPD6653	Approved
0.6339	Remote Similarity	NPD7054	Approved
0.6339	Remote Similarity	NPD5844	Phase 1
0.6325	Remote Similarity	NPD2438	Suspended
0.6308	Remote Similarity	NPD4107	Approved
0.6304	Remote Similarity	NPD7472	Approved
0.6303	Remote Similarity	NPD7097	Phase 1
0.6301	Remote Similarity	NPD957	Approved
0.6298	Remote Similarity	NPD5242	Approved
0.6296	Remote Similarity	NPD411	Approved
0.6294	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD2797	Approved
0.6287	Remote Similarity	NPD5763	Approved
0.6287	Remote Similarity	NPD5762	Approved
0.6279	Remote Similarity	NPD6273	Approved
0.6279	Remote Similarity	NPD5049	Phase 3
0.6278	Remote Similarity	NPD7199	Phase 2
0.6276	Remote Similarity	NPD4482	Phase 3
0.6265	Remote Similarity	NPD4308	Phase 3
0.6264	Remote Similarity	NPD7458	Discontinued
0.6257	Remote Similarity	NPD1511	Approved
0.625	Remote Similarity	NPD7286	Phase 2
0.625	Remote Similarity	NPD37	Approved
0.625	Remote Similarity	NPD4534	Discontinued
0.6243	Remote Similarity	NPD5711	Approved
0.6243	Remote Similarity	NPD5710	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