NPASS Compound

Structure

NPC474255 OpenBabel07101718202D 34 38 0 0 1 0 0 0 0 0999 V2000 -2.4675 -3.6675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5881 -4.6602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5663 -0.7521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1697 1.8597 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0815 -1.7195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9037 0.4855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1537 -1.9535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1537 1.9535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0377 -0.9855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1870 -3.4587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2670 -3.0668 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5081 -5.0522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3663 -1.7319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1464 -2.0741 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9037 -0.4855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7446 -0.9709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7446 0.9709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3307 1.3855 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3307 -1.3855 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0815 1.7195 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 -1.7986 -0.2299 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1464 2.0741 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1717 -0.4855 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6286 -6.0449 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1148 -2.3950 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5198 -0.9226 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3075 -4.4514 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5822 -2.0486 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9839 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0310 0.7129 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9210 2.7065 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 11 2 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 5 14 1 0 0 0 0 5 16 1 0 0 0 0 6 15 1 0 0 0 0 6 17 2 0 0 0 0 7 14 1 0 0 0 0 7 19 1 0 0 0 0 8 23 1 0 0 0 0 9 15 1 0 0 0 0 9 25 2 0 0 0 0 10 11 1 0 0 0 0 10 29 1 0 0 0 0 12 26 2 0 0 0 0 12 29 1 0 0 0 0 13 27 2 0 0 0 0 13 30 1 0 0 0 0 14 11 1 1 0 0 0 15 16 2 0 0 0 0 16 31 1 0 0 0 0 17 20 1 0 0 0 0 17 31 1 0 0 0 0 18 8 1 1 0 0 0 18 21 1 0 0 0 0 18 32 1 0 0 0 0 19 24 1 6 0 0 0 19 30 1 0 0 0 0 20 23 1 1 0 0 0 20 33 1 0 0 0 0 21 24 1 6 0 0 0 21 34 1 0 0 0 0 22 28 2 0 0 0 0 22 32 1 0 0 0 0 23 4 1 1 0 0 0 23 33 1 0 0 0 0 24 22 1 6 0 0 0 24 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	474.15
Volume:	450.325
LogP:	2.951
LogD:	1.717
LogS:	-4.472
# Rotatable Bonds:	7
TPSA:	134.17
# H-Bond Aceptor:	10
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.205
Synthetic Accessibility Score:	6.636
Fsp3:	0.583
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.134
MDCK Permeability:	5.956759923719801e-05
Pgp-inhibitor:	0.019
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.036
20% Bioavailability (F20%):	0.027
30% Bioavailability (F30%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.595
Plasma Protein Binding (PPB):	64.9190673828125%
Volume Distribution (VD):	1.385
Pgp-substrate:	35.714210510253906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.075
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.138
CYP2C9-inhibitor:	0.025
CYP2C9-substrate:	0.021
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.142
CYP3A4-inhibitor:	0.244
CYP3A4-substrate:	0.362

ADMET: Excretion

Clearance (CL):	2.9
Half-life (T1/2):	0.327

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.975
Drug-inuced Liver Injury (DILI):	0.977
AMES Toxicity:	0.984
Rat Oral Acute Toxicity:	0.616
Maximum Recommended Daily Dose:	0.932
Skin Sensitization:	0.536
Carcinogencity:	0.774
Eye Corrosion:	0.056
Eye Irritation:	0.063
Respiratory Toxicity:	0.916

Download Data

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

Natural Product: NPC474255

Natural Product ID:	NPC474255
*Common Name:**	GZCGPNRLCLQQFO-PTAFGJLESA-N
IUPAC Name:	n.a.
Synonyms:	17-Acetoxylophotoxin
Standard InCHIKey:	GZCGPNRLCLQQFO-PTAFGJLESA-N
Standard InCHI:	InChI=1S/C24H26O10/c1-11(10-29-12(2)26)14-5-16-15(9-25)6-17(31-16)20-23(4,33-20)8-18-21-24(34-21,22(28)32-18)19(7-14)30-13(3)27/h6,9,14,18-21H,1,5,7-8,10H2,2-4H3/t14-,18-,19+,20+,21-,23+,24-/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)C(=C)COC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464326
PubChem CID:	16099476
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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	=	14500.0	nM	PMID[490075]
NPT81	Cell Line	A549	Homo sapiens	GI50	=	17900.0	nM	PMID[490075]

☑ 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 NPC474255 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	418
0.1-0.2	1685
0.2-0.3	4634
0.3-0.4	9932
0.4-0.5	9908
0.5-0.6	7001
0.6-0.7	8261
0.7-0.8	820
0.8-0.85	14
0.85-0.9	6
0.9-0.95	7
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474220
1.0	High Similarity	NPC471618
0.9929	High Similarity	NPC475904
0.9929	High Similarity	NPC474270
0.9857	High Similarity	NPC475864
0.9787	High Similarity	NPC474317
0.9645	High Similarity	NPC195920
0.9507	High Similarity	NPC37488
0.9452	High Similarity	NPC474378
0.9452	High Similarity	NPC474219
0.9231	High Similarity	NPC110305
0.9155	High Similarity	NPC282973
0.8958	High Similarity	NPC248795
0.8951	High Similarity	NPC474615
0.8658	High Similarity	NPC104924
0.8601	High Similarity	NPC200718
0.8581	High Similarity	NPC254198
0.8581	High Similarity	NPC22248
0.8552	High Similarity	NPC286130
0.8521	High Similarity	NPC136340
0.8442	Intermediate Similarity	NPC470380
0.8435	Intermediate Similarity	NPC107571
0.8322	Intermediate Similarity	NPC45947
0.8288	Intermediate Similarity	NPC159786
0.8239	Intermediate Similarity	NPC137570
0.8231	Intermediate Similarity	NPC303217
0.8219	Intermediate Similarity	NPC106247
0.821	Intermediate Similarity	NPC473753
0.821	Intermediate Similarity	NPC473766
0.8176	Intermediate Similarity	NPC473368
0.8158	Intermediate Similarity	NPC218712
0.8158	Intermediate Similarity	NPC86935
0.8158	Intermediate Similarity	NPC261733
0.8158	Intermediate Similarity	NPC307346
0.8158	Intermediate Similarity	NPC267004
0.8146	Intermediate Similarity	NPC473152
0.8125	Intermediate Similarity	NPC475381
0.8125	Intermediate Similarity	NPC333139
0.8125	Intermediate Similarity	NPC305016
0.8082	Intermediate Similarity	NPC471545
0.8065	Intermediate Similarity	NPC19747
0.8054	Intermediate Similarity	NPC473268
0.8049	Intermediate Similarity	NPC472895
0.8027	Intermediate Similarity	NPC474425
0.8027	Intermediate Similarity	NPC474426
0.8027	Intermediate Similarity	NPC474407
0.8025	Intermediate Similarity	NPC18135
0.8012	Intermediate Similarity	NPC191828
0.8	Intermediate Similarity	NPC286722
0.8	Intermediate Similarity	NPC302392
0.8	Intermediate Similarity	NPC221809
0.7975	Intermediate Similarity	NPC261184
0.7975	Intermediate Similarity	NPC123088
0.7975	Intermediate Similarity	NPC276735
0.7959	Intermediate Similarity	NPC45358
0.795	Intermediate Similarity	NPC237155
0.795	Intermediate Similarity	NPC475295
0.795	Intermediate Similarity	NPC473473
0.7937	Intermediate Similarity	NPC126723
0.7937	Intermediate Similarity	NPC263265
0.7937	Intermediate Similarity	NPC278010
0.7937	Intermediate Similarity	NPC107646
0.7937	Intermediate Similarity	NPC474542
0.7937	Intermediate Similarity	NPC209364
0.7937	Intermediate Similarity	NPC60973
0.7937	Intermediate Similarity	NPC295608
0.7937	Intermediate Similarity	NPC250769
0.7935	Intermediate Similarity	NPC62799
0.7922	Intermediate Similarity	NPC84479
0.7914	Intermediate Similarity	NPC469846
0.7914	Intermediate Similarity	NPC475039
0.7914	Intermediate Similarity	NPC476035
0.7914	Intermediate Similarity	NPC285567
0.7914	Intermediate Similarity	NPC14499
0.7901	Intermediate Similarity	NPC25255
0.7891	Intermediate Similarity	NPC17681
0.7879	Intermediate Similarity	NPC270312
0.7879	Intermediate Similarity	NPC476861
0.7879	Intermediate Similarity	NPC279768
0.7879	Intermediate Similarity	NPC476850
0.7875	Intermediate Similarity	NPC131725
0.787	Intermediate Similarity	NPC472665
0.7866	Intermediate Similarity	NPC56358
0.7862	Intermediate Similarity	NPC184391
0.7857	Intermediate Similarity	NPC80635
0.7853	Intermediate Similarity	NPC193798
0.7853	Intermediate Similarity	NPC470939
0.7838	Intermediate Similarity	NPC471544
0.7838	Intermediate Similarity	NPC97740
0.7838	Intermediate Similarity	NPC473344
0.7826	Intermediate Similarity	NPC104736
0.7823	Intermediate Similarity	NPC21460
0.7818	Intermediate Similarity	NPC121995
0.7812	Intermediate Similarity	NPC114880
0.7811	Intermediate Similarity	NPC167340
0.7805	Intermediate Similarity	NPC283209
0.7798	Intermediate Similarity	NPC144288
0.7798	Intermediate Similarity	NPC469848
0.7793	Intermediate Similarity	NPC216810
0.7791	Intermediate Similarity	NPC472653
0.7791	Intermediate Similarity	NPC287559
0.7785	Intermediate Similarity	NPC211625
0.7784	Intermediate Similarity	NPC470995
0.7778	Intermediate Similarity	NPC304692
0.7778	Intermediate Similarity	NPC188377
0.7778	Intermediate Similarity	NPC65735
0.7778	Intermediate Similarity	NPC81405
0.7778	Intermediate Similarity	NPC187149
0.7771	Intermediate Similarity	NPC224418
0.7771	Intermediate Similarity	NPC179015
0.7771	Intermediate Similarity	NPC173149
0.7771	Intermediate Similarity	NPC472651
0.7764	Intermediate Similarity	NPC214541
0.7764	Intermediate Similarity	NPC75310
0.7764	Intermediate Similarity	NPC44675
0.7758	Intermediate Similarity	NPC476858
0.7758	Intermediate Similarity	NPC476857
0.7758	Intermediate Similarity	NPC472664
0.7758	Intermediate Similarity	NPC476860
0.7758	Intermediate Similarity	NPC476856
0.7756	Intermediate Similarity	NPC10302
0.7756	Intermediate Similarity	NPC105381
0.775	Intermediate Similarity	NPC75906
0.7748	Intermediate Similarity	NPC146872
0.7744	Intermediate Similarity	NPC197596
0.7744	Intermediate Similarity	NPC68848
0.7744	Intermediate Similarity	NPC117986
0.7744	Intermediate Similarity	NPC188649
0.7744	Intermediate Similarity	NPC5079
0.7742	Intermediate Similarity	NPC223415
0.7742	Intermediate Similarity	NPC470741
0.7742	Intermediate Similarity	NPC205071
0.7738	Intermediate Similarity	NPC294512
0.7738	Intermediate Similarity	NPC159232
0.7736	Intermediate Similarity	NPC46551
0.773	Intermediate Similarity	NPC116639
0.773	Intermediate Similarity	NPC477403
0.773	Intermediate Similarity	NPC140952
0.7725	Intermediate Similarity	NPC271235
0.7725	Intermediate Similarity	NPC472652
0.7722	Intermediate Similarity	NPC473428
0.7716	Intermediate Similarity	NPC469485
0.7716	Intermediate Similarity	NPC41880
0.7711	Intermediate Similarity	NPC475779
0.7711	Intermediate Similarity	NPC23387
0.7707	Intermediate Similarity	NPC276676
0.7702	Intermediate Similarity	NPC308555
0.7697	Intermediate Similarity	NPC476197
0.7697	Intermediate Similarity	NPC234660
0.7697	Intermediate Similarity	NPC51568
0.7697	Intermediate Similarity	NPC39986
0.7697	Intermediate Similarity	NPC288602
0.7697	Intermediate Similarity	NPC88841
0.7697	Intermediate Similarity	NPC14822
0.7697	Intermediate Similarity	NPC134254
0.7697	Intermediate Similarity	NPC302369
0.7692	Intermediate Similarity	NPC1848
0.7692	Intermediate Similarity	NPC137295
0.7688	Intermediate Similarity	NPC240214
0.7688	Intermediate Similarity	NPC191104
0.7683	Intermediate Similarity	NPC335761
0.7679	Intermediate Similarity	NPC88593
0.7676	Intermediate Similarity	NPC244862
0.7676	Intermediate Similarity	NPC67345
0.7673	Intermediate Similarity	NPC329180
0.7669	Intermediate Similarity	NPC173544
0.7669	Intermediate Similarity	NPC36655
0.7669	Intermediate Similarity	NPC261597
0.7669	Intermediate Similarity	NPC299038
0.7669	Intermediate Similarity	NPC470625
0.7669	Intermediate Similarity	NPC88007
0.7669	Intermediate Similarity	NPC472283
0.7669	Intermediate Similarity	NPC246841
0.7669	Intermediate Similarity	NPC1408
0.7669	Intermediate Similarity	NPC195954
0.7667	Intermediate Similarity	NPC470740
0.7665	Intermediate Similarity	NPC476853
0.7658	Intermediate Similarity	NPC10088
0.7658	Intermediate Similarity	NPC71821
0.7647	Intermediate Similarity	NPC236532
0.764	Intermediate Similarity	NPC44577
0.764	Intermediate Similarity	NPC475777
0.764	Intermediate Similarity	NPC268905
0.7636	Intermediate Similarity	NPC95472
0.7636	Intermediate Similarity	NPC18986
0.7636	Intermediate Similarity	NPC49009
0.7636	Intermediate Similarity	NPC472668
0.7636	Intermediate Similarity	NPC239270
0.7636	Intermediate Similarity	NPC303210
0.7625	Intermediate Similarity	NPC88445
0.7625	Intermediate Similarity	NPC156189
0.7622	Intermediate Similarity	NPC472779
0.7622	Intermediate Similarity	NPC475967
0.7622	Intermediate Similarity	NPC474932
0.7619	Intermediate Similarity	NPC95567
0.7619	Intermediate Similarity	NPC471554
0.7619	Intermediate Similarity	NPC193881
0.7619	Intermediate Similarity	NPC323137
0.7619	Intermediate Similarity	NPC473355
0.7619	Intermediate Similarity	NPC471573

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 NPC474255 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	1083
0.2-0.3	2310
0.3-0.4	2784
0.4-0.5	1791
0.5-0.6	625
0.6-0.7	205
0.7-0.8	6
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
0.8125	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD920	Approved
0.7486	Intermediate Similarity	NPD8434	Phase 2
0.747	Intermediate Similarity	NPD919	Approved
0.7421	Intermediate Similarity	NPD6799	Approved
0.7375	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD7075	Discontinued
0.7278	Intermediate Similarity	NPD1247	Approved
0.7273	Intermediate Similarity	NPD6801	Discontinued
0.7261	Intermediate Similarity	NPD1471	Phase 3
0.7256	Intermediate Similarity	NPD6599	Discontinued
0.725	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD3926	Phase 2
0.7186	Intermediate Similarity	NPD5402	Approved
0.7186	Intermediate Similarity	NPD3817	Phase 2
0.7178	Intermediate Similarity	NPD5403	Approved
0.717	Intermediate Similarity	NPD1243	Approved
0.716	Intermediate Similarity	NPD5401	Approved
0.7152	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD6765	Approved
0.7102	Intermediate Similarity	NPD6764	Approved
0.7089	Intermediate Similarity	NPD2796	Approved
0.7081	Intermediate Similarity	NPD3887	Approved
0.7059	Intermediate Similarity	NPD6832	Phase 2
0.7041	Intermediate Similarity	NPD3882	Suspended
0.7019	Intermediate Similarity	NPD4628	Phase 3
0.7018	Intermediate Similarity	NPD5494	Approved
0.6974	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD6784	Approved
0.6944	Remote Similarity	NPD6785	Approved
0.6937	Remote Similarity	NPD2344	Approved
0.6936	Remote Similarity	NPD6808	Phase 2
0.6923	Remote Similarity	NPD5761	Phase 2
0.6923	Remote Similarity	NPD5760	Phase 2
0.691	Remote Similarity	NPD6559	Discontinued
0.6857	Remote Similarity	NPD2403	Approved
0.6848	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD2353	Approved
0.6832	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD7819	Suspended
0.6818	Remote Similarity	NPD1019	Discontinued
0.6813	Remote Similarity	NPD2799	Discontinued
0.6805	Remote Similarity	NPD7411	Suspended
0.6802	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD3749	Approved
0.6795	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD3226	Approved
0.678	Remote Similarity	NPD3751	Discontinued
0.678	Remote Similarity	NPD3818	Discontinued
0.6772	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.677	Remote Similarity	NPD1551	Phase 2
0.6768	Remote Similarity	NPD2309	Approved
0.6766	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD2313	Discontinued
0.6748	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD2532	Approved
0.6747	Remote Similarity	NPD2534	Approved
0.6747	Remote Similarity	NPD2533	Approved
0.6746	Remote Similarity	NPD4380	Phase 2
0.6744	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.673	Remote Similarity	NPD447	Suspended
0.673	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.673	Remote Similarity	NPD6355	Discontinued
0.6711	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD9092	Discovery
0.6708	Remote Similarity	NPD7033	Discontinued
0.6707	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD17	Approved
0.6687	Remote Similarity	NPD1549	Phase 2
0.6685	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9717	Approved
0.6667	Remote Similarity	NPD1934	Approved
0.6667	Remote Similarity	NPD6280	Approved
0.6667	Remote Similarity	NPD6166	Phase 2
0.6667	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6279	Approved
0.6667	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2354	Approved
0.6648	Remote Similarity	NPD3787	Discontinued
0.6646	Remote Similarity	NPD2800	Approved
0.6632	Remote Similarity	NPD8285	Discontinued
0.6628	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD6002	Phase 3
0.6626	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD6005	Phase 3
0.6626	Remote Similarity	NPD6004	Phase 3
0.6626	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD1933	Approved
0.6621	Remote Similarity	NPD2067	Discontinued
0.6607	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6233	Phase 2
0.6603	Remote Similarity	NPD5647	Approved
0.659	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6576	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD6797	Phase 2
0.6558	Remote Similarity	NPD1608	Approved
0.6548	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD6798	Discontinued
0.6538	Remote Similarity	NPD7251	Discontinued
0.6536	Remote Similarity	NPD7473	Discontinued
0.6532	Remote Similarity	NPD2801	Approved
0.6524	Remote Similarity	NPD2346	Discontinued
0.6517	Remote Similarity	NPD8404	Phase 2
0.6503	Remote Similarity	NPD1510	Phase 2
0.6503	Remote Similarity	NPD3748	Approved
0.6503	Remote Similarity	NPD7808	Phase 3
0.65	Remote Similarity	NPD2163	Approved
0.6497	Remote Similarity	NPD2798	Approved
0.6494	Remote Similarity	NPD5353	Approved
0.6488	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD5953	Discontinued
0.648	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD1876	Approved
0.6467	Remote Similarity	NPD8312	Approved
0.6467	Remote Similarity	NPD8313	Approved
0.6467	Remote Similarity	NPD6190	Approved
0.6463	Remote Similarity	NPD2935	Discontinued
0.6463	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD6232	Discontinued
0.646	Remote Similarity	NPD1240	Approved
0.646	Remote Similarity	NPD4307	Phase 2
0.6452	Remote Similarity	NPD3972	Approved
0.645	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.645	Remote Similarity	NPD3146	Approved
0.6448	Remote Similarity	NPD7685	Pre-registration
0.6447	Remote Similarity	NPD9545	Approved
0.6446	Remote Similarity	NPD2654	Approved
0.6443	Remote Similarity	NPD1241	Discontinued
0.6438	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD7972	Discontinued
0.6433	Remote Similarity	NPD3267	Approved
0.6433	Remote Similarity	NPD1203	Approved
0.6433	Remote Similarity	NPD3266	Approved
0.6429	Remote Similarity	NPD7074	Phase 3
0.6425	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.642	Remote Similarity	NPD230	Phase 1
0.6416	Remote Similarity	NPD6385	Approved
0.6416	Remote Similarity	NPD6386	Approved
0.6412	Remote Similarity	NPD1512	Approved
0.64	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD4062	Phase 3
0.6389	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.638	Remote Similarity	NPD1607	Approved
0.6374	Remote Similarity	NPD7054	Approved
0.6369	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD8150	Discontinued
0.6364	Remote Similarity	NPD4967	Phase 2
0.6364	Remote Similarity	NPD4966	Approved
0.6364	Remote Similarity	NPD7768	Phase 2
0.6364	Remote Similarity	NPD4965	Approved
0.6353	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD7097	Phase 1
0.6339	Remote Similarity	NPD7472	Approved
0.6337	Remote Similarity	NPD957	Approved
0.6335	Remote Similarity	NPD3764	Approved
0.6335	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD411	Approved
0.6335	Remote Similarity	NPD3268	Approved
0.6327	Remote Similarity	NPD7435	Discontinued
0.6327	Remote Similarity	NPD2182	Approved
0.6319	Remote Similarity	NPD7799	Discontinued
0.6316	Remote Similarity	NPD5049	Phase 3
0.6313	Remote Similarity	NPD6959	Discontinued
0.631	Remote Similarity	NPD3750	Approved
0.631	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6307	Remote Similarity	NPD2296	Approved
0.6303	Remote Similarity	NPD4308	Phase 3
0.6299	Remote Similarity	NPD5585	Approved
0.6294	Remote Similarity	NPD1511	Approved
0.6292	Remote Similarity	NPD6234	Discontinued
0.6289	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD5958	Discontinued
0.6287	Remote Similarity	NPD2897	Discontinued
0.6284	Remote Similarity	NPD5844	Phase 1
0.6284	Remote Similarity	NPD7286	Phase 2
0.628	Remote Similarity	NPD6653	Approved
0.628	Remote Similarity	NPD6651	Approved
0.6269	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD2438	Suspended
0.6259	Remote Similarity	NPD1358	Approved
0.6258	Remote Similarity	NPD3142	Approved
0.6258	Remote Similarity	NPD3140	Approved
0.6257	Remote Similarity	NPD4662	Approved
0.6257	Remote Similarity	NPD4661	Approved
0.6256	Remote Similarity	NPD4107	Approved
0.625	Remote Similarity	NPD9494	Approved
0.6243	Remote Similarity	NPD5242	Approved
0.6235	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6229	Remote Similarity	NPD5890	Approved
0.6229	Remote Similarity	NPD958	Approved
0.6229	Remote Similarity	NPD5889	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