NPASS Compound

Structure

NPC114513 OpenBabel07101718182D 26 30 0 0 1 0 0 0 0 0999 V2000 2.6270 2.4119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0711 -0.8935 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6327 3.2478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1302 2.6012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5741 2.9105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0925 0.1999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0925 1.8262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2051 1.4196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5633 0.8262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0484 1.6173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7967 1.4196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7967 0.6065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3884 0.6065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3884 1.4196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5009 1.8262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2051 0.6065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9898 1.2800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5009 0.1999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7526 0.0995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9599 0.2804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7526 1.9266 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5009 2.8262 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5009 -0.8001 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9751 -0.8754 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0711 0.1065 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 2 25 1 0 0 0 0 3 4 1 0 0 0 0 3 5 1 0 0 0 0 4 10 1 0 0 0 0 5 21 1 0 0 0 0 6 12 2 0 0 0 0 6 13 1 0 0 0 0 7 11 2 0 0 0 0 7 14 1 0 0 0 0 8 15 1 0 0 0 0 8 16 2 0 0 0 0 9 10 2 0 0 0 0 9 26 1 0 0 0 0 10 17 1 0 0 0 0 11 12 1 0 0 0 0 11 15 1 0 0 0 0 12 18 1 0 0 0 0 13 14 2 0 0 0 0 13 19 1 0 0 0 0 14 21 1 0 0 0 0 15 22 2 0 0 0 0 16 18 1 0 0 0 0 16 25 1 0 0 0 0 17 20 2 0 0 0 0 17 21 1 0 0 0 0 18 23 2 0 0 0 0 19 20 1 0 0 0 0 19 24 2 0 0 0 0 20 26 1 0 0 0 0 21 1 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	348.1
Volume:	349.213
LogP:	3.351
LogD:	2.566
LogS:	-5.746
# Rotatable Bonds:	1
TPSA:	73.58
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.79
Synthetic Accessibility Score:	3.689
Fsp3:	0.286
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.136
MDCK Permeability:	2.901863626902923e-05
Pgp-inhibitor:	0.957
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.928
30% Bioavailability (F30%):	0.175

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	90.23340606689453%
Volume Distribution (VD):	1.37
Pgp-substrate:	4.3985724449157715%

ADMET: Metabolism

CYP1A2-inhibitor:	0.865
CYP1A2-substrate:	0.914
CYP2C19-inhibitor:	0.913
CYP2C19-substrate:	0.112
CYP2C9-inhibitor:	0.87
CYP2C9-substrate:	0.233
CYP2D6-inhibitor:	0.49
CYP2D6-substrate:	0.193
CYP3A4-inhibitor:	0.816
CYP3A4-substrate:	0.248

ADMET: Excretion

Clearance (CL):	2.465
Half-life (T1/2):	0.114

ADMET: Toxicity

hERG Blockers:	0.103
Human Hepatotoxicity (H-HT):	0.722
Drug-inuced Liver Injury (DILI):	0.486
AMES Toxicity:	0.553
Rat Oral Acute Toxicity:	0.837
Maximum Recommended Daily Dose:	0.954
Skin Sensitization:	0.184
Carcinogencity:	0.961
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.325

Download Data

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

Natural Product: NPC114513

Natural Product ID:	NPC114513
*Common Name:**	RGVWNPNSTILHHK-NRFANRHFSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	RGVWNPNSTILHHK-NRFANRHFSA-N
Standard InCHI:	InChI=1S/C21H16O5/c1-21-5-3-4-10-9-26-20(17(10)21)19(24)13-6-12-11(7-14(13)21)15(22)8-16(25-2)18(12)23/h6-9H,3-5H2,1-2H3/t21-/m0/s1
SMILES:	C[C@]12CCCc3coc(c23)C(=O)c2cc3c(cc12)C(=O)C=C(C3=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL344243
PubChem CID:	10497902
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones

*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
NPO32702	xestospongia sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11908959]
NPO32702	xestospongia sp.	Species	Petrosiidae	Eukaryota	n.a.	Caledonian	n.a.	PMID[1453184]
NPO32702	xestospongia sp.	Species	Petrosiidae	Eukaryota	n.a.	Thai	n.a.	PMID[14640515]
NPO32702	xestospongia sp.	Species	Petrosiidae	Eukaryota	n.a.	thai	n.a.	PMID[15217287]
NPO32702	xestospongia sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1710256]
NPO32702	xestospongia sp.	Species	Petrosiidae	Eukaryota	n.a.	coral reef habitat at a depth of approximately 20 m from the sea bed surface, at Sangalaki, Indonesia (2 04 59 N, 118 23 41 E)	1996-MAR	PMID[20503979]
NPO32702	xestospongia sp.	Species	Petrosiidae	Eukaryota	n.a.	Indonesia	n.a.	PMID[20503979]
NPO32702	xestospongia sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[31260310]
NPO32702	xestospongia sp.	Species	Petrosiidae	Eukaryota	n.a.	Philippine	n.a.	PMID[7473578]
NPO32702	xestospongia sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[7798966]

☑ 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	2
Others	2

Activity Type	# Activity
Cell Line	2
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	28000.0	nM	PMID[505143]
NPT6399	Cell Line	XRS6	Cricetulus griseus	IC50	=	4300.0	nM	PMID[505143]
NPT5376	Individual Protein	DNA topoisomerase II	Drosophila melanogaster	IC90	=	143000.0	nM	PMID[505143]
NPT2	Others	Unspecified		Ratio	=	3.0	n.a.	PMID[505143]

☑ 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 NPC114513 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	415
0.1-0.2	1680
0.2-0.3	3659
0.3-0.4	9723
0.4-0.5	9669
0.5-0.6	6291
0.6-0.7	9362
0.7-0.8	1831
0.8-0.85	48
0.85-0.9	10
0.9-0.95	7
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC245522
0.9504	High Similarity	NPC478166
0.9441	High Similarity	NPC192069
0.9315	High Similarity	NPC282793
0.9122	High Similarity	NPC469966
0.9122	High Similarity	NPC88958
0.8904	High Similarity	NPC281398
0.8792	High Similarity	NPC144010
0.8742	High Similarity	NPC179170
0.8733	High Similarity	NPC145830
0.8699	High Similarity	NPC117674
0.8639	High Similarity	NPC93241
0.8639	High Similarity	NPC27798
0.8618	High Similarity	NPC25351
0.8553	High Similarity	NPC10429
0.8514	High Similarity	NPC290038
0.8506	High Similarity	NPC221992
0.8483	Intermediate Similarity	NPC265181
0.8483	Intermediate Similarity	NPC233707
0.8481	Intermediate Similarity	NPC472784
0.8472	Intermediate Similarity	NPC307401
0.8462	Intermediate Similarity	NPC324117
0.8456	Intermediate Similarity	NPC233763
0.8429	Intermediate Similarity	NPC59502
0.8414	Intermediate Similarity	NPC177262
0.8411	Intermediate Similarity	NPC95526
0.8375	Intermediate Similarity	NPC44602
0.8375	Intermediate Similarity	NPC473945
0.8356	Intermediate Similarity	NPC202260
0.8355	Intermediate Similarity	NPC472298
0.8344	Intermediate Similarity	NPC478163
0.8333	Intermediate Similarity	NPC209858
0.8333	Intermediate Similarity	NPC299094
0.8333	Intermediate Similarity	NPC10051
0.8333	Intermediate Similarity	NPC178382
0.8323	Intermediate Similarity	NPC478161
0.8323	Intermediate Similarity	NPC478159
0.8312	Intermediate Similarity	NPC27615
0.8311	Intermediate Similarity	NPC263337
0.8288	Intermediate Similarity	NPC186647
0.8228	Intermediate Similarity	NPC472781
0.8228	Intermediate Similarity	NPC472782
0.8217	Intermediate Similarity	NPC472823
0.8194	Intermediate Similarity	NPC44606
0.8176	Intermediate Similarity	NPC472780
0.8176	Intermediate Similarity	NPC476035
0.8176	Intermediate Similarity	NPC14499
0.8176	Intermediate Similarity	NPC475039
0.8176	Intermediate Similarity	NPC472783
0.8171	Intermediate Similarity	NPC167340
0.8163	Intermediate Similarity	NPC290601
0.8158	Intermediate Similarity	NPC71821
0.8144	Intermediate Similarity	NPC472533
0.8125	Intermediate Similarity	NPC164295
0.8125	Intermediate Similarity	NPC239134
0.8125	Intermediate Similarity	NPC279596
0.8116	Intermediate Similarity	NPC97566
0.8101	Intermediate Similarity	NPC123153
0.8095	Intermediate Similarity	NPC471670
0.8079	Intermediate Similarity	NPC199044
0.8079	Intermediate Similarity	NPC238843
0.8069	Intermediate Similarity	NPC293253
0.8065	Intermediate Similarity	NPC472787
0.8054	Intermediate Similarity	NPC18904
0.8052	Intermediate Similarity	NPC472839
0.805	Intermediate Similarity	NPC472299
0.8042	Intermediate Similarity	NPC208389
0.8038	Intermediate Similarity	NPC7059
0.8037	Intermediate Similarity	NPC302392
0.8027	Intermediate Similarity	NPC22644
0.8027	Intermediate Similarity	NPC217914
0.8026	Intermediate Similarity	NPC185456
0.8026	Intermediate Similarity	NPC472836
0.8025	Intermediate Similarity	NPC472786
0.8025	Intermediate Similarity	NPC473766
0.8025	Intermediate Similarity	NPC75310
0.8025	Intermediate Similarity	NPC473753
0.8025	Intermediate Similarity	NPC41689
0.8025	Intermediate Similarity	NPC23559
0.8014	Intermediate Similarity	NPC470406
0.8013	Intermediate Similarity	NPC471613
0.8	Intermediate Similarity	NPC471003
0.8	Intermediate Similarity	NPC228842
0.8	Intermediate Similarity	NPC212257
0.7987	Intermediate Similarity	NPC473368
0.7987	Intermediate Similarity	NPC252208
0.7975	Intermediate Similarity	NPC104736
0.7975	Intermediate Similarity	NPC41880
0.7974	Intermediate Similarity	NPC62799
0.7974	Intermediate Similarity	NPC471292
0.7974	Intermediate Similarity	NPC262198
0.7972	Intermediate Similarity	NPC428300
0.7972	Intermediate Similarity	NPC26532
0.7963	Intermediate Similarity	NPC475779
0.7962	Intermediate Similarity	NPC471863
0.7961	Intermediate Similarity	NPC53016
0.7961	Intermediate Similarity	NPC158871
0.7959	Intermediate Similarity	NPC474659
0.7953	Intermediate Similarity	NPC472358
0.7949	Intermediate Similarity	NPC272590
0.7945	Intermediate Similarity	NPC183103
0.7943	Intermediate Similarity	NPC51079
0.7937	Intermediate Similarity	NPC8389
0.7937	Intermediate Similarity	NPC287559
0.7935	Intermediate Similarity	NPC474107
0.7935	Intermediate Similarity	NPC280025
0.7933	Intermediate Similarity	NPC61157
0.7933	Intermediate Similarity	NPC473681
0.7933	Intermediate Similarity	NPC148374
0.7933	Intermediate Similarity	NPC218204
0.7933	Intermediate Similarity	NPC56197
0.7933	Intermediate Similarity	NPC470407
0.7927	Intermediate Similarity	NPC88593
0.7925	Intermediate Similarity	NPC81405
0.7925	Intermediate Similarity	NPC304692
0.7922	Intermediate Similarity	NPC224418
0.7919	Intermediate Similarity	NPC471996
0.7917	Intermediate Similarity	NPC198904
0.7917	Intermediate Similarity	NPC50583
0.7911	Intermediate Similarity	NPC472785
0.7908	Intermediate Similarity	NPC56731
0.7902	Intermediate Similarity	NPC246392
0.7898	Intermediate Similarity	NPC475777
0.7898	Intermediate Similarity	NPC189773
0.7898	Intermediate Similarity	NPC294511
0.7898	Intermediate Similarity	NPC246164
0.7898	Intermediate Similarity	NPC121615
0.7895	Intermediate Similarity	NPC201297
0.7888	Intermediate Similarity	NPC79571
0.7887	Intermediate Similarity	NPC473885
0.7887	Intermediate Similarity	NPC471074
0.7885	Intermediate Similarity	NPC226578
0.7877	Intermediate Similarity	NPC471817
0.7877	Intermediate Similarity	NPC473982
0.7877	Intermediate Similarity	NPC471995
0.7875	Intermediate Similarity	NPC140952
0.7874	Intermediate Similarity	NPC163867
0.7866	Intermediate Similarity	NPC298071
0.7862	Intermediate Similarity	NPC57552
0.7862	Intermediate Similarity	NPC3898
0.7857	Intermediate Similarity	NPC478160
0.7853	Intermediate Similarity	NPC308156
0.7853	Intermediate Similarity	NPC132054
0.7852	Intermediate Similarity	NPC232996
0.7852	Intermediate Similarity	NPC42400
0.7848	Intermediate Similarity	NPC24232
0.7847	Intermediate Similarity	NPC327527
0.7847	Intermediate Similarity	NPC329707
0.7847	Intermediate Similarity	NPC476917
0.7843	Intermediate Similarity	NPC472840
0.7843	Intermediate Similarity	NPC478164
0.7838	Intermediate Similarity	NPC23894
0.7826	Intermediate Similarity	NPC250076
0.7826	Intermediate Similarity	NPC212918
0.7818	Intermediate Similarity	NPC472660
0.7815	Intermediate Similarity	NPC90296
0.7812	Intermediate Similarity	NPC472283
0.7808	Intermediate Similarity	NPC61788
0.7806	Intermediate Similarity	NPC250331
0.7806	Intermediate Similarity	NPC471346
0.7806	Intermediate Similarity	NPC302987
0.7805	Intermediate Similarity	NPC316262
0.7805	Intermediate Similarity	NPC279768
0.7805	Intermediate Similarity	NPC314653
0.78	Intermediate Similarity	NPC301341
0.7799	Intermediate Similarity	NPC41719
0.7799	Intermediate Similarity	NPC290927
0.7792	Intermediate Similarity	NPC308006
0.7778	Intermediate Similarity	NPC243577
0.7778	Intermediate Similarity	NPC184391
0.7778	Intermediate Similarity	NPC18986
0.7778	Intermediate Similarity	NPC313368
0.7778	Intermediate Similarity	NPC177925
0.7778	Intermediate Similarity	NPC68848
0.7778	Intermediate Similarity	NPC474737
0.7771	Intermediate Similarity	NPC159927
0.7771	Intermediate Similarity	NPC46551
0.7771	Intermediate Similarity	NPC469335
0.777	Intermediate Similarity	NPC243704
0.7764	Intermediate Similarity	NPC474611
0.7764	Intermediate Similarity	NPC294300
0.7764	Intermediate Similarity	NPC201127
0.7764	Intermediate Similarity	NPC104380
0.7764	Intermediate Similarity	NPC317900
0.7764	Intermediate Similarity	NPC217602
0.7764	Intermediate Similarity	NPC476404
0.7764	Intermediate Similarity	NPC473282
0.7764	Intermediate Similarity	NPC67197
0.7762	Intermediate Similarity	NPC179354
0.7758	Intermediate Similarity	NPC255787
0.7758	Intermediate Similarity	NPC291742
0.7758	Intermediate Similarity	NPC191012
0.7756	Intermediate Similarity	NPC19747
0.7756	Intermediate Similarity	NPC93666
0.7756	Intermediate Similarity	NPC478018
0.7754	Intermediate Similarity	NPC79202
0.7754	Intermediate Similarity	NPC59035
0.775	Intermediate Similarity	NPC60973
0.7748	Intermediate Similarity	NPC474722
0.7744	Intermediate Similarity	NPC277618

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 NPC114513 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	370
0.1-0.2	1006
0.2-0.3	1414
0.3-0.4	2720
0.4-0.5	2119
0.5-0.6	1097
0.6-0.7	376
0.7-0.8	47
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8483	Intermediate Similarity	NPD1471	Phase 3
0.7748	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD3972	Approved
0.758	Intermediate Similarity	NPD6273	Approved
0.7547	Intermediate Similarity	NPD3226	Approved
0.7532	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2346	Discontinued
0.7514	Intermediate Similarity	NPD8434	Phase 2
0.7484	Intermediate Similarity	NPD7003	Approved
0.7427	Intermediate Similarity	NPD6765	Approved
0.7427	Intermediate Similarity	NPD6764	Approved
0.7397	Intermediate Similarity	NPD1876	Approved
0.7343	Intermediate Similarity	NPD1651	Approved
0.7329	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD7458	Discontinued
0.7305	Intermediate Similarity	NPD1247	Approved
0.729	Intermediate Similarity	NPD2344	Approved
0.7285	Intermediate Similarity	NPD8032	Phase 2
0.7284	Intermediate Similarity	NPD6599	Discontinued
0.7273	Intermediate Similarity	NPD3748	Approved
0.7267	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD4628	Phase 3
0.7257	Intermediate Similarity	NPD6784	Approved
0.7257	Intermediate Similarity	NPD6785	Approved
0.7193	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD919	Approved
0.717	Intermediate Similarity	NPD7236	Approved
0.7163	Intermediate Similarity	NPD1241	Discontinued
0.7161	Intermediate Similarity	NPD2799	Discontinued
0.7152	Intermediate Similarity	NPD7819	Suspended
0.7152	Intermediate Similarity	NPD5760	Phase 2
0.7152	Intermediate Similarity	NPD5761	Phase 2
0.7134	Intermediate Similarity	NPD7411	Suspended
0.7124	Intermediate Similarity	NPD2979	Phase 3
0.7115	Intermediate Similarity	NPD2796	Approved
0.7114	Intermediate Similarity	NPD3267	Approved
0.7114	Intermediate Similarity	NPD3266	Approved
0.7108	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD2309	Approved
0.7105	Intermediate Similarity	NPD2313	Discontinued
0.7101	Intermediate Similarity	NPD6959	Discontinued
0.7099	Intermediate Similarity	NPD920	Approved
0.7081	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD1281	Approved
0.7063	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD7239	Suspended
0.7048	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD3750	Approved
0.7041	Intermediate Similarity	NPD5494	Approved
0.7013	Intermediate Similarity	NPD4307	Phase 2
0.7	Intermediate Similarity	NPD3887	Approved
0.6993	Remote Similarity	NPD6798	Discontinued
0.6993	Remote Similarity	NPD3268	Approved
0.6988	Remote Similarity	NPD6279	Approved
0.6988	Remote Similarity	NPD6280	Approved
0.6986	Remote Similarity	NPD5691	Approved
0.6981	Remote Similarity	NPD1243	Approved
0.698	Remote Similarity	NPD5327	Phase 3
0.6975	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD6832	Phase 2
0.6968	Remote Similarity	NPD6355	Discontinued
0.6959	Remote Similarity	NPD6808	Phase 2
0.6954	Remote Similarity	NPD5844	Phase 1
0.6954	Remote Similarity	NPD2798	Approved
0.6933	Remote Similarity	NPD1283	Approved
0.6932	Remote Similarity	NPD6559	Discontinued
0.6928	Remote Similarity	NPD7095	Approved
0.6928	Remote Similarity	NPD7008	Discontinued
0.6928	Remote Similarity	NPD5889	Approved
0.6928	Remote Similarity	NPD5890	Approved
0.6923	Remote Similarity	NPD3749	Approved
0.6923	Remote Similarity	NPD7075	Discontinued
0.6919	Remote Similarity	NPD3926	Phase 2
0.6914	Remote Similarity	NPD6799	Approved
0.6903	Remote Similarity	NPD4060	Phase 1
0.6901	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD2531	Phase 2
0.6899	Remote Similarity	NPD2438	Suspended
0.6897	Remote Similarity	NPD7177	Discontinued
0.6892	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD6801	Discontinued
0.6879	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2800	Approved
0.6871	Remote Similarity	NPD2533	Approved
0.6871	Remote Similarity	NPD2534	Approved
0.6871	Remote Similarity	NPD2532	Approved
0.6864	Remote Similarity	NPD3882	Suspended
0.6855	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD2353	Approved
0.6835	Remote Similarity	NPD4308	Phase 3
0.6832	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD5049	Phase 3
0.6813	Remote Similarity	NPD2897	Discontinued
0.6795	Remote Similarity	NPD4140	Approved
0.6792	Remote Similarity	NPD4476	Approved
0.6792	Remote Similarity	NPD2935	Discontinued
0.6792	Remote Similarity	NPD6099	Approved
0.6792	Remote Similarity	NPD6100	Approved
0.6792	Remote Similarity	NPD4477	Approved
0.6791	Remote Similarity	NPD4107	Approved
0.6788	Remote Similarity	NPD3873	Phase 3
0.6788	Remote Similarity	NPD3869	Phase 3
0.6776	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD3764	Approved
0.6766	Remote Similarity	NPD6585	Discontinued
0.6765	Remote Similarity	NPD7768	Phase 2
0.6765	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5951	Approved
0.6757	Remote Similarity	NPD3024	Approved
0.6757	Remote Similarity	NPD3025	Approved
0.6757	Remote Similarity	NPD5585	Approved
0.6752	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD1611	Approved
0.6731	Remote Similarity	NPD6233	Phase 2
0.673	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD8166	Discontinued
0.6713	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD4626	Approved
0.6711	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD17	Approved
0.6708	Remote Similarity	NPD1549	Phase 2
0.6706	Remote Similarity	NPD3817	Phase 2
0.6705	Remote Similarity	NPD8127	Discontinued
0.6688	Remote Similarity	NPD3140	Approved
0.6688	Remote Similarity	NPD3142	Approved
0.6687	Remote Similarity	NPD2354	Approved
0.6687	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD1551	Phase 2
0.6687	Remote Similarity	NPD5403	Approved
0.6667	Remote Similarity	NPD1470	Approved
0.6667	Remote Similarity	NPD7028	Phase 2
0.6667	Remote Similarity	NPD3026	Approved
0.6667	Remote Similarity	NPD6232	Discontinued
0.6667	Remote Similarity	NPD2797	Approved
0.6667	Remote Similarity	NPD4482	Phase 3
0.6667	Remote Similarity	NPD7057	Phase 3
0.6667	Remote Similarity	NPD4380	Phase 2
0.6667	Remote Similarity	NPD5401	Approved
0.6667	Remote Similarity	NPD7058	Phase 2
0.6667	Remote Similarity	NPD7294	Phase 1
0.6667	Remote Similarity	NPD3023	Approved
0.6667	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD7473	Discontinued
0.6647	Remote Similarity	NPD710	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD3057	Approved
0.6625	Remote Similarity	NPD1510	Phase 2
0.6624	Remote Similarity	NPD7961	Discontinued
0.6623	Remote Similarity	NPD6287	Discontinued
0.6621	Remote Similarity	NPD5535	Approved
0.661	Remote Similarity	NPD2163	Approved
0.661	Remote Similarity	NPD3751	Discontinued
0.6608	Remote Similarity	NPD2296	Approved
0.6608	Remote Similarity	NPD5402	Approved
0.6605	Remote Similarity	NPD4534	Discontinued
0.6604	Remote Similarity	NPD1607	Approved
0.66	Remote Similarity	NPD1778	Approved
0.66	Remote Similarity	NPD2932	Approved
0.66	Remote Similarity	NPD3019	Approved
0.6591	Remote Similarity	NPD6166	Phase 2
0.6591	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD7577	Discontinued
0.6587	Remote Similarity	NPD7427	Discontinued
0.6584	Remote Similarity	NPD5404	Approved
0.6584	Remote Similarity	NPD5406	Approved
0.6584	Remote Similarity	NPD5405	Approved
0.6584	Remote Similarity	NPD5408	Approved
0.6579	Remote Similarity	NPD1608	Approved
0.6576	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD2968	Approved
0.6575	Remote Similarity	NPD8312	Approved
0.6575	Remote Similarity	NPD8313	Approved
0.6575	Remote Similarity	NPD2971	Approved
0.6573	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD2182	Approved
0.657	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD8285	Discontinued
0.6545	Remote Similarity	NPD2972	Approved
0.6545	Remote Similarity	NPD3533	Approved
0.6543	Remote Similarity	NPD5762	Approved
0.6543	Remote Similarity	NPD5763	Approved
0.6541	Remote Similarity	NPD5735	Approved
0.6541	Remote Similarity	NPD1933	Approved
0.6536	Remote Similarity	NPD4359	Approved
0.6534	Remote Similarity	NPD7184	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