NPASS Compound

Structure

NPC42470 OpenBabel07101718192D 24 25 0 0 1 0 0 0 0 0999 V2000 2.0257 1.5580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5257 2.4240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7526 -2.2660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7526 1.2660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4198 -1.0598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4198 0.0598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5257 -1.6920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0186 0.8688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0257 1.5580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0834 -1.5229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0834 0.5229 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0186 -1.8688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5257 0.6920 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0859 -2.8634 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8968 1.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 -1.5878 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 12 1 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 5 6 1 0 0 0 0 5 7 2 0 0 0 0 6 13 2 0 0 0 0 7 14 1 0 0 0 0 8 13 1 0 0 0 0 8 16 1 0 0 0 0 9 15 1 0 0 0 0 9 16 1 0 0 0 0 10 15 2 0 0 0 0 11 17 1 0 0 0 0 11 18 1 0 0 0 0 14 4 1 6 0 0 0 14 18 1 0 0 0 0 15 20 1 0 0 0 0 16 21 2 0 0 0 0 17 12 1 6 0 0 0 17 19 1 0 0 0 0 18 22 2 0 0 0 0 19 10 1 1 0 0 0 19 24 1 0 0 0 0 20 23 2 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	330.18
Volume:	356.705
LogP:	3.391
LogD:	2.368
LogS:	-3.382
# Rotatable Bonds:	0
TPSA:	67.51
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.713
Synthetic Accessibility Score:	5.539
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.644
MDCK Permeability:	1.647634053369984e-05
Pgp-inhibitor:	0.024
Pgp-substrate:	0.522
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.141
Plasma Protein Binding (PPB):	92.95690155029297%
Volume Distribution (VD):	1.396
Pgp-substrate:	11.772068977355957%

ADMET: Metabolism

CYP1A2-inhibitor:	0.212
CYP1A2-substrate:	0.337
CYP2C19-inhibitor:	0.112
CYP2C19-substrate:	0.333
CYP2C9-inhibitor:	0.679
CYP2C9-substrate:	0.882
CYP2D6-inhibitor:	0.036
CYP2D6-substrate:	0.387
CYP3A4-inhibitor:	0.203
CYP3A4-substrate:	0.311

ADMET: Excretion

Clearance (CL):	13.761
Half-life (T1/2):	0.927

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.129
Drug-inuced Liver Injury (DILI):	0.933
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.826
Maximum Recommended Daily Dose:	0.04
Skin Sensitization:	0.543
Carcinogencity:	0.823
Eye Corrosion:	0.047
Eye Irritation:	0.038
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC42470

Natural Product ID:	NPC42470
*Common Name:**	Sarcostolide E
IUPAC Name:	(1S,2R,5S,6E,8Z)-5,9-dimethyl-2-propan-2-yl-15-oxabicyclo[11.2.1]hexadeca-6,8,13(16)-triene-4,11,14-trione
Synonyms:	Sarcostolide E
Standard InCHIKey:	BMKPIWHFMRABEY-PKOCSPPNSA-N
Standard InCHI:	InChI=1S/C20H26O4/c1-12(2)17-11-18(22)14(4)7-5-6-13(3)8-16(21)9-15-10-19(17)24-20(15)23/h5-7,10,12,14,17,19H,8-9,11H2,1-4H3/b7-5+,13-6-/t14-,17+,19+/m0/s1
SMILES:	O=C1C/C(=CC=C[C@H](C)C(=O)C[C@@H]([C@H]2C=C(C1)C(=O)O2)C(C)C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL488480
PubChem CID:	25015065
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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
NPO29001	Sarcophyton stolidotum	Species	Orchidaceae	Eukaryota	n.a.	taiwanese soft coral	n.a.	PMID[18537291]
NPO29001	Sarcophyton stolidotum	Species	Orchidaceae	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
ED50	1
Others	2

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	Inhibition	=	16.75	%	PMID[570262]
NPT1183	Cell Line	WiDr	Homo sapiens	Inhibition	=	27.48	%	PMID[570262]
NPT1184	Cell Line	Daoy	Homo sapiens	ED50	=	5.5	ug ml-1	PMID[570262]

☑ 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 NPC42470 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	208
0.1-0.2	1175
0.2-0.3	5303
0.3-0.4	13087
0.4-0.5	12687
0.5-0.6	6502
0.6-0.7	3065
0.7-0.8	618
0.8-0.85	42
0.85-0.9	1
0.9-0.95	8
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9467	High Similarity	NPC57744
0.9342	High Similarity	NPC128276
0.9221	High Similarity	NPC178277
0.9067	High Similarity	NPC259599
0.9067	High Similarity	NPC294434
0.9067	High Similarity	NPC15499
0.9067	High Similarity	NPC117746
0.8987	High Similarity	NPC471325
0.8701	High Similarity	NPC244166
0.859	High Similarity	NPC123360
0.8571	High Similarity	NPC476355
0.8519	High Similarity	NPC325031
0.85	High Similarity	NPC264227
0.85	High Similarity	NPC472965
0.85	High Similarity	NPC63649
0.8415	Intermediate Similarity	NPC173609
0.8354	Intermediate Similarity	NPC472967
0.8354	Intermediate Similarity	NPC266159
0.8333	Intermediate Similarity	NPC215364
0.8333	Intermediate Similarity	NPC474758
0.8333	Intermediate Similarity	NPC140287
0.8312	Intermediate Similarity	NPC163003
0.8293	Intermediate Similarity	NPC281949
0.8293	Intermediate Similarity	NPC25684
0.8293	Intermediate Similarity	NPC301477
0.8272	Intermediate Similarity	NPC270126
0.825	Intermediate Similarity	NPC470240
0.825	Intermediate Similarity	NPC65603
0.825	Intermediate Similarity	NPC476794
0.8235	Intermediate Similarity	NPC261721
0.8235	Intermediate Similarity	NPC279859
0.8235	Intermediate Similarity	NPC107787
0.8235	Intermediate Similarity	NPC38576
0.8193	Intermediate Similarity	NPC35556
0.8158	Intermediate Similarity	NPC218477
0.8148	Intermediate Similarity	NPC108816
0.8148	Intermediate Similarity	NPC93763
0.814	Intermediate Similarity	NPC478144
0.814	Intermediate Similarity	NPC160138
0.8125	Intermediate Similarity	NPC235906
0.8118	Intermediate Similarity	NPC78089
0.8118	Intermediate Similarity	NPC189311
0.8095	Intermediate Similarity	NPC193198
0.8095	Intermediate Similarity	NPC475989
0.8095	Intermediate Similarity	NPC475947
0.8095	Intermediate Similarity	NPC474703
0.8095	Intermediate Similarity	NPC39588
0.8077	Intermediate Similarity	NPC129665
0.8072	Intermediate Similarity	NPC141810
0.8068	Intermediate Similarity	NPC469372
0.8052	Intermediate Similarity	NPC265574
0.8046	Intermediate Similarity	NPC471047
0.8046	Intermediate Similarity	NPC226863
0.8046	Intermediate Similarity	NPC469628
0.8046	Intermediate Similarity	NPC475906
0.8046	Intermediate Similarity	NPC469631
0.8046	Intermediate Similarity	NPC469653
0.8025	Intermediate Similarity	NPC41780
0.8025	Intermediate Similarity	NPC141789
0.8025	Intermediate Similarity	NPC187568
0.8025	Intermediate Similarity	NPC97516
0.8025	Intermediate Similarity	NPC171204
0.8025	Intermediate Similarity	NPC476028
0.8023	Intermediate Similarity	NPC284902
0.8023	Intermediate Similarity	NPC234038
0.8	Intermediate Similarity	NPC329852
0.8	Intermediate Similarity	NPC30486
0.8	Intermediate Similarity	NPC226669
0.8	Intermediate Similarity	NPC193351
0.8	Intermediate Similarity	NPC477129
0.8	Intermediate Similarity	NPC138408
0.8	Intermediate Similarity	NPC115786
0.8	Intermediate Similarity	NPC155587
0.8	Intermediate Similarity	NPC477130
0.8	Intermediate Similarity	NPC149869
0.7978	Intermediate Similarity	NPC284185
0.7976	Intermediate Similarity	NPC85772
0.7976	Intermediate Similarity	NPC200513
0.7975	Intermediate Similarity	NPC474705
0.7975	Intermediate Similarity	NPC295633
0.7975	Intermediate Similarity	NPC58956
0.7975	Intermediate Similarity	NPC269206
0.7955	Intermediate Similarity	NPC115179
0.7955	Intermediate Similarity	NPC106040
0.7955	Intermediate Similarity	NPC212598
0.7952	Intermediate Similarity	NPC474510
0.7952	Intermediate Similarity	NPC69271
0.7952	Intermediate Similarity	NPC74673
0.7952	Intermediate Similarity	NPC302426
0.7952	Intermediate Similarity	NPC281132
0.7949	Intermediate Similarity	NPC67183
0.7931	Intermediate Similarity	NPC478145
0.7931	Intermediate Similarity	NPC475703
0.7927	Intermediate Similarity	NPC299235
0.7927	Intermediate Similarity	NPC267231
0.7927	Intermediate Similarity	NPC471220
0.7922	Intermediate Similarity	NPC470256
0.7912	Intermediate Similarity	NPC209355
0.7907	Intermediate Similarity	NPC21471
0.7907	Intermediate Similarity	NPC261380
0.7907	Intermediate Similarity	NPC177932
0.7907	Intermediate Similarity	NPC33570
0.7907	Intermediate Similarity	NPC125290
0.7907	Intermediate Similarity	NPC161957
0.7882	Intermediate Similarity	NPC170377
0.7882	Intermediate Similarity	NPC53867
0.7882	Intermediate Similarity	NPC250315
0.7882	Intermediate Similarity	NPC318468
0.7865	Intermediate Similarity	NPC144133
0.7865	Intermediate Similarity	NPC469595
0.7865	Intermediate Similarity	NPC471818
0.7865	Intermediate Similarity	NPC62815
0.7865	Intermediate Similarity	NPC253144
0.7865	Intermediate Similarity	NPC212679
0.7865	Intermediate Similarity	NPC220454
0.7865	Intermediate Similarity	NPC179394
0.7865	Intermediate Similarity	NPC473448
0.7848	Intermediate Similarity	NPC84038
0.7831	Intermediate Similarity	NPC617
0.7831	Intermediate Similarity	NPC182550
0.7831	Intermediate Similarity	NPC469690
0.7831	Intermediate Similarity	NPC469620
0.7826	Intermediate Similarity	NPC172998
0.7826	Intermediate Similarity	NPC299396
0.7826	Intermediate Similarity	NPC301596
0.7821	Intermediate Similarity	NPC470693
0.7816	Intermediate Similarity	NPC475461
0.7816	Intermediate Similarity	NPC469483
0.7816	Intermediate Similarity	NPC305475
0.7816	Intermediate Similarity	NPC261253
0.7816	Intermediate Similarity	NPC474045
0.7805	Intermediate Similarity	NPC7563
0.7805	Intermediate Similarity	NPC116177
0.7805	Intermediate Similarity	NPC474760
0.7805	Intermediate Similarity	NPC320630
0.7805	Intermediate Similarity	NPC180290
0.7802	Intermediate Similarity	NPC476596
0.7792	Intermediate Similarity	NPC472266
0.7792	Intermediate Similarity	NPC194871
0.7791	Intermediate Similarity	NPC196487
0.7791	Intermediate Similarity	NPC475100
0.7791	Intermediate Similarity	NPC82297
0.7791	Intermediate Similarity	NPC476804
0.7791	Intermediate Similarity	NPC14575
0.7778	Intermediate Similarity	NPC150978
0.7778	Intermediate Similarity	NPC300312
0.7778	Intermediate Similarity	NPC329826
0.7778	Intermediate Similarity	NPC111114
0.7778	Intermediate Similarity	NPC261607
0.7778	Intermediate Similarity	NPC74103
0.7778	Intermediate Similarity	NPC70595
0.7778	Intermediate Similarity	NPC123177
0.7778	Intermediate Similarity	NPC469414
0.7765	Intermediate Similarity	NPC94200
0.7765	Intermediate Similarity	NPC221231
0.7765	Intermediate Similarity	NPC471326
0.7763	Intermediate Similarity	NPC470688
0.7753	Intermediate Similarity	NPC295312
0.7753	Intermediate Similarity	NPC284561
0.7753	Intermediate Similarity	NPC5509
0.775	Intermediate Similarity	NPC472956
0.7738	Intermediate Similarity	NPC276356
0.7738	Intermediate Similarity	NPC223904
0.7727	Intermediate Similarity	NPC475678
0.7717	Intermediate Similarity	NPC234339
0.7717	Intermediate Similarity	NPC273197
0.7717	Intermediate Similarity	NPC295347
0.7711	Intermediate Similarity	NPC192006
0.7701	Intermediate Similarity	NPC165162
0.7701	Intermediate Similarity	NPC65661
0.7701	Intermediate Similarity	NPC255307
0.7701	Intermediate Similarity	NPC474369
0.7701	Intermediate Similarity	NPC99395
0.7701	Intermediate Similarity	NPC197903
0.7701	Intermediate Similarity	NPC474547
0.7692	Intermediate Similarity	NPC476597
0.7692	Intermediate Similarity	NPC476598
0.7692	Intermediate Similarity	NPC469645
0.7692	Intermediate Similarity	NPC476049
0.7692	Intermediate Similarity	NPC475657
0.7692	Intermediate Similarity	NPC469692
0.7683	Intermediate Similarity	NPC27205
0.7683	Intermediate Similarity	NPC473223
0.7674	Intermediate Similarity	NPC131669
0.7674	Intermediate Similarity	NPC40746
0.7674	Intermediate Similarity	NPC169575
0.7674	Intermediate Similarity	NPC16488
0.7674	Intermediate Similarity	NPC118423
0.7674	Intermediate Similarity	NPC473390
0.7667	Intermediate Similarity	NPC51486
0.7667	Intermediate Similarity	NPC145666
0.7667	Intermediate Similarity	NPC475855
0.7667	Intermediate Similarity	NPC312042
0.7662	Intermediate Similarity	NPC248125
0.7647	Intermediate Similarity	NPC35089
0.7647	Intermediate Similarity	NPC39411
0.7647	Intermediate Similarity	NPC255580
0.7647	Intermediate Similarity	NPC10276
0.7647	Intermediate Similarity	NPC275507
0.764	Intermediate Similarity	NPC476805

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 NPC42470 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	193
0.1-0.2	1633
0.2-0.3	3732
0.3-0.4	2376
0.4-0.5	861
0.5-0.6	283
0.6-0.7	65
0.7-0.8	7
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
0.7976	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD5209	Approved
0.7907	Intermediate Similarity	NPD1694	Approved
0.7473	Intermediate Similarity	NPD5785	Approved
0.7349	Intermediate Similarity	NPD8039	Approved
0.734	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD5363	Approved
0.7089	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD5786	Approved
0.6989	Remote Similarity	NPD1695	Approved
0.6966	Remote Similarity	NPD4270	Approved
0.6966	Remote Similarity	NPD4269	Approved
0.6923	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD7838	Discovery
0.6897	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD5362	Discontinued
0.6889	Remote Similarity	NPD7154	Phase 3
0.6854	Remote Similarity	NPD5369	Approved
0.6848	Remote Similarity	NPD7334	Approved
0.6848	Remote Similarity	NPD5330	Approved
0.6848	Remote Similarity	NPD6684	Approved
0.6848	Remote Similarity	NPD7146	Approved
0.6848	Remote Similarity	NPD7521	Approved
0.6848	Remote Similarity	NPD6409	Approved
0.6778	Remote Similarity	NPD6435	Approved
0.6771	Remote Similarity	NPD5779	Approved
0.6771	Remote Similarity	NPD5778	Approved
0.6768	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD4252	Approved
0.6739	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD5207	Approved
0.6737	Remote Similarity	NPD46	Approved
0.6737	Remote Similarity	NPD6698	Approved
0.6702	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD6903	Approved
0.6702	Remote Similarity	NPD5737	Approved
0.6702	Remote Similarity	NPD6672	Approved
0.6701	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD7900	Approved
0.6667	Remote Similarity	NPD5694	Approved
0.6667	Remote Similarity	NPD5693	Phase 1
0.6635	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD6101	Approved
0.6604	Remote Similarity	NPD6371	Approved
0.66	Remote Similarity	NPD4225	Approved
0.6598	Remote Similarity	NPD6399	Phase 3
0.6591	Remote Similarity	NPD4756	Discovery
0.6571	Remote Similarity	NPD6686	Approved
0.6562	Remote Similarity	NPD5692	Phase 3
0.6556	Remote Similarity	NPD5368	Approved
0.6556	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7902	Approved
0.6495	Remote Similarity	NPD7983	Approved
0.6495	Remote Similarity	NPD5284	Approved
0.6495	Remote Similarity	NPD5281	Approved
0.6495	Remote Similarity	NPD6411	Approved
0.6495	Remote Similarity	NPD6050	Approved
0.6449	Remote Similarity	NPD2067	Discontinued
0.6436	Remote Similarity	NPD7638	Approved
0.6421	Remote Similarity	NPD3573	Approved
0.6396	Remote Similarity	NPD7115	Discovery
0.6389	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD4821	Approved
0.6374	Remote Similarity	NPD4819	Approved
0.6374	Remote Similarity	NPD4822	Approved
0.6374	Remote Similarity	NPD4820	Approved
0.6373	Remote Similarity	NPD7639	Approved
0.6373	Remote Similarity	NPD6648	Approved
0.6373	Remote Similarity	NPD7640	Approved
0.6364	Remote Similarity	NPD5282	Discontinued
0.6364	Remote Similarity	NPD7748	Approved
0.6346	Remote Similarity	NPD6647	Phase 2
0.6344	Remote Similarity	NPD5332	Approved
0.6344	Remote Similarity	NPD5331	Approved
0.6341	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD4271	Approved
0.6333	Remote Similarity	NPD4268	Approved
0.6321	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5279	Phase 3
0.6304	Remote Similarity	NPD4790	Discontinued
0.63	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.63	Remote Similarity	NPD5695	Phase 3
0.6289	Remote Similarity	NPD6673	Approved
0.6289	Remote Similarity	NPD6080	Approved
0.6289	Remote Similarity	NPD6904	Approved
0.6275	Remote Similarity	NPD5696	Approved
0.6239	Remote Similarity	NPD6650	Approved
0.6239	Remote Similarity	NPD6649	Approved
0.6238	Remote Similarity	NPD7839	Suspended
0.6204	Remote Similarity	NPD2182	Approved
0.6186	Remote Similarity	NPD5208	Approved
0.6176	Remote Similarity	NPD6083	Phase 2
0.6176	Remote Similarity	NPD6084	Phase 2
0.6173	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD5697	Approved
0.6162	Remote Similarity	NPD7637	Suspended
0.6162	Remote Similarity	NPD7515	Phase 2
0.6147	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD4249	Approved
0.6146	Remote Similarity	NPD3618	Phase 1
0.6139	Remote Similarity	NPD5654	Approved
0.6122	Remote Similarity	NPD6051	Approved
0.6122	Remote Similarity	NPD5370	Suspended
0.6111	Remote Similarity	NPD6881	Approved
0.6111	Remote Similarity	NPD6011	Approved
0.6111	Remote Similarity	NPD6899	Approved
0.6105	Remote Similarity	NPD3666	Approved
0.6105	Remote Similarity	NPD3133	Approved
0.6105	Remote Similarity	NPD3665	Phase 1
0.6105	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD4250	Approved
0.6082	Remote Similarity	NPD4251	Approved
0.6075	Remote Similarity	NPD6008	Approved
0.6067	Remote Similarity	NPD4058	Approved
0.6064	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD6013	Approved
0.6055	Remote Similarity	NPD6372	Approved
0.6055	Remote Similarity	NPD6373	Approved
0.6055	Remote Similarity	NPD6014	Approved
0.6055	Remote Similarity	NPD6012	Approved
0.6053	Remote Similarity	NPD6927	Phase 3
0.604	Remote Similarity	NPD6001	Approved
0.6036	Remote Similarity	NPD6053	Discontinued
0.6022	Remote Similarity	NPD4695	Discontinued
0.6019	Remote Similarity	NPD5959	Approved
0.6	Remote Similarity	NPD7102	Approved
0.6	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5344	Discontinued
0.6	Remote Similarity	NPD6079	Approved
0.6	Remote Similarity	NPD7331	Phase 2
0.6	Remote Similarity	NPD7290	Approved
0.6	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6883	Approved
0.5984	Remote Similarity	NPD7260	Phase 2
0.5981	Remote Similarity	NPD5909	Discontinued
0.598	Remote Similarity	NPD4629	Approved
0.598	Remote Similarity	NPD5210	Approved
0.5979	Remote Similarity	NPD4623	Approved
0.5979	Remote Similarity	NPD4519	Discontinued
0.5979	Remote Similarity	NPD6098	Approved
0.596	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD6847	Approved
0.5946	Remote Similarity	NPD8130	Phase 1
0.5946	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD6617	Approved
0.5946	Remote Similarity	NPD6869	Approved
0.5938	Remote Similarity	NPD3668	Phase 3
0.593	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD5739	Approved
0.5926	Remote Similarity	NPD6675	Approved
0.5926	Remote Similarity	NPD7128	Approved
0.5926	Remote Similarity	NPD6402	Approved
0.5922	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD5222	Approved
0.5922	Remote Similarity	NPD5221	Approved
0.5922	Remote Similarity	NPD4697	Phase 3
0.5909	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.59	Remote Similarity	NPD3672	Approved
0.59	Remote Similarity	NPD3673	Approved
0.5895	Remote Similarity	NPD3667	Approved
0.5893	Remote Similarity	NPD8297	Approved
0.5893	Remote Similarity	NPD6882	Approved
0.5889	Remote Similarity	NPD4687	Approved
0.5882	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD7341	Phase 2
0.5872	Remote Similarity	NPD6614	Approved
0.5872	Remote Similarity	NPD5701	Approved
0.5865	Remote Similarity	NPD5173	Approved
0.5859	Remote Similarity	NPD4518	Approved
0.5851	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5844	Remote Similarity	NPD28	Approved
0.5844	Remote Similarity	NPD29	Approved
0.5843	Remote Similarity	NPD5276	Approved
0.5842	Remote Similarity	NPD8035	Phase 2
0.5842	Remote Similarity	NPD8034	Phase 2
0.5841	Remote Similarity	NPD6858	Approved
0.5841	Remote Similarity	NPD7094	Approved
0.5833	Remote Similarity	NPD164	Approved
0.5833	Remote Similarity	NPD6110	Phase 1
0.5818	Remote Similarity	NPD7320	Approved
0.5816	Remote Similarity	NPD5690	Phase 2
0.5816	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD5280	Approved
0.5816	Remote Similarity	NPD4694	Approved
0.5816	Remote Similarity	NPD6422	Discontinued
0.58	Remote Similarity	NPD4753	Phase 2
0.58	Remote Similarity	NPD5328	Approved
0.5794	Remote Similarity	NPD7632	Discontinued
0.5794	Remote Similarity	NPD5211	Phase 2
0.5773	Remote Similarity	NPD4786	Approved
0.5769	Remote Similarity	NPD7732	Phase 3
0.5766	Remote Similarity	NPD6413	Approved
0.5765	Remote Similarity	NPD3197	Phase 1
0.5763	Remote Similarity	NPD8513	Phase 3
0.5763	Remote Similarity	NPD8516	Approved
0.5763	Remote Similarity	NPD8515	Approved
0.5763	Remote Similarity	NPD8517	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