NPASS Compound

Structure

NPC268502 OpenBabel07101718312D 25 26 0 0 1 0 0 0 0 0999 V2000 3.5050 -0.3105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3496 -3.2083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0567 -3.9154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7355 0.4914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0908 -1.7247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9885 -2.5012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2814 -3.2083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8320 -0.7588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7638 -1.2765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0567 -1.9836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7297 -1.5353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3155 -2.9495 0.0000 C 0 0 0 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 5.4368 -0.8282 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 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 13 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 6 23 1 0 0 0 0 7 11 1 0 0 0 0 7 15 1 0 0 0 0 8 10 1 0 0 0 0 8 16 1 0 0 0 0 9 12 1 0 0 0 0 9 17 1 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 20 1 0 0 0 0 13 15 2 0 0 0 0 13 16 1 0 0 0 0 14 2 1 1 0 0 0 14 18 1 0 0 0 0 15 19 1 0 0 0 0 16 21 2 0 0 0 0 17 14 1 6 0 0 0 17 24 1 0 0 0 0 18 22 2 0 0 0 0 18 23 1 0 0 0 0 20 5 1 1 0 0 0 20 25 1 0 0 0 0 24 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	352.22
Volume:	373.405
LogP:	3.751
LogD:	2.805
LogS:	-3.993
# Rotatable Bonds:	5
TPSA:	61.83
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.435
Synthetic Accessibility Score:	4.755
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.565
MDCK Permeability:	2.1487445337697864e-05
Pgp-inhibitor:	0.963
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.036
30% Bioavailability (F30%):	0.153

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.777
Plasma Protein Binding (PPB):	68.01712799072266%
Volume Distribution (VD):	1.543
Pgp-substrate:	39.2798957824707%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.736
CYP2C19-inhibitor:	0.06
CYP2C19-substrate:	0.932
CYP2C9-inhibitor:	0.057
CYP2C9-substrate:	0.177
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.607
CYP3A4-inhibitor:	0.719
CYP3A4-substrate:	0.498

ADMET: Excretion

Clearance (CL):	7.108
Half-life (T1/2):	0.299

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.347
Drug-inuced Liver Injury (DILI):	0.548
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.394
Maximum Recommended Daily Dose:	0.469
Skin Sensitization:	0.047
Carcinogencity:	0.87
Eye Corrosion:	0.03
Eye Irritation:	0.044
Respiratory Toxicity:	0.78

Download Data

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

Natural Product: NPC268502

Natural Product ID:	NPC268502
*Common Name:**	Diacarperoxide A
IUPAC Name:	methyl (2R)-2-[(3R,6R)-6-methyl-6-[2-(2,6,6-trimethyl-3-oxocyclohexen-1-yl)ethyl]dioxan-3-yl]propanoate
Synonyms:
Standard InCHIKey:	QUCBMVALSQJJDY-WIBUTAKZSA-N
Standard InCHI:	InChI=1S/C20H32O5/c1-13-15(19(3,4)10-8-16(13)21)7-11-20(5)12-9-17(24-25-20)14(2)18(22)23-6/h14,17H,7-12H2,1-6H3/t14-,17-,20-/m1/s1
SMILES:	CC1=C(CC[C@]2(C)CC[C@H]([C@@H](C)C(=O)OC)OO2)C(C)(C)CCC1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL496650
PubChem CID:	25017959
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO9347	Diacarnus megaspinorhabdosa	Species	Podospongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18672931]
NPO9347	Diacarnus megaspinorhabdosa	Species	Podospongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
EC50	1
IC50	2
Others	4

Activity Type	# Activity
Cell Line	1
Organism	4
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1864	Cell Line	L5178Y	Mus musculus	EC50	>	10.0	ug.mL-1	PMID[490693]
NPT176	Organism	Artemia salina	Artemia salina	Activity	=	35.0	%	PMID[490693]
NPT176	Organism	Artemia salina	Artemia salina	Activity	=	55.0	%	PMID[490693]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1900.0	nM	PMID[490694]
NPT1666	Organism	Plasmodium falciparum D6	Plasmodium falciparum D6	IC50	=	2000.0	nM	PMID[490694]
NPT2	Others	Unspecified		Ratio IC50	=	6.8	n.a.	PMID[490694]
NPT2	Others	Unspecified		Ratio IC50	=	6.5	n.a.	PMID[490694]

☑ 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 NPC268502 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	1676
0.2-0.3	6799
0.3-0.4	14550
0.4-0.5	8521
0.5-0.6	7116
0.6-0.7	3543
0.7-0.8	249
0.8-0.85	19
0.85-0.9	6
0.9-0.95	5
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC254996
0.9589	High Similarity	NPC152754
0.9589	High Similarity	NPC59602
0.9589	High Similarity	NPC476987
0.9359	High Similarity	NPC475193
0.9359	High Similarity	NPC120158
0.8974	High Similarity	NPC476988
0.8947	High Similarity	NPC476264
0.8947	High Similarity	NPC476325
0.8889	High Similarity	NPC475181
0.8734	High Similarity	NPC172309
0.8734	High Similarity	NPC117960
0.8734	High Similarity	NPC14044
0.8642	High Similarity	NPC471343
0.8571	High Similarity	NPC476985
0.8571	High Similarity	NPC475744
0.8571	High Similarity	NPC474316
0.8519	High Similarity	NPC476100
0.8519	High Similarity	NPC476983
0.8481	Intermediate Similarity	NPC308545
0.8481	Intermediate Similarity	NPC82488
0.8312	Intermediate Similarity	NPC330016
0.8214	Intermediate Similarity	NPC476104
0.8214	Intermediate Similarity	NPC476982
0.8214	Intermediate Similarity	NPC262085
0.8182	Intermediate Similarity	NPC167145
0.8148	Intermediate Similarity	NPC274522
0.8148	Intermediate Similarity	NPC476265
0.8125	Intermediate Similarity	NPC476986
0.8125	Intermediate Similarity	NPC470905
0.8101	Intermediate Similarity	NPC474447
0.8101	Intermediate Similarity	NPC266119
0.8095	Intermediate Similarity	NPC471344
0.8	Intermediate Similarity	NPC122847
0.7973	Intermediate Similarity	NPC215987
0.7973	Intermediate Similarity	NPC306805
0.7952	Intermediate Similarity	NPC475395
0.7952	Intermediate Similarity	NPC476984
0.7931	Intermediate Similarity	NPC471342
0.7931	Intermediate Similarity	NPC469866
0.7875	Intermediate Similarity	NPC239127
0.7875	Intermediate Similarity	NPC469514
0.7816	Intermediate Similarity	NPC80335
0.7805	Intermediate Similarity	NPC113363
0.7778	Intermediate Similarity	NPC469867
0.7765	Intermediate Similarity	NPC469407
0.775	Intermediate Similarity	NPC255060
0.7738	Intermediate Similarity	NPC474605
0.7738	Intermediate Similarity	NPC476292
0.7722	Intermediate Similarity	NPC474543
0.7722	Intermediate Similarity	NPC238425
0.7722	Intermediate Similarity	NPC472018
0.7711	Intermediate Similarity	NPC474956
0.7683	Intermediate Similarity	NPC121200
0.7671	Intermediate Similarity	NPC472021
0.7667	Intermediate Similarity	NPC477436
0.7667	Intermediate Similarity	NPC477435
0.764	Intermediate Similarity	NPC161638
0.7625	Intermediate Similarity	NPC474551
0.7619	Intermediate Similarity	NPC282293
0.7619	Intermediate Similarity	NPC79277
0.7619	Intermediate Similarity	NPC475481
0.759	Intermediate Similarity	NPC622
0.759	Intermediate Similarity	NPC276647
0.7586	Intermediate Similarity	NPC229717
0.7582	Intermediate Similarity	NPC477439
0.7561	Intermediate Similarity	NPC281296
0.7561	Intermediate Similarity	NPC472300
0.7534	Intermediate Similarity	NPC472019
0.7534	Intermediate Similarity	NPC472020
0.7534	Intermediate Similarity	NPC226602
0.7529	Intermediate Similarity	NPC70479
0.75	Intermediate Similarity	NPC477438
0.75	Intermediate Similarity	NPC477437
0.747	Intermediate Similarity	NPC321514
0.7468	Intermediate Similarity	NPC69462
0.7442	Intermediate Similarity	NPC271784
0.7442	Intermediate Similarity	NPC108045
0.7442	Intermediate Similarity	NPC475622
0.7419	Intermediate Similarity	NPC98874
0.7412	Intermediate Similarity	NPC475665
0.7412	Intermediate Similarity	NPC327002
0.7391	Intermediate Similarity	NPC471078
0.7391	Intermediate Similarity	NPC473435
0.7391	Intermediate Similarity	NPC473280
0.7391	Intermediate Similarity	NPC473431
0.7391	Intermediate Similarity	NPC470697
0.7386	Intermediate Similarity	NPC195640
0.7386	Intermediate Similarity	NPC220478
0.7381	Intermediate Similarity	NPC28319
0.7381	Intermediate Similarity	NPC471299
0.7381	Intermediate Similarity	NPC150646
0.7363	Intermediate Similarity	NPC473944
0.7363	Intermediate Similarity	NPC36491
0.7356	Intermediate Similarity	NPC109512
0.7342	Intermediate Similarity	NPC107130
0.734	Intermediate Similarity	NPC26413
0.734	Intermediate Similarity	NPC89225
0.7333	Intermediate Similarity	NPC280833
0.7333	Intermediate Similarity	NPC284561
0.7326	Intermediate Similarity	NPC321289
0.7326	Intermediate Similarity	NPC327969
0.732	Intermediate Similarity	NPC470954
0.7317	Intermediate Similarity	NPC199445
0.7317	Intermediate Similarity	NPC60718
0.7312	Intermediate Similarity	NPC148523
0.7303	Intermediate Similarity	NPC471739
0.7303	Intermediate Similarity	NPC38885
0.7303	Intermediate Similarity	NPC197333
0.7303	Intermediate Similarity	NPC181327
0.7294	Intermediate Similarity	NPC469920
0.7292	Intermediate Similarity	NPC477870
0.7292	Intermediate Similarity	NPC476213
0.7292	Intermediate Similarity	NPC477871
0.7292	Intermediate Similarity	NPC476246
0.7283	Intermediate Similarity	NPC271652
0.7283	Intermediate Similarity	NPC476416
0.7273	Intermediate Similarity	NPC189311
0.7273	Intermediate Similarity	NPC76333
0.7273	Intermediate Similarity	NPC323765
0.7273	Intermediate Similarity	NPC476330
0.7263	Intermediate Similarity	NPC264378
0.7262	Intermediate Similarity	NPC178852
0.7262	Intermediate Similarity	NPC478247
0.7262	Intermediate Similarity	NPC471220
0.7262	Intermediate Similarity	NPC478246
0.7262	Intermediate Similarity	NPC74410
0.7253	Intermediate Similarity	NPC477149
0.7253	Intermediate Similarity	NPC477147
0.725	Intermediate Similarity	NPC472017
0.7241	Intermediate Similarity	NPC193198
0.7241	Intermediate Similarity	NPC477373
0.7241	Intermediate Similarity	NPC475989
0.7241	Intermediate Similarity	NPC469561
0.7241	Intermediate Similarity	NPC69469
0.7237	Intermediate Similarity	NPC474552
0.7234	Intermediate Similarity	NPC167193
0.7234	Intermediate Similarity	NPC476797
0.7234	Intermediate Similarity	NPC151725
0.7234	Intermediate Similarity	NPC471153
0.7234	Intermediate Similarity	NPC122324
0.7234	Intermediate Similarity	NPC472806
0.7234	Intermediate Similarity	NPC106425
0.7229	Intermediate Similarity	NPC40353
0.7229	Intermediate Similarity	NPC180886
0.7216	Intermediate Similarity	NPC476235
0.7216	Intermediate Similarity	NPC476126
0.7209	Intermediate Similarity	NPC278459
0.7209	Intermediate Similarity	NPC90055
0.7209	Intermediate Similarity	NPC474955
0.7204	Intermediate Similarity	NPC124207
0.7204	Intermediate Similarity	NPC476415
0.7195	Intermediate Similarity	NPC166797
0.7195	Intermediate Similarity	NPC306928
0.7195	Intermediate Similarity	NPC470299
0.7191	Intermediate Similarity	NPC73038
0.7191	Intermediate Similarity	NPC322159
0.7191	Intermediate Similarity	NPC70555
0.7191	Intermediate Similarity	NPC477478
0.7191	Intermediate Similarity	NPC70422
0.7191	Intermediate Similarity	NPC477479
0.7191	Intermediate Similarity	NPC104961
0.7188	Intermediate Similarity	NPC475202
0.7188	Intermediate Similarity	NPC475385
0.7188	Intermediate Similarity	NPC475392
0.7188	Intermediate Similarity	NPC54705
0.7176	Intermediate Similarity	NPC158565
0.7176	Intermediate Similarity	NPC476177
0.7176	Intermediate Similarity	NPC192329
0.7176	Intermediate Similarity	NPC471740
0.7176	Intermediate Similarity	NPC246458
0.7176	Intermediate Similarity	NPC327674
0.7176	Intermediate Similarity	NPC469620
0.7174	Intermediate Similarity	NPC150383
0.7174	Intermediate Similarity	NPC474631
0.7174	Intermediate Similarity	NPC73457
0.7174	Intermediate Similarity	NPC6255
0.7174	Intermediate Similarity	NPC235704
0.7174	Intermediate Similarity	NPC218301
0.7174	Intermediate Similarity	NPC471588
0.7159	Intermediate Similarity	NPC100391
0.7159	Intermediate Similarity	NPC474359
0.7159	Intermediate Similarity	NPC320801
0.7158	Intermediate Similarity	NPC2049
0.7158	Intermediate Similarity	NPC53844
0.7158	Intermediate Similarity	NPC124246
0.7143	Intermediate Similarity	NPC316500
0.7143	Intermediate Similarity	NPC97577
0.7143	Intermediate Similarity	NPC469546
0.7143	Intermediate Similarity	NPC214387
0.7143	Intermediate Similarity	NPC474570
0.7143	Intermediate Similarity	NPC474700
0.7143	Intermediate Similarity	NPC50070
0.7143	Intermediate Similarity	NPC165711
0.7128	Intermediate Similarity	NPC108141
0.7128	Intermediate Similarity	NPC473648
0.7128	Intermediate Similarity	NPC88310
0.7126	Intermediate Similarity	NPC100297
0.7126	Intermediate Similarity	NPC240302
0.7125	Intermediate Similarity	NPC477448

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 NPC268502 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	198
0.1-0.2	2228
0.2-0.3	3972
0.3-0.4	1869
0.4-0.5	485
0.5-0.6	265
0.6-0.7	122
0.7-0.8	11
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
0.7386	Intermediate Similarity	NPD7521	Approved
0.7386	Intermediate Similarity	NPD7334	Approved
0.7386	Intermediate Similarity	NPD6409	Approved
0.7386	Intermediate Similarity	NPD5330	Approved
0.7386	Intermediate Similarity	NPD7146	Approved
0.7386	Intermediate Similarity	NPD6684	Approved
0.7363	Intermediate Similarity	NPD6411	Approved
0.7222	Intermediate Similarity	NPD6903	Approved
0.7222	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5737	Approved
0.7222	Intermediate Similarity	NPD6672	Approved
0.7204	Intermediate Similarity	NPD7900	Approved
0.7204	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6101	Approved
0.7051	Intermediate Similarity	NPD7341	Phase 2
0.7021	Intermediate Similarity	NPD7748	Approved
0.6989	Remote Similarity	NPD7515	Phase 2
0.6979	Remote Similarity	NPD7902	Approved
0.6979	Remote Similarity	NPD6083	Phase 2
0.6979	Remote Similarity	NPD6084	Phase 2
0.6957	Remote Similarity	NPD6673	Approved
0.6957	Remote Similarity	NPD6080	Approved
0.6957	Remote Similarity	NPD6904	Approved
0.6947	Remote Similarity	NPD5695	Phase 3
0.6932	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3573	Approved
0.6915	Remote Similarity	NPD6399	Phase 3
0.6889	Remote Similarity	NPD1694	Approved
0.6842	Remote Similarity	NPD5282	Discontinued
0.6832	Remote Similarity	NPD6675	Approved
0.6832	Remote Similarity	NPD7128	Approved
0.6832	Remote Similarity	NPD5739	Approved
0.6832	Remote Similarity	NPD6402	Approved
0.6809	Remote Similarity	NPD6050	Approved
0.6771	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD5778	Approved
0.6737	Remote Similarity	NPD5779	Approved
0.6735	Remote Similarity	NPD5696	Approved
0.6706	Remote Similarity	NPD8039	Approved
0.6702	Remote Similarity	NPD5692	Phase 3
0.6699	Remote Similarity	NPD7320	Approved
0.6699	Remote Similarity	NPD6899	Approved
0.6699	Remote Similarity	NPD6881	Approved
0.6667	Remote Similarity	NPD5208	Approved
0.6635	Remote Similarity	NPD6373	Approved
0.6635	Remote Similarity	NPD6372	Approved
0.6632	Remote Similarity	NPD5694	Approved
0.6632	Remote Similarity	NPD5284	Approved
0.6632	Remote Similarity	NPD5693	Phase 1
0.6632	Remote Similarity	NPD5281	Approved
0.663	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.663	Remote Similarity	NPD6098	Approved
0.6629	Remote Similarity	NPD5369	Approved
0.6602	Remote Similarity	NPD5701	Approved
0.6602	Remote Similarity	NPD5697	Approved
0.6598	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD4753	Phase 2
0.6596	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD3666	Approved
0.6593	Remote Similarity	NPD3665	Phase 1
0.6593	Remote Similarity	NPD3133	Approved
0.6571	Remote Similarity	NPD7102	Approved
0.6571	Remote Similarity	NPD7290	Approved
0.6571	Remote Similarity	NPD6883	Approved
0.6543	Remote Similarity	NPD7331	Phase 2
0.6531	Remote Similarity	NPD7732	Phase 3
0.6526	Remote Similarity	NPD5207	Approved
0.6526	Remote Similarity	NPD46	Approved
0.6526	Remote Similarity	NPD5785	Approved
0.6526	Remote Similarity	NPD6698	Approved
0.6517	Remote Similarity	NPD4695	Discontinued
0.6509	Remote Similarity	NPD6649	Approved
0.6509	Remote Similarity	NPD6869	Approved
0.6509	Remote Similarity	NPD6847	Approved
0.6509	Remote Similarity	NPD6617	Approved
0.6509	Remote Similarity	NPD6650	Approved
0.6509	Remote Similarity	NPD8130	Phase 1
0.6505	Remote Similarity	NPD6008	Approved
0.6477	Remote Similarity	NPD3617	Approved
0.6476	Remote Similarity	NPD6013	Approved
0.6476	Remote Similarity	NPD6014	Approved
0.6476	Remote Similarity	NPD6012	Approved
0.6465	Remote Similarity	NPD4755	Approved
0.6452	Remote Similarity	NPD3618	Phase 1
0.6452	Remote Similarity	NPD5279	Phase 3
0.6449	Remote Similarity	NPD8297	Approved
0.6449	Remote Similarity	NPD6882	Approved
0.6442	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD6412	Phase 2
0.6429	Remote Similarity	NPD5654	Approved
0.6421	Remote Similarity	NPD5328	Approved
0.6413	Remote Similarity	NPD3668	Phase 3
0.6413	Remote Similarity	NPD4786	Approved
0.6392	Remote Similarity	NPD4202	Approved
0.6381	Remote Similarity	NPD6686	Approved
0.6381	Remote Similarity	NPD6011	Approved
0.6374	Remote Similarity	NPD3667	Approved
0.6374	Remote Similarity	NPD4223	Phase 3
0.6374	Remote Similarity	NPD4221	Approved
0.6374	Remote Similarity	NPD6435	Approved
0.6374	Remote Similarity	NPD5209	Approved
0.6364	Remote Similarity	NPD7115	Discovery
0.6355	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD5329	Approved
0.6344	Remote Similarity	NPD5363	Approved
0.6337	Remote Similarity	NPD4696	Approved
0.6337	Remote Similarity	NPD5285	Approved
0.6337	Remote Similarity	NPD5286	Approved
0.6337	Remote Similarity	NPD4700	Approved
0.6333	Remote Similarity	NPD5368	Approved
0.6333	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD6001	Approved
0.6321	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.63	Remote Similarity	NPD5959	Approved
0.6292	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD6079	Approved
0.6263	Remote Similarity	NPD5210	Approved
0.6263	Remote Similarity	NPD4629	Approved
0.6262	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD6371	Approved
0.6238	Remote Similarity	NPD4225	Approved
0.6237	Remote Similarity	NPD4197	Approved
0.6214	Remote Similarity	NPD5226	Approved
0.6214	Remote Similarity	NPD5225	Approved
0.6214	Remote Similarity	NPD5211	Phase 2
0.6214	Remote Similarity	NPD5224	Approved
0.6214	Remote Similarity	NPD4633	Approved
0.62	Remote Similarity	NPD7614	Phase 1
0.6196	Remote Similarity	NPD4270	Approved
0.6196	Remote Similarity	NPD4269	Approved
0.6195	Remote Similarity	NPD6319	Approved
0.6174	Remote Similarity	NPD8328	Phase 3
0.6163	Remote Similarity	NPD5777	Approved
0.6154	Remote Similarity	NPD5174	Approved
0.6154	Remote Similarity	NPD6052	Approved
0.6154	Remote Similarity	NPD5175	Approved
0.6145	Remote Similarity	NPD3704	Approved
0.6129	Remote Similarity	NPD7154	Phase 3
0.6126	Remote Similarity	NPD6274	Approved
0.6122	Remote Similarity	NPD8035	Phase 2
0.6122	Remote Similarity	NPD7983	Approved
0.6122	Remote Similarity	NPD8034	Phase 2
0.6122	Remote Similarity	NPD7637	Suspended
0.6121	Remote Similarity	NPD7492	Approved
0.6118	Remote Similarity	NPD4137	Phase 3
0.6117	Remote Similarity	NPD5223	Approved
0.6111	Remote Similarity	NPD4634	Approved
0.6106	Remote Similarity	NPD7100	Approved
0.6106	Remote Similarity	NPD7101	Approved
0.6105	Remote Similarity	NPD6422	Discontinued
0.6105	Remote Similarity	NPD4623	Approved
0.6105	Remote Similarity	NPD4690	Approved
0.6105	Remote Similarity	NPD5205	Approved
0.6105	Remote Similarity	NPD4689	Approved
0.6105	Remote Similarity	NPD5786	Approved
0.6105	Remote Similarity	NPD5690	Phase 2
0.6105	Remote Similarity	NPD4694	Approved
0.6105	Remote Similarity	NPD4519	Discontinued
0.6105	Remote Similarity	NPD4688	Approved
0.6105	Remote Similarity	NPD4138	Approved
0.6105	Remote Similarity	NPD4693	Phase 3
0.6105	Remote Similarity	NPD5280	Approved
0.6095	Remote Similarity	NPD5141	Approved
0.6091	Remote Similarity	NPD4632	Approved
0.6087	Remote Similarity	NPD4692	Approved
0.6087	Remote Similarity	NPD4139	Approved
0.6082	Remote Similarity	NPD6051	Approved
0.6078	Remote Similarity	NPD7638	Approved
0.6075	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD6616	Approved
0.6064	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD6059	Approved
0.6053	Remote Similarity	NPD6054	Approved
0.6047	Remote Similarity	NPD4747	Approved
0.6047	Remote Similarity	NPD4691	Approved
0.604	Remote Similarity	NPD7839	Suspended
0.604	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.604	Remote Similarity	NPD4697	Phase 3
0.604	Remote Similarity	NPD5222	Approved
0.604	Remote Similarity	NPD5221	Approved
0.6038	Remote Similarity	NPD4768	Approved
0.6038	Remote Similarity	NPD4767	Approved
0.6024	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD5733	Approved
0.6022	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD7640	Approved
0.6019	Remote Similarity	NPD7639	Approved
0.6018	Remote Similarity	NPD6335	Approved
0.6017	Remote Similarity	NPD7078	Approved
0.6017	Remote Similarity	NPD8293	Discontinued
0.6	Remote Similarity	NPD6909	Approved
0.6	Remote Similarity	NPD6908	Approved
0.6	Remote Similarity	NPD4754	Approved
0.6	Remote Similarity	NPD6053	Discontinued
0.6	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6	Remote Similarity	NPD229	Approved
0.5981	Remote Similarity	NPD6614	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