NPASS Compound

Structure

NPC122847 OpenBabel07101718182D 26 26 0 0 1 0 0 0 0 0999 V2000 -2.7285 2.5872 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 -6.8510 1.1037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5922 0.1378 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 -4.2121 0.3966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9533 1.3625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5391 -0.0517 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 -5.1780 0.1378 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 -2.9873 1.6213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2802 0.9142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 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 -5.8851 0.8449 0.0000 C 0 0 0 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 -1.3143 1.1730 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 -5.6263 1.8108 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 14 2 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 6 24 1 0 0 0 0 7 8 1 0 0 0 0 7 11 1 0 0 0 0 8 14 1 0 0 0 0 9 12 1 0 0 0 0 9 16 1 0 0 0 0 10 13 1 0 0 0 0 10 17 1 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 13 20 1 0 0 0 0 14 16 1 0 0 0 0 15 2 1 1 0 0 0 15 18 1 0 0 0 0 16 21 2 0 0 0 0 17 15 1 6 0 0 0 17 25 1 0 0 0 0 18 22 2 0 0 0 0 18 24 1 0 0 0 0 19 23 1 0 0 0 0 20 5 1 1 0 0 0 20 26 1 0 0 0 0 25 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	370.24
Volume:	390.752
LogP:	2.397
LogD:	2.182
LogS:	-3.737
# Rotatable Bonds:	11
TPSA:	82.06
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.36
Synthetic Accessibility Score:	4.352
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	3
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.573
MDCK Permeability:	2.45056926360121e-05
Pgp-inhibitor:	0.88
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.418
Plasma Protein Binding (PPB):	57.27628707885742%
Volume Distribution (VD):	0.581
Pgp-substrate:	60.16252136230469%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.728
CYP2C19-inhibitor:	0.262
CYP2C19-substrate:	0.839
CYP2C9-inhibitor:	0.306
CYP2C9-substrate:	0.147
CYP2D6-inhibitor:	0.022
CYP2D6-substrate:	0.526
CYP3A4-inhibitor:	0.489
CYP3A4-substrate:	0.289

ADMET: Excretion

Clearance (CL):	8.483
Half-life (T1/2):	0.484

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.507
Drug-inuced Liver Injury (DILI):	0.584
AMES Toxicity:	0.204
Rat Oral Acute Toxicity:	0.104
Maximum Recommended Daily Dose:	0.033
Skin Sensitization:	0.918
Carcinogencity:	0.773
Eye Corrosion:	0.099
Eye Irritation:	0.122
Respiratory Toxicity:	0.736

Download Data

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

Natural Product: NPC122847

Natural Product ID:	NPC122847
*Common Name:**	Aikupikoxide D
IUPAC Name:	methyl (2S)-2-[(3S,6R)-6-(8-hydroxy-8-methyl-4-methylidene-3-oxononyl)-6-methyldioxan-3-yl]propanoate
Synonyms:	Aikupikoxide D
Standard InCHIKey:	VQXVFFWQWCQNFB-KNBMTAEXSA-N
Standard InCHI:	InChI=1S/C20H34O6/c1-14(8-7-11-19(3,4)23)16(21)9-12-20(5)13-10-17(25-26-20)15(2)18(22)24-6/h15,17,23H,1,7-13H2,2-6H3/t15-,17-,20-/m0/s1
SMILES:	COC(=O)[C@H]([C@@H]1CC[C@](OO1)(C)CCC(=O)C(=C)CCCC(O)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL494392
PubChem CID:	10893988
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
NPO32571	diacarnus erythraenus	Species	Podospongiidae	Eukaryota	n.a.	Red Sea	n.a.	PMID[11678661]
NPO32571	diacarnus erythraenus	Species	Podospongiidae	Eukaryota	n.a.	Red Sea	n.a.	PMID[14738401]

☑ 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	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	>	1.0	ug.mL-1	PMID[458898]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	1.0	ug.mL-1	PMID[458898]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	1.0	ug.mL-1	PMID[458898]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	1.0	ug.mL-1	PMID[458899]
NPT168	Cell Line	P388	Mus musculus	IC50	>	1.0	ug.mL-1	PMID[458899]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	1.0	ug.mL-1	PMID[458899]

☑ 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 NPC122847 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	170
0.1-0.2	1583
0.2-0.3	6318
0.3-0.4	14410
0.4-0.5	9151
0.5-0.6	7365
0.6-0.7	3525
0.7-0.8	139
0.8-0.85	28
0.85-0.9	7
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8701	High Similarity	NPC308545
0.8701	High Similarity	NPC82488
0.8571	High Similarity	NPC476986
0.8571	High Similarity	NPC470905
0.8553	High Similarity	NPC469514
0.8462	Intermediate Similarity	NPC113363
0.8442	Intermediate Similarity	NPC476325
0.8442	Intermediate Similarity	NPC476264
0.8442	Intermediate Similarity	NPC469867
0.8375	Intermediate Similarity	NPC475395
0.8375	Intermediate Similarity	NPC476984
0.8333	Intermediate Similarity	NPC121200
0.8312	Intermediate Similarity	NPC476985
0.8312	Intermediate Similarity	NPC475744
0.8312	Intermediate Similarity	NPC474316
0.8289	Intermediate Similarity	NPC330016
0.825	Intermediate Similarity	NPC172309
0.825	Intermediate Similarity	NPC117960
0.825	Intermediate Similarity	NPC14044
0.8228	Intermediate Similarity	NPC19841
0.8205	Intermediate Similarity	NPC281296
0.8169	Intermediate Similarity	NPC474552
0.8158	Intermediate Similarity	NPC167145
0.8148	Intermediate Similarity	NPC474605
0.8148	Intermediate Similarity	NPC476292
0.8077	Intermediate Similarity	NPC266119
0.8077	Intermediate Similarity	NPC474447
0.8049	Intermediate Similarity	NPC476983
0.8	Intermediate Similarity	NPC268502
0.8	Intermediate Similarity	NPC254996
0.7976	Intermediate Similarity	NPC476104
0.7949	Intermediate Similarity	NPC199445
0.7949	Intermediate Similarity	NPC60718
0.7945	Intermediate Similarity	NPC306805
0.7945	Intermediate Similarity	NPC215987
0.7901	Intermediate Similarity	NPC476265
0.7901	Intermediate Similarity	NPC274522
0.7887	Intermediate Similarity	NPC472021
0.7857	Intermediate Similarity	NPC471344
0.7848	Intermediate Similarity	NPC152754
0.7848	Intermediate Similarity	NPC59602
0.7848	Intermediate Similarity	NPC476987
0.7848	Intermediate Similarity	NPC239127
0.7831	Intermediate Similarity	NPC69469
0.7805	Intermediate Similarity	NPC476988
0.7765	Intermediate Similarity	NPC475181
0.7765	Intermediate Similarity	NPC476982
0.7765	Intermediate Similarity	NPC262085
0.7746	Intermediate Similarity	NPC226602
0.7746	Intermediate Similarity	NPC472019
0.7746	Intermediate Similarity	NPC475821
0.7746	Intermediate Similarity	NPC472020
0.7738	Intermediate Similarity	NPC471343
0.7722	Intermediate Similarity	NPC255060
0.7703	Intermediate Similarity	NPC476330
0.7701	Intermediate Similarity	NPC471342
0.7701	Intermediate Similarity	NPC469866
0.7692	Intermediate Similarity	NPC238425
0.7692	Intermediate Similarity	NPC472018
0.7692	Intermediate Similarity	NPC474543
0.7619	Intermediate Similarity	NPC476100
0.7595	Intermediate Similarity	NPC474551
0.7595	Intermediate Similarity	NPC48641
0.759	Intermediate Similarity	NPC475481
0.759	Intermediate Similarity	NPC79277
0.7558	Intermediate Similarity	NPC469483
0.7529	Intermediate Similarity	NPC120158
0.7529	Intermediate Similarity	NPC475193
0.7529	Intermediate Similarity	NPC9868
0.7528	Intermediate Similarity	NPC329952
0.7473	Intermediate Similarity	NPC475900
0.7471	Intermediate Similarity	NPC201658
0.747	Intermediate Similarity	NPC103634
0.747	Intermediate Similarity	NPC469920
0.7442	Intermediate Similarity	NPC261380
0.7436	Intermediate Similarity	NPC69462
0.7412	Intermediate Similarity	NPC475989
0.7391	Intermediate Similarity	NPC39859
0.7391	Intermediate Similarity	NPC76862
0.7391	Intermediate Similarity	NPC470883
0.7391	Intermediate Similarity	NPC158416
0.7386	Intermediate Similarity	NPC476707
0.7386	Intermediate Similarity	NPC56413
0.7386	Intermediate Similarity	NPC476706
0.7356	Intermediate Similarity	NPC162071
0.7342	Intermediate Similarity	NPC126061
0.7333	Intermediate Similarity	NPC470373
0.7333	Intermediate Similarity	NPC470325
0.7333	Intermediate Similarity	NPC470379
0.7333	Intermediate Similarity	NPC53642
0.7333	Intermediate Similarity	NPC184063
0.7326	Intermediate Similarity	NPC3464
0.7326	Intermediate Similarity	NPC72464
0.7326	Intermediate Similarity	NPC475963
0.7326	Intermediate Similarity	NPC151176
0.7312	Intermediate Similarity	NPC40812
0.7308	Intermediate Similarity	NPC107130
0.7303	Intermediate Similarity	NPC253618
0.7303	Intermediate Similarity	NPC168679
0.7303	Intermediate Similarity	NPC12872
0.7303	Intermediate Similarity	NPC77001
0.7294	Intermediate Similarity	NPC85772
0.7284	Intermediate Similarity	NPC474419
0.7283	Intermediate Similarity	NPC322188
0.7283	Intermediate Similarity	NPC210214
0.7273	Intermediate Similarity	NPC197333
0.7262	Intermediate Similarity	NPC51507
0.7262	Intermediate Similarity	NPC233377
0.7253	Intermediate Similarity	NPC308656
0.7253	Intermediate Similarity	NPC473234
0.7253	Intermediate Similarity	NPC473263
0.7253	Intermediate Similarity	NPC473273
0.7253	Intermediate Similarity	NPC475302
0.7253	Intermediate Similarity	NPC60386
0.7241	Intermediate Similarity	NPC125290
0.7241	Intermediate Similarity	NPC47958
0.7241	Intermediate Similarity	NPC255307
0.7241	Intermediate Similarity	NPC149725
0.7241	Intermediate Similarity	NPC165162
0.7241	Intermediate Similarity	NPC304509
0.7237	Intermediate Similarity	NPC469926
0.7234	Intermediate Similarity	NPC308567
0.7234	Intermediate Similarity	NPC474793
0.7234	Intermediate Similarity	NPC261377
0.7234	Intermediate Similarity	NPC83895
0.7234	Intermediate Similarity	NPC187761
0.7234	Intermediate Similarity	NPC255592
0.7229	Intermediate Similarity	NPC11796
0.7229	Intermediate Similarity	NPC218817
0.7222	Intermediate Similarity	NPC65359
0.7222	Intermediate Similarity	NPC19087
0.7215	Intermediate Similarity	NPC472017
0.7209	Intermediate Similarity	NPC128429
0.7209	Intermediate Similarity	NPC11620
0.7209	Intermediate Similarity	NPC1761
0.7209	Intermediate Similarity	NPC52609
0.7204	Intermediate Similarity	NPC476009
0.7191	Intermediate Similarity	NPC58219
0.7191	Intermediate Similarity	NPC53158
0.7191	Intermediate Similarity	NPC177629
0.7191	Intermediate Similarity	NPC477302
0.7176	Intermediate Similarity	NPC141810
0.7176	Intermediate Similarity	NPC281949
0.7176	Intermediate Similarity	NPC286229
0.7176	Intermediate Similarity	NPC301477
0.7176	Intermediate Similarity	NPC25684
0.7176	Intermediate Similarity	NPC470241
0.7174	Intermediate Similarity	NPC71589
0.716	Intermediate Similarity	NPC160540
0.7159	Intermediate Similarity	NPC309757
0.7159	Intermediate Similarity	NPC475461
0.7159	Intermediate Similarity	NPC474762
0.7159	Intermediate Similarity	NPC476015
0.7159	Intermediate Similarity	NPC475019
0.7159	Intermediate Similarity	NPC185638
0.7159	Intermediate Similarity	NPC305475
0.7159	Intermediate Similarity	NPC236692
0.7159	Intermediate Similarity	NPC477994
0.7159	Intermediate Similarity	NPC150755
0.7159	Intermediate Similarity	NPC477993
0.7159	Intermediate Similarity	NPC261721
0.7159	Intermediate Similarity	NPC474949
0.7159	Intermediate Similarity	NPC238593
0.7143	Intermediate Similarity	NPC276647
0.7143	Intermediate Similarity	NPC469627
0.7143	Intermediate Similarity	NPC184463
0.7143	Intermediate Similarity	NPC261607
0.7143	Intermediate Similarity	NPC622
0.7143	Intermediate Similarity	NPC250753
0.7143	Intermediate Similarity	NPC617
0.7143	Intermediate Similarity	NPC111114
0.7143	Intermediate Similarity	NPC300312
0.7143	Intermediate Similarity	NPC476705
0.7128	Intermediate Similarity	NPC111348
0.7126	Intermediate Similarity	NPC141193
0.7126	Intermediate Similarity	NPC165287
0.7126	Intermediate Similarity	NPC96259
0.7126	Intermediate Similarity	NPC114979
0.7126	Intermediate Similarity	NPC191476
0.7126	Intermediate Similarity	NPC158756
0.7126	Intermediate Similarity	NPC295799
0.7126	Intermediate Similarity	NPC70424
0.7126	Intermediate Similarity	NPC474780
0.7126	Intermediate Similarity	NPC243618
0.7125	Intermediate Similarity	NPC474590
0.7111	Intermediate Similarity	NPC206001
0.7111	Intermediate Similarity	NPC307411
0.7111	Intermediate Similarity	NPC38392
0.7111	Intermediate Similarity	NPC218927
0.7111	Intermediate Similarity	NPC52198
0.7111	Intermediate Similarity	NPC92974
0.7111	Intermediate Similarity	NPC117405
0.7111	Intermediate Similarity	NPC474951
0.7111	Intermediate Similarity	NPC97577
0.7108	Intermediate Similarity	NPC474433
0.7108	Intermediate Similarity	NPC474003
0.7089	Intermediate Similarity	NPC477449
0.7089	Intermediate Similarity	NPC469914
0.7089	Intermediate Similarity	NPC477448
0.7083	Intermediate Similarity	NPC477871

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 NPC122847 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	167
0.1-0.2	2250
0.2-0.3	3834
0.3-0.4	1909
0.4-0.5	581
0.5-0.6	325
0.6-0.7	81
0.7-0.8	3
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
0.7381	Intermediate Similarity	NPD5369	Approved
0.7111	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD6101	Approved
0.7045	Intermediate Similarity	NPD5363	Approved
0.6989	Remote Similarity	NPD5282	Discontinued
0.6957	Remote Similarity	NPD6411	Approved
0.6915	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4269	Approved
0.6897	Remote Similarity	NPD6435	Approved
0.6897	Remote Similarity	NPD4270	Approved
0.686	Remote Similarity	NPD5368	Approved
0.6848	Remote Similarity	NPD6698	Approved
0.6848	Remote Similarity	NPD46	Approved
0.6848	Remote Similarity	NPD5785	Approved
0.6795	Remote Similarity	NPD7341	Phase 2
0.6778	Remote Similarity	NPD5786	Approved
0.6709	Remote Similarity	NPD7331	Phase 2
0.6702	Remote Similarity	NPD6399	Phase 3
0.6702	Remote Similarity	NPD5779	Approved
0.6702	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD4252	Approved
0.6629	Remote Similarity	NPD7154	Phase 3
0.6628	Remote Similarity	NPD4238	Approved
0.6628	Remote Similarity	NPD4802	Phase 2
0.6598	Remote Similarity	NPD7902	Approved
0.6596	Remote Similarity	NPD8035	Phase 2
0.6596	Remote Similarity	NPD7983	Approved
0.6596	Remote Similarity	NPD8034	Phase 2
0.6569	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6371	Approved
0.6495	Remote Similarity	NPD7839	Suspended
0.6477	Remote Similarity	NPD4821	Approved
0.6477	Remote Similarity	NPD4819	Approved
0.6477	Remote Similarity	NPD4820	Approved
0.6477	Remote Similarity	NPD4822	Approved
0.6458	Remote Similarity	NPD7748	Approved
0.6444	Remote Similarity	NPD5362	Discontinued
0.6444	Remote Similarity	NPD4788	Approved
0.6437	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6084	Phase 2
0.6429	Remote Similarity	NPD6083	Phase 2
0.6421	Remote Similarity	NPD7515	Phase 2
0.6392	Remote Similarity	NPD5695	Phase 3
0.6364	Remote Similarity	NPD5696	Approved
0.6351	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD6899	Approved
0.6346	Remote Similarity	NPD6881	Approved
0.6346	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD6649	Approved
0.6321	Remote Similarity	NPD6650	Approved
0.6311	Remote Similarity	NPD5739	Approved
0.6311	Remote Similarity	NPD6402	Approved
0.6311	Remote Similarity	NPD6675	Approved
0.6311	Remote Similarity	NPD7128	Approved
0.6304	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD7900	Approved
0.6289	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD6372	Approved
0.6286	Remote Similarity	NPD6373	Approved
0.625	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4271	Approved
0.625	Remote Similarity	NPD5281	Approved
0.625	Remote Similarity	NPD5697	Approved
0.625	Remote Similarity	NPD4268	Approved
0.625	Remote Similarity	NPD7909	Approved
0.625	Remote Similarity	NPD5284	Approved
0.6237	Remote Similarity	NPD7521	Approved
0.6237	Remote Similarity	NPD6422	Discontinued
0.6237	Remote Similarity	NPD6684	Approved
0.6237	Remote Similarity	NPD7146	Approved
0.6237	Remote Similarity	NPD6409	Approved
0.6237	Remote Similarity	NPD7334	Approved
0.6237	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD5330	Approved
0.6226	Remote Similarity	NPD7290	Approved
0.6226	Remote Similarity	NPD7102	Approved
0.6226	Remote Similarity	NPD6883	Approved
0.6211	Remote Similarity	NPD1695	Approved
0.6211	Remote Similarity	NPD5370	Suspended
0.62	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.62	Remote Similarity	NPD4225	Approved
0.619	Remote Similarity	NPD7320	Approved
0.619	Remote Similarity	NPD6686	Approved
0.6182	Remote Similarity	NPD7115	Discovery
0.6168	Remote Similarity	NPD6847	Approved
0.6168	Remote Similarity	NPD6617	Approved
0.6168	Remote Similarity	NPD6869	Approved
0.6168	Remote Similarity	NPD8130	Phase 1
0.6154	Remote Similarity	NPD3198	Approved
0.6154	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD7838	Discovery
0.6136	Remote Similarity	NPD4756	Discovery
0.6132	Remote Similarity	NPD6014	Approved
0.6132	Remote Similarity	NPD6012	Approved
0.6132	Remote Similarity	NPD6013	Approved
0.6129	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD1694	Approved
0.6111	Remote Similarity	NPD6882	Approved
0.6111	Remote Similarity	NPD8297	Approved
0.6111	Remote Similarity	NPD4695	Discontinued
0.6105	Remote Similarity	NPD6672	Approved
0.6105	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD5737	Approved
0.6105	Remote Similarity	NPD6903	Approved
0.6095	Remote Similarity	NPD5701	Approved
0.6067	Remote Similarity	NPD3732	Approved
0.6064	Remote Similarity	NPD3618	Phase 1
0.6061	Remote Similarity	NPD4629	Approved
0.6061	Remote Similarity	NPD5210	Approved
0.6049	Remote Similarity	NPD3197	Phase 1
0.6042	Remote Similarity	NPD4753	Phase 2
0.6038	Remote Similarity	NPD6011	Approved
0.6022	Remote Similarity	NPD3666	Approved
0.6022	Remote Similarity	NPD3133	Approved
0.6022	Remote Similarity	NPD4786	Approved
0.6022	Remote Similarity	NPD3665	Phase 1
0.6019	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3573	Approved
0.598	Remote Similarity	NPD5285	Approved
0.598	Remote Similarity	NPD5286	Approved
0.598	Remote Similarity	NPD4696	Approved
0.5978	Remote Similarity	NPD3667	Approved
0.5978	Remote Similarity	NPD5209	Approved
0.5943	Remote Similarity	NPD6412	Phase 2
0.5941	Remote Similarity	NPD4755	Approved
0.5926	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5921	Remote Similarity	NPD3196	Approved
0.5921	Remote Similarity	NPD4266	Approved
0.5921	Remote Similarity	NPD3194	Approved
0.5921	Remote Similarity	NPD3728	Approved
0.5921	Remote Similarity	NPD3730	Approved
0.5921	Remote Similarity	NPD3195	Phase 2
0.5918	Remote Similarity	NPD6079	Approved
0.5918	Remote Similarity	NPD7637	Suspended
0.5915	Remote Similarity	NPD634	Phase 3
0.5914	Remote Similarity	NPD5331	Approved
0.5914	Remote Similarity	NPD5332	Approved
0.5909	Remote Similarity	NPD8039	Approved
0.5904	Remote Similarity	NPD3704	Approved
0.59	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD5279	Phase 3
0.5877	Remote Similarity	NPD6319	Approved
0.5876	Remote Similarity	NPD6904	Approved
0.5876	Remote Similarity	NPD5328	Approved
0.5876	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD6080	Approved
0.5876	Remote Similarity	NPD6673	Approved
0.5872	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.587	Remote Similarity	NPD4790	Discontinued
0.5867	Remote Similarity	NPD3186	Phase 1
0.5865	Remote Similarity	NPD4633	Approved
0.5865	Remote Similarity	NPD5224	Approved
0.5865	Remote Similarity	NPD5211	Phase 2
0.5865	Remote Similarity	NPD5225	Approved
0.5865	Remote Similarity	NPD5226	Approved
0.5862	Remote Similarity	NPD8328	Phase 3
0.5859	Remote Similarity	NPD4202	Approved
0.5841	Remote Similarity	NPD7641	Discontinued
0.5833	Remote Similarity	NPD4250	Approved
0.5833	Remote Similarity	NPD4251	Approved
0.5833	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD4700	Approved
0.5818	Remote Similarity	NPD6053	Discontinued
0.5812	Remote Similarity	NPD7492	Approved
0.581	Remote Similarity	NPD5174	Approved
0.581	Remote Similarity	NPD5175	Approved
0.5806	Remote Similarity	NPD4223	Phase 3
0.5806	Remote Similarity	NPD4221	Approved
0.5804	Remote Similarity	NPD6274	Approved
0.5789	Remote Similarity	NPD5329	Approved
0.5789	Remote Similarity	NPD3172	Approved
0.5789	Remote Similarity	NPD7100	Approved
0.5789	Remote Similarity	NPD7101	Approved
0.5783	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5783	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.578	Remote Similarity	NPD4634	Approved
0.5778	Remote Similarity	NPD6116	Phase 1
0.5769	Remote Similarity	NPD5344	Discontinued
0.5769	Remote Similarity	NPD5223	Approved
0.5766	Remote Similarity	NPD4632	Approved
0.5766	Remote Similarity	NPD8133	Approved
0.5765	Remote Similarity	NPD229	Approved
0.5763	Remote Similarity	NPD6616	Approved
0.5761	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD6050	Approved
0.5755	Remote Similarity	NPD5141	Approved
0.5753	Remote Similarity	NPD622	Approved
0.5739	Remote Similarity	NPD6054	Approved
0.573	Remote Similarity	NPD3702	Approved
0.5729	Remote Similarity	NPD6098	Approved
0.5729	Remote Similarity	NPD5690	Phase 2
0.5729	Remote Similarity	NPD4249	Approved
0.5728	Remote Similarity	NPD7638	Approved
0.5726	Remote Similarity	NPD7642	Approved
0.5714	Remote Similarity	NPD7078	Approved
0.5714	Remote Similarity	NPD8139	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