NPASS Compound

Structure

NPC475395 OpenBabel07101718302D 25 26 0 0 1 0 0 0 0 0999 V2000 -4.7297 0.9142 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 -2.5391 -1.9836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2802 -1.0176 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 -4.9192 -1.7247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1780 -0.7588 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 -3.9533 -1.9836 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 -1.8320 -0.7588 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 -4.4709 -0.0517 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 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 -3.2462 -1.2765 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 -3.5050 -0.3105 0.0000 C 0 0 3 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 -3.2462 0.6554 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 18 1 0 0 0 0 4 18 1 0 0 0 0 6 23 1 0 0 0 0 7 8 1 0 0 0 0 7 10 1 0 0 0 0 8 14 1 0 0 0 0 9 11 1 0 0 0 0 9 16 1 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 12 13 1 0 0 0 0 12 19 1 0 0 0 0 13 20 1 0 0 0 0 14 20 1 0 0 0 0 15 2 1 1 0 0 0 15 17 1 0 0 0 0 16 15 1 6 0 0 0 16 24 1 0 0 0 0 17 21 2 0 0 0 0 17 23 1 0 0 0 0 18 20 1 0 0 0 0 19 5 1 1 0 0 0 19 25 1 0 0 0 0 20 22 1 0 0 0 0 24 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	354.24
Volume:	376.041
LogP:	3.514
LogD:	3.356
LogS:	-4.796
# Rotatable Bonds:	6
TPSA:	64.99
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.46
Synthetic Accessibility Score:	4.707
Fsp3:	0.85
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:	-4.627
MDCK Permeability:	2.342136576771736e-05
Pgp-inhibitor:	0.091
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.35
Plasma Protein Binding (PPB):	56.70450973510742%
Volume Distribution (VD):	1.632
Pgp-substrate:	58.13136672973633%

ADMET: Metabolism

CYP1A2-inhibitor:	0.045
CYP1A2-substrate:	0.858
CYP2C19-inhibitor:	0.298
CYP2C19-substrate:	0.928
CYP2C9-inhibitor:	0.155
CYP2C9-substrate:	0.162
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.844
CYP3A4-inhibitor:	0.762
CYP3A4-substrate:	0.628

ADMET: Excretion

Clearance (CL):	7.052
Half-life (T1/2):	0.098

ADMET: Toxicity

hERG Blockers:	0.139
Human Hepatotoxicity (H-HT):	0.333
Drug-inuced Liver Injury (DILI):	0.26
AMES Toxicity:	0.048
Rat Oral Acute Toxicity:	0.088
Maximum Recommended Daily Dose:	0.065
Skin Sensitization:	0.324
Carcinogencity:	0.532
Eye Corrosion:	0.007
Eye Irritation:	0.065
Respiratory Toxicity:	0.954

Download Data

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

Natural Product: NPC475395

Natural Product ID:	NPC475395
*Common Name:**	Aikupikoxide B
IUPAC Name:	methyl (2S)-2-[(3S,6R)-6-[2-(1-hydroxy-2,2-dimethyl-6-methylidenecyclohexyl)ethyl]-6-methyldioxan-3-yl]propanoate
Synonyms:
Standard InCHIKey:	OHYYIYQJXHASNH-CAHGDOEDSA-N
Standard InCHI:	InChI=1S/C20H34O5/c1-14-8-7-10-18(3,4)20(14,22)13-12-19(5)11-9-16(24-25-19)15(2)17(21)23-6/h15-16,22H,1,7-13H2,2-6H3/t15-,16-,19+,20?/m0/s1
SMILES:	COC(=O)[C@H]([C@@H]1CC[C@](OO1)(C)CCC1(O)C(=C)CCCC1(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL504808
PubChem CID:	11111009
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[509960]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	1.0	ug.mL-1	PMID[509960]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	1.0	ug.mL-1	PMID[509960]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	1.0	ug.mL-1	PMID[509961]
NPT168	Cell Line	P388	Mus musculus	IC50	>	1.0	ug.mL-1	PMID[509961]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	1.0	ug.mL-1	PMID[509961]

☑ 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 NPC475395 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	189
0.1-0.2	1416
0.2-0.3	5387
0.3-0.4	13717
0.4-0.5	9049
0.5-0.6	6866
0.6-0.7	5167
0.7-0.8	852
0.8-0.85	30
0.85-0.9	13
0.9-0.95	7
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476984
0.95	High Similarity	NPC476104
0.9474	High Similarity	NPC470905
0.9474	High Similarity	NPC476986
0.9375	High Similarity	NPC471344
0.9211	High Similarity	NPC475744
0.9211	High Similarity	NPC476985
0.9211	High Similarity	NPC474316
0.9091	High Similarity	NPC469867
0.9	High Similarity	NPC474605
0.9	High Similarity	NPC476292
0.8889	High Similarity	NPC476983
0.875	High Similarity	NPC476265
0.875	High Similarity	NPC274522
0.8706	High Similarity	NPC471342
0.8706	High Similarity	NPC469866
0.8642	High Similarity	NPC117960
0.8642	High Similarity	NPC14044
0.8642	High Similarity	NPC172309
0.8571	High Similarity	NPC476982
0.8571	High Similarity	NPC262085
0.8434	Intermediate Similarity	NPC476100
0.8415	Intermediate Similarity	NPC476988
0.8395	Intermediate Similarity	NPC308545
0.8395	Intermediate Similarity	NPC82488
0.8375	Intermediate Similarity	NPC122847
0.825	Intermediate Similarity	NPC152754
0.825	Intermediate Similarity	NPC476987
0.825	Intermediate Similarity	NPC59602
0.8148	Intermediate Similarity	NPC474433
0.8148	Intermediate Similarity	NPC476325
0.8148	Intermediate Similarity	NPC476264
0.814	Intermediate Similarity	NPC475181
0.8118	Intermediate Similarity	NPC471343
0.8068	Intermediate Similarity	NPC77001
0.8068	Intermediate Similarity	NPC253618
0.8049	Intermediate Similarity	NPC121200
0.8025	Intermediate Similarity	NPC469514
0.8	Intermediate Similarity	NPC18819
0.8	Intermediate Similarity	NPC243347
0.8	Intermediate Similarity	NPC46610
0.7952	Intermediate Similarity	NPC268502
0.7952	Intermediate Similarity	NPC254996
0.7952	Intermediate Similarity	NPC192999
0.7952	Intermediate Similarity	NPC476438
0.7931	Intermediate Similarity	NPC322159
0.7927	Intermediate Similarity	NPC281296
0.7912	Intermediate Similarity	NPC469982
0.7907	Intermediate Similarity	NPC120158
0.7907	Intermediate Similarity	NPC475193
0.7848	Intermediate Similarity	NPC91369
0.7841	Intermediate Similarity	NPC134197
0.7831	Intermediate Similarity	NPC321514
0.7831	Intermediate Similarity	NPC269543
0.7831	Intermediate Similarity	NPC247783
0.7821	Intermediate Similarity	NPC36616
0.7821	Intermediate Similarity	NPC290445
0.7805	Intermediate Similarity	NPC474447
0.7791	Intermediate Similarity	NPC69469
0.7791	Intermediate Similarity	NPC471037
0.7778	Intermediate Similarity	NPC330016
0.7766	Intermediate Similarity	NPC174663
0.7765	Intermediate Similarity	NPC327002
0.7765	Intermediate Similarity	NPC475951
0.7753	Intermediate Similarity	NPC104560
0.7753	Intermediate Similarity	NPC255176
0.775	Intermediate Similarity	NPC72343
0.7738	Intermediate Similarity	NPC263951
0.7727	Intermediate Similarity	NPC475007
0.7727	Intermediate Similarity	NPC198761
0.7727	Intermediate Similarity	NPC473226
0.7727	Intermediate Similarity	NPC73038
0.7727	Intermediate Similarity	NPC185638
0.7727	Intermediate Similarity	NPC187545
0.7701	Intermediate Similarity	NPC130966
0.7701	Intermediate Similarity	NPC263974
0.7692	Intermediate Similarity	NPC471901
0.7683	Intermediate Similarity	NPC199445
0.7683	Intermediate Similarity	NPC39362
0.7683	Intermediate Similarity	NPC60718
0.7674	Intermediate Similarity	NPC471159
0.7674	Intermediate Similarity	NPC123880
0.7667	Intermediate Similarity	NPC57954
0.7667	Intermediate Similarity	NPC213832
0.7667	Intermediate Similarity	NPC194642
0.766	Intermediate Similarity	NPC253586
0.766	Intermediate Similarity	NPC472851
0.7654	Intermediate Similarity	NPC167145
0.764	Intermediate Similarity	NPC171722
0.7634	Intermediate Similarity	NPC134067
0.7634	Intermediate Similarity	NPC205173
0.7634	Intermediate Similarity	NPC266899
0.7632	Intermediate Similarity	NPC474552
0.7619	Intermediate Similarity	NPC239098
0.7619	Intermediate Similarity	NPC179028
0.7609	Intermediate Similarity	NPC287118
0.7609	Intermediate Similarity	NPC199543
0.7609	Intermediate Similarity	NPC471902
0.7609	Intermediate Similarity	NPC473690
0.7604	Intermediate Similarity	NPC39683
0.7604	Intermediate Similarity	NPC111292
0.759	Intermediate Similarity	NPC476601
0.7582	Intermediate Similarity	NPC469400
0.7579	Intermediate Similarity	NPC474793
0.7579	Intermediate Similarity	NPC316598
0.7558	Intermediate Similarity	NPC209318
0.7558	Intermediate Similarity	NPC14203
0.7558	Intermediate Similarity	NPC229584
0.7558	Intermediate Similarity	NPC223330
0.7556	Intermediate Similarity	NPC211162
0.7556	Intermediate Similarity	NPC471900
0.7556	Intermediate Similarity	NPC16377
0.7556	Intermediate Similarity	NPC183374
0.7556	Intermediate Similarity	NPC146937
0.7556	Intermediate Similarity	NPC56413
0.7553	Intermediate Similarity	NPC116457
0.7553	Intermediate Similarity	NPC242848
0.7553	Intermediate Similarity	NPC132824
0.7551	Intermediate Similarity	NPC239162
0.7529	Intermediate Similarity	NPC327674
0.7528	Intermediate Similarity	NPC472505
0.7528	Intermediate Similarity	NPC470955
0.7528	Intermediate Similarity	NPC70661
0.7528	Intermediate Similarity	NPC9231
0.7528	Intermediate Similarity	NPC475753
0.7528	Intermediate Similarity	NPC470415
0.7527	Intermediate Similarity	NPC23621
0.7527	Intermediate Similarity	NPC184006
0.7527	Intermediate Similarity	NPC78580
0.7526	Intermediate Similarity	NPC164551
0.7526	Intermediate Similarity	NPC475091
0.75	Intermediate Similarity	NPC471588
0.75	Intermediate Similarity	NPC472814
0.75	Intermediate Similarity	NPC282616
0.75	Intermediate Similarity	NPC474718
0.75	Intermediate Similarity	NPC37047
0.75	Intermediate Similarity	NPC180733
0.75	Intermediate Similarity	NPC177037
0.75	Intermediate Similarity	NPC198054
0.75	Intermediate Similarity	NPC471747
0.75	Intermediate Similarity	NPC966
0.75	Intermediate Similarity	NPC41971
0.75	Intermediate Similarity	NPC165064
0.75	Intermediate Similarity	NPC6255
0.75	Intermediate Similarity	NPC108371
0.75	Intermediate Similarity	NPC475416
0.75	Intermediate Similarity	NPC155120
0.75	Intermediate Similarity	NPC324341
0.75	Intermediate Similarity	NPC36491
0.75	Intermediate Similarity	NPC228784
0.75	Intermediate Similarity	NPC238227
0.75	Intermediate Similarity	NPC288833
0.75	Intermediate Similarity	NPC295799
0.75	Intermediate Similarity	NPC477521
0.7474	Intermediate Similarity	NPC474395
0.7474	Intermediate Similarity	NPC254496
0.7473	Intermediate Similarity	NPC155479
0.7471	Intermediate Similarity	NPC145143
0.7471	Intermediate Similarity	NPC170985
0.7449	Intermediate Similarity	NPC72151
0.7449	Intermediate Similarity	NPC90177
0.7447	Intermediate Similarity	NPC53565
0.7447	Intermediate Similarity	NPC210214
0.7447	Intermediate Similarity	NPC23241
0.7447	Intermediate Similarity	NPC195715
0.7444	Intermediate Similarity	NPC128644
0.7444	Intermediate Similarity	NPC264005
0.7444	Intermediate Similarity	NPC269360
0.7444	Intermediate Similarity	NPC231599
0.7444	Intermediate Similarity	NPC33768
0.7442	Intermediate Similarity	NPC157895
0.7442	Intermediate Similarity	NPC104120
0.7442	Intermediate Similarity	NPC148685
0.7439	Intermediate Similarity	NPC472018
0.7439	Intermediate Similarity	NPC238425
0.7439	Intermediate Similarity	NPC474543
0.7436	Intermediate Similarity	NPC215987
0.7436	Intermediate Similarity	NPC306805
0.7436	Intermediate Similarity	NPC476330
0.7423	Intermediate Similarity	NPC282524
0.7423	Intermediate Similarity	NPC75941
0.7423	Intermediate Similarity	NPC236585
0.7423	Intermediate Similarity	NPC242666
0.7419	Intermediate Similarity	NPC118490
0.7419	Intermediate Similarity	NPC476416
0.7419	Intermediate Similarity	NPC115021
0.7419	Intermediate Similarity	NPC243866
0.7419	Intermediate Similarity	NPC147272
0.7416	Intermediate Similarity	NPC76333
0.7416	Intermediate Similarity	NPC52628
0.7416	Intermediate Similarity	NPC329738
0.7416	Intermediate Similarity	NPC201655
0.7416	Intermediate Similarity	NPC164424
0.7407	Intermediate Similarity	NPC235586
0.7396	Intermediate Similarity	NPC164349
0.7391	Intermediate Similarity	NPC477147
0.7391	Intermediate Similarity	NPC214844
0.7391	Intermediate Similarity	NPC169933
0.7391	Intermediate Similarity	NPC86372
0.7391	Intermediate Similarity	NPC153853

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 NPC475395 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	177
0.1-0.2	1932
0.2-0.3	3818
0.3-0.4	2134
0.4-0.5	617
0.5-0.6	274
0.6-0.7	191
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
0.75	Intermediate Similarity	NPD6411	Approved
0.7312	Intermediate Similarity	NPD8034	Phase 2
0.7312	Intermediate Similarity	NPD8035	Phase 2
0.7283	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD6101	Approved
0.7234	Intermediate Similarity	NPD5778	Approved
0.7234	Intermediate Similarity	NPD5779	Approved
0.7222	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD6399	Phase 3
0.699	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD7748	Approved
0.6947	Remote Similarity	NPD7637	Suspended
0.6947	Remote Similarity	NPD7515	Phase 2
0.6939	Remote Similarity	NPD7902	Approved
0.6869	Remote Similarity	NPD4225	Approved
0.6818	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD7128	Approved
0.6796	Remote Similarity	NPD6402	Approved
0.6796	Remote Similarity	NPD6675	Approved
0.6796	Remote Similarity	NPD5739	Approved
0.6778	Remote Similarity	NPD5369	Approved
0.6768	Remote Similarity	NPD6084	Phase 2
0.6768	Remote Similarity	NPD6083	Phase 2
0.6735	Remote Similarity	NPD5695	Phase 3
0.6705	Remote Similarity	NPD6116	Phase 1
0.6703	Remote Similarity	NPD4269	Approved
0.6703	Remote Similarity	NPD4270	Approved
0.6703	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4821	Approved
0.6667	Remote Similarity	NPD6899	Approved
0.6667	Remote Similarity	NPD4822	Approved
0.6667	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD7320	Approved
0.6667	Remote Similarity	NPD5785	Approved
0.6667	Remote Similarity	NPD4819	Approved
0.6667	Remote Similarity	NPD4820	Approved
0.6667	Remote Similarity	NPD6881	Approved
0.6636	Remote Similarity	NPD7115	Discovery
0.6634	Remote Similarity	NPD7639	Approved
0.6634	Remote Similarity	NPD7640	Approved
0.6633	Remote Similarity	NPD7900	Approved
0.6633	Remote Similarity	NPD5282	Discontinued
0.6633	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.663	Remote Similarity	NPD4788	Approved
0.663	Remote Similarity	NPD7154	Phase 3
0.663	Remote Similarity	NPD5362	Discontinued
0.6604	Remote Similarity	NPD6372	Approved
0.6604	Remote Similarity	NPD6373	Approved
0.6598	Remote Similarity	NPD7983	Approved
0.6596	Remote Similarity	NPD7334	Approved
0.6596	Remote Similarity	NPD7521	Approved
0.6596	Remote Similarity	NPD5330	Approved
0.6596	Remote Similarity	NPD6409	Approved
0.6596	Remote Similarity	NPD7146	Approved
0.6596	Remote Similarity	NPD6684	Approved
0.6596	Remote Similarity	NPD5786	Approved
0.6591	Remote Similarity	NPD6117	Approved
0.6571	Remote Similarity	NPD5701	Approved
0.6571	Remote Similarity	NPD5697	Approved
0.6566	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD4786	Approved
0.6542	Remote Similarity	NPD7102	Approved
0.6542	Remote Similarity	NPD7290	Approved
0.6542	Remote Similarity	NPD6883	Approved
0.6535	Remote Similarity	NPD7638	Approved
0.6535	Remote Similarity	NPD5696	Approved
0.6522	Remote Similarity	NPD3667	Approved
0.6522	Remote Similarity	NPD6435	Approved
0.6514	Remote Similarity	NPD8133	Approved
0.6505	Remote Similarity	NPD5211	Phase 2
0.65	Remote Similarity	NPD7839	Suspended
0.6495	Remote Similarity	NPD46	Approved
0.6495	Remote Similarity	NPD6698	Approved
0.6489	Remote Similarity	NPD5363	Approved
0.6484	Remote Similarity	NPD4252	Approved
0.6484	Remote Similarity	NPD5368	Approved
0.6484	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD6869	Approved
0.6481	Remote Similarity	NPD6649	Approved
0.6481	Remote Similarity	NPD6617	Approved
0.6481	Remote Similarity	NPD8130	Phase 1
0.6481	Remote Similarity	NPD6847	Approved
0.6481	Remote Similarity	NPD6650	Approved
0.6477	Remote Similarity	NPD3702	Approved
0.6458	Remote Similarity	NPD6672	Approved
0.6458	Remote Similarity	NPD6903	Approved
0.6458	Remote Similarity	NPD5737	Approved
0.6458	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6695	Phase 3
0.6449	Remote Similarity	NPD6014	Approved
0.6449	Remote Similarity	NPD6013	Approved
0.6449	Remote Similarity	NPD6012	Approved
0.6444	Remote Similarity	NPD6697	Approved
0.6444	Remote Similarity	NPD6118	Approved
0.6444	Remote Similarity	NPD6115	Approved
0.6444	Remote Similarity	NPD6114	Approved
0.6444	Remote Similarity	NPD4268	Approved
0.6444	Remote Similarity	NPD4271	Approved
0.6436	Remote Similarity	NPD4755	Approved
0.6429	Remote Similarity	NPD5284	Approved
0.6429	Remote Similarity	NPD5281	Approved
0.6422	Remote Similarity	NPD6882	Approved
0.6422	Remote Similarity	NPD8297	Approved
0.6421	Remote Similarity	NPD3618	Phase 1
0.6421	Remote Similarity	NPD6422	Discontinued
0.6421	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD4753	Phase 2
0.6392	Remote Similarity	NPD5328	Approved
0.6389	Remote Similarity	NPD6371	Approved
0.6383	Remote Similarity	NPD3666	Approved
0.6383	Remote Similarity	NPD3133	Approved
0.6383	Remote Similarity	NPD3665	Phase 1
0.6381	Remote Similarity	NPD5141	Approved
0.6364	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4202	Approved
0.6355	Remote Similarity	NPD6011	Approved
0.6354	Remote Similarity	NPD3573	Approved
0.633	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD1694	Approved
0.6311	Remote Similarity	NPD5285	Approved
0.6311	Remote Similarity	NPD5286	Approved
0.6311	Remote Similarity	NPD4700	Approved
0.6311	Remote Similarity	NPD4696	Approved
0.6304	Remote Similarity	NPD7525	Registered
0.6304	Remote Similarity	NPD6930	Phase 2
0.6304	Remote Similarity	NPD4695	Discontinued
0.6304	Remote Similarity	NPD6931	Approved
0.6296	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD8039	Approved
0.6263	Remote Similarity	NPD6079	Approved
0.6262	Remote Similarity	NPD6412	Phase 2
0.6261	Remote Similarity	NPD6921	Approved
0.625	Remote Similarity	NPD5279	Phase 3
0.625	Remote Similarity	NPD4623	Approved
0.625	Remote Similarity	NPD6098	Approved
0.625	Remote Similarity	NPD4519	Discontinued
0.6239	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD6904	Approved
0.6224	Remote Similarity	NPD6673	Approved
0.6224	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD6080	Approved
0.6211	Remote Similarity	NPD3668	Phase 3
0.6196	Remote Similarity	NPD6929	Approved
0.6196	Remote Similarity	NPD7645	Phase 2
0.6195	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5224	Approved
0.619	Remote Similarity	NPD5225	Approved
0.619	Remote Similarity	NPD4633	Approved
0.619	Remote Similarity	NPD7632	Discontinued
0.619	Remote Similarity	NPD5226	Approved
0.6186	Remote Similarity	NPD7750	Discontinued
0.6186	Remote Similarity	NPD7524	Approved
0.618	Remote Similarity	NPD6926	Approved
0.618	Remote Similarity	NPD6924	Approved
0.6174	Remote Similarity	NPD6319	Approved
0.617	Remote Similarity	NPD4223	Phase 3
0.617	Remote Similarity	NPD4221	Approved
0.6167	Remote Similarity	NPD7319	Approved
0.6163	Remote Similarity	NPD229	Approved
0.6154	Remote Similarity	NPD8328	Phase 3
0.6146	Remote Similarity	NPD5329	Approved
0.6136	Remote Similarity	NPD6081	Approved
0.6136	Remote Similarity	NPD5777	Approved
0.6132	Remote Similarity	NPD5174	Approved
0.6132	Remote Similarity	NPD5175	Approved
0.6118	Remote Similarity	NPD4224	Phase 2
0.6111	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD6274	Approved
0.6105	Remote Similarity	NPD5332	Approved
0.6105	Remote Similarity	NPD5331	Approved
0.6102	Remote Similarity	NPD7492	Approved
0.61	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.61	Remote Similarity	NPD5693	Phase 1
0.61	Remote Similarity	NPD6050	Approved
0.6095	Remote Similarity	NPD5344	Discontinued
0.6095	Remote Similarity	NPD5223	Approved
0.6091	Remote Similarity	NPD4634	Approved
0.6087	Remote Similarity	NPD7101	Approved
0.6087	Remote Similarity	NPD7100	Approved
0.6087	Remote Similarity	NPD4802	Phase 2
0.6087	Remote Similarity	NPD4238	Approved
0.6078	Remote Similarity	NPD4629	Approved
0.6078	Remote Similarity	NPD5210	Approved
0.6071	Remote Similarity	NPD4632	Approved
0.6064	Remote Similarity	NPD4790	Discontinued
0.6061	Remote Similarity	NPD6051	Approved
0.605	Remote Similarity	NPD6616	Approved
0.605	Remote Similarity	NPD7507	Approved
0.6044	Remote Similarity	NPD6933	Approved
0.6042	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD4197	Approved
0.6036	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD6054	Approved
0.6034	Remote Similarity	NPD6059	Approved
0.6023	Remote Similarity	NPD4244	Approved
0.6023	Remote Similarity	NPD4245	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