NPASS Compound

Structure

NPC261253 OpenBabel07101718182D 26 28 0 0 1 0 0 0 0 0999 V2000 3.8722 -0.1939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3361 -1.0023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4340 -5.9033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9357 -2.4356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7631 -0.3577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3506 -2.7848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4424 -1.8237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1586 -3.8596 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5871 -1.0888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0969 -3.6320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8006 -0.5287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6084 -3.3999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3139 -4.3303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3708 -1.0207 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8351 -5.0250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2462 -3.5438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9459 -1.9851 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3135 -2.7403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9655 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9041 -1.8659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7632 -2.9332 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8362 -0.4828 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7962 -4.9332 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2616 -2.9231 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2750 -4.2385 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 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 6 7 1 0 0 0 0 6 16 1 0 0 0 0 7 19 1 0 0 0 0 8 10 1 0 0 0 0 8 16 2 0 0 0 0 9 11 1 0 0 0 0 9 17 1 0 0 0 0 10 21 1 0 0 0 0 11 22 1 0 0 0 0 12 18 1 0 0 0 0 12 21 1 0 0 0 0 13 16 1 0 0 0 0 13 25 1 0 0 0 0 14 20 2 0 0 0 0 15 23 2 0 0 0 0 15 25 1 0 0 0 0 17 20 1 0 0 0 0 17 21 1 6 0 0 0 18 20 1 0 0 0 0 18 24 2 0 0 0 0 19 22 1 6 0 0 0 19 26 1 0 0 0 0 21 4 1 6 0 0 0 22 5 1 6 0 0 0 22 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	360.23
Volume:	388.014
LogP:	3.43
LogD:	3.338
LogS:	-4.192
# Rotatable Bonds:	3
TPSA:	55.9
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.314
Synthetic Accessibility Score:	4.937
Fsp3:	0.727
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:	-4.651
MDCK Permeability:	2.1139823729754426e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.446
30% Bioavailability (F30%):	0.609

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.889
Plasma Protein Binding (PPB):	63.13982009887695%
Volume Distribution (VD):	0.812
Pgp-substrate:	35.392333984375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.035
CYP1A2-substrate:	0.164
CYP2C19-inhibitor:	0.165
CYP2C19-substrate:	0.871
CYP2C9-inhibitor:	0.085
CYP2C9-substrate:	0.032
CYP2D6-inhibitor:	0.036
CYP2D6-substrate:	0.115
CYP3A4-inhibitor:	0.667
CYP3A4-substrate:	0.653

ADMET: Excretion

Clearance (CL):	7.616
Half-life (T1/2):	0.816

ADMET: Toxicity

hERG Blockers:	0.061
Human Hepatotoxicity (H-HT):	0.173
Drug-inuced Liver Injury (DILI):	0.624
AMES Toxicity:	0.241
Rat Oral Acute Toxicity:	0.345
Maximum Recommended Daily Dose:	0.922
Skin Sensitization:	0.909
Carcinogencity:	0.904
Eye Corrosion:	0.118
Eye Irritation:	0.084
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC261253

Natural Product ID:	NPC261253
*Common Name:**	ZOSAKIHZJAHFSI-RZJRGZLOSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ZOSAKIHZJAHFSI-RZJRGZLOSA-N
Standard InCHI:	InChI=1S/C22H32O4/c1-14(2)20-17-9-11-22(5)19(26-22)7-6-16(13-25-15(3)23)8-10-21(17,4)12-18(20)24/h8,17,19H,6-7,9-13H2,1-5H3/b16-8-/t17-,19+,21-,22+/m1/s1
SMILES:	CC(=O)OC/C/1=CC[C@]2(C)CC(=O)C(=C(C)C)[C@H]2CC[C@]2([C@H](CC1)O2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1098399
PubChem CID:	46887666
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001760] Dolabellane and neodolabellane diterpenoids

*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
NPO32701	Eunicea	Genus	Plexauridae	Eukaryota	n.a.	southwestern Caribbean	n.a.	PMID[20384296]

☑ 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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	30600.0	nM	PMID[472765]

☑ 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 NPC261253 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	219
0.1-0.2	1458
0.2-0.3	5617
0.3-0.4	13688
0.4-0.5	9617
0.5-0.6	6655
0.6-0.7	4317
0.7-0.8	1066
0.8-0.85	50
0.85-0.9	7
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474045
0.9512	High Similarity	NPC469676
0.875	High Similarity	NPC221282
0.869	High Similarity	NPC475622
0.869	High Similarity	NPC108045
0.8659	High Similarity	NPC469690
0.8659	High Similarity	NPC469620
0.85	High Similarity	NPC469691
0.85	High Similarity	NPC167049
0.8488	Intermediate Similarity	NPC474547
0.8471	Intermediate Similarity	NPC170377
0.8333	Intermediate Similarity	NPC290651
0.8295	Intermediate Similarity	NPC475703
0.8256	Intermediate Similarity	NPC475842
0.8222	Intermediate Similarity	NPC62815
0.8182	Intermediate Similarity	NPC137253
0.8182	Intermediate Similarity	NPC50637
0.8171	Intermediate Similarity	NPC469669
0.8171	Intermediate Similarity	NPC469678
0.8171	Intermediate Similarity	NPC475771
0.8148	Intermediate Similarity	NPC92909
0.8148	Intermediate Similarity	NPC107783
0.814	Intermediate Similarity	NPC35556
0.8132	Intermediate Similarity	NPC473944
0.8118	Intermediate Similarity	NPC474510
0.8111	Intermediate Similarity	NPC166919
0.8095	Intermediate Similarity	NPC128276
0.809	Intermediate Similarity	NPC231889
0.8085	Intermediate Similarity	NPC477949
0.8068	Intermediate Similarity	NPC235792
0.8046	Intermediate Similarity	NPC193198
0.8046	Intermediate Similarity	NPC272814
0.8046	Intermediate Similarity	NPC53867
0.8046	Intermediate Similarity	NPC475989
0.8025	Intermediate Similarity	NPC477084
0.8023	Intermediate Similarity	NPC471325
0.8023	Intermediate Similarity	NPC141810
0.8022	Intermediate Similarity	NPC475748
0.8022	Intermediate Similarity	NPC312042
0.8	Intermediate Similarity	NPC269841
0.8	Intermediate Similarity	NPC469608
0.7978	Intermediate Similarity	NPC122502
0.7978	Intermediate Similarity	NPC64153
0.7976	Intermediate Similarity	NPC57744
0.7976	Intermediate Similarity	NPC186109
0.7959	Intermediate Similarity	NPC169843
0.7957	Intermediate Similarity	NPC476267
0.7952	Intermediate Similarity	NPC244166
0.7935	Intermediate Similarity	NPC20713
0.7935	Intermediate Similarity	NPC472705
0.7917	Intermediate Similarity	NPC54705
0.7907	Intermediate Similarity	NPC47747
0.7895	Intermediate Similarity	NPC213947
0.7895	Intermediate Similarity	NPC170143
0.7895	Intermediate Similarity	NPC108475
0.7889	Intermediate Similarity	NPC474765
0.7889	Intermediate Similarity	NPC478145
0.7889	Intermediate Similarity	NPC478144
0.7882	Intermediate Similarity	NPC471220
0.7882	Intermediate Similarity	NPC474005
0.7879	Intermediate Similarity	NPC470979
0.7879	Intermediate Similarity	NPC470975
0.7879	Intermediate Similarity	NPC103088
0.7872	Intermediate Similarity	NPC33473
0.7865	Intermediate Similarity	NPC189311
0.7865	Intermediate Similarity	NPC197903
0.7865	Intermediate Similarity	NPC215364
0.7865	Intermediate Similarity	NPC99395
0.7865	Intermediate Similarity	NPC78089
0.7857	Intermediate Similarity	NPC226242
0.7849	Intermediate Similarity	NPC475657
0.7849	Intermediate Similarity	NPC475838
0.7849	Intermediate Similarity	NPC228451
0.7849	Intermediate Similarity	NPC125674
0.7843	Intermediate Similarity	NPC475495
0.7841	Intermediate Similarity	NPC318468
0.7835	Intermediate Similarity	NPC475099
0.7831	Intermediate Similarity	NPC474758
0.7826	Intermediate Similarity	NPC473448
0.7826	Intermediate Similarity	NPC469718
0.7826	Intermediate Similarity	NPC329857
0.7816	Intermediate Similarity	NPC42470
0.7812	Intermediate Similarity	NPC222303
0.7812	Intermediate Similarity	NPC470188
0.7812	Intermediate Similarity	NPC471932
0.7812	Intermediate Similarity	NPC264378
0.7802	Intermediate Similarity	NPC224652
0.78	Intermediate Similarity	NPC471601
0.7791	Intermediate Similarity	NPC178277
0.7791	Intermediate Similarity	NPC471299
0.7791	Intermediate Similarity	NPC617
0.7778	Intermediate Similarity	NPC284902
0.7778	Intermediate Similarity	NPC107787
0.7778	Intermediate Similarity	NPC220478
0.7767	Intermediate Similarity	NPC475277
0.7767	Intermediate Similarity	NPC473522
0.7767	Intermediate Similarity	NPC477093
0.7766	Intermediate Similarity	NPC474247
0.7766	Intermediate Similarity	NPC140543
0.7766	Intermediate Similarity	NPC161998
0.7766	Intermediate Similarity	NPC90453
0.7766	Intermediate Similarity	NPC473316
0.7766	Intermediate Similarity	NPC473330
0.7766	Intermediate Similarity	NPC38830
0.7766	Intermediate Similarity	NPC477131
0.7755	Intermediate Similarity	NPC475320
0.7753	Intermediate Similarity	NPC149869
0.7753	Intermediate Similarity	NPC238197
0.7753	Intermediate Similarity	NPC474359
0.7753	Intermediate Similarity	NPC475100
0.7732	Intermediate Similarity	NPC471413
0.7727	Intermediate Similarity	NPC475936
0.7727	Intermediate Similarity	NPC200513
0.7723	Intermediate Similarity	NPC61411
0.7717	Intermediate Similarity	NPC78008
0.7717	Intermediate Similarity	NPC151770
0.7717	Intermediate Similarity	NPC475971
0.7717	Intermediate Similarity	NPC4986
0.7708	Intermediate Similarity	NPC100912
0.7708	Intermediate Similarity	NPC47834
0.7708	Intermediate Similarity	NPC110937
0.7701	Intermediate Similarity	NPC474739
0.7692	Intermediate Similarity	NPC160138
0.7684	Intermediate Similarity	NPC476487
0.7684	Intermediate Similarity	NPC474490
0.7684	Intermediate Similarity	NPC474947
0.7684	Intermediate Similarity	NPC476488
0.7684	Intermediate Similarity	NPC67584
0.7684	Intermediate Similarity	NPC281134
0.7683	Intermediate Similarity	NPC469660
0.7674	Intermediate Similarity	NPC253749
0.7674	Intermediate Similarity	NPC299235
0.7674	Intermediate Similarity	NPC474341
0.7667	Intermediate Similarity	NPC96621
0.7667	Intermediate Similarity	NPC137033
0.766	Intermediate Similarity	NPC135776
0.766	Intermediate Similarity	NPC476598
0.766	Intermediate Similarity	NPC476597
0.7654	Intermediate Similarity	NPC276290
0.7653	Intermediate Similarity	NPC471412
0.7647	Intermediate Similarity	NPC27205
0.7647	Intermediate Similarity	NPC271070
0.7647	Intermediate Similarity	NPC471934
0.764	Intermediate Similarity	NPC250315
0.764	Intermediate Similarity	NPC222358
0.764	Intermediate Similarity	NPC257358
0.764	Intermediate Similarity	NPC474472
0.764	Intermediate Similarity	NPC11620
0.7634	Intermediate Similarity	NPC471818
0.7634	Intermediate Similarity	NPC251385
0.7634	Intermediate Similarity	NPC161638
0.7634	Intermediate Similarity	NPC474761
0.7634	Intermediate Similarity	NPC49946
0.7634	Intermediate Similarity	NPC51004
0.7634	Intermediate Similarity	NPC37607
0.7634	Intermediate Similarity	NPC306168
0.7634	Intermediate Similarity	NPC476004
0.7634	Intermediate Similarity	NPC179394
0.7634	Intermediate Similarity	NPC301969
0.7634	Intermediate Similarity	NPC144133
0.7634	Intermediate Similarity	NPC49342
0.7629	Intermediate Similarity	NPC72647
0.7629	Intermediate Similarity	NPC107806
0.7629	Intermediate Similarity	NPC98868
0.7629	Intermediate Similarity	NPC221615
0.7629	Intermediate Similarity	NPC252295
0.7624	Intermediate Similarity	NPC470192
0.7619	Intermediate Similarity	NPC294434
0.7619	Intermediate Similarity	NPC477204
0.7619	Intermediate Similarity	NPC476355
0.7619	Intermediate Similarity	NPC117746
0.7619	Intermediate Similarity	NPC140287
0.7619	Intermediate Similarity	NPC259599
0.7619	Intermediate Similarity	NPC15499
0.7614	Intermediate Similarity	NPC79277
0.7614	Intermediate Similarity	NPC301477
0.7614	Intermediate Similarity	NPC281949
0.7614	Intermediate Similarity	NPC25684
0.7614	Intermediate Similarity	NPC475481
0.7614	Intermediate Similarity	NPC325031
0.7609	Intermediate Similarity	NPC474471
0.7609	Intermediate Similarity	NPC475902
0.7609	Intermediate Similarity	NPC281516
0.7609	Intermediate Similarity	NPC226863
0.7609	Intermediate Similarity	NPC227379
0.7604	Intermediate Similarity	NPC230800
0.7604	Intermediate Similarity	NPC29952
0.7604	Intermediate Similarity	NPC118159
0.7604	Intermediate Similarity	NPC213078
0.7604	Intermediate Similarity	NPC476315
0.7604	Intermediate Similarity	NPC279621
0.7604	Intermediate Similarity	NPC202833
0.7604	Intermediate Similarity	NPC476275
0.7604	Intermediate Similarity	NPC477354
0.7604	Intermediate Similarity	NPC475380
0.7604	Intermediate Similarity	NPC24956
0.7604	Intermediate Similarity	NPC58052
0.7604	Intermediate Similarity	NPC18019
0.7604	Intermediate Similarity	NPC209297
0.7604	Intermediate Similarity	NPC111684

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 NPC261253 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	206
0.1-0.2	2002
0.2-0.3	3979
0.3-0.4	2003
0.4-0.5	549
0.5-0.6	280
0.6-0.7	114
0.7-0.8	17
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
0.7727	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD1695	Approved
0.7634	Intermediate Similarity	NPD6698	Approved
0.7634	Intermediate Similarity	NPD5785	Approved
0.7634	Intermediate Similarity	NPD46	Approved
0.7629	Intermediate Similarity	NPD7638	Approved
0.7582	Intermediate Similarity	NPD6409	Approved
0.7582	Intermediate Similarity	NPD7146	Approved
0.7582	Intermediate Similarity	NPD6684	Approved
0.7582	Intermediate Similarity	NPD5330	Approved
0.7582	Intermediate Similarity	NPD7521	Approved
0.7582	Intermediate Similarity	NPD7334	Approved
0.7551	Intermediate Similarity	NPD7640	Approved
0.7551	Intermediate Similarity	NPD7639	Approved
0.7528	Intermediate Similarity	NPD5209	Approved
0.75	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD1694	Approved
0.7471	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD5737	Approved
0.7419	Intermediate Similarity	NPD6672	Approved
0.7419	Intermediate Similarity	NPD6903	Approved
0.7404	Intermediate Similarity	NPD6371	Approved
0.7368	Intermediate Similarity	NPD5693	Phase 1
0.7353	Intermediate Similarity	NPD6008	Approved
0.7158	Intermediate Similarity	NPD6904	Approved
0.7158	Intermediate Similarity	NPD6080	Approved
0.7158	Intermediate Similarity	NPD6673	Approved
0.7143	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD8039	Approved
0.7115	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5363	Approved
0.7083	Intermediate Similarity	NPD7838	Discovery
0.7065	Intermediate Similarity	NPD5362	Discontinued
0.7048	Intermediate Similarity	NPD6686	Approved
0.7033	Intermediate Similarity	NPD5369	Approved
0.701	Intermediate Similarity	NPD6050	Approved
0.7	Intermediate Similarity	NPD7115	Discovery
0.7	Intermediate Similarity	NPD6083	Phase 2
0.7	Intermediate Similarity	NPD6084	Phase 2
0.6979	Remote Similarity	NPD6051	Approved
0.697	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5695	Phase 3
0.6957	Remote Similarity	NPD4269	Approved
0.6957	Remote Similarity	NPD4270	Approved
0.6957	Remote Similarity	NPD6435	Approved
0.6952	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD6053	Discontinued
0.6939	Remote Similarity	NPD6399	Phase 3
0.6915	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD5692	Phase 3
0.6893	Remote Similarity	NPD7632	Discontinued
0.6882	Remote Similarity	NPD7154	Phase 3
0.6875	Remote Similarity	NPD5208	Approved
0.6869	Remote Similarity	NPD5282	Discontinued
0.6842	Remote Similarity	NPD5786	Approved
0.6842	Remote Similarity	NPD6098	Approved
0.6837	Remote Similarity	NPD5694	Approved
0.6822	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD4250	Approved
0.6771	Remote Similarity	NPD4251	Approved
0.6765	Remote Similarity	NPD5696	Approved
0.6759	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD4822	Approved
0.6739	Remote Similarity	NPD5368	Approved
0.6739	Remote Similarity	NPD4819	Approved
0.6739	Remote Similarity	NPD4821	Approved
0.6739	Remote Similarity	NPD4252	Approved
0.6739	Remote Similarity	NPD4820	Approved
0.6739	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5207	Approved
0.67	Remote Similarity	NPD6001	Approved
0.67	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.67	Remote Similarity	NPD7900	Approved
0.67	Remote Similarity	NPD7748	Approved
0.6699	Remote Similarity	NPD6648	Approved
0.6698	Remote Similarity	NPD6675	Approved
0.6698	Remote Similarity	NPD7128	Approved
0.6698	Remote Similarity	NPD6402	Approved
0.6698	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD4249	Approved
0.6667	Remote Similarity	NPD7637	Suspended
0.6636	Remote Similarity	NPD6412	Phase 2
0.6635	Remote Similarity	NPD5344	Discontinued
0.6632	Remote Similarity	NPD3665	Phase 1
0.6632	Remote Similarity	NPD3666	Approved
0.6632	Remote Similarity	NPD3133	Approved
0.66	Remote Similarity	NPD5778	Approved
0.66	Remote Similarity	NPD5779	Approved
0.6574	Remote Similarity	NPD6899	Approved
0.6574	Remote Similarity	NPD7320	Approved
0.6574	Remote Similarity	NPD6881	Approved
0.6526	Remote Similarity	NPD5332	Approved
0.6526	Remote Similarity	NPD5331	Approved
0.6525	Remote Similarity	NPD7507	Approved
0.6522	Remote Similarity	NPD4271	Approved
0.6522	Remote Similarity	NPD4268	Approved
0.6514	Remote Similarity	NPD6372	Approved
0.6514	Remote Similarity	NPD6373	Approved
0.6505	Remote Similarity	NPD5959	Approved
0.6505	Remote Similarity	NPD7902	Approved
0.65	Remote Similarity	NPD5281	Approved
0.65	Remote Similarity	NPD5284	Approved
0.65	Remote Similarity	NPD7515	Phase 2
0.65	Remote Similarity	NPD7983	Approved
0.6495	Remote Similarity	NPD3618	Phase 1
0.6495	Remote Similarity	NPD5279	Phase 3
0.6489	Remote Similarity	NPD4790	Discontinued
0.6481	Remote Similarity	NPD5697	Approved
0.6481	Remote Similarity	NPD5701	Approved
0.6471	Remote Similarity	NPD5654	Approved
0.6465	Remote Similarity	NPD4753	Phase 2
0.6465	Remote Similarity	NPD5328	Approved
0.6458	Remote Similarity	NPD4786	Approved
0.6458	Remote Similarity	NPD3668	Phase 3
0.6455	Remote Similarity	NPD7290	Approved
0.6455	Remote Similarity	NPD6883	Approved
0.6455	Remote Similarity	NPD7102	Approved
0.6442	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD4225	Approved
0.6429	Remote Similarity	NPD4632	Approved
0.6429	Remote Similarity	NPD3573	Approved
0.6422	Remote Similarity	NPD6011	Approved
0.6421	Remote Similarity	NPD3667	Approved
0.6421	Remote Similarity	NPD4223	Phase 3
0.6421	Remote Similarity	NPD4221	Approved
0.6396	Remote Similarity	NPD6650	Approved
0.6396	Remote Similarity	NPD8130	Phase 1
0.6396	Remote Similarity	NPD6617	Approved
0.6396	Remote Similarity	NPD6649	Approved
0.6396	Remote Similarity	NPD6847	Approved
0.6396	Remote Similarity	NPD6869	Approved
0.6396	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD5329	Approved
0.6364	Remote Similarity	NPD6012	Approved
0.6364	Remote Similarity	NPD7319	Approved
0.6364	Remote Similarity	NPD6014	Approved
0.6364	Remote Similarity	NPD6013	Approved
0.6356	Remote Similarity	NPD7604	Phase 2
0.6355	Remote Similarity	NPD6052	Approved
0.6354	Remote Similarity	NPD6695	Phase 3
0.6339	Remote Similarity	NPD8297	Approved
0.6339	Remote Similarity	NPD6882	Approved
0.6337	Remote Similarity	NPD6079	Approved
0.6337	Remote Similarity	NPD6411	Approved
0.6289	Remote Similarity	NPD4197	Approved
0.6289	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD4202	Approved
0.6261	Remote Similarity	NPD6009	Approved
0.626	Remote Similarity	NPD7260	Phase 2
0.625	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6319	Approved
0.6207	Remote Similarity	NPD7328	Approved
0.6207	Remote Similarity	NPD7327	Approved
0.6207	Remote Similarity	NPD7331	Phase 2
0.619	Remote Similarity	NPD4755	Approved
0.6186	Remote Similarity	NPD5983	Phase 2
0.6182	Remote Similarity	NPD6614	Approved
0.618	Remote Similarity	NPD4137	Phase 3
0.6176	Remote Similarity	NPD8034	Phase 2
0.6176	Remote Similarity	NPD8035	Phase 2
0.6167	Remote Similarity	NPD7492	Approved
0.6163	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD5690	Phase 2
0.6162	Remote Similarity	NPD4689	Approved
0.6162	Remote Similarity	NPD4138	Approved
0.6162	Remote Similarity	NPD4688	Approved
0.6162	Remote Similarity	NPD5205	Approved
0.6162	Remote Similarity	NPD5280	Approved
0.6162	Remote Similarity	NPD4690	Approved
0.6162	Remote Similarity	NPD4693	Phase 3
0.6162	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD4694	Approved
0.6162	Remote Similarity	NPD4623	Approved
0.6162	Remote Similarity	NPD4519	Discontinued
0.6154	Remote Similarity	NPD5210	Approved
0.6154	Remote Similarity	NPD7516	Approved
0.6154	Remote Similarity	NPD4629	Approved
0.6139	Remote Similarity	NPD6101	Approved
0.6139	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD6336	Discontinued
0.6116	Remote Similarity	NPD6616	Approved
0.6111	Remote Similarity	NPD5211	Phase 2
0.6111	Remote Similarity	NPD4747	Approved
0.6111	Remote Similarity	NPD4691	Approved
0.6102	Remote Similarity	NPD8377	Approved
0.6102	Remote Similarity	NPD6054	Approved
0.6102	Remote Similarity	NPD6059	Approved
0.6102	Remote Similarity	NPD8294	Approved
0.61	Remote Similarity	NPD7750	Discontinued
0.61	Remote Similarity	NPD7524	Approved
0.6095	Remote Similarity	NPD5222	Approved
0.6095	Remote Similarity	NPD7839	Suspended
0.6095	Remote Similarity	NPD4697	Phase 3
0.6095	Remote Similarity	NPD5221	Approved
0.6095	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD7341	Phase 2
0.6087	Remote Similarity	NPD5733	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