NPASS Compound

Structure

NPC475947 OpenBabel07101718232D 30 31 0 0 1 0 0 0 0 0999 V2000 -13.3540 1.1726 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6386 -1.6637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5408 -1.9771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0122 3.1579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3431 2.4147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9904 2.9499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3649 2.6226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6595 3.6931 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6958 1.8795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6376 3.4852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7177 2.0874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3068 4.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0485 1.3443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2849 4.0204 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0704 1.5522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.5450 2.7603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.5450 1.7603 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7431 -0.6691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6272 -1.5704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.5939 3.0694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6092 -0.1691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.0062 2.2603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8182 -2.1582 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.0062 2.2603 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0933 1.7796 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.5939 1.4513 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 -2.5227 -0.5759 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 19 1 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 13 15 1 0 0 0 0 14 20 1 0 0 0 0 16 17 1 0 0 0 0 16 20 2 0 0 0 0 17 1 1 1 0 0 0 17 28 1 0 0 0 0 18 2 1 1 0 0 0 18 22 1 0 0 0 0 18 29 1 0 0 0 0 19 25 2 0 0 0 0 19 30 1 0 0 0 0 20 23 1 0 0 0 0 21 15 1 1 0 0 0 21 22 1 0 0 0 0 21 24 1 0 0 0 0 22 30 1 1 0 0 0 23 26 2 0 0 0 0 23 28 1 0 0 0 0 24 27 2 0 0 0 0 24 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	422.27
Volume:	448.743
LogP:	6.741
LogD:	4.272
LogS:	-3.964
# Rotatable Bonds:	15
TPSA:	85.97
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.309
Synthetic Accessibility Score:	3.725
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.834
MDCK Permeability:	2.5624794943723828e-05
Pgp-inhibitor:	0.933
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.271
Plasma Protein Binding (PPB):	97.12678527832031%
Volume Distribution (VD):	1.956
Pgp-substrate:	2.6819684505462646%

ADMET: Metabolism

CYP1A2-inhibitor:	0.501
CYP1A2-substrate:	0.137
CYP2C19-inhibitor:	0.392
CYP2C19-substrate:	0.072
CYP2C9-inhibitor:	0.34
CYP2C9-substrate:	0.948
CYP2D6-inhibitor:	0.913
CYP2D6-substrate:	0.202
CYP3A4-inhibitor:	0.868
CYP3A4-substrate:	0.179

ADMET: Excretion

Clearance (CL):	3.934
Half-life (T1/2):	0.23

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.706
Drug-inuced Liver Injury (DILI):	0.875
AMES Toxicity:	0.029
Rat Oral Acute Toxicity:	0.155
Maximum Recommended Daily Dose:	0.036
Skin Sensitization:	0.935
Carcinogencity:	0.068
Eye Corrosion:	0.161
Eye Irritation:	0.132
Respiratory Toxicity:	0.734

Download Data

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

Natural Product: NPC475947

Natural Product ID:	NPC475947
*Common Name:**	Ancepsenolide Acetate
IUPAC Name:	[(2S,3S,4R)-2-methyl-4-[12-[(2S)-2-methyl-5-oxo-2H-furan-4-yl]dodecyl]-5-oxooxolan-3-yl] acetate
Synonyms:	Ancepsenolide Acetate
Standard InCHIKey:	FXNASNSEMIBZQX-MOXQZVSFSA-N
Standard InCHI:	InChI=1S/C24H38O6/c1-17-16-20(23(26)28-17)14-12-10-8-6-4-5-7-9-11-13-15-21-22(30-19(3)25)18(2)29-24(21)27/h16-18,21-22H,4-15H2,1-3H3/t17-,18-,21+,22+/m0/s1
SMILES:	CC1C=C(C(=O)O1)CCCCCCCCCCCCC2C(C(OC2=O)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL519309
PubChem CID:	23427796
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols [CHEMONTID:0002518] Annonaceous acetogenins

*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
NPO1816	Pterogorgia citrina	Species	Gorgoniidae	Eukaryota	n.a.	Caribbean	n.a.	PMID[7911157]
NPO1816	Pterogorgia citrina	Species	Gorgoniidae	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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[528517]

☑ 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 NPC475947 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	194
0.1-0.2	1247
0.2-0.3	5661
0.3-0.4	13562
0.4-0.5	11273
0.5-0.6	6788
0.6-0.7	2893
0.7-0.8	947
0.8-0.85	117
0.85-0.9	14
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9146	High Similarity	NPC469483
0.8846	High Similarity	NPC123360
0.8765	High Similarity	NPC471325
0.8659	High Similarity	NPC173609
0.8625	High Similarity	NPC128276
0.859	High Similarity	NPC476355
0.859	High Similarity	NPC140287
0.8519	High Similarity	NPC178277
0.85	High Similarity	NPC57744
0.85	High Similarity	NPC97516
0.8488	Intermediate Similarity	NPC475906
0.8488	Intermediate Similarity	NPC469653
0.8488	Intermediate Similarity	NPC471047
0.8488	Intermediate Similarity	NPC469631
0.8488	Intermediate Similarity	NPC469628
0.8434	Intermediate Similarity	NPC475690
0.8415	Intermediate Similarity	NPC223904
0.8354	Intermediate Similarity	NPC474758
0.8333	Intermediate Similarity	NPC163003
0.8333	Intermediate Similarity	NPC318468
0.8333	Intermediate Similarity	NPC84038
0.8315	Intermediate Similarity	NPC469692
0.8315	Intermediate Similarity	NPC469645
0.8313	Intermediate Similarity	NPC281949
0.8313	Intermediate Similarity	NPC25684
0.8313	Intermediate Similarity	NPC141810
0.8313	Intermediate Similarity	NPC301477
0.8293	Intermediate Similarity	NPC270126
0.8272	Intermediate Similarity	NPC141789
0.8272	Intermediate Similarity	NPC41780
0.8272	Intermediate Similarity	NPC474760
0.8272	Intermediate Similarity	NPC187568
0.8272	Intermediate Similarity	NPC171204
0.8272	Intermediate Similarity	NPC476794
0.8272	Intermediate Similarity	NPC476028
0.8272	Intermediate Similarity	NPC470240
0.8256	Intermediate Similarity	NPC279859
0.8256	Intermediate Similarity	NPC284902
0.8256	Intermediate Similarity	NPC107787
0.8256	Intermediate Similarity	NPC38576
0.825	Intermediate Similarity	NPC469414
0.825	Intermediate Similarity	NPC329826
0.8235	Intermediate Similarity	NPC115786
0.8228	Intermediate Similarity	NPC474705
0.8222	Intermediate Similarity	NPC476267
0.8222	Intermediate Similarity	NPC473316
0.8222	Intermediate Similarity	NPC121825
0.8222	Intermediate Similarity	NPC473330
0.8222	Intermediate Similarity	NPC140543
0.8202	Intermediate Similarity	NPC284185
0.8193	Intermediate Similarity	NPC281132
0.8171	Intermediate Similarity	NPC108816
0.8171	Intermediate Similarity	NPC93763
0.8161	Intermediate Similarity	NPC266957
0.8161	Intermediate Similarity	NPC475703
0.8148	Intermediate Similarity	NPC235906
0.814	Intermediate Similarity	NPC470755
0.814	Intermediate Similarity	NPC78089
0.814	Intermediate Similarity	NPC215364
0.8125	Intermediate Similarity	NPC15499
0.8125	Intermediate Similarity	NPC259599
0.8125	Intermediate Similarity	NPC117746
0.8125	Intermediate Similarity	NPC294434
0.8095	Intermediate Similarity	NPC42470
0.809	Intermediate Similarity	NPC475748
0.809	Intermediate Similarity	NPC80875
0.809	Intermediate Similarity	NPC253144
0.8072	Intermediate Similarity	NPC617
0.8072	Intermediate Similarity	NPC473980
0.8072	Intermediate Similarity	NPC473981
0.8072	Intermediate Similarity	NPC19841
0.8068	Intermediate Similarity	NPC476803
0.8068	Intermediate Similarity	NPC476805
0.8068	Intermediate Similarity	NPC226863
0.8065	Intermediate Similarity	NPC208233
0.8052	Intermediate Similarity	NPC472266
0.8049	Intermediate Similarity	NPC65603
0.8046	Intermediate Similarity	NPC261721
0.8046	Intermediate Similarity	NPC305475
0.8046	Intermediate Similarity	NPC469910
0.8046	Intermediate Similarity	NPC475461
0.8043	Intermediate Similarity	NPC35498
0.8025	Intermediate Similarity	NPC193351
0.8025	Intermediate Similarity	NPC155587
0.8025	Intermediate Similarity	NPC226669
0.8025	Intermediate Similarity	NPC244166
0.8025	Intermediate Similarity	NPC138408
0.8023	Intermediate Similarity	NPC158756
0.8023	Intermediate Similarity	NPC163093
0.8023	Intermediate Similarity	NPC41856
0.8022	Intermediate Similarity	NPC471147
0.8022	Intermediate Similarity	NPC469632
0.8	Intermediate Similarity	NPC11332
0.8	Intermediate Similarity	NPC85772
0.8	Intermediate Similarity	NPC269206
0.8	Intermediate Similarity	NPC475159
0.8	Intermediate Similarity	NPC261607
0.8	Intermediate Similarity	NPC150978
0.8	Intermediate Similarity	NPC58956
0.8	Intermediate Similarity	NPC473712
0.8	Intermediate Similarity	NPC300312
0.8	Intermediate Similarity	NPC473529
0.8	Intermediate Similarity	NPC473780
0.8	Intermediate Similarity	NPC145914
0.8	Intermediate Similarity	NPC123177
0.8	Intermediate Similarity	NPC73310
0.8	Intermediate Similarity	NPC180363
0.8	Intermediate Similarity	NPC65930
0.8	Intermediate Similarity	NPC329829
0.8	Intermediate Similarity	NPC295633
0.8	Intermediate Similarity	NPC94875
0.8	Intermediate Similarity	NPC74103
0.8	Intermediate Similarity	NPC35556
0.8	Intermediate Similarity	NPC111114
0.8	Intermediate Similarity	NPC131002
0.8	Intermediate Similarity	NPC70595
0.7978	Intermediate Similarity	NPC130359
0.7978	Intermediate Similarity	NPC14901
0.7978	Intermediate Similarity	NPC295312
0.7976	Intermediate Similarity	NPC302426
0.7955	Intermediate Similarity	NPC72513
0.7955	Intermediate Similarity	NPC178215
0.7955	Intermediate Similarity	NPC231889
0.7955	Intermediate Similarity	NPC160138
0.7952	Intermediate Similarity	NPC11796
0.7952	Intermediate Similarity	NPC299235
0.7952	Intermediate Similarity	NPC475699
0.7952	Intermediate Similarity	NPC218817
0.7949	Intermediate Similarity	NPC218477
0.7935	Intermediate Similarity	NPC475659
0.7931	Intermediate Similarity	NPC231009
0.7931	Intermediate Similarity	NPC477014
0.7931	Intermediate Similarity	NPC107986
0.7931	Intermediate Similarity	NPC477013
0.7931	Intermediate Similarity	NPC197903
0.7931	Intermediate Similarity	NPC223871
0.7931	Intermediate Similarity	NPC82795
0.7931	Intermediate Similarity	NPC473478
0.7931	Intermediate Similarity	NPC473651
0.7931	Intermediate Similarity	NPC471567
0.7931	Intermediate Similarity	NPC1083
0.7931	Intermediate Similarity	NPC125290
0.7931	Intermediate Similarity	NPC66346
0.7931	Intermediate Similarity	NPC473669
0.7931	Intermediate Similarity	NPC103284
0.7931	Intermediate Similarity	NPC33570
0.7931	Intermediate Similarity	NPC120398
0.7931	Intermediate Similarity	NPC110710
0.7931	Intermediate Similarity	NPC255307
0.7931	Intermediate Similarity	NPC99395
0.7931	Intermediate Similarity	NPC283085
0.7931	Intermediate Similarity	NPC132496
0.7931	Intermediate Similarity	NPC21471
0.7931	Intermediate Similarity	NPC286338
0.7912	Intermediate Similarity	NPC165383
0.7912	Intermediate Similarity	NPC476300
0.7907	Intermediate Similarity	NPC40746
0.7907	Intermediate Similarity	NPC144415
0.7907	Intermediate Similarity	NPC170286
0.7907	Intermediate Similarity	NPC215294
0.7907	Intermediate Similarity	NPC475989
0.7907	Intermediate Similarity	NPC169575
0.7907	Intermediate Similarity	NPC253801
0.7901	Intermediate Similarity	NPC474551
0.7895	Intermediate Similarity	NPC185141
0.7895	Intermediate Similarity	NPC46998
0.7895	Intermediate Similarity	NPC133907
0.7895	Intermediate Similarity	NPC110443
0.7895	Intermediate Similarity	NPC128733
0.7889	Intermediate Similarity	NPC473448
0.7889	Intermediate Similarity	NPC474232
0.7889	Intermediate Similarity	NPC51004
0.7889	Intermediate Similarity	NPC312042
0.7882	Intermediate Similarity	NPC475481
0.7882	Intermediate Similarity	NPC79277
0.7875	Intermediate Similarity	NPC129665
0.7865	Intermediate Similarity	NPC233551
0.7865	Intermediate Similarity	NPC21208
0.7865	Intermediate Similarity	NPC475902
0.7865	Intermediate Similarity	NPC48338
0.7865	Intermediate Similarity	NPC20339
0.7865	Intermediate Similarity	NPC40376
0.7865	Intermediate Similarity	NPC475819
0.7865	Intermediate Similarity	NPC280621
0.7857	Intermediate Similarity	NPC472965
0.7857	Intermediate Similarity	NPC99651
0.7857	Intermediate Similarity	NPC471299
0.7857	Intermediate Similarity	NPC182550
0.7857	Intermediate Similarity	NPC264227
0.7857	Intermediate Similarity	NPC63649
0.7849	Intermediate Similarity	NPC473859
0.7841	Intermediate Similarity	NPC134885
0.7841	Intermediate Similarity	NPC171174
0.7841	Intermediate Similarity	NPC204686
0.7841	Intermediate Similarity	NPC114694
0.7841	Intermediate Similarity	NPC142117
0.7841	Intermediate Similarity	NPC134865
0.7841	Intermediate Similarity	NPC279267
0.7841	Intermediate Similarity	NPC62118
0.7841	Intermediate Similarity	NPC112685

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 NPC475947 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	1839
0.2-0.3	3964
0.3-0.4	2157
0.4-0.5	655
0.5-0.6	291
0.6-0.7	52
0.7-0.8	15
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	NPD1733	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5785	Approved
0.75	Intermediate Similarity	NPD46	Approved
0.75	Intermediate Similarity	NPD6698	Approved
0.7386	Intermediate Similarity	NPD5209	Approved
0.7333	Intermediate Similarity	NPD5363	Approved
0.7333	Intermediate Similarity	NPD1694	Approved
0.732	Intermediate Similarity	NPD4225	Approved
0.7204	Intermediate Similarity	NPD1695	Approved
0.7125	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6371	Approved
0.7111	Intermediate Similarity	NPD7154	Phase 3
0.7053	Intermediate Similarity	NPD7983	Approved
0.7	Intermediate Similarity	NPD4269	Approved
0.7	Intermediate Similarity	NPD4270	Approved
0.6977	Remote Similarity	NPD8039	Approved
0.6957	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD7838	Discovery
0.6923	Remote Similarity	NPD5362	Discontinued
0.6923	Remote Similarity	NPD6686	Approved
0.6889	Remote Similarity	NPD5369	Approved
0.6882	Remote Similarity	NPD5786	Approved
0.6778	Remote Similarity	NPD4252	Approved
0.6727	Remote Similarity	NPD7115	Discovery
0.6634	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD5778	Approved
0.6633	Remote Similarity	NPD5779	Approved
0.663	Remote Similarity	NPD6435	Approved
0.6593	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD5282	Discontinued
0.6562	Remote Similarity	NPD6903	Approved
0.6556	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD5330	Approved
0.6526	Remote Similarity	NPD7146	Approved
0.6526	Remote Similarity	NPD7334	Approved
0.6526	Remote Similarity	NPD6684	Approved
0.6526	Remote Similarity	NPD6409	Approved
0.6526	Remote Similarity	NPD7521	Approved
0.6495	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD6101	Approved
0.6489	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD4251	Approved
0.6458	Remote Similarity	NPD4250	Approved
0.6436	Remote Similarity	NPD7839	Suspended
0.6422	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD4820	Approved
0.6413	Remote Similarity	NPD5368	Approved
0.6413	Remote Similarity	NPD4822	Approved
0.6413	Remote Similarity	NPD4819	Approved
0.6413	Remote Similarity	NPD4821	Approved
0.6392	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD5737	Approved
0.6392	Remote Similarity	NPD6672	Approved
0.6383	Remote Similarity	NPD5331	Approved
0.6383	Remote Similarity	NPD5332	Approved
0.6374	Remote Similarity	NPD4268	Approved
0.6374	Remote Similarity	NPD4271	Approved
0.6364	Remote Similarity	NPD6411	Approved
0.6355	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD4249	Approved
0.6344	Remote Similarity	NPD4790	Discontinued
0.6337	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.633	Remote Similarity	NPD2067	Discontinued
0.6327	Remote Similarity	NPD5370	Suspended
0.6311	Remote Similarity	NPD7638	Approved
0.625	Remote Similarity	NPD6648	Approved
0.625	Remote Similarity	NPD7640	Approved
0.625	Remote Similarity	NPD7639	Approved
0.6238	Remote Similarity	NPD7900	Approved
0.6238	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD6053	Discontinued
0.6207	Remote Similarity	NPD8517	Approved
0.6207	Remote Similarity	NPD8516	Approved
0.6207	Remote Similarity	NPD8515	Approved
0.6207	Remote Similarity	NPD8513	Phase 3
0.62	Remote Similarity	NPD5693	Phase 1
0.62	Remote Similarity	NPD7637	Suspended
0.62	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5344	Discontinued
0.6182	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD6399	Phase 3
0.6116	Remote Similarity	NPD7319	Approved
0.6105	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6104	Remote Similarity	NPD6927	Phase 3
0.61	Remote Similarity	NPD5207	Approved
0.6091	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD4756	Discovery
0.6078	Remote Similarity	NPD7748	Approved
0.6058	Remote Similarity	NPD6083	Phase 2
0.6058	Remote Similarity	NPD6084	Phase 2
0.6058	Remote Similarity	NPD7902	Approved
0.6047	Remote Similarity	NPD7331	Phase 2
0.602	Remote Similarity	NPD6422	Discontinued
0.6019	Remote Similarity	NPD5695	Phase 3
0.6	Remote Similarity	NPD6080	Approved
0.6	Remote Similarity	NPD6673	Approved
0.6	Remote Similarity	NPD5696	Approved
0.6	Remote Similarity	NPD6051	Approved
0.6	Remote Similarity	NPD6904	Approved
0.6	Remote Similarity	NPD7507	Approved
0.6	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3197	Phase 1
0.5982	Remote Similarity	NPD2204	Approved
0.5982	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD7642	Approved
0.5966	Remote Similarity	NPD7830	Approved
0.5966	Remote Similarity	NPD7829	Approved
0.5963	Remote Similarity	NPD6008	Approved
0.595	Remote Similarity	NPD8074	Phase 3
0.5929	Remote Similarity	NPD8297	Approved
0.5922	Remote Similarity	NPD6001	Approved
0.5917	Remote Similarity	NPD7492	Approved
0.5906	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD28	Approved
0.5897	Remote Similarity	NPD29	Approved
0.5882	Remote Similarity	NPD6050	Approved
0.5882	Remote Similarity	NPD7515	Phase 2
0.5876	Remote Similarity	NPD6110	Phase 1
0.5868	Remote Similarity	NPD6616	Approved
0.5862	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD7500	Approved
0.5856	Remote Similarity	NPD6881	Approved
0.5856	Remote Similarity	NPD6899	Approved
0.5856	Remote Similarity	NPD7320	Approved
0.5851	Remote Similarity	NPD3732	Approved
0.5847	Remote Similarity	NPD6054	Approved
0.5841	Remote Similarity	NPD6649	Approved
0.5841	Remote Similarity	NPD6650	Approved
0.5841	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.582	Remote Similarity	NPD7078	Approved
0.5818	Remote Similarity	NPD6675	Approved
0.5818	Remote Similarity	NPD7128	Approved
0.5818	Remote Similarity	NPD5739	Approved
0.5818	Remote Similarity	NPD6402	Approved
0.581	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD6373	Approved
0.5804	Remote Similarity	NPD6372	Approved
0.58	Remote Similarity	NPD3573	Approved
0.5784	Remote Similarity	NPD5692	Phase 3
0.578	Remote Similarity	NPD6647	Phase 2
0.578	Remote Similarity	NPD6052	Approved
0.5772	Remote Similarity	NPD7736	Approved
0.5766	Remote Similarity	NPD6412	Phase 2
0.5766	Remote Similarity	NPD5697	Approved
0.5752	Remote Similarity	NPD7102	Approved
0.5752	Remote Similarity	NPD6883	Approved
0.5752	Remote Similarity	NPD7290	Approved
0.575	Remote Similarity	NPD6370	Approved
0.5747	Remote Similarity	NPD7341	Phase 2
0.5747	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD5208	Approved
0.573	Remote Similarity	NPD229	Approved
0.5728	Remote Similarity	NPD5694	Approved
0.5726	Remote Similarity	NPD7505	Discontinued
0.5714	Remote Similarity	NPD6059	Approved
0.5714	Remote Similarity	NPD6125	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6319	Approved
0.5702	Remote Similarity	NPD6847	Approved
0.5702	Remote Similarity	NPD6617	Approved
0.5702	Remote Similarity	NPD6869	Approved
0.5702	Remote Similarity	NPD8130	Phase 1
0.57	Remote Similarity	NPD3618	Phase 1
0.57	Remote Similarity	NPD6098	Approved
0.57	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5691	Remote Similarity	NPD8293	Discontinued
0.5688	Remote Similarity	NPD7632	Discontinued
0.5679	Remote Similarity	NPD3196	Approved
0.5679	Remote Similarity	NPD3195	Phase 2
0.5679	Remote Similarity	NPD4266	Approved
0.5679	Remote Similarity	NPD3194	Approved
0.5678	Remote Similarity	NPD7327	Approved
0.5678	Remote Similarity	NPD7328	Approved
0.5678	Remote Similarity	NPD7641	Discontinued
0.5673	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD6015	Approved
0.5667	Remote Similarity	NPD8444	Approved
0.5667	Remote Similarity	NPD6016	Approved
0.5664	Remote Similarity	NPD6012	Approved
0.5664	Remote Similarity	NPD6013	Approved
0.5664	Remote Similarity	NPD6413	Approved
0.5664	Remote Similarity	NPD6014	Approved
0.566	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD3133	Approved
0.5657	Remote Similarity	NPD3665	Phase 1
0.5657	Remote Similarity	NPD3666	Approved
0.5652	Remote Similarity	NPD6882	Approved
0.5647	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5645	Remote Similarity	NPD8336	Approved
0.5645	Remote Similarity	NPD8337	Approved
0.5635	Remote Similarity	NPD7260	Phase 2
0.563	Remote Similarity	NPD7516	Approved
0.5625	Remote Similarity	NPD5701	Approved
0.562	Remote Similarity	NPD5988	Approved
0.561	Remote Similarity	NPD8451	Approved
0.561	Remote Similarity	NPD8273	Phase 1

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