NPASS Compound

Structure

CID324762 OpenBabel06191716172D 26 27 0 0 1 0 0 0 0 0999 V2000 6.0246 3.3371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5387 1.7549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8115 -0.2156 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2840 2.4467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6217 1.3129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7116 1.1612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0344 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9113 2.1008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2178 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7981 0.8644 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5541 1.8270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5541 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6637 2.7405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8249 2.3976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0344 0.3489 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0843 1.5071 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9185 2.2264 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9605 1.8270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9605 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2573 0.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4803 1.4781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2968 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8581 2.4261 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2103 1.2103 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2758 2.9402 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 5 17 1 0 0 0 0 6 8 1 0 0 0 0 6 10 1 0 0 0 0 7 9 1 0 0 0 0 7 11 1 0 0 0 0 8 14 2 0 0 0 0 9 15 2 0 0 0 0 10 16 1 0 0 0 0 11 18 1 0 0 0 0 12 15 1 0 0 0 0 13 18 2 0 0 0 0 13 25 1 0 0 0 0 16 4 1 1 0 0 0 17 23 2 0 0 0 0 17 25 1 0 0 0 0 19 12 1 6 0 0 0 19 20 1 0 0 0 0 19 26 1 0 0 0 0 20 16 1 1 0 0 0 20 21 1 0 0 0 0 21 18 1 6 0 0 0 21 22 1 0 0 0 0 22 24 2 0 0 0 0 22 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	360.23
Volume:	393.934
LogP:	5.248
LogD:	4.33
LogS:	-4.258
# Rotatable Bonds:	6
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.389
Synthetic Accessibility Score:	5.769
Fsp3:	0.636
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.727
MDCK Permeability:	3.6062076105736196e-05
Pgp-inhibitor:	0.985
Pgp-substrate:	0.062
Human Intestinal Absorption (HIA):	0.043
20% Bioavailability (F20%):	0.727
30% Bioavailability (F30%):	0.698

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.973
Plasma Protein Binding (PPB):	87.48233795166016%
Volume Distribution (VD):	1.132
Pgp-substrate:	15.712621688842773%

ADMET: Metabolism

CYP1A2-inhibitor:	0.334
CYP1A2-substrate:	0.052
CYP2C19-inhibitor:	0.285
CYP2C19-substrate:	0.433
CYP2C9-inhibitor:	0.285
CYP2C9-substrate:	0.078
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.06
CYP3A4-inhibitor:	0.718
CYP3A4-substrate:	0.307

ADMET: Excretion

Clearance (CL):	4.487
Half-life (T1/2):	0.391

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.937
Drug-inuced Liver Injury (DILI):	0.698
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.069
Maximum Recommended Daily Dose:	0.748
Skin Sensitization:	0.956
Carcinogencity:	0.31
Eye Corrosion:	0.013
Eye Irritation:	0.121
Respiratory Toxicity:	0.877

Download Data

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

Natural Product: NPC324762

Natural Product ID:	NPC324762
*Common Name:**	Dilopholide
IUPAC Name:	[(Z)-[(1S,3E,8S,11R)-3-methyl-11-[(2S)-6-methylhept-5-en-2-yl]-9-oxo-10-oxabicyclo[6.2.1]undec-3-en-7-ylidene]methyl] acetate
Synonyms:	Dilopholide
Standard InCHIKey:	DFKHRBLZEJCJLU-ZBXWVNBDSA-N
Standard InCHI:	InChI=1S/C22H32O4/c1-14(2)8-6-10-16(4)20-19-12-15(3)9-7-11-18(13-25-17(5)23)21(20)22(24)26-19/h8-9,13,16,19-21H,6-7,10-12H2,1-5H3/b15-9+,18-13-/t16-,19-,20-,21+/m0/s1
SMILES:	CC(=CCC[C@@H]([C@H]1[C@@H]2C/C(=C/CC/C(=C/OC(=O)C)/[C@H]1C(=O)O2)/C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL515304
PubChem CID:	44584504
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001245] Gamma butyrolactones

*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
NPO29273	Dilophus ligulatus	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8277314]
NPO29273	Dilophus ligulatus	Species	Dictyotaceae	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
ED50	4

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	1.5	ug ml-1	PMID[513026]
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.5	ug ml-1	PMID[513026]
NPT168	Cell Line	P388	Mus musculus	ED50	=	12.0	ug ml-1	PMID[513026]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	3.3	ug ml-1	PMID[513026]

☑ 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 NPC324762 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	181
0.1-0.2	1196
0.2-0.3	6274
0.3-0.4	16691
0.4-0.5	8937
0.5-0.6	6680
0.6-0.7	2364
0.7-0.8	349
0.8-0.85	19
0.85-0.9	5
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8873	High Similarity	NPC472955
0.8472	Intermediate Similarity	NPC144511
0.8472	Intermediate Similarity	NPC296522
0.8472	Intermediate Similarity	NPC199557
0.8289	Intermediate Similarity	NPC474527
0.8289	Intermediate Similarity	NPC471726
0.8267	Intermediate Similarity	NPC140287
0.8182	Intermediate Similarity	NPC470240
0.8182	Intermediate Similarity	NPC476794
0.8108	Intermediate Similarity	NPC475310
0.8026	Intermediate Similarity	NPC476355
0.8026	Intermediate Similarity	NPC472966
0.8025	Intermediate Similarity	NPC52609
0.8025	Intermediate Similarity	NPC1761
0.8	Intermediate Similarity	NPC129665
0.8	Intermediate Similarity	NPC39411
0.8	Intermediate Similarity	NPC255580
0.8	Intermediate Similarity	NPC163003
0.8	Intermediate Similarity	NPC471325
0.7949	Intermediate Similarity	NPC97516
0.7949	Intermediate Similarity	NPC195785
0.7949	Intermediate Similarity	NPC15975
0.7922	Intermediate Similarity	NPC475861
0.7922	Intermediate Similarity	NPC226669
0.7922	Intermediate Similarity	NPC193351
0.7922	Intermediate Similarity	NPC138408
0.7922	Intermediate Similarity	NPC155587
0.7895	Intermediate Similarity	NPC472956
0.7895	Intermediate Similarity	NPC135703
0.7848	Intermediate Similarity	NPC35574
0.7848	Intermediate Similarity	NPC128276
0.7848	Intermediate Similarity	NPC474341
0.7821	Intermediate Similarity	NPC472967
0.7821	Intermediate Similarity	NPC235906
0.7821	Intermediate Similarity	NPC266159
0.7821	Intermediate Similarity	NPC472959
0.7821	Intermediate Similarity	NPC123360
0.7778	Intermediate Similarity	NPC281949
0.7778	Intermediate Similarity	NPC301477
0.7778	Intermediate Similarity	NPC141810
0.7778	Intermediate Similarity	NPC25684
0.775	Intermediate Similarity	NPC178277
0.775	Intermediate Similarity	NPC617
0.775	Intermediate Similarity	NPC182550
0.7733	Intermediate Similarity	NPC5714
0.7722	Intermediate Similarity	NPC187568
0.7722	Intermediate Similarity	NPC474760
0.7722	Intermediate Similarity	NPC107668
0.7722	Intermediate Similarity	NPC57744
0.7722	Intermediate Similarity	NPC171204
0.7722	Intermediate Similarity	NPC141789
0.7722	Intermediate Similarity	NPC65603
0.7722	Intermediate Similarity	NPC476028
0.7722	Intermediate Similarity	NPC41780
0.7711	Intermediate Similarity	NPC474776
0.7711	Intermediate Similarity	NPC295799
0.7711	Intermediate Similarity	NPC100391
0.7683	Intermediate Similarity	NPC173609
0.7683	Intermediate Similarity	NPC35556
0.7683	Intermediate Similarity	NPC89555
0.7662	Intermediate Similarity	NPC269206
0.7662	Intermediate Similarity	NPC58956
0.7662	Intermediate Similarity	NPC470237
0.7662	Intermediate Similarity	NPC295633
0.7654	Intermediate Similarity	NPC276356
0.7654	Intermediate Similarity	NPC304795
0.7647	Intermediate Similarity	NPC471739
0.7625	Intermediate Similarity	NPC93763
0.7625	Intermediate Similarity	NPC218817
0.7625	Intermediate Similarity	NPC11796
0.7625	Intermediate Similarity	NPC108816
0.7619	Intermediate Similarity	NPC329738
0.7619	Intermediate Similarity	NPC78089
0.7595	Intermediate Similarity	NPC12740
0.7595	Intermediate Similarity	NPC110461
0.7595	Intermediate Similarity	NPC61863
0.759	Intermediate Similarity	NPC475842
0.759	Intermediate Similarity	NPC475622
0.759	Intermediate Similarity	NPC108045
0.759	Intermediate Similarity	NPC475947
0.759	Intermediate Similarity	NPC318468
0.7564	Intermediate Similarity	NPC469641
0.7564	Intermediate Similarity	NPC474551
0.7564	Intermediate Similarity	NPC469643
0.7561	Intermediate Similarity	NPC52861
0.7561	Intermediate Similarity	NPC470241
0.7531	Intermediate Similarity	NPC470244
0.7531	Intermediate Similarity	NPC469690
0.7531	Intermediate Similarity	NPC472965
0.7531	Intermediate Similarity	NPC264227
0.7531	Intermediate Similarity	NPC469620
0.7531	Intermediate Similarity	NPC270126
0.7531	Intermediate Similarity	NPC63649
0.7531	Intermediate Similarity	NPC470239
0.7531	Intermediate Similarity	NPC89128
0.7529	Intermediate Similarity	NPC107787
0.75	Intermediate Similarity	NPC476804
0.75	Intermediate Similarity	NPC115786
0.75	Intermediate Similarity	NPC320630
0.75	Intermediate Similarity	NPC139566
0.75	Intermediate Similarity	NPC116177
0.75	Intermediate Similarity	NPC165287
0.75	Intermediate Similarity	NPC7563
0.747	Intermediate Similarity	NPC475936
0.7468	Intermediate Similarity	NPC474419
0.7468	Intermediate Similarity	NPC244166
0.7467	Intermediate Similarity	NPC194871
0.7442	Intermediate Similarity	NPC167877
0.7439	Intermediate Similarity	NPC74673
0.7439	Intermediate Similarity	NPC223904
0.7439	Intermediate Similarity	NPC200446
0.7439	Intermediate Similarity	NPC69271
0.7439	Intermediate Similarity	NPC103634
0.7439	Intermediate Similarity	NPC281132
0.7439	Intermediate Similarity	NPC302426
0.7439	Intermediate Similarity	NPC469920
0.7436	Intermediate Similarity	NPC238425
0.7436	Intermediate Similarity	NPC472018
0.7436	Intermediate Similarity	NPC167145
0.7436	Intermediate Similarity	NPC474543
0.7412	Intermediate Similarity	NPC235792
0.7412	Intermediate Similarity	NPC255307
0.7407	Intermediate Similarity	NPC472960
0.7407	Intermediate Similarity	NPC267231
0.7381	Intermediate Similarity	NPC272814
0.7381	Intermediate Similarity	NPC53867
0.7381	Intermediate Similarity	NPC475989
0.7381	Intermediate Similarity	NPC470948
0.7381	Intermediate Similarity	NPC39588
0.7381	Intermediate Similarity	NPC474703
0.7375	Intermediate Similarity	NPC41017
0.7375	Intermediate Similarity	NPC474447
0.7375	Intermediate Similarity	NPC239127
0.7375	Intermediate Similarity	NPC279537
0.7356	Intermediate Similarity	NPC477128
0.7349	Intermediate Similarity	NPC475481
0.7349	Intermediate Similarity	NPC79277
0.7349	Intermediate Similarity	NPC286229
0.7349	Intermediate Similarity	NPC207188
0.7349	Intermediate Similarity	NPC475665
0.7349	Intermediate Similarity	NPC42470
0.7342	Intermediate Similarity	NPC294434
0.7342	Intermediate Similarity	NPC474758
0.7342	Intermediate Similarity	NPC15499
0.7342	Intermediate Similarity	NPC259599
0.7342	Intermediate Similarity	NPC117746
0.7342	Intermediate Similarity	NPC330016
0.7326	Intermediate Similarity	NPC475461
0.7326	Intermediate Similarity	NPC50637
0.7326	Intermediate Similarity	NPC150755
0.7326	Intermediate Similarity	NPC305475
0.7326	Intermediate Similarity	NPC284902
0.7317	Intermediate Similarity	NPC19841
0.7317	Intermediate Similarity	NPC209995
0.7317	Intermediate Similarity	NPC158565
0.7317	Intermediate Similarity	NPC471740
0.7294	Intermediate Similarity	NPC472957
0.7294	Intermediate Similarity	NPC114979
0.7294	Intermediate Similarity	NPC191476
0.7294	Intermediate Similarity	NPC96259
0.7294	Intermediate Similarity	NPC159635
0.7294	Intermediate Similarity	NPC141193
0.7294	Intermediate Similarity	NPC472958
0.7284	Intermediate Similarity	NPC476264
0.7284	Intermediate Similarity	NPC476325
0.7273	Intermediate Similarity	NPC101622
0.7273	Intermediate Similarity	NPC307411
0.7273	Intermediate Similarity	NPC22301
0.7273	Intermediate Similarity	NPC477448
0.7273	Intermediate Similarity	NPC477449
0.7262	Intermediate Similarity	NPC7414
0.7262	Intermediate Similarity	NPC178676
0.7253	Intermediate Similarity	NPC273197
0.7253	Intermediate Similarity	NPC234339
0.725	Intermediate Similarity	NPC471491
0.725	Intermediate Similarity	NPC255060
0.7241	Intermediate Similarity	NPC475703
0.7241	Intermediate Similarity	NPC38885
0.7241	Intermediate Similarity	NPC237540
0.7241	Intermediate Similarity	NPC179659
0.7241	Intermediate Similarity	NPC74139
0.7241	Intermediate Similarity	NPC478144
0.7241	Intermediate Similarity	NPC474765
0.7241	Intermediate Similarity	NPC231889
0.7237	Intermediate Similarity	NPC469868
0.7237	Intermediate Similarity	NPC472266
0.7229	Intermediate Similarity	NPC195424
0.7222	Intermediate Similarity	NPC477615
0.7215	Intermediate Similarity	NPC107783
0.7215	Intermediate Similarity	NPC92909
0.7209	Intermediate Similarity	NPC470223
0.7209	Intermediate Similarity	NPC21471
0.7209	Intermediate Similarity	NPC125290
0.7209	Intermediate Similarity	NPC165162
0.7209	Intermediate Similarity	NPC161957
0.7209	Intermediate Similarity	NPC472686
0.7209	Intermediate Similarity	NPC474369
0.7209	Intermediate Similarity	NPC475206
0.7209	Intermediate Similarity	NPC33570
0.7209	Intermediate Similarity	NPC215364

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 NPC324762 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	164
0.1-0.2	1851
0.2-0.3	4041
0.3-0.4	2163
0.4-0.5	581
0.5-0.6	269
0.6-0.7	69
0.7-0.8	12
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
0.7805	Intermediate Similarity	NPD7154	Phase 3
0.7561	Intermediate Similarity	NPD5369	Approved
0.7381	Intermediate Similarity	NPD5362	Discontinued
0.7262	Intermediate Similarity	NPD4270	Approved
0.7262	Intermediate Similarity	NPD6435	Approved
0.7262	Intermediate Similarity	NPD4269	Approved
0.7126	Intermediate Similarity	NPD5786	Approved
0.7045	Intermediate Similarity	NPD4250	Approved
0.7045	Intermediate Similarity	NPD4251	Approved
0.7033	Intermediate Similarity	NPD6399	Phase 3
0.7024	Intermediate Similarity	NPD4252	Approved
0.7024	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD5368	Approved
0.7011	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD5363	Approved
0.6988	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD6684	Approved
0.6932	Remote Similarity	NPD7521	Approved
0.6932	Remote Similarity	NPD4249	Approved
0.6932	Remote Similarity	NPD6409	Approved
0.6932	Remote Similarity	NPD7334	Approved
0.6932	Remote Similarity	NPD7146	Approved
0.6932	Remote Similarity	NPD5330	Approved
0.6889	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD6101	Approved
0.6889	Remote Similarity	NPD1695	Approved
0.686	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD8039	Approved
0.6824	Remote Similarity	NPD4822	Approved
0.6824	Remote Similarity	NPD4820	Approved
0.6824	Remote Similarity	NPD4821	Approved
0.6824	Remote Similarity	NPD4819	Approved
0.6818	Remote Similarity	NPD1694	Approved
0.6818	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD5785	Approved
0.6786	Remote Similarity	NPD4268	Approved
0.6786	Remote Similarity	NPD4271	Approved
0.6782	Remote Similarity	NPD5331	Approved
0.6782	Remote Similarity	NPD5332	Approved
0.6778	Remote Similarity	NPD6672	Approved
0.6778	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD5737	Approved
0.6778	Remote Similarity	NPD6903	Approved
0.6774	Remote Similarity	NPD5282	Discontinued
0.6744	Remote Similarity	NPD4790	Discontinued
0.6742	Remote Similarity	NPD6422	Discontinued
0.6739	Remote Similarity	NPD6411	Approved
0.6702	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD5779	Approved
0.663	Remote Similarity	NPD6698	Approved
0.663	Remote Similarity	NPD46	Approved
0.6596	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD7900	Approved
0.6571	Remote Similarity	NPD28	Approved
0.6571	Remote Similarity	NPD29	Approved
0.6559	Remote Similarity	NPD7983	Approved
0.6538	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD5209	Approved
0.6458	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD7748	Approved
0.641	Remote Similarity	NPD3197	Phase 1
0.6392	Remote Similarity	NPD7902	Approved
0.6374	Remote Similarity	NPD6098	Approved
0.6373	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD6904	Approved
0.6344	Remote Similarity	NPD6080	Approved
0.6344	Remote Similarity	NPD5370	Suspended
0.6344	Remote Similarity	NPD6673	Approved
0.6333	Remote Similarity	NPD4786	Approved
0.6333	Remote Similarity	NPD3668	Phase 3
0.6301	Remote Similarity	NPD4266	Approved
0.6301	Remote Similarity	NPD3196	Approved
0.6301	Remote Similarity	NPD3195	Phase 2
0.6301	Remote Similarity	NPD3194	Approved
0.6292	Remote Similarity	NPD3667	Approved
0.6289	Remote Similarity	NPD7839	Suspended
0.6279	Remote Similarity	NPD4756	Discovery
0.6277	Remote Similarity	NPD5207	Approved
0.6275	Remote Similarity	NPD6008	Approved
0.625	Remote Similarity	NPD7331	Phase 2
0.6224	Remote Similarity	NPD6083	Phase 2
0.6224	Remote Similarity	NPD6084	Phase 2
0.6211	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD8035	Phase 2
0.6211	Remote Similarity	NPD6050	Approved
0.6211	Remote Similarity	NPD8034	Phase 2
0.6211	Remote Similarity	NPD7637	Suspended
0.6211	Remote Similarity	NPD7515	Phase 2
0.6186	Remote Similarity	NPD5695	Phase 3
0.6164	Remote Similarity	NPD3172	Approved
0.6162	Remote Similarity	NPD4225	Approved
0.6162	Remote Similarity	NPD5696	Approved
0.6146	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD5343	Approved
0.6105	Remote Similarity	NPD5692	Phase 3
0.6104	Remote Similarity	NPD3198	Approved
0.6082	Remote Similarity	NPD6001	Approved
0.6075	Remote Similarity	NPD6053	Discontinued
0.6067	Remote Similarity	NPD4695	Discontinued
0.6064	Remote Similarity	NPD5208	Approved
0.6049	Remote Similarity	NPD3704	Approved
0.6042	Remote Similarity	NPD5693	Phase 1
0.6042	Remote Similarity	NPD5694	Approved
0.6038	Remote Similarity	NPD6371	Approved
0.6022	Remote Similarity	NPD3618	Phase 1
0.6	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6051	Approved
0.6	Remote Similarity	NPD7638	Approved
0.5981	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD3133	Approved
0.5978	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD3666	Approved
0.5978	Remote Similarity	NPD3665	Phase 1
0.5962	Remote Similarity	NPD7128	Approved
0.5962	Remote Similarity	NPD6402	Approved
0.5962	Remote Similarity	NPD6675	Approved
0.5962	Remote Similarity	NPD5739	Approved
0.5957	Remote Similarity	NPD3573	Approved
0.5943	Remote Similarity	NPD6373	Approved
0.5943	Remote Similarity	NPD6372	Approved
0.5942	Remote Similarity	NPD2699	Approved
0.5941	Remote Similarity	NPD7639	Approved
0.5941	Remote Similarity	NPD7640	Approved
0.5938	Remote Similarity	NPD3673	Approved
0.5938	Remote Similarity	NPD3672	Approved
0.5938	Remote Similarity	NPD7838	Discovery
0.5926	Remote Similarity	NPD7341	Phase 2
0.5922	Remote Similarity	NPD6052	Approved
0.5914	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.589	Remote Similarity	NPD6927	Phase 3
0.5888	Remote Similarity	NPD2067	Discontinued
0.5876	Remote Similarity	NPD5284	Approved
0.5876	Remote Similarity	NPD5281	Approved
0.5875	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.587	Remote Similarity	NPD6110	Phase 1
0.5867	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5857	Remote Similarity	NPD3174	Discontinued
0.5851	Remote Similarity	NPD5279	Phase 3
0.5849	Remote Similarity	NPD6881	Approved
0.5849	Remote Similarity	NPD6899	Approved
0.5849	Remote Similarity	NPD7320	Approved
0.5849	Remote Similarity	NPD6686	Approved
0.5843	Remote Similarity	NPD3732	Approved
0.5842	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD6650	Approved
0.5833	Remote Similarity	NPD6649	Approved
0.5833	Remote Similarity	NPD5328	Approved
0.5824	Remote Similarity	NPD857	Phase 3
0.5823	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5783	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD5701	Approved
0.5755	Remote Similarity	NPD5697	Approved
0.5747	Remote Similarity	NPD6924	Approved
0.5747	Remote Similarity	NPD6926	Approved
0.5741	Remote Similarity	NPD7290	Approved
0.5741	Remote Similarity	NPD7102	Approved
0.5741	Remote Similarity	NPD6883	Approved
0.5732	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7115	Discovery
0.5714	Remote Similarity	NPD229	Approved
0.5714	Remote Similarity	NPD6097	Approved
0.5714	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6079	Approved
0.5714	Remote Similarity	NPD6096	Approved
0.5701	Remote Similarity	NPD6011	Approved
0.57	Remote Similarity	NPD5654	Approved
0.5699	Remote Similarity	NPD6695	Phase 3
0.5698	Remote Similarity	NPD5777	Approved
0.5694	Remote Similarity	NPD6125	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD6847	Approved
0.5688	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD6869	Approved
0.5688	Remote Similarity	NPD6617	Approved
0.5688	Remote Similarity	NPD8130	Phase 1
0.5688	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.567	Remote Similarity	NPD4753	Phase 2
0.5667	Remote Similarity	NPD4238	Approved
0.5667	Remote Similarity	NPD4802	Phase 2
0.5652	Remote Similarity	NPD8517	Approved
0.5652	Remote Similarity	NPD8516	Approved
0.5652	Remote Similarity	NPD8513	Phase 3
0.5652	Remote Similarity	NPD8515	Approved
0.5648	Remote Similarity	NPD6014	Approved
0.5648	Remote Similarity	NPD6012	Approved
0.5648	Remote Similarity	NPD6013	Approved
0.5647	Remote Similarity	NPD6922	Approved
0.5647	Remote Similarity	NPD6923	Approved
0.5647	Remote Similarity	NPD4137	Phase 3
0.5644	Remote Similarity	NPD4697	Phase 3
0.5644	Remote Similarity	NPD7732	Phase 3
0.5644	Remote Similarity	NPD1989	Approved
0.5641	Remote Similarity	NPD8779	Phase 3
0.5638	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD6882	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