NPASS Compound

Structure

NPC3436 OpenBabel07101718282D 24 26 0 0 1 0 0 0 0 0999 V2000 -0.1428 2.6321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6820 2.8291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2539 -1.5576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2826 -0.6029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6040 0.2802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6276 1.9397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6276 -0.9397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4507 1.2531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6428 1.7660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0566 1.9019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8350 0.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4936 1.4397 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4936 -0.4397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8356 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1107 -0.4962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6428 -0.7660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.0469 1.7628 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2597 2.0825 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0504 -0.8382 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0406 1.9992 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4410 1.1139 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2816 -1.0554 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 9 1 0 0 0 0 2 10 1 0 0 0 0 4 5 1 0 0 0 0 4 16 1 0 0 0 0 5 17 1 0 0 0 0 6 9 1 0 0 0 0 6 12 1 0 0 0 0 7 13 2 0 0 0 0 7 16 1 0 0 0 0 8 11 1 0 0 0 0 8 22 1 0 0 0 0 9 17 1 1 0 0 0 10 18 2 0 0 0 0 10 22 1 0 0 0 0 11 14 2 0 0 0 0 11 15 1 0 0 0 0 12 14 1 0 0 0 0 12 19 1 1 0 0 0 13 14 1 0 0 0 0 13 23 1 0 0 0 0 15 20 2 0 0 0 0 15 23 1 0 0 0 0 16 3 1 1 0 0 0 16 24 1 0 0 0 0 17 21 1 1 0 0 0 17 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	338.14
Volume:	327.905
LogP:	1.628
LogD:	1.363
LogS:	-2.53
# Rotatable Bonds:	3
TPSA:	106.2
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.795
Synthetic Accessibility Score:	5.715
Fsp3:	0.647
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.08
MDCK Permeability:	1.9687644453370012e-05
Pgp-inhibitor:	0.023
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.192
20% Bioavailability (F20%):	0.913
30% Bioavailability (F30%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.766
Plasma Protein Binding (PPB):	74.3302993774414%
Volume Distribution (VD):	0.782
Pgp-substrate:	26.931840896606445%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.712
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.467
CYP2C9-inhibitor:	0.054
CYP2C9-substrate:	0.193
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.187
CYP3A4-inhibitor:	0.081
CYP3A4-substrate:	0.211

ADMET: Excretion

Clearance (CL):	11.034
Half-life (T1/2):	0.61

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.805
Drug-inuced Liver Injury (DILI):	0.975
AMES Toxicity:	0.897
Rat Oral Acute Toxicity:	0.919
Maximum Recommended Daily Dose:	0.029
Skin Sensitization:	0.422
Carcinogencity:	0.935
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.924

Download Data

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

Natural Product: NPC3436

Natural Product ID:	NPC3436
*Common Name:**	LGGOIMAXQUUDCN-JHVPGQBHSA-N
IUPAC Name:	n.a.
Synonyms:	Hirsutinolide-13-Oacetate
Standard InCHIKey:	LGGOIMAXQUUDCN-JHVPGQBHSA-N
Standard InCHI:	InChI=1S/C17H22O7/c1-9-6-12(19)14-11(8-22-10(2)18)15(20)23-13(14)7-16(3)4-5-17(9,21)24-16/h7,9,12,19,21H,4-6,8H2,1-3H3/b13-7+/t9-,12+,16-,17+/m1/s1
SMILES:	CC(=O)OCC1=C2[C@@H](O)C[C@@H](C)[C@]3(O[C@](/C=C2/OC1=O)(C)CC3)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2062869
PubChem CID:	70696890
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001983] Dihydrofurans [CHEMONTID:0001982] Furanones [CHEMONTID:0002223] Butenolides

*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
NPO33276	vernonia cinerea	Species	Asteraceae	Eukaryota	flower	n.a.	n.a.	PMID[22850207]

☑ 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	2
Others	7

Activity Type	# Activity
Cell Line	4
Individual Protein	2
Others	2
PROTEIN COMPLEX	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	99.3	%	PMID[534452]
NPT113	Cell Line	RAW264.7	Mus musculus	Survival	=	18.0	%	PMID[534452]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	2700.0	nM	PMID[534452]
NPT71	Cell Line	HEK293	Homo sapiens	Survival	=	55.0	%	PMID[534452]
NPT4097	Individual Protein	Signal transducer and activator of transcription 1	Mus musculus	Activity	=	60.0	%	PMID[534453]
NPT6622	Individual Protein	Signal transducer and activator of transcription 3	Mus musculus	Activity	=	28.0	%	PMID[534453]
NPT2	Others	Unspecified		Inhibition	=	90.3	%	PMID[534452]
NPT2	Others	Unspecified		IC50	=	10200.0	nM	PMID[534452]
NPT23324	PROTEIN COMPLEX	Signal transducer and activator of transcription 1/ 3	Mus musculus	Activity	=	43.0	%	PMID[534453]

☑ 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 NPC3436 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	188
0.1-0.2	1209
0.2-0.3	4573
0.3-0.4	11515
0.4-0.5	15337
0.5-0.6	6818
0.6-0.7	2698
0.7-0.8	332
0.8-0.85	9
0.85-0.9	5
0.9-0.95	8
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9882	High Similarity	NPC470520
0.9881	High Similarity	NPC225283
0.9767	High Similarity	NPC59646
0.9655	High Similarity	NPC470521
0.9425	High Similarity	NPC32494
0.9425	High Similarity	NPC175842
0.9222	High Similarity	NPC473333
0.9121	High Similarity	NPC2666
0.8977	High Similarity	NPC64913
0.8977	High Similarity	NPC242877
0.8901	High Similarity	NPC471492
0.871	High Similarity	NPC471490
0.8652	High Similarity	NPC260343
0.8163	Intermediate Similarity	NPC291500
0.8163	Intermediate Similarity	NPC140591
0.8163	Intermediate Similarity	NPC189609
0.8163	Intermediate Similarity	NPC303653
0.8163	Intermediate Similarity	NPC197835
0.8125	Intermediate Similarity	NPC471462
0.8	Intermediate Similarity	NPC474338
0.7912	Intermediate Similarity	NPC471185
0.7864	Intermediate Similarity	NPC38154
0.7857	Intermediate Similarity	NPC187268
0.7816	Intermediate Similarity	NPC315394
0.7778	Intermediate Similarity	NPC469872
0.7778	Intermediate Similarity	NPC469864
0.7717	Intermediate Similarity	NPC130030
0.7708	Intermediate Similarity	NPC471483
0.7674	Intermediate Similarity	NPC470686
0.7667	Intermediate Similarity	NPC112868
0.7653	Intermediate Similarity	NPC301596
0.7653	Intermediate Similarity	NPC299396
0.7634	Intermediate Similarity	NPC475461
0.7634	Intermediate Similarity	NPC305475
0.7629	Intermediate Similarity	NPC469632
0.7609	Intermediate Similarity	NPC475706
0.7604	Intermediate Similarity	NPC2882
0.7604	Intermediate Similarity	NPC158061
0.7573	Intermediate Similarity	NPC81630
0.7527	Intermediate Similarity	NPC255307
0.7527	Intermediate Similarity	NPC470755
0.7526	Intermediate Similarity	NPC472954
0.7526	Intermediate Similarity	NPC189651
0.7526	Intermediate Similarity	NPC475098
0.75	Intermediate Similarity	NPC474809
0.7475	Intermediate Similarity	NPC172998
0.7475	Intermediate Similarity	NPC230800
0.7474	Intermediate Similarity	NPC472378
0.7474	Intermediate Similarity	NPC475819
0.7474	Intermediate Similarity	NPC476805
0.7473	Intermediate Similarity	NPC474894
0.7447	Intermediate Similarity	NPC261721
0.7447	Intermediate Similarity	NPC311163
0.7423	Intermediate Similarity	NPC261607
0.7423	Intermediate Similarity	NPC111114
0.7423	Intermediate Similarity	NPC300312
0.7419	Intermediate Similarity	NPC191476
0.7419	Intermediate Similarity	NPC114979
0.7419	Intermediate Similarity	NPC158756
0.7412	Intermediate Similarity	NPC232812
0.7396	Intermediate Similarity	NPC212598
0.7396	Intermediate Similarity	NPC295312
0.7396	Intermediate Similarity	NPC51358
0.7396	Intermediate Similarity	NPC307092
0.7374	Intermediate Similarity	NPC304886
0.7374	Intermediate Similarity	NPC234339
0.7374	Intermediate Similarity	NPC273197
0.7368	Intermediate Similarity	NPC72513
0.7368	Intermediate Similarity	NPC160138
0.7368	Intermediate Similarity	NPC191283
0.7353	Intermediate Similarity	NPC133907
0.7353	Intermediate Similarity	NPC469851
0.7353	Intermediate Similarity	NPC128733
0.7353	Intermediate Similarity	NPC46998
0.7353	Intermediate Similarity	NPC244456
0.7353	Intermediate Similarity	NPC110443
0.7353	Intermediate Similarity	NPC469657
0.7353	Intermediate Similarity	NPC185141
0.7347	Intermediate Similarity	NPC125674
0.7347	Intermediate Similarity	NPC228451
0.7347	Intermediate Similarity	NPC40821
0.7347	Intermediate Similarity	NPC469692
0.7347	Intermediate Similarity	NPC32862
0.7347	Intermediate Similarity	NPC469645
0.7347	Intermediate Similarity	NPC475838
0.7347	Intermediate Similarity	NPC272293
0.7347	Intermediate Similarity	NPC156553
0.734	Intermediate Similarity	NPC261380
0.734	Intermediate Similarity	NPC165162
0.734	Intermediate Similarity	NPC11804
0.734	Intermediate Similarity	NPC67081
0.734	Intermediate Similarity	NPC471223
0.7333	Intermediate Similarity	NPC475074
0.7327	Intermediate Similarity	NPC141191
0.7327	Intermediate Similarity	NPC203627
0.7326	Intermediate Similarity	NPC37929
0.7326	Intermediate Similarity	NPC64234
0.7326	Intermediate Similarity	NPC4299
0.732	Intermediate Similarity	NPC129419
0.732	Intermediate Similarity	NPC475879
0.732	Intermediate Similarity	NPC232426
0.732	Intermediate Similarity	NPC475855
0.732	Intermediate Similarity	NPC473448
0.732	Intermediate Similarity	NPC281942
0.7312	Intermediate Similarity	NPC40746
0.7312	Intermediate Similarity	NPC475714
0.7312	Intermediate Similarity	NPC473390
0.7312	Intermediate Similarity	NPC169575
0.7312	Intermediate Similarity	NPC44261
0.7312	Intermediate Similarity	NPC131669
0.73	Intermediate Similarity	NPC288350
0.73	Intermediate Similarity	NPC173329
0.73	Intermediate Similarity	NPC16967
0.7292	Intermediate Similarity	NPC26078
0.7292	Intermediate Similarity	NPC472809
0.7292	Intermediate Similarity	NPC476803
0.7292	Intermediate Similarity	NPC472810
0.7292	Intermediate Similarity	NPC473658
0.7292	Intermediate Similarity	NPC471956
0.7283	Intermediate Similarity	NPC475944
0.7283	Intermediate Similarity	NPC78677
0.7283	Intermediate Similarity	NPC325031
0.7283	Intermediate Similarity	NPC59994
0.7283	Intermediate Similarity	NPC315731
0.7273	Intermediate Similarity	NPC96541
0.7273	Intermediate Similarity	NPC121825
0.7273	Intermediate Similarity	NPC470255
0.7273	Intermediate Similarity	NPC191521
0.7273	Intermediate Similarity	NPC167219
0.7273	Intermediate Similarity	NPC474247
0.7263	Intermediate Similarity	NPC469483
0.7263	Intermediate Similarity	NPC469910
0.7263	Intermediate Similarity	NPC150755
0.7263	Intermediate Similarity	NPC116575
0.7255	Intermediate Similarity	NPC288876
0.7253	Intermediate Similarity	NPC471537
0.7245	Intermediate Similarity	NPC141831
0.7238	Intermediate Similarity	NPC469852
0.7234	Intermediate Similarity	NPC141193
0.7234	Intermediate Similarity	NPC471301
0.7234	Intermediate Similarity	NPC476804
0.7234	Intermediate Similarity	NPC82297
0.7234	Intermediate Similarity	NPC96259
0.7228	Intermediate Similarity	NPC475709
0.7228	Intermediate Similarity	NPC53844
0.7228	Intermediate Similarity	NPC169205
0.7216	Intermediate Similarity	NPC268298
0.7216	Intermediate Similarity	NPC470734
0.7216	Intermediate Similarity	NPC212664
0.7212	Intermediate Similarity	NPC471938
0.7209	Intermediate Similarity	NPC101622
0.7209	Intermediate Similarity	NPC475004
0.7204	Intermediate Similarity	NPC474439
0.7204	Intermediate Similarity	NPC474028
0.7204	Intermediate Similarity	NPC229825
0.7204	Intermediate Similarity	NPC11383
0.7204	Intermediate Similarity	NPC471298
0.7204	Intermediate Similarity	NPC323251
0.7204	Intermediate Similarity	NPC89555
0.7204	Intermediate Similarity	NPC310450
0.7204	Intermediate Similarity	NPC475046
0.7204	Intermediate Similarity	NPC474959
0.72	Intermediate Similarity	NPC220221
0.72	Intermediate Similarity	NPC476487
0.72	Intermediate Similarity	NPC469873
0.72	Intermediate Similarity	NPC13924
0.72	Intermediate Similarity	NPC476488
0.7191	Intermediate Similarity	NPC329852
0.7188	Intermediate Similarity	NPC45409
0.7188	Intermediate Similarity	NPC313658
0.7188	Intermediate Similarity	NPC316138
0.7172	Intermediate Similarity	NPC475912
0.7172	Intermediate Similarity	NPC472812
0.7172	Intermediate Similarity	NPC205034
0.7172	Intermediate Similarity	NPC162615
0.7172	Intermediate Similarity	NPC475302
0.7172	Intermediate Similarity	NPC152778
0.7172	Intermediate Similarity	NPC29798
0.7172	Intermediate Similarity	NPC476049
0.7172	Intermediate Similarity	NPC282644
0.717	Intermediate Similarity	NPC469853
0.7158	Intermediate Similarity	NPC474424
0.7158	Intermediate Similarity	NPC471494
0.7157	Intermediate Similarity	NPC278673
0.7157	Intermediate Similarity	NPC474440
0.7143	Intermediate Similarity	NPC93763
0.7143	Intermediate Similarity	NPC108816
0.7143	Intermediate Similarity	NPC474232
0.7143	Intermediate Similarity	NPC469368
0.7143	Intermediate Similarity	NPC309190
0.7143	Intermediate Similarity	NPC121099
0.7143	Intermediate Similarity	NPC100487
0.7143	Intermediate Similarity	NPC315765
0.7143	Intermediate Similarity	NPC474816
0.7143	Intermediate Similarity	NPC179394
0.7143	Intermediate Similarity	NPC144133
0.7143	Intermediate Similarity	NPC471937
0.7143	Intermediate Similarity	NPC209135
0.7143	Intermediate Similarity	NPC326753
0.7143	Intermediate Similarity	NPC469403

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 NPC3436 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	1622
0.2-0.3	3807
0.3-0.4	2540
0.4-0.5	719
0.5-0.6	252
0.6-0.7	48
0.7-0.8	1
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
0.7143	Intermediate Similarity	NPD7838	Discovery
0.7053	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.699	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.699	Remote Similarity	NPD4225	Approved
0.6947	Remote Similarity	NPD7154	Phase 3
0.6907	Remote Similarity	NPD4249	Approved
0.6837	Remote Similarity	NPD4251	Approved
0.6837	Remote Similarity	NPD4250	Approved
0.6733	Remote Similarity	NPD7983	Approved
0.6697	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD5779	Approved
0.6635	Remote Similarity	NPD7839	Suspended
0.6634	Remote Similarity	NPD5785	Approved
0.6634	Remote Similarity	NPD46	Approved
0.6634	Remote Similarity	NPD6698	Approved
0.6633	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD4822	Approved
0.6632	Remote Similarity	NPD4819	Approved
0.6632	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD4821	Approved
0.6632	Remote Similarity	NPD4820	Approved
0.6602	Remote Similarity	NPD5282	Discontinued
0.6569	Remote Similarity	NPD7637	Suspended
0.6552	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD6371	Approved
0.6495	Remote Similarity	NPD5209	Approved
0.6465	Remote Similarity	NPD5363	Approved
0.6449	Remote Similarity	NPD6648	Approved
0.6429	Remote Similarity	NPD5362	Discontinued
0.6421	Remote Similarity	NPD4268	Approved
0.6421	Remote Similarity	NPD4271	Approved
0.6404	Remote Similarity	NPD6053	Discontinued
0.6389	Remote Similarity	NPD5344	Discontinued
0.6373	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD6101	Approved
0.6339	Remote Similarity	NPD6686	Approved
0.6327	Remote Similarity	NPD4270	Approved
0.6327	Remote Similarity	NPD4269	Approved
0.6316	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD5331	Approved
0.6263	Remote Similarity	NPD5332	Approved
0.625	Remote Similarity	NPD8513	Phase 3
0.625	Remote Similarity	NPD8515	Approved
0.625	Remote Similarity	NPD6411	Approved
0.625	Remote Similarity	NPD8516	Approved
0.625	Remote Similarity	NPD8517	Approved
0.6238	Remote Similarity	NPD5786	Approved
0.6224	Remote Similarity	NPD5369	Approved
0.6224	Remote Similarity	NPD4790	Discontinued
0.6214	Remote Similarity	NPD1695	Approved
0.62	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD7505	Discontinued
0.6162	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD7639	Approved
0.6147	Remote Similarity	NPD7640	Approved
0.6146	Remote Similarity	NPD4756	Discovery
0.6122	Remote Similarity	NPD4252	Approved
0.6116	Remote Similarity	NPD7503	Approved
0.61	Remote Similarity	NPD6695	Phase 3
0.6055	Remote Similarity	NPD7638	Approved
0.605	Remote Similarity	NPD7115	Discovery
0.6	Remote Similarity	NPD7327	Approved
0.6	Remote Similarity	NPD6435	Approved
0.6	Remote Similarity	NPD7328	Approved
0.6	Remote Similarity	NPD8074	Phase 3
0.5984	Remote Similarity	NPD8033	Approved
0.598	Remote Similarity	NPD1694	Approved
0.598	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.595	Remote Similarity	NPD7516	Approved
0.5918	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5906	Remote Similarity	NPD7319	Approved
0.5905	Remote Similarity	NPD5370	Suspended
0.5902	Remote Similarity	NPD8377	Approved
0.5902	Remote Similarity	NPD8294	Approved
0.5865	Remote Similarity	NPD7524	Approved
0.5865	Remote Similarity	NPD7750	Discontinued
0.5862	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD8380	Approved
0.5854	Remote Similarity	NPD8378	Approved
0.5854	Remote Similarity	NPD8379	Approved
0.5854	Remote Similarity	NPD8296	Approved
0.5854	Remote Similarity	NPD8335	Approved
0.58	Remote Similarity	NPD5368	Approved
0.58	Remote Similarity	NPD6930	Phase 2
0.58	Remote Similarity	NPD6931	Approved
0.5794	Remote Similarity	NPD7507	Approved
0.5794	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD8039	Approved
0.576	Remote Similarity	NPD7830	Approved
0.576	Remote Similarity	NPD7829	Approved
0.5752	Remote Similarity	NPD7632	Discontinued
0.5739	Remote Similarity	NPD4211	Phase 1
0.573	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD969	Suspended
0.5702	Remote Similarity	NPD6647	Phase 2
0.57	Remote Similarity	NPD6929	Approved
0.568	Remote Similarity	NPD8080	Discontinued
0.5678	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5678	Remote Similarity	NPD2067	Discontinued
0.5676	Remote Similarity	NPD6083	Phase 2
0.5676	Remote Similarity	NPD6084	Phase 2
0.5673	Remote Similarity	NPD1696	Phase 3
0.567	Remote Similarity	NPD6926	Approved
0.567	Remote Similarity	NPD6924	Approved
0.5669	Remote Similarity	NPD8273	Phase 1
0.5669	Remote Similarity	NPD8451	Approved
0.5667	Remote Similarity	NPD368	Approved
0.5656	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5656	Remote Similarity	NPD7500	Approved
0.5648	Remote Similarity	NPD7087	Discontinued
0.5644	Remote Similarity	NPD7514	Phase 3
0.5644	Remote Similarity	NPD7332	Phase 2
0.5641	Remote Similarity	NPD7320	Approved
0.5636	Remote Similarity	NPD5695	Phase 3
0.5635	Remote Similarity	NPD7642	Approved
0.563	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.563	Remote Similarity	NPD2204	Approved
0.5625	Remote Similarity	NPD8448	Approved
0.5607	Remote Similarity	NPD6051	Approved
0.5603	Remote Similarity	NPD5739	Approved
0.5603	Remote Similarity	NPD6402	Approved
0.5603	Remote Similarity	NPD7128	Approved
0.5603	Remote Similarity	NPD6675	Approved
0.56	Remote Similarity	NPD8444	Approved
0.56	Remote Similarity	NPD7322	Clinical (unspecified phase)

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