NPASS Compound

Structure

NPC474154 OpenBabel07101719142D 32 35 0 0 1 0 0 0 0 0999 V2000 -1.6815 0.9708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4703 -1.2766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8462 -0.5329 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6874 -4.6407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2342 -3.8386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3262 0.3553 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2355 -1.2197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7914 -1.7489 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9159 -1.0997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8408 -1.4562 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5223 -0.4854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6815 -1.9416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5217 -3.8967 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8116 -0.4854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6815 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8408 -1.4562 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5223 -1.4562 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2355 -2.9690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7824 -2.1669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7914 -2.4398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4254 -4.2514 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8408 -0.4854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7505 -2.0944 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.5142 -1.4452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2661 -3.7660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8408 -0.4854 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.3630 -1.9416 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8792 -2.7718 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4979 -5.2195 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 4.4108 -2.8060 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 5 26 1 0 0 0 0 6 27 1 0 0 0 0 7 8 1 0 0 0 0 7 10 1 0 0 0 0 8 21 1 0 0 0 0 9 11 1 0 0 0 0 9 17 1 0 0 0 0 10 25 1 0 0 0 0 11 27 1 0 0 0 0 12 16 1 0 0 0 0 12 18 2 0 0 0 0 13 17 2 0 0 0 0 13 18 1 0 0 0 0 14 19 1 0 0 0 0 14 22 1 0 0 0 0 15 20 1 0 0 0 0 15 27 1 0 0 0 0 16 23 2 0 0 0 0 17 23 1 0 0 0 0 18 28 1 0 0 0 0 19 20 2 0 0 0 0 19 21 1 0 0 0 0 20 24 1 0 0 0 0 21 29 2 0 0 0 0 22 26 1 0 0 0 0 22 30 1 6 0 0 0 23 31 1 0 0 0 0 24 25 1 0 0 0 0 24 32 1 0 0 0 0 26 32 1 0 0 0 0 27 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	442.27
Volume:	472.091
LogP:	4.595
LogD:	3.611
LogS:	-4.418
# Rotatable Bonds:	1
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.596
Synthetic Accessibility Score:	5.486
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.813
MDCK Permeability:	1.7667911379248835e-05
Pgp-inhibitor:	0.63
Pgp-substrate:	0.471
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.981
30% Bioavailability (F30%):	0.291

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.796
Plasma Protein Binding (PPB):	93.46017456054688%
Volume Distribution (VD):	1.67
Pgp-substrate:	3.124500036239624%

ADMET: Metabolism

CYP1A2-inhibitor:	0.041
CYP1A2-substrate:	0.454
CYP2C19-inhibitor:	0.166
CYP2C19-substrate:	0.806
CYP2C9-inhibitor:	0.462
CYP2C9-substrate:	0.825
CYP2D6-inhibitor:	0.218
CYP2D6-substrate:	0.759
CYP3A4-inhibitor:	0.862
CYP3A4-substrate:	0.445

ADMET: Excretion

Clearance (CL):	10.861
Half-life (T1/2):	0.122

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.352
Drug-inuced Liver Injury (DILI):	0.068
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.716
Maximum Recommended Daily Dose:	0.942
Skin Sensitization:	0.101
Carcinogencity:	0.054
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC474154

Natural Product ID:	NPC474154
*Common Name:**	Cystoseirol
IUPAC Name:	(9R)-9-hydroxy-12-[(6-hydroxy-2,8-dimethyl-3,4-dihydrochromen-2-yl)methyl]-2,2,10,10-tetramethyl-11-oxabicyclo[5.4.1]dodec-7(12)-en-6-one
Synonyms:	Cystoseirol
Standard InCHIKey:	ZTHCYPHYCZDHSI-PCHNOXPDSA-N
Standard InCHI:	InChI=1S/C27H38O5/c1-16-12-18(28)13-17-9-11-27(6,31-23(16)17)15-20-19-14-22(30)26(4,5)32-24(20)25(2,3)10-7-8-21(19)29/h12-13,22,24,28,30H,7-11,14-15H2,1-6H3/t22-,24?,27?/m1/s1
SMILES:	CC1=CC(=CC2=C1OC(CC2)(C)CC3=C4CC(C(OC3C(CCCC4=O)(C)C)(C)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463050
PubChem CID:	44567072
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans

*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
NPO10682	Cystoseira mediterranea	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2045820]
NPO10682	Cystoseira mediterranea	Species	Sargassaceae	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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	Inhibition	=	73.0	%	PMID[458761]

☑ 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 NPC474154 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	348
0.1-0.2	1321
0.2-0.3	3298
0.3-0.4	7679
0.4-0.5	11389
0.5-0.6	4319
0.6-0.7	10248
0.7-0.8	4027
0.8-0.85	57
0.85-0.9	10
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8768	High Similarity	NPC474246
0.8768	High Similarity	NPC474143
0.8759	High Similarity	NPC59654
0.8623	High Similarity	NPC271832
0.8593	High Similarity	NPC474130
0.8561	High Similarity	NPC475880
0.8519	High Similarity	NPC204535
0.8519	High Similarity	NPC46586
0.8478	Intermediate Similarity	NPC319422
0.8478	Intermediate Similarity	NPC477214
0.8478	Intermediate Similarity	NPC477211
0.8478	Intermediate Similarity	NPC477212
0.8451	Intermediate Similarity	NPC477210
0.844	Intermediate Similarity	NPC251549
0.8394	Intermediate Similarity	NPC276962
0.8394	Intermediate Similarity	NPC190086
0.8392	Intermediate Similarity	NPC476018
0.8392	Intermediate Similarity	NPC475029
0.8356	Intermediate Similarity	NPC475063
0.8356	Intermediate Similarity	NPC475044
0.8345	Intermediate Similarity	NPC474943
0.8345	Intermediate Similarity	NPC475005
0.8333	Intermediate Similarity	NPC477213
0.8333	Intermediate Similarity	NPC194847
0.8333	Intermediate Similarity	NPC21797
0.831	Intermediate Similarity	NPC118253
0.8298	Intermediate Similarity	NPC196621
0.8296	Intermediate Similarity	NPC232295
0.8288	Intermediate Similarity	NPC475045
0.8286	Intermediate Similarity	NPC201419
0.8264	Intermediate Similarity	NPC475011
0.8261	Intermediate Similarity	NPC147896
0.8248	Intermediate Similarity	NPC49441
0.8222	Intermediate Similarity	NPC32152
0.8219	Intermediate Similarity	NPC476025
0.8219	Intermediate Similarity	NPC475028
0.8212	Intermediate Similarity	NPC91902
0.8182	Intermediate Similarity	NPC317601
0.8182	Intermediate Similarity	NPC329427
0.8176	Intermediate Similarity	NPC184053
0.8165	Intermediate Similarity	NPC3629
0.8162	Intermediate Similarity	NPC474131
0.8151	Intermediate Similarity	NPC98804
0.8129	Intermediate Similarity	NPC474237
0.8125	Intermediate Similarity	NPC470871
0.8121	Intermediate Similarity	NPC329493
0.8101	Intermediate Similarity	NPC471976
0.8092	Intermediate Similarity	NPC473133
0.8092	Intermediate Similarity	NPC470670
0.8092	Intermediate Similarity	NPC47388
0.8085	Intermediate Similarity	NPC95034
0.8085	Intermediate Similarity	NPC142087
0.8082	Intermediate Similarity	NPC278832
0.8082	Intermediate Similarity	NPC64157
0.8067	Intermediate Similarity	NPC316691
0.8013	Intermediate Similarity	NPC471600
0.8013	Intermediate Similarity	NPC84721
0.8	Intermediate Similarity	NPC471677
0.8	Intermediate Similarity	NPC69539
0.7975	Intermediate Similarity	NPC196448
0.7974	Intermediate Similarity	NPC85773
0.7971	Intermediate Similarity	NPC473875
0.7959	Intermediate Similarity	NPC474610
0.7958	Intermediate Similarity	NPC473993
0.7947	Intermediate Similarity	NPC474599
0.7941	Intermediate Similarity	NPC238176
0.7941	Intermediate Similarity	NPC187993
0.7933	Intermediate Similarity	NPC164599
0.7922	Intermediate Similarity	NPC10097
0.7919	Intermediate Similarity	NPC76312
0.7919	Intermediate Similarity	NPC475012
0.7911	Intermediate Similarity	NPC164427
0.7908	Intermediate Similarity	NPC474302
0.7898	Intermediate Similarity	NPC469405
0.7895	Intermediate Similarity	NPC18886
0.7887	Intermediate Similarity	NPC476022
0.7887	Intermediate Similarity	NPC474945
0.7885	Intermediate Similarity	NPC472420
0.7885	Intermediate Similarity	NPC473131
0.7885	Intermediate Similarity	NPC244577
0.7885	Intermediate Similarity	NPC263384
0.7885	Intermediate Similarity	NPC472422
0.7885	Intermediate Similarity	NPC471676
0.7885	Intermediate Similarity	NPC474023
0.7885	Intermediate Similarity	NPC474021
0.7885	Intermediate Similarity	NPC470675
0.7875	Intermediate Similarity	NPC472630
0.7875	Intermediate Similarity	NPC472631
0.7871	Intermediate Similarity	NPC139966
0.7871	Intermediate Similarity	NPC307052
0.7871	Intermediate Similarity	NPC472628
0.7862	Intermediate Similarity	NPC258073
0.7862	Intermediate Similarity	NPC223787
0.7857	Intermediate Similarity	NPC14875
0.7857	Intermediate Similarity	NPC202494
0.7853	Intermediate Similarity	NPC263212
0.7852	Intermediate Similarity	NPC474114
0.7852	Intermediate Similarity	NPC474050
0.7852	Intermediate Similarity	NPC473931
0.7848	Intermediate Similarity	NPC175192
0.7848	Intermediate Similarity	NPC471116
0.7848	Intermediate Similarity	NPC326910
0.7848	Intermediate Similarity	NPC477958
0.7847	Intermediate Similarity	NPC206028
0.7843	Intermediate Similarity	NPC474044
0.7843	Intermediate Similarity	NPC212697
0.784	Intermediate Similarity	NPC329669
0.784	Intermediate Similarity	NPC472278
0.784	Intermediate Similarity	NPC7483
0.784	Intermediate Similarity	NPC473313
0.7834	Intermediate Similarity	NPC475790
0.7834	Intermediate Similarity	NPC256141
0.7834	Intermediate Similarity	NPC138288
0.7829	Intermediate Similarity	NPC276565
0.7826	Intermediate Similarity	NPC30655
0.7826	Intermediate Similarity	NPC45124
0.7826	Intermediate Similarity	NPC74854
0.7826	Intermediate Similarity	NPC472634
0.7826	Intermediate Similarity	NPC474186
0.7823	Intermediate Similarity	NPC27394
0.7821	Intermediate Similarity	NPC37348
0.7812	Intermediate Similarity	NPC95936
0.7812	Intermediate Similarity	NPC473990
0.7812	Intermediate Similarity	NPC250214
0.7808	Intermediate Similarity	NPC27578
0.7808	Intermediate Similarity	NPC289624
0.7806	Intermediate Similarity	NPC191634
0.7805	Intermediate Similarity	NPC6588
0.7805	Intermediate Similarity	NPC477154
0.7805	Intermediate Similarity	NPC117854
0.7805	Intermediate Similarity	NPC158761
0.78	Intermediate Similarity	NPC79372
0.7799	Intermediate Similarity	NPC472626
0.7799	Intermediate Similarity	NPC209614
0.7799	Intermediate Similarity	NPC10754
0.7799	Intermediate Similarity	NPC317383
0.7799	Intermediate Similarity	NPC470328
0.7799	Intermediate Similarity	NPC78492
0.7799	Intermediate Similarity	NPC215917
0.7799	Intermediate Similarity	NPC20530
0.7799	Intermediate Similarity	NPC208152
0.7793	Intermediate Similarity	NPC163169
0.7793	Intermediate Similarity	NPC123
0.7792	Intermediate Similarity	NPC187282
0.7792	Intermediate Similarity	NPC290133
0.7792	Intermediate Similarity	NPC24136
0.7791	Intermediate Similarity	NPC473286
0.7786	Intermediate Similarity	NPC476165
0.7785	Intermediate Similarity	NPC209760
0.7785	Intermediate Similarity	NPC298692
0.7785	Intermediate Similarity	NPC223701
0.7785	Intermediate Similarity	NPC7989
0.7785	Intermediate Similarity	NPC301233
0.7785	Intermediate Similarity	NPC470331
0.7785	Intermediate Similarity	NPC74924
0.7785	Intermediate Similarity	NPC293286
0.7785	Intermediate Similarity	NPC100134
0.7785	Intermediate Similarity	NPC472583
0.7778	Intermediate Similarity	NPC296144
0.7778	Intermediate Similarity	NPC472402
0.7778	Intermediate Similarity	NPC213900
0.7778	Intermediate Similarity	NPC28784
0.7778	Intermediate Similarity	NPC220912
0.7778	Intermediate Similarity	NPC469642
0.7778	Intermediate Similarity	NPC469683
0.7771	Intermediate Similarity	NPC474772
0.7771	Intermediate Similarity	NPC472423
0.7771	Intermediate Similarity	NPC46564
0.7771	Intermediate Similarity	NPC262039
0.7771	Intermediate Similarity	NPC207346
0.7771	Intermediate Similarity	NPC474744
0.7771	Intermediate Similarity	NPC278476
0.7771	Intermediate Similarity	NPC319910
0.7771	Intermediate Similarity	NPC262038
0.7771	Intermediate Similarity	NPC472636
0.7771	Intermediate Similarity	NPC254412
0.777	Intermediate Similarity	NPC281169
0.777	Intermediate Similarity	NPC51087
0.777	Intermediate Similarity	NPC291119
0.777	Intermediate Similarity	NPC161856
0.7764	Intermediate Similarity	NPC174953
0.7764	Intermediate Similarity	NPC475886
0.7764	Intermediate Similarity	NPC474287
0.7764	Intermediate Similarity	NPC475784
0.7762	Intermediate Similarity	NPC474944
0.7756	Intermediate Similarity	NPC88886
0.7756	Intermediate Similarity	NPC223988
0.7756	Intermediate Similarity	NPC104172
0.7756	Intermediate Similarity	NPC266499
0.7754	Intermediate Similarity	NPC283616
0.775	Intermediate Similarity	NPC27337
0.775	Intermediate Similarity	NPC36852
0.775	Intermediate Similarity	NPC162869
0.775	Intermediate Similarity	NPC156057
0.775	Intermediate Similarity	NPC472598
0.775	Intermediate Similarity	NPC474055
0.775	Intermediate Similarity	NPC475267
0.775	Intermediate Similarity	NPC474836
0.775	Intermediate Similarity	NPC477833
0.775	Intermediate Similarity	NPC78225

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 NPC474154 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	308
0.1-0.2	898
0.2-0.3	1751
0.3-0.4	2576
0.4-0.5	1964
0.5-0.6	1071
0.6-0.7	516
0.7-0.8	66
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
0.7842	Intermediate Similarity	NPD3496	Discontinued
0.78	Intermediate Similarity	NPD2424	Discontinued
0.7794	Intermediate Similarity	NPD6671	Approved
0.7673	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD6100	Approved
0.7667	Intermediate Similarity	NPD6099	Approved
0.7582	Intermediate Similarity	NPD4628	Phase 3
0.7582	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD7985	Registered
0.75	Intermediate Similarity	NPD1934	Approved
0.7484	Intermediate Similarity	NPD4380	Phase 2
0.7453	Intermediate Similarity	NPD2801	Approved
0.7434	Intermediate Similarity	NPD2935	Discontinued
0.7423	Intermediate Similarity	NPD7075	Discontinued
0.74	Intermediate Similarity	NPD6355	Discontinued
0.7379	Intermediate Similarity	NPD6696	Suspended
0.7362	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4060	Phase 1
0.7315	Intermediate Similarity	NPD6798	Discontinued
0.7315	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD7157	Approved
0.7284	Intermediate Similarity	NPD6844	Discontinued
0.7278	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2346	Discontinued
0.7273	Intermediate Similarity	NPD1778	Approved
0.7267	Intermediate Similarity	NPD6233	Phase 2
0.7262	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD6166	Phase 2
0.7255	Intermediate Similarity	NPD2799	Discontinued
0.7248	Intermediate Similarity	NPD7095	Approved
0.7237	Intermediate Similarity	NPD6653	Approved
0.7235	Intermediate Similarity	NPD5844	Phase 1
0.7235	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD7340	Approved
0.7229	Intermediate Similarity	NPD5494	Approved
0.7212	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD7458	Discontinued
0.72	Intermediate Similarity	NPD2313	Discontinued
0.72	Intermediate Similarity	NPD3268	Approved
0.7195	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD5402	Approved
0.7193	Intermediate Similarity	NPD7074	Phase 3
0.719	Intermediate Similarity	NPD7097	Phase 1
0.7179	Intermediate Similarity	NPD2800	Approved
0.7162	Intermediate Similarity	NPD5647	Approved
0.7161	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3882	Suspended
0.7151	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7033	Discontinued
0.7143	Intermediate Similarity	NPD8651	Approved
0.7143	Intermediate Similarity	NPD1398	Phase 1
0.7135	Intermediate Similarity	NPD7054	Approved
0.7135	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7819	Suspended
0.7115	Intermediate Similarity	NPD1549	Phase 2
0.7114	Intermediate Similarity	NPD9494	Approved
0.7114	Intermediate Similarity	NPD2861	Phase 2
0.7102	Intermediate Similarity	NPD8434	Phase 2
0.7099	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6032	Approved
0.7095	Intermediate Similarity	NPD2797	Approved
0.7093	Intermediate Similarity	NPD7472	Approved
0.7086	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6959	Discontinued
0.708	Intermediate Similarity	NPD290	Approved
0.7076	Intermediate Similarity	NPD3751	Discontinued
0.7076	Intermediate Similarity	NPD3818	Discontinued
0.7075	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6801	Discontinued
0.7071	Intermediate Similarity	NPD7843	Approved
0.7069	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD447	Suspended
0.7055	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD3823	Discontinued
0.7051	Intermediate Similarity	NPD2344	Approved
0.7051	Intermediate Similarity	NPD6004	Phase 3
0.7051	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD5762	Approved
0.7051	Intermediate Similarity	NPD6002	Phase 3
0.7051	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD5763	Approved
0.7051	Intermediate Similarity	NPD6005	Phase 3
0.7045	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD3787	Discontinued
0.7029	Intermediate Similarity	NPD8313	Approved
0.7029	Intermediate Similarity	NPD8312	Approved
0.7029	Intermediate Similarity	NPD2684	Approved
0.7025	Intermediate Similarity	NPD4110	Phase 3
0.7025	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD1241	Discontinued
0.7011	Intermediate Similarity	NPD6559	Discontinued
0.7011	Intermediate Similarity	NPD7251	Discontinued
0.7007	Intermediate Similarity	NPD1608	Approved
0.7	Intermediate Similarity	NPD1511	Approved
0.6994	Remote Similarity	NPD3226	Approved
0.6994	Remote Similarity	NPD2651	Approved
0.6994	Remote Similarity	NPD2649	Approved
0.6993	Remote Similarity	NPD1613	Approved
0.6993	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD8127	Discontinued
0.6981	Remote Similarity	NPD6190	Approved
0.6974	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD7808	Phase 3
0.6966	Remote Similarity	NPD5585	Approved
0.6957	Remote Similarity	NPD2533	Approved
0.6957	Remote Similarity	NPD2532	Approved
0.6957	Remote Similarity	NPD2534	Approved
0.6957	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6797	Phase 2
0.6951	Remote Similarity	NPD6599	Discontinued
0.6939	Remote Similarity	NPD1535	Discovery
0.6939	Remote Similarity	NPD1091	Approved
0.6928	Remote Similarity	NPD8455	Phase 2
0.6928	Remote Similarity	NPD4062	Phase 3
0.6918	Remote Similarity	NPD8166	Discontinued
0.6918	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD4626	Approved
0.6918	Remote Similarity	NPD7976	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD1512	Approved
0.6914	Remote Similarity	NPD6273	Approved
0.6909	Remote Similarity	NPD7411	Suspended
0.6903	Remote Similarity	NPD6651	Approved
0.6899	Remote Similarity	NPD4534	Discontinued
0.6894	Remote Similarity	NPD6799	Approved
0.6892	Remote Similarity	NPD1481	Phase 2
0.6892	Remote Similarity	NPD3972	Approved
0.6886	Remote Similarity	NPD3817	Phase 2
0.6884	Remote Similarity	NPD968	Approved
0.6879	Remote Similarity	NPD2796	Approved
0.6879	Remote Similarity	NPD4476	Approved
0.6879	Remote Similarity	NPD4477	Approved
0.6875	Remote Similarity	NPD2309	Approved
0.6867	Remote Similarity	NPD3267	Approved
0.6867	Remote Similarity	NPD3266	Approved
0.6855	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD4661	Approved
0.6852	Remote Similarity	NPD4662	Approved
0.6849	Remote Similarity	NPD5691	Approved
0.6849	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD1651	Approved
0.6846	Remote Similarity	NPD4749	Approved
0.6842	Remote Similarity	NPD6832	Phase 2
0.6839	Remote Similarity	NPD5124	Phase 1
0.6839	Remote Similarity	NPD5735	Approved
0.6839	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD1653	Approved
0.6828	Remote Similarity	NPD7644	Approved
0.6824	Remote Similarity	NPD1611	Approved
0.6821	Remote Similarity	NPD7473	Discontinued
0.6821	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD8032	Phase 2
0.6816	Remote Similarity	NPD8150	Discontinued
0.6815	Remote Similarity	NPD1510	Phase 2
0.6815	Remote Similarity	NPD4308	Phase 3
0.681	Remote Similarity	NPD2676	Approved
0.681	Remote Similarity	NPD2675	Approved
0.681	Remote Similarity	NPD5049	Phase 3
0.6807	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD17	Approved
0.6797	Remote Similarity	NPD4625	Phase 3
0.6797	Remote Similarity	NPD3027	Phase 3
0.6792	Remote Similarity	NPD970	Clinical (unspecified phase)
0.679	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD1247	Approved
0.6779	Remote Similarity	NPD9717	Approved
0.6776	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6782	Approved
0.6774	Remote Similarity	NPD3620	Phase 2
0.6774	Remote Similarity	NPD6777	Approved
0.6774	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD1240	Approved
0.6774	Remote Similarity	NPD6776	Approved
0.6774	Remote Similarity	NPD6778	Approved
0.6774	Remote Similarity	NPD6781	Approved
0.6774	Remote Similarity	NPD4140	Approved
0.6774	Remote Similarity	NPD6779	Approved
0.6774	Remote Similarity	NPD6780	Approved
0.677	Remote Similarity	NPD3887	Approved
0.677	Remote Similarity	NPD2354	Approved
0.6768	Remote Similarity	NPD5403	Approved
0.6755	Remote Similarity	NPD7435	Discontinued
0.6755	Remote Similarity	NPD1203	Approved
0.6753	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD4538	Approved
0.6752	Remote Similarity	NPD4536	Approved
0.6752	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6674	Discontinued
0.6744	Remote Similarity	NPD6232	Discontinued
0.6736	Remote Similarity	NPD2629	Approved
0.6733	Remote Similarity	NPD4359	Approved
0.6733	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD1529	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