NPASS Compound

Structure

NPC164750 OpenBabel07101719142D 35 39 0 0 1 0 0 0 0 0999 V2000 -4.1369 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3685 -1.2248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7350 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2350 -1.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8690 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8690 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7350 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0029 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0029 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6994 -1.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8690 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1369 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2709 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7350 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4049 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0029 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1369 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0084 -2.9190 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 -2.4049 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2788 -1.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 18 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 7 10 1 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 8 21 1 0 0 0 0 9 13 1 0 0 0 0 9 22 1 0 0 0 0 10 26 1 0 0 0 0 11 29 1 0 0 0 0 12 27 1 0 0 0 0 13 28 1 0 0 0 0 14 20 1 0 0 0 0 14 23 1 0 0 0 0 15 19 2 0 0 0 0 15 33 1 0 0 0 0 16 30 2 0 0 0 0 17 31 2 0 0 0 0 17 34 1 0 0 0 0 18 32 2 0 0 0 0 18 35 1 0 0 0 0 19 20 1 0 0 0 0 19 24 1 0 0 0 0 20 34 1 6 0 0 0 21 26 1 0 0 0 0 21 29 1 6 0 0 0 22 27 1 6 0 0 0 22 29 1 0 0 0 0 23 27 1 6 0 0 0 23 28 1 0 0 0 0 24 25 1 0 0 0 0 24 28 1 6 0 0 0 25 33 1 0 0 0 0 25 35 1 1 0 0 0 27 5 1 6 0 0 0 28 6 1 6 0 0 0 29 16 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.3
Volume:	509.553
LogP:	4.134
LogD:	3.579
LogS:	-4.352
# Rotatable Bonds:	5
TPSA:	78.9
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.382
Synthetic Accessibility Score:	5.223
Fsp3:	0.828
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:	-4.696
MDCK Permeability:	5.376046465244144e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.928
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.986
Plasma Protein Binding (PPB):	63.21986770629883%
Volume Distribution (VD):	2.431
Pgp-substrate:	34.09153366088867%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.082
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.448
CYP2C9-inhibitor:	0.053
CYP2C9-substrate:	0.013
CYP2D6-inhibitor:	0.813
CYP2D6-substrate:	0.071
CYP3A4-inhibitor:	0.73
CYP3A4-substrate:	0.474

ADMET: Excretion

Clearance (CL):	3.946
Half-life (T1/2):	0.05

ADMET: Toxicity

hERG Blockers:	0.723
Human Hepatotoxicity (H-HT):	0.504
Drug-inuced Liver Injury (DILI):	0.216
AMES Toxicity:	0.928
Rat Oral Acute Toxicity:	0.982
Maximum Recommended Daily Dose:	0.919
Skin Sensitization:	0.94
Carcinogencity:	0.967
Eye Corrosion:	0.848
Eye Irritation:	0.099
Respiratory Toxicity:	0.989

Download Data

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

Natural Product: NPC164750

Natural Product ID:	NPC164750
*Common Name:**	(1S,4S,5As,5Bs,7As,11Ar,11Bs,13As,13Br)-11A-Formyl-5B,8,8,13A-Tetramethyl-1,4,5,5A,5B,6,7,7A,8,9,10,11,11A,11B,12,13,13A,13B-Octadecahydrochryseno[2,1-C]Furan-1,4-Diyl Diacetate
IUPAC Name:	[(1S,4S,5aS,5bS,7aS,11aR,11bS,13aS,13bR)-1-acetyloxy-11a-formyl-5b,8,8,13a-tetramethyl-1,4,5,5a,6,7,7a,9,10,11,11b,12,13,13b-tetradecahydrophenanthro[2,1-e][2]benzofuran-4-yl] acetate
Synonyms:
Standard InCHIKey:	GVYVUZXCYYBRKS-GJTCYCQFSA-N
Standard InCHI:	InChI=1S/C29H42O6/c1-17(31)34-20-14-23-27(5)12-8-21-26(3,4)10-7-11-29(21,16-30)22(27)9-13-28(23,6)24-19(20)15-33-25(24)35-18(2)32/h15-16,20-25H,7-14H2,1-6H3/t20-,21-,22-,23-,24+,25-,27+,28-,29+/m0/s1
SMILES:	CC(=O)O[C@H]1C[C@H]2[C@]3(C)CC[C@H]4C(C)(C)CCC[C@]4(C=O)[C@H]3CC[C@]2(C)[C@@H]2C1=CO[C@H]2OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL572703
PubChem CID:	25158951
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids [CHEMONTID:0002883] Scalarane sesterterpenoids

*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
NPO32965	smenospongia sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497955]
NPO32965	smenospongia sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16252912]
NPO32965	smenospongia sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18973387]

☑ 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
MIC	6
Others	1

Activity Type	# Activity
Cell Line	1
Individual Protein	1
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	LC50	=	17.5	ug.mL-1	PMID[485712]
NPT4391	Individual Protein	Isocitrate lyase	Magnaporthe oryzae (strain 70-15 / FGSC 8958) (Rice blast fungus)(Pyricularia oryzae)	IC50	>	100.0	ug.mL-1	PMID[485712]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[485712]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	100.0	ug.mL-1	PMID[485712]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	100.0	ug.mL-1	PMID[485712]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	>	100.0	ug.mL-1	PMID[485712]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	>	100.0	ug.mL-1	PMID[485712]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[485712]

☑ 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 NPC164750 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	278
0.1-0.2	2022
0.2-0.3	5733
0.3-0.4	14718
0.4-0.5	8726
0.5-0.6	6510
0.6-0.7	3933
0.7-0.8	768
0.8-0.85	2
0.85-0.9	4
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9213	High Similarity	NPC144069
0.9101	High Similarity	NPC288952
0.8817	High Similarity	NPC163902
0.8817	High Similarity	NPC246860
0.8511	High Similarity	NPC120539
0.8454	Intermediate Similarity	NPC97867
0.8081	Intermediate Similarity	NPC476768
0.79	Intermediate Similarity	NPC257726
0.79	Intermediate Similarity	NPC204054
0.7872	Intermediate Similarity	NPC98270
0.7849	Intermediate Similarity	NPC170862
0.783	Intermediate Similarity	NPC112457
0.78	Intermediate Similarity	NPC94905
0.78	Intermediate Similarity	NPC317573
0.78	Intermediate Similarity	NPC8954
0.78	Intermediate Similarity	NPC319692
0.78	Intermediate Similarity	NPC325960
0.7788	Intermediate Similarity	NPC476763
0.7788	Intermediate Similarity	NPC476764
0.7766	Intermediate Similarity	NPC475509
0.7732	Intermediate Similarity	NPC293044
0.7723	Intermediate Similarity	NPC10057
0.7714	Intermediate Similarity	NPC476762
0.7714	Intermediate Similarity	NPC476761
0.7714	Intermediate Similarity	NPC476760
0.7692	Intermediate Similarity	NPC476770
0.7629	Intermediate Similarity	NPC4309
0.7629	Intermediate Similarity	NPC224145
0.7619	Intermediate Similarity	NPC222161
0.7604	Intermediate Similarity	NPC472505
0.7596	Intermediate Similarity	NPC134077
0.7576	Intermediate Similarity	NPC160506
0.7576	Intermediate Similarity	NPC474631
0.757	Intermediate Similarity	NPC90946
0.757	Intermediate Similarity	NPC300614
0.757	Intermediate Similarity	NPC325054
0.7553	Intermediate Similarity	NPC226988
0.7551	Intermediate Similarity	NPC50070
0.7549	Intermediate Similarity	NPC151681
0.7549	Intermediate Similarity	NPC121402
0.7549	Intermediate Similarity	NPC158347
0.7549	Intermediate Similarity	NPC224356
0.7549	Intermediate Similarity	NPC132753
0.7549	Intermediate Similarity	NPC175351
0.7545	Intermediate Similarity	NPC157441
0.7528	Intermediate Similarity	NPC12680
0.7526	Intermediate Similarity	NPC175293
0.7526	Intermediate Similarity	NPC46912
0.7526	Intermediate Similarity	NPC33768
0.7526	Intermediate Similarity	NPC162107
0.7525	Intermediate Similarity	NPC280877
0.7524	Intermediate Similarity	NPC132395
0.7524	Intermediate Similarity	NPC471208
0.7524	Intermediate Similarity	NPC471365
0.7524	Intermediate Similarity	NPC471364
0.75	Intermediate Similarity	NPC475061
0.75	Intermediate Similarity	NPC472303
0.75	Intermediate Similarity	NPC476759
0.75	Intermediate Similarity	NPC475700
0.75	Intermediate Similarity	NPC474185
0.75	Intermediate Similarity	NPC199543
0.75	Intermediate Similarity	NPC474971
0.75	Intermediate Similarity	NPC63249
0.75	Intermediate Similarity	NPC31522
0.7475	Intermediate Similarity	NPC169933
0.7475	Intermediate Similarity	NPC475776
0.7475	Intermediate Similarity	NPC474728
0.7474	Intermediate Similarity	NPC471037
0.7455	Intermediate Similarity	NPC194951
0.7455	Intermediate Similarity	NPC12046
0.7451	Intermediate Similarity	NPC112654
0.7451	Intermediate Similarity	NPC311166
0.7451	Intermediate Similarity	NPC472362
0.7451	Intermediate Similarity	NPC154526
0.7451	Intermediate Similarity	NPC472363
0.7449	Intermediate Similarity	NPC16377
0.7429	Intermediate Similarity	NPC476769
0.7426	Intermediate Similarity	NPC91010
0.7426	Intermediate Similarity	NPC477722
0.7423	Intermediate Similarity	NPC12774
0.7423	Intermediate Similarity	NPC9892
0.7423	Intermediate Similarity	NPC187545
0.7423	Intermediate Similarity	NPC185638
0.7423	Intermediate Similarity	NPC118266
0.7423	Intermediate Similarity	NPC329943
0.7423	Intermediate Similarity	NPC10005
0.7423	Intermediate Similarity	NPC2783
0.7423	Intermediate Similarity	NPC91525
0.7423	Intermediate Similarity	NPC471369
0.7407	Intermediate Similarity	NPC88744
0.7407	Intermediate Similarity	NPC230888
0.7404	Intermediate Similarity	NPC20113
0.7404	Intermediate Similarity	NPC477720
0.7404	Intermediate Similarity	NPC228251
0.7404	Intermediate Similarity	NPC161527
0.7404	Intermediate Similarity	NPC219285
0.7404	Intermediate Similarity	NPC477968
0.7404	Intermediate Similarity	NPC477971
0.7404	Intermediate Similarity	NPC477972
0.74	Intermediate Similarity	NPC470590
0.74	Intermediate Similarity	NPC60755
0.74	Intermediate Similarity	NPC471901
0.74	Intermediate Similarity	NPC77099
0.74	Intermediate Similarity	NPC289479
0.74	Intermediate Similarity	NPC285184
0.74	Intermediate Similarity	NPC65513
0.7396	Intermediate Similarity	NPC71626
0.7396	Intermediate Similarity	NPC471367
0.7396	Intermediate Similarity	NPC470011
0.7383	Intermediate Similarity	NPC475611
0.7379	Intermediate Similarity	NPC472188
0.7379	Intermediate Similarity	NPC76266
0.7374	Intermediate Similarity	NPC475049
0.7364	Intermediate Similarity	NPC270586
0.7364	Intermediate Similarity	NPC470311
0.7358	Intermediate Similarity	NPC254202
0.7347	Intermediate Similarity	NPC264005
0.7347	Intermediate Similarity	NPC269360
0.7347	Intermediate Similarity	NPC305029
0.734	Intermediate Similarity	NPC304194
0.7339	Intermediate Similarity	NPC91583
0.7339	Intermediate Similarity	NPC240125
0.7339	Intermediate Similarity	NPC473844
0.7339	Intermediate Similarity	NPC51947
0.7339	Intermediate Similarity	NPC471250
0.7333	Intermediate Similarity	NPC471075
0.7327	Intermediate Similarity	NPC287118
0.7327	Intermediate Similarity	NPC277721
0.7327	Intermediate Similarity	NPC169343
0.7327	Intermediate Similarity	NPC473690
0.7327	Intermediate Similarity	NPC12297
0.7327	Intermediate Similarity	NPC471902
0.7327	Intermediate Similarity	NPC267266
0.732	Intermediate Similarity	NPC264317
0.732	Intermediate Similarity	NPC294438
0.732	Intermediate Similarity	NPC474013
0.7315	Intermediate Similarity	NPC283849
0.7315	Intermediate Similarity	NPC473538
0.7312	Intermediate Similarity	NPC63020
0.7308	Intermediate Similarity	NPC471366
0.7308	Intermediate Similarity	NPC476800
0.7308	Intermediate Similarity	NPC472186
0.7308	Intermediate Similarity	NPC473154
0.7308	Intermediate Similarity	NPC318917
0.7308	Intermediate Similarity	NPC469986
0.73	Intermediate Similarity	NPC113989
0.73	Intermediate Similarity	NPC198818
0.73	Intermediate Similarity	NPC328141
0.73	Intermediate Similarity	NPC101651
0.73	Intermediate Similarity	NPC8062
0.73	Intermediate Similarity	NPC120840
0.73	Intermediate Similarity	NPC471370
0.73	Intermediate Similarity	NPC471371
0.73	Intermediate Similarity	NPC159748
0.7297	Intermediate Similarity	NPC100383
0.7283	Intermediate Similarity	NPC92489
0.7282	Intermediate Similarity	NPC327179
0.7281	Intermediate Similarity	NPC471249
0.7281	Intermediate Similarity	NPC469822
0.7273	Intermediate Similarity	NPC475501
0.7273	Intermediate Similarity	NPC274507
0.7273	Intermediate Similarity	NPC477128
0.7273	Intermediate Similarity	NPC474845
0.7273	Intermediate Similarity	NPC476766
0.7273	Intermediate Similarity	NPC474719
0.7273	Intermediate Similarity	NPC472302
0.7264	Intermediate Similarity	NPC94919
0.7264	Intermediate Similarity	NPC165250
0.7263	Intermediate Similarity	NPC475951
0.7257	Intermediate Similarity	NPC137414
0.7255	Intermediate Similarity	NPC209868
0.7255	Intermediate Similarity	NPC84893
0.7255	Intermediate Similarity	NPC272635
0.7255	Intermediate Similarity	NPC169751
0.7255	Intermediate Similarity	NPC88507
0.7255	Intermediate Similarity	NPC303863
0.7255	Intermediate Similarity	NPC269729
0.7248	Intermediate Similarity	NPC476765
0.7248	Intermediate Similarity	NPC476123
0.7248	Intermediate Similarity	NPC284807
0.7248	Intermediate Similarity	NPC177246
0.7248	Intermediate Similarity	NPC28198
0.7245	Intermediate Similarity	NPC244174
0.7245	Intermediate Similarity	NPC471368
0.7245	Intermediate Similarity	NPC471042
0.7245	Intermediate Similarity	NPC85698
0.7238	Intermediate Similarity	NPC472187
0.7238	Intermediate Similarity	NPC476767
0.7238	Intermediate Similarity	NPC473204
0.7238	Intermediate Similarity	NPC470906
0.7238	Intermediate Similarity	NPC473545
0.7234	Intermediate Similarity	NPC471475
0.7234	Intermediate Similarity	NPC305835
0.7228	Intermediate Similarity	NPC187722
0.7228	Intermediate Similarity	NPC49420
0.7228	Intermediate Similarity	NPC475416
0.7228	Intermediate Similarity	NPC329842
0.7222	Intermediate Similarity	NPC127790
0.7222	Intermediate Similarity	NPC252296
0.7216	Intermediate Similarity	NPC219011

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 NPC164750 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	265
0.1-0.2	2263
0.2-0.3	3849
0.3-0.4	1954
0.4-0.5	486
0.5-0.6	264
0.6-0.7	58
0.7-0.8	11
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
0.7576	Intermediate Similarity	NPD8034	Phase 2
0.7576	Intermediate Similarity	NPD8035	Phase 2
0.7387	Intermediate Similarity	NPD8133	Approved
0.732	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD7900	Approved
0.7255	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7507	Approved
0.7091	Intermediate Similarity	NPD6686	Approved
0.7087	Intermediate Similarity	NPD7748	Approved
0.7048	Intermediate Similarity	NPD7902	Approved
0.701	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.699	Remote Similarity	NPD6399	Phase 3
0.6967	Remote Similarity	NPD7319	Approved
0.6931	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7515	Phase 2
0.6822	Remote Similarity	NPD7638	Approved
0.6759	Remote Similarity	NPD7640	Approved
0.6759	Remote Similarity	NPD7639	Approved
0.6733	Remote Similarity	NPD5330	Approved
0.6733	Remote Similarity	NPD7521	Approved
0.6733	Remote Similarity	NPD6684	Approved
0.6733	Remote Similarity	NPD7334	Approved
0.6733	Remote Similarity	NPD6409	Approved
0.6733	Remote Similarity	NPD7146	Approved
0.661	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD6672	Approved
0.6602	Remote Similarity	NPD6903	Approved
0.6602	Remote Similarity	NPD5737	Approved
0.6579	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD7327	Approved
0.6555	Remote Similarity	NPD7328	Approved
0.6549	Remote Similarity	NPD6412	Phase 2
0.6529	Remote Similarity	NPD8033	Approved
0.65	Remote Similarity	NPD7516	Approved
0.6495	Remote Similarity	NPD6116	Phase 1
0.6489	Remote Similarity	NPD5777	Approved
0.6446	Remote Similarity	NPD8377	Approved
0.6446	Remote Similarity	NPD8294	Approved
0.6423	Remote Similarity	NPD8328	Phase 3
0.6415	Remote Similarity	NPD5693	Phase 1
0.641	Remote Similarity	NPD6882	Approved
0.6404	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD8380	Approved
0.6393	Remote Similarity	NPD8296	Approved
0.6393	Remote Similarity	NPD8379	Approved
0.6393	Remote Similarity	NPD8335	Approved
0.6393	Remote Similarity	NPD8378	Approved
0.6392	Remote Similarity	NPD6117	Approved
0.6381	Remote Similarity	NPD6051	Approved
0.6373	Remote Similarity	NPD4786	Approved
0.6373	Remote Similarity	NPD3668	Phase 3
0.6354	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD3573	Approved
0.6339	Remote Similarity	NPD7632	Discontinued
0.6337	Remote Similarity	NPD3667	Approved
0.6333	Remote Similarity	NPD7115	Discovery
0.6316	Remote Similarity	NPD6402	Approved
0.6316	Remote Similarity	NPD6008	Approved
0.6316	Remote Similarity	NPD5739	Approved
0.6316	Remote Similarity	NPD6675	Approved
0.6316	Remote Similarity	NPD7128	Approved
0.6311	Remote Similarity	NPD1694	Approved
0.6293	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD4788	Approved
0.6263	Remote Similarity	NPD6118	Approved
0.6263	Remote Similarity	NPD6114	Approved
0.6263	Remote Similarity	NPD6697	Approved
0.6263	Remote Similarity	NPD6115	Approved
0.626	Remote Similarity	NPD7503	Approved
0.625	Remote Similarity	NPD6098	Approved
0.6239	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD6904	Approved
0.6226	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD6080	Approved
0.6226	Remote Similarity	NPD6673	Approved
0.622	Remote Similarity	NPD7736	Approved
0.6216	Remote Similarity	NPD4225	Approved
0.6207	Remote Similarity	NPD6881	Approved
0.6207	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD7320	Approved
0.6207	Remote Similarity	NPD6899	Approved
0.6154	Remote Similarity	NPD6373	Approved
0.6154	Remote Similarity	NPD6372	Approved
0.6126	Remote Similarity	NPD6084	Phase 2
0.6126	Remote Similarity	NPD6083	Phase 2
0.6121	Remote Similarity	NPD5697	Approved
0.6121	Remote Similarity	NPD5701	Approved
0.6111	Remote Similarity	NPD6411	Approved
0.6102	Remote Similarity	NPD7290	Approved
0.6102	Remote Similarity	NPD6883	Approved
0.6102	Remote Similarity	NPD7102	Approved
0.6095	Remote Similarity	NPD3618	Phase 1
0.6075	Remote Similarity	NPD5328	Approved
0.6068	Remote Similarity	NPD6011	Approved
0.6058	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.605	Remote Similarity	NPD6847	Approved
0.605	Remote Similarity	NPD6650	Approved
0.605	Remote Similarity	NPD8130	Phase 1
0.605	Remote Similarity	NPD6869	Approved
0.605	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.605	Remote Similarity	NPD6649	Approved
0.605	Remote Similarity	NPD6617	Approved
0.604	Remote Similarity	NPD7645	Phase 2
0.6036	Remote Similarity	NPD4697	Phase 3
0.6032	Remote Similarity	NPD7122	Discontinued
0.6017	Remote Similarity	NPD6012	Approved
0.6017	Remote Similarity	NPD6014	Approved
0.6017	Remote Similarity	NPD6013	Approved
0.6016	Remote Similarity	NPD8293	Discontinued
0.6	Remote Similarity	NPD8516	Approved
0.6	Remote Similarity	NPD8515	Approved
0.6	Remote Similarity	NPD8513	Phase 3
0.6	Remote Similarity	NPD6053	Discontinued
0.6	Remote Similarity	NPD8517	Approved
0.6	Remote Similarity	NPD8297	Approved
0.5981	Remote Similarity	NPD5208	Approved
0.598	Remote Similarity	NPD7525	Registered
0.5979	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD6079	Approved
0.5963	Remote Similarity	NPD6050	Approved
0.596	Remote Similarity	NPD8039	Approved
0.5952	Remote Similarity	NPD6370	Approved
0.5948	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD5695	Phase 3
0.5938	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD6009	Approved
0.5929	Remote Similarity	NPD5696	Approved
0.5926	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD6101	Approved
0.5922	Remote Similarity	NPD1780	Approved
0.5922	Remote Similarity	NPD1779	Approved
0.5909	Remote Similarity	NPD4202	Approved
0.5906	Remote Similarity	NPD6067	Discontinued
0.5905	Remote Similarity	NPD3133	Approved
0.5905	Remote Similarity	NPD3665	Phase 1
0.5905	Remote Similarity	NPD3666	Approved
0.5893	Remote Similarity	NPD7732	Phase 3
0.5872	Remote Similarity	NPD5692	Phase 3
0.5859	Remote Similarity	NPD7492	Approved
0.5856	Remote Similarity	NPD6001	Approved
0.5841	Remote Similarity	NPD4755	Approved
0.5825	Remote Similarity	NPD4695	Discontinued
0.5818	Remote Similarity	NPD5694	Approved
0.5816	Remote Similarity	NPD6081	Approved
0.5814	Remote Similarity	NPD6616	Approved
0.581	Remote Similarity	NPD7154	Phase 3
0.58	Remote Similarity	NPD3702	Approved
0.5794	Remote Similarity	NPD6059	Approved
0.5794	Remote Similarity	NPD6054	Approved
0.5789	Remote Similarity	NPD4224	Phase 2
0.5785	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD5211	Phase 2
0.5769	Remote Similarity	NPD7078	Approved
0.5766	Remote Similarity	NPD5778	Approved
0.5766	Remote Similarity	NPD5779	Approved
0.576	Remote Similarity	NPD6335	Approved
0.5752	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD5222	Approved
0.5752	Remote Similarity	NPD5221	Approved
0.5752	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5739	Remote Similarity	NPD4696	Approved
0.5739	Remote Similarity	NPD5285	Approved
0.5739	Remote Similarity	NPD4700	Approved
0.5739	Remote Similarity	NPD5286	Approved
0.5727	Remote Similarity	NPD5207	Approved
0.5726	Remote Similarity	NPD6868	Approved
0.5726	Remote Similarity	NPD6940	Discontinued
0.5726	Remote Similarity	NPD6274	Approved
0.5714	Remote Similarity	NPD7101	Approved
0.5714	Remote Similarity	NPD4245	Approved
0.5714	Remote Similarity	NPD4244	Approved
0.5714	Remote Similarity	NPD7100	Approved
0.5702	Remote Similarity	NPD5173	Approved
0.5691	Remote Similarity	NPD4632	Approved
0.5691	Remote Similarity	NPD6858	Approved
0.5691	Remote Similarity	NPD7094	Approved
0.569	Remote Similarity	NPD5223	Approved
0.568	Remote Similarity	NPD6317	Approved
0.5678	Remote Similarity	NPD5141	Approved
0.5676	Remote Similarity	NPD5281	Approved
0.5676	Remote Similarity	NPD5284	Approved
0.5676	Remote Similarity	NPD7637	Suspended
0.5673	Remote Similarity	NPD6928	Phase 2
0.567	Remote Similarity	NPD5360	Phase 3
0.567	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD6942	Approved
0.5644	Remote Similarity	NPD3703	Phase 2
0.5644	Remote Similarity	NPD7339	Approved
0.5641	Remote Similarity	NPD5225	Approved
0.5641	Remote Similarity	NPD5224	Approved
0.5641	Remote Similarity	NPD5226	Approved
0.5641	Remote Similarity	NPD4633	Approved
0.5636	Remote Similarity	NPD4753	Phase 2
0.5635	Remote Similarity	NPD6314	Approved
0.5635	Remote Similarity	NPD6313	Approved
0.5631	Remote Similarity	NPD3617	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