NPASS Compound

Structure

NPC472466 OpenBabel07101719252D 27 29 0 0 1 0 0 0 0 0999 V2000 -1.2601 -1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4680 3.2382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3427 1.1797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7824 3.9303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9975 1.0707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9543 1.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1622 2.8781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8564 2.5180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -0.9511 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2601 2.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5506 2.1579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 1.9511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0032 1.5909 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.3090 1.9511 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1132 3.1871 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.5016 2.4669 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7953 0.6128 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2601 2.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8042 4.1382 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8074 2.8270 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 13 2 0 0 0 0 3 14 1 0 0 0 0 4 21 1 0 0 0 0 5 22 1 0 0 0 0 6 7 1 0 0 0 0 6 12 1 0 0 0 0 7 16 1 0 0 0 0 8 9 2 0 0 0 0 8 17 1 0 0 0 0 9 21 1 0 0 0 0 10 15 1 0 0 0 0 10 18 1 0 0 0 0 11 21 1 0 0 0 0 11 27 1 0 0 0 0 12 1 1 1 0 0 0 12 19 1 0 0 0 0 13 17 1 0 0 0 0 14 23 2 0 0 0 0 14 27 1 0 0 0 0 15 13 1 6 0 0 0 15 20 1 0 0 0 0 16 19 1 0 0 0 0 16 22 1 1 0 0 0 17 24 1 0 0 0 0 18 22 1 1 0 0 0 18 25 1 0 0 0 0 19 20 1 0 0 0 0 20 22 1 0 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	378.24
Volume:	399.441
LogP:	1.574
LogD:	2.459
LogS:	-2.861
# Rotatable Bonds:	7
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.488
Synthetic Accessibility Score:	5.321
Fsp3:	0.773
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:	-4.829
MDCK Permeability:	0.00011906528379768133
Pgp-inhibitor:	0.0
Pgp-substrate:	0.6
Human Intestinal Absorption (HIA):	0.81
20% Bioavailability (F20%):	0.425
30% Bioavailability (F30%):	0.063

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.232
Plasma Protein Binding (PPB):	69.47025299072266%
Volume Distribution (VD):	0.771
Pgp-substrate:	28.29933738708496%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.191
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.759
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.081
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.069
CYP3A4-inhibitor:	0.492
CYP3A4-substrate:	0.375

ADMET: Excretion

Clearance (CL):	2.1
Half-life (T1/2):	0.527

ADMET: Toxicity

hERG Blockers:	0.055
Human Hepatotoxicity (H-HT):	0.659
Drug-inuced Liver Injury (DILI):	0.309
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.203
Maximum Recommended Daily Dose:	0.975
Skin Sensitization:	0.059
Carcinogencity:	0.005
Eye Corrosion:	0.003
Eye Irritation:	0.04
Respiratory Toxicity:	0.808

Download Data

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

Natural Product: NPC472466

Natural Product ID:	NPC472466
*Common Name:**	UXICUUKBZBBBOI-VBWCVHTESA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	UXICUUKBZBBBOI-VBWCVHTESA-N
Standard InCHI:	InChI=1S/C22H34O5/c1-12-6-7-16-19(12)20-15(10-18(25)22(16,20)5)13(2)17(24)8-9-21(4,26)11-27-14(3)23/h8-9,12,15-20,24-26H,2,6-7,10-11H2,1,3-5H3/b9-8+/t12-,15+,16+,17?,18-,19-,20+,21?,22+/m1/s1
SMILES:	CC(=O)OCC(/C=C/C(C(=C)[C@@H]1C[C@H]([C@]2([C@@H]1[C@@H]1[C@H](C)CC[C@H]21)C)O)O)(O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3425784
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001595] Spatane and 4,10-secospatane diterpenoids

*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
NPO5780	Stoechospermum marginatum	Species	Dictyotaceae	Eukaryota	n.a.	At a depth of 510 m, Gulf of Mannar near Mandapam coast (9 16'N, 79 12'E), Tamilnadu, India	2013-May	PMID[25978960]
NPO5780	Stoechospermum marginatum	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
IC50	3
MIC	4
Others	4

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	2
Organism	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1970	Cell Line	THP-1	Homo sapiens	IC50	=	67.02	ug.mL-1	PMID[447420]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	200.0	ug.mL-1	PMID[447420]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	200.0	ug.mL-1	PMID[447420]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	IZ	=	12.33	mm	PMID[447420]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	IZ	=	12.0	mm	PMID[447420]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	10.33	mm	PMID[447420]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	13.0	mm	PMID[447420]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	99.84	ug.mL-1	PMID[447420]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	143.59	ug.mL-1	PMID[447420]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	=	200.0	ug.mL-1	PMID[447420]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	400.0	ug.mL-1	PMID[447420]

☑ 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 NPC472466 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	202
0.1-0.2	1378
0.2-0.3	5636
0.3-0.4	16110
0.4-0.5	8660
0.5-0.6	7453
0.6-0.7	3058
0.7-0.8	186
0.8-0.85	7
0.85-0.9	3
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9882	High Similarity	NPC472468
0.9655	High Similarity	NPC472467
0.9048	High Similarity	NPC472465
0.8929	High Similarity	NPC472471
0.8721	High Similarity	NPC472473
0.8696	High Similarity	NPC472469
0.8372	Intermediate Similarity	NPC472470
0.8333	Intermediate Similarity	NPC472472
0.8333	Intermediate Similarity	NPC310643
0.8222	Intermediate Similarity	NPC477668
0.809	Intermediate Similarity	NPC477667
0.8	Intermediate Similarity	NPC113639
0.7816	Intermediate Similarity	NPC40049
0.7816	Intermediate Similarity	NPC476439
0.7723	Intermediate Similarity	NPC475623
0.7723	Intermediate Similarity	NPC473694
0.7723	Intermediate Similarity	NPC475334
0.7701	Intermediate Similarity	NPC126969
0.7692	Intermediate Similarity	NPC23748
0.7692	Intermediate Similarity	NPC49208
0.7692	Intermediate Similarity	NPC471340
0.7647	Intermediate Similarity	NPC288502
0.7647	Intermediate Similarity	NPC121518
0.7647	Intermediate Similarity	NPC475335
0.7647	Intermediate Similarity	NPC475331
0.7647	Intermediate Similarity	NPC80809
0.7647	Intermediate Similarity	NPC201144
0.7647	Intermediate Similarity	NPC103298
0.7647	Intermediate Similarity	NPC181104
0.7634	Intermediate Similarity	NPC311163
0.7629	Intermediate Similarity	NPC281775
0.7629	Intermediate Similarity	NPC90453
0.7619	Intermediate Similarity	NPC181298
0.7619	Intermediate Similarity	NPC22301
0.7614	Intermediate Similarity	NPC186109
0.7609	Intermediate Similarity	NPC186155
0.7609	Intermediate Similarity	NPC78673
0.7609	Intermediate Similarity	NPC160517
0.7579	Intermediate Similarity	NPC477215
0.7579	Intermediate Similarity	NPC476388
0.7579	Intermediate Similarity	NPC299527
0.7576	Intermediate Similarity	NPC475033
0.7576	Intermediate Similarity	NPC182811
0.7576	Intermediate Similarity	NPC475032
0.7573	Intermediate Similarity	NPC60315
0.7553	Intermediate Similarity	NPC316629
0.7553	Intermediate Similarity	NPC245004
0.7551	Intermediate Similarity	NPC240838
0.7551	Intermediate Similarity	NPC220221
0.7549	Intermediate Similarity	NPC474775
0.7528	Intermediate Similarity	NPC3852
0.7527	Intermediate Similarity	NPC11804
0.7527	Intermediate Similarity	NPC471494
0.7526	Intermediate Similarity	NPC470187
0.7524	Intermediate Similarity	NPC475274
0.75	Intermediate Similarity	NPC476317
0.75	Intermediate Similarity	NPC274458
0.75	Intermediate Similarity	NPC108682
0.75	Intermediate Similarity	NPC469957
0.75	Intermediate Similarity	NPC224532
0.75	Intermediate Similarity	NPC65700
0.75	Intermediate Similarity	NPC472820
0.75	Intermediate Similarity	NPC472263
0.75	Intermediate Similarity	NPC469959
0.7476	Intermediate Similarity	NPC473577
0.7476	Intermediate Similarity	NPC474550
0.7476	Intermediate Similarity	NPC475585
0.7476	Intermediate Similarity	NPC200861
0.7475	Intermediate Similarity	NPC113433
0.7473	Intermediate Similarity	NPC471661
0.7451	Intermediate Similarity	NPC470972
0.7451	Intermediate Similarity	NPC214714
0.7451	Intermediate Similarity	NPC200672
0.7449	Intermediate Similarity	NPC473258
0.7449	Intermediate Similarity	NPC39453
0.7449	Intermediate Similarity	NPC474922
0.7447	Intermediate Similarity	NPC137253
0.7447	Intermediate Similarity	NPC61527
0.7444	Intermediate Similarity	NPC226226
0.7444	Intermediate Similarity	NPC86971
0.7444	Intermediate Similarity	NPC476701
0.7444	Intermediate Similarity	NPC55304
0.7426	Intermediate Similarity	NPC79631
0.7423	Intermediate Similarity	NPC234335
0.7423	Intermediate Similarity	NPC471747
0.7416	Intermediate Similarity	NPC84360
0.7416	Intermediate Similarity	NPC476703
0.7404	Intermediate Similarity	NPC29389
0.7404	Intermediate Similarity	NPC475290
0.7404	Intermediate Similarity	NPC469960
0.7404	Intermediate Similarity	NPC186668
0.7404	Intermediate Similarity	NPC93026
0.7404	Intermediate Similarity	NPC472818
0.7404	Intermediate Similarity	NPC265502
0.74	Intermediate Similarity	NPC469432
0.74	Intermediate Similarity	NPC231751
0.74	Intermediate Similarity	NPC477949
0.74	Intermediate Similarity	NPC476057
0.74	Intermediate Similarity	NPC347923
0.7396	Intermediate Similarity	NPC20946
0.7396	Intermediate Similarity	NPC232747
0.7383	Intermediate Similarity	NPC71680
0.7379	Intermediate Similarity	NPC472821
0.7374	Intermediate Similarity	NPC292178
0.7374	Intermediate Similarity	NPC86893
0.7368	Intermediate Similarity	NPC471657
0.7368	Intermediate Similarity	NPC45957
0.7363	Intermediate Similarity	NPC80622
0.7358	Intermediate Similarity	NPC170221
0.7358	Intermediate Similarity	NPC10064
0.7356	Intermediate Similarity	NPC477085
0.7356	Intermediate Similarity	NPC234527
0.7356	Intermediate Similarity	NPC14352
0.7353	Intermediate Similarity	NPC295110
0.7353	Intermediate Similarity	NPC475617
0.7353	Intermediate Similarity	NPC268829
0.7353	Intermediate Similarity	NPC150923
0.7353	Intermediate Similarity	NPC25177
0.7353	Intermediate Similarity	NPC222875
0.7353	Intermediate Similarity	NPC247701
0.7353	Intermediate Similarity	NPC155974
0.7353	Intermediate Similarity	NPC26557
0.7339	Intermediate Similarity	NPC216665
0.7333	Intermediate Similarity	NPC27949
0.7333	Intermediate Similarity	NPC475980
0.7333	Intermediate Similarity	NPC260814
0.7333	Intermediate Similarity	NPC323249
0.7333	Intermediate Similarity	NPC39547
0.7327	Intermediate Similarity	NPC474957
0.7327	Intermediate Similarity	NPC79449
0.7326	Intermediate Similarity	NPC4299
0.7326	Intermediate Similarity	NPC254845
0.732	Intermediate Similarity	NPC476004
0.732	Intermediate Similarity	NPC474761
0.732	Intermediate Similarity	NPC473448
0.7312	Intermediate Similarity	NPC231601
0.7312	Intermediate Similarity	NPC474809
0.7312	Intermediate Similarity	NPC161045
0.7312	Intermediate Similarity	NPC260852
0.7312	Intermediate Similarity	NPC320548
0.7308	Intermediate Similarity	NPC473543
0.7308	Intermediate Similarity	NPC472819
0.7308	Intermediate Similarity	NPC472822
0.7308	Intermediate Similarity	NPC152966
0.73	Intermediate Similarity	NPC57664
0.73	Intermediate Similarity	NPC276103
0.73	Intermediate Similarity	NPC471903
0.73	Intermediate Similarity	NPC98165
0.73	Intermediate Similarity	NPC54248
0.729	Intermediate Similarity	NPC6206
0.729	Intermediate Similarity	NPC15551
0.7283	Intermediate Similarity	NPC316844
0.7283	Intermediate Similarity	NPC474894
0.7283	Intermediate Similarity	NPC88735
0.7282	Intermediate Similarity	NPC70369
0.7282	Intermediate Similarity	NPC475956
0.7282	Intermediate Similarity	NPC252242
0.7273	Intermediate Similarity	NPC471659
0.7273	Intermediate Similarity	NPC309178
0.7273	Intermediate Similarity	NPC469491
0.7264	Intermediate Similarity	NPC308191
0.7264	Intermediate Similarity	NPC472218
0.7264	Intermediate Similarity	NPC472219
0.7264	Intermediate Similarity	NPC472217
0.7263	Intermediate Similarity	NPC293287
0.7263	Intermediate Similarity	NPC152808
0.7255	Intermediate Similarity	NPC130792
0.7255	Intermediate Similarity	NPC472826
0.7255	Intermediate Similarity	NPC38855
0.7255	Intermediate Similarity	NPC290802
0.7255	Intermediate Similarity	NPC473510
0.7255	Intermediate Similarity	NPC208358
0.7255	Intermediate Similarity	NPC475877
0.7253	Intermediate Similarity	NPC471537
0.7245	Intermediate Similarity	NPC177641
0.7245	Intermediate Similarity	NPC249034
0.7245	Intermediate Similarity	NPC208839
0.7245	Intermediate Similarity	NPC235051
0.7241	Intermediate Similarity	NPC477087
0.7241	Intermediate Similarity	NPC477086
0.7241	Intermediate Similarity	NPC41886
0.7238	Intermediate Similarity	NPC220217
0.7238	Intermediate Similarity	NPC119855
0.7238	Intermediate Similarity	NPC179891
0.7238	Intermediate Similarity	NPC470980
0.7234	Intermediate Similarity	NPC102048
0.7234	Intermediate Similarity	NPC116613
0.7228	Intermediate Similarity	NPC475894
0.7228	Intermediate Similarity	NPC254121
0.7228	Intermediate Similarity	NPC205143
0.7228	Intermediate Similarity	NPC107243
0.7228	Intermediate Similarity	NPC210337
0.7228	Intermediate Similarity	NPC161493
0.7216	Intermediate Similarity	NPC246028
0.7216	Intermediate Similarity	NPC133450
0.7212	Intermediate Similarity	NPC97487
0.7212	Intermediate Similarity	NPC473523
0.7212	Intermediate Similarity	NPC10232
0.7212	Intermediate Similarity	NPC183570
0.7212	Intermediate Similarity	NPC260809

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 NPC472466 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	177
0.1-0.2	1928
0.2-0.3	4073
0.3-0.4	2167
0.4-0.5	443
0.5-0.6	285
0.6-0.7	66
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
0.7889	Intermediate Similarity	NPD5332	Approved
0.7889	Intermediate Similarity	NPD5331	Approved
0.7889	Intermediate Similarity	NPD5362	Discontinued
0.7865	Intermediate Similarity	NPD4790	Discontinued
0.7556	Intermediate Similarity	NPD4820	Approved
0.7556	Intermediate Similarity	NPD4819	Approved
0.7556	Intermediate Similarity	NPD4822	Approved
0.7556	Intermediate Similarity	NPD4821	Approved
0.7556	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD4250	Approved
0.7553	Intermediate Similarity	NPD4251	Approved
0.7553	Intermediate Similarity	NPD7524	Approved
0.7527	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD4249	Approved
0.7423	Intermediate Similarity	NPD7637	Suspended
0.7333	Intermediate Similarity	NPD4271	Approved
0.7333	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4268	Approved
0.7312	Intermediate Similarity	NPD6695	Phase 3
0.7234	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD4269	Approved
0.7204	Intermediate Similarity	NPD4270	Approved
0.7143	Intermediate Similarity	NPD5785	Approved
0.713	Intermediate Similarity	NPD6371	Approved
0.7128	Intermediate Similarity	NPD7154	Phase 3
0.7097	Intermediate Similarity	NPD5369	Approved
0.7083	Intermediate Similarity	NPD5786	Approved
0.701	Intermediate Similarity	NPD7750	Discontinued
0.6989	Remote Similarity	NPD6930	Phase 2
0.6989	Remote Similarity	NPD4252	Approved
0.6989	Remote Similarity	NPD6931	Approved
0.6989	Remote Similarity	NPD7514	Phase 3
0.6979	Remote Similarity	NPD5363	Approved
0.697	Remote Similarity	NPD7838	Discovery
0.6961	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7640	Approved
0.6923	Remote Similarity	NPD7639	Approved
0.6923	Remote Similarity	NPD6933	Approved
0.69	Remote Similarity	NPD7983	Approved
0.6882	Remote Similarity	NPD6929	Approved
0.6869	Remote Similarity	NPD6051	Approved
0.6857	Remote Similarity	NPD5344	Discontinued
0.6852	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7328	Approved
0.6842	Remote Similarity	NPD6435	Approved
0.6842	Remote Similarity	NPD7327	Approved
0.6837	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD7638	Approved
0.681	Remote Similarity	NPD8033	Approved
0.6809	Remote Similarity	NPD7332	Phase 2
0.6783	Remote Similarity	NPD7516	Approved
0.6774	Remote Similarity	NPD7145	Approved
0.6737	Remote Similarity	NPD6902	Approved
0.6733	Remote Similarity	NPD7087	Discontinued
0.6724	Remote Similarity	NPD8377	Approved
0.6724	Remote Similarity	NPD8294	Approved
0.6703	Remote Similarity	NPD6926	Approved
0.6703	Remote Similarity	NPD6924	Approved
0.6701	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6053	Discontinued
0.6667	Remote Similarity	NPD5776	Phase 2
0.6667	Remote Similarity	NPD8296	Approved
0.6667	Remote Similarity	NPD8380	Approved
0.6667	Remote Similarity	NPD8335	Approved
0.6667	Remote Similarity	NPD8379	Approved
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD6932	Approved
0.6667	Remote Similarity	NPD4225	Approved
0.6667	Remote Similarity	NPD5779	Approved
0.6667	Remote Similarity	NPD7503	Approved
0.6667	Remote Similarity	NPD6925	Approved
0.6667	Remote Similarity	NPD8378	Approved
0.6634	Remote Similarity	NPD46	Approved
0.6634	Remote Similarity	NPD6698	Approved
0.6633	Remote Similarity	NPD6893	Approved
0.6632	Remote Similarity	NPD5368	Approved
0.6609	Remote Similarity	NPD7115	Discovery
0.6596	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6084	Phase 2
0.6571	Remote Similarity	NPD6083	Phase 2
0.6509	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD6399	Phase 3
0.6491	Remote Similarity	NPD4632	Approved
0.6486	Remote Similarity	NPD7320	Approved
0.6449	Remote Similarity	NPD6648	Approved
0.6446	Remote Similarity	NPD7507	Approved
0.6436	Remote Similarity	NPD6903	Approved
0.6404	Remote Similarity	NPD8297	Approved
0.6396	Remote Similarity	NPD6412	Phase 2
0.6392	Remote Similarity	NPD6898	Phase 1
0.6383	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD5695	Phase 3
0.6374	Remote Similarity	NPD7144	Approved
0.6374	Remote Similarity	NPD7143	Approved
0.6364	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD6683	Phase 2
0.6344	Remote Similarity	NPD4785	Approved
0.6344	Remote Similarity	NPD4784	Approved
0.6339	Remote Similarity	NPD6881	Approved
0.6339	Remote Similarity	NPD6686	Approved
0.6339	Remote Similarity	NPD6899	Approved
0.633	Remote Similarity	NPD7632	Discontinued
0.6316	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD5739	Approved
0.6306	Remote Similarity	NPD6402	Approved
0.6306	Remote Similarity	NPD7128	Approved
0.6306	Remote Similarity	NPD6675	Approved
0.6304	Remote Similarity	NPD7151	Approved
0.6304	Remote Similarity	NPD7152	Approved
0.6304	Remote Similarity	NPD7150	Approved
0.6303	Remote Similarity	NPD6319	Approved
0.629	Remote Similarity	NPD7319	Approved
0.6289	Remote Similarity	NPD7525	Registered
0.6277	Remote Similarity	NPD6942	Approved
0.6277	Remote Similarity	NPD7339	Approved
0.6264	Remote Similarity	NPD6922	Approved
0.6264	Remote Similarity	NPD6923	Approved
0.626	Remote Similarity	NPD7078	Approved
0.625	Remote Similarity	NPD6411	Approved
0.625	Remote Similarity	NPD5697	Approved
0.6238	Remote Similarity	NPD7521	Approved
0.6238	Remote Similarity	NPD7334	Approved
0.6238	Remote Similarity	NPD6684	Approved
0.6238	Remote Similarity	NPD6409	Approved
0.6238	Remote Similarity	NPD7146	Approved
0.6238	Remote Similarity	NPD5330	Approved
0.623	Remote Similarity	NPD7492	Approved
0.6228	Remote Similarity	NPD7102	Approved
0.6228	Remote Similarity	NPD7290	Approved
0.6228	Remote Similarity	NPD6883	Approved
0.6226	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD1695	Approved
0.6214	Remote Similarity	NPD5370	Suspended
0.6204	Remote Similarity	NPD5696	Approved
0.62	Remote Similarity	NPD4786	Approved
0.6195	Remote Similarity	NPD6011	Approved
0.6186	Remote Similarity	NPD6009	Approved
0.6186	Remote Similarity	NPD4195	Approved
0.6179	Remote Similarity	NPD6616	Approved
0.6174	Remote Similarity	NPD8130	Phase 1
0.6174	Remote Similarity	NPD6650	Approved
0.6174	Remote Similarity	NPD6649	Approved
0.6174	Remote Similarity	NPD6869	Approved
0.6174	Remote Similarity	NPD6847	Approved
0.6174	Remote Similarity	NPD6617	Approved
0.6168	Remote Similarity	NPD7839	Suspended
0.6167	Remote Similarity	NPD6054	Approved
0.6161	Remote Similarity	NPD6008	Approved
0.6161	Remote Similarity	NPD6640	Phase 3
0.6148	Remote Similarity	NPD7604	Phase 2
0.614	Remote Similarity	NPD6014	Approved
0.614	Remote Similarity	NPD6373	Approved
0.614	Remote Similarity	NPD6013	Approved
0.614	Remote Similarity	NPD6372	Approved
0.614	Remote Similarity	NPD6012	Approved
0.6132	Remote Similarity	NPD5282	Discontinued
0.6129	Remote Similarity	NPD4243	Approved
0.6122	Remote Similarity	NPD7509	Discontinued
0.6121	Remote Similarity	NPD6882	Approved
0.6117	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD5983	Phase 2
0.6106	Remote Similarity	NPD6685	Approved
0.6106	Remote Similarity	NPD5701	Approved
0.6105	Remote Similarity	NPD8264	Approved
0.6095	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD5284	Approved
0.6095	Remote Similarity	NPD5281	Approved
0.6087	Remote Similarity	NPD6420	Discontinued
0.608	Remote Similarity	NPD7736	Approved
0.6078	Remote Similarity	NPD6098	Approved
0.6075	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD6370	Approved
0.6058	Remote Similarity	NPD6080	Approved
0.6058	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD6673	Approved
0.6058	Remote Similarity	NPD4753	Phase 2
0.6058	Remote Similarity	NPD6101	Approved
0.6058	Remote Similarity	NPD6904	Approved
0.6048	Remote Similarity	NPD6336	Discontinued
0.604	Remote Similarity	NPD3665	Phase 1
0.604	Remote Similarity	NPD3666	Approved
0.604	Remote Similarity	NPD3133	Approved
0.6036	Remote Similarity	NPD5211	Phase 2
0.6034	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD6059	Approved
0.6	Remote Similarity	NPD8293	Discontinued
0.6	Remote Similarity	NPD5207	Approved
0.6	Remote Similarity	NPD7136	Phase 2
0.6	Remote Similarity	NPD3667	Approved
0.6	Remote Similarity	NPD5209	Approved
0.6	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD6015	Approved
0.5984	Remote Similarity	NPD6016	Approved
0.5962	Remote Similarity	NPD5737	Approved
0.5962	Remote Similarity	NPD6672	Approved
0.596	Remote Similarity	NPD4748	Discontinued
0.5948	Remote Similarity	NPD4634	Approved
0.5943	Remote Similarity	NPD6050	Approved
0.5943	Remote Similarity	NPD5693	Phase 1
0.5943	Remote Similarity	NPD5694	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