NPASS Compound

Structure

NPC475338 OpenBabel07101719512D 42 50 0 0 1 0 0 0 0 0999 V2000 0.3621 0.0577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3677 0.1956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4213 -0.0670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4367 0.3151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9903 0.7453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5836 1.6588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5316 -0.1499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5533 0.3889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5159 -3.0418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5159 -3.0396 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4025 -0.0637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5891 1.7634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2192 -1.3309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6649 -1.6283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2071 0.2337 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6679 -0.1720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5105 -0.6254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7988 -2.1283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6909 0.4000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1928 -2.3363 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0532 0.4312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9328 -0.2057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0546 0.2624 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9052 0.2390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2214 -2.3309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4080 0.0408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6649 -0.6283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0668 -0.1283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0668 0.0264 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0013 0.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9328 -0.6283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7988 -0.1283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0870 -0.8843 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9328 0.1038 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7988 -0.1283 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5105 -0.6276 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9328 -1.6283 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.0068 0.8498 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8179 0.3459 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 0.1950 -1.3363 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -3.1462 -2.7115 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 2 1 0 0 0 0 1 3 2 0 0 0 0 2 4 1 0 0 0 0 3 7 1 0 0 0 0 4 8 1 0 0 0 0 5 6 2 0 0 0 0 5 11 1 0 0 0 0 6 12 1 0 0 0 0 7 16 1 0 0 0 0 8 19 1 0 0 0 0 9 10 1 0 0 0 0 9 20 1 0 0 0 0 10 25 1 0 0 0 0 11 26 2 0 0 0 0 12 30 2 0 0 0 0 13 17 1 0 0 0 0 13 25 1 0 0 0 0 14 18 2 0 0 0 0 14 27 1 0 0 0 0 15 21 1 0 0 0 0 15 29 1 0 0 0 0 17 36 1 0 0 0 0 18 37 1 0 0 0 0 19 39 1 0 0 0 0 20 40 1 0 0 0 0 21 39 1 0 0 0 0 22 28 2 0 0 0 0 22 35 1 0 0 0 0 23 36 1 0 0 0 0 24 34 1 0 0 0 0 24 39 1 0 0 0 0 25 41 2 0 0 0 0 26 27 1 0 0 0 0 26 30 1 0 0 0 0 27 32 2 0 0 0 0 28 29 1 0 0 0 0 28 31 1 0 0 0 0 29 34 1 1 0 0 0 30 38 1 0 0 0 0 31 32 1 0 0 0 0 31 37 2 0 0 0 0 32 38 1 0 0 0 0 33 34 1 1 0 0 0 33 35 1 0 0 0 0 33 40 1 0 0 0 0 34 23 1 6 0 0 0 35 16 1 1 0 0 0 35 42 1 0 0 0 0 36 40 1 6 0 0 0 36 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	562.33
Volume:	592.043
LogP:	3.971
LogD:	3.352
LogS:	-3.59
# Rotatable Bonds:	1
TPSA:	61.46
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	9
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.338
Synthetic Accessibility Score:	7.035
Fsp3:	0.556
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.197
MDCK Permeability:	3.238611316191964e-05
Pgp-inhibitor:	0.987
Pgp-substrate:	0.642
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.989
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.859
Plasma Protein Binding (PPB):	89.12230682373047%
Volume Distribution (VD):	2.498
Pgp-substrate:	7.663353443145752%

ADMET: Metabolism

CYP1A2-inhibitor:	0.092
CYP1A2-substrate:	0.812
CYP2C19-inhibitor:	0.259
CYP2C19-substrate:	0.563
CYP2C9-inhibitor:	0.235
CYP2C9-substrate:	0.317
CYP2D6-inhibitor:	0.981
CYP2D6-substrate:	0.933
CYP3A4-inhibitor:	0.98
CYP3A4-substrate:	0.91

ADMET: Excretion

Clearance (CL):	10.004
Half-life (T1/2):	0.578

ADMET: Toxicity

hERG Blockers:	0.96
Human Hepatotoxicity (H-HT):	0.986
Drug-inuced Liver Injury (DILI):	0.047
AMES Toxicity:	0.771
Rat Oral Acute Toxicity:	0.879
Maximum Recommended Daily Dose:	0.98
Skin Sensitization:	0.7
Carcinogencity:	0.719
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC475338

Natural Product ID:	NPC475338
*Common Name:**	XYMOBPPDZDVIQE-WNYIVBKMSA-N
IUPAC Name:	n.a.
Synonyms:	Ent-12,34-Oxamanamine E
Standard InCHIKey:	XYMOBPPDZDVIQE-WNYIVBKMSA-N
Standard InCHI:	InChI=1S/C36H42N4O2/c41-25-10-9-20-40-33-34-23-36(40,17-13-25)42-35(33)16-7-3-1-2-4-8-19-39(24-34)21-15-29(34)28(22-35)31-32-27(14-18-37-31)26-11-5-6-12-30(26)38-32/h1,3,5-6,11-12,14,18,22,29,33,38H,2,4,7-10,13,15-17,19-21,23-24H2/b3-1-/t29-,33+,34-,35+,36-/m0/s1
SMILES:	O=C1CCCN2[C@@]3(CC1)O[C@]14[C@H]2[C@@]2(C3)CN(CCCC/C=CCC1)CC[C@H]2C(=C4)c1nccc2c1[nH]c1c2cccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503743
PubChem CID:	44566804
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001140] Harmala alkaloids

*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
NPO32531	sponge sp.	Species	n.a.	n.a.	n.a.	collected from vertical slopes between 33 and 40 m from Knife Cape, Manado Bay, Indonesia	2011-MAR	PMID[12828469]

☑ 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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	128.0	ug.mL-1	PMID[569100]

☑ 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 NPC475338 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	543
0.1-0.2	2372
0.2-0.3	14485
0.3-0.4	17982
0.4-0.5	3130
0.5-0.6	2175
0.6-0.7	1758
0.7-0.8	232
0.8-0.85	11
0.85-0.9	4
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC909
0.9851	High Similarity	NPC475258
0.9265	High Similarity	NPC473310
0.9257	High Similarity	NPC473757
0.9073	High Similarity	NPC472027
0.8636	High Similarity	NPC41679
0.8592	High Similarity	NPC473362
0.8592	High Similarity	NPC471506
0.8592	High Similarity	NPC166492
0.8479	Intermediate Similarity	NPC476491
0.8438	Intermediate Similarity	NPC473312
0.8396	Intermediate Similarity	NPC250835
0.8293	Intermediate Similarity	NPC265576
0.8227	Intermediate Similarity	NPC476492
0.821	Intermediate Similarity	NPC471891
0.8104	Intermediate Similarity	NPC475288
0.8095	Intermediate Similarity	NPC471564
0.8063	Intermediate Similarity	NPC6215
0.8018	Intermediate Similarity	NPC251936
0.7991	Intermediate Similarity	NPC81175
0.7991	Intermediate Similarity	NPC476493
0.7876	Intermediate Similarity	NPC476451
0.7864	Intermediate Similarity	NPC477714
0.7818	Intermediate Similarity	NPC477715
0.7788	Intermediate Similarity	NPC126066
0.7642	Intermediate Similarity	NPC232130
0.7632	Intermediate Similarity	NPC56109
0.7632	Intermediate Similarity	NPC191382
0.7602	Intermediate Similarity	NPC234078
0.7602	Intermediate Similarity	NPC221100
0.7566	Intermediate Similarity	NPC155444
0.7548	Intermediate Similarity	NPC62749
0.7545	Intermediate Similarity	NPC475422
0.7523	Intermediate Similarity	NPC67288
0.7523	Intermediate Similarity	NPC171317
0.7512	Intermediate Similarity	NPC11445
0.75	Intermediate Similarity	NPC162860
0.75	Intermediate Similarity	NPC478158
0.7489	Intermediate Similarity	NPC54420
0.7467	Intermediate Similarity	NPC472762
0.7465	Intermediate Similarity	NPC157828
0.7465	Intermediate Similarity	NPC195239
0.7465	Intermediate Similarity	NPC260900
0.7455	Intermediate Similarity	NPC87755
0.7454	Intermediate Similarity	NPC252338
0.7444	Intermediate Similarity	NPC475602
0.7421	Intermediate Similarity	NPC271862
0.7411	Intermediate Similarity	NPC478157
0.7409	Intermediate Similarity	NPC477065
0.7403	Intermediate Similarity	NPC314954
0.7399	Intermediate Similarity	NPC118940
0.7393	Intermediate Similarity	NPC213629
0.7393	Intermediate Similarity	NPC321708
0.7389	Intermediate Similarity	NPC281049
0.7373	Intermediate Similarity	NPC214428
0.7371	Intermediate Similarity	NPC470730
0.7371	Intermediate Similarity	NPC477175
0.7368	Intermediate Similarity	NPC2395
0.7364	Intermediate Similarity	NPC277350
0.7358	Intermediate Similarity	NPC472112
0.7352	Intermediate Similarity	NPC98715
0.7342	Intermediate Similarity	NPC477861
0.7339	Intermediate Similarity	NPC477177
0.7339	Intermediate Similarity	NPC475969
0.7339	Intermediate Similarity	NPC475859
0.7333	Intermediate Similarity	NPC15102
0.7327	Intermediate Similarity	NPC74413
0.7327	Intermediate Similarity	NPC293917
0.7321	Intermediate Similarity	NPC151976
0.7321	Intermediate Similarity	NPC87856
0.7321	Intermediate Similarity	NPC318299
0.7319	Intermediate Similarity	NPC325976
0.7318	Intermediate Similarity	NPC327592
0.7315	Intermediate Similarity	NPC227582
0.7311	Intermediate Similarity	NPC63199
0.7311	Intermediate Similarity	NPC196251
0.7311	Intermediate Similarity	NPC102338
0.7311	Intermediate Similarity	NPC111602
0.7308	Intermediate Similarity	NPC165743
0.7304	Intermediate Similarity	NPC229893
0.7301	Intermediate Similarity	NPC132211
0.7301	Intermediate Similarity	NPC36405
0.7297	Intermediate Similarity	NPC127677
0.7297	Intermediate Similarity	NPC258062
0.7293	Intermediate Similarity	NPC474896
0.729	Intermediate Similarity	NPC472113
0.7289	Intermediate Similarity	NPC267965
0.7289	Intermediate Similarity	NPC317752
0.7286	Intermediate Similarity	NPC472119
0.7286	Intermediate Similarity	NPC284678
0.7285	Intermediate Similarity	NPC238457
0.7285	Intermediate Similarity	NPC317373
0.7273	Intermediate Similarity	NPC235885
0.7269	Intermediate Similarity	NPC304926
0.7269	Intermediate Similarity	NPC476041
0.7269	Intermediate Similarity	NPC245916
0.7265	Intermediate Similarity	NPC223791
0.7265	Intermediate Similarity	NPC107077
0.7264	Intermediate Similarity	NPC17059
0.7261	Intermediate Similarity	NPC31097
0.7253	Intermediate Similarity	NPC33949
0.7252	Intermediate Similarity	NPC225821
0.7252	Intermediate Similarity	NPC46225
0.7246	Intermediate Similarity	NPC280852
0.7243	Intermediate Similarity	NPC473763
0.7243	Intermediate Similarity	NPC117244
0.7232	Intermediate Similarity	NPC123839
0.7227	Intermediate Similarity	NPC193761
0.7227	Intermediate Similarity	NPC476073
0.7227	Intermediate Similarity	NPC476874
0.7225	Intermediate Similarity	NPC204491
0.7225	Intermediate Similarity	NPC203614
0.722	Intermediate Similarity	NPC266249
0.7217	Intermediate Similarity	NPC94752
0.7212	Intermediate Similarity	NPC54744
0.7212	Intermediate Similarity	NPC145885
0.7212	Intermediate Similarity	NPC14113
0.7212	Intermediate Similarity	NPC84827
0.7212	Intermediate Similarity	NPC59269
0.7204	Intermediate Similarity	NPC472294
0.7202	Intermediate Similarity	NPC131887
0.7192	Intermediate Similarity	NPC21174
0.7192	Intermediate Similarity	NPC271797
0.7182	Intermediate Similarity	NPC300183
0.7182	Intermediate Similarity	NPC475506
0.7181	Intermediate Similarity	NPC474412
0.7177	Intermediate Similarity	NPC213468
0.7176	Intermediate Similarity	NPC326422
0.7174	Intermediate Similarity	NPC272174
0.717	Intermediate Similarity	NPC99939
0.717	Intermediate Similarity	NPC308931
0.7169	Intermediate Similarity	NPC241024
0.7169	Intermediate Similarity	NPC100321
0.7168	Intermediate Similarity	NPC75634
0.7166	Intermediate Similarity	NPC53534
0.7162	Intermediate Similarity	NPC473376
0.7161	Intermediate Similarity	NPC101543
0.7161	Intermediate Similarity	NPC469554
0.7149	Intermediate Similarity	NPC326363
0.7149	Intermediate Similarity	NPC69843
0.7149	Intermediate Similarity	NPC477176
0.7149	Intermediate Similarity	NPC470729
0.7149	Intermediate Similarity	NPC155143
0.7143	Intermediate Similarity	NPC469896
0.7137	Intermediate Similarity	NPC57690
0.7136	Intermediate Similarity	NPC199851
0.7136	Intermediate Similarity	NPC128265
0.7136	Intermediate Similarity	NPC249150
0.7136	Intermediate Similarity	NPC235684
0.7136	Intermediate Similarity	NPC81654
0.7136	Intermediate Similarity	NPC49196
0.7136	Intermediate Similarity	NPC294909
0.7136	Intermediate Similarity	NPC79129
0.7136	Intermediate Similarity	NPC195461
0.7136	Intermediate Similarity	NPC313985
0.7136	Intermediate Similarity	NPC254240
0.7136	Intermediate Similarity	NPC312870
0.7131	Intermediate Similarity	NPC70155
0.7124	Intermediate Similarity	NPC476818
0.7123	Intermediate Similarity	NPC473640
0.7123	Intermediate Similarity	NPC52557
0.7123	Intermediate Similarity	NPC50503
0.7119	Intermediate Similarity	NPC474877
0.7116	Intermediate Similarity	NPC329858
0.7089	Intermediate Similarity	NPC63031
0.7085	Intermediate Similarity	NPC475070
0.7083	Intermediate Similarity	NPC101350
0.7083	Intermediate Similarity	NPC472097
0.7082	Intermediate Similarity	NPC266192
0.7078	Intermediate Similarity	NPC81939
0.7075	Intermediate Similarity	NPC143533
0.7074	Intermediate Similarity	NPC470731
0.7073	Intermediate Similarity	NPC14812
0.7072	Intermediate Similarity	NPC162730
0.7072	Intermediate Similarity	NPC328596
0.7072	Intermediate Similarity	NPC328318
0.707	Intermediate Similarity	NPC175474
0.7069	Intermediate Similarity	NPC60621
0.7067	Intermediate Similarity	NPC314957
0.7064	Intermediate Similarity	NPC220151
0.7064	Intermediate Similarity	NPC133366
0.7064	Intermediate Similarity	NPC19692
0.7059	Intermediate Similarity	NPC63279
0.7056	Intermediate Similarity	NPC478077
0.7051	Intermediate Similarity	NPC55493
0.7051	Intermediate Similarity	NPC141428
0.7049	Intermediate Similarity	NPC475666
0.7049	Intermediate Similarity	NPC469734
0.7048	Intermediate Similarity	NPC82370
0.7048	Intermediate Similarity	NPC320968
0.7042	Intermediate Similarity	NPC235685
0.7042	Intermediate Similarity	NPC228835
0.7042	Intermediate Similarity	NPC258480
0.704	Intermediate Similarity	NPC317701
0.7039	Intermediate Similarity	NPC160105
0.7039	Intermediate Similarity	NPC56233
0.7037	Intermediate Similarity	NPC314333
0.7033	Intermediate Similarity	NPC203468
0.7033	Intermediate Similarity	NPC110500
0.7033	Intermediate Similarity	NPC149155

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 NPC475338 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	262
0.1-0.2	563
0.2-0.3	833
0.3-0.4	2236
0.4-0.5	2520
0.5-0.6	2036
0.6-0.7	652
0.7-0.8	48
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
0.7991	Intermediate Similarity	NPD7824	Approved
0.7965	Intermediate Similarity	NPD7791	Approved
0.7965	Intermediate Similarity	NPD7952	Approved
0.7965	Intermediate Similarity	NPD7790	Approved
0.7965	Intermediate Similarity	NPD7953	Approved
0.7965	Intermediate Similarity	NPD7950	Approved
0.7965	Intermediate Similarity	NPD7951	Approved
0.7965	Intermediate Similarity	NPD7789	Approved
0.7902	Intermediate Similarity	NPD7731	Approved
0.7902	Intermediate Similarity	NPD7730	Approved
0.7812	Intermediate Similarity	NPD7271	Approved
0.7632	Intermediate Similarity	NPD7781	Approved
0.7632	Intermediate Similarity	NPD7780	Approved
0.7558	Intermediate Similarity	NPD5426	Phase 3
0.7557	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD7665	Phase 2
0.7455	Intermediate Similarity	NPD7666	Phase 3
0.7432	Intermediate Similarity	NPD7470	Discontinued
0.7416	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD3394	Approved
0.7301	Intermediate Similarity	NPD3389	Approved
0.7301	Intermediate Similarity	NPD3393	Approved
0.7252	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.722	Intermediate Similarity	NPD2509	Approved
0.722	Intermediate Similarity	NPD2510	Approved
0.7212	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD6999	Discontinued
0.7168	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7618	Phase 3
0.7143	Intermediate Similarity	NPD7619	Phase 3
0.7136	Intermediate Similarity	NPD4601	Approved
0.7136	Intermediate Similarity	NPD4600	Approved
0.7136	Intermediate Similarity	NPD4500	Approved
0.7136	Intermediate Similarity	NPD4501	Approved
0.713	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD7001	Phase 3
0.713	Intermediate Similarity	NPD7957	Phase 1
0.713	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD2091	Phase 2
0.7123	Intermediate Similarity	NPD2096	Phase 2
0.7118	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD8093	Discontinued
0.7091	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD5003	Discontinued
0.7075	Intermediate Similarity	NPD2095	Phase 2
0.7075	Intermediate Similarity	NPD2094	Phase 2
0.7075	Intermediate Similarity	NPD2092	Phase 2
0.7062	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD6595	Phase 3
0.7048	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD6178	Phase 3
0.704	Intermediate Similarity	NPD4886	Phase 2
0.7037	Intermediate Similarity	NPD4499	Approved
0.7035	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD482	Approved
0.7023	Intermediate Similarity	NPD8431	Approved
0.702	Intermediate Similarity	NPD8358	Approved
0.7009	Intermediate Similarity	NPD8283	Approved
0.7009	Intermediate Similarity	NPD56	Approved
0.7009	Intermediate Similarity	NPD7717	Approved
0.7009	Intermediate Similarity	NPD7716	Approved
0.7009	Intermediate Similarity	NPD8282	Approved
0.7008	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7004	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD6165	Phase 2
0.6992	Remote Similarity	NPD6164	Phase 2
0.6991	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD3402	Phase 1
0.6983	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6277	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD5065	Approved
0.6949	Remote Similarity	NPD8289	Discontinued
0.6949	Remote Similarity	NPD7711	Discontinued
0.6947	Remote Similarity	NPD8322	Phase 2
0.6944	Remote Similarity	NPD3961	Discontinued
0.6943	Remote Similarity	NPD7455	Approved
0.6943	Remote Similarity	NPD7454	Approved
0.6943	Remote Similarity	NPD3330	Phase 1
0.6933	Remote Similarity	NPD5901	Discontinued
0.6933	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.693	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD5913	Phase 3
0.6923	Remote Similarity	NPD6664	Approved
0.692	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.692	Remote Similarity	NPD6978	Phase 2
0.692	Remote Similarity	NPD8073	Approved
0.692	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD8094	Discontinued
0.6909	Remote Similarity	NPD7944	Discontinued
0.6909	Remote Similarity	NPD4602	Approved
0.6906	Remote Similarity	NPD6479	Discontinued
0.6901	Remote Similarity	NPD5473	Discontinued
0.6895	Remote Similarity	NPD5482	Discontinued
0.689	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.686	Remote Similarity	NPD5891	Approved
0.6856	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD8247	Approved
0.6853	Remote Similarity	NPD8246	Approved
0.6847	Remote Similarity	NPD2837	Discontinued
0.6846	Remote Similarity	NPD7415	Suspended
0.6845	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.684	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD750	Phase 2
0.682	Remote Similarity	NPD5559	Phase 2
0.6814	Remote Similarity	NPD8072	Approved
0.681	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.681	Remote Similarity	NPD7970	Approved
0.6809	Remote Similarity	NPD6242	Discontinued
0.6808	Remote Similarity	NPD2144	Approved
0.6807	Remote Similarity	NPD7603	Discontinued
0.6806	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD2565	Phase 2
0.6804	Remote Similarity	NPD2564	Approved
0.6802	Remote Similarity	NPD7921	Approved
0.68	Remote Similarity	NPD5017	Discontinued
0.6791	Remote Similarity	NPD3038	Discontinued
0.6784	Remote Similarity	NPD8272	Phase 2
0.6783	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6615	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD3323	Discontinued
0.6774	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD8100	Phase 3
0.6773	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD2880	Discontinued
0.6771	Remote Similarity	NPD7948	Phase 1
0.6769	Remote Similarity	NPD8399	Phase 1
0.6769	Remote Similarity	NPD8423	Phase 2
0.6766	Remote Similarity	NPD7404	Approved
0.6761	Remote Similarity	NPD4075	Phase 2
0.6758	Remote Similarity	NPD7233	Approved
0.6758	Remote Similarity	NPD7234	Approved
0.6757	Remote Similarity	NPD8363	Approved
0.6757	Remote Similarity	NPD8364	Approved
0.6755	Remote Similarity	NPD8426	Approved
0.6755	Remote Similarity	NPD8425	Approved
0.6753	Remote Similarity	NPD5475	Discontinued
0.6752	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD8326	Phase 3
0.6752	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD8325	Phase 3
0.6751	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.673	Remote Similarity	NPD8428	Approved
0.673	Remote Similarity	NPD8429	Approved
0.673	Remote Similarity	NPD8427	Approved
0.6729	Remote Similarity	NPD4181	Approved
0.6728	Remote Similarity	NPD7564	Discontinued
0.6727	Remote Similarity	NPD6281	Approved
0.6724	Remote Similarity	NPD2411	Approved
0.6718	Remote Similarity	NPD7925	Phase 2
0.6718	Remote Similarity	NPD7924	Phase 2
0.6711	Remote Similarity	NPD8098	Approved
0.6705	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD7187	Phase 2
0.6694	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD7688	Phase 1
0.6693	Remote Similarity	NPD8101	Phase 3
0.6682	Remote Similarity	NPD5104	Approved
0.6682	Remote Similarity	NPD4427	Phase 2
0.6682	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD484	Approved
0.6681	Remote Similarity	NPD2008	Discontinued
0.668	Remote Similarity	NPD6530	Approved
0.668	Remote Similarity	NPD6531	Approved
0.6667	Remote Similarity	NPD7073	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8467	Approved
0.6667	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4885	Approved
0.6667	Remote Similarity	NPD8465	Approved
0.6667	Remote Similarity	NPD8466	Approved
0.6667	Remote Similarity	NPD2172	Phase 1
0.6667	Remote Similarity	NPD8119	Discontinued
0.6653	Remote Similarity	NPD4558	Phase 2
0.6652	Remote Similarity	NPD8063	Discontinued
0.6652	Remote Similarity	NPD4852	Phase 2
0.6652	Remote Similarity	NPD3905	Phase 3
0.6652	Remote Similarity	NPD8410	Clinical (unspecified phase)
0.664	Remote Similarity	NPD6992	Phase 2

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