NPASS Compound

Structure

NPC472272 OpenBabel07101718292D 25 28 0 0 1 0 0 0 0 0999 V2000 -1.2321 1.0185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3997 -1.9105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4942 0.0373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2172 1.6034 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7148 1.0829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8653 0.3880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5050 -0.6827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6397 -1.0707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2872 0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6182 0.3693 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2579 -0.7014 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0108 -0.7200 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3998 -1.9254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2471 0.0187 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8868 -1.0520 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9563 1.4863 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8477 -1.2329 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9127 -2.7839 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3999 -1.9404 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9781 1.6942 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 6 1 0 0 0 0 3 7 1 0 0 0 0 4 5 1 0 0 0 0 4 12 1 0 0 0 0 5 13 1 0 0 0 0 6 17 1 0 0 0 0 7 18 1 0 0 0 0 8 14 1 0 0 0 0 8 15 1 0 0 0 0 9 12 1 0 0 0 0 10 19 1 0 0 0 0 10 20 1 0 0 0 0 11 20 1 0 0 0 0 11 21 1 0 0 0 0 12 20 1 1 0 0 0 13 17 1 6 0 0 0 13 19 1 0 0 0 0 14 17 1 6 0 0 0 14 18 1 0 0 0 0 15 19 1 1 0 0 0 15 22 1 0 0 0 0 16 18 1 0 0 0 0 16 23 2 0 0 0 0 16 24 1 0 0 0 0 17 1 1 6 0 0 0 18 2 1 1 0 0 0 19 9 1 6 0 0 0 20 25 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	352.22
Volume:	361.565
LogP:	0.612
LogD:	0.965
LogS:	-2.967
# Rotatable Bonds:	2
TPSA:	97.99
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.611
Synthetic Accessibility Score:	5.854
Fsp3:	0.95
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.425
MDCK Permeability:	2.0152521756244823e-05
Pgp-inhibitor:	0.615
Pgp-substrate:	0.064
Human Intestinal Absorption (HIA):	0.261
20% Bioavailability (F20%):	0.282
30% Bioavailability (F30%):	0.192

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.666
Plasma Protein Binding (PPB):	74.0621566772461%
Volume Distribution (VD):	0.347
Pgp-substrate:	26.156356811523438%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.288
CYP2C19-inhibitor:	0.005
CYP2C19-substrate:	0.469
CYP2C9-inhibitor:	0.007
CYP2C9-substrate:	0.072
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.115
CYP3A4-inhibitor:	0.16
CYP3A4-substrate:	0.073

ADMET: Excretion

Clearance (CL):	2.478
Half-life (T1/2):	0.812

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.113
Drug-inuced Liver Injury (DILI):	0.083
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.923
Maximum Recommended Daily Dose:	0.91
Skin Sensitization:	0.94
Carcinogencity:	0.651
Eye Corrosion:	0.67
Eye Irritation:	0.764
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC472272

Natural Product ID:	NPC472272
*Common Name:**	DJQLZKDZWLXHRN-IZFMTULVSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DJQLZKDZWLXHRN-IZFMTULVSA-N
Standard InCHI:	InChI=1S/C20H32O5/c1-17-6-3-7-18(2,16(23)24)14(17)8-15(22)19-9-12(4-5-13(17)19)20(25,10-19)11-21/h12-15,21-22,25H,3-11H2,1-2H3,(H,23,24)/t12-,13+,14+,15+,17+,18-,19-,20+/m1/s1
SMILES:	OC[C@@]1(O)C[C@@]23C[C@H]1CC[C@H]3[C@]1([C@H](C[C@@H]2O)[C@@](C)(CCC1)C(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3357409
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:0003782] Kaurane 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
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	stem wood	n.a.	DOI[10.1021/np100247r]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10395501]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10425140]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[15568797]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	stem	Taipei Botanical Garden, Taipei, Taiwan, China	2006-MAR	PMID[20828184]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	fruits	n.a.	n.a.	PMID[25499882]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9584397]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9599260]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6333	Annona glabra	Species	Annonaceae	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	1
Others	1

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	390.0	nM	PMID[475865]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	90.0	%	PMID[475865]

☑ 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 NPC472272 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	382
0.1-0.2	3142
0.2-0.3	9562
0.3-0.4	13490
0.4-0.5	5598
0.5-0.6	4910
0.6-0.7	4221
0.7-0.8	1183
0.8-0.85	151
0.85-0.9	45
0.9-0.95	10
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9277	High Similarity	NPC476727
0.9277	High Similarity	NPC476726
0.9259	High Similarity	NPC121121
0.9	High Similarity	NPC224802
0.9	High Similarity	NPC324700
0.9	High Similarity	NPC34046
0.9	High Similarity	NPC80089
0.9	High Similarity	NPC171426
0.8953	High Similarity	NPC24705
0.8953	High Similarity	NPC56962
0.8902	High Similarity	NPC12933
0.8889	High Similarity	NPC80891
0.8889	High Similarity	NPC201276
0.8889	High Similarity	NPC320144
0.8875	High Similarity	NPC180199
0.8875	High Similarity	NPC207010
0.8875	High Similarity	NPC477919
0.8875	High Similarity	NPC317913
0.8851	High Similarity	NPC77756
0.8795	High Similarity	NPC317066
0.878	High Similarity	NPC477851
0.878	High Similarity	NPC470609
0.8765	High Similarity	NPC476732
0.8765	High Similarity	NPC199965
0.8765	High Similarity	NPC185465
0.8764	High Similarity	NPC470424
0.875	High Similarity	NPC4209
0.875	High Similarity	NPC52756
0.8721	High Similarity	NPC263802
0.869	High Similarity	NPC327451
0.8675	High Similarity	NPC469745
0.8652	High Similarity	NPC476189
0.8625	High Similarity	NPC212733
0.8605	High Similarity	NPC302111
0.8605	High Similarity	NPC80700
0.8588	High Similarity	NPC50438
0.8571	High Similarity	NPC116683
0.8571	High Similarity	NPC268040
0.8556	High Similarity	NPC470423
0.8537	High Similarity	NPC471045
0.8506	High Similarity	NPC239938
0.85	High Similarity	NPC167702
0.85	High Similarity	NPC280026
0.8488	Intermediate Similarity	NPC266651
0.8478	Intermediate Similarity	NPC471241
0.8452	Intermediate Similarity	NPC476071
0.8434	Intermediate Similarity	NPC476176
0.8415	Intermediate Similarity	NPC298168
0.8415	Intermediate Similarity	NPC143133
0.8395	Intermediate Similarity	NPC317242
0.8395	Intermediate Similarity	NPC159789
0.8375	Intermediate Similarity	NPC470610
0.8375	Intermediate Similarity	NPC153719
0.8372	Intermediate Similarity	NPC473336
0.8372	Intermediate Similarity	NPC471044
0.837	Intermediate Similarity	NPC476728
0.8353	Intermediate Similarity	NPC61107
0.8353	Intermediate Similarity	NPC154043
0.8353	Intermediate Similarity	NPC202688
0.8353	Intermediate Similarity	NPC60018
0.8353	Intermediate Similarity	NPC477935
0.8353	Intermediate Similarity	NPC289486
0.8353	Intermediate Similarity	NPC30583
0.8333	Intermediate Similarity	NPC472853
0.8333	Intermediate Similarity	NPC100078
0.8316	Intermediate Similarity	NPC244969
0.8316	Intermediate Similarity	NPC213528
0.8295	Intermediate Similarity	NPC202937
0.8293	Intermediate Similarity	NPC472487
0.8293	Intermediate Similarity	NPC472486
0.8293	Intermediate Similarity	NPC163597
0.828	Intermediate Similarity	NPC472273
0.8272	Intermediate Similarity	NPC48795
0.8272	Intermediate Similarity	NPC472854
0.8261	Intermediate Similarity	NPC470031
0.8256	Intermediate Similarity	NPC477285
0.8256	Intermediate Similarity	NPC111582
0.8256	Intermediate Similarity	NPC259173
0.8247	Intermediate Similarity	NPC166079
0.8242	Intermediate Similarity	NPC291373
0.8235	Intermediate Similarity	NPC58631
0.8222	Intermediate Similarity	NPC185529
0.8222	Intermediate Similarity	NPC472146
0.8214	Intermediate Similarity	NPC472310
0.8193	Intermediate Similarity	NPC128951
0.8193	Intermediate Similarity	NPC475031
0.8193	Intermediate Similarity	NPC185915
0.8193	Intermediate Similarity	NPC221420
0.8193	Intermediate Similarity	NPC171658
0.8193	Intermediate Similarity	NPC477227
0.8193	Intermediate Similarity	NPC105208
0.8193	Intermediate Similarity	NPC192046
0.8193	Intermediate Similarity	NPC302578
0.8172	Intermediate Similarity	NPC234564
0.8171	Intermediate Similarity	NPC21220
0.8171	Intermediate Similarity	NPC27349
0.8171	Intermediate Similarity	NPC24014
0.8171	Intermediate Similarity	NPC125767
0.8161	Intermediate Similarity	NPC291310
0.8152	Intermediate Similarity	NPC477495
0.8152	Intermediate Similarity	NPC277399
0.8148	Intermediate Similarity	NPC232112
0.814	Intermediate Similarity	NPC477936
0.814	Intermediate Similarity	NPC477286
0.814	Intermediate Similarity	NPC286719
0.814	Intermediate Similarity	NPC311642
0.814	Intermediate Similarity	NPC100366
0.814	Intermediate Similarity	NPC242771
0.814	Intermediate Similarity	NPC164289
0.8125	Intermediate Similarity	NPC251201
0.8125	Intermediate Similarity	NPC470172
0.8125	Intermediate Similarity	NPC232925
0.8125	Intermediate Similarity	NPC63588
0.8118	Intermediate Similarity	NPC261616
0.8095	Intermediate Similarity	NPC18857
0.8095	Intermediate Similarity	NPC329117
0.8095	Intermediate Similarity	NPC67657
0.8072	Intermediate Similarity	NPC5767
0.8072	Intermediate Similarity	NPC475742
0.8068	Intermediate Similarity	NPC131350
0.8065	Intermediate Similarity	NPC287354
0.8065	Intermediate Similarity	NPC305808
0.8065	Intermediate Similarity	NPC215570
0.8065	Intermediate Similarity	NPC62407
0.8061	Intermediate Similarity	NPC306776
0.8049	Intermediate Similarity	NPC304499
0.8043	Intermediate Similarity	NPC472231
0.8043	Intermediate Similarity	NPC472232
0.8043	Intermediate Similarity	NPC244356
0.8043	Intermediate Similarity	NPC161035
0.8043	Intermediate Similarity	NPC224060
0.8041	Intermediate Similarity	NPC471253
0.8041	Intermediate Similarity	NPC473406
0.8025	Intermediate Similarity	NPC156277
0.8025	Intermediate Similarity	NPC151018
0.8025	Intermediate Similarity	NPC320549
0.8025	Intermediate Similarity	NPC58057
0.8023	Intermediate Similarity	NPC73515
0.8023	Intermediate Similarity	NPC190940
0.8022	Intermediate Similarity	NPC476296
0.8022	Intermediate Similarity	NPC475056
0.8	Intermediate Similarity	NPC476379
0.8	Intermediate Similarity	NPC476734
0.8	Intermediate Similarity	NPC252032
0.8	Intermediate Similarity	NPC476435
0.8	Intermediate Similarity	NPC220379
0.8	Intermediate Similarity	NPC469941
0.8	Intermediate Similarity	NPC287452
0.8	Intermediate Similarity	NPC477854
0.8	Intermediate Similarity	NPC477820
0.8	Intermediate Similarity	NPC196197
0.8	Intermediate Similarity	NPC66407
0.8	Intermediate Similarity	NPC319671
0.7979	Intermediate Similarity	NPC477853
0.7978	Intermediate Similarity	NPC155531
0.7978	Intermediate Similarity	NPC215968
0.7978	Intermediate Similarity	NPC474448
0.7976	Intermediate Similarity	NPC264602
0.7976	Intermediate Similarity	NPC474404
0.7976	Intermediate Similarity	NPC23884
0.7976	Intermediate Similarity	NPC212453
0.7959	Intermediate Similarity	NPC327093
0.7955	Intermediate Similarity	NPC219535
0.7955	Intermediate Similarity	NPC477434
0.7955	Intermediate Similarity	NPC473299
0.7955	Intermediate Similarity	NPC237938
0.7952	Intermediate Similarity	NPC174964
0.7952	Intermediate Similarity	NPC243027
0.7952	Intermediate Similarity	NPC273366
0.7952	Intermediate Similarity	NPC195155
0.7952	Intermediate Similarity	NPC196136
0.7952	Intermediate Similarity	NPC155441
0.7952	Intermediate Similarity	NPC472311
0.7952	Intermediate Similarity	NPC158208
0.7952	Intermediate Similarity	NPC97534
0.7935	Intermediate Similarity	NPC473066
0.7931	Intermediate Similarity	NPC328007
0.7931	Intermediate Similarity	NPC102156
0.7931	Intermediate Similarity	NPC148740
0.7927	Intermediate Similarity	NPC310766
0.7917	Intermediate Similarity	NPC108371
0.7912	Intermediate Similarity	NPC220498
0.7912	Intermediate Similarity	NPC61688
0.7912	Intermediate Similarity	NPC200580
0.7912	Intermediate Similarity	NPC471459
0.7912	Intermediate Similarity	NPC67653
0.7907	Intermediate Similarity	NPC474714
0.7901	Intermediate Similarity	NPC477929
0.7895	Intermediate Similarity	NPC170978
0.7889	Intermediate Similarity	NPC5943
0.7889	Intermediate Similarity	NPC470920
0.7882	Intermediate Similarity	NPC472608
0.7872	Intermediate Similarity	NPC98639
0.7872	Intermediate Similarity	NPC263135
0.7872	Intermediate Similarity	NPC48330
0.7872	Intermediate Similarity	NPC288906
0.7865	Intermediate Similarity	NPC473350
0.7857	Intermediate Similarity	NPC471046
0.7849	Intermediate Similarity	NPC256104
0.7849	Intermediate Similarity	NPC182740

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 NPC472272 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	413
0.1-0.2	3462
0.2-0.3	3492
0.3-0.4	1076
0.4-0.5	286
0.5-0.6	190
0.6-0.7	171
0.7-0.8	44
0.8-0.85	8
0.85-0.9	4
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9	High Similarity	NPD6115	Approved
0.9	High Similarity	NPD6114	Approved
0.9	High Similarity	NPD6118	Approved
0.9	High Similarity	NPD6697	Approved
0.8875	High Similarity	NPD6116	Phase 1
0.875	High Similarity	NPD6117	Approved
0.85	High Similarity	NPD6113	Clinical (unspecified phase)
0.8395	Intermediate Similarity	NPD3703	Phase 2
0.8025	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD3702	Approved
0.7901	Intermediate Similarity	NPD4244	Approved
0.7901	Intermediate Similarity	NPD4245	Approved
0.7778	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3698	Phase 2
0.7778	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD5360	Phase 3
0.76	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD6081	Approved
0.759	Intermediate Similarity	NPD5777	Approved
0.747	Intermediate Similarity	NPD4789	Approved
0.7407	Intermediate Similarity	NPD4224	Phase 2
0.7368	Intermediate Similarity	NPD8034	Phase 2
0.7368	Intermediate Similarity	NPD8035	Phase 2
0.7358	Intermediate Similarity	NPD4632	Approved
0.7353	Intermediate Similarity	NPD6675	Approved
0.7353	Intermediate Similarity	NPD6402	Approved
0.7353	Intermediate Similarity	NPD7128	Approved
0.7353	Intermediate Similarity	NPD5739	Approved
0.7284	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD4787	Phase 1
0.7212	Intermediate Similarity	NPD6899	Approved
0.7212	Intermediate Similarity	NPD6881	Approved
0.7212	Intermediate Similarity	NPD7320	Approved
0.72	Intermediate Similarity	NPD8418	Phase 2
0.7176	Intermediate Similarity	NPD4758	Discontinued
0.7172	Intermediate Similarity	NPD4755	Approved
0.7143	Intermediate Similarity	NPD6373	Approved
0.7143	Intermediate Similarity	NPD6372	Approved
0.7129	Intermediate Similarity	NPD1700	Approved
0.7115	Intermediate Similarity	NPD5701	Approved
0.7115	Intermediate Similarity	NPD5697	Approved
0.7111	Intermediate Similarity	NPD6928	Phase 2
0.7103	Intermediate Similarity	NPD8297	Approved
0.7079	Intermediate Similarity	NPD3671	Phase 1
0.7079	Intermediate Similarity	NPD5364	Discontinued
0.7075	Intermediate Similarity	NPD4634	Approved
0.7075	Intermediate Similarity	NPD7102	Approved
0.7075	Intermediate Similarity	NPD6883	Approved
0.7075	Intermediate Similarity	NPD7290	Approved
0.7065	Intermediate Similarity	NPD4788	Approved
0.7048	Intermediate Similarity	NPD6011	Approved
0.703	Intermediate Similarity	NPD5286	Approved
0.703	Intermediate Similarity	NPD4696	Approved
0.703	Intermediate Similarity	NPD4700	Approved
0.703	Intermediate Similarity	NPD5285	Approved
0.7009	Intermediate Similarity	NPD6869	Approved
0.7009	Intermediate Similarity	NPD6650	Approved
0.7009	Intermediate Similarity	NPD6617	Approved
0.7009	Intermediate Similarity	NPD8130	Phase 1
0.7009	Intermediate Similarity	NPD6847	Approved
0.7009	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6649	Approved
0.7	Intermediate Similarity	NPD6009	Approved
0.6981	Remote Similarity	NPD6012	Approved
0.6981	Remote Similarity	NPD6014	Approved
0.6981	Remote Similarity	NPD6013	Approved
0.6979	Remote Similarity	NPD5328	Approved
0.6964	Remote Similarity	NPD6319	Approved
0.6961	Remote Similarity	NPD5223	Approved
0.6957	Remote Similarity	NPD7507	Approved
0.6944	Remote Similarity	NPD6882	Approved
0.6939	Remote Similarity	NPD4202	Approved
0.6931	Remote Similarity	NPD7638	Approved
0.6893	Remote Similarity	NPD5226	Approved
0.6893	Remote Similarity	NPD5211	Phase 2
0.6893	Remote Similarity	NPD5225	Approved
0.6893	Remote Similarity	NPD4633	Approved
0.6893	Remote Similarity	NPD5224	Approved
0.6887	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD8133	Approved
0.6875	Remote Similarity	NPD3198	Approved
0.6863	Remote Similarity	NPD7639	Approved
0.6863	Remote Similarity	NPD7640	Approved
0.6857	Remote Similarity	NPD6008	Approved
0.6837	Remote Similarity	NPD6079	Approved
0.6827	Remote Similarity	NPD4754	Approved
0.6827	Remote Similarity	NPD5174	Approved
0.6827	Remote Similarity	NPD5175	Approved
0.6783	Remote Similarity	NPD7604	Phase 2
0.678	Remote Similarity	NPD7319	Approved
0.6768	Remote Similarity	NPD6399	Phase 3
0.6768	Remote Similarity	NPD8171	Discontinued
0.6762	Remote Similarity	NPD5141	Approved
0.6754	Remote Similarity	NPD5983	Phase 2
0.6739	Remote Similarity	NPD7525	Registered
0.6731	Remote Similarity	NPD7632	Discontinued
0.6724	Remote Similarity	NPD7492	Approved
0.6698	Remote Similarity	NPD4767	Approved
0.6698	Remote Similarity	NPD4768	Approved
0.6695	Remote Similarity	NPD7736	Approved
0.6667	Remote Similarity	NPD6059	Approved
0.6667	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD6336	Discontinued
0.6667	Remote Similarity	NPD6054	Approved
0.6667	Remote Similarity	NPD7515	Phase 2
0.6637	Remote Similarity	NPD6335	Approved
0.6632	Remote Similarity	NPD4786	Approved
0.661	Remote Similarity	NPD8293	Discontinued
0.661	Remote Similarity	NPD7078	Approved
0.6607	Remote Similarity	NPD6940	Discontinued
0.6607	Remote Similarity	NPD6274	Approved
0.6579	Remote Similarity	NPD7100	Approved
0.6579	Remote Similarity	NPD7101	Approved
0.6574	Remote Similarity	NPD4730	Approved
0.6574	Remote Similarity	NPD5128	Approved
0.6574	Remote Similarity	NPD4729	Approved
0.6569	Remote Similarity	NPD5222	Approved
0.6569	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD4697	Phase 3
0.6569	Remote Similarity	NPD5221	Approved
0.6552	Remote Similarity	NPD6370	Approved
0.6549	Remote Similarity	NPD6317	Approved
0.6548	Remote Similarity	NPD7909	Approved
0.6514	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD5173	Approved
0.6495	Remote Similarity	NPD3618	Phase 1
0.6491	Remote Similarity	NPD6314	Approved
0.6491	Remote Similarity	NPD6313	Approved
0.6481	Remote Similarity	NPD6412	Phase 2
0.6466	Remote Similarity	NPD6016	Approved
0.6466	Remote Similarity	NPD6908	Approved
0.6466	Remote Similarity	NPD6015	Approved
0.6466	Remote Similarity	NPD6909	Approved
0.6465	Remote Similarity	NPD4753	Phase 2
0.6458	Remote Similarity	NPD3666	Approved
0.6458	Remote Similarity	NPD3133	Approved
0.6458	Remote Similarity	NPD3665	Phase 1
0.6455	Remote Similarity	NPD5135	Approved
0.6455	Remote Similarity	NPD5248	Approved
0.6455	Remote Similarity	NPD5249	Phase 3
0.6455	Remote Similarity	NPD5250	Approved
0.6455	Remote Similarity	NPD5247	Approved
0.6455	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD5251	Approved
0.6455	Remote Similarity	NPD5169	Approved
0.6429	Remote Similarity	NPD8298	Phase 2
0.6421	Remote Similarity	NPD3667	Approved
0.641	Remote Similarity	NPD5988	Approved
0.6404	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD5127	Approved
0.6396	Remote Similarity	NPD5216	Approved
0.6396	Remote Similarity	NPD5215	Approved
0.6396	Remote Similarity	NPD5217	Approved
0.6373	Remote Similarity	NPD7748	Approved
0.6364	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD7327	Approved
0.6348	Remote Similarity	NPD7328	Approved
0.6346	Remote Similarity	NPD7902	Approved
0.6344	Remote Similarity	NPD4802	Phase 2
0.6344	Remote Similarity	NPD4238	Approved
0.6337	Remote Similarity	NPD5284	Approved
0.6337	Remote Similarity	NPD5281	Approved
0.6327	Remote Similarity	NPD5330	Approved
0.6327	Remote Similarity	NPD7334	Approved
0.6327	Remote Similarity	NPD6409	Approved
0.6327	Remote Similarity	NPD7521	Approved
0.6327	Remote Similarity	NPD7146	Approved
0.6327	Remote Similarity	NPD6684	Approved
0.6325	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD1780	Approved
0.6316	Remote Similarity	NPD1779	Approved
0.6311	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD5695	Phase 3
0.6293	Remote Similarity	NPD7516	Approved
0.6286	Remote Similarity	NPD5696	Approved
0.6281	Remote Similarity	NPD6033	Approved
0.6261	Remote Similarity	NPD7115	Discovery
0.625	Remote Similarity	NPD4221	Approved
0.625	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4223	Phase 3
0.6239	Remote Similarity	NPD8294	Approved
0.6239	Remote Similarity	NPD8377	Approved
0.6228	Remote Similarity	NPD5167	Approved
0.6224	Remote Similarity	NPD5329	Approved
0.6211	Remote Similarity	NPD5368	Approved
0.62	Remote Similarity	NPD6903	Approved
0.6195	Remote Similarity	NPD6053	Discontinued
0.6186	Remote Similarity	NPD3669	Approved
0.6186	Remote Similarity	NPD8296	Approved
0.6186	Remote Similarity	NPD6921	Approved
0.6186	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD8335	Approved
0.6186	Remote Similarity	NPD8379	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