NPASS Compound

Structure

NPC100913 OpenBabel07101718332D 30 33 0 0 1 0 0 0 0 0999 V2000 -0.9708 -0.7102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0753 -3.8280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9715 1.6260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0215 1.4389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6552 -0.3219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7155 0.8606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7902 0.5752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4252 0.2020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5748 -0.3688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2098 -0.7419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1323 -1.8915 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4715 -2.2401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9299 -0.2733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1323 -1.1943 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9138 -3.3438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2846 -1.0273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5371 0.3028 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0753 -1.8915 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7244 -0.9396 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4215 -0.6585 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0691 -1.9713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6586 0.7098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0753 -1.1943 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4715 -0.8457 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7524 -3.8280 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1313 -1.3171 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7789 -2.6299 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9138 -2.3756 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1439 -2.2567 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 14 1 0 0 0 0 2 15 1 0 0 0 0 3 22 1 0 0 0 0 4 22 1 0 0 0 0 5 23 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 2 0 0 0 0 9 16 2 0 0 0 0 10 16 1 0 0 0 0 11 12 1 0 0 0 0 11 14 1 0 0 0 0 12 18 1 0 0 0 0 13 19 1 0 0 0 0 14 24 1 1 0 0 0 15 25 2 0 0 0 0 15 28 1 0 0 0 0 16 21 1 0 0 0 0 17 13 1 6 0 0 0 17 20 1 0 0 0 0 17 22 1 0 0 0 0 18 23 1 1 0 0 0 18 28 1 0 0 0 0 19 23 1 6 0 0 0 19 29 1 0 0 0 0 20 24 1 1 0 0 0 20 26 1 0 0 0 0 21 27 2 0 0 0 0 21 29 1 0 0 0 0 22 30 1 0 0 0 0 23 24 1 6 0 0 0 24 30 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.22
Volume:	428.993
LogP:	4.096
LogD:	3.295
LogS:	-4.316
# Rotatable Bonds:	5
TPSA:	82.06
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.76
Synthetic Accessibility Score:	5.481
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.936
MDCK Permeability:	3.60860358341597e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.018
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.874
30% Bioavailability (F30%):	0.971

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.18
Plasma Protein Binding (PPB):	88.4958267211914%
Volume Distribution (VD):	2.034
Pgp-substrate:	12.989850044250488%

ADMET: Metabolism

CYP1A2-inhibitor:	0.062
CYP1A2-substrate:	0.065
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.287
CYP2C9-inhibitor:	0.169
CYP2C9-substrate:	0.082
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.196
CYP3A4-inhibitor:	0.205
CYP3A4-substrate:	0.302

ADMET: Excretion

Clearance (CL):	8.182
Half-life (T1/2):	0.49

ADMET: Toxicity

hERG Blockers:	0.605
Human Hepatotoxicity (H-HT):	0.864
Drug-inuced Liver Injury (DILI):	0.95
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.117
Maximum Recommended Daily Dose:	0.134
Skin Sensitization:	0.359
Carcinogencity:	0.264
Eye Corrosion:	0.005
Eye Irritation:	0.23
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC100913

Natural Product ID:	NPC100913
*Common Name:**	NHAOANQCNDNNRY-VIJIUCOUSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NHAOANQCNDNNRY-VIJIUCOUSA-N
Standard InCHI:	InChI=1S/C24H32O6/c1-14-11-12-18(28-15(2)25)23(5)19(29-21(27)16-9-7-6-8-10-16)13-17-20(26)24(14,23)30-22(17,3)4/h6-10,14,17-20,26H,11-13H2,1-5H3/t14-,17-,18+,19+,20-,23+,24-/m1/s1
SMILES:	C[C@@H]1CC[C@@H]([C@@]2(C)[C@H](C[C@@H]3[C@H]([C@]12OC3(C)C)O)OC(=O)c1ccccc1)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL451784
PubChem CID:	24898038
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002051] Agarofurans

*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
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10346948]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[10346948]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170672]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[11809076]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	Seeds	n.a.	n.a.	PMID[18507472]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23421714]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27791375]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[9461657]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461657]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	Activity	<	50.0	%	PMID[512249]

☑ 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 NPC100913 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	275
0.1-0.2	1004
0.2-0.3	2141
0.3-0.4	4056
0.4-0.5	7895
0.5-0.6	11949
0.6-0.7	12699
0.7-0.8	2092
0.8-0.85	277
0.85-0.9	142
0.9-0.95	80
0.95-1	87

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC275592
0.9924	High Similarity	NPC118080
0.9924	High Similarity	NPC472576
0.9924	High Similarity	NPC27377
0.9924	High Similarity	NPC97947
0.9924	High Similarity	NPC87448
0.9924	High Similarity	NPC41481
0.9924	High Similarity	NPC291599
0.9848	High Similarity	NPC97667
0.9848	High Similarity	NPC171207
0.9848	High Similarity	NPC90614
0.9774	High Similarity	NPC16912
0.9704	High Similarity	NPC470152
0.9704	High Similarity	NPC475122
0.9704	High Similarity	NPC475759
0.9704	High Similarity	NPC241951
0.9632	High Similarity	NPC29704
0.9632	High Similarity	NPC473088
0.9632	High Similarity	NPC96903
0.9632	High Similarity	NPC469349
0.9632	High Similarity	NPC472568
0.9632	High Similarity	NPC158663
0.9632	High Similarity	NPC470157
0.9632	High Similarity	NPC171525
0.9632	High Similarity	NPC472575
0.9632	High Similarity	NPC472572
0.9632	High Similarity	NPC471104
0.9632	High Similarity	NPC472571
0.9632	High Similarity	NPC200471
0.9632	High Similarity	NPC177940
0.9632	High Similarity	NPC476973
0.9632	High Similarity	NPC174982
0.9632	High Similarity	NPC184817
0.9632	High Similarity	NPC470159
0.9632	High Similarity	NPC70403
0.963	High Similarity	NPC163087
0.9618	High Similarity	NPC474608
0.9559	High Similarity	NPC25768
0.9559	High Similarity	NPC11685
0.9559	High Similarity	NPC476974
0.9559	High Similarity	NPC472570
0.9559	High Similarity	NPC95265
0.9559	High Similarity	NPC57628
0.9559	High Similarity	NPC95810
0.9559	High Similarity	NPC472573
0.9559	High Similarity	NPC472569
0.9559	High Similarity	NPC188865
0.9559	High Similarity	NPC70716
0.9559	High Similarity	NPC125106
0.9559	High Similarity	NPC163719
0.9552	High Similarity	NPC472547
0.9549	High Similarity	NPC39549
0.9545	High Similarity	NPC291638
0.9545	High Similarity	NPC66761
0.9545	High Similarity	NPC17877
0.9545	High Similarity	NPC472577
0.9545	High Similarity	NPC195647
0.9474	High Similarity	NPC472551
0.9474	High Similarity	NPC472545
0.9424	High Similarity	NPC476975
0.9424	High Similarity	NPC92293
0.9424	High Similarity	NPC266265
0.9424	High Similarity	NPC471101
0.9424	High Similarity	NPC301556
0.9424	High Similarity	NPC270590
0.9424	High Similarity	NPC473215
0.942	High Similarity	NPC474935
0.9412	High Similarity	NPC34012
0.9403	High Similarity	NPC183122
0.9403	High Similarity	NPC283375
0.9357	High Similarity	NPC473214
0.9357	High Similarity	NPC470245
0.9353	High Similarity	NPC281717
0.9348	High Similarity	NPC472556
0.9343	High Similarity	NPC91703
0.9338	High Similarity	NPC224491
0.9333	High Similarity	NPC475652
0.9333	High Similarity	NPC214550
0.9333	High Similarity	NPC210591
0.9313	High Similarity	NPC147561
0.9291	High Similarity	NPC470153
0.9291	High Similarity	NPC471103
0.9275	High Similarity	NPC38696
0.9265	High Similarity	NPC473060
0.9265	High Similarity	NPC48017
0.9265	High Similarity	NPC473613
0.9265	High Similarity	NPC4341
0.9265	High Similarity	NPC43241
0.9265	High Similarity	NPC473758
0.9265	High Similarity	NPC473081
0.9265	High Similarity	NPC147880
0.9265	High Similarity	NPC211137
0.9265	High Similarity	NPC184747
0.9265	High Similarity	NPC473109
0.9265	High Similarity	NPC200592
0.9265	High Similarity	NPC473112
0.9265	High Similarity	NPC476094
0.9265	High Similarity	NPC473085
0.9203	High Similarity	NPC477894
0.9155	High Similarity	NPC51602
0.9143	High Similarity	NPC240115
0.9143	High Similarity	NPC473602
0.9143	High Similarity	NPC478263
0.9137	High Similarity	NPC34943
0.913	High Similarity	NPC472546
0.9111	High Similarity	NPC477893
0.9111	High Similarity	NPC477896
0.9097	High Similarity	NPC34066
0.9091	High Similarity	NPC472548
0.9091	High Similarity	NPC477905
0.9085	High Similarity	NPC469448
0.9078	High Similarity	NPC473760
0.9078	High Similarity	NPC217918
0.9071	High Similarity	NPC311825
0.9071	High Similarity	NPC92867
0.9071	High Similarity	NPC478264
0.9071	High Similarity	NPC127857
0.9065	High Similarity	NPC191082
0.9065	High Similarity	NPC473673
0.9065	High Similarity	NPC270498
0.9065	High Similarity	NPC147217
0.9065	High Similarity	NPC246480
0.9065	High Similarity	NPC475429
0.9065	High Similarity	NPC139067
0.9065	High Similarity	NPC177340
0.9037	High Similarity	NPC48929
0.9034	High Similarity	NPC106895
0.9021	High Similarity	NPC469415
0.9014	High Similarity	NPC60509
0.9014	High Similarity	NPC250046
0.9014	High Similarity	NPC81698
0.9008	High Similarity	NPC475933
0.9008	High Similarity	NPC470158
0.9007	High Similarity	NPC20255
0.9007	High Similarity	NPC209592
0.9007	High Similarity	NPC48599
0.9	High Similarity	NPC470231
0.9	High Similarity	NPC51314
0.9	High Similarity	NPC67777
0.8993	High Similarity	NPC192658
0.8993	High Similarity	NPC182869
0.8986	High Similarity	NPC183270
0.8986	High Similarity	NPC477904
0.8966	High Similarity	NPC472549
0.8966	High Similarity	NPC282239
0.8966	High Similarity	NPC132599
0.8966	High Similarity	NPC473670
0.8966	High Similarity	NPC473632
0.8966	High Similarity	NPC469730
0.8966	High Similarity	NPC469422
0.8966	High Similarity	NPC21410
0.8951	High Similarity	NPC161239
0.8951	High Similarity	NPC303429
0.8951	High Similarity	NPC7095
0.8951	High Similarity	NPC198455
0.8951	High Similarity	NPC91730
0.8951	High Similarity	NPC165260
0.8951	High Similarity	NPC222102
0.8951	High Similarity	NPC476173
0.8944	High Similarity	NPC132652
0.8939	High Similarity	NPC476971
0.8939	High Similarity	NPC476972
0.8936	High Similarity	NPC471100
0.8936	High Similarity	NPC471107
0.8936	High Similarity	NPC125882
0.8921	High Similarity	NPC266374
0.8913	High Similarity	NPC9905
0.8912	High Similarity	NPC469399
0.8905	High Similarity	NPC472374
0.8905	High Similarity	NPC472372
0.8897	High Similarity	NPC469477
0.8897	High Similarity	NPC133430
0.8889	High Similarity	NPC197037
0.8873	High Similarity	NPC312393
0.8864	High Similarity	NPC473082
0.8864	High Similarity	NPC476970
0.8864	High Similarity	NPC275576
0.8849	High Similarity	NPC87934
0.8849	High Similarity	NPC162613
0.8844	High Similarity	NPC472393
0.8836	High Similarity	NPC469398
0.8836	High Similarity	NPC26033
0.8836	High Similarity	NPC228204
0.8836	High Similarity	NPC473611
0.8819	High Similarity	NPC112216
0.8819	High Similarity	NPC31829
0.8811	High Similarity	NPC327031
0.8797	High Similarity	NPC169913
0.8784	High Similarity	NPC471102
0.8779	High Similarity	NPC473870
0.8779	High Similarity	NPC473871
0.8776	High Similarity	NPC217091
0.8767	High Similarity	NPC472030
0.8767	High Similarity	NPC473414
0.8767	High Similarity	NPC472658
0.8767	High Similarity	NPC472022
0.8767	High Similarity	NPC471135
0.8767	High Similarity	NPC472657
0.8767	High Similarity	NPC242262
0.8767	High Similarity	NPC11588

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 NPC100913 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	227
0.1-0.2	662
0.2-0.3	1376
0.3-0.4	2682
0.4-0.5	2387
0.5-0.6	1302
0.6-0.7	465
0.7-0.8	47
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8288	Intermediate Similarity	NPD7236	Approved
0.8201	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD7239	Suspended
0.795	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD7799	Discontinued
0.7879	Intermediate Similarity	NPD8407	Phase 2
0.7805	Intermediate Similarity	NPD8368	Discontinued
0.7784	Intermediate Similarity	NPD8434	Phase 2
0.773	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD2629	Approved
0.7667	Intermediate Similarity	NPD4628	Phase 3
0.763	Intermediate Similarity	NPD4198	Discontinued
0.7591	Intermediate Similarity	NPD7741	Discontinued
0.7588	Intermediate Similarity	NPD8361	Approved
0.7588	Intermediate Similarity	NPD8435	Approved
0.7588	Intermediate Similarity	NPD8360	Approved
0.7569	Intermediate Similarity	NPD7008	Discontinued
0.7547	Intermediate Similarity	NPD7058	Phase 2
0.7547	Intermediate Similarity	NPD7057	Phase 3
0.7519	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD3764	Approved
0.7482	Intermediate Similarity	NPD5126	Approved
0.7482	Intermediate Similarity	NPD5125	Phase 3
0.7471	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD8127	Discontinued
0.7434	Intermediate Similarity	NPD8166	Discontinued
0.7426	Intermediate Similarity	NPD5951	Approved
0.7419	Intermediate Similarity	NPD6273	Approved
0.7415	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD5844	Phase 1
0.7386	Intermediate Similarity	NPD6190	Approved
0.7358	Intermediate Similarity	NPD37	Approved
0.7347	Intermediate Similarity	NPD7961	Discontinued
0.733	Intermediate Similarity	NPD8485	Approved
0.7329	Intermediate Similarity	NPD4966	Approved
0.7329	Intermediate Similarity	NPD4965	Approved
0.7329	Intermediate Similarity	NPD4967	Phase 2
0.7273	Intermediate Similarity	NPD7274	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD8150	Discontinued
0.7239	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6234	Discontinued
0.7239	Intermediate Similarity	NPD2182	Approved
0.7234	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD5760	Phase 2
0.7205	Intermediate Similarity	NPD5761	Phase 2
0.7183	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD7458	Discontinued
0.717	Intermediate Similarity	NPD6591	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7228	Approved
0.7134	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD6599	Discontinued
0.7124	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD6663	Approved
0.7113	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7819	Suspended
0.7097	Intermediate Similarity	NPD7003	Approved
0.7088	Intermediate Similarity	NPD7497	Discontinued
0.7083	Intermediate Similarity	NPD7473	Discontinued
0.7076	Intermediate Similarity	NPD6765	Approved
0.7076	Intermediate Similarity	NPD6764	Approved
0.7075	Intermediate Similarity	NPD5736	Approved
0.7073	Intermediate Similarity	NPD7075	Discontinued
0.7063	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD6858	Approved
0.7029	Intermediate Similarity	NPD7094	Approved
0.7025	Intermediate Similarity	NPD2532	Approved
0.7025	Intermediate Similarity	NPD2533	Approved
0.7025	Intermediate Similarity	NPD2534	Approved
0.7021	Intermediate Similarity	NPD7610	Discontinued
0.702	Intermediate Similarity	NPD230	Phase 1
0.702	Intermediate Similarity	NPD6355	Discontinued
0.7019	Intermediate Similarity	NPD4380	Phase 2
0.7014	Intermediate Similarity	NPD6287	Discontinued
0.7006	Intermediate Similarity	NPD6232	Discontinued
0.6994	Remote Similarity	NPD8313	Approved
0.6994	Remote Similarity	NPD8312	Approved
0.6988	Remote Similarity	NPD5494	Approved
0.6977	Remote Similarity	NPD7240	Approved
0.6977	Remote Similarity	NPD6559	Discontinued
0.6962	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD5402	Approved
0.6948	Remote Similarity	NPD2935	Discontinued
0.6946	Remote Similarity	NPD7199	Phase 2
0.694	Remote Similarity	NPD164	Approved
0.6937	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6801	Discontinued
0.6914	Remote Similarity	NPD6785	Approved
0.6914	Remote Similarity	NPD6784	Approved
0.6909	Remote Similarity	NPD7768	Phase 2
0.6903	Remote Similarity	NPD2346	Discontinued
0.6903	Remote Similarity	NPD5762	Approved
0.6903	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6004	Phase 3
0.6903	Remote Similarity	NPD6005	Phase 3
0.6903	Remote Similarity	NPD5763	Approved
0.6903	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6002	Phase 3
0.6903	Remote Similarity	NPD7266	Discontinued
0.6894	Remote Similarity	NPD1238	Approved
0.6893	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.689	Remote Similarity	NPD8455	Phase 2
0.689	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6233	Phase 2
0.6879	Remote Similarity	NPD7685	Pre-registration
0.6879	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4110	Phase 3
0.6879	Remote Similarity	NPD3750	Approved
0.6878	Remote Similarity	NPD8462	Phase 1
0.6875	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7095	Approved
0.6866	Remote Similarity	NPD1929	Approved
0.6866	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD1930	Approved
0.6866	Remote Similarity	NPD6647	Phase 2
0.6861	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD6799	Approved
0.6853	Remote Similarity	NPD9545	Approved
0.6852	Remote Similarity	NPD3226	Approved
0.6848	Remote Similarity	NPD3817	Phase 2
0.6842	Remote Similarity	NPD4140	Approved
0.6842	Remote Similarity	NPD3818	Discontinued
0.6839	Remote Similarity	NPD5405	Approved
0.6839	Remote Similarity	NPD5404	Approved
0.6839	Remote Similarity	NPD5406	Approved
0.6839	Remote Similarity	NPD5408	Approved
0.6838	Remote Similarity	NPD6685	Approved
0.6832	Remote Similarity	NPD5403	Approved
0.6829	Remote Similarity	NPD1934	Approved
0.6821	Remote Similarity	NPD6798	Discontinued
0.6813	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD5401	Approved
0.6812	Remote Similarity	NPD2067	Discontinued
0.6781	Remote Similarity	NPD4806	Approved
0.6781	Remote Similarity	NPD4807	Approved
0.6776	Remote Similarity	NPD7715	Approved
0.6776	Remote Similarity	NPD7714	Approved
0.6776	Remote Similarity	NPD8032	Phase 2
0.6774	Remote Similarity	NPD2799	Discontinued
0.6774	Remote Similarity	NPD7305	Phase 1
0.6774	Remote Similarity	NPD3748	Approved
0.6768	Remote Similarity	NPD7411	Suspended
0.6767	Remote Similarity	NPD2066	Phase 3
0.6766	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5306	Approved
0.6759	Remote Similarity	NPD5305	Approved
0.6752	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.674	Remote Similarity	NPD6534	Approved
0.674	Remote Similarity	NPD6535	Approved
0.6738	Remote Similarity	NPD6010	Discontinued
0.6736	Remote Similarity	NPD8404	Phase 2
0.6731	Remote Similarity	NPD6100	Approved
0.6731	Remote Similarity	NPD6099	Approved
0.6731	Remote Similarity	NPD2438	Suspended
0.6726	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD6166	Phase 2
0.6725	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD7700	Phase 2
0.6721	Remote Similarity	NPD7699	Phase 2
0.672	Remote Similarity	NPD7435	Discontinued
0.6714	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD3094	Phase 2
0.6711	Remote Similarity	NPD2313	Discontinued
0.6711	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.671	Remote Similarity	NPD7097	Phase 1
0.6708	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD7028	Phase 2
0.6707	Remote Similarity	NPD3882	Suspended
0.6706	Remote Similarity	NPD7229	Phase 3
0.6691	Remote Similarity	NPD1237	Approved
0.6691	Remote Similarity	NPD5909	Discontinued
0.6688	Remote Similarity	NPD5735	Approved
0.6687	Remote Similarity	NPD2801	Approved
0.6684	Remote Similarity	NPD8320	Phase 1
0.6684	Remote Similarity	NPD8319	Approved
0.6667	Remote Similarity	NPD7033	Discontinued
0.6667	Remote Similarity	NPD7074	Phase 3
0.6667	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2575	Approved
0.6667	Remote Similarity	NPD3749	Approved
0.6667	Remote Similarity	NPD7713	Phase 3
0.6667	Remote Similarity	NPD6085	Phase 2
0.6667	Remote Similarity	NPD4308	Phase 3
0.6647	Remote Similarity	NPD3751	Discontinued
0.6645	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD6653	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