NPASS Compound

Structure

NPC472651 OpenBabel07101719252D 38 44 0 0 1 0 0 0 0 0999 V2000 0.8724 -5.1320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5387 -1.4657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2217 -3.0276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5486 -3.3736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8462 -2.4429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2777 -0.5797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6925 -1.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9315 -1.3059 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4983 -3.6438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4871 -1.9490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1962 -1.4657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0392 -4.6215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3850 -0.9772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9543 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9235 -3.1784 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2337 -3.5665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6925 -0.9772 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6925 -1.9543 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8462 -0.4886 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5387 -0.4886 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8462 0.4886 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6925 0.9772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6925 -0.9772 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6218 -2.2563 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8462 -2.4429 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.9772 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8462 -0.4886 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8195 -5.0877 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7000 -4.4252 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8462 0.4886 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6925 1.9543 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4429 -2.1521 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6218 -0.6752 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0648 -3.6446 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5387 0.4886 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6991 -2.9918 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 13 1 0 0 0 0 2 24 1 0 0 0 0 5 27 1 0 0 0 0 6 8 1 0 0 0 0 6 15 1 0 0 0 0 7 9 2 0 0 0 0 7 14 1 0 0 0 0 8 24 1 0 0 0 0 9 33 1 0 0 0 0 10 16 1 0 0 0 0 10 17 1 0 0 0 0 11 14 2 0 0 0 0 11 33 1 0 0 0 0 12 25 1 0 0 0 0 12 34 1 0 0 0 0 13 29 2 0 0 0 0 13 35 1 0 0 0 0 14 21 1 0 0 0 0 15 26 1 1 0 0 0 15 27 1 0 0 0 0 16 26 1 6 0 0 0 16 35 1 0 0 0 0 17 30 2 0 0 0 0 17 37 1 0 0 0 0 18 19 1 0 0 0 0 18 20 1 0 0 0 0 18 34 1 6 0 0 0 19 25 1 1 0 0 0 19 26 1 0 0 0 0 20 27 1 6 0 0 0 20 31 1 0 0 0 0 21 24 1 6 0 0 0 21 36 1 0 0 0 0 22 23 1 0 0 0 0 22 28 1 1 0 0 0 22 38 1 0 0 0 0 23 32 2 0 0 0 0 23 36 1 0 0 0 0 24 28 1 6 0 0 0 25 3 1 1 0 0 0 25 37 1 0 0 0 0 26 4 1 1 0 0 0 27 28 1 6 0 0 0 28 38 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	530.22
Volume:	507.669
LogP:	2.756
LogD:	2.012
LogS:	-4.844
# Rotatable Bonds:	3
TPSA:	134.03
# H-Bond Aceptor:	10
# H-Bond Donor:	1
# Rings:	7
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.345
Synthetic Accessibility Score:	6.038
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.329
MDCK Permeability:	4.2964009480783716e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.154
Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	0.432
30% Bioavailability (F30%):	0.873

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.564
Plasma Protein Binding (PPB):	70.657958984375%
Volume Distribution (VD):	1.329
Pgp-substrate:	29.76314353942871%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.097
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.215
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.007
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.079
CYP3A4-inhibitor:	0.59
CYP3A4-substrate:	0.344

ADMET: Excretion

Clearance (CL):	6.501
Half-life (T1/2):	0.692

ADMET: Toxicity

hERG Blockers:	0.096
Human Hepatotoxicity (H-HT):	0.644
Drug-inuced Liver Injury (DILI):	0.817
AMES Toxicity:	0.155
Rat Oral Acute Toxicity:	0.923
Maximum Recommended Daily Dose:	0.267
Skin Sensitization:	0.201
Carcinogencity:	0.178
Eye Corrosion:	0.023
Eye Irritation:	0.021
Respiratory Toxicity:	0.959

Download Data

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

Natural Product: NPC472651

Natural Product ID:	NPC472651
*Common Name:**	VBQCGTLLLFBLDL-SBUVEFCSSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VBQCGTLLLFBLDL-SBUVEFCSSA-N
Standard InCHI:	InChI=1S/C28H34O10/c1-13(29)35-16-10-17(30)37-25(3)12-34-18-19(25)26(16,4)15-6-8-24(2)21(14-7-9-33-11-14)36-23(32)22-28(24,38-22)27(15,5)20(18)31/h7,9,11,15-16,18-22,31H,6,8,10,12H2,1-5H3/t15-,16+,18-,19+,20-,21+,22-,24+,25+,26+,27+,28-/m1/s1
SMILES:	CC(=O)O[C@H]1CC(=O)O[C@@]2([C@H]3[C@@]1(C)[C@H]1CC[C@@]4([C@]5([C@@]1([C@@H]([C@@H]3OC2)O)C)O[C@@H]5C(=O)O[C@H]4c1ccoc1)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581388
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

*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
NPO32927.1	Dysoxylum mollissimum	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[25781655]

☑ 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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	GI	<	50.0	%	PMID[502422]
NPT81	Cell Line	A549	Homo sapiens	GI	<	50.0	%	PMID[502422]
NPT116	Cell Line	HL-60	Homo sapiens	GI	<	50.0	%	PMID[502422]

☑ 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 NPC472651 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	378
0.1-0.2	1443
0.2-0.3	3345
0.3-0.4	5615
0.4-0.5	10546
0.5-0.6	10606
0.6-0.7	9241
0.7-0.8	1107
0.8-0.85	249
0.85-0.9	122
0.9-0.95	43
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9936	High Similarity	NPC472652
0.9684	High Similarity	NPC271235
0.9551	High Similarity	NPC472653
0.9497	High Similarity	NPC476850
0.9497	High Similarity	NPC476853
0.9497	High Similarity	NPC476861
0.9494	High Similarity	NPC123088
0.9487	High Similarity	NPC475967
0.943	High Similarity	NPC39986
0.943	High Similarity	NPC134254
0.943	High Similarity	NPC302369
0.9427	High Similarity	NPC335761
0.9423	High Similarity	NPC299038
0.9423	High Similarity	NPC45101
0.9375	High Similarity	NPC472775
0.9375	High Similarity	NPC472774
0.9371	High Similarity	NPC476856
0.9371	High Similarity	NPC476857
0.9371	High Similarity	NPC476858
0.9367	High Similarity	NPC5079
0.9359	High Similarity	NPC126723
0.9317	High Similarity	NPC471397
0.9313	High Similarity	NPC23387
0.9308	High Similarity	NPC472773
0.9308	High Similarity	NPC51568
0.9308	High Similarity	NPC234660
0.9308	High Similarity	NPC469846
0.9304	High Similarity	NPC25255
0.9299	High Similarity	NPC187149
0.9295	High Similarity	NPC44675
0.9295	High Similarity	NPC214541
0.9259	High Similarity	NPC82602
0.9255	High Similarity	NPC173516
0.9255	High Similarity	NPC472282
0.925	High Similarity	NPC271657
0.925	High Similarity	NPC476860
0.925	High Similarity	NPC276551
0.9245	High Similarity	NPC193798
0.9245	High Similarity	NPC472771
0.9245	High Similarity	NPC117986
0.9241	High Similarity	NPC237155
0.9226	High Similarity	NPC18135
0.9198	High Similarity	NPC160651
0.9193	High Similarity	NPC470875
0.9187	High Similarity	NPC469338
0.9187	High Similarity	NPC477405
0.9187	High Similarity	NPC292389
0.9182	High Similarity	NPC470789
0.9177	High Similarity	NPC286722
0.9177	High Similarity	NPC261597
0.9177	High Similarity	NPC36655
0.9141	High Similarity	NPC470995
0.913	High Similarity	NPC469849
0.913	High Similarity	NPC470940
0.9125	High Similarity	NPC149896
0.9125	High Similarity	NPC96443
0.9125	High Similarity	NPC82851
0.9125	High Similarity	NPC69028
0.9125	High Similarity	NPC200782
0.9125	High Similarity	NPC290400
0.9125	High Similarity	NPC18347
0.9119	High Similarity	NPC475295
0.9119	High Similarity	NPC473473
0.9114	High Similarity	NPC209364
0.9114	High Similarity	NPC107646
0.9108	High Similarity	NPC57998
0.9085	High Similarity	NPC169299
0.9085	High Similarity	NPC160818
0.9062	High Similarity	NPC305016
0.9062	High Similarity	NPC477402
0.9062	High Similarity	NPC475381
0.9057	High Similarity	NPC472772
0.9057	High Similarity	NPC472776
0.9057	High Similarity	NPC472777
0.9057	High Similarity	NPC472778
0.9045	High Similarity	NPC268905
0.9006	High Similarity	NPC263432
0.9006	High Similarity	NPC329938
0.9006	High Similarity	NPC470939
0.9	High Similarity	NPC477403
0.8994	High Similarity	NPC263265
0.897	High Similarity	NPC159232
0.8968	High Similarity	NPC221809
0.8957	High Similarity	NPC472141
0.8951	High Similarity	NPC472139
0.8938	High Similarity	NPC167142
0.8938	High Similarity	NPC249021
0.8931	High Similarity	NPC264943
0.8924	High Similarity	NPC476201
0.8924	High Similarity	NPC469503
0.8924	High Similarity	NPC75906
0.8922	High Similarity	NPC262386
0.8909	High Similarity	NPC472659
0.8896	High Similarity	NPC470182
0.8882	High Similarity	NPC475226
0.8876	High Similarity	NPC470938
0.8875	High Similarity	NPC60973
0.8868	High Similarity	NPC282445
0.8862	High Similarity	NPC236004
0.8854	High Similarity	NPC195325
0.8854	High Similarity	NPC125182
0.8854	High Similarity	NPC69647
0.8848	High Similarity	NPC472766
0.8848	High Similarity	NPC472765
0.8846	High Similarity	NPC470941
0.8841	High Similarity	NPC97574
0.8841	High Similarity	NPC93172
0.883	High Similarity	NPC105395
0.883	High Similarity	NPC247563
0.883	High Similarity	NPC242068
0.8827	High Similarity	NPC191828
0.882	High Similarity	NPC475066
0.882	High Similarity	NPC472283
0.8812	High Similarity	NPC476262
0.8812	High Similarity	NPC469336
0.8788	High Similarity	NPC473753
0.8788	High Similarity	NPC473766
0.8788	High Similarity	NPC100333
0.8788	High Similarity	NPC472764
0.8773	High Similarity	NPC470792
0.8773	High Similarity	NPC188649
0.8773	High Similarity	NPC207978
0.8773	High Similarity	NPC211777
0.8765	High Similarity	NPC472671
0.8765	High Similarity	NPC307383
0.8758	High Similarity	NPC469485
0.8757	High Similarity	NPC478177
0.875	High Similarity	NPC94763
0.875	High Similarity	NPC178932
0.8743	High Similarity	NPC285227
0.8734	High Similarity	NPC472654
0.8727	High Similarity	NPC478178
0.8727	High Similarity	NPC475779
0.8726	High Similarity	NPC250228
0.8726	High Similarity	NPC255414
0.872	High Similarity	NPC288602
0.872	High Similarity	NPC476197
0.872	High Similarity	NPC198047
0.872	High Similarity	NPC472669
0.872	High Similarity	NPC88841
0.8704	High Similarity	NPC173544
0.8696	High Similarity	NPC155939
0.8696	High Similarity	NPC469850
0.8696	High Similarity	NPC141538
0.8696	High Similarity	NPC296807
0.8696	High Similarity	NPC281258
0.869	High Similarity	NPC469848
0.8688	High Similarity	NPC44577
0.8679	High Similarity	NPC476122
0.8679	High Similarity	NPC156189
0.8675	High Similarity	NPC476224
0.8662	High Similarity	NPC346
0.8659	High Similarity	NPC472767
0.8659	High Similarity	NPC472668
0.8654	High Similarity	NPC86935
0.8654	High Similarity	NPC476944
0.8654	High Similarity	NPC251865
0.865	High Similarity	NPC472779
0.8639	High Similarity	NPC471632
0.8639	High Similarity	NPC471437
0.8634	High Similarity	NPC302054
0.8634	High Similarity	NPC237259
0.8634	High Similarity	NPC34421
0.8634	High Similarity	NPC98206
0.8634	High Similarity	NPC253201
0.8623	High Similarity	NPC327922
0.8616	High Similarity	NPC470791
0.8616	High Similarity	NPC470790
0.8614	High Similarity	NPC121995
0.8614	High Similarity	NPC307781
0.8614	High Similarity	NPC472670
0.8614	High Similarity	NPC214600
0.8614	High Similarity	NPC149945
0.8606	High Similarity	NPC224394
0.8606	High Similarity	NPC285567
0.8606	High Similarity	NPC419
0.8606	High Similarity	NPC663
0.8606	High Similarity	NPC283209
0.8599	High Similarity	NPC5676
0.859	High Similarity	NPC476946
0.8589	High Similarity	NPC197137
0.8589	High Similarity	NPC470118
0.8589	High Similarity	NPC88007
0.8589	High Similarity	NPC194499
0.8589	High Similarity	NPC214495
0.8589	High Similarity	NPC470119
0.858	High Similarity	NPC92979
0.858	High Similarity	NPC35000
0.8571	High Similarity	NPC29695
0.8571	High Similarity	NPC33938
0.8571	High Similarity	NPC147168
0.8571	High Similarity	NPC476940
0.8571	High Similarity	NPC472672
0.8571	High Similarity	NPC302392
0.8571	High Similarity	NPC182427
0.8571	High Similarity	NPC476939
0.8563	High Similarity	NPC478179
0.8562	High Similarity	NPC469335
0.8562	High Similarity	NPC196864
0.8562	High Similarity	NPC477404

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 NPC472651 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	319
0.1-0.2	1007
0.2-0.3	2273
0.3-0.4	2748
0.4-0.5	1776
0.5-0.6	778
0.6-0.7	234
0.7-0.8	13
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
0.8466	Intermediate Similarity	NPD5760	Phase 2
0.8466	Intermediate Similarity	NPD5761	Phase 2
0.8343	Intermediate Similarity	NPD8434	Phase 2
0.7941	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD6764	Approved
0.7753	Intermediate Similarity	NPD6765	Approved
0.7602	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD6785	Approved
0.7582	Intermediate Similarity	NPD6784	Approved
0.7572	Intermediate Similarity	NPD7075	Discontinued
0.7427	Intermediate Similarity	NPD6599	Discontinued
0.741	Intermediate Similarity	NPD4628	Phase 3
0.7391	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD6559	Discontinued
0.7341	Intermediate Similarity	NPD6801	Discontinued
0.7299	Intermediate Similarity	NPD7819	Suspended
0.7287	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD8404	Phase 2
0.7257	Intermediate Similarity	NPD3817	Phase 2
0.7176	Intermediate Similarity	NPD6799	Approved
0.7159	Intermediate Similarity	NPD5402	Approved
0.7143	Intermediate Similarity	NPD3751	Discontinued
0.7135	Intermediate Similarity	NPD919	Approved
0.7119	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD3882	Suspended
0.7111	Intermediate Similarity	NPD3787	Discontinued
0.7104	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD5844	Phase 1
0.7095	Intermediate Similarity	NPD5494	Approved
0.7074	Intermediate Similarity	NPD8150	Discontinued
0.7056	Intermediate Similarity	NPD8127	Discontinued
0.7052	Intermediate Similarity	NPD5403	Approved
0.7049	Intermediate Similarity	NPD3818	Discontinued
0.7049	Intermediate Similarity	NPD7799	Discontinued
0.7043	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD5401	Approved
0.7033	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD6166	Phase 2
0.7033	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD4380	Phase 2
0.7027	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD4966	Approved
0.7022	Intermediate Similarity	NPD4967	Phase 2
0.7022	Intermediate Similarity	NPD4965	Approved
0.7006	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD8312	Approved
0.7005	Intermediate Similarity	NPD8313	Approved
0.6995	Remote Similarity	NPD7473	Discontinued
0.6989	Remote Similarity	NPD7251	Discontinued
0.6989	Remote Similarity	NPD7685	Pre-registration
0.6983	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD3749	Approved
0.6978	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD8407	Phase 2
0.6961	Remote Similarity	NPD1247	Approved
0.6957	Remote Similarity	NPD7228	Approved
0.6954	Remote Similarity	NPD920	Approved
0.6952	Remote Similarity	NPD7808	Phase 3
0.6949	Remote Similarity	NPD1934	Approved
0.6944	Remote Similarity	NPD6234	Discontinued
0.6935	Remote Similarity	NPD6797	Phase 2
0.6928	Remote Similarity	NPD6355	Discontinued
0.6923	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6232	Discontinued
0.6923	Remote Similarity	NPD1471	Phase 3
0.6919	Remote Similarity	NPD7236	Approved
0.6919	Remote Similarity	NPD7435	Discontinued
0.6905	Remote Similarity	NPD2799	Discontinued
0.6901	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD8368	Discontinued
0.6897	Remote Similarity	NPD6273	Approved
0.6893	Remote Similarity	NPD7411	Suspended
0.6882	Remote Similarity	NPD7074	Phase 3
0.6875	Remote Similarity	NPD3226	Approved
0.6872	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD7199	Phase 2
0.6854	Remote Similarity	NPD37	Approved
0.6839	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD2534	Approved
0.6839	Remote Similarity	NPD2532	Approved
0.6839	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD2533	Approved
0.6828	Remote Similarity	NPD7054	Approved
0.6824	Remote Similarity	NPD5763	Approved
0.6824	Remote Similarity	NPD5762	Approved
0.6824	Remote Similarity	NPD2346	Discontinued
0.6818	Remote Similarity	NPD7239	Suspended
0.6809	Remote Similarity	NPD7240	Approved
0.6793	Remote Similarity	NPD3926	Phase 2
0.6791	Remote Similarity	NPD7472	Approved
0.678	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD6190	Approved
0.6744	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.673	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD1465	Phase 2
0.6722	Remote Similarity	NPD2801	Approved
0.6716	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD7874	Approved
0.6714	Remote Similarity	NPD7907	Approved
0.6706	Remote Similarity	NPD7033	Discontinued
0.6699	Remote Similarity	NPD4111	Phase 1
0.6687	Remote Similarity	NPD7095	Approved
0.6686	Remote Similarity	NPD1549	Phase 2
0.6685	Remote Similarity	NPD6959	Discontinued
0.6685	Remote Similarity	NPD7458	Discontinued
0.6683	Remote Similarity	NPD6781	Approved
0.6683	Remote Similarity	NPD6780	Approved
0.6683	Remote Similarity	NPD6777	Approved
0.6683	Remote Similarity	NPD6778	Approved
0.6683	Remote Similarity	NPD6782	Approved
0.6683	Remote Similarity	NPD6776	Approved
0.6683	Remote Similarity	NPD6779	Approved
0.6667	Remote Similarity	NPD6099	Approved
0.6667	Remote Similarity	NPD7497	Discontinued
0.6667	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2796	Approved
0.6667	Remote Similarity	NPD1551	Phase 2
0.6667	Remote Similarity	NPD6100	Approved
0.6649	Remote Similarity	NPD8435	Approved
0.6649	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD7768	Phase 2
0.6647	Remote Similarity	NPD6798	Discontinued
0.6634	Remote Similarity	NPD8320	Phase 1
0.6634	Remote Similarity	NPD8319	Approved
0.6632	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.663	Remote Similarity	NPD8455	Phase 2
0.6628	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD6832	Phase 2
0.6619	Remote Similarity	NPD4665	Approved
0.6617	Remote Similarity	NPD3057	Approved
0.661	Remote Similarity	NPD1512	Approved
0.6607	Remote Similarity	NPD6233	Phase 2
0.66	Remote Similarity	NPD4107	Approved
0.6596	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.659	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD7930	Approved
0.6584	Remote Similarity	NPD7698	Approved
0.6584	Remote Similarity	NPD7696	Phase 3
0.6584	Remote Similarity	NPD7697	Approved
0.6573	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.657	Remote Similarity	NPD2935	Discontinued
0.6564	Remote Similarity	NPD8360	Approved
0.6564	Remote Similarity	NPD8361	Approved
0.6561	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD7229	Phase 3
0.6554	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD7870	Phase 2
0.6552	Remote Similarity	NPD1243	Approved
0.6552	Remote Similarity	NPD2800	Approved
0.6552	Remote Similarity	NPD7871	Phase 2
0.655	Remote Similarity	NPD7097	Phase 1
0.655	Remote Similarity	NPD8285	Discontinued
0.6548	Remote Similarity	NPD2313	Discontinued
0.6548	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD7701	Phase 2
0.6535	Remote Similarity	NPD2972	Approved
0.6535	Remote Similarity	NPD3533	Approved
0.6533	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD6002	Phase 3
0.6532	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD6005	Phase 3
0.6532	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD2344	Approved
0.6532	Remote Similarity	NPD6004	Phase 3
0.6529	Remote Similarity	NPD447	Suspended
0.6522	Remote Similarity	NPD7783	Phase 2
0.6522	Remote Similarity	NPD7801	Approved
0.6522	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.652	Remote Similarity	NPD7999	Approved
0.6517	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD3750	Approved
0.6514	Remote Similarity	NPD4110	Phase 3
0.6497	Remote Similarity	NPD1511	Approved
0.6485	Remote Similarity	NPD4482	Phase 3
0.6477	Remote Similarity	NPD2354	Approved
0.6477	Remote Similarity	NPD3887	Approved
0.6471	Remote Similarity	NPD5711	Approved
0.6471	Remote Similarity	NPD4060	Phase 1
0.6471	Remote Similarity	NPD5710	Approved
0.6467	Remote Similarity	NPD7057	Phase 3
0.6467	Remote Similarity	NPD7058	Phase 2
0.6463	Remote Similarity	NPD1608	Approved
0.645	Remote Similarity	NPD8485	Approved
0.645	Remote Similarity	NPD3764	Approved
0.6436	Remote Similarity	NPD4580	Approved
0.6433	Remote Similarity	NPD1933	Approved
0.6432	Remote Similarity	NPD6534	Approved
0.6432	Remote Similarity	NPD6535	Approved
0.6429	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD8151	Discontinued
0.642	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.642	Remote Similarity	NPD7003	Approved
0.6418	Remote Similarity	NPD7699	Phase 2
0.6418	Remote Similarity	NPD7700	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