NPASS Compound

Structure

NPC472702 OpenBabel07101719522D 40 42 0 0 1 0 0 0 0 0999 V2000 -1.8176 1.9952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0845 1.2637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2517 -5.3321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2112 -5.3321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4944 1.2042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0455 -0.1509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8757 -2.2389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6976 -1.0287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4460 1.5925 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8844 1.3263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2939 -1.6621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9730 0.5323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8176 0.5323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5202 -4.0652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2517 -3.6429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5964 0.0494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2386 -0.9220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5507 -0.1992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9296 0.5679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4783 -1.2899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3649 -0.1992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2399 1.2637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5202 -4.9098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3788 0.3676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9373 -1.3966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0883 1.0441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2517 -0.2645 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9346 0.2136 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0640 -0.8577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8951 -0.7069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1385 -0.1992 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3649 -0.0685 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2204 -0.8153 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1385 -0.0685 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7073 0.4616 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.5770 -0.3347 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9871 -2.2723 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4280 -1.3621 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5020 1.2808 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 22 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 23 1 0 0 0 0 5 24 1 0 0 0 0 6 24 1 0 0 0 0 7 25 1 0 0 0 0 8 25 1 0 0 0 0 9 26 1 0 0 0 0 10 26 1 0 0 0 0 11 31 1 0 0 0 0 12 13 1 0 0 0 0 12 18 1 0 0 0 0 13 22 2 0 0 0 0 14 15 1 0 0 0 0 14 23 2 0 0 0 0 15 27 1 0 0 0 0 16 19 1 0 0 0 0 16 24 2 0 0 0 0 17 20 1 0 0 0 0 17 25 2 0 0 0 0 18 31 1 0 0 0 0 19 32 1 0 0 0 0 21 27 1 0 0 0 0 21 32 1 0 0 0 0 26 28 1 0 0 0 0 27 31 1 6 0 0 0 28 34 1 0 0 0 0 28 36 2 0 0 0 0 29 32 1 0 0 0 0 29 33 1 0 0 0 0 29 37 2 0 0 0 0 30 33 1 0 0 0 0 30 34 1 0 0 0 0 30 38 2 0 0 0 0 31 34 1 6 0 0 0 32 35 1 6 0 0 0 33 20 1 6 0 0 0 33 40 1 0 0 0 0 34 35 1 1 0 0 0 35 39 1 0 0 0 0 35 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	552.38
Volume:	613.742
LogP:	8.743
LogD:	6.043
LogS:	-4.644
# Rotatable Bonds:	11
TPSA:	80.67
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.21
Synthetic Accessibility Score:	6.171
Fsp3:	0.686
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.095
MDCK Permeability:	1.3495320672518574e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.024
Human Intestinal Absorption (HIA):	0.095
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	0.973

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.099
Plasma Protein Binding (PPB):	81.93029022216797%
Volume Distribution (VD):	3.956
Pgp-substrate:	8.630294799804688%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.833
CYP2C19-inhibitor:	0.4
CYP2C19-substrate:	0.927
CYP2C9-inhibitor:	0.348
CYP2C9-substrate:	0.006
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.026
CYP3A4-inhibitor:	0.797
CYP3A4-substrate:	0.923

ADMET: Excretion

Clearance (CL):	10.051
Half-life (T1/2):	0.133

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.98
Drug-inuced Liver Injury (DILI):	0.947
AMES Toxicity:	0.919
Rat Oral Acute Toxicity:	0.902
Maximum Recommended Daily Dose:	0.017
Skin Sensitization:	0.061
Carcinogencity:	0.846
Eye Corrosion:	0.007
Eye Irritation:	0.037
Respiratory Toxicity:	0.451

Download Data

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

Natural Product: NPC472702

Natural Product ID:	NPC472702
*Common Name:**	IFUPNXPBDBNEAO-SVROTJEJSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	IFUPNXPBDBNEAO-SVROTJEJSA-N
Standard InCHI:	InChI=1S/C35H52O5/c1-22(2)13-12-18-31(11)27(15-14-23(3)4)21-32(19-16-24(5)6)29(37)33(20-17-25(7)8)30(38)34(31,28(36)26(9)10)35(32,39)40-33/h13-14,16-17,26-27,39H,12,15,18-21H2,1-11H3/t27-,31+,32+,33+,34+,35?/m0/s1
SMILES:	CC(=CCC[C@]1(C)[C@@H](CC=C(C)C)C[C@]2(C3([C@]1(C(=O)C(C)C)C(=O)[C@](O3)(C2=O)CC=C(C)C)O)CC=C(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581606
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids

*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
NPO19915	Hypericum henryi	Species	Hypericaceae	Eukaryota	aerial parts	Yunnan, China	n.a.	PMID[25871261]
NPO19915	Hypericum henryi	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19915	Hypericum henryi	Species	Hypericaceae	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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[476187]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	40000.0	nM	PMID[476187]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[476187]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	40000.0	nM	PMID[476187]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	40000.0	nM	PMID[476187]

☑ 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 NPC472702 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	216
0.1-0.2	1525
0.2-0.3	6194
0.3-0.4	13437
0.4-0.5	9785
0.5-0.6	7580
0.6-0.7	3834
0.7-0.8	120
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472685
0.9892	High Similarity	NPC474802
0.8137	Intermediate Similarity	NPC46761
0.8037	Intermediate Similarity	NPC220705
0.7843	Intermediate Similarity	NPC269492
0.7757	Intermediate Similarity	NPC32006
0.7757	Intermediate Similarity	NPC85529
0.7732	Intermediate Similarity	NPC472686
0.7732	Intermediate Similarity	NPC290329
0.7658	Intermediate Similarity	NPC193948
0.7647	Intermediate Similarity	NPC293086
0.7615	Intermediate Similarity	NPC469508
0.7547	Intermediate Similarity	NPC323441
0.75	Intermediate Similarity	NPC325769
0.75	Intermediate Similarity	NPC188291
0.7478	Intermediate Similarity	NPC318751
0.7453	Intermediate Similarity	NPC472727
0.7453	Intermediate Similarity	NPC472728
0.7451	Intermediate Similarity	NPC327515
0.7449	Intermediate Similarity	NPC251170
0.7431	Intermediate Similarity	NPC472645
0.7431	Intermediate Similarity	NPC471332
0.7431	Intermediate Similarity	NPC471333
0.7429	Intermediate Similarity	NPC472690
0.7429	Intermediate Similarity	NPC470834
0.7429	Intermediate Similarity	NPC477267
0.7429	Intermediate Similarity	NPC472689
0.7429	Intermediate Similarity	NPC477268
0.7414	Intermediate Similarity	NPC268958
0.7404	Intermediate Similarity	NPC134067
0.7387	Intermediate Similarity	NPC23497
0.7358	Intermediate Similarity	NPC177680
0.7358	Intermediate Similarity	NPC472730
0.7358	Intermediate Similarity	NPC472729
0.7358	Intermediate Similarity	NPC153776
0.7353	Intermediate Similarity	NPC263977
0.7333	Intermediate Similarity	NPC272411
0.7333	Intermediate Similarity	NPC223169
0.7328	Intermediate Similarity	NPC297179
0.7315	Intermediate Similarity	NPC163249
0.7308	Intermediate Similarity	NPC477439
0.7304	Intermediate Similarity	NPC207217
0.7304	Intermediate Similarity	NPC270478
0.7297	Intermediate Similarity	NPC29827
0.7297	Intermediate Similarity	NPC469845
0.7295	Intermediate Similarity	NPC476851
0.7292	Intermediate Similarity	NPC28319
0.7281	Intermediate Similarity	NPC326264
0.7281	Intermediate Similarity	NPC472929
0.7273	Intermediate Similarity	NPC469569
0.7265	Intermediate Similarity	NPC472933
0.7264	Intermediate Similarity	NPC254496
0.7264	Intermediate Similarity	NPC472731
0.7264	Intermediate Similarity	NPC273269
0.7264	Intermediate Similarity	NPC285513
0.7264	Intermediate Similarity	NPC472732
0.7263	Intermediate Similarity	NPC266124
0.7241	Intermediate Similarity	NPC472927
0.7238	Intermediate Similarity	NPC477437
0.7238	Intermediate Similarity	NPC477438
0.7236	Intermediate Similarity	NPC476852
0.7222	Intermediate Similarity	NPC115862
0.7222	Intermediate Similarity	NPC472643
0.7217	Intermediate Similarity	NPC247069
0.7212	Intermediate Similarity	NPC477436
0.7212	Intermediate Similarity	NPC477435
0.7207	Intermediate Similarity	NPC220974
0.7203	Intermediate Similarity	NPC472076
0.7203	Intermediate Similarity	NPC472075
0.7196	Intermediate Similarity	NPC471330
0.7196	Intermediate Similarity	NPC471331
0.7196	Intermediate Similarity	NPC203388
0.7196	Intermediate Similarity	NPC109059
0.7196	Intermediate Similarity	NPC288
0.7196	Intermediate Similarity	NPC472687
0.7196	Intermediate Similarity	NPC99657
0.7182	Intermediate Similarity	NPC13385
0.7182	Intermediate Similarity	NPC472228
0.7182	Intermediate Similarity	NPC2436
0.7182	Intermediate Similarity	NPC135854
0.7182	Intermediate Similarity	NPC470251
0.7182	Intermediate Similarity	NPC13149
0.7182	Intermediate Similarity	NPC284865
0.7182	Intermediate Similarity	NPC216245
0.7182	Intermediate Similarity	NPC472227
0.7179	Intermediate Similarity	NPC204552
0.7179	Intermediate Similarity	NPC17772
0.7179	Intermediate Similarity	NPC188667
0.7177	Intermediate Similarity	NPC100390
0.7177	Intermediate Similarity	NPC102316
0.7177	Intermediate Similarity	NPC254614
0.717	Intermediate Similarity	NPC121036
0.717	Intermediate Similarity	NPC472733
0.717	Intermediate Similarity	NPC472674
0.717	Intermediate Similarity	NPC472734
0.7168	Intermediate Similarity	NPC272898
0.7168	Intermediate Similarity	NPC473036
0.7167	Intermediate Similarity	NPC472078
0.7167	Intermediate Similarity	NPC472077
0.7158	Intermediate Similarity	NPC78935
0.7157	Intermediate Similarity	NPC269677
0.7156	Intermediate Similarity	NPC53222
0.7156	Intermediate Similarity	NPC470840
0.7155	Intermediate Similarity	NPC235539
0.7155	Intermediate Similarity	NPC134869
0.7155	Intermediate Similarity	NPC152199
0.7154	Intermediate Similarity	NPC264192
0.7143	Intermediate Similarity	NPC212812
0.7143	Intermediate Similarity	NPC469844
0.7143	Intermediate Similarity	NPC160413
0.7143	Intermediate Similarity	NPC258674
0.7143	Intermediate Similarity	NPC44963
0.7143	Intermediate Similarity	NPC102822
0.7143	Intermediate Similarity	NPC472684
0.7143	Intermediate Similarity	NPC477046
0.7143	Intermediate Similarity	NPC189237
0.713	Intermediate Similarity	NPC472972
0.713	Intermediate Similarity	NPC477091
0.713	Intermediate Similarity	NPC474271
0.7129	Intermediate Similarity	NPC6979
0.7129	Intermediate Similarity	NPC477479
0.7129	Intermediate Similarity	NPC477478
0.7117	Intermediate Similarity	NPC475414
0.7117	Intermediate Similarity	NPC173172
0.7117	Intermediate Similarity	NPC475494
0.7117	Intermediate Similarity	NPC292588
0.7105	Intermediate Similarity	NPC43775
0.7105	Intermediate Similarity	NPC34315
0.7105	Intermediate Similarity	NPC38159
0.7103	Intermediate Similarity	NPC27105
0.7094	Intermediate Similarity	NPC27999
0.7094	Intermediate Similarity	NPC477116
0.7094	Intermediate Similarity	NPC472934
0.7094	Intermediate Similarity	NPC97908
0.7094	Intermediate Similarity	NPC287343
0.7094	Intermediate Similarity	NPC122033
0.7094	Intermediate Similarity	NPC470854
0.7094	Intermediate Similarity	NPC474654
0.7091	Intermediate Similarity	NPC320154
0.7091	Intermediate Similarity	NPC33973
0.7091	Intermediate Similarity	NPC474330
0.7091	Intermediate Similarity	NPC90177
0.7091	Intermediate Similarity	NPC470839
0.7091	Intermediate Similarity	NPC474207
0.7091	Intermediate Similarity	NPC179208
0.7091	Intermediate Similarity	NPC275583
0.7091	Intermediate Similarity	NPC70967
0.7091	Intermediate Similarity	NPC194323
0.7087	Intermediate Similarity	NPC472688
0.7087	Intermediate Similarity	NPC472676
0.7075	Intermediate Similarity	NPC31021
0.7075	Intermediate Similarity	NPC316215
0.7075	Intermediate Similarity	NPC248574
0.7073	Intermediate Similarity	NPC476859
0.7069	Intermediate Similarity	NPC18547
0.7069	Intermediate Similarity	NPC117712
0.7069	Intermediate Similarity	NPC474906
0.7069	Intermediate Similarity	NPC473798
0.7064	Intermediate Similarity	NPC475867
0.7064	Intermediate Similarity	NPC473514
0.7064	Intermediate Similarity	NPC270155
0.7064	Intermediate Similarity	NPC124211
0.7063	Intermediate Similarity	NPC242486
0.7063	Intermediate Similarity	NPC15215
0.7059	Intermediate Similarity	NPC112038
0.7059	Intermediate Similarity	NPC230016
0.7059	Intermediate Similarity	NPC171722
0.7059	Intermediate Similarity	NPC38885
0.7054	Intermediate Similarity	NPC475176
0.7054	Intermediate Similarity	NPC3316
0.7054	Intermediate Similarity	NPC144854
0.7049	Intermediate Similarity	NPC225049
0.7043	Intermediate Similarity	NPC89227
0.7043	Intermediate Similarity	NPC151216
0.7043	Intermediate Similarity	NPC170212
0.7043	Intermediate Similarity	NPC265499
0.7043	Intermediate Similarity	NPC147180
0.7043	Intermediate Similarity	NPC264634
0.7043	Intermediate Similarity	NPC101825
0.7043	Intermediate Similarity	NPC205534
0.7043	Intermediate Similarity	NPC17138
0.7043	Intermediate Similarity	NPC215643
0.7043	Intermediate Similarity	NPC221511
0.704	Intermediate Similarity	NPC6274
0.704	Intermediate Similarity	NPC33378
0.704	Intermediate Similarity	NPC254146
0.7037	Intermediate Similarity	NPC164349
0.7034	Intermediate Similarity	NPC106644
0.7034	Intermediate Similarity	NPC470776
0.703	Intermediate Similarity	NPC79573
0.7027	Intermediate Similarity	NPC137657
0.7027	Intermediate Similarity	NPC118911
0.7027	Intermediate Similarity	NPC40170
0.7027	Intermediate Similarity	NPC96268
0.7018	Intermediate Similarity	NPC163314
0.7018	Intermediate Similarity	NPC470065
0.7016	Intermediate Similarity	NPC476854
0.7009	Intermediate Similarity	NPC328374
0.7009	Intermediate Similarity	NPC120708
0.7009	Intermediate Similarity	NPC259306

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 NPC472702 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	183
0.1-0.2	2050
0.2-0.3	4161
0.3-0.4	1906
0.4-0.5	474
0.5-0.6	209
0.6-0.7	154
0.7-0.8	13
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
0.7203	Intermediate Similarity	NPD6059	Approved
0.7203	Intermediate Similarity	NPD6054	Approved
0.7143	Intermediate Similarity	NPD7320	Approved
0.7117	Intermediate Similarity	NPD6675	Approved
0.7117	Intermediate Similarity	NPD7128	Approved
0.7117	Intermediate Similarity	NPD5739	Approved
0.7117	Intermediate Similarity	NPD6402	Approved
0.7083	Intermediate Similarity	NPD6370	Approved
0.708	Intermediate Similarity	NPD6373	Approved
0.708	Intermediate Similarity	NPD6372	Approved
0.7043	Intermediate Similarity	NPD6882	Approved
0.7	Intermediate Similarity	NPD6015	Approved
0.7	Intermediate Similarity	NPD6016	Approved
0.6992	Remote Similarity	NPD8293	Discontinued
0.6991	Remote Similarity	NPD6881	Approved
0.6991	Remote Similarity	NPD6899	Approved
0.6967	Remote Similarity	NPD7492	Approved
0.6957	Remote Similarity	NPD6650	Approved
0.6957	Remote Similarity	NPD6649	Approved
0.6957	Remote Similarity	NPD8130	Phase 1
0.6942	Remote Similarity	NPD5988	Approved
0.6935	Remote Similarity	NPD7736	Approved
0.6911	Remote Similarity	NPD6616	Approved
0.6903	Remote Similarity	NPD5697	Approved
0.6903	Remote Similarity	NPD5701	Approved
0.6897	Remote Similarity	NPD8297	Approved
0.6887	Remote Similarity	NPD6399	Phase 3
0.6881	Remote Similarity	NPD5696	Approved
0.687	Remote Similarity	NPD6883	Approved
0.687	Remote Similarity	NPD7290	Approved
0.687	Remote Similarity	NPD7102	Approved
0.6855	Remote Similarity	NPD7078	Approved
0.6842	Remote Similarity	NPD6011	Approved
0.6822	Remote Similarity	NPD5282	Discontinued
0.681	Remote Similarity	NPD6869	Approved
0.681	Remote Similarity	NPD6847	Approved
0.681	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6617	Approved
0.68	Remote Similarity	NPD6033	Approved
0.6796	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD4755	Approved
0.6789	Remote Similarity	NPD7902	Approved
0.6783	Remote Similarity	NPD6012	Approved
0.6783	Remote Similarity	NPD6013	Approved
0.6783	Remote Similarity	NPD6014	Approved
0.6748	Remote Similarity	NPD8328	Phase 3
0.6697	Remote Similarity	NPD4697	Phase 3
0.6667	Remote Similarity	NPD5286	Approved
0.6667	Remote Similarity	NPD6008	Approved
0.6667	Remote Similarity	NPD4700	Approved
0.6667	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD7748	Approved
0.6667	Remote Similarity	NPD5285	Approved
0.6667	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6084	Phase 2
0.6636	Remote Similarity	NPD6083	Phase 2
0.6635	Remote Similarity	NPD6098	Approved
0.6607	Remote Similarity	NPD5223	Approved
0.6606	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD5695	Phase 3
0.6604	Remote Similarity	NPD6904	Approved
0.6604	Remote Similarity	NPD6673	Approved
0.6604	Remote Similarity	NPD6080	Approved
0.6604	Remote Similarity	NPD5328	Approved
0.6571	Remote Similarity	NPD3573	Approved
0.6552	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD5225	Approved
0.6549	Remote Similarity	NPD4633	Approved
0.6549	Remote Similarity	NPD5226	Approved
0.6549	Remote Similarity	NPD5224	Approved
0.6549	Remote Similarity	NPD5211	Phase 2
0.6545	Remote Similarity	NPD5222	Approved
0.6545	Remote Similarity	NPD5221	Approved
0.6545	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD5329	Approved
0.6535	Remote Similarity	NPD4695	Discontinued
0.6529	Remote Similarity	NPD6009	Approved
0.6514	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD7900	Approved
0.6509	Remote Similarity	NPD6672	Approved
0.6509	Remote Similarity	NPD5737	Approved
0.6504	Remote Similarity	NPD6319	Approved
0.6491	Remote Similarity	NPD5174	Approved
0.6491	Remote Similarity	NPD4754	Approved
0.6491	Remote Similarity	NPD5175	Approved
0.6486	Remote Similarity	NPD5173	Approved
0.6481	Remote Similarity	NPD6050	Approved
0.6481	Remote Similarity	NPD8035	Phase 2
0.6481	Remote Similarity	NPD8034	Phase 2
0.6481	Remote Similarity	NPD6411	Approved
0.6481	Remote Similarity	NPD6079	Approved
0.6476	Remote Similarity	NPD3618	Phase 1
0.6475	Remote Similarity	NPD6335	Approved
0.6455	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD4629	Approved
0.6455	Remote Similarity	NPD5210	Approved
0.6452	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD6274	Approved
0.6442	Remote Similarity	NPD4197	Approved
0.6442	Remote Similarity	NPD4786	Approved
0.6441	Remote Similarity	NPD4634	Approved
0.6435	Remote Similarity	NPD5141	Approved
0.6423	Remote Similarity	NPD7101	Approved
0.6423	Remote Similarity	NPD7100	Approved
0.6408	Remote Similarity	NPD3667	Approved
0.6393	Remote Similarity	NPD6317	Approved
0.6389	Remote Similarity	NPD5692	Phase 3
0.6379	Remote Similarity	NPD4767	Approved
0.6379	Remote Similarity	NPD4768	Approved
0.6364	Remote Similarity	NPD6001	Approved
0.6341	Remote Similarity	NPD6314	Approved
0.6341	Remote Similarity	NPD6313	Approved
0.633	Remote Similarity	NPD7515	Phase 2
0.633	Remote Similarity	NPD5281	Approved
0.633	Remote Similarity	NPD5284	Approved
0.633	Remote Similarity	NPD5693	Phase 1
0.633	Remote Similarity	NPD5694	Approved
0.6321	Remote Similarity	NPD4694	Approved
0.6321	Remote Similarity	NPD5280	Approved
0.6321	Remote Similarity	NPD5690	Phase 2
0.632	Remote Similarity	NPD6908	Approved
0.632	Remote Similarity	NPD6909	Approved
0.6311	Remote Similarity	NPD6868	Approved
0.6296	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD4753	Phase 2
0.6296	Remote Similarity	NPD6101	Approved
0.6296	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD4225	Approved
0.6281	Remote Similarity	NPD4632	Approved
0.6273	Remote Similarity	NPD4202	Approved
0.6271	Remote Similarity	NPD5128	Approved
0.6271	Remote Similarity	NPD4729	Approved
0.6271	Remote Similarity	NPD4730	Approved
0.626	Remote Similarity	NPD7115	Discovery
0.625	Remote Similarity	NPD4223	Phase 3
0.625	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4221	Approved
0.6239	Remote Similarity	NPD5207	Approved
0.622	Remote Similarity	NPD7604	Phase 2
0.619	Remote Similarity	NPD5983	Phase 2
0.6186	Remote Similarity	NPD6614	Approved
0.6176	Remote Similarity	NPD3617	Approved
0.6174	Remote Similarity	NPD1700	Approved
0.6167	Remote Similarity	NPD5250	Approved
0.6167	Remote Similarity	NPD5251	Approved
0.6167	Remote Similarity	NPD5249	Phase 3
0.6167	Remote Similarity	NPD5169	Approved
0.6167	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD5135	Approved
0.6167	Remote Similarity	NPD5248	Approved
0.6167	Remote Similarity	NPD5247	Approved
0.6154	Remote Similarity	NPD5369	Approved
0.6132	Remote Similarity	NPD3668	Phase 3
0.6126	Remote Similarity	NPD5778	Approved
0.6126	Remote Similarity	NPD5779	Approved
0.6124	Remote Similarity	NPD6336	Discontinued
0.6121	Remote Similarity	NPD5091	Approved
0.6116	Remote Similarity	NPD5215	Approved
0.6116	Remote Similarity	NPD5217	Approved
0.6116	Remote Similarity	NPD5127	Approved
0.6116	Remote Similarity	NPD5216	Approved
0.6107	Remote Similarity	NPD7319	Approved
0.6083	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD8513	Phase 3
0.6063	Remote Similarity	NPD8517	Approved
0.6063	Remote Similarity	NPD8515	Approved
0.6063	Remote Similarity	NPD8516	Approved
0.6058	Remote Similarity	NPD7525	Registered
0.6055	Remote Similarity	NPD6903	Approved
0.605	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.605	Remote Similarity	NPD6412	Phase 2
0.6042	Remote Similarity	NPD7331	Phase 2
0.6019	Remote Similarity	NPD5786	Approved
0.6019	Remote Similarity	NPD5205	Approved
0.6019	Remote Similarity	NPD4688	Approved
0.6019	Remote Similarity	NPD4623	Approved
0.6019	Remote Similarity	NPD6409	Approved
0.6019	Remote Similarity	NPD7521	Approved
0.6019	Remote Similarity	NPD4690	Approved
0.6019	Remote Similarity	NPD4519	Discontinued
0.6019	Remote Similarity	NPD4689	Approved
0.6019	Remote Similarity	NPD4693	Phase 3
0.6019	Remote Similarity	NPD5279	Phase 3
0.6019	Remote Similarity	NPD4138	Approved
0.6019	Remote Similarity	NPD7334	Approved
0.6019	Remote Similarity	NPD6684	Approved
0.6019	Remote Similarity	NPD7146	Approved
0.6019	Remote Similarity	NPD5330	Approved
0.6018	Remote Similarity	NPD5654	Approved
0.6	Remote Similarity	NPD7638	Approved
0.6	Remote Similarity	NPD7507	Approved
0.6	Remote Similarity	NPD5168	Approved
0.5981	Remote Similarity	NPD3133	Approved
0.5981	Remote Similarity	NPD3665	Phase 1
0.5981	Remote Similarity	NPD3666	Approved
0.5969	Remote Similarity	NPD6067	Discontinued
0.5968	Remote Similarity	NPD5167	Approved
0.5965	Remote Similarity	NPD7614	Phase 1
0.5948	Remote Similarity	NPD7639	Approved
0.5948	Remote Similarity	NPD7640	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