NPASS Compound

Structure

NPC7752 OpenBabel07101719122D 43 45 0 0 1 0 0 0 0 0999 V2000 -7.7942 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 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 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 13 21 1 0 0 0 0 14 22 1 0 0 0 0 15 21 2 0 0 0 0 15 23 1 0 0 0 0 16 21 1 0 0 0 0 16 25 2 0 0 0 0 17 22 2 0 0 0 0 17 24 1 0 0 0 0 18 23 2 0 0 0 0 18 25 1 0 0 0 0 19 24 2 0 0 0 0 19 26 1 0 0 0 0 20 34 1 0 0 0 0 22 28 1 0 0 0 0 23 35 1 0 0 0 0 24 36 1 0 0 0 0 25 41 1 0 0 0 0 26 28 2 0 0 0 0 26 42 1 0 0 0 0 27 20 1 1 0 0 0 27 29 1 0 0 0 0 27 43 1 0 0 0 0 28 32 1 0 0 0 0 29 30 1 0 0 0 0 29 37 1 1 0 0 0 30 31 1 0 0 0 0 30 38 1 1 0 0 0 31 33 1 0 0 0 0 31 39 1 6 0 0 0 32 40 2 0 0 0 0 32 41 1 0 0 0 0 33 42 1 1 0 0 0 33 43 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	604.32
Volume:	623.102
LogP:	6.282
LogD:	4.291
LogS:	-3.856
# Rotatable Bonds:	18
TPSA:	166.14
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.086
Synthetic Accessibility Score:	4.111
Fsp3:	0.606
Lipinski Rule-of-5:	Rejected
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:	-5.714
MDCK Permeability:	2.5283532522735186e-05
Pgp-inhibitor:	0.447
Pgp-substrate:	0.968
Human Intestinal Absorption (HIA):	0.829
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.026
Plasma Protein Binding (PPB):	99.70677185058594%
Volume Distribution (VD):	0.598
Pgp-substrate:	0.8246524930000305%

ADMET: Metabolism

CYP1A2-inhibitor:	0.521
CYP1A2-substrate:	0.114
CYP2C19-inhibitor:	0.379
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.349
CYP2C9-substrate:	0.964
CYP2D6-inhibitor:	0.942
CYP2D6-substrate:	0.144
CYP3A4-inhibitor:	0.267
CYP3A4-substrate:	0.013

ADMET: Excretion

Clearance (CL):	6.225
Half-life (T1/2):	0.45

ADMET: Toxicity

hERG Blockers:	0.511
Human Hepatotoxicity (H-HT):	0.036
Drug-inuced Liver Injury (DILI):	0.036
AMES Toxicity:	0.232
Rat Oral Acute Toxicity:	0.017
Maximum Recommended Daily Dose:	0.724
Skin Sensitization:	0.966
Carcinogencity:	0.022
Eye Corrosion:	0.003
Eye Irritation:	0.377
Respiratory Toxicity:	0.06

Download Data

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

Natural Product: NPC7752

Natural Product ID:	NPC7752
*Common Name:**	(3-Heptyl-5-Hydroxyphenyl) 2-Heptyl-4-Hydroxy-6-[(2S,3R,4S,5R,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]Oxybenzoate
IUPAC Name:	(3-heptyl-5-hydroxyphenyl) 2-heptyl-4-hydroxy-6-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzoate
Synonyms:
Standard InCHIKey:	BOTABODRPOJDQC-FLHDZCCQSA-N
Standard InCHI:	InChI=1S/C33H48O10/c1-3-5-7-9-11-13-21-15-23(35)18-25(16-21)41-32(40)28-22(14-12-10-8-6-4-2)17-24(36)19-26(28)42-33-31(39)30(38)29(37)27(20-34)43-33/h15-19,27,29-31,33-39H,3-14,20H2,1-2H3/t27-,29+,30+,31-,33-/m1/s1
SMILES:	CCCCCCCc1cc(O)cc(c1)OC(=O)c1c(CCCCCCC)cc(cc1O[C@@H]1O[C@H](CO)[C@@H]([C@@H]([C@H]1O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL455232
PubChem CID:	24878794
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

*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
NPO33495	Acremonium sp. BCC 14080	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[18363379]

☑ 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	6

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	25000.0	nM	PMID[509009]
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	=	13900.0	nM	PMID[509009]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	43200.0	nM	PMID[509009]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	>	10000.0	nM	PMID[509009]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	IC50	=	7200.0	nM	PMID[509009]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	4400.0	nM	PMID[509009]

☑ 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 NPC7752 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	364
0.1-0.2	1496
0.2-0.3	3267
0.3-0.4	7317
0.4-0.5	10012
0.5-0.6	5223
0.6-0.7	4968
0.7-0.8	6637
0.8-0.85	2719
0.85-0.9	618
0.9-0.95	74
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9873	High Similarity	NPC249977
0.9383	High Similarity	NPC298778
0.9375	High Similarity	NPC99216
0.9367	High Similarity	NPC328093
0.9329	High Similarity	NPC63105
0.9317	High Similarity	NPC178851
0.9299	High Similarity	NPC127406
0.9295	High Similarity	NPC185103
0.9241	High Similarity	NPC43638
0.9241	High Similarity	NPC257309
0.9212	High Similarity	NPC470454
0.9212	High Similarity	NPC199533
0.9212	High Similarity	NPC474345
0.9212	High Similarity	NPC68381
0.9207	High Similarity	NPC288152
0.9207	High Similarity	NPC9002
0.9207	High Similarity	NPC257011
0.9207	High Similarity	NPC137871
0.9202	High Similarity	NPC259905
0.9182	High Similarity	NPC279732
0.9177	High Similarity	NPC261866
0.9172	High Similarity	NPC106625
0.9167	High Similarity	NPC473631
0.9167	High Similarity	NPC293227
0.9167	High Similarity	NPC473717
0.9167	High Similarity	NPC475662
0.9162	High Similarity	NPC84494
0.9162	High Similarity	NPC245059
0.9152	High Similarity	NPC213052
0.9146	High Similarity	NPC199079
0.9146	High Similarity	NPC210808
0.9141	High Similarity	NPC298847
0.913	High Similarity	NPC300537
0.913	High Similarity	NPC127782
0.9114	High Similarity	NPC99233
0.9108	High Similarity	NPC259182
0.9108	High Similarity	NPC121001
0.9107	High Similarity	NPC470452
0.9107	High Similarity	NPC470453
0.9107	High Similarity	NPC477860
0.9107	High Similarity	NPC470448
0.9107	High Similarity	NPC164047
0.9107	High Similarity	NPC475161
0.9091	High Similarity	NPC5029
0.9091	High Similarity	NPC271385
0.9091	High Similarity	NPC30432
0.9091	High Similarity	NPC76128
0.9091	High Similarity	NPC111536
0.9085	High Similarity	NPC473202
0.9085	High Similarity	NPC222455
0.908	High Similarity	NPC70441
0.9068	High Similarity	NPC101636
0.9062	High Similarity	NPC73511
0.9062	High Similarity	NPC308265
0.9062	High Similarity	NPC43761
0.9059	High Similarity	NPC473686
0.9059	High Similarity	NPC221140
0.9059	High Similarity	NPC475220
0.9059	High Similarity	NPC229817
0.9059	High Similarity	NPC475352
0.9057	High Similarity	NPC206378
0.9051	High Similarity	NPC299435
0.9051	High Similarity	NPC260604
0.9045	High Similarity	NPC70016
0.9045	High Similarity	NPC215921
0.9045	High Similarity	NPC190217
0.9042	High Similarity	NPC46958
0.903	High Similarity	NPC76047
0.9024	High Similarity	NPC116745
0.9018	High Similarity	NPC475979
0.9018	High Similarity	NPC294722
0.9012	High Similarity	NPC473043
0.9012	High Similarity	NPC298171
0.9012	High Similarity	NPC216752
0.9006	High Similarity	NPC246469
0.9006	High Similarity	NPC271270
0.9006	High Similarity	NPC97285
0.9006	High Similarity	NPC142860
0.9006	High Similarity	NPC271479
0.9	High Similarity	NPC161749
0.9	High Similarity	NPC177742
0.9	High Similarity	NPC6985
0.9	High Similarity	NPC197896
0.9	High Similarity	NPC23817
0.9	High Similarity	NPC156457
0.9	High Similarity	NPC258035
0.9	High Similarity	NPC313163
0.8994	High Similarity	NPC26195
0.8994	High Similarity	NPC470604
0.8994	High Similarity	NPC27408
0.8994	High Similarity	NPC72649
0.8994	High Similarity	NPC470605
0.8994	High Similarity	NPC95090
0.8994	High Similarity	NPC169248
0.8994	High Similarity	NPC97052
0.8994	High Similarity	NPC39351
0.8994	High Similarity	NPC470603
0.8987	High Similarity	NPC259767
0.8987	High Similarity	NPC88484
0.8981	High Similarity	NPC106025
0.8981	High Similarity	NPC191154
0.8981	High Similarity	NPC307780
0.8981	High Similarity	NPC477240
0.8981	High Similarity	NPC309979
0.8981	High Similarity	NPC214454
0.8976	High Similarity	NPC472386
0.8974	High Similarity	NPC199335
0.897	High Similarity	NPC43587
0.897	High Similarity	NPC293629
0.8968	High Similarity	NPC237208
0.8963	High Similarity	NPC262222
0.8963	High Similarity	NPC236934
0.8963	High Similarity	NPC68592
0.8963	High Similarity	NPC5778
0.8963	High Similarity	NPC298666
0.8957	High Similarity	NPC243930
0.8957	High Similarity	NPC309025
0.8957	High Similarity	NPC19709
0.8957	High Similarity	NPC29830
0.8957	High Similarity	NPC222936
0.8957	High Similarity	NPC88023
0.8957	High Similarity	NPC124155
0.8957	High Similarity	NPC257566
0.8957	High Similarity	NPC284960
0.8951	High Similarity	NPC224530
0.8951	High Similarity	NPC85707
0.8951	High Similarity	NPC216496
0.8951	High Similarity	NPC303913
0.8951	High Similarity	NPC259957
0.8951	High Similarity	NPC159579
0.8951	High Similarity	NPC48093
0.8951	High Similarity	NPC129217
0.8947	High Similarity	NPC241847
0.8944	High Similarity	NPC138811
0.8944	High Similarity	NPC22062
0.8944	High Similarity	NPC473634
0.8938	High Similarity	NPC170475
0.8938	High Similarity	NPC45165
0.8931	High Similarity	NPC29763
0.8931	High Similarity	NPC210003
0.8931	High Similarity	NPC87304
0.8931	High Similarity	NPC83283
0.8931	High Similarity	NPC39360
0.8931	High Similarity	NPC211158
0.8931	High Similarity	NPC268950
0.8931	High Similarity	NPC108706
0.8931	High Similarity	NPC143851
0.8931	High Similarity	NPC78021
0.8929	High Similarity	NPC475233
0.8929	High Similarity	NPC475246
0.8924	High Similarity	NPC134819
0.8922	High Similarity	NPC175230
0.8922	High Similarity	NPC472054
0.8922	High Similarity	NPC25724
0.8922	High Similarity	NPC263119
0.8922	High Similarity	NPC46640
0.8922	High Similarity	NPC34436
0.8922	High Similarity	NPC98776
0.8922	High Similarity	NPC166674
0.8922	High Similarity	NPC172033
0.8922	High Similarity	NPC88560
0.8922	High Similarity	NPC219600
0.8917	High Similarity	NPC270160
0.8917	High Similarity	NPC237440
0.8917	High Similarity	NPC476684
0.8916	High Similarity	NPC44328
0.8916	High Similarity	NPC244776
0.8916	High Similarity	NPC177731
0.8916	High Similarity	NPC105095
0.8916	High Similarity	NPC116864
0.8916	High Similarity	NPC79056
0.891	High Similarity	NPC302989
0.891	High Similarity	NPC23084
0.8909	High Similarity	NPC477502
0.8909	High Similarity	NPC229729
0.8903	High Similarity	NPC29577
0.8903	High Similarity	NPC134621
0.8902	High Similarity	NPC22832
0.8902	High Similarity	NPC165720
0.8902	High Similarity	NPC311830
0.8896	High Similarity	NPC475382
0.8896	High Similarity	NPC131745
0.8896	High Similarity	NPC189142
0.8896	High Similarity	NPC27942
0.8896	High Similarity	NPC259834
0.8896	High Similarity	NPC472876
0.8896	High Similarity	NPC22324
0.8896	High Similarity	NPC44947
0.8896	High Similarity	NPC190450
0.8896	High Similarity	NPC77660
0.8895	High Similarity	NPC65489
0.8889	High Similarity	NPC231254
0.8889	High Similarity	NPC472320
0.8889	High Similarity	NPC473623
0.8889	High Similarity	NPC470358
0.8889	High Similarity	NPC110349
0.8889	High Similarity	NPC153342
0.8882	High Similarity	NPC65003
0.8882	High Similarity	NPC129827
0.8882	High Similarity	NPC60966

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 NPC7752 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	318
0.1-0.2	907
0.2-0.3	1794
0.3-0.4	2566
0.4-0.5	1895
0.5-0.6	1048
0.6-0.7	412
0.7-0.8	165
0.8-0.85	39
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9	High Similarity	NPD4381	Clinical (unspecified phase)
0.8916	High Similarity	NPD7074	Phase 3
0.8855	High Similarity	NPD7804	Clinical (unspecified phase)
0.8855	High Similarity	NPD7054	Approved
0.8812	High Similarity	NPD7819	Suspended
0.8802	High Similarity	NPD7472	Approved
0.8757	High Similarity	NPD7808	Phase 3
0.8698	High Similarity	NPD7251	Discontinued
0.8683	High Similarity	NPD3818	Discontinued
0.865	High Similarity	NPD7075	Discontinued
0.8647	High Similarity	NPD4338	Clinical (unspecified phase)
0.8639	High Similarity	NPD6797	Phase 2
0.8588	High Similarity	NPD6559	Discontinued
0.8519	High Similarity	NPD1934	Approved
0.8476	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8395	Intermediate Similarity	NPD4380	Phase 2
0.8382	Intermediate Similarity	NPD8312	Approved
0.8382	Intermediate Similarity	NPD8313	Approved
0.8343	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8343	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8343	Intermediate Similarity	NPD6166	Phase 2
0.8304	Intermediate Similarity	NPD5844	Phase 1
0.8303	Intermediate Similarity	NPD3817	Phase 2
0.8303	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD6801	Discontinued
0.828	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8274	Intermediate Similarity	NPD6959	Discontinued
0.8242	Intermediate Similarity	NPD1465	Phase 2
0.8225	Intermediate Similarity	NPD6232	Discontinued
0.8217	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD7473	Discontinued
0.8166	Intermediate Similarity	NPD7199	Phase 2
0.8165	Intermediate Similarity	NPD1549	Phase 2
0.814	Intermediate Similarity	NPD7228	Approved
0.8137	Intermediate Similarity	NPD6799	Approved
0.8133	Intermediate Similarity	NPD2801	Approved
0.8121	Intermediate Similarity	NPD7411	Suspended
0.8103	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD7783	Phase 2
0.8086	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD2532	Approved
0.8086	Intermediate Similarity	NPD2533	Approved
0.8086	Intermediate Similarity	NPD2534	Approved
0.8085	Intermediate Similarity	NPD8151	Discontinued
0.8084	Intermediate Similarity	NPD5402	Approved
0.8072	Intermediate Similarity	NPD37	Approved
0.8061	Intermediate Similarity	NPD6599	Discontinued
0.8047	Intermediate Similarity	NPD6234	Discontinued
0.8036	Intermediate Similarity	NPD4965	Approved
0.8036	Intermediate Similarity	NPD4966	Approved
0.8036	Intermediate Similarity	NPD4967	Phase 2
0.8036	Intermediate Similarity	NPD7768	Phase 2
0.8025	Intermediate Similarity	NPD1511	Approved
0.8024	Intermediate Similarity	NPD8455	Phase 2
0.8023	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD3749	Approved
0.7988	Intermediate Similarity	NPD5403	Approved
0.7965	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD3750	Approved
0.795	Intermediate Similarity	NPD4628	Phase 3
0.7944	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD1653	Approved
0.7929	Intermediate Similarity	NPD3882	Suspended
0.7927	Intermediate Similarity	NPD1512	Approved
0.7925	Intermediate Similarity	NPD2796	Approved
0.7914	Intermediate Similarity	NPD7435	Discontinued
0.7866	Intermediate Similarity	NPD5401	Approved
0.7862	Intermediate Similarity	NPD1510	Phase 2
0.7853	Intermediate Similarity	NPD7685	Pre-registration
0.7829	Intermediate Similarity	NPD3751	Discontinued
0.7821	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD3787	Discontinued
0.7791	Intermediate Similarity	NPD5494	Approved
0.7784	Intermediate Similarity	NPD3226	Approved
0.7771	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD7874	Approved
0.776	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD6776	Approved
0.7754	Intermediate Similarity	NPD6779	Approved
0.7754	Intermediate Similarity	NPD6778	Approved
0.7754	Intermediate Similarity	NPD6780	Approved
0.7754	Intermediate Similarity	NPD6781	Approved
0.7754	Intermediate Similarity	NPD6782	Approved
0.7754	Intermediate Similarity	NPD6777	Approved
0.7753	Intermediate Similarity	NPD7240	Approved
0.773	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD7697	Approved
0.7725	Intermediate Similarity	NPD7696	Phase 3
0.7725	Intermediate Similarity	NPD7698	Approved
0.7722	Intermediate Similarity	NPD1240	Approved
0.7702	Intermediate Similarity	NPD1551	Phase 2
0.7702	Intermediate Similarity	NPD2935	Discontinued
0.7684	Intermediate Similarity	NPD7870	Phase 2
0.7684	Intermediate Similarity	NPD7871	Phase 2
0.768	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7656	Intermediate Similarity	NPD7701	Phase 2
0.764	Intermediate Similarity	NPD3748	Approved
0.7625	Intermediate Similarity	NPD1607	Approved
0.7622	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD7584	Approved
0.7602	Intermediate Similarity	NPD7930	Approved
0.76	Intermediate Similarity	NPD5710	Approved
0.76	Intermediate Similarity	NPD5711	Approved
0.7593	Intermediate Similarity	NPD6099	Approved
0.7593	Intermediate Similarity	NPD6100	Approved
0.7592	Intermediate Similarity	NPD8319	Approved
0.7592	Intermediate Similarity	NPD8320	Phase 1
0.759	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD6832	Phase 2
0.7579	Intermediate Similarity	NPD6823	Phase 2
0.7565	Intermediate Similarity	NPD7585	Approved
0.7561	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD7700	Phase 2
0.7553	Intermediate Similarity	NPD7699	Phase 2
0.7546	Intermediate Similarity	NPD7266	Discontinued
0.7546	Intermediate Similarity	NPD2346	Discontinued
0.7545	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD8434	Phase 2
0.7541	Intermediate Similarity	NPD8150	Discontinued
0.7538	Intermediate Similarity	NPD7801	Approved
0.7513	Intermediate Similarity	NPD7583	Approved
0.75	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1613	Approved
0.7487	Intermediate Similarity	NPD6534	Approved
0.7487	Intermediate Similarity	NPD6535	Approved
0.7471	Intermediate Similarity	NPD7458	Discontinued
0.7471	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD920	Approved
0.7455	Intermediate Similarity	NPD1243	Approved
0.7455	Intermediate Similarity	NPD2800	Approved
0.7453	Intermediate Similarity	NPD1933	Approved
0.7453	Intermediate Similarity	NPD230	Phase 1
0.7429	Intermediate Similarity	NPD919	Approved
0.7423	Intermediate Similarity	NPD7033	Discontinued
0.7403	Intermediate Similarity	NPD5953	Discontinued
0.7401	Intermediate Similarity	NPD7229	Phase 3
0.7389	Intermediate Similarity	NPD7286	Phase 2
0.7389	Intermediate Similarity	NPD1203	Approved
0.7381	Intermediate Similarity	NPD7390	Discontinued
0.7376	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD6674	Discontinued
0.7349	Intermediate Similarity	NPD1652	Phase 2
0.7346	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD6355	Discontinued
0.7346	Intermediate Similarity	NPD447	Suspended
0.7337	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD2799	Discontinued
0.7317	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD6651	Approved
0.7296	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD6273	Approved
0.7292	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD4060	Phase 1
0.7283	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD2797	Approved
0.7268	Intermediate Similarity	NPD7680	Approved
0.7267	Intermediate Similarity	NPD3268	Approved
0.7267	Intermediate Similarity	NPD6798	Discontinued
0.7263	Intermediate Similarity	NPD3926	Phase 2
0.7262	Intermediate Similarity	NPD6190	Approved
0.725	Intermediate Similarity	NPD4908	Phase 1
0.725	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD6213	Phase 3
0.7249	Intermediate Similarity	NPD6212	Phase 3
0.7247	Intermediate Similarity	NPD8127	Discontinued
0.7244	Intermediate Similarity	NPD1091	Approved
0.7239	Intermediate Similarity	NPD5124	Phase 1
0.7239	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD3027	Phase 3
0.7197	Intermediate Similarity	NPD1608	Approved
0.7197	Intermediate Similarity	NPD9717	Approved
0.7194	Intermediate Similarity	NPD7999	Approved
0.7178	Intermediate Similarity	NPD943	Approved
0.716	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD2313	Discontinued
0.7159	Intermediate Similarity	NPD4288	Approved
0.7151	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1610	Phase 2
0.7134	Intermediate Similarity	NPD422	Phase 1
0.7128	Intermediate Similarity	NPD5006	Approved
0.7128	Intermediate Similarity	NPD5005	Approved
0.7127	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD2344	Approved
0.7125	Intermediate Similarity	NPD2798	Approved
0.712	Intermediate Similarity	NPD4363	Phase 3
0.712	Intermediate Similarity	NPD4360	Phase 2
0.7117	Intermediate Similarity	NPD6233	Phase 2
0.7108	Intermediate Similarity	NPD4308	Phase 3
0.7099	Intermediate Similarity	NPD4625	Phase 3

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