NPASS Compound

Structure

NPC474401 OpenBabel07101719152D 39 42 0 0 1 0 0 0 0 0999 V2000 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9817 -1.9319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0158 -1.6730 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 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6888 -1.2247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 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 -2.7570 -0.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 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 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 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 -4.4300 -0.2588 0.0000 C 0 0 0 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 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 0.0000 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 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 3 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 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1371 0.4483 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 -1.0000 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 -4.2575 0.6088 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 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 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 6 1 0 0 0 0 3 7 2 0 0 0 0 4 5 1 0 0 0 0 4 8 1 0 0 0 0 5 11 2 0 0 0 0 6 15 2 0 0 0 0 7 15 1 0 0 0 0 8 20 1 0 0 0 0 9 10 1 0 0 0 0 9 17 2 0 0 0 0 10 18 2 0 0 0 0 11 27 1 0 0 0 0 12 16 2 0 0 0 0 12 17 1 0 0 0 0 13 28 1 0 0 0 0 14 16 1 0 0 0 0 14 36 1 0 0 0 0 15 24 1 0 0 0 0 16 18 1 0 0 0 0 17 29 1 0 0 0 0 18 37 1 0 0 0 0 19 13 1 1 0 0 0 19 21 1 0 0 0 0 19 38 1 0 0 0 0 20 27 1 0 0 0 0 20 30 2 0 0 0 0 21 22 1 0 0 0 0 21 31 1 6 0 0 0 22 23 1 0 0 0 0 22 32 1 1 0 0 0 23 25 1 0 0 0 0 23 39 1 6 0 0 0 24 33 2 0 0 0 0 24 39 1 0 0 0 0 25 37 1 1 0 0 0 25 38 1 0 0 0 0 26 27 1 0 0 0 0 26 34 2 0 0 0 0 26 36 1 0 0 0 0 27 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	544.16
Volume:	520.44
LogP:	1.789
LogD:	1.446
LogS:	-3.021
# Rotatable Bonds:	10
TPSA:	189.28
# H-Bond Aceptor:	12
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.172
Synthetic Accessibility Score:	4.337
Fsp3:	0.37
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:	-6.111
MDCK Permeability:	2.799024514388293e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.048
Human Intestinal Absorption (HIA):	0.607
20% Bioavailability (F20%):	0.871
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.16
Plasma Protein Binding (PPB):	93.5730972290039%
Volume Distribution (VD):	0.652
Pgp-substrate:	5.742419719696045%

ADMET: Metabolism

CYP1A2-inhibitor:	0.058
CYP1A2-substrate:	0.08
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.082
CYP2C9-inhibitor:	0.031
CYP2C9-substrate:	0.236
CYP2D6-inhibitor:	0.106
CYP2D6-substrate:	0.099
CYP3A4-inhibitor:	0.286
CYP3A4-substrate:	0.21

ADMET: Excretion

Clearance (CL):	2.445
Half-life (T1/2):	0.949

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.104
Drug-inuced Liver Injury (DILI):	0.96
AMES Toxicity:	0.429
Rat Oral Acute Toxicity:	0.052
Maximum Recommended Daily Dose:	0.002
Skin Sensitization:	0.031
Carcinogencity:	0.288
Eye Corrosion:	0.003
Eye Irritation:	0.155
Respiratory Toxicity:	0.008

Download Data

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

Natural Product: NPC474401

Natural Product ID:	NPC474401
*Common Name:**	4-Hydroxytremulacin
IUPAC Name:	[(2S,3R,4S,5S,6R)-4,5-dihydroxy-2-[4-hydroxy-2-[(1-hydroxy-6-oxocyclohex-2-ene-1-carbonyl)oxymethyl]phenoxy]-6-(hydroxymethyl)oxan-3-yl] benzoate
Synonyms:	4-Hydroxytremulacin
Standard InCHIKey:	MDHRUEIHSUOCAT-LFMHJWGUSA-N
Standard InCHI:	InChI=1S/C27H28O12/c28-13-19-21(31)22(32)23(39-24(33)15-6-2-1-3-7-15)25(38-19)37-18-10-9-17(29)12-16(18)14-36-26(34)27(35)11-5-4-8-20(27)30/h1-3,5-7,9-12,19,21-23,25,28-29,31-32,35H,4,8,13-14H2/t19-,21-,22+,23-,25-,27?/m1/s1
SMILES:	C1CC(=O)C(C=C1)(C(=O)OCC2=C(C=CC(=C2)O)OC3C(C(C(C(O3)CO)O)O)OC(=O)C4=CC=CC=C4)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL466559
PubChem CID:	16086547
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic glycosides

*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
NPO9317	Itoa orientalis	Species	Salicaceae	Eukaryota	bark, twigs, and leaves	n.a.	n.a.	PMID[18412396]
NPO9317	Itoa orientalis	Species	Salicaceae	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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	Inhibition	=	53.0	%	PMID[468892]

☑ 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 NPC474401 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	1534
0.2-0.3	3774
0.3-0.4	8321
0.4-0.5	9801
0.5-0.6	4693
0.6-0.7	6681
0.7-0.8	6548
0.8-0.85	853
0.85-0.9	101
0.9-0.95	17
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476026
1.0	High Similarity	NPC474441
1.0	High Similarity	NPC474398
0.9801	High Similarity	NPC231475
0.9801	High Similarity	NPC57072
0.9675	High Similarity	NPC475183
0.9597	High Similarity	NPC131874
0.9551	High Similarity	NPC475174
0.9545	High Similarity	NPC71780
0.9487	High Similarity	NPC280923
0.9463	High Similarity	NPC22137
0.9408	High Similarity	NPC279281
0.9408	High Similarity	NPC230439
0.9408	High Similarity	NPC299761
0.9408	High Similarity	NPC92153
0.9396	High Similarity	NPC4958
0.9396	High Similarity	NPC92054
0.9396	High Similarity	NPC140722
0.9338	High Similarity	NPC93619
0.9329	High Similarity	NPC474422
0.925	High Similarity	NPC280385
0.9216	High Similarity	NPC215811
0.9156	High Similarity	NPC299435
0.9156	High Similarity	NPC260604
0.9139	High Similarity	NPC83975
0.9091	High Similarity	NPC183536
0.9091	High Similarity	NPC34965
0.9018	High Similarity	NPC470438
0.8993	High Similarity	NPC65833
0.8993	High Similarity	NPC31081
0.8993	High Similarity	NPC245219
0.8931	High Similarity	NPC132737
0.891	High Similarity	NPC185103
0.8896	High Similarity	NPC471214
0.8889	High Similarity	NPC302989
0.882	High Similarity	NPC127415
0.8812	High Similarity	NPC217950
0.875	High Similarity	NPC328093
0.8742	High Similarity	NPC145319
0.8742	High Similarity	NPC177742
0.8735	High Similarity	NPC101191
0.8735	High Similarity	NPC210094
0.8735	High Similarity	NPC237435
0.8735	High Similarity	NPC43211
0.8735	High Similarity	NPC477848
0.8735	High Similarity	NPC49344
0.8735	High Similarity	NPC264735
0.8735	High Similarity	NPC135277
0.8735	High Similarity	NPC115760
0.8718	High Similarity	NPC475890
0.8704	High Similarity	NPC80068
0.8704	High Similarity	NPC121703
0.8696	High Similarity	NPC224530
0.8696	High Similarity	NPC216496
0.8696	High Similarity	NPC282169
0.8696	High Similarity	NPC159579
0.8696	High Similarity	NPC85707
0.8696	High Similarity	NPC48093
0.8696	High Similarity	NPC259957
0.8696	High Similarity	NPC129217
0.8683	High Similarity	NPC472380
0.8683	High Similarity	NPC233994
0.8683	High Similarity	NPC211532
0.8683	High Similarity	NPC268533
0.8683	High Similarity	NPC198324
0.8683	High Similarity	NPC472385
0.8683	High Similarity	NPC472382
0.8683	High Similarity	NPC472384
0.8679	High Similarity	NPC307938
0.8679	High Similarity	NPC323593
0.8679	High Similarity	NPC203500
0.8679	High Similarity	NPC261866
0.8671	High Similarity	NPC470331
0.8667	High Similarity	NPC210808
0.8667	High Similarity	NPC244776
0.8667	High Similarity	NPC155763
0.8667	High Similarity	NPC199079
0.8667	High Similarity	NPC116864
0.8667	High Similarity	NPC235260
0.8667	High Similarity	NPC20505
0.8667	High Similarity	NPC245014
0.8667	High Similarity	NPC84265
0.8667	High Similarity	NPC282987
0.8654	High Similarity	NPC182350
0.865	High Similarity	NPC178281
0.865	High Similarity	NPC72016
0.865	High Similarity	NPC19240
0.865	High Similarity	NPC85751
0.865	High Similarity	NPC139060
0.865	High Similarity	NPC205824
0.865	High Similarity	NPC129264
0.865	High Similarity	NPC277205
0.8642	High Similarity	NPC27942
0.8625	High Similarity	NPC60966
0.8625	High Similarity	NPC54802
0.8625	High Similarity	NPC108831
0.8625	High Similarity	NPC313163
0.8625	High Similarity	NPC156457
0.8625	High Similarity	NPC135391
0.8625	High Similarity	NPC133671
0.8625	High Similarity	NPC43638
0.8625	High Similarity	NPC182634
0.8625	High Similarity	NPC78263
0.8625	High Similarity	NPC197304
0.8625	High Similarity	NPC77672
0.8625	High Similarity	NPC161749
0.8625	High Similarity	NPC197896
0.8625	High Similarity	NPC258035
0.8623	High Similarity	NPC81042
0.8623	High Similarity	NPC223426
0.8623	High Similarity	NPC214621
0.8623	High Similarity	NPC34267
0.8614	High Similarity	NPC288152
0.8614	High Similarity	NPC175107
0.8614	High Similarity	NPC137871
0.8614	High Similarity	NPC254540
0.8614	High Similarity	NPC476405
0.8614	High Similarity	NPC153755
0.8614	High Similarity	NPC117260
0.8614	High Similarity	NPC9002
0.8614	High Similarity	NPC190003
0.8614	High Similarity	NPC257011
0.8614	High Similarity	NPC211594
0.8614	High Similarity	NPC472386
0.8614	High Similarity	NPC172807
0.8608	High Similarity	NPC88484
0.8608	High Similarity	NPC259767
0.8606	High Similarity	NPC138927
0.8598	High Similarity	NPC56077
0.8598	High Similarity	NPC70441
0.8598	High Similarity	NPC253662
0.8598	High Similarity	NPC21100
0.8598	High Similarity	NPC197285
0.8598	High Similarity	NPC88789
0.8598	High Similarity	NPC308404
0.8598	High Similarity	NPC179950
0.8598	High Similarity	NPC274618
0.8598	High Similarity	NPC145038
0.8598	High Similarity	NPC118284
0.8598	High Similarity	NPC276222
0.8598	High Similarity	NPC281131
0.8591	High Similarity	NPC320259
0.859	High Similarity	NPC111785
0.8589	High Similarity	NPC168822
0.8589	High Similarity	NPC183672
0.8588	High Similarity	NPC36138
0.858	High Similarity	NPC472994
0.858	High Similarity	NPC195685
0.858	High Similarity	NPC477628
0.858	High Similarity	NPC210961
0.858	High Similarity	NPC270675
0.858	High Similarity	NPC477629
0.8571	High Similarity	NPC74319
0.8571	High Similarity	NPC61904
0.8571	High Similarity	NPC73511
0.8571	High Similarity	NPC111929
0.8571	High Similarity	NPC138915
0.8571	High Similarity	NPC472459
0.8571	High Similarity	NPC104677
0.8571	High Similarity	NPC41121
0.8571	High Similarity	NPC472991
0.8571	High Similarity	NPC472992
0.8571	High Similarity	NPC287872
0.8571	High Similarity	NPC144097
0.8571	High Similarity	NPC320283
0.8571	High Similarity	NPC43761
0.8563	High Similarity	NPC4390
0.8563	High Similarity	NPC169977
0.8563	High Similarity	NPC42773
0.8563	High Similarity	NPC45522
0.8563	High Similarity	NPC21666
0.8563	High Similarity	NPC24043
0.8563	High Similarity	NPC101026
0.8562	High Similarity	NPC170475
0.8562	High Similarity	NPC265480
0.8562	High Similarity	NPC149368
0.8562	High Similarity	NPC127406
0.8562	High Similarity	NPC242756
0.8554	High Similarity	NPC44558
0.8554	High Similarity	NPC34287
0.8554	High Similarity	NPC206123
0.8554	High Similarity	NPC149011
0.8554	High Similarity	NPC204937
0.8554	High Similarity	NPC471416
0.8554	High Similarity	NPC105511
0.8553	High Similarity	NPC210003
0.8553	High Similarity	NPC39360
0.8553	High Similarity	NPC83283
0.8553	High Similarity	NPC143851
0.8553	High Similarity	NPC29763
0.8545	High Similarity	NPC317489
0.8545	High Similarity	NPC149244
0.8545	High Similarity	NPC58716
0.8545	High Similarity	NPC116745
0.8545	High Similarity	NPC84362
0.8545	High Similarity	NPC45618
0.8545	High Similarity	NPC173637
0.8545	High Similarity	NPC223424
0.8545	High Similarity	NPC52550
0.8545	High Similarity	NPC48640

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 NPC474401 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	316
0.1-0.2	874
0.2-0.3	1858
0.3-0.4	2611
0.4-0.5	1943
0.5-0.6	1019
0.6-0.7	385
0.7-0.8	132
0.8-0.85	11
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8735	High Similarity	NPD4338	Clinical (unspecified phase)
0.8734	High Similarity	NPD5402	Approved
0.8625	High Similarity	NPD4381	Clinical (unspecified phase)
0.8408	Intermediate Similarity	NPD5403	Approved
0.8393	Intermediate Similarity	NPD6797	Phase 2
0.8343	Intermediate Similarity	NPD7251	Discontinued
0.8333	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8294	Intermediate Similarity	NPD7808	Phase 3
0.828	Intermediate Similarity	NPD5401	Approved
0.8274	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8274	Intermediate Similarity	NPD7054	Approved
0.8246	Intermediate Similarity	NPD8313	Approved
0.8246	Intermediate Similarity	NPD8312	Approved
0.8235	Intermediate Similarity	NPD6559	Discontinued
0.8225	Intermediate Similarity	NPD7472	Approved
0.8225	Intermediate Similarity	NPD7074	Phase 3
0.8214	Intermediate Similarity	NPD3818	Discontinued
0.8171	Intermediate Similarity	NPD7075	Discontinued
0.8107	Intermediate Similarity	NPD3751	Discontinued
0.8025	Intermediate Similarity	NPD4380	Phase 2
0.8012	Intermediate Similarity	NPD1653	Approved
0.8	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD6166	Phase 2
0.7988	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD3817	Phase 2
0.7927	Intermediate Similarity	NPD6801	Discontinued
0.788	Intermediate Similarity	NPD7435	Discontinued
0.7875	Intermediate Similarity	NPD6799	Approved
0.787	Intermediate Similarity	NPD3787	Discontinued
0.7861	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD1934	Approved
0.7814	Intermediate Similarity	NPD6779	Approved
0.7814	Intermediate Similarity	NPD6782	Approved
0.7814	Intermediate Similarity	NPD6776	Approved
0.7814	Intermediate Similarity	NPD6777	Approved
0.7814	Intermediate Similarity	NPD6781	Approved
0.7814	Intermediate Similarity	NPD6778	Approved
0.7814	Intermediate Similarity	NPD6780	Approved
0.7771	Intermediate Similarity	NPD8455	Phase 2
0.7771	Intermediate Similarity	NPD1551	Phase 2
0.7771	Intermediate Similarity	NPD2801	Approved
0.7771	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD2935	Discontinued
0.7742	Intermediate Similarity	NPD1933	Approved
0.7714	Intermediate Similarity	NPD7685	Pre-registration
0.7688	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD3750	Approved
0.7682	Intermediate Similarity	NPD1203	Approved
0.7679	Intermediate Similarity	NPD3882	Suspended
0.7673	Intermediate Similarity	NPD1549	Phase 2
0.7669	Intermediate Similarity	NPD1512	Approved
0.7665	Intermediate Similarity	NPD7819	Suspended
0.7651	Intermediate Similarity	NPD7411	Suspended
0.7651	Intermediate Similarity	NPD1091	Approved
0.7644	Intermediate Similarity	NPD5844	Phase 1
0.764	Intermediate Similarity	NPD6190	Approved
0.7632	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD7874	Approved
0.7611	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD7266	Discontinued
0.761	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD8150	Discontinued
0.7594	Intermediate Similarity	NPD7696	Phase 3
0.7594	Intermediate Similarity	NPD7697	Approved
0.7594	Intermediate Similarity	NPD7698	Approved
0.759	Intermediate Similarity	NPD6599	Discontinued
0.7578	Intermediate Similarity	NPD4628	Phase 3
0.7553	Intermediate Similarity	NPD7871	Phase 2
0.7553	Intermediate Similarity	NPD7870	Phase 2
0.7546	Intermediate Similarity	NPD1511	Approved
0.7542	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD6535	Approved
0.7541	Intermediate Similarity	NPD6534	Approved
0.754	Intermediate Similarity	NPD6823	Phase 2
0.7532	Intermediate Similarity	NPD6832	Phase 2
0.753	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD7701	Phase 2
0.7516	Intermediate Similarity	NPD447	Suspended
0.7516	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8434	Phase 2
0.75	Intermediate Similarity	NPD6233	Phase 2
0.7442	Intermediate Similarity	NPD5494	Approved
0.7436	Intermediate Similarity	NPD2313	Discontinued
0.7425	Intermediate Similarity	NPD3226	Approved
0.7419	Intermediate Similarity	NPD7699	Phase 2
0.7419	Intermediate Similarity	NPD7700	Phase 2
0.7412	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD7801	Approved
0.7409	Intermediate Similarity	NPD7783	Phase 2
0.7407	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD6844	Discontinued
0.7394	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD2346	Discontinued
0.7375	Intermediate Similarity	NPD3748	Approved
0.7375	Intermediate Similarity	NPD1510	Phase 2
0.7375	Intermediate Similarity	NPD7033	Discontinued
0.7371	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7768	Phase 2
0.7368	Intermediate Similarity	NPD9717	Approved
0.7362	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD1465	Phase 2
0.7329	Intermediate Similarity	NPD2796	Approved
0.7326	Intermediate Similarity	NPD3749	Approved
0.7325	Intermediate Similarity	NPD6798	Discontinued
0.7305	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD6959	Discontinued
0.7288	Intermediate Similarity	NPD7228	Approved
0.7277	Intermediate Similarity	NPD8320	Phase 1
0.7277	Intermediate Similarity	NPD8319	Approved
0.7273	Intermediate Similarity	NPD3225	Approved
0.7267	Intermediate Similarity	NPD4308	Phase 3
0.725	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7458	Discontinued
0.7216	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD411	Approved
0.7204	Intermediate Similarity	NPD6213	Phase 3
0.7204	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD6212	Phase 3
0.7202	Intermediate Similarity	NPD7584	Approved
0.72	Intermediate Similarity	NPD7199	Phase 2
0.7193	Intermediate Similarity	NPD37	Approved
0.7188	Intermediate Similarity	NPD6355	Discontinued
0.7184	Intermediate Similarity	NPD6234	Discontinued
0.7179	Intermediate Similarity	NPD2798	Approved
0.7175	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD4965	Approved
0.7168	Intermediate Similarity	NPD4967	Phase 2
0.7168	Intermediate Similarity	NPD4966	Approved
0.716	Intermediate Similarity	NPD2799	Discontinued
0.7159	Intermediate Similarity	NPD6232	Discontinued
0.7135	Intermediate Similarity	NPD7473	Discontinued
0.7134	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD8151	Discontinued
0.7125	Intermediate Similarity	NPD1240	Approved
0.7125	Intermediate Similarity	NPD1613	Approved
0.7125	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD2797	Approved
0.7107	Intermediate Similarity	NPD3268	Approved
0.7107	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD7585	Approved
0.707	Intermediate Similarity	NPD1019	Discontinued
0.7037	Intermediate Similarity	NPD1607	Approved
0.7026	Intermediate Similarity	NPD7583	Approved
0.7025	Intermediate Similarity	NPD2861	Phase 2
0.702	Intermediate Similarity	NPD9493	Approved
0.7019	Intermediate Similarity	NPD4060	Phase 1
0.7019	Intermediate Similarity	NPD4307	Phase 2
0.7013	Intermediate Similarity	NPD3496	Discontinued
0.6994	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7097	Phase 1
0.6989	Remote Similarity	NPD919	Approved
0.6975	Remote Similarity	NPD230	Phase 1
0.6974	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4062	Phase 3
0.6941	Remote Similarity	NPD6273	Approved
0.6941	Remote Similarity	NPD5049	Phase 3
0.694	Remote Similarity	NPD7240	Approved
0.6937	Remote Similarity	NPD7095	Approved
0.6927	Remote Similarity	NPD3926	Phase 2
0.6923	Remote Similarity	NPD1608	Approved
0.6923	Remote Similarity	NPD1481	Phase 2
0.691	Remote Similarity	NPD1247	Approved
0.6909	Remote Similarity	NPD6099	Approved
0.6909	Remote Similarity	NPD6100	Approved
0.6906	Remote Similarity	NPD7799	Discontinued
0.6905	Remote Similarity	NPD2354	Approved
0.6905	Remote Similarity	NPD3887	Approved
0.6894	Remote Similarity	NPD3764	Approved
0.6886	Remote Similarity	NPD1652	Phase 2
0.6885	Remote Similarity	NPD5953	Discontinued
0.6882	Remote Similarity	NPD4661	Approved
0.6882	Remote Similarity	NPD2532	Approved
0.6882	Remote Similarity	NPD2534	Approved
0.6882	Remote Similarity	NPD2533	Approved
0.6882	Remote Similarity	NPD4662	Approved
0.6879	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD4340	Discontinued
0.6871	Remote Similarity	NPD5124	Phase 1
0.6871	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD5763	Approved
0.6867	Remote Similarity	NPD5762	Approved
0.6867	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD2344	Approved
0.6866	Remote Similarity	NPD7930	Approved
0.6859	Remote Similarity	NPD1535	Discovery
0.6855	Remote Similarity	NPD5647	Approved
0.6839	Remote Similarity	NPD1778	Approved
0.6829	Remote Similarity	NPD6653	Approved
0.6826	Remote Similarity	NPD2424	Discontinued

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